#=============================================================================
data_global
loop_
_journal_name_full                 'European Journal of Chemistry'
_journal_coden_ASTM                EJCUA9
_journal_volume                    17
_journal_issue                     1
_journal_year                      2026
_journal_page_first                1
_journal_page_last                 12
#============================================================================= 
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bi183
_database_code_depnum_ccdc_archive 'CCDC 822753'
loop_
_audit_author_name
_audit_author_address
'Bojidarka Ivanova' 'Dortmund University of Technollogy'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.	2026-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'4-Phenyl-pyridine (bis)mandelate (bis)mandelic acid'
_chemical_name_common            
'4-Phenyl-pyridine (bis)mandelate (bis)mandelic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 N O6'
_chemical_formula_weight         459.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.080(3)
_cell_length_b                   14.395(3)
_cell_length_c                   19.408(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.648(7)
_cell_angle_gamma                90.00
_cell_volume                     4739.6(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3668
_cell_measurement_theta_min      0.958
_cell_measurement_theta_max      0.987

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1936
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9584
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 'THETM01_ALERT_3_A  due to low teta=22.13 instead of 25.03o (authomatized datacollection)' 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5830
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         22.13
_reflns_number_total             5830
_reflns_number_gt                3846
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker GIS'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker APEX2'
_computing_publication_material  'Acta Crystallogr. A64 (2008) 112--122'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0788P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5830
_refine_ls_number_parameters     614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1848
_refine_ls_wR_factor_gt          0.1642
_refine_ls_goodness_of_fit_ref   1.359
_refine_ls_restrained_S_all      1.359
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.37393(15) 0.9218(2) 0.67176(13) 0.0763(8) Uani 1 1 d . . .
H1 H 0.3371 0.9222 0.6391 0.114 Uiso 1 1 calc R . .
O3 O 0.09233(15) 0.9299(2) 0.67172(12) 0.0755(8) Uani 1 1 d . . .
H2 H 0.0629 0.9216 0.6345 0.113 Uiso 1 1 calc R . .
O12 O 0.82338(16) 0.89202(19) 0.54595(13) 0.0748(8) Uani 1 1 d . . .
O1 O 0.25800(16) 0.91040(19) 0.58139(13) 0.0766(8) Uani 1 1 d . . .
O9 O 0.70184(15) 0.8705(2) 0.45924(14) 0.0784(8) Uani 1 1 d . . .
H3 H 0.7394 0.8861 0.4888 0.118 Uiso 1 1 calc R . .
O2 O 0.13174(16) 0.8982(2) 0.54318(14) 0.0809(9) Uani 1 1 d . . .
O11 O 0.94884(16) 0.8852(2) 0.58580(14) 0.0780(8) Uani 1 1 d . . .
O10 O 0.98857(17) 0.9075(2) 0.45503(13) 0.0820(8) Uani 1 1 d . . .
H4 H 1.0172 0.9076 0.4932 0.123 Uiso 1 1 calc R . .
O4 O 0.58179(16) 0.9219(2) 0.67953(15) 0.0893(9) Uani 1 1 d . . .
H5 H 0.5855 0.9021 0.6393 0.134 Uiso 1 1 calc R . .
O8 O 0.63143(15) 0.8905(2) 0.54696(16) 0.0843(9) Uani 1 1 d . . .
O5 O 0.44936(16) 0.9366(2) 0.58702(16) 0.0920(9) Uani 1 1 d . . .
O7 O 0.49682(16) 0.8428(3) 0.46756(19) 0.1075(11) Uani 1 1 d . . .
H6 H 0.5049 0.8736 0.5045 0.161 Uiso 1 1 calc R . .
C47 C 0.9143(2) 0.7661(2) 0.44870(16) 0.0519(9) Uani 1 1 d . . .
C31 C 0.50444(19) 0.7909(2) 0.71206(17) 0.0514(9) Uani 1 1 d . . .
C23 C 0.1741(2) 0.7923(3) 0.68697(17) 0.0560(9) Uani 1 1 d . . .
C14 C 0.7993(2) 0.8636(2) 0.89851(19) 0.0550(9) Uani 1 1 d . . .
C3 C 0.2889(2) 0.8666(2) 0.23159(18) 0.0512(9) Uani 1 1 d . . .
C39 C 0.5827(2) 0.7309(3) 0.42523(18) 0.0573(10) Uani 1 1 d . . .
C17 C 0.8215(2) 0.8717(2) 0.82814(17) 0.0533(9) Uani 1 1 d . . .
C6 C 0.2636(2) 0.8748(2) 0.30187(17) 0.0524(9) Uani 1 1 d . . .
C29 C 0.1670(2) 0.8936(3) 0.66544(17) 0.0591(10) Uani 1 1 d . . .
H7 H 0.2068 0.9302 0.6961 0.071 Uiso 1 1 calc R . .
C32 C 0.5197(2) 0.7310(3) 0.66130(18) 0.0632(10) Uani 1 1 d . . .
H8 H 0.5370 0.7543 0.6199 0.076 Uiso 1 1 calc R . .
C53 C 0.9155(2) 0.8689(2) 0.46365(18) 0.0576(10) Uani 1 1 d . . .
H9 H 0.8744 0.8996 0.4304 0.069 Uiso 1 1 calc R . .
N1 N 0.8717(4) 0.8806(3) 0.7006(3) 0.1135(18) Uani 1 1 d . . .
H10 H 0.8889 0.8836 0.6596 0.136 Uiso 1 1 calc R . .
C30 C 0.1866(3) 0.9021(3) 0.5906(2) 0.0642(10) Uani 1 1 d . . .
N2 N 0.2109(4) 0.8915(3) 0.4282(2) 0.1029(15) Uani 1 1 d . . .
H11 H 0.1930 0.8968 0.4688 0.124 Uiso 1 1 calc R . .
C52 C 0.8481(2) 0.7233(3) 0.41524(19) 0.0662(10) Uani 1 1 d . . .
H12 H 0.8023 0.7589 0.4011 0.079 Uiso 1 1 calc R . .
C54 C 0.8946(3) 0.8840(2) 0.5371(2) 0.0597(10) Uani 1 1 d . . .
C38 C 0.4410(2) 0.9216(2) 0.6466(2) 0.0641(11) Uani 1 1 d . . .
C37 C 0.5098(2) 0.8937(3) 0.7004(2) 0.0662(11) Uani 1 1 d . . .
H13 H 0.5029 0.9258 0.7450 0.079 Uiso 1 1 calc R . .
C46 C 0.6369(2) 0.8687(3) 0.4882(2) 0.0648(10) Uani 1 1 d . . .
C33 C 0.5104(2) 0.6370(3) 0.6691(2) 0.0733(11) Uani 1 1 d . . .
H14 H 0.5210 0.5960 0.6329 0.088 Uiso 1 1 calc R . .
C36 C 0.4805(2) 0.7553(3) 0.77164(19) 0.0704(11) Uani 1 1 d . . .
H15 H 0.4699 0.7962 0.8079 0.084 Uiso 1 1 calc R . .
C44 C 0.5710(2) 0.6650(3) 0.47403(19) 0.0747(12) Uani 1 1 d . . .
H16 H 0.5506 0.6829 0.5156 0.090 Uiso 1 1 calc R . .
C13 C 0.8447(2) 0.8158(3) 0.9498(2) 0.0677(11) Uani 1 1 d . . .
H17 H 0.8929 0.7889 0.9399 0.081 Uiso 1 1 calc R . .
C48 C 0.9799(2) 0.7126(3) 0.4685(2) 0.0728(11) Uani 1 1 d . . .
H18 H 1.0262 0.7405 0.4914 0.087 Uiso 1 1 calc R . .
C28 C 0.2442(2) 0.7558(3) 0.71986(19) 0.0725(12) Uani 1 1 d . . .
H19 H 0.2890 0.7949 0.7294 0.087 Uiso 1 1 calc R . .
C24 C 0.1109(2) 0.7334(3) 0.6736(2) 0.0742(11) Uani 1 1 d . . .
H20 H 0.0626 0.7563 0.6505 0.089 Uiso 1 1 calc R . .
C40 C 0.6109(2) 0.7027(3) 0.3661(2) 0.0755(12) Uani 1 1 d . . .
H21 H 0.6195 0.7475 0.3319 0.091 Uiso 1 1 calc R . .
C34 C 0.4864(2) 0.6022(3) 0.7279(2) 0.0736(12) Uani 1 1 d . . .
H22 H 0.4799 0.5371 0.7329 0.088 Uiso 1 1 calc R . .
C45 C 0.5684(2) 0.8314(3) 0.4389(2) 0.0736(11) Uani 1 1 d . . .
H23 H 0.5655 0.8664 0.3942 0.088 Uiso 1 1 calc R . .
C50 C 0.9127(4) 0.5772(3) 0.4217(2) 0.0886(14) Uani 1 1 d . . .
H24 H 0.9122 0.5124 0.4123 0.106 Uiso 1 1 calc R . .
C22 C 0.8993(3) 0.8673(3) 0.8165(2) 0.0775(12) Uani 1 1 d . . .
H25 H 0.9383 0.8618 0.8553 0.093 Uiso 1 1 calc R . .
C35 C 0.4716(2) 0.6607(3) 0.7797(2) 0.0774(12) Uani 1 1 d . . .
H26 H 0.4552 0.6367 0.8213 0.093 Uiso 1 1 calc R . .
C51 C 0.8482(3) 0.6292(3) 0.4022(2) 0.0842(13) Uani 1 1 d . . .
H27 H 0.8022 0.6006 0.3793 0.101 Uiso 1 1 calc R . .
C42 C 0.6167(3) 0.5483(3) 0.4031(3) 0.0862(13) Uani 1 1 d . . .
H28 H 0.6292 0.4851 0.3953 0.103 Uiso 1 1 calc R . .
C10 C 0.2859(4) 0.9066(3) 0.4247(2) 0.0965(17) Uani 1 1 d . . .
H29 H 0.3199 0.9230 0.4651 0.116 Uiso 1 1 calc R . .
C19 C 0.7949(4) 0.8871(3) 0.7027(3) 0.104(2) Uani 1 1 d . . .
H30 H 0.7596 0.8947 0.6616 0.125 Uiso 1 1 calc R . .
C18 C 0.7664(3) 0.8820(3) 0.7703(2) 0.0838(13) Uani 1 1 d . . .
H31 H 0.7117 0.8858 0.7747 0.101 Uiso 1 1 calc R . .
C43 C 0.5886(3) 0.5729(3) 0.4631(2) 0.0887(14) Uani 1 1 d . . .
H32 H 0.5810 0.5274 0.4971 0.106 Uiso 1 1 calc R . .
C49 C 0.9785(3) 0.6180(3) 0.4550(2) 0.0894(13) Uani 1 1 d . . .
H33 H 1.0238 0.5814 0.4690 0.107 Uiso 1 1 calc R . .
C25 C 0.1168(3) 0.6418(3) 0.6932(2) 0.0918(14) Uani 1 1 d . . .
H34 H 0.0723 0.6022 0.6843 0.110 Uiso 1 1 calc R . .
C11 C 0.3157(3) 0.8982(3) 0.3592(2) 0.0814(13) Uani 1 1 d . . .
H35 H 0.3699 0.9083 0.3551 0.098 Uiso 1 1 calc R . .
C41 C 0.6270(3) 0.6121(4) 0.3548(2) 0.0886(14) Uani 1 1 d . . .
H36 H 0.6457 0.5940 0.3126 0.106 Uiso 1 1 calc R . .
C12 C 0.8220(4) 0.8061(3) 1.0150(2) 0.0948(15) Uani 1 1 d . . .
H37 H 0.8546 0.7719 1.0491 0.114 Uiso 1 1 calc R . .
C27 C 0.2494(3) 0.6646(4) 0.7386(2) 0.0861(13) Uani 1 1 d . . .
H38 H 0.2976 0.6409 0.7611 0.103 Uiso 1 1 calc R . .
C26 C 0.1862(3) 0.6068(3) 0.7255(2) 0.0940(14) Uani 1 1 d . . .
H39 H 0.1902 0.5432 0.7385 0.113 Uiso 1 1 calc R . .
C7 C 0.1870(3) 0.8606(3) 0.3130(2) 0.0872(14) Uani 1 1 d . . .
H40 H 0.1497 0.8439 0.2748 0.105 Uiso 1 1 calc R . .
C9 C 0.3343(3) 0.8487(3) 0.1007(3) 0.0988(15) Uiso 1 1 d . . .
H41 H 0.3502 0.8432 0.0556 0.119 Uiso 1 1 calc R . .
C4 C 0.2381(3) 0.8439(4) 0.1751(2) 0.0964(16) Uani 1 1 d . . .
H42 H 0.1843 0.8335 0.1807 0.116 Uiso 1 1 calc R . .
C2 C 0.3648(2) 0.8798(4) 0.2197(2) 0.1022(17) Uani 1 1 d . . .
H43 H 0.4031 0.8961 0.2571 0.123 Uiso 1 1 calc R . .
C15 C 0.7320(3) 0.9040(4) 0.9161(3) 0.1055(16) Uani 1 1 d . . .
H44 H 0.6992 0.9388 0.8825 0.127 Uiso 1 1 calc R . .
C20 C 0.7568(5) 0.8427(5) 1.0312(3) 0.123(2) Uani 1 1 d . . .
H45 H 0.7410 0.8337 1.0761 0.148 Uiso 1 1 calc R . .
C21 C 0.9228(4) 0.8705(4) 0.7531(3) 0.1092(19) Uani 1 1 d . . .
H46 H 0.9771 0.8653 0.7474 0.131 Uiso 1 1 calc R . .
C5 C 0.2621(3) 0.8353(4) 0.1089(2) 0.1109(17) Uani 1 1 d . . .
H47 H 0.2249 0.8197 0.0703 0.133 Uiso 1 1 calc R . .
C8 C 0.1627(4) 0.8694(4) 0.3759(3) 0.1138(19) Uani 1 1 d . . .
H48 H 0.1088 0.8591 0.3815 0.137 Uiso 1 1 calc R . .
C1 C 0.3875(3) 0.8698(4) 0.1528(3) 0.127(2) Uani 1 1 d . . .
H49 H 0.4410 0.8783 0.1453 0.152 Uiso 1 1 calc R . .
C16 C 0.7113(4) 0.8946(5) 0.9823(4) 0.142(2) Uani 1 1 d . . .
H50 H 0.6652 0.9244 0.9943 0.170 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O6 0.0689(17) 0.088(2) 0.0757(18) -0.0034(16) 0.0249(15) 0.0024(16)
O3 0.0819(19) 0.096(2) 0.0512(16) -0.0097(14) 0.0168(13) 0.0256(17)
O12 0.0707(19) 0.089(2) 0.0684(18) -0.0108(14) 0.0253(15) -0.0086(15)
O1 0.0717(19) 0.099(2) 0.0613(17) 0.0078(14) 0.0181(14) -0.0003(16)
O9 0.0674(18) 0.093(2) 0.0779(19) -0.0196(16) 0.0207(15) -0.0188(16)
O2 0.0718(19) 0.122(2) 0.0496(17) 0.0083(15) 0.0109(14) 0.0112(17)
O11 0.0703(19) 0.113(2) 0.0523(17) -0.0077(15) 0.0119(14) -0.0054(16)
O10 0.097(2) 0.092(2) 0.0604(17) -0.0031(15) 0.0241(15) -0.0286(17)
O4 0.0740(18) 0.093(2) 0.105(2) -0.0195(18) 0.0265(17) -0.0363(16)
O8 0.0703(19) 0.098(2) 0.089(2) -0.0351(17) 0.0273(16) -0.0179(15)
O5 0.092(2) 0.105(2) 0.086(2) 0.0304(18) 0.0411(17) 0.0232(17)
O7 0.0622(19) 0.109(3) 0.150(3) -0.045(2) 0.009(2) -0.0052(17)
C47 0.064(2) 0.054(2) 0.039(2) 0.0016(17) 0.0160(18) -0.003(2)
C31 0.051(2) 0.058(2) 0.045(2) -0.0068(18) 0.0067(17) -0.0058(18)
C23 0.064(3) 0.065(3) 0.041(2) -0.0021(18) 0.0113(18) -0.005(2)
C14 0.058(2) 0.047(2) 0.061(2) -0.0075(18) 0.013(2) 0.0013(19)
C3 0.055(2) 0.043(2) 0.056(2) -0.0020(16) 0.0072(19) -0.0004(17)
C39 0.058(2) 0.066(3) 0.047(2) -0.008(2) 0.0002(18) -0.0138(19)
C17 0.070(3) 0.042(2) 0.048(2) -0.0033(16) 0.009(2) 0.0011(18)
C6 0.072(3) 0.041(2) 0.043(2) 0.0022(16) 0.006(2) 0.0002(18)
C29 0.061(2) 0.070(3) 0.046(2) -0.0052(18) 0.0084(18) 0.000(2)
C32 0.078(3) 0.064(3) 0.048(2) -0.0021(19) 0.0125(19) -0.007(2)
C53 0.063(2) 0.061(2) 0.052(2) -0.0003(18) 0.0203(18) -0.015(2)
N1 0.216(6) 0.062(3) 0.069(3) 0.000(2) 0.043(4) -0.004(4)
C30 0.077(3) 0.059(2) 0.060(3) 0.0047(19) 0.021(2) 0.010(2)
N2 0.186(5) 0.066(3) 0.064(3) 0.004(2) 0.045(3) 0.008(3)
C52 0.062(3) 0.073(3) 0.064(2) -0.009(2) 0.010(2) -0.002(2)
C54 0.072(3) 0.054(2) 0.056(3) -0.0013(18) 0.019(2) -0.010(2)
C38 0.073(3) 0.048(2) 0.077(3) 0.000(2) 0.033(3) 0.000(2)
C37 0.063(3) 0.071(3) 0.067(3) -0.014(2) 0.018(2) -0.017(2)
C46 0.060(3) 0.057(3) 0.079(3) -0.009(2) 0.016(2) -0.008(2)
C33 0.093(3) 0.066(3) 0.063(3) -0.011(2) 0.014(2) -0.003(2)
C36 0.077(3) 0.085(3) 0.052(2) -0.008(2) 0.019(2) -0.004(2)
C44 0.104(3) 0.075(3) 0.045(2) -0.002(2) 0.011(2) -0.013(3)
C13 0.074(3) 0.068(3) 0.061(3) 0.002(2) 0.006(2) 0.005(2)
C48 0.076(3) 0.067(3) 0.074(3) 0.008(2) 0.004(2) -0.002(2)
C28 0.061(3) 0.086(3) 0.069(3) 0.017(2) 0.002(2) -0.008(2)
C24 0.073(3) 0.075(3) 0.073(3) -0.008(2) 0.000(2) -0.001(2)
C40 0.093(3) 0.076(3) 0.058(3) 0.000(2) 0.010(2) -0.018(2)
C34 0.071(3) 0.068(3) 0.081(3) 0.010(2) 0.005(2) -0.005(2)
C45 0.067(3) 0.068(3) 0.084(3) -0.005(2) 0.003(2) -0.008(2)
C50 0.118(4) 0.059(3) 0.095(3) -0.003(3) 0.040(3) -0.004(3)
C22 0.084(3) 0.090(3) 0.061(3) -0.013(2) 0.022(2) -0.014(2)
C35 0.081(3) 0.093(4) 0.062(3) 0.015(3) 0.023(2) -0.005(3)
C51 0.091(4) 0.081(4) 0.082(3) -0.021(3) 0.017(3) -0.025(3)
C42 0.091(3) 0.074(3) 0.089(4) -0.021(3) -0.008(3) -0.009(3)
C10 0.171(5) 0.054(3) 0.055(3) -0.002(2) -0.026(3) -0.029(3)
C19 0.183(6) 0.047(3) 0.069(4) -0.001(2) -0.041(4) 0.020(4)
C18 0.120(4) 0.068(3) 0.059(3) -0.003(2) -0.007(3) 0.020(3)
C43 0.120(4) 0.074(3) 0.069(3) 0.019(2) -0.006(3) -0.019(3)
C49 0.091(4) 0.074(4) 0.104(4) 0.017(3) 0.014(3) 0.015(3)
C25 0.093(4) 0.072(4) 0.110(4) -0.012(3) 0.008(3) -0.018(3)
C11 0.119(4) 0.066(3) 0.057(3) 0.002(2) 0.002(3) -0.026(3)
C41 0.103(4) 0.096(4) 0.070(3) -0.022(3) 0.022(3) -0.017(3)
C12 0.137(5) 0.093(4) 0.053(3) 0.007(2) 0.005(3) -0.017(3)
C27 0.078(3) 0.090(4) 0.088(3) 0.030(3) -0.002(2) 0.006(3)
C26 0.113(4) 0.075(3) 0.096(4) 0.018(3) 0.022(3) 0.004(3)
C7 0.077(3) 0.129(4) 0.060(3) 0.002(2) 0.024(2) 0.011(3)
C4 0.067(3) 0.166(5) 0.056(3) -0.008(3) 0.007(2) -0.016(3)
C2 0.062(3) 0.162(5) 0.083(3) -0.033(3) 0.011(3) -0.015(3)
C15 0.094(4) 0.132(5) 0.094(4) -0.005(3) 0.024(3) 0.033(3)
C20 0.159(6) 0.134(6) 0.088(4) -0.024(4) 0.065(5) -0.044(5)
C21 0.154(5) 0.113(4) 0.069(4) -0.019(3) 0.050(4) -0.031(4)
C5 0.106(4) 0.160(5) 0.063(3) -0.016(3) -0.008(3) -0.017(4)
C8 0.122(5) 0.158(5) 0.068(4) 0.004(3) 0.039(3) 0.022(4)
C1 0.068(3) 0.185(6) 0.137(5) -0.019(4) 0.054(3) -0.004(3)
C16 0.108(5) 0.189(7) 0.141(6) -0.042(5) 0.069(4) 0.013(4)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 C38 1.295(4) . ?
O6 H1 0.8400 . ?
O3 C29 1.397(4) . ?
O3 H2 0.8400 . ?
O12 C54 1.254(4) . ?
O1 C30 1.258(4) . ?
O9 C46 1.301(4) . ?
O9 H3 0.8400 . ?
O2 C30 1.237(4) . ?
O11 C54 1.245(4) . ?
O10 C53 1.393(4) . ?
O10 H4 0.8400 . ?
O4 C37 1.399(4) . ?
O4 H5 0.8400 . ?
O8 C46 1.198(4) . ?
O5 C38 1.202(4) . ?
O7 C45 1.411(4) . ?
O7 H6 0.8400 . ?
C47 C48 1.377(5) . ?
C47 C52 1.382(5) . ?
C47 C53 1.507(5) . ?
C31 C32 1.358(5) . ?
C31 C36 1.370(5) . ?
C31 C37 1.500(5) . ?
C23 C24 1.374(5) . ?
C23 C28 1.393(5) . ?
C23 C29 1.518(5) . ?
C14 C15 1.367(5) . ?
C14 C13 1.374(5) . ?
C14 C17 1.464(5) . ?
C3 C2 1.355(5) . ?
C3 C4 1.358(5) . ?
C3 C6 1.482(5) . ?
C39 C40 1.357(5) . ?
C39 C44 1.371(5) . ?
C39 C45 1.496(5) . ?
C17 C22 1.376(5) . ?
C17 C18 1.387(5) . ?
C6 C7 1.366(5) . ?
C6 C11 1.383(5) . ?
C29 C30 1.533(5) . ?
C29 H7 1.0000 . ?
C32 C33 1.372(5) . ?
C32 H8 0.9500 . ?
C53 C54 1.524(5) . ?
C53 H9 1.0000 . ?
N1 C21 1.270(6) . ?
N1 C19 1.321(6) . ?
N1 H10 0.8800 . ?
N2 C8 1.271(6) . ?
N2 C10 1.307(6) . ?
N2 H11 0.8800 . ?
C52 C51 1.378(5) . ?
C52 H12 0.9500 . ?
C38 C37 1.533(5) . ?
C37 H13 1.0000 . ?
C46 C45 1.519(5) . ?
C33 C34 1.353(5) . ?
C33 H14 0.9500 . ?
C36 C35 1.381(5) . ?
C36 H15 0.9500 . ?
C44 C43 1.381(6) . ?
C44 H16 0.9500 . ?
C13 C12 1.373(6) . ?
C13 H17 0.9500 . ?
C48 C49 1.385(6) . ?
C48 H18 0.9500 . ?
C28 C27 1.363(6) . ?
C28 H19 0.9500 . ?
C24 C25 1.374(6) . ?
C24 H20 0.9500 . ?
C40 C41 1.356(6) . ?
C40 H21 0.9500 . ?
C34 C35 1.358(5) . ?
C34 H22 0.9500 . ?
C45 H23 1.0000 . ?
C50 C51 1.349(6) . ?
C50 C49 1.363(6) . ?
C50 H24 0.9500 . ?
C22 C21 1.338(6) . ?
C22 H25 0.9500 . ?
C35 H26 0.9500 . ?
C51 H27 0.9500 . ?
C42 C41 1.339(6) . ?
C42 C43 1.357(6) . ?
C42 H28 0.9500 . ?
C10 C11 1.430(6) . ?
C10 H29 0.9500 . ?
C19 C18 1.452(7) . ?
C19 H30 0.9500 . ?
C18 H31 0.9500 . ?
C43 H32 0.9500 . ?
C49 H33 0.9500 . ?
C25 C26 1.371(6) . ?
C25 H34 0.9500 . ?
C11 H35 0.9500 . ?
C41 H36 0.9500 . ?
C12 C20 1.303(7) . ?
C12 H37 0.9500 . ?
C27 C26 1.363(6) . ?
C27 H38 0.9500 . ?
C26 H39 0.9500 . ?
C7 C8 1.342(6) . ?
C7 H40 0.9500 . ?
C9 C5 1.277(6) . ?
C9 C1 1.313(6) . ?
C9 H41 0.9500 . ?
C4 C5 1.398(6) . ?
C4 H42 0.9500 . ?
C2 C1 1.404(6) . ?
C2 H43 0.9500 . ?
C15 C16 1.378(7) . ?
C15 H44 0.9500 . ?
C20 C16 1.376(8) . ?
C20 H45 0.9500 . ?
C21 H46 0.9500 . ?
C5 H47 0.9500 . ?
C8 H48 0.9500 . ?
C1 H49 0.9500 . ?
C16 H50 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C38 O6 H1 109.5 . . ?
C29 O3 H2 109.5 . . ?
C46 O9 H3 109.5 . . ?
C53 O10 H4 109.5 . . ?
C37 O4 H5 109.5 . . ?
C45 O7 H6 109.5 . . ?
C48 C47 C52 118.4(3) . . ?
C48 C47 C53 120.2(3) . . ?
C52 C47 C53 121.4(3) . . ?
C32 C31 C36 118.4(4) . . ?
C32 C31 C37 119.8(3) . . ?
C36 C31 C37 121.7(3) . . ?
C24 C23 C28 118.0(4) . . ?
C24 C23 C29 120.3(4) . . ?
C28 C23 C29 121.7(3) . . ?
C15 C14 C13 116.9(4) . . ?
C15 C14 C17 121.1(4) . . ?
C13 C14 C17 122.0(3) . . ?
C2 C3 C4 115.5(4) . . ?
C2 C3 C6 122.1(3) . . ?
C4 C3 C6 122.4(3) . . ?
C40 C39 C44 118.1(4) . . ?
C40 C39 C45 121.4(4) . . ?
C44 C39 C45 120.5(4) . . ?
C22 C17 C18 116.7(4) . . ?
C22 C17 C14 120.6(3) . . ?
C18 C17 C14 122.6(4) . . ?
C7 C6 C11 116.7(4) . . ?
C7 C6 C3 121.3(3) . . ?
C11 C6 C3 122.0(4) . . ?
O3 C29 C23 112.4(3) . . ?
O3 C29 C30 110.8(3) . . ?
C23 C29 C30 108.6(3) . . ?
O3 C29 H7 108.3 . . ?
C23 C29 H7 108.3 . . ?
C30 C29 H7 108.3 . . ?
C31 C32 C33 120.8(3) . . ?
C31 C32 H8 119.6 . . ?
C33 C32 H8 119.6 . . ?
O10 C53 C47 111.2(3) . . ?
O10 C53 C54 111.4(3) . . ?
C47 C53 C54 108.7(3) . . ?
O10 C53 H9 108.5 . . ?
C47 C53 H9 108.5 . . ?
C54 C53 H9 108.5 . . ?
C21 N1 C19 125.1(5) . . ?
C21 N1 H10 117.4 . . ?
C19 N1 H10 117.4 . . ?
O2 C30 O1 124.2(4) . . ?
O2 C30 C29 118.1(4) . . ?
O1 C30 C29 117.6(4) . . ?
C8 N2 C10 123.2(5) . . ?
C8 N2 H11 118.4 . . ?
C10 N2 H11 118.4 . . ?
C51 C52 C47 120.5(4) . . ?
C51 C52 H12 119.8 . . ?
C47 C52 H12 119.8 . . ?
O11 C54 O12 122.9(3) . . ?
O11 C54 C53 118.5(3) . . ?
O12 C54 C53 118.5(4) . . ?
O5 C38 O6 124.8(4) . . ?
O5 C38 C37 122.4(3) . . ?
O6 C38 C37 112.7(3) . . ?
O4 C37 C31 113.6(3) . . ?
O4 C37 C38 110.9(3) . . ?
C31 C37 C38 107.8(3) . . ?
O4 C37 H13 108.1 . . ?
C31 C37 H13 108.1 . . ?
C38 C37 H13 108.1 . . ?
O8 C46 O9 124.7(4) . . ?
O8 C46 C45 123.6(4) . . ?
O9 C46 C45 111.6(4) . . ?
C34 C33 C32 120.5(4) . . ?
C34 C33 H14 119.7 . . ?
C32 C33 H14 119.7 . . ?
C31 C36 C35 120.8(4) . . ?
C31 C36 H15 119.6 . . ?
C35 C36 H15 119.6 . . ?
C39 C44 C43 120.4(4) . . ?
C39 C44 H16 119.8 . . ?
C43 C44 H16 119.8 . . ?
C12 C13 C14 121.6(4) . . ?
C12 C13 H17 119.2 . . ?
C14 C13 H17 119.2 . . ?
C47 C48 C49 120.1(4) . . ?
C47 C48 H18 120.0 . . ?
C49 C48 H18 120.0 . . ?
C27 C28 C23 120.8(4) . . ?
C27 C28 H19 119.6 . . ?
C23 C28 H19 119.6 . . ?
C23 C24 C25 120.6(4) . . ?
C23 C24 H20 119.7 . . ?
C25 C24 H20 119.7 . . ?
C41 C40 C39 121.6(4) . . ?
C41 C40 H21 119.2 . . ?
C39 C40 H21 119.2 . . ?
C33 C34 C35 119.7(4) . . ?
C33 C34 H22 120.1 . . ?
C35 C34 H22 120.1 . . ?
O7 C45 C39 110.4(3) . . ?
O7 C45 C46 110.5(3) . . ?
C39 C45 C46 108.9(3) . . ?
O7 C45 H23 109.0 . . ?
C39 C45 H23 109.0 . . ?
C46 C45 H23 109.0 . . ?
C51 C50 C49 119.7(4) . . ?
C51 C50 H24 120.1 . . ?
C49 C50 H24 120.2 . . ?
C21 C22 C17 123.2(5) . . ?
C21 C22 H25 118.4 . . ?
C17 C22 H25 118.4 . . ?
C34 C35 C36 119.7(4) . . ?
C34 C35 H26 120.2 . . ?
C36 C35 H26 120.2 . . ?
C50 C51 C52 120.8(4) . . ?
C50 C51 H27 119.6 . . ?
C52 C51 H27 119.6 . . ?
C41 C42 C43 120.6(4) . . ?
C41 C42 H28 119.7 . . ?
C43 C42 H28 119.7 . . ?
N2 C10 C11 118.9(4) . . ?
N2 C10 H29 120.5 . . ?
C11 C10 H29 120.5 . . ?
N1 C19 C18 117.6(4) . . ?
N1 C19 H30 121.2 . . ?
C18 C19 H30 121.2 . . ?
C17 C18 C19 118.0(4) . . ?
C17 C18 H31 121.0 . . ?
C19 C18 H31 121.0 . . ?
C42 C43 C44 119.2(4) . . ?
C42 C43 H32 120.4 . . ?
C44 C43 H32 120.4 . . ?
C50 C49 C48 120.6(4) . . ?
C50 C49 H33 119.7 . . ?
C48 C49 H33 119.7 . . ?
C26 C25 C24 120.8(4) . . ?
C26 C25 H34 119.6 . . ?
C24 C25 H34 119.6 . . ?
C6 C11 C10 118.3(4) . . ?
C6 C11 H35 120.9 . . ?
C10 C11 H35 120.9 . . ?
C42 C41 C40 120.1(4) . . ?
C42 C41 H36 120.0 . . ?
C40 C41 H36 120.0 . . ?
C20 C12 C13 121.4(5) . . ?
C20 C12 H37 119.3 . . ?
C13 C12 H37 119.3 . . ?
C28 C27 C26 120.9(4) . . ?
C28 C27 H38 119.6 . . ?
C26 C27 H38 119.6 . . ?
C27 C26 C25 119.0(4) . . ?
C27 C26 H39 120.5 . . ?
C25 C26 H39 120.5 . . ?
C8 C7 C6 122.2(5) . . ?
C8 C7 H40 118.9 . . ?
C6 C7 H40 118.9 . . ?
C5 C9 C1 122.1(5) . . ?
C5 C9 H41 118.9 . . ?
C1 C9 H41 118.9 . . ?
C3 C4 C5 122.4(4) . . ?
C3 C4 H42 118.8 . . ?
C5 C4 H42 118.8 . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 H43 119.5 . . ?
C1 C2 H43 119.5 . . ?
C14 C15 C16 120.3(5) . . ?
C14 C15 H44 119.9 . . ?
C16 C15 H44 119.9 . . ?
C12 C20 C16 118.9(6) . . ?
C12 C20 H45 120.6 . . ?
C16 C20 H45 120.6 . . ?
N1 C21 C22 119.4(6) . . ?
N1 C21 H46 120.3 . . ?
C22 C21 H46 120.3 . . ?
C9 C5 C4 119.3(5) . . ?
C9 C5 H47 120.3 . . ?
C4 C5 H47 120.3 . . ?
N2 C8 C7 120.7(5) . . ?
N2 C8 H48 119.7 . . ?
C7 C8 H48 119.7 . . ?
C9 C1 C2 119.7(5) . . ?
C9 C1 H49 120.2 . . ?
C2 C1 H49 120.2 . . ?
C20 C16 C15 120.8(5) . . ?
C20 C16 H50 119.6 . . ?
C15 C16 H50 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        22.13
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.039