#==============================================================================
data_global
loop_
_journal_name_full                 'European Journal of Chemistry'
_journal_coden_ASTM                EJCUA9
_journal_volume                    10
_journal_issue                     2
_journal_year                      2019
_journal_page_first                139
_journal_page_last                 145
#===============================================================================

####################################################################### 
# 
# 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_crystal
_database_code_depnum_ccdc_archive 'CCDC 883173'
_audit_update_record             
;
2012-05-22 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;
#TrackingRef 'eg054.cif'

_chemical_name_systematic 
'3-(2-hydroxy-phenylimino)-1,3-diphenyl-propan-1-one '
_chemical_name_common 
'3-(2-hydroxy-phenylimino)-1,3-diphenyl-propan-1-one '
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_weight         315.36
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
#_symmetry_Int_Tables_number ?

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
_cell_length_a                   9.051(3)
_cell_length_b                   10.245(3)
_cell_length_c                   11.016(3)
_cell_angle_alpha                69.28(2)
_cell_angle_beta                 81.66(2)
_cell_angle_gamma                64.25(2)
_cell_volume                     860.5(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4143
_cell_measurement_theta_min       2.33
_cell_measurement_theta_max      27.99
_cell_measurement_temperature    293(2)

_exptl_crystal_F_000             332
_exptl_crystal_density_diffrn    1.217
_exptl_absorpt_coefficient_mu    0.078
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.375
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?


_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
STOE Imaging Plate Diffractometer System (IPDS)
;

_diffrn_radiation_wavelength     0.71069
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_method       ?
_diffrn_reflns_number            4364
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_number_total             4364
_reflns_number_gt                4143
_reflns_threshold_expression     I>2\s(I)

_refine_ls_structure_factor_coef ?
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1304

_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_number_reflns         4143
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_weighting_scheme      ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_shift/su_max          ?
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O(1) 0.3290(1) 0.3968(1) 0.9112(1) 0.051(1)
C(16) 0.7509(1) -0.0439(1) 1.2283(1) 0.053(1)
C(11) 0.6519(1) 0.1119(1) 1.1818(1) 0.040(1)
N(10) 0.4996(1) 0.1771(1) 1.1171(1) 0.045(1)
C(13) 0.8598(1) 0.1639(2) 1.2450(1) 0.053(1)
C(1) 0.3869(1) 0.1221(1) 1.1274(1) 0.041(1)
C(4) 0.0838(1) 0.4073(1) 0.8493(1) 0.046(1)
C(12) 0.7084(1) 0.2163(1) 1.1893(1) 0.045(1)
C(3) 0.2307(1) 0.3337(1) 0.9357(1) 0.043(1)
O(2) 0.6054(1) 0.3662(1) 1.1401(1) 0.074(1)
C(2) 0.2563(1) 0.1963(1) 1.0404(1) 0.045(1)
C(17) 0.3949(1) -0.0164(1) 1.2385(1) 0.042(1)
C(15) 0.9015(2) -0.0950(2) 1.2844(1) 0.062(1)
C(18) 0.3914(2) -0.0146(2) 1.3644(1) 0.054(1)
C(20) 0.3964(2) -0.2660(2) 1.4476(1) 0.071(1)
C(22) 0.3973(2) -0.1429(1) 1.2179(1) 0.052(1)
C(8) -0.1991(2) 0.4706(2) 0.8133(2) 0.080(1)
C(19) 0.3914(2) -0.1397(2) 1.4684(1) 0.067(1)
C(14) 0.9554(1) 0.0083(2) 1.2934(1) 0.060(1)
C(21) 0.4004(2) -0.2687(2) 1.3234(2) 0.066(1)
C(9) -0.0624(2) 0.3941(2) 0.8941(1) 0.061(1)
C(7) -0.1903(3) 0.5571(2) 0.6885(2) 0.090(1)
C(5) 0.0919(2) 0.4957(2) 0.7219(1) 0.068(1)
C(6) -0.0468(3) 0.5698(2) 0.6419(2) 0.092(1)
H(16) 0.7112(18) -0.1151(17) 1.2174(14) 0.065(4)
H(22) 0.3972(20) -0.1425(18) 1.1290(16) 0.073(4)
H(18) 0.3867(18) 0.0823(18) 1.3769(14) 0.068(4)
H(2) 0.1756(15) 0.1525(14) 1.0547(12) 0.049(3)
H(21) 0.4018(19) -0.3563(19) 1.3060(15) 0.075(4)
H(9) -0.0727(20) 0.3366(19) 0.9915(16) 0.079(5)
H(13) 0.8939(18) 0.2407(18) 1.2536(15) 0.071(4)
H(19) 0.3932(22) -0.1372(20) 1.5576(19) 0.088(5)
H(15) 0.9663(21) -0.2079(21) 1.3077(16) 0.082(5)
H(211) 0.6523(21) 0.4325(20) 1.1357(16) 0.081(5)
H(14) 1.0618(19) -0.0265(16) 1.3293(14) 0.062(4)
H(8) -0.2995(40) 0.4590(31) 0.8445(28) 0.150(9)
H(5) 0.1963(19) 0.5028(18) 0.6886(15) 0.068(4)
H(20) 0.3881(28) -0.3500(26) 1.5213(24) 0.124(7)
H(6) -0.0279(25) 0.6223(25) 0.5556(22) 0.107(6)
H(7) -0.2870(29) 0.6099(27) 0.6359(23) 0.121(7)
H(10) 0.4728(18) 0.2696(18) 1.0594(15) 0.064(4)

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
O(1) 0.053(1) 0.042(1) 0.057(1) -0.005(1) -0.008(1) -0.024(1)
C(16) 0.047(1) 0.042(1) 0.064(1) -0.015(1) -0.004(1) -0.015(1)
C(11) 0.037(1) 0.041(1) 0.040(1) -0.008(1) -0.002(1) -0.017(1)
N(10) 0.044(1) 0.038(1) 0.048(1) -0.002(1) -0.011(1) -0.019(1)
C(13) 0.041(1) 0.057(1) 0.063(1) -0.013(1) -0.003(1) -0.025(1)
C(1) 0.043(1) 0.040(1) 0.040(1) -0.010(1) -0.002(1) -0.019(1)
C(4) 0.049(1) 0.039(1) 0.048(1) -0.013(1) -0.011(1) -0.012(1)
C(12) 0.039(1) 0.040(1) 0.051(1) -0.007(1) -0.002(1) -0.018(1)
C(3) 0.044(1) 0.039(1) 0.044(1) -0.011(1) -0.004(1) -0.016(1)
O(2) 0.049(1) 0.039(1) 0.127(1) -0.005(1) -0.024(1) -0.021(1)
C(2) 0.046(1) 0.046(1) 0.045(1) -0.007(1) -0.006(1) -0.024(1)
C(17) 0.039(1) 0.041(1) 0.041(1) -0.006(1) -0.003(1) -0.018(1)
C(15) 0.046(1) 0.046(1) 0.074(1) -0.008(1) -0.009(1) -0.008(1)
C(18) 0.059(1) 0.064(1) 0.044(1) -0.014(1) 0.000(1) -0.032(1)
C(20) 0.066(1) 0.065(1) 0.060(1) 0.013(1) -0.008(1) -0.033(1)
C(22) 0.059(1) 0.045(1) 0.051(1) -0.012(1) -0.001(1) -0.022(1)
C(8) 0.050(1) 0.083(1) 0.102(1) -0.042(1) -0.022(1) -0.007(1)
C(19) 0.069(1) 0.087(1) 0.041(1) -0.005(1) -0.003(1) -0.041(1)
C(14) 0.038(1) 0.065(1) 0.065(1) -0.008(1) -0.010(1) -0.018(1)
C(21) 0.069(1) 0.044(1) 0.079(1) -0.006(1) -0.006(1) -0.026(1)
C(9) 0.045(1) 0.069(1) 0.065(1) -0.027(1) -0.008(1) -0.013(1)
C(7) 0.082(1) 0.067(1) 0.104(1) -0.025(1) -0.054(1) -0.002(1)
C(5) 0.087(1) 0.059(1) 0.054(1) -0.003(1) -0.020(1) -0.031(1)
C(6) 0.124(2) 0.070(1) 0.066(1) 0.002(1) -0.045(1) -0.031(1)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(1) C(3) 1.2603(13)
C(16) C(15) 1.382(2)
C(16) C(11) 1.388(2)
C(16) H(16) 0.988(14)
C(11) C(12) 1.400(2)
C(11) N(10) 1.4148(14)
N(10) C(1) 1.3395(13)
N(10) H(10) 0.88(2)
C(13) C(14) 1.381(2)
C(13) C(12) 1.384(2)
C(13) H(13) 1.00(2)
C(1) C(2) 1.387(2)
C(1) C(17) 1.4916(14)
C(4) C(5) 1.387(2)
C(4) C(9) 1.390(2)
C(4) C(3) 1.494(2)
C(12) O(2) 1.3542(14)
C(3) C(2) 1.418(2)
O(2) H(211) 0.93(2)
C(2) H(2) 0.980(12)
C(17) C(22) 1.383(2)
C(17) C(18) 1.390(2)
C(15) C(14) 1.38(2)
C(15) H(15) 1.00(2)
C(18) C(19) 1.384(2)
C(18) H(18) 1.03(2)
C(20) C(21) 1.372(2)
C(20) C(19) 1.374(2)
C(20) H(20) 0.97(2)
C(22) C(21) 1.390(2)
C(22) H(22) 0.98(2)
C(8) C(7) 1.359(3)
C(8) C(9) 1.387(2)
C(8) H(8) 0.97(3)
C(19) H(19) 0.99(2)
C(14) H(14) 0.96(2)
C(21) H(21) 0.98(2)
C(9) H(9) 1.04(2)
C(7) C(6) 1.369(3)
C(7) H(7) 0.95(2)
C(5) C(6) 1.395(2)
C(5) H(5) 0.99(2)
C(6) H(6) 0.95(2)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(15) C(16) C(11) 120.06(11)
C(15) C(16) H(16) 122.1(9)
C(11) C(16) H(16) 117.8(9)
C(16) C(11) C(12) 119.30(10)
C(16) C(11) N(10) 124.81(10)
C(12) C(11) N(10) 115.73(9)
C(1) N(10) C(11) 131.00(9)
C(1) N(10) H(10) 113.1(9)
C(11) N(10) H(10) 115.9(9)
C(14) C(13) C(12) 119.91(11)
C(14) C(13) H(13) 121.7(9)
C(12) C(13) H(13) 118.3(9)
N(10) C(1) C(2) 121.32(9)
N(10) C(1) C(17) 119.86(9)
C(2) C(1) C(17) 118.72(9)
C(5) C(4) C(9) 119.08(12)
C(5) C(4) C(3) 118.99(11)
C(9) C(4) C(3) 121.89(11)
O(2) C(12) C(13) 124.31(10)
O(2) C(12) C(11) 115.56(9)
C(13) C(12) C(11) 120.13(10)
O(1) C(3) C(2) 122.40(9)
O(1) C(3) C(4) 117.87(9)
C(2) C(3) C(4) 119.73(9)
C(12) O(2) H(211) 113.3(11)
C(1) C(2) C(3) 123.71(10)
C(1) C(2) H(2) 117.6(7)
C(3) C(2) H(2) 118.7(7)
C(22) C(17) C(18) 119.74(10)
C(22) C(17) C(1) 121.01(10)
C(18) C(17) C(1) 119.17(10)
C(14) C(15) C(16) 120.37(11)
C(14) C(15) H(15) 125.9(9)
C(16) C(15) H(15) 113.5(9)
C(19) C(18) C(17) 119.81(13)
C(19) C(18) H(18) 122.1(8)
C(17) C(18) H(18) 118.1(8)
C(21) C(20) C(19) 120.16(12)
C(21) C(20) H(20) 120.4(14)
C(19) C(20) H(20) 119.3(14)
C(17) C(22) C(21) 119.69(12)
C(17) C(22) H(22) 119.4(9)
C(21) C(22) H(22) 121.0(9)
C(7) C(8) C(9) 120.1(2)
C(7) C(8) H(8) 120(2)
C(9) C(8) H(8) 120(2)
C(20) C(19) C(18) 120.26(13)
C(20) C(19) H(19) 121.4(10)
C(18) C(19) H(19) 118.3(10)
C(15) C(14) C(13) 120.21(11)
C(15) C(14) H(14) 120.7(8)
C(13) C(14) H(14) 119.1(8)
C(20) C(21) C(22) 120.31(13)
C(20) C(21) H(21) 121.7(9)
C(22) C(21) H(21) 117.9(9)
C(8) C(9) C(4) 120.4(2)
C(8) C(9) H(9) 119.7(9)
C(4) C(9) H(9) 119.5(9)
C(8) C(7) C(6) 120.35(14)
C(8) C(7) H(7) 118.1(14)
C(6) C(7) H(7) 121.5(14)
C(4) C(5) C(6) 119.4(2)
C(4) C(5) H(5) 119.5(9)
C(6) C(5) H(5) 121.1(9)
C(7) C(6) C(5) 120.6(2)
C(7) C(6) H(6) 126.0(12)
C(5) C(6) H(6) 113.3(13)


_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.233