data_global
_audit_creation_method                  'APEX2 v2012.4-3'

_publ_requested_journal                 ?

_publ_contact_author_name              Ass. Prof. Alya M. Al-Etaibi  
_publ_contact_author_address            
;
;
_publ_contact_author_email              ?
_publ_contact_author_fax                ?
_publ_contact_author_phone              ?

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_I
_chemical_name_systematic               ?
_chemical_name_common                   Prof_Nouria_N2_Alya_18_02_13
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C16 H16 N4 O2'
_chemical_formula_iupac                 ?
_chemical_formula_weight                296.33

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_name_H-M_alt               'P 1 21/n 1'
_space_group_name_Hall                  '-P 2yn'
loop_
    _space_group_symop_operation_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                          7.6301(2)
_cell_length_b                          16.7825(5)
_cell_length_c                          11.6116(4)
_cell_angle_alpha                       90
_cell_angle_beta                        90.891(2)
_cell_angle_gamma                       90
_cell_volume                            1486.71(8)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           4211
_cell_measurement_theta_min             4.6312
_cell_measurement_theta_max             66.5529
_cell_measurement_temperature           296.(2)

_exptl_crystal_description              Block
_exptl_crystal_colour                   'clear light orange'
_exptl_crystal_size_max                 0.210
_exptl_crystal_size_mid                 0.140
_exptl_crystal_size_min                 0.040
_exptl_crystal_density_diffrn           1.324
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    624

_exptl_absorpt_coefficient_mu           0.740
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min         0.85
_exptl_absorpt_correction_T_max         0.97

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             296.(2)

_diffrn_source                          ?
_diffrn_source_type                     ?

_diffrn_radiation_type                  ?
_diffrn_radiation_wavelength            1.54178
_diffrn_radiation_monochromator         ?

_diffrn_measurement_device_type         ?
_diffrn_measurement_method              ?

_diffrn_detector_area_resol_mean        8.3333

_diffrn_reflns_number                   6530
_diffrn_reflns_av_R_equivalents         0.0854
_diffrn_reflns_av_sigmaI/netI           0.0517
_diffrn_reflns_theta_min                4.63
_diffrn_reflns_theta_max                66.60
_diffrn_reflns_theta_full               66.60
_diffrn_measured_fraction_theta_max     0.979
_diffrn_measured_fraction_theta_full    0.979
_diffrn_reflns_limit_h_min              -9
_diffrn_reflns_limit_h_max              8
_diffrn_reflns_limit_k_min              -19
_diffrn_reflns_limit_k_max              19
_diffrn_reflns_limit_l_min              -13
_diffrn_reflns_limit_l_max              8

_refine_special_details                 
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total                    2565
_reflns_number_gt                       2250
_reflns_threshold_expression            >2sigma(I)

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0513
_refine_ls_R_factor_gt                  0.0477
_refine_ls_wR_factor_gt                 0.1341
_refine_ls_wR_factor_ref                0.1398
_refine_ls_goodness_of_fit_ref          1.040
_refine_ls_restrained_S_all             1.040
_refine_ls_number_reflns                2565
_refine_ls_number_parameters            201
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           mixed
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
    'calc w=1/[σ²(Fo²)+(0.0965P)²+0.0669P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap

_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.242
_refine_diff_density_min                -0.199
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection              
    'Bruker Instrument Service v2012.4.0.0'
_computing_cell_refinement              'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_reduction               'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution           'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics           ?
_computing_publication_material         ?

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 -0.45063(15) 0.83328(6) 1.15067(11) 0.0735(4) Uani d . 1 . .
    O O2 0.08223(12) 0.85888(5) 0.98722(8) 0.0544(3) Uani d . 1 . .
    N N4 -0.18250(14) 0.84713(6) 1.07087(8) 0.0447(3) Uani d . 1 . .
    C C7 -0.01478(15) 0.72774(7) 1.02551(9) 0.0398(3) Uani d . 1 . .
    N N2 0.12111(13) 0.69001(6) 0.98130(8) 0.0421(3) Uani d . 1 . .
    N N1 0.24974(13) 0.73075(6) 0.93839(9) 0.0453(3) Uani d . 1 . .
    H H1 0.2464 0.7819 0.9406 0.054 Uiso calc R 1 . .
    C C16 -0.2842(2) 0.96037(9) 0.95261(13) 0.0627(4) Uani d . 1 . .
    H H16A -0.2116 0.9429 0.8907 0.094 Uiso calc R 1 . .
    H H16B -0.2931 1.0174 0.9511 0.094 Uiso calc R 1 . .
    H H16C -0.3989 0.9375 0.9438 0.094 Uiso calc R 1 . .
    C C15 -0.20420(18) 0.93432(7) 1.06570(11) 0.0508(3) Uani d . 1 . .
    H H15A -0.0908 0.9596 1.0761 0.061 Uiso calc R 1 . .
    H H15B -0.2786 0.9514 1.128 0.061 Uiso calc R 1 . .
    C C11 -0.03146(15) 0.81460(7) 1.02615(9) 0.0419(3) Uani d . 1 . .
    C C1 0.39397(15) 0.69261(7) 0.88854(9) 0.0416(3) Uani d . 1 . .
    C C6 0.40880(18) 0.61085(8) 0.88387(12) 0.0516(3) Uani d . 1 . .
    H H6 0.3225 0.5786 0.915 0.062 Uiso calc R 1 . .
    C C5 0.55356(19) 0.57727(9) 0.83225(13) 0.0602(4) Uani d . 1 . .
    H H5 0.564 0.5221 0.8285 0.072 Uiso calc R 1 . .
    C C4 0.68232(19) 0.62476(9) 0.78636(12) 0.0576(4) Uani d . 1 . .
    H H4 0.7789 0.6017 0.7517 0.069 Uiso calc R 1 . .
    N N3 -0.54854(18) 0.63530(8) 1.20162(13) 0.0717(4) Uani d . 1 . .
    C C14 -0.43510(18) 0.67084(8) 1.16377(12) 0.0509(3) Uani d . 1 . .
    C C9 -0.29367(16) 0.71534(8) 1.11637(10) 0.0427(3) Uani d . 1 . .
    C C10 -0.31843(17) 0.80158(8) 1.11559(11) 0.0480(3) Uani d . 1 . .
    C C8 -0.15064(15) 0.67858(7) 1.07193(9) 0.0399(3) Uani d . 1 . .
    C C12 -0.13207(17) 0.58952(7) 1.07314(11) 0.0465(3) Uani d . 1 . .
    H H12A -0.0686 0.5729 1.0055 0.056 Uiso calc R 1 . .
    H H12B -0.2476 0.5655 1.0691 0.056 Uiso calc R 1 . .
    C C13 -0.0366(2) 0.55967(9) 1.17988(14) 0.0675(4) Uani d . 1 . .
    H H13A 0.0786 0.5826 1.1836 0.101 Uiso calc R 1 . .
    H H13B -0.0273 0.5027 1.1767 0.101 Uiso calc R 1 . .
    H H13C -0.1005 0.5748 1.247 0.101 Uiso calc R 1 . .
    C C2 0.52359(17) 0.74063(8) 0.84299(11) 0.0481(3) Uani d . 1 . .
    H H2 0.5138 0.7958 0.8467 0.058 Uiso calc R 1 . .
    C C3 0.66768(18) 0.70603(10) 0.79197(11) 0.0552(4) Uani d . 1 . .
    H H3 0.7548 0.7381 0.7614 0.066 Uiso calc R 1 . .


_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C10 . 1.2162(16) ?
    O2 C11 . 1.2334(15) ?
    N4 C11 . 1.3835(15) ?
    N4 C10 . 1.3952(17) ?
    N4 C15 . 1.4737(16) ?
    C7 N2 . 1.3252(15) ?
    C7 C8 . 1.4363(16) ?
    C7 C11 . 1.4633(17) ?
    N2 N1 . 1.3016(14) ?
    N1 C1 . 1.4056(15) ?
    N1 H1 . 0.86 ?
    C16 C15 . 1.504(2) ?
    C16 H16A . 0.96 ?
    C16 H16B . 0.96 ?
    C16 H16C . 0.96 ?
    C15 H15A . 0.97 ?
    C15 H15B . 0.97 ?
    C1 C6 . 1.3780(18) ?
    C1 C2 . 1.3869(17) ?
    C6 C5 . 1.3847(19) ?
    C6 H6 . 0.93 ?
    C5 C4 . 1.379(2) ?
    C5 H5 . 0.93 ?
    C4 C3 . 1.370(2) ?
    C4 H4 . 0.93 ?
    N3 C14 . 1.1446(18) ?
    C14 C9 . 1.4296(17) ?
    C9 C8 . 1.3621(16) ?
    C9 C10 . 1.4596(18) ?
    C8 C12 . 1.5014(17) ?
    C12 C13 . 1.513(2) ?
    C12 H12A . 0.97 ?
    C12 H12B . 0.97 ?
    C13 H13A . 0.96 ?
    C13 H13B . 0.96 ?
    C13 H13C . 0.96 ?
    C2 C3 . 1.3847(19) ?
    C2 H2 . 0.93 ?
    C3 H3 . 0.93 ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C11 N4 C10 . . 123.50(10) ?
    C11 N4 C15 . . 118.05(10) ?
    C10 N4 C15 . . 118.39(10) ?
    N2 C7 C8 . . 116.39(11) ?
    N2 C7 C11 . . 123.14(11) ?
    C8 C7 C11 . . 120.46(10) ?
    N1 N2 C7 . . 119.77(10) ?
    N2 N1 C1 . . 121.22(10) ?
    N2 N1 H1 . . 119.4 ?
    C1 N1 H1 . . 119.4 ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    N4 C15 C16 . . 111.58(11) ?
    N4 C15 H15A . . 109.3 ?
    C16 C15 H15A . . 109.3 ?
    N4 C15 H15B . . 109.3 ?
    C16 C15 H15B . . 109.3 ?
    H15A C15 H15B . . 108.0 ?
    O2 C11 N4 . . 119.64(11) ?
    O2 C11 C7 . . 122.45(11) ?
    N4 C11 C7 . . 117.90(10) ?
    C6 C1 C2 . . 120.27(11) ?
    C6 C1 N1 . . 122.34(11) ?
    C2 C1 N1 . . 117.39(11) ?
    C1 C6 C5 . . 119.27(12) ?
    C1 C6 H6 . . 120.4 ?
    C5 C6 H6 . . 120.4 ?
    C4 C5 C6 . . 120.66(13) ?
    C4 C5 H5 . . 119.7 ?
    C6 C5 H5 . . 119.7 ?
    C3 C4 C5 . . 119.87(12) ?
    C3 C4 H4 . . 120.1 ?
    C5 C4 H4 . . 120.1 ?
    N3 C14 C9 . . 179.88(18) ?
    C8 C9 C14 . . 121.55(11) ?
    C8 C9 C10 . . 123.44(11) ?
    C14 C9 C10 . . 114.96(10) ?
    O1 C10 N4 . . 120.68(12) ?
    O1 C10 C9 . . 122.66(12) ?
    N4 C10 C9 . . 116.66(10) ?
    C9 C8 C7 . . 117.98(11) ?
    C9 C8 C12 . . 121.56(11) ?
    C7 C8 C12 . . 120.45(10) ?
    C8 C12 C13 . . 112.43(11) ?
    C8 C12 H12A . . 109.1 ?
    C13 C12 H12A . . 109.1 ?
    C8 C12 H12B . . 109.1 ?
    C13 C12 H12B . . 109.1 ?
    H12A C12 H12B . . 107.9 ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C12 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C3 C2 C1 . . 119.68(13) ?
    C3 C2 H2 . . 120.2 ?
    C1 C2 H2 . . 120.2 ?
    C4 C3 C2 . . 120.24(13) ?
    C4 C3 H3 . . 119.9 ?
    C2 C3 H3 . . 119.9 ?

loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C8 C7 N2 N1 . . . . -179.54(9) ?
    C11 C7 N2 N1 . . . . 1.76(16) ?
    C7 N2 N1 C1 . . . . -178.57(10) ?
    C11 N4 C15 C16 . . . . 86.03(14) ?
    C10 N4 C15 C16 . . . . -91.08(14) ?
    C10 N4 C11 O2 . . . . 179.35(11) ?
    C15 N4 C11 O2 . . . . 2.41(16) ?
    C10 N4 C11 C7 . . . . 0.32(16) ?
    C15 N4 C11 C7 . . . . -176.62(10) ?
    N2 C7 C11 O2 . . . . -1.39(17) ?
    C8 C7 C11 O2 . . . . 179.96(10) ?
    N2 C7 C11 N4 . . . . 177.61(10) ?
    C8 C7 C11 N4 . . . . -1.04(15) ?
    N2 N1 C1 C6 . . . . -1.04(17) ?
    N2 N1 C1 C2 . . . . 178.83(10) ?
    C2 C1 C6 C5 . . . . -0.62(19) ?
    N1 C1 C6 C5 . . . . 179.25(12) ?
    C1 C6 C5 C4 . . . . 0.3(2) ?
    C6 C5 C4 C3 . . . . 0.2(2) ?
    N3 C14 C9 C8 . . . . -140.(100) ?
    N3 C14 C9 C10 . . . . 40.(80) ?
    C11 N4 C10 O1 . . . . -177.79(12) ?
    C15 N4 C10 O1 . . . . -0.86(18) ?
    C11 N4 C10 C9 . . . . 1.50(17) ?
    C15 N4 C10 C9 . . . . 178.43(10) ?
    C8 C9 C10 O1 . . . . 176.43(13) ?
    C14 C9 C10 O1 . . . . -1.25(19) ?
    C8 C9 C10 N4 . . . . -2.85(17) ?
    C14 C9 C10 N4 . . . . 179.47(10) ?
    C14 C9 C8 C7 . . . . 179.71(10) ?
    C10 C9 C8 C7 . . . . 2.19(16) ?
    C14 C9 C8 C12 . . . . -1.57(17) ?
    C10 C9 C8 C12 . . . . -179.10(11) ?
    N2 C7 C8 C9 . . . . -178.94(10) ?
    C11 C7 C8 C9 . . . . -0.20(15) ?
    N2 C7 C8 C12 . . . . 2.33(15) ?
    C11 C7 C8 C12 . . . . -178.93(10) ?
    C9 C8 C12 C13 . . . . -91.33(14) ?
    C7 C8 C12 C13 . . . . 87.35(14) ?
    C6 C1 C2 C3 . . . . 0.45(18) ?
    N1 C1 C2 C3 . . . . -179.42(11) ?
    C5 C4 C3 C2 . . . . -0.4(2) ?
    C1 C2 C3 C4 . . . . 0.04(19) ?

