#------------------------------------------------------------------------------
#$Date: 2022-02-16 05:14:00 +0200 (Wed, 16 Feb 2022) $
#$Revision: 272988 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244039.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244039
loop_
_publ_author_name
'El Kalai, Fouad'
'Baydere, Cemile'
'Dege, Necmi'
'Abudunia, Abdulmalik'
'Benchat, Noureddine'
'Karrouchi, Khalid'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of 2-oxo-2-phenylethyl
 3-nitroso-2-phenylimidazo[1,2-a]pyridine-8-carboxylate
;
_journal_coeditor_code           WM5632
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022001517
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C22 H15 N3 O4'
_chemical_formula_moiety         'C22 H15 N3 O4'
_chemical_formula_sum            'C22 H15 N3 O4'
_chemical_formula_weight         385.37
_chemical_name_systematic
;
2-Oxo-2-phenylethyl
3-nitroso-2-phenylimidazo[1,2-a]pyridine-8-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90.566(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9256(14)
_cell_length_b                   14.8256(14)
_cell_length_c                   7.6787(6)
_cell_measurement_reflns_used    18578
_cell_measurement_temperature    296
_cell_measurement_theta_max      32.77
_cell_measurement_theta_min      1.88
_cell_volume                     1812.9(3)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2012)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2012)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 2012)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020), PLATON (Spek, 2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), SHELXL (Sheldrick, 2015b),
PLATON (Spek, 2020) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            27945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.915
_diffrn_reflns_theta_min         2.558
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           45
_diffrn_source_power             2.25
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9690
_exptl_absorpt_correction_T_min  0.9456
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2012)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       rod
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.562
_exptl_crystal_size_mid          0.377
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         6703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0506P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                3040
_reflns_number_total             6703
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5632sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2244039
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O3 0.63005(6) 0.31601(7) 0.48667(14) 0.0542(3) Uani d 1 . .
O O2 0.58609(6) 0.39797(6) 0.25605(15) 0.0595(3) Uani d 1 . .
N N3 0.40012(7) 0.34790(7) 0.20621(16) 0.0441(3) Uani d 1 . .
N N2 0.39287(6) 0.19477(7) 0.20006(16) 0.0435(3) Uani d 1 . .
O O4 0.75836(8) 0.26469(8) 0.30406(19) 0.0788(4) Uani d 1 . .
O O1 0.25639(7) 0.09653(7) 0.0672(2) 0.0780(4) Uani d 1 . .
N N1 0.25076(8) 0.18024(9) 0.06361(19) 0.0599(4) Uani d 1 . .
C C14 0.58089(8) 0.33230(9) 0.34708(19) 0.0416(3) Uani d 1 . .
C C12 0.52135(8) 0.25563(8) 0.31845(18) 0.0414(3) Uani d 1 . .
C C13 0.44102(8) 0.27009(8) 0.24261(18) 0.0404(3) Uani d 1 . .
C C7 0.32472(8) 0.32353(9) 0.13986(19) 0.0441(3) Uani d 1 . .
C C17 0.86457(9) 0.34187(9) 0.46238(19) 0.0464(3) Uani d 1 . .
C C8 0.31681(8) 0.22879(9) 0.1315(2) 0.0465(3) Uani d 1 . .
C C6 0.26278(8) 0.39215(9) 0.08286(19) 0.0459(3) Uani d 1 . .
C C11 0.54667(9) 0.16813(9) 0.3493(2) 0.0483(3) Uani d 1 . .
H H11 0.598339 0.157821 0.403177 0.058 Uiso calc 1 . .
C C16 0.77582(9) 0.32058(9) 0.4145(2) 0.0495(3) Uani d 1 . .
C C15 0.70537(8) 0.36842(9) 0.5070(2) 0.0498(3) Uani d 1 . .
H H15A 0.719202 0.375040 0.629688 0.060 Uiso calc 1 . .
H H15B 0.697194 0.428055 0.457752 0.060 Uiso calc 1 . .
C C18 0.88553(9) 0.40814(10) 0.5833(2) 0.0524(4) Uani d 1 . .
H H18 0.843669 0.443252 0.632786 0.063 Uiso calc 1 . .
C C9 0.42025(9) 0.10793(9) 0.2257(2) 0.0508(4) Uani d 1 . .
H H9 0.387103 0.059250 0.191712 0.061 Uiso calc 1 . .
C C10 0.49660(9) 0.09435(9) 0.3016(2) 0.0529(4) Uani d 1 . .
H H10 0.515667 0.035964 0.321857 0.063 Uiso calc 1 . .
C C5 0.28989(9) 0.47829(10) 0.0411(2) 0.0537(4) Uani d 1 . .
H H5 0.346539 0.492649 0.052027 0.064 Uiso calc 1 . .
C C4 0.23357(10) 0.54324(11) -0.0168(2) 0.0618(4) Uani d 1 . .
H H4 0.252468 0.600751 -0.044788 0.074 Uiso calc 1 . .
C C19 0.96856(10) 0.42184(11) 0.6299(3) 0.0645(4) Uani d 1 . .
H H19 0.982383 0.465939 0.711376 0.077 Uiso calc 1 . .
C C3 0.14938(11) 0.52236(12) -0.0328(2) 0.0669(5) Uani d 1 . .
H H3 0.111528 0.565477 -0.073272 0.080 Uiso calc 1 . .
C C1 0.17725(9) 0.37247(11) 0.0689(3) 0.0633(4) Uani d 1 . .
H H1 0.157736 0.315422 0.098519 0.076 Uiso calc 1 . .
C C22 0.92826(10) 0.29109(11) 0.3880(2) 0.0639(4) Uani d 1 . .
H H22 0.914895 0.247016 0.306093 0.077 Uiso calc 1 . .
C C20 1.03132(10) 0.37028(13) 0.5559(3) 0.0719(5) Uani d 1 . .
H H20 1.087105 0.379435 0.588214 0.086 Uiso calc 1 . .
C C2 0.12162(10) 0.43762(13) 0.0113(3) 0.0727(5) Uani d 1 . .
H H2 0.064726 0.424057 0.002223 0.087 Uiso calc 1 . .
C C21 1.01088(11) 0.30541(13) 0.4343(3) 0.0736(5) Uani d 1 . .
H H21 1.053005 0.271212 0.383457 0.088 Uiso calc 1 . .
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'
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
C14 O3 C15 . . 117.98(11) ?
C7 N3 C13 . . 105.94(10) ?
C9 N2 C13 . . 123.04(11) ?
C9 N2 C8 . . 131.29(11) ?
C13 N2 C8 . . 105.67(10) ?
O1 N1 C8 . . 117.36(12) ?
O2 C14 O3 . . 124.53(12) ?
O2 C14 C12 . . 125.28(12) ?
O3 C14 C12 . . 110.15(11) ?
C11 C12 C13 . . 118.33(11) ?
C11 C12 C14 . . 120.41(11) ?
C13 C12 C14 . . 120.94(11) ?
N3 C13 N2 . . 111.88(10) ?
N3 C13 C12 . . 130.17(11) ?
N2 C13 C12 . . 117.93(11) ?
N3 C7 C8 . . 111.24(11) ?
N3 C7 C6 . . 121.04(11) ?
C8 C7 C6 . . 127.70(11) ?
C18 C17 C22 . . 119.06(13) ?
C18 C17 C16 . . 122.36(13) ?
C22 C17 C16 . . 118.53(13) ?
N1 C8 N2 . . 127.33(12) ?
N1 C8 C7 . . 127.34(12) ?
N2 C8 C7 . . 105.26(10) ?
C5 C6 C1 . . 118.72(13) ?
C5 C6 C7 . . 119.55(12) ?
C1 C6 C7 . . 121.73(13) ?
C12 C11 C10 . . 121.69(12) ?
C12 C11 H11 . . 119.2 ?
C10 C11 H11 . . 119.2 ?
O4 C16 C17 . . 121.74(14) ?
O4 C16 C15 . . 118.84(13) ?
C17 C16 C15 . . 119.41(12) ?
O3 C15 C16 . . 108.54(11) ?
O3 C15 H15A . . 110.0 ?
C16 C15 H15A . . 110.0 ?
O3 C15 H15B . . 110.0 ?
C16 C15 H15B . . 110.0 ?
H15A C15 H15B . . 108.4 ?
C19 C18 C17 . . 119.98(15) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C10 C9 N2 . . 118.84(12) ?
C10 C9 H9 . . 120.6 ?
N2 C9 H9 . . 120.6 ?
C9 C10 C11 . . 120.11(13) ?
C9 C10 H10 . . 119.9 ?
C11 C10 H10 . . 119.9 ?
C4 C5 C6 . . 120.80(14) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C3 C4 C5 . . 119.83(15) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C18 C19 C20 . . 120.37(16) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C2 C3 C4 . . 119.82(14) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C2 C1 C6 . . 120.06(16) ?
C2 C1 H1 . . 120.0 ?
C6 C1 H1 . . 120.0 ?
C21 C22 C17 . . 120.64(16) ?
C21 C22 H22 . . 119.7 ?
C17 C22 H22 . . 119.7 ?
C21 C20 C19 . . 119.80(15) ?
C21 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C3 C2 C1 . . 120.74(15) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C22 C21 C20 . . 120.14(17) ?
C22 C21 H21 . . 119.9 ?
C20 C21 H21 . . 119.9 ?
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
O3 C14 . 1.3431(16) ?
O3 C15 . 1.4365(16) ?
O2 C14 . 1.2018(16) ?
N3 C7 . 1.3491(16) ?
N3 C13 . 1.3526(16) ?
N2 C9 . 1.3729(17) ?
N2 C13 . 1.3918(16) ?
N2 C8 . 1.4092(16) ?
O4 C16 . 1.2157(17) ?
O1 N1 . 1.2446(16) ?
N1 C8 . 1.3732(17) ?
C14 C12 . 1.4951(18) ?
C12 C11 . 1.3783(18) ?
C12 C13 . 1.4166(18) ?
C7 C8 . 1.4115(19) ?
C7 C6 . 1.4803(18) ?
C17 C18 . 1.390(2) ?
C17 C22 . 1.391(2) ?
C17 C16 . 1.4907(19) ?
C6 C5 . 1.387(2) ?
C6 C1 . 1.396(2) ?
C11 C10 . 1.4002(19) ?
C11 H11 . 0.9300 ?
C16 C15 . 1.511(2) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C18 C19 . 1.381(2) ?
C18 H18 . 0.9300 ?
C9 C10 . 1.3581(19) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C5 C4 . 1.386(2) ?
C5 H5 . 0.9300 ?
C4 C3 . 1.380(2) ?
C4 H4 . 0.9300 ?
C19 C20 . 1.385(3) ?
C19 H19 . 0.9300 ?
C3 C2 . 1.375(3) ?
C3 H3 . 0.9300 ?
C1 C2 . 1.381(2) ?
C1 H1 . 0.9300 ?
C22 C21 . 1.376(2) ?
C22 H22 . 0.9300 ?
C20 C21 . 1.377(3) ?
C20 H20 . 0.9300 ?
C2 H2 . 0.9300 ?
C21 H21 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C15 H15A O4 4_566 0.97 2.54 3.1257(19) 118.8 yes
C15 H15B O1 2_655 0.97 2.61 3.4841(18) 149.7 yes
C9 H9 O2 2_645 0.93 2.46 3.1176(16) 127.7 yes
C10 H10 O2 2_645 0.93 2.67 3.2243(17) 118.6 yes
C9 H9 O1 . 0.93 2.35 2.8736(18) 115.5 yes
C1 H1 N1 . 0.93 2.51 3.081(2) 120.1 yes
C22 H22 Cg4 4_565 0.93 2.80 3.657(2) 153 yes
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
C15 O3 C14 O2 . . . . -14.9(2) ?
C15 O3 C14 C12 . . . . 163.13(11) ?
O2 C14 C12 C11 . . . . 141.14(16) ?
O3 C14 C12 C11 . . . . -36.82(19) ?
O2 C14 C12 C13 . . . . -32.3(2) ?
O3 C14 C12 C13 . . . . 149.69(13) ?
C7 N3 C13 N2 . . . . 0.14(16) ?
C7 N3 C13 C12 . . . . -178.13(15) ?
C9 N2 C13 N3 . . . . -179.58(13) ?
C8 N2 C13 N3 . . . . 0.31(16) ?
C9 N2 C13 C12 . . . . -1.1(2) ?
C8 N2 C13 C12 . . . . 178.82(12) ?
C11 C12 C13 N3 . . . . 176.84(15) ?
C14 C12 C13 N3 . . . . -9.5(2) ?
C11 C12 C13 N2 . . . . -1.3(2) ?
C14 C12 C13 N2 . . . . 172.27(13) ?
C13 N3 C7 C8 . . . . -0.56(17) ?
C13 N3 C7 C6 . . . . -179.33(13) ?
O1 N1 C8 N2 . . . . 2.6(2) ?
O1 N1 C8 C7 . . . . 179.29(16) ?
C9 N2 C8 N1 . . . . -3.5(3) ?
C13 N2 C8 N1 . . . . 176.62(15) ?
C9 N2 C8 C7 . . . . 179.26(15) ?
C13 N2 C8 C7 . . . . -0.61(15) ?
N3 C7 C8 N1 . . . . -176.49(15) ?
C6 C7 C8 N1 . . . . 2.2(3) ?
N3 C7 C8 N2 . . . . 0.74(17) ?
C6 C7 C8 N2 . . . . 179.42(14) ?
N3 C7 C6 C5 . . . . 21.9(2) ?
C8 C7 C6 C5 . . . . -156.69(16) ?
N3 C7 C6 C1 . . . . -158.46(15) ?
C8 C7 C6 C1 . . . . 23.0(3) ?
C13 C12 C11 C10 . . . . 2.5(2) ?
C14 C12 C11 C10 . . . . -171.16(15) ?
C18 C17 C16 O4 . . . . 177.35(15) ?
C22 C17 C16 O4 . . . . -5.1(2) ?
C18 C17 C16 C15 . . . . -3.6(2) ?
C22 C17 C16 C15 . . . . 173.89(14) ?
C14 O3 C15 C16 . . . . -89.28(14) ?
O4 C16 C15 O3 . . . . 19.49(19) ?
C17 C16 C15 O3 . . . . -159.56(12) ?
C22 C17 C18 C19 . . . . -1.0(2) ?
C16 C17 C18 C19 . . . . 176.52(14) ?
C13 N2 C9 C10 . . . . 2.4(2) ?
C8 N2 C9 C10 . . . . -177.50(15) ?
N2 C9 C10 C11 . . . . -1.2(2) ?
C12 C11 C10 C9 . . . . -1.2(3) ?
C1 C6 C5 C4 . . . . -1.3(2) ?
C7 C6 C5 C4 . . . . 178.39(15) ?
C6 C5 C4 C3 . . . . 0.2(3) ?
C17 C18 C19 C20 . . . . 0.4(2) ?
C5 C4 C3 C2 . . . . 1.0(3) ?
C5 C6 C1 C2 . . . . 1.2(3) ?
C7 C6 C1 C2 . . . . -178.44(16) ?
C18 C17 C22 C21 . . . . 0.7(2) ?
C16 C17 C22 C21 . . . . -176.95(16) ?
C18 C19 C20 C21 . . . . 0.4(3) ?
C4 C3 C2 C1 . . . . -1.0(3) ?
C6 C1 C2 C3 . . . . -0.1(3) ?
C17 C22 C21 C20 . . . . 0.2(3) ?
C19 C20 C21 C22 . . . . -0.8(3) ?

_cod_database_fobs_code 2244039
