#------------------------------------------------------------------------------
#$Date: 2021-03-06 08:18:51 +0200 (Sat, 06 Mar 2021) $
#$Revision: 262791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243767.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_2243767
loop_
_publ_author_name
'Allah, Omyma A. Abd'
'Kaur, Manpreet'
'Akkurt, Mehmet'
'Mohamed, Shaaban K.'
'Tamam, Asmaa H. A.'
'Elgarhy, Sahar M. I.'
'Jasinski, Jerry P.'
_publ_section_title
;
 Crystal structures of
 1-(4-chlorophenyl)-4-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic
 acid and
 4-(4-methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile
;
_journal_coeditor_code           YZ2005
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              351
_journal_page_last               355
_journal_paper_doi               10.1107/S2056989021002140
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C24 H22 N2 O3'
_chemical_formula_moiety         'C24 H22 N2 O3'
_chemical_formula_sum            'C24 H22 N2 O3'
_chemical_formula_weight         386.43
_chemical_name_systematic
4-(4-Methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile
_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
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.797(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.3486(2)
_cell_length_b                   13.9969(3)
_cell_length_c                   27.5353(5)
_cell_measurement_reflns_used    3849
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.7530
_cell_measurement_theta_min      4.2730
_cell_volume                     3979.69(14)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015a)
;
_computing_structure_solution
;
ShelXT (Sheldrick, 2015b)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15107
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.435
_diffrn_reflns_theta_min         3.544
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         7579
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0487
_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)+(0.0628P)²+0.1965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                5380
_reflns_number_total             7579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2005sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243767
_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 O1A 0.36261(17) 0.53971(14) 0.33466(6) 0.0704(5) Uani d 1 . .
O O2A 0.78343(15) 0.78301(13) 0.24000(6) 0.0635(4) Uani d 1 . .
O O3A 0.5360(2) 0.99458(16) 0.43140(8) 0.0866(6) Uani d 1 . .
N N1A 0.40024(16) 0.60665(14) 0.26190(6) 0.0490(4) Uani d 1 . .
N N2A 0.6257(3) 0.56408(18) 0.41665(8) 0.0773(6) Uani d 1 . .
C C1A 0.4369(2) 0.57641(15) 0.30847(7) 0.0502(5) Uani d 1 . .
C C2A 0.5814(2) 0.58943(16) 0.32306(7) 0.0499(5) Uani d 1 . .
H H2A 0.628554 0.537522 0.306612 0.060 Uiso calc 1 . .
C C3A 0.63700(18) 0.68516(15) 0.30610(7) 0.0462(4) Uani d 1 . .
H H3A 0.733419 0.678557 0.307960 0.055 Uiso calc 1 . .
C C4A 0.59327(19) 0.69818(15) 0.25308(7) 0.0440(4) Uani d 1 . .
C C5A 0.6773(2) 0.75536(16) 0.22368(8) 0.0509(5) Uani d 1 . .
C C6A 0.6240(7) 0.7794(6) 0.1737(2) 0.093(3) Uani d 0.670(11) A 1
H H6A1 0.647523 0.846564 0.167295 0.112 Uiso calc 0.670(11) A 1
H H6A2 0.669856 0.739274 0.150722 0.112 Uiso calc 0.670(11) A 1
C C7A 0.4928(5) 0.7699(5) 0.16172(18) 0.0727(19) Uani d 0.670(11) A 1
H H7A1 0.478234 0.768970 0.125825 0.087 Uiso calc 0.670(11) A 1
H H7A2 0.447588 0.826567 0.173844 0.087 Uiso calc 0.670(11) A 1
C C8A 0.4343(10) 0.6823(10) 0.1818(3) 0.058(3) Uani d 0.670(11) A 1
H H8A1 0.454564 0.627035 0.161223 0.070 Uiso calc 0.670(11) A 1
H H8A2 0.338993 0.689814 0.180160 0.070 Uiso calc 0.670(11) A 1
C C6AA 0.6417(13) 0.7776(12) 0.1706(4) 0.081(6) Uani d 0.330(11) A 2
H H6A3 0.609006 0.843920 0.167569 0.097 Uiso calc 0.330(11) A 2
H H6A4 0.719692 0.772369 0.151825 0.097 Uiso calc 0.330(11) A 2
C C7AA 0.5411(9) 0.7106(9) 0.1504(2) 0.062(3) Uani d 0.330(11) A 2
H H7A3 0.587817 0.655632 0.137269 0.074 Uiso calc 0.330(11) A 2
H H7A4 0.496696 0.743252 0.122131 0.074 Uiso calc 0.330(11) A 2
C C8AA 0.4327(18) 0.668(2) 0.1804(5) 0.054(5) Uani d 0.330(11) A 2
H H8A3 0.354750 0.708882 0.177077 0.064 Uiso calc 0.330(11) A 2
H H8A4 0.408875 0.603398 0.167990 0.064 Uiso calc 0.330(11) A 2
C C9A 0.48142(19) 0.66155(15) 0.23353(7) 0.0454(4) Uani d 1 . .
C C10A 0.60548(19) 0.76995(15) 0.33746(7) 0.0453(4) Uani d 1 . .
C C11A 0.6939(2) 0.79817(18) 0.37505(8) 0.0580(5) Uani d 1 . .
H H11A 0.773514 0.764736 0.380089 0.070 Uiso calc 1 . .
C C12A 0.6683(2) 0.8734(2) 0.40504(9) 0.0664(6) Uani d 1 . .
H H12A 0.730490 0.891710 0.430239 0.080 Uiso calc 1 . .
C C13A 0.5529(2) 0.92254(17) 0.39877(9) 0.0594(6) Uani d 1 . .
C C14A 0.4648(2) 0.89723(17) 0.36131(9) 0.0588(5) Uani d 1 . .
H H14A 0.385742 0.931387 0.356279 0.071 Uiso calc 1 . .
C C15A 0.4919(2) 0.82139(17) 0.33077(8) 0.0528(5) Uani d 1 . .
H H15A 0.430961 0.804786 0.304833 0.063 Uiso calc 1 . .
C C16A 0.2677(2) 0.58533(16) 0.24393(7) 0.0478(5) Uani d 1 . .
C C17A 0.2392(2) 0.50222(18) 0.21912(10) 0.0633(6) Uani d 1 . .
H H17A 0.305254 0.456910 0.214024 0.076 Uiso calc 1 . .
C C18A 0.1124(3) 0.48517(19) 0.20156(10) 0.0689(7) Uani d 1 . .
H H18A 0.092331 0.427678 0.184344 0.083 Uiso calc 1 . .
C C19A 0.0151(2) 0.55004(18) 0.20862(8) 0.0574(5) Uani d 1 . .
C C20A 0.0455(2) 0.63227(18) 0.23423(8) 0.0568(5) Uani d 1 . .
H H20A -0.020731 0.677108 0.239908 0.068 Uiso calc 1 . .
C C21A 0.1721(2) 0.65056(16) 0.25189(7) 0.0521(5) Uani d 1 . .
H H21A 0.192371 0.707754 0.269352 0.062 Uiso calc 1 . .
C C22A 0.6045(2) 0.57437(17) 0.37597(8) 0.0578(5) Uani d 1 . .
C C23A 0.4110(3) 1.0295(3) 0.43679(13) 0.0962(10) Uani d 1 . .
H H23A 0.378518 1.060752 0.406571 0.144 Uiso calc 1 . .
H H23B 0.413342 1.075712 0.463558 0.144 Uiso calc 1 . .
H H23C 0.353668 0.976341 0.444030 0.144 Uiso calc 1 . .
C C24A -0.1230(3) 0.5333(2) 0.18813(11) 0.0803(8) Uani d 1 . .
H H24A -0.183518 0.561316 0.210066 0.120 Uiso calc 1 . .
H H24B -0.139106 0.464541 0.185086 0.120 Uiso calc 1 . .
H H24C -0.135458 0.563409 0.156018 0.120 Uiso calc 1 . .
O O1B 0.88611(15) 0.55891(11) 0.33264(6) 0.0597(4) Uani d 1 . .
O O2B 1.17002(16) 0.19933(11) 0.42029(6) 0.0623(4) Uani d 1 . .
O O3B 0.61297(18) 0.20781(13) 0.49274(7) 0.0735(5) Uani d 1 . .
N N1B 1.05243(16) 0.52114(12) 0.38701(6) 0.0442(4) Uani d 1 . .
N N2B 0.7586(3) 0.37087(19) 0.27435(9) 0.0866(8) Uani d 1 . .
C C1B 0.96338(19) 0.50067(15) 0.34912(7) 0.0445(4) Uani d 1 . .
C C2B 0.9722(2) 0.40016(16) 0.32852(7) 0.0473(5) Uani d 1 . .
H H2B 1.045583 0.399447 0.306669 0.057 Uiso calc 1 . .
C C3B 0.99990(19) 0.32262(14) 0.36769(7) 0.0445(4) Uani d 1 . .
H H3B 1.028406 0.263711 0.350848 0.053 Uiso calc 1 . .
C C4B 1.11285(18) 0.35722(14) 0.40066(6) 0.0409(4) Uani d 1 . .
C C5B 1.19280(19) 0.28396(15) 0.42658(7) 0.0459(4) Uani d 1 . .
C C6B 1.3012(2) 0.31731(17) 0.46160(8) 0.0566(5) Uani d 1 . .
H H6BA 1.372469 0.270099 0.462105 0.068 Uiso calc 1 . .
H H6BB 1.269539 0.320138 0.494725 0.068 Uiso calc 1 . .
C C7B 1.3531(2) 0.41394(17) 0.44876(8) 0.0546(5) Uani d 1 . .
H H7BA 1.398831 0.408795 0.418402 0.066 Uiso calc 1 . .
H H7BB 1.416456 0.435436 0.475017 0.066 Uiso calc 1 . .
C C8B 1.2457(2) 0.48714(16) 0.44186(7) 0.0496(5) Uani d 1 . .
H H8BA 1.213782 0.503444 0.473927 0.060 Uiso calc 1 . .
H H8BB 1.280653 0.546139 0.427828 0.060 Uiso calc 1 . .
C C9B 1.13513(18) 0.45094(14) 0.40896(6) 0.0409(4) Uani d 1 . .
C C10B 0.88665(18) 0.29520(14) 0.39738(7) 0.0438(4) Uani d 1 . .
C C11B 0.8175(2) 0.36257(15) 0.42189(8) 0.0490(5) Uani d 1 . .
H H11B 0.834148 0.428504 0.417023 0.059 Uiso calc 1 . .
C C12B 0.7244(2) 0.33612(16) 0.45338(8) 0.0529(5) Uani d 1 . .
H H12B 0.677947 0.383529 0.469731 0.064 Uiso calc 1 . .
C C13B 0.6998(2) 0.24062(16) 0.46077(8) 0.0524(5) Uani d 1 . .
C C14B 0.7626(2) 0.17243(16) 0.43470(9) 0.0596(6) Uani d 1 . .
H H14B 0.742172 0.106745 0.438278 0.072 Uiso calc 1 . .
C C15B 0.8550(2) 0.19959(16) 0.40346(8) 0.0552(5) Uani d 1 . .
H H15B 0.897639 0.152078 0.385788 0.066 Uiso calc 1 . .
C C16B 1.05339(19) 0.61852(14) 0.40490(7) 0.0439(4) Uani d 1 . .
C C17B 1.0002(2) 0.64075(17) 0.44792(8) 0.0591(5) Uani d 1 . .
H H17B 0.964595 0.591822 0.466862 0.071 Uiso calc 1 . .
C C18B 0.9988(3) 0.73479(19) 0.46353(9) 0.0659(6) Uani d 1 . .
H H18B 0.963120 0.749395 0.493561 0.079 Uiso calc 1 . .
C C19B 1.0478(2) 0.80763(17) 0.43663(9) 0.0593(6) Uani d 1 . .
C C20B 1.1019(3) 0.78322(18) 0.39393(10) 0.0700(7) Uani d 1 . .
H H20B 1.137513 0.831935 0.374852 0.084 Uiso calc 1 . .
C C21B 1.1056(3) 0.68946(17) 0.37820(8) 0.0617(6) Uani d 1 . .
H H21B 1.144360 0.674336 0.348844 0.074 Uiso calc 1 . .
C C22B 0.8523(2) 0.38295(17) 0.29799(8) 0.0599(6) Uani d 1 . .
C C23B 0.5890(3) 0.2675(2) 0.53236(9) 0.0676(6) Uani d 1 . .
H H23D 0.541756 0.324436 0.520484 0.101 Uiso calc 1 . .
H H23E 0.671532 0.286706 0.549044 0.101 Uiso calc 1 . .
H H23F 0.537152 0.232836 0.555109 0.101 Uiso calc 1 . .
C C24B 1.0432(3) 0.9097(2) 0.45374(13) 0.0892(9) Uani d 1 . .
H H24D 0.989531 0.913847 0.481671 0.134 Uiso calc 1 . .
H H24E 1.006030 0.950037 0.427298 0.134 Uiso calc 1 . .
H H24F 1.131171 0.931536 0.463385 0.134 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 0.0181 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'
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
C13A O3A C23A . . 119.0(2) ?
C1A N1A C9A . . 122.95(18) ?
C1A N1A C16A . . 116.59(17) ?
C9A N1A C16A . . 120.30(16) ?
O1A C1A N1A . . 122.7(2) ?
O1A C1A C2A . . 123.00(19) ?
N1A C1A C2A . . 114.25(17) ?
C22A C2A C1A . . 109.44(18) ?
C22A C2A C3A . . 112.57(19) ?
C1A C2A C3A . . 113.61(16) ?
C22A C2A H2A . . 106.9 ?
C1A C2A H2A . . 106.9 ?
C3A C2A H2A . . 106.9 ?
C4A C3A C10A . . 113.21(16) ?
C4A C3A C2A . . 107.67(17) ?
C10A C3A C2A . . 114.14(17) ?
C4A C3A H3A . . 107.1 ?
C10A C3A H3A . . 107.1 ?
C2A C3A H3A . . 107.1 ?
C9A C4A C5A . . 120.91(18) ?
C9A C4A C3A . . 122.37(18) ?
C5A C4A C3A . . 116.70(18) ?
O2A C5A C4A . . 121.5(2) ?
O2A C5A C6A . . 122.6(3) ?
C4A C5A C6A . . 116.0(3) ?
O2A C5A C6AA . . 116.4(6) ?
C4A C5A C6AA . . 122.0(6) ?
C7A C6A C5A . . 119.8(5) ?
C7A C6A H6A1 . . 107.4 ?
C5A C6A H6A1 . . 107.4 ?
C7A C6A H6A2 . . 107.4 ?
C5A C6A H6A2 . . 107.4 ?
H6A1 C6A H6A2 . . 106.9 ?
C6A C7A C8A . . 114.0(6) ?
C6A C7A H7A1 . . 108.7 ?
C8A C7A H7A1 . . 108.7 ?
C6A C7A H7A2 . . 108.7 ?
C8A C7A H7A2 . . 108.7 ?
H7A1 C7A H7A2 . . 107.6 ?
C7A C8A C9A . . 113.4(7) ?
C7A C8A H8A1 . . 108.9 ?
C9A C8A H8A1 . . 108.9 ?
C7A C8A H8A2 . . 108.9 ?
C9A C8A H8A2 . . 108.9 ?
H8A1 C8A H8A2 . . 107.7 ?
C7AA C6AA C5A . . 110.6(11) ?
C7AA C6AA H6A3 . . 109.5 ?
C5A C6AA H6A3 . . 109.5 ?
C7AA C6AA H6A4 . . 109.5 ?
C5A C6AA H6A4 . . 109.5 ?
H6A3 C6AA H6A4 . . 108.1 ?
C6AA C7AA C8AA . . 123.9(12) ?
C6AA C7AA H7A3 . . 106.4 ?
C8AA C7AA H7A3 . . 106.4 ?
C6AA C7AA H7A4 . . 106.4 ?
C8AA C7AA H7A4 . . 106.4 ?
H7A3 C7AA H7A4 . . 106.4 ?
C9A C8AA C7AA . . 109.2(12) ?
C9A C8AA H8A3 . . 109.8 ?
C7AA C8AA H8A3 . . 109.8 ?
C9A C8AA H8A4 . . 109.8 ?
C7AA C8AA H8A4 . . 109.8 ?
H8A3 C8AA H8A4 . . 108.3 ?
C4A C9A N1A . . 120.92(18) ?
C4A C9A C8A . . 121.5(4) ?
N1A C9A C8A . . 117.5(4) ?
C4A C9A C8AA . . 125.8(7) ?
N1A C9A C8AA . . 113.1(7) ?
C15A C10A C11A . . 117.6(2) ?
C15A C10A C3A . . 123.09(18) ?
C11A C10A C3A . . 119.35(18) ?
C12A C11A C10A . . 121.4(2) ?
C12A C11A H11A . . 119.3 ?
C10A C11A H11A . . 119.3 ?
C11A C12A C13A . . 120.4(2) ?
C11A C12A H12A . . 119.8 ?
C13A C12A H12A . . 119.8 ?
O3A C13A C14A . . 125.0(2) ?
O3A C13A C12A . . 115.6(2) ?
C14A C13A C12A . . 119.4(2) ?
C13A C14A C15A . . 119.9(2) ?
C13A C14A H14A . . 120.1 ?
C15A C14A H14A . . 120.1 ?
C10A C15A C14A . . 121.4(2) ?
C10A C15A H15A . . 119.3 ?
C14A C15A H15A . . 119.3 ?
C17A C16A C21A . . 120.6(2) ?
C17A C16A N1A . . 120.6(2) ?
C21A C16A N1A . . 118.7(2) ?
C16A C17A C18A . . 119.1(2) ?
C16A C17A H17A . . 120.4 ?
C18A C17A H17A . . 120.4 ?
C19A C18A C17A . . 121.3(2) ?
C19A C18A H18A . . 119.3 ?
C17A C18A H18A . . 119.3 ?
C20A C19A C18A . . 118.6(2) ?
C20A C19A C24A . . 119.8(2) ?
C18A C19A C24A . . 121.6(2) ?
C19A C20A C21A . . 120.8(2) ?
C19A C20A H20A . . 119.6 ?
C21A C20A H20A . . 119.6 ?
C16A C21A C20A . . 119.5(2) ?
C16A C21A H21A . . 120.2 ?
C20A C21A H21A . . 120.2 ?
N2A C22A C2A . . 178.0(3) ?
O3A C23A H23A . . 109.5 ?
O3A C23A H23B . . 109.5 ?
H23A C23A H23B . . 109.5 ?
O3A C23A H23C . . 109.5 ?
H23A C23A H23C . . 109.5 ?
H23B C23A H23C . . 109.5 ?
C19A C24A H24A . . 109.5 ?
C19A C24A H24B . . 109.5 ?
H24A C24A H24B . . 109.5 ?
C19A C24A H24C . . 109.5 ?
H24A C24A H24C . . 109.5 ?
H24B C24A H24C . . 109.5 ?
C13B O3B C23B . . 116.91(19) ?
C1B N1B C9B . . 122.42(17) ?
C1B N1B C16B . . 116.28(16) ?
C9B N1B C16B . . 121.24(15) ?
O1B C1B N1B . . 122.5(2) ?
O1B C1B C2B . . 122.54(18) ?
N1B C1B C2B . . 114.93(16) ?
C22B C2B C1B . . 107.18(18) ?
C22B C2B C3B . . 113.26(19) ?
C1B C2B C3B . . 113.74(15) ?
C22B C2B H2B . . 107.5 ?
C1B C2B H2B . . 107.5 ?
C3B C2B H2B . . 107.5 ?
C4B C3B C10B . . 110.53(15) ?
C4B C3B C2B . . 107.16(17) ?
C10B C3B C2B . . 116.00(16) ?
C4B C3B H3B . . 107.6 ?
C10B C3B H3B . . 107.6 ?
C2B C3B H3B . . 107.6 ?
C9B C4B C5B . . 120.73(17) ?
C9B C4B C3B . . 122.01(17) ?
C5B C4B C3B . . 117.10(18) ?
O2B C5B C4B . . 120.75(19) ?
O2B C5B C6B . . 121.47(19) ?
C4B C5B C6B . . 117.77(18) ?
C5B C6B C7B . . 113.01(18) ?
C5B C6B H6BA . . 109.0 ?
C7B C6B H6BA . . 109.0 ?
C5B C6B H6BB . . 109.0 ?
C7B C6B H6BB . . 109.0 ?
H6BA C6B H6BB . . 107.8 ?
C6B C7B C8B . . 111.51(18) ?
C6B C7B H7BA . . 109.3 ?
C8B C7B H7BA . . 109.3 ?
C6B C7B H7BB . . 109.3 ?
C8B C7B H7BB . . 109.3 ?
H7BA C7B H7BB . . 108.0 ?
C9B C8B C7B . . 111.81(18) ?
C9B C8B H8BA . . 109.3 ?
C7B C8B H8BA . . 109.3 ?
C9B C8B H8BB . . 109.3 ?
C7B C8B H8BB . . 109.3 ?
H8BA C8B H8BB . . 107.9 ?
C4B C9B N1B . . 120.81(17) ?
C4B C9B C8B . . 123.09(18) ?
N1B C9B C8B . . 116.10(18) ?
C11B C10B C15B . . 117.5(2) ?
C11B C10B C3B . . 122.08(18) ?
C15B C10B C3B . . 120.23(19) ?
C10B C11B C12B . . 121.7(2) ?
C10B C11B H11B . . 119.2 ?
C12B C11B H11B . . 119.2 ?
C13B C12B C11B . . 119.6(2) ?
C13B C12B H12B . . 120.2 ?
C11B C12B H12B . . 120.2 ?
O3B C13B C12B . . 123.5(2) ?
O3B C13B C14B . . 116.8(2) ?
C12B C13B C14B . . 119.7(2) ?
C15B C14B C13B . . 120.1(2) ?
C15B C14B H14B . . 119.9 ?
C13B C14B H14B . . 119.9 ?
C14B C15B C10B . . 121.2(2) ?
C14B C15B H15B . . 119.4 ?
C10B C15B H15B . . 119.4 ?
C21B C16B C17B . . 119.6(2) ?
C21B C16B N1B . . 119.62(19) ?
C17B C16B N1B . . 120.78(19) ?
C16B C17B C18B . . 119.7(2) ?
C16B C17B H17B . . 120.1 ?
C18B C17B H17B . . 120.1 ?
C19B C18B C17B . . 121.7(2) ?
C19B C18B H18B . . 119.2 ?
C17B C18B H18B . . 119.2 ?
C18B C19B C20B . . 117.4(2) ?
C18B C19B C24B . . 120.9(3) ?
C20B C19B C24B . . 121.7(3) ?
C19B C20B C21B . . 121.6(2) ?
C19B C20B H20B . . 119.2 ?
C21B C20B H20B . . 119.2 ?
C16B C21B C20B . . 120.0(2) ?
C16B C21B H21B . . 120.0 ?
C20B C21B H21B . . 120.0 ?
N2B C22B C2B . . 179.0(3) ?
O3B C23B H23D . . 109.5 ?
O3B C23B H23E . . 109.5 ?
H23D C23B H23E . . 109.5 ?
O3B C23B H23F . . 109.5 ?
H23D C23B H23F . . 109.5 ?
H23E C23B H23F . . 109.5 ?
C19B C24B H24D . . 109.5 ?
C19B C24B H24E . . 109.5 ?
H24D C24B H24E . . 109.5 ?
C19B C24B H24F . . 109.5 ?
H24D C24B H24F . . 109.5 ?
H24E C24B H24F . . 109.5 ?
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
O1A C1A . 1.204(3) ?
O2A C5A . 1.222(3) ?
O3A C13A . 1.369(3) ?
O3A C23A . 1.400(4) ?
N1A C1A . 1.380(3) ?
N1A C9A . 1.412(3) ?
N1A C16A . 1.458(3) ?
N2A C22A . 1.136(3) ?
C1A C2A . 1.533(3) ?
C2A C22A . 1.476(3) ?
C2A C3A . 1.543(3) ?
C2A H2A . 1.0000 ?
C3A C4A . 1.510(3) ?
C3A C10A . 1.516(3) ?
C3A H3A . 1.0000 ?
C4A C9A . 1.345(3) ?
C4A C5A . 1.465(3) ?
C5A C6A . 1.487(6) ?
C5A C6AA . 1.515(13) ?
C6A C7A . 1.382(7) ?
C6A H6A1 . 0.9900 ?
C6A H6A2 . 0.9900 ?
C7A C8A . 1.490(10) ?
C7A H7A1 . 0.9900 ?
C7A H7A2 . 0.9900 ?
C8A C9A . 1.503(7) ?
C8A H8A1 . 0.9900 ?
C8A H8A2 . 0.9900 ?
C6AA C7AA . 1.481(13) ?
C6AA H6A3 . 0.9900 ?
C6AA H6A4 . 0.9900 ?
C7AA C8AA . 1.556(13) ?
C7AA H7A3 . 0.9900 ?
C7AA H7A4 . 0.9900 ?
C8AA C9A . 1.518(14) ?
C8AA H8A3 . 0.9900 ?
C8AA H8A4 . 0.9900 ?
C10A C15A . 1.380(3) ?
C10A C11A . 1.392(3) ?
C11A C12A . 1.375(4) ?
C11A H11A . 0.9500 ?
C12A C13A . 1.379(4) ?
C12A H12A . 0.9500 ?
C13A C14A . 1.377(3) ?
C14A C15A . 1.394(3) ?
C14A H14A . 0.9500 ?
C15A H15A . 0.9500 ?
C16A C17A . 1.371(3) ?
C16A C21A . 1.374(3) ?
C17A C18A . 1.388(4) ?
C17A H17A . 0.9500 ?
C18A C19A . 1.380(4) ?
C18A H18A . 0.9500 ?
C19A C20A . 1.375(4) ?
C19A C24A . 1.519(3) ?
C20A C21A . 1.391(3) ?
C20A H20A . 0.9500 ?
C21A H21A . 0.9500 ?
C23A H23A . 0.9800 ?
C23A H23B . 0.9800 ?
C23A H23C . 0.9800 ?
C24A H24A . 0.9800 ?
C24A H24B . 0.9800 ?
C24A H24C . 0.9800 ?
O1B C1B . 1.209(2) ?
O2B C5B . 1.218(3) ?
O3B C13B . 1.378(3) ?
O3B C23B . 1.409(3) ?
N1B C1B . 1.376(3) ?
N1B C9B . 1.412(3) ?
N1B C16B . 1.449(3) ?
N2B C22B . 1.145(3) ?
C1B C2B . 1.522(3) ?
C2B C22B . 1.471(3) ?
C2B C3B . 1.544(3) ?
C2B H2B . 1.0000 ?
C3B C4B . 1.511(3) ?
C3B C10B . 1.522(3) ?
C3B H3B . 1.0000 ?
C4B C9B . 1.349(3) ?
C4B C5B . 1.472(3) ?
C5B C6B . 1.504(3) ?
C6B C7B . 1.506(3) ?
C6B H6BA . 0.9900 ?
C6B H6BB . 0.9900 ?
C7B C8B . 1.514(3) ?
C7B H7BA . 0.9900 ?
C7B H7BB . 0.9900 ?
C8B C9B . 1.500(3) ?
C8B H8BA . 0.9900 ?
C8B H8BB . 0.9900 ?
C10B C11B . 1.386(3) ?
C10B C15B . 1.391(3) ?
C11B C12B . 1.388(3) ?
C11B H11B . 0.9500 ?
C12B C13B . 1.378(3) ?
C12B H12B . 0.9500 ?
C13B C14B . 1.382(3) ?
C14B C15B . 1.381(3) ?
C14B H14B . 0.9500 ?
C15B H15B . 0.9500 ?
C16B C21B . 1.368(3) ?
C16B C17B . 1.374(3) ?
C17B C18B . 1.385(3) ?
C17B H17B . 0.9500 ?
C18B C19B . 1.376(4) ?
C18B H18B . 0.9500 ?
C19B C20B . 1.378(4) ?
C19B C24B . 1.506(3) ?
C20B C21B . 1.383(4) ?
C20B H20B . 0.9500 ?
C21B H21B . 0.9500 ?
C23B H23D . 0.9800 ?
C23B H23E . 0.9800 ?
C23B H23F . 0.9800 ?
C24B H24D . 0.9800 ?
C24B H24E . 0.9800 ?
C24B H24F . 0.9800 ?
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
C21A H21A N2B 2_655 0.95 2.65 3.258(4) 122.7 yes
C14B H14B O3A 1_545 0.95 2.65 3.417(3) 138.7 yes
C3A H3A O1B 1_555 1.00 2.37 3.171(2) 136 yes
C23B H23E Cg9 3_766 0.98 2.93 3.868(3) 160 yes
C23B H23F Cg4 3_666 0.98 2.74 3.710(3) 169 yes

_cod_database_fobs_code 2243767
