#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/09/7240996.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7240996
loop_
_publ_author_name
'P. George, Christy'
'Thorat, Sridhar Hanamant'
'Shaligram, Parth S.'
'Suresha, P. R.'
'Gonnade, Rajesh G.'
_publ_section_title
;
 Drug-Drug Cocrystals of Anticancer Drugs Erlotinib-Furosemide and
 Gefitinib-Mefenamic acid for Alternative Multi-Drug Treatment
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00353K
_journal_year                    2020
_chemical_formula_moiety         'C22 H24 Cl F N4 O3, C15 H15 N1 O2, H2 O'
_chemical_formula_sum            'C37 H41 Cl F N5 O6'
_chemical_formula_weight         706.20
_chemical_name_systematic        'Gefitinib-mefenamic acid cocrystal'
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-02-15 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.132(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9083(7)
_cell_length_b                   7.6817(5)
_cell_length_c                   41.588(3)
_cell_measurement_reflns_used    5596
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.98
_cell_measurement_theta_min      2.21
_cell_volume                     3464.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            40768
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.878
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol-acetonitrile mixture'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0908
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0597P)²+13.2995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1998
_refine_ls_wR_factor_ref         0.2177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4764
_reflns_number_total             6829
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00353k2.cif
_cod_data_source_block           GIF_MEF_H2O
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240996
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.997
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.11466(13) 1.1043(2) 0.62819(3) 0.0531(4) Uani 1 1 d . . . . .
F1 F -0.1003(3) 1.0024(4) 0.58429(7) 0.0436(8) Uani 1 1 d . . . . .
N1 N 0.4575(3) 0.8190(5) 0.45141(9) 0.0262(9) Uani 1 1 d . . . . .
C2 C 0.3480(4) 0.8745(6) 0.45869(11) 0.0303(11) Uani 1 1 d . . . . .
H2 H 0.2932 0.9189 0.4413 0.036 Uiso 1 1 calc R U . . .
N3 N 0.3079(4) 0.8741(5) 0.48766(9) 0.0315(9) Uani 1 1 d . . . . .
C4 C 0.3849(4) 0.8131(6) 0.51244(11) 0.0270(10) Uani 1 1 d . . . . .
N4 N 0.3466(4) 0.8153(5) 0.54232(10) 0.0295(9) Uani 1 1 d . . . . .
H4N H 0.400(4) 0.795(6) 0.5580(11) 0.018(12) Uiso 1 1 d . . . . .
C5 C 0.5887(4) 0.6745(6) 0.53245(10) 0.0244(10) Uani 1 1 d . . . . .
H5 H 0.5664 0.6661 0.5539 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7026(4) 0.6168(6) 0.52559(10) 0.0241(10) Uani 1 1 d . . . . .
O6 O 0.7891(3) 0.5448(4) 0.54747(7) 0.0281(7) Uani 1 1 d . . . . .
C7 C 0.7364(4) 0.6294(6) 0.49347(10) 0.0222(9) Uani 1 1 d . . . . .
O7 O 0.8514(3) 0.5714(4) 0.49012(7) 0.0265(7) Uani 1 1 d . . . . .
C8 C 0.6548(4) 0.6947(6) 0.46910(11) 0.0240(10) Uani 1 1 d . . . . .
H8 H 0.6765 0.7001 0.4476 0.029 Uiso 1 1 calc R U . . .
C9 C 0.5381(4) 0.7537(5) 0.47620(10) 0.0220(9) Uani 1 1 d . . . . .
C10 C 0.5048(4) 0.7463(6) 0.50769(10) 0.0235(10) Uani 1 1 d . . . . .
C11 C 0.2291(4) 0.8695(6) 0.55102(11) 0.0285(10) Uani 1 1 d . . . . .
C12 C 0.2294(4) 0.9500(6) 0.58096(11) 0.0299(11) Uani 1 1 d . . . . .
H12 H 0.3048 0.9736 0.5939 0.036 Uiso 1 1 calc R U . . .
C13 C 0.1164(5) 0.9956(6) 0.59173(11) 0.0307(11) Uani 1 1 d . . . . .
C14 C 0.0096(4) 0.9609(6) 0.57301(12) 0.0309(11) Uani 1 1 d . . . . .
C15 C 0.0079(5) 0.8861(7) 0.54327(13) 0.0371(12) Uani 1 1 d . . . . .
H15 H -0.0682 0.8652 0.5305 0.044 Uiso 1 1 calc R U . . .
C16 C 0.1191(5) 0.8408(6) 0.53186(13) 0.0356(12) Uani 1 1 d . . . . .
H16 H 0.1195 0.7903 0.5110 0.043 Uiso 1 1 calc R U . . .
C17 C 0.7630(4) 0.5406(6) 0.58048(10) 0.0278(10) Uani 1 1 d . . . . .
H17A H 0.6874 0.4718 0.5824 0.033 Uiso 1 1 calc R U . . .
H17B H 0.7495 0.6602 0.5882 0.033 Uiso 1 1 calc R U . . .
C18 C 0.8701(5) 0.4594(6) 0.60035(10) 0.0295(11) Uani 1 1 d . . . . .
H18A H 0.9432 0.5355 0.6000 0.035 Uiso 1 1 calc R U . . .
H18B H 0.8893 0.3461 0.5907 0.035 Uiso 1 1 calc R U . . .
C19 C 0.8443(5) 0.4314(6) 0.63498(11) 0.0299(11) Uani 1 1 d . . . . .
H19A H 0.7805 0.3402 0.6355 0.036 Uiso 1 1 calc R U . . .
H19B H 0.9204 0.3887 0.6477 0.036 Uiso 1 1 calc R U . . .
N20 N 0.8023(3) 0.5905(5) 0.65037(8) 0.0222(8) Uani 1 1 d . . . . .
C21 C 0.7622(5) 0.5487(6) 0.68162(10) 0.0290(11) Uani 1 1 d . . . . .
H21A H 0.8319 0.4992 0.6959 0.035 Uiso 1 1 calc R U . . .
H21B H 0.6957 0.4605 0.6789 0.035 Uiso 1 1 calc R U . . .
C22 C 0.7150(5) 0.7124(6) 0.69703(12) 0.0326(11) Uani 1 1 d . . . . .
H22A H 0.6439 0.7601 0.6830 0.039 Uiso 1 1 calc R U . . .
H22B H 0.6869 0.6829 0.7182 0.039 Uiso 1 1 calc R U . . .
O23 O 0.8104(3) 0.8404(5) 0.70140(8) 0.0401(9) Uani 1 1 d . . . . .
C24 C 0.8561(5) 0.8796(7) 0.67129(13) 0.0369(12) Uani 1 1 d . . . . .
H24A H 0.9240 0.9651 0.6750 0.044 Uiso 1 1 calc R U . . .
H24B H 0.7894 0.9338 0.6566 0.044 Uiso 1 1 calc R U . . .
C25 C 0.9024(5) 0.7209(6) 0.65524(11) 0.0307(11) Uani 1 1 d . . . . .
H25A H 0.9300 0.7533 0.6341 0.037 Uiso 1 1 calc R U . . .
H25B H 0.9736 0.6710 0.6689 0.037 Uiso 1 1 calc R U . . .
C26 C 0.8957(5) 0.5951(7) 0.45907(11) 0.0324(11) Uani 1 1 d . . . . .
H26A H 0.8415 0.5332 0.4425 0.049 Uiso 1 1 calc R U . . .
H26B H 0.9796 0.5487 0.4597 0.049 Uiso 1 1 calc R U . . .
H26C H 0.8961 0.7194 0.4538 0.049 Uiso 1 1 calc R U . . .
C27 C 0.5276(4) 0.7228(6) 0.37596(10) 0.0241(10) Uani 1 1 d . . . . .
C28 C 0.5120(4) 0.7272(5) 0.34038(10) 0.0183(9) Uani 1 1 d . . . . .
C29 C 0.4311(4) 0.8494(5) 0.32465(10) 0.0223(9) Uani 1 1 d . . . . .
H29 H 0.3937 0.9331 0.3373 0.027 Uiso 1 1 calc R U . . .
C30 C 0.4035(4) 0.8528(6) 0.29139(10) 0.0254(10) Uani 1 1 d . . . . .
H30 H 0.3492 0.9381 0.2813 0.030 Uiso 1 1 calc R U . . .
C31 C 0.4573(4) 0.7284(6) 0.27299(10) 0.0240(10) Uani 1 1 d . . . . .
H31 H 0.4381 0.7274 0.2502 0.029 Uiso 1 1 calc R U . . .
C32 C 0.5379(4) 0.6068(6) 0.28750(9) 0.0212(9) Uani 1 1 d . . . . .
H32 H 0.5737 0.5236 0.2744 0.025 Uiso 1 1 calc R U . . .
C33 C 0.5684(4) 0.6029(5) 0.32119(10) 0.0187(9) Uani 1 1 d . . . . .
N33 N 0.6510(4) 0.4822(5) 0.33513(9) 0.0238(8) Uani 1 1 d . . . . .
H33N H 0.652(4) 0.465(6) 0.3563(12) 0.028(13) Uiso 1 1 d . . . . .
C34 C 0.7042(4) 0.3503(5) 0.31691(9) 0.0192(9) Uani 1 1 d . . . . .
C35 C 0.6679(4) 0.1777(6) 0.32082(10) 0.0244(10) Uani 1 1 d . . . . .
H35 H 0.6101 0.1502 0.3356 0.029 Uiso 1 1 calc R U . . .
C36 C 0.7166(4) 0.0468(6) 0.30304(11) 0.0273(10) Uani 1 1 d . . . . .
H36 H 0.6936 -0.0709 0.3060 0.033 Uiso 1 1 calc R U . . .
C37 C 0.7984(4) 0.0873(6) 0.28107(11) 0.0268(10) Uani 1 1 d . . . . .
H37 H 0.8297 -0.0028 0.2686 0.032 Uiso 1 1 calc R U . . .
C38 C 0.8362(4) 0.2605(6) 0.27686(10) 0.0224(9) Uani 1 1 d . . . . .
C39 C 0.7904(4) 0.3924(5) 0.29545(10) 0.0194(9) Uani 1 1 d . . . . .
C40 C 0.9245(4) 0.3010(6) 0.25251(11) 0.0308(11) Uani 1 1 d . . . . .
H40A H 0.8946 0.4020 0.2396 0.046 Uiso 1 1 calc R U . . .
H40B H 0.9307 0.2004 0.2383 0.046 Uiso 1 1 calc R U . . .
H40C H 1.0060 0.3271 0.2638 0.046 Uiso 1 1 calc R U . . .
C41 C 0.8349(4) 0.5780(6) 0.29238(11) 0.0275(10) Uani 1 1 d . . . . .
H41A H 0.7997 0.6267 0.2716 0.041 Uiso 1 1 calc R U . . .
H41B H 0.9251 0.5791 0.2934 0.041 Uiso 1 1 calc R U . . .
H41C H 0.8089 0.6484 0.3101 0.041 Uiso 1 1 calc R U . . .
O42 O 0.4801(3) 0.8537(4) 0.39058(7) 0.0334(8) Uani 1 1 d . . . . .
O43 O 0.5808(4) 0.6013(5) 0.39148(8) 0.0437(10) Uani 1 1 d . . . . .
H42O H 0.473(5) 0.831(8) 0.4210(13) 0.053(16) Uiso 1 1 d . . . . .
O44 O 0.4990(5) 0.2326(8) 0.39608(13) 0.0775(16) Uani 1 1 d G . . . .
H6A H 0.4271 0.2147 0.3866 0.116 Uiso 1 1 d G U . . .
H6B H 0.5200 0.3374 0.3930 0.116 Uiso 1 1 d G U . . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C9 117.6(4) . . ?
C2 N1 H42O 115(2) . . ?
C9 N1 H42O 128(2) . . ?
N3 C2 N1 126.6(4) . . ?
N3 C2 H2 116.7 . . ?
N1 C2 H2 116.7 . . ?
C2 N3 C4 117.3(4) . . ?
N3 C4 N4 118.2(4) . . ?
N3 C4 C10 121.5(4) . . ?
N4 C4 C10 120.3(4) . . ?
C4 N4 C11 127.5(4) . . ?
C4 N4 H4N 117(3) . . ?
C11 N4 H4N 115(3) . . ?
C6 C5 C10 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C10 C5 H5 119.9 . . ?
O6 C6 C5 124.8(4) . . ?
O6 C6 C7 115.1(4) . . ?
C5 C6 C7 120.1(4) . . ?
C6 O6 C17 117.2(3) . . ?
O7 C7 C8 125.5(4) . . ?
O7 C7 C6 114.2(4) . . ?
C8 C7 C6 120.3(4) . . ?
C7 O7 C26 117.1(3) . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
N1 C9 C10 120.5(4) . . ?
N1 C9 C8 118.6(4) . . ?
C10 C9 C8 120.9(4) . . ?
C9 C10 C5 119.1(4) . . ?
C9 C10 C4 116.5(4) . . ?
C5 C10 C4 124.5(4) . . ?
C16 C11 C12 120.4(4) . . ?
C16 C11 N4 123.5(4) . . ?
C12 C11 N4 116.1(4) . . ?
C11 C12 C13 118.7(5) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 Cl1 120.5(4) . . ?
C12 C13 Cl1 119.5(4) . . ?
C13 C14 C15 122.1(4) . . ?
C13 C14 F1 119.1(4) . . ?
C15 C14 F1 118.8(4) . . ?
C14 C15 C16 119.1(5) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 119.8(5) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
O6 C17 C18 108.4(4) . . ?
O6 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
O6 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 C19 111.9(4) . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
N20 C19 C18 113.2(4) . . ?
N20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
N20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.8 . . ?
C21 N20 C19 110.1(3) . . ?
C21 N20 C25 108.4(3) . . ?
C19 N20 C25 111.2(4) . . ?
N20 C21 C22 110.0(4) . . ?
N20 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
N20 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
O23 C22 C21 110.3(4) . . ?
O23 C22 H22A 109.6 . . ?
C21 C22 H22A 109.6 . . ?
O23 C22 H22B 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C24 O23 C22 110.5(4) . . ?
O23 C24 C25 112.5(4) . . ?
O23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
O23 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
N20 C25 C24 109.4(4) . . ?
N20 C25 H25A 109.8 . . ?
C24 C25 H25A 109.8 . . ?
N20 C25 H25B 109.8 . . ?
C24 C25 H25B 109.8 . . ?
H25A C25 H25B 108.2 . . ?
O7 C26 H26A 109.5 . . ?
O7 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O7 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O43 C27 O42 121.4(4) . . ?
O43 C27 C28 122.5(4) . . ?
O42 C27 C28 116.1(4) . . ?
C29 C28 C33 118.4(4) . . ?
C29 C28 C27 119.0(4) . . ?
C33 C28 C27 122.5(4) . . ?
C30 C29 C28 122.5(4) . . ?
C30 C29 H29 118.7 . . ?
C28 C29 H29 118.7 . . ?
C29 C30 C31 118.5(4) . . ?
C29 C30 H30 120.7 . . ?
C31 C30 H30 120.7 . . ?
C32 C31 C30 120.7(4) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C33 121.6(4) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
N33 C33 C32 120.6(4) . . ?
N33 C33 C28 121.2(4) . . ?
C32 C33 C28 118.3(4) . . ?
C33 N33 C34 122.7(3) . . ?
C33 N33 H33N 117(3) . . ?
C34 N33 H33N 117(3) . . ?
C35 C34 C39 120.7(4) . . ?
C35 C34 N33 118.4(4) . . ?
C39 C34 N33 120.9(4) . . ?
C36 C35 C34 119.8(4) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C37 C36 C35 120.1(4) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 120.9(4) . . ?
C36 C37 H37 119.5 . . ?
C38 C37 H37 119.5 . . ?
C39 C38 C37 119.3(4) . . ?
C39 C38 C40 121.0(4) . . ?
C37 C38 C40 119.8(4) . . ?
C38 C39 C34 119.2(4) . . ?
C38 C39 C41 119.9(4) . . ?
C34 C39 C41 120.9(4) . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C27 O42 H42O 115(3) . . ?
H6A O44 H6B 109.5 . . ?
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
Cl1 C13 1.733(5) . ?
F1 C14 1.371(5) . ?
N1 C2 1.333(6) . ?
N1 C9 1.376(5) . ?
N1 H42O 1.30(5) . ?
C2 N3 1.325(6) . ?
C2 H2 0.9500 . ?
N3 C4 1.342(6) . ?
C4 N4 1.353(6) . ?
C4 C10 1.438(6) . ?
N4 C11 1.431(6) . ?
N4 H4N 0.84(5) . ?
C5 C6 1.378(6) . ?
C5 C10 1.415(6) . ?
C5 H5 0.9500 . ?
C6 O6 1.357(5) . ?
C6 C7 1.426(6) . ?
O6 C17 1.432(5) . ?
C7 O7 1.353(5) . ?
C7 C8 1.370(6) . ?
O7 C26 1.438(5) . ?
C8 C9 1.412(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(6) . ?
C11 C16 1.385(7) . ?
C11 C12 1.390(6) . ?
C12 C13 1.400(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.357(7) . ?
C14 C15 1.362(7) . ?
C15 C16 1.393(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.493(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.512(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N20 1.475(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
N20 C21 1.451(5) . ?
N20 C25 1.479(6) . ?
C21 C22 1.525(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O23 1.429(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O23 C24 1.429(6) . ?
C24 C25 1.503(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 O43 1.242(5) . ?
C27 O42 1.310(5) . ?
C27 C28 1.472(6) . ?
C28 C29 1.402(6) . ?
C28 C33 1.425(5) . ?
C29 C30 1.384(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.392(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.377(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.405(6) . ?
C32 H32 0.9500 . ?
C33 N33 1.377(5) . ?
N33 C34 1.425(5) . ?
N33 H33N 0.89(5) . ?
C34 C35 1.399(6) . ?
C34 C39 1.402(6) . ?
C35 C36 1.387(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.379(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.409(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.399(6) . ?
C38 C40 1.503(6) . ?
C39 C41 1.516(6) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
O42 H42O 1.29(5) . ?
O44 H6A 0.8500 . ?
O44 H6B 0.8502 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C2 N3 0.2(7) . . . . ?
N1 C2 N3 C4 0.5(7) . . . . ?
C2 N3 C4 N4 178.5(4) . . . . ?
C2 N3 C4 C10 -1.6(7) . . . . ?
N3 C4 N4 C11 2.8(7) . . . . ?
C10 C4 N4 C11 -177.0(4) . . . . ?
C10 C5 C6 O6 -179.5(4) . . . . ?
C10 C5 C6 C7 0.1(7) . . . . ?
C5 C6 O6 C17 -4.7(6) . . . . ?
C7 C6 O6 C17 175.7(4) . . . . ?
O6 C6 C7 O7 -1.6(6) . . . . ?
C5 C6 C7 O7 178.8(4) . . . . ?
O6 C6 C7 C8 177.9(4) . . . . ?
C5 C6 C7 C8 -1.7(7) . . . . ?
C8 C7 O7 C26 6.1(6) . . . . ?
C6 C7 O7 C26 -174.4(4) . . . . ?
O7 C7 C8 C9 -178.9(4) . . . . ?
C6 C7 C8 C9 1.7(7) . . . . ?
C2 N1 C9 C10 0.2(6) . . . . ?
C2 N1 C9 C8 -179.8(4) . . . . ?
C7 C8 C9 N1 179.9(4) . . . . ?
C7 C8 C9 C10 -0.1(7) . . . . ?
N1 C9 C10 C5 178.5(4) . . . . ?
C8 C9 C10 C5 -1.6(6) . . . . ?
N1 C9 C10 C4 -1.2(6) . . . . ?
C8 C9 C10 C4 178.7(4) . . . . ?
C6 C5 C10 C9 1.5(6) . . . . ?
C6 C5 C10 C4 -178.8(4) . . . . ?
N3 C4 C10 C9 2.0(6) . . . . ?
N4 C4 C10 C9 -178.2(4) . . . . ?
N3 C4 C10 C5 -177.7(4) . . . . ?
N4 C4 C10 C5 2.1(7) . . . . ?
C4 N4 C11 C16 36.2(7) . . . . ?
C4 N4 C11 C12 -145.8(5) . . . . ?
C16 C11 C12 C13 2.2(7) . . . . ?
N4 C11 C12 C13 -175.8(4) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C11 C12 C13 Cl1 -177.3(4) . . . . ?
C12 C13 C14 C15 -1.7(8) . . . . ?
Cl1 C13 C14 C15 175.5(4) . . . . ?
C12 C13 C14 F1 178.4(4) . . . . ?
Cl1 C13 C14 F1 -4.4(6) . . . . ?
C13 C14 C15 C16 1.2(8) . . . . ?
F1 C14 C15 C16 -178.9(4) . . . . ?
C12 C11 C16 C15 -2.7(7) . . . . ?
N4 C11 C16 C15 175.1(5) . . . . ?
C14 C15 C16 C11 1.0(8) . . . . ?
C6 O6 C17 C18 -179.1(4) . . . . ?
O6 C17 C18 C19 -173.7(4) . . . . ?
C17 C18 C19 N20 -53.0(6) . . . . ?
C18 C19 N20 C21 171.6(4) . . . . ?
C18 C19 N20 C25 -68.3(5) . . . . ?
C19 N20 C21 C22 -178.2(4) . . . . ?
C25 N20 C21 C22 59.9(5) . . . . ?
N20 C21 C22 O23 -59.9(5) . . . . ?
C21 C22 O23 C24 56.8(5) . . . . ?
C22 O23 C24 C25 -56.7(5) . . . . ?
C21 N20 C25 C24 -58.2(5) . . . . ?
C19 N20 C25 C24 -179.4(4) . . . . ?
O23 C24 C25 N20 57.2(5) . . . . ?
O43 C27 C28 C29 167.7(4) . . . . ?
O42 C27 C28 C29 -11.1(6) . . . . ?
O43 C27 C28 C33 -7.2(7) . . . . ?
O42 C27 C28 C33 174.0(4) . . . . ?
C33 C28 C29 C30 0.5(6) . . . . ?
C27 C28 C29 C30 -174.6(4) . . . . ?
C28 C29 C30 C31 0.8(7) . . . . ?
C29 C30 C31 C32 -1.2(7) . . . . ?
C30 C31 C32 C33 0.3(7) . . . . ?
C31 C32 C33 N33 -178.8(4) . . . . ?
C31 C32 C33 C28 1.0(6) . . . . ?
C29 C28 C33 N33 178.4(4) . . . . ?
C27 C28 C33 N33 -6.7(6) . . . . ?
C29 C28 C33 C32 -1.4(6) . . . . ?
C27 C28 C33 C32 173.5(4) . . . . ?
C32 C33 N33 C34 -3.6(6) . . . . ?
C28 C33 N33 C34 176.6(4) . . . . ?
C33 N33 C34 C35 -109.7(5) . . . . ?
C33 N33 C34 C39 70.0(6) . . . . ?
C39 C34 C35 C36 -0.7(7) . . . . ?
N33 C34 C35 C36 179.0(4) . . . . ?
C34 C35 C36 C37 -1.5(7) . . . . ?
C35 C36 C37 C38 1.6(7) . . . . ?
C36 C37 C38 C39 0.5(7) . . . . ?
C36 C37 C38 C40 -179.4(4) . . . . ?
C37 C38 C39 C34 -2.5(6) . . . . ?
C40 C38 C39 C34 177.3(4) . . . . ?
C37 C38 C39 C41 177.0(4) . . . . ?
C40 C38 C39 C41 -3.1(6) . . . . ?
C35 C34 C39 C38 2.7(6) . . . . ?
N33 C34 C39 C38 -177.0(4) . . . . ?
C35 C34 C39 C41 -176.9(4) . . . . ?
N33 C34 C39 C41 3.5(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341545
