#------------------------------------------------------------------------------
#$Date: 2020-05-23 08:14:15 +0300 (Sat, 23 May 2020) $
#$Revision: 252316 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243402.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_2243402
loop_
_publ_author_name
'George, Christy P.'
'Sangtani, Ekta'
'Gonnade, Rajesh G.'
_publ_section_title
;
 Crystal structure of a 1:1 co-crystal of the anticancer drug gefitinib
 with azelaic acid
;
_journal_coeditor_code           PK2627
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              884
_journal_page_last               888
_journal_paper_doi               10.1107/S2056989020006623
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C22 H24 Cl F N4 O3, C9 H16 O4'
_chemical_formula_moiety         'C22 H24 Cl F N4 O3, C9 H16 O4'
_chemical_formula_sum            'C31 H40 Cl F N4 O7'
_chemical_formula_weight         635.12
_chemical_name_common
;
Gefitinib--azelaic acid (1/1)
;
_chemical_name_systematic
;
Quinazolin-4-amine--nonanedioic acid (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.311(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7716(10)
_cell_length_b                   7.4153(13)
_cell_length_c                   38.175(7)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.35
_cell_measurement_theta_min      2.53
_cell_volume                     3046.7(8)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2016)
;
_computing_molecular_graphics
;
ORTEP3 (Farrugia, 2012), Mercury 2020.1 (Macrae et
al.,  2020)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2020), publCIF
(Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1615
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            92337
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.429
_diffrn_source                   'micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       'Thin Needle'
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         7338
_refine_ls_number_restraints     126
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0452
_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)+(0.0458P)²+1.2854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1103
_reflns_number_gt                5413
_reflns_number_total             7338
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2627sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2243402
_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   0.950
_shelx_estimated_absorpt_t_max   0.993
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'
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
N N1 0.47579(12) 0.8204(2) 0.55135(4) 0.0133(3) Uani d 1 . .
C C2 0.36066(14) 0.8699(2) 0.54311(5) 0.0148(4) Uani d 1 . .
H H2 0.3136 0.9129 0.5619 0.018 Uiso calc 1 . .
N N3 0.30169(12) 0.8670(2) 0.51143(4) 0.0144(3) Uani d 1 . .
C C4 0.36644(14) 0.8072(2) 0.48478(4) 0.0113(3) Uani d 1 . .
C C5 0.56600(14) 0.6768(2) 0.46286(4) 0.0111(3) Uani d 1 . .
H H5 0.5318 0.6671 0.4396 0.013 Uiso calc 1 . .
C C6 0.68614(14) 0.6245(2) 0.47037(4) 0.0109(3) Uani d 1 . .
C C7 0.73862(13) 0.6397(2) 0.50508(4) 0.0116(3) Uani d 1 . .
C C8 0.66847(14) 0.7041(2) 0.53159(4) 0.0117(3) Uani d 1 . .
H H8 0.7033 0.7129 0.5548 0.014 Uiso calc 1 . .
C C9 0.54411(14) 0.7573(2) 0.52418(4) 0.0115(3) Uani d 1 . .
C C10 0.49287(14) 0.7456(2) 0.48986(4) 0.0108(3) Uani d 1 . .
N N11 0.31164(12) 0.8064(2) 0.45205(4) 0.0129(3) Uani d 1 . .
H H11 0.3547(17) 0.784(3) 0.4348(5) 0.018(5) Uiso d 1 . .
C C12 0.1907(2) 0.8603(3) 0.44138(7) 0.0084(5) Uani d 0.915(7) A 1
C C13 0.1724(2) 0.9202(3) 0.40659(7) 0.0103(5) Uani d 0.915(7) A 1
H H13 0.2409 0.9296 0.3918 0.012 Uiso calc 0.915(7) A 1
C C14 0.0538(2) 0.9655(3) 0.39399(6) 0.0126(5) Uani d 0.915(7) A 1
C C15 -0.0455(2) 0.9516(5) 0.41588(7) 0.0121(6) Uani d 0.915(7) A 1
C C16 -0.0294(2) 0.8968(3) 0.45021(8) 0.0114(5) Uani d 0.915(7) A 1
H H16 -0.0984 0.8906 0.4649 0.014 Uiso calc 0.915(7) A 1
C C17 0.0893(2) 0.8503(3) 0.46331(6) 0.0103(5) Uani d 0.915(7) A 1
H H17 0.1014 0.8120 0.4870 0.012 Uiso calc 0.915(7) A 1
Cl Cl1 0.03309(6) 1.0446(3) 0.35140(2) 0.0239(3) Uani d 0.915(7) A 1
F F1 -0.1656(19) 0.981(6) 0.4079(9) 0.0207(5) Uani d 0.085(7) A 1
C C12' 0.165(3) 0.869(4) 0.4489(8) 0.0084(5) Uani d 0.085(7) A 2
C C13' 0.180(3) 0.904(3) 0.4171(9) 0.0103(5) Uani d 0.085(7) A 2
H H13' 0.2607 0.8997 0.4082 0.012 Uiso calc 0.085(7) A 2
C C14' 0.088(3) 0.944(3) 0.3964(9) 0.0126(5) Uani d 0.085(7) A 2
C C15' -0.034(2) 0.956(6) 0.4083(11) 0.0121(6) Uani d 0.085(7) A 2
C C16' -0.038(3) 0.918(4) 0.4387(10) 0.0114(5) Uani d 0.085(7) A 2
H H16' -0.1167 0.9307 0.4489 0.014 Uiso calc 0.085(7) A 2
C C17' 0.051(3) 0.863(4) 0.4588(8) 0.0103(5) Uani d 0.085(7) A 2
H H17' 0.0340 0.8158 0.4813 0.012 Uiso calc 0.085(7) A 2
Cl Cl1' 0.0350(8) 0.977(3) 0.3483(3) 0.0239(3) Uani d 0.085(7) A 2
F F1' -0.15929(17) 0.9946(5) 0.40135(6) 0.0207(5) Uani d 0.915(7) A 2
O O18 0.76536(10) 0.55753(17) 0.44664(3) 0.0146(3) Uani d 1 . .
C C19 0.71844(14) 0.5374(3) 0.41114(4) 0.0140(3) Uani d 1 . .
H H19A 0.6840 0.6529 0.4021 0.017 Uiso calc 1 . .
H H19B 0.6523 0.4447 0.4096 0.017 Uiso calc 1 . .
C C20 0.82895(15) 0.4798(3) 0.39031(5) 0.0167(4) Uani d 1 . .
H H20A 0.8851 0.5844 0.3879 0.020 Uiso calc 1 . .
H H20B 0.8755 0.3852 0.4036 0.020 Uiso calc 1 . .
C C21 0.79365(15) 0.4080(2) 0.35412(5) 0.0162(4) Uani d 1 . .
H H21A 0.8708 0.3825 0.3418 0.019 Uiso calc 1 . .
H H21B 0.7492 0.2923 0.3567 0.019 Uiso calc 1 . .
N N22 0.71453(13) 0.5303(2) 0.33193(4) 0.0170(3) Uani d 1 . .
C C23 0.69993(18) 0.4460(3) 0.29657(5) 0.0252(4) Uani d 1 . .
H H23A 0.6568 0.3287 0.2985 0.030 Uiso calc 1 . .
H H23B 0.7829 0.4231 0.2873 0.030 Uiso calc 1 . .
C C24 0.6265(2) 0.5668(4) 0.27160(6) 0.0392(6) Uani d 1 . .
H H24A 0.6195 0.5091 0.2482 0.047 Uiso calc 1 . .
H H24B 0.5415 0.5827 0.2801 0.047 Uiso calc 1 . .
O O25 0.68388(16) 0.7383(3) 0.26857(4) 0.0467(5) Uani d 1 . .
C C26 0.6932(2) 0.8207(3) 0.30238(6) 0.0426(6) Uani d 1 . .
H H26A 0.6088 0.8361 0.3113 0.051 Uiso calc 1 . .
H H26B 0.7306 0.9419 0.3002 0.051 Uiso calc 1 . .
C C27 0.77011(19) 0.7117(3) 0.32823(5) 0.0261(4) Uani d 1 . .
H H27A 0.8558 0.7002 0.3201 0.031 Uiso calc 1 . .
H H27B 0.7740 0.7734 0.3512 0.031 Uiso calc 1 . .
O O28 0.85921(10) 0.58683(17) 0.50862(3) 0.0148(3) Uani d 1 . .
C C29 0.92077(14) 0.6098(3) 0.54230(5) 0.0162(4) Uani d 1 . .
H H29A 0.9179 0.7371 0.5491 0.024 Uiso calc 1 . .
H H29B 1.0075 0.5712 0.5412 0.024 Uiso calc 1 . .
H H29C 0.8790 0.5367 0.5597 0.024 Uiso calc 1 . .
O O30 0.58731(10) 0.86845(18) 0.61271(3) 0.0181(3) Uani d 1 . .
H H30 0.533(2) 0.852(4) 0.5915(7) 0.056(8) Uiso d 1 . .
O O31 0.41210(11) 0.90780(19) 0.64135(4) 0.0238(3) Uani d 1 . .
C C32 0.52448(15) 0.9063(2) 0.64073(5) 0.0169(4) Uani d 1 . .
C C33 0.60896(16) 0.9548(3) 0.67194(5) 0.0209(4) Uani d 1 . .
H H33A 0.6142 1.0879 0.6735 0.025 Uiso calc 1 . .
H H33B 0.6934 0.9093 0.6676 0.025 Uiso calc 1 . .
C C34 0.57017(16) 0.8827(3) 0.70716(5) 0.0200(4) Uani d 1 . .
H H34A 0.5747 0.7494 0.7073 0.024 Uiso calc 1 B 1
H H34B 0.4834 0.9184 0.7112 0.024 Uiso calc 1 B 1
C C35 0.6584(3) 0.9608(5) 0.73679(8) 0.0196(6) Uani d 0.770(4) C 1
H H35A 0.7449 0.9243 0.7324 0.023 Uiso calc 0.770(4) C 1
H H35B 0.6546 1.0941 0.7360 0.023 Uiso calc 0.770(4) C 1
C C36 0.6250(3) 0.8968(3) 0.77317(6) 0.0178(6) Uani d 0.770(4) C 1
H H36A 0.6289 0.7634 0.7740 0.021 Uiso calc 0.770(4) C 1
H H36B 0.5388 0.9335 0.7777 0.021 Uiso calc 0.770(4) C 1
C C37 0.7126(2) 0.9744(4) 0.80178(8) 0.0186(6) Uani d 0.770(4) C 1
H H37A 0.7989 0.9407 0.7967 0.022 Uiso calc 0.770(4) C 1
H H37B 0.7070 1.1077 0.8011 0.022 Uiso calc 0.770(4) C 1
C C38 0.6847(2) 0.9101(3) 0.83854(7) 0.0174(6) Uani d 0.770(4) C 1
H H38A 0.6933 0.7772 0.8394 0.021 Uiso calc 0.770(4) C 1
H H38B 0.5973 0.9397 0.8432 0.021 Uiso calc 0.770(4) C 1
C C39 0.7695(3) 0.9931(5) 0.86770(8) 0.0150(7) Uani d 0.770(4) C 1
H H39A 0.7688 1.1260 0.8653 0.018 Uiso calc 0.770(4) C 1
H H39B 0.7366 0.9625 0.8908 0.018 Uiso calc 0.770(4) C 1
C C35' 0.6128(9) 0.9559(19) 0.7400(3) 0.0196(6) Uani d 0.230(4) C 2
H H35C 0.6048 1.0888 0.7387 0.023 Uiso calc 0.230(4) C 2
H H35D 0.7025 0.9281 0.7433 0.023 Uiso calc 0.230(4) C 2
C C36' 0.5482(8) 0.8921(13) 0.7725(2) 0.023(2) Uani d 0.230(4) C 2
H H36C 0.5562 0.7594 0.7743 0.027 Uiso calc 0.230(4) C 2
H H36D 0.4586 0.9209 0.7698 0.027 Uiso calc 0.230(4) C 2
C C37' 0.6007(7) 0.9780(13) 0.8072(2) 0.023(2) Uani d 0.230(4) C 2
H H37C 0.5988 1.1109 0.8048 0.028 Uiso calc 0.230(4) C 2
H H37D 0.5456 0.9453 0.8264 0.028 Uiso calc 0.230(4) C 2
C C38' 0.7281(8) 0.9218(12) 0.8171(3) 0.0139(19) Uani d 0.230(4) C 2
H H38C 0.7850 0.9748 0.8002 0.017 Uiso calc 0.230(4) C 2
H H38D 0.7333 0.7890 0.8149 0.017 Uiso calc 0.230(4) C 2
C C39' 0.7737(12) 0.9740(19) 0.8538(3) 0.019(2) Uani d 0.230(4) C 2
H H39C 0.7657 1.1065 0.8559 0.023 Uiso calc 0.230(4) C 2
H H39D 0.7161 0.9199 0.8705 0.023 Uiso calc 0.230(4) C 2
C C40 0.90344(15) 0.9248(2) 0.86617(5) 0.0153(4) Uani d 1 . .
O O41 0.97487(11) 1.00506(19) 0.84437(3) 0.0235(3) Uani d 1 . .
H H41 1.060(2) 0.950(2) 0.8463(4) 0.035 Uiso calc 1 . .
O O42 0.93796(11) 0.80413(19) 0.88602(3) 0.0224(3) Uani d 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'
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'
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
C2 N1 C9 . . 116.13(14) ?
N1 C2 N3 . . 128.05(15) ?
N1 C2 H2 . . 116.0 ?
N3 C2 H2 . . 116.0 ?
C4 N3 C2 . . 116.72(14) ?
N3 C4 N11 . . 118.80(14) ?
N3 C4 C10 . . 121.53(15) ?
N11 C4 C10 . . 119.66(14) ?
C6 C5 C10 . . 119.83(15) ?
C6 C5 H5 . . 120.1 ?
C10 C5 H5 . . 120.1 ?
O18 C6 C5 . . 125.13(15) ?
O18 C6 C7 . . 114.31(13) ?
C5 C6 C7 . . 120.56(14) ?
O28 C7 C8 . . 125.43(15) ?
O28 C7 C6 . . 114.31(14) ?
C8 C7 C6 . . 120.26(14) ?
C7 C8 C9 . . 119.64(15) ?
C7 C8 H8 . . 120.2 ?
C9 C8 H8 . . 120.2 ?
N1 C9 C10 . . 121.46(14) ?
N1 C9 C8 . . 118.33(15) ?
C10 C9 C8 . . 120.21(14) ?
C9 C10 C5 . . 119.48(14) ?
C9 C10 C4 . . 116.09(14) ?
C5 C10 C4 . . 124.43(15) ?
C4 N11 C12 . . 128.84(17) ?
C4 N11 C12' . . 116.5(11) ?
C4 N11 H11 . . 119.4(13) ?
C12 N11 H11 . . 111.4(13) ?
C12' N11 H11 . . 123.9(17) ?
C17 C12 C13 . . 119.82(19) ?
C17 C12 N11 . . 123.1(3) ?
C13 C12 N11 . . 117.1(2) ?
C14 C13 C12 . . 119.7(2) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
C15 C14 C13 . . 119.6(2) ?
C15 C14 Cl1 . . 121.1(2) ?
C13 C14 Cl1 . . 119.2(2) ?
F1 C15 C16 . . 110.4(15) ?
F1 C15 C14 . . 127.9(16) ?
C16 C15 C14 . . 121.6(2) ?
C15 C16 C17 . . 119.50(19) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C16 C17 C12 . . 119.7(2) ?
C16 C17 H17 . . 120.1 ?
C12 C17 H17 . . 120.1 ?
C13' C12' C17' . . 116(3) ?
C13' C12' N11 . . 89(2) ?
C17' C12' N11 . . 152(3) ?
C12' C13' C14' . . 122(3) ?
C12' C13' H13' . . 119.2 ?
C14' C13' H13' . . 119.2 ?
C13' C14' C15' . . 122(3) ?
C13' C14' Cl1' . . 145(3) ?
C15' C14' Cl1' . . 93(2) ?
C16' C15' F1' . . 99(3) ?
C16' C15' C14' . . 112(3) ?
F1' C15' C14' . . 149(4) ?
C15' C16' C17' . . 127(3) ?
C15' C16' H16' . . 116.4 ?
C17' C16' H16' . . 116.4 ?
C16' C17' C12' . . 121(3) ?
C16' C17' H17' . . 119.7 ?
C12' C17' H17' . . 119.7 ?
C6 O18 C19 . . 117.35(12) ?
O18 C19 C20 . . 105.66(12) ?
O18 C19 H19A . . 110.6 ?
C20 C19 H19A . . 110.6 ?
O18 C19 H19B . . 110.6 ?
C20 C19 H19B . . 110.6 ?
H19A C19 H19B . . 108.7 ?
C21 C20 C19 . . 113.76(13) ?
C21 C20 H20A . . 108.8 ?
C19 C20 H20A . . 108.8 ?
C21 C20 H20B . . 108.8 ?
C19 C20 H20B . . 108.8 ?
H20A C20 H20B . . 107.7 ?
N22 C21 C20 . . 115.03(15) ?
N22 C21 H21A . . 108.5 ?
C20 C21 H21A . . 108.5 ?
N22 C21 H21B . . 108.5 ?
C20 C21 H21B . . 108.5 ?
H21A C21 H21B . . 107.5 ?
C27 N22 C21 . . 112.56(14) ?
C27 N22 C23 . . 108.83(15) ?
C21 N22 C23 . . 107.32(14) ?
N22 C23 C24 . . 110.88(17) ?
N22 C23 H23A . . 109.5 ?
C24 C23 H23A . . 109.5 ?
N22 C23 H23B . . 109.5 ?
C24 C23 H23B . . 109.5 ?
H23A C23 H23B . . 108.1 ?
O25 C24 C23 . . 111.37(19) ?
O25 C24 H24A . . 109.4 ?
C23 C24 H24A . . 109.4 ?
O25 C24 H24B . . 109.4 ?
C23 C24 H24B . . 109.4 ?
H24A C24 H24B . . 108.0 ?
C24 O25 C26 . . 108.91(17) ?
O25 C26 C27 . . 112.41(18) ?
O25 C26 H26A . . 109.1 ?
C27 C26 H26A . . 109.1 ?
O25 C26 H26B . . 109.1 ?
C27 C26 H26B . . 109.1 ?
H26A C26 H26B . . 107.9 ?
N22 C27 C26 . . 109.72(18) ?
N22 C27 H27A . . 109.7 ?
C26 C27 H27A . . 109.7 ?
N22 C27 H27B . . 109.7 ?
C26 C27 H27B . . 109.7 ?
H27A C27 H27B . . 108.2 ?
C7 O28 C29 . . 117.44(13) ?
O28 C29 H29A . . 109.5 ?
O28 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
O28 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C32 O30 H30 . . 112.8(15) ?
O31 C32 O30 . . 124.29(17) ?
O31 C32 C33 . . 123.51(16) ?
O30 C32 C33 . . 112.16(14) ?
C32 C33 C34 . . 115.76(15) ?
C32 C33 H33A . . 108.3 ?
C34 C33 H33A . . 108.3 ?
C32 C33 H33B . . 108.3 ?
C34 C33 H33B . . 108.3 ?
H33A C33 H33B . . 107.4 ?
C35' C34 C33 . . 123.6(5) ?
C33 C34 C35 . . 109.25(18) ?
C33 C34 H34A . . 109.8 ?
C35 C34 H34A . . 109.8 ?
C33 C34 H34B . . 109.8 ?
C35 C34 H34B . . 109.8 ?
H34A C34 H34B . . 108.3 ?
C36 C35 C34 . . 112.7(2) ?
C36 C35 H35A . . 109.1 ?
C34 C35 H35A . . 109.1 ?
C36 C35 H35B . . 109.1 ?
C34 C35 H35B . . 109.1 ?
H35A C35 H35B . . 107.8 ?
C35 C36 C37 . . 111.9(2) ?
C35 C36 H36A . . 109.2 ?
C37 C36 H36A . . 109.2 ?
C35 C36 H36B . . 109.2 ?
C37 C36 H36B . . 109.2 ?
H36A C36 H36B . . 107.9 ?
C38 C37 C36 . . 113.7(2) ?
C38 C37 H37A . . 108.8 ?
C36 C37 H37A . . 108.8 ?
C38 C37 H37B . . 108.8 ?
C36 C37 H37B . . 108.8 ?
H37A C37 H37B . . 107.7 ?
C37 C38 C39 . . 114.0(2) ?
C37 C38 H38A . . 108.7 ?
C39 C38 H38A . . 108.7 ?
C37 C38 H38B . . 108.7 ?
C39 C38 H38B . . 108.7 ?
H38A C38 H38B . . 107.6 ?
C40 C39 C38 . . 111.9(2) ?
C40 C39 H39A . . 109.2 ?
C38 C39 H39A . . 109.2 ?
C40 C39 H39B . . 109.2 ?
C38 C39 H39B . . 109.2 ?
H39A C39 H39B . . 107.9 ?
C34 C35' C36' . . 117.2(8) ?
C34 C35' H35C . . 108.0 ?
C36' C35' H35C . . 108.0 ?
C34 C35' H35D . . 108.0 ?
C36' C35' H35D . . 108.0 ?
H35C C35' H35D . . 107.2 ?
C35' C36' C37' . . 113.9(8) ?
C35' C36' H36C . . 108.8 ?
C37' C36' H36C . . 108.8 ?
C35' C36' H36D . . 108.8 ?
C37' C36' H36D . . 108.8 ?
H36C C36' H36D . . 107.7 ?
C38' C37' C36' . . 114.0(7) ?
C38' C37' H37C . . 108.8 ?
C36' C37' H37C . . 108.8 ?
C38' C37' H37D . . 108.8 ?
C36' C37' H37D . . 108.8 ?
H37C C37' H37D . . 107.6 ?
C37' C38' C39' . . 115.5(8) ?
C37' C38' H38C . . 108.4 ?
C39' C38' H38C . . 108.4 ?
C37' C38' H38D . . 108.4 ?
C39' C38' H38D . . 108.4 ?
H38C C38' H38D . . 107.5 ?
C40 C39' C38' . . 119.4(8) ?
C40 C39' H39C . . 107.5 ?
C38' C39' H39C . . 107.5 ?
C40 C39' H39D . . 107.5 ?
C38' C39' H39D . . 107.5 ?
H39C C39' H39D . . 107.0 ?
O42 C40 O41 . . 124.03(16) ?
O42 C40 C39' . . 129.0(6) ?
O41 C40 C39' . . 104.8(5) ?
O42 C40 C39 . . 118.8(2) ?
O41 C40 C39 . . 117.10(19) ?
C40 O41 H41 . . 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
N1 C2 . 1.319(2) ?
N1 C9 . 1.378(2) ?
C2 N3 . 1.343(2) ?
C2 H2 . 0.9500 ?
N3 C4 . 1.333(2) ?
C4 N11 . 1.360(2) ?
C4 C10 . 1.442(2) ?
C5 C6 . 1.370(2) ?
C5 C10 . 1.417(2) ?
C5 H5 . 0.9500 ?
C6 O18 . 1.3631(19) ?
C6 C7 . 1.424(2) ?
C7 O28 . 1.3585(18) ?
C7 C8 . 1.373(2) ?
C8 C9 . 1.414(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.404(2) ?
N11 C12 . 1.408(2) ?
N11 C12' . 1.64(3) ?
N11 H11 . 0.84(2) ?
C12 C17 . 1.404(3) ?
C12 C13 . 1.407(3) ?
C13 C14 . 1.389(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.387(3) ?
C14 Cl1 . 1.734(3) ?
C15 F1 . 1.335(19) ?
C15 C16 . 1.377(3) ?
C16 C17 . 1.397(3) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C12' C13' . 1.26(4) ?
C12' C17' . 1.31(3) ?
C13' C14' . 1.27(4) ?
C13' H13' . 0.9500 ?
C14' C15' . 1.41(4) ?
C14' Cl1' . 1.92(3) ?
C15' C16' . 1.20(4) ?
C15' F1' . 1.395(19) ?
C16' C17' . 1.27(4) ?
C16' H16' . 0.9500 ?
C17' H17' . 0.9500 ?
O18 C19 . 1.435(2) ?
C19 C20 . 1.519(2) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 C21 . 1.515(2) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 N22 . 1.486(2) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
N22 C27 . 1.482(2) ?
N22 C23 . 1.490(2) ?
C23 C24 . 1.509(3) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 O25 . 1.421(3) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
O25 C26 . 1.428(3) ?
C26 C27 . 1.499(3) ?
C26 H26A . 0.9900 ?
C26 H26B . 0.9900 ?
C27 H27A . 0.9900 ?
C27 H27B . 0.9900 ?
O28 C29 . 1.433(2) ?
C29 H29A . 0.9800 ?
C29 H29B . 0.9800 ?
C29 H29C . 0.9800 ?
O30 C32 . 1.319(2) ?
O30 H30 . 0.99(3) ?
O31 C32 . 1.212(2) ?
C32 C33 . 1.513(2) ?
C33 C34 . 1.521(3) ?
C33 H33A . 0.9900 ?
C33 H33B . 0.9900 ?
C34 C35' . 1.426(12) ?
C34 C35 . 1.559(4) ?
C34 H34A . 0.9900 ?
C34 H34B . 0.9900 ?
C35 C36 . 1.525(4) ?
C35 H35A . 0.9900 ?
C35 H35B . 0.9900 ?
C36 C37 . 1.527(4) ?
C36 H36A . 0.9900 ?
C36 H36B . 0.9900 ?
C37 C38 . 1.524(4) ?
C37 H37A . 0.9900 ?
C37 H37B . 0.9900 ?
C38 C39 . 1.540(4) ?
C38 H38A . 0.9900 ?
C38 H38B . 0.9900 ?
C39 C40 . 1.533(4) ?
C39 H39A . 0.9900 ?
C39 H39B . 0.9900 ?
C35' C36' . 1.522(14) ?
C35' H35C . 0.9900 ?
C35' H35D . 0.9900 ?
C36' C37' . 1.556(12) ?
C36' H36C . 0.9900 ?
C36' H36D . 0.9900 ?
C37' C38' . 1.469(11) ?
C37' H37C . 0.9900 ?
C37' H37D . 0.9900 ?
C38' C39' . 1.516(15) ?
C38' H38C . 0.9900 ?
C38' H38D . 0.9900 ?
C39' C40 . 1.501(13) ?
C39' H39C . 0.9900 ?
C39' H39D . 0.9900 ?
C40 O42 . 1.221(2) ?
C40 O41 . 1.300(2) ?
O41 H41 . 1.01(2) ?
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
N11 H11 O42 4_575 0.84(2) 2.20(2) 3.025(2) 169.6(18)
O41 H41 N22 4_676 1.01 1.78 2.6566(19) 144
O30 H30 N1 . 0.99(3) 1.65(3) 2.6135(19) 166(2)
C5 H5 O42 4_575 0.95 2.25 3.194(2) 170
C2 H2 F1 3_576 0.95 2.15 3.07(3) 163
C2 H2 F1' 3_576 0.95 2.32 3.253(3) 166
C29 H29B O18 3_766 0.98 2.65 3.6101(19) 167
C23 H23B O25 2_645 0.99 2.57 3.220(2) 123
C27 H27B F1 1_655 0.99 2.71 3.68(4) 166
C39 H39A O30 2_656 0.99 2.50 3.255(4) 133
C21 H21B O31 3_666 0.99 2.29 3.234(2) 160
C13 H13 O30 3_676 0.95 2.39 3.139(3) 135
C13' H13' O30 3_676 0.95 2.53 3.268(3) 135
Cg2 . Cg2 3_666 . . 3.5358(11) 0.03(8)
Cg2 . Cg3 3_666 . . 3.7909(11) 1.04(7)
Cg2 . Cg3 3_676 . . 3.7530(11) 1.04(7)
Cg3 . Cg3 3_666 . . 3.7934(11) 0.03(7)
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
C9 N1 C2 N3 . . . . -0.2(3) ?
N1 C2 N3 C4 . . . . -0.1(3) ?
C2 N3 C4 N11 . . . . -178.27(15) ?
C2 N3 C4 C10 . . . . 1.1(2) ?
C10 C5 C6 O18 . . . . -179.65(15) ?
C10 C5 C6 C7 . . . . -0.4(2) ?
O18 C6 C7 O28 . . . . 0.7(2) ?
C5 C6 C7 O28 . . . . -178.59(15) ?
O18 C6 C7 C8 . . . . -179.53(15) ?
C5 C6 C7 C8 . . . . 1.2(3) ?
O28 C7 C8 C9 . . . . 179.02(15) ?
C6 C7 C8 C9 . . . . -0.7(2) ?
C2 N1 C9 C10 . . . . -0.5(2) ?
C2 N1 C9 C8 . . . . 179.41(16) ?
C7 C8 C9 N1 . . . . 179.62(15) ?
C7 C8 C9 C10 . . . . -0.5(2) ?
N1 C9 C10 C5 . . . . -178.89(15) ?
C8 C9 C10 C5 . . . . 1.2(2) ?
N1 C9 C10 C4 . . . . 1.4(2) ?
C8 C9 C10 C4 . . . . -178.49(15) ?
C6 C5 C10 C9 . . . . -0.7(2) ?
C6 C5 C10 C4 . . . . 178.92(16) ?
N3 C4 C10 C9 . . . . -1.7(2) ?
N11 C4 C10 C9 . . . . 177.61(15) ?
N3 C4 C10 C5 . . . . 178.60(16) ?
N11 C4 C10 C5 . . . . -2.1(3) ?
N3 C4 N11 C12 . . . . -0.6(3) ?
C10 C4 N11 C12 . . . . -179.94(18) ?
N3 C4 N11 C12' . . . . -3.5(12) ?
C10 C4 N11 C12' . . . . 177.1(11) ?
C4 N11 C12 C17 . . . . -29.1(3) ?
C4 N11 C12 C13 . . . . 153.23(19) ?
C17 C12 C13 C14 . . . . -1.3(3) ?
N11 C12 C13 C14 . . . . 176.4(2) ?
C12 C13 C14 C15 . . . . 0.1(3) ?
C12 C13 C14 Cl1 . . . . 178.38(17) ?
C13 C14 C15 F1 . . . . -177(2) ?
Cl1 C14 C15 F1 . . . . 5(2) ?
C13 C14 C15 C16 . . . . 1.2(4) ?
Cl1 C14 C15 C16 . . . . -177.0(2) ?
F1 C15 C16 C17 . . . . 176.9(19) ?
C14 C15 C16 C17 . . . . -1.3(4) ?
C15 C16 C17 C12 . . . . 0.1(4) ?
C13 C12 C17 C16 . . . . 1.2(3) ?
N11 C12 C17 C16 . . . . -176.4(2) ?
C4 N11 C12' C13' . . . . 158.5(10) ?
C4 N11 C12' C17' . . . . -49(5) ?
C17' C12' C13' C14' . . . . 5(2) ?
N11 C12' C13' C14' . . . . 171.7(16) ?
C12' C13' C14' C15' . . . . 1(2) ?
C12' C13' C14' Cl1' . . . . -168(3) ?
C13' C14' C15' C16' . . . . -2(5) ?
Cl1' C14' C15' C16' . . . . 171(4) ?
C13' C14' C15' F1' . . . . 177(6) ?
Cl1' C14' C15' F1' . . . . -10(7) ?
F1' C15' C16' C17' . . . . 177(3) ?
C14' C15' C16' C17' . . . . -4(6) ?
C15' C16' C17' C12' . . . . 11(6) ?
C13' C12' C17' C16' . . . . -11(4) ?
N11 C12' C17' C16' . . . . -161(4) ?
C5 C6 O18 C19 . . . . -1.1(2) ?
C7 C6 O18 C19 . . . . 179.61(14) ?
C6 O18 C19 C20 . . . . 174.33(14) ?
O18 C19 C20 C21 . . . . 166.04(15) ?
C19 C20 C21 N22 . . . . 54.0(2) ?
C20 C21 N22 C27 . . . . 54.86(19) ?
C20 C21 N22 C23 . . . . 174.57(15) ?
C27 N22 C23 C24 . . . . -54.7(2) ?
C21 N22 C23 C24 . . . . -176.76(17) ?
N22 C23 C24 O25 . . . . 57.9(2) ?
C23 C24 O25 C26 . . . . -59.2(2) ?
C24 O25 C26 C27 . . . . 60.6(2) ?
C21 N22 C27 C26 . . . . 173.58(15) ?
C23 N22 C27 C26 . . . . 54.74(19) ?
O25 C26 C27 N22 . . . . -59.3(2) ?
C8 C7 O28 C29 . . . . -3.9(2) ?
C6 C7 O28 C29 . . . . 175.88(15) ?
O31 C32 C33 C34 . . . . 41.3(3) ?
O30 C32 C33 C34 . . . . -140.79(17) ?
C32 C33 C34 C35' . . . . -160.0(6) ?
C32 C33 C34 C35 . . . . -174.15(19) ?
C33 C34 C35 C36 . . . . 179.3(2) ?
C34 C35 C36 C37 . . . . 179.9(2) ?
C35 C36 C37 C38 . . . . -178.5(2) ?
C36 C37 C38 C39 . . . . -177.9(2) ?
C37 C38 C39 C40 . . . . -69.0(3) ?
C33 C34 C35' C36' . . . . 169.2(6) ?
C34 C35' C36' C37' . . . . 179.8(8) ?
C35' C36' C37' C38' . . . . -67.5(11) ?
C36' C37' C38' C39' . . . . -169.1(9) ?
C37' C38' C39' C40 . . . . -179.1(9) ?
C38' C39' C40 O42 . . . . -103.4(10) ?
C38' C39' C40 O41 . . . . 60.0(11) ?
C38 C39 C40 O42 . . . . -99.5(3) ?
C38 C39 C40 O41 . . . . 83.0(3) ?

_cod_database_fobs_code 2243402
