#------------------------------------------------------------------------------
#$Date: 2022-01-06 23:14:58 +0200 (Thu, 06 Jan 2022) $
#$Revision: 271839 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/39/7243945.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_7243945
loop_
_publ_author_name
'Ito, Sho'
'White, Fraser J.'
'Okunishi, Eiji'
'Aoyama, Yoshitaka'
'Yamano, Akihito'
'Sato, Hiroyasu'
'Ferrara, Joseph D.'
'Jasnowski, Michał'
'Meyer, Mathias'
_publ_section_title
;
 Structure determination of small molecule compounds by an electron
 diffractometer for 3D ED/MicroED
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              8622
_journal_page_last               8630
_journal_paper_doi               10.1039/D1CE01172C
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C22 H24 Cl F N4 O3'
_chemical_formula_sum            'C22 H24 Cl F N4 O3'
_chemical_formula_weight         446.90
_chemical_name_systematic
N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                93.78(4)
_cell_angle_beta                 97.00(4)
_cell_angle_gamma                101.72(4)
_cell_formula_units_Z            2
_cell_length_a                   9.146(4)
_cell_length_b                   9.990(5)
_cell_length_c                   13.028(5)
_cell_measurement_reflns_used    529
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.8620
_cell_measurement_theta_min      0.1120
_cell_volume                     1151.8(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.825
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  60.00   1.00    4.00    --    0.00   0.00   0.00   70
  2  ω    -10.00  55.00   1.00    4.00    --    0.00   0.00   0.00   65
  3  ω    -11.00  45.00   1.00    2.00    --    0.00   0.00   0.00   56
  4  ω    -20.00  50.00   1.00    4.00    --    0.00   0.00   0.00   70
  5  ω    -36.00  30.00   1.00   10.00    --    0.00   0.00   0.00   66
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0022725000
_diffrn_orient_matrix_UB_12      -0.0016188000
_diffrn_orient_matrix_UB_13      0.0004356000
_diffrn_orient_matrix_UB_21      -0.0002073000
_diffrn_orient_matrix_UB_22      -0.0013945000
_diffrn_orient_matrix_UB_23      -0.0017063000
_diffrn_orient_matrix_UB_31      0.0016739000
_diffrn_orient_matrix_UB_32      -0.0014411000
_diffrn_orient_matrix_UB_33      0.0008365000
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.825
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7277
_diffrn_reflns_point_group_measured_fraction_full 0.825
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        0.734
_diffrn_reflns_theta_max         0.734
_diffrn_reflns_theta_min         0.097
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       plate
_exptl_crystal_F_000             179
_exptl_crystal_size_max          0.0003
_exptl_crystal_size_mid          0.0003
_exptl_crystal_size_min          0.0001
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       171(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   2.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.167
_refine_ls_R_factor_all          0.2080
_refine_ls_R_factor_gt           0.1545
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3466
_refine_ls_wR_factor_ref         0.3697
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1322
_reflns_number_total             2117
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01172c1.cif
_cod_data_source_block           gefitinib
_cod_depositor_comments
'Adding full bibliography for 7243939--7243951.cif.'
_cod_database_code               7243945
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H24 Cl F N4 O3'
_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.
;
_reflns_odcompleteness_completeness 83.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.73
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C22(H22A,H22B), C16(H16A,H16B), C18(H18A,H18B), C21(H21A,
 H21B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 N25(H25), C11(H11), C4(H4), C1(H1), C14(H14), C10(H10), C7(H7)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.064
_oxdiff_exptl_absorpt_empirical_full_min 0.290
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N25 N -0.8686(13) -0.3459(12) -0.3689(7) 0.074(4) Uani 1 1 d . . . . .
H25 H -0.859805 -0.403888 -0.323751 0.088 Uiso 1 1 calc R U . . .
C11 C -0.9787(18) -0.0023(13) -0.3410(9) 0.096(5) Uani 1 1 d . . . . .
H11 H -0.973952 0.078640 -0.373056 0.115 Uiso 1 1 calc R U . . .
O29 O -0.2577(19) -0.5571(15) 0.1459(7) 0.080(4) Uani 1 1 d . . . . .
C8 C -0.8274(15) -0.3822(11) -0.4638(7) 0.061(4) Uani 1 1 d . . . . .
C6 C -0.7623(15) -0.5065(11) -0.4767(7) 0.062(4) Uani 1 1 d . . . . .
N24 N -0.8501(14) -0.3048(10) -0.5442(7) 0.060(3) Uani 1 1 d . . . . .
O27 O -0.5712(14) -0.8557(11) -0.5243(7) 0.074(4) Uani 1 1 d . . . . .
C4 C -0.6641(12) -0.6559(11) -0.5976(7) 0.055(3) Uani 1 1 d . . . . .
H4 H -0.645504 -0.679002 -0.664346 0.066 Uiso 1 1 calc R U . . .
C9 C -0.9221(12) -0.2324(11) -0.3326(7) 0.050(3) Uani 1 1 d . . . . .
C5 C -0.7267(15) -0.5384(11) -0.5773(7) 0.062(4) Uani 1 1 d . . . . .
C17 C -0.596(2) -0.8693(15) -0.1657(8) 0.108(6) Uani 1 1 d . . . . .
H17A H -0.652639 -0.885601 -0.107773 0.130 Uiso 1 1 calc R U . . .
H17B H -0.611363 -0.955773 -0.208205 0.130 Uiso 1 1 calc R U . . .
C2 C -0.6596(14) -0.7026(10) -0.4103(6) 0.054(4) Uani 1 1 d . . . . .
C22 C -0.2314(18) -0.5107(15) 0.0474(10) 0.094(5) Uani 1 1 d . . . . .
H22A H -0.128605 -0.458347 0.053141 0.113 Uiso 1 1 calc R U . . .
H22B H -0.298229 -0.449604 0.028777 0.113 Uiso 1 1 calc R U . . .
C3 C -0.6294(13) -0.7392(11) -0.5147(7) 0.055(3) Uani 1 1 d . . . . .
C16 C -0.6606(19) -0.7632(13) -0.2322(7) 0.097(5) Uani 1 1 d . . . . .
H16A H -0.768348 -0.774965 -0.231498 0.116 Uiso 1 1 calc R U . . .
H16B H -0.612040 -0.669936 -0.205087 0.116 Uiso 1 1 calc R U . . .
N26 N -0.4055(18) -0.7116(14) -0.0437(7) 0.065(4) Uani 1 1 d . . . . .
C12 C -1.0462(17) -0.0175(14) -0.2462(9) 0.091(5) Uani 1 1 d . . . . .
C15 C -0.5363(18) -0.8979(14) -0.6220(8) 0.091(5) Uani 1 1 d . . . . .
H15A H -0.624818 -0.911992 -0.672642 0.136 Uiso 1 1 calc R U . . .
H15B H -0.501561 -0.982075 -0.618059 0.136 Uiso 1 1 calc R U . . .
H15C H -0.458766 -0.828306 -0.641889 0.136 Uiso 1 1 calc R U . . .
C18 C -0.4330(18) -0.8240(13) -0.1246(9) 0.080(5) Uani 1 1 d . . . . .
H18A H -0.396337 -0.900765 -0.097056 0.096 Uiso 1 1 calc R U . . .
H18B H -0.377258 -0.795243 -0.180974 0.096 Uiso 1 1 calc R U . . .
O28 O -0.6277(13) -0.7922(10) -0.3387(6) 0.067(3) Uani 1 1 d . . . . .
N23 N -0.7522(15) -0.4573(12) -0.6592(6) 0.078(4) Uani 1 1 d . . . . .
C1 C -0.7273(15) -0.5931(10) -0.3938(7) 0.062(4) Uani 1 1 d . . . . .
H1 H -0.751729 -0.573319 -0.328055 0.075 Uiso 1 1 calc R U . . .
C21 C -0.408(2) -0.6373(19) 0.1399(8) 0.105(6) Uani 1 1 d . . . . .
H21A H -0.480709 -0.581063 0.123197 0.126 Uiso 1 1 calc R U . . .
H21B H -0.423374 -0.673422 0.205955 0.126 Uiso 1 1 calc R U . . .
C14 C -0.9877(16) -0.2428(13) -0.2409(8) 0.080(5) Uani 1 1 d . . . . .
H14 H -0.990821 -0.322978 -0.208018 0.096 Uiso 1 1 calc R U . . .
C10 C -0.9199(14) -0.1104(11) -0.3854(7) 0.063(4) Uani 1 1 d . . . . .
H10 H -0.880465 -0.102224 -0.447767 0.076 Uiso 1 1 calc R U . . .
C7 C -0.8094(16) -0.3494(13) -0.6356(7) 0.075(5) Uani 1 1 d . . . . .
H7 H -0.824206 -0.295621 -0.689993 0.090 Uiso 1 1 calc R U . . .
C19 C -0.256(2) -0.6269(18) -0.0393(9) 0.103(6) Uani 1 1 d . . . . .
H19A H -0.244629 -0.588905 -0.105259 0.123 Uiso 1 1 calc R U . . .
H19B H -0.180742 -0.682126 -0.026165 0.123 Uiso 1 1 calc R U . . .
C20 C -0.4267(17) -0.7538(14) 0.0556(8) 0.083(4) Uani 1 1 d . . . . .
H20A H -0.355305 -0.810458 0.075367 0.099 Uiso 1 1 calc R U . . .
H20B H -0.527229 -0.810422 0.051524 0.099 Uiso 1 1 calc R U . . .
C13 C -1.0493(15) -0.1386(13) -0.1958(8) 0.071(4) Uani 1 1 d . . . . .
Cl31 Cl -1.1263(10) -0.1517(8) -0.0817(6) 0.140(4) Uani 1 1 d . . . . .
F30 F -1.1004(17) 0.0885(13) -0.2067(8) 0.107(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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
C8 N25 H25 114.0 . . ?
C8 N25 C9 132.0(9) . . ?
C9 N25 H25 114.0 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.5(11) . . ?
C22 O29 C21 110.4(10) . . ?
N25 C8 C6 119.5(8) . . ?
N24 C8 N25 119.1(8) . . ?
N24 C8 C6 121.4(8) . . ?
C5 C6 C8 115.8(8) . . ?
C5 C6 C1 118.6(8) . . ?
C1 C6 C8 125.5(8) . . ?
C8 N24 C7 115.3(8) . . ?
C3 O27 C15 118.5(8) . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.4(8) . . ?
C3 C4 H4 119.8 . . ?
N25 C9 C14 116.9(9) . . ?
N25 C9 C10 124.4(9) . . ?
C14 C9 C10 118.6(8) . . ?
C6 C5 C4 120.0(8) . . ?
N23 C5 C6 121.7(8) . . ?
N23 C5 C4 118.3(8) . . ?
H17A C17 H17B 107.7 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C18 C17 C16 113.8(14) . . ?
O28 C2 C3 114.3(7) . . ?
C1 C2 C3 119.1(8) . . ?
C1 C2 O28 126.3(8) . . ?
O29 C22 H22A 108.8 . . ?
O29 C22 H22B 108.8 . . ?
O29 C22 C19 113.6(12) . . ?
H22A C22 H22B 107.7 . . ?
C19 C22 H22A 108.8 . . ?
C19 C22 H22B 108.8 . . ?
O27 C3 C4 126.1(8) . . ?
O27 C3 C2 114.4(8) . . ?
C4 C3 C2 119.4(8) . . ?
C17 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
O28 C16 C17 105.7(8) . . ?
O28 C16 H16A 110.6 . . ?
O28 C16 H16B 110.6 . . ?
C18 N26 C19 111.2(11) . . ?
C20 N26 C18 113.9(13) . . ?
C20 N26 C19 109.5(10) . . ?
C13 C12 C11 119.8(9) . . ?
F30 C12 C11 118.3(12) . . ?
F30 C12 C13 121.8(11) . . ?
O27 C15 H15A 109.5 . . ?
O27 C15 H15B 109.5 . . ?
O27 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
N26 C18 C17 111.9(11) . . ?
N26 C18 H18A 109.2 . . ?
N26 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C2 O28 C16 117.0(7) . . ?
C7 N23 C5 115.5(8) . . ?
C6 C1 H1 118.9 . . ?
C2 C1 C6 122.3(8) . . ?
C2 C1 H1 118.9 . . ?
O29 C21 H21A 110.2 . . ?
O29 C21 H21B 110.2 . . ?
O29 C21 C20 107.5(11) . . ?
H21A C21 H21B 108.5 . . ?
C20 C21 H21A 110.2 . . ?
C20 C21 H21B 110.2 . . ?
C9 C14 H14 118.2 . . ?
C9 C14 C13 123.7(10) . . ?
C13 C14 H14 118.2 . . ?
C11 C10 C9 119.1(10) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N24 C7 H7 114.9 . . ?
N23 C7 N24 130.2(9) . . ?
N23 C7 H7 114.9 . . ?
C22 C19 H19A 109.8 . . ?
C22 C19 H19B 109.8 . . ?
N26 C19 C22 109.3(12) . . ?
N26 C19 H19A 109.8 . . ?
N26 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
N26 C20 C21 114.5(12) . . ?
N26 C20 H20A 108.6 . . ?
N26 C20 H20B 108.6 . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C12 C13 Cl31 118.7(8) . . ?
C14 C13 C12 118.3(10) . . ?
C14 C13 Cl31 123.0(10) . . ?
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
N25 H25 0.8600 . ?
N25 C8 1.383(12) . ?
N25 C9 1.400(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.450(16) . ?
C11 C10 1.421(14) . ?
O29 C22 1.424(15) . ?
O29 C21 1.432(19) . ?
C8 C6 1.491(12) . ?
C8 N24 1.363(12) . ?
C6 C5 1.420(12) . ?
C6 C1 1.473(12) . ?
N24 C7 1.365(12) . ?
O27 C3 1.379(12) . ?
O27 C15 1.408(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.430(12) . ?
C4 C3 1.449(12) . ?
C9 C14 1.401(13) . ?
C9 C10 1.437(13) . ?
C5 N23 1.406(12) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.573(15) . ?
C17 C18 1.49(2) . ?
C2 C3 1.458(11) . ?
C2 O28 1.382(11) . ?
C2 C1 1.380(11) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C19 1.528(17) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 O28 1.477(12) . ?
N26 C18 1.449(15) . ?
N26 C19 1.45(2) . ?
N26 C20 1.410(14) . ?
C12 C13 1.411(16) . ?
C12 F30 1.355(13) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N23 C7 1.325(12) . ?
C1 H1 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C20 1.515(17) . ?
C14 H14 0.9300 . ?
C14 C13 1.409(13) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C13 Cl31 1.722(12) . ?
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
N25 C8 C6 C5 178.4(11) . . . . ?
N25 C8 C6 C1 -4(2) . . . . ?
N25 C8 N24 C7 -178.6(11) . . . . ?
N25 C9 C14 C13 -178.7(12) . . . . ?
N25 C9 C10 C11 179.4(11) . . . . ?
C11 C12 C13 C14 -1(2) . . . . ?
C11 C12 C13 Cl31 178.5(10) . . . . ?
O29 C22 C19 N26 54.6(15) . . . . ?
O29 C21 C20 N26 -59.6(14) . . . . ?
C8 N25 C9 C14 164.9(13) . . . . ?
C8 N25 C9 C10 -12(2) . . . . ?
C8 C6 C5 C4 -179.8(13) . . . . ?
C8 C6 C5 N23 -0.2(17) . . . . ?
C8 C6 C1 C2 -176.4(13) . . . . ?
C8 N24 C7 N23 1(2) . . . . ?
C6 C8 N24 C7 0.1(18) . . . . ?
C6 C5 N23 C7 0.8(18) . . . . ?
N24 C8 C6 C5 -0.2(18) . . . . ?
N24 C8 C6 C1 177.1(12) . . . . ?
C4 C5 N23 C7 -179.6(13) . . . . ?
C9 N25 C8 C6 175.2(13) . . . . ?
C9 N25 C8 N24 -6.1(19) . . . . ?
C9 C14 C13 C12 1(2) . . . . ?
C9 C14 C13 Cl31 -178.7(10) . . . . ?
C5 C6 C1 C2 0.9(18) . . . . ?
C5 C4 C3 O27 178.9(12) . . . . ?
C5 C4 C3 C2 0.3(17) . . . . ?
C5 N23 C7 N24 -1(2) . . . . ?
C17 C16 O28 C2 -173.4(13) . . . . ?
C22 O29 C21 C20 56.4(14) . . . . ?
C3 C4 C5 C6 -3.1(18) . . . . ?
C3 C4 C5 N23 177.2(11) . . . . ?
C3 C2 O28 C16 -178.1(11) . . . . ?
C3 C2 C1 C6 -3.7(18) . . . . ?
C16 C17 C18 N26 70.5(14) . . . . ?
C12 C11 C10 C9 -2.7(19) . . . . ?
C15 O27 C3 C4 2.3(19) . . . . ?
C15 O27 C3 C2 -179.0(10) . . . . ?
C18 C17 C16 O28 85.3(13) . . . . ?
C18 N26 C19 C22 -179.6(9) . . . . ?
C18 N26 C20 C21 -176.4(13) . . . . ?
O28 C2 C3 O27 -1.2(15) . . . . ?
O28 C2 C3 C4 177.5(12) . . . . ?
O28 C2 C1 C6 -177.4(12) . . . . ?
C1 C6 C5 C4 2.6(16) . . . . ?
C1 C6 C5 N23 -177.8(13) . . . . ?
C1 C2 C3 O27 -175.7(13) . . . . ?
C1 C2 C3 C4 3.1(16) . . . . ?
C1 C2 O28 C16 -4.1(19) . . . . ?
C21 O29 C22 C19 -57.4(16) . . . . ?
C14 C9 C10 C11 2.5(18) . . . . ?
C10 C11 C12 C13 2(2) . . . . ?
C10 C11 C12 F30 179.8(13) . . . . ?
C10 C9 C14 C13 -1.5(18) . . . . ?
C19 N26 C18 C17 -152.4(12) . . . . ?
C19 N26 C20 C21 58.4(14) . . . . ?
C20 N26 C18 C17 83.4(13) . . . . ?
C20 N26 C19 C22 -52.9(14) . . . . ?
F30 C12 C13 C14 -178.7(13) . . . . ?
F30 C12 C13 Cl31 1(2) . . . . ?
