#------------------------------------------------------------------------------
#$Date: 2022-06-06 05:04:36 +0300 (Mon, 06 Jun 2022) $
#$Revision: 275823 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158659.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_7158659
loop_
_publ_author_name
'Edmonds, Anthony K.'
'Oakes, Catherine S.'
'Hassell-Hart, Storm'
'Bruyère, Didier'
'Tizzard, Graham J.'
'Coles, Simon J.'
'Felix, Robert'
'Maple, Hannah J.'
'Marsh, Graham P.'
'Spencer, John'
_publ_section_title
;
 Scale-up and optimization of the synthesis of dual CBP/BRD4 inhibitor
 ISOX-DUAL.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4021
_journal_page_last               4029
_journal_paper_doi               10.1039/d2ob00609j
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C17 H19 F N4 O3'
_chemical_formula_sum            'C17 H19 F N4 O3'
_chemical_formula_weight         346.36
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2021-09-15 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.7490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.59320(10)
_cell_length_b                   7.25830(10)
_cell_length_c                   31.5918(4)
_cell_measurement_reflns_used    15025
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.8190
_cell_measurement_theta_min      2.8900
_cell_volume                     3263.76(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -142.00  37.00   0.50    0.75    --  -52.30  55.00-100.00  358
  2  ω    -75.00 -26.00   0.50    3.00    --  -90.00  55.00-100.00   98
  3  ω   -173.00 -90.00   0.50    3.00    --  -90.00  55.00-100.00  166
  4  ω    -19.00   6.00   0.50    0.75    --    5.00  55.00-100.00   50
  5  ω    -83.00  91.00   0.50    0.75    --    5.00   0.00-180.00  348
  6  ω   -157.00-123.00   0.50    3.00    --  -90.00  49.00-180.00   68
  7  ω   -153.00  -2.00   0.50    3.00    --  -90.00  20.00 -30.00  302
  8  ω   -170.00-136.00   0.50    3.00    --  -90.00  30.00 120.00   68
  9  ω    -55.00 -29.00   0.50    3.00    --  -90.00  30.00 120.00   52
 10  ω   -143.00 -94.00   0.50    3.00    --  -90.00  39.00-120.00   98
 11  ω   -178.00-152.00   0.50    3.00    --  -90.00  39.00-120.00   52
 12  ω    -57.00 -15.00   0.50    3.00    --  -90.00  39.00-120.00   84
 13  ω   -112.00  -1.00   0.50    3.00    --  -90.00  49.00-180.00  222
 14  ω   -174.00-144.00   0.50    3.00    --  -90.00  10.00 120.00   60
 15  ω    -43.00  -2.00   0.50    3.00    --  -90.00  10.00 120.00   82
 16  ω   -162.00  -2.00   0.50    3.00    --  -90.00  49.00 -60.00  320
 17  ω   -105.00 -22.00   0.50    3.00    --  -90.00  30.00   0.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_device_type
'Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0629723000
_diffrn_orient_matrix_UB_12      0.1704814000
_diffrn_orient_matrix_UB_13      0.0001031000
_diffrn_orient_matrix_UB_21      -0.0023405000
_diffrn_orient_matrix_UB_22      -0.0304395000
_diffrn_orient_matrix_UB_23      -0.0484909000
_diffrn_orient_matrix_UB_31      -0.0880123000
_diffrn_orient_matrix_UB_32      0.1226360000
_diffrn_orient_matrix_UB_33      -0.0121947000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            31409
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.052
_diffrn_reflns_theta_min         3.119
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_recrystallization_method
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0424
_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)+(0.0263P)²+3.4647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5663
_reflns_number_total             6140
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00609j2.cif
_cod_data_source_block           20
_cod_depositor_comments
'Adding full bibliography for 7158654--7158659.cif.'
_cod_database_code               7158659
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H16 F N4 O3'
_chemical_oxdiff_usercomment     AKE-052
_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_max   0.982
_shelx_estimated_absorpt_t_min   0.900
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C57(H57A,H57B), C58(H58A,H58B), C62(H62A,H62B), C61(H61A,H61B),
  C60(H60A,H60B), C59(H59A,H59B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C17(H17), C15(H15), C14(H14), C53(H53), C55(H55),
 C56(H56), C67(H67), C65(H65), C64(H64)
;
_olex2_date_sample_data_collection 2019-04-04
_olex2_date_sample_submission    2019-03-12
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id AKE-052
_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 1.761
_oxdiff_exptl_absorpt_empirical_full_min 0.808
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_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
F1 F 0.20530(9) 0.17173(18) 0.72796(4) 0.0345(3) Uani 1 1 d . . . . .
O3 O 0.25372(10) 0.0336(2) 0.28040(4) 0.0298(3) Uani 1 1 d . . . . .
O1 O 0.12558(9) -0.1974(2) 0.42235(4) 0.0262(3) Uani 1 1 d . . . . .
O2 O 0.04134(8) -0.1503(2) 0.46970(4) 0.0264(3) Uani 1 1 d . . . . .
N2 N 0.31055(11) -0.1848(2) 0.44470(5) 0.0192(3) Uani 1 1 d . . . . .
H2 H 0.2647(15) -0.189(3) 0.4234(7) 0.023 Uiso 1 1 d . U . . .
N3 N 0.32830(10) -0.1593(2) 0.35896(5) 0.0186(3) Uani 1 1 d . . . . .
N1 N 0.11863(10) -0.1543(2) 0.45964(5) 0.0192(3) Uani 1 1 d . . . . .
N4 N 0.15301(11) 0.1573(2) 0.65568(5) 0.0225(3) Uani 1 1 d . . . . .
C1 C 0.29309(12) -0.1261(2) 0.48273(6) 0.0168(3) Uani 1 1 d . . . . .
C2 C 0.20211(12) -0.1094(2) 0.49168(6) 0.0175(4) Uani 1 1 d . . . . .
C3 C 0.18900(12) -0.0554(2) 0.53243(6) 0.0172(3) Uani 1 1 d . . . . .
H3 H 0.127014 -0.047511 0.537109 0.021 Uiso 1 1 calc R U . . .
C4 C 0.26426(12) -0.0132(2) 0.56609(6) 0.0170(4) Uani 1 1 d . . . . .
C5 C 0.35450(12) -0.0245(2) 0.55721(6) 0.0187(4) Uani 1 1 d . . . . .
H5 H 0.407396 0.007802 0.579376 0.022 Uiso 1 1 calc R U . . .
C6 C 0.36868(12) -0.0803(2) 0.51778(6) 0.0184(4) Uani 1 1 d . . . . .
H6 H 0.431149 -0.088623 0.513728 0.022 Uiso 1 1 calc R U . . .
C7 C 0.40404(12) -0.1890(3) 0.43582(6) 0.0207(4) Uani 1 1 d . . . . .
H7A H 0.445709 -0.268736 0.457215 0.025 Uiso 1 1 calc R U . . .
H7B H 0.431010 -0.063294 0.438073 0.025 Uiso 1 1 calc R U . . .
C8 C 0.39652(12) -0.2642(3) 0.39010(6) 0.0208(4) Uani 1 1 d . . . . .
H8A H 0.458640 -0.257075 0.382427 0.025 Uiso 1 1 calc R U . . .
H8B H 0.377293 -0.395223 0.389094 0.025 Uiso 1 1 calc R U . . .
C9 C 0.29403(13) -0.2578(3) 0.31817(6) 0.0234(4) Uani 1 1 d . . . . .
H9A H 0.267674 -0.378487 0.323941 0.028 Uiso 1 1 calc R U . . .
H9B H 0.346420 -0.279740 0.303527 0.028 Uiso 1 1 calc R U . . .
C10 C 0.21881(14) -0.1420(3) 0.28944(6) 0.0268(4) Uani 1 1 d . . . . .
H10A H 0.194692 -0.208040 0.261801 0.032 Uiso 1 1 calc R U . . .
H10B H 0.165825 -0.124713 0.303945 0.032 Uiso 1 1 calc R U . . .
C11 C 0.28967(14) 0.1293(3) 0.31998(6) 0.0263(4) Uani 1 1 d . . . . .
H11A H 0.237957 0.152898 0.334950 0.032 Uiso 1 1 calc R U . . .
H11B H 0.315301 0.249767 0.313489 0.032 Uiso 1 1 calc R U . . .
C12 C 0.36593(13) 0.0199(3) 0.34948(6) 0.0224(4) Uani 1 1 d . . . . .
H12A H 0.419276 0.001246 0.335274 0.027 Uiso 1 1 calc R U . . .
H12B H 0.389130 0.088408 0.376844 0.027 Uiso 1 1 calc R U . . .
C13 C 0.25152(12) 0.0364(2) 0.60994(6) 0.0178(4) Uani 1 1 d . . . . .
C17 C 0.16848(12) 0.1141(2) 0.61646(6) 0.0194(4) Uani 1 1 d . . . . .
H17 H 0.119773 0.137974 0.591680 0.023 Uiso 1 1 calc R U . . .
C16 C 0.22228(14) 0.1236(3) 0.68894(6) 0.0237(4) Uani 1 1 d . . . . .
C15 C 0.30842(14) 0.0484(3) 0.68785(6) 0.0236(4) Uani 1 1 d . . . . .
H15 H 0.355376 0.028012 0.713489 0.028 Uiso 1 1 calc R U . . .
C14 C 0.32231(13) 0.0043(3) 0.64718(6) 0.0216(4) Uani 1 1 d . . . . .
H14 H 0.380322 -0.048168 0.644396 0.026 Uiso 1 1 calc R U . . .
F51 F 0.51508(8) 0.63440(17) 0.72622(3) 0.0313(3) Uani 1 1 d . . . . .
O53 O -0.00674(10) 0.4665(2) 0.26729(4) 0.0292(3) Uani 1 1 d . . . . .
O51 O 0.29951(9) 0.3072(2) 0.41966(4) 0.0279(3) Uani 1 1 d . . . . .
O52 O 0.42842(8) 0.3458(2) 0.46793(4) 0.0260(3) Uani 1 1 d . . . . .
N52 N 0.13532(10) 0.3193(2) 0.44110(5) 0.0195(3) Uani 1 1 d . . . . .
H52 H 0.1623(15) 0.309(3) 0.4199(7) 0.023 Uiso 1 1 d . U . . .
N53 N 0.02901(10) 0.3116(2) 0.35276(5) 0.0200(3) Uani 1 1 d . . . . .
N51 N 0.34150(10) 0.3449(2) 0.45726(5) 0.0193(3) Uani 1 1 d . . . . .
N54 N 0.49671(10) 0.6335(2) 0.65379(5) 0.0216(3) Uani 1 1 d . . . . .
C51 C 0.18833(12) 0.3764(2) 0.47944(6) 0.0173(4) Uani 1 1 d . . . . .
C52 C 0.28806(12) 0.3900(2) 0.48914(6) 0.0172(4) Uani 1 1 d . . . . .
C53 C 0.33952(12) 0.4415(2) 0.53011(6) 0.0171(3) Uani 1 1 d . . . . .
H53 H 0.406126 0.445936 0.535264 0.020 Uiso 1 1 calc R U . . .
C54 C 0.29580(12) 0.4861(2) 0.56331(5) 0.0165(3) Uani 1 1 d . . . . .
C55 C 0.19708(12) 0.4791(2) 0.55391(6) 0.0185(4) Uani 1 1 d . . . . .
H55 H 0.164979 0.512539 0.575859 0.022 Uiso 1 1 calc R U . . .
C56 C 0.14560(12) 0.4254(2) 0.51403(6) 0.0183(4) Uani 1 1 d . . . . .
H56 H 0.079072 0.420973 0.509463 0.022 Uiso 1 1 calc R U . . .
C57 C 0.03335(12) 0.3149(3) 0.43185(6) 0.0220(4) Uani 1 1 d . . . . .
H57A H 0.008472 0.442019 0.431225 0.026 Uiso 1 1 calc R U . . .
H57B H 0.011948 0.245790 0.454901 0.026 Uiso 1 1 calc R U . . .
C58 C -0.00339(13) 0.2224(3) 0.38812(6) 0.0219(4) Uani 1 1 d . . . . .
H58A H 0.017143 0.092086 0.390004 0.026 Uiso 1 1 calc R U . . .
H58B H -0.072936 0.223826 0.381535 0.026 Uiso 1 1 calc R U . . .
C62 C 0.00692(15) 0.1975(3) 0.31367(6) 0.0273(4) Uani 1 1 d . . . . .
H62A H -0.061603 0.174534 0.305599 0.033 Uiso 1 1 calc R U . . .
H62B H 0.039119 0.077077 0.319541 0.033 Uiso 1 1 calc R U . . .
C61 C 0.03797(16) 0.2920(3) 0.27648(7) 0.0322(5) Uani 1 1 d . . . . .
H61A H 0.106961 0.309260 0.284043 0.039 Uiso 1 1 calc R U . . .
H61B H 0.022314 0.213192 0.250307 0.039 Uiso 1 1 calc R U . . .
C60 C 0.01580(14) 0.5797(3) 0.30491(6) 0.0271(4) Uani 1 1 d . . . . .
H60A H -0.015225 0.700899 0.298496 0.033 Uiso 1 1 calc R U . . .
H60B H 0.084530 0.600341 0.312744 0.033 Uiso 1 1 calc R U . . .
C59 C -0.01529(13) 0.4925(3) 0.34271(6) 0.0233(4) Uani 1 1 d . . . . .
H59A H 0.001990 0.573629 0.368432 0.028 Uiso 1 1 calc R U . . .
H59B H -0.084462 0.478304 0.335598 0.028 Uiso 1 1 calc R U . . .
C63 C 0.35081(12) 0.5332(2) 0.60742(6) 0.0177(4) Uani 1 1 d . . . . .
C67 C 0.44220(12) 0.5991(2) 0.61435(6) 0.0188(4) Uani 1 1 d . . . . .
H67 H 0.467875 0.621362 0.589689 0.023 Uiso 1 1 calc R U . . .
C66 C 0.45844(13) 0.6019(3) 0.68684(6) 0.0223(4) Uani 1 1 d . . . . .
C65 C 0.36848(14) 0.5422(3) 0.68520(6) 0.0238(4) Uani 1 1 d . . . . .
H65 H 0.344989 0.526281 0.710719 0.029 Uiso 1 1 calc R U . . .
C64 C 0.31386(13) 0.5063(3) 0.64433(6) 0.0206(4) Uani 1 1 d . . . . .
H64 H 0.251234 0.463464 0.641277 0.025 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O3 C11 109.82(14) . . ?
C1 N2 H2 116.8(15) . . ?
C1 N2 C7 123.24(15) . . ?
C7 N2 H2 117.5(15) . . ?
C8 N3 C9 113.04(14) . . ?
C8 N3 C12 111.80(14) . . ?
C9 N3 C12 108.89(14) . . ?
O1 N1 C2 119.32(14) . . ?
O2 N1 O1 121.20(14) . . ?
O2 N1 C2 119.48(14) . . ?
C16 N4 C17 116.02(16) . . ?
N2 C1 C2 124.85(16) . . ?
N2 C1 C6 120.06(16) . . ?
C6 C1 C2 115.07(15) . . ?
C1 C2 N1 121.55(15) . . ?
C3 C2 N1 116.38(15) . . ?
C3 C2 C1 122.02(16) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.52(16) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 116.90(16) . . ?
C3 C4 C13 122.01(16) . . ?
C5 C4 C13 121.07(15) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 C4 122.32(16) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 H6 118.9 . . ?
C5 C6 C1 122.14(16) . . ?
C5 C6 H6 118.9 . . ?
N2 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
N2 C7 C8 108.43(14) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
N3 C8 C7 110.45(14) . . ?
N3 C8 H8A 109.6 . . ?
N3 C8 H8B 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N3 C9 H9A 110.0 . . ?
N3 C9 H9B 110.0 . . ?
N3 C9 C10 108.60(15) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
O3 C10 C9 111.86(16) . . ?
O3 C10 H10A 109.2 . . ?
O3 C10 H10B 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 H11A 109.4 . . ?
O3 C11 H11B 109.4 . . ?
O3 C11 C12 111.32(16) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
N3 C12 C11 109.52(15) . . ?
N3 C12 H12A 109.8 . . ?
N3 C12 H12B 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C17 C13 C4 121.97(16) . . ?
C17 C13 C14 116.54(16) . . ?
C14 C13 C4 121.48(16) . . ?
N4 C17 C13 124.01(17) . . ?
N4 C17 H17 118.0 . . ?
C13 C17 H17 118.0 . . ?
F1 C16 C15 118.41(17) . . ?
N4 C16 F1 114.68(17) . . ?
N4 C16 C15 126.91(17) . . ?
C16 C15 H15 122.1 . . ?
C16 C15 C14 115.90(17) . . ?
C14 C15 H15 122.1 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.62(17) . . ?
C15 C14 H14 119.7 . . ?
C60 O53 C61 109.38(15) . . ?
C51 N52 H52 117.2(14) . . ?
C51 N52 C57 123.10(15) . . ?
C57 N52 H52 118.1(14) . . ?
C58 N53 C62 110.32(15) . . ?
C58 N53 C59 111.19(14) . . ?
C62 N53 C59 108.64(14) . . ?
O51 N51 C52 119.33(14) . . ?
O52 N51 O51 121.44(14) . . ?
O52 N51 C52 119.22(14) . . ?
C66 N54 C67 115.93(16) . . ?
N52 C51 C52 124.79(16) . . ?
N52 C51 C56 120.39(16) . . ?
C56 C51 C52 114.81(15) . . ?
C51 C52 N51 121.29(15) . . ?
C53 C52 N51 116.45(15) . . ?
C53 C52 C51 122.23(16) . . ?
C52 C53 H53 119.2 . . ?
C54 C53 C52 121.51(16) . . ?
C54 C53 H53 119.2 . . ?
C53 C54 C55 117.04(16) . . ?
C53 C54 C63 121.43(16) . . ?
C55 C54 C63 121.49(15) . . ?
C54 C55 H55 118.9 . . ?
C56 C55 C54 122.11(16) . . ?
C56 C55 H55 118.9 . . ?
C51 C56 H56 118.9 . . ?
C55 C56 C51 122.25(16) . . ?
C55 C56 H56 118.9 . . ?
N52 C57 H57A 109.8 . . ?
N52 C57 H57B 109.8 . . ?
N52 C57 C58 109.41(15) . . ?
H57A C57 H57B 108.2 . . ?
C58 C57 H57A 109.8 . . ?
C58 C57 H57B 109.8 . . ?
N53 C58 C57 112.99(15) . . ?
N53 C58 H58A 109.0 . . ?
N53 C58 H58B 109.0 . . ?
C57 C58 H58A 109.0 . . ?
C57 C58 H58B 109.0 . . ?
H58A C58 H58B 107.8 . . ?
N53 C62 H62A 109.5 . . ?
N53 C62 H62B 109.5 . . ?
N53 C62 C61 110.52(17) . . ?
H62A C62 H62B 108.1 . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
O53 C61 C62 111.04(16) . . ?
O53 C61 H61A 109.4 . . ?
O53 C61 H61B 109.4 . . ?
C62 C61 H61A 109.4 . . ?
C62 C61 H61B 109.4 . . ?
H61A C61 H61B 108.0 . . ?
O53 C60 H60A 109.3 . . ?
O53 C60 H60B 109.3 . . ?
O53 C60 C59 111.42(16) . . ?
H60A C60 H60B 108.0 . . ?
C59 C60 H60A 109.3 . . ?
C59 C60 H60B 109.3 . . ?
N53 C59 C60 110.60(16) . . ?
N53 C59 H59A 109.5 . . ?
N53 C59 H59B 109.5 . . ?
C60 C59 H59A 109.5 . . ?
C60 C59 H59B 109.5 . . ?
H59A C59 H59B 108.1 . . ?
C67 C63 C54 121.90(16) . . ?
C67 C63 C64 116.69(16) . . ?
C64 C63 C54 121.37(16) . . ?
N54 C67 C63 124.14(17) . . ?
N54 C67 H67 117.9 . . ?
C63 C67 H67 117.9 . . ?
F51 C66 C65 118.33(16) . . ?
N54 C66 F51 114.92(16) . . ?
N54 C66 C65 126.75(17) . . ?
C66 C65 H65 121.8 . . ?
C66 C65 C64 116.32(17) . . ?
C64 C65 H65 121.8 . . ?
C63 C64 H64 119.9 . . ?
C65 C64 C63 120.12(17) . . ?
C65 C64 H64 119.9 . . ?
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
F1 C16 1.356(2) . ?
O3 C10 1.425(2) . ?
O3 C11 1.425(2) . ?
O1 N1 1.2444(19) . ?
O2 N1 1.2379(19) . ?
N2 H2 0.84(2) . ?
N2 C1 1.351(2) . ?
N2 C7 1.452(2) . ?
N3 C8 1.451(2) . ?
N3 C9 1.462(2) . ?
N3 C12 1.468(2) . ?
N1 C2 1.439(2) . ?
N4 C17 1.345(2) . ?
N4 C16 1.310(2) . ?
C1 C2 1.422(2) . ?
C1 C6 1.419(2) . ?
C2 C3 1.399(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(2) . ?
C4 C5 1.408(2) . ?
C4 C13 1.482(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.369(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.525(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.515(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.510(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.392(2) . ?
C13 C14 1.403(3) . ?
C17 H17 0.9500 . ?
C16 C15 1.378(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.382(3) . ?
C14 H14 0.9500 . ?
F51 C66 1.354(2) . ?
O53 C61 1.425(3) . ?
O53 C60 1.422(2) . ?
O51 N51 1.2408(19) . ?
O52 N51 1.2385(19) . ?
N52 H52 0.85(2) . ?
N52 C51 1.350(2) . ?
N52 C57 1.452(2) . ?
N53 C58 1.457(2) . ?
N53 C62 1.463(2) . ?
N53 C59 1.467(2) . ?
N51 C52 1.441(2) . ?
N54 C67 1.345(2) . ?
N54 C66 1.309(2) . ?
C51 C52 1.423(2) . ?
C51 C56 1.418(2) . ?
C52 C53 1.396(2) . ?
C53 H53 0.9500 . ?
C53 C54 1.381(2) . ?
C54 C55 1.406(2) . ?
C54 C63 1.487(2) . ?
C55 H55 0.9500 . ?
C55 C56 1.373(2) . ?
C56 H56 0.9500 . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C57 C58 1.523(2) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C62 C61 1.514(3) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C60 C59 1.507(3) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C63 C67 1.388(2) . ?
C63 C64 1.402(2) . ?
C67 H67 0.9500 . ?
C66 C65 1.373(3) . ?
C65 H65 0.9500 . ?
C65 C64 1.384(3) . ?
C64 H64 0.9500 . ?
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
F1 C16 C15 C14 -179.12(17) . . . . ?
O3 C11 C12 N3 -58.7(2) . . . . ?
O1 N1 C2 C1 -4.7(3) . . . . ?
O1 N1 C2 C3 177.66(16) . . . . ?
O2 N1 C2 C1 174.92(16) . . . . ?
O2 N1 C2 C3 -2.7(2) . . . . ?
N2 C1 C2 N1 -0.4(3) . . . . ?
N2 C1 C2 C3 177.14(17) . . . . ?
N2 C1 C6 C5 -178.43(17) . . . . ?
N2 C7 C8 N3 53.9(2) . . . . ?
N3 C9 C10 O3 59.4(2) . . . . ?
N1 C2 C3 C4 178.45(16) . . . . ?
N4 C16 C15 C14 0.0(3) . . . . ?
C1 N2 C7 C8 179.54(16) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C3 C4 C13 -177.33(16) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C3 C4 C13 C17 -26.1(3) . . . . ?
C3 C4 C13 C14 152.79(18) . . . . ?
C4 C5 C6 C1 1.7(3) . . . . ?
C4 C13 C17 N4 178.40(16) . . . . ?
C4 C13 C14 C15 -178.77(17) . . . . ?
C5 C4 C13 C17 155.76(17) . . . . ?
C5 C4 C13 C14 -25.4(3) . . . . ?
C6 C1 C2 N1 -178.83(15) . . . . ?
C6 C1 C2 C3 -1.3(2) . . . . ?
C7 N2 C1 C2 175.96(17) . . . . ?
C7 N2 C1 C6 -5.6(3) . . . . ?
C8 N3 C9 C10 176.16(15) . . . . ?
C8 N3 C12 C11 -175.24(15) . . . . ?
C9 N3 C8 C7 -160.37(15) . . . . ?
C9 N3 C12 C11 59.14(19) . . . . ?
C10 O3 C11 C12 57.6(2) . . . . ?
C11 O3 C10 C9 -58.3(2) . . . . ?
C12 N3 C8 C7 76.32(18) . . . . ?
C12 N3 C9 C10 -58.94(19) . . . . ?
C13 C4 C5 C6 176.11(17) . . . . ?
C17 N4 C16 F1 178.82(16) . . . . ?
C17 N4 C16 C15 -0.3(3) . . . . ?
C17 C13 C14 C15 0.2(3) . . . . ?
C16 N4 C17 C13 0.6(3) . . . . ?
C16 C15 C14 C13 0.1(3) . . . . ?
C14 C13 C17 N4 -0.5(3) . . . . ?
F51 C66 C65 C64 -178.45(16) . . . . ?
O53 C60 C59 N53 58.5(2) . . . . ?
O51 N51 C52 C51 5.6(3) . . . . ?
O51 N51 C52 C53 -176.37(16) . . . . ?
O52 N51 C52 C51 -174.87(16) . . . . ?
O52 N51 C52 C53 3.1(2) . . . . ?
N52 C51 C52 N51 1.1(3) . . . . ?
N52 C51 C52 C53 -176.81(17) . . . . ?
N52 C51 C56 C55 178.09(17) . . . . ?
N52 C57 C58 N53 -56.7(2) . . . . ?
N53 C62 C61 O53 -58.9(2) . . . . ?
N51 C52 C53 C54 -179.42(16) . . . . ?
N54 C66 C65 C64 2.2(3) . . . . ?
C51 N52 C57 C58 -173.25(16) . . . . ?
C51 C52 C53 C54 -1.4(3) . . . . ?
C52 C51 C56 C55 -0.9(3) . . . . ?
C52 C53 C54 C55 -0.6(3) . . . . ?
C52 C53 C54 C63 177.36(16) . . . . ?
C53 C54 C55 C56 1.8(3) . . . . ?
C53 C54 C63 C67 23.6(3) . . . . ?
C53 C54 C63 C64 -153.94(18) . . . . ?
C54 C55 C56 C51 -1.1(3) . . . . ?
C54 C63 C67 N54 -175.98(16) . . . . ?
C54 C63 C64 C65 176.57(17) . . . . ?
C55 C54 C63 C67 -158.52(17) . . . . ?
C55 C54 C63 C64 23.9(3) . . . . ?
C56 C51 C52 N51 -179.98(16) . . . . ?
C56 C51 C52 C53 2.1(3) . . . . ?
C57 N52 C51 C52 -177.26(17) . . . . ?
C57 N52 C51 C56 3.9(3) . . . . ?
C58 N53 C62 C61 178.39(16) . . . . ?
C58 N53 C59 C60 -177.67(15) . . . . ?
C62 N53 C58 C57 169.10(15) . . . . ?
C62 N53 C59 C60 -56.1(2) . . . . ?
C61 O53 C60 C59 -59.1(2) . . . . ?
C60 O53 C61 C62 59.1(2) . . . . ?
C59 N53 C58 C57 -70.30(19) . . . . ?
C59 N53 C62 C61 56.3(2) . . . . ?
C63 C54 C55 C56 -176.12(17) . . . . ?
C67 N54 C66 F51 178.92(15) . . . . ?
C67 N54 C66 C65 -1.7(3) . . . . ?
C67 C63 C64 C65 -1.1(3) . . . . ?
C66 N54 C67 C63 -0.4(3) . . . . ?
C66 C65 C64 C63 -0.6(3) . . . . ?
C64 C63 C67 N54 1.7(3) . . . . ?
