# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20180117_WangCui_C33HN4F3O2Br_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1887392'
loop_
_audit_author_name
_audit_author_address
'cui wang'
;Lanzhou University
China
;
_audit_update_record             
;
2019-03-01 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H23 Br F3 N4 O2'
_chemical_formula_weight         644.46

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'
Br Br -0.6763 1.2805 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.9148(3)
_cell_length_b                   10.2958(3)
_cell_length_c                   14.4151(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.169(2)
_cell_angle_gamma                90
_cell_volume                     1389.92(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9855
_cell_measurement_theta_min      4.77
_cell_measurement_theta_max      66.61

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             654
_exptl_transmission_factor_min   0.3820
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.529
_shelx_estimated_absorpt_T_min   0.517
_shelx_estimated_absorpt_T_max   0.632
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            17466
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.246
_diffrn_reflns_theta_max         66.660
_diffrn_reflns_theta_full        66.660
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4870
_reflns_number_gt                4707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.981

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0190P)²+0.3775P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2098 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4870
_refine_ls_number_parameters     389
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.94889(4) -0.01396(4) 0.28939(3) 0.03577(12) Uani 1 1 d . . . . .
C1 C 0.8243(3) 0.1284(3) 0.2833(3) 0.0251(7) Uani 1 1 d . . . . .
C2 C 0.7479(4) 0.1768(3) 0.1923(3) 0.0272(7) Uani 1 1 d . . . . .
H2 H 0.7611 0.1419 0.1349 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6518(4) 0.2768(4) 0.1851(3) 0.0261(7) Uani 1 1 d . . . . .
H3 H 0.5969 0.3099 0.1225 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6364(3) 0.3281(3) 0.2698(3) 0.0222(7) Uani 1 1 d . . . . .
C5 C 0.7150(3) 0.2807(3) 0.3620(3) 0.0243(7) Uani 1 1 d . . . . .
H5 H 0.7041 0.3174 0.4196 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8096(3) 0.1787(3) 0.3686(3) 0.0248(7) Uani 1 1 d . . . . .
H6 H 0.8636 0.1440 0.4308 0.030 Uiso 1 1 calc R U . . .
C7 C 0.1177(4) 0.3437(4) -0.0164(3) 0.0312(8) Uani 1 1 d . . . . .
H7 H 0.1083 0.3615 -0.0829 0.037 Uiso 1 1 calc R U . . .
C8 C 0.1059(4) 0.2180(4) 0.0134(3) 0.0313(8) Uani 1 1 d . . . . .
H8 H 0.0899 0.1486 -0.0324 0.038 Uiso 1 1 calc R U . . .
C9 C 0.1172(4) 0.1932(3) 0.1096(3) 0.0327(8) Uani 1 1 d . . . . .
H9 H 0.1074 0.1068 0.1296 0.039 Uiso 1 1 calc R U . . .
C10 C 0.1428(4) 0.2930(4) 0.1775(3) 0.0289(8) Uani 1 1 d . . . . .
H10 H 0.1510 0.2744 0.2437 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1566(3) 0.4207(3) 0.1494(3) 0.0216(7) Uani 1 1 d . . . . .
C12 C 0.1437(3) 0.4442(3) 0.0521(3) 0.0271(8) Uani 1 1 d . . . . .
H12 H 0.1527 0.5305 0.0317 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4163(3) 0.7298(3) 0.1310(2) 0.0202(7) Uani 1 1 d . . . . .
C14 C 0.5406(4) 0.7899(3) 0.1267(3) 0.0273(7) Uani 1 1 d . . . . .
H14 H 0.6312 0.7527 0.1600 0.033 Uiso 1 1 calc R U . . .
C15 C 0.5315(4) 0.9041(4) 0.0735(3) 0.0326(8) Uani 1 1 d . . . . .
H15 H 0.6162 0.9448 0.0710 0.039 Uiso 1 1 calc R U . . .
C16 C 0.4007(4) 0.9587(3) 0.0243(3) 0.0337(9) Uani 1 1 d . . . . .
H16 H 0.3955 1.0375 -0.0111 0.040 Uiso 1 1 calc R U . . .
C17 C 0.2770(4) 0.8986(3) 0.0265(3) 0.0299(8) Uani 1 1 d . . . . .
H17 H 0.1865 0.9349 -0.0087 0.036 Uiso 1 1 calc R U . . .
C18 C 0.2852(4) 0.7849(3) 0.0801(3) 0.0245(7) Uani 1 1 d . . . . .
H18 H 0.2000 0.7445 0.0819 0.029 Uiso 1 1 calc R U . . .
C19 C 0.5109(3) 0.6898(3) 0.4114(3) 0.0245(7) Uani 1 1 d . . . . .
C20 C 0.6109(4) 0.6102(4) 0.4756(3) 0.0308(8) Uani 1 1 d . . . . .
H20 H 0.5851 0.5264 0.4915 0.037 Uiso 1 1 calc R U . . .
C21 C 0.7502(4) 0.6551(4) 0.5164(3) 0.0413(10) Uani 1 1 d . . . . .
H21 H 0.8197 0.6019 0.5613 0.050 Uiso 1 1 calc R U . . .
C22 C 0.7886(4) 0.7761(5) 0.4923(3) 0.0404(10) Uani 1 1 d . . . . .
H22 H 0.8852 0.8033 0.5191 0.048 Uiso 1 1 calc R U . . .
C23 C 0.6892(4) 0.8589(4) 0.4297(3) 0.0329(8) Uani 1 1 d . . . . .
H23 H 0.7154 0.9426 0.4136 0.039 Uiso 1 1 calc R U . . .
C24 C 0.5501(3) 0.8141(3) 0.3917(2) 0.0248(7) Uani 1 1 d . . . . .
C25 C 0.4376(3) 0.4450(3) 0.3044(3) 0.0216(7) Uani 1 1 d . . . . .
C26 C 0.3534(3) 0.5690(3) 0.2603(2) 0.0199(7) Uani 1 1 d . . . . .
C27 C 0.4317(3) 0.6092(3) 0.1904(2) 0.0179(6) Uani 1 1 d . . . . .
C28 C 0.3591(3) 0.6658(3) 0.3457(2) 0.0217(7) Uani 1 1 d . . . . .
C29 C 0.1912(3) 0.5357(3) 0.2201(3) 0.0223(7) Uani 1 1 d . . . . .
H29 H 0.1394 0.6135 0.1840 0.027 Uiso 1 1 calc R U . . .
C30 C 0.1579(3) 0.5238(3) 0.3174(3) 0.0242(7) Uani 1 1 d . . . . .
H30 H 0.1776 0.4324 0.3417 0.029 Uiso 1 1 calc R U . . .
C31 C 0.0039(4) 0.5556(4) 0.3054(3) 0.0328(9) Uani 1 1 d . . . . .
C32 C 0.4339(4) 1.0128(3) 0.2941(3) 0.0342(9) Uani 1 1 d . . . . .
H32A H 0.3382 1.0371 0.2510 0.051 Uiso 1 1 calc R U . . .
H32B H 0.5013 1.0184 0.2574 0.051 Uiso 1 1 calc R U . . .
H32C H 0.4640 1.0720 0.3503 0.051 Uiso 1 1 calc R U . . .
C33 C 0.3129(3) 0.8042(3) 0.3032(3) 0.0228(7) Uani 1 1 d . . . . .
F1 F -0.0372(2) 0.6741(2) 0.2707(2) 0.0470(6) Uani 1 1 d . . . . .
F2 F -0.0210(2) 0.5442(3) 0.39052(19) 0.0487(6) Uani 1 1 d . . . . .
F3 F -0.0836(2) 0.4724(3) 0.24233(18) 0.0454(6) Uani 1 1 d . . . . .
N1 N 0.2570(3) 0.6110(3) 0.3894(2) 0.0258(6) Uani 1 1 d . . . . .
N2 N 0.5343(3) 0.5314(3) 0.1926(2) 0.0223(6) Uani 1 1 d . . . . .
N3 N 0.5392(3) 0.4332(3) 0.2607(2) 0.0228(6) Uani 1 1 d . . . . .
N4 N 0.4312(3) 0.8806(3) 0.3287(2) 0.0249(6) Uani 1 1 d . . . . .
O1 O 0.1930(2) 0.8365(2) 0.25371(18) 0.0279(5) Uani 1 1 d . . . . .
O2 O 0.4182(2) 0.3714(2) 0.36490(18) 0.0270(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1 C1 1.901(3) . ?
C1 C2 1.375(5) . ?
C1 C6 1.385(5) . ?
C2 C3 1.383(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 N3 1.426(4) . ?
C5 C6 1.391(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.381(6) . ?
C7 C12 1.394(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(5) . ?
C11 C29 1.527(5) . ?
C12 H12 0.9500 . ?
C13 C18 1.387(5) . ?
C13 C14 1.399(5) . ?
C13 C27 1.487(5) . ?
C14 C15 1.390(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.382(5) . ?
C19 C24 1.394(5) . ?
C19 C28 1.512(5) . ?
C20 C21 1.390(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(5) . ?
C23 H23 0.9500 . ?
C24 N4 1.408(4) . ?
C25 O2 1.217(4) . ?
C25 N3 1.358(4) . ?
C25 C26 1.544(4) . ?
C26 C27 1.518(4) . ?
C26 C29 1.558(4) . ?
C26 C28 1.570(5) . ?
C27 N2 1.287(4) . ?
C28 N1 1.469(4) . ?
C28 C33 1.559(5) . ?
C29 C30 1.548(5) . ?
C29 H29 1.0000 . ?
C30 N1 1.476(4) . ?
C30 C31 1.515(5) . ?
C30 H30 1.0000 . ?
C31 F1 1.331(5) . ?
C31 F2 1.334(5) . ?
C31 F3 1.340(4) . ?
C32 N4 1.453(5) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 O1 1.214(4) . ?
C33 N4 1.359(4) . ?
N2 N3 1.399(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 C1 C6 121.8(3) . . ?
C2 C1 Br1 118.0(3) . . ?
C6 C1 Br1 120.2(3) . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 N3 118.4(3) . . ?
C5 C4 N3 120.3(3) . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C8 C7 C12 119.4(4) . . ?
C8 C7 H7 120.3 . . ?
C12 C7 H7 120.3 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 118.2(3) . . ?
C12 C11 C29 117.8(3) . . ?
C10 C11 C29 123.9(3) . . ?
C11 C12 C7 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C18 C13 C14 118.8(3) . . ?
C18 C13 C27 123.2(3) . . ?
C14 C13 C27 118.1(3) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 120.8(3) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C24 119.6(3) . . ?
C20 C19 C28 132.1(3) . . ?
C24 C19 C28 108.1(3) . . ?
C19 C20 C21 118.8(4) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C22 C21 C20 120.8(4) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 121.5(3) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 117.0(4) . . ?
C24 C23 H23 121.5 . . ?
C22 C23 H23 121.5 . . ?
C23 C24 C19 122.3(3) . . ?
C23 C24 N4 127.4(3) . . ?
C19 C24 N4 110.3(3) . . ?
O2 C25 N3 126.4(3) . . ?
O2 C25 C26 128.2(3) . . ?
N3 C25 C26 105.4(3) . . ?
C27 C26 C25 100.0(2) . . ?
C27 C26 C29 120.2(3) . . ?
C25 C26 C29 108.9(2) . . ?
C27 C26 C28 116.9(3) . . ?
C25 C26 C28 109.1(3) . . ?
C29 C26 C28 101.4(2) . . ?
N2 C27 C13 117.7(3) . . ?
N2 C27 C26 112.7(3) . . ?
C13 C27 C26 129.2(3) . . ?
N1 C28 C19 118.6(3) . . ?
N1 C28 C33 111.4(3) . . ?
C19 C28 C33 101.5(3) . . ?
N1 C28 C26 103.9(3) . . ?
C19 C28 C26 111.5(3) . . ?
C33 C28 C26 110.0(3) . . ?
C11 C29 C30 118.4(3) . . ?
C11 C29 C26 113.4(3) . . ?
C30 C29 C26 100.5(3) . . ?
C11 C29 H29 108.0 . . ?
C30 C29 H29 108.0 . . ?
C26 C29 H29 108.0 . . ?
N1 C30 C31 111.2(3) . . ?
N1 C30 C29 107.3(2) . . ?
C31 C30 C29 112.7(3) . . ?
N1 C30 H30 108.5 . . ?
C31 C30 H30 108.5 . . ?
C29 C30 H30 108.5 . . ?
F1 C31 F2 107.5(3) . . ?
F1 C31 F3 106.3(3) . . ?
F2 C31 F3 107.1(3) . . ?
F1 C31 C30 114.5(3) . . ?
F2 C31 C30 111.1(3) . . ?
F3 C31 C30 110.1(3) . . ?
N4 C32 H32A 109.5 . . ?
N4 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N4 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O1 C33 N4 126.2(3) . . ?
O1 C33 C28 125.9(3) . . ?
N4 C33 C28 107.9(3) . . ?
C28 N1 C30 109.0(3) . . ?
C27 N2 N3 108.2(3) . . ?
C25 N3 N2 113.7(2) . . ?
C25 N3 C4 127.3(3) . . ?
N2 N3 C4 118.6(3) . . ?
C33 N4 C24 111.0(3) . . ?
C33 N4 C32 124.1(3) . . ?
C24 N4 C32 124.8(3) . . ?

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
C6 C1 C2 C3 -1.2(5) . . . . ?
Br1 C1 C2 C3 177.3(3) . . . . ?
C1 C2 C3 C4 1.4(5) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C2 C3 C4 N3 178.5(3) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
N3 C4 C5 C6 -179.6(3) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
Br1 C1 C6 C5 -178.3(2) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C12 C7 C8 C9 1.1(5) . . . . ?
C7 C8 C9 C10 -1.0(5) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C9 C10 C11 C29 -177.2(3) . . . . ?
C10 C11 C12 C7 0.0(5) . . . . ?
C29 C11 C12 C7 177.5(3) . . . . ?
C8 C7 C12 C11 -0.6(5) . . . . ?
C18 C13 C14 C15 1.2(5) . . . . ?
C27 C13 C14 C15 -178.9(3) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C17 -1.0(6) . . . . ?
C15 C16 C17 C18 1.5(5) . . . . ?
C14 C13 C18 C17 -0.7(5) . . . . ?
C27 C13 C18 C17 179.4(3) . . . . ?
C16 C17 C18 C13 -0.6(5) . . . . ?
C24 C19 C20 C21 -2.2(5) . . . . ?
C28 C19 C20 C21 171.1(4) . . . . ?
C19 C20 C21 C22 -1.0(6) . . . . ?
C20 C21 C22 C23 2.4(6) . . . . ?
C21 C22 C23 C24 -0.7(6) . . . . ?
C22 C23 C24 C19 -2.6(5) . . . . ?
C22 C23 C24 N4 178.8(3) . . . . ?
C20 C19 C24 C23 4.1(5) . . . . ?
C28 C19 C24 C23 -170.7(3) . . . . ?
C20 C19 C24 N4 -177.1(3) . . . . ?
C28 C19 C24 N4 8.1(4) . . . . ?
O2 C25 C26 C27 -178.9(3) . . . . ?
N3 C25 C26 C27 0.5(3) . . . . ?
O2 C25 C26 C29 -52.0(4) . . . . ?
N3 C25 C26 C29 127.4(3) . . . . ?
O2 C25 C26 C28 57.8(4) . . . . ?
N3 C25 C26 C28 -122.7(3) . . . . ?
C18 C13 C27 N2 145.3(3) . . . . ?
C14 C13 C27 N2 -34.7(5) . . . . ?
C18 C13 C27 C26 -42.6(5) . . . . ?
C14 C13 C27 C26 137.4(3) . . . . ?
C25 C26 C27 N2 -0.3(3) . . . . ?
C29 C26 C27 N2 -119.2(3) . . . . ?
C28 C26 C27 N2 117.2(3) . . . . ?
C25 C26 C27 C13 -172.7(3) . . . . ?
C29 C26 C27 C13 68.4(4) . . . . ?
C28 C26 C27 C13 -55.2(4) . . . . ?
C20 C19 C28 N1 53.1(5) . . . . ?
C24 C19 C28 N1 -133.0(3) . . . . ?
C20 C19 C28 C33 175.4(4) . . . . ?
C24 C19 C28 C33 -10.7(3) . . . . ?
C20 C19 C28 C26 -67.5(5) . . . . ?
C24 C19 C28 C26 106.4(3) . . . . ?
C27 C26 C28 N1 171.2(3) . . . . ?
C25 C26 C28 N1 -76.3(3) . . . . ?
C29 C26 C28 N1 38.5(3) . . . . ?
C27 C26 C28 C19 -59.9(4) . . . . ?
C25 C26 C28 C19 52.6(3) . . . . ?
C29 C26 C28 C19 167.4(3) . . . . ?
C27 C26 C28 C33 52.0(3) . . . . ?
C25 C26 C28 C33 164.4(2) . . . . ?
C29 C26 C28 C33 -80.8(3) . . . . ?
C12 C11 C29 C30 160.2(3) . . . . ?
C10 C11 C29 C30 -22.5(4) . . . . ?
C12 C11 C29 C26 -82.5(4) . . . . ?
C10 C11 C29 C26 94.9(4) . . . . ?
C27 C26 C29 C11 61.4(4) . . . . ?
C25 C26 C29 C11 -53.0(4) . . . . ?
C28 C26 C29 C11 -167.9(3) . . . . ?
C27 C26 C29 C30 -171.3(3) . . . . ?
C25 C26 C29 C30 74.4(3) . . . . ?
C28 C26 C29 C30 -40.5(3) . . . . ?
C11 C29 C30 N1 153.5(3) . . . . ?
C26 C29 C30 N1 29.5(3) . . . . ?
C11 C29 C30 C31 -83.7(4) . . . . ?
C26 C29 C30 C31 152.3(3) . . . . ?
N1 C30 C31 F1 62.5(4) . . . . ?
C29 C30 C31 F1 -58.1(4) . . . . ?
N1 C30 C31 F2 -59.5(4) . . . . ?
C29 C30 C31 F2 179.9(3) . . . . ?
N1 C30 C31 F3 -177.9(3) . . . . ?
C29 C30 C31 F3 61.5(4) . . . . ?
N1 C28 C33 O1 -44.8(5) . . . . ?
C19 C28 C33 O1 -172.0(3) . . . . ?
C26 C28 C33 O1 69.8(4) . . . . ?
N1 C28 C33 N4 137.2(3) . . . . ?
C19 C28 C33 N4 10.0(3) . . . . ?
C26 C28 C33 N4 -108.2(3) . . . . ?
C19 C28 N1 C30 -145.0(3) . . . . ?
C33 C28 N1 C30 97.8(3) . . . . ?
C26 C28 N1 C30 -20.5(3) . . . . ?
C31 C30 N1 C28 -129.5(3) . . . . ?
C29 C30 N1 C28 -5.8(3) . . . . ?
C13 C27 N2 N3 173.3(3) . . . . ?
C26 C27 N2 N3 0.0(4) . . . . ?
O2 C25 N3 N2 178.9(3) . . . . ?
C26 C25 N3 N2 -0.6(4) . . . . ?
O2 C25 N3 C4 5.5(6) . . . . ?
C26 C25 N3 C4 -174.0(3) . . . . ?
C27 N2 N3 C25 0.4(4) . . . . ?
C27 N2 N3 C4 174.4(3) . . . . ?
C3 C4 N3 C25 132.1(4) . . . . ?
C5 C4 N3 C25 -48.9(5) . . . . ?
C3 C4 N3 N2 -41.0(4) . . . . ?
C5 C4 N3 N2 138.0(3) . . . . ?
O1 C33 N4 C24 176.2(3) . . . . ?
C28 C33 N4 C24 -5.8(4) . . . . ?
O1 C33 N4 C32 -4.5(5) . . . . ?
C28 C33 N4 C32 173.4(3) . . . . ?
C23 C24 N4 C33 177.4(3) . . . . ?
C19 C24 N4 C33 -1.3(4) . . . . ?
C23 C24 N4 C32 -1.8(5) . . . . ?
C19 C24 N4 C32 179.4(3) . . . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.044



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20180118_WangCui_C33N4F3O2Br1H_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1887393'
loop_
_audit_author_name
_audit_author_address
'cui wang'
;Lanzhou University
China
;
_audit_update_record             
;
2018-12-26 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H23 Br F3 N4 O2'
_chemical_formula_weight         644.46

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'
Br Br -0.6763 1.2805 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.1503(6)
_cell_length_b                   7.5835(4)
_cell_length_c                   17.6260(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.768(2)
_cell_angle_gamma                90
_cell_volume                     1353.83(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9589
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      66.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_F_000             654
_exptl_transmission_factor_min   0.3820
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.596
_shelx_estimated_absorpt_T_min   0.510
_shelx_estimated_absorpt_T_max   0.625
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            12779
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.365
_diffrn_reflns_theta_max         66.561
_diffrn_reflns_theta_full        66.561
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4680
_reflns_number_gt                4544
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.970

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+0.3411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(8)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4680
_refine_ls_number_parameters     389
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0621
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.95306(3) 1.04591(5) 0.83263(2) 0.03481(12) Uani 1 1 d . . . . .
C1 C 0.0530(4) 0.6828(5) 0.9700(2) 0.0307(8) Uani 1 1 d . . . . .
H1 H -0.0105 0.7368 0.9998 0.037 Uiso 1 1 calc R U . . .
C2 C 0.0124(4) 0.5886(5) 0.9052(2) 0.0305(9) Uani 1 1 d . . . . .
H2 H -0.0791 0.5772 0.8909 0.037 Uiso 1 1 calc R U . . .
C3 C 0.1044(3) 0.5111(5) 0.86123(19) 0.0243(8) Uani 1 1 d . . . . .
H3 H 0.0755 0.4475 0.8168 0.029 Uiso 1 1 calc R U . . .
C4 C 0.2393(3) 0.5254(5) 0.88151(16) 0.0171(6) Uani 1 1 d . . . . .
C5 C 0.2778(4) 0.6179(5) 0.94724(19) 0.0236(7) Uani 1 1 d . . . . .
H5 H 0.3691 0.6267 0.9626 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1860(4) 0.6978(5) 0.9911(2) 0.0290(8) Uani 1 1 d . . . . .
H6 H 0.2145 0.7624 1.0353 0.035 Uiso 1 1 calc R U . . .
C7 C 0.1239(3) 0.7614(5) 0.64047(19) 0.0189(7) Uani 1 1 d . . . . .
C8 C 0.0331(3) 0.6636(5) 0.5952(2) 0.0241(7) Uani 1 1 d . . . . .
H8 H 0.0430 0.5396 0.5905 0.029 Uiso 1 1 calc R U . . .
C9 C -0.0720(4) 0.7501(5) 0.5571(2) 0.0282(8) Uani 1 1 d . . . . .
H9 H -0.1347 0.6837 0.5265 0.034 Uiso 1 1 calc R U . . .
C10 C -0.0876(4) 0.9299(5) 0.5625(2) 0.0284(8) Uani 1 1 d . . . . .
H10 H -0.1604 0.9872 0.5364 0.034 Uiso 1 1 calc R U . . .
C11 C 0.0046(3) 1.0258(6) 0.60667(19) 0.0287(8) Uani 1 1 d . . . . .
H11 H -0.0045 1.1501 0.6102 0.034 Uiso 1 1 calc R U . . .
C12 C 0.1097(4) 0.9429(5) 0.6457(2) 0.0243(7) Uani 1 1 d . . . . .
H12 H 0.1721 1.0101 0.6760 0.029 Uiso 1 1 calc R U . . .
C13 C 0.4855(3) 0.3303(4) 0.64809(19) 0.0200(7) Uani 1 1 d . . . . .
C14 C 0.4016(4) 0.2855(5) 0.5863(2) 0.0264(8) Uani 1 1 d . . . . .
H14 H 0.3115 0.2597 0.5928 0.032 Uiso 1 1 calc R U . . .
C15 C 0.4507(4) 0.2784(6) 0.5144(2) 0.0316(9) Uani 1 1 d . . . . .
H15 H 0.3933 0.2494 0.4714 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5818(4) 0.3132(5) 0.5050(2) 0.0323(9) Uani 1 1 d . . . . .
H16 H 0.6135 0.3078 0.4555 0.039 Uiso 1 1 calc R U . . .
C17 C 0.6690(4) 0.3562(5) 0.5668(2) 0.0282(8) Uani 1 1 d . . . . .
H17 H 0.7596 0.3794 0.5603 0.034 Uiso 1 1 calc R U . . .
C18 C 0.6189(3) 0.3639(4) 0.63795(19) 0.0210(7) Uani 1 1 d . . . . .
C19 C 0.6049(3) 0.7657(5) 0.8463(2) 0.0187(7) Uani 1 1 d . . . . .
H19 H 0.5607 0.7056 0.8846 0.022 Uiso 1 1 calc R U . . .
C20 C 0.5503(3) 0.7673(4) 0.77153(19) 0.0173(7) Uani 1 1 d . . . . .
C21 C 0.6162(3) 0.8567(5) 0.71647(19) 0.0223(7) Uani 1 1 d . . . . .
H21 H 0.5788 0.8600 0.6656 0.027 Uiso 1 1 calc R U . . .
C22 C 0.7351(3) 0.9409(5) 0.7343(2) 0.0240(7) Uani 1 1 d . . . . .
H22 H 0.7797 1.0010 0.6962 0.029 Uiso 1 1 calc R U . . .
C23 C 0.7872(3) 0.9358(5) 0.8083(2) 0.0231(7) Uani 1 1 d . . . . .
C24 C 0.7235(3) 0.8516(5) 0.86511(19) 0.0207(7) Uani 1 1 d . . . . .
H24 H 0.7601 0.8525 0.9161 0.025 Uiso 1 1 calc R U . . .
C25 C 0.3727(3) 0.4989(4) 0.75702(18) 0.0172(7) Uani 1 1 d . . . . .
C26 C 0.3437(3) 0.4341(4) 0.83888(18) 0.0171(6) Uani 1 1 d . . . . .
H26 H 0.4283 0.4445 0.8709 0.020 Uiso 1 1 calc R U . . .
C27 C 0.3205(3) 0.2360(4) 0.82410(19) 0.0186(7) Uani 1 1 d . . . . .
H27 H 0.2275 0.2173 0.8034 0.022 Uiso 1 1 calc R U . . .
C28 C 0.4644(3) 0.3444(4) 0.73221(19) 0.0189(7) Uani 1 1 d . . . . .
C29 C 0.2440(3) 0.5054(4) 0.70575(17) 0.0172(7) Uani 1 1 d . . . . .
C30 C 0.8264(3) 0.4411(6) 0.7183(2) 0.0326(9) Uani 1 1 d . . . . .
H30A H 0.8784 0.3519 0.6932 0.049 Uiso 1 1 calc R U . . .
H30B H 0.8531 0.4437 0.7727 0.049 Uiso 1 1 calc R U . . .
H30C H 0.8419 0.5570 0.6960 0.049 Uiso 1 1 calc R U . . .
C31 C 0.3463(4) 0.1254(5) 0.8950(2) 0.0270(9) Uani 1 1 d . . . . .
C32 C 0.6081(3) 0.3758(4) 0.76677(19) 0.0189(7) Uani 1 1 d . . . . .
C33 C 0.4218(3) 0.6855(4) 0.74770(18) 0.0164(7) Uani 1 1 d . . . . .
F1 F 0.3363(3) -0.0466(3) 0.87761(15) 0.0386(6) Uani 1 1 d . . . . .
F2 F 0.2562(2) 0.1573(3) 0.94578(12) 0.0383(6) Uani 1 1 d . . . . .
F3 F 0.4638(2) 0.1507(4) 0.92976(14) 0.0459(6) Uani 1 1 d . . . . .
N1 N 0.4099(3) 0.1875(4) 0.76675(16) 0.0204(6) Uani 1 1 d . . . . .
N2 N 0.6874(3) 0.3975(4) 0.70782(16) 0.0217(6) Uani 1 1 d . . . . .
N3 N 0.3409(3) 0.7813(4) 0.70597(16) 0.0192(6) Uani 1 1 d . . . . .
N4 N 0.2317(3) 0.6769(4) 0.68106(16) 0.0189(6) Uani 1 1 d . . . . .
O1 O 0.1671(2) 0.3862(3) 0.69042(13) 0.0220(5) Uani 1 1 d . . . . .
O2 O 0.6441(2) 0.3807(3) 0.83393(14) 0.0241(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1 C23 1.903(3) . ?
C1 C6 1.382(6) . ?
C1 C2 1.387(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(5) . ?
C4 C26 1.507(4) . ?
C5 C6 1.388(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.387(5) . ?
C7 C8 1.393(5) . ?
C7 N4 1.420(4) . ?
C8 C9 1.387(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.380(5) . ?
C13 C18 1.400(5) . ?
C13 C28 1.516(5) . ?
C14 C15 1.394(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(5) . ?
C17 H17 0.9500 . ?
C18 N2 1.397(5) . ?
C19 C24 1.389(5) . ?
C19 C20 1.396(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(5) . ?
C20 C33 1.480(5) . ?
C21 C22 1.382(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(5) . ?
C24 H24 0.9500 . ?
C25 C33 1.513(5) . ?
C25 C29 1.540(4) . ?
C25 C26 1.570(5) . ?
C25 C28 1.576(5) . ?
C26 C27 1.540(5) . ?
C26 H26 1.0000 . ?
C27 N1 1.449(4) . ?
C27 C31 1.513(5) . ?
C27 H27 1.0000 . ?
C28 N1 1.462(4) . ?
C28 C32 1.561(5) . ?
C29 O1 1.213(4) . ?
C29 N4 1.375(5) . ?
C30 N2 1.450(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 F3 1.318(5) . ?
C31 F1 1.342(4) . ?
C31 F2 1.344(5) . ?
C32 O2 1.216(4) . ?
C32 N2 1.365(4) . ?
C33 N3 1.290(4) . ?
N3 N4 1.409(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
C6 C1 C2 119.7(3) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 C26 118.7(3) . . ?
C3 C4 C26 123.1(3) . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 119.6(4) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C12 C7 C8 119.9(3) . . ?
C12 C7 N4 119.6(3) . . ?
C8 C7 N4 120.5(3) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 121.5(4) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 118.9(3) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 119.9(3) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C14 C13 C18 119.7(3) . . ?
C14 C13 C28 132.0(3) . . ?
C18 C13 C28 108.2(3) . . ?
C13 C14 C15 119.2(4) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 121.3(4) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 117.7(4) . . ?
C18 C17 H17 121.2 . . ?
C16 C17 H17 121.2 . . ?
C17 C18 N2 127.9(3) . . ?
C17 C18 C13 121.6(3) . . ?
N2 C18 C13 110.5(3) . . ?
C24 C19 C20 120.3(3) . . ?
C24 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 118.9(3) . . ?
C21 C20 C33 117.5(3) . . ?
C19 C20 C33 123.5(3) . . ?
C22 C21 C20 121.3(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 118.6(3) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C22 C23 C24 122.0(3) . . ?
C22 C23 Br1 118.8(3) . . ?
C24 C23 Br1 119.2(3) . . ?
C23 C24 C19 118.9(3) . . ?
C23 C24 H24 120.6 . . ?
C19 C24 H24 120.6 . . ?
C33 C25 C29 100.3(3) . . ?
C33 C25 C26 118.4(3) . . ?
C29 C25 C26 110.3(2) . . ?
C33 C25 C28 117.4(3) . . ?
C29 C25 C28 110.8(3) . . ?
C26 C25 C28 99.9(2) . . ?
C4 C26 C27 115.4(3) . . ?
C4 C26 C25 119.6(3) . . ?
C27 C26 C25 100.7(2) . . ?
C4 C26 H26 106.8 . . ?
C27 C26 H26 106.8 . . ?
C25 C26 H26 106.8 . . ?
N1 C27 C31 110.6(3) . . ?
N1 C27 C26 105.7(3) . . ?
C31 C27 C26 112.6(3) . . ?
N1 C27 H27 109.3 . . ?
C31 C27 H27 109.3 . . ?
C26 C27 H27 109.3 . . ?
N1 C28 C13 115.6(3) . . ?
N1 C28 C32 109.3(3) . . ?
C13 C28 C32 101.8(3) . . ?
N1 C28 C25 104.1(3) . . ?
C13 C28 C25 116.6(3) . . ?
C32 C28 C25 109.4(3) . . ?
O1 C29 N4 126.2(3) . . ?
O1 C29 C25 128.0(3) . . ?
N4 C29 C25 105.8(3) . . ?
N2 C30 H30A 109.5 . . ?
N2 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N2 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
F3 C31 F1 107.5(3) . . ?
F3 C31 F2 107.4(3) . . ?
F1 C31 F2 106.4(3) . . ?
F3 C31 C27 113.9(3) . . ?
F1 C31 C27 110.1(3) . . ?
F2 C31 C27 111.2(3) . . ?
O2 C32 N2 125.7(3) . . ?
O2 C32 C28 126.7(3) . . ?
N2 C32 C28 107.7(3) . . ?
N3 C33 C20 116.2(3) . . ?
N3 C33 C25 112.8(3) . . ?
C20 C33 C25 130.7(3) . . ?
C27 N1 C28 110.8(3) . . ?
C32 N2 C18 111.4(3) . . ?
C32 N2 C30 123.2(3) . . ?
C18 N2 C30 125.3(3) . . ?
C33 N3 N4 108.6(3) . . ?
C29 N4 N3 112.3(3) . . ?
C29 N4 C7 129.6(3) . . ?
N3 N4 C7 117.9(3) . . ?

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
C6 C1 C2 C3 -0.6(6) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 C26 175.9(3) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C26 C4 C5 C6 -176.9(3) . . . . ?
C2 C1 C6 C5 -0.2(6) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
C12 C7 C8 C9 -1.2(5) . . . . ?
N4 C7 C8 C9 179.2(3) . . . . ?
C7 C8 C9 C10 0.6(6) . . . . ?
C8 C9 C10 C11 0.4(6) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C10 C11 C12 C7 0.3(5) . . . . ?
C8 C7 C12 C11 0.8(5) . . . . ?
N4 C7 C12 C11 -179.6(3) . . . . ?
C18 C13 C14 C15 -1.5(5) . . . . ?
C28 C13 C14 C15 -178.0(4) . . . . ?
C13 C14 C15 C16 0.9(6) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
C16 C17 C18 N2 177.4(4) . . . . ?
C16 C17 C18 C13 -0.1(5) . . . . ?
C14 C13 C18 C17 1.1(5) . . . . ?
C28 C13 C18 C17 178.4(3) . . . . ?
C14 C13 C18 N2 -176.9(3) . . . . ?
C28 C13 C18 N2 0.4(4) . . . . ?
C24 C19 C20 C21 -0.3(5) . . . . ?
C24 C19 C20 C33 -177.3(3) . . . . ?
C19 C20 C21 C22 1.1(5) . . . . ?
C33 C20 C21 C22 178.3(3) . . . . ?
C20 C21 C22 C23 -0.4(5) . . . . ?
C21 C22 C23 C24 -1.0(6) . . . . ?
C21 C22 C23 Br1 178.3(3) . . . . ?
C22 C23 C24 C19 1.8(5) . . . . ?
Br1 C23 C24 C19 -177.6(3) . . . . ?
C20 C19 C24 C23 -1.1(5) . . . . ?
C5 C4 C26 C27 125.5(3) . . . . ?
C3 C4 C26 C27 -49.8(4) . . . . ?
C5 C4 C26 C25 -114.1(3) . . . . ?
C3 C4 C26 C25 70.6(4) . . . . ?
C33 C25 C26 C4 61.6(4) . . . . ?
C29 C25 C26 C4 -53.0(4) . . . . ?
C28 C25 C26 C4 -169.7(3) . . . . ?
C33 C25 C26 C27 -170.9(3) . . . . ?
C29 C25 C26 C27 74.5(3) . . . . ?
C28 C25 C26 C27 -42.2(3) . . . . ?
C4 C26 C27 N1 165.3(3) . . . . ?
C25 C26 C27 N1 35.0(3) . . . . ?
C4 C26 C27 C31 -73.8(4) . . . . ?
C25 C26 C27 C31 155.9(3) . . . . ?
C14 C13 C28 N1 54.2(5) . . . . ?
C18 C13 C28 N1 -122.6(3) . . . . ?
C14 C13 C28 C32 172.5(4) . . . . ?
C18 C13 C28 C32 -4.3(3) . . . . ?
C14 C13 C28 C25 -68.5(5) . . . . ?
C18 C13 C28 C25 114.6(3) . . . . ?
C33 C25 C28 N1 164.8(3) . . . . ?
C29 C25 C28 N1 -80.8(3) . . . . ?
C26 C25 C28 N1 35.5(3) . . . . ?
C33 C25 C28 C13 -66.6(4) . . . . ?
C29 C25 C28 C13 47.8(4) . . . . ?
C26 C25 C28 C13 164.0(3) . . . . ?
C33 C25 C28 C32 48.1(4) . . . . ?
C29 C25 C28 C32 162.5(3) . . . . ?
C26 C25 C28 C32 -81.3(3) . . . . ?
C33 C25 C29 O1 177.0(3) . . . . ?
C26 C25 C29 O1 -57.4(4) . . . . ?
C28 C25 C29 O1 52.2(4) . . . . ?
C33 C25 C29 N4 -3.9(3) . . . . ?
C26 C25 C29 N4 121.7(3) . . . . ?
C28 C25 C29 N4 -128.7(3) . . . . ?
N1 C27 C31 F3 64.4(4) . . . . ?
C26 C27 C31 F3 -53.6(4) . . . . ?
N1 C27 C31 F1 -56.4(4) . . . . ?
C26 C27 C31 F1 -174.5(3) . . . . ?
N1 C27 C31 F2 -174.2(3) . . . . ?
C26 C27 C31 F2 67.8(4) . . . . ?
N1 C28 C32 O2 -50.6(4) . . . . ?
C13 C28 C32 O2 -173.3(3) . . . . ?
C25 C28 C32 O2 62.7(4) . . . . ?
N1 C28 C32 N2 129.6(3) . . . . ?
C13 C28 C32 N2 6.9(3) . . . . ?
C25 C28 C32 N2 -117.1(3) . . . . ?
C21 C20 C33 N3 -45.3(4) . . . . ?
C19 C20 C33 N3 131.7(3) . . . . ?
C21 C20 C33 C25 127.3(4) . . . . ?
C19 C20 C33 C25 -55.6(5) . . . . ?
C29 C25 C33 N3 3.1(3) . . . . ?
C26 C25 C33 N3 -116.8(3) . . . . ?
C28 C25 C33 N3 123.2(3) . . . . ?
C29 C25 C33 C20 -169.8(3) . . . . ?
C26 C25 C33 C20 70.3(4) . . . . ?
C28 C25 C33 C20 -49.7(5) . . . . ?
C31 C27 N1 C28 -135.1(3) . . . . ?
C26 C27 N1 C28 -12.9(3) . . . . ?
C13 C28 N1 C27 -144.0(3) . . . . ?
C32 C28 N1 C27 102.0(3) . . . . ?
C25 C28 N1 C27 -14.8(3) . . . . ?
O2 C32 N2 C18 173.0(3) . . . . ?
C28 C32 N2 C18 -7.1(4) . . . . ?
O2 C32 N2 C30 -4.0(5) . . . . ?
C28 C32 N2 C30 175.8(3) . . . . ?
C17 C18 N2 C32 -173.4(4) . . . . ?
C13 C18 N2 C32 4.4(4) . . . . ?
C17 C18 N2 C30 3.6(6) . . . . ?
C13 C18 N2 C30 -178.6(3) . . . . ?
C20 C33 N3 N4 172.9(3) . . . . ?
C25 C33 N3 N4 -1.0(4) . . . . ?
O1 C29 N4 N3 -177.1(3) . . . . ?
C25 C29 N4 N3 3.8(3) . . . . ?
O1 C29 N4 C7 8.0(6) . . . . ?
C25 C29 N4 C7 -171.2(3) . . . . ?
C33 N3 N4 C29 -1.9(4) . . . . ?
C33 N3 N4 C7 173.7(3) . . . . ?
C12 C7 N4 C29 155.6(3) . . . . ?
C8 C7 N4 C29 -24.8(5) . . . . ?
C12 C7 N4 N3 -19.1(4) . . . . ?
C8 C7 N4 N3 160.5(3) . . . . ?

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.047



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20180308_WANGCui_C32HO2N4F3Cl__a
_database_code_depnum_ccdc_archive 'CCDC 1887394'
loop_
_audit_author_name
_audit_author_address
'cui wang'
;Lanzhou University
China
;
_audit_update_record             
;
2018-12-26 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H23 Cl F3 N4 O2'
_chemical_formula_weight         600.00

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1089(5)
_cell_length_b                   12.9197(6)
_cell_length_c                   14.1096(7)
_cell_angle_alpha                105.902(2)
_cell_angle_beta                 108.629(2)
_cell_angle_gamma                106.656(2)
_cell_volume                     1531.34(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      66.58

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             618
_exptl_transmission_factor_min   0.3820
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.569
_shelx_estimated_absorpt_T_min   0.650
_shelx_estimated_absorpt_T_max   0.744
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 1.000 1.000 199 36 ' '
_platon_squeeze_details          
;
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            27781
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.611
_diffrn_reflns_theta_max         67.021
_diffrn_reflns_theta_full        67.021
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5387
_reflns_number_gt                4717
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.3899P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5387
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1455
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.8374(2) 0.88949(17) 0.25736(18) 0.0308(4) Uani 1 1 d . . . . .
C2 C 0.8666(3) 0.8639(2) 0.1668(2) 0.0430(5) Uani 1 1 d . . . . .
H2 H 0.8004 0.7928 0.1038 0.052 Uiso 1 1 calc R U . . .
C3 C 0.9946(3) 0.9439(2) 0.1690(3) 0.0567(7) Uani 1 1 d . . . . .
H3 H 1.0164 0.9264 0.1072 0.068 Uiso 1 1 calc R U . . .
C4 C 1.0903(3) 1.0480(2) 0.2593(3) 0.0551(7) Uani 1 1 d . . . . .
H4 H 1.1766 1.1024 0.2594 0.066 Uiso 1 1 calc R U . . .
C5 C 1.0601(3) 1.0727(2) 0.3497(2) 0.0479(6) Uani 1 1 d . . . . .
H5 H 1.1262 1.1443 0.4123 0.057 Uiso 1 1 calc R U . . .
C6 C 0.9347(2) 0.99433(18) 0.34986(19) 0.0362(5) Uani 1 1 d . . . . .
H6 H 0.9145 1.0114 0.4124 0.043 Uiso 1 1 calc R U . . .
C7 C 0.63069(19) 0.69129(15) 0.20385(14) 0.0208(4) Uani 1 1 d . . . . .
C8 C 0.51445(19) 0.65384(15) 0.24883(14) 0.0198(4) Uani 1 1 d . . . . .
C9 C 0.5450(2) 0.77261(15) 0.32949(14) 0.0227(4) Uani 1 1 d . . . . .
C10 C 0.4622(2) 0.80039(15) 0.39573(15) 0.0235(4) Uani 1 1 d . . . . .
C11 C 0.4757(2) 0.76889(18) 0.48348(17) 0.0318(4) Uani 1 1 d . . . . .
H11 H 0.5357 0.7261 0.5004 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4017(3) 0.79998(19) 0.54645(18) 0.0356(5) Uani 1 1 d . . . . .
H12 H 0.4116 0.7789 0.6070 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3135(2) 0.86144(18) 0.52192(18) 0.0344(5) Uani 1 1 d . . . . .
H13 H 0.2634 0.8829 0.5658 0.041 Uiso 1 1 calc R U . . .
C14 C 0.2980(2) 0.89173(18) 0.43359(18) 0.0342(5) Uani 1 1 d . . . . .
H14 H 0.2364 0.9333 0.4162 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3723(2) 0.86136(17) 0.37061(16) 0.0294(4) Uani 1 1 d . . . . .
H15 H 0.3618 0.8823 0.3099 0.035 Uiso 1 1 calc R U . . .
C16 C 0.34905(19) 0.58172(15) 0.15331(14) 0.0206(4) Uani 1 1 d . . . . .
C17 C 0.22552(19) 0.57176(15) 0.19854(14) 0.0227(4) Uani 1 1 d . . . . .
C18 C 0.2980(2) 0.63235(16) 0.07114(14) 0.0241(4) Uani 1 1 d . . . . .
C19 C 0.3531(2) 0.65740(18) -0.00113(16) 0.0306(4) Uani 1 1 d . . . . .
H19 H 0.4426 0.6476 -0.0013 0.037 Uiso 1 1 calc R U . . .
C20 C 0.2756(3) 0.6974(2) -0.07422(17) 0.0381(5) Uani 1 1 d . . . . .
H20 H 0.3131 0.7155 -0.1241 0.046 Uiso 1 1 calc R U . . .
C21 C 0.1441(3) 0.7107(2) -0.07427(18) 0.0405(5) Uani 1 1 d . . . . .
H21 H 0.0917 0.7368 -0.1252 0.049 Uiso 1 1 calc R U . . .
C22 C 0.0878(2) 0.68696(19) -0.00197(17) 0.0345(5) Uani 1 1 d . . . . .
H22 H -0.0018 0.6968 -0.0019 0.041 Uiso 1 1 calc R U . . .
C23 C 0.1665(2) 0.64814(16) 0.07054(15) 0.0255(4) Uani 1 1 d . . . . .
C24 C 0.0013(2) 0.6217(2) 0.17227(17) 0.0341(5) Uani 1 1 d . . . . .
H24A H -0.0909 0.5911 0.1040 0.051 Uiso 1 1 calc R U . . .
H24B H 0.0262 0.7041 0.2151 0.051 Uiso 1 1 calc R U . . .
H24C H -0.0170 0.5746 0.2144 0.051 Uiso 1 1 calc R U . . .
C25 C 0.4647(2) 0.44907(16) 0.18613(14) 0.0229(4) Uani 1 1 d . . . . .
H25 H 0.5478 0.4486 0.1624 0.028 Uiso 1 1 calc R U . . .
C26 C 0.53071(19) 0.55844(15) 0.29397(14) 0.0213(4) Uani 1 1 d . . . . .
H26 H 0.4567 0.5445 0.3269 0.026 Uiso 1 1 calc R U . . .
C27 C 0.6861(2) 0.58517(15) 0.38020(14) 0.0222(4) Uani 1 1 d . . . . .
C28 C 0.8192(2) 0.61284(19) 0.36504(16) 0.0303(4) Uani 1 1 d . . . . .
H28 H 0.8147 0.6145 0.2972 0.036 Uiso 1 1 calc R U . . .
C29 C 0.9589(2) 0.6382(2) 0.44791(17) 0.0347(5) Uani 1 1 d . . . . .
H29 H 1.0496 0.6582 0.4373 0.042 Uiso 1 1 calc R U . . .
C30 C 0.9640(2) 0.63384(18) 0.54523(16) 0.0301(4) Uani 1 1 d . . . . .
C31 C 0.8340(2) 0.60254(18) 0.56183(16) 0.0303(4) Uani 1 1 d . . . . .
H31 H 0.8384 0.5970 0.6284 0.036 Uiso 1 1 calc R U . . .
C32 C 0.6967(2) 0.57928(17) 0.47905(15) 0.0264(4) Uani 1 1 d . . . . .
H32 H 0.6065 0.5586 0.4902 0.032 Uiso 1 1 calc R U . . .
C33 C 0.3983(2) 0.33394(17) 0.19584(16) 0.0310(4) Uani 1 1 d . . . . .
Cl1 Cl 1.13940(6) 0.66826(6) 0.64981(4) 0.04534(19) Uani 1 1 d . . . . .
F1 F 0.50859(16) 0.31650(11) 0.26466(12) 0.0531(4) Uani 1 1 d . . . . .
F2 F 0.33802(17) 0.24206(10) 0.09997(11) 0.0491(4) Uani 1 1 d . . . . .
F3 F 0.29076(17) 0.32560(11) 0.23079(13) 0.0515(4) Uani 1 1 d . . . . .
N1 N 0.70755(18) 0.81099(13) 0.25905(13) 0.0264(3) Uani 1 1 d . . . . .
N2 N 0.65288(19) 0.85801(14) 0.33347(13) 0.0289(4) Uani 1 1 d . . . . .
N3 N 0.12854(17) 0.61440(14) 0.14752(13) 0.0255(3) Uani 1 1 d . . . . .
N4 N 0.34564(16) 0.46318(13) 0.10451(12) 0.0230(3) Uani 1 1 d . . . . .
O1 O 0.21442(14) 0.53141(12) 0.26534(11) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.65209(14) 0.62787(11) 0.13326(10) 0.0246(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.376(3) . ?
C1 C6 1.398(3) . ?
C1 N1 1.422(2) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O2 1.226(2) . ?
C7 N1 1.366(2) . ?
C7 C8 1.528(2) . ?
C8 C9 1.514(2) . ?
C8 C26 1.559(2) . ?
C8 C16 1.568(2) . ?
C9 N2 1.283(2) . ?
C9 C10 1.480(2) . ?
C10 C11 1.385(3) . ?
C10 C15 1.389(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 N4 1.482(2) . ?
C16 C18 1.505(2) . ?
C16 C17 1.564(2) . ?
C17 O1 1.215(2) . ?
C17 N3 1.363(2) . ?
C18 C19 1.376(3) . ?
C18 C23 1.399(3) . ?
C19 C20 1.397(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 N3 1.395(3) . ?
C24 N3 1.457(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 N4 1.471(2) . ?
C25 C33 1.510(3) . ?
C25 C26 1.546(2) . ?
C25 H25 1.0000 . ?
C26 C27 1.518(2) . ?
C26 H26 1.0000 . ?
C27 C32 1.389(3) . ?
C27 C28 1.390(3) . ?
C28 C29 1.393(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.375(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.374(3) . ?
C30 Cl1 1.7423(18) . ?
C31 C32 1.384(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 F3 1.319(2) . ?
C33 F2 1.338(2) . ?
C33 F1 1.345(2) . ?
N1 N2 1.411(2) . ?

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 C1 C6 120.5(2) . . ?
C2 C1 N1 121.14(19) . . ?
C6 C1 N1 118.39(19) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
O2 C7 N1 126.58(17) . . ?
O2 C7 C8 127.60(16) . . ?
N1 C7 C8 105.82(14) . . ?
C9 C8 C7 100.59(14) . . ?
C9 C8 C26 117.36(14) . . ?
C7 C8 C26 112.70(13) . . ?
C9 C8 C16 116.63(13) . . ?
C7 C8 C16 110.29(14) . . ?
C26 C8 C16 99.72(13) . . ?
N2 C9 C10 118.64(16) . . ?
N2 C9 C8 112.60(16) . . ?
C10 C9 C8 128.65(16) . . ?
C11 C10 C15 119.68(17) . . ?
C11 C10 C9 121.07(16) . . ?
C15 C10 C9 119.24(17) . . ?
C12 C11 C10 119.78(18) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.03(19) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 119.81(19) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 120.26(19) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
N4 C16 C18 113.65(14) . . ?
N4 C16 C17 109.48(14) . . ?
C18 C16 C17 101.69(13) . . ?
N4 C16 C8 103.58(13) . . ?
C18 C16 C8 117.66(15) . . ?
C17 C16 C8 110.82(14) . . ?
O1 C17 N3 125.43(16) . . ?
O1 C17 C16 126.91(16) . . ?
N3 C17 C16 107.64(15) . . ?
C19 C18 C23 119.50(17) . . ?
C19 C18 C16 131.54(16) . . ?
C23 C18 C16 108.87(16) . . ?
C18 C19 C20 119.17(18) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 121.44(19) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 117.63(19) . . ?
C21 C22 H22 121.2 . . ?
C23 C22 H22 121.2 . . ?
C22 C23 N3 127.96(18) . . ?
C22 C23 C18 122.00(19) . . ?
N3 C23 C18 109.97(15) . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N4 C25 C33 110.27(15) . . ?
N4 C25 C26 106.48(13) . . ?
C33 C25 C26 113.23(16) . . ?
N4 C25 H25 108.9 . . ?
C33 C25 H25 108.9 . . ?
C26 C25 H25 108.9 . . ?
C27 C26 C25 116.50(14) . . ?
C27 C26 C8 118.05(14) . . ?
C25 C26 C8 100.56(13) . . ?
C27 C26 H26 107.0 . . ?
C25 C26 H26 107.0 . . ?
C8 C26 H26 107.0 . . ?
C32 C27 C28 117.65(16) . . ?
C32 C27 C26 118.75(16) . . ?
C28 C27 C26 123.59(16) . . ?
C27 C28 C29 120.92(18) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 119.18(18) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C31 C30 C29 121.59(17) . . ?
C31 C30 Cl1 119.23(15) . . ?
C29 C30 Cl1 119.18(15) . . ?
C30 C31 C32 118.29(18) . . ?
C30 C31 H31 120.9 . . ?
C32 C31 H31 120.9 . . ?
C31 C32 C27 122.30(17) . . ?
C31 C32 H32 118.9 . . ?
C27 C32 H32 118.9 . . ?
F3 C33 F2 107.10(17) . . ?
F3 C33 F1 107.17(17) . . ?
F2 C33 F1 105.54(15) . . ?
F3 C33 C25 114.68(16) . . ?
F2 C33 C25 111.22(17) . . ?
F1 C33 C25 110.62(16) . . ?
C7 N1 N2 112.57(15) . . ?
C7 N1 C1 129.48(16) . . ?
N2 N1 C1 117.76(15) . . ?
C9 N2 N1 108.39(15) . . ?
C17 N3 C23 111.77(15) . . ?
C17 N3 C24 122.59(16) . . ?
C23 N3 C24 125.64(16) . . ?
C25 N4 C16 108.66(13) . . ?

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
C6 C1 C2 C3 0.2(4) . . . . ?
N1 C1 C2 C3 179.7(2) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
N1 C1 C6 C5 -179.07(19) . . . . ?
O2 C7 C8 C9 -178.68(16) . . . . ?
N1 C7 C8 C9 1.61(17) . . . . ?
O2 C7 C8 C26 55.5(2) . . . . ?
N1 C7 C8 C26 -124.19(15) . . . . ?
O2 C7 C8 C16 -55.0(2) . . . . ?
N1 C7 C8 C16 125.34(15) . . . . ?
C7 C8 C9 N2 -1.13(19) . . . . ?
C26 C8 C9 N2 121.47(17) . . . . ?
C16 C8 C9 N2 -120.36(17) . . . . ?
C7 C8 C9 C10 174.92(17) . . . . ?
C26 C8 C9 C10 -62.5(2) . . . . ?
C16 C8 C9 C10 55.7(2) . . . . ?
N2 C9 C10 C11 -112.4(2) . . . . ?
C8 C9 C10 C11 71.8(3) . . . . ?
N2 C9 C10 C15 66.2(2) . . . . ?
C8 C9 C10 C15 -109.6(2) . . . . ?
C15 C10 C11 C12 -1.0(3) . . . . ?
C9 C10 C11 C12 177.54(18) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C9 C10 C15 C14 -177.85(18) . . . . ?
C9 C8 C16 N4 -168.35(15) . . . . ?
C7 C8 C16 N4 77.78(16) . . . . ?
C26 C8 C16 N4 -40.95(16) . . . . ?
C9 C8 C16 C18 65.3(2) . . . . ?
C7 C8 C16 C18 -48.55(19) . . . . ?
C26 C8 C16 C18 -167.28(15) . . . . ?
C9 C8 C16 C17 -51.0(2) . . . . ?
C7 C8 C16 C17 -164.90(14) . . . . ?
C26 C8 C16 C17 76.37(16) . . . . ?
N4 C16 C17 O1 56.9(2) . . . . ?
C18 C16 C17 O1 177.36(17) . . . . ?
C8 C16 C17 O1 -56.8(2) . . . . ?
N4 C16 C17 N3 -121.79(15) . . . . ?
C18 C16 C17 N3 -1.28(18) . . . . ?
C8 C16 C17 N3 124.58(15) . . . . ?
N4 C16 C18 C19 -58.9(3) . . . . ?
C17 C16 C18 C19 -176.5(2) . . . . ?
C8 C16 C18 C19 62.3(3) . . . . ?
N4 C16 C18 C23 117.52(16) . . . . ?
C17 C16 C18 C23 -0.02(18) . . . . ?
C8 C16 C18 C23 -121.23(17) . . . . ?
C23 C18 C19 C20 -0.4(3) . . . . ?
C16 C18 C19 C20 175.69(19) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
C19 C20 C21 C22 1.0(4) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C21 C22 C23 N3 -177.25(19) . . . . ?
C21 C22 C23 C18 -0.4(3) . . . . ?
C19 C18 C23 C22 0.9(3) . . . . ?
C16 C18 C23 C22 -176.04(17) . . . . ?
C19 C18 C23 N3 178.25(17) . . . . ?
C16 C18 C23 N3 1.3(2) . . . . ?
N4 C25 C26 C27 -161.31(15) . . . . ?
C33 C25 C26 C27 77.3(2) . . . . ?
N4 C25 C26 C8 -32.45(17) . . . . ?
C33 C25 C26 C8 -153.79(14) . . . . ?
C9 C8 C26 C27 -61.3(2) . . . . ?
C7 C8 C26 C27 54.8(2) . . . . ?
C16 C8 C26 C27 171.76(14) . . . . ?
C9 C8 C26 C25 170.82(14) . . . . ?
C7 C8 C26 C25 -73.03(17) . . . . ?
C16 C8 C26 C25 43.90(15) . . . . ?
C25 C26 C27 C32 -116.01(19) . . . . ?
C8 C26 C27 C32 124.14(18) . . . . ?
C25 C26 C27 C28 62.5(2) . . . . ?
C8 C26 C27 C28 -57.4(2) . . . . ?
C32 C27 C28 C29 -2.4(3) . . . . ?
C26 C27 C28 C29 179.09(18) . . . . ?
C27 C28 C29 C30 1.0(3) . . . . ?
C28 C29 C30 C31 1.5(3) . . . . ?
C28 C29 C30 Cl1 -178.79(17) . . . . ?
C29 C30 C31 C32 -2.4(3) . . . . ?
Cl1 C30 C31 C32 177.93(15) . . . . ?
C30 C31 C32 C27 0.8(3) . . . . ?
C28 C27 C32 C31 1.6(3) . . . . ?
C26 C27 C32 C31 -179.89(17) . . . . ?
N4 C25 C33 F3 -63.0(2) . . . . ?
C26 C25 C33 F3 56.2(2) . . . . ?
N4 C25 C33 F2 58.8(2) . . . . ?
C26 C25 C33 F2 177.93(15) . . . . ?
N4 C25 C33 F1 175.70(15) . . . . ?
C26 C25 C33 F1 -65.1(2) . . . . ?
O2 C7 N1 N2 178.60(16) . . . . ?
C8 C7 N1 N2 -1.69(19) . . . . ?
O2 C7 N1 C1 -6.6(3) . . . . ?
C8 C7 N1 C1 173.08(18) . . . . ?
C2 C1 N1 C7 28.0(3) . . . . ?
C6 C1 N1 C7 -152.50(19) . . . . ?
C2 C1 N1 N2 -157.46(19) . . . . ?
C6 C1 N1 N2 22.0(3) . . . . ?
C10 C9 N2 N1 -176.29(15) . . . . ?
C8 C9 N2 N1 0.2(2) . . . . ?
C7 N1 N2 C9 1.0(2) . . . . ?
C1 N1 N2 C9 -174.44(16) . . . . ?
O1 C17 N3 C23 -176.49(17) . . . . ?
C16 C17 N3 C23 2.2(2) . . . . ?
O1 C17 N3 C24 3.1(3) . . . . ?
C16 C17 N3 C24 -178.20(16) . . . . ?
C22 C23 N3 C17 174.88(19) . . . . ?
C18 C23 N3 C17 -2.3(2) . . . . ?
C22 C23 N3 C24 -4.7(3) . . . . ?
C18 C23 N3 C24 178.14(17) . . . . ?
C33 C25 N4 C16 130.04(16) . . . . ?
C26 C25 N4 C16 6.83(19) . . . . ?
C18 C16 N4 C25 150.54(15) . . . . ?
C17 C16 N4 C25 -96.53(16) . . . . ?
C8 C16 N4 C25 21.71(18) . . . . ?

_refine_diff_density_max         0.669
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.064



