# Electronic Supplementary Material (ESI) for Green 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_lq-hb-zq-02062
_database_code_depnum_ccdc_archive 'CCDC 1898392'
loop_
_audit_author_name
_audit_author_address
'Bo Han'
;Chengdu University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-10-16 downloaded from the CCDC.
;
_audit_creation_date             2018-01-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 F3 O3'
_chemical_formula_sum            'C23 H17 F3 O3'
_chemical_formula_weight         398.36
_chemical_melting_point          ?
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.2218(6)
_cell_length_b                   13.2420(4)
_cell_length_c                   17.2998(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3945.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5114
_cell_measurement_temperature    293.8(2)
_cell_measurement_theta_max      72.3270
_cell_measurement_theta_min      4.1440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11346
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.427
_diffrn_reflns_theta_min         4.928
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.8(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    9.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   77.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   57.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega    0.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   94.0000 -158.1318 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921 -125.0000  -30.0000 66

#__ type_ start__ end____ width___ exp.time_
  6 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921  -38.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   88.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega   43.00   98.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
  9 omega   42.00   92.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
 10 omega   70.00  100.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
 11 omega   49.00   88.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 12 omega   42.00  115.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0162154000
_diffrn_orient_matrix_UB_12      -0.0396108000
_diffrn_orient_matrix_UB_13      0.0821760000
_diffrn_orient_matrix_UB_21      0.0871094000
_diffrn_orient_matrix_UB_22      0.0228495000
_diffrn_orient_matrix_UB_23      -0.0106249000
_diffrn_orient_matrix_UB_31      -0.0124981000
_diffrn_orient_matrix_UB_32      0.1069276000
_diffrn_orient_matrix_UB_33      0.0326367000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3139
_reflns_number_total             3809
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3809
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0650
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0996P)²+0.9268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1709
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H00a,H00c)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H00B), C13(H00F), C5(H00H), C1(H00I), C19(H00J), C15(H00K), C2(H00M),
 C3(H00N), C4(H00O), C17(H00P), C18(H00Q), C16(H00R)
2.c Idealised Me refined as rotating group:
 C22(H00d,H00e,H00g)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
F001 F 0.24797(11) 0.55283(11) 0.65592(8) 0.0777(5) Uani 1 1 d . . . . .
O002 O 0.44052(9) 0.29012(11) 0.58735(9) 0.0536(4) Uani 1 1 d . . . . .
F003 F 0.31833(10) 0.42420(12) 0.68087(7) 0.0767(5) Uani 1 1 d . . . . .
F004 F 0.20944(10) 0.40703(13) 0.62311(10) 0.0834(5) Uani 1 1 d . . . . .
O005 O 0.31582(9) 0.24479(11) 0.57416(10) 0.0624(5) Uani 1 1 d . . . . .
O006 O 0.42082(14) 0.46932(13) 0.27845(9) 0.0788(6) Uani 1 1 d . . . . .
C007 C 0.35839(10) 0.40040(13) 0.51948(10) 0.0358(4) Uani 1 1 d . . . . .
C008 C 0.31248(10) 0.47768(13) 0.55076(10) 0.0373(4) Uani 1 1 d . . . . .
C009 C 0.39316(10) 0.41403(13) 0.44717(10) 0.0356(4) Uani 1 1 d . . . . .
C00A C 0.33776(11) 0.58318(13) 0.44017(10) 0.0370(4) Uani 1 1 d . . . . .
C00B C 0.30231(11) 0.56738(13) 0.51129(10) 0.0384(4) Uani 1 1 d . . . . .
H00B H 0.2714 0.6178 0.5326 0.046 Uiso 1 1 calc R . . . .
C00C C 0.38282(10) 0.50617(13) 0.40816(10) 0.0366(4) Uani 1 1 d . . . . .
C00D C 0.43997(11) 0.33079(14) 0.41224(10) 0.0402(4) Uani 1 1 d . . . . .
C00E C 0.36840(11) 0.30253(14) 0.56267(11) 0.0421(4) Uani 1 1 d . . . . .
C00F C 0.42176(12) 0.52509(15) 0.33199(11) 0.0476(5) Uani 1 1 d . . . . .
H00F H 0.4488 0.5854 0.3263 0.057 Uiso 1 1 calc R . . . .
C00G C 0.32349(11) 0.68083(14) 0.39969(11) 0.0407(4) Uani 1 1 d . . . . .
C00H C 0.33191(14) 0.77143(15) 0.43918(12) 0.0507(5) Uani 1 1 d . . . . .
H00H H 0.3480 0.7710 0.4905 0.061 Uiso 1 1 calc R . . . .
C00I C 0.29762(13) 0.68334(16) 0.32337(11) 0.0501(5) Uani 1 1 d . . . . .
H00I H 0.2913 0.6233 0.2962 0.060 Uiso 1 1 calc R . . . .
C00J C 0.40440(14) 0.24219(16) 0.38920(14) 0.0560(5) Uani 1 1 d . . . . .
H00J H 0.3514 0.2335 0.3968 0.067 Uiso 1 1 calc R . . . .
C00K C 0.51929(12) 0.34166(18) 0.40118(13) 0.0527(5) Uani 1 1 d . . . . .
H00K H 0.5439 0.4008 0.4167 0.063 Uiso 1 1 calc R . . . .
C00L C 0.27245(14) 0.46567(16) 0.62734(12) 0.0519(5) Uani 1 1 d . . . . .
C00M C 0.28127(16) 0.77467(18) 0.28759(14) 0.0630(6) Uani 1 1 d . . . . .
H00M H 0.2637 0.7757 0.2368 0.076 Uiso 1 1 calc R . . . .
C00N C 0.29110(17) 0.86363(18) 0.32741(14) 0.0671(7) Uani 1 1 d . . . . .
H00N H 0.2806 0.9249 0.3033 0.081 Uiso 1 1 calc R . . . .
C00O C 0.31649(16) 0.86242(16) 0.40283(14) 0.0630(6) Uani 1 1 d . . . . .
H00O H 0.3233 0.9228 0.4294 0.076 Uiso 1 1 calc R . . . .
C00P C 0.52645(18) 0.1779(2) 0.34397(15) 0.0741(8) Uani 1 1 d . . . . .
H00P H 0.5554 0.1268 0.3210 0.089 Uiso 1 1 calc R . . . .
C00Q C 0.4478(2) 0.16633(19) 0.35478(16) 0.0743(8) Uani 1 1 d . . . . .
H00Q H 0.4235 0.1071 0.3389 0.089 Uiso 1 1 calc R . . . .
C00R C 0.56173(15) 0.2655(2) 0.36745(15) 0.0700(7) Uani 1 1 d . . . . .
H00R H 0.6149 0.2735 0.3605 0.084 Uiso 1 1 calc R . . . .
C00S C 0.45640(18) 0.19656(19) 0.63017(17) 0.0744(8) Uani 1 1 d . . . . .
H00A H 0.4139 0.1832 0.6655 0.089 Uiso 1 1 calc R . . . .
H00C H 0.5034 0.2049 0.6605 0.089 Uiso 1 1 calc R . . . .
C00T C 0.4658(2) 0.1096(2) 0.5770(2) 0.0947(11) Uani 1 1 d . . . . .
H00D H 0.5030 0.1264 0.5377 0.142 Uiso 1 1 calc GR . . . .
H00E H 0.4168 0.0942 0.5533 0.142 Uiso 1 1 calc GR . . . .
H00G H 0.4838 0.0520 0.6056 0.142 Uiso 1 1 calc GR . . . .


_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
F001 C00L 1.325(3) . ?
O002 C00E 1.324(2) . ?
O002 C00S 1.469(3) . ?
F003 C00L 1.336(3) . ?
F004 C00L 1.336(3) . ?
O005 C00E 1.202(2) . ?
O006 C00F 1.185(3) . ?
C007 C008 1.402(2) . ?
C007 C009 1.399(2) . ?
C007 C00E 1.506(2) . ?
C008 C00B 1.381(2) . ?
C008 C00L 1.502(3) . ?
C009 C00C 1.406(2) . ?
C009 C00D 1.493(2) . ?
C00A C00B 1.389(3) . ?
C00A C00C 1.396(2) . ?
C00A C00G 1.491(2) . ?
C00B H00B 0.9300 . ?
C00C C00F 1.500(2) . ?
C00D C00J 1.382(3) . ?
C00D C00K 1.387(3) . ?
C00F H00F 0.9300 . ?
C00G C00H 1.388(3) . ?
C00G C00I 1.394(3) . ?
C00H H00H 0.9300 . ?
C00H C00O 1.385(3) . ?
C00I H00I 0.9300 . ?
C00I C00M 1.387(3) . ?
C00J H00J 0.9300 . ?
C00J C00Q 1.386(3) . ?
C00K H00K 0.9300 . ?
C00K C00R 1.375(3) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.375(4) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.376(4) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.376(5) . ?
C00P C00R 1.371(4) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S H00A 0.9700 . ?
C00S H00C 0.9700 . ?
C00S C00T 1.483(5) . ?
C00T H00D 0.9600 . ?
C00T H00E 0.9600 . ?
C00T H00G 0.9600 . ?

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
C00E O002 C00S 116.23(18) . . ?
C008 C007 C00E 120.08(16) . . ?
C009 C007 C008 119.51(15) . . ?
C009 C007 C00E 120.39(16) . . ?
C007 C008 C00L 121.47(16) . . ?
C00B C008 C007 120.55(16) . . ?
C00B C008 C00L 117.97(16) . . ?
C007 C009 C00C 119.16(16) . . ?
C007 C009 C00D 119.86(15) . . ?
C00C C009 C00D 120.99(16) . . ?
C00B C00A C00C 119.04(16) . . ?
C00B C00A C00G 118.31(16) . . ?
C00C C00A C00G 122.61(16) . . ?
C008 C00B C00A 120.78(16) . . ?
C008 C00B H00B 119.6 . . ?
C00A C00B H00B 119.6 . . ?
C009 C00C C00F 120.68(16) . . ?
C00A C00C C009 120.94(16) . . ?
C00A C00C C00F 118.36(16) . . ?
C00J C00D C009 120.26(18) . . ?
C00J C00D C00K 119.00(19) . . ?
C00K C00D C009 120.73(18) . . ?
O002 C00E C007 111.97(15) . . ?
O005 C00E O002 125.08(18) . . ?
O005 C00E C007 122.92(18) . . ?
O006 C00F C00C 125.2(2) . . ?
O006 C00F H00F 117.4 . . ?
C00C C00F H00F 117.4 . . ?
C00H C00G C00A 120.08(16) . . ?
C00H C00G C00I 118.61(18) . . ?
C00I C00G C00A 121.23(18) . . ?
C00G C00H H00H 119.7 . . ?
C00O C00H C00G 120.6(2) . . ?
C00O C00H H00H 119.7 . . ?
C00G C00I H00I 119.7 . . ?
C00M C00I C00G 120.6(2) . . ?
C00M C00I H00I 119.7 . . ?
C00D C00J H00J 120.0 . . ?
C00D C00J C00Q 120.0(2) . . ?
C00Q C00J H00J 120.0 . . ?
C00D C00K H00K 119.8 . . ?
C00R C00K C00D 120.4(2) . . ?
C00R C00K H00K 119.8 . . ?
F001 C00L F003 106.72(18) . . ?
F001 C00L F004 105.57(19) . . ?
F001 C00L C008 112.52(16) . . ?
F003 C00L F004 106.23(18) . . ?
F003 C00L C008 112.55(18) . . ?
F004 C00L C008 112.71(18) . . ?
C00I C00M H00M 120.1 . . ?
C00N C00M C00I 119.9(2) . . ?
C00N C00M H00M 120.1 . . ?
C00M C00N H00N 119.9 . . ?
C00M C00N C00O 120.3(2) . . ?
C00O C00N H00N 119.9 . . ?
C00H C00O H00O 119.9 . . ?
C00N C00O C00H 120.1(2) . . ?
C00N C00O H00O 119.9 . . ?
C00Q C00P H00P 120.3 . . ?
C00R C00P H00P 120.3 . . ?
C00R C00P C00Q 119.4(2) . . ?
C00J C00Q H00Q 119.7 . . ?
C00P C00Q C00J 120.5(3) . . ?
C00P C00Q H00Q 119.7 . . ?
C00K C00R H00R 119.6 . . ?
C00P C00R C00K 120.7(2) . . ?
C00P C00R H00R 119.6 . . ?
O002 C00S H00A 109.4 . . ?
O002 C00S H00C 109.4 . . ?
O002 C00S C00T 111.3(2) . . ?
H00A C00S H00C 108.0 . . ?
C00T C00S H00A 109.4 . . ?
C00T C00S H00C 109.4 . . ?
C00S C00T H00D 109.5 . . ?
C00S C00T H00E 109.5 . . ?
C00S C00T H00G 109.5 . . ?
H00D C00T H00E 109.5 . . ?
H00D C00T H00G 109.5 . . ?
H00E C00T H00G 109.5 . . ?

_olex2_date_sample_data_collection 2018-01-19
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_yxq-zq-1206
_database_code_depnum_ccdc_archive 'CCDC 1898394'
loop_
_audit_author_name
_audit_author_address
'Bo Han'
;Chengdu University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-10-16 downloaded from the CCDC.
;
_audit_creation_date             2016-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 F3 N O2'
_chemical_formula_sum            'C17 H12 F3 N O2'
_chemical_formula_weight         319.28
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9917(5)
_cell_length_b                   8.3050(6)
_cell_length_c                   11.8750(7)
_cell_angle_alpha                107.623(6)
_cell_angle_beta                 97.098(5)
_cell_angle_gamma                91.682(5)
_cell_volume                     743.55(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2962
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.5320
_cell_measurement_theta_min      5.6280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.025
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_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       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6956
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.750
_diffrn_reflns_theta_min         5.593
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9726
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000 -180.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000 -150.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -77.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
  6 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -77.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  8 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -38.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
  9 omega   87.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 78

#__ type_ start__ end____ width___ exp.time_
 17 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 20 omega   41.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
 21 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 22 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 23 omega   39.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000    0.0000 138

#__ type_ start__ end____ width___ exp.time_
 24 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
 25 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
 26 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   38.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
 27 omega    9.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000   30.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1035881000
_diffrn_orient_matrix_UB_12      -0.1562989000
_diffrn_orient_matrix_UB_13      -0.0112277000
_diffrn_orient_matrix_UB_21      0.1455805000
_diffrn_orient_matrix_UB_22      0.1120485000
_diffrn_orient_matrix_UB_23      0.0889824000
_diffrn_orient_matrix_UB_31      -0.0774741000
_diffrn_orient_matrix_UB_32      -0.0330421000
_diffrn_orient_matrix_UB_33      0.1041583000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2509
_reflns_number_total             2880
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1050P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.1702
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00H(H00H), C00I(H00I), C00K(H00K),
 C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00N(H00F,H00G,H00J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
F001 F 0.34114(18) 0.3345(2) 0.69191(10) 0.0749(4) Uani 1 1 d . . . . .
F002 F 0.14162(17) 0.3405(2) 0.55984(12) 0.0795(5) Uani 1 1 d . . . . .
O003 O 0.7768(2) 0.38886(19) 0.69693(12) 0.0606(4) Uani 1 1 d . . . . .
F004 F 0.2184(2) 0.1032(2) 0.57393(15) 0.0951(6) Uani 1 1 d . . . . .
O005 O 0.6219(2) 0.1555(2) 0.68842(15) 0.0755(5) Uani 1 1 d . . . . .
C006 C 0.3373(2) 0.2292(2) 0.37245(15) 0.0413(4) Uani 1 1 d . . . . .
C007 C 0.4463(2) 0.2296(2) 0.28853(15) 0.0411(4) Uani 1 1 d . . . . .
C008 C 0.3995(2) 0.2521(2) 0.49246(15) 0.0427(4) Uani 1 1 d . . . . .
C009 C 0.3861(2) 0.1964(2) 0.15922(15) 0.0429(4) Uani 1 1 d . . . . .
C00A C 0.5732(2) 0.2743(2) 0.52885(15) 0.0439(4) Uani 1 1 d . . . . .
C00B C 0.6181(2) 0.2609(3) 0.32945(16) 0.0482(4) Uani 1 1 d . . . . .
H00B H 0.6927 0.2676 0.2765 0.058 Uiso 1 1 calc R . . . .
C00C C 0.6802(2) 0.2822(3) 0.44675(17) 0.0502(4) Uani 1 1 d . . . . .
H00C H 0.7960 0.3022 0.4715 0.060 Uiso 1 1 calc R . . . .
C00D C 0.2788(3) 0.0551(3) 0.09466(17) 0.0521(5) Uani 1 1 d . . . . .
H00D H 0.2402 -0.0181 0.1331 0.063 Uiso 1 1 calc R . . . .
C00E C 0.1581(2) 0.1983(3) 0.33193(16) 0.0541(5) Uani 1 1 d . . . . .
N00F N 0.0171(2) 0.1712(4) 0.29948(18) 0.0826(7) Uani 1 1 d . . . . .
C00G C 0.6556(3) 0.2660(2) 0.64763(16) 0.0501(4) Uani 1 1 d . . . . .
C00H C 0.4427(3) 0.3027(3) 0.09942(18) 0.0574(5) Uani 1 1 d . . . . .
H00H H 0.5147 0.3977 0.1410 0.069 Uiso 1 1 calc R . . . .
C00I C 0.2292(3) 0.0229(3) -0.02626(18) 0.0614(5) Uani 1 1 d . . . . .
H00I H 0.1571 -0.0718 -0.0686 0.074 Uiso 1 1 calc R . . . .
C00J C 0.2761(3) 0.2550(3) 0.57938(17) 0.0547(5) Uani 1 1 d . . . . .
C00K C 0.2855(3) 0.1294(3) -0.08445(18) 0.0638(6) Uani 1 1 d . . . . .
H00K H 0.2514 0.1077 -0.1657 0.077 Uiso 1 1 calc R . . . .
C00L C 0.3929(3) 0.2683(3) -0.02136(19) 0.0682(6) Uani 1 1 d . . . . .
H00L H 0.4324 0.3400 -0.0606 0.082 Uiso 1 1 calc R . . . .
C00M C 0.8826(4) 0.3744(4) 0.8029(2) 0.0765(7) Uani 1 1 d . . . . .
H00A H 0.9405 0.2705 0.7826 0.092 Uiso 1 1 calc R . . . .
H00E H 0.8132 0.3718 0.8639 0.092 Uiso 1 1 calc R . . . .
C00N C 1.0069(3) 0.5219(4) 0.8476(2) 0.0792(7) Uani 1 1 d . . . . .
H00F H 1.0607 0.5355 0.7828 0.119 Uiso 1 1 calc GR . . . .
H00G H 1.0905 0.5044 0.9073 0.119 Uiso 1 1 calc GR . . . .
H00J H 0.9503 0.6218 0.8818 0.119 Uiso 1 1 calc GR . . . .


_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
F001 C00J 1.329(2) . ?
F002 C00J 1.340(3) . ?
O003 C00G 1.327(2) . ?
O003 C00M 1.466(2) . ?
F004 C00J 1.310(2) . ?
O005 C00G 1.199(2) . ?
C006 C007 1.403(2) . ?
C006 C008 1.403(2) . ?
C006 C00E 1.443(2) . ?
C007 C009 1.490(2) . ?
C007 C00B 1.388(3) . ?
C008 C00A 1.391(3) . ?
C008 C00J 1.509(3) . ?
C009 C00D 1.390(3) . ?
C009 C00H 1.387(3) . ?
C00A C00C 1.389(3) . ?
C00A C00G 1.503(2) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.376(3) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00I 1.382(3) . ?
C00E N00F 1.137(3) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.379(3) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.374(3) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.374(3) . ?
C00L H00L 0.9300 . ?
C00M H00A 0.9700 . ?
C00M H00E 0.9700 . ?
C00M C00N 1.474(4) . ?
C00N H00F 0.9600 . ?
C00N H00G 0.9600 . ?
C00N H00J 0.9600 . ?

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
C00G O003 C00M 115.32(17) . . ?
C007 C006 C008 121.44(15) . . ?
C007 C006 C00E 118.44(15) . . ?
C008 C006 C00E 120.08(15) . . ?
C006 C007 C009 123.10(15) . . ?
C00B C007 C006 117.55(16) . . ?
C00B C007 C009 119.35(15) . . ?
C006 C008 C00J 119.11(16) . . ?
C00A C008 C006 119.31(15) . . ?
C00A C008 C00J 121.58(16) . . ?
C00D C009 C007 121.20(16) . . ?
C00H C009 C007 120.21(16) . . ?
C00H C009 C00D 118.53(17) . . ?
C008 C00A C00G 123.81(16) . . ?
C00C C00A C008 119.04(16) . . ?
C00C C00A C00G 116.57(16) . . ?
C007 C00B H00B 119.4 . . ?
C00C C00B C007 121.29(17) . . ?
C00C C00B H00B 119.4 . . ?
C00A C00C H00C 119.4 . . ?
C00B C00C C00A 121.22(17) . . ?
C00B C00C H00C 119.4 . . ?
C009 C00D H00D 119.8 . . ?
C00I C00D C009 120.42(19) . . ?
C00I C00D H00D 119.8 . . ?
N00F C00E C006 178.9(3) . . ?
O003 C00G C00A 111.64(15) . . ?
O005 C00G O003 124.67(18) . . ?
O005 C00G C00A 123.54(18) . . ?
C009 C00H H00H 119.8 . . ?
C00L C00H C009 120.38(19) . . ?
C00L C00H H00H 119.8 . . ?
C00D C00I H00I 119.7 . . ?
C00K C00I C00D 120.5(2) . . ?
C00K C00I H00I 119.7 . . ?
F001 C00J F002 104.28(17) . . ?
F001 C00J C008 112.94(17) . . ?
F002 C00J C008 111.71(16) . . ?
F004 C00J F001 107.61(18) . . ?
F004 C00J F002 106.93(19) . . ?
F004 C00J C008 112.82(17) . . ?
C00I C00K H00K 120.3 . . ?
C00L C00K C00I 119.31(19) . . ?
C00L C00K H00K 120.3 . . ?
C00H C00L H00L 119.6 . . ?
C00K C00L C00H 120.8(2) . . ?
C00K C00L H00L 119.6 . . ?
O003 C00M H00A 110.1 . . ?
O003 C00M H00E 110.1 . . ?
O003 C00M C00N 108.2(2) . . ?
H00A C00M H00E 108.4 . . ?
C00N C00M H00A 110.1 . . ?
C00N C00M H00E 110.1 . . ?
C00M C00N H00F 109.5 . . ?
C00M C00N H00G 109.5 . . ?
C00M C00N H00J 109.5 . . ?
H00F C00N H00G 109.5 . . ?
H00F C00N H00J 109.5 . . ?
H00G C00N H00J 109.5 . . ?

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
C006 C007 C009 C00D -50.7(2) . . . . ?
C006 C007 C009 C00H 132.2(2) . . . . ?
C006 C007 C00B C00C 3.2(3) . . . . ?
C006 C008 C00A C00C 3.4(3) . . . . ?
C006 C008 C00A C00G -167.63(16) . . . . ?
C006 C008 C00J F001 -157.59(17) . . . . ?
C006 C008 C00J F002 -40.4(2) . . . . ?
C006 C008 C00J F004 80.1(2) . . . . ?
C007 C006 C008 C00A -0.6(3) . . . . ?
C007 C006 C008 C00J 178.43(16) . . . . ?
C007 C009 C00D C00I -177.59(18) . . . . ?
C007 C009 C00H C00L 177.2(2) . . . . ?
C007 C00B C00C C00A -0.4(3) . . . . ?
C008 C006 C007 C009 176.54(16) . . . . ?
C008 C006 C007 C00B -2.7(3) . . . . ?
C008 C00A C00C C00B -3.0(3) . . . . ?
C008 C00A C00G O003 -136.87(19) . . . . ?
C008 C00A C00G O005 47.3(3) . . . . ?
C009 C007 C00B C00C -176.06(17) . . . . ?
C009 C00D C00I C00K 0.2(3) . . . . ?
C009 C00H C00L C00K 0.5(4) . . . . ?
C00A C008 C00J F001 21.4(3) . . . . ?
C00A C008 C00J F002 138.57(18) . . . . ?
C00A C008 C00J F004 -100.9(2) . . . . ?
C00B C007 C009 C00D 128.5(2) . . . . ?
C00B C007 C009 C00H -48.5(3) . . . . ?
C00C C00A C00G O003 51.9(2) . . . . ?
C00C C00A C00G O005 -123.9(2) . . . . ?
C00D C009 C00H C00L 0.1(3) . . . . ?
C00D C00I C00K C00L 0.4(4) . . . . ?
C00E C006 C007 C009 -1.2(3) . . . . ?
C00E C006 C007 C00B 179.51(17) . . . . ?
C00E C006 C008 C00A 177.15(17) . . . . ?
C00E C006 C008 C00J -3.8(3) . . . . ?
C00G O003 C00M C00N -178.6(2) . . . . ?
C00G C00A C00C C00B 168.71(18) . . . . ?
C00H C009 C00D C00I -0.5(3) . . . . ?
C00I C00K C00L C00H -0.8(4) . . . . ?
C00J C008 C00A C00C -175.56(18) . . . . ?
C00J C008 C00A C00G 13.4(3) . . . . ?
C00M O003 C00G O005 5.5(3) . . . . ?
C00M O003 C00G C00A -170.26(19) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_date_sample_data_collection 2016-12-07
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_lq-hb-zq-02061
_database_code_depnum_ccdc_archive 'CCDC 1898393'
loop_
_audit_author_name
_audit_author_address
'Bo Han'
;Chengdu University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-10-16 downloaded from the CCDC.
;
_audit_creation_date             2018-01-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 Br N O2'
_chemical_formula_sum            'C22 H15 Br N O2'
_chemical_formula_weight         405.26
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.8840(6)
_cell_length_b                   7.2300(2)
_cell_length_c                   32.8613(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.675(3)
_cell_angle_gamma                90
_cell_volume                     3773.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4245
_cell_measurement_temperature    292.4(5)
_cell_measurement_theta_max      72.3090
_cell_measurement_theta_min      5.3720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            10640
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.534
_diffrn_reflns_theta_min         5.385
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.4(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000   60.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   98.00   1.0000    3.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega  100.00  178.00   1.0000    3.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  109.00   1.0000    3.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000    3.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   91.00   1.0000    3.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00   98.00   1.0000    3.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   98.00   1.0000    3.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 14 omega   41.00  126.00   1.0000    3.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00  177.00   1.0000    3.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  120.0000 138

#__ type_ start__ end____ width___ exp.time_
 16 omega  -33.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -38.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
 17 omega   18.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   38.0000  -60.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0810389000
_diffrn_orient_matrix_UB_12      0.0795430000
_diffrn_orient_matrix_UB_13      -0.0184419000
_diffrn_orient_matrix_UB_21      -0.0352519000
_diffrn_orient_matrix_UB_22      -0.0366985000
_diffrn_orient_matrix_UB_23      -0.0431493000
_diffrn_orient_matrix_UB_31      -0.0397794000
_diffrn_orient_matrix_UB_32      0.1942416000
_diffrn_orient_matrix_UB_33      -0.0005976000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3126
_reflns_number_total             3658
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1151P)²+1.7496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1688
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C5(H5), C1(H1), C19(H19), C2(H2), C15(H15), C18(H18),
 C17(H17), C16(H16), C21(H21)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.61815(3) 1.30356(5) 0.51970(2) 0.0798(2) Uani 1 1 d . . . . .
O2 O 0.59558(15) 0.0557(3) 0.32001(8) 0.0719(7) Uani 1 1 d . . . . .
O1 O 0.5159(2) 0.2441(5) 0.28385(9) 0.0993(11) Uani 1 1 d . . . . .
C11 C 0.65113(15) 0.3884(4) 0.36424(8) 0.0459(5) Uani 1 1 d . . . . .
N1 N 0.80606(16) 0.6163(4) 0.41894(10) 0.0689(7) Uani 1 1 d . . . . .
C12 C 0.65738(15) 0.5318(4) 0.39278(8) 0.0467(5) Uani 1 1 d . . . . .
C14 C 0.72757(16) 0.2804(4) 0.35300(9) 0.0485(6) Uani 1 1 d . . . . .
C13 C 0.74040(17) 0.5798(4) 0.40824(9) 0.0518(6) Uani 1 1 d . . . . .
C7 C 0.58726(17) 0.6397(4) 0.40431(8) 0.0501(6) Uani 1 1 d . . . . .
C6 C 0.59369(17) 0.7960(4) 0.43264(9) 0.0494(6) Uani 1 1 d . . . . .
C10 C 0.57307(16) 0.3544(4) 0.34564(8) 0.0491(6) Uani 1 1 d . . . . .
C4 C 0.5618(2) 1.1140(4) 0.44850(10) 0.0596(7) Uani 1 1 d . . . . .
H4 H 0.5370 1.2261 0.4413 0.072 Uiso 1 1 calc R . . . .
C8 C 0.50999(18) 0.5969(5) 0.38553(10) 0.0583(7) Uani 1 1 d . . . . .
H8 H 0.4621 0.6626 0.3927 0.070 Uiso 1 1 calc R . . . .
C9 C 0.50362(17) 0.4606(5) 0.35686(10) 0.0580(7) Uani 1 1 d . . . . .
H9 H 0.4517 0.4379 0.3445 0.070 Uiso 1 1 calc R . . . .
C20 C 0.55944(18) 0.2144(4) 0.31290(9) 0.0543(7) Uani 1 1 d . . . . .
C5 C 0.55581(19) 0.9636(4) 0.42277(9) 0.0573(7) Uani 1 1 d . . . . .
H5 H 0.5259 0.9746 0.3984 0.069 Uiso 1 1 calc R . . . .
C1 C 0.6350(2) 0.7825(4) 0.47027(9) 0.0575(7) Uani 1 1 d . . . . .
H1 H 0.6591 0.6704 0.4779 0.069 Uiso 1 1 calc R . . . .
C19 C 0.76050(18) 0.1489(5) 0.37935(11) 0.0615(7) Uani 1 1 d . . . . .
H19 H 0.7369 0.1328 0.4049 0.074 Uiso 1 1 calc R . . . .
C3 C 0.60481(19) 1.0965(4) 0.48485(9) 0.0581(7) Uani 1 1 d . . . . .
C2 C 0.6408(2) 0.9302(5) 0.49617(10) 0.0630(7) Uani 1 1 d . . . . .
H2 H 0.6687 0.9188 0.5211 0.076 Uiso 1 1 calc R . . . .
C15 C 0.7650(2) 0.3057(5) 0.31574(12) 0.0692(9) Uani 1 1 d . . . . .
H15 H 0.7444 0.3951 0.2979 0.083 Uiso 1 1 calc R . . . .
C18 C 0.8281(2) 0.0417(5) 0.36800(15) 0.0779(11) Uani 1 1 d . . . . .
H18 H 0.8491 -0.0477 0.3857 0.093 Uiso 1 1 calc R . . . .
C17 C 0.8640(2) 0.0656(6) 0.33141(15) 0.0844(12) Uani 1 1 d . . . . .
H17 H 0.9095 -0.0071 0.3240 0.101 Uiso 1 1 calc R . . . .
C16 C 0.8330(3) 0.1980(6) 0.30498(15) 0.0877(13) Uani 1 1 d . . . . .
H16 H 0.8581 0.2149 0.2798 0.105 Uiso 1 1 calc R . . . .
C21 C 0.5864(3) -0.0857(7) 0.28873(17) 0.1082(18) Uani 1 1 d . . . . .
H21 H 0.5385 -0.1004 0.2725 0.130 Uiso 1 1 calc R . . . .
C22 C 0.6567(4) -0.1945(9) 0.2860(2) 0.131(3) Uani 1 1 d . . . . .
H22A H 0.7013 -0.1251 0.2737 0.197 Uiso 1 1 calc GR . . . .
H22B H 0.6441 -0.3011 0.2696 0.197 Uiso 1 1 calc GR . . . .
H22C H 0.6741 -0.2334 0.3127 0.197 Uiso 1 1 calc GR . . . .


_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 C3 1.895(3) . ?
O2 C20 1.303(4) . ?
O2 C21 1.455(4) . ?
O1 C20 1.191(4) . ?
C11 C12 1.401(4) . ?
C11 C14 1.494(4) . ?
C11 C10 1.398(4) . ?
N1 C13 1.128(4) . ?
C12 C13 1.450(4) . ?
C12 C7 1.415(4) . ?
C14 C19 1.384(4) . ?
C14 C15 1.379(5) . ?
C7 C6 1.467(4) . ?
C7 C8 1.402(4) . ?
C6 C5 1.390(4) . ?
C6 C1 1.396(4) . ?
C10 C9 1.397(4) . ?
C10 C20 1.491(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(5) . ?
C4 C3 1.375(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.366(4) . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.368(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.379(5) . ?
C3 C2 1.380(5) . ?
C2 H2 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.382(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.348(6) . ?
C17 H17 0.9300 . ?
C17 C16 1.379(7) . ?
C16 H16 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.370(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
C20 O2 C21 116.8(3) . . ?
C12 C11 C14 120.1(2) . . ?
C10 C11 C12 118.6(2) . . ?
C10 C11 C14 121.3(2) . . ?
C11 C12 C13 118.0(2) . . ?
C11 C12 C7 122.5(2) . . ?
C7 C12 C13 119.3(3) . . ?
C19 C14 C11 120.4(3) . . ?
C15 C14 C11 120.7(3) . . ?
C15 C14 C19 118.9(3) . . ?
N1 C13 C12 177.6(3) . . ?
C12 C7 C6 123.1(2) . . ?
C8 C7 C12 116.6(3) . . ?
C8 C7 C6 120.2(3) . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 C1 117.7(3) . . ?
C1 C6 C7 122.4(3) . . ?
C11 C10 C20 123.7(3) . . ?
C9 C10 C11 119.1(3) . . ?
C9 C10 C20 117.1(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 H8 119.3 . . ?
C10 C9 H9 119.1 . . ?
C8 C9 C10 121.7(3) . . ?
C8 C9 H9 119.1 . . ?
O2 C20 C10 114.1(2) . . ?
O1 C20 O2 123.6(3) . . ?
O1 C20 C10 122.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C1 H1 119.2 . . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 H1 119.2 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C4 C3 Br1 120.2(2) . . ?
C4 C3 C2 121.0(3) . . ?
C2 C3 Br1 118.8(2) . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.9(4) . . ?
C16 C15 H15 120.0 . . ?
C19 C18 H18 119.7 . . ?
C17 C18 C19 120.5(4) . . ?
C17 C18 H18 119.7 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.9 . . ?
O2 C21 H21 124.0 . . ?
C22 C21 O2 112.0(4) . . ?
C22 C21 H21 124.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
