# Electronic Supplementary Material (ESI) for ChemComm.
# 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_201805262
_database_code_depnum_ccdc_archive 'CCDC 1915398'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Jiang'
;Henan University
China
;
_audit_update_record             
;
2019-05-11 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_audit_creation_date             2018-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 F N2 O4 S'
_chemical_formula_sum            'C23 H21 F N2 O4 S'
_chemical_formula_weight         440.48
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N3S1
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'
S S 0.3331 0.5567 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.17133(16)
_cell_length_b                   14.8909(5)
_cell_length_c                   22.8926(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2103.76(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2453
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9230
_cell_measurement_theta_min      3.8810
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.781
_exptl_absorpt_coefficient_mu    1.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73612
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7878
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.958
_diffrn_reflns_theta_min         3.541
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -15.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -180.0000 174

#__ type_ start__ end____ width___ exp.time_
  2 omega -105.00  -73.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega    7.00   33.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
  4 omega  -52.00  -21.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   30.0000 62

#__ type_ start__ end____ width___ exp.time_
  5 omega   26.00   74.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 96

#__ type_ start__ end____ width___ exp.time_
  6 omega   -4.00   22.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
  7 omega  -32.00   12.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -60.0000 88

#__ type_ start__ end____ width___ exp.time_
  8 omega   20.00  107.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  120.0000 174

#__ type_ start__ end____ width___ exp.time_
  9 omega   57.00   82.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
 10 omega   60.00  106.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 92

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   68.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
 12 omega   48.00   84.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
 13 omega   46.00   92.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
 14 omega  118.00  175.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 114

#__ type_ start__ end____ width___ exp.time_
 15 omega   38.00  138.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 200

#__ type_ start__ end____ width___ exp.time_
 16 omega   42.00   84.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00  101.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 120

#__ type_ start__ end____ width___ exp.time_
 18 omega   53.00   80.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0088367000
_diffrn_orient_matrix_UB_12      -0.0553560000
_diffrn_orient_matrix_UB_13      -0.0567952000
_diffrn_orient_matrix_UB_21      -0.0120171000
_diffrn_orient_matrix_UB_22      0.0873764000
_diffrn_orient_matrix_UB_23      -0.0359004000
_diffrn_orient_matrix_UB_31      0.2491678000
_diffrn_orient_matrix_UB_32      0.0022761000
_diffrn_orient_matrix_UB_33      -0.0037911000
_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         0.706
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3123
_reflns_number_total             3984
_reflns_odcompleteness_completeness 99.86
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.074
_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)+(0.0386P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1137
_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. Restrained distances
 C12A-C11A
 1.38 with sigma of 0.02
 C13A-C12A
 1.38 with sigma of 0.02
 C11-S1
 1.6 with sigma of 0.02
 N2-H2A
 0.87 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C14) \\sim Ueq, Uanis(C14A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(C14) = Uanis(C14A)
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
Uanis(F1) = Uanis(F1A)
Uanis(C11) = Uanis(C11A)
4. Others
 Sof(C14A)=Sof(C13A)=Sof(H13A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(C16A)=
 Sof(H16A)=Sof(C15A)=Sof(H15A)=Sof(F1A)=1-FVAR(1)
 Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(C15)=Sof(H15)=
 Sof(C16)=Sof(H16)=Sof(F1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C13A(H13A), C12A(H12A),
 C16A(H16A), C15A(H15A), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21),
 C22(H22)
5.c Fitted hexagon refined as free rotating group:
 C14A(C13A,C12A,C11A,C16A,C15A)
5.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C -0.0603(8) 0.4713(3) 0.2132(2) 0.0591(12) Uani 1 1 d . . . . .
H1 H -0.0698 0.4134 0.1984 0.071 Uiso 1 1 calc R . . . .
C2 C -0.1989(8) 0.5381(4) 0.1935(2) 0.0687(15) Uani 1 1 d . . . . .
H2 H -0.2991 0.5253 0.1643 0.082 Uiso 1 1 calc R . . . .
C3 C -0.1889(8) 0.6228(4) 0.2168(2) 0.0656(14) Uani 1 1 d . . . . .
H3 H -0.2869 0.6661 0.2041 0.079 Uiso 1 1 calc R . . . .
C4 C -0.0369(8) 0.6455(3) 0.2585(2) 0.0564(12) Uani 1 1 d . . . . .
H4 H -0.0301 0.7032 0.2738 0.068 Uiso 1 1 calc R . . . .
C5 C 0.1047(6) 0.5793(3) 0.27660(18) 0.0438(10) Uani 1 1 d . . . . .
C6 C 0.0908(6) 0.4920(3) 0.25496(17) 0.0452(10) Uani 1 1 d . . . . .
C7 C 0.2508(7) 0.4322(3) 0.28496(18) 0.0441(9) Uani 1 1 d . . . . .
C8 C 0.3801(7) 0.4983(3) 0.32166(18) 0.0479(10) Uani 1 1 d . . . . .
C9 C 0.1353(8) 0.3694(3) 0.32851(19) 0.0523(11) Uani 1 1 d . . . . .
H9A H 0.0342 0.3315 0.3074 0.063 Uiso 1 1 calc R . . . .
H9B H 0.2417 0.3308 0.3470 0.063 Uiso 1 1 calc R . . . .
C10 C 0.3948(8) 0.3768(3) 0.2443(2) 0.0635(13) Uani 1 1 d . . . . .
H10A H 0.4629 0.4157 0.2164 0.095 Uiso 1 1 calc GR . . . .
H10B H 0.3079 0.3332 0.2242 0.095 Uiso 1 1 calc GR . . . .
H10C H 0.5039 0.3466 0.2669 0.095 Uiso 1 1 calc GR . . . .
C11 C 0.254(5) 0.643(3) 0.4280(11) 0.0539(14) Uani 0.61(2) 1 d D . P A 1
C12 C 0.400(4) 0.601(3) 0.4648(14) 0.071(3) Uani 0.61(2) 1 d . . P A 1
H12 H 0.5384 0.5870 0.4515 0.085 Uiso 0.61(2) 1 calc R . P A 1
C13 C 0.339(3) 0.5799(19) 0.5217(10) 0.081(4) Uani 0.61(2) 1 d . . P A 1
H13 H 0.4328 0.5504 0.5471 0.097 Uiso 0.61(2) 1 calc R . P A 1
C14 C 0.138(3) 0.6039(11) 0.5383(6) 0.076(3) Uani 0.61(2) 1 d . U P A 1
C14A C 0.055(4) 0.6186(17) 0.5314(9) 0.076(3) Uani 0.39(2) 1 d . U P A 2
C13A C 0.262(5) 0.584(3) 0.5221(16) 0.081(4) Uani 0.39(2) 1 d DG . P A 2
H13A H 0.3310 0.5521 0.5515 0.097 Uiso 0.39(2) 1 calc R . P A 2
C12A C 0.365(6) 0.598(5) 0.469(2) 0.071(3) Uani 0.39(2) 1 d DG . P A 2
H12A H 0.5036 0.5755 0.4628 0.085 Uiso 0.39(2) 1 calc R . P A 2
C11A C 0.262(8) 0.647(4) 0.4251(16) 0.0539(14) Uani 0.39(2) 1 d DG . P A 2
C16A C 0.055(7) 0.681(3) 0.4344(10) 0.065(3) Uani 0.39(2) 1 d G . P A 2
H16A H -0.0137 0.7132 0.4050 0.078 Uiso 0.39(2) 1 calc R . P A 2
C15A C -0.048(4) 0.6669(17) 0.4875(11) 0.079(4) Uani 0.39(2) 1 d G . P A 2
H15A H -0.1863 0.6898 0.4937 0.094 Uiso 0.39(2) 1 calc R . P A 2
C15 C -0.009(3) 0.6441(12) 0.5040(8) 0.079(4) Uani 0.61(2) 1 d . U P A 1
H15 H -0.1462 0.6581 0.5182 0.094 Uiso 0.61(2) 1 calc R . P A 1
C16 C 0.049(4) 0.6643(16) 0.4466(7) 0.065(3) Uani 0.61(2) 1 d . U P A 1
H16 H -0.0493 0.6916 0.4214 0.078 Uiso 0.61(2) 1 calc R . P A 1
C17 C 0.0273(7) 0.3933(3) 0.43208(18) 0.0433(9) Uani 1 1 d . . . . .
C18 C 0.2097(7) 0.3555(3) 0.45706(19) 0.0528(11) Uani 1 1 d . . . . .
H18 H 0.3313 0.3446 0.4342 0.063 Uiso 1 1 calc R . . . .
C19 C 0.2130(7) 0.3337(3) 0.51611(19) 0.0518(11) Uani 1 1 d . . . . .
H19 H 0.3355 0.3068 0.5321 0.062 Uiso 1 1 calc R . . . .
C20 C 0.0376(7) 0.3513(3) 0.55108(18) 0.0494(10) Uani 1 1 d . . . . .
C21 C -0.1436(7) 0.3894(3) 0.5264(2) 0.0550(12) Uani 1 1 d . . . . .
H21 H -0.2642 0.4009 0.5496 0.066 Uiso 1 1 calc R . . . .
C22 C -0.1492(7) 0.4107(3) 0.46796(19) 0.0494(10) Uani 1 1 d . . . . .
H22 H -0.2728 0.4371 0.4523 0.059 Uiso 1 1 calc R . . . .
C23 C 0.2133(9) 0.3049(5) 0.6378(2) 0.092(2) Uani 1 1 d . . . . .
H23A H 0.1836 0.2948 0.6784 0.138 Uiso 1 1 calc GR . . . .
H23B H 0.3196 0.3516 0.6340 0.138 Uiso 1 1 calc GR . . . .
H23C H 0.2676 0.2507 0.6205 0.138 Uiso 1 1 calc GR . . . .
F1 F 0.073(3) 0.5841(13) 0.5951(6) 0.127(5) Uani 0.61(2) 1 d . U P A 1
F1A F -0.036(5) 0.603(2) 0.5813(10) 0.127(5) Uani 0.39(2) 1 d . . P A 2
N1 N 0.2864(6) 0.5839(2) 0.31559(16) 0.0480(9) Uani 1 1 d . . . . .
N2 N 0.0197(7) 0.4189(3) 0.37291(17) 0.0534(10) Uani 1 1 d D . . . .
H2A H -0.102(5) 0.438(3) 0.3628(19) 0.046(13) Uiso 1 1 d D . . . .
O1 O 0.5322(5) 0.4812(2) 0.35306(15) 0.0660(9) Uani 1 1 d . . . . .
O2 O 0.5845(5) 0.6738(3) 0.36042(17) 0.0826(12) Uani 1 1 d . . . . .
O3 O 0.2393(7) 0.7468(2) 0.33562(18) 0.0854(13) Uani 1 1 d . . . . .
O4 O 0.0242(6) 0.3305(3) 0.60964(13) 0.0703(10) Uani 1 1 d . . . . .
S1 S 0.3570(2) 0.67185(8) 0.35767(6) 0.0578(3) Uani 1 1 d 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 H1 0.9300 . ?
C1 C2 1.387(7) . ?
C1 C6 1.369(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(6) . ?
C5 C6 1.394(6) . ?
C5 N1 1.434(5) . ?
C6 C7 1.496(6) . ?
C7 C8 1.520(6) . ?
C7 C9 1.542(6) . ?
C7 C10 1.528(6) . ?
C8 N1 1.406(5) . ?
C8 O1 1.209(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 N2 1.444(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.382(12) . ?
C11 C16 1.371(12) . ?
C11 S1 1.785(14) . ?
C12 H12 0.9300 . ?
C12 C13 1.393(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.344(17) . ?
C14 C15 1.342(15) . ?
C14 F1 1.393(18) . ?
C14A C13A 1.3900 . ?
C14A C15A 1.3900 . ?
C14A F1A 1.29(3) . ?
C13A H13A 0.9300 . ?
C13A C12A 1.3900 . ?
C12A H12A 0.9300 . ?
C12A C11A 1.3900 . ?
C11A C16A 1.3900 . ?
C11A S1 1.69(2) . ?
C16A H16A 0.9300 . ?
C16A C15A 1.3900 . ?
C15A H15A 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.396(14) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(6) . ?
C17 C22 1.389(6) . ?
C17 N2 1.408(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(6) . ?
C20 C21 1.375(6) . ?
C20 O4 1.378(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(6) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 O4 1.387(6) . ?
N1 S1 1.684(4) . ?
N2 H2A 0.84(2) . ?
O2 S1 1.405(3) . ?
O3 S1 1.424(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 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
C6 C1 C2 119.1(5) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(5) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.6(5) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.6(5) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 N1 130.4(4) . . ?
C6 C5 N1 108.3(4) . . ?
C1 C6 C5 119.9(4) . . ?
C1 C6 C7 129.5(4) . . ?
C5 C6 C7 110.5(4) . . ?
C6 C7 C8 102.4(3) . . ?
C6 C7 C9 110.6(3) . . ?
C6 C7 C10 115.2(4) . . ?
C8 C7 C9 106.1(3) . . ?
C8 C7 C10 112.4(4) . . ?
C10 C7 C9 109.5(4) . . ?
N1 C8 C7 108.4(3) . . ?
O1 C8 C7 126.8(4) . . ?
O1 C8 N1 124.7(4) . . ?
C7 C9 H9A 109.2 . . ?
C7 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N2 C9 C7 111.9(3) . . ?
N2 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 S1 115.2(17) . . ?
C16 C11 C12 121.2(8) . . ?
C16 C11 S1 123.5(17) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.7(10) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 121.5 . . ?
C14 C13 C12 116.9(11) . . ?
C14 C13 H13 121.5 . . ?
C13 C14 F1 118.3(13) . . ?
C15 C14 C13 125.3(11) . . ?
C15 C14 F1 116.4(12) . . ?
C13A C14A C15A 120.0 . . ?
F1A C14A C13A 118(2) . . ?
F1A C14A C15A 122(2) . . ?
C14A C13A H13A 120.0 . . ?
C14A C13A C12A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A C13A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C11A S1 128(3) . . ?
C16A C11A C12A 120.0 . . ?
C16A C11A S1 112(3) . . ?
C11A C16A H16A 120.0 . . ?
C15A C16A C11A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C14 C15 H15 120.9 . . ?
C14 C15 C16 118.3(10) . . ?
C16 C15 H15 120.9 . . ?
C11 C16 C15 118.5(10) . . ?
C11 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C18 C17 C22 118.0(4) . . ?
C18 C17 N2 122.4(4) . . ?
C22 C17 N2 119.5(4) . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.6(4) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.7(4) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C21 118.7(4) . . ?
C19 C20 O4 124.9(4) . . ?
C21 C20 O4 116.3(4) . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.0(4) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.8(4) . . ?
C21 C22 H22 119.6 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
C5 N1 S1 126.6(3) . . ?
C8 N1 C5 109.9(3) . . ?
C8 N1 S1 122.8(3) . . ?
C9 N2 H2A 115(3) . . ?
C17 N2 C9 121.5(4) . . ?
C17 N2 H2A 113(3) . . ?
C20 O4 C23 117.6(4) . . ?
N1 S1 C11 103.7(15) . . ?
N1 S1 C11A 105(2) . . ?
O2 S1 C11 108.7(11) . . ?
O2 S1 C11A 108.0(18) . . ?
O2 S1 N1 107.5(2) . . ?
O2 S1 O3 120.7(3) . . ?
O3 S1 C11 109.1(10) . . ?
O3 S1 C11A 108.7(17) . . ?
O3 S1 N1 105.9(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O3 0.93 2.28 2.881(6) 122.1 .
N2 H2A O1 0.84(2) 2.35(3) 3.181(5) 168(4) 1_455

_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_zgk22075a
_database_code_depnum_ccdc_archive 'CCDC 1915399'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Jiang'
;Henan University
China
;
_audit_update_record             
;
2019-05-11 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_audit_creation_date             2018-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C24 H20 Br F3 N2 O2), H2 O'
_chemical_formula_sum            'C48 H42 Br2 F6 N4 O5'
_chemical_formula_weight         1028.67
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N2F3Br1
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'

_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   26.455(2)
_cell_length_b                   6.3246(2)
_cell_length_c                   14.0068(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.467(9)
_cell_angle_gamma                90
_cell_volume                     2209.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.7970
_cell_measurement_theta_min      5.6200
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.679
_exptl_absorpt_coefficient_mu    3.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80800
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5109
_diffrn_reflns_point_group_measured_fraction_full 0.737
_diffrn_reflns_point_group_measured_fraction_max 0.718
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.764
_diffrn_reflns_theta_min         3.347
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -104.00  -11.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000  -30.0000 186

#__ type_ start__ end____ width___ exp.time_
  2 omega  -68.00  -41.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega  -99.00  -25.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   90.0000 148

#__ type_ start__ end____ width___ exp.time_
  4 omega   50.00   75.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
  5 omega   58.00   85.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -126.0000   76.0000 54

#__ type_ start__ end____ width___ exp.time_
  6 omega   79.00  109.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega   -1.00   65.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 132

#__ type_ start__ end____ width___ exp.time_
  8 omega   57.00   92.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00  101.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  120.0000 116

#__ type_ start__ end____ width___ exp.time_
 10 omega    2.00   38.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  150.0000 72

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   73.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
 12 omega  111.00  167.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
 13 omega   43.00  108.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 130

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00   86.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 88

#__ type_ start__ end____ width___ exp.time_
 15 omega   38.00   90.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 104

#__ type_ start__ end____ width___ exp.time_
 16 omega   48.00   90.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
 17 omega   94.00  156.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 124

#__ type_ start__ end____ width___ exp.time_
 18 omega   47.00   85.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 76

#__ type_ start__ end____ width___ exp.time_
 19 omega   61.00  109.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
 20 omega  104.00  177.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 146

#__ type_ start__ end____ width___ exp.time_
 21 omega  -65.00  -39.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 22 omega  -60.00  -26.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  150.0000 68

#__ type_ start__ end____ width___ exp.time_
 23 omega   23.00   49.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 24 omega   73.00   99.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 25 omega   -8.00   -7.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  106.0000   68.0072 2
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0254781000
_diffrn_orient_matrix_UB_12      -0.0131809000
_diffrn_orient_matrix_UB_13      -0.0840061000
_diffrn_orient_matrix_UB_21      -0.0559431000
_diffrn_orient_matrix_UB_22      0.0173970000
_diffrn_orient_matrix_UB_23      -0.0808803000
_diffrn_orient_matrix_UB_31      0.0052995000
_diffrn_orient_matrix_UB_32      0.2427336000
_diffrn_orient_matrix_UB_33      0.0011786000
_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         0.334
_reflns_Friedel_fraction_full    0.417
_reflns_Friedel_fraction_max     0.398
_reflns_number_gt                2726
_reflns_number_total             3058
_reflns_odcompleteness_completeness 99.91
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 627 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.067
_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)+(0.0620P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1114
_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, All O(H) groups
2. Restrained distances
 N2-H2
 0.87 with sigma of 0.02
3.a Free rotating group:
 O3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C21(H21)
3.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.36504(3) 0.38463(10) 0.55548(5) 0.0623(2) Uani 1 1 d . . . . .
C1 C 0.3990(2) 0.8100(9) 0.2256(4) 0.0408(12) Uani 1 1 d . . . . .
C2 C 0.3761(2) 0.9663(8) 0.2857(4) 0.0374(11) Uani 1 1 d . . . . .
C3 C 0.3467(2) 1.1208(9) 0.2037(4) 0.0400(11) Uani 1 1 d . . . . .
C4 C 0.3532(2) 1.0605(10) 0.1130(4) 0.0419(12) Uani 1 1 d . . . . .
C5 C 0.3311(3) 1.1741(11) 0.0251(5) 0.0532(15) Uani 1 1 d . . . . .
H5 H 0.3356 1.1323 -0.0352 0.064 Uiso 1 1 calc R . . . .
C6 C 0.3021(3) 1.3526(12) 0.0300(5) 0.0621(18) Uani 1 1 d . . . . .
H6 H 0.2865 1.4316 -0.0284 0.075 Uiso 1 1 calc R . . . .
C7 C 0.2954(2) 1.4175(12) 0.1196(5) 0.0634(18) Uani 1 1 d . . . . .
H7 H 0.2756 1.5384 0.1207 0.076 Uiso 1 1 calc R . . . .
C8 C 0.3184(2) 1.3017(9) 0.2076(5) 0.0495(13) Uani 1 1 d . . . . .
H8 H 0.3147 1.3455 0.2683 0.059 Uiso 1 1 calc R . . . .
C9 C 0.3328(2) 0.5950(10) 0.4568(4) 0.0476(13) Uani 1 1 d . . . . .
C10 C 0.3646(2) 0.7014(9) 0.4113(4) 0.0408(12) Uani 1 1 d . . . . .
H10 H 0.4012 0.6745 0.4313 0.049 Uiso 1 1 calc R . . . .
C11 C 0.3417(2) 0.8471(9) 0.3363(4) 0.0394(13) Uani 1 1 d . . . . .
C12 C 0.2864(2) 0.8793(16) 0.3064(4) 0.0559(14) Uani 1 1 d . . . . .
H12 H 0.2699 0.9715 0.2535 0.067 Uiso 1 1 calc R . . . .
C13 C 0.2558(2) 0.7737(14) 0.3554(6) 0.069(2) Uani 1 1 d . . . . .
H13 H 0.2193 0.8009 0.3368 0.083 Uiso 1 1 calc R . . . .
C14 C 0.2790(2) 0.6304(12) 0.4307(5) 0.0581(17) Uani 1 1 d . . . . .
H14 H 0.2586 0.5592 0.4632 0.070 Uiso 1 1 calc R . . . .
C15 C 0.4239(2) 1.0771(9) 0.3689(4) 0.0416(12) Uani 1 1 d . . . . .
H15A H 0.4093 1.1587 0.4124 0.050 Uiso 1 1 calc R . . . .
H15B H 0.4467 0.9685 0.4103 0.050 Uiso 1 1 calc R . . . .
C16 C 0.4973(2) 1.1435(9) 0.2972(4) 0.0417(12) Uani 1 1 d . . . . .
C17 C 0.5271(2) 0.9591(10) 0.3350(5) 0.0494(14) Uani 1 1 d . . . . .
H17 H 0.5180 0.8736 0.3808 0.059 Uiso 1 1 calc R . . . .
C18 C 0.5698(2) 0.9050(14) 0.3040(5) 0.0556(14) Uani 1 1 d . . . . .
H18 H 0.5893 0.7833 0.3300 0.067 Uiso 1 1 calc R . . . .
C19 C 0.5844(2) 1.0257(12) 0.2360(5) 0.0537(15) Uani 1 1 d . . . . .
C20 C 0.5550(2) 1.2084(10) 0.1977(4) 0.0467(13) Uani 1 1 d . . . . .
C21 C 0.5114(2) 1.2642(9) 0.2280(4) 0.0417(12) Uani 1 1 d . . . . .
H21 H 0.4917 1.3847 0.2010 0.050 Uiso 1 1 calc R . . . .
C22 C 0.5691(3) 1.3433(12) 0.1221(5) 0.0610(19) Uani 1 1 d . . . . .
C23 C 0.6652(3) 0.8376(14) 0.2587(7) 0.083(3) Uani 1 1 d . . . . .
H23A H 0.6945 0.8347 0.2328 0.125 Uiso 1 1 calc GR . . . .
H23B H 0.6498 0.6989 0.2541 0.125 Uiso 1 1 calc GR . . . .
H23C H 0.6780 0.8820 0.3282 0.125 Uiso 1 1 calc GR . . . .
C24 C 0.4020(3) 0.7733(13) 0.0521(5) 0.068(2) Uani 1 1 d . . . . .
H24A H 0.4215 0.8716 0.0254 0.103 Uiso 1 1 calc GR . . . .
H24B H 0.3713 0.7227 -0.0017 0.103 Uiso 1 1 calc GR . . . .
H24C H 0.4248 0.6563 0.0825 0.103 Uiso 1 1 calc GR . . . .
F1 F 0.56011(18) 1.2466(8) 0.0333(3) 0.0755(12) Uani 1 1 d . . . . .
F2 F 0.62167(15) 1.3948(11) 0.1536(3) 0.0838(12) Uani 1 1 d . . . . .
F3 F 0.5425(2) 1.5247(7) 0.1038(4) 0.0791(13) Uani 1 1 d . . . . .
N1 N 0.38455(17) 0.8779(10) 0.1278(3) 0.0451(9) Uani 1 1 d . . . . .
N2 N 0.45654(19) 1.2151(8) 0.3318(4) 0.0442(11) Uani 1 1 d D . . . .
H2 H 0.4396(16) 1.320(5) 0.297(3) 0.021(12) Uiso 1 1 d D . . . .
O1 O 0.42579(18) 0.6524(7) 0.2597(3) 0.0518(10) Uani 1 1 d . . . . .
O2 O 0.6260(2) 0.9800(10) 0.2017(4) 0.0775(16) Uani 1 1 d . . . . .
O3 O 0.5000 0.5642(12) 0.5000 0.0620(17) Uani 1 2 d S T P . .
H3 H 0.5080 0.4830 0.5512 0.093 Uiso 1 1 d G . . . .


_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 C9 1.903(6) . ?
C1 C2 1.547(7) . ?
C1 N1 1.362(7) . ?
C1 O1 1.224(7) . ?
C2 C3 1.511(7) . ?
C2 C11 1.528(7) . ?
C2 C15 1.569(7) . ?
C3 C4 1.391(8) . ?
C3 C8 1.379(8) . ?
C4 C5 1.376(8) . ?
C4 N1 1.397(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(10) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(8) . ?
C9 C14 1.366(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(8) . ?
C11 C12 1.394(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.371(10) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 N2 1.441(7) . ?
C16 C17 1.408(8) . ?
C16 C21 1.379(8) . ?
C16 N2 1.398(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(9) . ?
C19 C20 1.396(9) . ?
C19 O2 1.371(7) . ?
C20 C21 1.400(8) . ?
C20 C22 1.499(9) . ?
C21 H21 0.9300 . ?
C22 F1 1.335(8) . ?
C22 F2 1.352(8) . ?
C22 F3 1.325(9) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 O2 1.404(9) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24 N1 1.450(7) . ?
N2 H2 0.86(2) . ?
O3 H3 0.8500 . ?

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
N1 C1 C2 108.4(5) . . ?
O1 C1 C2 126.0(5) . . ?
O1 C1 N1 125.6(5) . . ?
C1 C2 C15 109.0(4) . . ?
C3 C2 C1 101.3(4) . . ?
C3 C2 C11 115.9(4) . . ?
C3 C2 C15 111.0(4) . . ?
C11 C2 C1 109.9(4) . . ?
C11 C2 C15 109.4(4) . . ?
C4 C3 C2 109.2(5) . . ?
C8 C3 C2 131.0(5) . . ?
C8 C3 C4 119.8(5) . . ?
C3 C4 N1 109.8(5) . . ?
C5 C4 C3 122.0(6) . . ?
C5 C4 N1 128.2(5) . . ?
C4 C5 H5 121.3 . . ?
C4 C5 C6 117.3(6) . . ?
C6 C5 H5 121.3 . . ?
C5 C6 H6 119.0 . . ?
C5 C6 C7 121.9(6) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.8(7) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C7 119.1(6) . . ?
C3 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 Br1 118.7(4) . . ?
C14 C9 Br1 118.9(5) . . ?
C14 C9 C10 122.3(6) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.7(5) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C2 120.3(4) . . ?
C10 C11 C12 118.6(5) . . ?
C12 C11 C2 121.1(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.3(7) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.7(6) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C13 118.3(6) . . ?
C9 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C2 C15 H15A 108.4 . . ?
C2 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
N2 C15 C2 115.7(4) . . ?
N2 C15 H15A 108.4 . . ?
N2 C15 H15B 108.4 . . ?
C21 C16 C17 118.4(5) . . ?
C21 C16 N2 119.0(5) . . ?
N2 C16 C17 122.5(5) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0(6) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.1 . . ?
C19 C18 C17 121.9(7) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C20 118.6(6) . . ?
O2 C19 C18 124.7(7) . . ?
O2 C19 C20 116.7(6) . . ?
C19 C20 C21 120.1(6) . . ?
C19 C20 C22 120.4(6) . . ?
C21 C20 C22 119.5(6) . . ?
C16 C21 C20 121.1(5) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
F1 C22 C20 112.8(6) . . ?
F1 C22 F2 104.9(5) . . ?
F2 C22 C20 112.2(6) . . ?
F3 C22 C20 112.9(5) . . ?
F3 C22 F1 107.3(6) . . ?
F3 C22 F2 106.1(6) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
C1 N1 C4 111.4(5) . . ?
C1 N1 C24 122.7(6) . . ?
C4 N1 C24 125.9(5) . . ?
C15 N2 H2 114(3) . . ?
C16 N2 C15 123.6(5) . . ?
C16 N2 H2 112(3) . . ?
C19 O2 C23 117.6(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.86(2) 2.17(3) 2.964(7) 155(4) 1_565
O3 H3 N2 0.85 2.33 3.153(8) 164.5 2_646

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
Br1 C9 C10 C11 177.0(4) . . . . ?
Br1 C9 C14 C13 -176.3(6) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C1 C2 C3 C8 -178.5(6) . . . . ?
C1 C2 C11 C10 65.5(6) . . . . ?
C1 C2 C11 C12 -113.0(6) . . . . ?
C1 C2 C15 N2 66.4(6) . . . . ?
C2 C1 N1 C4 -1.5(6) . . . . ?
C2 C1 N1 C24 176.5(6) . . . . ?
C2 C3 C4 C5 -179.2(5) . . . . ?
C2 C3 C4 N1 -0.1(6) . . . . ?
C2 C3 C8 C7 179.3(6) . . . . ?
C2 C11 C12 C13 -178.1(7) . . . . ?
C2 C15 N2 C16 -80.8(7) . . . . ?
C3 C2 C11 C10 179.4(5) . . . . ?
C3 C2 C11 C12 1.0(8) . . . . ?
C3 C2 C15 N2 -44.3(6) . . . . ?
C3 C4 C5 C6 0.0(9) . . . . ?
C3 C4 N1 C1 1.0(6) . . . . ?
C3 C4 N1 C24 -176.9(6) . . . . ?
C4 C3 C8 C7 1.8(9) . . . . ?
C4 C5 C6 C7 0.5(10) . . . . ?
C5 C4 N1 C1 -179.9(6) . . . . ?
C5 C4 N1 C24 2.2(10) . . . . ?
C5 C6 C7 C8 0.1(10) . . . . ?
C6 C7 C8 C3 -1.2(10) . . . . ?
C8 C3 C4 C5 -1.2(9) . . . . ?
C8 C3 C4 N1 178.0(5) . . . . ?
C9 C10 C11 C2 179.8(5) . . . . ?
C9 C10 C11 C12 -1.7(8) . . . . ?
C10 C9 C14 C13 1.3(11) . . . . ?
C10 C11 C12 C13 3.3(10) . . . . ?
C11 C2 C3 C4 -119.6(5) . . . . ?
C11 C2 C3 C8 62.7(8) . . . . ?
C11 C2 C15 N2 -173.4(5) . . . . ?
C11 C12 C13 C14 -2.8(13) . . . . ?
C12 C13 C14 C9 0.4(12) . . . . ?
C14 C9 C10 C11 -0.6(9) . . . . ?
C15 C2 C3 C4 114.9(5) . . . . ?
C15 C2 C3 C8 -62.9(7) . . . . ?
C15 C2 C11 C10 -54.2(6) . . . . ?
C15 C2 C11 C12 127.3(6) . . . . ?
C16 C17 C18 C19 -0.5(10) . . . . ?
C17 C16 C21 C20 -1.5(8) . . . . ?
C17 C16 N2 C15 -30.1(8) . . . . ?
C17 C18 C19 C20 0.2(10) . . . . ?
C17 C18 C19 O2 -179.5(6) . . . . ?
C18 C19 C20 C21 -0.5(9) . . . . ?
C18 C19 C20 C22 -179.2(6) . . . . ?
C18 C19 O2 C23 -18.5(10) . . . . ?
C19 C20 C21 C16 1.2(9) . . . . ?
C19 C20 C22 F1 66.8(8) . . . . ?
C19 C20 C22 F2 -51.5(8) . . . . ?
C19 C20 C22 F3 -171.3(6) . . . . ?
C20 C19 O2 C23 161.9(6) . . . . ?
C21 C16 C17 C18 1.2(9) . . . . ?
C21 C16 N2 C15 154.0(5) . . . . ?
C21 C20 C22 F1 -111.9(7) . . . . ?
C21 C20 C22 F2 129.8(6) . . . . ?
C21 C20 C22 F3 10.0(9) . . . . ?
C22 C20 C21 C16 179.9(5) . . . . ?
N1 C1 C2 C3 1.3(6) . . . . ?
N1 C1 C2 C11 124.3(5) . . . . ?
N1 C1 C2 C15 -115.8(5) . . . . ?
N1 C4 C5 C6 -179.0(6) . . . . ?
N2 C16 C17 C18 -174.7(6) . . . . ?
N2 C16 C21 C20 174.5(5) . . . . ?
O1 C1 C2 C3 -178.9(5) . . . . ?
O1 C1 C2 C11 -55.9(7) . . . . ?
O1 C1 C2 C15 64.0(7) . . . . ?
O1 C1 N1 C4 178.8(5) . . . . ?
O1 C1 N1 C24 -3.2(9) . . . . ?
O2 C19 C20 C21 179.2(6) . . . . ?
O2 C19 C20 C22 0.5(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
