# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 2391754'
loop_
_audit_author_name
_audit_author_address
'Yang WeiJing'
;Henan Normal University
China
;
_audit_update_record             
;
2024-10-17 deposited with the CCDC.	2025-02-21 downloaded from the CCDC.
;
_audit_creation_date             2024-09-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H25 Br F N3 O6'
_chemical_formula_sum            'C18 H25 Br F N3 O6'
_chemical_formula_weight         478.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.5596(3)
_cell_length_b                   9.8290(2)
_cell_length_c                   22.2609(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.72
_cell_angle_gamma                90
_cell_volume                     2244.54(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7971
_cell_measurement_temperature    292.97(16)
_cell_measurement_theta_max      71.9760
_cell_measurement_theta_min      4.0850
_shelx_estimated_absorpt_T_max   0.780
_shelx_estimated_absorpt_T_min   0.670
_exptl_absorpt_coefficient_mu    2.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7830
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.563
_diffrn_reflns_theta_max         66.563
_diffrn_reflns_theta_min         4.088
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.97(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -167.00-141.00   0.50    6.00    --  -95.00 -79.00 -35.00   52
  2  ω   -137.00 -87.00   0.50    6.00    --  -95.00 -79.00 -35.00  100
  3  ω     26.00  51.00   0.50    6.00    --   99.00 -55.00-179.00   50
  4  ω    112.00 171.00   0.50    6.00    --   99.00  55.00 -36.00  118
  5  ω    136.00 169.00   0.50    6.00    --   99.00  91.00-170.00   66
  6  ω    -19.00  17.00   0.50    4.00    --  -45.24  19.00  90.00   72
  7  ω    -13.00  29.00   0.50    4.00    --  -45.24  19.00 -90.00   84
  8  ω     -7.00  32.00   0.50    4.00    --  -45.24  19.00-180.00   78
  9  ω    -19.00  29.00   0.50    4.00    --   45.24 -19.00  30.00   96
 10  ω    -27.00  -1.00   0.50    4.00    --   45.24 -79.00 -35.00   52
 11  ω      3.00  64.00   0.50    4.00    --   45.24 -79.00 -35.00  122
 12  ω     27.00  52.00   0.50    6.00    --   99.00 -45.00 120.00   50
 13  ω    109.00 143.00   0.50    6.00    --   99.00  77.00 120.00   68
 14  ω     26.00  51.00   0.50    6.00    --   99.00 -45.00 -30.00   50
 15  ω     82.00 156.00   0.50    6.00    --   99.00  61.00   0.00  148
 16  ω     33.00  65.00   0.50    6.00    --   99.00-125.00  90.00   64
 17  ω     70.00  97.00   0.50    6.00    --   99.00-125.00  90.00   54
 18  ω     83.00 108.00   0.50    6.00    --   99.00  77.00 120.00   50
 19  ω     27.00  68.00   0.50    6.00    --   99.00 -61.00 -30.00   82
 20  ω    119.00 170.00   0.50    6.00    --   99.00  15.00 -90.00  102
 21  ω     26.00  56.00   0.50    6.00    --   99.00 -61.00  60.00   60
 22  ω     78.00 111.00   0.50    6.00    --   99.00  15.00 -90.00   66
 23  ω     28.00  69.00   0.50    6.00    --   99.00 -61.00  90.00   82
 24  ω     27.00  67.00   0.50    6.00    --   99.00 -61.00 -60.00   80
 25  ω     35.00  73.00   0.50    6.00    --   99.00 -94.00-180.00   76
 26  ω     27.00  53.00   0.50    6.00    --   99.00 -45.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0304264000
_diffrn_orient_matrix_UB_12      -0.0220514000
_diffrn_orient_matrix_UB_13      -0.1185674000
_diffrn_orient_matrix_UB_21      0.0915954000
_diffrn_orient_matrix_UB_22      0.0241849000
_diffrn_orient_matrix_UB_23      -0.0599180000
_diffrn_orient_matrix_UB_31      0.1093850000
_diffrn_orient_matrix_UB_32      -0.0140173000
_diffrn_orient_matrix_UB_33      0.0832046000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                6720
_reflns_number_total             7830
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.334
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.254
_refine_ls_abs_structure_details 
;
 Flack x determined using 2275 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         7830
_refine_ls_number_restraints     453
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0860
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1663P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2183
_refine_ls_wR_factor_ref         0.2276
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.505(3)
 0.495(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid bond restraints
 C3, C4
 with sigma for 1-2 distances of 0.008 and sigma for 1-3 distances of 0.008
 Br1, C3
 with sigma for 1-2 distances of 0.0007 and sigma for 1-3 distances of 0.0007
4. Uiso/Uaniso restraints and constraints
C3 \\sim C4: within 2A with sigma of 0.006 and sigma for terminal atoms of
0.012 within 2A
Br2 \\sim C26: within 2A with sigma of 0.008 and sigma for terminal atoms of
0.016 within 2A
Br1 \\sim C3: within 2A with sigma of 0.0008 and sigma for terminal atoms of
0.0016 within 2A
5. Rigid body (RIGU) restrains
 Br1, F1, O1, O2, O3, O4, O5, O6, N2, N3, H3, C1, C2, H2, C3, C4, H4, C5, H5,
 N1, C7, C8, C10, C11, C12, H12A, H12B, H12C, C13, C14, H14A, H14B, H14C, C15,
 H15A, H15B, H15C, C16, H16A, H16B, H16C, C17, C18, H18A, H18B, H18C, C19, H19A,
  H19B, H19C, C20, H20A, H20B, H20C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.007
 Br2, F2, O7, O8, O9, O10, O11, O12, N7, N6, H6, C21, H21A, H21B, H21C, C22,
 C23, C24, C25, H25, C26, C27, H27, C28, H28, N5, C31, C32, C33, H33A, H33B,
 H33C, C34, C35, H35A, H35B, H35C, C36, H36A, H36B, H36C, C37, H37A, H37B, H37C,
  C38, C39, H39A, H39B, H39C, C40, H40A, H40B, H40C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.007
6.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C4(H4), C5(H5), N6(H6), C25(H25), C27(H27), C28(H28)
6.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,
 H21B,H21C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C),
 C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C)
;
_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 0.02337(12) 0.51140(14) -0.17421(4) 0.1107(3) Uani 1 1 d . U . . .
F1 F 0.2875(4) 0.3740(3) 0.05185(17) 0.0590(9) Uani 1 1 d . . . . .
O1 O 0.2953(4) 0.6478(4) 0.1520(2) 0.0636(9) Uani 1 1 d . . . . .
O2 O 0.1921(4) 0.4506(5) 0.1460(2) 0.0729(10) Uani 1 1 d . . . . .
O3 O 0.5053(4) 0.4695(5) 0.15302(19) 0.0640(10) Uani 1 1 d . . . . .
O4 O 0.6315(4) 0.5706(4) 0.09571(19) 0.0561(9) Uani 1 1 d . . . . .
O5 O 0.4921(4) 0.4073(3) -0.0204(2) 0.0593(10) Uani 1 1 d . . . . .
O6 O 0.5132(4) 0.5963(4) -0.07584(15) 0.0527(7) Uani 1 1 d . . . . .
N2 N 0.4157(4) 0.5690(4) 0.06162(18) 0.0452(7) Uani 1 1 d . . . . .
N3 N 0.4340(5) 0.6164(4) 0.00630(19) 0.0455(8) Uani 1 1 d . . . . .
H3 H 0.415586 0.698939 -0.005292 0.055 Uiso 1 1 calc R U . . .
C1 C 0.1826(5) 0.5783(5) 0.0106(3) 0.0488(9) Uani 1 1 d . . . . .
C2 C 0.1567(5) 0.5158(6) -0.0485(2) 0.0584(11) Uani 1 1 d . . . . .
H2 H 0.199362 0.437962 -0.056981 0.070 Uiso 1 1 calc R U . . .
C3 C 0.0610(12) 0.5824(13) -0.0926(4) 0.1063(6) Uani 1 1 d . U . . .
C4 C -0.0094(10) 0.6902(11) -0.0793(4) 0.0976(13) Uani 1 1 d . U . . .
H4 H -0.074889 0.731778 -0.109010 0.117 Uiso 1 1 calc R U . . .
C5 C 0.0237(8) 0.7326(8) -0.0189(4) 0.0791(15) Uani 1 1 d . . . . .
H5 H -0.021738 0.806589 -0.008495 0.095 Uiso 1 1 calc R U . . .
N1 N 0.1146(6) 0.6777(5) 0.0260(3) 0.0681(11) Uani 1 1 d . . . . .
C7 C 0.2540(5) 0.5322(5) 0.1271(2) 0.0520(8) Uani 1 1 d . . . . .
C8 C 0.2908(5) 0.5098(5) 0.0637(2) 0.0488(7) Uani 1 1 d . . . . .
C10 C 0.5223(5) 0.5269(6) 0.1086(2) 0.0485(8) Uani 1 1 d . . . . .
C11 C 0.4833(5) 0.5262(5) -0.0301(2) 0.0465(8) Uani 1 1 d . . . . .
C12 C 0.5830(12) 0.6370(7) -0.1654(3) 0.109(3) Uani 1 1 d . . . . .
H12A H 0.497765 0.666437 -0.187093 0.164 Uiso 1 1 calc R U . . .
H12B H 0.630565 0.605919 -0.194518 0.164 Uiso 1 1 calc R U . . .
H12C H 0.628684 0.711681 -0.142024 0.164 Uiso 1 1 calc R U . . .
C13 C 0.5708(6) 0.5242(6) -0.1227(2) 0.0554(8) Uani 1 1 d . . . . .
C14 C 0.6990(6) 0.4641(7) -0.0915(3) 0.0705(16) Uani 1 1 d . . . . .
H14A H 0.751417 0.531899 -0.066076 0.106 Uiso 1 1 calc R U . . .
H14B H 0.742705 0.432798 -0.122089 0.106 Uiso 1 1 calc R U . . .
H14C H 0.685455 0.388988 -0.066167 0.106 Uiso 1 1 calc R U . . .
C15 C 0.4754(11) 0.4126(8) -0.1554(3) 0.0866(19) Uani 1 1 d . . . . .
H15A H 0.490866 0.330036 -0.131789 0.130 Uiso 1 1 calc R U . . .
H15B H 0.489016 0.396588 -0.195991 0.130 Uiso 1 1 calc R U . . .
H15C H 0.387310 0.442015 -0.158850 0.130 Uiso 1 1 calc R U . . .
C16 C 0.8489(7) 0.5845(12) 0.0967(4) 0.101(2) Uani 1 1 d . . . . .
H16A H 0.931238 0.538703 0.109302 0.151 Uiso 1 1 calc R U . . .
H16B H 0.862170 0.680977 0.101222 0.151 Uiso 1 1 calc R U . . .
H16C H 0.810088 0.563578 0.054176 0.151 Uiso 1 1 calc R U . . .
C17 C 0.7604(5) 0.5383(7) 0.1362(3) 0.0647(9) Uani 1 1 d . . . . .
C18 C 0.7709(9) 0.3846(8) 0.1449(5) 0.094(3) Uani 1 1 d . . . . .
H18A H 0.857966 0.361208 0.166719 0.141 Uiso 1 1 calc R U . . .
H18B H 0.751001 0.340813 0.105201 0.141 Uiso 1 1 calc R U . . .
H18C H 0.710425 0.354806 0.168249 0.141 Uiso 1 1 calc R U . . .
C19 C 0.7739(10) 0.6151(10) 0.1959(5) 0.101(2) Uani 1 1 d . . . . .
H19A H 0.733240 0.564365 0.223074 0.152 Uiso 1 1 calc R U . . .
H19B H 0.732509 0.702244 0.187594 0.152 Uiso 1 1 calc R U . . .
H19C H 0.864659 0.627492 0.215169 0.152 Uiso 1 1 calc R U . . .
C20 C 0.2711(9) 0.6747(9) 0.2108(3) 0.092(2) Uani 1 1 d . . . . .
H20A H 0.186689 0.640297 0.212068 0.138 Uiso 1 1 calc R U . . .
H20B H 0.273739 0.771090 0.217973 0.138 Uiso 1 1 calc R U . . .
H20C H 0.336494 0.630968 0.242217 0.138 Uiso 1 1 calc R U . . .
Br2 Br 0.70780(11) 0.51363(10) 0.67981(3) 0.1032(3) Uani 1 1 d . U . . .
F2 F 0.7448(4) 0.6426(3) 0.45256(16) 0.0595(8) Uani 1 1 d . . . . .
O7 O 0.5491(5) 0.5714(5) 0.3614(2) 0.0779(12) Uani 1 1 d . . . . .
O8 O 0.6433(5) 0.3663(4) 0.3542(2) 0.0626(10) Uani 1 1 d . . . . .
O9 O 0.8573(4) 0.5427(4) 0.34948(19) 0.0629(10) Uani 1 1 d . . . . .
O10 O 1.0389(4) 0.4378(5) 0.40948(19) 0.0610(9) Uani 1 1 d . . . . .
O11 O 1.0245(5) 0.6036(3) 0.5248(2) 0.0663(13) Uani 1 1 d . . . . .
O12 O 1.0900(5) 0.4139(4) 0.5822(2) 0.0650(11) Uani 1 1 d . . . . .
N7 N 0.8561(4) 0.4449(5) 0.4427(2) 0.0510(8) Uani 1 1 d . . . . .
N6 N 0.9327(4) 0.3940(4) 0.4980(2) 0.0465(9) Uani 1 1 d . . . . .
H6 H 0.926840 0.310843 0.509040 0.056 Uiso 1 1 calc R U . . .
C21 C 0.5418(9) 0.3384(9) 0.2980(3) 0.081(2) Uani 1 1 d . . . . .
H21A H 0.549541 0.401874 0.266285 0.122 Uiso 1 1 calc R U . . .
H21B H 0.457523 0.347690 0.306814 0.122 Uiso 1 1 calc R U . . .
H21C H 0.551919 0.247454 0.284142 0.122 Uiso 1 1 calc R U . . .
C22 C 0.6338(6) 0.4854(6) 0.3810(2) 0.0547(9) Uani 1 1 d . . . . .
C23 C 0.7323(5) 0.5007(5) 0.4429(2) 0.0487(7) Uani 1 1 d . . . . .
C24 C 0.6757(5) 0.4481(5) 0.4948(3) 0.0517(9) Uani 1 1 d . . . . .
C25 C 0.7107(6) 0.4994(7) 0.5509(2) 0.0583(11) Uani 1 1 d . . . . .
H25 H 0.769831 0.570965 0.559592 0.070 Uiso 1 1 calc R U . . .
C26 C 0.6571(6) 0.4439(5) 0.5974(2) 0.0550(9) Uani 1 1 d . U . . .
C27 C 0.5778(7) 0.3321(6) 0.5851(3) 0.0665(11) Uani 1 1 d . . . . .
H27 H 0.545944 0.289690 0.615846 0.080 Uiso 1 1 calc R U . . .
C28 C 0.5473(7) 0.2850(7) 0.5247(3) 0.0713(12) Uani 1 1 d . . . . .
H28 H 0.487529 0.214368 0.514495 0.086 Uiso 1 1 calc R U . . .
N5 N 0.6001(5) 0.3366(5) 0.4798(2) 0.0607(9) Uani 1 1 d . . . . .
C31 C 0.9150(5) 0.4793(5) 0.3955(2) 0.0524(9) Uani 1 1 d . . . . .
C32 C 1.0182(5) 0.4839(5) 0.5336(2) 0.0472(9) Uani 1 1 d . . . . .
C33 C 1.1280(9) 0.5977(6) 0.6577(3) 0.0759(16) Uani 1 1 d . . . . .
H33A H 1.189562 0.630458 0.693662 0.114 Uiso 1 1 calc R U . . .
H33B H 1.051328 0.565488 0.669244 0.114 Uiso 1 1 calc R U . . .
H33C H 1.104807 0.670245 0.628222 0.114 Uiso 1 1 calc R U . . .
C34 C 1.1895(6) 0.4805(6) 0.6285(3) 0.0650(10) Uani 1 1 d . . . . .
C35 C 1.2501(10) 0.3664(8) 0.6723(4) 0.093(2) Uani 1 1 d . . . . .
H35A H 1.343232 0.376386 0.682951 0.139 Uiso 1 1 calc R U . . .
H35B H 1.227466 0.280175 0.652353 0.139 Uiso 1 1 calc R U . . .
H35C H 1.217961 0.370655 0.709113 0.139 Uiso 1 1 calc R U . . .
C36 C 1.2942(8) 0.5386(9) 0.5962(4) 0.0838(17) Uani 1 1 d . . . . .
H36A H 1.265538 0.625050 0.577831 0.126 Uiso 1 1 calc R U . . .
H36B H 1.305886 0.476569 0.564608 0.126 Uiso 1 1 calc R U . . .
H36C H 1.375325 0.549796 0.626179 0.126 Uiso 1 1 calc R U . . .
C37 C 1.1290(9) 0.6267(8) 0.3600(4) 0.087(2) Uani 1 1 d . . . . .
H37A H 1.048711 0.653746 0.332289 0.131 Uiso 1 1 calc R U . . .
H37B H 1.200712 0.650141 0.342284 0.131 Uiso 1 1 calc R U . . .
H37C H 1.138365 0.672847 0.398779 0.131 Uiso 1 1 calc R U . . .
C38 C 1.1281(6) 0.4792(7) 0.3699(3) 0.0659(9) Uani 1 1 d . . . . .
C39 C 1.2604(8) 0.4240(11) 0.4070(4) 0.097(2) Uani 1 1 d . . . . .
H39A H 1.329611 0.466679 0.392778 0.145 Uiso 1 1 calc R U . . .
H39B H 1.263679 0.327352 0.401229 0.145 Uiso 1 1 calc R U . . .
H39C H 1.270091 0.443487 0.450130 0.145 Uiso 1 1 calc R U . . .
C40 C 1.0886(8) 0.4024(8) 0.3086(3) 0.0815(18) Uani 1 1 d . . . . .
H40A H 1.101184 0.306572 0.316064 0.122 Uiso 1 1 calc R U . . .
H40B H 1.141304 0.432486 0.281505 0.122 Uiso 1 1 calc R U . . .
H40C H 0.998450 0.419866 0.289819 0.122 Uiso 1 1 calc R U . . .


_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 1.898(10) . ?
F1 C8 1.360(5) . ?
O1 C7 1.294(7) . ?
O1 C20 1.418(9) . ?
O2 C7 1.173(7) . ?
O3 C10 1.188(7) . ?
O4 C10 1.324(7) . ?
O4 C17 1.478(7) . ?
O5 C11 1.188(6) . ?
O6 C11 1.329(6) . ?
O6 C13 1.503(6) . ?
N2 N3 1.373(6) . ?
N2 C8 1.452(7) . ?
N2 C10 1.405(6) . ?
N3 H3 0.8600 . ?
N3 C11 1.382(6) . ?
C1 C2 1.418(8) . ?
C1 N1 1.306(8) . ?
C1 C8 1.586(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(12) . ?
C3 C4 1.367(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(13) . ?
C5 H5 0.9300 . ?
C5 N1 1.325(9) . ?
C7 C8 1.566(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 C13 1.486(9) . ?
C13 C14 1.489(8) . ?
C13 C15 1.549(10) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C17 1.497(11) . ?
C17 C18 1.524(10) . ?
C17 C19 1.506(12) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
Br2 C26 1.913(5) . ?
F2 C23 1.413(6) . ?
O7 C22 1.232(8) . ?
O8 C21 1.467(9) . ?
O8 C22 1.329(7) . ?
O9 C31 1.230(7) . ?
O10 C31 1.335(7) . ?
O10 C38 1.490(8) . ?
O11 C32 1.197(6) . ?
O12 C32 1.352(6) . ?
O12 C34 1.443(7) . ?
N7 N6 1.394(6) . ?
N7 C23 1.418(7) . ?
N7 C31 1.385(7) . ?
N6 H6 0.8600 . ?
N6 C32 1.374(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.526(7) . ?
C23 C24 1.511(8) . ?
C24 C25 1.317(8) . ?
C24 N5 1.350(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.401(8) . ?
C26 C27 1.370(9) . ?
C27 H27 0.9300 . ?
C27 C28 1.385(10) . ?
C28 H28 0.9300 . ?
C28 N5 1.353(9) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C33 C34 1.539(9) . ?
C34 C35 1.524(10) . ?
C34 C36 1.564(12) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C37 C38 1.468(10) . ?
C38 C39 1.543(10) . ?
C38 C40 1.528(9) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 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
C7 O1 C20 116.3(5) . . ?
C10 O4 C17 121.5(4) . . ?
C11 O6 C13 119.7(4) . . ?
N3 N2 C8 119.1(4) . . ?
N3 N2 C10 120.6(4) . . ?
C10 N2 C8 115.6(4) . . ?
N2 N3 H3 121.3 . . ?
N2 N3 C11 117.4(4) . . ?
C11 N3 H3 121.3 . . ?
C2 C1 C8 117.0(5) . . ?
N1 C1 C2 124.8(5) . . ?
N1 C1 C8 117.7(5) . . ?
C1 C2 H2 123.3 . . ?
C3 C2 C1 113.5(7) . . ?
C3 C2 H2 123.3 . . ?
C2 C3 Br1 117.0(8) . . ?
C4 C3 Br1 119.4(7) . . ?
C4 C3 C2 123.5(8) . . ?
C3 C4 H4 122.5 . . ?
C3 C4 C5 115.0(8) . . ?
C5 C4 H4 122.5 . . ?
C4 C5 H5 117.1 . . ?
N1 C5 C4 125.9(8) . . ?
N1 C5 H5 117.1 . . ?
C1 N1 C5 116.9(6) . . ?
O1 C7 C8 112.2(4) . . ?
O2 C7 O1 127.4(6) . . ?
O2 C7 C8 120.4(5) . . ?
F1 C8 N2 111.6(4) . . ?
F1 C8 C1 107.0(4) . . ?
F1 C8 C7 108.2(4) . . ?
N2 C8 C1 107.8(4) . . ?
N2 C8 C7 113.2(4) . . ?
C7 C8 C1 108.9(4) . . ?
O3 C10 O4 130.2(5) . . ?
O3 C10 N2 120.5(5) . . ?
O4 C10 N2 109.2(4) . . ?
O5 C11 O6 128.8(5) . . ?
O5 C11 N3 123.3(5) . . ?
O6 C11 N3 107.9(4) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
O6 C13 C15 109.6(5) . . ?
C12 C13 O6 101.7(5) . . ?
C12 C13 C14 112.7(7) . . ?
C12 C13 C15 111.9(5) . . ?
C14 C13 O6 109.6(4) . . ?
C14 C13 C15 110.9(6) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
O4 C17 C16 101.0(5) . . ?
O4 C17 C18 108.6(5) . . ?
O4 C17 C19 108.1(6) . . ?
C16 C17 C18 109.8(7) . . ?
C16 C17 C19 115.1(7) . . ?
C19 C17 C18 113.3(7) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 O8 C21 115.4(5) . . ?
C31 O10 C38 120.0(4) . . ?
C32 O12 C34 121.1(4) . . ?
N6 N7 C23 118.6(4) . . ?
C31 N7 N6 119.0(4) . . ?
C31 N7 C23 119.2(4) . . ?
N7 N6 H6 121.9 . . ?
C32 N6 N7 116.3(4) . . ?
C32 N6 H6 121.9 . . ?
O8 C21 H21A 109.5 . . ?
O8 C21 H21B 109.5 . . ?
O8 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O7 C22 O8 124.9(5) . . ?
O7 C22 C23 122.3(5) . . ?
O8 C22 C23 112.6(5) . . ?
F2 C23 N7 109.2(4) . . ?
F2 C23 C22 104.7(4) . . ?
F2 C23 C24 105.2(4) . . ?
N7 C23 C22 113.0(4) . . ?
N7 C23 C24 113.7(4) . . ?
C24 C23 C22 110.4(4) . . ?
C25 C24 C23 121.4(5) . . ?
C25 C24 N5 124.2(6) . . ?
N5 C24 C23 114.0(5) . . ?
C24 C25 H25 120.7 . . ?
C24 C25 C26 118.7(6) . . ?
C26 C25 H25 120.7 . . ?
C25 C26 Br2 119.9(4) . . ?
C27 C26 Br2 119.8(5) . . ?
C27 C26 C25 120.0(5) . . ?
C26 C27 H27 121.6 . . ?
C26 C27 C28 116.9(6) . . ?
C28 C27 H27 121.6 . . ?
C27 C28 H28 118.3 . . ?
N5 C28 C27 123.4(6) . . ?
N5 C28 H28 118.3 . . ?
C24 N5 C28 116.4(5) . . ?
O9 C31 O10 127.8(5) . . ?
O9 C31 N7 122.2(5) . . ?
O10 C31 N7 109.9(4) . . ?
O11 C32 O12 126.1(5) . . ?
O11 C32 N6 126.3(5) . . ?
O12 C32 N6 107.6(4) . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
O12 C34 C33 109.4(5) . . ?
O12 C34 C35 104.3(5) . . ?
O12 C34 C36 108.1(6) . . ?
C33 C34 C36 109.6(6) . . ?
C35 C34 C33 115.9(6) . . ?
C35 C34 C36 109.1(7) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
O10 C38 C39 101.9(5) . . ?
O10 C38 C40 108.4(5) . . ?
C37 C38 O10 112.8(6) . . ?
C37 C38 C39 113.0(7) . . ?
C37 C38 C40 111.3(6) . . ?
C40 C38 C39 108.9(6) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
Br1 C3 C4 C5 179.0(8) . . . . ?
O1 C7 C8 F1 158.4(4) . . . . ?
O1 C7 C8 N2 34.2(6) . . . . ?
O1 C7 C8 C1 -85.7(5) . . . . ?
O2 C7 C8 F1 -23.8(6) . . . . ?
O2 C7 C8 N2 -148.0(5) . . . . ?
O2 C7 C8 C1 92.1(6) . . . . ?
N2 N3 C11 O5 11.3(7) . . . . ?
N2 N3 C11 O6 -170.1(4) . . . . ?
N3 N2 C8 F1 88.8(5) . . . . ?
N3 N2 C8 C1 -28.4(5) . . . . ?
N3 N2 C8 C7 -148.9(4) . . . . ?
N3 N2 C10 O3 -170.0(5) . . . . ?
N3 N2 C10 O4 14.4(6) . . . . ?
C1 C2 C3 Br1 177.6(6) . . . . ?
C1 C2 C3 C4 -5.5(15) . . . . ?
C2 C1 N1 C5 -7.5(9) . . . . ?
C2 C1 C8 F1 -31.3(6) . . . . ?
C2 C1 C8 N2 88.8(5) . . . . ?
C2 C1 C8 C7 -148.0(5) . . . . ?
C2 C3 C4 C5 2.1(17) . . . . ?
C3 C4 C5 N1 -0.8(15) . . . . ?
C4 C5 N1 C1 3.4(12) . . . . ?
N1 C1 C2 C3 8.4(10) . . . . ?
N1 C1 C8 F1 141.1(5) . . . . ?
N1 C1 C8 N2 -98.7(6) . . . . ?
N1 C1 C8 C7 24.4(6) . . . . ?
C8 N2 N3 C11 -90.6(5) . . . . ?
C8 N2 C10 O3 -14.4(7) . . . . ?
C8 N2 C10 O4 170.0(4) . . . . ?
C8 C1 C2 C3 -179.7(7) . . . . ?
C8 C1 N1 C5 -179.3(6) . . . . ?
C10 O4 C17 C16 169.5(6) . . . . ?
C10 O4 C17 C18 54.1(8) . . . . ?
C10 O4 C17 C19 -69.3(8) . . . . ?
C10 N2 N3 C11 64.1(6) . . . . ?
C10 N2 C8 F1 -67.2(5) . . . . ?
C10 N2 C8 C1 175.6(4) . . . . ?
C10 N2 C8 C7 55.1(5) . . . . ?
C11 O6 C13 C12 177.7(6) . . . . ?
C11 O6 C13 C14 -62.7(6) . . . . ?
C11 O6 C13 C15 59.2(6) . . . . ?
C13 O6 C11 O5 -2.3(8) . . . . ?
C13 O6 C11 N3 179.3(4) . . . . ?
C17 O4 C10 O3 6.8(9) . . . . ?
C17 O4 C10 N2 -178.2(5) . . . . ?
C20 O1 C7 O2 4.9(9) . . . . ?
C20 O1 C7 C8 -177.5(5) . . . . ?
Br2 C26 C27 C28 -178.6(5) . . . . ?
F2 C23 C24 C25 -37.5(7) . . . . ?
F2 C23 C24 N5 149.6(4) . . . . ?
O7 C22 C23 F2 -27.5(7) . . . . ?
O7 C22 C23 N7 -146.3(6) . . . . ?
O7 C22 C23 C24 85.2(7) . . . . ?
O8 C22 C23 F2 157.8(5) . . . . ?
O8 C22 C23 N7 39.0(7) . . . . ?
O8 C22 C23 C24 -89.5(6) . . . . ?
N7 N6 C32 O11 7.3(9) . . . . ?
N7 N6 C32 O12 -175.4(5) . . . . ?
N7 C23 C24 C25 81.9(7) . . . . ?
N7 C23 C24 N5 -90.9(6) . . . . ?
N6 N7 C23 F2 93.4(5) . . . . ?
N6 N7 C23 C22 -150.5(4) . . . . ?
N6 N7 C23 C24 -23.7(6) . . . . ?
N6 N7 C31 O9 -169.1(5) . . . . ?
N6 N7 C31 O10 8.7(6) . . . . ?
C21 O8 C22 O7 -1.3(9) . . . . ?
C21 O8 C22 C23 173.2(6) . . . . ?
C22 C23 C24 C25 -149.9(5) . . . . ?
C22 C23 C24 N5 37.3(6) . . . . ?
C23 N7 N6 C32 -91.2(6) . . . . ?
C23 N7 C31 O9 -9.3(8) . . . . ?
C23 N7 C31 O10 168.5(4) . . . . ?
C23 C24 C25 C26 -178.4(5) . . . . ?
C23 C24 N5 C28 179.8(5) . . . . ?
C24 C25 C26 Br2 179.0(5) . . . . ?
C24 C25 C26 C27 4.9(9) . . . . ?
C25 C24 N5 C28 7.1(9) . . . . ?
C25 C26 C27 C28 -4.5(9) . . . . ?
C26 C27 C28 N5 5.6(10) . . . . ?
C27 C28 N5 C24 -6.7(9) . . . . ?
N5 C24 C25 C26 -6.3(9) . . . . ?
C31 O10 C38 C37 52.2(7) . . . . ?
C31 O10 C38 C39 173.7(6) . . . . ?
C31 O10 C38 C40 -71.5(7) . . . . ?
C31 N7 N6 C32 68.7(6) . . . . ?
C31 N7 C23 F2 -66.5(6) . . . . ?
C31 N7 C23 C22 49.6(6) . . . . ?
C31 N7 C23 C24 176.4(4) . . . . ?
C32 O12 C34 C33 58.0(8) . . . . ?
C32 O12 C34 C35 -177.4(6) . . . . ?
C32 O12 C34 C36 -61.3(7) . . . . ?
C34 O12 C32 O11 -2.8(10) . . . . ?
C34 O12 C32 N6 179.9(5) . . . . ?
C38 O10 C31 O9 5.9(9) . . . . ?
C38 O10 C31 N7 -171.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.959
_oxdiff_exptl_absorpt_empirical_full_min 0.488
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.505(3)
2 0.495(3)

