# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_MKT_Sif_7_4_2022_pre2_autored
_database_code_depnum_ccdc_archive 'CCDC 2168153'
loop_
_audit_author_name
_audit_author_address
'Mathias Kirk Thoegersen'
;Aarhus University
Denmark
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_audit_creation_date             2022-04-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C18 H8 Br Cl F2 O3'
_chemical_formula_sum            'C18 H8 Br Cl F2 O3'
_chemical_formula_weight         425.615
_chemical_oxdiff_formula         C20H8O2ClBrF2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.3118(7)
_cell_length_b                   8.4520(5)
_cell_length_c                   12.0667(8)
_cell_angle_alpha                80.772(5)
_cell_angle_beta                 79.030(6)
_cell_angle_gamma                72.149(6)
_cell_volume                     787.41(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4231
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.3430
_cell_measurement_theta_min      3.4930
_exptl_absorpt_coefficient_mu    2.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull whiteish colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_description       irregular
_exptl_crystal_F_000             420.138
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.9972
_diffrn_reflns_Laue_measured_fraction_max 0.8761
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8373
_diffrn_reflns_point_group_measured_fraction_full 0.9972
_diffrn_reflns_point_group_measured_fraction_max 0.8761
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.91
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.8761
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  88.00   0.75    3.58    --   14.97  55.00  40.00  112
  2  ω    -58.00  43.25   0.75    3.58    --   14.97 -55.00-102.00  135
  3  ω    -12.00  86.25   0.75    3.58    --   14.97  57.00-180.00  131
  4  ω    -17.00  13.00   0.75    3.58    --  -15.75 -77.00 150.00   40
  5  ω    -11.00  14.50   0.75    3.58    --  -15.75  77.00   0.00   34
  6  ω   -104.00 -77.75   0.75    3.58    --  -15.75-178.00  30.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0065414000
_diffrn_orient_matrix_UB_12      -0.0634527000
_diffrn_orient_matrix_UB_13      -0.0340009000
_diffrn_orient_matrix_UB_21      0.0768387000
_diffrn_orient_matrix_UB_22      -0.0484266000
_diffrn_orient_matrix_UB_23      0.0203772000
_diffrn_orient_matrix_UB_31      -0.0477099000
_diffrn_orient_matrix_UB_32      -0.0386725000
_diffrn_orient_matrix_UB_33      0.0453548000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3693
_reflns_number_total             4361
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.2433
_refine_diff_density_min         -1.1602
_refine_diff_density_rms         0.1305
_refine_ls_d_res_high            0.6917
_refine_ls_d_res_low             6.1064
_refine_ls_goodness_of_fit_ref   1.0351
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.0351
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.4722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1114
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L),
 C00M(H00M), C00O(H00O)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br01 Br 0.96378(4) 0.00740(4) 0.23016(2) 0.02575(10) Uani 1.000000 .
Cl02 Cl 0.79906(9) 0.36427(9) 0.62716(5) 0.02236(15) Uani 1.000000 .
F1 F 0.6097(3) 0.8763(3) 0.09375(16) 0.0405(5) Uani 1.000000 .
F004 F 0.4012(3) 0.8111(3) 0.05239(17) 0.0457(5) Uani 1.000000 .
O005 O 0.5673(3) 0.6331(3) 0.16916(16) 0.0267(5) Uani 1.000000 .
O006 O 0.9237(3) 0.5172(3) 0.28248(16) 0.0328(5) Uani 1.000000 .
O007 O 0.6664(3) 0.6741(3) -0.01836(16) 0.0334(5) Uani 1.000000 .
C008 C 0.7559(3) 0.3612(3) 0.4074(2) 0.0176(5) Uani 1.000000 .
C009 C 0.5562(4) 0.2708(3) 0.5607(2) 0.0198(5) Uani 1.000000 .
H009 H 0.5169(4) 0.2532(3) 0.6397(2) 0.0237(6) Uiso 1.000000 R
C00A C 0.8962(4) 0.4406(3) 0.3730(2) 0.0200(5) Uani 1.000000 .
H00A H 0.9700(4) 0.4300(3) 0.4267(2) 0.0240(6) Uiso 1.000000 R
C00B C 0.6946(4) 0.3285(3) 0.5248(2) 0.0181(5) Uani 1.000000 .
C00C C 0.4698(4) 0.2365(3) 0.4804(2) 0.0182(5) Uani 1.000000 .
C00D C 0.6776(3) 0.3209(3) 0.32827(19) 0.0169(5) Uani 1.000000 .
C00E C 0.7446(4) 0.3420(4) 0.2042(2) 0.0200(5) Uani 1.000000 .
C00F C 0.5347(4) 0.2563(3) 0.3627(2) 0.0186(5) Uani 1.000000 .
C00G C 0.8708(4) 0.2166(4) 0.1470(2) 0.0225(6) Uani 1.000000 .
C00H C 0.4526(4) 0.2136(4) 0.2843(2) 0.0222(6) Uani 1.000000 .
H00H H 0.4956(4) 0.2244(4) 0.2055(2) 0.0266(7) Uiso 1.000000 R
C00I C 0.9336(4) 0.2396(4) 0.0319(2) 0.0277(7) Uani 1.000000 .
H00I H 1.0200(4) 0.1514(4) -0.0026(2) 0.0332(8) Uiso 1.000000 R
C00J C 0.3122(4) 0.1568(4) 0.3206(3) 0.0268(6) Uani 1.000000 .
H00J H 0.2577(4) 0.1292(4) 0.2670(3) 0.0322(7) Uiso 1.000000 R
C00K C 0.6862(4) 0.4869(4) 0.1364(2) 0.0221(6) Uani 1.000000 .
C00L C 0.2478(4) 0.1390(4) 0.4374(3) 0.0269(6) Uani 1.000000 .
H00L H 0.1501(4) 0.0994(4) 0.4618(3) 0.0322(7) Uiso 1.000000 R
C00M C 0.3238(4) 0.1780(3) 0.5154(2) 0.0233(6) Uani 1.000000 .
H00M H 0.2787(4) 0.1658(3) 0.5938(2) 0.0279(7) Uiso 1.000000 R
C00N C 0.7481(4) 0.5116(4) 0.0221(2) 0.0261(6) Uani 1.000000 .
C00O C 0.8714(4) 0.3904(4) -0.0334(2) 0.0303(7) Uani 1.000000 .
H00O H 0.9124(4) 0.4079(4) -0.1121(2) 0.0364(9) Uiso 1.000000 R
C00P C 0.5607(5) 0.7486(4) 0.0737(3) 0.0321(7) Uani 1.000000 .


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
Br01 C00G 1.902(3) . ?
Cl02 C00B 1.749(3) . ?
F1 C00P 1.334(4) . ?
F004 C00P 1.326(4) . ?
O005 C00K 1.385(4) . ?
O005 C00P 1.383(3) . ?
O006 C00A 1.197(3) . ?
O007 C00N 1.388(4) . ?
O007 C00P 1.384(4) . ?
C008 C00A 1.480(4) . ?
C008 C00B 1.425(3) . ?
C008 C00D 1.388(4) . ?
C009 C00B 1.354(4) . ?
C009 C00C 1.422(4) . ?
C00C C00F 1.422(3) . ?
C00C C00M 1.416(4) . ?
C00D C00E 1.497(3) . ?
C00D C00F 1.421(4) . ?
C00E C00G 1.407(4) . ?
C00E C00K 1.368(4) . ?
C00F C00H 1.414(4) . ?
C00G C00I 1.392(4) . ?
C00H C00J 1.366(4) . ?
C00I C00O 1.393(5) . ?
C00J C00L 1.411(4) . ?
C00K C00N 1.383(4) . ?
C00L C00M 1.359(4) . ?
C00N C00O 1.365(5) . ?

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
C00P O005 C00K 106.2(2) . . ?
C00P O007 C00N 106.7(2) . . ?
C00B C008 C00A 119.7(2) . . ?
C00D C008 C00A 122.0(2) . . ?
C00D C008 C00B 118.3(2) . . ?
C00C C009 C00B 120.1(2) . . ?
C008 C00A O006 124.8(3) . . ?
C008 C00B Cl02 119.6(2) . . ?
C009 C00B Cl02 118.28(18) . . ?
C009 C00B C008 122.1(2) . . ?
C00F C00C C009 119.3(2) . . ?
C00M C00C C009 121.3(2) . . ?
C00M C00C C00F 119.3(3) . . ?
C00E C00D C008 120.4(2) . . ?
C00F C00D C008 121.2(2) . . ?
C00F C00D C00E 118.5(2) . . ?
C00G C00E C00D 123.7(2) . . ?
C00K C00E C00D 122.1(3) . . ?
C00K C00E C00G 114.1(2) . . ?
C00D C00F C00C 118.8(2) . . ?
C00H C00F C00C 118.7(2) . . ?
C00H C00F C00D 122.5(2) . . ?
C00E C00G Br01 118.95(19) . . ?
C00I C00G Br01 118.2(2) . . ?
C00I C00G C00E 122.8(3) . . ?
C00J C00H C00F 120.7(2) . . ?
C00O C00I C00G 120.9(3) . . ?
C00L C00J C00H 120.2(3) . . ?
C00E C00K O005 127.3(2) . . ?
C00N C00K O005 109.1(3) . . ?
C00N C00K C00E 123.5(3) . . ?
C00M C00L C00J 120.8(3) . . ?
C00L C00M C00C 120.3(3) . . ?
C00K C00N O007 108.0(3) . . ?
C00O C00N O007 129.6(3) . . ?
C00O C00N C00K 122.4(3) . . ?
C00N C00O C00I 116.2(2) . . ?
F004 C00P F1 106.7(3) . . ?
O005 C00P F1 109.1(3) . . ?
O005 C00P F004 110.2(3) . . ?
O007 C00P F1 110.3(3) . . ?
O007 C00P F004 110.5(3) . . ?
O007 C00P O005 109.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br01 C00G C00E C00D -0.1(3) . . . . ?
Br01 C00G C00E C00K -179.8(2) . . . . ?
Br01 C00G C00I C00O -179.6(2) . . . . ?
Cl02 C00B C008 C00A -6.0(3) . . . . ?
Cl02 C00B C008 C00D 175.7(2) . . . . ?
Cl02 C00B C009 C00C -178.6(2) . . . . ?
F1 C00P O005 C00K -117.9(3) . . . . ?
F1 C00P O007 C00N 116.8(3) . . . . ?
F004 C00P O005 C00K 125.2(3) . . . . ?
F004 C00P O007 C00N -125.4(2) . . . . ?
O005 C00K C00E C00D 2.7(3) . . . . ?
O005 C00K C00E C00G -177.7(3) . . . . ?
O005 C00K C00N O007 -0.7(2) . . . . ?
O005 C00K C00N C00O 178.0(2) . . . . ?
O005 C00P O007 C00N -3.5(3) . . . . ?
O006 C00A C008 C00B -156.8(3) . . . . ?
O006 C00A C008 C00D 21.4(4) . . . . ?
O007 C00N C00K C00E -177.2(2) . . . . ?
O007 C00N C00O C00I 177.7(3) . . . . ?
C008 C00B C009 C00C 1.7(3) . . . . ?
C008 C00D C00E C00G 89.4(3) . . . . ?
C008 C00D C00E C00K -90.9(3) . . . . ?
C008 C00D C00F C00C 1.3(3) . . . . ?
C008 C00D C00F C00H -179.7(3) . . . . ?
C009 C00C C00F C00D -4.3(3) . . . . ?
C009 C00C C00F C00H 176.8(3) . . . . ?
C009 C00C C00M C00L -177.1(3) . . . . ?
C00C C00F C00D C00E -179.8(2) . . . . ?
C00C C00F C00H C00J 1.0(3) . . . . ?
C00C C00M C00L C00J -0.3(3) . . . . ?
C00D C00E C00G C00I -178.9(3) . . . . ?
C00D C00E C00K C00N 178.6(3) . . . . ?
C00D C00F C00H C00J -177.9(3) . . . . ?
C00E C00G C00I C00O -0.8(3) . . . . ?
C00E C00K C00N C00O 1.5(3) . . . . ?
C00F C00H C00J C00L -0.4(3) . . . . ?
C00G C00I C00O C00N 0.3(3) . . . . ?
C00H C00J C00L C00M 0.0(4) . . . . ?
C00I C00O C00N C00K -0.6(3) . . . . ?


_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.756
####################################################################### 
# 
# 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_MKT_NMR_01_03_2021_autored
_database_code_depnum_ccdc_archive 'CCDC 2169123'
loop_
_audit_author_name
_audit_author_address
'Mathias Kirk Thoegersen'
;Aarhus University
Denmark
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_audit_creation_date             2022-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         '0.57(C17 H16 Br2 O2)'
_chemical_formula_sum            'C9.714 H9.143 Br1.143 O1.143'
_chemical_formula_weight         235.50
_chemical_absolute_configuration ad
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   10.6752(2)
_cell_length_b                   11.9710(4)
_cell_length_c                   12.2865(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1570.13(8)
_cell_formula_units_Z            7
_cell_measurement_reflns_used    11138
_cell_measurement_temperature    100
_cell_measurement_theta_max      35.9100
_cell_measurement_theta_min      2.3610
_exptl_absorpt_coefficient_mu    5.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  1.00000
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.7433
_exptl_crystal_description       sphere
_exptl_crystal_F_000             814.2057
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_size_rad          0.400
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26846
_diffrn_reflns_theta_full        28.2788
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.38
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  84.00   1.00    7.50    --   38.99 -86.00-159.00  115
  2  ω     84.00 130.00   1.00    7.50    --   38.99 110.00  43.00   46
  3  ω   -130.00 -84.00   1.00    7.50    --  -39.46-110.00 -51.00   46
  4  ω   -100.00 -37.00   1.00    7.50    --   -0.23 178.00-150.00   63
  5  ω     -6.00  56.00   1.00    7.50    --   -0.23-110.00 -51.00   62
  6  ω    -42.00  43.00   1.00    7.50    --   -0.23 -77.00-180.00   85
  7  ω     -5.00  42.00   1.00    7.50    --   38.99  77.00 -90.00   47
  8  ω     -5.00  42.00   1.00    7.50    --   38.99  77.00-180.00   47
  9  ω     -5.00  42.00   1.00    7.50    --   38.99  77.00  90.00   47
 10  ω   -140.00 -82.00   1.00    7.50    --  -39.46 -77.00 -30.00   58
 11  ω    -42.00  -8.00   1.00    7.50    --   -0.23 -77.00 120.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0096886000
_diffrn_orient_matrix_UB_12      0.0577477000
_diffrn_orient_matrix_UB_13      0.0098326000
_diffrn_orient_matrix_UB_21      -0.0315884000
_diffrn_orient_matrix_UB_22      -0.0048446000
_diffrn_orient_matrix_UB_23      0.0505403000
_diffrn_orient_matrix_UB_31      0.0576911000
_diffrn_orient_matrix_UB_32      -0.0123440000
_diffrn_orient_matrix_UB_33      0.0260371000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         1.000
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              16
_reflns_limit_l_min              -16
_reflns_number_gt                3619
_reflns_number_total             3897
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.23
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.9974
_refine_diff_density_min         -0.8464
_refine_diff_density_rms         0.1245
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.015(11)
_refine_ls_d_res_high            0.7501
_refine_ls_d_res_low             8.5741
_refine_ls_goodness_of_fit_ref   1.0319
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.0319
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+0.1374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0715
_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 Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00C(H00C), C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I)
2.c Idealised Me refined as rotating group:
 C00J(H00a,H00b,H00f), C00K(H00j,H00k,H00l), C00L(H00m,H00n,H00o)
;
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_refinement_flags_posn
Br1 Br 0.18168(2) 0.32696(3) 0.61046(2) 0.01318(9) Uani 1.000000 .
Br Br 0.57330(3) 0.18115(3) 0.93915(3) 0.02092(10) Uani 1.000000 .
O003 O 0.14163(19) 0.4882(2) 0.7829(2) 0.0166(5) Uani 1.000000 .
O004 O 0.4372(2) 0.2348(2) 0.54257(19) 0.0225(6) Uani 1.000000 .
C005 C 0.3047(3) 0.3807(3) 0.7091(2) 0.0091(6) Uani 1.000000 .
C006 C 0.4297(3) 0.3421(3) 0.7075(2) 0.0089(6) Uani 1.000000 .
C007 C 0.3481(3) 0.4949(3) 0.8654(3) 0.0148(7) Uani 1.000000 .
H007 H 0.3213(3) 0.5460(3) 0.9198(3) 0.0178(9) Uiso 1.000000 R
C008 C 0.2635(3) 0.4565(3) 0.7870(3) 0.0131(7) Uani 1.000000 .
C009 C 0.7394(3) 0.4097(3) 0.7275(3) 0.0114(7) Uani 1.000000 .
C00A C 0.6500(3) 0.3500(3) 0.7883(3) 0.0110(7) Uani 1.000000 .
C00B C 0.6916(3) 0.2647(3) 0.8568(2) 0.0129(7) Uani 1.000000 .
C00C C 0.4793(3) 0.2588(3) 0.6292(3) 0.0139(7) Uani 1.000000 .
H00C H 0.5531(3) 0.2203(3) 0.6506(3) 0.0167(9) Uiso 1.000000 R
C00D C 0.4716(3) 0.4579(3) 0.8635(3) 0.0145(7) Uani 1.000000 .
H00D H 0.5287(3) 0.4850(3) 0.9166(3) 0.0174(9) Uiso 1.000000 R
C00E C 0.8653(3) 0.3798(3) 0.7370(3) 0.0138(7) Uani 1.000000 .
H00E H 0.9259(3) 0.4182(3) 0.6945(3) 0.0165(9) Uiso 1.000000 R
C00F C 0.5133(3) 0.3826(3) 0.7862(3) 0.0121(7) Uani 1.000000 .
C00G C 0.7008(3) 0.5036(3) 0.6510(3) 0.0135(7) Uani 1.000000 .
H00G H 0.6129(3) 0.5253(3) 0.6693(3) 0.0162(8) Uiso 1.000000 R
C00H C 0.9043(3) 0.2964(3) 0.8063(3) 0.0172(8) Uani 1.000000 .
H00H H 0.9910(3) 0.2796(3) 0.8124(3) 0.0206(9) Uiso 1.000000 R
C00I C 0.8175(3) 0.2364(3) 0.8675(3) 0.0156(7) Uani 1.000000 .
H00I H 0.8434(3) 0.1781(3) 0.9149(3) 0.0187(8) Uiso 1.000000 R
C00J C 0.1004(3) 0.5664(3) 0.8645(3) 0.0174(8) Uani 1.000000 .
H00a H 0.0118(6) 0.5840(14) 0.8528(11) 0.0260(11) Uiso 1.000000 GR
H00b H 0.1112(18) 0.5333(7) 0.9369(3) 0.0260(11) Uiso 1.000000 GR
H00f H 0.1502(14) 0.6349(7) 0.8594(12) 0.0260(11) Uiso 1.000000 GR
C00K C 0.7025(3) 0.4644(3) 0.5332(3) 0.0208(8) Uani 1.000000 .
H00j H 0.7846(8) 0.4322(17) 0.5163(6) 0.0311(12) Uiso 1.000000 GR
H00k H 0.6374(15) 0.4078(14) 0.5224(5) 0.0311(12) Uiso 1.000000 GR
H00l H 0.687(2) 0.5281(5) 0.4850(3) 0.0311(12) Uiso 1.000000 GR
C00L C 0.7835(4) 0.6074(3) 0.6646(3) 0.0289(9) Uani 1.000000 .
H00m H 0.7863(18) 0.6287(12) 0.7416(4) 0.0434(14) Uiso 1.000000 GR
H00n H 0.8685(7) 0.5908(7) 0.6391(19) 0.0434(14) Uiso 1.000000 GR
H00o H 0.7486(13) 0.6691(7) 0.6218(16) 0.0434(14) Uiso 1.000000 GR


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 C005 1.899(3) . ?
Br C00B 1.903(3) . ?
O003 C008 1.356(4) . ?
O003 C00J 1.440(4) . ?
O004 C00C 1.190(4) . ?
C005 C006 1.412(4) . ?
C005 C008 1.390(4) . ?
C006 C00C 1.483(4) . ?
C006 C00F 1.403(4) . ?
C007 C008 1.398(4) . ?
C007 C00D 1.391(4) . ?
C009 C00A 1.407(4) . ?
C009 C00E 1.396(4) . ?
C009 C00G 1.522(4) . ?
C00A C00B 1.395(4) . ?
C00A C00F 1.511(4) . ?
C00B C00I 1.393(4) . ?
C00D C00F 1.383(4) . ?
C00E C00H 1.376(5) . ?
C00G C00K 1.521(5) . ?
C00G C00L 1.533(5) . ?
C00H C00I 1.392(5) . ?

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
C00J O003 C008 116.7(3) . . ?
C006 C005 Br1 122.2(2) . . ?
C008 C005 Br1 116.2(2) . . ?
C008 C005 C006 121.4(3) . . ?
C00C C006 C005 124.5(3) . . ?
C00F C006 C005 118.6(3) . . ?
C00F C006 C00C 116.9(3) . . ?
C00D C007 C008 119.8(3) . . ?
C005 C008 O003 117.4(3) . . ?
C007 C008 O003 123.6(3) . . ?
C007 C008 C005 119.0(3) . . ?
C00E C009 C00A 118.5(3) . . ?
C00G C009 C00A 121.4(3) . . ?
C00G C009 C00E 120.1(3) . . ?
C00B C00A C009 118.5(3) . . ?
C00F C00A C009 121.0(3) . . ?
C00F C00A C00B 120.4(3) . . ?
C00A C00B Br 119.6(2) . . ?
C00I C00B Br 117.5(2) . . ?
C00I C00B C00A 122.8(3) . . ?
C006 C00C O004 127.4(3) . . ?
C00F C00D C007 121.6(3) . . ?
C00H C00E C009 121.9(3) . . ?
C00A C00F C006 122.5(3) . . ?
C00D C00F C006 119.6(3) . . ?
C00D C00F C00A 117.9(3) . . ?
C00K C00G C009 110.9(3) . . ?
C00L C00G C009 112.1(3) . . ?
C00L C00G C00K 110.3(3) . . ?
C00I C00H C00E 120.5(3) . . ?
C00H C00I C00B 117.7(3) . . ?

_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 2.004
_oxdiff_exptl_absorpt_empirical_full_min 0.616
