# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_sample3_auto
_database_code_depnum_ccdc_archive 'CCDC 2244530'
loop_
_audit_author_name
_audit_author_address
'Seiji Shirakawa and Kazunobu Igawa'
;Nagasaki University
Japan
;
_audit_update_record             
;
2023-02-25 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;
_audit_creation_date             2022-07-06
_audit_creation_method           
;
Olex2 1.5-ac5-020
(compiled 2021.11.16 svn.r5db059d7 for Rigaku Oxford Diffraction, GUI svn.r6430)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        4b-pCl
_chemical_formula_moiety         '2(C10 H9 Br Cl N O2)'
_chemical_formula_sum            'C20 H18 Br2 Cl2 N2 O4'
_chemical_formula_weight         581.08
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H9BrClNO2
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'
Cl Cl 0.3639 0.7018 '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      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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.47910(10)
_cell_length_b                   14.1480(4)
_cell_length_c                   27.7407(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2150.41(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7744
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5200
_cell_measurement_theta_min      3.1710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.41a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            10628
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.614
_diffrn_reflns_theta_min         3.186
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    103.00 128.00   0.50    0.06    --  107.00  15.00-150.00   50
  2  ω     99.00 129.00   0.50    0.06    --  107.00  15.00 -90.00   60
  3  ω     99.00 128.00   0.50    0.06    --  107.00  15.00 -60.00   58
  4  ω    -11.00  30.00   0.50    0.05    --  -44.46  38.00 -30.00   82
  5  ω    -12.00  31.00   0.50    0.05    --  -44.46  38.00-150.00   86
  6  ω    -73.00 -33.00   0.50    0.06    -- -104.00  77.00 -30.00   80
  7  ω    -93.00 -67.00   0.50    0.06    -- -104.00 116.00  55.00   52
  8  ω    -57.00 -31.00   0.50    0.06    -- -104.00 116.00  55.00   52
  9  ω    -71.00 -26.00   0.50    0.05    --  -44.46 100.00 -29.00   90
 10  ω   -123.00 -40.00   0.50    0.05    --  -44.46 -26.00  44.00  166
 11  ω   -159.00 -95.00   0.50    0.06    -- -104.00 -26.00  44.00  128
 12  ω   -132.00 -97.00   0.50    0.06    -- -104.00 -15.00 -60.00   70
 13  ω   -128.00-100.00   0.50    0.06    -- -104.00 -15.00 -90.00   56
 14  ω   -123.00 -97.00   0.50    0.06    -- -104.00 -15.00-120.00   52
 15  ω     34.00  62.00   0.50    0.06    --  107.00 -77.00-180.00   56
 16  ω     42.00  68.00   0.50    0.06    --  107.00 -77.00 -90.00   52
 17  ω     41.00  67.00   0.50    0.06    --  107.00 -77.00 -60.00   52
 18  ω     33.00  88.00   0.50    0.06    --  107.00 -95.00   0.00  110
 19  ω     60.00  91.00   0.50    0.06    --  107.00-125.00 -30.00   62
 20  ω     34.00  61.00   0.50    0.06    --  107.00-100.00-133.00   54
 21  ω     69.00  94.00   0.50    0.06    --  107.00-100.00-133.00   50
;
_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      0.0566111000
_diffrn_orient_matrix_UB_12      -0.1055552000
_diffrn_orient_matrix_UB_13      0.0078108000
_diffrn_orient_matrix_UB_21      -0.0782546000
_diffrn_orient_matrix_UB_22      -0.0211244000
_diffrn_orient_matrix_UB_23      -0.0522399000
_diffrn_orient_matrix_UB_31      0.2638784000
_diffrn_orient_matrix_UB_32      0.0164226000
_diffrn_orient_matrix_UB_33      -0.0172484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                4135
_reflns_number_total             4281
_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 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 1639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0264
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+0.2980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0693
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C9(H9), N2(H2), C15(H15), C16(H16), C18(H18),
 C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.56771(10) 0.29701(3) 0.16578(2) 0.02829(12) Uani 1 1 d . . . . .
Cl1 Cl 0.88216(17) 0.66827(6) 0.40448(3) 0.02188(19) Uani 1 1 d . . . . .
O1 O 0.4788(4) 0.29876(18) 0.27612(9) 0.0159(5) Uani 1 1 d . . . . .
N1 N 0.7781(6) 0.1934(2) 0.27560(11) 0.0186(6) Uani 1 1 d . . . . .
H1 H 0.851144 0.138259 0.278113 0.022 Uiso 1 1 calc R U . . .
C1 C 0.6436(7) 0.3953(3) 0.21325(12) 0.0184(7) Uani 1 1 d . . . . .
H1A H 0.788871 0.431258 0.202535 0.022 Uiso 1 1 calc R U . . .
H1B H 0.504859 0.439947 0.215565 0.022 Uiso 1 1 calc R U . . .
O2 O 0.3832(5) 0.14767(18) 0.29203(9) 0.0184(5) Uani 1 1 d . . . . .
C2 C 0.6928(6) 0.3523(3) 0.26254(12) 0.0144(7) Uani 1 1 d . . . . .
C3 C 0.9066(7) 0.2805(2) 0.26385(13) 0.0172(7) Uani 1 1 d . . . . .
H3A H 0.989538 0.276034 0.232221 0.021 Uiso 1 1 calc R U . . .
H3B H 1.027668 0.297038 0.288963 0.021 Uiso 1 1 calc R U . . .
C4 C 0.7302(7) 0.4337(3) 0.29808(12) 0.0159(7) Uani 1 1 d . . . . .
C5 C 0.5649(7) 0.4526(3) 0.33497(12) 0.0176(7) Uani 1 1 d . . . . .
H5 H 0.422195 0.414881 0.338003 0.021 Uiso 1 1 calc R U . . .
C6 C 0.6058(7) 0.5263(3) 0.36764(13) 0.0200(7) Uani 1 1 d . . . . .
H6 H 0.492667 0.539176 0.392745 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8161(7) 0.5800(2) 0.36239(13) 0.0178(7) Uani 1 1 d . . . . .
C8 C 0.9789(7) 0.5644(3) 0.32524(13) 0.0198(8) Uani 1 1 d . . . . .
H8 H 1.118818 0.603430 0.321603 0.024 Uiso 1 1 calc R U . . .
C9 C 0.9349(8) 0.4904(3) 0.29314(13) 0.0206(7) Uani 1 1 d . . . . .
H9 H 1.046533 0.478844 0.267602 0.025 Uiso 1 1 calc R U . . .
C10 C 0.5397(7) 0.2054(2) 0.28216(12) 0.0148(7) Uani 1 1 d . . . . .
Br2 Br 0.93002(7) -0.14846(2) 0.50309(2) 0.01994(11) Uani 1 1 d . . . . .
Cl2 Cl 0.70021(19) 0.26088(6) 0.61385(3) 0.0242(2) Uani 1 1 d . . . . .
N2 N 0.5375(6) 0.0361(2) 0.37183(10) 0.0161(6) Uani 1 1 d . . . . .
H2 H 0.455827 0.060674 0.347546 0.019 Uiso 1 1 calc R U . . .
O3 O 0.8547(4) -0.00596(18) 0.41610(8) 0.0156(5) Uani 1 1 d . . . . .
O4 O 0.9252(5) 0.03574(18) 0.33899(9) 0.0195(5) Uani 1 1 d . . . . .
C11 C 0.6407(6) -0.1168(3) 0.46543(13) 0.0157(7) Uani 1 1 d . . . . .
H11A H 0.629903 -0.159574 0.437271 0.019 Uiso 1 1 calc R U . . .
H11B H 0.493261 -0.126513 0.485443 0.019 Uiso 1 1 calc R U . . .
C12 C 0.6481(6) -0.0145(2) 0.44798(12) 0.0144(7) Uani 1 1 d . . . . .
C13 C 0.4228(7) 0.0053(3) 0.41590(12) 0.0161(7) Uani 1 1 d . . . . .
H13A H 0.324382 -0.052581 0.410814 0.019 Uiso 1 1 calc R U . . .
H13B H 0.318042 0.055308 0.429834 0.019 Uiso 1 1 calc R U . . .
C14 C 0.6677(6) 0.0554(2) 0.48937(12) 0.0142(7) Uani 1 1 d . . . . .
C15 C 0.8564(6) 0.1213(2) 0.49237(13) 0.0157(7) Uani 1 1 d . . . . .
H15 H 0.978343 0.122933 0.468049 0.019 Uiso 1 1 calc R U . . .
C16 C 0.8676(7) 0.1849(3) 0.53080(14) 0.0197(8) Uani 1 1 d . . . . .
H16 H 0.997328 0.229209 0.532974 0.024 Uiso 1 1 calc R U . . .
C17 C 0.6881(7) 0.1825(2) 0.56550(13) 0.0161(7) Uani 1 1 d . . . . .
C18 C 0.4978(7) 0.1187(3) 0.56340(14) 0.0197(8) Uani 1 1 d . . . . .
H18 H 0.375564 0.117991 0.587683 0.024 Uiso 1 1 calc R U . . .
C19 C 0.4887(7) 0.0553(3) 0.52481(13) 0.0181(7) Uani 1 1 d . . . . .
H19 H 0.357877 0.011402 0.522795 0.022 Uiso 1 1 calc R U . . .
C20 C 0.7791(7) 0.0240(2) 0.37133(12) 0.0157(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.960(4) . ?
Cl1 C7 1.747(4) . ?
O1 C2 1.446(4) . ?
O1 C10 1.373(4) . ?
N1 C3 1.455(5) . ?
N1 C10 1.330(5) . ?
C1 C2 1.521(5) . ?
O2 C10 1.215(5) . ?
C2 C3 1.552(5) . ?
C2 C4 1.529(5) . ?
C4 C5 1.393(5) . ?
C4 C9 1.386(5) . ?
C5 C6 1.400(5) . ?
C6 C7 1.388(5) . ?
C7 C8 1.381(5) . ?
C8 C9 1.395(5) . ?
Br2 C11 1.950(3) . ?
Cl2 C17 1.742(4) . ?
N2 C13 1.442(4) . ?
N2 C20 1.335(5) . ?
O3 C12 1.441(4) . ?
O3 C20 1.376(4) . ?
O4 C20 1.214(4) . ?
C11 C12 1.527(5) . ?
C12 C13 1.548(5) . ?
C12 C14 1.519(5) . ?
C14 C15 1.394(5) . ?
C14 C19 1.389(5) . ?
C15 C16 1.396(5) . ?
C16 C17 1.376(5) . ?
C17 C18 1.380(5) . ?
C18 C19 1.398(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
C10 O1 C2 109.8(3) . . ?
C10 N1 C3 113.5(3) . . ?
C2 C1 Br1 110.9(2) . . ?
O1 C2 C1 107.5(3) . . ?
O1 C2 C3 105.2(3) . . ?
O1 C2 C4 109.6(3) . . ?
C1 C2 C3 114.7(3) . . ?
C1 C2 C4 107.6(3) . . ?
C4 C2 C3 112.1(3) . . ?
N1 C3 C2 101.2(3) . . ?
C5 C4 C2 122.1(3) . . ?
C9 C4 C2 118.7(3) . . ?
C9 C4 C5 119.2(3) . . ?
C4 C5 C6 121.0(4) . . ?
C7 C6 C5 118.2(3) . . ?
C6 C7 Cl1 119.6(3) . . ?
C8 C7 Cl1 118.6(3) . . ?
C8 C7 C6 121.8(3) . . ?
C7 C8 C9 119.0(4) . . ?
C4 C9 C8 120.7(3) . . ?
N1 C10 O1 110.1(3) . . ?
O2 C10 O1 120.2(3) . . ?
O2 C10 N1 129.7(3) . . ?
C20 N2 C13 113.7(3) . . ?
C20 O3 C12 110.1(3) . . ?
C12 C11 Br2 111.5(2) . . ?
O3 C12 C11 107.1(3) . . ?
O3 C12 C13 105.0(3) . . ?
O3 C12 C14 110.7(3) . . ?
C11 C12 C13 109.4(3) . . ?
C14 C12 C11 112.3(3) . . ?
C14 C12 C13 111.9(3) . . ?
N2 C13 C12 101.2(3) . . ?
C15 C14 C12 122.2(3) . . ?
C19 C14 C12 119.0(3) . . ?
C19 C14 C15 118.8(3) . . ?
C14 C15 C16 120.6(3) . . ?
C17 C16 C15 119.1(3) . . ?
C16 C17 Cl2 119.7(3) . . ?
C16 C17 C18 121.8(3) . . ?
C18 C17 Cl2 118.5(3) . . ?
C17 C18 C19 118.6(3) . . ?
C14 C19 C18 121.1(3) . . ?
N2 C20 O3 109.2(3) . . ?
O4 C20 N2 130.1(4) . . ?
O4 C20 O3 120.7(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 1.648
_oxdiff_exptl_absorpt_empirical_full_min 0.733
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate-Hexane'
####################################################################### 
# 
# 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_sample2_auto
_database_code_depnum_ccdc_archive 'CCDC 2244531'
loop_
_audit_author_name
_audit_author_address
'Seiji Shirakawa and Kazunobu Igawa'
;Nagasaki University
Japan
;
_audit_update_record             
;
2023-02-25 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;
_audit_creation_date             2022-07-06
_audit_creation_method           
;
Olex2 1.5-ac5-020
(compiled 2021.11.16 svn.r5db059d7 for Rigaku Oxford Diffraction, GUI svn.r6430)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        4d-OCF3
_chemical_formula_moiety         'C11 H9 Br F3 N O3'
_chemical_formula_sum            'C11 H9 Br F3 N O3'
_chemical_formula_weight         340.10
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C11H9BrF3NO3
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                   12.3801(2)
_cell_length_b                   5.46613(14)
_cell_length_c                   18.0363(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.6831(18)
_cell_angle_gamma                90
_cell_volume                     1218.01(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4847
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6090
_cell_measurement_theta_min      2.4880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.41a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6540
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.110
_diffrn_reflns_theta_min         2.455
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     94.00 119.00   0.50    0.09    --  107.00  61.00-150.00   50
  2  ω     95.00 121.00   0.50    0.09    --  107.00  61.00-180.00   52
  3  ω    129.00 174.00   0.50    0.09    --  107.00  61.00-150.00   90
  4  ω    148.00 175.00   0.50    0.09    --  107.00  45.00 -30.00   54
  5  ω    -60.00 -35.00   0.50    0.05    --  -44.46 -52.00 136.47   50
  6  ω    -94.00 -42.00   0.50    0.05    --  -44.46 -52.00 125.27  104
  7  ω    -96.00 -70.00   0.50    0.05    --  -44.46 -52.00 136.47   52
  8  ω    -62.00 -36.00   0.50    0.05    --  -44.46 -48.00 152.10   52
  9  ω   -115.00 -81.00   0.50    0.05    --  -44.46 -47.00 162.02   68
 10  ω    -63.00 -38.00   0.50    0.05    --  -44.46 -47.00 162.02   50
 11  ω    -58.00 -33.00   0.50    0.05    --  -44.46 -52.00  56.99   50
 12  ω    -76.00 -36.00   0.50    0.05    --  -44.46 -38.00  60.00   80
 13  ω   -115.00 -89.00   0.50    0.05    --  -44.46 -38.00  60.00   52
 14  ω    -68.00 -36.00   0.50    0.05    --  -44.46 -38.00-150.00   64
 15  ω    -79.00 -34.00   0.50    0.05    --  -44.46 -51.00-165.99   90
 16  ω   -108.00 -82.00   0.50    0.05    --  -44.46 -51.00-165.99   52
 17  ω   -115.00 -90.00   0.50    0.09    -- -104.00 -62.00-107.23   50
 18  ω   -116.00 -91.00   0.50    0.09    -- -104.00 -61.00-120.00   50
 19  ω   -115.00 -90.00   0.50    0.09    -- -104.00 -61.00-180.00   50
 20  ω   -115.00 -90.00   0.50    0.09    -- -104.00 -61.00-150.00   50
 21  ω   -174.00-136.00   0.50    0.09    -- -104.00 -61.00-180.00   76
 22  ω   -175.00-139.00   0.50    0.09    -- -104.00 -61.00-150.00   72
 23  ω   -168.00-142.00   0.50    0.09    -- -104.00 -62.00-107.23   52
 24  ω   -171.00-145.00   0.50    0.09    -- -104.00 -59.00-125.54   52
 25  ω   -126.00 -93.00   0.50    0.09    -- -104.00 -59.00-125.54   66
 26  ω   -116.00 -91.00   0.50    0.09    -- -104.00 -59.00-134.31   50
 27  ω   -117.00 -92.00   0.50    0.09    -- -104.00 -58.00-172.85   50
 28  ω   -115.00 -90.00   0.50    0.09    -- -104.00 -61.00 120.00   50
 29  ω   -115.00 -90.00   0.50    0.09    -- -104.00 -61.00 150.00   50
 30  ω   -124.00 -91.00   0.50    0.09    -- -104.00 -58.00 161.27   66
 31  ω   -118.00 -93.00   0.50    0.09    -- -104.00 -58.00 168.14   50
 32  ω   -118.00 -93.00   0.50    0.09    -- -104.00 -57.00 179.39   50
 33  ω   -175.00-149.00   0.50    0.09    -- -104.00 -58.00 161.27   52
 34  ω   -172.00-146.00   0.50    0.09    -- -104.00 -58.00 168.14   52
 35  ω   -168.00-141.00   0.50    0.09    -- -104.00 -49.00 117.13   54
 36  ω   -121.00 -93.00   0.50    0.09    -- -104.00 -49.00 117.13   56
 37  ω   -119.00 -94.00   0.50    0.09    -- -104.00 -46.00-101.41   50
 38  ω   -122.00 -96.00   0.50    0.09    -- -104.00 -46.00-111.79   52
 39  ω   -131.00-105.00   0.50    0.09    -- -104.00 -45.00-150.00   52
 40  ω   -118.00 -93.00   0.50    0.09    -- -104.00 -45.00-180.00   50
 41  ω   -171.00-145.00   0.50    0.09    -- -104.00 -46.00-101.41   52
 42  ω   -121.00 -96.00   0.50    0.09    -- -104.00 -43.00-175.24   50
 43  ω   -118.00 -93.00   0.50    0.09    -- -104.00 -45.00 120.00   50
 44  ω   -122.00 -96.00   0.50    0.09    -- -104.00 -43.00 176.36   52
 45  ω   -123.00 -97.00   0.50    0.09    -- -104.00 -43.00 167.51   52
 46  ω   -126.00 -97.00   0.50    0.09    -- -104.00 -30.00  90.00   58
 47  ω   -128.00-103.00   0.50    0.09    -- -104.00 -15.00-120.00   50
 48  ω   -120.00 -95.00   0.50    0.09    -- -104.00 -30.00-180.00   50
 49  ω    -27.00   2.00   0.50    0.05    --   44.46 -38.00  30.00   58
 50  ω     36.00  99.00   0.50    0.09    --  107.00-125.00 -90.00  126
 51  ω     35.00  83.00   0.50    0.09    --  107.00 -95.00-150.00   96
 52  ω     34.00  59.00   0.50    0.09    --  107.00 -95.00-180.00   50
 53  ω     68.00  93.00   0.50    0.09    --  107.00 -95.00-180.00   50
 54  ω      3.00  74.00   0.50    0.05    --   44.46 -99.00 -60.00  142
 55  ω     57.00  84.00   0.50    0.09    --  107.00 -95.00 150.00   54
 56  ω     35.00  74.00   0.50    0.09    --  107.00 -95.00 120.00   78
;
_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      -0.1233760000
_diffrn_orient_matrix_UB_12      -0.0350339000
_diffrn_orient_matrix_UB_13      0.0004956000
_diffrn_orient_matrix_UB_21      0.0092721000
_diffrn_orient_matrix_UB_22      -0.0091618000
_diffrn_orient_matrix_UB_23      0.0854904000
_diffrn_orient_matrix_UB_31      -0.0153191000
_diffrn_orient_matrix_UB_32      0.2797031000
_diffrn_orient_matrix_UB_33      0.0029076000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.833
_reflns_Friedel_fraction_max     0.805
_reflns_number_gt                2137
_reflns_number_total             2195
_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 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.037(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+0.6125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0620
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.65793(2) 0.23425(8) 0.79417(2) 0.02026(13) Uani 1 1 d . . . . .
F1 F 0.0865(2) 0.4831(8) 0.60397(16) 0.0450(9) Uani 1 1 d . . . . .
O1 O 0.45017(18) 0.2710(6) 0.89391(13) 0.0147(6) Uani 1 1 d . . . . .
N1 N 0.3614(2) 0.5714(7) 0.94519(17) 0.0166(7) Uani 1 1 d . . . . .
H1 H 0.314579 0.644799 0.972410 0.020 Uiso 1 1 calc R U . . .
C1 C 0.6001(3) 0.4993(8) 0.8520(2) 0.0166(8) Uani 1 1 d . . . . .
H1A H 0.632135 0.490471 0.903635 0.020 Uiso 1 1 calc R U . . .
H1B H 0.621212 0.657904 0.830723 0.020 Uiso 1 1 calc R U . . .
F2 F 0.11719(19) 0.5910(6) 0.49234(13) 0.0307(6) Uani 1 1 d . . . . .
O2 O 0.2547(2) 0.5003(7) 0.56668(15) 0.0245(7) Uani 1 1 d . . . . .
C2 C 0.4775(3) 0.4878(8) 0.8528(2) 0.0136(7) Uani 1 1 d . . . . .
F3 F 0.1552(3) 0.8330(7) 0.58404(18) 0.0370(8) Uani 1 1 d . . . . .
O3 O 0.3232(2) 0.1690(5) 0.97196(15) 0.0200(7) Uani 1 1 d . . . . .
C3 C 0.4364(3) 0.7022(9) 0.90006(18) 0.0164(9) Uani 1 1 d . . . . .
H3A H 0.496097 0.778670 0.931078 0.020 Uiso 1 1 calc R U . . .
H3B H 0.399033 0.828628 0.868622 0.020 Uiso 1 1 calc R U . . .
C4 C 0.4206(3) 0.4817(8) 0.7757(2) 0.0149(8) Uani 1 1 d . . . . .
C5 C 0.3473(3) 0.2976(7) 0.7547(2) 0.0183(10) Uani 1 1 d . . . . .
H5 H 0.335573 0.167300 0.788050 0.022 Uiso 1 1 calc R U . . .
C6 C 0.2909(3) 0.3016(8) 0.6856(2) 0.0210(10) Uani 1 1 d . . . . .
H6 H 0.241280 0.175061 0.671230 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3088(3) 0.4945(9) 0.6380(2) 0.0195(8) Uani 1 1 d . . . . .
C8 C 0.3826(3) 0.6773(8) 0.6566(2) 0.0199(10) Uani 1 1 d . . . . .
H8 H 0.394927 0.805682 0.622587 0.024 Uiso 1 1 calc R U . . .
C9 C 0.4387(3) 0.6700(7) 0.7259(2) 0.0171(9) Uani 1 1 d . . . . .
H9 H 0.489829 0.794466 0.739457 0.021 Uiso 1 1 calc R U . . .
C10 C 0.1548(4) 0.5997(12) 0.5627(3) 0.0251(11) Uani 1 1 d . . . . .
C11 C 0.3714(3) 0.3292(8) 0.9407(2) 0.0154(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.948(4) . ?
F1 C10 1.325(6) . ?
O1 C2 1.449(5) . ?
O1 C11 1.368(4) . ?
N1 C3 1.461(5) . ?
N1 C11 1.332(6) . ?
C1 C2 1.520(5) . ?
F2 C10 1.325(5) . ?
O2 C7 1.413(4) . ?
O2 C10 1.349(6) . ?
C2 C3 1.554(6) . ?
C2 C4 1.519(5) . ?
F3 C10 1.332(6) . ?
O3 C11 1.218(5) . ?
C4 C5 1.391(6) . ?
C4 C9 1.394(6) . ?
C5 C6 1.388(5) . ?
C6 C7 1.386(6) . ?
C7 C8 1.381(6) . ?
C8 C9 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
C11 O1 C2 108.9(3) . . ?
C11 N1 C3 112.8(3) . . ?
C2 C1 Br1 112.1(3) . . ?
C10 O2 C7 115.9(3) . . ?
O1 C2 C1 107.8(3) . . ?
O1 C2 C3 103.9(3) . . ?
O1 C2 C4 109.9(3) . . ?
C1 C2 C3 109.7(3) . . ?
C4 C2 C1 113.4(3) . . ?
C4 C2 C3 111.7(3) . . ?
N1 C3 C2 100.3(4) . . ?
C5 C4 C2 121.5(4) . . ?
C5 C4 C9 119.2(3) . . ?
C9 C4 C2 119.3(3) . . ?
C6 C5 C4 121.0(4) . . ?
C7 C6 C5 118.4(4) . . ?
C6 C7 O2 119.7(4) . . ?
C8 C7 O2 118.1(4) . . ?
C8 C7 C6 122.1(4) . . ?
C7 C8 C9 118.7(4) . . ?
C8 C9 C4 120.6(4) . . ?
F1 C10 F2 108.8(4) . . ?
F1 C10 O2 113.1(5) . . ?
F1 C10 F3 106.8(4) . . ?
F2 C10 O2 107.5(4) . . ?
F2 C10 F3 107.8(5) . . ?
F3 C10 O2 112.6(5) . . ?
N1 C11 O1 109.9(3) . . ?
O3 C11 O1 120.5(4) . . ?
O3 C11 N1 129.5(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 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.741
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane-Hexane'
