# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_SS-C20H20Br2N2O2-298K
_database_code_depnum_ccdc_archive 'CCDC 2389142'
loop_
_audit_author_name
_audit_author_address
'Xin Shen'
;Nanchang University
China
;
_audit_update_record             
;
2024-10-07 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 Br2 N2 O2'
_chemical_formula_sum            'C20 H20 Br2 N2 O2'
_chemical_formula_weight         480.20
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
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                   5.9191(3)
_cell_length_b                   19.0670(7)
_cell_length_c                   9.0123(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1017.12(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2369
_cell_measurement_temperature    298.01(10)
_cell_measurement_theta_max      71.6240
_cell_measurement_theta_min      4.6250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4211
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.937
_diffrn_reflns_theta_min         4.638
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     58.00  92.00   0.50    0.05    --   75.18 167.00  95.00   68
  2  ω     69.00 110.00   0.50    0.05    --   60.54  30.00 -90.00   82
  3  ω     11.00  38.00   0.50    0.05    --   60.54 -30.00   0.00   54
  4  ω     11.00  37.00   0.50    0.05    --   60.54 -30.00 -90.00   52
  5  ω     11.00  36.00   0.50    0.05    --   60.54 -30.00-180.00   50
  6  ω     37.00  80.00   0.50    0.05    --   75.18 -94.00-120.00   86
  7  ω     66.00  91.00   0.50    0.05    --   60.54-167.00  75.00   50
  8  ω     34.00  78.00   0.50    0.05    --   75.18-115.00-138.00   88
  9  ω     47.00  73.00   0.50    0.05    --   60.54-115.00-138.00   52
 10  ω   -117.00 -75.00   0.50    0.05    --  -75.50-125.00  90.00   84
 11  ω   -114.00 -89.00   0.50    0.05    --  -74.13-125.00 150.00   50
 12  ω    -87.00 -61.00   0.50    0.05    --  -74.13-167.00  75.00   52
 13  ω   -118.00 -79.00   0.50    0.05    --  -74.13-125.00  30.00   78
 14  ω   -108.00 -82.00   0.50    0.05    --  -74.13-125.00 -60.00   52
 15  ω   -101.00 -73.00   0.50    0.05    --  -74.13-125.00-150.00   56
 16  ω   -106.00 -81.00   0.50    0.05    --  -74.13 -30.00  90.00   50
 17  ω   -119.00 -94.00   0.50    0.05    --  -74.13 -30.00  30.00   50
 18  ω    -51.00 -26.00   0.50    0.05    --  -60.72 115.00 -49.00   50
 19  ω    -84.00 -38.00   0.50    0.05    --  -60.72 167.00  95.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0196786000
_diffrn_orient_matrix_UB_12      0.0710847000
_diffrn_orient_matrix_UB_13      0.0801410000
_diffrn_orient_matrix_UB_21      0.2559404000
_diffrn_orient_matrix_UB_22      -0.0115454000
_diffrn_orient_matrix_UB_23      0.0186033000
_diffrn_orient_matrix_UB_31      0.0424617000
_diffrn_orient_matrix_UB_32      0.0366691000
_diffrn_orient_matrix_UB_33      -0.1498627000
_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         0.545
_reflns_Friedel_fraction_full    0.810
_reflns_Friedel_fraction_max     0.752
_reflns_number_gt                1272
_reflns_number_total             1721
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.681
_refine_diff_density_min         -1.020
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details 
;
 Flack x determined using 349 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1721
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0730
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1621
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C4(H4), C2(H2)
2.d Fitted hexagon refined as free rotating group:
 C1(C6,C5,C4,C3,C2)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.5107(3) 0.21182(8) 0.82910(14) 0.0866(6) Uani 1 1 d . . . . .
N1 N 0.3775(17) 0.4336(4) 0.2911(11) 0.058(3) Uani 1 1 d . . . . .
O1 O 0.0221(19) 0.4238(5) 0.4597(11) 0.082(3) Uani 1 1 d . . . . .
H1 H 0.098468 0.435862 0.388253 0.124 Uiso 1 1 calc R U . . .
C7 C 0.470(2) 0.3877(5) 0.3742(11) 0.054(3) Uani 1 1 d . . . . .
H7 H 0.617518 0.373667 0.353408 0.065 Uiso 1 1 calc R U . . .
C1 C 0.3531(12) 0.3561(3) 0.5011(7) 0.049(3) Uani 1 1 d G . . . .
C6 C 0.1375(12) 0.3780(3) 0.5409(8) 0.056(3) Uani 1 1 d G . . . .
C5 C 0.0338(10) 0.3502(4) 0.6661(9) 0.061(3) Uani 1 1 d G . . . .
H5 H -0.110471 0.364840 0.692696 0.074 Uiso 1 1 calc R U . . .
C4 C 0.1456(13) 0.3004(4) 0.7515(7) 0.068(3) Uani 1 1 d G . . . .
H4 H 0.076198 0.281733 0.835249 0.081 Uiso 1 1 calc R U . . .
C3 C 0.3612(13) 0.2784(3) 0.7117(7) 0.058(3) Uani 1 1 d G . . . .
C2 C 0.4650(10) 0.3063(3) 0.5865(8) 0.051(3) Uani 1 1 d G . . . .
H2 H 0.609235 0.291602 0.559920 0.062 Uiso 1 1 calc R U . . .
C8 C 0.507(3) 0.4599(5) 0.1633(12) 0.063(3) Uani 1 1 d . . . . .
H8 H 0.665036 0.445006 0.171197 0.075 Uiso 1 1 calc R U . . .
C9 C 0.402(3) 0.4299(7) 0.0239(15) 0.090(5) Uani 1 1 d . . . . .
H9A H 0.241400 0.439723 0.023480 0.108 Uiso 1 1 calc R U . . .
H9B H 0.421621 0.379345 0.023261 0.108 Uiso 1 1 calc R U . . .
C10 C 0.511(5) 0.4612(7) -0.1162(14) 0.110(6) Uani 1 1 d . . . . .
H10A H 0.669147 0.448329 -0.119890 0.132 Uiso 1 1 calc R U . . .
H10B H 0.437286 0.442172 -0.203575 0.132 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.1027(12) 0.0968(10) 0.0603(9) 0.0135(7) -0.0111(11) 0.0124(11)
N1 0.060(6) 0.049(5) 0.063(7) 0.008(4) -0.003(5) -0.004(4)
O1 0.057(6) 0.078(5) 0.112(7) 0.014(5) -0.001(7) 0.016(6)
C7 0.045(7) 0.056(5) 0.061(7) -0.012(5) -0.004(6) -0.019(6)
C1 0.046(6) 0.048(5) 0.054(8) -0.007(5) -0.006(6) -0.004(5)
C6 0.047(7) 0.047(6) 0.074(9) -0.010(6) -0.002(6) 0.001(5)
C5 0.047(7) 0.067(6) 0.070(7) -0.017(6) 0.010(8) -0.005(6)
C4 0.074(9) 0.081(9) 0.048(7) -0.017(7) 0.006(7) -0.013(7)
C3 0.059(7) 0.062(6) 0.051(8) -0.022(6) 0.001(6) -0.004(6)
C2 0.048(6) 0.055(5) 0.052(6) -0.016(4) -0.003(6) -0.003(5)
C8 0.062(7) 0.053(5) 0.073(7) 0.001(5) -0.001(11) -0.017(6)
C9 0.130(16) 0.063(7) 0.076(10) -0.011(7) 0.000(10) -0.034(8)
C10 0.167(16) 0.097(9) 0.066(8) -0.014(7) 0.001(14) -0.053(15)

_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 1.875(5) . ?
N1 C7 1.277(14) . ?
N1 C8 1.472(14) . ?
O1 H1 0.8200 . ?
O1 C6 1.328(10) . ?
C7 H7 0.9300 . ?
C7 C1 1.467(12) . ?
C1 C6 1.3900 . ?
C1 C2 1.3900 . ?
C6 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C3 1.3900 . ?
C3 C2 1.3900 . ?
C2 H2 0.9300 . ?
C8 C8 1.531(19) 2_665 ?
C8 H8 0.9800 . ?
C8 C9 1.514(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.54(2) . ?
C10 C10 1.49(3) 2_665 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 N1 C8 117.9(11) . . ?
C6 O1 H1 109.5 . . ?
N1 C7 H7 118.8 . . ?
N1 C7 C1 122.4(11) . . ?
C1 C7 H7 118.8 . . ?
C6 C1 C7 120.8(7) . . ?
C6 C1 C2 120.0 . . ?
C2 C1 C7 119.1(7) . . ?
O1 C6 C1 121.9(7) . . ?
O1 C6 C5 118.1(7) . . ?
C5 C6 C1 120.0 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 Br1 119.4(4) . . ?
C4 C3 C2 120.0 . . ?
C2 C3 Br1 120.5(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
N1 C8 C8 108.2(10) . 2_665 ?
N1 C8 H8 110.0 . . ?
N1 C8 C9 107.9(10) . . ?
C8 C8 H8 110.0 2_665 . ?
C9 C8 C8 110.8(9) . 2_665 ?
C9 C8 H8 110.0 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C8 C9 C10 111.3(11) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C10 C10 C9 110.6(16) 2_665 . ?
C10 C10 H10A 109.5 2_665 . ?
C10 C10 H10B 109.5 2_665 . ?
H10A C10 H10B 108.1 . . ?

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 C2 C1 -179.5(5) . . . . ?
N1 C7 C1 C6 -3.4(12) . . . . ?
N1 C7 C1 C2 180.0(8) . . . . ?
N1 C8 C9 C10 173.6(15) . . . . ?
O1 C6 C5 C4 177.9(8) . . . . ?
C7 N1 C8 C8 -132.1(14) . . . 2_665 ?
C7 N1 C8 C9 107.9(12) . . . . ?
C7 C1 C6 O1 5.6(9) . . . . ?
C7 C1 C6 C5 -176.6(7) . . . . ?
C7 C1 C2 C3 176.7(7) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 Br1 179.5(5) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C2 C1 C6 O1 -177.8(9) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C8 N1 C7 C1 -177.7(8) . . . . ?
C8 C8 C9 C10 55(2) 2_665 . . . ?
C8 C9 C10 C10 -57(3) . . . 2_665 ?

_shelx_res_file                  
;
TITL SS-C20H20Br2N2O2-298K_a.res in P2(1)2(1)2
    SS-C20H20Br2N2O2-298K.res
    created by SHELXL-2018/3 at 10:52:29 on 11-Sep-2024
REM Old TITL SS-C20H20Br2N2O2-298K in P2(1)2(1)2
REM SHELXT solution in P2(1)2(1)2: R1 0.170, Rweak 0.038, Alpha 0.017
REM <I/s> 0.278 for 16 systematic absences, Orientation as input
REM Flack x = 0.032 ( 0.057 ) from 406 Parsons' quotients
REM Formula found by SHELXT: C10 O1 O Br
CELL 1.54184 5.9191 19.067 9.0123 90 90 90
ZERR 2 0.0003 0.0007 0.0005 0 0 0
LATT -1
SYMM -X,-Y,+Z
SYMM 0.5-X,0.5+Y,-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br N O
UNIT 40 40 4 4 4

L.S. 4
PLAN  4
TEMP 25
CONF
BOND
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\SS-C20H20Br2N2O2-298K.hkl">
REM </olex2.extras>

WGHT    0.020000    4.000000
FVAR       0.60601
BR1   3    0.510705    0.211817    0.829101    11.00000    0.10275    0.09675 =
         0.06025    0.01355   -0.01112    0.01240
N1    4    0.377538    0.433644    0.291128    11.00000    0.06021    0.04921 =
         0.06327    0.00806   -0.00254   -0.00431
O1    5    0.022077    0.423795    0.459734    11.00000    0.05730    0.07826 =
         0.11190    0.01361   -0.00070    0.01592
AFIX 147
H1    2    0.098468    0.435862    0.388253    11.00000   -1.50000
AFIX   0
C7    1    0.470348    0.387652    0.374157    11.00000    0.04524    0.05641 =
         0.06134   -0.01235   -0.00419   -0.01892
AFIX  43
H7    2    0.617518    0.373667    0.353408    11.00000   -1.20000
AFIX  66
C1    1    0.353140    0.356076    0.501122    11.00000    0.04640    0.04777 =
         0.05375   -0.00694   -0.00610   -0.00379
C6    1    0.137540    0.378015    0.540899    11.00000    0.04673    0.04681 =
         0.07366   -0.01047   -0.00199    0.00145
C5    1    0.033780    0.350161    0.666083    11.00000    0.04697    0.06733 =
         0.06955   -0.01667    0.01022   -0.00498
AFIX  43
H5    2   -0.110471    0.364840    0.692696    11.00000   -1.20000
AFIX  65
C4    1    0.145621    0.300368    0.751492    11.00000    0.07352    0.08148 =
         0.04760   -0.01655    0.00636   -0.01311
AFIX  43
H4    2    0.076198    0.281733    0.835249    11.00000   -1.20000
AFIX  65
C3    1    0.361222    0.278429    0.711717    11.00000    0.05928    0.06233 =
         0.05125   -0.02216    0.00082   -0.00369
C2    1    0.464983    0.306282    0.586533    11.00000    0.04792    0.05462 =
         0.05176   -0.01620   -0.00297   -0.00315
AFIX  43
H2    2    0.609235    0.291602    0.559920    11.00000   -1.20000
AFIX   0
C8    1    0.507044    0.459914    0.163312    11.00000    0.06223    0.05341 =
         0.07250    0.00148   -0.00100   -0.01729
AFIX  13
H8    2    0.665036    0.445006    0.171197    11.00000   -1.20000
AFIX   0
C9    1    0.402165    0.429858    0.023864    11.00000    0.12980    0.06303 =
         0.07616   -0.01122    0.00030   -0.03380
AFIX  23
H9A   2    0.241400    0.439723    0.023480    11.00000   -1.20000
H9B   2    0.421621    0.379345    0.023261    11.00000   -1.20000
AFIX   0
C10   1    0.510695    0.461190   -0.116163    11.00000    0.16689    0.09684 =
         0.06625   -0.01429    0.00131   -0.05268
AFIX  23
H10A  2    0.669147    0.448329   -0.119890    11.00000   -1.20000
H10B  2    0.437286    0.442172   -0.203575    11.00000   -1.20000
AFIX   0
HKLF 4




REM  SS-C20H20Br2N2O2-298K_a.res in P2(1)2(1)2
REM wR2 = 0.1621, GooF = S = 1.154, Restrained GooF = 1.154 for all data
REM R1 = 0.0730 for 1272 Fo > 4sig(Fo) and 0.0936 for all 1721 data
REM 107 parameters refined using 0 restraints

END

WGHT      0.1403      0.0000

REM Highest difference peak  0.681,  deepest hole -1.020,  1-sigma level  0.118
Q1    1   0.5084  0.1787  0.7550  11.00000  0.05    0.68
Q2    1   0.5194  0.1742  0.8946  11.00000  0.05    0.52
Q3    1   0.3900  0.2387  0.8819  11.00000  0.05    0.52
Q4    1   0.6140  0.2455  0.8789  11.00000  0.05    0.51
;
_shelx_res_checksum              67252
_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 8.653
_oxdiff_exptl_absorpt_empirical_full_min 0.107
####################################################################### 
# 
# 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_RR-C20H20Br2N2O2-298K
_database_code_depnum_ccdc_archive 'CCDC 2411527'
loop_
_audit_author_name
_audit_author_address
'Xin Shen'
;Nanchang University
China
;
_audit_update_record             
;
2024-12-19 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_audit_creation_date             2024-12-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 Br2 N2 O2'
_chemical_formula_sum            'C20 H20 Br2 N2 O2'
_chemical_formula_weight         480.20
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
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                   5.92480(10)
_cell_length_b                   19.0854(3)
_cell_length_c                   9.01350(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1019.22(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2665
_cell_measurement_temperature    297.90(10)
_cell_measurement_theta_max      75.4640
_cell_measurement_theta_min      2.2750
_shelx_estimated_absorpt_T_max   0.626
_shelx_estimated_absorpt_T_min   0.626
_exptl_absorpt_coefficient_mu    5.174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3307
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.644
_diffrn_reflns_theta_min         4.634
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.90(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     56.00 178.00   0.50    0.05    --  108.36   9.00-127.00  244
  2  ω     70.00 110.00   0.50    0.05    --  108.36-121.00 -52.00   80
  3  ω     41.00  68.00   0.50    0.05    --  108.36 -61.00  90.00   54
  4  ω     -7.00  32.00   0.50    0.10    --  -45.20  19.00 -60.00   78
  5  ω    -24.00   3.00   0.50    0.10    --  -45.20  19.00  90.00   54
  6  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00  60.00   80
  7  ω   -123.00 -55.00   0.50    0.05    -- -102.00 141.00 107.00  136
  8  ω    -76.00 -34.00   0.50    0.05    -- -102.00 121.00  30.00   84
  9  ω    -84.00 -52.00   0.50    0.10    --  -45.20 121.00  30.00   64
 10  ω   -117.00 -61.00   0.50    0.10    --  -45.20 -57.00-150.00  112
;
_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      -0.0489005000
_diffrn_orient_matrix_UB_12      0.0077397000
_diffrn_orient_matrix_UB_13      -0.1670387000
_diffrn_orient_matrix_UB_21      -0.2550665000
_diffrn_orient_matrix_UB_22      -0.0054608000
_diffrn_orient_matrix_UB_23      0.0311079000
_diffrn_orient_matrix_UB_31      -0.0126711000
_diffrn_orient_matrix_UB_32      0.0801736000
_diffrn_orient_matrix_UB_33      0.0182690000
_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         0.552
_reflns_Friedel_fraction_full    0.845
_reflns_Friedel_fraction_max     0.765
_reflns_number_gt                1732
_reflns_number_total             1880
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 573 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       0.030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.070
_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)+(0.0720P)²+0.2101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1243
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C4(H4), C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.48907(12) 0.78834(4) 0.17114(6) 0.0841(4) Uani 1 1 d . . . . .
O1 O 0.9785(7) 0.5750(2) 0.5396(6) 0.0823(12) Uani 1 1 d . . . . .
H1 H 0.903540 0.563196 0.611841 0.123 Uiso 1 1 calc R U . . .
N1 N 0.6195(7) 0.5669(2) 0.7074(5) 0.0596(11) Uani 1 1 d . . . . .
C2 C 0.5366(8) 0.6939(2) 0.4131(5) 0.0507(10) Uani 1 1 d . . . . .
H2 H 0.393102 0.709382 0.439216 0.061 Uiso 1 1 calc R U . . .
C1 C 0.6445(8) 0.6433(2) 0.4990(5) 0.0495(10) Uani 1 1 d . . . . .
C7 C 0.5276(8) 0.6128(2) 0.6261(5) 0.0514(9) Uani 1 1 d . . . . .
H7 H 0.381640 0.627442 0.647853 0.062 Uiso 1 1 calc R U . . .
C4 C 0.8550(10) 0.7002(3) 0.2489(6) 0.0633(13) Uani 1 1 d . . . . .
H4 H 0.924376 0.719036 0.165327 0.076 Uiso 1 1 calc R U . . .
C6 C 0.8632(8) 0.6219(2) 0.4603(7) 0.0582(12) Uani 1 1 d . . . . .
C3 C 0.6423(9) 0.7212(3) 0.2890(5) 0.0573(11) Uani 1 1 d . . . . .
C8 C 0.4956(10) 0.5401(2) 0.8360(5) 0.0631(12) Uani 1 1 d . . . . .
H8 H 0.337765 0.555106 0.828889 0.076 Uiso 1 1 calc R U . . .
C5 C 0.9646(8) 0.6509(3) 0.3341(6) 0.0645(13) Uani 1 1 d . . . . .
H5 H 1.108918 0.636520 0.307314 0.077 Uiso 1 1 calc R U . . .
C9 C 0.5980(14) 0.5701(3) 0.9770(7) 0.086(2) Uani 1 1 d . . . . .
H9A H 0.758845 0.560603 0.977863 0.103 Uiso 1 1 calc R U . . .
H9B H 0.577930 0.620578 0.977365 0.103 Uiso 1 1 calc R U . . .
C10 C 0.4923(19) 0.5397(4) 1.1155(7) 0.103(2) Uani 1 1 d . . . . .
H10A H 0.335099 0.553642 1.120867 0.124 Uiso 1 1 calc R U . . .
H10B H 0.568871 0.558027 1.202313 0.124 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0999(6) 0.0938(5) 0.0586(4) 0.0115(3) -0.0106(4) 0.0105(4)
O1 0.055(2) 0.0676(19) 0.124(4) 0.015(2) 0.001(3) 0.0161(19)
N1 0.058(2) 0.047(2) 0.074(3) 0.0036(19) 0.001(2) -0.0084(18)
C2 0.045(2) 0.058(2) 0.049(2) -0.0117(18) -0.0021(19) 0.0020(18)
C1 0.045(2) 0.048(2) 0.056(2) -0.008(2) -0.005(2) -0.0031(18)
C7 0.044(2) 0.053(2) 0.058(2) -0.0069(18) 0.000(2) -0.006(2)
C4 0.066(3) 0.073(3) 0.051(2) -0.010(2) 0.008(2) -0.012(3)
C6 0.047(2) 0.048(2) 0.080(3) -0.008(2) -0.004(2) 0.001(2)
C3 0.063(3) 0.061(3) 0.048(2) -0.008(2) -0.001(2) -0.003(2)
C8 0.070(3) 0.051(2) 0.068(3) 0.0007(19) 0.005(4) -0.010(2)
C5 0.043(2) 0.071(3) 0.079(3) -0.021(3) 0.007(3) 0.002(2)
C9 0.118(6) 0.066(3) 0.074(4) -0.006(3) 0.003(4) -0.034(4)
C10 0.154(7) 0.093(4) 0.064(3) -0.010(3) 0.001(5) -0.034(6)

_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 1.896(5) . ?
O1 H1 0.8200 . ?
O1 C6 1.333(6) . ?
N1 C7 1.265(6) . ?
N1 C8 1.464(6) . ?
C2 H2 0.9300 . ?
C2 C1 1.393(6) . ?
C2 C3 1.384(7) . ?
C1 C7 1.460(7) . ?
C1 C6 1.403(7) . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.371(8) . ?
C4 C5 1.378(8) . ?
C6 C5 1.400(8) . ?
C8 C8 1.531(9) 2_665 ?
C8 H8 0.9800 . ?
C8 C9 1.521(8) . ?
C5 H5 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.513(10) . ?
C10 C10 1.516(15) 2_665 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
C6 O1 H1 109.5 . . ?
C7 N1 C8 119.0(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C3 C2 C1 120.1(4) . . ?
C2 C1 C7 119.7(4) . . ?
C2 C1 C6 119.2(5) . . ?
C6 C1 C7 121.1(4) . . ?
N1 C7 C1 121.8(4) . . ?
N1 C7 H7 119.1 . . ?
C1 C7 H7 119.1 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(5) . . ?
C5 C4 H4 120.5 . . ?
O1 C6 C1 122.4(5) . . ?
O1 C6 C5 118.7(5) . . ?
C5 C6 C1 118.9(5) . . ?
C2 C3 Br1 119.4(4) . . ?
C4 C3 Br1 119.3(4) . . ?
C4 C3 C2 121.3(5) . . ?
N1 C8 C8 109.4(4) . 2_665 ?
N1 C8 H8 109.0 . . ?
N1 C8 C9 109.3(4) . . ?
C8 C8 H8 109.0 2_665 . ?
C9 C8 C8 111.3(4) . 2_665 ?
C9 C8 H8 109.0 . . ?
C4 C5 C6 121.4(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 112.3(5) . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 C10 111.0(7) . 2_665 ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C10 C10 H10A 109.4 2_665 . ?
C10 C10 H10B 109.4 2_665 . ?
H10A C10 H10B 108.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.89 2.615(6) 146.4 . yes

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
O1 C6 C5 C4 -179.1(5) . . . . ?
N1 C8 C9 C10 -174.8(7) . . . . ?
C2 C1 C7 N1 -179.7(4) . . . . ?
C2 C1 C6 O1 178.3(4) . . . . ?
C2 C1 C6 C5 -1.4(7) . . . . ?
C1 C2 C3 Br1 178.5(3) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
C1 C6 C5 C4 0.6(7) . . . . ?
C7 N1 C8 C8 131.4(6) . . . 2_665 ?
C7 N1 C8 C9 -106.5(6) . . . . ?
C7 C1 C6 O1 -2.7(7) . . . . ?
C7 C1 C6 C5 177.6(4) . . . . ?
C6 C1 C7 N1 1.2(7) . . . . ?
C3 C2 C1 C7 -177.4(4) . . . . ?
C3 C2 C1 C6 1.6(7) . . . . ?
C3 C4 C5 C6 0.0(8) . . . . ?
C8 N1 C7 C1 178.0(4) . . . . ?
C8 C8 C9 C10 -53.9(8) 2_665 . . . ?
C8 C9 C10 C10 55.6(13) . . . 2_665 ?
C5 C4 C3 Br1 -179.3(4) . . . . ?
C5 C4 C3 C2 0.1(7) . . . . ?

_shelx_res_file                  
;
TITL RR-C20H20Br2N2O2-298K.res in P2(1)2(1)2
    RR-C20H20Br2N2O2-298K.res
    created by SHELXL-2018/3 at 10:46:33 on 16-Dec-2024
REM Old TITL RR-C20H20Br2N2O2-298K in P2(1)2(1)2
REM SHELXT solution in P2(1)2(1)2
REM R1 0.169, Rweak 0.036, Alpha 0.007, Orientation as input
REM Flack x = 0.147 ( 0.023 ) from Parsons' quotients
REM Formula found by SHELXT: C10 N2 Br
CELL 1.54184 5.9248 19.0854 9.0135 90 90 90
ZERR 2 0.0001 0.0003 0.0001 0 0 0
LATT -1
SYMM -X,-Y,+Z
SYMM 0.5-X,0.5+Y,-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br N O
UNIT 40 40 4 4 4

L.S. 4
PLAN  15
SIZE 0.1 0.1 0.1
TEMP 25
CONF
HTAB O1 N1
BOND $H
LIST 6
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\RR-C20H20Br2N2O2-298K.hkl">
REM </olex2.extras>

WGHT    0.072000    0.210100
EXTI    0.029752
FVAR       0.92634
BR1   3    0.489066    0.788343    0.171142    11.00000    0.09991    0.09382 =
         0.05860    0.01149   -0.01065    0.01053
O1    5    0.978495    0.575041    0.539592    11.00000    0.05504    0.06764 =
         0.12430    0.01530    0.00120    0.01613
AFIX 147
H1    2    0.903540    0.563196    0.611841    11.00000   -1.50000
AFIX   0
N1    4    0.619504    0.566874    0.707406    11.00000    0.05809    0.04723 =
         0.07361    0.00364    0.00057   -0.00835
C2    1    0.536554    0.693918    0.413099    11.00000    0.04521    0.05790 =
         0.04890   -0.01165   -0.00208    0.00201
AFIX  43
H2    2    0.393102    0.709382    0.439216    11.00000   -1.20000
AFIX   0
C1    1    0.644504    0.643344    0.498955    11.00000    0.04516    0.04752 =
         0.05573   -0.00806   -0.00508   -0.00312
C7    1    0.527614    0.612772    0.626079    11.00000    0.04401    0.05276 =
         0.05753   -0.00688   -0.00012   -0.00568
AFIX  43
H7    2    0.381640    0.627442    0.647853    11.00000   -1.20000
AFIX   0
C4    1    0.855012    0.700228    0.248880    11.00000    0.06620    0.07265 =
         0.05105   -0.01050    0.00847   -0.01197
AFIX  43
H4    2    0.924376    0.719036    0.165327    11.00000   -1.20000
AFIX   0
C6    1    0.863193    0.621872    0.460257    11.00000    0.04701    0.04772 =
         0.07982   -0.00783   -0.00365    0.00089
C3    1    0.642310    0.721201    0.289021    11.00000    0.06265    0.06124 =
         0.04789   -0.00838   -0.00142   -0.00334
C8    1    0.495575    0.540091    0.835963    11.00000    0.07043    0.05080 =
         0.06808    0.00069    0.00502   -0.01020
AFIX  13
H8    2    0.337765    0.555106    0.828889    11.00000   -1.20000
AFIX   0
C5    1    0.964569    0.650867    0.334143    11.00000    0.04339    0.07103 =
         0.07894   -0.02056    0.00699    0.00176
AFIX  43
H5    2    1.108918    0.636520    0.307314    11.00000   -1.20000
AFIX   0
C9    1    0.598039    0.570139    0.977003    11.00000    0.11771    0.06557 =
         0.07417   -0.00603    0.00329   -0.03447
AFIX  23
H9A   2    0.758845    0.560603    0.977863    11.00000   -1.20000
H9B   2    0.577930    0.620578    0.977365    11.00000   -1.20000
AFIX   0
C10   1    0.492282    0.539651    1.115520    11.00000    0.15352    0.09265 =
         0.06380   -0.00966    0.00071   -0.03430
AFIX  23
H10A  2    0.335099    0.553642    1.120867    11.00000   -1.20000
H10B  2    0.568871    0.558027    1.202313    11.00000   -1.20000
AFIX   0
HKLF 4




REM  RR-C20H20Br2N2O2-298K.res in P2(1)2(1)2
REM wR2 = 0.1243, GooF = S = 1.070, Restrained GooF = 1.070 for all data
REM R1 = 0.0435 for 1732 Fo > 4sig(Fo) and 0.0457 for all 1880 data
REM 120 parameters refined using 0 restraints

END

WGHT      0.0720      0.2101

REM Highest difference peak  0.350,  deepest hole -0.469,  1-sigma level  0.071
Q1    1   0.4920  0.8030  0.2421  11.00000  0.05    0.35
Q2    1   0.6083  0.7672  0.1541  11.00000  0.05    0.35
Q3    1   0.3883  0.7575  0.1480  11.00000  0.05    0.26
Q4    1   0.4990  0.5486  1.1701  11.00000  0.05    0.21
Q5    1   0.4193  0.6405  1.1803  11.00000  0.05    0.21
Q6    1   1.0010  0.5390  0.8396  11.00000  0.05    0.21
Q7    1   0.5024  0.8028  0.0829  11.00000  0.05    0.20
Q8    1   0.4987  0.7033  0.3404  11.00000  0.05    0.20
Q9    1   1.0316  0.7041  0.2214  11.00000  0.05    0.20
Q10   1   0.9882  0.7022  0.5132  11.00000  0.05    0.20
Q11   1   1.1267  0.7156  0.1145  11.00000  0.05    0.18
Q12   1   0.4257  0.6950  0.6437  11.00000  0.05    0.18
Q13   1   0.9849  0.5579  0.7780  11.00000  0.05    0.18
Q14   1   0.6201  0.6392  1.1558  11.00000  0.05    0.17
Q15   1   0.9264  0.5560  0.4720  11.00000  0.05    0.17
;
_shelx_res_checksum              87853
_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 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.731
####################################################################### 
# 
# 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_Rac-C20H20Br2N2O2-298K
_database_code_depnum_ccdc_archive 'CCDC 2411528'
loop_
_audit_author_name
_audit_author_address
'Xin Shen'
;Nanchang University
China
;
_audit_update_record             
;
2024-12-19 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_audit_creation_date             2024-12-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 Br2 N2 O2'
_chemical_formula_sum            'C20 H20 Br2 N2 O2'
_chemical_formula_weight         480.20
_chemical_absolute_configuration na
_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'
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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
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                   5.9364(2)
_cell_length_b                   19.0616(8)
_cell_length_c                   9.0086(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1019.39(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2190
_cell_measurement_temperature    297.98(10)
_cell_measurement_theta_max      73.9310
_cell_measurement_theta_min      2.3570
_shelx_estimated_absorpt_T_max   0.626
_shelx_estimated_absorpt_T_min   0.626
_exptl_absorpt_coefficient_mu    5.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3315
_diffrn_reflns_point_group_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.243
_diffrn_reflns_theta_min         4.640
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  83.00   0.50    0.05    --   45.20-108.00 -86.00   98
  2  ω     37.00  63.00   0.50    0.06    --  108.36 -61.00-150.00   52
  3  ω     47.00  95.00   0.50    0.06    --  108.36-108.00 -86.00   96
  4  ω     38.00  68.00   0.50    0.06    --  108.36 -61.00-120.00   60
  5  ω     66.00 105.00   0.50    0.06    --  108.36 -94.00 -60.00   78
  6  ω     47.00  73.00   0.50    0.06    --  108.36 -61.00  60.00   52
  7  ω     36.00 110.00   0.50    0.05    --   45.20  57.00-180.00  148
  8  ω     -4.00  26.00   0.50    0.05    --  -45.20  19.00 -90.00   60
  9  ω     -7.00  30.00   0.50    0.05    --  -45.20  19.00  30.00   74
 10  ω   -175.00 -98.00   0.50    0.06    -- -102.00 -20.00  86.00  154
 11  ω   -128.00 -54.00   0.50    0.06    -- -102.00-154.00-146.00  148
;
_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      0.0669395000
_diffrn_orient_matrix_UB_12      0.0475042000
_diffrn_orient_matrix_UB_13      -0.1310727000
_diffrn_orient_matrix_UB_21      -0.0117876000
_diffrn_orient_matrix_UB_22      0.0646796000
_diffrn_orient_matrix_UB_23      0.1022892000
_diffrn_orient_matrix_UB_31      0.2503516000
_diffrn_orient_matrix_UB_32      -0.0096852000
_diffrn_orient_matrix_UB_33      0.0401807000
_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         0.507
_reflns_Friedel_fraction_full    0.792
_reflns_Friedel_fraction_max     0.705
_reflns_number_gt                1570
_reflns_number_total             1821
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.969
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details 
;
 Flack x determined using 458 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.31(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1821
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0678
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1233P)²+0.2716P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1912
_refine_ls_wR_factor_ref         0.1978
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C4(H4), C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.4854(2) 0.21249(6) 0.82901(10) 0.0872(5) Uani 1 1 d . . . . .
N1 N 0.6187(13) 0.4332(3) 0.2925(9) 0.0650(18) Uani 1 1 d . . . . .
O1 O 0.9775(11) 0.4237(4) 0.4594(10) 0.0855(19) Uani 1 1 d . . . . .
H1 H 0.898037 0.437516 0.390895 0.128 Uiso 1 1 calc R U . . .
C2 C 0.5358(12) 0.3068(4) 0.5865(7) 0.0515(15) Uani 1 1 d . . . . .
H2 H 0.393177 0.291187 0.559581 0.062 Uiso 1 1 calc R U . . .
C1 C 0.6421(13) 0.3566(4) 0.5020(9) 0.0532(16) Uani 1 1 d . . . . .
C7 C 0.5243(13) 0.3871(4) 0.3729(8) 0.0546(15) Uani 1 1 d . . . . .
H7 H 0.378923 0.372426 0.350281 0.065 Uiso 1 1 calc R U . . .
C3 C 0.6389(13) 0.2798(5) 0.7116(8) 0.0591(18) Uani 1 1 d . . . . .
C4 C 0.8506(16) 0.2987(5) 0.7507(10) 0.068(2) Uani 1 1 d . . . . .
H4 H 0.920537 0.278560 0.832680 0.081 Uiso 1 1 calc R U . . .
C6 C 0.8633(13) 0.3779(4) 0.5410(11) 0.0607(19) Uani 1 1 d . . . . .
C5 C 0.9605(12) 0.3486(5) 0.6663(11) 0.069(2) Uani 1 1 d . . . . .
H5 H 1.104016 0.362947 0.694421 0.082 Uiso 1 1 calc R U . . .
C8 C 0.4940(17) 0.4597(4) 0.1630(9) 0.071(2) Uani 1 1 d . . . . .
H8 H 0.336328 0.444773 0.169448 0.085 Uiso 1 1 calc R U . . .
C9 C 0.599(3) 0.4303(6) 0.0218(13) 0.101(4) Uani 1 1 d . . . . .
H9A H 0.758852 0.441263 0.020683 0.121 Uiso 1 1 calc R U . . .
H9B H 0.583692 0.379642 0.021401 0.121 Uiso 1 1 calc R U . . .
C10 C 0.491(3) 0.4599(7) -0.1155(12) 0.118(5) Uani 1 1 d . . . . .
H10A H 0.333180 0.446336 -0.118582 0.141 Uiso 1 1 calc R U . . .
H10B H 0.564101 0.441079 -0.203052 0.141 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.1177(8) 0.0935(9) 0.0504(6) 0.0113(4) 0.0113(6) -0.0121(6)
N1 0.082(4) 0.044(4) 0.069(5) 0.007(3) 0.007(4) 0.011(3)
O1 0.071(3) 0.069(3) 0.116(6) 0.011(4) 0.000(4) -0.013(3)
C2 0.055(3) 0.056(4) 0.044(3) -0.011(3) -0.001(3) 0.000(3)
C1 0.061(4) 0.051(4) 0.048(4) -0.006(3) 0.002(3) 0.009(3)
C7 0.065(3) 0.046(3) 0.053(3) -0.008(3) -0.005(3) 0.004(3)
C3 0.074(4) 0.065(5) 0.038(3) -0.008(3) 0.004(3) 0.002(4)
C4 0.084(5) 0.071(6) 0.048(4) -0.012(4) -0.016(4) 0.009(4)
C6 0.060(4) 0.046(4) 0.076(5) -0.007(4) 0.002(4) -0.001(3)
C5 0.055(3) 0.073(5) 0.078(6) -0.025(5) -0.013(4) 0.004(3)
C8 0.099(5) 0.052(4) 0.062(5) -0.001(4) -0.004(6) 0.016(4)
C9 0.153(11) 0.071(6) 0.079(7) -0.017(6) -0.006(8) 0.044(7)
C10 0.197(15) 0.097(8) 0.059(5) -0.011(6) -0.013(9) 0.059(10)

_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 1.896(9) . ?
N1 C7 1.269(11) . ?
N1 C8 1.471(11) . ?
O1 H1 0.8200 . ?
O1 C6 1.329(11) . ?
C2 H2 0.9300 . ?
C2 C1 1.370(11) . ?
C2 C3 1.382(10) . ?
C1 C7 1.477(11) . ?
C1 C6 1.419(11) . ?
C7 H7 0.9300 . ?
C3 C4 1.354(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(13) . ?
C6 C5 1.385(13) . ?
C5 H5 0.9300 . ?
C8 C8 1.538(17) 2_665 ?
C8 H8 0.9800 . ?
C8 C9 1.525(13) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.505(16) . ?
C10 C10 1.53(3) 2_665 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 N1 C8 117.9(8) . . ?
C6 O1 H1 109.5 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.5(7) . . ?
C3 C2 H2 119.8 . . ?
C2 C1 C7 119.5(7) . . ?
C2 C1 C6 119.1(8) . . ?
C6 C1 C7 121.4(8) . . ?
N1 C7 C1 120.9(7) . . ?
N1 C7 H7 119.5 . . ?
C1 C7 H7 119.5 . . ?
C2 C3 Br1 119.6(6) . . ?
C4 C3 Br1 118.7(7) . . ?
C4 C3 C2 121.6(8) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(8) . . ?
C5 C4 H4 120.7 . . ?
O1 C6 C1 121.6(9) . . ?
O1 C6 C5 120.2(7) . . ?
C5 C6 C1 118.2(8) . . ?
C4 C5 C6 122.0(7) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
N1 C8 C8 108.7(7) . 2_665 ?
N1 C8 H8 109.5 . . ?
N1 C8 C9 109.2(7) . . ?
C8 C8 H8 109.5 2_665 . ?
C9 C8 C8 110.4(7) . 2_665 ?
C9 C8 H8 109.5 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 111.9(9) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 C10 110.0(13) . 2_665 ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C10 C10 H10A 109.7 2_665 . ?
C10 C10 H10B 109.7 2_665 . ?
H10A C10 H10B 108.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.88 2.614(10) 147.9 . yes

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(6) . . . . ?
N1 C8 C9 C10 -175.6(13) . . . . ?
O1 C6 C5 C4 -177.4(8) . . . . ?
C2 C1 C7 N1 -179.9(7) . . . . ?
C2 C1 C6 O1 177.2(7) . . . . ?
C2 C1 C6 C5 -1.8(12) . . . . ?
C2 C3 C4 C5 2.8(13) . . . . ?
C1 C2 C3 Br1 178.6(6) . . . . ?
C1 C2 C3 C4 -3.2(12) . . . . ?
C1 C6 C5 C4 1.5(12) . . . . ?
C7 N1 C8 C8 132.1(10) . . . 2_665 ?
C7 N1 C8 C9 -107.4(10) . . . . ?
C7 C1 C6 O1 -3.1(12) . . . . ?
C7 C1 C6 C5 177.9(6) . . . . ?
C3 C2 C1 C7 -177.2(6) . . . . ?
C3 C2 C1 C6 2.5(11) . . . . ?
C3 C4 C5 C6 -2.1(13) . . . . ?
C6 C1 C7 N1 0.4(11) . . . . ?
C8 N1 C7 C1 178.1(6) . . . . ?
C8 C8 C9 C10 -56.2(16) 2_665 . . . ?
C8 C9 C10 C10 58(2) . . . 2_665 ?

_shelx_res_file                  
;
TITL Rac-C20H20Br2N2O2-298K.res in P2(1)2(1)2
    Rac-C20H20Br2N2O2-298K.res
    created by SHELXL-2018/3 at 11:05:24 on 16-Dec-2024
REM Old TITL Rac-C20H20Br2N2O2-298K in P2(1)2(1)2
REM SHELXT solution in P2(1)2(1)2
REM R1 0.232, Rweak 0.103, Alpha 0.017, Orientation as input
REM Flack x = 0.407 ( 0.039 ) from Parsons' quotients
REM Formula found by SHELXT: C10 N2 Br
CELL 1.54184 5.9364 19.0616 9.0086 90 90 90
ZERR 2 0.0002 0.0008 0.0003 0 0 0
LATT -1
SYMM -X,-Y,+Z
SYMM 0.5-X,0.5+Y,-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br N O
UNIT 40 40 4 4 4

L.S. 20
PLAN  15
SIZE 0.1 0.1 0.1
TEMP 25
CONF
HTAB O1 N1
BOND $H
LIST 6
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\Rac-C20H20Br2N2O2-298K.hkl">
REM </olex2.extras>

WGHT    0.123300    0.271600
FVAR       0.78671
BR1   3    0.485411    0.212491    0.829011    11.00000    0.11767    0.09354 =
         0.05042    0.01126    0.01131   -0.01209
N1    4    0.618671    0.433173    0.292473    11.00000    0.08153    0.04416 =
         0.06938    0.00727    0.00737    0.01097
O1    5    0.977543    0.423744    0.459388    11.00000    0.07095    0.06908 =
         0.11641    0.01088    0.00016   -0.01337
AFIX 147
H1    2    0.898037    0.437516    0.390895    11.00000   -1.50000
AFIX   0
C2    1    0.535801    0.306848    0.586529    11.00000    0.05494    0.05611 =
         0.04359   -0.01059   -0.00122   -0.00010
AFIX  43
H2    2    0.393177    0.291187    0.559581    11.00000   -1.20000
AFIX   0
C1    1    0.642070    0.356562    0.502007    11.00000    0.06093    0.05074 =
         0.04792   -0.00615    0.00164    0.00933
C7    1    0.524295    0.387131    0.372917    11.00000    0.06458    0.04614 =
         0.05300   -0.00831   -0.00513    0.00394
AFIX  43
H7    2    0.378923    0.372426    0.350281    11.00000   -1.20000
AFIX   0
C3    1    0.638942    0.279787    0.711561    11.00000    0.07447    0.06454 =
         0.03840   -0.00834    0.00364    0.00159
C4    1    0.850641    0.298712    0.750719    11.00000    0.08417    0.07128 =
         0.04817   -0.01182   -0.01574    0.00926
AFIX  43
H4    2    0.920537    0.278560    0.832680    11.00000   -1.20000
AFIX   0
C6    1    0.863293    0.377862    0.541010    11.00000    0.05986    0.04586 =
         0.07632   -0.00736    0.00155   -0.00096
C5    1    0.960501    0.348590    0.666299    11.00000    0.05546    0.07277 =
         0.07765   -0.02546   -0.01329    0.00408
AFIX  43
H5    2    1.104016    0.362947    0.694421    11.00000   -1.20000
AFIX   0
C8    1    0.494004    0.459695    0.163036    11.00000    0.09873    0.05173 =
         0.06211   -0.00122   -0.00357    0.01611
AFIX  13
H8    2    0.336328    0.444773    0.169448    11.00000   -1.20000
AFIX   0
C9    1    0.599301    0.430297    0.021770    11.00000    0.15286    0.07068 =
         0.07927   -0.01655   -0.00575    0.04445
AFIX  23
H9A   2    0.758852    0.441263    0.020683    11.00000   -1.20000
H9B   2    0.583692    0.379642    0.021401    11.00000   -1.20000
AFIX   0
C10   1    0.490589    0.459911   -0.115534    11.00000    0.19716    0.09713 =
         0.05945   -0.01107   -0.01344    0.05912
AFIX  23
H10A  2    0.333180    0.446336   -0.118582    11.00000   -1.20000
H10B  2    0.564101    0.441079   -0.203052    11.00000   -1.20000
AFIX   0
HKLF 4




REM  Rac-C20H20Br2N2O2-298K.res in P2(1)2(1)2
REM wR2 = 0.1978, GooF = S = 1.081, Restrained GooF = 1.081 for all data
REM R1 = 0.0678 for 1570 Fo > 4sig(Fo) and 0.0731 for all 1821 data
REM 119 parameters refined using 0 restraints

END

WGHT      0.1233      0.2716

REM Highest difference peak  0.679,  deepest hole -0.969,  1-sigma level  0.148
Q1    1   0.2648  0.2170  0.8290  11.00000  0.05    0.68
Q2    1   0.6814  0.2184  0.8354  11.00000  0.05    0.66
Q3    1   0.4865  0.2648  0.8341  11.00000  0.05    0.58
Q4    1   0.5060  0.1539  0.8285  11.00000  0.05    0.36
Q5    1   0.2889  0.4529  0.1691  11.00000  0.05    0.34
Q6    1   1.2110  0.4435  0.5145  11.00000  0.05    0.33
Q7    1   0.7857  0.2111  0.9486  11.00000  0.05    0.31
Q8    1   0.7915  0.5044  0.5603  11.00000  0.05    0.28
Q9    1   0.2792  0.3318  0.3303  11.00000  0.05    0.28
Q10   1   0.1890  0.2861  0.4216  11.00000  0.05    0.28
Q11   1   0.7995  0.4405  0.2965  11.00000  0.05    0.27
Q12   1   0.1841  0.4794  0.2571  11.00000  0.05    0.26
Q13   1   0.7952  0.2959  0.4193  11.00000  0.05    0.26
Q14   1   0.6850  0.2872  0.0409  11.00000  0.05    0.26
Q15   1   0.3076  0.3181  0.5463  11.00000  0.05    0.26
;
_shelx_res_checksum              66342
_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 3.386
_oxdiff_exptl_absorpt_empirical_full_min 0.390
