data_global
_audit_creation_date                               2022-02-25
_audit_creation_method                            'by CrystalStructure 4.3'
_audit_update_record                               2022-05-13
#==============================================================================
# TEXT
_publ_section_references
;
    Rigaku (2019). CrystalStructure. Version 4.3. 
    Rigaku Corporation, Tokyo, Japan.

    Sheldrick, G. M. (2014). Acta Cryst. (2014). A70, C1437.
    SHELXT Version 2014/5

    Sheldrick, G.M. (2008) SHELXL Version 2016/6, Acta Cryst. A64, 112-122.

    Rigaku Oxford Diffraction (2021), CrysAlisPro. version 1.171.41.99a.
    Rigaku Corporation, Tokyo, Japan
;
#==============================================================================
data_C21H14BrF3
#==============================================================================
# CHEMICAL DATA
_chemical_formula_sum                             'C21 H14 Br F3'
_chemical_formula_moiety                          'C21 H14 Br F3'
_chemical_formula_weight                           403.24
_chemical_absolute_configuration                  'ad'
#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system                        monoclinic
_space_group_name_H-M_alt                         'P 1 21 1'
_space_group_name_Hall                            'P 2yb'
_space_group_IT_number                             4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1   '+X,+Y,+Z'
2   '-X,1/2+Y,-Z'
#------------------------------------------------------------------------------
_cell_length_a                                     9.1554(4)
_cell_length_b                                     7.1034(3)
_cell_length_c                                     13.5438(6)
_cell_angle_alpha                                  90.0000
_cell_angle_beta                                   103.113(4)
_cell_angle_gamma                                  90.0000
_cell_volume                                       857.85(7)
_cell_formula_units_Z                              2
_cell_measurement_reflns_used                      6335
_cell_measurement_theta_min                        2.26
_cell_measurement_theta_max                        31.11
_cell_measurement_temperature                      93
#------------------------------------------------------------------------------
_exptl_crystal_description                         needle
_exptl_crystal_colour                              colorless
_exptl_crystal_size_max                            0.131
_exptl_crystal_size_mid                            0.066
_exptl_crystal_size_min                            0.037
_exptl_crystal_density_diffrn                      1.561
_exptl_crystal_density_method                     'not measured'
_exptl_crystal_F_000                               404.00
_exptl_absorpt_coefficient_mu                      2.433
_exptl_absorpt_correction_type                     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min                    0.847
_exptl_absorpt_correction_T_max                    0.914
#==============================================================================
# EXPERIMENTAL DATA
_diffrn_ambient_temperature                        93
_diffrn_radiation_type                            'Mo K\a'
_diffrn_radiation_wavelength                       0.71073
_diffrn_measurement_device_type                   'Rigaku XtaLAB Synergy'
_diffrn_measurement_method                         ω
_diffrn_detector_area_resol_mean                   10.000
_diffrn_reflns_number                              13715
_diffrn_reflns_av_unetI/netI                       0.0494
_diffrn_reflns_av_R_equivalents                    0.0457
_diffrn_reflns_theta_max                           31.010
_diffrn_reflns_theta_min                           2.284
_diffrn_reflns_theta_full                          25.242
_diffrn_measured_fraction_theta_max                0.851
_diffrn_measured_fraction_theta_full               0.999
_diffrn_reflns_Laue_measured_fraction_max          0.851
_diffrn_reflns_Laue_measured_fraction_full         0.999
_diffrn_reflns_point_group_measured_fraction_max   0.791
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_limit_h_min                        -13
_diffrn_reflns_limit_h_max                         10
_diffrn_reflns_limit_k_min                        -10
_diffrn_reflns_limit_k_max                         9
_diffrn_reflns_limit_l_min                        -18
_diffrn_reflns_limit_l_max                         17
_diffrn_standards_number                           0
_diffrn_standards_interval_count                   .
_reflns_number_total                               4344
_reflns_number_gt                                  3899
_reflns_threshold_expression                       F²>2.0σ(F²)
_reflns_Friedel_coverage          0.733
_reflns_Friedel_fraction_max      0.722
_reflns_Friedel_fraction_full     0.999
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef                   Fsqd
_refine_ls_R_factor_all                            0.0370
_refine_ls_R_factor_gt                             0.0297
_refine_ls_wR_factor_ref                           0.0564
_refine_ls_wR_factor_gt                            0.0547
_refine_ls_number_restraints                       1
_refine_ls_hydrogen_treatment                      constr
_refine_ls_number_reflns                           4344
_refine_ls_number_parameters                       226
_refine_ls_goodness_of_fit_ref                     1.000
_refine_ls_weighting_scheme                        calc
_refine_ls_weighting_details
                        'w = 1/[σ²(Fo²)+0.3650P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens                     geom
_atom_sites_solution_primary                       direct
_atom_sites_solution_secondary                     difmap
_refine_ls_shift/su_max                            0.001
_refine_diff_density_max                           0.30
_refine_diff_density_min                          -0.33
_refine_ls_extinction_method                       none
_refine_ls_abs_structure_details
;
 Flack x determined using 1533 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack                    -0.005(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS
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 -0.04220(3) 0.08098(5) 0.75253(2) 0.02580(9) Uani 1 1 d . . . . .
F1 F 0.55140(19) 0.4506(2) 0.54165(13) 0.0213(4) Uani 1 1 d . . . . .
F2 F 0.3527(2) 0.2801(3) 0.52137(14) 0.0238(4) Uani 1 1 d . . . . .
F3 F 0.33563(18) 0.5709(4) 0.47638(11) 0.0257(4) Uani 1 1 d . . . . .
C1 C 0.3905(3) 0.5072(4) 0.6544(2) 0.0137(6) Uani 1 1 d . . . . .
C2 C 0.4851(3) 0.3769(4) 0.7254(2) 0.0143(6) Uani 1 1 d . . . . .
C3 C 0.5637(4) 0.2706(4) 0.7812(2) 0.0209(6) Uani 1 1 d . . . . .
H3 H 0.625168 0.187463 0.824918 0.025 Uiso 1 1 calc R U . . .
C4 C 0.4073(3) 0.4521(4) 0.5479(2) 0.0187(6) Uani 1 1 d . . . . .
C5 C 0.2227(3) 0.4829(4) 0.6552(2) 0.0155(6) Uani 1 1 d . . . . .
C6 C 0.1755(3) 0.3261(4) 0.7002(2) 0.0158(6) Uani 1 1 d . . . . .
H6 H 0.245026 0.239769 0.734823 0.019 Uiso 1 1 calc R U . . .
C7 C 0.0226(3) 0.2990(4) 0.6930(2) 0.0183(6) Uani 1 1 d . . . . .
C8 C -0.0835(4) 0.4237(5) 0.6423(3) 0.0243(7) Uani 1 1 d . . . . .
H8 H -0.185107 0.403006 0.637771 0.029 Uiso 1 1 calc R U . . .
C9 C -0.0355(3) 0.5794(8) 0.5984(2) 0.0280(6) Uani 1 1 d . . . . .
H9 H -0.105687 0.665705 0.564498 0.034 Uiso 1 1 calc R U . . .
C10 C 0.1164(3) 0.6104(5) 0.6038(2) 0.0221(7) Uani 1 1 d . . . . .
H10 H 0.146842 0.716005 0.573168 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4474(4) 0.7129(4) 0.6755(2) 0.0146(6) Uani 1 1 d . . . . .
H11A H 0.540965 0.725915 0.654002 0.018 Uiso 1 1 calc R U . . .
H11B H 0.375146 0.796962 0.634014 0.018 Uiso 1 1 calc R U . . .
C12 C 0.4726(3) 0.7765(4) 0.7846(2) 0.0144(6) Uani 1 1 d . . . . .
C13 C 0.6194(4) 0.7782(4) 0.8498(2) 0.0161(6) Uani 1 1 d . . . . .
C14 C 0.7487(4) 0.7090(4) 0.8212(2) 0.0189(6) Uani 1 1 d . . . . .
H14 H 0.739039 0.657361 0.756938 0.023 Uiso 1 1 calc R U . . .
C15 C 0.8872(4) 0.7160(5) 0.8852(3) 0.0269(7) Uani 1 1 d . . . . .
H15 H 0.969836 0.667676 0.864619 0.032 Uiso 1 1 calc R U . . .
C16 C 0.9056(4) 0.7966(5) 0.9831(3) 0.0305(8) Uani 1 1 d . . . . .
H16 H 1.000115 0.803048 1.026408 0.037 Uiso 1 1 calc R U . . .
C17 C 0.7838(4) 0.8643(5) 1.0130(2) 0.0277(8) Uani 1 1 d . . . . .
H17 H 0.796512 0.917473 1.077114 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6385(4) 0.8564(4) 0.9496(2) 0.0194(6) Uani 1 1 d . . . . .
C19 C 0.5109(4) 0.9224(4) 0.9818(2) 0.0231(7) Uani 1 1 d . . . . .
H19 H 0.522353 0.972388 1.046581 0.028 Uiso 1 1 calc R U . . .
C20 C 0.3727(4) 0.9138(4) 0.9199(3) 0.0251(7) Uani 1 1 d . . . . .
H20 H 0.289980 0.955493 0.942881 0.030 Uiso 1 1 calc R U . . .
C21 C 0.3530(4) 0.8417(4) 0.8205(2) 0.0195(6) Uani 1 1 d . . . . .
H21 H 0.257291 0.838400 0.778492 0.023 Uiso 1 1 calc R U . . .
#==============================================================================
_computing_data_collection
                                   'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_cell_refinement
                                   'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction
                                   'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_structure_solution
                                      'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement
                                      'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_publication_material
                                          'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics                     'CrystalStructure 4.3'
#==============================================================================
# MOLECULAR GEOMETRY
_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 C7 1.902(3) . ?
F1 C4 1.341(3) . ?
F2 C4 1.338(3) . ?
F3 C4 1.340(4) . ?
C1 C2 1.468(4) . ?
C1 C4 1.535(4) . ?
C1 C5 1.548(4) . ?
C1 C11 1.556(4) . ?
C2 C3 1.188(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.385(4) . ?
C5 C10 1.395(4) . ?
C6 C7 1.395(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(5) . ?
C8 C9 1.374(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.511(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C21 1.376(4) . ?
C12 C13 1.431(4) . ?
C13 C14 1.414(4) . ?
C13 C18 1.435(4) . ?
C14 C15 1.365(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.419(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.357(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.412(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.417(4) . ?
C19 C20 1.351(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.414(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 C4 106.6(2) . . ?
C2 C1 C5 111.3(2) . . ?
C4 C1 C5 106.9(2) . . ?
C2 C1 C11 110.4(3) . . ?
C4 C1 C11 108.1(2) . . ?
C5 C1 C11 113.2(2) . . ?
C3 C2 C1 178.4(3) . . ?
C2 C3 H3 180.0 . . ?
F2 C4 F3 106.8(3) . . ?
F2 C4 F1 106.8(2) . . ?
F3 C4 F1 106.6(2) . . ?
F2 C4 C1 112.0(2) . . ?
F3 C4 C1 112.4(2) . . ?
F1 C4 C1 111.8(2) . . ?
C6 C5 C10 119.3(3) . . ?
C6 C5 C1 120.1(3) . . ?
C10 C5 C1 120.3(3) . . ?
C5 C6 C7 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 Br1 118.9(2) . . ?
C6 C7 Br1 119.2(2) . . ?
C9 C8 C7 118.4(3) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C10 121.2(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C5 119.9(3) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?
C12 C11 C1 115.5(2) . . ?
C12 C11 H11A 108.4 . . ?
C1 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C1 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C21 C12 C13 119.4(3) . . ?
C21 C12 C11 119.2(3) . . ?
C13 C12 C11 121.3(3) . . ?
C14 C13 C12 123.7(3) . . ?
C14 C13 C18 117.5(3) . . ?
C12 C13 C18 118.8(3) . . ?
C15 C14 C13 121.8(3) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 122.0(3) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C19 121.9(3) . . ?
C17 C18 C13 119.0(3) . . ?
C19 C18 C13 119.1(3) . . ?
C20 C19 C18 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C12 C21 C20 121.3(3) . . ?
C12 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
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
C2 C1 C4 F2 64.9(3) . . . . ?
C5 C1 C4 F2 -54.2(3) . . . . ?
C11 C1 C4 F2 -176.4(2) . . . . ?
C2 C1 C4 F3 -174.8(2) . . . . ?
C5 C1 C4 F3 66.0(3) . . . . ?
C11 C1 C4 F3 -56.2(3) . . . . ?
C2 C1 C4 F1 -54.9(3) . . . . ?
C5 C1 C4 F1 -174.0(2) . . . . ?
C11 C1 C4 F1 63.8(3) . . . . ?
C2 C1 C5 C6 -14.1(4) . . . . ?
C4 C1 C5 C6 101.9(3) . . . . ?
C11 C1 C5 C6 -139.2(3) . . . . ?
C2 C1 C5 C10 171.1(3) . . . . ?
C4 C1 C5 C10 -72.9(3) . . . . ?
C11 C1 C5 C10 46.0(4) . . . . ?
C10 C5 C6 C7 0.0(4) . . . . ?
C1 C5 C6 C7 -174.8(3) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C5 C6 C7 Br1 178.8(2) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
Br1 C7 C8 C9 -179.1(3) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?
C8 C9 C10 C5 -0.6(5) . . . . ?
C6 C5 C10 C9 0.2(5) . . . . ?
C1 C5 C10 C9 175.0(3) . . . . ?
C2 C1 C11 C12 -50.4(3) . . . . ?
C4 C1 C11 C12 -166.6(3) . . . . ?
C5 C1 C11 C12 75.2(3) . . . . ?
C1 C11 C12 C21 -83.5(3) . . . . ?
C1 C11 C12 C13 99.4(3) . . . . ?
C21 C12 C13 C14 178.0(3) . . . . ?
C11 C12 C13 C14 -4.9(4) . . . . ?
C21 C12 C13 C18 -2.9(4) . . . . ?
C11 C12 C13 C18 174.2(3) . . . . ?
C12 C13 C14 C15 178.9(3) . . . . ?
C18 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 -1.0(5) . . . . ?
C14 C15 C16 C17 0.9(5) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 C19 178.2(3) . . . . ?
C16 C17 C18 C13 -1.4(5) . . . . ?
C14 C13 C18 C17 1.3(4) . . . . ?
C12 C13 C18 C17 -177.9(3) . . . . ?
C14 C13 C18 C19 -178.3(3) . . . . ?
C12 C13 C18 C19 2.6(4) . . . . ?
C17 C18 C19 C20 179.9(3) . . . . ?
C13 C18 C19 C20 -0.5(4) . . . . ?
C18 C19 C20 C21 -1.3(5) . . . . ?
C13 C12 C21 C20 1.2(4) . . . . ?
C11 C12 C21 C20 -175.9(3) . . . . ?
C19 C20 C21 C12 0.9(5) . . . . ?
#==============================================================================
# Additional structures and associated data_C21H14BrF3 identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.
#==============================================================================
#     End of CIF
#==============================================================================
