
data_CB2214

_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C21 H17 Br O2'
_chemical_formula_sum
 'C21 H17 Br O2'
_chemical_formula_weight          381.26

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'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system       monoclinic
_space_group_IT_number            5
_space_group_name_H-M_alt         'I 2'
_space_group_name_Hall            'I 2y'

_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.
;

loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z'
 'x+1/2, y+1/2, z+1/2'
 '-x+1/2, y+1/2, -z+1/2'

_cell_length_a                    14.0980(3)
_cell_length_b                    7.50617(16)
_cell_length_c                    16.0950(3)
_cell_angle_alpha                 90
_cell_angle_beta                  92.4017(17)
_cell_angle_gamma                 90
_cell_volume                      1701.71(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     5058
_cell_measurement_theta_min       4.0530
_cell_measurement_theta_max       72.6900

_exptl_crystal_description        blocks
_exptl_crystal_colour             Colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.488
_exptl_crystal_F_000              776
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.301
_exptl_crystal_size_mid           0.203
_exptl_crystal_size_min           0.055
_exptl_absorpt_coefficient_mu     3.363
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    analytical
_exptl_absorpt_correction_T_min   0.516
_exptl_absorpt_correction_T_max   0.841
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_source                    'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type   'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method        'omega scans'
_diffrn_detector_area_resol_mean  10.4115
_diffrn_reflns_number             7173
_diffrn_reflns_av_unetI/netI      0.0264
_diffrn_reflns_av_R_equivalents   0.0224
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          4.085
_diffrn_reflns_theta_max          73.745
_diffrn_reflns_theta_full         67.684
_diffrn_measured_fraction_theta_max   0.983
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.983
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.932
_diffrn_reflns_point_group_measured_fraction_full  0.962
_reflns_number_total              3205
_reflns_number_gt                 3071
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.756
_reflns_Friedel_fraction_max      0.872
_reflns_Friedel_fraction_full     0.920

_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.
;

_computing_data_collection        'CrysAlisPro, Rigaku OD'
_computing_cell_refinement        'CrysAlisPro, Rigaku OD'
_computing_data_reduction         'CrysAlisPro, Rigaku OD'
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0149P)²+3.2096P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef        0.00029(6)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
;
 Flack x determined using 1269 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.032(11)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          3205
_refine_ls_number_parameters      218
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0376
_refine_ls_R_factor_gt            0.0342
_refine_ls_wR_factor_ref          0.0748
_refine_ls_wR_factor_gt           0.0715
_refine_ls_goodness_of_fit_ref    1.070
_refine_ls_restrained_S_all       1.070
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000

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
C1 C 0.6121(3) 0.3646(6) 0.1001(3) 0.0375(10) Uani 1 1 d . . . . .
H1A H 0.575437 0.407624 0.049446 0.045 Uiso 1 1 calc R U . . .
C2 C 0.6051(4) 0.1649(7) 0.1068(3) 0.0515(13) Uani 1 1 d . . . . .
H2A H 0.538351 0.131811 0.118756 0.062 Uiso 1 1 calc R U . . .
Br2 Br 0.63685(4) 0.06464(9) -0.00188(3) 0.0617(2) Uani 1 1 d . . . . .
C3 C 0.6706(4) 0.0905(9) 0.1736(3) 0.0618(15) Uani 1 1 d . . . . .
H3A H 0.663973 -0.040817 0.174606 0.074 Uiso 1 1 calc R U . . .
H3B H 0.651970 0.136816 0.228166 0.074 Uiso 1 1 calc R U . . .
C4 C 0.7730(4) 0.1379(8) 0.1608(3) 0.0602(16) Uani 1 1 d . . . . .
H4A H 0.809265 0.125264 0.214545 0.072 Uiso 1 1 calc R U . . .
H4B H 0.799419 0.051654 0.121434 0.072 Uiso 1 1 calc R U . . .
C5 C 0.7877(3) 0.3225(7) 0.1283(3) 0.0441(11) Uani 1 1 d . . . . .
C6 C 0.8800(4) 0.3870(11) 0.1225(4) 0.075(2) Uani 1 1 d . . . . .
H6A H 0.932171 0.313812 0.139764 0.090 Uiso 1 1 calc R U . . .
C7 C 0.8966(5) 0.5560(17) 0.0919(5) 0.105(3) Uani 1 1 d . . . . .
H7A H 0.959866 0.598242 0.088615 0.126 Uiso 1 1 calc R U . . .
C8 C 0.8225(7) 0.6618(10) 0.0666(5) 0.102(3) Uani 1 1 d . . . . .
H8A H 0.834157 0.778835 0.047013 0.122 Uiso 1 1 calc R U . . .
C9 C 0.7303(4) 0.5996(7) 0.0693(3) 0.0601(15) Uani 1 1 d . . . . .
H9A H 0.678884 0.673049 0.050474 0.072 Uiso 1 1 calc R U . . .
C10 C 0.7128(3) 0.4297(6) 0.0995(3) 0.0362(9) Uani 1 1 d . . . . .
O11 O 0.5699(2) 0.4327(5) 0.17528(17) 0.0436(8) Uani 1 1 d . . . . .
C12 C 0.4895(3) 0.5281(6) 0.1676(2) 0.0370(11) Uani 1 1 d . . . . .
O12 O 0.4525(2) 0.5652(9) 0.10240(17) 0.0674(11) Uani 1 1 d . . . . .
C13 C 0.4528(2) 0.5662(9) 0.2516(2) 0.0343(8) Uani 1 1 d . . . . .
C14 C 0.4645(4) 0.4404(7) 0.3125(3) 0.0458(11) Uani 1 1 d . . . . .
H14A H 0.498121 0.333986 0.301239 0.055 Uiso 1 1 calc R U . . .
C15 C 0.4277(5) 0.4659(8) 0.3915(3) 0.0612(15) Uani 1 1 d . . . . .
H15A H 0.435225 0.376039 0.432820 0.073 Uiso 1 1 calc R U . . .
C16 C 0.3814(4) 0.6197(7) 0.4084(3) 0.0522(14) Uani 1 1 d . . . . .
H16A H 0.357020 0.636341 0.461996 0.063 Uiso 1 1 calc R U . . .
C17 C 0.3688(3) 0.7545(7) 0.3484(3) 0.0426(11) Uani 1 1 d . . . . .
C18 C 0.3216(3) 0.9143(8) 0.3668(3) 0.0513(13) Uani 1 1 d . . . . .
H18A H 0.296391 0.930006 0.420102 0.062 Uiso 1 1 calc R U . . .
C19 C 0.3118(3) 1.0454(10) 0.3097(3) 0.0612(15) Uani 1 1 d . . . . .
H19A H 0.279731 1.152247 0.323104 0.073 Uiso 1 1 calc R U . . .
C20 C 0.3490(4) 1.0247(8) 0.2299(3) 0.0578(15) Uani 1 1 d . . . . .
H20A H 0.342635 1.118636 0.190544 0.069 Uiso 1 1 calc R U . . .
C21 C 0.3939(3) 0.8704(7) 0.2090(3) 0.0448(11) Uani 1 1 d . . . . .
H21A H 0.417930 0.857487 0.155064 0.054 Uiso 1 1 calc R U . . .
C22 C 0.4048(3) 0.7297(6) 0.2676(3) 0.0356(9) Uani 1 1 d . . . . .

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
C1 0.035(2) 0.053(3) 0.0251(19) -0.0036(18) 0.0052(16) 0.0124(19)
C2 0.047(3) 0.066(3) 0.042(3) -0.019(2) 0.021(2) -0.016(2)
Br2 0.0546(3) 0.0796(4) 0.0517(3) -0.0316(3) 0.0101(2) -0.0058(3)
C3 0.099(4) 0.046(4) 0.043(2) 0.003(2) 0.023(2) 0.001(3)
C4 0.072(4) 0.064(4) 0.043(3) 0.000(2) -0.008(2) 0.028(3)
C5 0.036(2) 0.059(3) 0.037(2) -0.018(2) 0.0011(18) 0.006(2)
C6 0.039(3) 0.118(6) 0.069(4) -0.054(4) 0.005(3) -0.007(3)
C7 0.086(5) 0.132(7) 0.101(5) -0.085(6) 0.059(4) -0.063(6)
C8 0.145(8) 0.061(5) 0.106(6) -0.042(4) 0.092(6) -0.047(5)
C9 0.091(4) 0.036(3) 0.057(3) -0.007(2) 0.042(3) 0.002(3)
C10 0.041(2) 0.041(3) 0.028(2) -0.0069(17) 0.0128(17) 0.0027(19)
O11 0.0366(16) 0.069(2) 0.0256(14) -0.0053(14) 0.0058(12) 0.0166(15)
C12 0.0336(19) 0.043(3) 0.034(2) -0.0015(18) 0.0035(15) 0.0055(18)
O12 0.073(2) 0.097(3) 0.0313(15) -0.006(2) -0.0002(14) 0.047(3)
C13 0.0305(16) 0.039(2) 0.0337(18) -0.003(2) 0.0065(13) 0.000(2)
C14 0.052(3) 0.045(3) 0.041(2) 0.007(2) 0.015(2) 0.008(2)
C15 0.077(4) 0.064(4) 0.045(3) 0.013(3) 0.031(3) 0.010(3)
C16 0.054(3) 0.068(4) 0.036(2) -0.004(2) 0.022(2) 0.001(2)
C17 0.029(2) 0.058(3) 0.042(2) -0.013(2) 0.0088(17) -0.0003(19)
C18 0.041(2) 0.062(4) 0.051(3) -0.023(3) 0.005(2) 0.008(2)
C19 0.053(3) 0.058(4) 0.072(3) -0.026(3) -0.004(2) 0.020(3)
C20 0.063(3) 0.054(4) 0.055(3) -0.004(3) -0.008(2) 0.017(3)
C21 0.045(3) 0.048(3) 0.041(2) -0.001(2) 0.000(2) 0.008(2)
C22 0.027(2) 0.042(3) 0.038(2) -0.0092(19) 0.0044(16) -0.0011(17)

_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
C1 O11 1.463(5) . ?
C1 C10 1.501(6) . ?
C1 C2 1.506(7) . ?
C2 C3 1.496(8) . ?
C2 Br2 1.973(4) . ?
C3 C4 1.510(8) . ?
C4 C5 1.499(8) . ?
C5 C10 1.392(6) . ?
C5 C6 1.395(8) . ?
C6 C7 1.385(14) . ?
C7 C8 1.361(14) . ?
C8 C9 1.384(10) . ?
C9 C10 1.391(7) . ?
O11 C12 1.342(5) . ?
C12 O12 1.186(5) . ?
C12 C13 1.495(5) . ?
C13 C14 1.365(7) . ?
C13 C22 1.430(7) . ?
C14 C15 1.407(7) . ?
C15 C16 1.360(7) . ?
C16 C17 1.406(7) . ?
C17 C18 1.409(7) . ?
C17 C22 1.428(6) . ?
C18 C19 1.349(9) . ?
C19 C20 1.415(7) . ?
C20 C21 1.368(7) . ?
C21 C22 1.420(7) . ?

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
O11 C1 C10 108.0(3) . . ?
O11 C1 C2 104.9(4) . . ?
C10 C1 C2 112.9(4) . . ?
C3 C2 C1 112.5(4) . . ?
C3 C2 Br2 109.8(4) . . ?
C1 C2 Br2 107.3(3) . . ?
C2 C3 C4 112.3(4) . . ?
C5 C4 C3 114.4(5) . . ?
C10 C5 C6 118.3(6) . . ?
C10 C5 C4 122.5(5) . . ?
C6 C5 C4 119.1(6) . . ?
C7 C6 C5 120.9(7) . . ?
C8 C7 C6 120.1(6) . . ?
C7 C8 C9 120.3(7) . . ?
C8 C9 C10 120.1(7) . . ?
C9 C10 C5 120.2(5) . . ?
C9 C10 C1 118.8(5) . . ?
C5 C10 C1 121.0(4) . . ?
C12 O11 C1 118.8(3) . . ?
O12 C12 O11 123.1(4) . . ?
O12 C12 C13 126.8(4) . . ?
O11 C12 C13 110.0(3) . . ?
C14 C13 C22 120.6(4) . . ?
C14 C13 C12 118.7(5) . . ?
C22 C13 C12 120.7(4) . . ?
C13 C14 C15 121.1(5) . . ?
C16 C15 C14 119.7(5) . . ?
C15 C16 C17 121.5(4) . . ?
C16 C17 C18 121.1(4) . . ?
C16 C17 C22 119.5(4) . . ?
C18 C17 C22 119.5(5) . . ?
C19 C18 C17 120.9(5) . . ?
C18 C19 C20 120.4(6) . . ?
C21 C20 C19 120.6(6) . . ?
C20 C21 C22 120.3(5) . . ?
C21 C22 C17 118.3(4) . . ?
C21 C22 C13 123.9(4) . . ?
C17 C22 C13 117.7(4) . . ?

_refine_diff_density_max    0.672
_refine_diff_density_min   -0.812
_refine_diff_density_rms    0.052



#===END
