data_tkd-589
_audit_creation_date               2023-04-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number       '2019/2'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C13 H10 Br2 O2'
_chemical_formula_sum              'C13 H10 Br2 O2'
_chemical_formula_weight           358.03
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C H O Br '
_chemical_oxdiff_usercomment       'yellow block'
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'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     9.50840(10)
_cell_length_b                     10.35540(10)
_cell_length_c                     13.20560(10)
_cell_angle_alpha                  90
_cell_angle_beta                   93.0920(10)
_cell_angle_gamma                  90
_cell_volume                       1298.37(2)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      8349
_cell_measurement_temperature      298
_cell_measurement_theta_max        77.5080
_cell_measurement_theta_min        4.2500
_shelx_estimated_absorpt_T_max     0.236
_shelx_estimated_absorpt_T_min     0.189
_exptl_absorpt_coefficient_mu      7.820
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.14418
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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      1.832
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               696
_exptl_crystal_preparation         'as per the reaction scheme'
_exptl_crystal_recrystallization_method  'slow evaporation'
_exptl_crystal_size_max            0.32
_exptl_crystal_size_mid            0.27
_exptl_crystal_size_min            0.26
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0611
_diffrn_reflns_av_unetI/netI       0.0531
_diffrn_reflns_Laue_measured_fraction_full  0.995
_diffrn_reflns_Laue_measured_fraction_max  0.969
_diffrn_reflns_limit_h_max         12
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         16
_diffrn_reflns_limit_l_min         -16
_diffrn_reflns_number              10087
_diffrn_reflns_point_group_measured_fraction_full  0.995
_diffrn_reflns_point_group_measured_fraction_max  0.969
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           77.809
_diffrn_reflns_theta_min           5.432
_diffrn_ambient_environment        air
_diffrn_ambient_temperature        297.56(14)
_diffrn_detector                   'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean   5.8140
_diffrn_detector_type              'Pilatus 200K'
_diffrn_measured_fraction_theta_full  0.995
_diffrn_measured_fraction_theta_max  0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -64.00  27.00   0.50    0.50    --  -38.50  81.00-154.00  182
  2  ω    -16.00  75.00   0.50    0.50    --   49.31 -81.00  82.00  182
  3  ω     42.00 133.00   0.50    1.00    --  107.46 -81.00  82.00  182
  4  ω    103.00 173.00   0.50    1.00    --  107.46  81.00-154.00  140
  5  ω    -42.00  28.00   0.50    0.50    --  -38.50  37.00-150.00  140
  6  ω    -17.00  53.00   0.50    0.50    --   49.31 -37.00-180.00  140
  7  ω     46.00 116.00   0.50    0.50    --   49.31  37.00 -30.00  140
  8  ω     46.00 116.00   0.50    0.50    --   49.31  37.00-150.00  140
  9  ω     43.00 113.00   0.50    1.00    --  107.46-125.00  90.00  140
 10  ω     43.00 113.00   0.50    1.00    --  107.46-125.00 -30.00  140
 11  ω     43.00 112.00   0.50    1.00    --  107.46 -45.00-120.00  138
 12  ω    103.00 172.00   0.50    1.00    --  107.46  77.00 -90.00  138
 13  ω     39.00 107.00   0.50    1.00    --  107.46 -94.00-180.00  136
 14  ω    103.00 172.00   0.50    1.00    --  107.46  77.00 -30.00  138
 15  ω     43.00 112.00   0.50    1.00    --  107.46 -45.00-180.00  138
 16  ω     39.00 107.00   0.50    1.00    --  107.46 -94.00-150.00  136
 17  ω    104.00 158.00   0.50    1.00    --  107.46  77.00 150.00  108
 18  ω     39.00 111.00   0.50    1.00    --  107.46 -30.00-150.00  144
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type   
 'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0660837000
_diffrn_orient_matrix_UB_12        -0.0623204000
_diffrn_orient_matrix_UB_13        0.0921246000
_diffrn_orient_matrix_UB_21        -0.0180064000
_diffrn_orient_matrix_UB_22        -0.1278316000
_diffrn_orient_matrix_UB_23        -0.0589566000
_diffrn_orient_matrix_UB_31        0.1470668000
_diffrn_orient_matrix_UB_32        -0.0436743000
_diffrn_orient_matrix_UB_33        0.0411111000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             'Cu K\a'
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2486
_reflns_number_total               2681
_reflns_odcompleteness_completeness  99.49
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       68.13
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection         'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction          'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           1.281
_refine_diff_density_min           -0.824
_refine_diff_density_rms           0.111
_refine_ls_extinction_coef         0.0043(4)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref     1.054
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       156
_refine_ls_number_reflns           2681
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0587
_refine_ls_R_factor_gt             0.0509
_refine_ls_restrained_S_all        1.054
_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)+(0.0874P)²+1.5258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1442
_refine_ls_wR_factor_ref           0.1471
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C12(H12)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 0.46551(5) 0.47579(5) 0.25532(5) 0.0685(2) Uani 1 1 d . . . . .
 Br2 Br 0.68189(6) 0.51171(5) 0.08337(3) 0.0633(2) Uani 1 1 d . . . . .
 O1 O 0.7704(4) 0.6697(3) 0.2649(2) 0.0616(8) Uani 1 1 d . . . . .
 O2 O 0.9393(4) 0.4894(3) 0.8763(2) 0.0569(7) Uani 1 1 d . . . . .
 C1 C 0.6624(4) 0.4684(3) 0.2233(3) 0.0403(7) Uani 1 1 d . . . . .
 H1 H 0.698612 0.381025 0.236202 0.048 Uiso 1 1 calc R U . . .
 C2 C 0.7400(3) 0.5631(3) 0.2952(3) 0.0398(7) Uani 1 1 d . . . . .
 C3 C 0.7731(4) 0.5206(3) 0.4001(3) 0.0379(7) Uani 1 1 d . . . . .
 C4 C 0.7537(4) 0.3909(3) 0.4337(3) 0.0439(7) Uani 1 1 d . . . . .
 H4 H 0.720320 0.328419 0.387846 0.053 Uiso 1 1 calc R U . . .
 C5 C 0.7837(4) 0.3580(3) 0.5328(3) 0.0457(8) Uani 1 1 d . . . . .
 H5 H 0.770275 0.273153 0.553281 0.055 Uiso 1 1 calc R U . . .
 C6 C 0.8345(3) 0.4495(3) 0.6044(2) 0.0381(7) Uani 1 1 d . . . . .
 C7 C 0.8558(3) 0.5792(3) 0.5720(3) 0.0394(7) Uani 1 1 d . . . . .
 C8 C 0.8247(3) 0.6111(3) 0.4694(3) 0.0422(7) Uani 1 1 d . . . . .
 H8 H 0.839301 0.695284 0.447778 0.051 Uiso 1 1 calc R U . . .
 C9 C 0.9079(4) 0.6711(4) 0.6440(3) 0.0512(8) Uani 1 1 d . . . . .
 H9 H 0.924739 0.755261 0.623392 0.061 Uiso 1 1 calc R U . . .
 C10 C 0.9337(4) 0.6382(4) 0.7426(3) 0.0524(9) Uani 1 1 d . . . . .
 H10 H 0.967255 0.700023 0.788962 0.063 Uiso 1 1 calc R U . . .
 C11 C 0.9095(4) 0.5093(4) 0.7757(3) 0.0436(8) Uani 1 1 d . . . . .
 C12 C 0.8632(3) 0.4166(3) 0.7075(3) 0.0421(7) Uani 1 1 d . . . . .
 H12 H 0.850682 0.332101 0.728988 0.050 Uiso 1 1 calc R U . . .
 C13 C 0.9360(5) 0.3598(5) 0.9116(3) 0.0614(10) Uani 1 1 d . . . . .
 H13A H 1.001430 0.308687 0.875835 0.092 Uiso 1 1 calc R U . . .
 H13B H 0.842773 0.325471 0.899796 0.092 Uiso 1 1 calc R U . . .
 H13C H 0.961571 0.357765 0.982870 0.092 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Br1 C1 1.943(3) . ?
 Br2 C1 1.920(4) . ?
 O1 C2 1.214(4) . ?
 O2 C11 1.359(5) . ?
 O2 C13 1.421(5) . ?
 C1 H1 0.9800 . ?
 C1 C2 1.527(5) . ?
 C2 C3 1.471(5) . ?
 C3 C4 1.430(4) . ?
 C3 C8 1.381(5) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.367(5) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.406(4) . ?
 C6 C7 1.428(5) . ?
 C6 C12 1.415(5) . ?
 C7 C8 1.411(5) . ?
 C7 C9 1.416(5) . ?
 C8 H8 0.9300 . ?
 C9 H9 0.9300 . ?
 C9 C10 1.355(6) . ?
 C10 H10 0.9300 . ?
 C10 C11 1.427(6) . ?
 C11 C12 1.373(5) . ?
 C12 H12 0.9300 . ?
 C13 H13A 0.9600 . ?
 C13 H13B 0.9600 . ?
 C13 H13C 0.9600 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C11 O2 C13 117.2(3) . . ?
 Br1 C1 H1 109.4 . . ?
 Br2 C1 Br1 110.13(16) . . ?
 Br2 C1 H1 109.4 . . ?
 C2 C1 Br1 106.2(2) . . ?
 C2 C1 Br2 112.4(2) . . ?
 C2 C1 H1 109.4 . . ?
 O1 C2 C1 119.6(3) . . ?
 O1 C2 C3 122.6(3) . . ?
 C3 C2 C1 117.7(3) . . ?
 C4 C3 C2 123.3(3) . . ?
 C8 C3 C2 118.1(3) . . ?
 C8 C3 C4 118.7(3) . . ?
 C3 C4 H4 119.8 . . ?
 C5 C4 C3 120.5(3) . . ?
 C5 C4 H4 119.8 . . ?
 C4 C5 H5 119.3 . . ?
 C4 C5 C6 121.5(3) . . ?
 C6 C5 H5 119.3 . . ?
 C5 C6 C7 118.8(3) . . ?
 C5 C6 C12 121.7(3) . . ?
 C12 C6 C7 119.5(3) . . ?
 C8 C7 C6 118.9(3) . . ?
 C8 C7 C9 122.4(3) . . ?
 C9 C7 C6 118.7(3) . . ?
 C3 C8 C7 121.7(3) . . ?
 C3 C8 H8 119.1 . . ?
 C7 C8 H8 119.1 . . ?
 C7 C9 H9 119.5 . . ?
 C10 C9 C7 121.0(4) . . ?
 C10 C9 H9 119.5 . . ?
 C9 C10 H10 119.8 . . ?
 C9 C10 C11 120.3(3) . . ?
 C11 C10 H10 119.8 . . ?
 O2 C11 C10 114.4(3) . . ?
 O2 C11 C12 125.3(4) . . ?
 C12 C11 C10 120.3(3) . . ?
 C6 C12 H12 120.0 . . ?
 C11 C12 C6 120.1(3) . . ?
 C11 C12 H12 120.0 . . ?
 O2 C13 H13A 109.5 . . ?
 O2 C13 H13B 109.5 . . ?
 O2 C13 H13C 109.5 . . ?
 H13A C13 H13B 109.5 . . ?
 H13A C13 H13C 109.5 . . ?
 H13B C13 H13C 109.5 . . ?

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 C1 C2 O1 -100.2(3) . . . . ?
 Br1 C1 C2 C3 78.9(3) . . . . ?
 Br2 C1 C2 O1 20.3(4) . . . . ?
 Br2 C1 C2 C3 -160.6(2) . . . . ?
 O1 C2 C3 C4 -172.2(4) . . . . ?
 O1 C2 C3 C8 8.2(5) . . . . ?
 O2 C11 C12 C6 179.4(4) . . . . ?
 C1 C2 C3 C4 8.8(5) . . . . ?
 C1 C2 C3 C8 -170.9(3) . . . . ?
 C2 C3 C4 C5 -178.7(3) . . . . ?
 C2 C3 C8 C7 178.4(3) . . . . ?
 C3 C4 C5 C6 -0.1(6) . . . . ?
 C4 C3 C8 C7 -1.2(5) . . . . ?
 C4 C5 C6 C7 -0.5(5) . . . . ?
 C4 C5 C6 C12 178.8(3) . . . . ?
 C5 C6 C7 C8 0.3(5) . . . . ?
 C5 C6 C7 C9 -179.5(3) . . . . ?
 C5 C6 C12 C11 -178.5(3) . . . . ?
 C6 C7 C8 C3 0.6(5) . . . . ?
 C6 C7 C9 C10 -1.8(5) . . . . ?
 C7 C6 C12 C11 0.8(5) . . . . ?
 C7 C9 C10 C11 0.5(6) . . . . ?
 C8 C3 C4 C5 1.0(5) . . . . ?
 C8 C7 C9 C10 178.4(3) . . . . ?
 C9 C7 C8 C3 -179.6(3) . . . . ?
 C9 C10 C11 O2 -179.9(4) . . . . ?
 C9 C10 C11 C12 1.6(6) . . . . ?
 C10 C11 C12 C6 -2.2(5) . . . . ?
 C12 C6 C7 C8 -179.0(3) . . . . ?
 C12 C6 C7 C9 1.1(5) . . . . ?
 C13 O2 C11 C10 -171.7(3) . . . . ?
 C13 O2 C11 C12 6.8(6) . . . . ?

_olex2_exptl_crystal_mounting_method  'mounted on a loop'
_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  2.470
_oxdiff_exptl_absorpt_empirical_full_min  0.412
