data_yc-7br_auto
_audit_creation_date               2023-06-13
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number       '2018/3'
_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. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C14 H11 Br F3 N O'
_chemical_formula_sum              'C14 H11 Br F3 N O'
_chemical_formula_weight           346.15
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C H O N F 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'
 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             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                     12.6437(2)
_cell_length_b                     8.2123(2)
_cell_length_c                     13.1511(2)
_cell_angle_alpha                  90
_cell_angle_beta                   106.061(2)
_cell_angle_gamma                  90
_cell_volume                       1312.23(4)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      6150
_cell_measurement_temperature      273.15
_cell_measurement_theta_max        75.3740
_cell_measurement_theta_min        4.3010
_shelx_estimated_absorpt_T_max     0.609
_shelx_estimated_absorpt_T_min     0.546
_exptl_absorpt_coefficient_mu      4.584
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.47616
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colorless
_exptl_crystal_density_diffrn      1.752
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               688
_exptl_crystal_size_max            0.15
_exptl_crystal_size_mid            0.13
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0379
_diffrn_reflns_av_unetI/netI       0.0315
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.947
_diffrn_reflns_limit_h_max         15
_diffrn_reflns_limit_h_min         -15
_diffrn_reflns_limit_k_max         9
_diffrn_reflns_limit_k_min         -3
_diffrn_reflns_limit_l_max         16
_diffrn_reflns_limit_l_min         -16
_diffrn_reflns_number              8179
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.947
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           76.589
_diffrn_reflns_theta_min           4.294
_diffrn_ambient_temperature        273.15
_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  0.947
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -44.00 -19.00   0.50    0.06    --  -46.85  10.00 -13.00   50
  2  ω    -80.00 -54.00   0.50    0.26    --  -95.00  10.00 -13.00   52
  3  ω    -68.00 -29.00   0.50    0.26    --  -95.00 125.00  90.00   78
  4  ω   -107.00 -81.00   0.50    0.26    --  -95.00 125.00  90.00   52
  5  ω   -121.00 -33.00   0.50    0.06    --  -46.85 -10.00 172.00  176
  6  ω   -170.00 -73.00   0.50    0.26    --  -95.00 -10.00 172.00  194
  7  ω     -4.00  27.00   0.50    0.06    --   46.85 -10.00 172.00   62
  8  ω     25.00 118.00   0.50    0.06    --   46.85  10.00 -13.00  186
  9  ω     36.00 122.00   0.50    0.26    --  107.00 -45.00 -30.00  172
 10  ω     86.00 129.00   0.50    0.26    --  107.00  10.00 -13.00   86
 11  ω     41.00 122.00   0.50    0.26    --  107.00 -45.00  60.00  162
 12  ω     31.00  94.00   0.50    0.26    --  107.00 -10.00 172.00  126
 13  ω     35.00  90.00   0.50    0.06    --   46.85-125.00  60.00  110
 14  ω     36.00  67.00   0.50    0.26    --  107.00 -94.00 -90.00   62
 15  ω     71.00  98.00   0.50    0.26    --  107.00 -94.00 -90.00   54
 16  ω     79.00 104.00   0.50    0.26    --  107.00 -94.00-150.00   50
 17  ω     64.00  97.00   0.50    0.26    --  107.00 -94.00-180.00   66
 18  ω     37.00  62.00   0.50    0.26    --  107.00 -94.00-180.00   50
 19  ω     66.00  92.00   0.50    0.26    --  107.00-125.00-180.00   52
;
_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        -0.1030300000
_diffrn_orient_matrix_UB_12        0.0054144000
_diffrn_orient_matrix_UB_13        0.0408730000
_diffrn_orient_matrix_UB_21        0.0737765000
_diffrn_orient_matrix_UB_22        0.0228645000
_diffrn_orient_matrix_UB_23        0.1139658000
_diffrn_orient_matrix_UB_31        -0.0061299000
_diffrn_orient_matrix_UB_32        0.1857885000
_diffrn_orient_matrix_UB_33        -0.0154574000
_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           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2343
_reflns_number_total               2608
_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 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection         'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction          'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics      'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max           0.806
_refine_diff_density_min           -0.587
_refine_diff_density_rms           0.081
_refine_ls_extinction_coef         0.0011(3)
_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     1.076
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       182
_refine_ls_number_reflns           2608
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0514
_refine_ls_R_factor_gt             0.0475
_refine_ls_restrained_S_all        1.076
_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)+(0.0886P)²+0.6516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1381
_refine_ls_wR_factor_ref           0.1443
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       direct
_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 -0.04411(3) 0.42766(5) 0.12802(3) 0.0699(2) Uani 1 1 d . . . . .
 F1 F 0.72848(18) 0.4460(4) 0.3173(2) 0.0858(8) Uani 1 1 d . . . . .
 F2 F 0.6578(2) 0.2531(4) 0.2146(3) 0.1027(9) Uani 1 1 d . . . . .
 F3 F 0.6310(2) 0.4963(5) 0.1602(2) 0.1117(11) Uani 1 1 d . . . . .
 O1 O 0.11599(19) 0.2230(3) 0.05679(18) 0.0653(6) Uani 1 1 d . . . . .
 N1 N 0.23344(18) 0.3375(3) 0.20325(17) 0.0441(5) Uani 1 1 d . . . . .
 C1 C 0.2379(2) 0.3303(3) 0.3766(2) 0.0457(6) Uani 1 1 d . . . . .
 C2 C 0.1966(3) 0.3334(4) 0.4641(2) 0.0533(7) Uani 1 1 d . . . . .
 H2 H 0.243612 0.325080 0.532225 0.064 Uiso 1 1 calc R U . . .
 C3 C 0.0846(3) 0.3490(4) 0.4481(3) 0.0565(7) Uani 1 1 d . . . . .
 H3 H 0.055454 0.347173 0.505724 0.068 Uiso 1 1 calc R U . . .
 C4 C 0.0148(3) 0.3677(4) 0.3463(3) 0.0561(7) Uani 1 1 d . . . . .
 H4 H -0.060316 0.380827 0.337054 0.067 Uiso 1 1 calc R U . . .
 C5 C 0.0551(2) 0.3669(3) 0.2588(2) 0.0469(6) Uani 1 1 d . . . . .
 C6 C 0.1671(2) 0.3413(3) 0.2729(2) 0.0415(5) Uani 1 1 d . . . . .
 C7 C 0.3486(2) 0.3255(4) 0.3687(2) 0.0501(6) Uani 1 1 d . . . . .
 H7 H 0.411831 0.319980 0.425168 0.060 Uiso 1 1 calc R U . . .
 C8 C 0.3454(2) 0.3306(4) 0.2655(2) 0.0461(6) Uani 1 1 d . . . . .
 C9 C 0.4353(2) 0.3276(4) 0.2110(2) 0.0491(6) Uani 1 1 d . . . . .
 H9 H 0.453182 0.213314 0.202208 0.059 Uiso 1 1 calc R U . . .
 C10 C 0.3917(3) 0.4002(5) 0.1017(3) 0.0589(8) Uani 1 1 d . . . . .
 H10A H 0.373896 0.514092 0.107601 0.071 Uiso 1 1 calc R U . . .
 H10B H 0.447906 0.393966 0.064336 0.071 Uiso 1 1 calc R U . . .
 C11 C 0.2902(3) 0.3097(5) 0.0401(2) 0.0601(8) Uani 1 1 d . . . . .
 H11A H 0.257505 0.369028 -0.024762 0.072 Uiso 1 1 calc R U . . .
 H11B H 0.312544 0.203964 0.020468 0.072 Uiso 1 1 calc R U . . .
 C12 C 0.2037(2) 0.2845(4) 0.0970(2) 0.0488(6) Uani 1 1 d . . . . .
 C13 C 0.5379(3) 0.4078(4) 0.2828(2) 0.0506(6) Uani 1 1 d . . . . .
 H13A H 0.521006 0.520716 0.293175 0.061 Uiso 1 1 calc R U . . .
 H13B H 0.555172 0.354781 0.351403 0.061 Uiso 1 1 calc R U . . .
 C14 C 0.6373(3) 0.4026(4) 0.2436(3) 0.0566(7) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Br1 C5 1.894(3) . ?
 F1 C14 1.333(4) . ?
 F2 C14 1.332(4) . ?
 F3 C14 1.324(4) . ?
 O1 C12 1.199(4) . ?
 N1 C6 1.404(3) . ?
 N1 C8 1.427(3) . ?
 N1 C12 1.412(3) . ?
 C1 C2 1.390(4) . ?
 C1 C6 1.412(4) . ?
 C1 C7 1.431(4) . ?
 C2 H2 0.9300 . ?
 C2 C3 1.379(5) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.394(5) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.380(4) . ?
 C5 C6 1.393(4) . ?
 C7 H7 0.9300 . ?
 C7 C8 1.347(4) . ?
 C8 C9 1.502(4) . ?
 C9 H9 0.9800 . ?
 C9 C10 1.512(4) . ?
 C9 C13 1.527(4) . ?
 C10 H10A 0.9700 . ?
 C10 H10B 0.9700 . ?
 C10 C11 1.511(5) . ?
 C11 H11A 0.9700 . ?
 C11 H11B 0.9700 . ?
 C11 C12 1.500(4) . ?
 C13 H13A 0.9700 . ?
 C13 H13B 0.9700 . ?
 C13 C14 1.486(4) . ?

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 N1 C8 107.7(2) . . ?
 C6 N1 C12 127.5(2) . . ?
 C12 N1 C8 120.4(2) . . ?
 C2 C1 C6 121.0(3) . . ?
 C2 C1 C7 131.3(3) . . ?
 C6 C1 C7 107.7(2) . . ?
 C1 C2 H2 120.6 . . ?
 C3 C2 C1 118.7(3) . . ?
 C3 C2 H2 120.6 . . ?
 C2 C3 H3 119.7 . . ?
 C2 C3 C4 120.5(3) . . ?
 C4 C3 H3 119.7 . . ?
 C3 C4 H4 119.4 . . ?
 C5 C4 C3 121.2(3) . . ?
 C5 C4 H4 119.4 . . ?
 C4 C5 Br1 116.8(2) . . ?
 C4 C5 C6 119.1(3) . . ?
 C6 C5 Br1 123.6(2) . . ?
 N1 C6 C1 107.1(2) . . ?
 C5 C6 N1 133.3(2) . . ?
 C5 C6 C1 119.2(2) . . ?
 C1 C7 H7 125.8 . . ?
 C8 C7 C1 108.4(2) . . ?
 C8 C7 H7 125.8 . . ?
 N1 C8 C9 119.2(2) . . ?
 C7 C8 N1 109.1(2) . . ?
 C7 C8 C9 131.7(3) . . ?
 C8 C9 H9 107.5 . . ?
 C8 C9 C10 108.8(2) . . ?
 C8 C9 C13 108.8(2) . . ?
 C10 C9 H9 107.5 . . ?
 C10 C9 C13 116.2(3) . . ?
 C13 C9 H9 107.5 . . ?
 C9 C10 H10A 109.6 . . ?
 C9 C10 H10B 109.6 . . ?
 H10A C10 H10B 108.1 . . ?
 C11 C10 C9 110.3(3) . . ?
 C11 C10 H10A 109.6 . . ?
 C11 C10 H10B 109.6 . . ?
 C10 C11 H11A 108.4 . . ?
 C10 C11 H11B 108.4 . . ?
 H11A C11 H11B 107.5 . . ?
 C12 C11 C10 115.4(3) . . ?
 C12 C11 H11A 108.4 . . ?
 C12 C11 H11B 108.4 . . ?
 O1 C12 N1 121.8(3) . . ?
 O1 C12 C11 123.4(3) . . ?
 N1 C12 C11 114.8(2) . . ?
 C9 C13 H13A 108.4 . . ?
 C9 C13 H13B 108.4 . . ?
 H13A C13 H13B 107.5 . . ?
 C14 C13 C9 115.4(3) . . ?
 C14 C13 H13A 108.4 . . ?
 C14 C13 H13B 108.4 . . ?
 F1 C14 C13 112.6(3) . . ?
 F2 C14 F1 104.9(3) . . ?
 F2 C14 C13 112.1(3) . . ?
 F3 C14 F1 106.8(3) . . ?
 F3 C14 F2 105.7(3) . . ?
 F3 C14 C13 114.1(3) . . ?

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 C5 C6 N1 -6.1(4) . . . . ?
 Br1 C5 C6 C1 166.7(2) . . . . ?
 N1 C8 C9 C10 22.9(4) . . . . ?
 N1 C8 C9 C13 150.5(3) . . . . ?
 C1 C2 C3 C4 -2.4(5) . . . . ?
 C1 C7 C8 N1 -0.4(3) . . . . ?
 C1 C7 C8 C9 -179.4(3) . . . . ?
 C2 C1 C6 N1 179.0(3) . . . . ?
 C2 C1 C6 C5 4.5(4) . . . . ?
 C2 C1 C7 C8 -177.6(3) . . . . ?
 C2 C3 C4 C5 1.6(5) . . . . ?
 C3 C4 C5 Br1 -170.2(2) . . . . ?
 C3 C4 C5 C6 2.3(4) . . . . ?
 C4 C5 C6 N1 -178.1(3) . . . . ?
 C4 C5 C6 C1 -5.3(4) . . . . ?
 C6 N1 C8 C7 1.7(3) . . . . ?
 C6 N1 C8 C9 -179.2(2) . . . . ?
 C6 N1 C12 O1 -6.0(5) . . . . ?
 C6 N1 C12 C11 174.7(3) . . . . ?
 C6 C1 C2 C3 -0.6(4) . . . . ?
 C6 C1 C7 C8 -1.0(3) . . . . ?
 C7 C1 C2 C3 175.6(3) . . . . ?
 C7 C1 C6 N1 2.0(3) . . . . ?
 C7 C1 C6 C5 -172.5(3) . . . . ?
 C7 C8 C9 C10 -158.2(3) . . . . ?
 C7 C8 C9 C13 -30.6(4) . . . . ?
 C8 N1 C6 C1 -2.2(3) . . . . ?
 C8 N1 C6 C5 171.2(3) . . . . ?
 C8 N1 C12 O1 147.5(3) . . . . ?
 C8 N1 C12 C11 -31.8(4) . . . . ?
 C8 C9 C10 C11 -56.4(3) . . . . ?
 C8 C9 C13 C14 175.3(3) . . . . ?
 C9 C10 C11 C12 49.2(4) . . . . ?
 C9 C13 C14 F1 -168.2(3) . . . . ?
 C9 C13 C14 F2 -50.2(4) . . . . ?
 C9 C13 C14 F3 69.9(4) . . . . ?
 C10 C9 C13 C14 -61.4(4) . . . . ?
 C10 C11 C12 O1 175.7(3) . . . . ?
 C10 C11 C12 N1 -4.9(4) . . . . ?
 C12 N1 C6 C1 154.0(3) . . . . ?
 C12 N1 C6 C5 -32.6(5) . . . . ?
 C12 N1 C8 C7 -156.5(3) . . . . ?
 C12 N1 C8 C9 22.6(4) . . . . ?
 C13 C9 C10 C11 -179.7(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  3.402
_oxdiff_exptl_absorpt_empirical_full_min  0.425
