data_wguo3a
_audit_creation_date               2020-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_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           'C17 H14 Br N O'
_chemical_formula_sum              'C17 H14 Br N O'
_chemical_formula_weight           328.20
_chemical_absolute_configuration   ad
_chemical_melting_point            ?
_chemical_oxdiff_formula           'Br C30 H28 O4 N F3'
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        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     7.31665(16)
_cell_length_b                     11.3190(2)
_cell_length_c                     9.31501(20)
_cell_angle_alpha                  90
_cell_angle_beta                   111.743(2)
_cell_angle_gamma                  90
_cell_volume                       716.56(3)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      3381
_cell_measurement_temperature      100.01(10)
_cell_measurement_theta_max        72.3270
_cell_measurement_theta_min        6.3790
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      3.856
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.92547
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.521
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               332
_exptl_crystal_size_max            0.1
_exptl_crystal_size_mid            0.08
_exptl_crystal_size_min            0.03
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0206
_diffrn_reflns_av_unetI/netI       0.0311
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.981
_diffrn_reflns_limit_h_max         8
_diffrn_reflns_limit_h_min         -9
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         6
_diffrn_reflns_limit_l_min         -11
_diffrn_reflns_number              4098
_diffrn_reflns_point_group_measured_fraction_full  0.935
_diffrn_reflns_point_group_measured_fraction_max  0.904
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           72.535
_diffrn_reflns_theta_min           5.112
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100.01(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   5.1788
_diffrn_detector_type              Atlas
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     31.00 135.00   1.00    2.00    --  104.18 -61.00  30.00  104
  2  ω    -67.00  23.00   1.00    1.00    --  -40.20  57.00-120.00   90
  3  ω   -114.00 -20.00   1.00    1.00    --  -40.20 -57.00  90.00   94
  4  ω    -24.00  65.00   1.00    1.00    --   40.20 -37.00 -60.00   89
  5  ω     42.00 135.00   1.00    2.00    --  104.18 -61.00 150.00   93
  6  ω     26.00 109.00   1.00    2.00    --  104.18-111.00  30.00   83
  7  ω    109.00 149.00   1.00    2.00    --  104.18 111.00 150.00   40
  8  ω     60.00 164.00   1.00    2.00    --  104.18  15.00-120.00  104
  9  ω     76.00 176.00   1.00    2.00    --  104.18  30.00 120.00  100
 10  ω     66.00 108.00   1.00    2.00    --  104.18-111.00-180.00   42
 11  ω     29.00 108.00   1.00    2.00    --  104.18-111.00 -30.00   79
;
_diffrn_measurement_device         'kappa diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.1233265000
_diffrn_orient_matrix_UB_12        -0.0899242000
_diffrn_orient_matrix_UB_13        -0.1216876000
_diffrn_orient_matrix_UB_21        -0.1828334000
_diffrn_orient_matrix_UB_22        0.0324516000
_diffrn_orient_matrix_UB_23        0.0362790000
_diffrn_orient_matrix_UB_31        -0.0528445000
_diffrn_orient_matrix_UB_32        0.0969568000
_diffrn_orient_matrix_UB_33        -0.1246320000
_diffrn_oxdiff_digest_frames
;
01db8714ebf869f4cd414b0d6525045b9f0002920e8
;
_diffrn_oxdiff_digest_hkl
;
016aed5a92ad8b4382cb6d50da1336d861d54f
;
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_current             0.80
_diffrn_source_power               0.040
_diffrn_source_target              Cu
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage             50
_reflns_Friedel_coverage           0.749
_reflns_Friedel_fraction_full      0.865
_reflns_Friedel_fraction_max       0.818
_reflns_number_gt                  2526
_reflns_number_total               2571
_reflns_odcompleteness_completeness  99.85
_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 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection         'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction          'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.238
_refine_diff_density_min           -0.325
_refine_diff_density_rms           0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.023(16)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       182
_refine_ls_number_reflns           2571
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0219
_refine_ls_R_factor_gt             0.0214
_refine_ls_restrained_S_all        1.033
_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)+(0.0324P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0537
_refine_ls_wR_factor_ref           0.0540
_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:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 0.62920(4) 0.81514(4) 0.09006(3) 0.02126(10) Uani 1 1 d . . . . .
 O12 O 0.2919(4) 0.3919(2) 0.4528(3) 0.0221(5) Uani 1 1 d . . . . .
 N1 N -0.0266(4) 0.2687(2) 0.2730(3) 0.0166(5) Uani 1 1 d . . . . .
 C1 C -0.1619(5) 0.2454(3) 0.3421(3) 0.0192(6) Uani 1 1 d . . . . .
 H1 H -0.2451 0.3027 0.3611 0.023 Uiso 1 1 calc R . . . .
 C2 C -0.1579(5) 0.1287(3) 0.3786(4) 0.0228(7) Uani 1 1 d . . . . .
 H2 H -0.2368 0.0908 0.4261 0.027 Uiso 1 1 calc R . . . .
 C3 C -0.0121(5) 0.0740(3) 0.3318(3) 0.0186(6) Uani 1 1 d . . . . .
 C4 C 0.0681(5) 0.1640(3) 0.2677(3) 0.0156(6) Uani 1 1 d . . . . .
 C5 C 0.2145(5) 0.1422(3) 0.2092(4) 0.0207(7) Uani 1 1 d . . . . .
 H5 H 0.2681 0.2040 0.1680 0.025 Uiso 1 1 calc R . . . .
 C6 C 0.2788(5) 0.0262(3) 0.2137(4) 0.0250(7) Uani 1 1 d . . . . .
 H6 H 0.3779 0.0083 0.1740 0.030 Uiso 1 1 calc R . . . .
 C7 C 0.2006(5) -0.0650(3) 0.2757(4) 0.0275(8) Uani 1 1 d . . . . .
 H7 H 0.2473 -0.1434 0.2770 0.033 Uiso 1 1 calc R . . . .
 C8 C 0.0563(5) -0.0422(3) 0.3349(4) 0.0240(7) Uani 1 1 d . . . . .
 H8 H 0.0044 -0.1043 0.3770 0.029 Uiso 1 1 calc R . . . .
 C9 C 0.0142(5) 0.3803(3) 0.2154(4) 0.0172(6) Uani 1 1 d . . . . .
 H9 H 0.0142 0.3680 0.1091 0.021 Uiso 1 1 calc R . . . .
 C10 C 0.2177(5) 0.4263(3) 0.3201(4) 0.0164(6) Uani 1 1 d . . . . .
 C11 C 0.3150(5) 0.5183(3) 0.2582(4) 0.0149(6) Uani 1 1 d . . . . .
 C12 C 0.4746(5) 0.5794(3) 0.3638(3) 0.0174(6) Uani 1 1 d . . . . .
 H12 H 0.5190 0.5594 0.4703 0.021 Uiso 1 1 calc R . . . .
 C13 C 0.5689(5) 0.6683(3) 0.3160(3) 0.0171(6) Uani 1 1 d . . . . .
 H13 H 0.6750 0.7109 0.3885 0.021 Uiso 1 1 calc R . . . .
 C14 C 0.5041(4) 0.6936(3) 0.1588(3) 0.0152(6) Uani 1 1 d . . . . .
 C15 C 0.3495(5) 0.6327(3) 0.0501(3) 0.0177(6) Uani 1 1 d . . . . .
 H15 H 0.3108 0.6497 -0.0569 0.021 Uiso 1 1 calc R . . . .
 C16 C 0.2526(4) 0.5463(3) 0.1011(3) 0.0161(6) Uani 1 1 d . . . . .
 H16 H 0.1433 0.5060 0.0287 0.019 Uiso 1 1 calc R . . . .
 C17 C -0.1379(5) 0.4754(3) 0.2082(4) 0.0229(7) Uani 1 1 d . . . . .
 H17A H -0.2697 0.4470 0.1450 0.034 Uiso 1 1 calc GR . . . .
 H17B H -0.1091 0.5475 0.1621 0.034 Uiso 1 1 calc GR . . . .
 H17C H -0.1321 0.4927 0.3129 0.034 Uiso 1 1 calc GR . . . .


_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 C14 1.891(3) . ?
 O12 C10 1.215(4) . ?
 N1 C1 1.391(4) . ?
 N1 C4 1.383(4) . ?
 N1 C9 1.447(4) . ?
 C1 H1 0.9500 . ?
 C1 C2 1.361(5) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.434(5) . ?
 C3 C4 1.414(5) . ?
 C3 C8 1.403(5) . ?
 C4 C5 1.392(5) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.390(5) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.404(6) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.384(6) . ?
 C8 H8 0.9500 . ?
 C9 H9 1.0000 . ?
 C9 C10 1.536(4) . ?
 C9 C17 1.532(5) . ?
 C10 C11 1.493(5) . ?
 C11 C12 1.399(5) . ?
 C11 C16 1.398(4) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.384(5) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.392(4) . ?
 C14 C15 1.390(4) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.391(5) . ?
 C16 H16 0.9500 . ?
 C17 H17A 0.9800 . ?
 C17 H17B 0.9800 . ?
 C17 H17C 0.9800 . ?

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
 C1 N1 C9 128.1(3) . . ?
 C4 N1 C1 107.8(3) . . ?
 C4 N1 C9 124.1(3) . . ?
 N1 C1 H1 124.9 . . ?
 C2 C1 N1 110.3(3) . . ?
 C2 C1 H1 124.9 . . ?
 C1 C2 H2 126.5 . . ?
 C1 C2 C3 107.1(3) . . ?
 C3 C2 H2 126.5 . . ?
 C4 C3 C2 106.8(3) . . ?
 C8 C3 C2 134.3(3) . . ?
 C8 C3 C4 118.9(3) . . ?
 N1 C4 C3 108.1(3) . . ?
 N1 C4 C5 129.4(3) . . ?
 C5 C4 C3 122.5(3) . . ?
 C4 C5 H5 121.4 . . ?
 C6 C5 C4 117.2(3) . . ?
 C6 C5 H5 121.4 . . ?
 C5 C6 H6 119.3 . . ?
 C5 C6 C7 121.4(3) . . ?
 C7 C6 H6 119.3 . . ?
 C6 C7 H7 119.5 . . ?
 C8 C7 C6 121.0(3) . . ?
 C8 C7 H7 119.5 . . ?
 C3 C8 H8 120.5 . . ?
 C7 C8 C3 119.0(3) . . ?
 C7 C8 H8 120.5 . . ?
 N1 C9 H9 108.7 . . ?
 N1 C9 C10 110.2(3) . . ?
 N1 C9 C17 112.6(3) . . ?
 C10 C9 H9 108.7 . . ?
 C17 C9 H9 108.7 . . ?
 C17 C9 C10 107.9(3) . . ?
 O12 C10 C9 120.0(3) . . ?
 O12 C10 C11 121.2(3) . . ?
 C11 C10 C9 118.6(3) . . ?
 C12 C11 C10 117.8(3) . . ?
 C16 C11 C10 123.0(3) . . ?
 C16 C11 C12 119.2(3) . . ?
 C11 C12 H12 119.4 . . ?
 C13 C12 C11 121.3(3) . . ?
 C13 C12 H12 119.4 . . ?
 C12 C13 H13 120.9 . . ?
 C12 C13 C14 118.1(3) . . ?
 C14 C13 H13 120.9 . . ?
 C13 C14 Br1 119.1(2) . . ?
 C15 C14 Br1 118.7(2) . . ?
 C15 C14 C13 122.2(3) . . ?
 C14 C15 H15 120.7 . . ?
 C14 C15 C16 118.7(3) . . ?
 C16 C15 H15 120.7 . . ?
 C11 C16 H16 119.8 . . ?
 C15 C16 C11 120.5(3) . . ?
 C15 C16 H16 119.8 . . ?
 C9 C17 H17A 109.5 . . ?
 C9 C17 H17B 109.5 . . ?
 C9 C17 H17C 109.5 . . ?
 H17A C17 H17B 109.5 . . ?
 H17A C17 H17C 109.5 . . ?
 H17B C17 H17C 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 C14 C15 C16 -177.6(2) . . . . ?
 O12 C10 C11 C12 -11.5(5) . . . . ?
 O12 C10 C11 C16 169.1(3) . . . . ?
 N1 C1 C2 C3 0.4(4) . . . . ?
 N1 C4 C5 C6 -177.6(3) . . . . ?
 N1 C9 C10 O12 -22.1(4) . . . . ?
 N1 C9 C10 C11 161.5(3) . . . . ?
 C1 N1 C4 C3 1.1(3) . . . . ?
 C1 N1 C4 C5 179.9(3) . . . . ?
 C1 N1 C9 C10 109.4(4) . . . . ?
 C1 N1 C9 C17 -11.1(4) . . . . ?
 C1 C2 C3 C4 0.3(3) . . . . ?
 C1 C2 C3 C8 -178.3(3) . . . . ?
 C2 C3 C4 N1 -0.8(3) . . . . ?
 C2 C3 C4 C5 -179.7(3) . . . . ?
 C2 C3 C8 C7 178.7(3) . . . . ?
 C3 C4 C5 C6 1.0(5) . . . . ?
 C4 N1 C1 C2 -0.9(4) . . . . ?
 C4 N1 C9 C10 -70.4(4) . . . . ?
 C4 N1 C9 C17 169.1(3) . . . . ?
 C4 C3 C8 C7 0.3(4) . . . . ?
 C4 C5 C6 C7 -0.5(5) . . . . ?
 C5 C6 C7 C8 -0.1(5) . . . . ?
 C6 C7 C8 C3 0.2(5) . . . . ?
 C8 C3 C4 N1 178.0(3) . . . . ?
 C8 C3 C4 C5 -0.9(4) . . . . ?
 C9 N1 C1 C2 179.3(3) . . . . ?
 C9 N1 C4 C3 -179.1(3) . . . . ?
 C9 N1 C4 C5 -0.3(5) . . . . ?
 C9 C10 C11 C12 164.9(3) . . . . ?
 C9 C10 C11 C16 -14.4(4) . . . . ?
 C10 C11 C12 C13 -178.1(3) . . . . ?
 C10 C11 C16 C15 -179.8(3) . . . . ?
 C11 C12 C13 C14 -1.7(5) . . . . ?
 C12 C11 C16 C15 0.8(5) . . . . ?
 C12 C13 C14 Br1 179.7(2) . . . . ?
 C12 C13 C14 C15 -0.1(5) . . . . ?
 C13 C14 C15 C16 2.1(5) . . . . ?
 C14 C15 C16 C11 -2.5(5) . . . . ?
 C16 C11 C12 C13 1.3(5) . . . . ?
 C17 C9 C10 O12 101.2(4) . . . . ?
 C17 C9 C10 C11 -75.3(4) . . . . ?

_olex2_date_sample_data_collection  2020-06-30
_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  1.360
_oxdiff_exptl_absorpt_empirical_full_min  0.866
