 
data_shelx
 
_audit_creation_method            'SHELXL-2018/1'
_shelx_SHELXL_version_number      '2018/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H15 Br N2 O3' 
_chemical_formula_weight          435.27

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'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 '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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_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+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    9.1130(3)
_cell_length_b                    12.4570(5)
_cell_length_c                    16.9890(7)
_cell_angle_alpha                 90
_cell_angle_beta                  100.217(2)
_cell_angle_gamma                 90
_cell_volume                      1898.02(13)
_cell_formula_units_Z             4
_cell_measurement_temperature     298(2)
_cell_measurement_reflns_used     9972
_cell_measurement_theta_min       2.44
_cell_measurement_theta_max       26.12
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'color less'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.523          
_exptl_crystal_F_000              880
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.21
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.16
_exptl_absorpt_coefficient_mu     2.192
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    'none'
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       298(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             49066
_diffrn_reflns_av_unetI/netI      0.0349
_diffrn_reflns_av_R_equivalents   0.0708
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          2.436
_diffrn_reflns_theta_max          27.563
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              4368
_reflns_number_gt                 2975
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0637P)²+0.8710P] 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      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4368
_refine_ls_number_parameters      253
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0744
_refine_ls_R_factor_gt            0.0397
_refine_ls_wR_factor_ref          0.1170
_refine_ls_wR_factor_gt           0.0997
_refine_ls_goodness_of_fit_ref    0.958
_refine_ls_restrained_S_all       0.958
_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
Br1 Br 0.79524(3) 0.35289(3) 0.36632(2) 0.06552(15) Uani 1 1 d . . . . .
O3 O 0.6614(2) 0.57368(16) 0.38294(14) 0.0597(5) Uani 1 1 d . . . . .
N1 N 0.1636(2) 0.45802(17) 0.40395(15) 0.0518(6) Uani 1 1 d . . . . .
N2 N 0.2397(3) 0.24850(18) 0.39270(19) 0.0560(6) Uani 1 1 d . . . . .
O1 O 0.2396(3) 0.2069(2) 0.45670(18) 0.0878(8) Uani 1 1 d . . . . .
O2 O 0.1539(3) 0.2285(2) 0.33140(18) 0.0885(8) Uani 1 1 d . . . . .
C8 C 0.4119(3) 0.5205(2) 0.39030(16) 0.0426(6) Uani 1 1 d . . . . .
C16 C 0.5332(3) 0.1859(2) 0.37593(16) 0.0431(6) Uani 1 1 d . . . . .
C10 C 0.1524(3) 0.7582(2) 0.39188(16) 0.0454(6) Uani 1 1 d . . . . .
C6 C 0.4939(3) 0.3018(2) 0.38059(15) 0.0414(6) Uani 1 1 d . . . . .
C7 C 0.3538(3) 0.33164(19) 0.38902(16) 0.0427(6) Uani 1 1 d . . . . .
C4 C 0.5585(3) 0.4926(2) 0.38210(16) 0.0445(6) Uani 1 1 d . . . . .
C9 C 0.3067(3) 0.4387(2) 0.39494(16) 0.0425(6) Uani 1 1 d . . . . .
C2 C 0.2158(3) 0.64832(19) 0.39757(17) 0.0447(6) Uani 1 1 d . . . . .
C3 C 0.3609(3) 0.62766(19) 0.39252(16) 0.0453(6) Uani 1 1 d . . . . .
H3 H 0.426619 0.684276 0.390512 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5978(3) 0.3860(2) 0.37735(16) 0.0450(6) Uani 1 1 d . . . . .
C11 C 0.0404(3) 0.7872(2) 0.43294(18) 0.0539(7) Uani 1 1 d . . . . .
H11 H 0.003017 0.736821 0.464661 0.065 Uiso 1 1 calc R U . . .
C1 C 0.1224(3) 0.5588(2) 0.40522(18) 0.0519(7) Uani 1 1 d . . . . .
H1 H 0.024972 0.572783 0.411599 0.062 Uiso 1 1 calc R U . . .
C15 C 0.2048(4) 0.8349(2) 0.34381(18) 0.0526(7) Uani 1 1 d . . . . .
H15 H 0.279481 0.816828 0.315334 0.063 Uiso 1 1 calc R U . . .
C12 C -0.0167(4) 0.8904(2) 0.4273(2) 0.0639(8) Uani 1 1 d . . . . .
H12 H -0.091164 0.909133 0.455749 0.077 Uiso 1 1 calc R U . . .
C14 C 0.1461(4) 0.9376(2) 0.33825(19) 0.0628(8) Uani 1 1 d . . . . .
H14 H 0.181558 0.988257 0.306029 0.075 Uiso 1 1 calc R U . . .
C13 C 0.0359(4) 0.9652(2) 0.3800(2) 0.0649(9) Uani 1 1 d . . . . .
H13 H -0.002996 1.034435 0.376207 0.078 Uiso 1 1 calc R U . . .
C17 C 0.5970(4) 0.1311(2) 0.4435(2) 0.0624(8) Uani 1 1 d . . . . .
H17 H 0.619213 0.166945 0.492188 0.075 Uiso 1 1 calc R U . . .
C19 C 0.5968(4) -0.0306(3) 0.3702(2) 0.0669(9) Uani 1 1 d . . . . .
H19 H 0.619741 -0.103180 0.368378 0.080 Uiso 1 1 calc R U . . .
C21 C 0.4994(5) 0.1296(3) 0.3053(2) 0.0700(9) Uani 1 1 d . . . . .
H21 H 0.454894 0.164533 0.258738 0.084 Uiso 1 1 calc R U . . .
C18 C 0.6283(4) 0.0234(3) 0.4394(2) 0.0732(10) Uani 1 1 d . . . . .
H18 H 0.672133 -0.012593 0.485579 0.088 Uiso 1 1 calc R U . . .
C20 C 0.5317(5) 0.0211(3) 0.3034(2) 0.0793(11) Uani 1 1 d . . . . .
H20 H 0.508231 -0.016459 0.255515 0.095 Uiso 1 1 calc R U . . .
C22 C 0.6699(4) 0.6185(3) 0.3071(2) 0.0801(11) Uani 1 1 d . . . . .
H22A H 0.744007 0.674052 0.313322 0.120 Uiso 1 1 calc R U . . .
H22B H 0.696527 0.563449 0.272616 0.120 Uiso 1 1 calc R U . . .
H22C H 0.574803 0.648206 0.283914 0.120 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 C5 1.888(3) . ?
O3 C4 1.377(3) . ?
O3 C22 1.419(4) . ?
N1 C1 1.311(3) . ?
N1 C9 1.361(3) . ?
N2 O1 1.205(3) . ?
N2 O2 1.212(4) . ?
N2 C7 1.477(4) . ?
C8 C4 1.411(4) . ?
C8 C9 1.411(4) . ?
C8 C3 1.416(3) . ?
C16 C17 1.373(4) . ?
C16 C21 1.377(4) . ?
C16 C6 1.492(3) . ?
C10 C11 1.383(4) . ?
C10 C15 1.394(4) . ?
C10 C2 1.482(3) . ?
C6 C7 1.362(4) . ?
C6 C5 1.420(4) . ?
C7 C9 1.410(3) . ?
C4 C5 1.381(4) . ?
C2 C3 1.364(4) . ?
C2 C1 1.423(4) . ?
C3 H3 0.9300 . ?
C11 C12 1.384(4) . ?
C11 H11 0.9300 . ?
C1 H1 0.9300 . ?
C15 C14 1.384(4) . ?
C15 H15 0.9300 . ?
C12 C13 1.372(5) . ?
C12 H12 0.9300 . ?
C14 C13 1.372(5) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C17 C18 1.376(4) . ?
C17 H17 0.9300 . ?
C19 C18 1.340(5) . ?
C19 C20 1.348(5) . ?
C19 H19 0.9300 . ?
C21 C20 1.385(5) . ?
C21 H21 0.9300 . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C4 O3 C22 115.2(2) . . ?
C1 N1 C9 117.0(2) . . ?
O1 N2 O2 125.7(3) . . ?
O1 N2 C7 117.0(3) . . ?
O2 N2 C7 117.3(3) . . ?
C4 C8 C9 119.5(2) . . ?
C4 C8 C3 123.8(2) . . ?
C9 C8 C3 116.7(2) . . ?
C17 C16 C21 118.1(3) . . ?
C17 C16 C6 120.4(3) . . ?
C21 C16 C6 121.3(2) . . ?
C11 C10 C15 118.5(2) . . ?
C11 C10 C2 121.5(2) . . ?
C15 C10 C2 120.1(2) . . ?
C7 C6 C5 116.5(2) . . ?
C7 C6 C16 120.5(2) . . ?
C5 C6 C16 123.0(2) . . ?
C6 C7 C9 124.7(2) . . ?
C6 C7 N2 119.6(2) . . ?
C9 C7 N2 115.8(2) . . ?
O3 C4 C5 121.5(2) . . ?
O3 C4 C8 118.2(2) . . ?
C5 C4 C8 120.2(2) . . ?
N1 C9 C7 119.0(2) . . ?
N1 C9 C8 123.5(2) . . ?
C7 C9 C8 117.4(2) . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 C10 122.7(2) . . ?
C1 C2 C10 119.8(2) . . ?
C2 C3 C8 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C8 C3 H3 119.8 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 Br1 118.5(2) . . ?
C6 C5 Br1 119.71(19) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N1 C1 C2 124.9(2) . . ?
N1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C14 C15 C10 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C16 C21 C20 120.1(3) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C19 C18 C17 121.3(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
 
_refine_diff_density_max    0.596
_refine_diff_density_min   -0.507
_refine_diff_density_rms    0.051



