# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_e
_audit_block_doi                 10.5517/cc1jpyx2
_database_code_depnum_ccdc_archive 'CCDC 1421285'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Br N O'
_chemical_formula_weight         366.24

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   5.6160(8)
_cell_length_b                   13.1439(19)
_cell_length_c                   22.937(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1693.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    562
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      20.28

_exptl_crystal_description       rodlike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             780
_exptl_absorpt_coefficient_mu    2.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_T_max  0.649
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2926
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         23.26
_reflns_number_total             2246
_reflns_number_gt                1525
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0581P)²+0.5684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0072(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_number_reflns         2246
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.1826(3) 0.49989(10) -0.04517(4) 0.1485(7) Uani 1 1 d . . .
O1 O 0.4110(9) 0.2162(4) 0.1514(2) 0.0732(14) Uani 1 1 d . . .
N1 N 0.4437(10) 0.1068(5) 0.2584(3) 0.0667(17) Uani 1 1 d . . .
C1 C -0.0593(17) -0.0551(8) 0.2847(6) 0.102(3) Uani 1 1 d . . .
H1 H -0.1624 -0.0679 0.3156 0.122 Uiso 1 1 calc R . .
C2 C -0.082(2) -0.1072(8) 0.2339(7) 0.110(4) Uani 1 1 d . . .
H2 H -0.1988 -0.1569 0.2305 0.132 Uiso 1 1 calc R . .
C3 C 0.065(2) -0.0880(8) 0.1879(6) 0.108(3) Uani 1 1 d . . .
H3 H 0.0394 -0.1225 0.1531 0.130 Uiso 1 1 calc R . .
C4 C 0.2491(18) -0.0189(7) 0.1912(4) 0.090(3) Uani 1 1 d . . .
H4 H 0.3506 -0.0081 0.1597 0.108 Uiso 1 1 calc R . .
C5 C 0.2777(13) 0.0339(5) 0.2432(3) 0.0643(19) Uani 1 1 d . . .
C6 C 0.1235(15) 0.0194(6) 0.2904(3) 0.072(2) Uani 1 1 d . . .
C7 C 0.3965(15) 0.1380(6) 0.3140(4) 0.071(2) Uani 1 1 d . . .
C8 C 0.5200(18) 0.2105(7) 0.3471(4) 0.093(3) Uani 1 1 d . . .
H8 H 0.6533 0.2441 0.3326 0.111 Uiso 1 1 calc R . .
C9 C 0.432(3) 0.2293(9) 0.4026(6) 0.125(4) Uani 1 1 d . . .
H9 H 0.5116 0.2752 0.4266 0.150 Uiso 1 1 calc R . .
C10 C 0.232(3) 0.1822(10) 0.4228(5) 0.128(5) Uani 1 1 d . . .
H10 H 0.1773 0.1984 0.4599 0.153 Uiso 1 1 calc R . .
C11 C 0.111(2) 0.1132(9) 0.3912(4) 0.109(3) Uani 1 1 d . . .
H11 H -0.0261 0.0829 0.4057 0.130 Uiso 1 1 calc R . .
C12 C 0.1982(15) 0.0883(6) 0.3355(3) 0.070(2) Uani 1 1 d . . .
C13 C 0.6455(15) 0.1371(6) 0.2235(4) 0.082(2) Uani 1 1 d . . .
H13A H 0.6840 0.0826 0.1967 0.098 Uiso 1 1 calc R . .
H13B H 0.7817 0.1469 0.2489 0.098 Uiso 1 1 calc R . .
C14 C 0.6040(13) 0.2343(6) 0.1889(3) 0.075(2) Uani 1 1 d . . .
H14A H 0.5682 0.2903 0.2150 0.090 Uiso 1 1 calc R . .
H14B H 0.7451 0.2516 0.1666 0.090 Uiso 1 1 calc R . .
C15 C 0.1684(14) 0.2672(6) 0.0755(3) 0.068(2) Uani 1 1 d . . .
H15 H 0.0722 0.2117 0.0843 0.082 Uiso 1 1 calc R . .
C16 C 0.1136(15) 0.3302(7) 0.0301(3) 0.083(2) Uani 1 1 d . . .
H16 H -0.0198 0.3168 0.0073 0.099 Uiso 1 1 calc R . .
C17 C 0.2526(17) 0.4128(7) 0.0177(3) 0.081(3) Uani 1 1 d . . .
C18 C 0.4510(17) 0.4321(6) 0.0507(4) 0.083(2) Uani 1 1 d . . .
H18 H 0.5474 0.4874 0.0418 0.099 Uiso 1 1 calc R . .
C19 C 0.5089(14) 0.3698(6) 0.0972(3) 0.070(2) Uani 1 1 d . . .
H19 H 0.6408 0.3839 0.1203 0.084 Uiso 1 1 calc R . .
C20 C 0.3699(14) 0.2877(6) 0.1084(3) 0.0597(18) 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 C17 1.882(8) . ?
O1 C20 1.383(8) . ?
O1 C14 1.404(8) . ?
N1 C7 1.365(10) . ?
N1 C5 1.381(9) . ?
N1 C13 1.443(9) . ?
C1 C2 1.359(14) . ?
C1 C6 1.424(12) . ?
C2 C3 1.362(14) . ?
C3 C4 1.379(13) . ?
C4 C5 1.390(11) . ?
C5 C6 1.399(10) . ?
C6 C12 1.437(10) . ?
C7 C12 1.383(10) . ?
C7 C8 1.402(11) . ?
C8 C9 1.389(15) . ?
C9 C10 1.364(16) . ?
C10 C11 1.346(15) . ?
C11 C12 1.406(12) . ?
C13 C14 1.523(10) . ?
C15 C16 1.367(10) . ?
C15 C20 1.386(10) . ?
C16 C17 1.367(11) . ?
C17 C18 1.370(11) . ?
C18 C19 1.383(10) . ?
C19 C20 1.355(10) . ?

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
C20 O1 C14 116.8(6) . . ?
C7 N1 C5 108.2(6) . . ?
C7 N1 C13 125.9(7) . . ?
C5 N1 C13 125.6(7) . . ?
C2 C1 C6 119.4(10) . . ?
C1 C2 C3 121.0(11) . . ?
C2 C3 C4 122.3(11) . . ?
C3 C4 C5 117.5(10) . . ?
N1 C5 C4 129.8(8) . . ?
N1 C5 C6 108.5(7) . . ?
C4 C5 C6 121.6(8) . . ?
C5 C6 C1 118.0(8) . . ?
C5 C6 C12 106.9(8) . . ?
C1 C6 C12 135.1(9) . . ?
N1 C7 C12 110.3(7) . . ?
N1 C7 C8 127.9(9) . . ?
C12 C7 C8 121.8(9) . . ?
C9 C8 C7 116.3(10) . . ?
C10 C9 C8 121.6(12) . . ?
C11 C10 C9 122.6(12) . . ?
C10 C11 C12 118.1(11) . . ?
C7 C12 C11 119.6(10) . . ?
C7 C12 C6 106.0(7) . . ?
C11 C12 C6 134.4(10) . . ?
N1 C13 C14 113.6(7) . . ?
O1 C14 C13 107.2(6) . . ?
C16 C15 C20 118.7(7) . . ?
C15 C16 C17 120.8(8) . . ?
C16 C17 C18 119.7(8) . . ?
C16 C17 Br1 121.5(7) . . ?
C18 C17 Br1 118.8(7) . . ?
C17 C18 C19 120.5(8) . . ?
C20 C19 C18 118.8(7) . . ?
C19 C20 O1 125.4(7) . . ?
C19 C20 C15 121.5(7) . . ?
O1 C20 C15 113.1(7) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        23.26
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.050
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c
_audit_block_doi                 10.5517/cc1jpyy3
_database_code_depnum_ccdc_archive 'CCDC 1421286'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 Br N'
_chemical_formula_weight         301.20

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   16.0499(9)
_cell_length_b                   7.6796(3)
_cell_length_c                   22.6554(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2792.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    983
_cell_measurement_theta_min      2.9345
_cell_measurement_theta_max      28.8714

_exptl_crystal_description       rodlike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    2.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_T_max  0.704
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7796
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         28.94
_reflns_number_total             3231
_reflns_number_gt                1542
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0534P)²+1.0552P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3231
_refine_ls_number_parameters     164
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.14910(4) 0.67749(6) 0.01103(3) 0.0970(3) Uani 1 1 d U . .
N1 N 0.0678(2) -0.0439(4) 0.13363(13) 0.0515(8) Uani 1 1 d . . .
C1 C 0.0941(3) 0.2736(5) 0.1330(2) 0.0757(14) Uani 1 1 d U . .
H1A H 0.1147 0.2657 0.1731 0.091 Uiso 1 1 calc R . .
H1B H 0.0350 0.2994 0.1347 0.091 Uiso 1 1 calc R . .
C2 C 0.0915(3) 0.4825(6) 0.0510(2) 0.0863(15) Uani 1 1 d U . .
H2A H 0.0369 0.5202 0.0643 0.104 Uiso 1 1 calc R . .
H2B H 0.0841 0.3868 0.0236 0.104 Uiso 1 1 calc R . .
C3 C -0.0655(3) -0.0603(7) 0.0779(2) 0.0792(14) Uani 1 1 d . . .
C4 C -0.1384(4) -0.1569(10) 0.0753(3) 0.110(2) Uani 1 1 d . . .
H4A H -0.1778 -0.1280 0.0469 0.132 Uiso 1 1 calc R . .
C5 C -0.1552(4) -0.2952(10) 0.1132(3) 0.109(2) Uani 1 1 d . . .
H5A H -0.2052 -0.3555 0.1096 0.131 Uiso 1 1 calc R . .
C6 C -0.0990(3) -0.3442(6) 0.1562(2) 0.0837(16) Uani 1 1 d . . .
H6A H -0.1105 -0.4369 0.1813 0.100 Uiso 1 1 calc R . .
C7 C 0.1444(4) -0.3451(6) 0.2731(2) 0.0857(16) Uani 1 1 d . . .
H7A H 0.1594 -0.4156 0.3047 0.103 Uiso 1 1 calc R . .
C8 C 0.1983(3) -0.2173(6) 0.2539(2) 0.0748(13) Uani 1 1 d . . .
H8A H 0.2493 -0.2038 0.2728 0.090 Uiso 1 1 calc R . .
C9 C 0.0689(3) -0.3693(5) 0.2460(2) 0.0696(13) Uani 1 1 d . . .
H9A H 0.0327 -0.4557 0.2591 0.084 Uiso 1 1 calc R . .
C10 C 0.1065(3) 0.1012(5) 0.10268(17) 0.0602(11) Uani 1 1 d . . .
H10A H 0.0836 0.1079 0.0631 0.072 Uiso 1 1 calc R . .
H10B H 0.1658 0.0788 0.0991 0.072 Uiso 1 1 calc R . .
C11 C -0.0096(3) -0.1129(5) 0.12161(17) 0.0558(10) Uani 1 1 d . . .
C12 C 0.1399(3) 0.4255(6) 0.1006(2) 0.0716(12) Uani 1 1 d U . .
H12A H 0.1481 0.5218 0.1277 0.086 Uiso 1 1 calc R . .
H12B H 0.1942 0.3863 0.0873 0.086 Uiso 1 1 calc R . .
C13 C -0.0242(3) -0.2515(5) 0.16122(19) 0.0569(10) Uani 1 1 d . . .
C14 C 0.1787(3) -0.1094(5) 0.20760(18) 0.0587(11) Uani 1 1 d . . .
H14A H 0.2154 -0.0236 0.1950 0.070 Uiso 1 1 calc R . .
C15 C 0.1032(3) -0.1325(4) 0.18068(16) 0.0480(9) Uani 1 1 d . . .
C16 C 0.0471(3) -0.2634(4) 0.19893(17) 0.0512(10) 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 C2 1.979(5) . ?
N1 C11 1.378(5) . ?
N1 C15 1.386(5) . ?
N1 C10 1.456(5) . ?
C1 C10 1.505(5) . ?
C1 C12 1.561(6) . ?
C2 C12 1.435(6) . ?
C3 C4 1.387(7) . ?
C3 C11 1.395(6) . ?
C4 C5 1.393(9) . ?
C5 C6 1.380(8) . ?
C6 C13 1.400(6) . ?
C7 C9 1.370(7) . ?
C7 C8 1.379(7) . ?
C8 C14 1.373(6) . ?
C9 C16 1.386(6) . ?
C11 C13 1.412(6) . ?
C13 C16 1.431(6) . ?
C14 C15 1.368(5) . ?
C15 C16 1.411(5) . ?

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 N1 C15 109.5(3) . . ?
C11 N1 C10 125.7(3) . . ?
C15 N1 C10 124.8(3) . . ?
C10 C1 C12 112.4(3) . . ?
C12 C2 Br1 109.7(4) . . ?
C4 C3 C11 114.7(5) . . ?
C3 C4 C5 123.0(6) . . ?
C6 C5 C4 121.1(5) . . ?
C5 C6 C13 118.7(5) . . ?
C9 C7 C8 120.7(4) . . ?
C14 C8 C7 121.8(5) . . ?
C7 C9 C16 119.2(4) . . ?
N1 C10 C1 113.4(3) . . ?
N1 C11 C3 127.5(4) . . ?
N1 C11 C13 108.3(4) . . ?
C3 C11 C13 124.3(4) . . ?
C2 C12 C1 109.9(4) . . ?
C6 C13 C11 118.3(5) . . ?
C6 C13 C16 134.6(4) . . ?
C11 C13 C16 107.2(3) . . ?
C15 C14 C8 117.7(4) . . ?
C14 C15 N1 130.0(4) . . ?
C14 C15 C16 121.8(4) . . ?
N1 C15 C16 108.3(4) . . ?
C9 C16 C15 118.8(4) . . ?
C9 C16 C13 134.3(4) . . ?
C15 C16 C13 106.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.875
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.058
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c4phbr
_audit_block_doi                 10.5517/cc1jpyz4
_database_code_depnum_ccdc_archive 'CCDC 1421287'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Br N O'
_chemical_formula_weight         394.30

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   9.5118(19)
_cell_length_b                   19.672(4)
_cell_length_c                   9.821(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.45(3)
_cell_angle_gamma                90.00
_cell_volume                     1837.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11169
_cell_measurement_theta_min      6.004
_cell_measurement_theta_max      55.25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    2.246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.469
_exptl_absorpt_correction_T_max  0.574
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17447
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4185
_reflns_number_gt                2838
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0732P)²+0.2140P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4185
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.42034(3) 0.024196(17) 0.75035(4) 0.07479(17) Uani 1 1 d . . .
N1 N 0.4787(2) 0.26762(10) 0.8861(2) 0.0431(5) Uani 1 1 d . . .
O1 O 0.1237(2) 0.15322(10) 0.93568(17) 0.0564(5) Uani 1 1 d . . .
C6 C 0.3936(3) 0.32341(12) 0.8606(2) 0.0406(5) Uani 1 1 d . . .
C12 C 0.6119(3) 0.29032(12) 0.9242(2) 0.0417(5) Uani 1 1 d . . .
C5 C 0.2521(3) 0.32635(14) 0.8232(3) 0.0513(6) Uani 1 1 d . . .
H5 H 0.1992 0.2870 0.8113 0.062 Uiso 1 1 calc R . .
C1 C 0.4735(3) 0.38281(12) 0.8818(2) 0.0413(5) Uani 1 1 d . . .
C7 C 0.6123(3) 0.36177(12) 0.9230(2) 0.0412(5) Uani 1 1 d . . .
C20 C -0.2481(3) 0.06431(14) 0.8101(3) 0.0531(6) Uani 1 1 d . . .
C17 C 0.0003(3) 0.12217(14) 0.9004(3) 0.0480(6) Uani 1 1 d . . .
C2 C 0.4096(3) 0.44571(14) 0.8607(3) 0.0523(6) Uani 1 1 d . . .
H2 H 0.4610 0.4856 0.8727 0.063 Uiso 1 1 calc R . .
C8 C 0.7360(3) 0.39588(14) 0.9581(3) 0.0531(7) Uani 1 1 d . . .
H8 H 0.7385 0.4431 0.9586 0.064 Uiso 1 1 calc R . .
C11 C 0.7309(3) 0.25281(15) 0.9585(3) 0.0530(6) Uani 1 1 d . . .
H11 H 0.7298 0.2055 0.9585 0.064 Uiso 1 1 calc R . .
C18 C -0.0446(3) 0.12893(16) 0.7656(3) 0.0573(7) Uani 1 1 d . . .
H18 H 0.0100 0.1531 0.7051 0.069 Uiso 1 1 calc R . .
C13 C 0.4386(3) 0.19666(13) 0.8746(3) 0.0503(6) Uani 1 1 d . . .
H13A H 0.5083 0.1728 0.8224 0.060 Uiso 1 1 calc R . .
H13B H 0.3493 0.1935 0.8251 0.060 Uiso 1 1 calc R . .
C4 C 0.1930(3) 0.38933(15) 0.8045(3) 0.0586(7) Uani 1 1 d . . .
H4 H 0.0983 0.3923 0.7792 0.070 Uiso 1 1 calc R . .
C3 C 0.2698(3) 0.44840(16) 0.8219(3) 0.0610(7) Uani 1 1 d . . .
H3 H 0.2266 0.4903 0.8073 0.073 Uiso 1 1 calc R . .
C21 C -0.2052(3) 0.05713(15) 0.9436(3) 0.0577(7) Uani 1 1 d . . .
H21 H -0.2601 0.0327 1.0034 0.069 Uiso 1 1 calc R . .
C9 C 0.8548(3) 0.35899(17) 0.9920(3) 0.0622(8) Uani 1 1 d . . .
H9 H 0.9381 0.3815 1.0147 0.075 Uiso 1 1 calc R . .
C15 C 0.3060(3) 0.18843(16) 1.0949(3) 0.0598(7) Uani 1 1 d . . .
H15A H 0.2887 0.2356 1.0709 0.072 Uiso 1 1 calc R . .
H15B H 0.3346 0.1871 1.1904 0.072 Uiso 1 1 calc R . .
C19 C -0.1692(3) 0.10012(15) 0.7206(3) 0.0591(7) Uani 1 1 d . . .
H19 H -0.1993 0.1050 0.6303 0.071 Uiso 1 1 calc R . .
C22 C -0.0805(3) 0.08604(15) 0.9893(3) 0.0551(7) Uani 1 1 d . . .
H22 H -0.0512 0.0811 1.0798 0.066 Uiso 1 1 calc R . .
C16 C 0.1696(3) 0.14907(16) 1.0765(3) 0.0575(7) Uani 1 1 d . . .
H16A H 0.1842 0.1019 1.1022 0.069 Uiso 1 1 calc R . .
H16B H 0.0984 0.1681 1.1343 0.069 Uiso 1 1 calc R . .
C10 C 0.8514(3) 0.28899(18) 0.9926(3) 0.0635(8) Uani 1 1 d . . .
H10 H 0.9329 0.2653 1.0167 0.076 Uiso 1 1 calc R . .
C14 C 0.4254(3) 0.16214(16) 1.0112(3) 0.0611(7) Uani 1 1 d . . .
H14A H 0.4122 0.1138 0.9964 0.073 Uiso 1 1 calc R . .
H14B H 0.5128 0.1681 1.0628 0.073 Uiso 1 1 calc R . .


_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 C20 1.898(3) . ?
N1 C6 1.383(3) . ?
N1 C12 1.386(3) . ?
N1 C13 1.451(3) . ?
O1 C17 1.360(3) . ?
O1 C16 1.442(3) . ?
C6 C5 1.387(4) . ?
C6 C1 1.407(3) . ?
C12 C11 1.385(4) . ?
C12 C7 1.406(3) . ?
C5 C4 1.371(4) . ?
C1 C2 1.392(4) . ?
C1 C7 1.432(3) . ?
C7 C8 1.390(3) . ?
C20 C19 1.366(4) . ?
C20 C21 1.370(4) . ?
C17 C22 1.375(4) . ?
C17 C18 1.387(4) . ?
C2 C3 1.375(4) . ?
C8 C9 1.377(4) . ?
C11 C10 1.383(4) . ?
C18 C19 1.376(4) . ?
C13 C14 1.511(4) . ?
C4 C3 1.381(4) . ?
C21 C22 1.380(4) . ?
C9 C10 1.378(5) . ?
C15 C14 1.511(4) . ?
C15 C16 1.517(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 C12 108.7(2) . . ?
C6 N1 C13 126.7(2) . . ?
C12 N1 C13 124.6(2) . . ?
C17 O1 C16 117.2(2) . . ?
N1 C6 C5 129.8(2) . . ?
N1 C6 C1 108.7(2) . . ?
C5 C6 C1 121.4(2) . . ?
C11 C12 N1 129.0(2) . . ?
C11 C12 C7 122.1(2) . . ?
N1 C12 C7 108.8(2) . . ?
C4 C5 C6 117.7(3) . . ?
C2 C1 C6 119.0(2) . . ?
C2 C1 C7 134.0(2) . . ?
C6 C1 C7 107.0(2) . . ?
C8 C7 C12 118.9(2) . . ?
C8 C7 C1 134.3(2) . . ?
C12 C7 C1 106.8(2) . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 Br1 120.0(2) . . ?
C21 C20 Br1 119.2(2) . . ?
O1 C17 C22 124.3(2) . . ?
O1 C17 C18 116.3(2) . . ?
C22 C17 C18 119.4(3) . . ?
C3 C2 C1 119.4(3) . . ?
C9 C8 C7 119.3(3) . . ?
C12 C11 C10 116.9(3) . . ?
C19 C18 C17 120.6(3) . . ?
N1 C13 C14 113.0(2) . . ?
C5 C4 C3 122.0(3) . . ?
C2 C3 C4 120.4(3) . . ?
C20 C21 C22 120.1(3) . . ?
C8 C9 C10 120.6(3) . . ?
C14 C15 C16 114.4(3) . . ?
C20 C19 C18 119.2(3) . . ?
C17 C22 C21 119.7(3) . . ?
O1 C16 C15 108.8(2) . . ?
C9 C10 C11 122.2(3) . . ?
C15 C14 C13 114.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.100
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c
_audit_block_doi                 10.5517/cc1jpz06
_database_code_depnum_ccdc_archive 'CCDC 1421288'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 Br N'
_chemical_formula_weight         316.23

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   17.503(4)
_cell_length_b                   8.0333(16)
_cell_length_c                   21.133(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2971.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3105
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      28.78

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    2.753
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.5651
_exptl_absorpt_correction_T_max  0.6117
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25212
_diffrn_reflns_av_R_equivalents  0.1382
_diffrn_reflns_av_sigmaI/netI    0.0890
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3399
_reflns_number_gt                1104
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1951P)²+0.0605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3399
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2594
_refine_ls_R_factor_gt           0.1050
_refine_ls_wR_factor_ref         0.3808
_refine_ls_wR_factor_gt          0.2872
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.003

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.1902(3) 0.7707(6) 0.0103(2) 0.1184(18) Uani 0.497(10) 1 d P . .
Br1' Br 0.21003(18) 0.6669(11) -0.0176(2) 0.134(3) Uani 0.503(10) 1 d P . .
N1 N 0.0962(4) 0.0069(7) 0.1480(3) 0.0790(17) Uani 1 1 d . . .
C5 C 0.0773(5) -0.2007(8) 0.2189(4) 0.078(2) Uani 1 1 d . . .
C3 C -0.0499(5) -0.2948(11) 0.1729(4) 0.094(2) Uani 1 1 d . . .
H3A H -0.0582 -0.3823 0.2009 0.112 Uiso 1 1 calc R . .
C4 C 0.0147(5) -0.2003(8) 0.1775(3) 0.0735(19) Uani 1 1 d . . .
C12 C 0.1275(5) -0.0696(8) 0.2004(4) 0.075(2) Uani 1 1 d . . .
C11 C 0.1947(5) -0.0352(10) 0.2305(4) 0.094(2) Uani 1 1 d . . .
H11A H 0.2274 0.0480 0.2163 0.113 Uiso 1 1 calc R . .
C51 C 0.0272(5) -0.0688(9) 0.1343(3) 0.077(2) Uani 1 1 d . . .
C13 C 0.1282(5) 0.1488(8) 0.1153(4) 0.088(2) Uani 1 1 d . . .
H13A H 0.1121 0.1462 0.0713 0.105 Uiso 1 1 calc R . .
H13B H 0.1835 0.1411 0.1161 0.105 Uiso 1 1 calc R . .
C8 C 0.0988(7) -0.2940(10) 0.2726(4) 0.100(3) Uani 1 1 d . . .
H8A H 0.0677 -0.3798 0.2871 0.121 Uiso 1 1 calc R . .
C14 C 0.1037(5) 0.3138(9) 0.1447(4) 0.098(3) Uani 1 1 d . . .
H14A H 0.1218 0.3198 0.1880 0.117 Uiso 1 1 calc R . .
H14B H 0.0484 0.3209 0.1453 0.117 Uiso 1 1 calc R . .
C10 C 0.2118(5) -0.1305(13) 0.2833(5) 0.105(3) Uani 1 1 d . . .
H10A H 0.2562 -0.1066 0.3057 0.126 Uiso 1 1 calc R . .
C16 C 0.0983(5) 0.4859(13) 0.0454(6) 0.123(3) Uani 1 1 d . . .
H16A H 0.0448 0.5056 0.0548 0.148 Uiso 1 1 calc R . .
H16B H 0.1009 0.3810 0.0228 0.148 Uiso 1 1 calc R . .
C6 C -0.0258(6) -0.0323(11) 0.0878(4) 0.097(2) Uani 1 1 d . . .
H6A H -0.0174 0.0545 0.0596 0.116 Uiso 1 1 calc R . .
C2 C -0.1019(6) -0.2597(13) 0.1270(6) 0.114(3) Uani 1 1 d . . .
H2A H -0.1458 -0.3246 0.1236 0.137 Uiso 1 1 calc R . .
C15 C 0.1370(5) 0.4609(9) 0.1060(4) 0.092(2) Uani 1 1 d . . .
H15A H 0.1329 0.5620 0.1309 0.111 Uiso 1 1 calc R . .
H15B H 0.1908 0.4405 0.0983 0.111 Uiso 1 1 calc R . .
C17 C 0.1280(12) 0.648(2) -0.0102(12) 0.357(19) Uani 1 1 d . . .
H17A H 0.1197 0.6105 -0.0527 0.428 Uiso 1 1 d R . .
H17B H 0.0865 0.7224 -0.0009 0.428 Uiso 1 1 d R . .
C9 C 0.1669(7) -0.2571(12) 0.3039(5) 0.114(3) Uani 1 1 d . . .
H9A H 0.1816 -0.3195 0.3389 0.136 Uiso 1 1 calc R . .
C1 C -0.0906(6) -0.1262(15) 0.0843(5) 0.111(3) Uani 1 1 d . . .
H1A H -0.1273 -0.1025 0.0538 0.133 Uiso 1 1 calc R . .


_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 Br1' 1.080(4) . ?
Br1 C17 1.530(17) . ?
Br1' C17 1.45(2) . ?
N1 C12 1.380(9) . ?
N1 C51 1.382(10) . ?
N1 C13 1.447(9) . ?
C5 C4 1.402(11) . ?
C5 C8 1.411(12) . ?
C5 C12 1.426(10) . ?
C3 C2 1.360(13) . ?
C3 C4 1.365(10) . ?
C4 C51 1.413(9) . ?
C12 C11 1.367(10) . ?
C11 C10 1.385(12) . ?
C51 C6 1.382(11) . ?
C13 C14 1.525(10) . ?
C8 C9 1.395(13) . ?
C14 C15 1.550(10) . ?
C10 C9 1.356(12) . ?
C16 C15 1.463(12) . ?
C16 C17 1.83(3) . ?
C6 C1 1.364(12) . ?
C2 C1 1.416(13) . ?

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
Br1' Br1 C17 65.0(9) . . ?
Br1 Br1' C17 72.7(8) . . ?
C12 N1 C51 108.6(6) . . ?
C12 N1 C13 125.5(7) . . ?
C51 N1 C13 125.8(7) . . ?
C4 C5 C8 135.4(8) . . ?
C4 C5 C12 108.0(7) . . ?
C8 C5 C12 116.6(8) . . ?
C2 C3 C4 119.4(9) . . ?
C3 C4 C5 133.6(8) . . ?
C3 C4 C51 119.9(8) . . ?
C5 C4 C51 106.5(7) . . ?
C11 C12 N1 128.8(7) . . ?
C11 C12 C5 123.5(8) . . ?
N1 C12 C5 107.7(7) . . ?
C12 C11 C10 116.7(8) . . ?
C6 C51 N1 129.9(7) . . ?
C6 C51 C4 120.9(8) . . ?
N1 C51 C4 109.2(7) . . ?
N1 C13 C14 112.4(6) . . ?
C9 C8 C5 119.8(8) . . ?
C13 C14 C15 110.0(6) . . ?
C9 C10 C11 123.2(9) . . ?
C15 C16 C17 121.9(8) . . ?
C1 C6 C51 118.7(9) . . ?
C3 C2 C1 121.1(9) . . ?
C16 C15 C14 113.1(8) . . ?
Br1' C17 Br1 42.4(6) . . ?
Br1' C17 C16 115.1(10) . . ?
Br1 C17 C16 118.6(12) . . ?
C10 C9 C8 120.1(9) . . ?
C6 C1 C2 120.1(9) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.941
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.093
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kac5phylbr
_audit_block_doi                 10.5517/cc1jpz17
_database_code_depnum_ccdc_archive 'CCDC 1421289'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 Br N O'
_chemical_formula_weight         408.33

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.368(4)
_cell_length_b                   9.0221(18)
_cell_length_c                   23.995(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.82(3)
_cell_angle_gamma                90.00
_cell_volume                     3877.3(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9761
_cell_measurement_theta_min      6.12
_cell_measurement_theta_max      55.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.582
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    2.131
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18432
_diffrn_reflns_av_R_equivalents  0.1185
_diffrn_reflns_av_sigmaI/netI    0.0879
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4446
_reflns_number_gt                2014
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0439P)²+1.9255P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4446
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1604
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.05631(3) -0.06860(6) 1.116258(19) 0.0937(2) Uani 1 1 d . . .
O1 O 0.76237(16) 0.0585(2) 0.95542(10) 0.0668(7) Uani 1 1 d . . .
N1 N 0.67882(17) 0.2158(3) 0.70882(11) 0.0534(7) Uani 1 1 d . . .
C6 C 0.6979(2) 0.0796(3) 0.63378(13) 0.0488(8) Uani 1 1 d . . .
C12 C 0.7550(2) 0.2130(3) 0.71253(13) 0.0499(9) Uani 1 1 d . . .
C7 C 0.7690(2) 0.1292(3) 0.66638(13) 0.0495(9) Uani 1 1 d . . .
C1 C 0.6433(2) 0.1345(3) 0.66138(13) 0.0490(8) Uani 1 1 d . . .
C14 C 0.6191(2) 0.1988(4) 0.79196(15) 0.0633(10) Uani 1 1 d . . .
H14A H 0.5893 0.2570 0.8126 0.076 Uiso 1 1 calc R . .
H14B H 0.5879 0.1185 0.7731 0.076 Uiso 1 1 calc R . .
C15 C 0.6840(2) 0.1328(4) 0.83464(14) 0.0628(10) Uani 1 1 d . . .
H15A H 0.7127 0.2125 0.8561 0.075 Uiso 1 1 calc R . .
H15B H 0.7162 0.0812 0.8140 0.075 Uiso 1 1 calc R . .
C11 C 0.8127(2) 0.2768(4) 0.75260(15) 0.0621(10) Uani 1 1 d . . .
H11 H 0.8031 0.3323 0.7829 0.075 Uiso 1 1 calc R . .
C2 C 0.5688(2) 0.1042(4) 0.64133(16) 0.0647(10) Uani 1 1 d . . .
H2 H 0.5333 0.1396 0.6603 0.078 Uiso 1 1 calc R . .
C17 C 0.7243(2) -0.0501(4) 0.91583(16) 0.0718(12) Uani 1 1 d . . .
H17A H 0.7059 -0.1295 0.9362 0.086 Uiso 1 1 calc R . .
H17B H 0.7582 -0.0921 0.8943 0.086 Uiso 1 1 calc R . .
C4 C 0.6004(3) -0.0335(4) 0.56438(17) 0.0754(12) Uani 1 1 d . . .
H4 H 0.5846 -0.0895 0.5314 0.091 Uiso 1 1 calc R . .
C5 C 0.6751(2) -0.0059(4) 0.58422(15) 0.0629(10) Uani 1 1 d . . .
H5 H 0.7100 -0.0434 0.5651 0.075 Uiso 1 1 calc R . .
C23 C 0.8283(2) 0.0196(4) 0.99060(14) 0.0562(10) Uani 1 1 d . . .
C9 C 0.8990(2) 0.1730(4) 0.70074(19) 0.0713(11) Uani 1 1 d . . .
H9 H 0.9482 0.1602 0.6976 0.086 Uiso 1 1 calc R . .
C20 C 0.9643(2) -0.0326(4) 1.06454(15) 0.0644(10) Uani 1 1 d . . .
C10 C 0.8840(2) 0.2553(4) 0.74594(17) 0.0694(11) Uani 1 1 d . . .
H10 H 0.9236 0.2969 0.7723 0.083 Uiso 1 1 calc R . .
C8 C 0.8421(2) 0.1103(4) 0.66078(16) 0.0615(10) Uani 1 1 d . . .
H8 H 0.8524 0.0561 0.6305 0.074 Uiso 1 1 calc R . .
C13 C 0.6401(2) 0.2961(4) 0.74659(15) 0.0642(10) Uani 1 1 d . . .
H13A H 0.5952 0.3406 0.7238 0.077 Uiso 1 1 calc R . .
H13B H 0.6720 0.3757 0.7651 0.077 Uiso 1 1 calc R . .
C18 C 0.8645(2) 0.1314(4) 1.02527(15) 0.0618(10) Uani 1 1 d . . .
H18 H 0.8427 0.2247 1.0238 0.074 Uiso 1 1 calc R . .
C22 C 0.8608(3) -0.1201(4) 0.99355(17) 0.0702(11) Uani 1 1 d . . .
H22 H 0.8370 -0.1966 0.9706 0.084 Uiso 1 1 calc R . .
C19 C 0.9321(2) 0.1069(4) 1.06185(16) 0.0653(11) Uani 1 1 d . . .
H19 H 0.9563 0.1833 1.0847 0.078 Uiso 1 1 calc R . .
C3 C 0.5481(2) 0.0208(5) 0.59277(17) 0.0759(12) Uani 1 1 d . . .
H3 H 0.4978 0.0002 0.5785 0.091 Uiso 1 1 calc R . .
C16 C 0.6606(2) 0.0255(4) 0.87635(16) 0.0706(11) Uani 1 1 d . . .
H16A H 0.6318 0.0793 0.8991 0.085 Uiso 1 1 calc R . .
H16B H 0.6283 -0.0494 0.8548 0.085 Uiso 1 1 calc R . .
C21 C 0.9283(3) -0.1445(4) 1.03047(18) 0.0736(12) Uani 1 1 d . . .
H21 H 0.9499 -0.2381 1.0325 0.088 Uiso 1 1 calc R . .


_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 C20 1.890(4) . ?
O1 C23 1.360(4) . ?
O1 C17 1.433(4) . ?
N1 C12 1.383(4) . ?
N1 C1 1.389(4) . ?
N1 C13 1.462(4) . ?
C6 C5 1.402(5) . ?
C6 C1 1.409(4) . ?
C6 C7 1.436(5) . ?
C12 C11 1.388(5) . ?
C12 C7 1.410(4) . ?
C7 C8 1.389(5) . ?
C1 C2 1.374(5) . ?
C14 C15 1.510(5) . ?
C14 C13 1.514(5) . ?
C15 C16 1.521(5) . ?
C11 C10 1.370(5) . ?
C2 C3 1.368(5) . ?
C17 C16 1.497(5) . ?
C4 C5 1.372(5) . ?
C4 C3 1.385(5) . ?
C23 C18 1.381(5) . ?
C23 C22 1.390(5) . ?
C9 C8 1.374(5) . ?
C9 C10 1.392(5) . ?
C20 C21 1.373(5) . ?
C20 C19 1.385(5) . ?
C18 C19 1.370(5) . ?
C22 C21 1.372(5) . ?

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
C23 O1 C17 118.1(3) . . ?
C12 N1 C1 109.1(3) . . ?
C12 N1 C13 126.4(3) . . ?
C1 N1 C13 124.4(3) . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 C7 134.3(3) . . ?
C1 C6 C7 106.9(3) . . ?
N1 C12 C11 130.0(3) . . ?
N1 C12 C7 108.5(3) . . ?
C11 C12 C7 121.5(3) . . ?
C8 C7 C12 119.4(4) . . ?
C8 C7 C6 133.6(3) . . ?
C12 C7 C6 107.0(3) . . ?
C2 C1 N1 129.9(3) . . ?
C2 C1 C6 121.6(3) . . ?
N1 C1 C6 108.5(3) . . ?
C15 C14 C13 115.3(3) . . ?
C14 C15 C16 113.7(3) . . ?
C10 C11 C12 117.6(3) . . ?
C3 C2 C1 118.3(4) . . ?
O1 C17 C16 107.8(3) . . ?
C5 C4 C3 121.0(4) . . ?
C4 C5 C6 118.8(3) . . ?
O1 C23 C18 115.4(3) . . ?
O1 C23 C22 125.4(3) . . ?
C18 C23 C22 119.2(4) . . ?
C8 C9 C10 120.8(4) . . ?
C21 C20 C19 119.8(4) . . ?
C21 C20 Br1 120.5(3) . . ?
C19 C20 Br1 119.7(3) . . ?
C11 C10 C9 121.8(4) . . ?
C9 C8 C7 118.9(4) . . ?
N1 C13 C14 113.2(3) . . ?
C19 C18 C23 121.0(4) . . ?
C21 C22 C23 119.7(4) . . ?
C18 C19 C20 119.5(4) . . ?
C2 C3 C4 121.5(4) . . ?
C17 C16 C15 114.3(3) . . ?
C22 C21 C20 120.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.101
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c
_audit_block_doi                 10.5517/cc1jpz28
_database_code_depnum_ccdc_archive 'CCDC 1421290'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 Br N'
_chemical_formula_weight         330.25

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   16.319(3)
_cell_length_b                   8.0724(16)
_cell_length_c                   24.455(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3221.5(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    2.543
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_T_max  0.700
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27947
_diffrn_reflns_av_R_equivalents  0.1764
_diffrn_reflns_av_sigmaI/netI    0.1022
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3687
_reflns_number_gt                1672
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0686P)²+1.8047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3687
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1730
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.1820
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34276(4) -0.30007(8) -0.02247(3) 0.1179(4) Uani 1 1 d . . .
N1 N 0.4226(2) 0.6295(4) 0.15087(15) 0.0728(10) Uani 1 1 d . . .
C18 C 0.3915(3) 0.7155(5) 0.19488(18) 0.0685(11) Uani 1 1 d . . .
C17 C 0.3191(3) 0.6920(6) 0.2225(2) 0.0831(14) Uani 1 1 d . . .
H17A H 0.2829 0.6080 0.2128 0.100 Uiso 1 1 calc R . .
C16 C 0.3021(4) 0.7979(7) 0.2652(2) 0.1012(17) Uani 1 1 d . . .
H16A H 0.2538 0.7842 0.2849 0.121 Uiso 1 1 calc R . .
C15 C 0.3553(4) 0.9241(8) 0.2795(2) 0.1068(19) Uani 1 1 d . . .
H15A H 0.3424 0.9934 0.3086 0.128 Uiso 1 1 calc R . .
C14 C 0.4265(4) 0.9480(6) 0.2514(2) 0.0978(17) Uani 1 1 d . . .
H14A H 0.4619 1.0335 0.2611 0.117 Uiso 1 1 calc R . .
C13 C 0.4456(3) 0.8438(5) 0.20825(19) 0.0731(12) Uani 1 1 d . . .
C12 C 0.5132(3) 0.8317(5) 0.1714(2) 0.0757(13) Uani 1 1 d . . .
C11 C 0.5858(4) 0.9206(7) 0.1640(3) 0.1022(18) Uani 1 1 d . . .
H11A H 0.5981 1.0107 0.1863 0.123 Uiso 1 1 calc R . .
C10 C 0.6388(4) 0.8726(10) 0.1232(3) 0.118(2) Uani 1 1 d . . .
H10A H 0.6872 0.9310 0.1178 0.141 Uiso 1 1 calc R . .
C9 C 0.6206(4) 0.7377(10) 0.0900(3) 0.1130(19) Uani 1 1 d . . .
H9A H 0.6575 0.7075 0.0628 0.136 Uiso 1 1 calc R . .
C8 C 0.5511(4) 0.6492(7) 0.0963(2) 0.0925(15) Uani 1 1 d . . .
H8A H 0.5401 0.5586 0.0740 0.111 Uiso 1 1 calc R . .
C7 C 0.4965(3) 0.6971(5) 0.13689(19) 0.0749(12) Uani 1 1 d . . .
C6 C 0.3843(3) 0.4866(5) 0.12493(18) 0.0768(12) Uani 1 1 d . . .
H6A H 0.4046 0.4771 0.0878 0.092 Uiso 1 1 calc R . .
H6B H 0.3256 0.5051 0.1230 0.092 Uiso 1 1 calc R . .
C5 C 0.3999(3) 0.3255(5) 0.15449(19) 0.0813(13) Uani 1 1 d . . .
H5A H 0.3816 0.3356 0.1921 0.098 Uiso 1 1 calc R . .
H5B H 0.4583 0.3033 0.1549 0.098 Uiso 1 1 calc R . .
C4 C 0.3555(3) 0.1808(5) 0.1275(2) 0.0784(13) Uani 1 1 d . . .
H4A H 0.3511 0.0912 0.1537 0.094 Uiso 1 1 calc R . .
H4B H 0.3004 0.2157 0.1181 0.094 Uiso 1 1 calc R . .
C3 C 0.3965(3) 0.1168(5) 0.07715(18) 0.0790(12) Uani 1 1 d . . .
H3A H 0.4527 0.0879 0.0857 0.095 Uiso 1 1 calc R . .
H3B H 0.3975 0.2036 0.0497 0.095 Uiso 1 1 calc R . .
C2 C 0.3527(3) -0.0355(5) 0.0536(2) 0.0790(13) Uani 1 1 d . . .
H2A H 0.3464 -0.1179 0.0822 0.095 Uiso 1 1 calc R . .
H2B H 0.2985 -0.0037 0.0413 0.095 Uiso 1 1 calc R . .
C1 C 0.3984(3) -0.1085(6) 0.0076(2) 0.0898(14) Uani 1 1 d . . .
H1A H 0.4525 -0.1409 0.0201 0.108 Uiso 1 1 calc R . .
H1B H 0.4051 -0.0258 -0.0208 0.108 Uiso 1 1 calc R . .


_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 1.939(5) . ?
N1 C7 1.367(6) . ?
N1 C18 1.377(5) . ?
N1 C6 1.458(5) . ?
C18 C17 1.375(7) . ?
C18 C13 1.400(6) . ?
C17 C16 1.378(7) . ?
C17 H17A 0.9300 . ?
C16 C15 1.383(8) . ?
C16 H16A 0.9300 . ?
C15 C14 1.363(8) . ?
C15 H15A 0.9300 . ?
C14 C13 1.385(7) . ?
C14 H14A 0.9300 . ?
C13 C12 1.428(7) . ?
C12 C11 1.397(7) . ?
C12 C7 1.402(6) . ?
C11 C10 1.376(8) . ?
C11 H11A 0.9300 . ?
C10 C9 1.390(9) . ?
C10 H10A 0.9300 . ?
C9 C8 1.349(8) . ?
C9 H9A 0.9300 . ?
C8 C7 1.389(7) . ?
C8 H8A 0.9300 . ?
C6 C5 1.509(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 C4 1.524(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 C3 1.492(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 C2 1.534(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 C1 1.472(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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
C7 N1 C18 108.7(4) . . ?
C7 N1 C6 125.8(4) . . ?
C18 N1 C6 125.5(4) . . ?
C17 C18 N1 129.2(4) . . ?
C17 C18 C13 122.0(4) . . ?
N1 C18 C13 108.8(4) . . ?
C18 C17 C16 117.4(5) . . ?
C18 C17 H17A 121.3 . . ?
C16 C17 H17A 121.3 . . ?
C17 C16 C15 121.5(6) . . ?
C17 C16 H16A 119.3 . . ?
C15 C16 H16A 119.3 . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C15 C14 C13 119.3(5) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C14 C13 C18 119.1(5) . . ?
C14 C13 C12 134.1(5) . . ?
C18 C13 C12 106.8(4) . . ?
C11 C12 C7 119.0(5) . . ?
C11 C12 C13 134.6(5) . . ?
C7 C12 C13 106.4(4) . . ?
C10 C11 C12 118.8(6) . . ?
C10 C11 H11A 120.6 . . ?
C12 C11 H11A 120.6 . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C8 C9 C10 121.9(6) . . ?
C8 C9 H9A 119.1 . . ?
C10 C9 H9A 119.1 . . ?
C9 C8 C7 118.2(6) . . ?
C9 C8 H8A 120.9 . . ?
C7 C8 H8A 120.9 . . ?
N1 C7 C8 129.3(5) . . ?
N1 C7 C12 109.3(4) . . ?
C8 C7 C12 121.4(5) . . ?
N1 C6 C5 113.6(3) . . ?
N1 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C5 C4 111.9(4) . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C3 C4 C5 114.2(4) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 C3 C2 112.2(4) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C1 C2 C3 111.8(4) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C2 C1 Br1 111.9(3) . . ?
C2 C1 H1A 109.2 . . ?
Br1 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
Br1 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.852
_refine_diff_density_rms         0.171
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c
_audit_block_doi                 10.5517/cc1jpz39
_database_code_depnum_ccdc_archive 'CCDC 1421291'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Br N O'
_chemical_formula_weight         422.35

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   5.7109(15)
_cell_length_b                   12.738(3)
_cell_length_c                   28.186(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.0210(10)
_cell_angle_gamma                90.00
_cell_volume                     2050.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1138
_cell_measurement_theta_min      3.1921
_cell_measurement_theta_max      29.2710

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    2.018
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.610
_exptl_absorpt_correction_T_max  0.695
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5309
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.1014
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         24.71
_reflns_number_total             2993
_reflns_number_gt                1419
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1224P)²+0.4156P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2993
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1661
_refine_ls_R_factor_gt           0.0816
_refine_ls_wR_factor_ref         0.2760
_refine_ls_wR_factor_gt          0.2197
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.0994(3) 0.97418(9) 1.06723(4) 0.1183(7) Uani 1 1 d . . .
O1 O 0.2778(11) 0.5697(4) 0.9633(2) 0.0729(17) Uani 1 1 d . . .
N1 N 0.7054(12) 0.1751(5) 0.7645(3) 0.0615(18) Uani 1 1 d . . .
C17 C 0.4619(15) 0.4527(6) 0.9093(3) 0.063(2) Uani 1 1 d . . .
H17A H 0.3181 0.4514 0.8909 0.075 Uiso 1 1 calc R . .
H17B H 0.4545 0.3964 0.9324 0.075 Uiso 1 1 calc R . .
C16 C 0.6667(15) 0.4345(6) 0.8767(3) 0.064(2) Uani 1 1 d . . .
H16A H 0.8098 0.4388 0.8951 0.076 Uiso 1 1 calc R . .
H16B H 0.6706 0.4904 0.8533 0.076 Uiso 1 1 calc R . .
C14 C 0.8673(15) 0.3147(6) 0.8179(3) 0.064(2) Uani 1 1 d . . .
H14A H 1.0093 0.3316 0.8352 0.076 Uiso 1 1 calc R . .
H14B H 0.8531 0.3645 0.7920 0.076 Uiso 1 1 calc R . .
C12 C 0.5260(15) 0.1051(6) 0.7742(3) 0.060(2) Uani 1 1 d . . .
C19 C 0.2497(16) 0.6646(6) 0.9857(3) 0.058(2) Uani 1 1 d . . .
C7 C 0.4009(15) 0.0915(6) 0.7324(4) 0.072(3) Uani 1 1 d . . .
C18 C 0.4811(16) 0.5559(6) 0.9346(3) 0.062(2) Uani 1 1 d . . .
H18A H 0.6204 0.5567 0.9543 0.074 Uiso 1 1 calc R . .
H18B H 0.4930 0.6126 0.9118 0.074 Uiso 1 1 calc R . .
C15 C 0.6630(15) 0.3280(6) 0.8503(3) 0.061(2) Uani 1 1 d . . .
H15A H 0.6631 0.2716 0.8734 0.074 Uiso 1 1 calc R . .
H15B H 0.5196 0.3228 0.8320 0.074 Uiso 1 1 calc R . .
C24 C 0.4028(17) 0.7467(7) 0.9815(3) 0.074(3) Uani 1 1 d . . .
H24 H 0.5337 0.7414 0.9620 0.089 Uiso 1 1 calc R . .
C13 C 0.8917(15) 0.2046(6) 0.7971(3) 0.070(2) Uani 1 1 d . . .
H13A H 1.0402 0.2000 0.7805 0.084 Uiso 1 1 calc R . .
H13B H 0.8955 0.1544 0.8229 0.084 Uiso 1 1 calc R . .
C10 C 0.278(2) -0.0140(8) 0.8139(6) 0.096(4) Uani 1 1 d . . .
H10 H 0.2371 -0.0501 0.8414 0.115 Uiso 1 1 calc R . .
C6 C 0.5071(16) 0.1578(6) 0.6967(3) 0.066(2) Uani 1 1 d . . .
C3 C 0.790(2) 0.2908(8) 0.6466(4) 0.084(3) Uani 1 1 d . . .
H3 H 0.8880 0.3341 0.6288 0.101 Uiso 1 1 calc R . .
C1 C 0.6993(15) 0.2058(6) 0.7180(3) 0.059(2) Uani 1 1 d . . .
C20 C 0.0521(17) 0.6734(7) 1.0139(3) 0.070(2) Uani 1 1 d . . .
H20 H -0.0498 0.6168 1.0169 0.084 Uiso 1 1 calc R . .
C23 C 0.358(2) 0.8400(7) 1.0074(4) 0.084(3) Uani 1 1 d . . .
H23 H 0.4634 0.8956 1.0060 0.100 Uiso 1 1 calc R . .
C5 C 0.4580(18) 0.1793(8) 0.6496(4) 0.083(3) Uani 1 1 d . . .
H5 H 0.3302 0.1480 0.6348 0.099 Uiso 1 1 calc R . .
C4 C 0.599(2) 0.2469(9) 0.6249(4) 0.086(3) Uani 1 1 d . . .
H4 H 0.5646 0.2631 0.5935 0.103 Uiso 1 1 calc R . .
C22 C 0.162(2) 0.8480(7) 1.0344(3) 0.071(2) Uani 1 1 d . . .
C8 C 0.208(2) 0.0220(7) 0.7334(5) 0.102(4) Uani 1 1 d . . .
H8 H 0.1185 0.0108 0.7063 0.122 Uiso 1 1 calc R . .
C11 C 0.4669(18) 0.0531(7) 0.8156(4) 0.081(3) Uani 1 1 d . . .
H11 H 0.5514 0.0631 0.8435 0.097 Uiso 1 1 calc R . .
C2 C 0.8437(17) 0.2733(6) 0.6930(3) 0.068(2) Uani 1 1 d . . .
H2 H 0.9717 0.3055 0.7074 0.082 Uiso 1 1 calc R . .
C21 C 0.0062(17) 0.7645(8) 1.0375(3) 0.077(3) Uani 1 1 d . . .
H21 H -0.1291 0.7708 1.0556 0.092 Uiso 1 1 calc R . .
C9 C 0.154(2) -0.0293(8) 0.7756(7) 0.118(6) Uani 1 1 d . . .
H9 H 0.0280 -0.0754 0.7766 0.141 Uiso 1 1 calc R . .


_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 C22 1.889(9) . ?
O1 C19 1.372(9) . ?
O1 C18 1.427(10) . ?
N1 C1 1.369(11) . ?
N1 C12 1.386(10) . ?
N1 C13 1.455(10) . ?
C17 C18 1.500(11) . ?
C17 C16 1.505(12) . ?
C16 C15 1.547(10) . ?
C14 C15 1.492(11) . ?
C14 C13 1.526(11) . ?
C12 C11 1.383(12) . ?
C12 C7 1.388(12) . ?
C19 C24 1.368(12) . ?
C19 C20 1.386(12) . ?
C7 C8 1.414(13) . ?
C7 C6 1.448(12) . ?
C24 C23 1.418(12) . ?
C10 C9 1.305(18) . ?
C10 C11 1.376(16) . ?
C6 C5 1.384(13) . ?
C6 C1 1.392(11) . ?
C3 C2 1.363(13) . ?
C3 C4 1.372(13) . ?
C1 C2 1.384(12) . ?
C20 C21 1.363(12) . ?
C23 C22 1.360(13) . ?
C5 C4 1.368(14) . ?
C22 C21 1.387(13) . ?
C8 C9 1.392(19) . ?

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
C19 O1 C18 117.7(7) . . ?
C1 N1 C12 110.8(8) . . ?
C1 N1 C13 123.3(7) . . ?
C12 N1 C13 125.5(8) . . ?
C18 C17 C16 111.7(7) . . ?
C17 C16 C15 114.7(7) . . ?
C15 C14 C13 114.3(7) . . ?
C11 C12 N1 131.0(9) . . ?
C11 C12 C7 122.1(9) . . ?
N1 C12 C7 106.9(8) . . ?
C24 C19 O1 123.9(8) . . ?
C24 C19 C20 120.5(8) . . ?
O1 C19 C20 115.5(8) . . ?
C12 C7 C8 117.5(11) . . ?
C12 C7 C6 107.6(8) . . ?
C8 C7 C6 134.9(11) . . ?
O1 C18 C17 108.6(7) . . ?
C14 C15 C16 112.6(7) . . ?
C19 C24 C23 118.8(9) . . ?
N1 C13 C14 114.4(7) . . ?
C9 C10 C11 123.1(13) . . ?
C5 C6 C1 119.1(10) . . ?
C5 C6 C7 134.3(10) . . ?
C1 C6 C7 106.7(8) . . ?
C2 C3 C4 122.6(11) . . ?
N1 C1 C2 130.5(8) . . ?
N1 C1 C6 107.9(8) . . ?
C2 C1 C6 121.6(9) . . ?
C21 C20 C19 120.4(9) . . ?
C22 C23 C24 119.9(9) . . ?
C4 C5 C6 119.5(10) . . ?
C3 C4 C5 120.0(10) . . ?
C23 C22 C21 120.4(9) . . ?
C23 C22 Br1 119.5(8) . . ?
C21 C22 Br1 120.1(8) . . ?
C9 C8 C7 118.9(13) . . ?
C10 C11 C12 117.3(11) . . ?
C3 C2 C1 117.1(10) . . ?
C20 C21 C22 119.9(9) . . ?
C10 C9 C8 121.1(12) . . ?

_diffrn_measured_fraction_theta_max 0.857
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.857
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.077
