# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a16584
_database_code_depnum_ccdc_archive 'CCDC 1821215'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Br N3 O'
_chemical_formula_sum            'C15 H12 Br N3 O'
_chemical_formula_weight         330.19

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   'P 21/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                   10.7721(7)
_cell_length_b                   9.4199(6)
_cell_length_c                   14.3014(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.313(4)
_cell_angle_gamma                90.00
_cell_volume                     1385.44(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    2.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4801
_exptl_absorpt_correction_T_max  0.9163
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_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            9360
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2442
_reflns_number_gt                1861
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0727P)²+0.9239P] 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         2442
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
C1 C 0.9054(4) 0.8642(4) 0.7427(3) 0.0267(9) Uani 1 1 d . . .
C2 C 0.9137(4) 0.8883(5) 0.6495(3) 0.0375(11) Uani 1 1 d . . .
H2 H 0.9845 0.9413 0.6408 0.045 Uiso 1 1 calc R . .
C3 C 0.8192(4) 0.8352(5) 0.5686(3) 0.0383(11) Uani 1 1 d . . .
C4 C 0.8333(6) 0.8572(7) 0.4667(3) 0.0679(17) Uani 1 1 d . . .
H4A H 0.9128 0.9111 0.4718 0.102 Uiso 1 1 calc R . .
H4B H 0.7580 0.9098 0.4262 0.102 Uiso 1 1 calc R . .
H4C H 0.8382 0.7647 0.4366 0.102 Uiso 1 1 calc R . .
C5 C 0.7156(4) 0.7642(5) 0.5833(3) 0.0403(12) Uani 1 1 d . . .
H5 H 0.6488 0.7305 0.5282 0.048 Uiso 1 1 calc R . .
C6 C 0.7056(4) 0.7403(4) 0.6753(3) 0.0295(10) Uani 1 1 d . . .
H6 H 0.6330 0.6901 0.6833 0.035 Uiso 1 1 calc R . .
C7 C 0.8018(4) 0.7895(4) 0.7566(3) 0.0230(9) Uani 1 1 d . . .
C8 C 0.7142(3) 0.8517(4) 0.8888(3) 0.0240(9) Uani 1 1 d . . .
C9 C 0.7238(4) 0.8301(4) 0.9911(3) 0.0262(9) Uani 1 1 d . . .
C10 C 0.6505(4) 0.9130(5) 1.0359(3) 0.0352(11) Uani 1 1 d . . .
H10 H 0.5970 0.9866 0.9998 0.042 Uiso 1 1 calc R . .
C11 C 0.6548(4) 0.8895(6) 1.1312(3) 0.0438(12) Uani 1 1 d . . .
H11 H 0.6025 0.9442 1.1608 0.053 Uiso 1 1 calc R . .
C12 C 0.7363(5) 0.7849(5) 1.1839(3) 0.0434(12) Uani 1 1 d . . .
H12 H 0.7398 0.7684 1.2502 0.052 Uiso 1 1 calc R . .
C13 C 0.8115(4) 0.7050(5) 1.1426(3) 0.0367(11) Uani 1 1 d . . .
H13 H 0.8678 0.6351 1.1808 0.044 Uiso 1 1 calc R . .
C14 C 0.8072(4) 0.7245(4) 1.0446(3) 0.0259(9) Uani 1 1 d . . .
C15 C 0.8715(3) 0.6576(4) 0.9115(3) 0.0231(9) Uani 1 1 d . . .
N1 N 0.7937(3) 0.7622(3) 0.8532(2) 0.0213(7) Uani 1 1 d . . .
N2 N 0.8811(3) 0.6387(3) 1.0037(2) 0.0275(8) Uani 1 1 d . . .
N3 N 0.9398(3) 0.5761(3) 0.8684(2) 0.0305(8) Uani 1 1 d . . .
H3A H 0.9913 0.5096 0.9023 0.037 Uiso 1 1 calc R . .
H3B H 0.9334 0.5888 0.8062 0.037 Uiso 1 1 calc R . .
O1 O 0.6437(3) 0.9392(3) 0.8346(2) 0.0343(7) Uani 1 1 d . . .
Br1 Br 1.03533(4) 0.93820(5) 0.85112(3) 0.0435(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.027(2) 0.026(2) 0.025(2) 0.0022(18) 0.0047(17) 0.0054(17)
C2 0.035(2) 0.043(3) 0.039(3) 0.016(2) 0.019(2) 0.006(2)
C3 0.051(3) 0.045(3) 0.020(2) 0.009(2) 0.012(2) 0.017(2)
C4 0.094(4) 0.087(5) 0.031(3) 0.014(3) 0.032(3) 0.026(4)
C5 0.047(3) 0.046(3) 0.021(2) -0.006(2) -0.001(2) 0.011(2)
C6 0.030(2) 0.032(2) 0.024(2) -0.0025(19) 0.0051(17) 0.0018(18)
C7 0.027(2) 0.023(2) 0.019(2) 0.0041(16) 0.0067(16) 0.0061(16)
C8 0.0215(18) 0.027(2) 0.025(2) 0.0008(18) 0.0089(16) 0.0014(17)
C9 0.0247(19) 0.032(2) 0.022(2) -0.0005(17) 0.0074(16) -0.0044(17)
C10 0.028(2) 0.050(3) 0.031(2) 0.001(2) 0.0133(19) 0.0066(19)
C11 0.039(3) 0.063(3) 0.036(3) -0.007(2) 0.022(2) 0.000(2)
C12 0.059(3) 0.052(3) 0.023(2) -0.002(2) 0.019(2) -0.008(3)
C13 0.050(3) 0.036(3) 0.023(2) 0.0045(19) 0.011(2) -0.002(2)
C14 0.035(2) 0.023(2) 0.020(2) -0.0011(17) 0.0072(17) -0.0066(17)
C15 0.028(2) 0.020(2) 0.020(2) 0.0014(16) 0.0054(16) 0.0007(16)
N1 0.0251(16) 0.0212(17) 0.0170(16) 0.0024(13) 0.0055(13) 0.0011(14)
N2 0.0379(19) 0.0248(19) 0.0185(18) 0.0022(15) 0.0064(14) 0.0019(15)
N3 0.045(2) 0.0266(19) 0.0186(17) 0.0072(14) 0.0068(15) 0.0107(16)
O1 0.0345(16) 0.0415(18) 0.0279(16) 0.0089(13) 0.0106(13) 0.0143(14)
Br1 0.0329(3) 0.0425(3) 0.0442(3) 0.0044(2) -0.0053(2) -0.0098(2)

_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
C1 C2 1.381(6) . ?
C1 C7 1.382(5) . ?
C1 Br1 1.887(4) . ?
C2 C3 1.387(6) . ?
C2 H2 0.9500 . ?
C3 C5 1.369(6) . ?
C3 C4 1.524(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.369(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(5) . ?
C6 H6 0.9500 . ?
C7 N1 1.433(5) . ?
C8 O1 1.228(4) . ?
C8 N1 1.401(5) . ?
C8 C9 1.450(5) . ?
C9 C10 1.394(6) . ?
C9 C14 1.405(5) . ?
C10 C11 1.368(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.363(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(6) . ?
C13 H13 0.9500 . ?
C14 N2 1.380(5) . ?
C15 N2 1.304(5) . ?
C15 N3 1.334(5) . ?
C15 N1 1.397(4) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?

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
C2 C1 C7 120.7(4) . . ?
C2 C1 Br1 119.1(3) . . ?
C7 C1 Br1 120.2(3) . . ?
C1 C2 C3 120.2(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C5 C3 C2 118.5(4) . . ?
C5 C3 C4 122.1(4) . . ?
C2 C3 C4 119.4(5) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 121.9(4) . . ?
C3 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C7 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C1 C7 C6 118.8(4) . . ?
C1 C7 N1 120.9(3) . . ?
C6 C7 N1 120.3(4) . . ?
O1 C8 N1 120.3(3) . . ?
O1 C8 C9 125.2(4) . . ?
N1 C8 C9 114.5(3) . . ?
C10 C9 C14 120.3(4) . . ?
C10 C9 C8 120.3(4) . . ?
C14 C9 C8 119.4(4) . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.0(4) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 121.0(4) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
N2 C14 C13 119.8(4) . . ?
N2 C14 C9 122.7(3) . . ?
C13 C14 C9 117.6(4) . . ?
N2 C15 N3 120.0(3) . . ?
N2 C15 N1 123.5(3) . . ?
N3 C15 N1 116.5(3) . . ?
C15 N1 C8 122.0(3) . . ?
C15 N1 C7 120.2(3) . . ?
C8 N1 C7 117.5(3) . . ?
C15 N2 C14 117.8(3) . . ?
C15 N3 H3A 120.0 . . ?
C15 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.261
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.082
####################################################################### 
# 
# 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_ch16585
_database_code_depnum_ccdc_archive 'CCDC 1821226'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Br N3 O'
_chemical_formula_sum            'C15 H12 Br N3 O'
_chemical_formula_weight         330.19

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   'P 21/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                   6.4056(2)
_cell_length_b                   22.7204(7)
_cell_length_c                   9.3434(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.885(2)
_cell_angle_gamma                90.00
_cell_volume                     1335.35(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    3.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2187
_exptl_absorpt_correction_T_max  0.4393
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_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            6954
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         25.07
_reflns_number_total             2348
_reflns_number_gt                2104
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0524P)²+0.3433P] 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         2348
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.201
_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
C1 C 0.8042(4) 0.07467(11) 1.2749(3) 0.0279(6) Uani 1 1 d . . .
C2 C 1.0012(4) 0.09676(12) 1.3386(3) 0.0317(6) Uani 1 1 d . . .
H2 H 1.0738 0.0809 1.4284 0.038 Uiso 1 1 calc R . .
C3 C 1.0934(4) 0.14186(12) 1.2723(3) 0.0301(6) Uani 1 1 d . . .
C4 C 1.3066(4) 0.16658(14) 1.3437(3) 0.0411(7) Uani 1 1 d . . .
H4A H 1.2958 0.2093 1.3592 0.049 Uiso 1 1 d R . .
H4B H 1.4047 0.1657 1.2798 0.049 Uiso 1 1 d R . .
H4C H 1.3780 0.1461 1.4420 0.049 Uiso 1 1 d R . .
C5 C 0.9830(4) 0.16315(11) 1.1404(3) 0.0276(6) Uani 1 1 d . . .
H5 H 1.0438 0.1940 1.0932 0.033 Uiso 1 1 calc R . .
C6 C 0.7866(4) 0.14079(11) 1.0755(3) 0.0253(5) Uani 1 1 d . . .
H6 H 0.7159 0.1562 0.9846 0.030 Uiso 1 1 calc R . .
C7 C 0.6919(4) 0.09582(11) 1.1427(3) 0.0233(5) Uani 1 1 d . . .
C8 C 0.3383(4) 0.09034(10) 0.9731(3) 0.0231(5) Uani 1 1 d . . .
C9 C -0.0193(4) 0.06586(11) 0.8514(3) 0.0253(5) Uani 1 1 d . . .
C10 C -0.0092(4) 0.11911(10) 0.7675(3) 0.0240(5) Uani 1 1 d . . .
C11 C -0.1853(4) 0.13763(12) 0.6634(3) 0.0304(6) Uani 1 1 d . . .
H11 H -0.3118 0.1148 0.6462 0.036 Uiso 1 1 calc R . .
C12 C -0.1738(4) 0.18858(13) 0.5870(3) 0.0346(6) Uani 1 1 d . . .
H12 H -0.2918 0.2009 0.5158 0.042 Uiso 1 1 calc R . .
C13 C 0.0122(4) 0.22246(12) 0.6139(3) 0.0345(6) Uani 1 1 d . . .
H13 H 0.0193 0.2578 0.5607 0.041 Uiso 1 1 calc R . .
C14 C 0.1840(4) 0.20527(12) 0.7162(3) 0.0318(6) Uani 1 1 d . . .
H14 H 0.3085 0.2289 0.7335 0.038 Uiso 1 1 calc R . .
C15 C 0.1779(4) 0.15299(11) 0.7957(3) 0.0241(5) Uani 1 1 d . . .
N1 N 0.4947(3) 0.07013(9) 1.0833(2) 0.0262(5) Uani 1 1 d . . .
H1 H 0.4678 0.0364 1.1222 0.031 Uiso 1 1 calc R . .
N2 N 0.1630(3) 0.05390(9) 0.9504(2) 0.0248(5) Uani 1 1 d . . .
H2A H 0.1682 0.0213 1.0019 0.030 Uiso 1 1 calc R . .
N3 N 0.3547(3) 0.13818(9) 0.9007(2) 0.0261(5) Uani 1 1 d . . .
O1 O -0.1747(3) 0.03272(8) 0.8408(2) 0.0318(4) Uani 1 1 d . . .
Br1 Br 0.68388(5) 0.014182(13) 1.37530(3) 0.03987(15) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0286(13) 0.0282(13) 0.0284(14) 0.0031(11) 0.0090(11) 0.0004(11)
C2 0.0276(13) 0.0401(16) 0.0264(14) 0.0013(12) 0.0020(11) 0.0019(12)
C3 0.0260(13) 0.0340(15) 0.0311(15) -0.0074(12) 0.0069(11) 0.0006(11)
C4 0.0261(14) 0.0530(19) 0.0434(18) -0.0055(14) 0.0046(13) -0.0071(13)
C5 0.0263(13) 0.0269(13) 0.0319(14) -0.0023(11) 0.0114(11) -0.0016(10)
C6 0.0252(12) 0.0254(13) 0.0266(13) 0.0015(11) 0.0082(10) 0.0029(10)
C7 0.0226(12) 0.0229(13) 0.0252(13) -0.0018(10) 0.0064(10) 0.0032(10)
C8 0.0243(12) 0.0210(12) 0.0251(13) -0.0020(10) 0.0075(10) -0.0016(10)
C9 0.0266(13) 0.0253(13) 0.0245(13) -0.0020(10) 0.0059(10) -0.0006(11)
C10 0.0290(13) 0.0215(13) 0.0219(13) -0.0015(10) 0.0057(10) -0.0020(10)
C11 0.0290(14) 0.0304(14) 0.0302(14) -0.0006(12) 0.0015(11) -0.0045(11)
C12 0.0366(15) 0.0327(14) 0.0305(15) 0.0058(12) -0.0038(12) 0.0005(12)
C13 0.0422(16) 0.0312(14) 0.0290(15) 0.0067(11) 0.0038(12) -0.0003(12)
C14 0.0324(14) 0.0279(14) 0.0344(15) 0.0057(11) 0.0046(12) -0.0061(11)
C15 0.0277(13) 0.0253(13) 0.0200(13) 0.0018(10) 0.0061(10) 0.0000(10)
N1 0.0252(11) 0.0237(11) 0.0286(12) 0.0053(9) 0.0025(9) -0.0021(9)
N2 0.0259(11) 0.0209(10) 0.0269(12) 0.0034(9) 0.0031(9) -0.0027(9)
N3 0.0233(10) 0.0246(11) 0.0301(12) 0.0029(9) 0.0042(9) -0.0034(9)
O1 0.0309(10) 0.0281(9) 0.0340(10) 0.0039(8) 0.0001(8) -0.0100(8)
Br1 0.0394(2) 0.0423(2) 0.0362(2) 0.01619(12) 0.00261(14) -0.00521(12)

_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
C1 C2 1.384(4) . ?
C1 C7 1.392(3) . ?
C1 Br1 1.907(3) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C5 1.387(4) . ?
C3 C4 1.510(4) . ?
C4 H4A 0.9859 . ?
C4 H4B 0.9451 . ?
C4 H4C 1.0540 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(3) . ?
C6 H6 0.9500 . ?
C7 N1 1.407(3) . ?
C8 N3 1.295(3) . ?
C8 N1 1.373(3) . ?
C8 N2 1.379(3) . ?
C9 O1 1.238(3) . ?
C9 N2 1.373(3) . ?
C9 C10 1.450(3) . ?
C10 C15 1.406(3) . ?
C10 C11 1.408(4) . ?
C11 C12 1.370(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.400(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.405(4) . ?
C14 H14 0.9500 . ?
C15 N3 1.393(3) . ?
N1 H1 0.8800 . ?
N2 H2A 0.8800 . ?

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
C2 C1 C7 122.2(2) . . ?
C2 C1 Br1 118.1(2) . . ?
C7 C1 Br1 119.73(19) . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C5 117.8(2) . . ?
C2 C3 C4 120.2(3) . . ?
C5 C3 C4 122.0(3) . . ?
C3 C4 H4A 110.4 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 100.8 . . ?
C3 C4 H4C 115.3 . . ?
H4A C4 H4C 109.7 . . ?
H4B C4 H4C 108.1 . . ?
C6 C5 C3 122.0(2) . . ?
C6 C5 H5 119.0 . . ?
C3 C5 H5 119.0 . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C1 C7 C6 117.1(2) . . ?
C1 C7 N1 118.8(2) . . ?
C6 C7 N1 124.0(2) . . ?
N3 C8 N1 123.6(2) . . ?
N3 C8 N2 124.6(2) . . ?
N1 C8 N2 111.9(2) . . ?
O1 C9 N2 120.2(2) . . ?
O1 C9 C10 125.6(2) . . ?
N2 C9 C10 114.2(2) . . ?
C15 C10 C11 120.6(2) . . ?
C15 C10 C9 118.6(2) . . ?
C11 C10 C9 120.7(2) . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
N3 C15 C14 118.5(2) . . ?
N3 C15 C10 123.4(2) . . ?
C14 C15 C10 118.1(2) . . ?
C8 N1 C7 129.1(2) . . ?
C8 N1 H1 115.5 . . ?
C7 N1 H1 115.5 . . ?
C9 N2 C8 123.3(2) . . ?
C9 N2 H2A 118.3 . . ?
C8 N2 H2A 118.3 . . ?
C8 N3 C15 115.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.162
