# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_18074
_database_code_depnum_ccdc_archive 'CCDC 1481433'
_audit_update_record             
;
2016-05-23 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'S-phenyl 2-(5-bromo-3-(dicyanomethyl)-2-oxoindolin-3-yl)ethanethioate'
_chemical_name_common            thioester
_chemical_melting_point          446
_chemical_formula_moiety         'C19 H12 Br N3 O2 S'
_chemical_formula_sum            'C19 H12 Br N3 O2 S'
_chemical_formula_weight         426.29

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'
S S 0.1246 0.1234 '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   'P b c a'

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                   11.1742(7)
_cell_length_b                   9.5722(6)
_cell_length_c                   34.645(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3705.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7667
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      24.98

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    2.349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3747
_exptl_absorpt_correction_T_max  0.7821
_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  'Bruker APEX2'
_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            18717
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3277
_reflns_number_gt                2733
_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)+(0.0647P)²+1.0254P] 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         3277
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_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 0.3915(2) 1.0583(3) 0.57973(8) 0.0306(6) Uani 1 1 d . . .
C2 C 0.3561(2) 1.0527(3) 0.54160(8) 0.0367(6) Uani 1 1 d . . .
H2 H 0.3231 1.1331 0.5296 0.044 Uiso 1 1 calc R . .
C3 C 0.3686(2) 0.9298(3) 0.52079(8) 0.0365(6) Uani 1 1 d . . .
H3 H 0.3444 0.9241 0.4946 0.044 Uiso 1 1 calc R . .
C4 C 0.4176(2) 0.8157(3) 0.53955(7) 0.0273(5) Uani 1 1 d . . .
C5 C 0.4515(2) 0.8223(3) 0.57826(6) 0.0239(5) Uani 1 1 d . . .
C6 C 0.4399(2) 0.9447(3) 0.59889(7) 0.0266(5) Uani 1 1 d . . .
H6 H 0.4640 0.9507 0.6251 0.032 Uiso 1 1 calc R . .
C7 C 0.5059(2) 0.6832(2) 0.58968(6) 0.0231(5) Uani 1 1 d . . .
C8 C 0.5001(2) 0.6006(3) 0.55100(7) 0.0275(5) Uani 1 1 d . . .
H1 H 0.4338 0.6501 0.4992 0.033 Uiso 1 1 d R . .
C9 C 0.6386(2) 0.7032(3) 0.60187(6) 0.0254(5) Uani 1 1 d . . .
H9 H 0.6411 0.7763 0.6225 0.030 Uiso 1 1 calc R . .
C10 C 0.7078(2) 0.7553(3) 0.56849(7) 0.0330(6) Uani 1 1 d . . .
C11 C 0.6951(2) 0.5759(3) 0.61735(7) 0.0318(6) Uani 1 1 d . . .
C12 C 0.4353(2) 0.5956(3) 0.61898(6) 0.0266(5) Uani 1 1 d . . .
H12A H 0.3520 0.5867 0.6096 0.032 Uiso 1 1 calc R . .
H12B H 0.4703 0.5006 0.6195 0.032 Uiso 1 1 calc R . .
C13 C 0.4315(2) 0.6502(3) 0.65979(7) 0.0279(5) Uani 1 1 d . . .
C14 C 0.3569(2) 0.6202(3) 0.73472(8) 0.0416(7) Uani 1 1 d . . .
C15 C 0.2813(3) 0.7228(3) 0.74801(9) 0.0518(8) Uani 1 1 d . . .
H15 H 0.2173 0.7553 0.7323 0.062 Uiso 1 1 calc R . .
C16 C 0.2994(3) 0.7786(4) 0.78458(9) 0.0592(9) Uani 1 1 d . . .
H16 H 0.2477 0.8498 0.7939 0.071 Uiso 1 1 calc R . .
C17 C 0.3909(3) 0.7320(4) 0.80725(9) 0.0555(9) Uani 1 1 d . . .
H17 H 0.4030 0.7710 0.8322 0.067 Uiso 1 1 calc R . .
C18 C 0.4653(3) 0.6287(4) 0.79399(9) 0.0603(10) Uani 1 1 d . . .
H18 H 0.5285 0.5958 0.8099 0.072 Uiso 1 1 calc R . .
C19 C 0.4494(3) 0.5724(4) 0.75796(9) 0.0557(9) Uani 1 1 d . . .
H19 H 0.5015 0.5010 0.7489 0.067 Uiso 1 1 calc R . .
N1 N 0.44576(19) 0.6833(2) 0.52453(5) 0.0305(5) Uani 1 1 d . . .
N2 N 0.7540(2) 0.7939(3) 0.54161(7) 0.0507(7) Uani 1 1 d . . .
N3 N 0.7386(2) 0.4807(3) 0.63073(7) 0.0495(7) Uani 1 1 d . . .
O1 O 0.53768(17) 0.48261(18) 0.54679(5) 0.0377(4) Uani 1 1 d . . .
O2 O 0.48833(18) 0.74721(19) 0.67179(5) 0.0396(5) Uani 1 1 d . . .
S1 S 0.33393(7) 0.54639(9) 0.68854(2) 0.0505(2) Uani 1 1 d . . .
Br1 Br 0.37573(3) 1.23035(3) 0.606809(9) 0.04468(14) 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
C1 C2 1.380(4) . ?
C1 C6 1.384(4) . ?
C1 Br1 1.903(3) . ?
C2 C3 1.387(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C4 N1 1.406(3) . ?
C5 C6 1.378(3) . ?
C5 C7 1.516(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.535(3) . ?
C7 C9 1.553(3) . ?
C7 C8 1.558(3) . ?
C8 O1 1.214(3) . ?
C8 N1 1.355(3) . ?
C9 C11 1.474(4) . ?
C9 C10 1.478(4) . ?
C9 H9 1.0000 . ?
C10 N2 1.127(3) . ?
C11 N3 1.132(3) . ?
C12 C13 1.508(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O2 1.200(3) . ?
C13 S1 1.780(2) . ?
C14 C15 1.375(4) . ?
C14 C19 1.388(4) . ?
C14 S1 1.768(3) . ?
C15 C16 1.390(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.364(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.371(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.371(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N1 H1 0.9414 . ?

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 C6 122.7(2) . . ?
C2 C1 Br1 118.6(2) . . ?
C6 C1 Br1 118.67(19) . . ?
C1 C2 C3 120.1(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 117.7(2) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 N1 128.8(2) . . ?
C5 C4 N1 109.6(2) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 C7 130.4(2) . . ?
C4 C5 C7 108.6(2) . . ?
C5 C6 C1 117.1(2) . . ?
C5 C6 H6 121.4 . . ?
C1 C6 H6 121.4 . . ?
C5 C7 C12 116.52(19) . . ?
C5 C7 C9 110.2(2) . . ?
C12 C7 C9 112.18(19) . . ?
C5 C7 C8 101.83(18) . . ?
C12 C7 C8 105.66(19) . . ?
C9 C7 C8 109.65(18) . . ?
O1 C8 N1 128.1(2) . . ?
O1 C8 C7 124.2(2) . . ?
N1 C8 C7 107.7(2) . . ?
C11 C9 C10 109.8(2) . . ?
C11 C9 C7 114.0(2) . . ?
C10 C9 C7 109.16(19) . . ?
C11 C9 H9 107.9 . . ?
C10 C9 H9 107.9 . . ?
C7 C9 H9 107.9 . . ?
N2 C10 C9 175.5(3) . . ?
N3 C11 C9 177.1(3) . . ?
C13 C12 C7 116.5(2) . . ?
C13 C12 H12A 108.2 . . ?
C7 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C7 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
O2 C13 C12 125.3(2) . . ?
O2 C13 S1 124.23(19) . . ?
C12 C13 S1 110.42(17) . . ?
C15 C14 C19 119.9(3) . . ?
C15 C14 S1 119.9(2) . . ?
C19 C14 S1 120.1(2) . . ?
C14 C15 C16 119.3(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 119.7(3) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
C8 N1 C4 112.11(19) . . ?
C8 N1 H1 119.8 . . ?
C4 N1 H1 128.1 . . ?
C14 S1 C13 101.22(13) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.055
_chemical_compound_source        Synthesized
####################################################################### 
# 
# 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_a18075
_database_code_depnum_ccdc_archive 'CCDC 1481435'
_audit_update_record             
;
2016-05-23 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2-(5-bromo-2-oxo-3-(2-oxo-2-phenylethyl)indolin-3-yl)malononitrile
_chemical_name_common            ketone
_chemical_melting_point          388
_chemical_formula_moiety         'C19 H12 Br N3 O2'
_chemical_formula_sum            'C19 H12 Br N3 O2'
_chemical_formula_weight         394.23

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'
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           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9365(8)
_cell_length_b                   10.0229(9)
_cell_length_c                   10.5846(10)
_cell_angle_alpha                72.6120(10)
_cell_angle_beta                 68.3510(10)
_cell_angle_gamma                78.5860(10)
_cell_volume                     836.80(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3615
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      24.94

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    2.474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5442
_exptl_absorpt_correction_T_max  0.7726
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  'Bruker APEX2'
_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            7437
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.08
_reflns_number_total             2952
_reflns_number_gt                2521
_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)+(0.0268P)²+0.3259P] 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         2952
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 1.3238(2) 0.2024(2) 0.5720(2) 0.0368(5) Uani 1 1 d . . .
C2 C 1.3644(2) 0.0703(2) 0.6457(2) 0.0409(5) Uani 1 1 d . . .
H2 H 1.4725 0.0346 0.6271 0.049 Uiso 1 1 calc R . .
C3 C 1.2449(2) -0.0095(2) 0.7475(2) 0.0387(5) Uani 1 1 d . . .
H3 H 1.2709 -0.0986 0.7983 0.046 Uiso 1 1 calc R . .
C4 C 1.0861(2) 0.0471(2) 0.77128(19) 0.0303(4) Uani 1 1 d . . .
C5 C 1.0459(2) 0.18026(19) 0.69527(19) 0.0271(4) Uani 1 1 d . . .
C6 C 1.1647(2) 0.2599(2) 0.5951(2) 0.0309(4) Uani 1 1 d . . .
H6 H 1.1392 0.3495 0.5447 0.037 Uiso 1 1 calc R . .
C7 C 0.8646(2) 0.21155(19) 0.74544(19) 0.0270(4) Uani 1 1 d . . .
C8 C 0.8118(2) 0.0816(2) 0.8699(2) 0.0302(4) Uani 1 1 d . . .
C9 C 0.7876(2) 0.2070(2) 0.6357(2) 0.0323(4) Uani 1 1 d . . .
H9 H 0.6713 0.2343 0.6732 0.039 Uiso 1 1 calc R . .
C10 C 0.8068(3) 0.0660(3) 0.6134(2) 0.0392(5) Uani 1 1 d . . .
C11 C 0.8530(3) 0.3101(2) 0.5014(2) 0.0379(5) Uani 1 1 d . . .
C12 C 0.7985(2) 0.35019(19) 0.78887(19) 0.0300(4) Uani 1 1 d . . .
H12A H 0.8434 0.4270 0.7101 0.036 Uiso 1 1 calc R . .
H12B H 0.6820 0.3626 0.8107 0.036 Uiso 1 1 calc R . .
C13 C 0.8367(2) 0.3579(2) 0.91384(19) 0.0294(4) Uani 1 1 d . . .
C14 C 0.7746(2) 0.4850(2) 0.96931(19) 0.0302(4) Uani 1 1 d . . .
C15 C 0.7039(3) 0.6058(2) 0.8985(2) 0.0448(5) Uani 1 1 d . . .
H15 H 0.6936 0.6087 0.8135 0.054 Uiso 1 1 calc R . .
C16 C 0.6490(3) 0.7215(2) 0.9543(3) 0.0526(6) Uani 1 1 d . . .
H16 H 0.6026 0.8024 0.9062 0.063 Uiso 1 1 calc R . .
C17 C 0.6624(3) 0.7180(2) 1.0800(2) 0.0472(6) Uani 1 1 d . . .
H17 H 0.6248 0.7962 1.1172 0.057 Uiso 1 1 calc R . .
C18 C 0.7314(3) 0.5992(3) 1.1511(2) 0.0485(6) Uani 1 1 d . . .
H18 H 0.7398 0.5970 1.2367 0.058 Uiso 1 1 calc R . .
C19 C 0.7884(3) 0.4829(2) 1.0964(2) 0.0395(5) Uani 1 1 d . . .
H19 H 0.8361 0.4031 1.1447 0.047 Uiso 1 1 calc R . .
N1 N 0.9059(3) 0.3919(2) 0.4014(2) 0.0575(5) Uani 1 1 d . . .
N2 N 0.8151(3) -0.0444(2) 0.6026(2) 0.0626(6) Uani 1 1 d . . .
N3 N 0.94535(19) -0.00995(16) 0.87005(17) 0.0334(4) Uani 1 1 d . . .
H3' H 0.9447 -0.0957 0.9271 0.040 Uiso 1 1 d R . .
O1 O 0.67358(17) 0.06563(15) 0.94665(15) 0.0438(4) Uani 1 1 d . . .
O2 O 0.91366(18) 0.25901(14) 0.96969(15) 0.0416(4) Uani 1 1 d . . .
Br1 Br 1.48924(3) 0.31175(3) 0.43287(3) 0.06004(12) 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
C1 C2 1.376(3) . ?
C1 C6 1.384(3) . ?
C1 Br1 1.904(2) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(3) . ?
C4 N3 1.400(2) . ?
C5 C6 1.374(3) . ?
C5 C7 1.507(3) . ?
C6 H6 0.9300 . ?
C7 C12 1.532(3) . ?
C7 C8 1.554(3) . ?
C7 C9 1.567(3) . ?
C8 O1 1.213(2) . ?
C8 N3 1.354(2) . ?
C9 C10 1.469(3) . ?
C9 C11 1.476(3) . ?
C9 H9 0.9800 . ?
C10 N2 1.131(3) . ?
C11 N1 1.133(3) . ?
C12 C13 1.509(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.218(2) . ?
C13 C14 1.484(3) . ?
C14 C15 1.389(3) . ?
C14 C19 1.390(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N3 H3' 0.8901 . ?

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 C6 122.14(19) . . ?
C2 C1 Br1 119.88(15) . . ?
C6 C1 Br1 117.98(16) . . ?
C1 C2 C3 120.21(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 118.03(19) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 121.41(18) . . ?
C3 C4 N3 128.93(18) . . ?
C5 C4 N3 109.64(16) . . ?
C6 C5 C4 120.53(18) . . ?
C6 C5 C7 130.84(17) . . ?
C4 C5 C7 108.62(16) . . ?
C5 C6 C1 117.68(19) . . ?
C5 C6 H6 121.2 . . ?
C1 C6 H6 121.2 . . ?
C5 C7 C12 116.44(15) . . ?
C5 C7 C8 101.87(14) . . ?
C12 C7 C8 112.28(15) . . ?
C5 C7 C9 112.38(15) . . ?
C12 C7 C9 107.60(15) . . ?
C8 C7 C9 105.76(15) . . ?
O1 C8 N3 127.76(18) . . ?
O1 C8 C7 124.75(17) . . ?
N3 C8 C7 107.40(15) . . ?
C10 C9 C11 110.68(17) . . ?
C10 C9 C7 112.80(16) . . ?
C11 C9 C7 110.94(16) . . ?
C10 C9 H9 107.4 . . ?
C11 C9 H9 107.4 . . ?
C7 C9 H9 107.4 . . ?
N2 C10 C9 176.4(2) . . ?
N1 C11 C9 176.9(2) . . ?
C13 C12 C7 113.67(15) . . ?
C13 C12 H12A 108.8 . . ?
C7 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C7 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
O2 C13 C14 121.18(18) . . ?
O2 C13 C12 119.87(17) . . ?
C14 C13 C12 118.92(16) . . ?
C15 C14 C19 119.00(19) . . ?
C15 C14 C13 122.39(18) . . ?
C19 C14 C13 118.61(18) . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C8 N3 C4 111.97(16) . . ?
C8 N3 H3' 124.4 . . ?
C4 N3 H3' 123.6 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.040
_chemical_compound_source        Synthesized
