# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_jc178_6

# This structure was measured,
# solved and refined by:
# Rino Schwenk

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_properties_physical    none
_chemical_formula_moiety         'C31 H30 N2 O2 S2'
_chemical_formula_sum            'C31 H30 N2 O2 S2'
_chemical_formula_weight         526.69
_chemical_absolute_configuration syn

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_int_tables_number      4

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

_cell_length_a                   8.9302(2)
_cell_length_b                   16.0650(4)
_cell_length_c                   9.8120(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.6160(10)
_cell_angle_gamma                90.00
_cell_volume                     1308.67(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6195
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      30.66

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 'chloroform / pentane'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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            15972
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         28.70
_reflns_number_total             6672
_reflns_number_gt                5784
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0335P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_number_reflns         6672
_refine_ls_number_parameters     338
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.022
_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
S1 S 0.46682(5) 0.99924(2) 0.92406(5) 0.01941(10) Uani 1 1 d . . .
S2 S -0.49010(5) 0.98777(2) 0.59723(4) 0.01846(9) Uani 1 1 d . . .
N2 N -0.15360(16) 0.91671(8) 0.73144(15) 0.0177(3) Uani 1 1 d . . .
C12 C -0.04309(19) 1.00186(10) 0.57869(17) 0.0173(3) Uani 1 1 d . . .
O2 O -0.60638(14) 1.05897(7) 0.54965(14) 0.0238(3) Uani 1 1 d . . .
N1 N 0.13728(16) 0.92030(8) 0.79088(15) 0.0173(3) Uani 1 1 d . . .
C5 C 0.02103(18) 0.99774(10) 0.94723(17) 0.0173(3) Uani 1 1 d . . .
O1 O 0.57988(15) 1.07110(7) 0.97917(14) 0.0264(3) Uani 1 1 d . . .
C4 C 0.0405(2) 1.05739(10) 1.05689(18) 0.0184(3) Uani 1 1 d . . .
H4 H -0.0474 1.0688 1.0865 0.022 Uiso 1 1 calc R . .
C7 C -0.17216(19) 0.97816(9) 0.61904(17) 0.0170(3) Uani 1 1 d . . .
C8 C -0.32093(19) 1.01616(10) 0.54832(18) 0.0181(3) Uani 1 1 d . . .
C11 C -0.0662(2) 1.06436(10) 0.47339(18) 0.0194(3) Uani 1 1 d . . .
H11 H 0.0207 1.0790 0.4442 0.023 Uiso 1 1 calc R . .
C2 C 0.3134(2) 1.08006(10) 1.08219(19) 0.0203(4) Uani 1 1 d . . .
H2 H 0.4131 1.1083 1.1264 0.024 Uiso 1 1 calc R . .
C1 C 0.29783(19) 1.01955(10) 0.97782(18) 0.0176(3) Uani 1 1 d . . .
C3 C 0.1836(2) 1.10010(10) 1.12330(18) 0.0207(4) Uani 1 1 d . . .
C14 C 0.15129(19) 0.97932(9) 0.90600(17) 0.0170(3) Uani 1 1 d . . .
C9 C -0.3414(2) 1.08002(10) 0.44835(18) 0.0202(4) Uani 1 1 d . . .
H9 H -0.4432 1.1065 0.4055 0.024 Uiso 1 1 calc R . .
C6 C -0.14037(19) 0.95603(10) 0.87222(17) 0.0183(3) Uani 1 1 d . . .
H6A H -0.1558 0.9130 0.9381 0.022 Uiso 1 1 calc R . .
H6B H -0.2270 0.9979 0.8536 0.022 Uiso 1 1 calc R . .
C15 C -0.00600(19) 0.86778(10) 0.76081(19) 0.0198(3) Uani 1 1 d . . .
H15A H -0.0192 0.8320 0.6750 0.024 Uiso 1 1 calc R . .
H15B H 0.0103 0.8310 0.8461 0.024 Uiso 1 1 calc R . .
C24 C -0.5729(2) 0.90566(10) 0.46668(18) 0.0177(3) Uani 1 1 d . . .
C13 C 0.12103(19) 0.96213(10) 0.65129(17) 0.0191(3) Uani 1 1 d . . .
H13A H 0.1382 0.9208 0.5836 0.023 Uiso 1 1 calc R . .
H13B H 0.2052 1.0055 0.6710 0.023 Uiso 1 1 calc R . .
C29 C -0.7211(2) 0.91801(11) 0.3552(2) 0.0237(4) Uani 1 1 d . . .
H29 H -0.7732 0.9705 0.3436 0.028 Uiso 1 1 calc R . .
C10 C -0.2122(2) 1.10565(10) 0.41030(18) 0.0212(4) Uani 1 1 d . . .
C22 C 0.7742(2) 0.86123(11) 1.2505(2) 0.0263(4) Uani 1 1 d . . .
H22 H 0.8682 0.8711 1.3349 0.032 Uiso 1 1 calc R . .
C23 C 0.6941(2) 0.92793(10) 1.16570(19) 0.0230(4) Uani 1 1 d . . .
H23 H 0.7332 0.9830 1.1910 0.028 Uiso 1 1 calc R . .
C18 C 0.5565(2) 0.91355(10) 1.04369(19) 0.0180(3) Uani 1 1 d . . .
C28 C -0.7925(2) 0.85305(11) 0.2609(2) 0.0263(4) Uani 1 1 d . . .
H28 H -0.8937 0.8615 0.1840 0.032 Uiso 1 1 calc R . .
C19 C 0.4985(2) 0.83359(10) 1.0057(2) 0.0258(4) Uani 1 1 d . . .
H19 H 0.4043 0.8241 0.9215 0.031 Uiso 1 1 calc R . .
C27 C -0.7185(2) 0.77552(11) 0.2770(2) 0.0241(4) Uani 1 1 d . . .
C26 C -0.5695(2) 0.76448(10) 0.3888(2) 0.0263(4) Uani 1 1 d . . .
H26 H -0.5171 0.7121 0.3998 0.032 Uiso 1 1 calc R . .
C25 C -0.4960(2) 0.82880(10) 0.4851(2) 0.0232(4) Uani 1 1 d . . .
H25 H -0.3949 0.8204 0.5623 0.028 Uiso 1 1 calc R . .
C20 C 0.5805(2) 0.76717(11) 1.0930(2) 0.0293(4) Uani 1 1 d . . .
H20 H 0.5403 0.7122 1.0685 0.035 Uiso 1 1 calc R . .
C21 C 0.7198(2) 0.78002(10) 1.2148(2) 0.0249(4) Uani 1 1 d . . .
C30 C 0.8084(3) 0.70718(12) 1.3054(2) 0.0394(5) Uani 1 1 d . . .
H30A H 0.7364 0.6767 1.3427 0.059 Uiso 1 1 calc R . .
H30B H 0.9019 0.7274 1.3880 0.059 Uiso 1 1 calc R . .
H30C H 0.8447 0.6700 1.2446 0.059 Uiso 1 1 calc R . .
C31 C -0.7980(3) 0.70425(12) 0.1760(2) 0.0358(5) Uani 1 1 d . . .
H31A H -0.7209 0.6792 0.1383 0.054 Uiso 1 1 calc R . .
H31B H -0.8914 0.7250 0.0940 0.054 Uiso 1 1 calc R . .
H31C H -0.8333 0.6623 0.2303 0.054 Uiso 1 1 calc R . .
C17 C -0.2335(2) 1.17678(11) 0.3043(2) 0.0298(4) Uani 1 1 d . . .
H17A H -0.1278 1.1997 0.3159 0.045 Uiso 1 1 calc R . .
H17B H -0.2995 1.2203 0.3245 0.045 Uiso 1 1 calc R . .
H17C H -0.2870 1.1565 0.2038 0.045 Uiso 1 1 calc R . .
C16 C 0.2004(2) 1.16709(12) 1.2359(2) 0.0286(4) Uani 1 1 d . . .
H16A H 0.0937 1.1818 1.2354 0.043 Uiso 1 1 calc R . .
H16B H 0.2506 1.2164 1.2122 0.043 Uiso 1 1 calc R . .
H16C H 0.2678 1.1466 1.3333 0.043 Uiso 1 1 calc R . .


_geom_special_details            
; 

 Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)

 - 0.0798 (0.0058) x + 10.9380 (0.0074) y + 6.7129 (0.0045) z = 14.8460 (0.0061) 

 *    0.0224 (0.0011)  C7
 *   -0.0248 (0.0011)  C8
 *    0.0042 (0.0011)  C9
 *    0.0188 (0.0011)  C10
 *   -0.0210 (0.0011)  C11
 *    0.0004 (0.0011)  C12

 Rms deviation of fitted atoms =   0.0179


 - 0.2801 (0.0057) x + 11.3944 (0.0070) y - 6.3107 (0.0047) z = 5.3831 (0.0114) 

 Angle to previous plane (with approximate esd) = 88.13 ( 0.04 )

 *   -0.0201 (0.0011)  C1
 *    0.0064 (0.0011)  C2
 *    0.0117 (0.0012)  C3
 *   -0.0158 (0.0012)  C4
 *    0.0020 (0.0011)  C5
 *    0.0158 (0.0011)  C14

 Rms deviation of fitted atoms =   0.0134

 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
S1 O1 1.4974(13) . ?
S1 C18 1.7948(17) . ?
S1 C1 1.8024(16) . ?
S2 O2 1.4992(12) . ?
S2 C24 1.7972(17) . ?
S2 C8 1.8041(16) . ?
N2 C7 1.4434(19) . ?
N2 C15 1.469(2) . ?
N2 C6 1.4835(19) . ?
C12 C11 1.400(2) . ?
C12 C7 1.402(2) . ?
C12 C13 1.514(2) . ?
N1 C14 1.4444(19) . ?
N1 C15 1.469(2) . ?
N1 C13 1.484(2) . ?
C5 C14 1.397(2) . ?
C5 C4 1.403(2) . ?
C5 C6 1.512(2) . ?
C4 C3 1.384(2) . ?
C7 C8 1.393(2) . ?
C8 C9 1.384(2) . ?
C11 C10 1.389(2) . ?
C2 C1 1.381(2) . ?
C2 C3 1.398(2) . ?
C1 C14 1.395(2) . ?
C3 C16 1.510(2) . ?
C9 C10 1.399(2) . ?
C24 C29 1.386(2) . ?
C24 C25 1.392(2) . ?
C29 C28 1.384(2) . ?
C10 C17 1.509(2) . ?
C22 C23 1.384(2) . ?
C22 C21 1.391(2) . ?
C23 C18 1.383(2) . ?
C18 C19 1.384(2) . ?
C28 C27 1.391(2) . ?
C19 C20 1.395(3) . ?
C27 C26 1.389(3) . ?
C27 C31 1.509(2) . ?
C26 C25 1.391(2) . ?
C20 C21 1.387(3) . ?
C21 C30 1.506(3) . ?

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
O1 S1 C18 106.03(8) . . ?
O1 S1 C1 106.30(7) . . ?
C18 S1 C1 99.63(7) . . ?
O2 S2 C24 106.38(8) . . ?
O2 S2 C8 106.03(7) . . ?
C24 S2 C8 99.27(7) . . ?
C7 N2 C15 110.98(12) . . ?
C7 N2 C6 111.57(12) . . ?
C15 N2 C6 106.69(13) . . ?
C11 C12 C7 119.34(15) . . ?
C11 C12 C13 120.21(14) . . ?
C7 C12 C13 120.43(14) . . ?
C14 N1 C15 110.63(12) . . ?
C14 N1 C13 112.05(12) . . ?
C15 N1 C13 107.03(13) . . ?
C14 C5 C4 119.06(15) . . ?
C14 C5 C6 120.75(14) . . ?
C4 C5 C6 120.17(13) . . ?
C3 C4 C5 122.13(15) . . ?
C8 C7 C12 118.21(14) . . ?
C8 C7 N2 120.02(13) . . ?
C12 C7 N2 121.76(14) . . ?
C9 C8 C7 122.03(14) . . ?
C9 C8 S2 118.12(13) . . ?
C7 C8 S2 119.68(12) . . ?
C10 C11 C12 122.03(15) . . ?
C1 C2 C3 120.57(16) . . ?
C2 C1 C14 121.31(14) . . ?
C2 C1 S1 118.56(13) . . ?
C14 C1 S1 119.93(12) . . ?
C4 C3 C2 118.03(15) . . ?
C4 C3 C16 121.58(16) . . ?
C2 C3 C16 120.40(16) . . ?
C1 C14 C5 118.80(14) . . ?
C1 C14 N1 119.60(13) . . ?
C5 C14 N1 121.60(14) . . ?
C8 C9 C10 120.06(16) . . ?
N2 C6 C5 112.12(12) . . ?
N2 C15 N1 112.59(13) . . ?
C29 C24 C25 120.79(16) . . ?
C29 C24 S2 118.69(13) . . ?
C25 C24 S2 120.29(14) . . ?
N1 C13 C12 111.93(12) . . ?
C28 C29 C24 119.35(16) . . ?
C11 C10 C9 118.13(15) . . ?
C11 C10 C17 121.89(15) . . ?
C9 C10 C17 119.98(16) . . ?
C23 C22 C21 121.31(18) . . ?
C18 C23 C22 119.27(16) . . ?
C23 C18 C19 120.86(16) . . ?
C23 C18 S1 118.55(13) . . ?
C19 C18 S1 120.24(14) . . ?
C29 C28 C27 121.11(18) . . ?
C18 C19 C20 119.04(18) . . ?
C26 C27 C28 118.70(16) . . ?
C26 C27 C31 120.25(16) . . ?
C28 C27 C31 121.05(17) . . ?
C27 C26 C25 121.14(16) . . ?
C26 C25 C24 118.91(17) . . ?
C21 C20 C19 121.10(16) . . ?
C20 C21 C22 118.41(16) . . ?
C20 C21 C30 120.19(17) . . ?
C22 C21 C30 121.41(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C5 C4 C3 1.6(2) . . . . ?
C6 C5 C4 C3 -176.73(15) . . . . ?
C11 C12 C7 C8 2.2(2) . . . . ?
C13 C12 C7 C8 -179.59(14) . . . . ?
C11 C12 C7 N2 -177.28(14) . . . . ?
C13 C12 C7 N2 1.0(2) . . . . ?
C15 N2 C7 C8 163.54(14) . . . . ?
C6 N2 C7 C8 -77.62(18) . . . . ?
C15 N2 C7 C12 -17.0(2) . . . . ?
C6 N2 C7 C12 101.82(17) . . . . ?
C12 C7 C8 C9 -4.7(2) . . . . ?
N2 C7 C8 C9 174.78(14) . . . . ?
C12 C7 C8 S2 -179.81(12) . . . . ?
N2 C7 C8 S2 -0.3(2) . . . . ?
O2 S2 C8 C9 -16.79(15) . . . . ?
C24 S2 C8 C9 93.34(14) . . . . ?
O2 S2 C8 C7 158.52(13) . . . . ?
C24 S2 C8 C7 -91.35(14) . . . . ?
C7 C12 C11 C10 2.0(2) . . . . ?
C13 C12 C11 C10 -176.29(15) . . . . ?
C3 C2 C1 C14 2.8(2) . . . . ?
C3 C2 C1 S1 177.61(13) . . . . ?
O1 S1 C1 C2 -14.92(15) . . . . ?
C18 S1 C1 C2 95.05(14) . . . . ?
O1 S1 C1 C14 159.97(13) . . . . ?
C18 S1 C1 C14 -90.06(14) . . . . ?
C5 C4 C3 C2 -2.4(2) . . . . ?
C5 C4 C3 C16 176.99(16) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C1 C2 C3 C16 -179.16(16) . . . . ?
C2 C1 C14 C5 -3.6(2) . . . . ?
S1 C1 C14 C5 -178.39(12) . . . . ?
C2 C1 C14 N1 176.01(14) . . . . ?
S1 C1 C14 N1 1.3(2) . . . . ?
C4 C5 C14 C1 1.5(2) . . . . ?
C6 C5 C14 C1 179.75(14) . . . . ?
C4 C5 C14 N1 -178.17(14) . . . . ?
C6 C5 C14 N1 0.1(2) . . . . ?
C15 N1 C14 C1 163.15(14) . . . . ?
C13 N1 C14 C1 -77.50(18) . . . . ?
C15 N1 C14 C5 -17.2(2) . . . . ?
C13 N1 C14 C5 102.14(16) . . . . ?
C7 C8 C9 C10 3.0(2) . . . . ?
S2 C8 C9 C10 178.24(12) . . . . ?
C7 N2 C6 C5 -73.20(17) . . . . ?
C15 N2 C6 C5 48.16(16) . . . . ?
C14 C5 C6 N2 -16.5(2) . . . . ?
C4 C5 C6 N2 161.73(14) . . . . ?
C7 N2 C15 N1 52.02(18) . . . . ?
C6 N2 C15 N1 -69.72(16) . . . . ?
C14 N1 C15 N2 52.99(18) . . . . ?
C13 N1 C15 N2 -69.34(16) . . . . ?
O2 S2 C24 C29 -2.30(14) . . . . ?
C8 S2 C24 C29 -112.15(13) . . . . ?
O2 S2 C24 C25 -176.79(12) . . . . ?
C8 S2 C24 C25 73.37(14) . . . . ?
C14 N1 C13 C12 -72.47(17) . . . . ?
C15 N1 C13 C12 48.97(16) . . . . ?
C11 C12 C13 N1 160.45(14) . . . . ?
C7 C12 C13 N1 -17.8(2) . . . . ?
C25 C24 C29 C28 -0.4(2) . . . . ?
S2 C24 C29 C28 -174.83(14) . . . . ?
C12 C11 C10 C9 -3.6(2) . . . . ?
C12 C11 C10 C17 175.90(16) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C8 C9 C10 C17 -178.38(16) . . . . ?
C21 C22 C23 C18 0.6(3) . . . . ?
C22 C23 C18 C19 -0.1(3) . . . . ?
C22 C23 C18 S1 -173.33(13) . . . . ?
O1 S1 C18 C23 6.19(16) . . . . ?
C1 S1 C18 C23 -103.99(14) . . . . ?
O1 S1 C18 C19 -167.09(13) . . . . ?
C1 S1 C18 C19 82.73(14) . . . . ?
C24 C29 C28 C27 0.5(3) . . . . ?
C23 C18 C19 C20 0.4(3) . . . . ?
S1 C18 C19 C20 173.48(14) . . . . ?
C29 C28 C27 C26 -0.8(3) . . . . ?
C29 C28 C27 C31 178.71(18) . . . . ?
C28 C27 C26 C25 1.0(3) . . . . ?
C31 C27 C26 C25 -178.48(17) . . . . ?
C27 C26 C25 C24 -0.9(3) . . . . ?
C29 C24 C25 C26 0.6(2) . . . . ?
S2 C24 C25 C26 174.97(13) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
C19 C20 C21 C22 1.5(3) . . . . ?
C19 C20 C21 C30 -178.59(18) . . . . ?
C23 C22 C21 C20 -1.3(3) . . . . ?
C23 C22 C21 C30 178.87(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046

_database_code_depnum_ccdc_archive 'CCDC 987100'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_jc191

# This structure was measured,
# solved and refined by:
# Rino Schwenk

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C31 H30 N2 O2 S2, C H2 Cl2'
_chemical_formula_sum            'C32 H32 Cl2 N2 O2 S2'
_chemical_formula_weight         611.62
_chemical_absolute_configuration syn

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'
Cl Cl 0.1484 0.1585 '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)
_symmetry_int_tables_number      4

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

_cell_length_a                   12.46120(10)
_cell_length_b                   9.16060(10)
_cell_length_c                   13.5717(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.8790(10)
_cell_angle_gamma                90.00
_cell_volume                     1490.12(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      30.66

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 'dichloromethane / pentane'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.391
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            18948
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         29.13
_reflns_number_total             7597
_reflns_number_gt                7078
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0489P)²+0.0029P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_number_reflns         7597
_refine_ls_number_parameters     365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.020
_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
S1 S 0.39028(3) 0.41671(4) 0.52378(3) 0.01573(8) Uani 1 1 d . . .
S2 S 0.26248(3) 0.05569(5) -0.05685(3) 0.01782(9) Uani 1 1 d . . .
O1 O 0.46748(10) 0.49231(16) 0.61342(8) 0.0229(3) Uani 1 1 d . . .
O2 O 0.18266(10) 0.03430(16) -0.16113(9) 0.0253(3) Uani 1 1 d . . .
N1 N 0.33270(11) 0.15161(15) 0.16477(9) 0.0142(3) Uani 1 1 d . . .
N2 N 0.30860(10) 0.27193(16) 0.31780(9) 0.0143(3) Uani 1 1 d . . .
C1 C 0.45748(12) 0.42696(19) 0.42217(10) 0.0141(3) Uani 1 1 d . . .
C2 C 0.55822(13) 0.49888(18) 0.44004(11) 0.0146(3) Uani 1 1 d . . .
H2 H 0.5842 0.5575 0.4996 0.017 Uiso 1 1 calc R . .
C3 C 0.62230(13) 0.48539(19) 0.37015(11) 0.0148(3) Uani 1 1 d . . .
C4 C 0.58326(12) 0.39315(18) 0.28622(11) 0.0140(3) Uani 1 1 d . . .
H4 H 0.6275 0.3798 0.2399 0.017 Uiso 1 1 calc R . .
C5 C 0.48164(13) 0.31983(18) 0.26779(11) 0.0141(3) Uani 1 1 d . . .
C6 C 0.44740(12) 0.21011(19) 0.18125(11) 0.0150(3) Uani 1 1 d . . .
H6A H 0.4530 0.2571 0.1171 0.018 Uiso 1 1 calc R . .
H6B H 0.5007 0.1276 0.1958 0.018 Uiso 1 1 calc R . .
C7 C 0.24827(13) 0.24205(18) 0.10067(11) 0.0144(3) Uani 1 1 d . . .
C8 C 0.21387(13) 0.21638(19) -0.00557(11) 0.0158(3) Uani 1 1 d . . .
C9 C 0.12805(14) 0.2963(2) -0.06862(12) 0.0212(3) Uani 1 1 d . . .
H9 H 0.1062 0.2777 -0.1402 0.025 Uiso 1 1 calc R . .
C10 C 0.07342(14) 0.4038(2) -0.02836(12) 0.0223(4) Uani 1 1 d . . .
C11 C 0.10476(13) 0.4258(2) 0.07793(12) 0.0197(3) Uani 1 1 d . . .
H11 H 0.0663 0.4962 0.1068 0.024 Uiso 1 1 calc R . .
C12 C 0.19154(13) 0.34591(19) 0.14182(11) 0.0148(3) Uani 1 1 d . . .
C13 C 0.21679(13) 0.3648(2) 0.25741(11) 0.0166(3) Uani 1 1 d . . .
H13A H 0.2360 0.4683 0.2746 0.020 Uiso 1 1 calc R . .
H13B H 0.1484 0.3425 0.2782 0.020 Uiso 1 1 calc R . .
C14 C 0.41591(12) 0.34114(18) 0.33479(11) 0.0138(3) Uani 1 1 d . . .
C15 C 0.30883(13) 0.13231(18) 0.26414(11) 0.0157(3) Uani 1 1 d . . .
H15A H 0.3657 0.0670 0.3076 0.019 Uiso 1 1 calc R . .
H15B H 0.2351 0.0848 0.2532 0.019 Uiso 1 1 calc R . .
C16 C 0.73259(13) 0.5633(2) 0.38867(12) 0.0202(3) Uani 1 1 d . . .
H16A H 0.7865 0.5198 0.4479 0.030 Uiso 1 1 calc R . .
H16B H 0.7227 0.6668 0.4021 0.030 Uiso 1 1 calc R . .
H16C H 0.7603 0.5539 0.3280 0.030 Uiso 1 1 calc R . .
C17 C -0.02066(17) 0.4918(3) -0.09566(14) 0.0358(5) Uani 1 1 d . . .
H17A H 0.0101 0.5707 -0.1284 0.054 Uiso 1 1 calc R . .
H17B H -0.0659 0.5335 -0.0539 0.054 Uiso 1 1 calc R . .
H17C H -0.0673 0.4284 -0.1484 0.054 Uiso 1 1 calc R . .
C18 C 0.27549(13) 0.53728(19) 0.47502(11) 0.0158(3) Uani 1 1 d . . .
C19 C 0.16972(14) 0.4814(2) 0.46649(12) 0.0188(3) Uani 1 1 d . . .
H19 H 0.1608 0.3838 0.4867 0.023 Uiso 1 1 calc R . .
C20 C 0.07692(14) 0.5701(2) 0.42798(12) 0.0194(3) Uani 1 1 d . . .
H20 H 0.0043 0.5320 0.4211 0.023 Uiso 1 1 calc R . .
C21 C 0.08920(14) 0.7133(2) 0.39960(12) 0.0208(3) Uani 1 1 d . . .
C22 C 0.19666(15) 0.7676(2) 0.41052(13) 0.0233(4) Uani 1 1 d . . .
H22 H 0.2059 0.8657 0.3915 0.028 Uiso 1 1 calc R . .
C23 C 0.28974(14) 0.6809(2) 0.44858(12) 0.0209(3) Uani 1 1 d . . .
H23 H 0.3625 0.7192 0.4565 0.025 Uiso 1 1 calc R . .
C24 C 0.38795(14) 0.12261(19) -0.08009(11) 0.0165(3) Uani 1 1 d . . .
C25 C 0.48767(14) 0.0519(2) -0.03416(11) 0.0198(3) Uani 1 1 d . . .
H25 H 0.4896 -0.0239 0.0141 0.024 Uiso 1 1 calc R . .
C26 C 0.58504(15) 0.0922(2) -0.05895(12) 0.0220(3) Uani 1 1 d . . .
H26 H 0.6534 0.0445 -0.0270 0.026 Uiso 1 1 calc R . .
C27 C 0.58241(14) 0.2023(2) -0.13035(13) 0.0208(3) Uani 1 1 d . . .
C28 C 0.48117(15) 0.2724(2) -0.17662(12) 0.0208(3) Uani 1 1 d . . .
H28 H 0.4787 0.3470 -0.2258 0.025 Uiso 1 1 calc R . .
C29 C 0.38478(14) 0.23347(19) -0.15120(12) 0.0184(3) Uani 1 1 d . . .
H29 H 0.3166 0.2822 -0.1821 0.022 Uiso 1 1 calc R . .
C30 C -0.01238(15) 0.8085(2) 0.35997(13) 0.0262(4) Uani 1 1 d . . .
H30A H -0.0774 0.7470 0.3299 0.039 Uiso 1 1 calc R . .
H30B H 0.0001 0.8751 0.3077 0.039 Uiso 1 1 calc R . .
H30C H -0.0258 0.8653 0.4166 0.039 Uiso 1 1 calc R . .
C31 C 0.68693(17) 0.2462(2) -0.15935(16) 0.0311(4) Uani 1 1 d . . .
H31A H 0.7500 0.1872 -0.1205 0.047 Uiso 1 1 calc R . .
H31B H 0.7026 0.3497 -0.1435 0.047 Uiso 1 1 calc R . .
H31C H 0.6759 0.2301 -0.2328 0.047 Uiso 1 1 calc R . .
Cl1 Cl 0.77294(5) 0.09034(7) 0.21832(5) 0.05219(17) Uani 1 1 d . . .
Cl2 Cl 0.98486(4) 0.19990(5) 0.34811(3) 0.02858(10) Uani 1 1 d . . .
C32 C 0.83947(15) 0.2315(2) 0.30042(14) 0.0261(4) Uani 1 1 d . . .
H32A H 0.8061 0.2393 0.3586 0.031 Uiso 1 1 calc R . .
H32B H 0.8270 0.3252 0.2628 0.031 Uiso 1 1 calc R . .


_geom_special_details            
; 

 Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)

  4.0957 (0.0077) x - 7.1960 (0.0037) y + 5.6238 (0.0080) z = 1.1603 (0.0051) 

 *    0.0152 (0.0011)  C1
 *    0.0107 (0.0011)  C2
 *   -0.0228 (0.0011)  C3
 *    0.0091 (0.0011)  C4
 *    0.0168 (0.0011)  C5
 *   -0.0290 (0.0011)  C14

 Rms deviation of fitted atoms =   0.0186


  8.9166 (0.0061) x + 6.3098 (0.0047) y - 4.1763 (0.0090) z = 3.3048 (0.0011) 

 Angle to previous plane (with approximate esd) = 68.47 ( 0.05 )

 *    0.0158 (0.0011)  C7
 *   -0.0092 (0.0012)  C8
 *   -0.0067 (0.0013)  C9
 *    0.0160 (0.0013)  C10
 *   -0.0094 (0.0013)  C11
 *   -0.0065 (0.0012)  C12

 Rms deviation of fitted atoms =   0.0113

 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
S1 O1 1.4982(12) . ?
S1 C18 1.7849(17) . ?
S1 C1 1.8010(14) . ?
S2 O2 1.5034(12) . ?
S2 C24 1.7860(17) . ?
S2 C8 1.8025(17) . ?
N1 C7 1.432(2) . ?
N1 C15 1.4691(19) . ?
N1 C6 1.485(2) . ?
N2 C14 1.440(2) . ?
N2 C15 1.472(2) . ?
N2 C13 1.480(2) . ?
C1 C2 1.379(2) . ?
C1 C14 1.399(2) . ?
C2 C3 1.402(2) . ?
C3 C4 1.395(2) . ?
C3 C16 1.507(2) . ?
C4 C5 1.394(2) . ?
C5 C14 1.394(2) . ?
C5 C6 1.516(2) . ?
C7 C12 1.390(2) . ?
C7 C8 1.407(2) . ?
C8 C9 1.382(2) . ?
C9 C10 1.391(3) . ?
C10 C11 1.402(2) . ?
C10 C17 1.508(2) . ?
C11 C12 1.394(2) . ?
C12 C13 1.523(2) . ?
C18 C23 1.388(2) . ?
C18 C19 1.389(2) . ?
C19 C20 1.393(2) . ?
C20 C21 1.388(3) . ?
C21 C22 1.398(2) . ?
C21 C30 1.510(2) . ?
C22 C23 1.384(3) . ?
C24 C25 1.389(2) . ?
C24 C29 1.394(2) . ?
C25 C26 1.395(2) . ?
C26 C27 1.392(3) . ?
C27 C28 1.402(3) . ?
C27 C31 1.515(2) . ?
C28 C29 1.384(2) . ?
Cl1 C32 1.7591(19) . ?
Cl2 C32 1.7729(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
O1 S1 C18 106.64(8) . . ?
O1 S1 C1 105.54(7) . . ?
C18 S1 C1 100.21(7) . . ?
O2 S2 C24 105.32(7) . . ?
O2 S2 C8 105.32(8) . . ?
C24 S2 C8 101.00(7) . . ?
C7 N1 C15 109.14(12) . . ?
C7 N1 C6 113.56(13) . . ?
C15 N1 C6 109.48(11) . . ?
C14 N2 C15 109.53(12) . . ?
C14 N2 C13 112.26(13) . . ?
C15 N2 C13 109.33(12) . . ?
C2 C1 C14 121.72(13) . . ?
C2 C1 S1 118.80(11) . . ?
C14 C1 S1 118.55(12) . . ?
C1 C2 C3 119.89(14) . . ?
C4 C3 C2 118.02(14) . . ?
C4 C3 C16 121.42(13) . . ?
C2 C3 C16 120.49(14) . . ?
C5 C4 C3 122.35(13) . . ?
C14 C5 C4 118.84(14) . . ?
C14 C5 C6 120.47(14) . . ?
C4 C5 C6 120.52(13) . . ?
N1 C6 C5 114.29(12) . . ?
C12 C7 C8 118.69(14) . . ?
C12 C7 N1 121.46(13) . . ?
C8 C7 N1 119.56(14) . . ?
C9 C8 C7 120.86(15) . . ?
C9 C8 S2 118.58(12) . . ?
C7 C8 S2 119.46(12) . . ?
C8 C9 C10 120.70(14) . . ?
C9 C10 C11 118.52(15) . . ?
C9 C10 C17 121.58(15) . . ?
C11 C10 C17 119.85(16) . . ?
C12 C11 C10 120.97(15) . . ?
C7 C12 C11 120.16(14) . . ?
C7 C12 C13 120.46(14) . . ?
C11 C12 C13 119.18(14) . . ?
N2 C13 C12 114.57(13) . . ?
C5 C14 C1 118.96(14) . . ?
C5 C14 N2 121.30(13) . . ?
C1 C14 N2 119.69(13) . . ?
N1 C15 N2 112.20(13) . . ?
C23 C18 C19 120.91(16) . . ?
C23 C18 S1 122.42(13) . . ?
C19 C18 S1 116.65(13) . . ?
C18 C19 C20 119.18(17) . . ?
C21 C20 C19 120.83(16) . . ?
C20 C21 C22 118.85(17) . . ?
C20 C21 C30 119.99(16) . . ?
C22 C21 C30 121.15(18) . . ?
C23 C22 C21 121.05(18) . . ?
C22 C23 C18 119.16(16) . . ?
C25 C24 C29 120.20(15) . . ?
C25 C24 S2 118.66(13) . . ?
C29 C24 S2 120.79(13) . . ?
C24 C25 C26 119.91(16) . . ?
C27 C26 C25 120.22(16) . . ?
C26 C27 C28 119.37(16) . . ?
C26 C27 C31 120.99(17) . . ?
C28 C27 C31 119.63(17) . . ?
C29 C28 C27 120.43(16) . . ?
C28 C29 C24 119.86(16) . . ?
Cl1 C32 Cl2 111.65(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C1 C2 -1.48(16) . . . . ?
C18 S1 C1 C2 109.14(14) . . . . ?
O1 S1 C1 C14 167.67(13) . . . . ?
C18 S1 C1 C14 -81.71(14) . . . . ?
C14 C1 C2 C3 -0.8(2) . . . . ?
S1 C1 C2 C3 168.02(13) . . . . ?
C1 C2 C3 C4 -2.8(2) . . . . ?
C1 C2 C3 C16 -179.98(16) . . . . ?
C2 C3 C4 C5 2.7(2) . . . . ?
C16 C3 C4 C5 179.86(15) . . . . ?
C3 C4 C5 C14 1.0(2) . . . . ?
C3 C4 C5 C6 -174.38(15) . . . . ?
C7 N1 C6 C5 84.99(16) . . . . ?
C15 N1 C6 C5 -37.26(18) . . . . ?
C14 C5 C6 N1 10.3(2) . . . . ?
C4 C5 C6 N1 -174.43(14) . . . . ?
C15 N1 C7 C12 28.2(2) . . . . ?
C6 N1 C7 C12 -94.27(17) . . . . ?
C15 N1 C7 C8 -145.52(14) . . . . ?
C6 N1 C7 C8 92.04(17) . . . . ?
C12 C7 C8 C9 2.3(2) . . . . ?
N1 C7 C8 C9 176.21(15) . . . . ?
C12 C7 C8 S2 -165.49(12) . . . . ?
N1 C7 C8 S2 8.4(2) . . . . ?
O2 S2 C8 C9 -7.10(15) . . . . ?
C24 S2 C8 C9 102.32(14) . . . . ?
O2 S2 C8 C7 161.01(12) . . . . ?
C24 S2 C8 C7 -89.58(13) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
S2 C8 C9 C10 167.70(14) . . . . ?
C8 C9 C10 C11 -2.1(3) . . . . ?
C8 C9 C10 C17 -179.76(19) . . . . ?
C9 C10 C11 C12 2.4(3) . . . . ?
C17 C10 C11 C12 -179.93(18) . . . . ?
C8 C7 C12 C11 -2.1(2) . . . . ?
N1 C7 C12 C11 -175.82(15) . . . . ?
C8 C7 C12 C13 172.81(15) . . . . ?
N1 C7 C12 C13 -0.9(2) . . . . ?
C10 C11 C12 C7 -0.3(3) . . . . ?
C10 C11 C12 C13 -175.23(16) . . . . ?
C14 N2 C13 C12 88.52(16) . . . . ?
C15 N2 C13 C12 -33.24(17) . . . . ?
C7 C12 C13 N2 3.6(2) . . . . ?
C11 C12 C13 N2 178.51(14) . . . . ?
C4 C5 C14 C1 -4.5(2) . . . . ?
C6 C5 C14 C1 170.85(14) . . . . ?
C4 C5 C14 N2 178.02(14) . . . . ?
C6 C5 C14 N2 -6.6(2) . . . . ?
C2 C1 C14 C5 4.5(2) . . . . ?
S1 C1 C14 C5 -164.32(12) . . . . ?
C2 C1 C14 N2 -178.00(15) . . . . ?
S1 C1 C14 N2 13.2(2) . . . . ?
C15 N2 C14 C5 29.79(19) . . . . ?
C13 N2 C14 C5 -91.85(17) . . . . ?
C15 N2 C14 C1 -147.65(14) . . . . ?
C13 N2 C14 C1 90.70(16) . . . . ?
C7 N1 C15 N2 -60.81(16) . . . . ?
C6 N1 C15 N2 64.05(16) . . . . ?
C14 N2 C15 N1 -59.36(16) . . . . ?
C13 N2 C15 N1 64.03(15) . . . . ?
O1 S1 C18 C23 53.51(14) . . . . ?
C1 S1 C18 C23 -56.24(14) . . . . ?
O1 S1 C18 C19 -125.19(12) . . . . ?
C1 S1 C18 C19 125.06(12) . . . . ?
C23 C18 C19 C20 1.9(2) . . . . ?
S1 C18 C19 C20 -179.39(11) . . . . ?
C18 C19 C20 C21 -0.9(2) . . . . ?
C19 C20 C21 C22 -0.2(2) . . . . ?
C19 C20 C21 C30 -178.80(14) . . . . ?
C20 C21 C22 C23 0.2(2) . . . . ?
C30 C21 C22 C23 178.84(15) . . . . ?
C21 C22 C23 C18 0.8(2) . . . . ?
C19 C18 C23 C22 -1.8(2) . . . . ?
S1 C18 C23 C22 179.52(12) . . . . ?
O2 S2 C24 C25 -127.50(13) . . . . ?
C8 S2 C24 C25 123.09(13) . . . . ?
O2 S2 C24 C29 45.75(15) . . . . ?
C8 S2 C24 C29 -63.66(14) . . . . ?
C29 C24 C25 C26 0.3(2) . . . . ?
S2 C24 C25 C26 173.54(13) . . . . ?
C24 C25 C26 C27 -0.6(3) . . . . ?
C25 C26 C27 C28 0.3(2) . . . . ?
C25 C26 C27 C31 -179.15(16) . . . . ?
C26 C27 C28 C29 0.4(2) . . . . ?
C31 C27 C28 C29 179.88(17) . . . . ?
C27 C28 C29 C24 -0.8(2) . . . . ?
C25 C24 C29 C28 0.5(2) . . . . ?
S2 C24 C29 C28 -172.67(13) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.051

_database_code_depnum_ccdc_archive 'CCDC 987101'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_jc269

# This structure was measured,
# solved and refined by:
# Rino Schwenk

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C17 H16 Br2 N2'
_chemical_formula_sum            'C17 H16 Br2 N2'
_chemical_formula_weight         408.14
_chemical_absolute_configuration ad

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_int_tables_number      4
_space_group_name_Hall           P2yb


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

_cell_length_a                   7.6662(11)
_cell_length_b                   8.3832(12)
_cell_length_c                   12.0468(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.193(2)
_cell_angle_gamma                90.00
_cell_volume                     769.70(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5443
_cell_measurement_theta_min      4.76
_cell_measurement_theta_max      31.23

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 'evaporation of ethyl acetate'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    5.260
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            23565
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_sigmaI/netI    0.0938
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.76
_diffrn_reflns_theta_max         34.33
_reflns_number_total             6413
_reflns_number_gt                4858
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0181P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(8)
_refine_ls_number_reflns         6413
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0619
_refine_ls_wR_factor_gt          0.0578
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_restrained_S_all      0.822
_refine_ls_shift/su_max          0.049
_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 1.01383(4) -0.14243(3) 0.02703(2) 0.02313(7) Uani 1 1 d . . .
Br2 Br 0.56145(4) 0.43782(3) 0.46426(2) 0.02111(7) Uani 1 1 d . . .
N1 N 0.8754(3) -0.0345(3) 0.24965(16) 0.0144(4) Uani 1 1 d . . .
N2 N 0.6936(3) 0.1205(3) 0.36265(17) 0.0150(4) Uani 1 1 d . . .
C1 C 0.8007(3) -0.0345(3) 0.0453(2) 0.0162(5) Uani 1 1 d . . .
C2 C 0.6875(4) -0.0027(3) -0.0489(2) 0.0202(6) Uani 1 1 d . . .
H2 H 0.7227 -0.0254 -0.1205 0.024 Uiso 1 1 calc R . .
C3 C 0.5211(4) 0.0625(3) -0.0405(2) 0.0199(6) Uani 1 1 d . . .
C4 C 0.4795(4) 0.1021(3) 0.0656(2) 0.0182(5) Uani 1 1 d . . .
H4 H 0.3681 0.1479 0.0732 0.022 Uiso 1 1 calc R . .
C5 C 0.5958(4) 0.0769(3) 0.1610(2) 0.0145(6) Uani 1 1 d . . .
C6 C 0.5462(4) 0.1295(3) 0.2738(2) 0.0166(5) Uani 1 1 d . . .
H6A H 0.5028 0.2408 0.2680 0.020 Uiso 1 1 calc R . .
H6B H 0.4492 0.0615 0.2945 0.020 Uiso 1 1 calc R . .
C7 C 0.8131(4) 0.2512(3) 0.3591(2) 0.0131(5) Uani 1 1 d . . .
C8 C 0.7751(3) 0.4023(3) 0.40021(19) 0.0152(5) Uani 1 1 d . . .
C9 C 0.8850(4) 0.5307(3) 0.3952(2) 0.0176(5) Uani 1 1 d . . .
H9 H 0.8526 0.6315 0.4226 0.021 Uiso 1 1 calc R . .
C10 C 1.0444(4) 0.5138(3) 0.3500(2) 0.0169(5) Uani 1 1 d . . .
C11 C 1.0874(3) 0.3638(4) 0.31329(18) 0.0147(5) Uani 1 1 d . . .
H11 H 1.1974 0.3488 0.2853 0.018 Uiso 1 1 calc R . .
C12 C 0.9742(4) 0.2345(3) 0.3161(2) 0.0140(5) Uani 1 1 d . . .
C13 C 1.0248(4) 0.0747(3) 0.2687(2) 0.0162(5) Uani 1 1 d . . .
H13A H 1.0743 0.0930 0.1972 0.019 Uiso 1 1 calc R . .
H13B H 1.1171 0.0246 0.3211 0.019 Uiso 1 1 calc R . .
C14 C 0.7592(4) 0.0049(3) 0.1530(2) 0.0148(5) Uani 1 1 d . . .
C15 C 0.7826(3) -0.0320(3) 0.3493(2) 0.0168(5) Uani 1 1 d . . .
H15A H 0.8673 -0.0516 0.4159 0.020 Uiso 1 1 calc R . .
H15B H 0.6949 -0.1191 0.3445 0.020 Uiso 1 1 calc R . .
C16 C 0.3929(5) 0.0850(4) -0.1423(2) 0.0301(8) Uani 1 1 d . . .
H16A H 0.4556 0.1194 -0.2049 0.045 Uiso 1 1 calc R . .
H16B H 0.3066 0.1664 -0.1274 0.045 Uiso 1 1 calc R . .
H16C H 0.3325 -0.0160 -0.1613 0.045 Uiso 1 1 calc R . .
C17 C 1.1605(4) 0.6555(3) 0.3398(2) 0.0211(6) Uani 1 1 d . . .
H17A H 1.2770 0.6194 0.3243 0.032 Uiso 1 1 calc R . .
H17B H 1.1707 0.7161 0.4097 0.032 Uiso 1 1 calc R . .
H17C H 1.1097 0.7236 0.2785 0.032 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. 

 Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)

  2.6571 (0.0072) x - 1.9835 (0.0086) y + 10.4205 (0.0064) z = 5.4177 (0.0068) 

 *   -0.0139 (0.0017)  C7
 *    0.0143 (0.0018)  C8
 *   -0.0003 (0.0018)  C9
 *   -0.0142 (0.0017)  C10
 *    0.0144 (0.0017)  C11
 *   -0.0003 (0.0018)  C12

 Rms deviation of fitted atoms =   0.0116


  3.1266 (0.0077) x + 7.6208 (0.0040) y - 1.5528 (0.0134) z = 2.1818 (0.0050) 

 Angle to previous plane (with approximate esd) = 81.30 ( 0.09 )

 *   -0.0118 (0.0018)  C1
 *    0.0227 (0.0019)  C2
 *   -0.0135 (0.0020)  C3
 *   -0.0063 (0.0020)  C4
 *    0.0171 (0.0019)  C5
 *   -0.0082 (0.0018)  C14

 Rms deviation of fitted atoms =   0.0144
;

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 1.901(2) . ?
Br2 C8 1.908(2) . ?
N1 C14 1.427(3) . ?
N1 C15 1.461(3) . ?
N1 C13 1.465(3) . ?
N2 C7 1.432(4) . ?
N2 C15 1.466(3) . ?
N2 C6 1.472(3) . ?
C1 C2 1.378(4) . ?
C1 C14 1.408(3) . ?
C2 C3 1.401(4) . ?
C3 C4 1.391(3) . ?
C3 C16 1.498(4) . ?
C4 C5 1.392(4) . ?
C5 C14 1.403(4) . ?
C5 C6 1.516(4) . ?
C7 C12 1.397(4) . ?
C7 C8 1.402(4) . ?
C8 C9 1.373(4) . ?
C9 C10 1.397(4) . ?
C10 C11 1.384(4) . ?
C10 C17 1.497(4) . ?
C11 C12 1.391(4) . ?
C12 C13 1.522(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
C14 N1 C15 110.55(19) . . ?
C14 N1 C13 113.0(2) . . ?
C15 N1 C13 107.71(19) . . ?
C7 N2 C15 110.9(2) . . ?
C7 N2 C6 112.5(2) . . ?
C15 N2 C6 107.2(2) . . ?
C2 C1 C14 121.9(2) . . ?
C2 C1 Br1 117.99(18) . . ?
C14 C1 Br1 120.0(2) . . ?
C1 C2 C3 120.9(2) . . ?
C4 C3 C2 117.4(3) . . ?
C4 C3 C16 121.8(3) . . ?
C2 C3 C16 120.8(2) . . ?
C3 C4 C5 122.2(3) . . ?
C4 C5 C14 120.3(2) . . ?
C4 C5 C6 119.7(2) . . ?
C14 C5 C6 119.9(3) . . ?
N2 C6 C5 112.9(2) . . ?
C12 C7 C8 116.6(3) . . ?
C12 C7 N2 121.9(2) . . ?
C8 C7 N2 121.5(2) . . ?
C9 C8 C7 122.8(2) . . ?
C9 C8 Br2 116.94(18) . . ?
C7 C8 Br2 120.3(2) . . ?
C8 C9 C10 120.3(2) . . ?
C11 C10 C9 117.7(2) . . ?
C11 C10 C17 122.0(2) . . ?
C9 C10 C17 120.3(3) . . ?
C10 C11 C12 122.0(2) . . ?
C11 C12 C7 120.6(3) . . ?
C11 C12 C13 119.5(2) . . ?
C7 C12 C13 119.9(2) . . ?
N1 C13 C12 112.5(2) . . ?
C5 C14 C1 117.1(2) . . ?
C5 C14 N1 121.8(2) . . ?
C1 C14 N1 121.0(2) . . ?
N1 C15 N2 112.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C3 -3.7(4) . . . . ?
Br1 C1 C2 C3 173.8(2) . . . . ?
C1 C2 C3 C4 3.7(4) . . . . ?
C1 C2 C3 C16 -175.2(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C16 C3 C4 C5 177.9(3) . . . . ?
C3 C4 C5 C14 -2.0(4) . . . . ?
C3 C4 C5 C6 177.2(3) . . . . ?
C7 N2 C6 C5 78.0(3) . . . . ?
C15 N2 C6 C5 -44.1(3) . . . . ?
C4 C5 C6 N2 -169.9(2) . . . . ?
C14 C5 C6 N2 9.3(4) . . . . ?
C15 N2 C7 C12 17.2(3) . . . . ?
C6 N2 C7 C12 -102.8(3) . . . . ?
C15 N2 C7 C8 -161.8(2) . . . . ?
C6 N2 C7 C8 78.2(3) . . . . ?
C12 C7 C8 C9 2.7(4) . . . . ?
N2 C7 C8 C9 -178.3(2) . . . . ?
C12 C7 C8 Br2 -178.46(19) . . . . ?
N2 C7 C8 Br2 0.6(3) . . . . ?
C7 C8 C9 C10 -1.5(4) . . . . ?
Br2 C8 C9 C10 179.63(19) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
C8 C9 C10 C17 177.2(2) . . . . ?
C9 C10 C11 C12 2.7(4) . . . . ?
C17 C10 C11 C12 -175.7(2) . . . . ?
C10 C11 C12 C7 -1.5(4) . . . . ?
C10 C11 C12 C13 176.7(2) . . . . ?
C8 C7 C12 C11 -1.2(4) . . . . ?
N2 C7 C12 C11 179.7(2) . . . . ?
C8 C7 C12 C13 -179.4(2) . . . . ?
N2 C7 C12 C13 1.5(4) . . . . ?
C14 N1 C13 C12 75.8(3) . . . . ?
C15 N1 C13 C12 -46.7(3) . . . . ?
C11 C12 C13 N1 -164.2(2) . . . . ?
C7 C12 C13 N1 14.0(3) . . . . ?
C4 C5 C14 C1 2.1(4) . . . . ?
C6 C5 C14 C1 -177.1(2) . . . . ?
C4 C5 C14 N1 -174.8(2) . . . . ?
C6 C5 C14 N1 6.0(4) . . . . ?
C2 C1 C14 C5 0.7(4) . . . . ?
Br1 C1 C14 C5 -176.73(19) . . . . ?
C2 C1 C14 N1 177.6(2) . . . . ?
Br1 C1 C14 N1 0.2(3) . . . . ?
C15 N1 C14 C5 15.8(3) . . . . ?
C13 N1 C14 C5 -105.0(3) . . . . ?
C15 N1 C14 C1 -160.9(2) . . . . ?
C13 N1 C14 C1 78.2(3) . . . . ?
C14 N1 C15 N2 -54.6(3) . . . . ?
C13 N1 C15 N2 69.3(3) . . . . ?
C7 N2 C15 N1 -53.2(3) . . . . ?
C6 N2 C15 N1 69.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        34.33
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.102

_database_code_depnum_ccdc_archive 'CCDC 987102'
