# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_kaw86
# (R,R)-1/(S,S)-2 

# start Validation Reply Form
_vrf_PLAT113_kaw86               
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New Space-group.       Pbcn       
RESPONSE: This quasiracemic material was designed to mimic true inversion
symmetry.  Thus , it is not surprising that this crystal structure
models high symmetry such as space group Pbcn. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 N2, C15 H12 Cl2 N2, C3 H6 O'
_chemical_formula_sum            'C35 H36 Cl2 N4 O'
_chemical_formula_weight         599.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   24.1816(6)
_cell_length_b                   10.4269(3)
_cell_length_c                   11.7456(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2961.53(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8161
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      66.91

_exptl_crystal_description       'transparent block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    2.248
_shelx_estimated_absorpt_T_min   0.524
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40264
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.656
_diffrn_reflns_theta_max         67.551
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5329
_reflns_number_gt                4381
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.988

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

All non-hydrogen atoms were located in a single difference density map and 
 refined with anisotropic displacement parameters.  All CH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom (1.5 x Uiso for methyl H atoms). 

The quasienatiomeric components organize with approximate inversioin
symmetry that mimics space group Pbcn. 
;

_computing_data_collection       APEX2
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_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. 

 All non-hydrogen atoms were located in a difference Fourier density map and 
 refined using anisotropic displacement parameter.  Each H atom
 was placed in calculated positions with Ueq = 1.2 x Uiso
 (1.5 x Uiso for methyl H atoms).  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+1.3199P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1694 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.021(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5329
_refine_ls_number_parameters     385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.5000 0.0000 0.5624(4) 0.0403(11) Uani 1 2 d S T P . .
N1A N 0.63391(12) -0.1549(3) 0.7466(3) 0.0247(7) Uani 1 1 d . . . . .
N2A N 0.69616(13) -0.1046(3) 0.9034(3) 0.0255(8) Uani 1 1 d . . . . .
C1A C 0.58881(15) -0.1566(3) 0.8282(3) 0.0229(8) Uani 1 1 d . . . . .
C2A C 0.53476(14) -0.1583(3) 0.7882(4) 0.0236(8) Uani 1 1 d . . . . .
H2A H 0.5280 -0.1551 0.7086 0.028 Uiso 1 1 calc R U . . .
C3A C 0.49086(16) -0.1647(4) 0.8625(3) 0.0260(9) Uani 1 1 d . . . . .
H3A H 0.4542 -0.1662 0.8333 0.031 Uiso 1 1 calc R U . . .
C4A C 0.49922(17) -0.1689(4) 0.9801(4) 0.0254(9) Uani 1 1 d . . . . .
C5A C 0.55355(17) -0.1643(4) 1.0196(3) 0.0265(8) Uani 1 1 d . . . . .
H5A H 0.5601 -0.1657 1.0993 0.032 Uiso 1 1 calc R U . . .
C6A C 0.59873(15) -0.1579(4) 0.9456(3) 0.0237(9) Uani 1 1 d . . . . .
C7A C 0.65665(16) -0.1459(4) 0.9920(4) 0.0290(9) Uani 1 1 d . . . . .
H7A1 H 0.6569 -0.0828 1.0550 0.035 Uiso 1 1 calc R U . . .
H7A2 H 0.6685 -0.2297 1.0232 0.035 Uiso 1 1 calc R U . . .
C8A C 0.68650(15) -0.1845(4) 0.8025(3) 0.0273(8) Uani 1 1 d . . . . .
H8A1 H 0.7171 -0.1713 0.7477 0.033 Uiso 1 1 calc R U . . .
H8A2 H 0.6867 -0.2759 0.8252 0.033 Uiso 1 1 calc R U . . .
C9A C 0.64035(15) -0.0281(4) 0.6927(3) 0.0254(9) Uani 1 1 d . . . . .
H9A1 H 0.6037 0.0035 0.6679 0.031 Uiso 1 1 calc R U . . .
H9A2 H 0.6640 -0.0365 0.6243 0.031 Uiso 1 1 calc R U . . .
C10A C 0.66600(14) 0.0684(3) 0.7734(3) 0.0229(9) Uani 1 1 d . . . . .
C11A C 0.66411(14) 0.1995(4) 0.7485(3) 0.0234(9) Uani 1 1 d . . . . .
H11A H 0.6491 0.2262 0.6776 0.028 Uiso 1 1 calc R U . . .
C12A C 0.68342(16) 0.2918(4) 0.8235(3) 0.0257(9) Uani 1 1 d . . . . .
C13A C 0.70608(15) 0.2501(4) 0.9263(4) 0.0294(9) Uani 1 1 d . . . . .
H13A H 0.7193 0.3114 0.9796 0.035 Uiso 1 1 calc R U . . .
C14A C 0.70949(16) 0.1212(4) 0.9515(4) 0.0274(10) Uani 1 1 d . . . . .
H14A H 0.7252 0.0948 1.0219 0.033 Uiso 1 1 calc R U . . .
C15A C 0.69026(14) 0.0288(4) 0.8752(3) 0.0234(9) Uani 1 1 d . . . . .
C16A C 0.68158(17) 0.4322(3) 0.7930(4) 0.0354(10) Uani 1 1 d . . . . .
H16A H 0.7147 0.4547 0.7493 0.053 Uiso 1 1 calc R U . . .
H16B H 0.6803 0.4836 0.8628 0.053 Uiso 1 1 calc R U . . .
H16C H 0.6486 0.4495 0.7471 0.053 Uiso 1 1 calc R U . . .
C17A C 0.45108(15) -0.1773(4) 1.0612(4) 0.0308(9) Uani 1 1 d . . . . .
H17A H 0.4168 -0.1561 1.0207 0.046 Uiso 1 1 calc R U . . .
H17B H 0.4566 -0.1167 1.1240 0.046 Uiso 1 1 calc R U . . .
H17C H 0.4485 -0.2646 1.0916 0.046 Uiso 1 1 calc R U . . .
C18A C 0.5000 0.0000 0.4598(5) 0.0303(15) Uani 1 2 d S T P . .
C19A C 0.44692(18) 0.0002(4) 0.3936(4) 0.0377(11) Uani 1 1 d . . . . .
H19A H 0.4156 0.0016 0.4464 0.056 Uiso 1 1 calc R U . . .
H19B H 0.4450 -0.0772 0.3464 0.056 Uiso 1 1 calc R U . . .
H19C H 0.4456 0.0762 0.3446 0.056 Uiso 1 1 calc R U . . .
Cl1B Cl 1.05523(4) 0.17589(10) 0.42716(10) 0.0366(3) Uani 1 1 d . . . . .
Cl2B Cl 0.82002(4) -0.45640(9) 0.71737(10) 0.0379(3) Uani 1 1 d . . . . .
O1B O 1.0000 0.0000 0.9370(4) 0.0344(10) Uani 1 2 d S T P . .
N1B N 0.86494(12) 0.1502(3) 0.7470(3) 0.0250(7) Uani 1 1 d . . . . .
N2B N 0.80403(13) 0.0943(3) 0.5913(3) 0.0252(7) Uani 1 1 d . . . . .
C1B C 0.91021(15) 0.1518(3) 0.6679(3) 0.0227(8) Uani 1 1 d . . . . .
C2B C 0.96404(15) 0.1551(3) 0.7097(4) 0.0242(8) Uani 1 1 d . . . . .
H2B H 0.9702 0.1525 0.7896 0.029 Uiso 1 1 calc R U . . .
C3B C 1.00869(16) 0.1621(4) 0.6363(4) 0.0261(9) Uani 1 1 d . . . . .
H3B H 1.0454 0.1648 0.6650 0.031 Uiso 1 1 calc R U . . .
C4B C 0.99878(17) 0.1653(4) 0.5203(4) 0.0258(9) Uani 1 1 d . . . . .
C5B C 0.94634(17) 0.1594(4) 0.4769(3) 0.0257(8) Uani 1 1 d . . . . .
H5B H 0.9408 0.1612 0.3969 0.031 Uiso 1 1 calc R U . . .
C6B C 0.90115(15) 0.1509(4) 0.5498(3) 0.0243(9) Uani 1 1 d . . . . .
C7B C 0.84338(16) 0.1341(4) 0.5022(3) 0.0282(9) Uani 1 1 d . . . . .
H7B1 H 0.8308 0.2160 0.4683 0.034 Uiso 1 1 calc R U . . .
H7B2 H 0.8441 0.0686 0.4412 0.034 Uiso 1 1 calc R U . . .
C8B C 0.81258(15) 0.1776(4) 0.6897(3) 0.0281(9) Uani 1 1 d . . . . .
H8B1 H 0.7818 0.1656 0.7441 0.034 Uiso 1 1 calc R U . . .
H8B2 H 0.8123 0.2682 0.6645 0.034 Uiso 1 1 calc R U . . .
C9B C 0.85868(15) 0.0264(4) 0.8050(3) 0.0249(8) Uani 1 1 d . . . . .
H9B1 H 0.8343 0.0370 0.8720 0.030 Uiso 1 1 calc R U . . .
H9B2 H 0.8953 -0.0032 0.8324 0.030 Uiso 1 1 calc R U . . .
C10B C 0.83419(14) -0.0741(3) 0.7257(3) 0.0218(8) Uani 1 1 d . . . . .
C11B C 0.83655(15) -0.2035(4) 0.7538(3) 0.0259(9) Uani 1 1 d . . . . .
H11B H 0.8517 -0.2293 0.8248 0.031 Uiso 1 1 calc R U . . .
C12B C 0.81695(16) -0.2949(4) 0.6785(4) 0.0283(9) Uani 1 1 d . . . . .
C13B C 0.79519(15) -0.2606(4) 0.5740(4) 0.0287(9) Uani 1 1 d . . . . .
H13B H 0.7832 -0.3241 0.5216 0.034 Uiso 1 1 calc R U . . .
C14B C 0.79123(16) -0.1324(4) 0.5476(4) 0.0274(10) Uani 1 1 d . . . . .
H14B H 0.7752 -0.1079 0.4771 0.033 Uiso 1 1 calc R U . . .
C15B C 0.81009(14) -0.0377(4) 0.6218(3) 0.0238(8) Uani 1 1 d . . . . .
C16B C 1.0000 0.0000 1.0406(5) 0.0263(14) Uani 1 2 d S T P . .
C17B C 1.05259(17) 0.0038(4) 1.1064(4) 0.0347(10) Uani 1 1 d . . . . .
H17F H 1.0624 -0.0831 1.1309 0.052 Uiso 1 1 calc R U . . .
H17D H 1.0479 0.0588 1.1735 0.052 Uiso 1 1 calc R U . . .
H17E H 1.0821 0.0384 1.0583 0.052 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C18A 1.205(7) . ?
N1A C1A 1.452(5) . ?
N1A C8A 1.464(5) . ?
N1A C9A 1.475(5) . ?
N2A C15A 1.438(5) . ?
N2A C8A 1.467(5) . ?
N2A C7A 1.476(5) . ?
C1A C2A 1.389(5) . ?
C1A C6A 1.400(6) . ?
C2A C3A 1.376(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.396(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.394(6) . ?
C4A C17A 1.507(5) . ?
C5A C6A 1.397(5) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.508(5) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C10A 1.515(5) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C15A 1.394(5) . ?
C10A C11A 1.398(5) . ?
C11A C12A 1.387(5) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.395(6) . ?
C12A C16A 1.508(5) . ?
C13A C14A 1.380(5) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.395(5) . ?
C14A H14A 0.9500 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C18A C19A 1.501(5) . ?
C18A C19A 1.501(5) 2_655 ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
Cl1B C4B 1.753(4) . ?
Cl2B C12B 1.746(4) . ?
O1B C16B 1.217(7) . ?
N1B C1B 1.435(5) . ?
N1B C8B 1.462(5) . ?
N1B C9B 1.468(5) . ?
N2B C15B 1.430(5) . ?
N2B C8B 1.460(5) . ?
N2B C7B 1.474(5) . ?
C1B C2B 1.392(5) . ?
C1B C6B 1.405(6) . ?
C2B C3B 1.383(5) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.384(5) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.368(6) . ?
C5B C6B 1.391(5) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.515(5) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B C10B 1.522(5) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B C11B 1.390(5) . ?
C10B C15B 1.405(5) . ?
C11B C12B 1.383(5) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.383(6) . ?
C13B C14B 1.375(6) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.394(5) . ?
C14B H14B 0.9500 . ?
C16B C17B 1.489(5) . ?
C16B C17B 1.489(5) 2_755 ?
C17B H17F 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?

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
C1A N1A C8A 110.7(3) . . ?
C1A N1A C9A 112.0(3) . . ?
C8A N1A C9A 106.8(3) . . ?
C15A N2A C8A 110.3(3) . . ?
C15A N2A C7A 112.4(3) . . ?
C8A N2A C7A 107.5(3) . . ?
C2A C1A C6A 119.6(4) . . ?
C2A C1A N1A 118.9(3) . . ?
C6A C1A N1A 121.4(3) . . ?
C3A C2A C1A 120.8(4) . . ?
C3A C2A H2A 119.6 . . ?
C1A C2A H2A 119.6 . . ?
C2A C3A C4A 121.1(4) . . ?
C2A C3A H3A 119.4 . . ?
C4A C3A H3A 119.4 . . ?
C5A C4A C3A 117.7(4) . . ?
C5A C4A C17A 121.3(4) . . ?
C3A C4A C17A 121.0(4) . . ?
C4A C5A C6A 122.1(4) . . ?
C4A C5A H5A 118.9 . . ?
C6A C5A H5A 118.9 . . ?
C5A C6A C1A 118.6(3) . . ?
C5A C6A C7A 120.4(3) . . ?
C1A C6A C7A 120.9(4) . . ?
N2A C7A C6A 111.8(3) . . ?
N2A C7A H7A1 109.3 . . ?
C6A C7A H7A1 109.3 . . ?
N2A C7A H7A2 109.3 . . ?
C6A C7A H7A2 109.3 . . ?
H7A1 C7A H7A2 107.9 . . ?
N1A C8A N2A 112.4(3) . . ?
N1A C8A H8A1 109.1 . . ?
N2A C8A H8A1 109.1 . . ?
N1A C8A H8A2 109.1 . . ?
N2A C8A H8A2 109.1 . . ?
H8A1 C8A H8A2 107.9 . . ?
N1A C9A C10A 111.7(3) . . ?
N1A C9A H9A1 109.3 . . ?
C10A C9A H9A1 109.3 . . ?
N1A C9A H9A2 109.3 . . ?
C10A C9A H9A2 109.3 . . ?
H9A1 C9A H9A2 107.9 . . ?
C15A C10A C11A 118.9(4) . . ?
C15A C10A C9A 120.8(3) . . ?
C11A C10A C9A 120.3(3) . . ?
C12A C11A C10A 122.3(4) . . ?
C12A C11A H11A 118.8 . . ?
C10A C11A H11A 118.8 . . ?
C11A C12A C13A 117.8(3) . . ?
C11A C12A C16A 120.9(4) . . ?
C13A C12A C16A 121.3(4) . . ?
C14A C13A C12A 120.8(4) . . ?
C14A C13A H13A 119.6 . . ?
C12A C13A H13A 119.6 . . ?
C13A C14A C15A 121.0(4) . . ?
C13A C14A H14A 119.5 . . ?
C15A C14A H14A 119.5 . . ?
C10A C15A C14A 119.1(4) . . ?
C10A C15A N2A 121.8(3) . . ?
C14A C15A N2A 119.1(4) . . ?
C12A C16A H16A 109.5 . . ?
C12A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C12A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C4A C17A H17A 109.5 . . ?
C4A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C4A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
O1A C18A C19A 121.2(3) . . ?
O1A C18A C19A 121.2(3) . 2_655 ?
C19A C18A C19A 117.6(5) . 2_655 ?
C18A C19A H19A 109.5 . . ?
C18A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C18A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C1B N1B C8B 111.1(3) . . ?
C1B N1B C9B 112.9(3) . . ?
C8B N1B C9B 107.2(3) . . ?
C15B N2B C8B 111.0(3) . . ?
C15B N2B C7B 112.5(3) . . ?
C8B N2B C7B 107.6(3) . . ?
C2B C1B C6B 119.6(4) . . ?
C2B C1B N1B 119.0(3) . . ?
C6B C1B N1B 121.3(3) . . ?
C3B C2B C1B 120.8(4) . . ?
C3B C2B H2B 119.6 . . ?
C1B C2B H2B 119.6 . . ?
C2B C3B C4B 118.6(4) . . ?
C2B C3B H3B 120.7 . . ?
C4B C3B H3B 120.7 . . ?
C5B C4B C3B 121.8(4) . . ?
C5B C4B Cl1B 119.5(3) . . ?
C3B C4B Cl1B 118.8(3) . . ?
C4B C5B C6B 120.1(4) . . ?
C4B C5B H5B 119.9 . . ?
C6B C5B H5B 119.9 . . ?
C5B C6B C1B 119.0(3) . . ?
C5B C6B C7B 120.3(3) . . ?
C1B C6B C7B 120.6(3) . . ?
N2B C7B C6B 111.5(3) . . ?
N2B C7B H7B1 109.3 . . ?
C6B C7B H7B1 109.3 . . ?
N2B C7B H7B2 109.3 . . ?
C6B C7B H7B2 109.3 . . ?
H7B1 C7B H7B2 108.0 . . ?
N2B C8B N1B 111.8(3) . . ?
N2B C8B H8B1 109.3 . . ?
N1B C8B H8B1 109.3 . . ?
N2B C8B H8B2 109.3 . . ?
N1B C8B H8B2 109.3 . . ?
H8B1 C8B H8B2 107.9 . . ?
N1B C9B C10B 111.2(3) . . ?
N1B C9B H9B1 109.4 . . ?
C10B C9B H9B1 109.4 . . ?
N1B C9B H9B2 109.4 . . ?
C10B C9B H9B2 109.4 . . ?
H9B1 C9B H9B2 108.0 . . ?
C11B C10B C15B 119.1(4) . . ?
C11B C10B C9B 120.5(3) . . ?
C15B C10B C9B 120.4(3) . . ?
C12B C11B C10B 120.2(4) . . ?
C12B C11B H11B 119.9 . . ?
C10B C11B H11B 119.9 . . ?
C11B C12B C13B 121.3(4) . . ?
C11B C12B Cl2B 118.9(3) . . ?
C13B C12B Cl2B 119.8(3) . . ?
C14B C13B C12B 118.6(4) . . ?
C14B C13B H13B 120.7 . . ?
C12B C13B H13B 120.7 . . ?
C13B C14B C15B 121.7(4) . . ?
C13B C14B H14B 119.2 . . ?
C15B C14B H14B 119.2 . . ?
C14B C15B C10B 119.1(4) . . ?
C14B C15B N2B 119.5(4) . . ?
C10B C15B N2B 121.4(4) . . ?
O1B C16B C17B 121.3(3) . . ?
O1B C16B C17B 121.3(3) . 2_755 ?
C17B C16B C17B 117.4(5) . 2_755 ?
C16B C17B H17F 109.5 . . ?
C16B C17B H17D 109.5 . . ?
H17F C17B H17D 109.5 . . ?
C16B C17B H17E 109.5 . . ?
H17F C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?

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
C8A N1A C1A C2A -166.2(3) . . . . ?
C9A N1A C1A C2A 74.6(4) . . . . ?
C8A N1A C1A C6A 13.1(5) . . . . ?
C9A N1A C1A C6A -106.1(4) . . . . ?
C6A C1A C2A C3A -1.7(6) . . . . ?
N1A C1A C2A C3A 177.6(3) . . . . ?
C1A C2A C3A C4A 0.4(6) . . . . ?
C2A C3A C4A C5A 1.0(6) . . . . ?
C2A C3A C4A C17A -179.3(4) . . . . ?
C3A C4A C5A C6A -1.0(6) . . . . ?
C17A C4A C5A C6A 179.3(4) . . . . ?
C4A C5A C6A C1A -0.3(6) . . . . ?
C4A C5A C6A C7A 176.6(4) . . . . ?
C2A C1A C6A C5A 1.6(5) . . . . ?
N1A C1A C6A C5A -177.7(3) . . . . ?
C2A C1A C6A C7A -175.3(3) . . . . ?
N1A C1A C6A C7A 5.4(5) . . . . ?
C15A N2A C7A C6A 74.0(4) . . . . ?
C8A N2A C7A C6A -47.5(4) . . . . ?
C5A C6A C7A N2A -164.0(3) . . . . ?
C1A C6A C7A N2A 12.8(5) . . . . ?
C1A N1A C8A N2A -51.2(4) . . . . ?
C9A N1A C8A N2A 70.9(4) . . . . ?
C15A N2A C8A N1A -52.7(4) . . . . ?
C7A N2A C8A N1A 70.1(4) . . . . ?
C1A N1A C9A C10A 74.1(4) . . . . ?
C8A N1A C9A C10A -47.3(4) . . . . ?
N1A C9A C10A C15A 12.5(5) . . . . ?
N1A C9A C10A C11A -165.4(3) . . . . ?
C15A C10A C11A C12A -2.8(5) . . . . ?
C9A C10A C11A C12A 175.2(3) . . . . ?
C10A C11A C12A C13A 1.0(5) . . . . ?
C10A C11A C12A C16A 179.0(3) . . . . ?
C11A C12A C13A C14A 0.5(6) . . . . ?
C16A C12A C13A C14A -177.5(4) . . . . ?
C12A C13A C14A C15A -0.2(6) . . . . ?
C11A C10A C15A C14A 3.1(5) . . . . ?
C9A C10A C15A C14A -174.9(3) . . . . ?
C11A C10A C15A N2A -176.7(3) . . . . ?
C9A C10A C15A N2A 5.3(5) . . . . ?
C13A C14A C15A C10A -1.7(6) . . . . ?
C13A C14A C15A N2A 178.1(4) . . . . ?
C8A N2A C15A C10A 13.8(5) . . . . ?
C7A N2A C15A C10A -106.1(4) . . . . ?
C8A N2A C15A C14A -165.9(3) . . . . ?
C7A N2A C15A C14A 74.1(4) . . . . ?
C8B N1B C1B C2B 166.4(3) . . . . ?
C9B N1B C1B C2B -73.1(4) . . . . ?
C8B N1B C1B C6B -13.2(5) . . . . ?
C9B N1B C1B C6B 107.3(4) . . . . ?
C6B C1B C2B C3B 2.3(5) . . . . ?
N1B C1B C2B C3B -177.3(3) . . . . ?
C1B C2B C3B C4B -0.3(6) . . . . ?
C2B C3B C4B C5B -1.1(7) . . . . ?
C2B C3B C4B Cl1B 179.3(3) . . . . ?
C3B C4B C5B C6B 0.4(6) . . . . ?
Cl1B C4B C5B C6B 180.0(3) . . . . ?
C4B C5B C6B C1B 1.6(6) . . . . ?
C4B C5B C6B C7B -175.3(4) . . . . ?
C2B C1B C6B C5B -2.9(6) . . . . ?
N1B C1B C6B C5B 176.6(3) . . . . ?
C2B C1B C6B C7B 173.9(3) . . . . ?
N1B C1B C6B C7B -6.5(5) . . . . ?
C15B N2B C7B C6B -75.4(4) . . . . ?
C8B N2B C7B C6B 47.2(4) . . . . ?
C5B C6B C7B N2B 165.4(3) . . . . ?
C1B C6B C7B N2B -11.5(5) . . . . ?
C15B N2B C8B N1B 52.7(4) . . . . ?
C7B N2B C8B N1B -70.9(4) . . . . ?
C1B N1B C8B N2B 52.2(4) . . . . ?
C9B N1B C8B N2B -71.6(4) . . . . ?
C1B N1B C9B C10B -74.3(4) . . . . ?
C8B N1B C9B C10B 48.4(4) . . . . ?
N1B C9B C10B C11B 165.0(3) . . . . ?
N1B C9B C10B C15B -13.4(5) . . . . ?
C15B C10B C11B C12B 2.0(5) . . . . ?
C9B C10B C11B C12B -176.5(3) . . . . ?
C10B C11B C12B C13B 0.6(6) . . . . ?
C10B C11B C12B Cl2B -179.4(3) . . . . ?
C11B C12B C13B C14B -2.6(6) . . . . ?
Cl2B C12B C13B C14B 177.4(3) . . . . ?
C12B C13B C14B C15B 2.0(6) . . . . ?
C13B C14B C15B C10B 0.6(6) . . . . ?
C13B C14B C15B N2B -178.8(4) . . . . ?
C11B C10B C15B C14B -2.6(5) . . . . ?
C9B C10B C15B C14B 175.9(3) . . . . ?
C11B C10B C15B N2B 176.8(3) . . . . ?
C9B C10B C15B N2B -4.8(5) . . . . ?
C8B N2B C15B C14B 165.2(3) . . . . ?
C7B N2B C15B C14B -74.0(4) . . . . ?
C8B N2B C15B C10B -14.1(5) . . . . ?
C7B N2B C15B C10B 106.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2B H2B O1B 0.95 2.46 3.241(5) 139.4 .
C2A H2A O1A 0.95 2.45 3.235(5) 139.4 .

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 986733'
#######################################################################
#
#                 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_14kaw08

# start Validation Reply Form

_vrf_PLAT111_14kaw08             
;
PROBLEM: ADDSYM Detects (Pseudo) Centre of Symmetry .....        100 %Fit  
RESPONSE: This crystal structure was designed to approximate inversion symmetry.
Given the handedness and chemical disimililarity of the components, the structure
can not organize with true inversion symmetry.
;
# end Validation Reply Form

# (S,S)-2/(R,R)-3 

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Br2 N2, C15 H12 Cl2 N2'
_chemical_formula_sum            'C30 H24 Br2 Cl2 N4'
_chemical_formula_weight         671.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.3103(2)
_cell_length_b                   10.2540(3)
_cell_length_c                   10.7089(3)
_cell_angle_alpha                83.053(1)
_cell_angle_beta                 77.266(2)
_cell_angle_gamma                80.846(1)
_cell_volume                     664.62(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8085
_cell_measurement_theta_min      4.249
_cell_measurement_theta_max      68.217

_exptl_crystal_description       'transparent block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.182
_exptl_absorpt_coefficient_mu    5.941
_shelx_estimated_absorpt_T_min   0.251
_shelx_estimated_absorpt_T_max   0.411
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14612
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.249
_diffrn_reflns_theta_max         68.212
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.859
_reflns_number_total             4174
_reflns_number_gt                4123
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     0.735
_reflns_Friedel_fraction_full    0.738

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

All non-hydrogen atoms were located in sequential difference
 density maps and refined with anisotropic displacement
 parameters.  All CH hydrogen atoms were placed in calculated
 positions with Ueq = 1.2 x Uiso to the corresponding C atom. 
 The atomic displacement parameters for C1A, C1B, C6A, and
 C6B were idealized (ISOR).
;

_computing_data_collection       APEX2
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+0.7001P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1728 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.044(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4174
_refine_ls_number_parameters     343
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.111
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.8787(2) -0.08132(11) 0.49254(12) 0.0147(3) Uani 1 1 d . . . . .
Cl2A Cl 0.3809(2) -0.29996(14) 1.36200(12) 0.0172(3) Uani 1 1 d . . . . .
N1A N 0.9527(7) -0.5648(4) 0.8572(5) 0.0087(9) Uani 1 1 d . . . . .
N2A N 1.1724(8) -0.4614(4) 0.9667(5) 0.0097(9) Uani 1 1 d . . . . .
C1A C 0.9326(9) -0.4468(5) 0.7730(5) 0.0064(10) Uani 1 1 d . U . . .
C2A C 0.7828(9) -0.4294(5) 0.6928(6) 0.0106(11) Uani 1 1 d . . . . .
H2A H 0.6906 -0.4954 0.6976 0.013 Uiso 1 1 calc R U . . .
C3A C 0.7640(9) -0.3192(5) 0.6064(5) 0.0110(11) Uani 1 1 d . . . . .
H3A H 0.6610 -0.3092 0.5521 0.013 Uiso 1 1 calc R U . . .
C4A C 0.8995(9) -0.2226(5) 0.6004(5) 0.0089(11) Uani 1 1 d . . . . .
C5A C 1.0476(9) -0.2372(6) 0.6795(6) 0.0112(11) Uani 1 1 d . . . . .
H5A H 1.1411 -0.1715 0.6724 0.013 Uiso 1 1 calc R U . . .
C6A C 1.0636(9) -0.3440(5) 0.7683(5) 0.0079(10) Uani 1 1 d . U . . .
C7A C 1.2118(9) -0.3540(6) 0.8640(5) 0.0116(11) Uani 1 1 d . . . . .
H7A1 H 1.3666 -0.3691 0.8178 0.014 Uiso 1 1 calc R U . . .
H7A2 H 1.1885 -0.2688 0.9030 0.014 Uiso 1 1 calc R U . . .
C8A C 1.1558(9) -0.5788(6) 0.9058(6) 0.0122(12) Uani 1 1 d . . . . .
H8A1 H 1.1609 -0.6574 0.9691 0.015 Uiso 1 1 calc R U . . .
H8A2 H 1.2830 -0.5936 0.8337 0.015 Uiso 1 1 calc R U . . .
C9A C 0.7693(9) -0.5693(5) 0.9688(5) 0.0102(11) Uani 1 1 d . . . . .
H9A1 H 0.7691 -0.6616 1.0087 0.012 Uiso 1 1 calc R U . . .
H9A2 H 0.6292 -0.5415 0.9396 0.012 Uiso 1 1 calc R U . . .
C10A C 0.7855(9) -0.4788(5) 1.0689(5) 0.0082(10) Uani 1 1 d . . . . .
C11A C 0.6039(10) -0.4433(5) 1.1637(5) 0.0103(11) Uani 1 1 d . . . . .
H11A H 0.4730 -0.4810 1.1713 0.012 Uiso 1 1 calc R U . . .
C12A C 0.6138(10) -0.3523(6) 1.2478(5) 0.0128(11) Uani 1 1 d . . . . .
C13A C 0.8072(10) -0.2995(5) 1.2416(5) 0.0126(12) Uani 1 1 d . . . . .
H13A H 0.8136 -0.2378 1.2996 0.015 Uiso 1 1 calc R U . . .
C14A C 0.9890(9) -0.3391(5) 1.1489(6) 0.0110(11) Uani 1 1 d . . . . .
H14A H 1.1225 -0.3053 1.1443 0.013 Uiso 1 1 calc R U . . .
C15A C 0.9797(9) -0.4273(5) 1.0627(5) 0.0083(10) Uani 1 1 d . . . . .
Br1B Br 0.60199(7) -0.15807(5) 0.95843(5) 0.02091(19) Uani 1 1 d . . . . .
Br2B Br 1.11061(9) 0.06119(6) 0.08328(6) 0.0280(2) Uani 1 1 d . . . . .
N1B N 0.5201(8) 0.3378(4) 0.5897(4) 0.0092(9) Uani 1 1 d . . . . .
N2B N 0.2983(7) 0.2351(4) 0.4812(4) 0.0099(9) Uani 1 1 d . . . . .
C1B C 0.5413(9) 0.2175(5) 0.6738(5) 0.0099(11) Uani 1 1 d . U . . .
C2B C 0.6887(9) 0.2037(5) 0.7558(5) 0.0091(11) Uani 1 1 d . . . . .
H2B H 0.7748 0.2723 0.7538 0.011 Uiso 1 1 calc R U . . .
C3B C 0.7112(9) 0.0910(5) 0.8404(5) 0.0092(11) Uani 1 1 d . . . . .
H3B H 0.8148 0.0807 0.8943 0.011 Uiso 1 1 calc R U . . .
C4B C 0.5803(10) -0.0053(5) 0.8445(6) 0.0112(11) Uani 1 1 d . . . . .
C5B C 0.4291(10) 0.0071(5) 0.7652(6) 0.0108(11) Uani 1 1 d . . . . .
H5B H 0.3399 -0.0605 0.7699 0.013 Uiso 1 1 calc R U . . .
C6B C 0.4093(9) 0.1207(5) 0.6778(5) 0.0090(11) Uani 1 1 d . U . . .
C7B C 0.2583(9) 0.1269(6) 0.5843(6) 0.0125(11) Uani 1 1 d . . . . .
H7B1 H 0.2826 0.0413 0.5459 0.015 Uiso 1 1 calc R U . . .
H7B2 H 0.1038 0.1416 0.6311 0.015 Uiso 1 1 calc R U . . .
C8B C 0.3170(10) 0.3536(6) 0.5409(6) 0.0150(12) Uani 1 1 d . . . . .
H8B1 H 0.3142 0.4316 0.4766 0.018 Uiso 1 1 calc R U . . .
H8B2 H 0.1897 0.3701 0.6126 0.018 Uiso 1 1 calc R U . . .
C9B C 0.7032(9) 0.3419(5) 0.4786(5) 0.0110(11) Uani 1 1 d . . . . .
H9B1 H 0.8433 0.3146 0.5078 0.013 Uiso 1 1 calc R U . . .
H9B2 H 0.7030 0.4339 0.4379 0.013 Uiso 1 1 calc R U . . .
C10B C 0.6864(9) 0.2509(5) 0.3807(5) 0.0084(11) Uani 1 1 d . . . . .
C11B C 0.8720(10) 0.2113(5) 0.2873(6) 0.0109(11) Uani 1 1 d . . . . .
H11B H 1.0051 0.2461 0.2813 0.013 Uiso 1 1 calc R U . . .
C12B C 0.8593(9) 0.1206(5) 0.2038(5) 0.0106(11) Uani 1 1 d . . . . .
C13B C 0.6680(9) 0.0678(5) 0.2104(5) 0.0108(11) Uani 1 1 d . . . . .
H13B H 0.6629 0.0052 0.1529 0.013 Uiso 1 1 calc R U . . .
C14B C 0.4849(10) 0.1072(5) 0.3017(5) 0.0116(11) Uani 1 1 d . . . . .
H14B H 0.3525 0.0721 0.3064 0.014 Uiso 1 1 calc R U . . .
C15B C 0.4920(10) 0.1990(5) 0.3882(5) 0.0095(11) 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
Cl1A C4A 1.747(6) . ?
Cl2A C12A 1.749(6) . ?
N1A C1A 1.425(7) . ?
N1A C8A 1.466(7) . ?
N1A C9A 1.471(8) . ?
N2A C15A 1.435(7) . ?
N2A C8A 1.464(7) . ?
N2A C7A 1.468(7) . ?
C1A C2A 1.390(8) . ?
C1A C6A 1.430(7) . ?
C2A C3A 1.378(8) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.394(8) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.374(8) . ?
C5A C6A 1.367(8) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.517(7) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C10A 1.530(7) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C11A 1.386(8) . ?
C10A C15A 1.395(8) . ?
C11A C12A 1.390(8) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.397(8) . ?
C13A C14A 1.383(8) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.385(8) . ?
C14A H14A 0.9500 . ?
Br1B C4B 1.872(5) . ?
Br2B C12B 1.880(6) . ?
N1B C1B 1.443(7) . ?
N1B C9B 1.466(8) . ?
N1B C8B 1.467(7) . ?
N2B C15B 1.426(7) . ?
N2B C8B 1.472(7) . ?
N2B C7B 1.477(7) . ?
C1B C6B 1.385(8) . ?
C1B C2B 1.395(8) . ?
C2B C3B 1.388(8) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.376(8) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.394(8) . ?
C5B C6B 1.411(8) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.517(7) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B C10B 1.516(7) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B C15B 1.396(8) . ?
C10B C11B 1.403(8) . ?
C11B C12B 1.388(8) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.384(8) . ?
C13B C14B 1.380(8) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.410(7) . ?
C14B H14B 0.9500 . ?

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
C1A N1A C8A 110.6(4) . . ?
C1A N1A C9A 113.4(4) . . ?
C8A N1A C9A 107.7(4) . . ?
C15A N2A C8A 111.3(4) . . ?
C15A N2A C7A 112.5(4) . . ?
C8A N2A C7A 107.3(4) . . ?
C2A C1A N1A 120.1(5) . . ?
C2A C1A C6A 118.3(5) . . ?
N1A C1A C6A 121.6(4) . . ?
C3A C2A C1A 121.9(5) . . ?
C3A C2A H2A 119.0 . . ?
C1A C2A H2A 119.0 . . ?
C2A C3A C4A 118.6(5) . . ?
C2A C3A H3A 120.7 . . ?
C4A C3A H3A 120.7 . . ?
C5A C4A C3A 120.5(5) . . ?
C5A C4A Cl1A 119.8(4) . . ?
C3A C4A Cl1A 119.7(4) . . ?
C6A C5A C4A 121.6(5) . . ?
C6A C5A H5A 119.2 . . ?
C4A C5A H5A 119.2 . . ?
C5A C6A C1A 118.9(5) . . ?
C5A C6A C7A 121.7(5) . . ?
C1A C6A C7A 119.4(5) . . ?
N2A C7A C6A 112.9(5) . . ?
N2A C7A H7A1 109.0 . . ?
C6A C7A H7A1 109.0 . . ?
N2A C7A H7A2 109.0 . . ?
C6A C7A H7A2 109.0 . . ?
H7A1 C7A H7A2 107.8 . . ?
N2A C8A N1A 112.0(4) . . ?
N2A C8A H8A1 109.2 . . ?
N1A C8A H8A1 109.2 . . ?
N2A C8A H8A2 109.2 . . ?
N1A C8A H8A2 109.2 . . ?
H8A1 C8A H8A2 107.9 . . ?
N1A C9A C10A 111.6(4) . . ?
N1A C9A H9A1 109.3 . . ?
C10A C9A H9A1 109.3 . . ?
N1A C9A H9A2 109.3 . . ?
C10A C9A H9A2 109.3 . . ?
H9A1 C9A H9A2 108.0 . . ?
C11A C10A C15A 119.5(5) . . ?
C11A C10A C9A 120.0(5) . . ?
C15A C10A C9A 120.5(5) . . ?
C10A C11A C12A 119.8(5) . . ?
C10A C11A H11A 120.1 . . ?
C12A C11A H11A 120.1 . . ?
C11A C12A C13A 121.0(5) . . ?
C11A C12A Cl2A 120.1(5) . . ?
C13A C12A Cl2A 118.9(4) . . ?
C14A C13A C12A 118.4(5) . . ?
C14A C13A H13A 120.8 . . ?
C12A C13A H13A 120.8 . . ?
C13A C14A C15A 121.1(5) . . ?
C13A C14A H14A 119.5 . . ?
C15A C14A H14A 119.5 . . ?
C14A C15A C10A 120.1(5) . . ?
C14A C15A N2A 118.2(5) . . ?
C10A C15A N2A 121.6(5) . . ?
C1B N1B C9B 112.8(4) . . ?
C1B N1B C8B 111.1(5) . . ?
C9B N1B C8B 107.7(4) . . ?
C15B N2B C8B 110.7(5) . . ?
C15B N2B C7B 111.2(4) . . ?
C8B N2B C7B 108.0(4) . . ?
C6B C1B C2B 120.6(5) . . ?
C6B C1B N1B 120.6(5) . . ?
C2B C1B N1B 118.8(5) . . ?
C3B C2B C1B 120.8(5) . . ?
C3B C2B H2B 119.6 . . ?
C1B C2B H2B 119.6 . . ?
C4B C3B C2B 118.7(5) . . ?
C4B C3B H3B 120.7 . . ?
C2B C3B H3B 120.7 . . ?
C3B C4B C5B 121.6(5) . . ?
C3B C4B Br1B 120.3(4) . . ?
C5B C4B Br1B 118.1(4) . . ?
C4B C5B C6B 119.5(5) . . ?
C4B C5B H5B 120.2 . . ?
C6B C5B H5B 120.2 . . ?
C1B C6B C5B 118.7(5) . . ?
C1B C6B C7B 122.3(5) . . ?
C5B C6B C7B 118.7(5) . . ?
N2B C7B C6B 111.0(4) . . ?
N2B C7B H7B1 109.4 . . ?
C6B C7B H7B1 109.4 . . ?
N2B C7B H7B2 109.4 . . ?
C6B C7B H7B2 109.4 . . ?
H7B1 C7B H7B2 108.0 . . ?
N1B C8B N2B 111.5(4) . . ?
N1B C8B H8B1 109.3 . . ?
N2B C8B H8B1 109.3 . . ?
N1B C8B H8B2 109.3 . . ?
N2B C8B H8B2 109.3 . . ?
H8B1 C8B H8B2 108.0 . . ?
N1B C9B C10B 111.2(4) . . ?
N1B C9B H9B1 109.4 . . ?
C10B C9B H9B1 109.4 . . ?
N1B C9B H9B2 109.4 . . ?
C10B C9B H9B2 109.4 . . ?
H9B1 C9B H9B2 108.0 . . ?
C15B C10B C11B 119.6(5) . . ?
C15B C10B C9B 120.5(5) . . ?
C11B C10B C9B 119.7(5) . . ?
C12B C11B C10B 119.3(5) . . ?
C12B C11B H11B 120.4 . . ?
C10B C11B H11B 120.4 . . ?
C13B C12B C11B 121.7(5) . . ?
C13B C12B Br2B 118.6(4) . . ?
C11B C12B Br2B 119.6(4) . . ?
C14B C13B C12B 119.0(5) . . ?
C14B C13B H13B 120.5 . . ?
C12B C13B H13B 120.5 . . ?
C13B C14B C15B 120.7(5) . . ?
C13B C14B H14B 119.6 . . ?
C15B C14B H14B 119.6 . . ?
C10B C15B C14B 119.5(5) . . ?
C10B C15B N2B 122.2(5) . . ?
C14B C15B N2B 118.2(5) . . ?

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
C8A N1A C1A C2A 164.7(5) . . . . ?
C9A N1A C1A C2A -74.2(6) . . . . ?
C8A N1A C1A C6A -15.4(7) . . . . ?
C9A N1A C1A C6A 105.7(5) . . . . ?
N1A C1A C2A C3A -177.5(5) . . . . ?
C6A C1A C2A C3A 2.6(8) . . . . ?
C1A C2A C3A C4A -0.2(8) . . . . ?
C2A C3A C4A C5A -0.3(8) . . . . ?
C2A C3A C4A Cl1A -179.7(4) . . . . ?
C3A C4A C5A C6A -1.7(8) . . . . ?
Cl1A C4A C5A C6A 177.7(4) . . . . ?
C4A C5A C6A C1A 4.0(8) . . . . ?
C4A C5A C6A C7A -174.2(5) . . . . ?
C2A C1A C6A C5A -4.4(8) . . . . ?
N1A C1A C6A C5A 175.7(5) . . . . ?
C2A C1A C6A C7A 173.9(5) . . . . ?
N1A C1A C6A C7A -6.0(7) . . . . ?
C15A N2A C7A C6A -77.4(5) . . . . ?
C8A N2A C7A C6A 45.3(6) . . . . ?
C5A C6A C7A N2A 168.3(5) . . . . ?
C1A C6A C7A N2A -10.0(7) . . . . ?
C15A N2A C8A N1A 52.6(6) . . . . ?
C7A N2A C8A N1A -70.8(6) . . . . ?
C1A N1A C8A N2A 54.6(6) . . . . ?
C9A N1A C8A N2A -69.8(6) . . . . ?
C1A N1A C9A C10A -75.5(5) . . . . ?
C8A N1A C9A C10A 47.2(5) . . . . ?
N1A C9A C10A C11A 163.6(4) . . . . ?
N1A C9A C10A C15A -13.8(6) . . . . ?
C15A C10A C11A C12A 2.9(7) . . . . ?
C9A C10A C11A C12A -174.6(5) . . . . ?
C10A C11A C12A C13A -2.5(8) . . . . ?
C10A C11A C12A Cl2A 176.5(4) . . . . ?
C11A C12A C13A C14A 0.5(8) . . . . ?
Cl2A C12A C13A C14A -178.5(4) . . . . ?
C12A C13A C14A C15A 1.1(8) . . . . ?
C13A C14A C15A C10A -0.6(8) . . . . ?
C13A C14A C15A N2A 178.2(5) . . . . ?
C11A C10A C15A C14A -1.4(7) . . . . ?
C9A C10A C15A C14A 176.0(5) . . . . ?
C11A C10A C15A N2A 179.8(5) . . . . ?
C9A C10A C15A N2A -2.7(7) . . . . ?
C8A N2A C15A C14A 165.3(5) . . . . ?
C7A N2A C15A C14A -74.3(6) . . . . ?
C8A N2A C15A C10A -15.9(7) . . . . ?
C7A N2A C15A C10A 104.5(5) . . . . ?
C9B N1B C1B C6B -107.0(6) . . . . ?
C8B N1B C1B C6B 14.0(7) . . . . ?
C9B N1B C1B C2B 76.4(6) . . . . ?
C8B N1B C1B C2B -162.6(5) . . . . ?
C6B C1B C2B C3B 2.0(8) . . . . ?
N1B C1B C2B C3B 178.6(5) . . . . ?
C1B C2B C3B C4B -1.9(8) . . . . ?
C2B C3B C4B C5B 0.8(8) . . . . ?
C2B C3B C4B Br1B -179.2(4) . . . . ?
C3B C4B C5B C6B 0.3(8) . . . . ?
Br1B C4B C5B C6B -179.7(4) . . . . ?
C2B C1B C6B C5B -0.9(8) . . . . ?
N1B C1B C6B C5B -177.4(5) . . . . ?
C2B C1B C6B C7B -175.7(5) . . . . ?
N1B C1B C6B C7B 7.8(8) . . . . ?
C4B C5B C6B C1B -0.2(8) . . . . ?
C4B C5B C6B C7B 174.7(5) . . . . ?
C15B N2B C7B C6B 76.9(5) . . . . ?
C8B N2B C7B C6B -44.7(6) . . . . ?
C1B C6B C7B N2B 8.7(7) . . . . ?
C5B C6B C7B N2B -166.1(5) . . . . ?
C1B N1B C8B N2B -53.1(6) . . . . ?
C9B N1B C8B N2B 70.8(6) . . . . ?
C15B N2B C8B N1B -51.8(6) . . . . ?
C7B N2B C8B N1B 70.2(6) . . . . ?
C1B N1B C9B C10B 74.5(5) . . . . ?
C8B N1B C9B C10B -48.4(5) . . . . ?
N1B C9B C10B C15B 13.7(7) . . . . ?
N1B C9B C10B C11B -161.8(4) . . . . ?
C15B C10B C11B C12B -0.1(8) . . . . ?
C9B C10B C11B C12B 175.5(5) . . . . ?
C10B C11B C12B C13B -0.2(8) . . . . ?
C10B C11B C12B Br2B -177.3(4) . . . . ?
C11B C12B C13B C14B 0.6(8) . . . . ?
Br2B C12B C13B C14B 177.7(4) . . . . ?
C12B C13B C14B C15B -0.6(8) . . . . ?
C11B C10B C15B C14B 0.0(7) . . . . ?
C9B C10B C15B C14B -175.5(5) . . . . ?
C11B C10B C15B N2B 179.8(5) . . . . ?
C9B C10B C15B N2B 4.3(8) . . . . ?
C13B C14B C15B C10B 0.3(8) . . . . ?
C13B C14B C15B N2B -179.4(5) . . . . ?
C8B N2B C15B C10B 14.2(7) . . . . ?
C7B N2B C15B C10B -105.8(5) . . . . ?
C8B N2B C15B C14B -166.0(5) . . . . ?
C7B N2B C15B C14B 73.9(6) . . . . ?

_refine_diff_density_max         0.668
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.109

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 986734'
#######################################################################
#
#                 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_kaw85
# (S,S)-1/(S,S)-2

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16.36 H16.07 Cl0.64 N2'
_chemical_formula_sum            'C16.36 H16.07 Cl0.64 N2'
_chemical_formula_weight         263.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.0409(2)
_cell_length_b                   8.0224(3)
_cell_length_c                   27.0534(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1311.08(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4932
_cell_measurement_theta_min      3.277
_cell_measurement_theta_max      66.890

_exptl_crystal_description       'transparent block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             556.6
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.783
_shelx_estimated_absorpt_T_min   0.551
_shelx_estimated_absorpt_T_max   0.664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.574
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII 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            17744
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.267
_diffrn_reflns_theta_max         67.401
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2351
_reflns_number_gt                2174
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.986

_computing_data_collection       APEX2
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
; 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

All non-hydrogen atoms were located in a single difference density map and 
 refined with anisotropic displacement parameters.  All CH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom (1.5 x Uiso for methyl H atoms).

The final model used for refined included disorder of methyl and Cl
 substituents. The occupancy factors associated with these 
 groups were fixed at unity and refined to give a 
 32:68 (Me:Cl) ratio of components.   
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+0.4106P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 833 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.049(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2351
_refine_ls_number_parameters     193
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_restrained_S_all      1.196
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.0292(14) 0.5838(11) 0.1832(2) 0.0299(14) Uani 0.322(5) 1 d D . P A 1
Cl2 Cl -0.0316(18) 1.2625(9) 0.4687(4) 0.0365(16) Uani 0.322(5) 1 d D . P A 1
N1 N -0.5810(4) 0.6909(3) 0.35219(9) 0.0310(6) Uani 1 1 d . . . . .
N2 N -0.3063(4) 0.5791(3) 0.40904(9) 0.0301(6) Uani 1 1 d . . . . .
C1 C -0.4275(5) 0.6663(4) 0.31200(10) 0.0287(6) Uani 1 1 d . . . . .
C2 C -0.4795(5) 0.7305(4) 0.26555(10) 0.0323(7) Uani 1 1 d . . . . .
H2 H -0.6126 0.7917 0.2610 0.039 Uiso 1 1 calc R U . . .
C3 C -0.3383(5) 0.7052(4) 0.22607(11) 0.0323(7) Uani 1 1 d . . . . .
H3 H -0.3750 0.7499 0.1946 0.039 Uiso 1 1 calc R U . . .
C4 C -0.1430(5) 0.6151(4) 0.23187(10) 0.0311(7) Uani 1 1 d D . . . .
C5 C -0.0896(5) 0.5541(4) 0.27829(10) 0.0298(7) Uani 1 1 d . . . . .
H5 H 0.0447 0.4944 0.2827 0.036 Uiso 1 1 calc R U . . .
C6 C -0.2297(5) 0.5790(4) 0.31852(10) 0.0279(6) Uani 1 1 d . . . . .
C7 C -0.1650(5) 0.5135(4) 0.36912(11) 0.0308(7) Uani 1 1 d . . . . .
H7A H -0.1747 0.3903 0.3689 0.037 Uiso 1 1 calc R U . . .
H7B H -0.0092 0.5442 0.3759 0.037 Uiso 1 1 calc R U . . .
C8 C -0.5365(5) 0.5730(4) 0.39207(11) 0.0333(7) Uani 1 1 d . . . . .
H8A H -0.5705 0.4589 0.3804 0.040 Uiso 1 1 calc R U . . .
H8B H -0.6357 0.5980 0.4202 0.040 Uiso 1 1 calc R U . . .
C9 C -0.5663(5) 0.8605(4) 0.37278(11) 0.0328(7) Uani 1 1 d . . . . .
H9A H -0.7039 0.8853 0.3912 0.039 Uiso 1 1 calc R U . . .
H9B H -0.5548 0.9414 0.3453 0.039 Uiso 1 1 calc R U . . .
C10 C -0.3694(5) 0.8828(4) 0.40705(10) 0.0287(7) Uani 1 1 d . . . . .
C11 C -0.3060(5) 1.0414(4) 0.42255(10) 0.0294(7) Uani 1 1 d . . . . .
H11 H -0.3908 1.1351 0.4124 0.035 Uiso 1 1 calc R U . . .
C12 C -0.1223(5) 1.0660(4) 0.45240(10) 0.0308(7) Uani 1 1 d D . . . .
C13 C -0.0045(5) 0.9265(4) 0.46893(10) 0.0316(6) Uani 1 1 d . . . . .
H13 H 0.1195 0.9407 0.4901 0.038 Uiso 1 1 calc R U . . .
C14 C -0.0674(5) 0.7696(4) 0.45463(10) 0.0295(6) Uani 1 1 d . . . . .
H14 H 0.0132 0.6758 0.4663 0.035 Uiso 1 1 calc R U . . .
C15 C -0.2483(5) 0.7450(4) 0.42308(10) 0.0283(6) Uani 1 1 d . . . . .
C16 C -0.048(3) 1.2395(15) 0.4667(7) 0.039(4) Uani 0.678(5) 1 d D . P A 2
H16A H 0.0910 1.2658 0.4497 0.058 Uiso 0.678(5) 1 calc R U P A 2
H16B H -0.0253 1.2446 0.5025 0.058 Uiso 0.678(5) 1 calc R U P A 2
H16C H -0.1617 1.3203 0.4571 0.058 Uiso 0.678(5) 1 calc R U P A 2
C17 C 0.005(3) 0.585(2) 0.1870(5) 0.049(5) Uani 0.678(5) 1 d D . P A 2
H17A H 0.1520 0.6320 0.1932 0.073 Uiso 0.678(5) 1 calc R U P A 2
H17B H -0.0604 0.6389 0.1579 0.073 Uiso 0.678(5) 1 calc R U P A 2
H17C H 0.0178 0.4649 0.1810 0.073 Uiso 0.678(5) 1 calc R U P A 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
Cl1 C4 1.697(7) . ?
Cl2 C12 1.727(8) . ?
N1 C1 1.443(4) . ?
N1 C8 1.460(4) . ?
N1 C9 1.472(4) . ?
N2 C15 1.428(4) . ?
N2 C8 1.465(4) . ?
N2 C7 1.474(4) . ?
C1 C2 1.394(4) . ?
C1 C6 1.396(4) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 C17 1.527(10) . ?
C5 C6 1.393(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.517(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.519(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.393(4) . ?
C10 C15 1.394(4) . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.399(4) . ?
C12 C16 1.513(11) . ?
C13 C14 1.371(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.401(4) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C1 N1 C8 110.5(2) . . ?
C1 N1 C9 111.9(2) . . ?
C8 N1 C9 107.9(2) . . ?
C15 N2 C8 110.3(2) . . ?
C15 N2 C7 112.7(2) . . ?
C8 N2 C7 108.0(2) . . ?
C2 C1 C6 119.5(3) . . ?
C2 C1 N1 119.0(3) . . ?
C6 C1 N1 121.6(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 C17 121.9(8) . . ?
C3 C4 C17 119.2(8) . . ?
C5 C4 Cl1 120.5(4) . . ?
C3 C4 Cl1 120.6(3) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 119.9(3) . . ?
C1 C6 C7 120.6(3) . . ?
N2 C7 C6 112.8(2) . . ?
N2 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N2 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 N2 112.6(2) . . ?
N1 C8 H8A 109.1 . . ?
N2 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
N2 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N1 C9 C10 112.8(2) . . ?
N1 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 119.1(3) . . ?
C11 C10 C9 120.4(3) . . ?
C15 C10 C9 120.5(3) . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 C16 121.1(8) . . ?
C13 C12 C16 120.2(9) . . ?
C11 C12 Cl2 122.2(4) . . ?
C13 C12 Cl2 119.1(4) . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C14 119.2(3) . . ?
C10 C15 N2 121.8(3) . . ?
C14 C15 N2 119.0(3) . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C8 N1 C1 C2 161.5(3) . . . . ?
C9 N1 C1 C2 -78.2(3) . . . . ?
C8 N1 C1 C6 -18.0(4) . . . . ?
C9 N1 C1 C6 102.3(3) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
N1 C1 C2 C3 -178.4(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C2 C3 C4 C17 178.0(9) . . . . ?
C2 C3 C4 Cl1 179.7(4) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C17 C4 C5 C6 -178.2(9) . . . . ?
Cl1 C4 C5 C6 -180.0(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 -178.9(3) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
N1 C1 C6 C5 178.1(3) . . . . ?
C2 C1 C6 C7 177.7(3) . . . . ?
N1 C1 C6 C7 -2.8(4) . . . . ?
C15 N2 C7 C6 -78.5(3) . . . . ?
C8 N2 C7 C6 43.6(3) . . . . ?
C5 C6 C7 N2 168.2(3) . . . . ?
C1 C6 C7 N2 -10.9(4) . . . . ?
C1 N1 C8 N2 54.3(3) . . . . ?
C9 N1 C8 N2 -68.3(3) . . . . ?
C15 N2 C8 N1 55.1(3) . . . . ?
C7 N2 C8 N1 -68.5(3) . . . . ?
C1 N1 C9 C10 -78.4(3) . . . . ?
C8 N1 C9 C10 43.4(3) . . . . ?
N1 C9 C10 C11 168.1(3) . . . . ?
N1 C9 C10 C15 -11.3(4) . . . . ?
C15 C10 C11 C12 1.8(4) . . . . ?
C9 C10 C11 C12 -177.7(3) . . . . ?
C10 C11 C12 C13 -2.8(4) . . . . ?
C10 C11 C12 C16 176.6(9) . . . . ?
C10 C11 C12 Cl2 175.9(5) . . . . ?
C11 C12 C13 C14 1.7(4) . . . . ?
C16 C12 C13 C14 -177.8(9) . . . . ?
Cl2 C12 C13 C14 -177.1(5) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C11 C10 C15 C14 0.5(4) . . . . ?
C9 C10 C15 C14 179.9(2) . . . . ?
C11 C10 C15 N2 179.2(3) . . . . ?
C9 C10 C15 N2 -1.4(4) . . . . ?
C13 C14 C15 C10 -1.6(4) . . . . ?
C13 C14 C15 N2 179.6(3) . . . . ?
C8 N2 C15 C10 -19.3(3) . . . . ?
C7 N2 C15 C10 101.4(3) . . . . ?
C8 N2 C15 C14 159.4(2) . . . . ?
C7 N2 C15 C14 -79.9(3) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 986735'
#######################################################################
#
#                 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_COCR
# (-)-1/(+/-)-3

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16.23 H15.68 Br0.77 N2, C15 H12 Br1.96 N2'
_chemical_formula_sum            'C31.23 H27.68 Br2.74 N4'
_chemical_formula_weight         677.57

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.3568(4)
_cell_length_b                   10.4138(7)
_cell_length_c                   10.7105(7)
_cell_angle_alpha                82.302(4)
_cell_angle_beta                 75.969(3)
_cell_angle_gamma                82.058(3)
_cell_volume                     677.53(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7874
_cell_measurement_theta_min      3.229
_cell_measurement_theta_max      71.345

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             338.8
_exptl_transmission_factor_min   0.280
_exptl_transmission_factor_max   0.477
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    4.105
_shelx_estimated_absorpt_T_min   0.280
_shelx_estimated_absorpt_T_max   0.477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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 APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            21743
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.971
_diffrn_reflns_theta_max         30.183
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             7721
_reflns_number_gt                6901
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.979

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

All non-hydrogen atoms were located in a single difference density map and 
 refined with anisotropic displacement parameters.  The C-methyl and 
 C-Br distances were restrained to 1.51(2) and 1.85(2) angstroms,
 respectively.  The atomic displacement paramters for carbon atom C17B
 were idealized using appropriate restraints (RIGU, ISOR, and DELU). 

All CH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom (1.5 x Uiso for methyl H atoms).  

The final model used for refined included disorder of (S,S)-methyl
 and (S,S)-Br substituents. The occupancy factors associated with these 
 groups were fixed at unity and refined to give a 
 60:40 (Me:Br) ratio of components.  
;

_computing_data_collection       APEX2
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.067(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7721
_refine_ls_number_parameters     365
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1A Br 0.99847(6) 0.30315(5) 0.34798(4) 0.03130(19) Uani 1 1 d . . . . .
Br2A Br 0.48750(6) 0.08153(4) 1.22664(4) 0.02147(17) Uani 0.962(3) 1 d . . . .
.
N1A N 0.1881(5) 0.4731(3) 0.7517(3) 0.0161(7) Uani 1 1 d . . . . .
N2A N 0.4099(5) 0.5756(3) 0.8561(3) 0.0153(7) Uani 1 1 d . . . . .
C1A C 0.3812(6) 0.4384(4) 0.6557(4) 0.0141(7) Uani 1 1 d . . . . .
C2A C 0.3716(7) 0.3495(4) 0.5704(4) 0.0179(8) Uani 1 1 d . . . . .
H2A H 0.2378 0.3157 0.5762 0.021 Uiso 1 1 calc R U . . .
C3A C 0.5525(7) 0.3105(4) 0.4788(4) 0.0186(8) Uani 1 1 d . . . . .
H3A H 0.5453 0.2494 0.4219 0.022 Uiso 1 1 calc R U . . .
C4A C 0.7467(7) 0.3620(4) 0.4705(4) 0.0189(8) Uani 1 1 d . . . . .
C5A C 0.7603(7) 0.4516(4) 0.5523(4) 0.0160(8) Uani 1 1 d . . . . .
H5A H 0.8938 0.4866 0.5442 0.019 Uiso 1 1 calc R U . . .
C6A C 0.5770(6) 0.4898(4) 0.6463(4) 0.0136(7) Uani 1 1 d . . . . .
C7A C 0.5936(7) 0.5805(4) 0.7429(4) 0.0162(8) Uani 1 1 d . . . . .
H7A1 H 0.7319 0.5551 0.7714 0.019 Uiso 1 1 calc R U . . .
H7A2 H 0.5959 0.6709 0.7003 0.019 Uiso 1 1 calc R U . . .
C8A C 0.2080(7) 0.5877(4) 0.8095(5) 0.0205(9) Uani 1 1 d . . . . .
H8A1 H 0.0812 0.6019 0.8829 0.025 Uiso 1 1 calc R U . . .
H8A2 H 0.2056 0.6649 0.7447 0.025 Uiso 1 1 calc R U . . .
C9A C 0.1457(7) 0.3658(4) 0.8568(4) 0.0184(8) Uani 1 1 d . . . . .
H9A1 H 0.1655 0.2821 0.8189 0.022 Uiso 1 1 calc R U . . .
H9A2 H -0.0073 0.3797 0.9064 0.022 Uiso 1 1 calc R U . . .
C10A C 0.2973(7) 0.3584(4) 0.9472(4) 0.0147(7) Uani 1 1 d . . . . .
C11A C 0.3168(7) 0.2462(4) 1.0342(4) 0.0170(8) Uani 1 1 d . . . . .
H11A H 0.2288 0.1783 1.0390 0.020 Uiso 1 1 calc R U . . .
C12A C 0.4638(7) 0.2340(4) 1.1131(4) 0.0152(8) Uani 1 1 d . . . . .
C13A C 0.5943(6) 0.3323(4) 1.1067(4) 0.0158(8) Uani 1 1 d . . . . .
H13A H 0.6967 0.3232 1.1596 0.019 Uiso 1 1 calc R U . . .
C14A C 0.5735(7) 0.4441(4) 1.0220(4) 0.0151(8) Uani 1 1 d . . . . .
H14A H 0.6602 0.5124 1.0186 0.018 Uiso 1 1 calc R U . . .
C15A C 0.4269(6) 0.4572(4) 0.9418(4) 0.0133(7) Uani 1 1 d . . . . .
Br1B Br 0.2531(3) -0.06029(18) 1.63538(16) 0.0232(4) Uani 0.387(3) 1 d D . P A
1
Br2B Br 0.7739(5) 0.1660(3) 0.7493(3) 0.0201(5) Uani 0.387(3) 1 d D . P A 1
N1B N 1.0561(6) -0.2229(4) 1.2293(4) 0.0177(7) Uani 1 1 d . . . . .
N2B N 0.8379(6) -0.3251(3) 1.1215(4) 0.0158(7) Uani 1 1 d . . . . .
C1B C 0.8622(6) -0.1907(4) 1.3260(4) 0.0155(8) Uani 1 1 d . . . . .
C2B C 0.8699(7) -0.1041(4) 1.4112(4) 0.0192(8) Uani 1 1 d . . . . .
H2B H 1.0031 -0.0701 1.4063 0.023 Uiso 1 1 calc R U . . .
C3B C 0.6869(8) -0.0661(4) 1.5036(4) 0.0217(8) Uani 1 1 d . U . . .
H3B H 0.6945 -0.0059 1.5612 0.026 Uiso 1 1 calc R U . . .
C4B C 0.4901(7) -0.1166(4) 1.5122(4) 0.0210(8) Uani 1 1 d D U . . .
C5B C 0.4833(7) -0.2059(4) 1.4286(4) 0.0180(7) Uani 1 1 d . U . . .
H5B H 0.3515 -0.2428 1.4361 0.022 Uiso 1 1 calc R U . . .
C6B C 0.6664(7) -0.2425(4) 1.3336(4) 0.0157(8) Uani 1 1 d . . . . .
C7B C 0.6511(7) -0.3302(4) 1.2353(4) 0.0170(8) Uani 1 1 d . . . . .
H7B1 H 0.6469 -0.4211 1.2765 0.020 Uiso 1 1 calc R U . . .
H7B2 H 0.5136 -0.3034 1.2062 0.020 Uiso 1 1 calc R U . . .
C8B C 1.0383(7) -0.3384(5) 1.1692(4) 0.0207(9) Uani 1 1 d . . . . .
H8B1 H 1.1661 -0.3519 1.0963 0.025 Uiso 1 1 calc R U . . .
H8B2 H 1.0397 -0.4161 1.2335 0.025 Uiso 1 1 calc R U . . .
C9B C 1.0994(7) -0.1154(4) 1.1258(4) 0.0182(8) Uani 1 1 d . . . . .
H9B1 H 1.2535 -0.1285 1.0778 0.022 Uiso 1 1 calc R U . . .
H9B2 H 1.0774 -0.0322 1.1648 0.022 Uiso 1 1 calc R U . . .
C10B C 0.9511(6) -0.1066(4) 1.0318(4) 0.0149(8) Uani 1 1 d . . . . .
C11B C 0.9346(7) 0.0031(4) 0.9445(4) 0.0183(8) Uani 1 1 d . . . . .
H11B H 1.0262 0.0694 0.9388 0.022 Uiso 1 1 calc R U . . .
C12B C 0.7881(7) 0.0187(4) 0.8654(4) 0.0179(8) Uani 1 1 d D . . . .
C13B C 0.6568(7) -0.0805(4) 0.8721(4) 0.0163(8) Uani 1 1 d . . . . .
H13B H 0.5550 -0.0714 0.8187 0.020 Uiso 1 1 calc R U . . .
C14B C 0.6755(7) -0.1922(4) 0.9568(4) 0.0166(8) Uani 1 1 d . . . . .
H14B H 0.5869 -0.2596 0.9601 0.020 Uiso 1 1 calc R U . . .
C15B C 0.8220(6) -0.2076(4) 1.0374(4) 0.0139(7) Uani 1 1 d . . . . .
C16B C 0.771(5) 0.1412(16) 0.7733(19) 0.024(4) Uani 0.613(3) 1 d D . P A 2
H16A H 0.9025 0.1418 0.7032 0.036 Uiso 0.613(3) 1 calc R U P A 2
H16B H 0.7557 0.2178 0.8202 0.036 Uiso 0.613(3) 1 calc R U P A 2
H16C H 0.6428 0.1433 0.7369 0.036 Uiso 0.613(3) 1 calc R U P A 2
C17B C 0.279(2) -0.0791(16) 1.6093(13) 0.031(2) Uani 0.613(3) 1 d D U P A 2
H17A H 0.1725 -0.1388 1.6104 0.047 Uiso 0.613(3) 1 calc R U P A 2
H17B H 0.2214 0.0103 1.5843 0.047 Uiso 0.613(3) 1 calc R U P A 2
H17C H 0.3088 -0.0845 1.6957 0.047 Uiso 0.613(3) 1 calc R U P A 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
Br1A C4A 1.893(4) . ?
Br2A C12A 1.878(4) . ?
N1A C1A 1.435(5) . ?
N1A C8A 1.450(6) . ?
N1A C9A 1.479(5) . ?
N2A C15A 1.442(5) . ?
N2A C7A 1.466(5) . ?
N2A C8A 1.470(5) . ?
C1A C6A 1.398(5) . ?
C1A C2A 1.401(6) . ?
C2A C3A 1.372(6) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.392(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.386(6) . ?
C5A C6A 1.393(6) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.522(6) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C10A 1.511(5) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C15A 1.392(5) . ?
C10A C11A 1.404(6) . ?
C11A C12A 1.387(6) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.389(6) . ?
C13A C14A 1.388(5) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.395(5) . ?
C14A H14A 0.9500 . ?
Br1B C4B 1.831(5) . ?
Br2B C12B 1.847(5) . ?
N1B C1B 1.437(5) . ?
N1B C8B 1.467(6) . ?
N1B C9B 1.470(6) . ?
N2B C15B 1.426(5) . ?
N2B C8B 1.467(5) . ?
N2B C7B 1.482(6) . ?
C1B C2B 1.379(6) . ?
C1B C6B 1.404(5) . ?
C2B C3B 1.382(6) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.401(6) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.387(6) . ?
C4B C17B 1.522(10) . ?
C5B C6B 1.393(6) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.512(6) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B C10B 1.524(5) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B C11B 1.385(6) . ?
C10B C15B 1.408(6) . ?
C11B C12B 1.384(6) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.400(6) . ?
C12B C16B 1.513(11) . ?
C13B C14B 1.386(6) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.396(6) . ?
C14B H14B 0.9500 . ?
C16B H16A 0.9800 . ?
C16B H16B 0.9800 . ?
C16B H16C 0.9800 . ?
C17B H17A 0.9800 . ?
C17B H17B 0.9800 . ?
C17B H17C 0.9800 . ?

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
C1A N1A C8A 111.4(3) . . ?
C1A N1A C9A 111.0(3) . . ?
C8A N1A C9A 107.7(3) . . ?
C15A N2A C7A 112.6(3) . . ?
C15A N2A C8A 110.2(3) . . ?
C7A N2A C8A 107.9(3) . . ?
C6A C1A C2A 119.7(4) . . ?
C6A C1A N1A 121.8(4) . . ?
C2A C1A N1A 118.5(3) . . ?
C3A C2A C1A 121.0(4) . . ?
C3A C2A H2A 119.5 . . ?
C1A C2A H2A 119.5 . . ?
C2A C3A C4A 118.8(4) . . ?
C2A C3A H3A 120.6 . . ?
C4A C3A H3A 120.6 . . ?
C5A C4A C3A 121.4(4) . . ?
C5A C4A Br1A 119.9(3) . . ?
C3A C4A Br1A 118.7(3) . . ?
C4A C5A C6A 119.6(4) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
C5A C6A C1A 119.4(4) . . ?
C5A C6A C7A 120.2(4) . . ?
C1A C6A C7A 120.3(4) . . ?
N2A C7A C6A 111.4(3) . . ?
N2A C7A H7A1 109.3 . . ?
C6A C7A H7A1 109.3 . . ?
N2A C7A H7A2 109.3 . . ?
C6A C7A H7A2 109.3 . . ?
H7A1 C7A H7A2 108.0 . . ?
N1A C8A N2A 112.3(3) . . ?
N1A C8A H8A1 109.1 . . ?
N2A C8A H8A1 109.1 . . ?
N1A C8A H8A2 109.1 . . ?
N2A C8A H8A2 109.1 . . ?
H8A1 C8A H8A2 107.9 . . ?
N1A C9A C10A 111.3(3) . . ?
N1A C9A H9A1 109.4 . . ?
C10A C9A H9A1 109.4 . . ?
N1A C9A H9A2 109.4 . . ?
C10A C9A H9A2 109.4 . . ?
H9A1 C9A H9A2 108.0 . . ?
C15A C10A C11A 119.0(4) . . ?
C15A C10A C9A 121.6(4) . . ?
C11A C10A C9A 119.4(4) . . ?
C12A C11A C10A 120.5(4) . . ?
C12A C11A H11A 119.8 . . ?
C10A C11A H11A 119.8 . . ?
C11A C12A C13A 120.4(4) . . ?
C11A C12A Br2A 119.1(3) . . ?
C13A C12A Br2A 120.4(3) . . ?
C14A C13A C12A 119.3(3) . . ?
C14A C13A H13A 120.3 . . ?
C12A C13A H13A 120.3 . . ?
C13A C14A C15A 120.8(4) . . ?
C13A C14A H14A 119.6 . . ?
C15A C14A H14A 119.6 . . ?
C10A C15A C14A 120.0(4) . . ?
C10A C15A N2A 121.2(3) . . ?
C14A C15A N2A 118.8(3) . . ?
C1B N1B C8B 111.2(3) . . ?
C1B N1B C9B 111.8(3) . . ?
C8B N1B C9B 107.8(3) . . ?
C15B N2B C8B 110.5(3) . . ?
C15B N2B C7B 112.5(3) . . ?
C8B N2B C7B 107.8(3) . . ?
C2B C1B C6B 119.8(4) . . ?
C2B C1B N1B 118.4(3) . . ?
C6B C1B N1B 121.8(4) . . ?
C1B C2B C3B 121.1(4) . . ?
C1B C2B H2B 119.5 . . ?
C3B C2B H2B 119.5 . . ?
C2B C3B C4B 119.8(4) . . ?
C2B C3B H3B 120.1 . . ?
C4B C3B H3B 120.1 . . ?
C5B C4B C3B 119.2(4) . . ?
C5B C4B C17B 117.2(7) . . ?
C3B C4B C17B 123.6(7) . . ?
C5B C4B Br1B 123.3(3) . . ?
C3B C4B Br1B 117.5(3) . . ?
C4B C5B C6B 121.1(4) . . ?
C4B C5B H5B 119.5 . . ?
C6B C5B H5B 119.5 . . ?
C5B C6B C1B 119.0(4) . . ?
C5B C6B C7B 120.5(4) . . ?
C1B C6B C7B 120.4(4) . . ?
N2B C7B C6B 111.9(3) . . ?
N2B C7B H7B1 109.2 . . ?
C6B C7B H7B1 109.2 . . ?
N2B C7B H7B2 109.2 . . ?
C6B C7B H7B2 109.2 . . ?
H7B1 C7B H7B2 107.9 . . ?
N2B C8B N1B 111.8(3) . . ?
N2B C8B H8B1 109.3 . . ?
N1B C8B H8B1 109.3 . . ?
N2B C8B H8B2 109.3 . . ?
N1B C8B H8B2 109.3 . . ?
H8B1 C8B H8B2 107.9 . . ?
N1B C9B C10B 112.0(3) . . ?
N1B C9B H9B1 109.2 . . ?
C10B C9B H9B1 109.2 . . ?
N1B C9B H9B2 109.2 . . ?
C10B C9B H9B2 109.2 . . ?
H9B1 C9B H9B2 107.9 . . ?
C11B C10B C15B 119.5(4) . . ?
C11B C10B C9B 120.5(4) . . ?
C15B C10B C9B 120.0(4) . . ?
C12B C11B C10B 121.8(4) . . ?
C12B C11B H11B 119.1 . . ?
C10B C11B H11B 119.1 . . ?
C11B C12B C13B 118.9(4) . . ?
C11B C12B C16B 120.4(10) . . ?
C13B C12B C16B 120.7(10) . . ?
C11B C12B Br2B 120.2(3) . . ?
C13B C12B Br2B 120.9(3) . . ?
C14B C13B C12B 119.9(4) . . ?
C14B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C13B C14B C15B 121.2(4) . . ?
C13B C14B H14B 119.4 . . ?
C15B C14B H14B 119.4 . . ?
C14B C15B C10B 118.7(4) . . ?
C14B C15B N2B 119.2(3) . . ?
C10B C15B N2B 122.1(3) . . ?
C12B C16B H16A 109.5 . . ?
C12B C16B H16B 109.5 . . ?
H16A C16B H16B 109.5 . . ?
C12B C16B H16C 109.5 . . ?
H16A C16B H16C 109.5 . . ?
H16B C16B H16C 109.5 . . ?
C4B C17B H17A 109.5 . . ?
C4B C17B H17B 109.5 . . ?
H17A C17B H17B 109.5 . . ?
C4B C17B H17C 109.5 . . ?
H17A C17B H17C 109.5 . . ?
H17B C17B H17C 109.5 . . ?

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
C8A N1A C1A C6A 15.0(5) . . . . ?
C9A N1A C1A C6A -105.0(4) . . . . ?
C8A N1A C1A C2A -165.7(3) . . . . ?
C9A N1A C1A C2A 74.3(4) . . . . ?
C6A C1A C2A C3A 0.9(6) . . . . ?
N1A C1A C2A C3A -178.4(4) . . . . ?
C1A C2A C3A C4A -0.7(6) . . . . ?
C2A C3A C4A C5A -0.2(6) . . . . ?
C2A C3A C4A Br1A 177.8(3) . . . . ?
C3A C4A C5A C6A 1.0(6) . . . . ?
Br1A C4A C5A C6A -176.9(3) . . . . ?
C4A C5A C6A C1A -0.8(6) . . . . ?
C4A C5A C6A C7A 175.6(4) . . . . ?
C2A C1A C6A C5A -0.1(6) . . . . ?
N1A C1A C6A C5A 179.2(3) . . . . ?
C2A C1A C6A C7A -176.6(4) . . . . ?
N1A C1A C6A C7A 2.8(6) . . . . ?
C15A N2A C7A C6A 74.0(4) . . . . ?
C8A N2A C7A C6A -47.9(4) . . . . ?
C5A C6A C7A N2A -161.7(3) . . . . ?
C1A C6A C7A N2A 14.7(5) . . . . ?
C1A N1A C8A N2A -51.4(5) . . . . ?
C9A N1A C8A N2A 70.5(4) . . . . ?
C15A N2A C8A N1A -53.6(5) . . . . ?
C7A N2A C8A N1A 69.7(4) . . . . ?
C1A N1A C9A C10A 76.2(4) . . . . ?
C8A N1A C9A C10A -45.9(4) . . . . ?
N1A C9A C10A C15A 11.2(6) . . . . ?
N1A C9A C10A C11A -165.4(4) . . . . ?
C15A C10A C11A C12A -0.3(6) . . . . ?
C9A C10A C11A C12A 176.4(4) . . . . ?
C10A C11A C12A C13A -0.3(6) . . . . ?
C10A C11A C12A Br2A -179.2(3) . . . . ?
C11A C12A C13A C14A 1.1(6) . . . . ?
Br2A C12A C13A C14A -180.0(3) . . . . ?
C12A C13A C14A C15A -1.4(6) . . . . ?
C11A C10A C15A C14A 0.0(6) . . . . ?
C9A C10A C15A C14A -176.6(4) . . . . ?
C11A C10A C15A N2A -178.7(4) . . . . ?
C9A C10A C15A N2A 4.7(6) . . . . ?
C13A C14A C15A C10A 0.8(6) . . . . ?
C13A C14A C15A N2A 179.5(4) . . . . ?
C7A N2A C15A C10A -105.3(4) . . . . ?
C8A N2A C15A C10A 15.3(5) . . . . ?
C7A N2A C15A C14A 76.0(4) . . . . ?
C8A N2A C15A C14A -163.4(4) . . . . ?
C8B N1B C1B C2B 165.7(4) . . . . ?
C9B N1B C1B C2B -73.8(4) . . . . ?
C8B N1B C1B C6B -15.8(5) . . . . ?
C9B N1B C1B C6B 104.7(4) . . . . ?
C6B C1B C2B C3B -0.7(6) . . . . ?
N1B C1B C2B C3B 177.9(4) . . . . ?
C1B C2B C3B C4B 0.5(6) . . . . ?
C2B C3B C4B C5B 0.9(6) . . . . ?
C2B C3B C4B C17B -179.0(8) . . . . ?
C2B C3B C4B Br1B -179.1(3) . . . . ?
C3B C4B C5B C6B -2.2(6) . . . . ?
C17B C4B C5B C6B 177.8(8) . . . . ?
Br1B C4B C5B C6B 177.9(3) . . . . ?
C4B C5B C6B C1B 2.0(6) . . . . ?
C4B C5B C6B C7B -174.3(4) . . . . ?
C2B C1B C6B C5B -0.6(6) . . . . ?
N1B C1B C6B C5B -179.1(3) . . . . ?
C2B C1B C6B C7B 175.8(4) . . . . ?
N1B C1B C6B C7B -2.7(6) . . . . ?
C15B N2B C7B C6B -74.8(4) . . . . ?
C8B N2B C7B C6B 47.3(4) . . . . ?
C5B C6B C7B N2B 162.5(3) . . . . ?
C1B C6B C7B N2B -13.8(5) . . . . ?
C15B N2B C8B N1B 53.8(5) . . . . ?
C7B N2B C8B N1B -69.5(4) . . . . ?
C1B N1B C8B N2B 52.3(5) . . . . ?
C9B N1B C8B N2B -70.5(4) . . . . ?
C1B N1B C9B C10B -76.9(4) . . . . ?
C8B N1B C9B C10B 45.5(4) . . . . ?
N1B C9B C10B C11B 166.5(4) . . . . ?
N1B C9B C10B C15B -10.5(5) . . . . ?
C15B C10B C11B C12B 2.4(6) . . . . ?
C9B C10B C11B C12B -174.6(4) . . . . ?
C10B C11B C12B C13B -1.4(7) . . . . ?
C10B C11B C12B C16B 178.6(12) . . . . ?
C10B C11B C12B Br2B -179.4(4) . . . . ?
C11B C12B C13B C14B -0.2(6) . . . . ?
C16B C12B C13B C14B 179.8(12) . . . . ?
Br2B C12B C13B C14B 177.8(4) . . . . ?
C12B C13B C14B C15B 0.7(6) . . . . ?
C13B C14B C15B C10B 0.3(6) . . . . ?
C13B C14B C15B N2B -179.0(4) . . . . ?
C11B C10B C15B C14B -1.9(6) . . . . ?
C9B C10B C15B C14B 175.1(4) . . . . ?
C11B C10B C15B N2B 177.5(4) . . . . ?
C9B C10B C15B N2B -5.5(6) . . . . ?
C8B N2B C15B C14B 163.9(4) . . . . ?
C7B N2B C15B C14B -75.5(4) . . . . ?
C8B N2B C15B C10B -15.4(5) . . . . ?
C7B N2B C15B C10B 105.2(4) . . . . ?

_refine_diff_density_max         0.807
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.094

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 986736'
#######################################################################
#
#                 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_TRCL01
# (rac)-2-I 

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Cl2 N2'
_chemical_formula_sum            'C15 H12 Cl2 N2'
_chemical_formula_weight         291.17

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8192(2)
_cell_length_b                   9.8988(3)
_cell_length_c                   18.2061(5)
_cell_angle_alpha                78.154(2)
_cell_angle_beta                 79.977(2)
_cell_angle_gamma                72.633(1)
_cell_volume                     1306.65(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7520
_cell_measurement_theta_min      3.198
_cell_measurement_theta_max      72.301

_exptl_crystal_description       'transparent needle'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   0.482
_exptl_transmission_factor_max   0.944
_exptl_crystal_size_max          .39
_exptl_crystal_size_mid          .21
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    0.482
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            33398
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.151
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4777
_reflns_number_gt                4228
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.


All non-hydrogen atoms were located in a single difference density map and 
 refined with anisotropic displacement parameters.  All CH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom (1.5 x Uiso for methyl H atoms). 
;

_computing_data_collection       APEX2
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0274P)²+0.5597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4777
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0623
_refine_ls_wR_factor_gt          0.0591
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.51556(5) -0.18858(4) 0.98434(2) 0.03279(10) Uani 1 1 d . . . . .
Cl2A Cl 1.17763(5) -0.27427(4) 0.50252(2) 0.03154(10) Uani 1 1 d . . . . .
N1A N 0.52084(16) -0.46884(12) 0.72277(7) 0.0239(3) Uani 1 1 d . . . . .
N2A N 0.42410(16) -0.23373(13) 0.64686(7) 0.0252(3) Uani 1 1 d . . . . .
C1A C 0.52212(18) -0.39872(15) 0.78475(8) 0.0217(3) Uani 1 1 d . . . . .
C2A C 0.59926(19) -0.48026(15) 0.84867(8) 0.0236(3) Uani 1 1 d . . . . .
H2A H 0.6529 -0.5803 0.8501 0.028 Uiso 1 1 calc R U . . .
C3A C 0.59904(19) -0.41785(16) 0.91013(8) 0.0253(3) Uani 1 1 d . . . . .
H3A H 0.6526 -0.4738 0.9535 0.030 Uiso 1 1 calc R U . . .
C4A C 0.51869(19) -0.27158(16) 0.90699(8) 0.0259(3) Uani 1 1 d . . . . .
C5A C 0.44308(18) -0.18852(15) 0.84428(8) 0.0250(3) Uani 1 1 d . . . . .
H5A H 0.3895 -0.0886 0.8433 0.030 Uiso 1 1 calc R U . . .
C6A C 0.44508(18) -0.25095(15) 0.78219(8) 0.0229(3) Uani 1 1 d . . . . .
C7A C 0.3684(2) -0.15832(15) 0.71243(8) 0.0269(3) Uani 1 1 d . . . . .
H7A1 H 0.2349 -0.1296 0.7223 0.032 Uiso 1 1 calc R U . . .
H7A2 H 0.4096 -0.0701 0.7007 0.032 Uiso 1 1 calc R U . . .
C8A C 0.3934(2) -0.37558(16) 0.67120(9) 0.0272(3) Uani 1 1 d . . . . .
H8A1 H 0.4055 -0.4210 0.6262 0.033 Uiso 1 1 calc R U . . .
H8A2 H 0.2687 -0.3650 0.6968 0.033 Uiso 1 1 calc R U . . .
C9A C 0.69831(19) -0.50587(14) 0.67728(8) 0.0235(3) Uani 1 1 d . . . . .
H9A1 H 0.7002 -0.5776 0.6462 0.028 Uiso 1 1 calc R U . . .
H9A2 H 0.7927 -0.5501 0.7115 0.028 Uiso 1 1 calc R U . . .
C10A C 0.74155(19) -0.37578(14) 0.62581(8) 0.0213(3) Uani 1 1 d . . . . .
C11A C 0.91606(19) -0.38403(15) 0.59028(8) 0.0240(3) Uani 1 1 d . . . . .
H11A H 1.0064 -0.4732 0.5947 0.029 Uiso 1 1 calc R U . . .
C12A C 0.95754(19) -0.26260(16) 0.54864(8) 0.0250(3) Uani 1 1 d . . . . .
C13A C 0.8285(2) -0.13063(16) 0.54177(8) 0.0267(3) Uani 1 1 d . . . . .
H13A H 0.8598 -0.0470 0.5144 0.032 Uiso 1 1 calc R U . . .
C14A C 0.6546(2) -0.12290(15) 0.57522(8) 0.0250(3) Uani 1 1 d . . . . .
H14A H 0.5652 -0.0333 0.5704 0.030 Uiso 1 1 calc R U . . .
C15A C 0.60802(19) -0.24492(14) 0.61612(8) 0.0215(3) Uani 1 1 d . . . . .
Cl1B Cl 0.61018(5) -0.29305(4) 0.40412(2) 0.03035(10) Uani 1 1 d . . . . .
Cl2B Cl 0.82894(5) 0.54341(3) 0.08167(2) 0.02474(9) Uani 1 1 d . . . . .
N1B N 1.15768(16) -0.14230(12) 0.15410(7) 0.0247(3) Uani 1 1 d . . . . .
N2B N 1.25297(16) -0.01734(12) 0.23423(7) 0.0230(3) Uani 1 1 d . . . . .
C1B C 1.02250(19) -0.17102(14) 0.21450(8) 0.0221(3) Uani 1 1 d . . . . .
C2B C 0.8923(2) -0.22941(15) 0.20022(8) 0.0260(3) Uani 1 1 d . . . . .
H2B H 0.8906 -0.2432 0.1503 0.031 Uiso 1 1 calc R U . . .
C3B C 0.7656(2) -0.26760(15) 0.25724(9) 0.0271(3) Uani 1 1 d . . . . .
H3B H 0.6779 -0.3079 0.2470 0.033 Uiso 1 1 calc R U . . .
C4B C 0.76921(19) -0.24578(14) 0.32963(8) 0.0248(3) Uani 1 1 d . . . . .
C5B C 0.89491(19) -0.18628(14) 0.34519(8) 0.0229(3) Uani 1 1 d . . . . .
H5B H 0.8945 -0.1719 0.3952 0.027 Uiso 1 1 calc R U . . .
C6B C 1.02233(18) -0.14737(14) 0.28774(8) 0.0214(3) Uani 1 1 d . . . . .
C7B C 1.15879(19) -0.07897(15) 0.30406(8) 0.0240(3) Uani 1 1 d . . . . .
H7B1 H 1.0959 -0.0026 0.3347 0.029 Uiso 1 1 calc R U . . .
H7B2 H 1.2483 -0.1523 0.3340 0.029 Uiso 1 1 calc R U . . .
C8B C 1.31066(19) -0.12431(15) 0.18370(9) 0.0266(3) Uani 1 1 d . . . . .
H8B1 H 1.3750 -0.2175 0.2115 0.032 Uiso 1 1 calc R U . . .
H8B2 H 1.3960 -0.0944 0.1410 0.032 Uiso 1 1 calc R U . . .
C9B C 1.0900(2) -0.01170(15) 0.10001(8) 0.0251(3) Uani 1 1 d . . . . .
H9B1 H 0.9717 -0.0112 0.0874 0.030 Uiso 1 1 calc R U . . .
H9B2 H 1.1749 -0.0124 0.0528 0.030 Uiso 1 1 calc R U . . .
C10B C 1.06945(18) 0.12295(14) 0.13205(8) 0.0211(3) Uani 1 1 d . . . . .
C11B C 0.97443(18) 0.25595(15) 0.09631(8) 0.0219(3) Uani 1 1 d . . . . .
H11B H 0.9275 0.2632 0.0505 0.026 Uiso 1 1 calc R U . . .
C12B C 0.94868(18) 0.37712(15) 0.12779(8) 0.0220(3) Uani 1 1 d . . . . .
C13B C 1.01400(18) 0.36937(15) 0.19492(8) 0.0220(3) Uani 1 1 d . . . . .
H13B H 0.9924 0.4532 0.2167 0.026 Uiso 1 1 calc R U . . .
C14B C 1.11101(18) 0.23806(15) 0.22984(8) 0.0218(3) Uani 1 1 d . . . . .
H14B H 1.1568 0.2317 0.2758 0.026 Uiso 1 1 calc R U . . .
C15B C 1.14224(18) 0.11482(14) 0.19815(8) 0.0205(3) 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
Cl1A C4A 1.7634(15) . ?
Cl2A C12A 1.7602(15) . ?
N1A C1A 1.4439(18) . ?
N1A C8A 1.4655(18) . ?
N1A C9A 1.4721(18) . ?
N2A C15A 1.4297(18) . ?
N2A C8A 1.4610(19) . ?
N2A C7A 1.4706(19) . ?
C1A C2A 1.392(2) . ?
C1A C6A 1.4001(19) . ?
C2A C3A 1.384(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.389(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.374(2) . ?
C5A C6A 1.391(2) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.508(2) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C10A 1.5183(19) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C11A 1.391(2) . ?
C10A C15A 1.4007(19) . ?
C11A C12A 1.378(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.389(2) . ?
C13A C14A 1.376(2) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.395(2) . ?
C14A H14A 0.9500 . ?
Cl1B C4B 1.7619(15) . ?
Cl2B C12B 1.7542(14) . ?
N1B C1B 1.4331(19) . ?
N1B C8B 1.4643(19) . ?
N1B C9B 1.4735(18) . ?
N2B C15B 1.4359(18) . ?
N2B C8B 1.4633(18) . ?
N2B C7B 1.4678(18) . ?
C1B C2B 1.394(2) . ?
C1B C6B 1.4000(19) . ?
C2B C3B 1.381(2) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.385(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.380(2) . ?
C5B C6B 1.391(2) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.5196(19) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B C10B 1.5169(19) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B C11B 1.393(2) . ?
C10B C15B 1.3964(19) . ?
C11B C12B 1.380(2) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.384(2) . ?
C13B C14B 1.382(2) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3939(19) . ?
C14B H14B 0.9500 . ?

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
C1A N1A C8A 110.75(11) . . ?
C1A N1A C9A 112.70(11) . . ?
C8A N1A C9A 106.75(11) . . ?
C15A N2A C8A 110.96(11) . . ?
C15A N2A C7A 112.79(11) . . ?
C8A N2A C7A 107.47(12) . . ?
C2A C1A C6A 119.50(13) . . ?
C2A C1A N1A 119.21(12) . . ?
C6A C1A N1A 121.29(12) . . ?
C3A C2A C1A 121.03(13) . . ?
C3A C2A H2A 119.5 . . ?
C1A C2A H2A 119.5 . . ?
C2A C3A C4A 118.51(14) . . ?
C2A C3A H3A 120.7 . . ?
C4A C3A H3A 120.7 . . ?
C5A C4A C3A 121.56(13) . . ?
C5A C4A Cl1A 118.70(11) . . ?
C3A C4A Cl1A 119.73(12) . . ?
C4A C5A C6A 119.92(13) . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A C1A 119.46(13) . . ?
C5A C6A C7A 119.66(13) . . ?
C1A C6A C7A 120.87(13) . . ?
N2A C7A C6A 111.75(11) . . ?
N2A C7A H7A1 109.3 . . ?
C6A C7A H7A1 109.3 . . ?
N2A C7A H7A2 109.3 . . ?
C6A C7A H7A2 109.3 . . ?
H7A1 C7A H7A2 107.9 . . ?
N2A C8A N1A 112.07(11) . . ?
N2A C8A H8A1 109.2 . . ?
N1A C8A H8A1 109.2 . . ?
N2A C8A H8A2 109.2 . . ?
N1A C8A H8A2 109.2 . . ?
H8A1 C8A H8A2 107.9 . . ?
N1A C9A C10A 112.25(11) . . ?
N1A C9A H9A1 109.2 . . ?
C10A C9A H9A1 109.2 . . ?
N1A C9A H9A2 109.2 . . ?
C10A C9A H9A2 109.2 . . ?
H9A1 C9A H9A2 107.9 . . ?
C11A C10A C15A 119.41(13) . . ?
C11A C10A C9A 120.21(12) . . ?
C15A C10A C9A 120.33(13) . . ?
C12A C11A C10A 119.82(13) . . ?
C12A C11A H11A 120.1 . . ?
C10A C11A H11A 120.1 . . ?
C11A C12A C13A 121.29(14) . . ?
C11A C12A Cl2A 119.62(11) . . ?
C13A C12A Cl2A 119.09(11) . . ?
C14A C13A C12A 118.99(13) . . ?
C14A C13A H13A 120.5 . . ?
C12A C13A H13A 120.5 . . ?
C13A C14A C15A 120.84(13) . . ?
C13A C14A H14A 119.6 . . ?
C15A C14A H14A 119.6 . . ?
C14A C15A C10A 119.51(13) . . ?
C14A C15A N2A 119.09(12) . . ?
C10A C15A N2A 121.39(13) . . ?
C1B N1B C8B 110.69(11) . . ?
C1B N1B C9B 112.99(11) . . ?
C8B N1B C9B 107.47(11) . . ?
C15B N2B C8B 110.58(11) . . ?
C15B N2B C7B 112.58(11) . . ?
C8B N2B C7B 107.57(11) . . ?
C2B C1B C6B 119.41(13) . . ?
C2B C1B N1B 118.76(13) . . ?
C6B C1B N1B 121.79(13) . . ?
C3B C2B C1B 121.34(14) . . ?
C3B C2B H2B 119.3 . . ?
C1B C2B H2B 119.3 . . ?
C2B C3B C4B 118.52(13) . . ?
C2B C3B H3B 120.7 . . ?
C4B C3B H3B 120.7 . . ?
C5B C4B C3B 121.39(14) . . ?
C5B C4B Cl1B 118.56(11) . . ?
C3B C4B Cl1B 120.05(11) . . ?
C4B C5B C6B 120.15(13) . . ?
C4B C5B H5B 119.9 . . ?
C6B C5B H5B 119.9 . . ?
C5B C6B C1B 119.18(13) . . ?
C5B C6B C7B 120.48(12) . . ?
C1B C6B C7B 120.34(13) . . ?
N2B C7B C6B 111.76(11) . . ?
N2B C7B H7B1 109.3 . . ?
C6B C7B H7B1 109.3 . . ?
N2B C7B H7B2 109.3 . . ?
C6B C7B H7B2 109.3 . . ?
H7B1 C7B H7B2 107.9 . . ?
N2B C8B N1B 111.90(11) . . ?
N2B C8B H8B1 109.2 . . ?
N1B C8B H8B1 109.2 . . ?
N2B C8B H8B2 109.2 . . ?
N1B C8B H8B2 109.2 . . ?
H8B1 C8B H8B2 107.9 . . ?
N1B C9B C10B 111.54(11) . . ?
N1B C9B H9B1 109.3 . . ?
C10B C9B H9B1 109.3 . . ?
N1B C9B H9B2 109.3 . . ?
C10B C9B H9B2 109.3 . . ?
H9B1 C9B H9B2 108.0 . . ?
C11B C10B C15B 119.37(13) . . ?
C11B C10B C9B 120.05(12) . . ?
C15B C10B C9B 120.56(12) . . ?
C12B C11B C10B 119.74(13) . . ?
C12B C11B H11B 120.1 . . ?
C10B C11B H11B 120.1 . . ?
C11B C12B C13B 121.32(13) . . ?
C11B C12B Cl2B 118.91(11) . . ?
C13B C12B Cl2B 119.78(11) . . ?
C14B C13B C12B 119.10(13) . . ?
C14B C13B H13B 120.4 . . ?
C12B C13B H13B 120.4 . . ?
C13B C14B C15B 120.55(13) . . ?
C13B C14B H14B 119.7 . . ?
C15B C14B H14B 119.7 . . ?
C14B C15B C10B 119.83(13) . . ?
C14B C15B N2B 118.31(12) . . ?
C10B C15B N2B 121.85(12) . . ?

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
C8A N1A C1A C2A 164.47(12) . . . . ?
C9A N1A C1A C2A -76.02(15) . . . . ?
C8A N1A C1A C6A -14.60(17) . . . . ?
C9A N1A C1A C6A 104.91(14) . . . . ?
C6A C1A C2A C3A 0.8(2) . . . . ?
N1A C1A C2A C3A -178.28(13) . . . . ?
C1A C2A C3A C4A 0.5(2) . . . . ?
C2A C3A C4A C5A -1.1(2) . . . . ?
C2A C3A C4A Cl1A 179.88(11) . . . . ?
C3A C4A C5A C6A 0.4(2) . . . . ?
Cl1A C4A C5A C6A 179.43(11) . . . . ?
C4A C5A C6A C1A 0.9(2) . . . . ?
C4A C5A C6A C7A -177.65(13) . . . . ?
C2A C1A C6A C5A -1.5(2) . . . . ?
N1A C1A C6A C5A 177.57(12) . . . . ?
C2A C1A C6A C7A 177.06(13) . . . . ?
N1A C1A C6A C7A -3.9(2) . . . . ?
C15A N2A C7A C6A -74.75(15) . . . . ?
C8A N2A C7A C6A 47.86(15) . . . . ?
C5A C6A C7A N2A 164.92(12) . . . . ?
C1A C6A C7A N2A -13.63(19) . . . . ?
C15A N2A C8A N1A 53.25(16) . . . . ?
C7A N2A C8A N1A -70.49(15) . . . . ?
C1A N1A C8A N2A 52.20(15) . . . . ?
C9A N1A C8A N2A -70.83(14) . . . . ?
C1A N1A C9A C10A -75.66(14) . . . . ?
C8A N1A C9A C10A 46.15(15) . . . . ?
N1A C9A C10A C11A 166.97(12) . . . . ?
N1A C9A C10A C15A -10.41(18) . . . . ?
C15A C10A C11A C12A 2.7(2) . . . . ?
C9A C10A C11A C12A -174.72(12) . . . . ?
C10A C11A C12A C13A 0.6(2) . . . . ?
C10A C11A C12A Cl2A -178.95(10) . . . . ?
C11A C12A C13A C14A -2.3(2) . . . . ?
Cl2A C12A C13A C14A 177.28(11) . . . . ?
C12A C13A C14A C15A 0.6(2) . . . . ?
C13A C14A C15A C10A 2.6(2) . . . . ?
C13A C14A C15A N2A -176.97(12) . . . . ?
C11A C10A C15A C14A -4.2(2) . . . . ?
C9A C10A C15A C14A 173.16(13) . . . . ?
C11A C10A C15A N2A 175.31(12) . . . . ?
C9A C10A C15A N2A -7.29(19) . . . . ?
C8A N2A C15A C14A 166.19(12) . . . . ?
C7A N2A C15A C14A -73.17(16) . . . . ?
C8A N2A C15A C10A -13.36(18) . . . . ?
C7A N2A C15A C10A 107.28(14) . . . . ?
C8B N1B C1B C2B -162.61(12) . . . . ?
C9B N1B C1B C2B 76.81(15) . . . . ?
C8B N1B C1B C6B 14.82(17) . . . . ?
C9B N1B C1B C6B -105.77(14) . . . . ?
C6B C1B C2B C3B -1.6(2) . . . . ?
N1B C1B C2B C3B 175.93(12) . . . . ?
C1B C2B C3B C4B 0.4(2) . . . . ?
C2B C3B C4B C5B 0.5(2) . . . . ?
C2B C3B C4B Cl1B -179.96(10) . . . . ?
C3B C4B C5B C6B -0.3(2) . . . . ?
Cl1B C4B C5B C6B -179.87(10) . . . . ?
C4B C5B C6B C1B -0.79(19) . . . . ?
C4B C5B C6B C7B 178.74(12) . . . . ?
C2B C1B C6B C5B 1.70(19) . . . . ?
N1B C1B C6B C5B -175.71(12) . . . . ?
C2B C1B C6B C7B -177.83(12) . . . . ?
N1B C1B C6B C7B 4.77(19) . . . . ?
C15B N2B C7B C6B 75.12(14) . . . . ?
C8B N2B C7B C6B -46.96(14) . . . . ?
C5B C6B C7B N2B -167.26(12) . . . . ?
C1B C6B C7B N2B 12.26(17) . . . . ?
C15B N2B C8B N1B -52.62(15) . . . . ?
C7B N2B C8B N1B 70.69(14) . . . . ?
C1B N1B C8B N2B -52.92(15) . . . . ?
C9B N1B C8B N2B 70.90(14) . . . . ?
C1B N1B C9B C10B 75.50(15) . . . . ?
C8B N1B C9B C10B -46.90(15) . . . . ?
N1B C9B C10B C11B -167.25(12) . . . . ?
N1B C9B C10B C15B 11.55(18) . . . . ?
C15B C10B C11B C12B -2.0(2) . . . . ?
C9B C10B C11B C12B 176.85(12) . . . . ?
C10B C11B C12B C13B -0.7(2) . . . . ?
C10B C11B C12B Cl2B 179.89(10) . . . . ?
C11B C12B C13B C14B 1.8(2) . . . . ?
Cl2B C12B C13B C14B -178.78(10) . . . . ?
C12B C13B C14B C15B -0.2(2) . . . . ?
C13B C14B C15B C10B -2.4(2) . . . . ?
C13B C14B C15B N2B 176.30(12) . . . . ?
C11B C10B C15B C14B 3.4(2) . . . . ?
C9B C10B C15B C14B -175.36(12) . . . . ?
C11B C10B C15B N2B -175.16(12) . . . . ?
C9B C10B C15B N2B 6.0(2) . . . . ?
C8B N2B C15B C14B -164.84(12) . . . . ?
C7B N2B C15B C14B 74.80(15) . . . . ?
C8B N2B C15B C10B 13.79(18) . . . . ?
C7B N2B C15B C10B -106.57(14) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 986737'
#######################################################################
#
#                 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_h07
# (+/-)-2-II

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Cl2 N2'
_chemical_formula_sum            'C15 H12 Cl2 N2'
_chemical_formula_weight         291.17

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.0853(5)
_cell_length_b                   13.6203(14)
_cell_length_c                   16.017(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.009(9)
_cell_angle_gamma                90
_cell_volume                     1326.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    46
_cell_measurement_theta_min      20.960
_cell_measurement_theta_max      45.011

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.475
_shelx_estimated_absorpt_T_min   0.703
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   'analytical face-indexed, Bruker Xscans'


_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 P4'
_diffrn_measurement_method       'θ/2θ\ scans'
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3429
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.545
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2423
_reflns_number_gt                1782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

All non-hydrogen atoms were located in sequential difference density
 maps and refined with anisotropic displacement parameters.  All
 CH hydrogen atoms were placed in calculated positions with
 Ueq = 1.2 x Uiso to the corresponding C atom. A portion of the
 molecule was modeled with two-part disorder- i.e., CL2 C14 C15 C13
 C12.  The occupancies of the two disordered sites were refined to 
 63:37.  The two C-Cl bonds were restrained to 1.75(1) angstroms
 (DFIX) and the two disordered fragments subjected to rigid 
 body restraints (RIGU).
 
;

_computing_data_collection       'Xscans (Bruker, 1999)'
_computing_cell_refinement       'Xscans (Bruker, 1999)'
_computing_data_reduction        
;
XPREP (Bruker, 2001) and XPREP (Bruker, 2001)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.1544P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2423
_refine_ls_number_parameters     236
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.009

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.20654(11) 0.05065(5) 0.42921(4) 0.0687(2) Uani 1 1 d . . . . .
Cl2 Cl -0.012(3) 0.0382(4) -0.1581(3) 0.1024(18) Uani 0.64(3) 1 d D U P A 1
N1 N -0.4330(3) 0.21182(12) 0.17707(11) 0.0446(4) Uani 1 1 d . . . . .
N2 N -0.1505(3) 0.31547(12) 0.12039(11) 0.0441(4) Uani 1 1 d . . . . .
C1 C -0.2753(3) 0.17623(14) 0.23842(12) 0.0387(5) Uani 1 1 d D . . . .
C2 C -0.3352(4) 0.09840(14) 0.28903(12) 0.0419(5) Uani 1 1 d D . . . .
H2 H -0.4752 0.0714 0.2825 0.050 Uiso 1 1 calc R U . . .
C3 C -0.1901(4) 0.06069(14) 0.34865(12) 0.0443(5) Uani 1 1 d D . . . .
H3 H -0.2308 0.0085 0.3822 0.053 Uiso 1 1 calc R U . . .
C4 C 0.0166(4) 0.10172(15) 0.35765(12) 0.0442(5) Uani 1 1 d D . . . .
C5 C 0.0790(4) 0.18033(14) 0.30915(12) 0.0440(5) Uani 1 1 d D . . . .
H5 H 0.2181 0.2078 0.3170 0.053 Uiso 1 1 calc R U . . .
C6 C -0.0670(3) 0.21819(14) 0.24861(12) 0.0388(5) Uani 1 1 d D . . . .
C7 C 0.0011(4) 0.30214(15) 0.19327(13) 0.0470(5) Uani 1 1 d . . . . .
H7A H 0.0060 0.3623 0.2257 0.056 Uiso 1 1 calc R U . . .
H7B H 0.1479 0.2897 0.1740 0.056 Uiso 1 1 calc R U . . .
C8 C -0.3749(4) 0.31066(15) 0.14964(14) 0.0497(6) Uani 1 1 d . . . . .
H8A H -0.4765 0.3309 0.1049 0.060 Uiso 1 1 calc R U . . .
H8B H -0.3898 0.3561 0.1957 0.060 Uiso 1 1 calc R U . . .
C9 C -0.4489(4) 0.14860(17) 0.10332(13) 0.0494(6) Uani 1 1 d . . . . .
H9A H -0.5919 0.1576 0.0757 0.059 Uiso 1 1 calc R U . A 1
H9B H -0.4374 0.0806 0.1208 0.059 Uiso 1 1 calc R U . A 1
C10 C -0.263(3) 0.1710(11) 0.0388(9) 0.040(3) Uani 0.64(3) 1 d . . P A 1
C11 C -0.1202(16) 0.2491(11) 0.0572(8) 0.036(2) Uani 0.64(3) 1 d . . P A 1
C12 C 0.056(3) 0.2619(12) 0.0044(10) 0.047(2) Uani 0.64(3) 1 d . U P A 1
H12 H 0.1511 0.3144 0.0147 0.056 Uiso 0.64(3) 1 calc R U P A 1
C13 C 0.098(2) 0.2009(9) -0.0622(7) 0.050(2) Uani 0.64(3) 1 d . U P A 1
H13 H 0.2153 0.2125 -0.0963 0.060 Uiso 0.64(3) 1 calc R U P A 1
C14 C -0.042(2) 0.1216(8) -0.0765(5) 0.047(2) Uani 0.64(3) 1 d D U P A 1
C15 C -0.215(2) 0.1057(9) -0.0257(8) 0.047(2) Uani 0.64(3) 1 d . U P A 1
H15 H -0.3018 0.0502 -0.0341 0.057 Uiso 0.64(3) 1 calc R U P A 1
Cl2A Cl -0.0712(16) 0.0323(7) -0.1577(6) 0.0840(16) Uani 0.36(3) 1 d D U P A 2
C10A C -0.270(5) 0.1583(19) 0.0542(14) 0.036(4) Uani 0.36(3) 1 d D . P A 2
C11A C -0.120(4) 0.235(2) 0.0542(14) 0.049(7) Uani 0.36(3) 1 d D . P A 2
C12A C 0.044(5) 0.247(2) -0.0027(19) 0.050(5) Uani 0.36(3) 1 d D U P A 2
H12A H 0.1428 0.2997 0.0011 0.060 Uiso 0.36(3) 1 calc R U P A 2
C13A C 0.054(3) 0.1781(16) -0.0655(12) 0.047(4) Uani 0.36(3) 1 d D U P A 2
H13A H 0.1683 0.1787 -0.1027 0.056 Uiso 0.36(3) 1 calc R U P A 2
C14A C -0.108(3) 0.1085(14) -0.0718(11) 0.044(3) Uani 0.36(3) 1 d D U P A 2
C15A C -0.274(3) 0.0984(17) -0.0170(12) 0.039(3) Uani 0.36(3) 1 d D U P A 2
H15A H -0.3859 0.0530 -0.0268 0.047 Uiso 0.36(3) 1 calc R U P A 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
Cl1 C4 1.744(2) . ?
Cl2 C14 1.747(5) . ?
N1 C1 1.434(3) . ?
N1 C9 1.462(3) . ?
N1 C8 1.463(3) . ?
N2 C11 1.375(13) . ?
N2 C8 1.461(3) . ?
N2 C7 1.473(3) . ?
N2 C11A 1.54(2) . ?
C1 C2 1.391(3) . ?
C1 C6 1.395(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C5 C6 1.391(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.513(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10A 1.37(3) . ?
C9 C10 1.586(15) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.400(13) . ?
C10 C15 1.403(13) . ?
C11 C12 1.401(11) . ?
C12 C13 1.382(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(8) . ?
C15 H15 0.9300 . ?
Cl2A C14A 1.743(9) . ?
C10A C11A 1.392(19) . ?
C10A C15A 1.402(18) . ?
C11A C12A 1.386(18) . ?
C12A C13A 1.384(16) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.367(12) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.369(11) . ?
C15A H15A 0.9300 . ?

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
C1 N1 C9 112.23(16) . . ?
C1 N1 C8 110.73(17) . . ?
C9 N1 C8 108.00(17) . . ?
C11 N2 C8 111.0(4) . . ?
C11 N2 C7 114.0(6) . . ?
C8 N2 C7 107.85(17) . . ?
C8 N2 C11A 109.1(8) . . ?
C7 N2 C11A 111.7(10) . . ?
C2 C1 C6 120.0(2) . . ?
C2 C1 N1 118.32(18) . . ?
C6 C1 N1 121.69(18) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 118.80(19) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 Cl1 119.21(16) . . ?
C5 C4 Cl1 119.30(18) . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.02(18) . . ?
C5 C6 C7 120.47(19) . . ?
C1 C6 C7 120.49(19) . . ?
N2 C7 C6 112.36(17) . . ?
N2 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N2 C8 N1 112.09(16) . . ?
N2 C8 H8A 109.2 . . ?
N1 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
N1 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10A C9 N1 112.1(9) . . ?
N1 C9 C10 112.6(5) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 119.4(11) . . ?
C11 C10 C9 117.5(10) . . ?
C15 C10 C9 122.1(10) . . ?
N2 C11 C10 123.7(8) . . ?
N2 C11 C12 119.3(9) . . ?
C10 C11 C12 116.9(11) . . ?
C13 C12 C11 123.7(12) . . ?
C13 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
C12 C13 C14 117.9(9) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C15 C14 C13 120.2(7) . . ?
C15 C14 Cl2 116.6(7) . . ?
C13 C14 Cl2 123.2(6) . . ?
C14 C15 C10 121.6(9) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C9 C10A C11A 127.4(18) . . ?
C9 C10A C15A 114.9(18) . . ?
C11A C10A C15A 115.4(17) . . ?
C12A C11A C10A 125.5(19) . . ?
C12A C11A N2 118.4(17) . . ?
C10A C11A N2 116.0(15) . . ?
C11A C12A C13A 116.5(18) . . ?
C11A C12A H12A 121.7 . . ?
C13A C12A H12A 121.8 . . ?
C14A C13A C12A 118.5(15) . . ?
C14A C13A H13A 120.8 . . ?
C12A C13A H13A 120.7 . . ?
C13A C14A C15A 124.7(12) . . ?
C13A C14A Cl2A 111.1(13) . . ?
C15A C14A Cl2A 124.2(12) . . ?
C14A C15A C10A 118.2(15) . . ?
C14A C15A H15A 120.9 . . ?
C10A C15A H15A 120.9 . . ?

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
C9 N1 C1 C2 -78.1(2) . . . . ?
C8 N1 C1 C2 161.18(17) . . . . ?
C9 N1 C1 C6 102.5(2) . . . . ?
C8 N1 C1 C6 -18.2(2) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
N1 C1 C2 C3 179.56(17) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 Cl1 -176.76(15) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
Cl1 C4 C5 C6 176.42(15) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -178.13(17) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
N1 C1 C6 C5 -179.92(17) . . . . ?
C2 C1 C6 C7 179.29(17) . . . . ?
N1 C1 C6 C7 -1.3(3) . . . . ?
C11 N2 C7 C6 -78.2(6) . . . . ?
C8 N2 C7 C6 45.5(2) . . . . ?
C11A N2 C7 C6 -74.4(9) . . . . ?
C5 C6 C7 N2 165.53(17) . . . . ?
C1 C6 C7 N2 -13.0(3) . . . . ?
C11 N2 C8 N1 56.4(7) . . . . ?
C7 N2 C8 N1 -69.0(2) . . . . ?
C11A N2 C8 N1 52.5(11) . . . . ?
C1 N1 C8 N2 54.0(2) . . . . ?
C9 N1 C8 N2 -69.2(2) . . . . ?
C1 N1 C9 C10A -73.7(15) . . . . ?
C8 N1 C9 C10A 48.7(15) . . . . ?
C1 N1 C9 C10 -82.7(8) . . . . ?
C8 N1 C9 C10 39.6(8) . . . . ?
C10A C9 C10 C11 -92(10) . . . . ?
N1 C9 C10 C11 -3.4(17) . . . . ?
C10A C9 C10 C15 76(9) . . . . ?
N1 C9 C10 C15 164.7(13) . . . . ?
C8 N2 C11 C10 -15.6(16) . . . . ?
C7 N2 C11 C10 106.4(14) . . . . ?
C11A N2 C11 C10 48(17) . . . . ?
C8 N2 C11 C12 160.8(12) . . . . ?
C7 N2 C11 C12 -77.2(15) . . . . ?
C11A N2 C11 C12 -135(19) . . . . ?
C15 C10 C11 N2 -178.3(13) . . . . ?
C9 C10 C11 N2 -10(2) . . . . ?
C15 C10 C11 C12 5(2) . . . . ?
C9 C10 C11 C12 173.6(14) . . . . ?
N2 C11 C12 C13 -178.3(13) . . . . ?
C10 C11 C12 C13 -2(3) . . . . ?
C11 C12 C13 C14 -1(2) . . . . ?
C12 C13 C14 C15 0.1(15) . . . . ?
C12 C13 C14 Cl2 179.9(11) . . . . ?
C13 C14 C15 C10 3.7(17) . . . . ?
Cl2 C14 C15 C10 -176.2(13) . . . . ?
C11 C10 C15 C14 -6(2) . . . . ?
C9 C10 C15 C14 -174.3(11) . . . . ?
N1 C9 C10A C11A -19(4) . . . . ?
C10 C9 C10A C11A 76(9) . . . . ?
N1 C9 C10A C15A 179.0(19) . . . . ?
C10 C9 C10A C15A -86(10) . . . . ?
C9 C10A C11A C12A -172(3) . . . . ?
C15A C10A C11A C12A -10(5) . . . . ?
C9 C10A C11A N2 4(4) . . . . ?
C15A C10A C11A N2 166(2) . . . . ?
C11 N2 C11A C12A 39(17) . . . . ?
C8 N2 C11A C12A 157(2) . . . . ?
C7 N2 C11A C12A -84(3) . . . . ?
C11 N2 C11A C10A -137(19) . . . . ?
C8 N2 C11A C10A -20(3) . . . . ?
C7 N2 C11A C10A 100(2) . . . . ?
C10A C11A C12A C13A 2(5) . . . . ?
N2 C11A C12A C13A -175(2) . . . . ?
C11A C12A C13A C14A 6(4) . . . . ?
C12A C13A C14A C15A -4(3) . . . . ?
C12A C13A C14A Cl2A 177(2) . . . . ?
C13A C14A C15A C10A -5(3) . . . . ?
Cl2A C14A C15A C10A 173(2) . . . . ?
C9 C10A C15A C14A 176(2) . . . . ?
C11A C10A C15A C14A 12(4) . . . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 986738'
#######################################################################
#
#                 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_kaw46
# (-)-4-Cl

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 Br2 N2, Cl, C H Cl3'
_chemical_formula_sum            'C16 H14 Br2 Cl4 N2'
_chemical_formula_weight         535.91


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.4113(1)
_cell_length_b                   9.0495(1)
_cell_length_c                   25.1456(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1914.03(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      3.515
_cell_measurement_theta_max      71.588

_exptl_crystal_description       'transparent block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.479
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    10.523
_shelx_estimated_absorpt_T_min   0.081
_shelx_estimated_absorpt_T_max   0.365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.201
_exptl_absorpt_correction_T_max  0.684
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16667
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.515
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3475
_reflns_number_gt                3460
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.991

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. These statistics refer to single and
 composite reflections containing twin component 1 only.

All non-hydrogen atoms were located in a single difference density map and 
 refined with anisotropic displacement parameters.  All CH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom (1.5 x Uiso for methyl H atoms).  The  
 NH hydrogen atom was located in a difference density map and
 refined using Ueq = 1.2 x Uiso and restrained with a N-H bond
 distance of 0.85(2) angstroms.
;

_computing_data_collection       APEX2
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+1.9080P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1443 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.451(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3475
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.222
_refine_ls_restrained_S_all      1.222
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.16858(7) -0.46740(6) -0.00461(2) 0.01498(17) Uani 1 1 d . . . . .
Br2 Br 0.51209(6) 0.35335(6) 0.05423(2) 0.01471(17) Uani 1 1 d . . . . .
Cl1 Cl 0.12472(17) -0.01219(15) 0.29478(5) 0.0158(3) Uani 1 1 d . . . . .
Cl2 Cl 0.6865(2) 0.03523(18) 0.31377(6) 0.0289(4) Uani 1 1 d . . . . .
Cl3 Cl 0.5250(2) 0.23773(16) 0.38387(6) 0.0233(3) Uani 1 1 d . . . . .
Cl4 Cl 0.4743(3) 0.25794(19) 0.27059(7) 0.0362(5) Uani 1 1 d . . . . .
N1 N -0.1878(6) 0.1000(5) 0.12553(17) 0.0096(9) Uani 1 1 d . . . . .
N2 N 0.0191(6) 0.0111(5) 0.18306(18) 0.0120(9) Uani 1 1 d D . . . .
H1 H 0.060(8) 0.015(8) 0.2134(15) 0.014 Uiso 1 1 d D U . . .
C1 C -0.1770(6) -0.0348(6) 0.0958(2) 0.0115(10) Uani 1 1 d . . . . .
C2 C -0.2554(6) -0.0419(6) 0.0468(2) 0.0120(11) Uani 1 1 d . . . . .
H2 H -0.3127 0.0416 0.0343 0.014 Uiso 1 1 calc R U . . .
C3 C -0.2507(6) -0.1687(7) 0.0165(2) 0.0137(11) Uani 1 1 d . . . . .
H3 H -0.3019 -0.1729 -0.0172 0.016 Uiso 1 1 calc R U . . .
C4 C -0.1688(7) -0.2904(6) 0.0364(2) 0.0135(10) Uani 1 1 d . . . . .
C5 C -0.0900(7) -0.2869(6) 0.0843(2) 0.0117(11) Uani 1 1 d . . . . .
H5 H -0.0356 -0.3720 0.0969 0.014 Uiso 1 1 calc R U . . .
C6 C -0.0907(6) -0.1560(6) 0.1146(2) 0.0108(10) Uani 1 1 d . . . . .
C7 C 0.0029(7) -0.1481(6) 0.1654(2) 0.0135(11) Uani 1 1 d . . . . .
H7A H 0.1097 -0.1913 0.1598 0.016 Uiso 1 1 calc R U . . .
H7B H -0.0516 -0.2060 0.1934 0.016 Uiso 1 1 calc R U . . .
C8 C -0.1443(6) 0.0802(6) 0.1804(2) 0.0113(10) Uani 1 1 d . . . . .
H8A H -0.2227 0.0154 0.1982 0.014 Uiso 1 1 calc R U . . .
H8B H -0.1438 0.1768 0.1988 0.014 Uiso 1 1 calc R U . . .
C9 C -0.0922(6) 0.2199(6) 0.1017(2) 0.0106(11) Uani 1 1 d . . . . .
H9A H -0.1251 0.3159 0.1170 0.013 Uiso 1 1 calc R U . . .
H9B H -0.1111 0.2233 0.0629 0.013 Uiso 1 1 calc R U . . .
C10 C 0.0831(6) 0.1947(6) 0.1124(2) 0.0096(10) Uani 1 1 d . . . . .
C11 C 0.1968(7) 0.2711(6) 0.0838(2) 0.0111(11) Uani 1 1 d . . . . .
H11 H 0.1655 0.3402 0.0573 0.013 Uiso 1 1 calc R U . . .
C12 C 0.3565(7) 0.2467(6) 0.0938(2) 0.0118(11) Uani 1 1 d . . . . .
C13 C 0.4074(6) 0.1492(6) 0.1323(2) 0.0125(11) Uani 1 1 d . . . . .
H13 H 0.5176 0.1348 0.1387 0.015 Uiso 1 1 calc R U . . .
C14 C 0.2947(7) 0.0724(6) 0.1615(2) 0.0124(11) Uani 1 1 d . . . . .
H14 H 0.3268 0.0048 0.1883 0.015 Uiso 1 1 calc R U . . .
C15 C 0.1335(7) 0.0953(6) 0.1512(2) 0.0110(11) Uani 1 1 d . . . . .
C16 C 0.5097(8) 0.1362(7) 0.3241(2) 0.0220(13) Uani 1 1 d . . . . .
H16 H 0.4186 0.0656 0.3271 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.905(5) . ?
Br2 C12 1.906(5) . ?
Cl2 C16 1.765(7) . ?
Cl3 C16 1.766(6) . ?
Cl4 C16 1.765(6) . ?
N1 C1 1.433(7) . ?
N1 C8 1.438(7) . ?
N1 C9 1.477(7) . ?
N2 C15 1.466(7) . ?
N2 C8 1.512(7) . ?
N2 C7 1.513(7) . ?
N2 H1 0.84(3) . ?
C1 C6 1.397(8) . ?
C1 C2 1.398(8) . ?
C2 C3 1.379(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(8) . ?
C5 C6 1.408(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.503(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.516(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.382(8) . ?
C10 C15 1.393(8) . ?
C11 C12 1.385(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(8) . ?
C13 C14 1.386(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(8) . ?
C14 H14 0.9500 . ?
C16 H16 1.0000 . ?

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
C1 N1 C8 112.2(4) . . ?
C1 N1 C9 112.3(4) . . ?
C8 N1 C9 110.0(4) . . ?
C15 N2 C8 110.9(4) . . ?
C15 N2 C7 113.2(4) . . ?
C8 N2 C7 107.4(4) . . ?
C15 N2 H1 102(5) . . ?
C8 N2 H1 114(5) . . ?
C7 N2 H1 110(5) . . ?
C6 C1 C2 120.4(5) . . ?
C6 C1 N1 121.7(5) . . ?
C2 C1 N1 118.0(5) . . ?
C3 C2 C1 120.8(5) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 118.2(5) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 122.4(5) . . ?
C5 C4 Br1 119.5(4) . . ?
C3 C4 Br1 118.1(4) . . ?
C4 C5 C6 119.4(5) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 118.7(5) . . ?
C1 C6 C7 121.5(5) . . ?
C5 C6 C7 119.8(5) . . ?
C6 C7 N2 110.0(4) . . ?
C6 C7 H7A 109.7 . . ?
N2 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
N2 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N1 C8 N2 109.0(4) . . ?
N1 C8 H8A 109.9 . . ?
N2 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
N2 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N1 C9 C10 110.3(5) . . ?
N1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C15 118.5(5) . . ?
C11 C10 C9 120.4(5) . . ?
C15 C10 C9 121.1(5) . . ?
C10 C11 C12 119.8(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 122.1(5) . . ?
C13 C12 Br2 118.5(4) . . ?
C11 C12 Br2 119.3(4) . . ?
C12 C13 C14 118.7(5) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C15 119.5(5) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C10 C15 C14 121.4(5) . . ?
C10 C15 N2 121.3(5) . . ?
C14 C15 N2 117.3(5) . . ?
Cl2 C16 Cl4 110.6(4) . . ?
Cl2 C16 Cl3 109.5(3) . . ?
Cl4 C16 Cl3 109.7(3) . . ?
Cl2 C16 H16 109.0 . . ?
Cl4 C16 H16 109.0 . . ?
Cl3 C16 H16 109.0 . . ?

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
C8 N1 C1 C6 -17.4(7) . . . . ?
C9 N1 C1 C6 107.1(6) . . . . ?
C8 N1 C1 C2 162.8(5) . . . . ?
C9 N1 C1 C2 -72.7(6) . . . . ?
C6 C1 C2 C3 0.7(8) . . . . ?
N1 C1 C2 C3 -179.5(5) . . . . ?
C1 C2 C3 C4 1.5(8) . . . . ?
C2 C3 C4 C5 -1.7(8) . . . . ?
C2 C3 C4 Br1 177.9(4) . . . . ?
C3 C4 C5 C6 -0.2(8) . . . . ?
Br1 C4 C5 C6 -179.9(4) . . . . ?
C2 C1 C6 C5 -2.6(8) . . . . ?
N1 C1 C6 C5 177.6(5) . . . . ?
C2 C1 C6 C7 176.2(5) . . . . ?
N1 C1 C6 C7 -3.6(8) . . . . ?
C4 C5 C6 C1 2.4(8) . . . . ?
C4 C5 C6 C7 -176.4(5) . . . . ?
C1 C6 C7 N2 -13.3(7) . . . . ?
C5 C6 C7 N2 165.4(5) . . . . ?
C15 N2 C7 C6 -74.5(6) . . . . ?
C8 N2 C7 C6 48.2(5) . . . . ?
C1 N1 C8 N2 54.4(6) . . . . ?
C9 N1 C8 N2 -71.3(5) . . . . ?
C15 N2 C8 N1 52.4(5) . . . . ?
C7 N2 C8 N1 -71.7(5) . . . . ?
C1 N1 C9 C10 -74.7(6) . . . . ?
C8 N1 C9 C10 51.0(6) . . . . ?
N1 C9 C10 C11 164.5(5) . . . . ?
N1 C9 C10 C15 -16.0(7) . . . . ?
C15 C10 C11 C12 0.6(8) . . . . ?
C9 C10 C11 C12 -179.8(5) . . . . ?
C10 C11 C12 C13 -0.9(8) . . . . ?
C10 C11 C12 Br2 -179.8(4) . . . . ?
C11 C12 C13 C14 0.5(8) . . . . ?
Br2 C12 C13 C14 179.4(4) . . . . ?
C12 C13 C14 C15 0.2(8) . . . . ?
C11 C10 C15 C14 0.1(8) . . . . ?
C9 C10 C15 C14 -179.5(5) . . . . ?
C11 C10 C15 N2 179.8(5) . . . . ?
C9 C10 C15 N2 0.2(8) . . . . ?
C13 C14 C15 C10 -0.4(8) . . . . ?
C13 C14 C15 N2 179.8(5) . . . . ?
C8 N2 C15 C10 -17.8(7) . . . . ?
C7 N2 C15 C10 103.0(6) . . . . ?
C8 N2 C15 C14 162.0(5) . . . . ?
C7 N2 C15 C14 -77.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1 Cl1 0.84(3) 2.13(3) 2.954(5) 167(7) .
C16 H16 Cl1 1.00 2.70 3.582(6) 147.9 .

_refine_diff_density_max         0.754
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.156

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 986739'
#######################################################################
#
#                 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_kaw78
# 8-Cl


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Cl2 N2'
_chemical_formula_sum            'C14 H10 Cl2 N2'
_chemical_formula_weight         277.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.7702(1)
_cell_length_b                   15.3388(2)
_cell_length_c                   13.9156(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.316(1)
_cell_angle_gamma                90.00
_cell_volume                     1228.15(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8040
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      59.19

_exptl_crystal_description       'transparent rhomboid'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    4.589
_shelx_estimated_absorpt_T_min   0.289
_shelx_estimated_absorpt_T_max   0.393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.426
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII 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            16883
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.296
_diffrn_reflns_theta_max         67.827
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2218
_reflns_number_gt                1748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

All non-hydrogen atoms were located in a single difference density map and 
 refined with anisotropic displacement parameters.  All CH and NH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom.  

;

_computing_data_collection       APEX2
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_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     
'w=1/[σ²(Fo²)+(0.0433P)²+0.4521P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2218
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.61970(15) 0.38089(6) 1.00062(5) 0.0947(3) Uani 1 1 d . . . . .
Cl2 Cl 0.05356(12) 0.31951(4) 0.17179(4) 0.0756(2) Uani 1 1 d . . . . .
N1 N 0.9683(3) 0.43727(15) 0.61767(15) 0.0674(6) Uani 1 1 d . . . . .
N2 N 0.6189(3) 0.38057(12) 0.54030(13) 0.0528(4) Uani 1 1 d . . . . .
C1 C 0.8846(4) 0.41985(15) 0.70783(16) 0.0542(5) Uani 1 1 d . . . . .
C2 C 1.0157(4) 0.44670(16) 0.79032(18) 0.0625(6) Uani 1 1 d . . . . .
H2 H 1.1578 0.4740 0.7845 0.075 Uiso 1 1 calc R U . . .
C3 C 0.9395(4) 0.43371(16) 0.87998(18) 0.0654(6) Uani 1 1 d . . . . .
H3 H 1.0295 0.4513 0.9348 0.078 Uiso 1 1 calc R U . . .
C4 C 0.7267(4) 0.39405(15) 0.88767(17) 0.0621(6) Uani 1 1 d . . . . .
C5 C 0.5949(4) 0.36539(15) 0.80655(16) 0.0577(6) Uani 1 1 d . . . . .
H5 H 0.4533 0.3378 0.8127 0.069 Uiso 1 1 calc R U . . .
C6 C 0.6739(4) 0.37783(13) 0.71689(15) 0.0502(5) Uani 1 1 d . . . . .
C7 C 0.5329(4) 0.34538(16) 0.62858(15) 0.0560(5) Uani 1 1 d . . . . .
H7A H 0.5394 0.2822 0.6268 0.067 Uiso 1 1 calc R U . . .
H7B H 0.3718 0.3623 0.6321 0.067 Uiso 1 1 calc R U . . .
C8 C 0.8334(4) 0.41819(17) 0.54307(18) 0.0640(6) Uani 1 1 d . . . . .
H8 H 0.8887 0.4316 0.4838 0.077 Uiso 1 1 calc R U . . .
C9 C 0.4856(4) 0.36645(13) 0.45157(15) 0.0497(5) Uani 1 1 d . . . . .
C10 C 0.5435(4) 0.40503(16) 0.36660(17) 0.0631(6) Uani 1 1 d . . . . .
H10 H 0.6719 0.4417 0.3671 0.076 Uiso 1 1 calc R U . . .
C11 C 0.4126(4) 0.38954(16) 0.28125(18) 0.0654(6) Uani 1 1 d . . . . .
H11 H 0.4553 0.4148 0.2245 0.078 Uiso 1 1 calc R U . . .
C12 C 0.2203(4) 0.33716(14) 0.27961(16) 0.0555(5) Uani 1 1 d . . . . .
C13 C 0.1560(4) 0.29964(15) 0.36318(17) 0.0583(6) Uani 1 1 d . . . . .
H13 H 0.0234 0.2651 0.3624 0.070 Uiso 1 1 calc R U . . .
C14 C 0.2894(4) 0.31345(15) 0.44839(16) 0.0562(5) Uani 1 1 d . . . . .
H14 H 0.2474 0.2869 0.5046 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.743(3) . ?
Cl2 C12 1.742(2) . ?
N1 C8 1.283(3) . ?
N1 C1 1.403(3) . ?
N2 C8 1.364(3) . ?
N2 C9 1.421(3) . ?
N2 C7 1.462(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.390(3) . ?
C2 C3 1.368(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C5 C6 1.373(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.507(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9300 . ?
C9 C10 1.385(3) . ?
C9 C14 1.392(3) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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
C8 N1 C1 116.8(2) . . ?
C8 N2 C9 121.32(19) . . ?
C8 N2 C7 119.81(18) . . ?
C9 N2 C7 118.55(17) . . ?
C2 C1 C6 119.2(2) . . ?
C2 C1 N1 118.7(2) . . ?
C6 C1 N1 122.10(19) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 Cl1 119.86(18) . . ?
C5 C4 Cl1 119.24(19) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 C7 119.9(2) . . ?
C1 C6 C7 120.1(2) . . ?
N2 C7 C6 111.51(18) . . ?
N2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 N2 127.8(2) . . ?
N1 C8 H8 116.1 . . ?
N2 C8 H8 116.1 . . ?
C10 C9 C14 118.1(2) . . ?
C10 C9 N2 121.8(2) . . ?
C14 C9 N2 120.2(2) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 Cl2 120.02(19) . . ?
C13 C12 Cl2 119.83(18) . . ?
C12 C13 C14 119.6(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C9 121.1(2) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?

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
C8 N1 C1 C2 -174.2(2) . . . . ?
C8 N1 C1 C6 4.8(3) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
N1 C1 C2 C3 178.1(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C2 C3 C4 Cl1 -177.26(19) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
Cl1 C4 C5 C6 177.97(17) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 179.0(2) . . . . ?
C2 C1 C6 C5 1.7(3) . . . . ?
N1 C1 C6 C5 -177.4(2) . . . . ?
C2 C1 C6 C7 -177.9(2) . . . . ?
N1 C1 C6 C7 3.0(3) . . . . ?
C8 N2 C7 C6 15.3(3) . . . . ?
C9 N2 C7 C6 -171.17(18) . . . . ?
C5 C6 C7 N2 167.87(19) . . . . ?
C1 C6 C7 N2 -12.5(3) . . . . ?
C1 N1 C8 N2 -1.9(4) . . . . ?
C9 N2 C8 N1 177.5(2) . . . . ?
C7 N2 C8 N1 -9.1(4) . . . . ?
C8 N2 C9 C10 -13.1(3) . . . . ?
C7 N2 C9 C10 173.4(2) . . . . ?
C8 N2 C9 C14 167.6(2) . . . . ?
C7 N2 C9 C14 -5.8(3) . . . . ?
C14 C9 C10 C11 -1.4(3) . . . . ?
N2 C9 C10 C11 179.3(2) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C10 C11 C12 Cl2 178.93(19) . . . . ?
C11 C12 C13 C14 -1.5(3) . . . . ?
Cl2 C12 C13 C14 179.67(17) . . . . ?
C12 C13 C14 C9 1.4(3) . . . . ?
C10 C9 C14 C13 0.0(3) . . . . ?
N2 C9 C14 C13 179.3(2) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 986740'
