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

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

data_314RICH
_database_code_depnum_ccdc_archive 'CCDC 718661'
_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2016-09-22 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cl8 N2'
_chemical_formula_weight         521.92

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           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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+'
'x+1/2, y+1/2, z+'
'-x+1/2, y+1/2, -z+'
'-x+, -y+, -z+'
'x+, -y+, z+'
'-x+1/2, -y+1/2, -z+'
'x+1/2, -y+1/2, z+'

_cell_length_a                   15.0733(19)
_cell_length_b                   9.1677(11)
_cell_length_c                   8.2639(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.462(2)
_cell_angle_gamma                90
_cell_volume                     1138.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2341
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.32
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.994
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.859
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5534
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.472
_diffrn_reflns_theta_max         24.972
_diffrn_reflns_theta_full        24.972
_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             1074
_reflns_number_gt                952
_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0455P)²+2.0041P] 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_number_reflns         1074
_refine_ls_number_parameters     70
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
H6 H 0.225(5) 0.0000 0.447(9) 0.12(3) Uiso 1 2 d S . P . .
C1 C 0.4362(3) 0.0000 0.3576(5) 0.0441(11) Uani 1 2 d S T P . .
H1 H 0.3799 0.0000 0.4096 0.053 Uiso 1 2 calc R U P . .
C2 C 0.4880(2) 0.1361(4) 0.4086(4) 0.0459(8) Uani 1 1 d . . . . .
H2 H 0.5424 0.1408 0.3513 0.055 Uiso 1 1 calc R U . . .
C3 C 0.1827(3) 0.1257(5) 0.2541(6) 0.0682(12) Uani 1 1 d . . . . .
H3 H 0.1934 0.2128 0.3098 0.082 Uiso 1 1 calc R U . . .
C4 C 0.1546(3) 0.1278(6) 0.0983(6) 0.0879(15) Uani 1 1 d . . . . .
H4 H 0.1439 0.2159 0.0445 0.105 Uiso 1 1 calc R U . . .
C5 C 0.1416(5) 0.0000 0.0187(8) 0.093(2) Uani 1 2 d S T P . .
H5 H 0.1237 0.0000 -0.0915 0.112 Uiso 1 2 calc R U P . .
CL1 Cl 0.41236(10) 0.0000 0.14218(15) 0.0670(5) Uani 1 2 d S T P . .
CL2 Cl 0.42043(9) 0.29203(12) 0.35784(13) 0.0850(5) Uani 1 1 d . . . . .
CL3 Cl 0.29018(9) 0.0000 0.68130(17) 0.0571(4) Uani 1 2 d S T P . .
N1 N 0.1957(3) 0.0000 0.3307(6) 0.0618(13) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.514(4) 6 ?
C1 C2 1.514(4) . ?
C1 CL1 1.789(5) . ?
C2 C2 1.526(6) 2_656 ?
C2 CL2 1.786(3) . ?
C3 N1 1.322(5) . ?
C3 C4 1.325(6) . ?
C4 C5 1.350(6) . ?
C5 C4 1.350(6) 6 ?
N1 C3 1.322(5) 6 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 111.0(4) 6 . ?
C2 C1 CL1 109.6(2) 6 . ?
C2 C1 CL1 109.6(2) . . ?
C1 C2 C2 110.7(2) . 2_656 ?
C1 C2 CL2 108.8(2) . . ?
C2 C2 CL2 108.63(19) 2_656 . ?
N1 C3 C4 120.2(4) . . ?
C3 C4 C5 118.9(5) . . ?
C4 C5 C4 120.4(6) 6 . ?
C3 N1 C3 121.3(5) . 6 ?

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
C2 C1 C2 C2 -56.7(5) 6 . . 2_656 ?
CL1 C1 C2 C2 -178.0(3) . . . 2_656 ?
C2 C1 C2 CL2 -176.0(2) 6 . . . ?
CL1 C1 C2 CL2 62.7(3) . . . . ?
N1 C3 C4 C5 -1.7(8) . . . . ?
C3 C4 C5 C4 2.0(12) . . . 6 ?
C4 C3 N1 C3 1.3(8) . . . 6 ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.058



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

data_9hch1
_database_code_depnum_ccdc_archive 'CCDC 1497417'
_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2016-09-22 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 Cl6, 2(C5 H6 N), 2(Br)'
_chemical_formula_sum            'C16 H18 Br2 Cl6 N2'
_chemical_formula_weight         610.84

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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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+'
'x+1/2, y+1/2, z+'
'-x+1/2, y+1/2, -z+'
'-x+, -y+, -z+'
'x+, -y+, z+'
'-x+1/2, -y+1/2, -z+'
'x+1/2, -y+1/2, z+'

_cell_length_a                   15.078(3)
_cell_length_b                   9.4943(19)
_cell_length_c                   8.2367(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.05(3)
_cell_angle_gamma                90
_cell_volume                     1172.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1401
_cell_measurement_theta_min      5.3880
_cell_measurement_theta_max      70.9590

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    10.717
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.25137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;

_exptl_absorpt_special_details   
;
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_detector_area_resol_mean 16.4335
_diffrn_reflns_number            1922
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.401
_diffrn_reflns_theta_max         71.342
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1176
_reflns_number_gt                1095
_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_publication_material  ?
_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)+(0.1000P)²] 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_number_reflns         1176
_refine_ls_number_parameters     70
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.012
_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 0.28928(2) 0.5000 0.19975(5) 0.048(2) Uani 1 2 d S T P . .
CL1 Cl 0.59539(8) 0.5000 0.35900(12) 0.063(2) Uani 1 2 d S T P . .
N1 N 0.3100(3) 0.0000 0.1700(5) 0.057(2) Uani 1 2 d S T P . .
C1 C 0.5670(2) 0.5000 0.1422(4) 0.042(2) Uani 1 2 d S T P . .
H1 H 0.6221 0.5000 0.0888 0.050 Uiso 1 2 calc R U P . .
CL2 Cl 0.58345(7) 0.21779(10) 0.14121(10) 0.076(2) Uani 1 1 d . . . . .
C2 C 0.51423(17) 0.3683(3) 0.0917(3) 0.043(2) Uani 1 1 d . . . . .
H2 H 0.4613 0.3633 0.1510 0.051 Uiso 1 1 calc R U . . .
C4 C 0.3239(2) 0.1215(4) 0.2461(5) 0.064(2) Uani 1 1 d . . . . .
H4 H 0.3127 0.2053 0.1893 0.077 Uiso 1 1 calc R U . . .
C5 C 0.3546(3) 0.1246(4) 0.4068(5) 0.075(2) Uani 1 1 d . . . . .
H5 H 0.3657 0.2099 0.4606 0.090 Uiso 1 1 calc R U . . .
C6 C 0.3688(5) 0.0000 0.4883(6) 0.075(3) Uani 1 2 d S T P . .
H6 H 0.3882 0.0000 0.5993 0.090 Uiso 1 2 calc R U P . .
H10 H 0.294(5) 0.0000 0.050(9) 0.112(2) Uiso 1 2 d S . P . .


_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 C1 1.792(3) . ?
N1 C4 1.319(4) 6 ?
N1 C4 1.319(4) . ?
N1 H10 0.99(8) . ?
C1 C2 1.517(3) 6_565 ?
C1 C2 1.517(3) . ?
C1 H1 0.9800 . ?
CL2 C2 1.791(3) . ?
C2 C2 1.526(5) 2_655 ?
C2 H2 0.9800 . ?
C4 C5 1.356(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9300 . ?
C6 C5 1.366(5) 6 ?
C6 H6 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
C4 N1 C4 122.0(4) 6 . ?
C4 N1 H10 118.9(3) 6 . ?
C4 N1 H10 118.9(3) . . ?
C2 C1 C2 111.1(3) 6_565 . ?
C2 C1 CL1 109.66(17) 6_565 . ?
C2 C1 CL1 109.66(17) . . ?
C2 C1 H1 108.8 6_565 . ?
C2 C1 H1 108.8 . . ?
CL1 C1 H1 108.8 . . ?
C1 C2 C2 110.85(18) . 2_655 ?
C1 C2 CL2 108.59(19) . . ?
C2 C2 CL2 108.76(14) 2_655 . ?
C1 C2 H2 109.5 . . ?
C2 C2 H2 109.5 2_655 . ?
CL2 C2 H2 109.5 . . ?
N1 C4 C5 120.3(3) . . ?
N1 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 118.7(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C5 120.0(5) . 6 ?
C5 C6 H6 120.0 . . ?
C5 C6 H6 120.0 6 . ?

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
C2 C1 C2 C2 56.3(4) 6_565 . . 2_655 ?
CL1 C1 C2 C2 177.7(2) . . . 2_655 ?
C2 C1 C2 CL2 175.71(15) 6_565 . . . ?
CL1 C1 C2 CL2 -62.9(2) . . . . ?
C4 N1 C4 C5 0.9(7) 6 . . . ?
N1 C4 C5 C6 -1.4(7) . . . . ?
C4 C5 C6 C5 1.8(9) . . . 6 ?

_refine_diff_density_max         0.523
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.100



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

data_3hch
_database_code_depnum_ccdc_archive 'CCDC 1497418'
_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2016-09-22 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 Br Cl6 N2'
_chemical_formula_weight         529.93

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

_cell_length_a                   7.4262(2)
_cell_length_b                   17.3301(5)
_cell_length_c                   17.0948(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.613(3)
_cell_angle_gamma                90
_cell_volume                     2189.50(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1928
_cell_measurement_theta_min      5.1140
_cell_measurement_theta_max      68.1670

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    9.324
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;

_exptl_absorpt_special_details   
;
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.4335
_diffrn_reflns_number            7594
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.641
_diffrn_reflns_theta_max         71.461
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4146
_reflns_number_gt                2612
_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] 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_number_reflns         4146
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1959
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.4618(2) 0.17200(7) 0.22162(11) 0.082(3) Uani 1 1 d . . . . .
BR1 Br -0.07688(7) 0.32622(3) 0.31974(3) 0.059(3) Uani 1 1 d . . . . .
N1 N 0.9701(7) 0.3117(3) 0.5998(3) 0.070(3) Uani 1 1 d . . . . .
CL2 Cl 0.3578(3) 0.17312(9) 0.40199(12) 0.094(3) Uani 1 1 d . . . . .
N2 N 0.8785(7) 0.1692(3) 0.5465(4) 0.077(3) Uani 1 1 d . . . . .
CL3 Cl 0.5135(3) 0.32589(10) 0.49582(8) 0.088(3) Uani 1 1 d . . . . .
C4 C 0.4673(7) 0.3983(3) 0.3556(3) 0.049(3) Uani 1 1 d . . . . .
H4 H 0.5996 0.3976 0.3574 0.059 Uiso 1 1 calc R U . . .
CL4 Cl 0.3990(2) 0.48280(8) 0.40391(8) 0.079(3) Uani 1 1 d . . . . .
CL5 Cl 0.4637(2) 0.48226(7) 0.22299(8) 0.073(3) Uani 1 1 d . . . . .
C5 C 0.3872(6) 0.3990(3) 0.2706(2) 0.044(3) Uani 1 1 d . . . . .
H5 H 0.2550 0.4007 0.2690 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4416(7) 0.3269(2) 0.2284(3) 0.048(3) Uani 1 1 d . . . . .
H6 H 0.5735 0.3262 0.2281 0.058 Uiso 1 1 calc R U . . .
CL6 Cl 0.3397(2) 0.32799(8) 0.12920(8) 0.077(3) Uani 1 1 d . . . . .
C1 C 0.3826(6) 0.2547(3) 0.2689(3) 0.051(3) Uani 1 1 d . . . . .
H1A H 0.2501 0.2533 0.2646 0.061 Uiso 1 1 calc R U . . .
H20 H 0.933(5) 0.248(2) 0.580(2) 0.041(3) Uiso 1 1 d . . . . .
C2 C 0.4535(6) 0.2538(3) 0.3556(3) 0.0549(13) Uani 1 1 d . . . . .
H2 H 0.5854 0.2482 0.3601 0.066 Uiso 1 1 calc R U . . .
C3 C 0.4054(7) 0.3279(3) 0.3973(3) 0.0551(13) Uani 1 1 d . . . . .
H3 H 0.2739 0.3304 0.3990 0.066 Uiso 1 1 calc R U . . .
C7 C 1.0429(9) 0.3610(5) 0.5527(4) 0.094(2) Uani 1 1 d . . . . .
H7 H 1.0569 0.3468 0.5011 0.113 Uiso 1 1 calc R U . . .
C8 C 1.0970(10) 0.4315(5) 0.5788(6) 0.103(2) Uani 1 1 d . . . . .
H8 H 1.1550 0.4647 0.5466 0.123 Uiso 1 1 calc R U . . .
C9 C 1.0662(10) 0.4536(4) 0.6523(6) 0.099(2) Uani 1 1 d . . . . .
H9 H 1.0970 0.5030 0.6702 0.118 Uiso 1 1 calc R U . . .
C10 C 0.9907(10) 0.4033(5) 0.6991(4) 0.097(2) Uani 1 1 d . . . . .
H10 H 0.9726 0.4171 0.7504 0.116 Uiso 1 1 calc R U . . .
C11 C 0.9410(9) 0.3326(4) 0.6716(4) 0.0785(18) Uani 1 1 d . . . . .
H11 H 0.8857 0.2983 0.7036 0.094 Uiso 1 1 calc R U . . .
C12 C 0.8370(9) 0.1130(4) 0.5930(4) 0.088(2) Uani 1 1 d . . . . .
H12 H 0.8489 0.1213 0.6470 0.106 Uiso 1 1 calc R U . . .
C13 C 0.7767(10) 0.0427(4) 0.5650(5) 0.101(2) Uani 1 1 d . . . . .
H13 H 0.7455 0.0044 0.5993 0.122 Uiso 1 1 calc R U . . .
C14 C 0.7631(10) 0.0295(5) 0.4859(5) 0.100(2) Uani 1 1 d . . . . .
H14 H 0.7255 -0.0182 0.4655 0.120 Uiso 1 1 calc R U . . .
C15 C 0.8051(10) 0.0867(5) 0.4383(4) 0.101(2) Uani 1 1 d . . . . .
H15 H 0.7945 0.0795 0.3841 0.122 Uiso 1 1 calc R U . . .
C16 C 0.8631(9) 0.1553(4) 0.4697(4) 0.088(2) Uani 1 1 d . . . . .
H16 H 0.8934 0.1943 0.4360 0.106 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 C1 1.774(5) . ?
N1 C11 1.318(8) . ?
N1 C7 1.325(8) . ?
N1 H20 1.18(4) . ?
CL2 C2 1.789(5) . ?
N2 C12 1.312(8) . ?
N2 C16 1.329(8) . ?
CL3 C3 1.794(5) . ?
C4 C3 1.507(6) . ?
C4 C5 1.516(6) . ?
C4 CL4 1.779(5) . ?
C4 H4 0.9800 . ?
CL5 C5 1.778(4) . ?
C5 C6 1.516(6) . ?
C5 H5 0.9800 . ?
C6 C1 1.515(6) . ?
C6 CL6 1.788(5) . ?
C6 H6 0.9800 . ?
C1 C2 1.524(7) . ?
C1 H1A 0.9800 . ?
C2 C3 1.527(7) . ?
C2 H2 0.9800 . ?
C3 H3 0.9800 . ?
C7 C8 1.350(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.355(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.342(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.352(9) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.369(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.339(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.357(9) . ?
C15 H15 0.9300 . ?
C16 H16 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
C11 N1 C7 120.2(6) . . ?
C11 N1 H20 118.1(19) . . ?
C7 N1 H20 121.6(19) . . ?
C12 N2 C16 117.5(6) . . ?
C3 C4 C5 110.5(4) . . ?
C3 C4 CL4 109.5(3) . . ?
C5 C4 CL4 109.6(3) . . ?
C3 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
CL4 C4 H4 109.1 . . ?
C4 C5 C6 110.6(4) . . ?
C4 C5 CL5 109.4(3) . . ?
C6 C5 CL5 109.8(3) . . ?
C4 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
CL5 C5 H5 109.0 . . ?
C1 C6 C5 111.1(4) . . ?
C1 C6 CL6 109.1(3) . . ?
C5 C6 CL6 109.6(3) . . ?
C1 C6 H6 109.0 . . ?
C5 C6 H6 109.0 . . ?
CL6 C6 H6 109.0 . . ?
C6 C1 C2 111.4(4) . . ?
C6 C1 CL1 109.6(3) . . ?
C2 C1 CL1 109.7(3) . . ?
C6 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
CL1 C1 H1A 108.7 . . ?
C1 C2 C3 111.8(4) . . ?
C1 C2 CL2 108.9(3) . . ?
C3 C2 CL2 109.2(3) . . ?
C1 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
CL2 C2 H2 109.0 . . ?
C4 C3 C2 111.3(4) . . ?
C4 C3 CL3 109.3(3) . . ?
C2 C3 CL3 108.5(3) . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
CL3 C3 H3 109.2 . . ?
N1 C7 C8 120.6(7) . . ?
N1 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.4(7) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 119.2(7) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 119.8(7) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
N1 C11 C10 120.6(6) . . ?
N1 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N2 C12 C13 122.5(7) . . ?
N2 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 119.0(7) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 118.6(7) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 119.5(7) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
N2 C16 C15 122.9(7) . . ?
N2 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?

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
C3 C4 C5 C6 -58.6(5) . . . . ?
CL4 C4 C5 C6 -179.3(3) . . . . ?
C3 C4 C5 CL5 -179.7(3) . . . . ?
CL4 C4 C5 CL5 59.6(4) . . . . ?
C4 C5 C6 C1 57.6(5) . . . . ?
CL5 C5 C6 C1 178.5(3) . . . . ?
C4 C5 C6 CL6 178.3(3) . . . . ?
CL5 C5 C6 CL6 -60.9(4) . . . . ?
C5 C6 C1 C2 -54.6(5) . . . . ?
CL6 C6 C1 C2 -175.5(3) . . . . ?
C5 C6 C1 CL1 -176.2(3) . . . . ?
CL6 C6 C1 CL1 62.9(4) . . . . ?
C6 C1 C2 C3 52.6(6) . . . . ?
CL1 C1 C2 C3 174.2(3) . . . . ?
C6 C1 C2 CL2 173.4(3) . . . . ?
CL1 C1 C2 CL2 -65.1(4) . . . . ?
C5 C4 C3 C2 56.6(5) . . . . ?
CL4 C4 C3 C2 177.4(3) . . . . ?
C5 C4 C3 CL3 176.5(3) . . . . ?
CL4 C4 C3 CL3 -62.7(4) . . . . ?
C1 C2 C3 C4 -53.9(6) . . . . ?
CL2 C2 C3 C4 -174.4(3) . . . . ?
C1 C2 C3 CL3 -174.2(3) . . . . ?
CL2 C2 C3 CL3 65.3(4) . . . . ?
C11 N1 C7 C8 3.6(10) . . . . ?
N1 C7 C8 C9 -4.1(12) . . . . ?
C7 C8 C9 C10 3.4(12) . . . . ?
C8 C9 C10 C11 -2.2(12) . . . . ?
C7 N1 C11 C10 -2.4(10) . . . . ?
C9 C10 C11 N1 1.7(11) . . . . ?
C16 N2 C12 C13 -1.1(11) . . . . ?
N2 C12 C13 C14 1.6(12) . . . . ?
C12 C13 C14 C15 -1.7(12) . . . . ?
C13 C14 C15 C16 1.3(12) . . . . ?
C12 N2 C16 C15 0.8(11) . . . . ?
C14 C15 C16 N2 -0.9(12) . . . . ?

_refine_diff_density_max         0.554
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.075



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

data_282r
_database_code_depnum_ccdc_archive 'CCDC 1497419'
_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2016-09-22 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 Cl6'
_chemical_formula_weight         290.81

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

_space_group_crystal_system      cubic
_space_group_IT_number           205
_space_group_name_H-M_alt        'P a -3'
_space_group_name_Hall           '-P 2ac 2ab 3'

_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+, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+'
'z+, x+, y+'
'z+1/2, -x+1/2, -y+'
'-z+1/2, -x+, y+1/2'
'-z+, x+1/2, -y+1/2'
'y+, z+, x+'
'-y+, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x+'
'-y+1/2, -z+, x+1/2'
'-x+, -y+, -z+'
'x-1/2, y+, -z-1/2'
'x+, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z+'
'-z+, -x+, -y+'
'-z-1/2, x-1/2, y+'
'z-1/2, x+, -y-1/2'
'z+, -x-1/2, y-1/2'
'-y+, -z+, -x+'
'y+, -z-1/2, x-1/2'
'-y-1/2, z-1/2, x+'
'y-1/2, z+, -x-1/2'

_cell_length_a                   10.0568(12)
_cell_length_b                   10.0568(12)
_cell_length_c                   10.0568(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1017.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2766
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      26.73
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.628
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_T_max  0.757
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6638
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.509
_diffrn_reflns_theta_max         24.902
_diffrn_reflns_theta_full        24.902
_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             300
_reflns_number_gt                298
_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)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_number_reflns         300
_refine_ls_number_parameters     19
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.1681
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.562
_refine_ls_restrained_S_all      1.562
_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
CL1 Cl 0.91839(8) 0.11550(7) 0.22245(7) 0.0371(7) Uani 1 1 d . . . . .
C1 C 0.9362(2) 0.0800(3) 0.3955(2) 0.0234(9) Uani 1 1 d . . . . .
H1 H 0.8779 0.1390 0.4466 0.028 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 C1 1.786(2) . ?
C1 C1 1.523(3) 19_646 ?
C1 C1 1.523(3) 22_665 ?
C1 H1 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 C1 C1 111.41(16) 19_646 22_665 ?
C1 C1 CL1 108.7(2) 19_646 . ?
C1 C1 CL1 108.95(19) 22_665 . ?
C1 C1 H1 109.3 19_646 . ?
C1 C1 H1 109.3 22_665 . ?
CL1 C1 H1 109.3 . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.060



