# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_NY-B376
_database_code_depnum_ccdc_archive 'CCDC 1470721'
_audit_update_record             
;
2016-03-26 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N2 O3'
_chemical_formula_weight         204.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   19.170(3)
_cell_length_b                   5.9569(10)
_cell_length_c                   7.7612(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     886.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    4231
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      26.92

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            8519
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.125
_diffrn_reflns_theta_max         27.187
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1865
_reflns_number_gt                1750
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_max     0.914
_reflns_Friedel_fraction_full    1.000

_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 APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  Yadokari-XG

_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)+(0.0485P)²+0.1839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 764 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1865
_refine_ls_number_parameters     168
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
C1 C 0.61655(11) 0.4198(4) 0.2334(3) 0.0209(5) Uani 1 1 d . . . . .
C2 C 0.54013(12) 0.3672(4) 0.2181(3) 0.0265(5) Uani 1 1 d . . . . .
H1 H 0.5105(18) 0.495(5) 0.199(4) 0.035(8) Uiso 1 1 d . . . . .
H2 H 0.5271(18) 0.284(5) 0.330(4) 0.041(8) Uiso 1 1 d . . . . .
C3 C 0.52875(13) 0.2141(5) 0.0606(4) 0.0319(6) Uani 1 1 d . . . . .
H3 H 0.537(2) 0.316(6) -0.054(5) 0.060(11) Uiso 1 1 d . . . . .
H4 H 0.4780(17) 0.163(5) 0.057(4) 0.036(8) Uiso 1 1 d . . . . .
C4 C 0.57694(14) 0.0079(4) 0.0526(4) 0.0286(5) Uani 1 1 d . . . . .
H5 H 0.572(2) -0.083(6) -0.042(5) 0.054(11) Uiso 1 1 d . . . . .
H6 H 0.565(2) -0.091(6) 0.158(5) 0.055(10) Uiso 1 1 d . . . . .
C5 C 0.65297(12) 0.0719(4) 0.0696(3) 0.0221(5) Uani 1 1 d . . . . .
C6 C 0.66561(11) 0.2701(4) 0.1578(3) 0.0194(5) Uani 1 1 d . . . . .
C7 C 0.72995(11) 0.3602(4) 0.1936(3) 0.0192(5) Uani 1 1 d . . . . .
C8 C 0.78894(10) 0.2435(4) 0.1363(3) 0.0213(5) Uani 1 1 d . . . . .
C9 C 0.77885(13) 0.0425(4) 0.0469(3) 0.0233(5) Uani 1 1 d . . . . .
H7 H 0.8197(16) -0.040(5) 0.000(4) 0.026(7) Uiso 1 1 d . . . . .
C10 C 0.71194(13) -0.0426(4) 0.0134(3) 0.0239(5) Uani 1 1 d . . . . .
H8 H 0.7076(15) -0.180(5) -0.047(4) 0.032(8) Uiso 1 1 d . . . . .
N1 N 0.64696(10) 0.5867(3) 0.3100(3) 0.0245(4) Uani 1 1 d . . . . .
N2 N 0.85854(10) 0.3257(4) 0.1721(3) 0.0243(5) Uani 1 1 d . . . . .
O1 O 0.72218(8) 0.5518(3) 0.2856(2) 0.0222(4) Uani 1 1 d . . . . .
O2 O 0.86393(9) 0.5036(3) 0.2517(3) 0.0314(4) Uani 1 1 d . . . . .
O3 O 0.90900(8) 0.2146(3) 0.1220(2) 0.0330(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.297(3) . ?
C1 C6 1.422(3) . ?
C1 C2 1.503(3) . ?
C2 C3 1.541(4) . ?
C2 H1 0.96(3) . ?
C2 H2 1.03(3) . ?
C3 C4 1.538(4) . ?
C3 H3 1.09(4) . ?
C3 H4 1.02(3) . ?
C4 C5 1.512(3) . ?
C4 H5 0.92(4) . ?
C4 H6 1.03(4) . ?
C5 C6 1.386(3) . ?
C5 C10 1.391(3) . ?
C6 C7 1.374(3) . ?
C7 O1 1.354(3) . ?
C7 C8 1.400(3) . ?
C8 C9 1.397(3) . ?
C8 N2 1.448(3) . ?
C9 C10 1.404(3) . ?
C9 H7 0.99(3) . ?
C10 H8 0.95(3) . ?
N1 O1 1.469(2) . ?
N2 O2 1.231(3) . ?
N2 O3 1.235(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C6 111.9(2) . . ?
N1 C1 C2 129.4(2) . . ?
C6 C1 C2 118.8(2) . . ?
C1 C2 C3 108.9(2) . . ?
C1 C2 H1 115(2) . . ?
C3 C2 H1 105.2(18) . . ?
C1 C2 H2 105.6(19) . . ?
C3 C2 H2 110.4(17) . . ?
H1 C2 H2 112(3) . . ?
C4 C3 C2 114.8(2) . . ?
C4 C3 H3 109(2) . . ?
C2 C3 H3 107(2) . . ?
C4 C3 H4 109.6(17) . . ?
C2 C3 H4 109.5(17) . . ?
H3 C3 H4 106(3) . . ?
C5 C4 C3 112.0(2) . . ?
C5 C4 H5 109(3) . . ?
C3 C4 H5 116(2) . . ?
C5 C4 H6 107(2) . . ?
C3 C4 H6 107(2) . . ?
H5 C4 H6 106(3) . . ?
C6 C5 C10 115.5(2) . . ?
C6 C5 C4 115.2(2) . . ?
C10 C5 C4 129.2(2) . . ?
C7 C6 C5 126.1(2) . . ?
C7 C6 C1 105.38(19) . . ?
C5 C6 C1 128.5(2) . . ?
O1 C7 C6 109.71(19) . . ?
O1 C7 C8 132.4(2) . . ?
C6 C7 C8 117.83(19) . . ?
C9 C8 C7 118.1(2) . . ?
C9 C8 N2 120.9(2) . . ?
C7 C8 N2 121.0(2) . . ?
C8 C9 C10 121.9(2) . . ?
C8 C9 H7 119.7(17) . . ?
C10 C9 H7 118.3(17) . . ?
C5 C10 C9 120.5(2) . . ?
C5 C10 H8 120.6(17) . . ?
C9 C10 H8 118.9(17) . . ?
C1 N1 O1 105.88(17) . . ?
O2 N2 O3 123.6(2) . . ?
O2 N2 C8 117.70(19) . . ?
O3 N2 C8 118.7(2) . . ?
C7 O1 N1 107.16(16) . . ?

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
N1 C1 C2 C3 157.5(2) . . . . ?
C6 C1 C2 C3 -23.4(3) . . . . ?
C1 C2 C3 C4 50.0(3) . . . . ?
C2 C3 C4 C5 -52.5(3) . . . . ?
C3 C4 C5 C6 25.9(3) . . . . ?
C3 C4 C5 C10 -155.9(2) . . . . ?
C10 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 C7 178.2(2) . . . . ?
C10 C5 C6 C1 -178.5(2) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
N1 C1 C6 C7 -0.3(3) . . . . ?
C2 C1 C6 C7 -179.6(2) . . . . ?
N1 C1 C6 C5 178.3(2) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C5 C6 C7 O1 -178.4(2) . . . . ?
C1 C6 C7 O1 0.2(2) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C1 C6 C7 C8 178.86(19) . . . . ?
O1 C7 C8 C9 178.0(2) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
O1 C7 C8 N2 -0.5(4) . . . . ?
C6 C7 C8 N2 -178.8(2) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
N2 C8 C9 C10 178.8(2) . . . . ?
C6 C5 C10 C9 0.2(3) . . . . ?
C4 C5 C10 C9 -177.9(2) . . . . ?
C8 C9 C10 C5 -0.3(4) . . . . ?
C6 C1 N1 O1 0.2(2) . . . . ?
C2 C1 N1 O1 179.4(2) . . . . ?
C9 C8 N2 O2 -179.8(2) . . . . ?
C7 C8 N2 O2 -1.3(3) . . . . ?
C9 C8 N2 O3 0.0(3) . . . . ?
C7 C8 N2 O3 178.5(2) . . . . ?
C6 C7 O1 N1 -0.1(2) . . . . ?
C8 C7 O1 N1 -178.4(2) . . . . ?
C1 N1 O1 C7 -0.1(2) . . . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_7-COOMe-8-Cl-Ts
_database_code_depnum_ccdc_archive 'CCDC 1470722'
_audit_update_record             
;
2016-03-26 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Cl N O5 S'
_chemical_formula_weight         407.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.0351(11)
_cell_length_b                   10.0395(11)
_cell_length_c                   10.3718(11)
_cell_angle_alpha                72.0480(10)
_cell_angle_beta                 81.2720(10)
_cell_angle_gamma                66.1780(10)
_cell_volume                     908.92(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5327
_cell_measurement_theta_min      2.065
_cell_measurement_theta_max      25.678

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.357
_shelx_estimated_absorpt_T_min   0.842
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            7866
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.065
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             3105
_reflns_number_gt                2876
_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 APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  Yadokari-XG
_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)+(0.0313P)²+0.5012P] 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         3105
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
C1 C 0.05427(16) 0.18216(16) 0.23280(14) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.02506(16) 0.13392(17) 0.11970(15) 0.0183(3) Uani 1 1 d . . . . .
H1 H -0.0054 0.2225 0.0393 0.022 Uiso 1 1 calc R U . . .
H2 H -0.0565 0.0986 0.1481 0.022 Uiso 1 1 calc R U . . .
C3 C 0.15747(18) 0.00790(19) 0.08005(16) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.1509 0.0126 -0.0156 0.027 Uiso 1 1 calc R U . . .
H4 H 0.1584 -0.0916 0.1374 0.027 Uiso 1 1 calc R U . . .
C4 C 0.29861(17) 0.02373(19) 0.09776(15) 0.0214(3) Uani 1 1 d . . . . .
H5 H 0.3834 -0.0551 0.0672 0.026 Uiso 1 1 calc R U . . .
H6 H 0.2973 0.1242 0.0427 0.026 Uiso 1 1 calc R U . . .
C5 C 0.31036(16) 0.00638(16) 0.24555(15) 0.0160(3) Uani 1 1 d . . . . .
C6 C 0.18531(16) 0.08319(16) 0.31521(15) 0.0142(3) Uani 1 1 d . . . . .
C7 C 0.18894(15) 0.05619(16) 0.45611(15) 0.0137(3) Uani 1 1 d . . . . .
C8 C 0.31542(16) -0.04440(16) 0.52611(15) 0.0148(3) Uani 1 1 d . . . . .
C9 C 0.43910(16) -0.11655(17) 0.45407(15) 0.0172(3) Uani 1 1 d . . . . .
H7 H 0.5258 -0.1844 0.5008 0.021 Uiso 1 1 calc R U . . .
C10 C 0.43665(16) -0.09036(17) 0.31538(15) 0.0170(3) Uani 1 1 d . . . . .
H8 H 0.5221 -0.1390 0.2675 0.020 Uiso 1 1 calc R U . . .
C11 C -0.24543(16) 0.53049(16) 0.37036(15) 0.0176(3) Uani 1 1 d . . . . .
C12 C -0.18123(16) 0.60078(17) 0.42293(16) 0.0193(3) Uani 1 1 d . . . . .
H9 H -0.1367 0.6658 0.3645 0.023 Uiso 1 1 calc R U . . .
C13 C -0.18324(16) 0.57437(17) 0.56223(16) 0.0204(3) Uani 1 1 d . . . . .
H10 H -0.1400 0.6224 0.5993 0.024 Uiso 1 1 calc R U . . .
C14 C -0.24747(17) 0.47888(17) 0.64881(16) 0.0205(3) Uani 1 1 d . . . . .
C15 C -0.31470(17) 0.41281(18) 0.59289(16) 0.0217(3) Uani 1 1 d . . . . .
H11 H -0.3618 0.3501 0.6510 0.026 Uiso 1 1 calc R U . . .
C16 C -0.31374(16) 0.43730(17) 0.45410(16) 0.0202(3) Uani 1 1 d . . . . .
H12 H -0.3589 0.3913 0.4166 0.024 Uiso 1 1 calc R U . . .
C17 C -0.2396(2) 0.4434(2) 0.79982(17) 0.0316(4) Uani 1 1 d . . . . .
H13 H -0.2502 0.5344 0.8237 0.047 Uiso 1 1 calc R U . . .
H14 H -0.1453 0.3631 0.8297 0.047 Uiso 1 1 calc R U . . .
H15 H -0.3182 0.4096 0.8445 0.047 Uiso 1 1 calc R U . . .
C18 C 0.32359(15) -0.07730(17) 0.67608(15) 0.0167(3) Uani 1 1 d . . . . .
C19 C 0.4230(2) -0.2692(2) 0.87422(17) 0.0345(4) Uani 1 1 d . . . . .
H16 H 0.3282 -0.2301 0.9201 0.052 Uiso 1 1 calc R U . . .
H17 H 0.4888 -0.2280 0.8936 0.052 Uiso 1 1 calc R U . . .
H18 H 0.4647 -0.3799 0.9070 0.052 Uiso 1 1 calc R U . . .
N1 N -0.02203(13) 0.30706(14) 0.26143(12) 0.0176(3) Uani 1 1 d . . . . .
O1 O -0.15267(11) 0.38445(12) 0.18089(11) 0.0207(2) Uani 1 1 d . . . . .
O2 O -0.14337(14) 0.63798(13) 0.13394(12) 0.0305(3) Uani 1 1 d . . . . .
O3 O -0.37243(13) 0.60047(14) 0.14082(12) 0.0314(3) Uani 1 1 d . . . . .
O4 O 0.26877(12) 0.01255(12) 0.74180(11) 0.0220(3) Uani 1 1 d . . . . .
O5 O 0.40399(12) -0.22431(12) 0.72945(11) 0.0251(3) Uani 1 1 d . . . . .
S1 S -0.23318(4) 0.55450(4) 0.19490(4) 0.02128(12) Uani 1 1 d . . . . .
Cl1 Cl 0.03154(4) 0.13654(4) 0.54686(3) 0.01579(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
C1 N1 1.277(2) . ?
C1 C6 1.486(2) . ?
C1 C2 1.505(2) . ?
C2 C3 1.527(2) . ?
C2 H1 0.9900 . ?
C2 H2 0.9900 . ?
C3 C4 1.531(2) . ?
C3 H3 0.9900 . ?
C3 H4 0.9900 . ?
C4 C5 1.506(2) . ?
C4 H5 0.9900 . ?
C4 H6 0.9900 . ?
C5 C10 1.387(2) . ?
C5 C6 1.406(2) . ?
C6 C7 1.405(2) . ?
C7 C8 1.397(2) . ?
C7 Cl1 1.7376(14) . ?
C8 C9 1.396(2) . ?
C8 C18 1.495(2) . ?
C9 C10 1.382(2) . ?
C9 H7 0.9500 . ?
C10 H8 0.9500 . ?
C11 C12 1.386(2) . ?
C11 C16 1.391(2) . ?
C11 S1 1.7523(16) . ?
C12 C13 1.385(2) . ?
C12 H9 0.9500 . ?
C13 C14 1.391(2) . ?
C13 H10 0.9500 . ?
C14 C15 1.396(2) . ?
C14 C17 1.502(2) . ?
C15 C16 1.383(2) . ?
C15 H11 0.9500 . ?
C16 H12 0.9500 . ?
C17 H13 0.9800 . ?
C17 H14 0.9800 . ?
C17 H15 0.9800 . ?
C18 O4 1.2022(19) . ?
C18 O5 1.3438(19) . ?
C19 O5 1.4471(19) . ?
C19 H16 0.9800 . ?
C19 H17 0.9800 . ?
C19 H18 0.9800 . ?
N1 O1 1.4593(15) . ?
O1 S1 1.6098(11) . ?
O2 S1 1.4231(13) . ?
O3 S1 1.4275(12) . ?

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
N1 C1 C6 115.80(13) . . ?
N1 C1 C2 125.06(13) . . ?
C6 C1 C2 119.06(12) . . ?
C1 C2 C3 112.94(13) . . ?
C1 C2 H1 109.0 . . ?
C3 C2 H1 109.0 . . ?
C1 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
H1 C2 H2 107.8 . . ?
C2 C3 C4 110.63(13) . . ?
C2 C3 H3 109.5 . . ?
C4 C3 H3 109.5 . . ?
C2 C3 H4 109.5 . . ?
C4 C3 H4 109.5 . . ?
H3 C3 H4 108.1 . . ?
C5 C4 C3 108.38(12) . . ?
C5 C4 H5 110.0 . . ?
C3 C4 H5 110.0 . . ?
C5 C4 H6 110.0 . . ?
C3 C4 H6 110.0 . . ?
H5 C4 H6 108.4 . . ?
C10 C5 C6 119.89(14) . . ?
C10 C5 C4 121.88(13) . . ?
C6 C5 C4 118.08(13) . . ?
C7 C6 C5 119.15(13) . . ?
C7 C6 C1 124.57(13) . . ?
C5 C6 C1 116.19(13) . . ?
C8 C7 C6 120.54(13) . . ?
C8 C7 Cl1 119.19(11) . . ?
C6 C7 Cl1 120.08(11) . . ?
C9 C8 C7 119.16(14) . . ?
C9 C8 C18 118.57(13) . . ?
C7 C8 C18 122.26(13) . . ?
C10 C9 C8 120.70(14) . . ?
C10 C9 H7 119.7 . . ?
C8 C9 H7 119.7 . . ?
C9 C10 C5 120.53(14) . . ?
C9 C10 H8 119.7 . . ?
C5 C10 H8 119.7 . . ?
C12 C11 C16 121.48(15) . . ?
C12 C11 S1 118.75(12) . . ?
C16 C11 S1 119.72(12) . . ?
C13 C12 C11 118.72(14) . . ?
C13 C12 H9 120.6 . . ?
C11 C12 H9 120.6 . . ?
C12 C13 C14 121.18(14) . . ?
C12 C13 H10 119.4 . . ?
C14 C13 H10 119.4 . . ?
C13 C14 C15 118.84(15) . . ?
C13 C14 C17 120.34(15) . . ?
C15 C14 C17 120.78(15) . . ?
C16 C15 C14 120.94(15) . . ?
C16 C15 H11 119.5 . . ?
C14 C15 H11 119.5 . . ?
C15 C16 C11 118.79(14) . . ?
C15 C16 H12 120.6 . . ?
C11 C16 H12 120.6 . . ?
C14 C17 H13 109.5 . . ?
C14 C17 H14 109.5 . . ?
H13 C17 H14 109.5 . . ?
C14 C17 H15 109.5 . . ?
H13 C17 H15 109.5 . . ?
H14 C17 H15 109.5 . . ?
O4 C18 O5 123.64(14) . . ?
O4 C18 C8 126.22(14) . . ?
O5 C18 C8 110.13(12) . . ?
O5 C19 H16 109.5 . . ?
O5 C19 H17 109.5 . . ?
H16 C19 H17 109.5 . . ?
O5 C19 H18 109.5 . . ?
H16 C19 H18 109.5 . . ?
H17 C19 H18 109.5 . . ?
C1 N1 O1 109.16(11) . . ?
N1 O1 S1 109.27(8) . . ?
C18 O5 C19 115.25(12) . . ?
O2 S1 O3 119.51(8) . . ?
O2 S1 O1 109.40(7) . . ?
O3 S1 O1 102.18(7) . . ?
O2 S1 C11 109.08(7) . . ?
O3 S1 C11 111.63(7) . . ?
O1 S1 C11 103.68(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
N1 C1 C2 C3 161.19(14) . . . . ?
C6 C1 C2 C3 -15.51(19) . . . . ?
C1 C2 C3 C4 -33.03(18) . . . . ?
C2 C3 C4 C5 62.71(17) . . . . ?
C3 C4 C5 C10 130.75(15) . . . . ?
C3 C4 C5 C6 -44.69(18) . . . . ?
C10 C5 C6 C7 -2.3(2) . . . . ?
C4 C5 C6 C7 173.24(13) . . . . ?
C10 C5 C6 C1 -178.88(13) . . . . ?
C4 C5 C6 C1 -3.34(19) . . . . ?
N1 C1 C6 C7 42.3(2) . . . . ?
C2 C1 C6 C7 -140.66(14) . . . . ?
N1 C1 C6 C5 -141.29(14) . . . . ?
C2 C1 C6 C5 35.71(19) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C1 C6 C7 C8 176.92(13) . . . . ?
C5 C6 C7 Cl1 -174.33(11) . . . . ?
C1 C6 C7 Cl1 1.94(19) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
Cl1 C7 C8 C9 175.82(10) . . . . ?
C6 C7 C8 C18 -179.51(12) . . . . ?
Cl1 C7 C8 C18 -4.49(19) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
C18 C8 C9 C10 179.67(13) . . . . ?
C8 C9 C10 C5 -1.0(2) . . . . ?
C6 C5 C10 C9 2.5(2) . . . . ?
C4 C5 C10 C9 -172.85(14) . . . . ?
C16 C11 C12 C13 1.3(2) . . . . ?
S1 C11 C12 C13 -176.13(11) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 -2.0(2) . . . . ?
C12 C13 C14 C17 175.84(15) . . . . ?
C13 C14 C15 C16 2.1(2) . . . . ?
C17 C14 C15 C16 -175.69(15) . . . . ?
C14 C15 C16 C11 -0.6(2) . . . . ?
C12 C11 C16 C15 -1.2(2) . . . . ?
S1 C11 C16 C15 176.24(11) . . . . ?
C9 C8 C18 O4 141.23(15) . . . . ?
C7 C8 C18 O4 -38.5(2) . . . . ?
C9 C8 C18 O5 -38.02(18) . . . . ?
C7 C8 C18 O5 142.30(14) . . . . ?
C6 C1 N1 O1 -174.96(11) . . . . ?
C2 C1 N1 O1 8.24(19) . . . . ?
C1 N1 O1 S1 -169.30(10) . . . . ?
O4 C18 O5 C19 -0.8(2) . . . . ?
C8 C18 O5 C19 178.48(14) . . . . ?
N1 O1 S1 O2 66.19(10) . . . . ?
N1 O1 S1 O3 -166.21(9) . . . . ?
N1 O1 S1 C11 -50.06(10) . . . . ?
C12 C11 S1 O2 4.89(14) . . . . ?
C16 C11 S1 O2 -172.60(12) . . . . ?
C12 C11 S1 O3 -129.36(12) . . . . ?
C16 C11 S1 O3 53.15(14) . . . . ?
C12 C11 S1 O1 121.37(12) . . . . ?
C16 C11 S1 O1 -56.12(13) . . . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_7-OMs-8-Cl-Ts-R
_database_code_depnum_ccdc_archive 'CCDC 1470723'
_audit_update_record             
;
2016-03-26 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Cl N O6 S2'
_chemical_formula_weight         443.90

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_
_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                   12.5262(12)
_cell_length_b                   9.5955(9)
_cell_length_c                   16.6342(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.049(3)
_cell_angle_gamma                90
_cell_volume                     1996.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9432
_cell_measurement_theta_min      4.31
_cell_measurement_theta_max      77.86

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.968
_shelx_estimated_absorpt_T_min   0.504
_shelx_estimated_absorpt_T_max   0.692
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5516
_exptl_absorpt_correction_T_max  0.6653
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            22548
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.533
_diffrn_reflns_theta_max         79.102
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4166
_reflns_number_gt                3776
_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       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.1178P)²+1.0550P] 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         4166
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1923
_refine_ls_wR_factor_gt          0.1779
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_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
C1 C 0.2617(2) 0.7460(3) 0.45708(15) 0.0366(5) Uani 1 1 d . . . . .
C2 C 0.3305(2) 0.7972(3) 0.52886(17) 0.0447(6) Uani 1 1 d . . . . .
H2A H 0.4065 0.7791 0.5191 0.054 Uiso 1 1 calc R U . . .
H2B H 0.3124 0.7435 0.5771 0.054 Uiso 1 1 calc R U . . .
C3 C 0.3163(3) 0.9514(3) 0.5456(2) 0.0509(7) Uani 1 1 d . . . . .
H3A H 0.3569 1.0069 0.5074 0.061 Uiso 1 1 calc R U . . .
H3B H 0.3443 0.9733 0.6009 0.061 Uiso 1 1 calc R U . . .
C4 C 0.1978(3) 0.9890(3) 0.53632(18) 0.0490(7) Uani 1 1 d . . . . .
H4A H 0.1571 0.9323 0.5739 0.059 Uiso 1 1 calc R U . . .
H4B H 0.1880 1.0885 0.5498 0.059 Uiso 1 1 calc R U . . .
C5 C 0.1563(2) 0.9622(3) 0.45110(16) 0.0396(6) Uani 1 1 d . . . . .
C6 C 0.1936(2) 0.8450(3) 0.40954(15) 0.0352(5) Uani 1 1 d . . . . .
C7 C 0.1593(2) 0.8257(3) 0.32790(15) 0.0346(5) Uani 1 1 d . . . . .
C8 C 0.0850(2) 0.9176(3) 0.29249(15) 0.0374(5) Uani 1 1 d . . . . .
C9 C 0.0469(2) 1.0295(3) 0.33418(18) 0.0431(6) Uani 1 1 d . . . . .
H9 H -0.0042 1.0907 0.3090 0.052 Uiso 1 1 calc R U . . .
C10 C 0.0833(2) 1.0520(3) 0.41261(19) 0.0449(6) Uani 1 1 d . . . . .
H10 H 0.0580 1.1303 0.4409 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3655(2) 0.3713(3) 0.37361(18) 0.0434(6) Uani 1 1 d . . . . .
C12 C 0.4678(3) 0.4277(4) 0.3710(2) 0.0556(8) Uani 1 1 d . . . . .
H12 H 0.5015 0.4700 0.4174 0.067 Uiso 1 1 calc R U . . .
C13 C 0.5190(3) 0.4210(5) 0.2998(2) 0.0645(10) Uani 1 1 d . . . . .
H13 H 0.5876 0.4621 0.2964 0.077 Uiso 1 1 calc R U . . .
C14 C 0.4716(3) 0.3550(5) 0.2334(2) 0.0617(9) Uani 1 1 d . . . . .
C15 C 0.3698(3) 0.3018(5) 0.2368(2) 0.0682(11) Uani 1 1 d . . . . .
H15 H 0.3365 0.2587 0.1906 0.082 Uiso 1 1 calc R U . . .
C16 C 0.3156(3) 0.3104(4) 0.3072(2) 0.0572(8) Uani 1 1 d . . . . .
H16 H 0.2450 0.2747 0.3094 0.069 Uiso 1 1 calc R U . . .
C17 C 0.5322(3) 0.3451(6) 0.1574(3) 0.0818(14) Uani 1 1 d . . . . .
H17A H 0.5764 0.2608 0.1593 0.123 Uiso 1 1 calc R U . . .
H17B H 0.5781 0.4272 0.1530 0.123 Uiso 1 1 calc R U . . .
H17C H 0.4814 0.3408 0.1106 0.123 Uiso 1 1 calc R U . . .
C18 C 0.0233(3) 1.0885(4) 0.10789(18) 0.0474(7) Uani 1 1 d . . . . .
H18A H 0.0492 1.1283 0.0583 0.071 Uiso 1 1 calc R U . . .
H18B H 0.0266 1.1594 0.1504 0.071 Uiso 1 1 calc R U . . .
H18C H -0.0508 1.0575 0.0982 0.071 Uiso 1 1 calc R U . . .
N1 N 0.25004(19) 0.6186(3) 0.43762(13) 0.0402(5) Uani 1 1 d . . . . .
O1 O 0.31739(16) 0.5350(2) 0.49286(12) 0.0447(5) Uani 1 1 d . . . . .
O2 O 0.3719(2) 0.3073(3) 0.52666(14) 0.0613(6) Uani 1 1 d . . . . .
O3 O 0.19457(19) 0.3398(2) 0.45548(14) 0.0535(5) Uani 1 1 d . . . . .
O4 O 0.04239(15) 0.8894(2) 0.21438(11) 0.0412(5) Uani 1 1 d . . . . .
O5 O 0.08896(17) 0.8402(2) 0.07896(12) 0.0493(5) Uani 1 1 d . . . . .
O6 O 0.20741(15) 0.9928(3) 0.16502(13) 0.0489(5) Uani 1 1 d . . . . .
S1 S 0.30465(6) 0.37479(7) 0.46576(4) 0.0446(2) Uani 1 1 d . . . . .
S2 S 0.10305(5) 0.94700(7) 0.13777(4) 0.0379(2) Uani 1 1 d . . . . .
Cl1 Cl 0.20586(5) 0.69227(7) 0.26983(4) 0.0423(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.271(4) . ?
C1 C6 1.477(4) . ?
C1 C2 1.517(4) . ?
C2 C3 1.517(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.526(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.506(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.388(4) . ?
C5 C6 1.412(4) . ?
C6 C7 1.415(3) . ?
C7 C8 1.390(4) . ?
C7 Cl1 1.724(3) . ?
C8 C9 1.377(4) . ?
C8 O4 1.405(3) . ?
C9 C10 1.376(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.371(4) . ?
C11 C12 1.393(5) . ?
C11 S1 1.748(3) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(6) . ?
C14 C17 1.512(5) . ?
C15 C16 1.387(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 S2 1.742(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 O1 1.455(3) . ?
O1 S1 1.608(2) . ?
O2 S1 1.437(2) . ?
O3 S1 1.421(2) . ?
O4 S2 1.6154(19) . ?
O5 S2 1.422(2) . ?
O6 S2 1.430(2) . ?

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
N1 C1 C6 115.3(2) . . ?
N1 C1 C2 124.4(3) . . ?
C6 C1 C2 120.0(2) . . ?
C1 C2 C3 113.1(3) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 109.6(3) . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 109.9(2) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C10 C5 C6 119.7(3) . . ?
C10 C5 C4 121.0(3) . . ?
C6 C5 C4 119.4(3) . . ?
C5 C6 C7 118.9(2) . . ?
C5 C6 C1 116.5(2) . . ?
C7 C6 C1 124.5(2) . . ?
C8 C7 C6 119.1(2) . . ?
C8 C7 Cl1 118.2(2) . . ?
C6 C7 Cl1 122.7(2) . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 O4 119.4(2) . . ?
C7 C8 O4 118.8(2) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C5 121.1(3) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
C16 C11 C12 121.5(3) . . ?
C16 C11 S1 120.8(2) . . ?
C12 C11 S1 117.7(2) . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 C17 121.2(4) . . ?
C13 C14 C17 119.0(4) . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 118.8(3) . . ?
C11 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S2 C18 H18A 109.5 . . ?
S2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 O1 108.3(2) . . ?
N1 O1 S1 107.74(16) . . ?
C8 O4 S2 119.49(17) . . ?
O3 S1 O2 120.49(16) . . ?
O3 S1 O1 109.92(13) . . ?
O2 S1 O1 100.83(13) . . ?
O3 S1 C11 110.85(14) . . ?
O2 S1 C11 110.04(15) . . ?
O1 S1 C11 102.85(13) . . ?
O5 S2 O6 121.18(14) . . ?
O5 S2 O4 104.46(13) . . ?
O6 S2 O4 108.39(11) . . ?
O5 S2 C18 108.51(15) . . ?
O6 S2 C18 110.58(16) . . ?
O4 S2 C18 101.84(13) . . ?

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
N1 C1 C2 C3 -171.0(3) . . . . ?
C6 C1 C2 C3 2.5(4) . . . . ?
C1 C2 C3 C4 42.1(4) . . . . ?
C2 C3 C4 C5 -62.1(3) . . . . ?
C3 C4 C5 C10 -141.6(3) . . . . ?
C3 C4 C5 C6 37.5(4) . . . . ?
C10 C5 C6 C7 3.0(4) . . . . ?
C4 C5 C6 C7 -176.1(2) . . . . ?
C10 C5 C6 C1 -173.4(2) . . . . ?
C4 C5 C6 C1 7.5(4) . . . . ?
N1 C1 C6 C5 145.1(3) . . . . ?
C2 C1 C6 C5 -28.9(4) . . . . ?
N1 C1 C6 C7 -31.1(4) . . . . ?
C2 C1 C6 C7 154.8(3) . . . . ?
C5 C6 C7 C8 -3.9(4) . . . . ?
C1 C6 C7 C8 172.3(2) . . . . ?
C5 C6 C7 Cl1 176.1(2) . . . . ?
C1 C6 C7 Cl1 -7.8(4) . . . . ?
C6 C7 C8 C9 2.2(4) . . . . ?
Cl1 C7 C8 C9 -177.7(2) . . . . ?
C6 C7 C8 O4 -173.1(2) . . . . ?
Cl1 C7 C8 O4 7.0(3) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
O4 C8 C9 C10 175.7(2) . . . . ?
C8 C9 C10 C5 -1.3(5) . . . . ?
C6 C5 C10 C9 -0.5(4) . . . . ?
C4 C5 C10 C9 178.6(3) . . . . ?
C16 C11 C12 C13 -0.2(6) . . . . ?
S1 C11 C12 C13 177.4(3) . . . . ?
C11 C12 C13 C14 -2.4(6) . . . . ?
C12 C13 C14 C15 3.4(7) . . . . ?
C12 C13 C14 C17 -177.7(4) . . . . ?
C13 C14 C15 C16 -1.8(7) . . . . ?
C17 C14 C15 C16 179.4(4) . . . . ?
C12 C11 C16 C15 1.8(6) . . . . ?
S1 C11 C16 C15 -175.7(3) . . . . ?
C14 C15 C16 C11 -0.8(7) . . . . ?
C6 C1 N1 O1 -176.6(2) . . . . ?
C2 C1 N1 O1 -2.9(4) . . . . ?
C1 N1 O1 S1 -178.23(18) . . . . ?
C9 C8 O4 S2 96.0(3) . . . . ?
C7 C8 O4 S2 -88.6(3) . . . . ?
N1 O1 S1 O3 -50.0(2) . . . . ?
N1 O1 S1 O2 -178.18(18) . . . . ?
N1 O1 S1 C11 68.15(19) . . . . ?
C16 C11 S1 O3 -14.0(3) . . . . ?
C12 C11 S1 O3 168.4(3) . . . . ?
C16 C11 S1 O2 121.8(3) . . . . ?
C12 C11 S1 O2 -55.8(3) . . . . ?
C16 C11 S1 O1 -131.4(3) . . . . ?
C12 C11 S1 O1 51.0(3) . . . . ?
C8 O4 S2 O5 143.8(2) . . . . ?
C8 O4 S2 O6 13.3(2) . . . . ?
C8 O4 S2 C18 -103.3(2) . . . . ?

_refine_diff_density_max         1.040
_refine_diff_density_min         -0.826
_refine_diff_density_rms         0.253

####################################################################### 
# 
# 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_B1182-2
_database_code_depnum_ccdc_archive 'CCDC 1470724'
_audit_update_record             
;
2016-03-26 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 Br Cl N O'
_chemical_formula_weight         316.62

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'
O O 0.0492 0.0322 '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                   10.5871(9)
_cell_length_b                   17.4471(15)
_cell_length_c                   7.3732(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.844(3)
_cell_angle_gamma                90
_cell_volume                     1296.42(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      4.39
_cell_measurement_theta_max      77.85

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    6.077
_shelx_estimated_absorpt_T_min   0.505
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5395
_exptl_absorpt_correction_T_max  0.6858
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            15100
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.387
_diffrn_reflns_theta_max         79.217
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2713
_reflns_number_gt                2386
_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       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0481P)²+3.5765P] 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         2713
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
C1 C 0.6091(4) 0.3649(2) 0.6633(7) 0.0411(10) Uani 1 1 d . . . . .
C2 C 0.7045(5) 0.3436(3) 0.5560(8) 0.0529(12) Uani 1 1 d . . . . .
H2A H 0.7324 0.2897 0.5855 0.063 Uiso 1 1 calc R U . . .
H2B H 0.7846 0.3761 0.6016 0.063 Uiso 1 1 calc R U . . .
C3 C 0.6474(5) 0.3524(3) 0.3420(8) 0.0528(13) Uani 1 1 d . . . . .
H3A H 0.5926 0.3071 0.2877 0.063 Uiso 1 1 calc R U . . .
H3B H 0.7203 0.3558 0.2845 0.063 Uiso 1 1 calc R U . . .
C4 C 0.5627(5) 0.4244(3) 0.2957(7) 0.0480(11) Uani 1 1 d . . . . .
H4A H 0.6165 0.4697 0.3536 0.058 Uiso 1 1 calc R U . . .
H4B H 0.5297 0.4321 0.1560 0.058 Uiso 1 1 calc R U . . .
C5 C 0.4470(5) 0.4157(2) 0.3740(6) 0.0382(9) Uani 1 1 d . . . . .
C6 C 0.4678(4) 0.3799(2) 0.5502(6) 0.0345(9) Uani 1 1 d . . . . .
C8 C 0.2282(4) 0.3889(2) 0.5125(6) 0.0332(8) Uani 1 1 d . . . . .
C7 C 0.3566(4) 0.3641(2) 0.6131(6) 0.0329(8) Uani 1 1 d . . . . .
C9 C 0.2138(5) 0.4272(3) 0.3413(6) 0.0410(10) Uani 1 1 d . . . . .
H9 H 0.1289 0.4461 0.2703 0.049 Uiso 1 1 calc R U . . .
C10 C 0.3207(5) 0.4385(3) 0.2719(6) 0.0438(11) Uani 1 1 d . . . . .
H10 H 0.3062 0.4625 0.1515 0.053 Uiso 1 1 calc R U . . .
C11 C 0.1024(4) 0.3762(2) 0.5743(6) 0.0345(8) Uani 1 1 d . . . . .
C12 C 0.1191(4) 0.4065(3) 0.7755(6) 0.0399(9) Uani 1 1 d . . . . .
H12A H 0.1540 0.4589 0.7869 0.060 Uiso 1 1 calc R U . . .
H12B H 0.1811 0.3735 0.8691 0.060 Uiso 1 1 calc R U . . .
H12C H 0.0329 0.4064 0.7990 0.060 Uiso 1 1 calc R U . . .
C13 C 0.0589(5) 0.2925(3) 0.5507(7) 0.0417(10) Uani 1 1 d . . . . .
H13A H 0.0347 0.2783 0.4158 0.063 Uiso 1 1 calc R U . . .
H13B H -0.0180 0.2856 0.5967 0.063 Uiso 1 1 calc R U . . .
H13C H 0.1319 0.2599 0.6246 0.063 Uiso 1 1 calc R U . . .
N1 N 0.6407(4) 0.3794(2) 0.8418(6) 0.0438(9) Uani 1 1 d . . . . .
O1 O -0.0055(3) 0.42014(18) 0.4526(4) 0.0438(7) Uani 1 1 d . . . . .
H14 H -0.0378 0.3969 0.3490 0.066 Uiso 1 1 calc R U . . .
Cl1 Cl 0.81073(12) 0.36683(9) 0.9649(2) 0.0638(4) Uani 1 1 d . . . . .
Br1 Br 0.38481(4) 0.29997(3) 0.83302(7) 0.04597(19) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.280(6) . ?
C1 C6 1.496(6) . ?
C1 C2 1.507(6) . ?
C2 C3 1.515(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.520(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.514(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.377(7) . ?
C5 C6 1.397(6) . ?
C6 C7 1.419(5) . ?
C8 C9 1.395(6) . ?
C8 C7 1.402(6) . ?
C8 C11 1.549(6) . ?
C7 Br1 1.917(4) . ?
C9 C10 1.392(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 O1 1.439(5) . ?
C11 C13 1.525(6) . ?
C11 C12 1.533(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 Cl1 1.764(4) . ?
O1 H14 0.8400 . ?

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
N1 C1 C6 116.1(4) . . ?
N1 C1 C2 125.6(4) . . ?
C6 C1 C2 117.9(4) . . ?
C1 C2 C3 113.8(4) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 109.7(4) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 108.8(4) . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C10 C5 C6 119.2(4) . . ?
C10 C5 C4 121.8(4) . . ?
C6 C5 C4 119.0(4) . . ?
C5 C6 C7 118.8(4) . . ?
C5 C6 C1 116.2(4) . . ?
C7 C6 C1 124.9(4) . . ?
C9 C8 C7 116.5(4) . . ?
C9 C8 C11 118.0(4) . . ?
C7 C8 C11 125.5(3) . . ?
C8 C7 C6 122.3(4) . . ?
C8 C7 Br1 120.2(3) . . ?
C6 C7 Br1 117.4(3) . . ?
C10 C9 C8 121.7(4) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C5 C10 C9 121.4(4) . . ?
C5 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
O1 C11 C13 106.5(3) . . ?
O1 C11 C12 104.7(3) . . ?
C13 C11 C12 112.4(4) . . ?
O1 C11 C8 109.3(3) . . ?
C13 C11 C8 111.1(3) . . ?
C12 C11 C8 112.4(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 N1 Cl1 114.1(3) . . ?
C11 O1 H14 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
N1 C1 C2 C3 -163.0(4) . . . . ?
C6 C1 C2 C3 9.1(6) . . . . ?
C1 C2 C3 C4 39.3(6) . . . . ?
C2 C3 C4 C5 -63.0(5) . . . . ?
C3 C4 C5 C10 -138.1(4) . . . . ?
C3 C4 C5 C6 38.5(5) . . . . ?
C10 C5 C6 C7 3.6(6) . . . . ?
C4 C5 C6 C7 -173.0(4) . . . . ?
C10 C5 C6 C1 -173.2(4) . . . . ?
C4 C5 C6 C1 10.2(5) . . . . ?
N1 C1 C6 C5 137.2(4) . . . . ?
C2 C1 C6 C5 -35.7(6) . . . . ?
N1 C1 C6 C7 -39.4(6) . . . . ?
C2 C1 C6 C7 147.7(4) . . . . ?
C9 C8 C7 C6 2.8(6) . . . . ?
C11 C8 C7 C6 -178.1(4) . . . . ?
C9 C8 C7 Br1 -172.2(3) . . . . ?
C11 C8 C7 Br1 6.8(5) . . . . ?
C5 C6 C7 C8 -5.5(6) . . . . ?
C1 C6 C7 C8 171.0(4) . . . . ?
C5 C6 C7 Br1 169.7(3) . . . . ?
C1 C6 C7 Br1 -13.8(5) . . . . ?
C7 C8 C9 C10 1.5(6) . . . . ?
C11 C8 C9 C10 -177.6(4) . . . . ?
C6 C5 C10 C9 0.6(6) . . . . ?
C4 C5 C10 C9 177.1(4) . . . . ?
C8 C9 C10 C5 -3.3(7) . . . . ?
C9 C8 C11 O1 -10.2(5) . . . . ?
C7 C8 C11 O1 170.7(4) . . . . ?
C9 C8 C11 C13 107.0(4) . . . . ?
C7 C8 C11 C13 -72.0(5) . . . . ?
C9 C8 C11 C12 -126.0(4) . . . . ?
C7 C8 C11 C12 54.9(5) . . . . ?
C6 C1 N1 Cl1 -175.9(3) . . . . ?
C2 C1 N1 Cl1 -3.7(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
O1 H14 Cl1 0.84 2.84 3.646(3) 160.6 1_454

_refine_diff_density_max         1.442
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.105

