# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1549958'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 Cl N O3 Se'
_chemical_formula_sum            'C28 H26 Cl N O3 Se'
_chemical_formula_weight         538.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.269(5)
_cell_length_b                   16.049(5)
_cell_length_c                   18.529(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2459.0(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5838
_cell_measurement_theta_min      27.01
_cell_measurement_theta_max      3.27

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.666
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   SADABS

_exptl_special_details           ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52923
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.981
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             4302
_reflns_number_gt                3966
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.965

_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.020(11)
_chemical_absolute_configuration Syn
_refine_ls_number_reflns         4302
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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
Se01 Se 0.49315(5) 0.82934(2) 0.27355(2) 0.01767(13) Uani 1 1 d . . . . .
Cl02 Cl 0.11737(14) 1.27439(6) 0.48187(6) 0.0295(3) Uani 1 1 d . . . . .
O003 O 0.1275(4) 0.97867(18) 0.14972(14) 0.0235(7) Uani 1 1 d . . . . .
O004 O 0.3757(3) 1.01454(16) 0.18884(13) 0.0153(6) Uani 1 1 d . . . . .
O005 O 0.3171(3) 0.84812(16) 0.43701(15) 0.0214(7) Uani 1 1 d . . . . .
N006 N 0.1031(4) 0.8647(2) 0.35905(17) 0.0148(7) Uani 1 1 d . . . . .
C007 C 0.3800(5) 1.0572(2) 0.3798(2) 0.0168(8) Uani 1 1 d . . . . .
C008 C -0.1202(5) 0.8882(2) 0.4469(2) 0.0175(9) Uani 1 1 d . . . . .
C009 C -0.0844(5) 0.9720(2) 0.4500(2) 0.0185(9) Uani 1 1 d . . . . .
H009 H 0.0035 0.9927 0.4243 0.022 Uiso 1 1 calc R U . . .
C010 C 0.1622(5) 0.6326(3) 0.2820(2) 0.0242(10) Uani 1 1 d . . . . .
H010 H 0.1255 0.5945 0.3161 0.029 Uiso 1 1 calc R U . . .
C011 C -0.0186(5) 0.8262(2) 0.4042(2) 0.0198(8) Uani 1 1 d . . . . .
H11A H 0.0343 0.7886 0.4378 0.024 Uiso 1 1 calc R U . . .
H11B H -0.0898 0.7932 0.3740 0.024 Uiso 1 1 calc R U . . .
C012 C 0.2510(5) 1.1206(2) 0.4831(2) 0.0204(9) Uani 1 1 d . . . . .
H012 H 0.2184 1.1178 0.5311 0.024 Uiso 1 1 calc R U . . .
C013 C -0.2522(5) 0.8583(3) 0.4855(2) 0.0201(9) Uani 1 1 d . . . . .
H013 H -0.2772 0.8018 0.4839 0.024 Uiso 1 1 calc R U . . .
C014 C -0.3083(5) 0.9956(3) 0.5300(2) 0.0210(9) Uani 1 1 d . . . . .
H014 H -0.3698 1.0314 0.5584 0.025 Uiso 1 1 calc R U . . .
C015 C 0.0772(5) 0.9026(2) 0.2918(2) 0.0142(9) Uani 1 1 d . . . . .
C016 C 0.2156(5) 0.9368(2) 0.2678(2) 0.0147(8) Uani 1 1 d . . . . .
C017 C 0.2767(5) 0.6916(2) 0.3014(2) 0.0189(9) Uani 1 1 d . . . . .
H017 H 0.3164 0.6934 0.3483 0.023 Uiso 1 1 calc R U . . .
C018 C -0.1779(5) 1.0255(3) 0.4909(2) 0.0214(9) Uani 1 1 d . . . . .
H018 H -0.1529 1.0820 0.4922 0.026 Uiso 1 1 calc R U . . .
C019 C 0.4039(5) 1.0549(2) 0.1199(2) 0.0226(10) Uani 1 1 d . . . . .
H01A H 0.3643 1.0193 0.0815 0.027 Uiso 1 1 calc R U . . .
H01B H 0.5192 1.0623 0.1130 0.027 Uiso 1 1 calc R U . . .
C020 C 0.2306(5) 0.9774(2) 0.1962(2) 0.0155(9) Uani 1 1 d . . . . .
C021 C 0.2719(5) 0.7448(3) 0.1804(2) 0.0236(10) Uani 1 1 d . . . . .
H021 H 0.3082 0.7829 0.1462 0.028 Uiso 1 1 calc R U . . .
C022 C 0.3304(5) 1.0545(2) 0.4516(2) 0.0191(9) Uani 1 1 d . . . . .
H022 H 0.3514 1.0071 0.4789 0.023 Uiso 1 1 calc R U . . .
C023 C 0.2205(5) 1.1909(2) 0.4427(2) 0.0183(9) Uani 1 1 d . . . . .
C024 C 0.3501(5) 0.9165(2) 0.3184(2) 0.0150(8) Uani 1 1 d . . . . .
C025 C 0.3211(6) 1.1386(3) 0.1151(2) 0.0280(11) Uani 1 1 d . . . . .
H02A H 0.3430 1.1632 0.0689 0.042 Uiso 1 1 calc R U . . .
H02B H 0.3612 1.1744 0.1526 0.042 Uiso 1 1 calc R U . . .
H02C H 0.2066 1.1314 0.1208 0.042 Uiso 1 1 calc R U . . .
C026 C 0.2629(5) 0.8728(2) 0.3799(2) 0.0151(9) Uani 1 1 d . . . . .
C027 C -0.0872(5) 0.8973(3) 0.2593(2) 0.0219(10) Uani 1 1 d . . . . .
H02D H -0.1580 0.8679 0.2915 0.033 Uiso 1 1 calc R U . . .
H02E H -0.0813 0.8682 0.2141 0.033 Uiso 1 1 calc R U . . .
H02F H -0.1284 0.9525 0.2514 0.033 Uiso 1 1 calc R U . . .
C028 C 0.1025(6) 0.6300(3) 0.2131(2) 0.0290(11) Uani 1 1 d . . . . .
H028 H 0.0243 0.5908 0.2009 0.035 Uiso 1 1 calc R U . . .
C029 C -0.3460(5) 0.9112(3) 0.5260(2) 0.0221(10) Uani 1 1 d . . . . .
H029 H -0.4350 0.8906 0.5509 0.027 Uiso 1 1 calc R U . . .
C030 C 0.4661(4) 0.9843(2) 0.3456(2) 0.0146(9) Uani 1 1 d . . . . .
H03A H 0.5393 0.9600 0.3807 0.018 Uiso 1 1 calc R U . . .
H03B H 0.5306 1.0043 0.3054 0.018 Uiso 1 1 calc R U . . .
C031 C 0.1580(6) 0.6854(3) 0.1613(2) 0.0295(11) Uani 1 1 d . . . . .
H031 H 0.1193 0.6828 0.1142 0.035 Uiso 1 1 calc R U . . .
C032 C 0.3486(5) 1.1291(2) 0.3409(2) 0.0192(9) Uani 1 1 d . . . . .
H032 H 0.3812 1.1323 0.2929 0.023 Uiso 1 1 calc R U . . .
C033 C 0.2698(5) 1.1962(3) 0.3717(2) 0.0237(10) Uani 1 1 d . . . . .
H033 H 0.2502 1.2442 0.3450 0.028 Uiso 1 1 calc R U . . .
C034 C 0.3319(5) 0.7480(2) 0.2500(2) 0.0165(9) 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
Se01 C034 1.917(4) . ?
Se01 C024 2.012(4) . ?
Cl02 C023 1.745(4) . ?
O003 C020 1.212(5) . ?
O004 C020 1.347(5) . ?
O004 C019 1.451(4) . ?
O005 C026 1.215(5) . ?
N006 C026 1.382(5) . ?
N006 C015 1.403(5) . ?
N006 C011 1.448(5) . ?
C007 C032 1.385(5) . ?
C007 C022 1.393(5) . ?
C007 C030 1.509(5) . ?
C008 C009 1.378(5) . ?
C008 C013 1.390(6) . ?
C008 C011 1.524(5) . ?
C009 C018 1.382(6) . ?
C010 C028 1.370(6) . ?
C010 C017 1.387(6) . ?
C012 C022 1.377(6) . ?
C012 C023 1.378(6) . ?
C013 C029 1.374(6) . ?
C014 C018 1.385(6) . ?
C014 C029 1.392(6) . ?
C015 C016 1.346(5) . ?
C015 C027 1.489(6) . ?
C016 C020 1.482(5) . ?
C016 C024 1.491(5) . ?
C017 C034 1.390(6) . ?
C019 C025 1.510(6) . ?
C021 C034 1.382(6) . ?
C021 C031 1.386(6) . ?
C023 C033 1.381(6) . ?
C024 C026 1.521(6) . ?
C024 C030 1.536(5) . ?
C028 C031 1.387(6) . ?
C032 C033 1.383(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
C034 Se01 C024 99.13(16) . . ?
C020 O004 C019 115.5(3) . . ?
C026 N006 C015 110.8(3) . . ?
C026 N006 C011 122.9(3) . . ?
C015 N006 C011 126.3(3) . . ?
C032 C007 C022 117.9(4) . . ?
C032 C007 C030 121.1(4) . . ?
C022 C007 C030 121.1(4) . . ?
C009 C008 C013 119.0(4) . . ?
C009 C008 C011 122.7(4) . . ?
C013 C008 C011 118.3(4) . . ?
C008 C009 C018 120.6(4) . . ?
C028 C010 C017 120.6(4) . . ?
N006 C011 C008 113.9(3) . . ?
C022 C012 C023 119.2(4) . . ?
C029 C013 C008 120.7(4) . . ?
C018 C014 C029 119.0(4) . . ?
C016 C015 N006 109.9(3) . . ?
C016 C015 C027 131.8(4) . . ?
N006 C015 C027 118.3(3) . . ?
C015 C016 C020 123.1(3) . . ?
C015 C016 C024 109.7(3) . . ?
C020 C016 C024 126.6(3) . . ?
C010 C017 C034 119.4(4) . . ?
C009 C018 C014 120.4(4) . . ?
O004 C019 C025 112.1(3) . . ?
O003 C020 O004 123.1(4) . . ?
O003 C020 C016 125.8(4) . . ?
O004 C020 C016 111.1(3) . . ?
C034 C021 C031 120.5(4) . . ?
C012 C022 C007 121.5(4) . . ?
C012 C023 C033 120.9(4) . . ?
C012 C023 Cl02 119.5(3) . . ?
C033 C023 Cl02 119.5(3) . . ?
C016 C024 C026 102.7(3) . . ?
C016 C024 C030 121.2(3) . . ?
C026 C024 C030 112.1(3) . . ?
C016 C024 Se01 109.3(2) . . ?
C026 C024 Se01 105.5(2) . . ?
C030 C024 Se01 105.1(2) . . ?
O005 C026 N006 124.4(4) . . ?
O005 C026 C024 128.9(4) . . ?
N006 C026 C024 106.6(3) . . ?
C010 C028 C031 120.4(4) . . ?
C013 C029 C014 120.3(4) . . ?
C007 C030 C024 113.1(3) . . ?
C021 C031 C028 119.3(4) . . ?
C033 C032 C007 121.5(4) . . ?
C023 C033 C032 119.0(4) . . ?
C021 C034 C017 119.8(4) . . ?
C021 C034 Se01 119.1(3) . . ?
C017 C034 Se01 121.0(3) . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.103

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_3aa
_database_code_depnum_ccdc_archive 'CCDC 1549957'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H26 Cl N O3 S'
_chemical_formula_sum            'C28 H26 Cl N O3 S'
_chemical_formula_weight         492.01
_chemical_absolute_configuration Syn
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.373(4)
_cell_length_b                   11.816(5)
_cell_length_c                   25.567(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2530(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5838
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      3.27
_cell_measurement_theta_min      27.01
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            70980
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.639
_diffrn_reflns_theta_min         3.086
_diffrn_ambient_temperature      140(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3921
_reflns_number_total             5838
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+0.5086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0939
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.54578(12) 0.91599(9) 0.24180(4) 0.0664(3) Uani 1 1 d . . . . .
S1 S 0.88490(10) 0.41240(8) 0.02815(3) 0.0478(2) Uani 1 1 d . . . . .
O1 O 0.9065(3) 0.68849(19) 0.02059(8) 0.0498(6) Uani 1 1 d . . . . .
O2 O 1.0577(4) 0.3542(2) 0.18481(11) 0.0755(8) Uani 1 1 d . . . . .
O3 O 0.8096(3) 0.3511(2) 0.15268(10) 0.0617(7) Uani 1 1 d . . . . .
N1 N 1.0784(3) 0.6524(2) 0.08833(9) 0.0381(6) Uani 1 1 d . . . . .
C1 C 1.4144(5) 0.4123(4) -0.00671(17) 0.0673(11) Uani 1 1 d . . . . .
H1 H 1.5231 0.4120 -0.0143 0.081 Uiso 1 1 calc R U . . .
C2 C 1.3569(5) 0.3455(4) 0.03267(16) 0.0654(11) Uani 1 1 d . . . . .
H10 H 1.4266 0.3008 0.0520 0.078 Uiso 1 1 calc R U . . .
C3 C 1.1942(5) 0.3443(3) 0.04383(14) 0.0531(9) Uani 1 1 d . . . . .
H11 H 1.1543 0.2980 0.0702 0.064 Uiso 1 1 calc R U . . .
C4 C 1.0932(4) 0.4126(3) 0.01535(11) 0.0418(8) Uani 1 1 d . . . . .
C5 C 0.8706(4) 0.5240(2) 0.07849(11) 0.0358(7) Uani 1 1 d . . . . .
C6 C 0.9484(4) 0.6313(3) 0.05751(12) 0.0361(7) Uani 1 1 d . . . . .
C7 C 1.1818(4) 0.7490(3) 0.07948(14) 0.0501(9) Uani 1 1 d . . . . .
H16 H 1.1714 0.7721 0.0432 0.060 Uiso 1 1 calc R U . . .
H17 H 1.2915 0.7254 0.0849 0.060 Uiso 1 1 calc R U . . .
C8 C 1.1488(4) 0.8501(3) 0.11396(13) 0.0450(8) Uani 1 1 d . . . . .
C9 C 1.0504(5) 0.8466(3) 0.15733(14) 0.0576(10) Uani 1 1 d . . . . .
H12 H 0.9967 0.7800 0.1655 0.069 Uiso 1 1 calc R U . . .
C10 C 1.0307(6) 0.9409(4) 0.18873(18) 0.0812(13) Uani 1 1 d . . . . .
H13 H 0.9628 0.9378 0.2175 0.097 Uiso 1 1 calc R U . . .
C11 C 1.1113(7) 1.0388(4) 0.1774(3) 0.106(2) Uani 1 1 d . . . . .
H2 H 1.1021 1.1015 0.1992 0.127 Uiso 1 1 calc R U . . .
C12 C 0.5944(4) 0.8092(3) 0.19774(12) 0.0406(8) Uani 1 1 d . . . . .
C13 C 0.5882(4) 0.8317(3) 0.14482(13) 0.0452(8) Uani 1 1 d . . . . .
H26 H 0.5619 0.9038 0.1330 0.054 Uiso 1 1 calc R U . . .
C14 C 0.6215(4) 0.7466(3) 0.10958(12) 0.0416(8) Uani 1 1 d . . . . .
H3 H 0.6177 0.7619 0.0739 0.050 Uiso 1 1 calc R U . . .
C15 C 0.6605(3) 0.6386(3) 0.12640(12) 0.0346(7) Uani 1 1 d . . . . .
C16 C 0.6680(4) 0.6193(3) 0.18013(13) 0.0420(8) Uani 1 1 d . . . . .
H4 H 0.6952 0.5477 0.1923 0.050 Uiso 1 1 calc R U . . .
C17 C 0.6359(4) 0.7040(3) 0.21573(13) 0.0483(9) Uani 1 1 d . . . . .
H5 H 0.6424 0.6900 0.2515 0.058 Uiso 1 1 calc R U . . .
C18 C 0.6920(4) 0.5457(3) 0.08727(13) 0.0400(8) Uani 1 1 d . . . . .
H7 H 0.6430 0.5659 0.0542 0.048 Uiso 1 1 calc R U . . .
H6 H 0.6421 0.4765 0.0994 0.048 Uiso 1 1 calc R U . . .
C19 C 1.3141(5) 0.4792(4) -0.03498(17) 0.0713(12) Uani 1 1 d . . . . .
H9 H 1.3541 0.5247 -0.0616 0.086 Uiso 1 1 calc R U . . .
C20 C 1.1544(4) 0.4794(3) -0.02402(14) 0.0574(10) Uani 1 1 d . . . . .
H8 H 1.0862 0.5253 -0.0434 0.069 Uiso 1 1 calc R U . . .
C21 C 0.9727(4) 0.4960(3) 0.12481(11) 0.0358(7) Uani 1 1 d . . . . .
C22 C 1.0940(3) 0.5707(3) 0.12751(11) 0.0387(7) Uani 1 1 d . . . . .
C23 C 1.2247(5) 0.9508(4) 0.1023(2) 0.0733(13) Uani 1 1 d . . . . .
H15 H 1.2895 0.9555 0.0729 0.088 Uiso 1 1 calc R U . . .
C24 C 1.2059(6) 1.0434(4) 0.1335(3) 0.103(2) Uani 1 1 d . . . . .
H14 H 1.2577 1.1105 0.1250 0.123 Uiso 1 1 calc R U . . .
C25 C 1.2331(4) 0.5747(4) 0.16334(14) 0.0637(11) Uani 1 1 d . . . . .
H19 H 1.2127 0.5276 0.1932 0.096 Uiso 1 1 calc R U . . .
H20 H 1.2502 0.6512 0.1746 0.096 Uiso 1 1 calc R U . . .
H18 H 1.3264 0.5478 0.1454 0.096 Uiso 1 1 calc R U . . .
C26 C 0.9566(5) 0.3950(3) 0.15751(13) 0.0487(9) Uani 1 1 d . . . . .
C27 C 0.7754(6) 0.2460(4) 0.1798(2) 0.0884(15) Uani 1 1 d . . . . .
H22 H 0.7597 0.2600 0.2169 0.106 Uiso 1 1 calc R U . . .
H21 H 0.8632 0.1932 0.1757 0.106 Uiso 1 1 calc R U . . .
C28 C 0.6278(7) 0.1991(4) 0.1563(2) 0.1071(19) Uani 1 1 d . . . . .
H24 H 0.5430 0.2533 0.1594 0.161 Uiso 1 1 calc R U . . .
H23 H 0.5985 0.1308 0.1742 0.161 Uiso 1 1 calc R U . . .
H25 H 0.6463 0.1827 0.1200 0.161 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 C12 1.740(3) . ?
S1 C4 1.774(3) . ?
S1 C5 1.846(3) . ?
O1 C6 1.213(3) . ?
O2 C26 1.198(4) . ?
O3 C26 1.341(4) . ?
O3 C27 1.452(4) . ?
N1 C6 1.366(4) . ?
N1 C7 1.450(4) . ?
N1 C22 1.398(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.367(6) . ?
C1 C19 1.362(6) . ?
C2 H10 0.9300 . ?
C2 C3 1.392(6) . ?
C3 H11 0.9300 . ?
C3 C4 1.377(5) . ?
C4 C20 1.378(5) . ?
C5 C6 1.523(4) . ?
C5 C18 1.534(4) . ?
C5 C21 1.497(4) . ?
C7 H16 0.9700 . ?
C7 H17 0.9700 . ?
C7 C8 1.511(5) . ?
C8 C9 1.382(5) . ?
C8 C23 1.381(5) . ?
C9 H12 0.9300 . ?
C9 C10 1.383(6) . ?
C10 H13 0.9300 . ?
C10 C11 1.370(7) . ?
C11 H2 0.9300 . ?
C11 C24 1.375(8) . ?
C12 C13 1.380(4) . ?
C12 C17 1.369(5) . ?
C13 H26 0.9300 . ?
C13 C14 1.379(4) . ?
C14 H3 0.9300 . ?
C14 C15 1.385(4) . ?
C15 C16 1.394(4) . ?
C15 C18 1.509(4) . ?
C16 H4 0.9300 . ?
C16 C17 1.379(4) . ?
C17 H5 0.9300 . ?
C18 H7 0.9700 . ?
C18 H6 0.9700 . ?
C19 H9 0.9300 . ?
C19 C20 1.366(5) . ?
C20 H8 0.9300 . ?
C21 C22 1.347(4) . ?
C21 C26 1.464(4) . ?
C22 C25 1.482(4) . ?
C23 H15 0.9300 . ?
C23 C24 1.363(7) . ?
C24 H14 0.9300 . ?
C25 H19 0.9600 . ?
C25 H20 0.9600 . ?
C25 H18 0.9600 . ?
C27 H22 0.9700 . ?
C27 H21 0.9700 . ?
C27 C28 1.482(7) . ?
C28 H24 0.9600 . ?
C28 H23 0.9600 . ?
C28 H25 0.9600 . ?

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 S1 C5 101.03(13) . . ?
C26 O3 C27 117.9(3) . . ?
C6 N1 C7 121.9(3) . . ?
C6 N1 C22 111.2(2) . . ?
C22 N1 C7 126.8(3) . . ?
C2 C1 H1 119.7 . . ?
C19 C1 H1 119.7 . . ?
C19 C1 C2 120.6(4) . . ?
C1 C2 H10 119.9 . . ?
C1 C2 C3 120.1(4) . . ?
C3 C2 H10 119.9 . . ?
C2 C3 H11 120.4 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H11 120.4 . . ?
C3 C4 S1 120.3(3) . . ?
C3 C4 C20 119.6(3) . . ?
C20 C4 S1 120.1(3) . . ?
C6 C5 S1 108.7(2) . . ?
C6 C5 C18 109.2(3) . . ?
C18 C5 S1 106.5(2) . . ?
C21 C5 S1 110.9(2) . . ?
C21 C5 C6 102.6(2) . . ?
C21 C5 C18 118.5(3) . . ?
O1 C6 N1 125.3(3) . . ?
O1 C6 C5 127.9(3) . . ?
N1 C6 C5 106.8(3) . . ?
N1 C7 H16 108.5 . . ?
N1 C7 H17 108.5 . . ?
N1 C7 C8 115.0(3) . . ?
H16 C7 H17 107.5 . . ?
C8 C7 H16 108.5 . . ?
C8 C7 H17 108.5 . . ?
C9 C8 C7 123.6(3) . . ?
C23 C8 C7 118.1(3) . . ?
C23 C8 C9 118.3(4) . . ?
C8 C9 H12 119.6 . . ?
C8 C9 C10 120.8(4) . . ?
C10 C9 H12 119.6 . . ?
C9 C10 H13 120.0 . . ?
C11 C10 C9 119.9(5) . . ?
C11 C10 H13 120.0 . . ?
C10 C11 H2 120.3 . . ?
C10 C11 C24 119.3(5) . . ?
C24 C11 H2 120.3 . . ?
C13 C12 Cl1 119.1(2) . . ?
C17 C12 Cl1 120.0(3) . . ?
C17 C12 C13 120.9(3) . . ?
C12 C13 H26 120.3 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H26 120.3 . . ?
C13 C14 H3 119.4 . . ?
C13 C14 C15 121.1(3) . . ?
C15 C14 H3 119.4 . . ?
C14 C15 C16 117.8(3) . . ?
C14 C15 C18 120.4(3) . . ?
C16 C15 C18 121.8(3) . . ?
C15 C16 H4 119.2 . . ?
C17 C16 C15 121.5(3) . . ?
C17 C16 H4 119.2 . . ?
C12 C17 C16 119.1(3) . . ?
C12 C17 H5 120.5 . . ?
C16 C17 H5 120.5 . . ?
C5 C18 H7 109.0 . . ?
C5 C18 H6 109.0 . . ?
C15 C18 C5 112.9(2) . . ?
C15 C18 H7 109.0 . . ?
C15 C18 H6 109.0 . . ?
H7 C18 H6 107.8 . . ?
C1 C19 H9 120.1 . . ?
C1 C19 C20 119.7(4) . . ?
C20 C19 H9 120.1 . . ?
C4 C20 H8 119.6 . . ?
C19 C20 C4 120.9(4) . . ?
C19 C20 H8 119.6 . . ?
C22 C21 C5 109.1(3) . . ?
C22 C21 C26 125.0(3) . . ?
C26 C21 C5 125.4(3) . . ?
N1 C22 C25 119.6(3) . . ?
C21 C22 N1 110.2(3) . . ?
C21 C22 C25 130.2(3) . . ?
C8 C23 H15 119.6 . . ?
C24 C23 C8 120.8(5) . . ?
C24 C23 H15 119.6 . . ?
C11 C24 H14 119.6 . . ?
C23 C24 C11 120.8(5) . . ?
C23 C24 H14 119.6 . . ?
C22 C25 H19 109.5 . . ?
C22 C25 H20 109.5 . . ?
C22 C25 H18 109.5 . . ?
H19 C25 H20 109.5 . . ?
H19 C25 H18 109.5 . . ?
H20 C25 H18 109.5 . . ?
O2 C26 O3 123.1(3) . . ?
O2 C26 C21 126.5(3) . . ?
O3 C26 C21 110.3(3) . . ?
O3 C27 H22 110.3 . . ?
O3 C27 H21 110.3 . . ?
O3 C27 C28 106.9(4) . . ?
H22 C27 H21 108.6 . . ?
C28 C27 H22 110.3 . . ?
C28 C27 H21 110.3 . . ?
C27 C28 H24 109.5 . . ?
C27 C28 H23 109.5 . . ?
C27 C28 H25 109.5 . . ?
H24 C28 H23 109.5 . . ?
H24 C28 H25 109.5 . . ?
H23 C28 H25 109.5 . . ?

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
C7 H16 O1 0.97 2.60 3.261(4) 125.6 2_565
C7 H16 O1 0.97 2.60 3.261(4) 125.6 2_565
C18 H6 O3 0.97 2.45 3.009(4) 116.2 .
C18 H6 O3 0.97 2.45 3.009(4) 116.2 .
C25 H19 Cl1 0.96 2.93 3.581(4) 126.1 3_745
C25 H19 Cl1 0.96 2.93 3.581(4) 126.1 3_745
C25 H19 O2 0.96 2.43 3.040(5) 120.8 .
C25 H19 O2 0.96 2.43 3.040(5) 120.8 .

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
Cl1 C12 C13 C14 -177.9(3) . . . . ?
Cl1 C12 C17 C16 177.5(3) . . . . ?
S1 C4 C20 C19 -178.9(3) . . . . ?
S1 C5 C6 O1 64.4(4) . . . . ?
S1 C5 C6 N1 -115.3(2) . . . . ?
S1 C5 C18 C15 -178.0(2) . . . . ?
S1 C5 C21 C22 112.5(2) . . . . ?
S1 C5 C21 C26 -59.7(3) . . . . ?
N1 C7 C8 C9 12.0(5) . . . . ?
N1 C7 C8 C23 -169.9(3) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C1 C19 C20 C4 0.0(6) . . . . ?
C2 C1 C19 C20 -0.2(6) . . . . ?
C2 C3 C4 S1 179.5(3) . . . . ?
C2 C3 C4 C20 0.9(5) . . . . ?
C3 C4 C20 C19 -0.3(5) . . . . ?
C4 S1 C5 C6 53.9(2) . . . . ?
C4 S1 C5 C18 171.5(2) . . . . ?
C4 S1 C5 C21 -58.2(2) . . . . ?
C5 S1 C4 C3 89.5(3) . . . . ?
C5 S1 C4 C20 -91.9(3) . . . . ?
C5 C21 C22 N1 3.5(3) . . . . ?
C5 C21 C22 C25 -175.0(3) . . . . ?
C5 C21 C26 O2 158.1(3) . . . . ?
C5 C21 C26 O3 -21.3(4) . . . . ?
C6 N1 C7 C8 98.3(4) . . . . ?
C6 N1 C22 C21 -2.1(3) . . . . ?
C6 N1 C22 C25 176.6(3) . . . . ?
C6 C5 C18 C15 -60.7(3) . . . . ?
C6 C5 C21 C22 -3.5(3) . . . . ?
C6 C5 C21 C26 -175.6(3) . . . . ?
C7 N1 C6 O1 0.2(5) . . . . ?
C7 N1 C6 C5 179.9(3) . . . . ?
C7 N1 C22 C21 177.8(3) . . . . ?
C7 N1 C22 C25 -3.6(5) . . . . ?
C7 C8 C9 C10 177.0(4) . . . . ?
C7 C8 C23 C24 -176.7(4) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C8 C23 C24 C11 0.2(7) . . . . ?
C9 C8 C23 C24 1.5(6) . . . . ?
C9 C10 C11 C24 2.7(7) . . . . ?
C10 C11 C24 C23 -2.3(8) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C12 C17 C16 -1.6(5) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C13 C14 C15 C18 178.3(3) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C14 C15 C18 C5 100.3(3) . . . . ?
C15 C16 C17 C12 0.6(5) . . . . ?
C16 C15 C18 C5 -80.3(4) . . . . ?
C17 C12 C13 C14 1.2(5) . . . . ?
C18 C5 C6 O1 -51.5(4) . . . . ?
C18 C5 C6 N1 128.8(3) . . . . ?
C18 C5 C21 C22 -123.8(3) . . . . ?
C18 C5 C21 C26 64.0(4) . . . . ?
C18 C15 C16 C17 -178.7(3) . . . . ?
C19 C1 C2 C3 0.8(6) . . . . ?
C21 C5 C6 O1 -178.1(3) . . . . ?
C21 C5 C6 N1 2.2(3) . . . . ?
C21 C5 C18 C15 56.2(4) . . . . ?
C22 N1 C6 O1 -180.0(3) . . . . ?
C22 N1 C6 C5 -0.3(3) . . . . ?
C22 N1 C7 C8 -81.5(4) . . . . ?
C22 C21 C26 O2 -12.8(5) . . . . ?
C22 C21 C26 O3 167.8(3) . . . . ?
C23 C8 C9 C10 -1.1(5) . . . . ?
C26 O3 C27 C28 -163.6(4) . . . . ?
C26 C21 C22 N1 175.7(3) . . . . ?
C26 C21 C22 C25 -2.8(5) . . . . ?
C27 O3 C26 O2 -3.3(5) . . . . ?
C27 O3 C26 C21 176.1(3) . . . . ?

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1549959'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        2014/7

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 Cl N O4'
_chemical_formula_sum            'C22 H22 Cl N O4'
_chemical_formula_weight         399.85

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

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

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

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

_cell_length_a                   13.4035(11)
_cell_length_b                   28.882(2)
_cell_length_c                   5.1236(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1983.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5838
_cell_measurement_theta_min      27.01
_cell_measurement_theta_max      3.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   SADABS

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60586
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.040
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3474
_reflns_number_gt                3103
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.968

_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0544P)²+0.4142P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
Refined as an inversion twin.
;

_refine_ls_abs_structure_Flack   0.02(8)
_chemical_absolute_configuration Syn
_refine_ls_number_reflns         3474
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_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
H25 H -0.144(2) 0.7304(10) 0.633(6) 0.034(9) Uiso 1 1 d . . . . .
Cl1 Cl 0.29288(6) 0.48559(2) 0.32602(16) 0.0391(2) Uani 1 1 d . . . . .
O1 O 0.21329(11) 0.74320(6) 0.3028(3) 0.0214(4) Uani 1 1 d . . . . .
O2 O -0.06574(12) 0.63071(6) -0.0176(4) 0.0263(4) Uani 1 1 d . . . . .
O4 O -0.09034(14) 0.72115(6) 0.6221(3) 0.0210(4) Uani 1 1 d . . . . .
C8 C 0.07315(17) 0.69797(8) 0.1428(5) 0.0165(5) Uani 1 1 d . . . . .
C10 C 0.12352(17) 0.73453(8) 0.3026(5) 0.0174(5) Uani 1 1 d . . . . .
O3 O -0.19190(12) 0.67440(6) 0.1348(4) 0.0270(4) Uani 1 1 d . . . . .
C21 C -0.10408(18) 0.66792(8) 0.1025(5) 0.0197(6) Uani 1 1 d . . . . .
C7 C 0.13271(18) 0.66967(8) -0.0465(5) 0.0192(5) Uani 1 1 d . . . . .
H7A H 0.1886 0.6882 -0.1060 0.023 Uiso 1 1 calc R U . . .
H7B H 0.0912 0.6632 -0.1972 0.023 Uiso 1 1 calc R U . . .
N1 N 0.05173(14) 0.75579(7) 0.4437(4) 0.0175(4) Uani 1 1 d . . . . .
C12 C 0.05890(19) 0.84137(9) 0.5019(5) 0.0207(5) Uani 1 1 d . . . . .
C1 C 0.17286(18) 0.62405(9) 0.0573(5) 0.0198(5) Uani 1 1 d . . . . .
C9 C -0.02416(17) 0.69884(8) 0.1989(5) 0.0176(5) Uani 1 1 d . . . . .
C5 C 0.1673(2) 0.55871(9) 0.3513(6) 0.0298(6) Uani 1 1 d . . . . .
H5 H 0.1387 0.5439 0.4941 0.036 Uiso 1 1 calc R U . . .
C24 C -0.11563(18) 0.77444(8) 0.2625(5) 0.0209(5) Uani 1 1 d . . . . .
H24A H -0.0857 0.7853 0.1037 0.031 Uiso 1 1 calc R U . . .
H24B H -0.1236 0.7999 0.3811 0.031 Uiso 1 1 calc R U . . .
H24C H -0.1797 0.7612 0.2248 0.031 Uiso 1 1 calc R U . . .
C11 C -0.04872(17) 0.73782(8) 0.3866(4) 0.0167(5) Uani 1 1 d . . . . .
C22 C -0.1370(2) 0.59725(10) -0.1150(7) 0.0396(8) Uani 1 1 d . . . . .
H22A H -0.1730 0.6099 -0.2630 0.047 Uiso 1 1 calc R U . . .
H22B H -0.1847 0.5893 0.0201 0.047 Uiso 1 1 calc R U . . .
C3 C 0.2876(2) 0.55992(10) 0.0082(6) 0.0332(7) Uani 1 1 d . . . . .
H3 H 0.3397 0.5458 -0.0814 0.040 Uiso 1 1 calc R U . . .
C15 C 0.0391(2) 0.92854(9) 0.2779(7) 0.0339(7) Uani 1 1 d . . . . .
H15 H 0.0328 0.9578 0.2034 0.041 Uiso 1 1 calc R U . . .
C20 C 0.07100(19) 0.79383(8) 0.6242(5) 0.0215(6) Uani 1 1 d . . . . .
H20A H 0.1385 0.7909 0.6908 0.026 Uiso 1 1 calc R U . . .
H20B H 0.0257 0.7913 0.7711 0.026 Uiso 1 1 calc R U . . .
C17 C -0.0067(2) 0.87367(9) 0.6050(6) 0.0298(6) Uani 1 1 d . . . . .
H17 H -0.0451 0.8660 0.7499 0.036 Uiso 1 1 calc R U . . .
C4 C 0.24488(19) 0.53858(9) 0.2190(5) 0.0266(6) Uani 1 1 d . . . . .
C13 C 0.11414(18) 0.85325(8) 0.2834(5) 0.0247(6) Uani 1 1 d . . . . .
H13 H 0.1586 0.8320 0.2125 0.030 Uiso 1 1 calc R U . . .
C6 C 0.13200(19) 0.60138(9) 0.2697(5) 0.0266(6) Uani 1 1 d . . . . .
H6 H 0.0796 0.6151 0.3598 0.032 Uiso 1 1 calc R U . . .
C14 C 0.10389(19) 0.89662(9) 0.1692(6) 0.0305(6) Uani 1 1 d . . . . .
H14 H 0.1403 0.9041 0.0207 0.037 Uiso 1 1 calc R U . . .
C2 C 0.25209(19) 0.60289(10) -0.0701(6) 0.0281(6) Uani 1 1 d . . . . .
H2 H 0.2820 0.6178 -0.2107 0.034 Uiso 1 1 calc R U . . .
C16 C -0.0157(2) 0.91737(10) 0.4942(6) 0.0370(8) Uani 1 1 d . . . . .
H16 H -0.0590 0.9390 0.5670 0.044 Uiso 1 1 calc R U . . .
C23 C -0.0793(3) 0.55530(11) -0.1953(11) 0.0690(13) Uani 1 1 d . . . . .
H23A H -0.1244 0.5323 -0.2619 0.103 Uiso 1 1 calc R U . . .
H23B H -0.0444 0.5430 -0.0471 0.103 Uiso 1 1 calc R U . . .
H23C H -0.0323 0.5636 -0.3286 0.103 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.748(3) . ?
O1 C10 1.229(3) . ?
O2 C21 1.341(3) . ?
O2 C22 1.447(3) . ?
O4 C11 1.414(3) . ?
C8 C9 1.336(3) . ?
C8 C10 1.497(3) . ?
C8 C7 1.499(3) . ?
C10 N1 1.351(3) . ?
O3 C21 1.203(3) . ?
C21 C9 1.479(3) . ?
C7 C1 1.519(3) . ?
N1 C20 1.459(3) . ?
N1 C11 1.472(3) . ?
C12 C13 1.385(4) . ?
C12 C17 1.387(4) . ?
C12 C20 1.518(4) . ?
C1 C6 1.383(4) . ?
C1 C2 1.388(4) . ?
C9 C11 1.517(3) . ?
C5 C4 1.371(4) . ?
C5 C6 1.385(4) . ?
C24 C11 1.525(3) . ?
C22 C23 1.495(4) . ?
C3 C4 1.369(4) . ?
C3 C2 1.389(4) . ?
C15 C16 1.369(5) . ?
C15 C14 1.384(4) . ?
C17 C16 1.389(4) . ?
C13 C14 1.389(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 C22 116.1(2) . . ?
C9 C8 C10 108.0(2) . . ?
C9 C8 C7 132.0(2) . . ?
C10 C8 C7 119.9(2) . . ?
O1 C10 N1 127.2(2) . . ?
O1 C10 C8 125.9(2) . . ?
N1 C10 C8 106.97(19) . . ?
O3 C21 O2 124.3(2) . . ?
O3 C21 C9 124.6(2) . . ?
O2 C21 C9 111.1(2) . . ?
C8 C7 C1 115.8(2) . . ?
C10 N1 C20 123.73(19) . . ?
C10 N1 C11 112.64(19) . . ?
C20 N1 C11 123.58(19) . . ?
C13 C12 C17 118.7(2) . . ?
C13 C12 C20 120.0(2) . . ?
C17 C12 C20 121.3(2) . . ?
C6 C1 C2 117.7(2) . . ?
C6 C1 C7 123.1(2) . . ?
C2 C1 C7 119.2(2) . . ?
C8 C9 C21 128.6(2) . . ?
C8 C9 C11 111.2(2) . . ?
C21 C9 C11 120.2(2) . . ?
C4 C5 C6 119.1(3) . . ?
O4 C11 N1 108.15(18) . . ?
O4 C11 C9 111.97(19) . . ?
N1 C11 C9 100.90(18) . . ?
O4 C11 C24 111.09(19) . . ?
N1 C11 C24 112.08(19) . . ?
C9 C11 C24 112.20(19) . . ?
O2 C22 C23 107.2(2) . . ?
C4 C3 C2 119.1(3) . . ?
C16 C15 C14 120.4(3) . . ?
N1 C20 C12 113.6(2) . . ?
C12 C17 C16 120.7(3) . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 Cl1 119.7(2) . . ?
C3 C4 Cl1 119.2(2) . . ?
C12 C13 C14 120.7(2) . . ?
C1 C6 C5 121.6(2) . . ?
C15 C14 C13 119.6(3) . . ?
C1 C2 C3 121.3(3) . . ?
C15 C16 C17 119.9(3) . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

