# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_OT5
_database_code_depnum_ccdc_archive 'CCDC 1538885'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'5-(2,6-dichlorobenzyl)-1,3,4-oxadiazole-2(3H)-thione, dimethyl sulfoxide solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 Cl2 N2 O S, C2 H6 O S'
_chemical_formula_sum            'C11 H12 Cl2 N2 O2 S2'
_chemical_formula_weight         339.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
S S 0.1246 0.1234 '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                   11.9557(4)
_cell_length_b                   13.5378(5)
_cell_length_c                   9.0424(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.981(2)
_cell_angle_gamma                90
_cell_volume                     1441.40(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9190
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      32.20

_exptl_crystal_description       'irregular block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.738
_shelx_estimated_absorpt_T_min   0.674
_shelx_estimated_absorpt_T_max   0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5898
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25302
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.774
_diffrn_reflns_theta_max         33.422
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5158
_reflns_number_gt                4355
_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, 2011)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
; 
'SHELXL-2014/7 (Sheldrick, 2014) & TITAN (Hunter & Simpson, 1999)'
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  
;
'SHELXL-2014/7 (Sheldrick, 2014), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010), WINGX (Farrugia 1997)
;

_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)+(0.0364P)²+0.3560P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5158
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
O1 O 0.79399(7) 0.25208(6) 0.65447(9) 0.01403(15) Uani 1 1 d . . . . .
C2 C 0.82971(9) 0.15638(8) 0.68466(13) 0.01312(19) Uani 1 1 d . . . . .
S2 S 0.93383(2) 0.12599(2) 0.82270(3) 0.01747(7) Uani 1 1 d . . . . .
N3 N 0.76487(8) 0.10139(7) 0.58277(11) 0.01555(18) Uani 1 1 d . . . . .
H3N H 0.7672(13) 0.0347(12) 0.5770(18) 0.019 Uiso 1 1 d . U . . .
N4 N 0.68671(9) 0.15751(7) 0.48605(12) 0.01728(19) Uani 1 1 d . . . . .
C5 C 0.70753(9) 0.24629(8) 0.53311(13) 0.0138(2) Uani 1 1 d . . . . .
C6 C 0.65078(10) 0.33878(8) 0.47070(13) 0.0151(2) Uani 1 1 d . . . . .
H6A H 0.5899 0.3218 0.3856 0.018 Uiso 1 1 calc R U . . .
H6B H 0.7069 0.3806 0.4313 0.018 Uiso 1 1 calc R U . . .
C1' C 0.60000(9) 0.39721(8) 0.58506(12) 0.01242(19) Uani 1 1 d . . . . .
C2' C 0.49530(9) 0.37217(8) 0.62358(13) 0.0146(2) Uani 1 1 d . . . . .
Cl2' Cl 0.42238(2) 0.26949(2) 0.54050(4) 0.02198(7) Uani 1 1 d . . . . .
C3' C 0.44607(10) 0.42584(9) 0.72637(14) 0.0178(2) Uani 1 1 d . . . . .
H3' H 0.3750 0.4064 0.7503 0.021 Uiso 1 1 calc R U . . .
C4' C 0.50223(11) 0.50831(9) 0.79361(13) 0.0181(2) Uani 1 1 d . . . . .
H4' H 0.4692 0.5459 0.8636 0.022 Uiso 1 1 calc R U . . .
C5' C 0.60624(10) 0.53603(8) 0.75911(13) 0.0162(2) Uani 1 1 d . . . . .
H5' H 0.6446 0.5927 0.8046 0.019 Uiso 1 1 calc R U . . .
C6' C 0.65371(9) 0.48016(8) 0.65746(13) 0.0138(2) Uani 1 1 d . . . . .
Cl6' Cl 0.78621(2) 0.51665(2) 0.62246(4) 0.02286(7) Uani 1 1 d . . . . .
S1S S 0.14221(2) 0.17089(2) 0.37647(3) 0.01347(6) Uani 1 1 d . . . . .
O1S O 0.23619(7) 0.09661(6) 0.42744(10) 0.01759(17) Uani 1 1 d . . . . .
C1S C 0.01513(11) 0.11512(9) 0.41410(15) 0.0210(2) Uani 1 1 d . . . . .
H2S1 H 0.0042 0.0511 0.3629 0.031 Uiso 1 1 calc R U . . .
H2S2 H -0.0496 0.1582 0.3775 0.031 Uiso 1 1 calc R U . . .
H2S3 H 0.0210 0.1053 0.5226 0.031 Uiso 1 1 calc R U . . .
C2S C 0.11128(12) 0.16210(10) 0.17699(14) 0.0234(3) Uani 1 1 d . . . . .
H3S1 H 0.1753 0.1882 0.1345 0.035 Uiso 1 1 calc R U . . .
H3S2 H 0.0428 0.2005 0.1390 0.035 Uiso 1 1 calc R U . . .
H3S3 H 0.0987 0.0928 0.1476 0.035 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
O1 C5 1.3732(14) . ?
O1 C2 1.3765(13) . ?
C2 N3 1.3253(15) . ?
C2 S2 1.6548(12) . ?
N3 N4 1.3899(13) . ?
N3 H3N 0.905(16) . ?
N4 C5 1.2849(15) . ?
C5 C6 1.4879(15) . ?
C6 C1' 1.5103(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C1' C2' 1.3979(15) . ?
C1' C6' 1.3987(15) . ?
C2' C3' 1.3885(17) . ?
C2' Cl2' 1.7406(12) . ?
Cl2' O1S 3.2695(9) . ?
C3' C4' 1.3876(18) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.3853(17) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.3856(16) . ?
C5' H5' 0.9500 . ?
C6' Cl6' 1.7400(11) . ?
S1S O1S 1.5188(8) . ?
S1S C1S 1.7814(12) . ?
S1S C2S 1.7814(13) . ?
C1S H2S1 0.9800 . ?
C1S H2S2 0.9800 . ?
C1S H2S3 0.9800 . ?
C2S H3S1 0.9800 . ?
C2S H3S2 0.9800 . ?
C2S H3S3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C2 105.63(8) . . ?
N3 C2 O1 105.48(9) . . ?
N3 C2 S2 131.12(9) . . ?
O1 C2 S2 123.41(8) . . ?
C2 N3 N4 112.26(9) . . ?
C2 N3 H3N 125.5(10) . . ?
N4 N3 H3N 122.2(10) . . ?
C5 N4 N3 103.44(9) . . ?
N4 C5 O1 113.19(10) . . ?
N4 C5 C6 127.75(11) . . ?
O1 C5 C6 119.06(10) . . ?
C5 C6 C1' 113.08(9) . . ?
C5 C6 H6A 109.0 . . ?
C1' C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C1' C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C2' C1' C6' 115.87(10) . . ?
C2' C1' C6 121.82(10) . . ?
C6' C1' C6 122.31(10) . . ?
C3' C2' C1' 122.80(10) . . ?
C3' C2' Cl2' 117.91(9) . . ?
C1' C2' Cl2' 119.29(9) . . ?
C2' Cl2' O1S 165.84(4) . . ?
C4' C3' C2' 119.03(11) . . ?
C4' C3' H3' 120.5 . . ?
C2' C3' H3' 120.5 . . ?
C5' C4' C3' 120.30(11) . . ?
C5' C4' H4' 119.9 . . ?
C3' C4' H4' 119.9 . . ?
C4' C5' C6' 119.23(11) . . ?
C4' C5' H5' 120.4 . . ?
C6' C5' H5' 120.4 . . ?
C5' C6' C1' 122.77(10) . . ?
C5' C6' Cl6' 117.14(9) . . ?
C1' C6' Cl6' 120.09(9) . . ?
O1S S1S C1S 105.78(5) . . ?
O1S S1S C2S 106.01(6) . . ?
C1S S1S C2S 97.52(7) . . ?
S1S O1S Cl2' 92.79(4) . . ?
S1S C1S H2S1 109.5 . . ?
S1S C1S H2S2 109.5 . . ?
H2S1 C1S H2S2 109.5 . . ?
S1S C1S H2S3 109.5 . . ?
H2S1 C1S H2S3 109.5 . . ?
H2S2 C1S H2S3 109.5 . . ?
S1S C2S H3S1 109.5 . . ?
S1S C2S H3S2 109.5 . . ?
H3S1 C2S H3S2 109.5 . . ?
S1S C2S H3S3 109.5 . . ?
H3S1 C2S H3S3 109.5 . . ?
H3S2 C2S H3S3 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
C5 O1 C2 N3 0.17(11) . . . . ?
C5 O1 C2 S2 179.86(8) . . . . ?
O1 C2 N3 N4 -0.26(12) . . . . ?
S2 C2 N3 N4 -179.91(9) . . . . ?
C2 N3 N4 C5 0.25(13) . . . . ?
N3 N4 C5 O1 -0.13(13) . . . . ?
N3 N4 C5 C6 179.08(11) . . . . ?
C2 O1 C5 N4 -0.02(13) . . . . ?
C2 O1 C5 C6 -179.31(10) . . . . ?
N4 C5 C6 C1' 123.26(13) . . . . ?
O1 C5 C6 C1' -57.58(14) . . . . ?
C5 C6 C1' C2' -79.98(13) . . . . ?
C5 C6 C1' C6' 100.85(12) . . . . ?
C6' C1' C2' C3' 0.40(16) . . . . ?
C6 C1' C2' C3' -178.82(10) . . . . ?
C6' C1' C2' Cl2' -179.51(8) . . . . ?
C6 C1' C2' Cl2' 1.27(14) . . . . ?
C3' C2' Cl2' O1S 7.1(2) . . . . ?
C1' C2' Cl2' O1S -173.00(12) . . . . ?
C1' C2' C3' C4' 0.40(17) . . . . ?
Cl2' C2' C3' C4' -179.69(9) . . . . ?
C2' C3' C4' C5' -0.42(17) . . . . ?
C3' C4' C5' C6' -0.37(17) . . . . ?
C4' C5' C6' C1' 1.25(17) . . . . ?
C4' C5' C6' Cl6' -178.30(9) . . . . ?
C2' C1' C6' C5' -1.24(16) . . . . ?
C6 C1' C6' C5' 177.98(10) . . . . ?
C2' C1' C6' Cl6' 178.30(8) . . . . ?
C6 C1' C6' Cl6' -2.49(15) . . . . ?
C1S S1S O1S Cl2' -145.01(5) . . . . ?
C2S S1S O1S Cl2' 112.13(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
C5' H5' O1S 0.95 2.59 3.2255(14) 124.6 2_656
N3 H3N O1S 0.905(16) 1.778(16) 2.6820(13) 176.0(15) 3_656
C3' H3' O1S 0.95 2.50 3.3580(15) 150.5 4_566
C1S H2S2 S2 0.98 2.96 3.6923(13) 132.0 4_465
C2S H3S1 S1S 0.98 2.99 3.6029(13) 122.0 4_565

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_OT3
_database_code_depnum_ccdc_archive 'CCDC 1538886'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2017-05-23 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         'C9 H7 Cl N2 O S'
_chemical_formula_sum            'C9 H7 Cl N2 O S'
_chemical_formula_weight         226.68

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      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                   12.7860(5)
_cell_length_b                   12.8784(5)
_cell_length_c                   13.3520(6)
_cell_angle_alpha                90
_cell_angle_beta                 116.878(2)
_cell_angle_gamma                90
_cell_volume                     1961.07(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    91(2)
_cell_measurement_reflns_used    9861
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.80

_exptl_crystal_description       'irregular block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.580
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.567
_shelx_estimated_absorpt_T_min   0.692
_shelx_estimated_absorpt_T_max   0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6522
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Bruker 2011)'
_exptl_absorpt_special_details   
;
?
;
_diffrn_ambient_temperature      91(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49037
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.1333
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.786
_diffrn_reflns_theta_max         29.052
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5234
_reflns_number_gt                4070
_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, 2011)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
;
'SHELXL-2014/7 (Sheldrick, 2014) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  
;
'SHELXL-2014/7 (Sheldrick, 2014), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010), WINGX (Farrugia 1997)
;

_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)+(0.0595P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5234
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
O1 O 0.04495(10) 0.35668(9) 0.29173(10) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.04311(14) 0.41440(12) 0.37751(14) 0.0171(3) Uani 1 1 d . . . . .
S12 S 0.15819(4) 0.47978(4) 0.46981(4) 0.02074(12) Uani 1 1 d . . . . .
N13 N -0.06499(13) 0.40575(11) 0.36505(12) 0.0183(3) Uani 1 1 d . . . . .
H13N H -0.0877(18) 0.4323(14) 0.4044(17) 0.022 Uiso 1 1 d . U . . .
N14 N -0.13613(12) 0.34697(11) 0.27320(12) 0.0199(3) Uani 1 1 d . . . . .
C15 C -0.06721(14) 0.31894(13) 0.23178(14) 0.0186(4) Uani 1 1 d . . . . .
C16 C -0.09444(16) 0.25345(14) 0.13175(15) 0.0241(4) Uani 1 1 d . . . . .
H16A H -0.1806 0.2486 0.0866 0.029 Uiso 1 1 calc R U . . .
H16B H -0.0639 0.1825 0.1565 0.029 Uiso 1 1 calc R U . . .
C11' C -0.04164(15) 0.29637(13) 0.05888(14) 0.0219(4) Uani 1 1 d . . . . .
C12' C -0.10600(16) 0.35993(13) -0.03326(15) 0.0235(4) Uani 1 1 d . . . . .
H11' H -0.1855 0.3752 -0.0524 0.028 Uiso 1 1 calc R U . . .
C13' C -0.05602(16) 0.40109(14) -0.09713(16) 0.0252(4) Uani 1 1 d . . . . .
H13' H -0.1005 0.4444 -0.1597 0.030 Uiso 1 1 calc R U . . .
C14' C 0.05951(16) 0.37844(13) -0.06871(14) 0.0215(4) Uani 1 1 d . . . . .
Cl14 Cl 0.12490(4) 0.43068(3) -0.14753(4) 0.02919(14) Uani 1 1 d . . . . .
C15' C 0.12620(15) 0.31481(14) 0.02231(15) 0.0238(4) Uani 1 1 d . . . . .
H15' H 0.2057 0.2997 0.0411 0.029 Uiso 1 1 calc R U . . .
C16' C 0.07416(15) 0.27427(14) 0.08452(15) 0.0235(4) Uani 1 1 d . . . . .
H16' H 0.1186 0.2302 0.1464 0.028 Uiso 1 1 calc R U . . .
O2 O 0.46121(10) 0.12814(8) 0.74751(9) 0.0174(3) Uani 1 1 d . . . . .
C22 C 0.46202(15) 0.06940(12) 0.83324(14) 0.0173(4) Uani 1 1 d . . . . .
S22 S 0.34550(4) 0.00495(3) 0.82391(4) 0.02066(12) Uani 1 1 d . . . . .
N23 N 0.56882(12) 0.07951(11) 0.91707(12) 0.0179(3) Uani 1 1 d . . . . .
H23N H 0.5960(17) 0.0561(14) 0.9870(16) 0.021 Uiso 1 1 d . U . . .
N24 N 0.63905(12) 0.14488(10) 0.88980(12) 0.0185(3) Uani 1 1 d . . . . .
C25 C 0.57094(14) 0.17170(12) 0.78855(14) 0.0161(3) Uani 1 1 d . . . . .
C26 C 0.59491(14) 0.24510(13) 0.71581(14) 0.0182(4) Uani 1 1 d . . . . .
H26A H 0.6807 0.2502 0.7428 0.022 Uiso 1 1 calc R U . . .
H26B H 0.5659 0.3149 0.7221 0.022 Uiso 1 1 calc R U . . .
C21' C 0.53773(14) 0.21251(12) 0.59352(14) 0.0171(3) Uani 1 1 d . . . . .
C22' C 0.43093(14) 0.25572(13) 0.51869(14) 0.0189(4) Uani 1 1 d . . . . .
H22' H 0.3966 0.3086 0.5438 0.023 Uiso 1 1 calc R U . . .
C23' C 0.37388(15) 0.22244(13) 0.40769(14) 0.0198(4) Uani 1 1 d . . . . .
H23' H 0.3010 0.2521 0.3569 0.024 Uiso 1 1 calc R U . . .
C24' C 0.42513(15) 0.14546(13) 0.37256(14) 0.0190(4) Uani 1 1 d . . . . .
Cl24 Cl 0.35023(4) 0.09978(3) 0.23472(4) 0.02529(13) Uani 1 1 d . . . . .
C25' C 0.53260(15) 0.10316(13) 0.44417(14) 0.0206(4) Uani 1 1 d . . . . .
H25' H 0.5677 0.0519 0.4180 0.025 Uiso 1 1 calc R U . . .
C26' C 0.58841(15) 0.13664(13) 0.55469(14) 0.0191(4) Uani 1 1 d . . . . .
H26' H 0.6620 0.1076 0.6046 0.023 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
O1 C12 1.3744(19) . ?
O1 C15 1.3769(19) . ?
C12 N13 1.320(2) . ?
C12 S12 1.6593(17) . ?
N13 N14 1.3769(19) . ?
N13 H13N 0.784(19) . ?
N14 C15 1.286(2) . ?
C15 C16 1.482(2) . ?
C16 C11' 1.517(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C11' C16' 1.390(2) . ?
C11' C12' 1.395(2) . ?
C12' C13' 1.382(3) . ?
C12' H11' 0.9500 . ?
C13' C14' 1.380(2) . ?
C13' H13' 0.9500 . ?
C14' C15' 1.392(2) . ?
C14' Cl14 1.7478(18) . ?
C15' C16' 1.380(3) . ?
C15' H15' 0.9500 . ?
C16' H16' 0.9500 . ?
O2 C22 1.3681(19) . ?
O2 C25 1.3742(19) . ?
C22 N23 1.324(2) . ?
C22 S22 1.6603(17) . ?
N23 N24 1.3939(19) . ?
N23 H23N 0.889(19) . ?
N24 C25 1.281(2) . ?
C25 C26 1.483(2) . ?
C26 C21' 1.516(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C21' C22' 1.393(2) . ?
C21' C26' 1.395(2) . ?
C22' C23' 1.391(2) . ?
C22' H22' 0.9500 . ?
C23' C24' 1.382(2) . ?
C23' H23' 0.9500 . ?
C24' C25' 1.382(2) . ?
C24' Cl24 1.7484(17) . ?
Cl24 S12 3.4259(6) 4_565 ?
C25' C26' 1.386(2) . ?
C25' H25' 0.9500 . ?
C26' H26' 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C15 105.64(12) . . ?
N13 C12 O1 105.11(14) . . ?
N13 C12 S12 131.51(14) . . ?
O1 C12 S12 123.36(12) . . ?
C12 N13 N14 113.02(14) . . ?
C12 N13 H13N 124.3(15) . . ?
N14 N13 H13N 122.7(15) . . ?
C15 N14 N13 103.43(14) . . ?
N14 C15 O1 112.77(14) . . ?
N14 C15 C16 128.32(15) . . ?
O1 C15 C16 118.91(15) . . ?
C15 C16 C11' 112.29(14) . . ?
C15 C16 H16A 109.1 . . ?
C11' C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C11' C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C16' C11' C12' 118.39(17) . . ?
C16' C11' C16 120.05(16) . . ?
C12' C11' C16 121.55(16) . . ?
C13' C12' C11' 121.09(17) . . ?
C13' C12' H11' 119.5 . . ?
C11' C12' H11' 119.5 . . ?
C14' C13' C12' 119.04(17) . . ?
C14' C13' H13' 120.5 . . ?
C12' C13' H13' 120.5 . . ?
C13' C14' C15' 121.43(17) . . ?
C13' C14' Cl14 119.81(14) . . ?
C15' C14' Cl14 118.76(14) . . ?
C16' C15' C14' 118.45(17) . . ?
C16' C15' H15' 120.8 . . ?
C14' C15' H15' 120.8 . . ?
C15' C16' C11' 121.60(16) . . ?
C15' C16' H16' 119.2 . . ?
C11' C16' H16' 119.2 . . ?
C22 O2 C25 105.78(12) . . ?
N23 C22 O2 105.53(14) . . ?
N23 C22 S22 131.32(14) . . ?
O2 C22 S22 123.13(12) . . ?
C22 N23 N24 112.24(14) . . ?
C22 N23 H23N 128.2(13) . . ?
N24 N23 H23N 119.1(12) . . ?
C25 N24 N23 103.16(13) . . ?
N24 C25 O2 113.27(14) . . ?
N24 C25 C26 128.31(15) . . ?
O2 C25 C26 118.36(14) . . ?
C25 C26 C21' 112.77(13) . . ?
C25 C26 H26A 109.0 . . ?
C21' C26 H26A 109.0 . . ?
C25 C26 H26B 109.0 . . ?
C21' C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C22' C21' C26' 118.86(16) . . ?
C22' C21' C26 120.08(15) . . ?
C26' C21' C26 121.02(15) . . ?
C23' C22' C21' 120.87(16) . . ?
C23' C22' H22' 119.6 . . ?
C21' C22' H22' 119.6 . . ?
C24' C23' C22' 118.81(15) . . ?
C24' C23' H23' 120.6 . . ?
C22' C23' H23' 120.6 . . ?
C23' C24' C25' 121.57(16) . . ?
C23' C24' Cl24 118.72(13) . . ?
C25' C24' Cl24 119.71(13) . . ?
C24' Cl24 S12 169.51(6) . 4_565 ?
C24' C25' C26' 119.09(16) . . ?
C24' C25' H25' 120.5 . . ?
C26' C25' H25' 120.5 . . ?
C25' C26' C21' 120.76(16) . . ?
C25' C26' H26' 119.6 . . ?
C21' C26' H26' 119.6 . . ?

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
C15 O1 C12 N13 1.29(16) . . . . ?
C15 O1 C12 S12 -177.42(12) . . . . ?
O1 C12 N13 N14 -1.51(18) . . . . ?
S12 C12 N13 N14 177.05(13) . . . . ?
C12 N13 N14 C15 1.08(19) . . . . ?
N13 N14 C15 O1 -0.18(18) . . . . ?
N13 N14 C15 C16 179.63(17) . . . . ?
C12 O1 C15 N14 -0.70(18) . . . . ?
C12 O1 C15 C16 179.47(14) . . . . ?
N14 C15 C16 C11' 136.72(19) . . . . ?
O1 C15 C16 C11' -43.5(2) . . . . ?
C15 C16 C11' C16' 83.9(2) . . . . ?
C15 C16 C11' C12' -94.87(19) . . . . ?
C16' C11' C12' C13' -0.7(3) . . . . ?
C16 C11' C12' C13' 178.08(16) . . . . ?
C11' C12' C13' C14' 0.1(3) . . . . ?
C12' C13' C14' C15' 0.3(3) . . . . ?
C12' C13' C14' Cl14 -179.39(14) . . . . ?
C13' C14' C15' C16' 0.0(3) . . . . ?
Cl14 C14' C15' C16' 179.67(14) . . . . ?
C14' C15' C16' C11' -0.6(3) . . . . ?
C12' C11' C16' C15' 1.0(3) . . . . ?
C16 C11' C16' C15' -177.82(16) . . . . ?
C25 O2 C22 N23 -0.90(16) . . . . ?
C25 O2 C22 S22 177.70(11) . . . . ?
O2 C22 N23 N24 0.81(18) . . . . ?
S22 C22 N23 N24 -177.62(12) . . . . ?
C22 N23 N24 C25 -0.37(18) . . . . ?
N23 N24 C25 O2 -0.24(18) . . . . ?
N23 N24 C25 C26 176.88(16) . . . . ?
C22 O2 C25 N24 0.73(18) . . . . ?
C22 O2 C25 C26 -176.70(14) . . . . ?
N24 C25 C26 C21' 144.49(17) . . . . ?
O2 C25 C26 C21' -38.5(2) . . . . ?
C25 C26 C21' C22' 97.53(18) . . . . ?
C25 C26 C21' C26' -80.21(19) . . . . ?
C26' C21' C22' C23' 1.5(2) . . . . ?
C26 C21' C22' C23' -176.28(14) . . . . ?
C21' C22' C23' C24' 0.0(2) . . . . ?
C22' C23' C24' C25' -1.7(2) . . . . ?
C22' C23' C24' Cl24 177.24(12) . . . . ?
C23' C24' Cl24 S12 -31.6(4) . . . 4_565 ?
C25' C24' Cl24 S12 147.4(3) . . . 4_565 ?
C23' C24' C25' C26' 2.0(3) . . . . ?
Cl24 C24' C25' C26' -176.97(13) . . . . ?
C24' C25' C26' C21' -0.5(3) . . . . ?
C22' C21' C26' C25' -1.3(2) . . . . ?
C26 C21' C26' C25' 176.51(15) . . . . ?

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
N13 H13N S12 0.784(19) 2.507(19) 3.2911(16) 178.9(19) 3_566
C26 H26A N14 0.99 2.52 3.382(2) 145.3 4_666
C26' H26' N14 0.95 2.61 3.416(2) 142.8 4_666
N23 H23N S22 0.889(19) 2.417(19) 3.3043(15) 175.4(17) 3_657

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_OT6
_database_code_depnum_ccdc_archive 'CCDC 1538884'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2017-05-23 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         'C9 H7 Br N2 O S'
_chemical_formula_sum            'C9 H7 Br N2 O S'
_chemical_formula_weight         271.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Br Br -0.2901 2.4595 '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                   4.7154(4)
_cell_length_b                   11.7528(9)
_cell_length_c                   17.8887(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.015(4)
_cell_angle_gamma                90
_cell_volume                     991.38(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    92(2)
_cell_measurement_reflns_used    6720
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      31.87

_exptl_crystal_description       'rectangular block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    4.322
_shelx_estimated_absorpt_T_min   0.252
_shelx_estimated_absorpt_T_max   0.583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4218
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      92(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16808
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.467
_diffrn_reflns_theta_max         33.282
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.817
_diffrn_measured_fraction_theta_full 0.804
_diffrn_reflns_Laue_measured_fraction_max 0.817
_diffrn_reflns_Laue_measured_fraction_full 0.804
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_point_group_measured_fraction_full 0.804
_reflns_number_total             3122
_reflns_number_gt                2165
_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, 2011)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2014), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010)
;

_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)+(0.0206P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3122
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0620
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_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
O1 O 0.8881(3) 0.80680(10) 0.15058(7) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.9056(4) 0.89098(14) 0.09790(10) 0.0141(4) Uani 1 1 d . . . . .
S2 S 0.70903(11) 1.00783(4) 0.10026(3) 0.01817(11) Uani 1 1 d . . . . .
N3 N 1.1056(4) 0.85699(13) 0.05233(9) 0.0177(3) Uani 1 1 d . . . . .
H3N H 1.153(5) 0.8924(17) 0.0200(12) 0.021 Uiso 1 1 d . U . . .
N4 N 1.2285(3) 0.75468(12) 0.07375(10) 0.0186(3) Uani 1 1 d . . . . .
C5 C 1.0912(4) 0.72828(14) 0.13239(10) 0.0137(4) Uani 1 1 d . . . . .
C6 C 1.1247(4) 0.62633(14) 0.18045(10) 0.0156(4) Uani 1 1 d . . . . .
H6A H 1.1169 0.6499 0.2335 0.019 Uiso 1 1 calc R U . . .
H6B H 1.3135 0.5923 0.1713 0.019 Uiso 1 1 calc R U . . .
C1' C 0.8979(4) 0.53683(14) 0.16642(10) 0.0130(3) Uani 1 1 d . . . . .
C2' C 0.7763(4) 0.47932(15) 0.22597(10) 0.0155(4) Uani 1 1 d . . . . .
H2' H 0.8256 0.4996 0.2757 0.019 Uiso 1 1 calc R U . . .
C3' C 0.5822(4) 0.39183(14) 0.21344(11) 0.0165(4) Uani 1 1 d . . . . .
H3' H 0.5003 0.3523 0.2544 0.020 Uiso 1 1 calc R U . . .
C4' C 0.5102(4) 0.36312(14) 0.14115(11) 0.0151(4) Uani 1 1 d . . . . .
Br4' Br 0.25001(4) 0.24233(2) 0.12378(2) 0.02067(6) Uani 1 1 d . . . . .
C5' C 0.6219(4) 0.42036(14) 0.08107(11) 0.0163(4) Uani 1 1 d . . . . .
H5' H 0.5673 0.4011 0.0315 0.020 Uiso 1 1 calc R U . . .
C6' C 0.8174(4) 0.50744(14) 0.09405(10) 0.0156(4) Uani 1 1 d . . . . .
H6' H 0.8968 0.5473 0.0528 0.019 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
O1 C2 1.369(2) . ?
O1 C5 1.369(2) . ?
C2 N3 1.309(2) . ?
C2 S2 1.6574(18) . ?
N3 N4 1.389(2) . ?
N3 H3N 0.75(2) . ?
N4 C5 1.271(3) . ?
C5 C6 1.483(2) . ?
C6 C1' 1.521(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C1' C2' 1.386(2) . ?
C1' C6' 1.393(2) . ?
C2' C3' 1.395(3) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.379(3) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.373(3) . ?
C4' Br4' 1.9017(18) . ?
Br4' S2 3.5296(5) 1_545 ?
C5' C6' 1.397(3) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C5 106.33(14) . . ?
N3 C2 O1 104.58(15) . . ?
N3 C2 S2 132.20(14) . . ?
O1 C2 S2 123.19(14) . . ?
C2 N3 N4 113.15(16) . . ?
C2 N3 H3N 121.9(18) . . ?
N4 N3 H3N 124.8(18) . . ?
C5 N4 N3 103.08(15) . . ?
N4 C5 O1 112.83(15) . . ?
N4 C5 C6 128.42(17) . . ?
O1 C5 C6 118.75(17) . . ?
C5 C6 C1' 112.87(14) . . ?
C5 C6 H6A 109.0 . . ?
C1' C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C1' C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C2' C1' C6' 118.74(16) . . ?
C2' C1' C6 120.11(15) . . ?
C6' C1' C6 121.09(16) . . ?
C1' C2' C3' 120.51(17) . . ?
C1' C2' H2' 119.7 . . ?
C3' C2' H2' 119.7 . . ?
C4' C3' C2' 119.52(17) . . ?
C4' C3' H3' 120.2 . . ?
C2' C3' H3' 120.2 . . ?
C5' C4' C3' 121.30(17) . . ?
C5' C4' Br4' 119.04(14) . . ?
C3' C4' Br4' 119.65(14) . . ?
C4' Br4' S2 101.93(5) . 1_545 ?
C4' C5' C6' 118.83(17) . . ?
C4' C5' H5' 120.6 . . ?
C6' C5' H5' 120.6 . . ?
C1' C6' C5' 121.07(17) . . ?
C1' C6' H6' 119.5 . . ?
C5' C6' H6' 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C2 N3 1.53(18) . . . . ?
C5 O1 C2 S2 -176.76(13) . . . . ?
O1 C2 N3 N4 -1.8(2) . . . . ?
S2 C2 N3 N4 176.29(14) . . . . ?
C2 N3 N4 C5 1.3(2) . . . . ?
N3 N4 C5 O1 -0.21(19) . . . . ?
N3 N4 C5 C6 179.37(18) . . . . ?
C2 O1 C5 N4 -0.83(19) . . . . ?
C2 O1 C5 C6 179.54(15) . . . . ?
N4 C5 C6 C1' -101.9(2) . . . . ?
O1 C5 C6 C1' 77.6(2) . . . . ?
C5 C6 C1' C2' -138.91(17) . . . . ?
C5 C6 C1' C6' 43.9(2) . . . . ?
C6' C1' C2' C3' 1.5(3) . . . . ?
C6 C1' C2' C3' -175.68(17) . . . . ?
C1' C2' C3' C4' -0.4(3) . . . . ?
C2' C3' C4' C5' -1.2(3) . . . . ?
C2' C3' C4' Br4' 179.04(13) . . . . ?
C3' C4' C5' C6' 1.5(3) . . . . ?
Br4' C4' C5' C6' -178.68(14) . . . . ?
C2' C1' C6' C5' -1.2(3) . . . . ?
C6 C1' C6' C5' 176.02(16) . . . . ?
C4' C5' C6' C1' -0.4(3) . . . . ?

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
C3' H3' O1 0.95 2.56 3.441(2) 155.1 2_645
N3 H3N S2 0.75(2) 2.54(2) 3.2773(17) 173(2) 3_775

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_OT2
_database_code_depnum_ccdc_archive 'CCDC 1538887'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2017-05-23 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         'C9 H7 Cl N2 O S'
_chemical_formula_sum            'C9 H7 Cl N2 O S'
_chemical_formula_weight         226.68

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

_cell_length_a                   4.8187(3)
_cell_length_b                   9.7550(6)
_cell_length_c                   20.3555(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     956.84(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    5612
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      32.51

_exptl_crystal_description       'rectangular plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.581
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10092
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.315
_diffrn_reflns_theta_max         33.334
_diffrn_reflns_theta_full        31.500
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3294
_reflns_number_gt                3088
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_max     0.851
_reflns_Friedel_fraction_full    0.961

_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, 2011)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) & TITAN (Hunter & Simpson, 1999)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.0475P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1178 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3294
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0677
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
O1 O 0.1652(2) 0.59431(11) 0.49816(5) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.3136(3) 0.61665(14) 0.44189(7) 0.0136(3) Uani 1 1 d . . . . .
S2 S 0.16692(9) 0.66819(4) 0.37257(2) 0.01835(10) Uani 1 1 d . . . . .
N3 N 0.5722(3) 0.58231(13) 0.45648(7) 0.0152(3) Uani 1 1 d . . . . .
H3N H 0.707(5) 0.5945(19) 0.4281(9) 0.018 Uiso 1 1 d . U . . .
N4 N 0.5978(3) 0.53313(14) 0.52046(6) 0.0171(3) Uani 1 1 d . . . . .
C5 C 0.3510(4) 0.54223(14) 0.54289(7) 0.0140(3) Uani 1 1 d . . . . .
C6 C 0.2436(4) 0.50415(17) 0.60883(7) 0.0171(3) Uani 1 1 d . . . . .
H6A H 0.0778 0.4452 0.6036 0.021 Uiso 1 1 calc R U . . .
H6B H 0.1862 0.5882 0.6324 0.021 Uiso 1 1 calc R U . . .
C1' C 0.4578(3) 0.42911(15) 0.64914(7) 0.0142(3) Uani 1 1 d . . . . .
C2' C 0.5385(3) 0.29521(15) 0.63443(8) 0.0159(3) Uani 1 1 d . . . . .
Cl2' Cl 0.39032(10) 0.21111(4) 0.56781(2) 0.02354(10) Uani 1 1 d . . . . .
C3' C 0.7362(4) 0.22605(16) 0.67139(8) 0.0186(3) Uani 1 1 d . . . . .
H3' H 0.7884 0.1351 0.6601 0.022 Uiso 1 1 calc R U . . .
C4' C 0.8567(4) 0.29084(16) 0.72479(8) 0.0198(3) Uani 1 1 d . . . . .
H4' H 0.9926 0.2445 0.7503 0.024 Uiso 1 1 calc R U . . .
C5' C 0.7782(4) 0.42402(16) 0.74101(8) 0.0190(3) Uani 1 1 d . . . . .
H5' H 0.8598 0.4686 0.7777 0.023 Uiso 1 1 calc R U . . .
C6' C 0.5811(4) 0.49127(15) 0.70348(7) 0.0171(3) Uani 1 1 d . . . . .
H6' H 0.5285 0.5820 0.7150 0.021 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
O1 C2 1.3678(18) . ?
O1 C5 1.3743(19) . ?
C2 N3 1.324(2) . ?
C2 S2 1.6563(16) . ?
N3 N4 1.3935(18) . ?
N3 Cl2' 3.2844(14) 4_556 ?
N3 H3N 0.88(2) . ?
N4 C5 1.277(2) . ?
N4 O1 2.835(2) 1_655 ?
C5 C6 1.486(2) . ?
C6 C1' 1.508(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C1' C6' 1.394(2) . ?
C1' C2' 1.395(2) . ?
C2' C3' 1.389(2) . ?
C2' Cl2' 1.7383(16) . ?
C3' C4' 1.385(2) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.393(2) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.384(2) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C5 105.85(12) . . ?
N3 C2 O1 105.30(13) . . ?
N3 C2 S2 132.03(13) . . ?
O1 C2 S2 122.59(12) . . ?
C2 N3 N4 112.33(14) . . ?
C2 N3 Cl2' 128.75(10) . 4_556 ?
N4 N3 Cl2' 78.43(8) . 4_556 ?
C2 N3 H3N 121.0(13) . . ?
N4 N3 H3N 126.6(14) . . ?
Cl2' N3 H3N 71.0(13) 4_556 . ?
C5 N4 N3 103.17(13) . . ?
C5 N4 O1 160.18(12) . 1_655 ?
N3 N4 O1 82.13(9) . 1_655 ?
N4 C5 O1 113.31(14) . . ?
N4 C5 C6 129.05(15) . . ?
O1 C5 C6 117.64(14) . . ?
C5 C6 C1' 112.00(14) . . ?
C5 C6 H6A 109.2 . . ?
C1' C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C1' C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6' C1' C2' 117.31(15) . . ?
C6' C1' C6 120.80(14) . . ?
C2' C1' C6 121.89(14) . . ?
C3' C2' C1' 121.98(15) . . ?
C3' C2' Cl2' 118.37(12) . . ?
C1' C2' Cl2' 119.66(13) . . ?
C4' C3' C2' 119.41(14) . . ?
C4' C3' H3' 120.3 . . ?
C2' C3' H3' 120.3 . . ?
C3' C4' C5' 119.86(16) . . ?
C3' C4' H4' 120.1 . . ?
C5' C4' H4' 120.1 . . ?
C6' C5' C4' 119.84(15) . . ?
C6' C5' H5' 120.1 . . ?
C4' C5' H5' 120.1 . . ?
C5' C6' C1' 121.60(14) . . ?
C5' C6' H6' 119.2 . . ?
C1' C6' H6' 119.2 . . ?

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
N3 H3N S2 0.88(2) 2.59(2) 3.4397(15) 163.5(17) 1_655
N3 H3N O1 0.88(2) 2.63(2) 2.9833(19) 105.4(14) 1_655

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.057

