# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1860486'
_audit_update_record             
;
2018-08-06 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H45 N6 O7 S2'
_chemical_formula_weight         858.00

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'

_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                   10.295(9)
_cell_length_b                   11.374(8)
_cell_length_c                   36.37(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4258(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4521
_cell_measurement_theta_min      2.1545
_cell_measurement_theta_max      29.8541

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.185
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16630
_diffrn_reflns_av_unetI/netI     0.3052
_diffrn_reflns_av_R_equivalents  0.1437
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         2.273
_diffrn_reflns_theta_max         28.324
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             10134
_reflns_number_gt                3740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.924
_reflns_Friedel_fraction_full    0.959

_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 (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)+(0.1691P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 933 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         10134
_refine_ls_number_parameters     552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3148
_refine_ls_R_factor_gt           0.1246
_refine_ls_wR_factor_ref         0.3622
_refine_ls_wR_factor_gt          0.2737
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
S001 S 0.8032(4) -0.0779(3) 0.68372(10) 0.0596(11) Uani 1 1 d . . . . .
S002 S 0.5333(4) -0.0174(3) 0.53878(10) 0.0606(11) Uani 1 1 d . . . . .
O001 O 0.6131(9) 0.2206(8) 0.6080(2) 0.057(2) Uani 1 1 d . . . . .
O201 O 0.9141(8) 0.2475(7) 0.6601(2) 0.050(2) Uani 1 1 d . . . . .
O701 O 0.7418(10) -0.1752(7) 0.6655(2) 0.061(3) Uani 1 1 d . . . . .
O601 O 0.7823(11) -0.0662(7) 0.7218(2) 0.066(3) Uani 1 1 d . . . . .
N007 N 0.7446(12) 0.0422(8) 0.6637(3) 0.058(3) Uani 1 1 d . . . . .
N008 N 0.7559(10) 0.3019(8) 0.7305(3) 0.043(2) Uani 1 1 d . . . . .
C009 C 0.6579(11) 0.4637(10) 0.7363(3) 0.038(3) Uani 1 1 d . . . . .
O401 O 0.5753(11) -0.0130(10) 0.5020(2) 0.085(3) Uani 1 1 d . . . . .
N16 N 0.6343(10) 0.3495(8) 0.7316(3) 0.047(3) Uani 1 1 d . . . . .
N012 N 0.6659(9) -0.0096(9) 0.5635(2) 0.044(2) Uani 1 1 d . . . . .
O301 O 0.4466(10) 0.0695(9) 0.5517(3) 0.081(3) Uani 1 1 d . . . . .
N014 N 0.5659(9) 0.5502(9) 0.7403(3) 0.055(3) Uani 1 1 d . . . . .
O501 O 0.9510(9) 0.6368(8) 0.7440(3) 0.073(3) Uani 1 1 d . . . . .
C011 C 0.8507(12) 0.3790(10) 0.7338(3) 0.041(3) Uani 1 1 d . . . . .
H011 H 0.939127 0.362454 0.733221 0.049 Uiso 1 1 calc R U . . .
N017 N 0.7363(11) 0.6816(9) 0.7473(3) 0.054(3) Uani 1 1 d . . . . .
H017 H 0.755351 0.753814 0.751692 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7769(13) 0.2448(11) 0.6544(3) 0.047(3) Uani 1 1 d . . . . .
H3 H 0.738793 0.323381 0.656996 0.056 Uiso 1 1 calc R U . . .
C019 C 0.7610(14) 0.1752(9) 0.7211(3) 0.048(3) Uani 1 1 d . . . . .
H01A H 0.704438 0.131226 0.737445 0.058 Uiso 1 1 calc R U . . .
H01B H 0.848864 0.145960 0.724140 0.058 Uiso 1 1 calc R U . . .
C020 C 0.7963(11) 0.4873(10) 0.7382(3) 0.037(3) Uani 1 1 d . . . . .
C2 C 0.7552(13) 0.0542(9) 0.6236(3) 0.046(3) Uani 1 1 d . . . . .
H2 H 0.841203 0.027798 0.615500 0.055 Uiso 1 1 calc R U . . .
C1 C 0.7177(14) 0.1591(9) 0.6817(3) 0.047(3) Uani 1 1 d . . . . .
H1 H 0.623419 0.171041 0.681150 0.057 Uiso 1 1 calc R U . . .
C023 C 0.4620(15) -0.1556(13) 0.5463(4) 0.062(4) Uani 1 1 d . . . . .
C024 C 0.6679(15) 0.4133(12) 0.5837(4) 0.058(4) Uani 1 1 d . . . . .
C025 C 0.6470(13) -0.0175(11) 0.6028(4) 0.055(4) Uani 1 1 d . . . . .
H02A H 0.650352 -0.099284 0.610317 0.066 Uiso 1 1 calc R U . . .
H02B H 0.562064 0.013280 0.609151 0.066 Uiso 1 1 calc R U . . .
C4 C 0.7414(13) 0.1890(12) 0.6169(3) 0.052(3) Uani 1 1 d . . . . .
H4 H 0.801690 0.215298 0.597674 0.062 Uiso 1 1 calc R U . . .
C027 C 0.5076(15) -0.2539(15) 0.5318(4) 0.067(4) Uani 1 1 d . . . . .
H027 H 0.579258 -0.250207 0.516300 0.081 Uiso 1 1 calc R U . . .
C028 C 0.8422(14) 0.6015(10) 0.7433(3) 0.045(3) Uani 1 1 d . . . . .
C029 C 0.6091(16) 0.6542(12) 0.7448(4) 0.060(4) Uani 1 1 d . . . . .
C030 C 1.1104(14) 0.3520(12) 0.6532(4) 0.057(4) Uani 1 1 d . . . . .
C031 C 0.7841(13) -0.0652(11) 0.5497(4) 0.056(4) Uani 1 1 d . . . . .
H03A H 0.764632 -0.104127 0.526631 0.067 Uiso 1 1 calc R U . . .
H03B H 0.811590 -0.124949 0.567079 0.067 Uiso 1 1 calc R U . . .
C032 C 0.6291(16) 0.4879(12) 0.6123(4) 0.064(4) Uani 1 1 d . . . . .
H032 H 0.559198 0.467078 0.627142 0.077 Uiso 1 1 calc R U . . .
C033 C 0.344(2) -0.3716(16) 0.5621(5) 0.079(5) Uani 1 1 d . . . . .
C034 C 0.4521(19) -0.3624(15) 0.5392(5) 0.078(5) Uani 1 1 d . . . . .
H034 H 0.487346 -0.429830 0.528672 0.094 Uiso 1 1 calc R U . . .
C035 C 0.9752(16) -0.0977(12) 0.6750(4) 0.063(4) Uani 1 1 d . . . . .
C036 C 1.1936(16) 0.2780(13) 0.6362(4) 0.064(4) Uani 1 1 d . . . . .
H036 H 1.161827 0.226601 0.618469 0.077 Uiso 1 1 calc R U . . .
C037 C 0.9670(15) 0.3535(12) 0.6449(5) 0.073(4) Uani 1 1 d . . . . .
H03C H 0.926306 0.421807 0.655968 0.087 Uiso 1 1 calc R U . . .
H03D H 0.952551 0.356185 0.618540 0.087 Uiso 1 1 calc R U . . .
C038 C 0.8957(14) 0.0204(13) 0.5436(4) 0.057(4) Uani 1 1 d . . . . .
C039 C 0.6941(19) 0.5922(14) 0.6186(4) 0.078(5) Uani 1 1 d . . . . .
H039 H 0.667123 0.641647 0.637493 0.094 Uiso 1 1 calc R U . . .
C040 C 1.2350(17) -0.134(2) 0.6702(5) 0.085(5) Uani 1 1 d . . . . .
C041 C 1.1911(18) -0.0195(16) 0.6707(4) 0.078(5) Uani 1 1 d . . . . .
H041 H 1.248371 0.043488 0.668773 0.093 Uiso 1 1 calc R U . . .
C042 C 0.6033(18) 0.2998(11) 0.5774(4) 0.068(4) Uani 1 1 d . . . . .
H04A H 0.512263 0.313775 0.572133 0.082 Uiso 1 1 calc R U . . .
H04B H 0.641472 0.262745 0.555913 0.082 Uiso 1 1 calc R U . . .
C043 C 1.295(2) 0.4263(18) 0.6893(5) 0.083(5) Uani 1 1 d . . . . .
H043 H 1.329121 0.478365 0.706411 0.099 Uiso 1 1 calc R U . . .
C044 C 1.1633(19) 0.4245(14) 0.6810(5) 0.081(5) Uani 1 1 d . . . . .
H044 H 1.107700 0.473019 0.694258 0.097 Uiso 1 1 calc R U . . .
C045 C 1.0585(15) -0.0016(13) 0.6741(4) 0.066(4) Uani 1 1 d . . . . .
H045 H 1.025488 0.074274 0.675775 0.079 Uiso 1 1 calc R U . . .
C046 C 0.3545(19) -0.1652(16) 0.5704(5) 0.091(5) Uani 1 1 d . . . . .
H046 H 0.320716 -0.098689 0.581761 0.109 Uiso 1 1 calc R U . . .
C047 C 0.302(2) -0.2718(16) 0.5766(5) 0.097(6) Uani 1 1 d . . . . .
H047 H 0.230201 -0.275625 0.592155 0.117 Uiso 1 1 calc R U . . .
C049 C 0.8308(19) 0.5555(17) 0.5684(5) 0.086(5) Uani 1 1 d . . . . .
H049 H 0.897276 0.580700 0.553038 0.103 Uiso 1 1 calc R U . . .
C050 C 0.286(2) -0.4887(14) 0.5699(5) 0.095(6) Uani 1 1 d . . . . .
H05A H 0.199773 -0.478454 0.579455 0.143 Uiso 1 1 calc R U . . .
H05B H 0.338249 -0.529308 0.587735 0.143 Uiso 1 1 calc R U . . .
H05C H 0.282324 -0.533984 0.547667 0.143 Uiso 1 1 calc R U . . .
C051 C 0.8740(15) 0.1212(13) 0.5249(4) 0.061(4) Uani 1 1 d . . . . .
H051 H 0.791661 0.136979 0.515574 0.074 Uiso 1 1 calc R U . . .
C052 C 0.769(2) 0.4512(14) 0.5615(4) 0.083(5) Uani 1 1 d . . . . .
H052 H 0.795117 0.405316 0.541623 0.099 Uiso 1 1 calc R U . . .
C053 C 1.1156(18) 0.077(2) 0.5512(5) 0.093(6) Uani 1 1 d . . . . .
H053 H 1.199295 0.060713 0.559468 0.112 Uiso 1 1 calc R U . . .
C054 C 1.089(2) 0.180(2) 0.5316(6) 0.112(8) Uani 1 1 d . . . . .
H054 H 1.154790 0.234337 0.527414 0.134 Uiso 1 1 calc R U . . .
C055 C 1.371(2) 0.347(2) 0.6708(6) 0.104(7) Uani 1 1 d . . . . .
H055 H 1.459104 0.342564 0.676779 0.125 Uiso 1 1 calc R U . . .
C056 C 0.795(2) 0.6222(14) 0.5977(6) 0.088(6) Uani 1 1 d . . . . .
H056 H 0.842452 0.689731 0.603319 0.105 Uiso 1 1 calc R U . . .
C057 C 1.154(2) -0.2262(17) 0.6722(5) 0.099(7) Uani 1 1 d . . . . .
H057 H 1.187424 -0.302144 0.673205 0.119 Uiso 1 1 calc R U . . .
C058 C 1.0179(14) 0.0005(18) 0.5578(4) 0.075(5) Uani 1 1 d . . . . .
H058 H 1.033130 -0.065977 0.572099 0.090 Uiso 1 1 calc R U . . .
C059 C 1.020(2) -0.2079(15) 0.6727(5) 0.089(6) Uani 1 1 d . . . . .
H059 H 0.962630 -0.271131 0.671449 0.107 Uiso 1 1 calc R U . . .
C060 C 0.974(2) 0.2007(16) 0.5195(5) 0.087(5) Uani 1 1 d . . . . .
H060 H 0.957070 0.270279 0.506928 0.104 Uiso 1 1 calc R U . . .
C061 C 1.324(2) 0.2765(17) 0.6444(6) 0.096(6) Uani 1 1 d . . . . .
H061 H 1.379962 0.226534 0.631668 0.115 Uiso 1 1 calc R U . . .
C062 C 1.390(2) -0.161(3) 0.6701(5) 0.160(12) Uani 1 1 d . . . . .
H06A H 1.420363 -0.167191 0.645187 0.240 Uiso 1 1 calc R U . . .
H06B H 1.406009 -0.234297 0.682621 0.240 Uiso 1 1 calc R U . . .
H06C H 1.435559 -0.099092 0.682418 0.240 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
S001 O601 1.409(8) . ?
S001 O701 1.437(9) . ?
S001 N007 1.661(11) . ?
S001 C035 1.813(17) . ?
S002 O401 1.407(10) . ?
S002 O301 1.412(11) . ?
S002 N012 1.637(10) . ?
S002 C023 1.756(15) . ?
O001 C4 1.407(16) . ?
O001 C042 1.435(15) . ?
O201 C3 1.428(15) . ?
O201 C037 1.434(15) . ?
N007 C2 1.471(16) . ?
N007 C1 1.507(15) . ?
N008 C011 1.317(15) . ?
N008 N16 1.365(14) . ?
N008 C019 1.482(14) . ?
C009 N16 1.333(14) . ?
C009 N014 1.374(14) . ?
C009 C020 1.451(16) . ?
N012 C025 1.443(15) . ?
N012 C031 1.461(16) . ?
N014 C029 1.274(16) . ?
O501 C028 1.190(15) . ?
C011 C020 1.363(15) . ?
C011 H011 0.9300 . ?
N017 C029 1.349(18) . ?
N017 C028 1.428(16) . ?
N017 H017 0.8600 . ?
C3 C1 1.519(17) . ?
C3 C4 1.550(17) . ?
C3 H3 0.9800 . ?
C019 C1 1.512(17) . ?
C019 H01A 0.9700 . ?
C019 H01B 0.9700 . ?
C020 C028 1.395(16) . ?
C2 C4 1.560(17) . ?
C2 C025 1.575(18) . ?
C2 H2 0.9800 . ?
C1 H1 0.9800 . ?
C023 C027 1.32(2) . ?
C023 C046 1.42(2) . ?
C024 C052 1.39(2) . ?
C024 C032 1.402(19) . ?
C024 C042 1.470(19) . ?
C025 H02A 0.9700 . ?
C025 H02B 0.9700 . ?
C4 H4 0.9800 . ?
C027 C034 1.39(2) . ?
C027 H027 0.9300 . ?
C030 C036 1.35(2) . ?
C030 C044 1.41(2) . ?
C030 C037 1.51(2) . ?
C031 C038 1.522(19) . ?
C031 H03A 0.9700 . ?
C031 H03B 0.9700 . ?
C032 C039 1.38(2) . ?
C032 H032 0.9300 . ?
C033 C047 1.33(2) . ?
C033 C034 1.39(2) . ?
C033 C050 1.49(2) . ?
C034 H034 0.9300 . ?
C035 C059 1.34(2) . ?
C035 C045 1.39(2) . ?
C036 C061 1.38(3) . ?
C036 H036 0.9300 . ?
C037 H03C 0.9700 . ?
C037 H03D 0.9700 . ?
C038 C051 1.353(19) . ?
C038 C058 1.38(2) . ?
C039 C056 1.34(2) . ?
C039 H039 0.9300 . ?
C040 C057 1.34(3) . ?
C040 C041 1.37(2) . ?
C040 C062 1.63(3) . ?
C041 C045 1.39(2) . ?
C041 H041 0.9300 . ?
C042 H04A 0.9700 . ?
C042 H04B 0.9700 . ?
C043 C055 1.37(3) . ?
C043 C044 1.39(3) . ?
C043 H043 0.9300 . ?
C044 H044 0.9300 . ?
C045 H045 0.9300 . ?
C046 C047 1.35(2) . ?
C046 H046 0.9300 . ?
C047 H047 0.9300 . ?
C049 C056 1.36(2) . ?
C049 C052 1.37(2) . ?
C049 H049 0.9300 . ?
C050 H05A 0.9600 . ?
C050 H05B 0.9600 . ?
C050 H05C 0.9600 . ?
C051 C060 1.38(2) . ?
C051 H051 0.9300 . ?
C052 H052 0.9300 . ?
C053 C058 1.35(2) . ?
C053 C054 1.40(3) . ?
C053 H053 0.9300 . ?
C054 C060 1.29(3) . ?
C054 H054 0.9300 . ?
C055 C061 1.34(3) . ?
C055 H055 0.9300 . ?
C056 H056 0.9300 . ?
C057 C059 1.40(3) . ?
C057 H057 0.9300 . ?
C058 H058 0.9300 . ?
C059 H059 0.9300 . ?
C060 H060 0.9300 . ?
C061 H061 0.9300 . ?
C062 H06A 0.9600 . ?
C062 H06B 0.9600 . ?
C062 H06C 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
O601 S001 O701 117.3(6) . . ?
O601 S001 N007 107.3(5) . . ?
O701 S001 N007 105.7(5) . . ?
O601 S001 C035 109.4(7) . . ?
O701 S001 C035 104.7(6) . . ?
N007 S001 C035 112.4(6) . . ?
O401 S002 O301 119.1(7) . . ?
O401 S002 N012 105.3(6) . . ?
O301 S002 N012 107.8(6) . . ?
O401 S002 C023 107.9(7) . . ?
O301 S002 C023 108.1(7) . . ?
N012 S002 C023 108.2(6) . . ?
C4 O001 C042 113.8(11) . . ?
C3 O201 C037 109.8(9) . . ?
C2 N007 C1 111.3(9) . . ?
C2 N007 S001 118.9(8) . . ?
C1 N007 S001 127.1(8) . . ?
C011 N008 N16 114.4(9) . . ?
C011 N008 C019 130.0(11) . . ?
N16 N008 C019 115.1(10) . . ?
N16 C009 N014 125.9(11) . . ?
N16 C009 C020 111.5(10) . . ?
N014 C009 C020 122.6(10) . . ?
C009 N16 N008 102.9(9) . . ?
C025 N012 C031 115.1(10) . . ?
C025 N012 S002 115.3(8) . . ?
C031 N012 S002 118.8(8) . . ?
C029 N014 C009 116.0(11) . . ?
N008 C011 C020 107.9(11) . . ?
N008 C011 H011 126.0 . . ?
C020 C011 H011 126.0 . . ?
C029 N017 C028 126.0(11) . . ?
C029 N017 H017 117.0 . . ?
C028 N017 H017 117.0 . . ?
O201 C3 C1 108.5(10) . . ?
O201 C3 C4 111.6(10) . . ?
C1 C3 C4 102.6(10) . . ?
O201 C3 H3 111.3 . . ?
C1 C3 H3 111.3 . . ?
C4 C3 H3 111.3 . . ?
N008 C019 C1 108.9(9) . . ?
N008 C019 H01A 109.9 . . ?
C1 C019 H01A 109.9 . . ?
N008 C019 H01B 109.9 . . ?
C1 C019 H01B 109.9 . . ?
H01A C019 H01B 108.3 . . ?
C011 C020 C028 135.9(12) . . ?
C011 C020 C009 103.3(10) . . ?
C028 C020 C009 120.8(11) . . ?
N007 C2 C4 103.9(8) . . ?
N007 C2 C025 112.1(10) . . ?
C4 C2 C025 111.7(10) . . ?
N007 C2 H2 109.7 . . ?
C4 C2 H2 109.7 . . ?
C025 C2 H2 109.7 . . ?
N007 C1 C019 117.6(10) . . ?
N007 C1 C3 102.1(9) . . ?
C019 C1 C3 115.0(11) . . ?
N007 C1 H1 107.2 . . ?
C019 C1 H1 107.2 . . ?
C3 C1 H1 107.2 . . ?
C027 C023 C046 117.3(14) . . ?
C027 C023 S002 123.2(13) . . ?
C046 C023 S002 119.4(13) . . ?
C052 C024 C032 117.3(14) . . ?
C052 C024 C042 121.5(13) . . ?
C032 C024 C042 121.2(15) . . ?
N012 C025 C2 110.3(10) . . ?
N012 C025 H02A 109.6 . . ?
C2 C025 H02A 109.6 . . ?
N012 C025 H02B 109.6 . . ?
C2 C025 H02B 109.6 . . ?
H02A C025 H02B 108.1 . . ?
O001 C4 C3 108.6(10) . . ?
O001 C4 C2 111.8(11) . . ?
C3 C4 C2 104.1(9) . . ?
O001 C4 H4 110.7 . . ?
C3 C4 H4 110.7 . . ?
C2 C4 H4 110.7 . . ?
C023 C027 C034 122.1(16) . . ?
C023 C027 H027 119.0 . . ?
C034 C027 H027 119.0 . . ?
O501 C028 C020 129.5(13) . . ?
O501 C028 N017 120.1(11) . . ?
C020 C028 N017 110.4(11) . . ?
N014 C029 N017 124.2(12) . . ?
C036 C030 C044 116.5(14) . . ?
C036 C030 C037 122.4(15) . . ?
C044 C030 C037 121.0(15) . . ?
N012 C031 C038 113.7(10) . . ?
N012 C031 H03A 108.8 . . ?
C038 C031 H03A 108.8 . . ?
N012 C031 H03B 108.8 . . ?
C038 C031 H03B 108.8 . . ?
H03A C031 H03B 107.7 . . ?
C039 C032 C024 120.4(16) . . ?
C039 C032 H032 119.8 . . ?
C024 C032 H032 119.8 . . ?
C047 C033 C034 116.0(17) . . ?
C047 C033 C050 123.7(19) . . ?
C034 C033 C050 120.3(18) . . ?
C027 C034 C033 120.7(16) . . ?
C027 C034 H034 119.6 . . ?
C033 C034 H034 119.6 . . ?
C059 C035 C045 121.6(16) . . ?
C059 C035 S001 117.6(13) . . ?
C045 C035 S001 120.6(11) . . ?
C030 C036 C061 121.9(16) . . ?
C030 C036 H036 119.1 . . ?
C061 C036 H036 119.1 . . ?
O201 C037 C030 106.6(11) . . ?
O201 C037 H03C 110.4 . . ?
C030 C037 H03C 110.4 . . ?
O201 C037 H03D 110.4 . . ?
C030 C037 H03D 110.4 . . ?
H03C C037 H03D 108.6 . . ?
C051 C038 C058 118.6(15) . . ?
C051 C038 C031 119.3(14) . . ?
C058 C038 C031 122.0(14) . . ?
C056 C039 C032 120.3(16) . . ?
C056 C039 H039 119.9 . . ?
C032 C039 H039 119.9 . . ?
C057 C040 C041 122.4(17) . . ?
C057 C040 C062 117(2) . . ?
C041 C040 C062 120(2) . . ?
C040 C041 C045 117.6(17) . . ?
C040 C041 H041 121.2 . . ?
C045 C041 H041 121.2 . . ?
O001 C042 C024 113.5(11) . . ?
O001 C042 H04A 108.9 . . ?
C024 C042 H04A 108.9 . . ?
O001 C042 H04B 108.9 . . ?
C024 C042 H04B 108.9 . . ?
H04A C042 H04B 107.7 . . ?
C055 C043 C044 116.5(17) . . ?
C055 C043 H043 121.8 . . ?
C044 C043 H043 121.8 . . ?
C043 C044 C030 122.7(16) . . ?
C043 C044 H044 118.7 . . ?
C030 C044 H044 118.7 . . ?
C041 C045 C035 119.7(14) . . ?
C041 C045 H045 120.2 . . ?
C035 C045 H045 120.2 . . ?
C047 C046 C023 119.2(17) . . ?
C047 C046 H046 120.4 . . ?
C023 C046 H046 120.4 . . ?
C033 C047 C046 124.7(19) . . ?
C033 C047 H047 117.6 . . ?
C046 C047 H047 117.6 . . ?
C056 C049 C052 120.4(17) . . ?
C056 C049 H049 119.8 . . ?
C052 C049 H049 119.8 . . ?
C033 C050 H05A 109.5 . . ?
C033 C050 H05B 109.5 . . ?
H05A C050 H05B 109.5 . . ?
C033 C050 H05C 109.5 . . ?
H05A C050 H05C 109.5 . . ?
H05B C050 H05C 109.5 . . ?
C038 C051 C060 120.2(15) . . ?
C038 C051 H051 119.9 . . ?
C060 C051 H051 119.9 . . ?
C049 C052 C024 120.7(15) . . ?
C049 C052 H052 119.7 . . ?
C024 C052 H052 119.7 . . ?
C058 C053 C054 118.9(18) . . ?
C058 C053 H053 120.6 . . ?
C054 C053 H053 120.6 . . ?
C060 C054 C053 120.5(19) . . ?
C060 C054 H054 119.8 . . ?
C053 C054 H054 119.8 . . ?
C061 C055 C043 122(2) . . ?
C061 C055 H055 118.8 . . ?
C043 C055 H055 118.8 . . ?
C039 C056 C049 120.8(16) . . ?
C039 C056 H056 119.6 . . ?
C049 C056 H056 119.6 . . ?
C040 C057 C059 119.8(17) . . ?
C040 C057 H057 120.1 . . ?
C059 C057 H057 120.1 . . ?
C053 C058 C038 120.6(17) . . ?
C053 C058 H058 119.7 . . ?
C038 C058 H058 119.7 . . ?
C035 C059 C057 118.6(19) . . ?
C035 C059 H059 120.7 . . ?
C057 C059 H059 120.7 . . ?
C054 C060 C051 121.1(19) . . ?
C054 C060 H060 119.4 . . ?
C051 C060 H060 119.4 . . ?
C055 C061 C036 120(2) . . ?
C055 C061 H061 120.0 . . ?
C036 C061 H061 120.0 . . ?
C040 C062 H06A 109.5 . . ?
C040 C062 H06B 109.5 . . ?
H06A C062 H06B 109.5 . . ?
C040 C062 H06C 109.5 . . ?
H06A C062 H06C 109.5 . . ?
H06B C062 H06C 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
O601 S001 N007 C2 179.2(9) . . . . ?
O701 S001 N007 C2 -54.8(11) . . . . ?
C035 S001 N007 C2 58.9(11) . . . . ?
O601 S001 N007 C1 19.8(13) . . . . ?
O701 S001 N007 C1 145.8(11) . . . . ?
C035 S001 N007 C1 -100.5(12) . . . . ?
N014 C009 N16 N008 -178.0(11) . . . . ?
C020 C009 N16 N008 -0.1(12) . . . . ?
C011 N008 N16 C009 -0.7(13) . . . . ?
C019 N008 N16 C009 -173.4(9) . . . . ?
O401 S002 N012 C025 -177.5(9) . . . . ?
O301 S002 N012 C025 54.4(10) . . . . ?
C023 S002 N012 C025 -62.3(11) . . . . ?
O401 S002 N012 C031 -34.6(11) . . . . ?
O301 S002 N012 C031 -162.7(9) . . . . ?
C023 S002 N012 C031 80.6(11) . . . . ?
N16 C009 N014 C029 179.5(12) . . . . ?
C020 C009 N014 C029 1.9(18) . . . . ?
N16 N008 C011 C020 1.2(13) . . . . ?
C019 N008 C011 C020 172.6(11) . . . . ?
C037 O201 C3 C1 -159.7(10) . . . . ?
C037 O201 C3 C4 88.0(12) . . . . ?
C011 N008 C019 C1 -104.2(15) . . . . ?
N16 N008 C019 C1 67.2(13) . . . . ?
N008 C011 C020 C028 179.5(13) . . . . ?
N008 C011 C020 C009 -1.1(12) . . . . ?
N16 C009 C020 C011 0.7(13) . . . . ?
N014 C009 C020 C011 178.7(11) . . . . ?
N16 C009 C020 C028 -179.8(10) . . . . ?
N014 C009 C020 C028 -1.8(17) . . . . ?
C1 N007 C2 C4 3.3(14) . . . . ?
S001 N007 C2 C4 -159.2(9) . . . . ?
C1 N007 C2 C025 -117.5(11) . . . . ?
S001 N007 C2 C025 80.0(12) . . . . ?
C2 N007 C1 C019 -153.6(11) . . . . ?
S001 N007 C1 C019 7.1(18) . . . . ?
C2 N007 C1 C3 -26.7(14) . . . . ?
S001 N007 C1 C3 134.0(10) . . . . ?
N008 C019 C1 N007 166.1(11) . . . . ?
N008 C019 C1 C3 45.7(15) . . . . ?
O201 C3 C1 N007 -79.6(12) . . . . ?
C4 C3 C1 N007 38.6(12) . . . . ?
O201 C3 C1 C019 48.9(13) . . . . ?
C4 C3 C1 C019 167.1(11) . . . . ?
O401 S002 C023 C027 38.3(15) . . . . ?
O301 S002 C023 C027 168.3(12) . . . . ?
N012 S002 C023 C027 -75.2(14) . . . . ?
O401 S002 C023 C046 -145.2(13) . . . . ?
O301 S002 C023 C046 -15.2(15) . . . . ?
N012 S002 C023 C046 101.3(13) . . . . ?
C031 N012 C025 C2 65.8(13) . . . . ?
S002 N012 C025 C2 -149.9(9) . . . . ?
N007 C2 C025 N012 -176.3(10) . . . . ?
C4 C2 C025 N012 67.5(13) . . . . ?
C042 O001 C4 C3 111.2(11) . . . . ?
C042 O001 C4 C2 -134.5(10) . . . . ?
O201 C3 C4 O001 -162.3(10) . . . . ?
C1 C3 C4 O001 81.7(12) . . . . ?
O201 C3 C4 C2 78.4(12) . . . . ?
C1 C3 C4 C2 -37.6(12) . . . . ?
N007 C2 C4 O001 -95.9(11) . . . . ?
C025 C2 C4 O001 25.2(13) . . . . ?
N007 C2 C4 C3 21.2(13) . . . . ?
C025 C2 C4 C3 142.2(10) . . . . ?
C046 C023 C027 C034 1(2) . . . . ?
S002 C023 C027 C034 177.8(11) . . . . ?
C011 C020 C028 O501 3(2) . . . . ?
C009 C020 C028 O501 -176.6(13) . . . . ?
C011 C020 C028 N017 -178.5(12) . . . . ?
C009 C020 C028 N017 2.2(15) . . . . ?
C029 N017 C028 O501 175.7(13) . . . . ?
C029 N017 C028 C020 -3.2(18) . . . . ?
C009 N014 C029 N017 -3(2) . . . . ?
C028 N017 C029 N014 4(2) . . . . ?
C025 N012 C031 C038 -97.9(13) . . . . ?
S002 N012 C031 C038 119.1(10) . . . . ?
C052 C024 C032 C039 -3(2) . . . . ?
C042 C024 C032 C039 177.6(13) . . . . ?
C023 C027 C034 C033 0(2) . . . . ?
C047 C033 C034 C027 -1(2) . . . . ?
C050 C033 C034 C027 -179.6(14) . . . . ?
O601 S001 C035 C059 93.4(13) . . . . ?
O701 S001 C035 C059 -33.2(14) . . . . ?
N007 S001 C035 C059 -147.5(12) . . . . ?
O601 S001 C035 C045 -81.1(12) . . . . ?
O701 S001 C035 C045 152.3(11) . . . . ?
N007 S001 C035 C045 38.0(13) . . . . ?
C044 C030 C036 C061 -3(2) . . . . ?
C037 C030 C036 C061 -179.2(14) . . . . ?
C3 O201 C037 C030 177.9(12) . . . . ?
C036 C030 C037 O201 71.3(18) . . . . ?
C044 C030 C037 O201 -105.1(15) . . . . ?
N012 C031 C038 C051 -48.5(16) . . . . ?
N012 C031 C038 C058 129.1(14) . . . . ?
C024 C032 C039 C056 -1(2) . . . . ?
C057 C040 C041 C045 1(2) . . . . ?
C062 C040 C041 C045 -174.3(14) . . . . ?
C4 O001 C042 C024 -61.7(16) . . . . ?
C052 C024 C042 O001 119.6(16) . . . . ?
C032 C024 C042 O001 -60.8(18) . . . . ?
C055 C043 C044 C030 -5(3) . . . . ?
C036 C030 C044 C043 4(2) . . . . ?
C037 C030 C044 C043 -179.5(14) . . . . ?
C040 C041 C045 C035 -3(2) . . . . ?
C059 C035 C045 C041 0(2) . . . . ?
S001 C035 C045 C041 174.3(11) . . . . ?
C027 C023 C046 C047 -2(3) . . . . ?
S002 C023 C046 C047 -178.7(15) . . . . ?
C034 C033 C047 C046 1(3) . . . . ?
C050 C033 C047 C046 178.7(18) . . . . ?
C023 C046 C047 C033 1(3) . . . . ?
C058 C038 C051 C060 1(2) . . . . ?
C031 C038 C051 C060 179.1(13) . . . . ?
C056 C049 C052 C024 1(3) . . . . ?
C032 C024 C052 C049 2(2) . . . . ?
C042 C024 C052 C049 -177.9(15) . . . . ?
C058 C053 C054 C060 -2(3) . . . . ?
C044 C043 C055 C061 4(3) . . . . ?
C032 C039 C056 C049 5(3) . . . . ?
C052 C049 C056 C039 -5(3) . . . . ?
C041 C040 C057 C059 4(3) . . . . ?
C062 C040 C057 C059 179.4(15) . . . . ?
C054 C053 C058 C038 4(3) . . . . ?
C051 C038 C058 C053 -4(2) . . . . ?
C031 C038 C058 C053 178.4(14) . . . . ?
C045 C035 C059 C057 5(2) . . . . ?
S001 C035 C059 C057 -169.5(13) . . . . ?
C040 C057 C059 C035 -7(3) . . . . ?
C053 C054 C060 C051 -1(3) . . . . ?
C038 C051 C060 C054 1(3) . . . . ?
C043 C055 C061 C036 -3(3) . . . . ?
C030 C036 C061 C055 2(2) . . . . ?

_refine_diff_density_max         1.441
_refine_diff_density_min         -0.478
_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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1860487'
_audit_update_record             
;
2018-08-06 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 C0 H20 Cl2 N4 O4'
_chemical_formula_sum            'C11 C0 H20 Cl2 N4 O4'
_chemical_formula_weight         343.21

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'
C C 0.0033 0.0016 '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                   5.4636(10)
_cell_length_b                   15.231(3)
_cell_length_c                   18.032(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1500.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    8678
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.91

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.454
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(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            14276
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  0.1015
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.750
_diffrn_reflns_theta_max         28.135
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3654
_reflns_number_gt                3336
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.996

_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0656P)²+1.2884P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1274 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3654
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5786(7) -0.2379(2) 0.32475(19) 0.0230(7) Uani 1 1 d . . . . .
H5 H 0.713461 -0.275850 0.340786 0.028 Uiso 1 1 calc R U . . .
C2 C 0.6405(9) -0.1989(3) 0.2480(2) 0.0340(10) Uani 1 1 d . . . . .
H1 H 0.782359 -0.228848 0.226404 0.041 Uiso 1 1 calc R U . . .
C3 C 0.7000(7) -0.1026(3) 0.2628(2) 0.0253(8) Uani 1 1 d . . . . .
H4 H 0.661535 -0.065927 0.219736 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5373(7) -0.0800(3) 0.3284(2) 0.0231(7) Uani 1 1 d . . . . .
H13 H 0.367377 -0.074577 0.311544 0.028 Uiso 1 1 calc R U . . .
N2 N 0.5620(6) -0.1599(2) 0.37630(16) 0.0222(6) Uani 1 1 d . . . . .
H12 H 0.432838 -0.165080 0.406037 0.027 Uiso 1 1 calc R U . . .
H11 H 0.696146 -0.156157 0.404145 0.027 Uiso 1 1 calc R U . . .
N4 N 0.2812(8) 0.0464(2) 0.53913(18) 0.0349(8) Uani 1 1 d . . . . .
H17 H 0.287669 0.030247 0.584782 0.042 Uiso 1 1 calc R U . . .
C5 C 0.6138(8) 0.0038(3) 0.3670(2) 0.0308(9) Uani 1 1 d . . . . .
H15 H 0.766338 -0.006633 0.393051 0.037 Uiso 1 1 calc R U . . .
H14 H 0.644025 0.048560 0.329822 0.037 Uiso 1 1 calc R U . . .
C6 C 0.2613(9) 0.0978(3) 0.3986(2) 0.0307(9) Uani 1 1 d . . . . .
H16 H 0.257920 0.114715 0.349005 0.037 Uiso 1 1 calc R U . . .
C7 C 0.1003(9) 0.1341(3) 0.4446(2) 0.0309(9) Uani 1 1 d . . . . .
C8 C 0.1047(8) 0.1065(3) 0.5213(2) 0.0293(9) Uani 1 1 d . . . . .
C9 C 0.4483(10) 0.0094(3) 0.4923(2) 0.0329(9) Uani 1 1 d . . . . .
C10 C 0.3456(8) -0.2913(3) 0.32173(19) 0.0271(8) Uani 1 1 d . . . . .
H6 H 0.206790 -0.251751 0.319196 0.032 Uiso 1 1 calc R U . . .
H7 H 0.345970 -0.326528 0.276903 0.032 Uiso 1 1 calc R U . . .
N3 N 0.4318(8) 0.0371(2) 0.42001(18) 0.0296(7) Uani 1 1 d . . . . .
C11 C -0.0787(12) 0.2033(4) 0.4213(3) 0.0471(12) Uani 1 1 d . . . . .
H19 H -0.176992 0.220169 0.463125 0.071 Uiso 1 1 calc R U . . .
H18 H 0.008483 0.253621 0.403111 0.071 Uiso 1 1 calc R U . . .
H20 H -0.182369 0.180589 0.382889 0.071 Uiso 1 1 calc R U . . .
N1 N 0.3163(10) -0.3492(3) 0.3859(2) 0.0497(12) Uani 1 1 d . . . . .
H10 H 0.177137 -0.379136 0.381588 0.075 Uiso 1 1 calc R U . . .
H8 H 0.441521 -0.386510 0.387935 0.075 Uiso 1 1 calc R U . . .
H9 H 0.312475 -0.317178 0.427149 0.075 Uiso 1 1 calc R U . . .
O1 O 0.4356(9) -0.2081(3) 0.20187(18) 0.0687(14) Uani 1 1 d . . . . .
H2 H 0.381627 -0.159432 0.191380 0.103 Uiso 1 1 calc R U . . .
O2 O 0.9465(6) -0.0946(2) 0.28308(17) 0.0371(7) Uani 1 1 d . . . . .
H3 H 1.033457 -0.106971 0.247528 0.056 Uiso 1 1 calc R U . . .
O3 O 0.5990(8) -0.0437(2) 0.51231(18) 0.0473(9) Uani 1 1 d . . . . .
O4 O -0.0384(7) 0.1343(3) 0.56869(18) 0.0453(9) Uani 1 1 d . . . . .
Cl1 Cl 0.5730(2) -0.32494(9) 0.53849(6) 0.0414(3) Uani 1 1 d . . . . .
Cl2 Cl 0.3284(2) -0.05765(7) 0.69499(6) 0.0366(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.511(6) . ?
C1 N2 1.512(4) . ?
C1 C2 1.545(5) . ?
C1 H5 0.9800 . ?
C2 O1 1.401(6) . ?
C2 C3 1.525(6) . ?
C2 H1 0.9800 . ?
C3 O2 1.401(5) . ?
C3 C4 1.518(5) . ?
C3 H4 0.9800 . ?
C4 N2 1.498(5) . ?
C4 C5 1.513(5) . ?
C4 H13 0.9800 . ?
N2 H12 0.8900 . ?
N2 H11 0.8900 . ?
N4 C9 1.365(6) . ?
N4 C8 1.367(6) . ?
N4 H17 0.8600 . ?
C5 N3 1.470(5) . ?
C5 H15 0.9700 . ?
C5 H14 0.9700 . ?
C6 C7 1.330(6) . ?
C6 N3 1.369(6) . ?
C6 H16 0.9300 . ?
C7 C8 1.445(6) . ?
C7 C11 1.498(6) . ?
C8 O4 1.234(5) . ?
C9 O3 1.210(6) . ?
C9 N3 1.373(5) . ?
C10 N1 1.463(5) . ?
C10 H6 0.9700 . ?
C10 H7 0.9700 . ?
C11 H19 0.9600 . ?
C11 H18 0.9600 . ?
C11 H20 0.9600 . ?
N1 H10 0.8900 . ?
N1 H8 0.8900 . ?
N1 H9 0.8900 . ?
O1 H2 0.8200 . ?
O2 H3 0.8200 . ?

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
C10 C1 N2 113.3(3) . . ?
C10 C1 C2 111.1(3) . . ?
N2 C1 C2 105.1(3) . . ?
C10 C1 H5 109.1 . . ?
N2 C1 H5 109.1 . . ?
C2 C1 H5 109.1 . . ?
O1 C2 C3 111.8(4) . . ?
O1 C2 C1 108.5(3) . . ?
C3 C2 C1 105.0(3) . . ?
O1 C2 H1 110.5 . . ?
C3 C2 H1 110.5 . . ?
C1 C2 H1 110.5 . . ?
O2 C3 C4 109.9(3) . . ?
O2 C3 C2 109.6(4) . . ?
C4 C3 C2 103.3(3) . . ?
O2 C3 H4 111.3 . . ?
C4 C3 H4 111.3 . . ?
C2 C3 H4 111.3 . . ?
N2 C4 C5 113.2(3) . . ?
N2 C4 C3 102.2(3) . . ?
C5 C4 C3 112.8(3) . . ?
N2 C4 H13 109.4 . . ?
C5 C4 H13 109.4 . . ?
C3 C4 H13 109.4 . . ?
C4 N2 C1 106.8(3) . . ?
C4 N2 H12 110.4 . . ?
C1 N2 H12 110.4 . . ?
C4 N2 H11 110.4 . . ?
C1 N2 H11 110.4 . . ?
H12 N2 H11 108.6 . . ?
C9 N4 C8 127.0(3) . . ?
C9 N4 H17 116.5 . . ?
C8 N4 H17 116.5 . . ?
N3 C5 C4 113.8(3) . . ?
N3 C5 H15 108.8 . . ?
C4 C5 H15 108.8 . . ?
N3 C5 H14 108.8 . . ?
C4 C5 H14 108.8 . . ?
H15 C5 H14 107.7 . . ?
C7 C6 N3 123.7(4) . . ?
C7 C6 H16 118.2 . . ?
N3 C6 H16 118.2 . . ?
C6 C7 C8 117.7(4) . . ?
C6 C7 C11 123.3(4) . . ?
C8 C7 C11 118.9(4) . . ?
O4 C8 N4 120.9(4) . . ?
O4 C8 C7 123.5(4) . . ?
N4 C8 C7 115.6(4) . . ?
O3 C9 N4 123.2(4) . . ?
O3 C9 N3 122.2(4) . . ?
N4 C9 N3 114.6(4) . . ?
N1 C10 C1 112.8(3) . . ?
N1 C10 H6 109.0 . . ?
C1 C10 H6 109.0 . . ?
N1 C10 H7 109.0 . . ?
C1 C10 H7 109.0 . . ?
H6 C10 H7 107.8 . . ?
C6 N3 C9 121.3(4) . . ?
C6 N3 C5 120.6(3) . . ?
C9 N3 C5 117.9(4) . . ?
C7 C11 H19 109.5 . . ?
C7 C11 H18 109.5 . . ?
H19 C11 H18 109.5 . . ?
C7 C11 H20 109.5 . . ?
H19 C11 H20 109.5 . . ?
H18 C11 H20 109.5 . . ?
C10 N1 H10 109.5 . . ?
C10 N1 H8 109.5 . . ?
H10 N1 H8 109.5 . . ?
C10 N1 H9 109.5 . . ?
H10 N1 H9 109.5 . . ?
H8 N1 H9 109.5 . . ?
C2 O1 H2 109.5 . . ?
C3 O2 H3 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
C10 C1 C2 O1 12.9(5) . . . . ?
N2 C1 C2 O1 -110.0(4) . . . . ?
C10 C1 C2 C3 132.6(4) . . . . ?
N2 C1 C2 C3 9.7(4) . . . . ?
O1 C2 C3 O2 -157.3(3) . . . . ?
C1 C2 C3 O2 85.2(4) . . . . ?
O1 C2 C3 C4 85.6(4) . . . . ?
C1 C2 C3 C4 -31.9(4) . . . . ?
O2 C3 C4 N2 -75.0(4) . . . . ?
C2 C3 C4 N2 41.9(4) . . . . ?
O2 C3 C4 C5 47.0(5) . . . . ?
C2 C3 C4 C5 163.8(3) . . . . ?
C5 C4 N2 C1 -158.0(3) . . . . ?
C3 C4 N2 C1 -36.4(4) . . . . ?
C10 C1 N2 C4 -104.9(3) . . . . ?
C2 C1 N2 C4 16.6(4) . . . . ?
N2 C4 C5 N3 -76.7(4) . . . . ?
C3 C4 C5 N3 167.8(3) . . . . ?
N3 C6 C7 C8 -0.9(7) . . . . ?
N3 C6 C7 C11 177.4(5) . . . . ?
C9 N4 C8 O4 179.0(5) . . . . ?
C9 N4 C8 C7 -1.2(7) . . . . ?
C6 C7 C8 O4 -178.6(4) . . . . ?
C11 C7 C8 O4 3.0(7) . . . . ?
C6 C7 C8 N4 1.6(6) . . . . ?
C11 C7 C8 N4 -176.7(4) . . . . ?
C8 N4 C9 O3 -179.7(5) . . . . ?
C8 N4 C9 N3 0.0(7) . . . . ?
N2 C1 C10 N1 -78.3(5) . . . . ?
C2 C1 C10 N1 163.7(4) . . . . ?
C7 C6 N3 C9 -0.4(7) . . . . ?
C7 C6 N3 C5 -176.2(4) . . . . ?
O3 C9 N3 C6 -179.5(5) . . . . ?
N4 C9 N3 C6 0.8(7) . . . . ?
O3 C9 N3 C5 -3.5(7) . . . . ?
N4 C9 N3 C5 176.8(4) . . . . ?
C4 C5 N3 C6 -93.4(5) . . . . ?
C4 C5 N3 C9 90.6(5) . . . . ?

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.076

