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

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

data_mo_Arnold294DMSO2_0m
_database_code_depnum_ccdc_archive 'CCDC 1420006'
_audit_update_record             
;
2015-08-21 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H27 N5 O5 S3'
_chemical_formula_weight         477.61

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.3651(3)
_cell_length_b                   19.5330(6)
_cell_length_c                   12.7944(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.8300(10)
_cell_angle_gamma                90
_cell_volume                     2201.68(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.376
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23543
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         29.218
_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             5953
_reflns_number_gt                4922
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0405P)²+0.8124P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5953
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
S1 S 1.22073(4) 0.10527(2) 0.66726(3) 0.01219(8) Uani 1 1 d . . . . .
S2 S 1.24061(4) -0.00900(2) 0.83477(3) 0.01185(8) Uani 1 1 d . . . . .
S3 S 0.85086(4) 0.66238(2) 0.55460(3) 0.01711(9) Uani 1 1 d . . . . .
N1 N 0.81528(13) 0.15003(6) 0.58935(10) 0.0129(2) Uani 1 1 d . . . . .
N2 N 1.06426(14) 0.14380(6) 0.60068(10) 0.0149(2) Uani 1 1 d . . . . .
N3 N 1.22802(13) 0.12833(6) 0.87847(10) 0.0140(2) Uani 1 1 d . . . . .
H3 H 1.3243 0.1379 0.9134 0.017 Uiso 1 1 calc R U . . .
N4 N 1.11236(14) 0.15745(6) 0.90298(10) 0.0143(2) Uani 1 1 d . . . . .
N5 N 0.98336(13) 0.13849(6) 0.83938(10) 0.0129(2) Uani 1 1 d . . . . .
O1 O 0.67498(12) -0.15870(5) 0.71890(8) 0.0170(2) Uani 1 1 d . . . . .
O2 O 1.34564(12) 0.15252(6) 0.69490(9) 0.0187(2) Uani 1 1 d . . . . .
O3 O 1.23528(12) 0.04304(5) 0.61109(8) 0.0168(2) Uani 1 1 d . . . . .
O4 O 1.23305(12) -0.01284(6) 0.94925(8) 0.0175(2) Uani 1 1 d . . . . .
O5 O 0.96886(12) 0.65274(6) 0.49836(9) 0.0185(2) Uani 1 1 d . . . . .
C1 C 0.56831(17) 0.09125(9) 0.55158(14) 0.0235(3) Uani 1 1 d . . . . .
H1A H 0.5237 0.1130 0.4787 0.035 Uiso 1 1 calc R U . . .
H1B H 0.4884 0.0819 0.5831 0.035 Uiso 1 1 calc R U . . .
H1C H 0.6171 0.0482 0.5434 0.035 Uiso 1 1 calc R U . . .
C2 C 0.68579(16) 0.13887(8) 0.62856(12) 0.0169(3) Uani 1 1 d . . . . .
H2A H 0.6377 0.1834 0.6329 0.020 Uiso 1 1 calc R U . . .
H2B H 0.7232 0.1189 0.7042 0.020 Uiso 1 1 calc R U . . .
C3 C 0.95595(15) 0.12938(7) 0.64177(11) 0.0119(3) Uani 1 1 d . . . . .
C4 C 1.00097(15) 0.08960(7) 0.75388(11) 0.0108(3) Uani 1 1 d . . . . .
C5 C 0.91212(15) 0.02407(7) 0.74732(11) 0.0110(3) Uani 1 1 d . . . . .
C6 C 0.88137(15) -0.01804(7) 0.65399(11) 0.0126(3) Uani 1 1 d . . . . .
H6 H 0.9142 -0.0047 0.5944 0.015 Uiso 1 1 calc R U . . .
C7 C 0.80367(16) -0.07876(7) 0.64772(11) 0.0138(3) Uani 1 1 d . . . . .
H7 H 0.7831 -0.1070 0.5839 0.017 Uiso 1 1 calc R U . . .
C8 C 0.75517(15) -0.09877(7) 0.73500(11) 0.0123(3) Uani 1 1 d . . . . .
C9 C 0.62620(18) -0.18230(8) 0.80706(13) 0.0197(3) Uani 1 1 d . . . . .
H9A H 0.7144 -0.1871 0.8751 0.030 Uiso 1 1 calc R U . . .
H9B H 0.5758 -0.2267 0.7870 0.030 Uiso 1 1 calc R U . . .
H9C H 0.5550 -0.1492 0.8196 0.030 Uiso 1 1 calc R U . . .
C10 C 0.86641(15) 0.00326(7) 0.83524(11) 0.0131(3) Uani 1 1 d . . . . .
H10 H 0.8892 0.0311 0.8998 0.016 Uiso 1 1 calc R U . . .
C11 C 0.78762(15) -0.05790(7) 0.82952(11) 0.0133(3) Uani 1 1 d . . . . .
H11 H 0.7562 -0.0716 0.8896 0.016 Uiso 1 1 calc R U . . .
C12 C 1.17649(15) 0.08049(7) 0.78975(11) 0.0107(2) Uani 1 1 d . . . . .
C13 C 1.43781(16) 0.00047(8) 0.85210(12) 0.0160(3) Uani 1 1 d . . . . .
H13A H 1.4788 0.0407 0.8983 0.024 Uiso 1 1 calc R U . . .
H13B H 1.4491 0.0063 0.7792 0.024 Uiso 1 1 calc R U . . .
H13C H 1.4933 -0.0405 0.8883 0.024 Uiso 1 1 calc R U . . .
C14 C 0.78243(17) 0.18705(8) 0.48292(12) 0.0162(3) Uani 1 1 d . . . . .
H14A H 0.8612 0.2225 0.4916 0.019 Uiso 1 1 calc R U . . .
H14B H 0.6835 0.2106 0.4653 0.019 Uiso 1 1 calc R U . . .
C15 C 0.77745(19) 0.14054(9) 0.38592(12) 0.0221(3) Uani 1 1 d . . . . .
H15A H 0.8767 0.1187 0.4010 0.033 Uiso 1 1 calc R U . . .
H15B H 0.7527 0.1678 0.3177 0.033 Uiso 1 1 calc R U . . .
H15C H 0.6998 0.1052 0.3767 0.033 Uiso 1 1 calc R U . . .
C16 C 0.67790(18) 0.68453(9) 0.44621(14) 0.0248(3) Uani 1 1 d . . . . .
H16A H 0.6962 0.7233 0.4037 0.037 Uiso 1 1 calc R U . . .
H16B H 0.6010 0.6973 0.4789 0.037 Uiso 1 1 calc R U . . .
H16C H 0.6419 0.6452 0.3967 0.037 Uiso 1 1 calc R U . . .
C17 C 0.8905(2) 0.74446(8) 0.61889(14) 0.0240(3) Uani 1 1 d . . . . .
H17A H 0.9871 0.7428 0.6808 0.036 Uiso 1 1 calc R U . . .
H17B H 0.8089 0.7573 0.6468 0.036 Uiso 1 1 calc R U . . .
H17C H 0.8974 0.7784 0.5644 0.036 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
S1 O2 1.4369(11) . ?
S1 O3 1.4418(11) . ?
S1 N2 1.6102(12) . ?
S1 C12 1.8173(13) . ?
S2 O4 1.4921(10) . ?
S2 C13 1.7934(14) . ?
S2 C12 1.8745(14) . ?
S3 O5 1.5210(11) . ?
S3 C17 1.7826(17) . ?
S3 C16 1.7917(16) . ?
N1 C3 1.3223(18) . ?
N1 C2 1.4774(18) . ?
N1 C14 1.4790(18) . ?
N2 C3 1.3215(18) . ?
N3 N4 1.3511(16) . ?
N3 C12 1.4223(17) . ?
N3 H3 0.8800 . ?
N4 N5 1.2617(17) . ?
N5 C4 1.5027(17) . ?
O1 C8 1.3682(17) . ?
O1 C9 1.4293(17) . ?
C1 C2 1.520(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5585(19) . ?
C4 C5 1.5135(19) . ?
C4 C12 1.5596(18) . ?
C5 C10 1.3930(18) . ?
C5 C6 1.3970(19) . ?
C6 C7 1.380(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3965(18) . ?
C7 H7 0.9500 . ?
C8 C11 1.3939(19) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.393(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.526(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
O2 S1 O3 117.22(6) . . ?
O2 S1 N2 110.41(7) . . ?
O3 S1 N2 110.69(6) . . ?
O2 S1 C12 111.32(6) . . ?
O3 S1 C12 107.04(6) . . ?
N2 S1 C12 98.51(6) . . ?
O4 S2 C13 105.88(6) . . ?
O4 S2 C12 103.39(6) . . ?
C13 S2 C12 98.68(7) . . ?
O5 S3 C17 104.99(7) . . ?
O5 S3 C16 105.95(7) . . ?
C17 S3 C16 97.59(8) . . ?
C3 N1 C2 125.04(12) . . ?
C3 N1 C14 118.45(11) . . ?
C2 N1 C14 116.51(11) . . ?
C3 N2 S1 111.93(10) . . ?
N4 N3 C12 112.34(11) . . ?
N4 N3 H3 123.8 . . ?
C12 N3 H3 123.8 . . ?
N5 N4 N3 113.23(11) . . ?
N4 N5 C4 109.78(11) . . ?
C8 O1 C9 117.59(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 111.55(12) . . ?
N1 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 N1 120.02(12) . . ?
N2 C3 C4 117.90(12) . . ?
N1 C3 C4 122.06(12) . . ?
N5 C4 C5 112.57(11) . . ?
N5 C4 C3 106.92(11) . . ?
C5 C4 C3 113.49(11) . . ?
N5 C4 C12 102.90(10) . . ?
C5 C4 C12 115.12(11) . . ?
C3 C4 C12 104.88(10) . . ?
C10 C5 C6 119.19(13) . . ?
C10 C5 C4 121.04(12) . . ?
C6 C5 C4 119.70(12) . . ?
C7 C6 C5 120.51(12) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.15(13) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
O1 C8 C11 124.59(12) . . ?
O1 C8 C7 115.46(12) . . ?
C11 C8 C7 119.95(13) . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C5 120.68(13) . . ?
C11 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C10 C11 C8 119.50(12) . . ?
C10 C11 H11 120.2 . . ?
C8 C11 H11 120.2 . . ?
N3 C12 C4 101.44(10) . . ?
N3 C12 S1 113.48(10) . . ?
C4 C12 S1 103.99(9) . . ?
N3 C12 S2 112.39(9) . . ?
C4 C12 S2 113.12(9) . . ?
S1 C12 S2 111.73(7) . . ?
S2 C13 H13A 109.5 . . ?
S2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 113.39(12) . . ?
N1 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
N1 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S3 C16 H16A 109.5 . . ?
S3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S3 C17 H17A 109.5 . . ?
S3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-4

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

data_mo_ArnoldAP270_0m
_database_code_depnum_ccdc_archive 'CCDC 1426767'
_audit_update_record             
;
2015-09-23 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H29 Cl2 N3 O7 S2'
_chemical_formula_weight         606.52

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9413(4)
_cell_length_b                   11.7201(5)
_cell_length_c                   13.5584(6)
_cell_angle_alpha                95.7270(10)
_cell_angle_beta                 94.0270(10)
_cell_angle_gamma                105.9920(10)
_cell_volume                     1351.91(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.444
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28474
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.822
_diffrn_reflns_theta_max         29.630
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7503
_reflns_number_gt                6629
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0372P)²+0.8360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7503
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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
S1 S 1.06551(3) 0.74277(2) 0.33187(2) 0.01156(6) Uani 1 1 d . . . . .
S2 S 0.95960(3) 0.69836(2) 0.10615(2) 0.01070(6) Uani 1 1 d . . . . .
Cl1 Cl 0.29844(6) 0.55969(4) 0.50091(3) 0.04241(11) Uani 1 1 d . . . . .
Cl2 Cl 0.27814(5) 0.67409(3) 0.69914(3) 0.03018(9) Uani 1 1 d . . . . .
C1 C 0.15556(15) 0.38934(11) 0.20058(11) 0.0201(3) Uani 1 1 d . . . . .
H1A H 0.2156 0.3324 0.2113 0.030 Uiso 1 1 calc R U . . .
H1B H 0.0500 0.3458 0.1700 0.030 Uiso 1 1 calc R U . . .
H1C H 0.1489 0.4335 0.2646 0.030 Uiso 1 1 calc R U . . .
C2 C 0.37553(13) 0.54554(10) 0.17079(10) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.43452(13) 0.63791(10) 0.11326(9) 0.0134(2) Uani 1 1 d . . . . .
H3 H 0.3763 0.6438 0.0536 0.016 Uiso 1 1 calc R U . . .
C4 C 0.57796(13) 0.72033(10) 0.14396(9) 0.0120(2) Uani 1 1 d . . . . .
H4 H 0.6177 0.7832 0.1053 0.014 Uiso 1 1 calc R U . . .
C5 C 0.66514(13) 0.71205(10) 0.23144(9) 0.0110(2) Uani 1 1 d . . . . .
C6 C 0.81749(12) 0.80687(9) 0.26594(9) 0.0103(2) Uani 1 1 d . . . . .
C7 C 0.97255(12) 0.79348(9) 0.22540(9) 0.0101(2) Uani 1 1 d . . . . .
C8 C 1.04741(13) 0.92293(9) 0.20648(9) 0.0107(2) Uani 1 1 d . . . . .
C9 C 1.19985(13) 0.98084(9) 0.17198(9) 0.0111(2) Uani 1 1 d . . . . .
C10 C 1.21194(13) 1.08740(10) 0.12883(9) 0.0127(2) Uani 1 1 d . . . . .
H10 H 1.1218 1.1145 0.1190 0.015 Uiso 1 1 calc R U . . .
C11 C 1.35235(13) 1.15288(10) 0.10064(9) 0.0135(2) Uani 1 1 d . . . . .
H11 H 1.3591 1.2256 0.0735 0.016 Uiso 1 1 calc R U . . .
C12 C 1.48491(13) 1.11182(10) 0.11209(9) 0.0121(2) Uani 1 1 d . . . . .
C13 C 1.75349(13) 1.13965(11) 0.08783(10) 0.0169(2) Uani 1 1 d . . . . .
H13A H 1.7857 1.1362 0.1578 0.025 Uiso 1 1 calc R U . . .
H13B H 1.8387 1.1941 0.0593 0.025 Uiso 1 1 calc R U . . .
H13C H 1.7288 1.0595 0.0507 0.025 Uiso 1 1 calc R U . . .
C14 C 0.46322(14) 0.53452(10) 0.25642(10) 0.0146(2) Uani 1 1 d . . . . .
H14 H 0.4251 0.4702 0.2939 0.018 Uiso 1 1 calc R U . . .
C15 C 0.60752(13) 0.61849(10) 0.28691(9) 0.0133(2) Uani 1 1 d . . . . .
H15 H 0.6668 0.6118 0.3459 0.016 Uiso 1 1 calc R U . . .
C16 C 0.85481(13) 0.82464(10) 0.38062(9) 0.0118(2) Uani 1 1 d . . . . .
C17 C 0.62696(14) 0.90409(11) 0.40522(10) 0.0164(2) Uani 1 1 d . . . . .
H17A H 0.5440 0.8726 0.4483 0.020 Uiso 1 1 calc R U . . .
H17B H 0.5899 0.8651 0.3363 0.020 Uiso 1 1 calc R U . . .
C18 C 0.65424(16) 1.03851(12) 0.40787(11) 0.0212(3) Uani 1 1 d . . . . .
H18A H 0.6892 1.0774 0.4762 0.032 Uiso 1 1 calc R U . . .
H18B H 0.5566 1.0547 0.3850 0.032 Uiso 1 1 calc R U . . .
H18C H 0.7345 1.0699 0.3641 0.032 Uiso 1 1 calc R U . . .
C19 C 0.81241(15) 0.89138(11) 0.54809(10) 0.0176(2) Uani 1 1 d . . . . .
H19A H 0.7776 0.9591 0.5779 0.021 Uiso 1 1 calc R U . . .
H19B H 0.9276 0.9126 0.5619 0.021 Uiso 1 1 calc R U . . .
C20 C 0.7391(2) 0.78084(13) 0.59646(12) 0.0331(4) Uani 1 1 d . . . . .
H20A H 0.6253 0.7573 0.5804 0.050 Uiso 1 1 calc R U . . .
H20B H 0.7643 0.7984 0.6689 0.050 Uiso 1 1 calc R U . . .
H20C H 0.7802 0.7154 0.5713 0.050 Uiso 1 1 calc R U . . .
C21 C 0.83832(14) 0.55189(10) 0.10954(10) 0.0156(2) Uani 1 1 d . . . . .
H21A H 0.8490 0.4997 0.0509 0.023 Uiso 1 1 calc R U . . .
H21B H 0.7292 0.5532 0.1095 0.023 Uiso 1 1 calc R U . . .
H21C H 0.8695 0.5215 0.1701 0.023 Uiso 1 1 calc R U . . .
C22 C 1.47386(13) 1.00463(10) 0.15094(9) 0.0134(2) Uani 1 1 d . . . . .
H22 H 1.5629 0.9756 0.1572 0.016 Uiso 1 1 calc R U . . .
C23 C 1.33183(13) 0.93963(10) 0.18072(9) 0.0131(2) Uani 1 1 d . . . . .
H23 H 1.3252 0.8666 0.2072 0.016 Uiso 1 1 calc R U . . .
C24 C 0.17883(19) 0.61522(13) 0.57989(12) 0.0283(3) Uani 1 1 d . . . . .
H24A H 0.1451 0.6786 0.5495 0.034 Uiso 1 1 calc R U . . .
H24B H 0.0841 0.5498 0.5866 0.034 Uiso 1 1 calc R U . . .
N1 N 0.77012(11) 0.87309(9) 0.43926(8) 0.01340(19) Uani 1 1 d . . . . .
N2 N 0.97550(12) 0.79299(9) 0.41799(8) 0.01436(19) Uani 1 1 d . . . . .
N3 N 0.95194(11) 0.98768(8) 0.21678(8) 0.01236(19) Uani 1 1 d . . . . .
O1 O 0.23153(10) 0.47129(8) 0.13608(7) 0.01903(19) Uani 1 1 d . . . . .
O2 O 1.61742(10) 1.18225(8) 0.08156(7) 0.01559(17) Uani 1 1 d . . . . .
O3 O 1.22967(10) 0.80187(8) 0.35078(7) 0.01705(18) Uani 1 1 d . . . . .
O4 O 1.11579(10) 0.69076(8) 0.09671(7) 0.01711(18) Uani 1 1 d . . . . .
O5 O 0.88852(10) 0.75525(8) 0.03429(7) 0.01520(17) Uani 1 1 d . . . . .
O6 O 0.80481(9) 0.91868(7) 0.23619(7) 0.01166(16) Uani 1 1 d . . . . .
O7 O 1.01789(11) 0.61409(8) 0.31791(7) 0.01783(18) 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
S1 O3 1.4323(9) . ?
S1 O7 1.4386(9) . ?
S1 N2 1.6165(11) . ?
S1 C7 1.8446(12) . ?
S2 O4 1.4373(9) . ?
S2 O5 1.4401(9) . ?
S2 C21 1.7668(12) . ?
S2 C7 1.8476(12) . ?
Cl1 C24 1.7661(17) . ?
Cl2 C24 1.7655(16) . ?
C1 O1 1.4284(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.3610(14) . ?
C2 C14 1.3918(18) . ?
C2 C3 1.4037(16) . ?
C3 C4 1.3833(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3995(17) . ?
C4 H4 0.9500 . ?
C5 C15 1.3933(16) . ?
C5 C6 1.5106(15) . ?
C6 O6 1.4401(13) . ?
C6 C16 1.5480(17) . ?
C6 C7 1.5681(15) . ?
C7 C8 1.5355(15) . ?
C8 N3 1.2948(14) . ?
C8 C9 1.4766(15) . ?
C9 C23 1.3949(15) . ?
C9 C10 1.4121(15) . ?
C10 C11 1.3807(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.4014(16) . ?
C11 H11 0.9500 . ?
C12 O2 1.3619(13) . ?
C12 C22 1.3916(16) . ?
C13 O2 1.4371(14) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3958(16) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 N2 1.3192(15) . ?
C16 N1 1.3264(15) . ?
C17 N1 1.4800(15) . ?
C17 C18 1.5226(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N1 1.4765(16) . ?
C19 C20 1.5167(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.3987(15) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N3 O6 1.3996(11) . ?

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
O3 S1 O7 117.39(6) . . ?
O3 S1 N2 109.17(6) . . ?
O7 S1 N2 110.65(6) . . ?
O3 S1 C7 112.52(5) . . ?
O7 S1 C7 107.66(5) . . ?
N2 S1 C7 97.68(5) . . ?
O4 S2 O5 119.04(6) . . ?
O4 S2 C21 107.64(5) . . ?
O5 S2 C21 109.36(6) . . ?
O4 S2 C7 105.27(5) . . ?
O5 S2 C7 104.15(5) . . ?
C21 S2 C7 111.24(6) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C14 124.60(11) . . ?
O1 C2 C3 115.21(11) . . ?
C14 C2 C3 120.19(10) . . ?
C4 C3 C2 119.63(11) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.64(11) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C15 C5 C4 119.41(10) . . ?
C15 C5 C6 121.08(11) . . ?
C4 C5 C6 119.48(10) . . ?
O6 C6 C5 108.27(9) . . ?
O6 C6 C16 107.74(9) . . ?
C5 C6 C16 112.40(9) . . ?
O6 C6 C7 104.00(8) . . ?
C5 C6 C7 119.51(9) . . ?
C16 C6 C7 104.12(9) . . ?
C8 C7 C6 99.81(8) . . ?
C8 C7 S1 115.97(8) . . ?
C6 C7 S1 101.91(7) . . ?
C8 C7 S2 106.59(8) . . ?
C6 C7 S2 118.68(8) . . ?
S1 C7 S2 113.53(6) . . ?
N3 C8 C9 116.54(10) . . ?
N3 C8 C7 111.77(9) . . ?
C9 C8 C7 131.48(10) . . ?
C23 C9 C10 118.24(10) . . ?
C23 C9 C8 125.04(10) . . ?
C10 C9 C8 116.70(10) . . ?
C11 C10 C9 121.20(10) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.85(10) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
O2 C12 C22 124.80(10) . . ?
O2 C12 C11 115.42(10) . . ?
C22 C12 C11 119.78(10) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C14 C15 119.66(11) . . ?
C2 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C5 C15 C14 120.44(11) . . ?
C5 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N2 C16 N1 121.10(11) . . ?
N2 C16 C6 118.05(10) . . ?
N1 C16 C6 120.83(10) . . ?
N1 C17 C18 112.36(10) . . ?
N1 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
N1 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 112.11(11) . . ?
N1 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
N1 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S2 C21 H21A 109.5 . . ?
S2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C22 C23 120.07(10) . . ?
C12 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C9 C23 C22 120.78(10) . . ?
C9 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
Cl2 C24 Cl1 111.66(9) . . ?
Cl2 C24 H24A 109.3 . . ?
Cl1 C24 H24A 109.3 . . ?
Cl2 C24 H24B 109.3 . . ?
Cl1 C24 H24B 109.3 . . ?
H24A C24 H24B 107.9 . . ?
C16 N1 C19 119.05(10) . . ?
C16 N1 C17 125.11(11) . . ?
C19 N1 C17 115.71(10) . . ?
C16 N2 S1 112.00(9) . . ?
C8 N3 O6 111.05(9) . . ?
C2 O1 C1 117.01(10) . . ?
C12 O2 C13 116.76(9) . . ?
N3 O6 C6 109.39(8) . . ?

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

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

data_mo_Arnold272LHS_0m
_database_code_depnum_ccdc_archive 'CCDC 1426768'
_audit_update_record             
;
2015-09-23 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H27 N3 O6 S2'
_chemical_formula_weight         505.59

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9873(5)
_cell_length_b                   11.0990(6)
_cell_length_c                   13.0584(7)
_cell_angle_alpha                70.5950(10)
_cell_angle_beta                 76.2910(10)
_cell_angle_gamma                83.975(2)
_cell_volume                     1193.09(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.268
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43008
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.693
_diffrn_reflns_theta_max         35.630
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10964
_reflns_number_gt                8929
_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.
;

# start Validation Reply Form
_vrf_PLAT094_mo_Arnold272LHS_0m  
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       5.09 Report
RESPONSE: ... The maximum residual electron results from the lone pair from the 4-valent sulphur (R2SO) as would be expected. 
;
# end Validation Reply Form





_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0578P)²+0.3521P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10964
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

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
S1 S 0.23238(3) 1.00844(2) 0.16124(2) 0.01372(5) Uani 1 1 d . . . . .
S2 S 0.24646(3) 0.83203(2) 0.39598(2) 0.01379(5) Uani 1 1 d . . . . .
N1 N 0.10475(10) 0.74937(9) 0.48084(7) 0.01772(15) Uani 1 1 d . . . . .
N2 N -0.13530(10) 0.68853(8) 0.48804(7) 0.01760(15) Uani 1 1 d . . . . .
N3 N 0.13529(9) 0.68120(8) 0.20648(7) 0.01513(14) Uani 1 1 d . . . . .
O1 O 0.83128(9) 0.62942(8) -0.02287(7) 0.02163(15) Uani 1 1 d . . . . .
O2 O -0.34670(10) 1.27380(7) 0.19124(6) 0.01950(14) Uani 1 1 d . . . . .
O3 O 0.22356(10) 0.99305(8) 0.05402(6) 0.02037(14) Uani 1 1 d . . . . .
O4 O 0.23673(10) 0.96049(8) 0.40071(6) 0.02114(15) Uani 1 1 d . . . . .
O5 O 0.38714(9) 0.76122(8) 0.41121(6) 0.01961(14) Uani 1 1 d . . . . .
O6 O -0.00597(8) 0.73339(7) 0.24900(6) 0.01517(12) Uani 1 1 d . . . . .
C1 C 0.96871(13) 0.65569(13) 0.00280(12) 0.0279(2) Uani 1 1 d . . . . .
H1A H 0.9673 0.7459 -0.0022 0.042 Uiso 1 1 calc R U . . .
H1B H 1.0580 0.6373 -0.0502 0.042 Uiso 1 1 calc R U . . .
H1C H 0.9747 0.6018 0.0784 0.042 Uiso 1 1 calc R U . . .
C2 C 0.69611(11) 0.65557(9) 0.04042(8) 0.01508(15) Uani 1 1 d . . . . .
C3 C 0.56370(11) 0.63659(9) 0.00919(8) 0.01566(16) Uani 1 1 d . . . . .
H3 H 0.5725 0.6060 -0.0519 0.019 Uiso 1 1 calc R U . . .
C4 C 0.42007(11) 0.66224(9) 0.06709(8) 0.01432(15) Uani 1 1 d . . . . .
H4 H 0.3311 0.6486 0.0455 0.017 Uiso 1 1 calc R U . . .
C5 C 0.40450(10) 0.70832(9) 0.15756(8) 0.01348(15) Uani 1 1 d . . . . .
C6 C 0.24861(10) 0.73937(8) 0.21326(8) 0.01296(14) Uani 1 1 d . . . . .
C7 C 0.19580(10) 0.84398(8) 0.26528(7) 0.01188(14) Uani 1 1 d . . . . .
C8 C 0.01892(10) 0.82061(8) 0.30412(7) 0.01239(14) Uani 1 1 d . . . . .
C9 C -0.08555(10) 0.93782(8) 0.27779(7) 0.01246(14) Uani 1 1 d . . . . .
C10 C -0.12982(12) 1.00690(10) 0.35254(8) 0.01655(16) Uani 1 1 d . . . . .
H10 H -0.1001 0.9765 0.4221 0.020 Uiso 1 1 calc R U . . .
C11 C -0.21709(12) 1.12002(10) 0.32635(8) 0.01794(17) Uani 1 1 d . . . . .
H11 H -0.2457 1.1670 0.3773 0.022 Uiso 1 1 calc R U . . .
C12 C -0.26189(11) 1.16351(9) 0.22492(8) 0.01432(15) Uani 1 1 d . . . . .
C13 C -0.37926(15) 1.35228(11) 0.26155(10) 0.0241(2) Uani 1 1 d . . . . .
H13A H -0.4388 1.3042 0.3346 0.036 Uiso 1 1 calc R U . . .
H13B H -0.4384 1.4286 0.2282 0.036 Uiso 1 1 calc R U . . .
H13C H -0.2830 1.3778 0.2701 0.036 Uiso 1 1 calc R U . . .
C14 C 0.68278(11) 0.69958(10) 0.13055(9) 0.01702(16) Uani 1 1 d . . . . .
H14 H 0.7719 0.7121 0.1526 0.020 Uiso 1 1 calc R U . . .
C15 C 0.53775(11) 0.72521(10) 0.18831(9) 0.01656(16) Uani 1 1 d . . . . .
H15 H 0.5294 0.7548 0.2499 0.020 Uiso 1 1 calc R U . . .
C16 C 0.43193(12) 1.02551(10) 0.15332(9) 0.01884(17) Uani 1 1 d . . . . .
H16A H 0.4934 0.9644 0.1198 0.028 Uiso 1 1 calc R U . . .
H16B H 0.4490 1.0087 0.2283 0.028 Uiso 1 1 calc R U . . .
H16C H 0.4621 1.1127 0.1076 0.028 Uiso 1 1 calc R U . . .
C17 C -0.00686(11) 0.74880(9) 0.43104(8) 0.01431(15) Uani 1 1 d . . . . .
C18 C -0.15212(13) 0.62492(12) 0.60917(9) 0.0249(2) Uani 1 1 d . . . . .
H18A H -0.0545 0.5798 0.6237 0.030 Uiso 1 1 calc R U . . .
H18B H -0.2322 0.5602 0.6351 0.030 Uiso 1 1 calc R U . . .
C19 C -0.19474(17) 0.71824(15) 0.67527(11) 0.0339(3) Uani 1 1 d . . . . .
H19A H -0.1124 0.7790 0.6536 0.051 Uiso 1 1 calc R U . . .
H19B H -0.2092 0.6710 0.7549 0.051 Uiso 1 1 calc R U . . .
H19C H -0.2900 0.7648 0.6599 0.051 Uiso 1 1 calc R U . . .
C20 C -0.26910(11) 0.68693(10) 0.44156(9) 0.01832(17) Uani 1 1 d . . . . .
H20A H -0.2580 0.7533 0.3677 0.022 Uiso 1 1 calc R U . . .
H20B H -0.3628 0.7085 0.4906 0.022 Uiso 1 1 calc R U . . .
C21 C -0.28767(14) 0.55750(11) 0.42950(13) 0.0291(2) Uani 1 1 d . . . . .
H21A H -0.2006 0.5401 0.3744 0.044 Uiso 1 1 calc R U . . .
H21B H -0.3830 0.5588 0.4050 0.044 Uiso 1 1 calc R U . . .
H21C H -0.2913 0.4906 0.5013 0.044 Uiso 1 1 calc R U . . .
C22 C -0.13226(10) 0.98189(9) 0.17636(7) 0.01310(14) Uani 1 1 d . . . . .
H22 H -0.1037 0.9350 0.1253 0.016 Uiso 1 1 calc R U . . .
C23 C -0.22005(11) 1.09380(9) 0.15017(8) 0.01397(15) Uani 1 1 d . . . . .
H23 H -0.2519 1.1232 0.0814 0.017 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
S1 O3 1.4866(8) . ?
S1 C16 1.7981(11) . ?
S1 C7 1.8847(9) . ?
S2 O5 1.4362(8) . ?
S2 O4 1.4402(8) . ?
S2 N1 1.6101(9) . ?
S2 C7 1.8284(9) . ?
N1 C17 1.3200(13) . ?
N2 C17 1.3258(12) . ?
N2 C20 1.4739(14) . ?
N2 C18 1.4800(14) . ?
N3 C6 1.2964(12) . ?
N3 O6 1.4074(10) . ?
O1 C2 1.3610(12) . ?
O1 C1 1.4352(15) . ?
O2 C12 1.3704(12) . ?
O2 C13 1.4275(13) . ?
O6 C8 1.4457(11) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C14 1.3933(14) . ?
C2 C3 1.4023(14) . ?
C3 C4 1.3865(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.4088(13) . ?
C4 H4 0.9500 . ?
C5 C15 1.3985(13) . ?
C5 C6 1.4809(13) . ?
C6 C7 1.5134(13) . ?
C7 C8 1.5712(13) . ?
C8 C9 1.5137(13) . ?
C8 C17 1.5539(13) . ?
C9 C10 1.3957(13) . ?
C9 C22 1.4000(13) . ?
C10 C11 1.3942(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.3917(13) . ?
C11 H11 0.9500 . ?
C12 C23 1.3999(13) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3955(14) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 C19 1.523(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5262(16) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.3863(13) . ?
C22 H22 0.9500 . ?
C23 H23 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
O3 S1 C16 106.05(5) . . ?
O3 S1 C7 104.21(4) . . ?
C16 S1 C7 101.79(4) . . ?
O5 S2 O4 116.72(5) . . ?
O5 S2 N1 109.28(5) . . ?
O4 S2 N1 111.39(5) . . ?
O5 S2 C7 113.40(4) . . ?
O4 S2 C7 105.94(4) . . ?
N1 S2 C7 98.64(4) . . ?
C17 N1 S2 111.79(7) . . ?
C17 N2 C20 124.94(8) . . ?
C17 N2 C18 118.45(9) . . ?
C20 N2 C18 116.47(8) . . ?
C6 N3 O6 110.88(8) . . ?
C2 O1 C1 116.80(9) . . ?
C12 O2 C13 117.03(8) . . ?
N3 O6 C8 109.86(7) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C14 124.69(9) . . ?
O1 C2 C3 115.62(9) . . ?
C14 C2 C3 119.69(9) . . ?
C4 C3 C2 120.29(9) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.78(9) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C15 C5 C4 118.10(8) . . ?
C15 C5 C6 123.43(8) . . ?
C4 C5 C6 118.45(8) . . ?
N3 C6 C5 117.47(8) . . ?
N3 C6 C7 112.55(8) . . ?
C5 C6 C7 129.40(8) . . ?
C6 C7 C8 100.69(7) . . ?
C6 C7 S2 119.47(6) . . ?
C8 C7 S2 101.48(6) . . ?
C6 C7 S1 112.32(6) . . ?
C8 C7 S1 110.20(6) . . ?
S2 C7 S1 111.22(5) . . ?
O6 C8 C9 110.30(7) . . ?
O6 C8 C17 108.64(7) . . ?
C9 C8 C17 112.09(7) . . ?
O6 C8 C7 104.07(7) . . ?
C9 C8 C7 116.32(7) . . ?
C17 C8 C7 104.85(7) . . ?
C10 C9 C22 119.29(8) . . ?
C10 C9 C8 119.96(8) . . ?
C22 C9 C8 120.67(8) . . ?
C11 C10 C9 120.79(9) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.44(9) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
O2 C12 C11 123.84(9) . . ?
O2 C12 C23 116.00(8) . . ?
C11 C12 C23 120.16(9) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C14 C15 119.62(9) . . ?
C2 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C5 121.50(9) . . ?
C14 C15 H15 119.3 . . ?
C5 C15 H15 119.3 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 N2 120.69(9) . . ?
N1 C17 C8 117.46(8) . . ?
N2 C17 C8 121.86(9) . . ?
N2 C18 C19 112.74(10) . . ?
N2 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
N2 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 112.56(9) . . ?
N2 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
N2 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C9 120.19(8) . . ?
C23 C22 H22 119.9 . . ?
C9 C22 H22 119.9 . . ?
C22 C23 C12 120.11(8) . . ?
C22 C23 H23 119.9 . . ?
C12 C23 H23 119.9 . . ?

_refine_diff_density_max         1.578
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4

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

data_mo_ArnoldAP272_1_0ma
_database_code_depnum_ccdc_archive 'CCDC 1426769'
_audit_update_record             
;
2015-09-23 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H27 N3 O6 S2'
_chemical_formula_weight         505.59

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.7894(15)
_cell_length_b                   14.752(2)
_cell_length_c                   14.5737(19)
_cell_angle_alpha                90
_cell_angle_beta                 113.86
_cell_angle_gamma                90
_cell_volume                     2318.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.276
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15611
_diffrn_reflns_av_unetI/netI     0.1213
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.059
_diffrn_reflns_theta_max         28.482
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.725
_diffrn_measured_fraction_theta_full 0.676
_diffrn_reflns_Laue_measured_fraction_max 0.725
_diffrn_reflns_Laue_measured_fraction_full 0.676
_diffrn_reflns_point_group_measured_fraction_max 0.725
_diffrn_reflns_point_group_measured_fraction_full 0.676
_reflns_number_total             4259
_reflns_number_gt                2748
_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.
;

# start Validation Reply Form
_vrf_PLAT019_mo_ArnoldAP272_1_0ma 
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0      0.932 Report
RESPONSE: ... The crystal used were not great diffractors so the data was slightly cut sort so empty frames were not collected. Several crystalisations were attempted and the sample presented here was the best. 
;
# end Validation Reply Form




_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0201P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4259
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0748
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   0.816
_refine_ls_restrained_S_all      0.816
_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
S1 S 0.97805(4) 0.92176(4) 0.16095(4) 0.01515(12) Uani 1 1 d . . . . .
S2 S 0.71783(4) 0.97871(4) 0.11779(4) 0.01354(12) Uani 1 1 d . . . . .
N1 N 0.75708(14) 0.73418(11) 0.14707(11) 0.0128(4) Uani 1 1 d . . . . .
N2 N 0.93178(14) 0.74299(12) -0.02809(12) 0.0152(4) Uani 1 1 d . . . . .
N3 N 1.01476(14) 0.84922(13) 0.09533(13) 0.0168(4) Uani 1 1 d . . . . .
O1 O 0.49627(12) 1.01162(10) -0.32562(11) 0.0202(3) Uani 1 1 d . . . . .
O2 O 0.92290(12) 0.78727(10) 0.61114(10) 0.0169(3) Uani 1 1 d . . . . .
O4 O 0.76407(12) 1.02560(10) 0.21605(10) 0.0171(3) Uani 1 1 d . . . . .
O5 O 0.73191(12) 0.74692(10) 0.04463(9) 0.0125(3) Uani 1 1 d . . . . .
O6 O 0.96532(13) 1.01100(10) 0.11978(11) 0.0206(3) Uani 1 1 d . . . . .
O7 O 1.05779(12) 0.91055(11) 0.26422(11) 0.0206(4) Uani 1 1 d . . . . .
C1 C 0.37186(18) 0.98199(16) -0.38236(16) 0.0239(5) Uani 1 1 d . . . . .
H1A H 0.3729 0.9198 -0.4058 0.036 Uiso 1 1 calc R U . . .
H1B H 0.3323 1.0221 -0.4402 0.036 Uiso 1 1 calc R U . . .
H1C H 0.3252 0.9838 -0.3400 0.036 Uiso 1 1 calc R U . . .
C2 C 0.56183(18) 0.96204(15) -0.24154(15) 0.0154(4) Uani 1 1 d . . . . .
C3 C 0.68399(18) 0.99106(15) -0.18783(16) 0.0190(5) Uani 1 1 d . . . . .
H30 H 0.7164 1.0405 -0.2114 0.023 Uiso 1 1 calc R U . . .
C4 C 0.75647(18) 0.94714(15) -0.10055(15) 0.0169(5) Uani 1 1 d . . . . .
H4 H 0.8396 0.9664 -0.0640 0.020 Uiso 1 1 calc R U . . .
C5 C 0.71017(17) 0.87512(14) -0.06494(14) 0.0125(4) Uani 1 1 d . . . . .
C6 C 0.79052(17) 0.82814(13) 0.03142(14) 0.0121(4) Uani 1 1 d . . . . .
C7 C 0.82001(16) 0.87988(13) 0.13163(14) 0.0113(4) Uani 1 1 d . . . . .
C8 C 0.80665(16) 0.80605(14) 0.19710(14) 0.0124(4) Uani 1 1 d . . . . .
C9 C 0.83387(17) 0.80793(14) 0.30559(14) 0.0122(4) Uani 1 1 d . . . . .
C10 C 0.89509(18) 0.87919(14) 0.36804(15) 0.0153(4) Uani 1 1 d . . . . .
H10 H 0.9168 0.9315 0.3406 0.018 Uiso 1 1 calc R U . . .
C11 C 0.92501(18) 0.87461(14) 0.47105(15) 0.0165(4) Uani 1 1 d . . . . .
H11 H 0.9664 0.9239 0.5132 0.020 Uiso 1 1 calc R U . . .
C12 C 0.89487(17) 0.79927(14) 0.51153(14) 0.0134(4) Uani 1 1 d . . . . .
C13 C 0.98732(19) 0.85976(15) 0.67675(15) 0.0212(5) Uani 1 1 d . . . . .
H13A H 1.0653 0.8718 0.6699 0.032 Uiso 1 1 calc R U . . .
H13B H 1.0052 0.8428 0.7462 0.032 Uiso 1 1 calc R U . . .
H13C H 0.9356 0.9144 0.6590 0.032 Uiso 1 1 calc R U . . .
C14 C 0.59039(17) 0.84580(14) -0.12032(15) 0.0134(4) Uani 1 1 d . . . . .
H14 H 0.5583 0.7954 -0.0979 0.016 Uiso 1 1 calc R U . . .
C15 C 0.51678(17) 0.88984(14) -0.20860(14) 0.0144(4) Uani 1 1 d . . . . .
H15 H 0.4345 0.8695 -0.2463 0.017 Uiso 1 1 calc R U . . .
C16 C 0.91930(17) 0.80483(14) 0.03270(14) 0.0139(4) Uani 1 1 d . . . . .
C17 C 0.58326(16) 0.91637(14) 0.10946(16) 0.0177(5) Uani 1 1 d . . . . .
H17A H 0.6014 0.8842 0.1727 0.026 Uiso 1 1 calc R U . . .
H17B H 0.5608 0.8724 0.0545 0.026 Uiso 1 1 calc R U . . .
H17C H 0.5141 0.9584 0.0966 0.026 Uiso 1 1 calc R U . . .
C18 C 0.83029(17) 0.72847(14) 0.44911(14) 0.0136(4) Uani 1 1 d . . . . .
H18 H 0.8070 0.6770 0.4766 0.016 Uiso 1 1 calc R U . . .
C19 C 0.80030(17) 0.73302(14) 0.34794(15) 0.0140(4) Uani 1 1 d . . . . .
H19 H 0.7560 0.6844 0.3059 0.017 Uiso 1 1 calc R U . . .
C20 C 0.83047(17) 0.69346(15) -0.10610(14) 0.0156(5) Uani 1 1 d . . . . .
H20A H 0.7538 0.7000 -0.0944 0.019 Uiso 1 1 calc R U . . .
H20B H 0.8515 0.6282 -0.1021 0.019 Uiso 1 1 calc R U . . .
C21 C 1.05810(17) 0.71949(15) -0.01734(16) 0.0193(5) Uani 1 1 d . . . . .
H21A H 1.1106 0.7745 0.0000 0.023 Uiso 1 1 calc R U . . .
H21B H 1.0550 0.6958 -0.0819 0.023 Uiso 1 1 calc R U . . .
C22 C 1.11395(18) 0.64934(16) 0.06320(15) 0.0223(5) Uani 1 1 d . . . . .
H22A H 1.1121 0.6714 0.1260 0.033 Uiso 1 1 calc R U . . .
H22B H 1.2000 0.6379 0.0730 0.033 Uiso 1 1 calc R U . . .
H22C H 1.0662 0.5930 0.0431 0.033 Uiso 1 1 calc R U . . .
C23 C 0.8076(2) 0.72881(15) -0.21013(15) 0.0209(5) Uani 1 1 d . . . . .
H3A H 0.7936 0.7944 -0.2125 0.031 Uiso 1 1 calc R U . . .
H3B H 0.7344 0.6989 -0.2600 0.031 Uiso 1 1 calc R U . . .
H3C H 0.8800 0.7159 -0.2249 0.031 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
S1 O7 1.4254(14) . ?
S1 O6 1.4291(16) . ?
S1 N3 1.6067(18) . ?
S1 C7 1.8416(19) . ?
S2 O4 1.4814(15) . ?
S2 C17 1.795(2) . ?
S2 C7 1.850(2) . ?
N1 C8 1.285(2) . ?
N1 O5 1.412(2) . ?
N2 C16 1.321(3) . ?
N2 C20 1.468(2) . ?
N2 C21 1.474(2) . ?
N3 C16 1.303(2) . ?
O1 C2 1.367(2) . ?
O1 C1 1.430(2) . ?
O2 C12 1.364(2) . ?
O2 C13 1.431(2) . ?
O5 C6 1.434(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C15 1.361(3) . ?
C2 C3 1.399(3) . ?
C3 C4 1.374(3) . ?
C3 H30 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C14 1.382(3) . ?
C5 C6 1.508(3) . ?
C6 C16 1.550(3) . ?
C6 C7 1.557(3) . ?
C7 C8 1.498(3) . ?
C8 C9 1.481(3) . ?
C9 C10 1.387(3) . ?
C9 C19 1.399(3) . ?
C10 C11 1.398(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.371(3) . ?
C11 H11 0.9500 . ?
C12 C18 1.392(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.372(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C23 1.521(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.502(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H3A 0.9800 . ?
C23 H3B 0.9800 . ?
C23 H3C 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
O7 S1 O6 117.55(9) . . ?
O7 S1 N3 109.25(9) . . ?
O6 S1 N3 111.80(9) . . ?
O7 S1 C7 112.30(8) . . ?
O6 S1 C7 106.68(9) . . ?
N3 S1 C7 97.43(9) . . ?
O4 S2 C17 105.92(9) . . ?
O4 S2 C7 107.08(8) . . ?
C17 S2 C7 97.03(9) . . ?
C8 N1 O5 110.05(17) . . ?
C16 N2 C20 125.94(17) . . ?
C16 N2 C21 118.23(17) . . ?
C20 N2 C21 115.83(16) . . ?
C16 N3 S1 112.79(14) . . ?
C2 O1 C1 115.51(18) . . ?
C12 O2 C13 116.67(16) . . ?
N1 O5 C6 110.26(14) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C15 C2 O1 125.10(17) . . ?
C15 C2 C3 120.15(19) . . ?
O1 C2 C3 114.7(2) . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H30 120.4 . . ?
C2 C3 H30 120.4 . . ?
C3 C4 C5 121.04(18) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C14 C5 C4 119.00(19) . . ?
C14 C5 C6 120.6(2) . . ?
C4 C5 C6 120.42(17) . . ?
O5 C6 C5 110.71(15) . . ?
O5 C6 C16 109.62(16) . . ?
C5 C6 C16 110.89(16) . . ?
O5 C6 C7 102.74(15) . . ?
C5 C6 C7 117.77(17) . . ?
C16 C6 C7 104.56(14) . . ?
C8 C7 C6 101.53(15) . . ?
C8 C7 S1 116.96(13) . . ?
C6 C7 S1 101.72(12) . . ?
C8 C7 S2 114.27(13) . . ?
C6 C7 S2 113.30(12) . . ?
S1 C7 S2 108.31(10) . . ?
N1 C8 C9 118.26(19) . . ?
N1 C8 C7 112.29(17) . . ?
C9 C8 C7 129.29(18) . . ?
C10 C9 C19 118.32(18) . . ?
C10 C9 C8 123.06(19) . . ?
C19 C9 C8 118.58(18) . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.30(19) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O2 C12 C11 124.75(18) . . ?
O2 C12 C18 115.54(19) . . ?
C11 C12 C18 119.71(18) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C14 C15 120.2(2) . . ?
C5 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C2 C15 C14 120.40(18) . . ?
C2 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N3 C16 N2 121.21(18) . . ?
N3 C16 C6 117.47(18) . . ?
N2 C16 C6 121.31(17) . . ?
S2 C17 H17A 109.5 . . ?
S2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C12 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C12 C18 H18 120.0 . . ?
C18 C19 C9 121.13(19) . . ?
C18 C19 H19 119.4 . . ?
C9 C19 H19 119.4 . . ?
N2 C20 C23 111.24(18) . . ?
N2 C20 H20A 109.4 . . ?
C23 C20 H20A 109.4 . . ?
N2 C20 H20B 109.4 . . ?
C23 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
N2 C21 C22 110.47(18) . . ?
N2 C21 H21A 109.6 . . ?
C22 C21 H21A 109.6 . . ?
N2 C21 H21B 109.6 . . ?
C22 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H3A 109.5 . . ?
C20 C23 H3B 109.5 . . ?
H3A C23 H3B 109.5 . . ?
C20 C23 H3C 109.5 . . ?
H3A C23 H3C 109.5 . . ?
H3B C23 H3C 109.5 . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1441502'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-08 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         'C18 H23 N3 O6 S'
_chemical_formula_sum            'C18 H23 N3 O6 S'
_chemical_formula_weight         409.45

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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   12.9462(7)
_cell_length_b                   14.7915(7)
_cell_length_c                   21.2167(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4062.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    27333
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       'Cut Block'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9284
_exptl_absorpt_correction_T_max  0.9690
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
SADABS was used to perform the Absorption correction
Estimated minimum and maximum transmission: 0.6091 0.7456
The given Tmin and Tmax were generated using the SHELX SIZE command
;


_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_reflns_number            26629
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.147
_diffrn_reflns_theta_max         27.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4679
_reflns_number_gt                3120
_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       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
 WINGX (Farrugia, 1998)
 Olex2 (Dolomanov et al., 2009)
;

_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)+(0.0643P)²+2.4800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4679
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1488
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.51558(19) 0.92032(15) 0.59027(11) 0.0179(5) Uani 1 1 d . . . . .
H1 H 0.5279 0.9135 0.5440 0.021 Uiso 1 1 calc R U . . .
C2 C 0.6130(2) 0.90164(15) 0.62929(10) 0.0185(5) Uani 1 1 d . . . . .
C3 C 0.6322(2) 0.98846(17) 0.66846(11) 0.0237(6) Uani 1 1 d . . . . .
C4 C 0.4431(2) 0.85096(16) 0.61528(11) 0.0205(5) Uani 1 1 d . . . . .
C5 C 0.7217(3) 1.0809(2) 0.74473(13) 0.0379(8) Uani 1 1 d . . . . .
H5A H 0.7942 1.0872 0.7588 0.046 Uiso 1 1 calc R U . . .
H5B H 0.7055 1.1325 0.7167 0.046 Uiso 1 1 calc R U . . .
C6 C 0.6526(3) 1.0830(2) 0.80001(15) 0.0474(9) Uani 1 1 d . . . . .
H6A H 0.5807 1.0783 0.7860 0.071 Uiso 1 1 calc R U . . .
H6B H 0.6624 1.1399 0.8229 0.071 Uiso 1 1 calc R U . . .
H6C H 0.6690 1.0322 0.8279 0.071 Uiso 1 1 calc R U . . .
C7 C 0.7792(2) 0.92053(19) 0.72752(12) 0.0304(7) Uani 1 1 d . . . . .
H7A H 0.7511 0.8630 0.7110 0.037 Uiso 1 1 calc R U . . .
H7B H 0.7813 0.9161 0.7741 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8878(2) 0.9335(2) 0.70284(14) 0.0409(8) Uani 1 1 d . . . . .
H8A H 0.8863 0.9369 0.6567 0.061 Uiso 1 1 calc R U . . .
H8B H 0.9308 0.8823 0.7159 0.061 Uiso 1 1 calc R U . . .
H8C H 0.9166 0.9896 0.7199 0.061 Uiso 1 1 calc R U . . .
C9 C 0.3370(2) 0.83961(17) 0.58938(12) 0.0237(6) Uani 1 1 d . . . . .
C10 C 0.1828(2) 0.7542(2) 0.59448(15) 0.0407(8) Uani 1 1 d . . . . .
H10A H 0.1756 0.7753 0.5504 0.049 Uiso 1 1 calc R U . . .
H10B H 0.1698 0.6883 0.5953 0.049 Uiso 1 1 calc R U . . .
C11 C 0.1078(3) 0.7999(3) 0.6340(2) 0.0732(13) Uani 1 1 d . . . . .
H11A H 0.1145 0.7783 0.6775 0.110 Uiso 1 1 calc R U . . .
H11B H 0.0380 0.7871 0.6185 0.110 Uiso 1 1 calc R U . . .
H11C H 0.1203 0.8652 0.6327 0.110 Uiso 1 1 calc R U . . .
C12 C 0.70502(19) 0.87355(16) 0.58979(11) 0.0192(5) Uani 1 1 d . . . . .
C13 C 0.7427(2) 0.93344(17) 0.54491(11) 0.0230(6) Uani 1 1 d . . . . .
H13 H 0.7095 0.9901 0.5393 0.028 Uiso 1 1 calc R U . . .
C14 C 0.8282(2) 0.91200(18) 0.50813(12) 0.0264(6) Uani 1 1 d . . . . .
H14 H 0.8528 0.9533 0.4773 0.032 Uiso 1 1 calc R U . . .
C15 C 0.8770(2) 0.82953(18) 0.51711(11) 0.0259(6) Uani 1 1 d . . . . .
C16 C 0.8388(2) 0.76784(18) 0.56059(12) 0.0260(6) Uani 1 1 d . . . . .
H16 H 0.8713 0.7107 0.5655 0.031 Uiso 1 1 calc R U . . .
C17 C 0.7531(2) 0.78968(16) 0.59689(11) 0.0219(6) Uani 1 1 d . . . . .
H17 H 0.7271 0.7474 0.6266 0.026 Uiso 1 1 calc R U . . .
C18 C 1.0139(3) 0.8661(2) 0.44567(15) 0.0448(8) Uani 1 1 d . . . . .
H18A H 0.9687 0.8820 0.4103 0.067 Uiso 1 1 calc R U . . .
H18B H 1.0783 0.8401 0.4295 0.067 Uiso 1 1 calc R U . . .
H18C H 1.0294 0.9205 0.4702 0.067 Uiso 1 1 calc R U . . .
N1 N 0.56922(18) 1.05672(14) 0.65971(10) 0.0271(5) Uani 1 1 d . . . . .
N2 N 0.47883(17) 0.80308(14) 0.66075(9) 0.0230(5) Uani 1 1 d . . . . .
N3 N 0.70967(18) 0.99526(15) 0.70933(10) 0.0293(5) Uani 1 1 d . . . . .
O1 O 0.48243(14) 1.09265(11) 0.55768(7) 0.0232(4) Uani 1 1 d . . . . .
O2 O 0.38004(14) 1.03208(11) 0.64479(8) 0.0272(4) Uani 1 1 d . . . . .
O3 O 0.58157(13) 0.82942(11) 0.67268(7) 0.0226(4) Uani 1 1 d . . . . .
O4 O 0.30539(14) 0.88721(12) 0.54763(8) 0.0298(5) Uani 1 1 d . . . . .
O5 O 0.28687(15) 0.77253(13) 0.61677(9) 0.0355(5) Uani 1 1 d . . . . .
O6 O 0.96342(15) 0.80192(13) 0.48475(8) 0.0344(5) Uani 1 1 d . . . . .
S1 S 0.47640(5) 1.03422(4) 0.61154(3) 0.01824(17) 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 C4 1.488(3) . ?
C1 C2 1.534(3) . ?
C1 S1 1.816(2) . ?
C1 H1 1.0000 . ?
C2 O3 1.468(3) . ?
C2 C12 1.514(3) . ?
C2 C3 1.550(3) . ?
C3 N1 1.311(3) . ?
C3 N3 1.329(3) . ?
C4 N2 1.283(3) . ?
C4 C9 1.489(4) . ?
C5 C6 1.475(5) . ?
C5 N3 1.481(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N3 1.477(3) . ?
C7 C8 1.513(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O4 1.203(3) . ?
C9 O5 1.320(3) . ?
C10 C11 1.450(5) . ?
C10 O5 1.453(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.389(3) . ?
C12 C17 1.396(3) . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 O6 1.375(3) . ?
C15 C16 1.389(4) . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 O6 1.420(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 S1 1.612(2) . ?
N2 O3 1.409(3) . ?
O1 S1 1.4349(16) . ?
O2 S1 1.4335(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 C2 101.65(19) . . ?
C4 C1 S1 112.01(17) . . ?
C2 C1 S1 105.23(15) . . ?
C4 C1 H1 112.4 . . ?
C2 C1 H1 112.4 . . ?
S1 C1 H1 112.4 . . ?
O3 C2 C12 111.45(19) . . ?
O3 C2 C1 103.96(19) . . ?
C12 C2 C1 113.43(19) . . ?
O3 C2 C3 108.13(18) . . ?
C12 C2 C3 113.4(2) . . ?
C1 C2 C3 105.79(19) . . ?
N1 C3 N3 120.2(2) . . ?
N1 C3 C2 117.5(2) . . ?
N3 C3 C2 122.2(2) . . ?
N2 C4 C1 114.9(2) . . ?
N2 C4 C9 123.2(2) . . ?
C1 C4 C9 121.9(2) . . ?
C6 C5 N3 111.0(3) . . ?
C6 C5 H5A 109.4 . . ?
N3 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
N3 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 C8 112.4(2) . . ?
N3 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N3 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 O5 126.6(3) . . ?
O4 C9 C4 121.3(2) . . ?
O5 C9 C4 112.1(2) . . ?
C11 C10 O5 110.2(3) . . ?
C11 C10 H10A 109.6 . . ?
O5 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
O5 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.9(2) . . ?
C13 C12 C2 118.7(2) . . ?
C17 C12 C2 122.3(2) . . ?
C12 C13 C14 121.3(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
O6 C15 C14 124.3(2) . . ?
O6 C15 C16 115.2(2) . . ?
C14 C15 C16 120.5(2) . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 N1 S1 113.24(17) . . ?
C4 N2 O3 108.8(2) . . ?
C3 N3 C7 125.0(2) . . ?
C3 N3 C5 118.3(2) . . ?
C7 N3 C5 116.3(2) . . ?
N2 O3 C2 110.52(17) . . ?
C9 O5 C10 116.9(2) . . ?
C15 O6 C18 117.9(2) . . ?
O2 S1 O1 116.91(11) . . ?
O2 S1 N1 109.95(11) . . ?
O1 S1 N1 109.88(11) . . ?
O2 S1 C1 110.16(11) . . ?
O1 S1 C1 110.22(10) . . ?
N1 S1 C1 98.09(11) . . ?

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
C4 C1 C2 O3 -3.1(2) . . . . ?
S1 C1 C2 O3 113.83(16) . . . . ?
C4 C1 C2 C12 118.1(2) . . . . ?
S1 C1 C2 C12 -124.95(18) . . . . ?
C4 C1 C2 C3 -116.9(2) . . . . ?
S1 C1 C2 C3 0.0(2) . . . . ?
O3 C2 C3 N1 -113.3(2) . . . . ?
C12 C2 C3 N1 122.6(2) . . . . ?
C1 C2 C3 N1 -2.4(3) . . . . ?
O3 C2 C3 N3 67.3(3) . . . . ?
C12 C2 C3 N3 -56.9(3) . . . . ?
C1 C2 C3 N3 178.1(2) . . . . ?
C2 C1 C4 N2 3.3(3) . . . . ?
S1 C1 C4 N2 -108.6(2) . . . . ?
C2 C1 C4 C9 -177.3(2) . . . . ?
S1 C1 C4 C9 70.8(3) . . . . ?
N2 C4 C9 O4 178.3(2) . . . . ?
C1 C4 C9 O4 -1.0(4) . . . . ?
N2 C4 C9 O5 -2.8(3) . . . . ?
C1 C4 C9 O5 177.9(2) . . . . ?
O3 C2 C12 C13 178.2(2) . . . . ?
C1 C2 C12 C13 61.3(3) . . . . ?
C3 C2 C12 C13 -59.5(3) . . . . ?
O3 C2 C12 C17 -1.8(3) . . . . ?
C1 C2 C12 C17 -118.7(2) . . . . ?
C3 C2 C12 C17 120.6(2) . . . . ?
C17 C12 C13 C14 -1.3(4) . . . . ?
C2 C12 C13 C14 178.8(2) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C13 C14 C15 O6 -178.3(2) . . . . ?
C13 C14 C15 C16 2.3(4) . . . . ?
O6 C15 C16 C17 178.5(2) . . . . ?
C14 C15 C16 C17 -2.0(4) . . . . ?
C15 C16 C17 C12 0.1(4) . . . . ?
C13 C12 C17 C16 1.6(4) . . . . ?
C2 C12 C17 C16 -178.5(2) . . . . ?
N3 C3 N1 S1 -176.7(2) . . . . ?
C2 C3 N1 S1 3.8(3) . . . . ?
C1 C4 N2 O3 -2.0(3) . . . . ?
C9 C4 N2 O3 178.7(2) . . . . ?
N1 C3 N3 C7 173.9(2) . . . . ?
C2 C3 N3 C7 -6.6(4) . . . . ?
N1 C3 N3 C5 0.7(4) . . . . ?
C2 C3 N3 C5 -179.9(2) . . . . ?
C8 C7 N3 C3 110.6(3) . . . . ?
C8 C7 N3 C5 -76.1(3) . . . . ?
C6 C5 N3 C3 82.6(3) . . . . ?
C6 C5 N3 C7 -91.3(3) . . . . ?
C4 N2 O3 C2 -0.3(2) . . . . ?
C12 C2 O3 N2 -120.2(2) . . . . ?
C1 C2 O3 N2 2.3(2) . . . . ?
C3 C2 O3 N2 114.4(2) . . . . ?
O4 C9 O5 C10 -0.1(4) . . . . ?
C4 C9 O5 C10 -179.0(2) . . . . ?
C11 C10 O5 C9 -95.3(3) . . . . ?
C14 C15 O6 C18 8.5(4) . . . . ?
C16 C15 O6 C18 -172.1(2) . . . . ?
C3 N1 S1 O2 111.7(2) . . . . ?
C3 N1 S1 O1 -118.2(2) . . . . ?
C3 N1 S1 C1 -3.2(2) . . . . ?
C4 C1 S1 O2 -3.5(2) . . . . ?
C2 C1 S1 O2 -113.12(16) . . . . ?
C4 C1 S1 O1 -133.97(17) . . . . ?
C2 C1 S1 O1 116.41(16) . . . . ?
C4 C1 S1 N1 111.30(18) . . . . ?
C2 C1 S1 N1 1.68(17) . . . . ?

_refine_diff_density_max         0.754
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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 1441503'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-08 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         'C27 H28 N4 O3 S'
_chemical_formula_sum            'C27 H28 N4 O3 S'
_chemical_formula_weight         488.59

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      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                   8.9260(8)
_cell_length_b                   15.4665(7)
_cell_length_c                   17.7890(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.900(3)
_cell_angle_gamma                90
_cell_volume                     2419.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    27399
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.1

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9441
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
SADABS was used to perform the Absorption correction
Estimated minimum and maximum transmission: 0.6540 0.7455
The given Tmin and Tmax were generated using the SHELX SIZE command
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_reflns_number            31632
_diffrn_reflns_av_unetI/netI     0.1474
_diffrn_reflns_av_R_equivalents  0.1765
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.987
_diffrn_reflns_theta_max         27.213
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5360
_reflns_number_gt                2847
_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       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
 WINGX (Farrugia, 1998)
 Olex2 (Dolomanov et al., 2009)
;

_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)+(0.0611P)²+0.9320P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0100(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5360
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.0734
_refine_ls_wR_factor_ref         0.1645
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0850(4) 0.3804(2) 0.16156(18) 0.0219(8) Uani 1 1 d . . . . .
C2 C 0.9150(4) 0.36928(19) 0.16331(18) 0.0209(8) Uani 1 1 d . . . . .
C3 C 0.8383(4) 0.45333(19) 0.1292(2) 0.0241(8) Uani 1 1 d . . . . .
H3 H 0.7804 0.4449 0.0764 0.029 Uiso 1 1 calc R U . . .
C4 C 1.3456(4) 0.3369(2) 0.1723(2) 0.0290(9) Uani 1 1 d . . . . .
H4A H 1.4105 0.2893 0.1966 0.035 Uiso 1 1 calc R U . . .
H4B H 1.3746 0.3902 0.2020 0.035 Uiso 1 1 calc R U . . .
C5 C 1.3755(5) 0.3496(2) 0.0914(2) 0.0385(10) Uani 1 1 d . . . . .
H5A H 1.4833 0.3629 0.0929 0.058 Uiso 1 1 calc R U . . .
H5B H 1.3491 0.2966 0.0619 0.058 Uiso 1 1 calc R U . . .
H5C H 1.3133 0.3976 0.0673 0.058 Uiso 1 1 calc R U . . .
C6 C 1.1543(4) 0.22811(19) 0.19995(19) 0.0231(8) Uani 1 1 d . . . . .
H6A H 1.0459 0.2239 0.2051 0.028 Uiso 1 1 calc R U . . .
H6B H 1.2162 0.2174 0.2508 0.028 Uiso 1 1 calc R U . . .
C7 C 1.1895(4) 0.1588(2) 0.14481(19) 0.0285(9) Uani 1 1 d . . . . .
H7A H 1.1670 0.1017 0.1640 0.043 Uiso 1 1 calc R U . . .
H7B H 1.1268 0.1682 0.0946 0.043 Uiso 1 1 calc R U . . .
H7C H 1.2973 0.1617 0.1403 0.043 Uiso 1 1 calc R U . . .
C8 C 0.8405(4) 0.29093(19) 0.11924(18) 0.0202(8) Uani 1 1 d . . . . .
C9 C 0.8753(4) 0.2703(2) 0.04825(19) 0.0246(8) Uani 1 1 d . . . . .
H9 H 0.9492 0.3034 0.0283 0.030 Uiso 1 1 calc R U . . .
C10 C 0.8035(4) 0.2020(2) 0.00613(19) 0.0245(8) Uani 1 1 d . . . . .
H10 H 0.8305 0.1874 -0.0417 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6928(4) 0.15520(19) 0.03362(18) 0.0219(8) Uani 1 1 d . . . . .
C12 C 0.6571(4) 0.1751(2) 0.10395(19) 0.0243(8) Uani 1 1 d . . . . .
H12 H 0.5813 0.1428 0.1232 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7318(4) 0.2422(2) 0.14669(19) 0.0234(8) Uani 1 1 d . . . . .
H13 H 0.7079 0.2548 0.1955 0.028 Uiso 1 1 calc R U . . .
C14 C 0.6510(6) 0.0618(3) -0.0758(2) 0.0456(11) Uani 1 1 d . . . . .
H14A H 0.5852 0.0138 -0.0968 0.068 Uiso 1 1 calc R U . . .
H14B H 0.6369 0.1105 -0.1116 0.068 Uiso 1 1 calc R U . . .
H14C H 0.7574 0.0431 -0.0679 0.068 Uiso 1 1 calc R U . . .
C15 C 0.9976(4) 0.3656(2) 0.30928(18) 0.0219(8) Uani 1 1 d . . . . .
C16 C 1.0224(4) 0.2870(2) 0.34667(18) 0.0230(8) Uani 1 1 d . . . . .
H16 H 0.9604 0.2385 0.3297 0.028 Uiso 1 1 calc R U . . .
C17 C 1.1389(4) 0.2795(2) 0.40929(19) 0.0263(8) Uani 1 1 d . . . . .
H17 H 1.1565 0.2256 0.4349 0.032 Uiso 1 1 calc R U . . .
C18 C 1.2284(5) 0.3494(2) 0.4344(2) 0.0337(9) Uani 1 1 d . . . . .
H18 H 1.3089 0.3433 0.4765 0.040 Uiso 1 1 calc R U . . .
C19 C 1.2016(5) 0.4287(2) 0.3983(2) 0.0340(10) Uani 1 1 d . . . . .
H19 H 1.2624 0.4774 0.4163 0.041 Uiso 1 1 calc R U . . .
C20 C 1.0862(4) 0.4368(2) 0.3361(2) 0.0295(9) Uani 1 1 d . . . . .
H20 H 1.0673 0.4913 0.3115 0.035 Uiso 1 1 calc R U . . .
C21 C 0.7372(4) 0.4770(2) 0.18516(19) 0.0241(8) Uani 1 1 d . . . . .
C22 C 0.6150(4) 0.5415(2) 0.1710(2) 0.0263(8) Uani 1 1 d . . . . .
C23 C 0.5132(4) 0.5510(2) 0.2215(2) 0.0278(9) Uani 1 1 d . . . . .
H23 H 0.5253 0.5169 0.2666 0.033 Uiso 1 1 calc R U . . .
C24 C 0.3941(5) 0.6096(2) 0.2069(2) 0.0317(9) Uani 1 1 d . . . . .
H24 H 0.3233 0.6144 0.2410 0.038 Uiso 1 1 calc R U . . .
C25 C 0.3793(5) 0.6608(2) 0.1428(2) 0.0428(11) Uani 1 1 d . . . . .
H25 H 0.2993 0.7020 0.1331 0.051 Uiso 1 1 calc R U . . .
C26 C 0.4802(5) 0.6525(3) 0.0923(3) 0.0490(12) Uani 1 1 d . . . . .
H26 H 0.4691 0.6878 0.0480 0.059 Uiso 1 1 calc R U . . .
C27 C 0.5971(5) 0.5931(2) 0.1062(2) 0.0402(10) Uani 1 1 d . . . . .
H27 H 0.6657 0.5875 0.0711 0.048 Uiso 1 1 calc R U . . .
N1 N 1.1320(4) 0.45858(17) 0.14510(17) 0.0287(7) Uani 1 1 d . . . . .
N2 N 1.1855(3) 0.31672(17) 0.17491(15) 0.0244(7) Uani 1 1 d . . . . .
N3 N 0.8788(3) 0.37147(16) 0.24294(15) 0.0220(7) Uani 1 1 d . . . . .
N4 N 0.7724(3) 0.43665(16) 0.24896(16) 0.0236(7) Uani 1 1 d . . . . .
O1 O 0.9880(3) 0.57226(14) 0.06034(14) 0.0340(7) Uani 1 1 d . . . . .
O2 O 1.0038(3) 0.58338(13) 0.19830(14) 0.0300(6) Uani 1 1 d . . . . .
O3 O 0.6120(3) 0.08831(14) -0.00423(13) 0.0285(6) Uani 1 1 d . . . . .
S1 S 0.99604(11) 0.52871(5) 0.13212(5) 0.0269(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 N2 1.326(4) . ?
C1 N1 1.329(4) . ?
C1 C2 1.532(5) . ?
C2 N3 1.507(4) . ?
C2 C8 1.532(4) . ?
C2 C3 1.544(4) . ?
C3 C21 1.500(5) . ?
C3 S1 1.822(3) . ?
C3 H3 1.0000 . ?
C4 N2 1.471(5) . ?
C4 C5 1.520(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N2 1.482(4) . ?
C6 C7 1.522(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.382(5) . ?
C8 C9 1.388(5) . ?
C9 C10 1.387(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(5) . ?
C10 H10 0.9500 . ?
C11 O3 1.370(4) . ?
C11 C12 1.378(5) . ?
C12 C13 1.388(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O3 1.436(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.386(4) . ?
C15 C20 1.392(5) . ?
C15 N3 1.447(4) . ?
C16 C17 1.392(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.372(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 N4 1.286(4) . ?
C21 C22 1.468(5) . ?
C22 C27 1.389(5) . ?
C22 C23 1.391(5) . ?
C23 C24 1.388(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(5) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
N1 S1 1.614(3) . ?
N3 N4 1.402(4) . ?
O1 S1 1.435(2) . ?
O2 S1 1.441(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 119.0(3) . . ?
N2 C1 C2 123.7(3) . . ?
N1 C1 C2 117.2(3) . . ?
N3 C2 C8 110.8(3) . . ?
N3 C2 C1 113.0(3) . . ?
C8 C2 C1 115.0(3) . . ?
N3 C2 C3 101.4(2) . . ?
C8 C2 C3 109.9(3) . . ?
C1 C2 C3 105.7(3) . . ?
C21 C3 C2 102.8(3) . . ?
C21 C3 S1 112.0(2) . . ?
C2 C3 S1 103.8(2) . . ?
C21 C3 H3 112.5 . . ?
C2 C3 H3 112.5 . . ?
S1 C3 H3 112.5 . . ?
N2 C4 C5 112.8(3) . . ?
N2 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 112.8(3) . . ?
N2 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 118.5(3) . . ?
C13 C8 C2 121.3(3) . . ?
C9 C8 C2 120.1(3) . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
O3 C11 C12 115.5(3) . . ?
O3 C11 C10 124.8(3) . . ?
C12 C11 C10 119.8(3) . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 121.0(3) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 119.7(3) . . ?
C16 C15 N3 118.7(3) . . ?
C20 C15 N3 121.6(3) . . ?
C15 C16 C17 119.5(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 120.3(3) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
N4 C21 C22 122.9(3) . . ?
N4 C21 C3 112.6(3) . . ?
C22 C21 C3 124.5(3) . . ?
C27 C22 C23 118.7(3) . . ?
C27 C22 C21 120.6(3) . . ?
C23 C22 C21 120.6(3) . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 119.5(4) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.3(4) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 120.2(4) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C22 120.4(4) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 119.8 . . ?
C1 N1 S1 112.6(3) . . ?
C1 N2 C4 117.9(3) . . ?
C1 N2 C6 125.7(3) . . ?
C4 N2 C6 116.1(3) . . ?
N4 N3 C15 113.2(2) . . ?
N4 N3 C2 110.2(2) . . ?
C15 N3 C2 121.3(3) . . ?
C21 N4 N3 110.3(3) . . ?
C11 O3 C14 117.6(3) . . ?
O1 S1 O2 116.07(14) . . ?
O1 S1 N1 111.35(16) . . ?
O2 S1 N1 110.35(16) . . ?
O1 S1 C3 110.77(16) . . ?
O2 S1 C3 109.13(16) . . ?
N1 S1 C3 97.60(15) . . ?

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
N2 C1 C2 N3 81.0(4) . . . . ?
N1 C1 C2 N3 -99.5(3) . . . . ?
N2 C1 C2 C8 -47.5(4) . . . . ?
N1 C1 C2 C8 132.0(3) . . . . ?
N2 C1 C2 C3 -168.9(3) . . . . ?
N1 C1 C2 C3 10.6(4) . . . . ?
N3 C2 C3 C21 -14.7(3) . . . . ?
C8 C2 C3 C21 102.6(3) . . . . ?
C1 C2 C3 C21 -132.7(3) . . . . ?
N3 C2 C3 S1 102.2(2) . . . . ?
C8 C2 C3 S1 -140.6(2) . . . . ?
C1 C2 C3 S1 -15.9(3) . . . . ?
N3 C2 C8 C13 11.9(4) . . . . ?
C1 C2 C8 C13 141.5(3) . . . . ?
C3 C2 C8 C13 -99.3(4) . . . . ?
N3 C2 C8 C9 -171.6(3) . . . . ?
C1 C2 C8 C9 -42.1(4) . . . . ?
C3 C2 C8 C9 77.1(4) . . . . ?
C13 C8 C9 C10 -0.5(5) . . . . ?
C2 C8 C9 C10 -177.0(3) . . . . ?
C8 C9 C10 C11 1.9(5) . . . . ?
C9 C10 C11 O3 178.0(3) . . . . ?
C9 C10 C11 C12 -1.8(5) . . . . ?
O3 C11 C12 C13 -179.6(3) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C9 C8 C13 C12 -1.1(5) . . . . ?
C2 C8 C13 C12 175.4(3) . . . . ?
C11 C12 C13 C8 1.2(5) . . . . ?
C20 C15 C16 C17 -1.9(5) . . . . ?
N3 C15 C16 C17 178.2(3) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C19 1.2(6) . . . . ?
C17 C18 C19 C20 -1.2(6) . . . . ?
C18 C19 C20 C15 -0.4(6) . . . . ?
C16 C15 C20 C19 2.0(5) . . . . ?
N3 C15 C20 C19 -178.2(3) . . . . ?
C2 C3 C21 N4 16.2(4) . . . . ?
S1 C3 C21 N4 -94.7(3) . . . . ?
C2 C3 C21 C22 -166.2(3) . . . . ?
S1 C3 C21 C22 82.9(4) . . . . ?
N4 C21 C22 C27 169.6(3) . . . . ?
C3 C21 C22 C27 -7.8(5) . . . . ?
N4 C21 C22 C23 -11.6(5) . . . . ?
C3 C21 C22 C23 171.1(3) . . . . ?
C27 C22 C23 C24 1.2(5) . . . . ?
C21 C22 C23 C24 -177.6(3) . . . . ?
C22 C23 C24 C25 -1.9(5) . . . . ?
C23 C24 C25 C26 1.4(6) . . . . ?
C24 C25 C26 C27 -0.3(7) . . . . ?
C25 C26 C27 C22 -0.4(7) . . . . ?
C23 C22 C27 C26 -0.1(6) . . . . ?
C21 C22 C27 C26 178.8(4) . . . . ?
N2 C1 N1 S1 -178.9(2) . . . . ?
C2 C1 N1 S1 1.6(4) . . . . ?
N1 C1 N2 C4 1.3(4) . . . . ?
C2 C1 N2 C4 -179.3(3) . . . . ?
N1 C1 N2 C6 174.8(3) . . . . ?
C2 C1 N2 C6 -5.7(5) . . . . ?
C5 C4 N2 C1 -74.1(4) . . . . ?
C5 C4 N2 C6 111.7(3) . . . . ?
C7 C6 N2 C1 121.4(4) . . . . ?
C7 C6 N2 C4 -65.0(4) . . . . ?
C16 C15 N3 N4 124.8(3) . . . . ?
C20 C15 N3 N4 -55.0(4) . . . . ?
C16 C15 N3 C2 -100.7(4) . . . . ?
C20 C15 N3 C2 79.4(4) . . . . ?
C8 C2 N3 N4 -106.2(3) . . . . ?
C1 C2 N3 N4 123.1(3) . . . . ?
C3 C2 N3 N4 10.4(3) . . . . ?
C8 C2 N3 C15 118.1(3) . . . . ?
C1 C2 N3 C15 -12.5(4) . . . . ?
C3 C2 N3 C15 -125.2(3) . . . . ?
C22 C21 N4 N3 172.3(3) . . . . ?
C3 C21 N4 N3 -10.0(4) . . . . ?
C15 N3 N4 C21 138.6(3) . . . . ?
C2 N3 N4 C21 -0.8(4) . . . . ?
C12 C11 O3 C14 -176.5(3) . . . . ?
C10 C11 O3 C14 3.6(5) . . . . ?
C1 N1 S1 O1 -126.7(2) . . . . ?
C1 N1 S1 O2 102.9(3) . . . . ?
C1 N1 S1 C3 -10.8(3) . . . . ?
C21 C3 S1 O1 -117.5(2) . . . . ?
C2 C3 S1 O1 132.3(2) . . . . ?
C21 C3 S1 O2 11.5(3) . . . . ?
C2 C3 S1 O2 -98.7(2) . . . . ?
C21 C3 S1 N1 126.2(2) . . . . ?
C2 C3 S1 N1 16.0(2) . . . . ?

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.073

