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

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

data_shashidhar_cu_p1bar_reprocess_a
_database_code_depnum_ccdc_archive 'CCDC 1541726'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;
_audit_creation_date             2017-03-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H22 N10 O6, 2(H2 O)'
_chemical_formula_sum            'C26 H26 N10 O8'
_chemical_formula_weight         606.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.428(4)
_cell_length_b                   10.364(7)
_cell_length_c                   10.401(6)
_cell_angle_alpha                60.81(2)
_cell_angle_beta                 86.52(3)
_cell_angle_gamma                88.14(3)
_cell_volume                     697.8(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    776
_cell_measurement_temperature    157.54
_cell_measurement_theta_max      18.828
_cell_measurement_theta_min      2.251
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1810 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.7174. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light white'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.048
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_unetI/netI     0.1651
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6795
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.246
_diffrn_ambient_temperature      157.54
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1069
_reflns_number_total             2401
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1642
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      0.918
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0661P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1668
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N006(H006), C1(H1), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4627(5) 0.6434(4) 0.7705(4) 0.0560(11) Uani 1 1 d . . . . .
O2 O 0.1315(4) 0.4933(3) 0.6600(3) 0.0403(9) Uani 1 1 d . . . . .
O3 O 0.2510(4) 0.7862(3) 0.4275(3) 0.0346(8) Uani 1 1 d . . . . .
N1 N 0.8027(5) 0.1741(4) 0.8556(3) 0.0294(10) Uani 1 1 d . . . . .
N2 N 0.7760(5) 0.0460(4) 0.9837(4) 0.0361(10) Uani 1 1 d . . . . .
N3 N 0.6456(5) 0.0698(4) 1.0620(4) 0.0376(11) Uani 1 1 d . . . . .
N4 N 0.4852(5) 0.4716(4) 0.6926(4) 0.0345(10) Uani 1 1 d . . . . .
H4 H 0.4283 0.4306 0.6499 0.041 Uiso 1 1 calc R . . . .
N006 N -0.0513(5) 0.7841(4) 0.4784(4) 0.0328(10) Uani 1 1 d . . . . .
H006 H -0.1575 0.7837 0.4454 0.039 Uiso 1 1 calc R . . . .
C1 C 0.5892(6) 0.2119(5) 0.9837(5) 0.0377(13) Uani 1 1 d . . . . .
H1 H 0.4959 0.2567 1.0152 0.045 Uiso 1 1 calc R . . . .
C2 C 0.6881(6) 0.2811(5) 0.8518(4) 0.0303(11) Uani 1 1 d . . . . .
C3 C 0.6733(6) 0.4342(5) 0.7248(5) 0.0360(12) Uani 1 1 d . . . . .
H3A H 0.7267 0.5054 0.7493 0.043 Uiso 1 1 calc R . . . .
H3B H 0.7411 0.4407 0.6369 0.043 Uiso 1 1 calc R . . . .
C4 C 0.3947(7) 0.5676(6) 0.7261(5) 0.0361(12) Uani 1 1 d . . . . .
C5 C 0.1951(7) 0.5775(5) 0.6973(4) 0.0335(12) Uani 1 1 d . . . . .
C6 C 0.0754(6) 0.6811(5) 0.7228(5) 0.0292(11) Uani 1 1 d . . . . .
C7 C -0.0480(6) 0.7732(5) 0.6210(5) 0.0309(12) Uani 1 1 d . . . . .
C8 C -0.1718(6) 0.8550(5) 0.6551(5) 0.0343(12) Uani 1 1 d . . . . .
H8 H -0.2554 0.9166 0.5847 0.041 Uiso 1 1 calc R . . . .
C9 C -0.1749(7) 0.8476(5) 0.7915(5) 0.0392(13) Uani 1 1 d . . . . .
H9 H -0.2620 0.9028 0.8154 0.047 Uiso 1 1 calc R . . . .
C10 C -0.0510(7) 0.7598(5) 0.8935(5) 0.0402(13) Uani 1 1 d . . . . .
H10 H -0.0530 0.7550 0.9871 0.048 Uiso 1 1 calc R . . . .
C11 C 0.0756(6) 0.6789(5) 0.8589(5) 0.0403(13) Uani 1 1 d . . . . .
H11 H 0.1632 0.6217 0.9276 0.048 Uiso 1 1 calc R . . . .
C12 C 0.9553(6) 0.1846(5) 0.7584(4) 0.0316(12) Uani 1 1 d . . . . .
H12A H 1.0289 0.0936 0.8079 0.038 Uiso 1 1 calc R . . . .
H12B H 1.0310 0.2689 0.7413 0.038 Uiso 1 1 calc R . . . .
C13 C 0.0955(6) 0.7949(5) 0.3908(5) 0.0305(12) Uani 1 1 d . . . . .
O1W O 0.6178(5) 0.8044(4) 0.3406(4) 0.0414(10) Uani 1 1 d . . . . .
H1WA H 0.630(8) 0.875(6) 0.261(6) 0.08(2) Uiso 1 1 d . . . . .
H1WB H 0.494(11) 0.788(8) 0.376(7) 0.13(3) Uiso 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
O1 C4 1.222(5) . ?
O2 C5 1.231(5) . ?
O3 C13 1.225(5) . ?
N1 N2 1.356(4) . ?
N1 C2 1.361(5) . ?
N1 C12 1.443(5) . ?
N2 N3 1.322(5) . ?
N3 C1 1.356(5) . ?
N4 H4 0.8800 . ?
N4 C3 1.453(5) . ?
N4 C4 1.353(6) . ?
N006 H006 0.8800 . ?
N006 C7 1.433(5) . ?
N006 C13 1.349(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.375(6) . ?
C2 C3 1.496(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.521(6) . ?
C5 C6 1.483(6) . ?
C6 C7 1.396(6) . ?
C6 C11 1.406(6) . ?
C7 C8 1.376(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(6) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.529(6) 2_666 ?
C13 C12 1.529(6) 2_666 ?
O1W H1WA 0.80(5) . ?
O1W H1WB 0.96(8) . ?

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 N1 C2 110.6(3) . . ?
N2 N1 C12 118.6(3) . . ?
C2 N1 C12 130.1(4) . . ?
N3 N2 N1 107.3(3) . . ?
N2 N3 C1 108.6(3) . . ?
C3 N4 H4 119.0 . . ?
C4 N4 H4 119.0 . . ?
C4 N4 C3 122.0(4) . . ?
C7 N006 H006 117.4 . . ?
C13 N006 H006 117.4 . . ?
C13 N006 C7 125.2(4) . . ?
N3 C1 H1 125.3 . . ?
N3 C1 C2 109.4(4) . . ?
C2 C1 H1 125.3 . . ?
N1 C2 C1 104.1(4) . . ?
N1 C2 C3 125.5(4) . . ?
C1 C2 C3 130.3(4) . . ?
N4 C3 C2 110.0(4) . . ?
N4 C3 H3A 109.7 . . ?
N4 C3 H3B 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O1 C4 N4 125.2(5) . . ?
O1 C4 C5 122.0(5) . . ?
N4 C4 C5 112.8(5) . . ?
O2 C5 C4 119.4(5) . . ?
O2 C5 C6 120.0(5) . . ?
C6 C5 C4 120.4(5) . . ?
C7 C6 C5 122.5(4) . . ?
C7 C6 C11 118.3(4) . . ?
C11 C6 C5 119.1(4) . . ?
C6 C7 N006 121.0(4) . . ?
C8 C7 N006 117.9(4) . . ?
C8 C7 C6 121.0(4) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.1(4) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.3(4) . . ?
C10 C11 H11 119.8 . . ?
N1 C12 H12A 108.7 . . ?
N1 C12 H12B 108.7 . . ?
N1 C12 C13 114.1(4) . 2_666 ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.7 2_666 . ?
C13 C12 H12B 108.7 2_666 . ?
O3 C13 N006 124.0(4) . . ?
O3 C13 C12 124.0(4) . 2_666 ?
N006 C13 C12 112.0(4) . 2_666 ?
H1WA O1W H1WB 112(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shashidhar_17sep15_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1541725'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;
_audit_creation_date             2017-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 O S, 0.25(C26 H22 N10 O6)'
_chemical_formula_sum            'C8.50 H11.50 N2.50 O2.50 S'
_chemical_formula_weight         220.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7434(5)
_cell_length_b                   9.8225(5)
_cell_length_c                   12.0241(6)
_cell_angle_alpha                92.357(2)
_cell_angle_beta                 104.697(3)
_cell_angle_gamma                106.384(2)
_cell_volume                     1060.01(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4294
_cell_measurement_temperature    153.54
_cell_measurement_theta_max      25.857
_cell_measurement_theta_min      2.965
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1351 before and 0.0522 after correction. The Ratio of minimum to maximum transmission is 0.9050. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.057
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14261
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.236
_diffrn_ambient_temperature      153.54
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2869
_reflns_number_total             3686
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+0.6227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1032
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Fixed Sof: S1B(0.85) H1BA(0.85) H1BB(0.85) H1BC(0.85) H1BD(0.15) H1BE(0.15)
 H1BF(0.15) H2BA(0.85) H2BB(0.85) H2BC(0.85) H2BD(0.15) H2BE(0.15) H2BF(0.15)
 S1(0.15)
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B)
3.b Me refined with riding coordinates:
 C1B(H1BA,H1BB,H1BC), C1B(H1BD,H1BE,H1BF), C2B(H2BA,H2BB,H2BC), C2B(H2BD,H2BE,
 H2BF)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N5(H5), C1(H1), C7(H7), C8(H8), C9(H9), C10(H10)
3.d Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C2A(H2AA,H2AB,H2AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.67090(7) 0.31061(7) 0.26481(6) 0.03623(19) Uani 1 1 d . . . . .
O1A O 0.54677(19) 0.32896(19) 0.31076(15) 0.0412(5) Uani 1 1 d . . . . .
C1A C 0.8341(3) 0.3673(3) 0.3841(2) 0.0461(7) Uani 1 1 d . . . . .
H1AA H 0.8547 0.4686 0.4104 0.069 Uiso 1 1 calc GR . . . .
H1AB H 0.9187 0.3538 0.3599 0.069 Uiso 1 1 calc GR . . . .
H1AC H 0.8188 0.3106 0.4475 0.069 Uiso 1 1 calc GR . . . .
C2A C 0.6486(3) 0.1246(3) 0.2531(2) 0.0436(7) Uani 1 1 d . . . . .
H2AA H 0.6439 0.0896 0.3276 0.065 Uiso 1 1 calc GR . . . .
H2AB H 0.7334 0.1072 0.2317 0.065 Uiso 1 1 calc GR . . . .
H2AC H 0.5563 0.0741 0.1935 0.065 Uiso 1 1 calc GR . . . .
S1B S 0.31332(10) 0.37210(7) 0.89020(7) 0.0392(2) Uani 0.85 1 d . . P A 1
O1B O 0.2560(3) 0.4236(3) 0.98302(19) 0.0804(8) Uani 1 1 d . . . . .
C1B C 0.4133(4) 0.2579(3) 0.9475(3) 0.0574(8) Uani 1 1 d . . . . .
H1BA H 0.4521 0.2227 0.8882 0.086 Uiso 0.85 1 calc R . P A 1
H1BB H 0.4964 0.3098 1.0140 0.086 Uiso 0.85 1 calc R . P A 1
H1BC H 0.3479 0.1769 0.9725 0.086 Uiso 0.85 1 calc R . P A 1
H1BD H 0.4005 0.1639 0.9082 0.086 Uiso 0.15 1 calc R . P A 2
H1BE H 0.4777 0.3323 0.9156 0.086 Uiso 0.15 1 calc R . P A 2
H1BF H 0.4591 0.2617 1.0306 0.086 Uiso 0.15 1 calc R . P A 2
C2B C 0.1549(4) 0.2486(4) 0.7935(3) 0.0769(12) Uani 1 1 d . . . . .
H2BA H 0.1838 0.2098 0.7297 0.115 Uiso 0.85 1 calc R . P A 1
H2BB H 0.1125 0.1706 0.8347 0.115 Uiso 0.85 1 calc R . P A 1
H2BC H 0.0806 0.2970 0.7626 0.115 Uiso 0.85 1 calc R . P A 1
H2BD H 0.1329 0.1451 0.7765 0.115 Uiso 0.15 1 calc R . P A 2
H2BE H 0.0640 0.2754 0.7638 0.115 Uiso 0.15 1 calc R . P A 2
H2BF H 0.2305 0.2981 0.7564 0.115 Uiso 0.15 1 calc R . P A 2
O1 O 0.44271(19) 0.22491(19) 0.69133(14) 0.0370(4) Uani 1 1 d . . . . .
O2 O 0.66463(18) 0.12590(16) 0.54636(13) 0.0302(4) Uani 1 1 d . . . . .
O3 O 0.83187(18) 0.45084(15) 0.66665(13) 0.0279(4) Uani 1 1 d . . . . .
N1 N 0.15211(19) 0.26228(17) 0.31114(14) 0.0191(4) Uani 1 1 d . . . . .
N2 N 0.0206(2) 0.15887(18) 0.26884(15) 0.0236(4) Uani 1 1 d . . . . .
N3 N -0.0055(2) 0.08697(19) 0.35498(16) 0.0278(4) Uani 1 1 d . . . . .
N4 N 0.4742(2) 0.29283(18) 0.51985(15) 0.0241(4) Uani 1 1 d . . . . .
H4 H 0.5244 0.2919 0.4686 0.029 Uiso 1 1 calc R . . . .
N5 N 0.7568(2) 0.41487(17) 0.83021(15) 0.0246(4) Uani 1 1 d . . . . .
H5 H 0.7205 0.4528 0.8793 0.030 Uiso 1 1 calc R . . . .
C1 C 0.1077(2) 0.1446(2) 0.45095(19) 0.0260(5) Uani 1 1 d . . . . .
H1 H 0.1154 0.1122 0.5250 0.031 Uiso 1 1 calc R . . . .
C2 C 0.2093(2) 0.2567(2) 0.42528(18) 0.0209(5) Uani 1 1 d . . . . .
C3 C 0.3534(2) 0.3569(2) 0.4962(2) 0.0277(5) Uani 1 1 d . . . . .
H3A H 0.3810 0.4414 0.4552 0.033 Uiso 1 1 calc R . . . .
H3B H 0.3407 0.3904 0.5707 0.033 Uiso 1 1 calc R . . . .
C4 C 0.5099(2) 0.2359(2) 0.61731(18) 0.0215(5) Uani 1 1 d . . . . .
C5 C 0.6428(2) 0.1773(2) 0.63088(18) 0.0216(5) Uani 1 1 d . . . . .
C6 C 0.7253(2) 0.1676(2) 0.75181(18) 0.0198(5) Uani 1 1 d . . . . .
C7 C 0.7505(2) 0.0373(2) 0.77335(19) 0.0231(5) Uani 1 1 d . . . . .
H7 H 0.7265 -0.0351 0.7105 0.028 Uiso 1 1 calc R . . . .
C8 C 0.8099(3) 0.0118(2) 0.88442(19) 0.0269(5) Uani 1 1 d . . . . .
H8 H 0.8256 -0.0780 0.8980 0.032 Uiso 1 1 calc R . . . .
C9 C 0.8463(3) 0.1167(2) 0.97556(19) 0.0287(5) Uani 1 1 d . . . . .
H9 H 0.8843 0.0983 1.0525 0.034 Uiso 1 1 calc R . . . .
C10 C 0.8276(3) 0.2487(2) 0.95542(19) 0.0271(5) Uani 1 1 d . . . . .
H10 H 0.8555 0.3215 1.0185 0.032 Uiso 1 1 calc R . . . .
C11 C 0.7688(2) 0.2757(2) 0.84419(18) 0.0205(5) Uani 1 1 d . . . . .
C12 C 0.2125(3) 0.3548(2) 0.23328(19) 0.0226(5) Uani 1 1 d . . . . .
H12A H 0.1574 0.3132 0.1524 0.027 Uiso 1 1 calc R . . . .
H12B H 0.3179 0.3591 0.2445 0.027 Uiso 1 1 calc R . . . .
C13 C 0.7964(2) 0.4937(2) 0.74825(18) 0.0200(5) Uani 1 1 d . . . . .
S1 S 0.2125(6) 0.2908(5) 0.9228(4) 0.0511(12) Uiso 0.15 1 d . . P A 2


_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
S1A O1A 1.5014(17) . ?
S1A C1A 1.781(3) . ?
S1A C2A 1.774(3) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
S1B O1B 1.497(2) . ?
S1B C1B 1.738(3) . ?
S1B C2B 1.767(3) . ?
O1B S1 1.364(5) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
C1B H1BD 0.9800 . ?
C1B H1BE 0.9800 . ?
C1B H1BF 0.9800 . ?
C1B S1 2.023(6) . ?
C2B H2BA 0.9800 . ?
C2B H2BB 0.9800 . ?
C2B H2BC 0.9800 . ?
C2B H2BD 0.9800 . ?
C2B H2BE 0.9800 . ?
C2B H2BF 0.9800 . ?
C2B S1 1.509(6) . ?
O1 C4 1.223(2) . ?
O2 C5 1.209(2) . ?
O3 C13 1.216(2) . ?
N1 N2 1.351(2) . ?
N1 C2 1.354(3) . ?
N1 C12 1.448(3) . ?
N2 N3 1.315(2) . ?
N3 C1 1.348(3) . ?
N4 H4 0.8800 . ?
N4 C3 1.458(3) . ?
N4 C4 1.328(3) . ?
N5 H5 0.8800 . ?
N5 C11 1.417(3) . ?
N5 C13 1.344(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.362(3) . ?
C2 C3 1.487(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.535(3) . ?
C5 C6 1.494(3) . ?
C6 C7 1.393(3) . ?
C6 C11 1.397(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.525(3) 2_666 ?
C13 C12 1.525(3) 2_666 ?

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
O1A S1A C1A 105.80(11) . . ?
O1A S1A C2A 105.86(12) . . ?
C2A S1A C1A 98.44(13) . . ?
S1A C1A H1AA 109.5 . . ?
S1A C1A H1AB 109.5 . . ?
S1A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
S1A C2A H2AA 109.5 . . ?
S1A C2A H2AB 109.5 . . ?
S1A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
O1B S1B C1B 107.90(15) . . ?
O1B S1B C2B 104.62(15) . . ?
C1B S1B C2B 100.53(19) . . ?
S1B C1B H1BA 109.5 . . ?
S1B C1B H1BB 109.5 . . ?
S1B C1B H1BC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
H1BD C1B H1BE 109.5 . . ?
H1BD C1B H1BF 109.5 . . ?
H1BE C1B H1BF 109.5 . . ?
S1 C1B H1BD 109.5 . . ?
S1 C1B H1BE 109.5 . . ?
S1 C1B H1BF 109.5 . . ?
S1B C2B H2BA 109.5 . . ?
S1B C2B H2BB 109.5 . . ?
S1B C2B H2BC 109.5 . . ?
H2BA C2B H2BB 109.5 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?
H2BD C2B H2BE 109.5 . . ?
H2BD C2B H2BF 109.5 . . ?
H2BE C2B H2BF 109.5 . . ?
S1 C2B H2BD 109.5 . . ?
S1 C2B H2BE 109.5 . . ?
S1 C2B H2BF 109.5 . . ?
N2 N1 C2 110.55(16) . . ?
N2 N1 C12 119.14(17) . . ?
C2 N1 C12 130.26(18) . . ?
N3 N2 N1 107.06(16) . . ?
N2 N3 C1 108.71(17) . . ?
C3 N4 H4 119.4 . . ?
C4 N4 H4 119.4 . . ?
C4 N4 C3 121.21(19) . . ?
C11 N5 H5 117.3 . . ?
C13 N5 H5 117.3 . . ?
C13 N5 C11 125.43(17) . . ?
N3 C1 H1 125.3 . . ?
N3 C1 C2 109.42(19) . . ?
C2 C1 H1 125.3 . . ?
N1 C2 C1 104.26(18) . . ?
N1 C2 C3 123.23(19) . . ?
C1 C2 C3 132.5(2) . . ?
N4 C3 C2 113.15(17) . . ?
N4 C3 H3A 108.9 . . ?
N4 C3 H3B 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
O1 C4 N4 124.7(2) . . ?
O1 C4 C5 120.44(19) . . ?
N4 C4 C5 114.84(18) . . ?
O2 C5 C4 119.86(19) . . ?
O2 C5 C6 123.01(19) . . ?
C6 C5 C4 116.48(17) . . ?
C7 C6 C5 116.47(18) . . ?
C7 C6 C11 118.83(19) . . ?
C11 C6 C5 124.55(18) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C6 C11 N5 123.15(18) . . ?
C10 C11 N5 117.23(18) . . ?
C10 C11 C6 119.63(19) . . ?
N1 C12 H12A 109.0 . . ?
N1 C12 H12B 109.0 . . ?
N1 C12 C13 113.03(17) . 2_666 ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.0 2_666 . ?
C13 C12 H12B 109.0 2_666 . ?
O3 C13 N5 125.13(19) . . ?
O3 C13 C12 122.88(18) . 2_666 ?
N5 C13 C12 111.97(17) . 2_666 ?
O1B S1 C1B 99.5(3) . . ?
O1B S1 C2B 128.5(4) . . ?
C2B S1 C1B 98.5(3) . . ?

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
O1 C4 C5 O2 145.1(2) . . . . ?
O1 C4 C5 C6 -25.9(3) . . . . ?
O2 C5 C6 C7 -40.7(3) . . . . ?
O2 C5 C6 C11 143.7(2) . . . . ?
N1 N2 N3 C1 0.4(2) . . . . ?
N1 C2 C3 N4 -103.6(2) . . . . ?
N2 N1 C2 C1 0.5(2) . . . . ?
N2 N1 C2 C3 179.97(18) . . . . ?
N2 N1 C12 C13 107.8(2) . . . 2_666 ?
N2 N3 C1 C2 -0.1(3) . . . . ?
N3 C1 C2 N1 -0.2(2) . . . . ?
N3 C1 C2 C3 -179.7(2) . . . . ?
N4 C4 C5 O2 -33.0(3) . . . . ?
N4 C4 C5 C6 156.01(18) . . . . ?
C1 C2 C3 N4 75.7(3) . . . . ?
C2 N1 N2 N3 -0.5(2) . . . . ?
C2 N1 C12 C13 -74.9(3) . . . 2_666 ?
C3 N4 C4 O1 4.0(3) . . . . ?
C3 N4 C4 C5 -178.06(17) . . . . ?
C4 N4 C3 C2 -95.2(2) . . . . ?
C4 C5 C6 C7 130.0(2) . . . . ?
C4 C5 C6 C11 -45.6(3) . . . . ?
C5 C6 C7 C8 -172.4(2) . . . . ?
C5 C6 C11 N5 -8.7(3) . . . . ?
C5 C6 C11 C10 171.7(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C6 C11 N5 175.78(19) . . . . ?
C7 C6 C11 C10 -3.8(3) . . . . ?
C7 C8 C9 C10 -2.0(3) . . . . ?
C8 C9 C10 C11 1.7(3) . . . . ?
C9 C10 C11 N5 -178.4(2) . . . . ?
C9 C10 C11 C6 1.2(3) . . . . ?
C11 N5 C13 O3 8.9(4) . . . . ?
C11 N5 C13 C12 -172.81(19) . . . 2_666 ?
C11 C6 C7 C8 3.5(3) . . . . ?
C12 N1 N2 N3 177.27(17) . . . . ?
C12 N1 C2 C1 -177.0(2) . . . . ?
C12 N1 C2 C3 2.5(3) . . . . ?
C13 N5 C11 C6 -44.9(3) . . . . ?
C13 N5 C11 C10 134.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
