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

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

data_rt_OLN_PZO
_database_code_depnum_ccdc_archive 'CCDC 1919072'
loop_
_audit_author_name
_audit_author_address
'Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N6 O2 S'
_chemical_formula_sum            'C22 H24 N6 O2 S'
_chemical_formula_weight         436.53

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                   9.1672(4)
_cell_length_b                   9.2117(5)
_cell_length_c                   14.8900(8)
_cell_angle_alpha                86.026(3)
_cell_angle_beta                 72.591(2)
_cell_angle_gamma                65.538(2)
_cell_volume                     1089.94(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9537
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.08

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19575
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.436
_diffrn_reflns_theta_max         28.115
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5280
_reflns_number_gt                4455
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1024P)²+0.1399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5280
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1560
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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 1.10873(18) 0.66226(17) 0.64116(10) 0.0342(3) Uani 1 1 d . . . . .
C2 C 0.97090(19) 0.77120(18) 0.71018(10) 0.0361(3) Uani 1 1 d . . . . .
C3 C 0.76295(17) 0.85449(16) 0.62916(9) 0.0326(3) Uani 1 1 d . . . . .
C4 C 0.84373(17) 0.76289(16) 0.54593(9) 0.0309(3) Uani 1 1 d . . . . .
C5 C 1.02579(17) 0.70621(16) 0.50122(9) 0.0304(3) Uani 1 1 d . . . . .
C6 C 0.72895(18) 0.73704(17) 0.50858(10) 0.0355(3) Uani 1 1 d . . . . .
H6 H 0.763324 0.674955 0.453286 0.043 Uiso 1 1 calc R U . . .
C7 C 0.56606(19) 0.81074(18) 0.56067(11) 0.0387(3) Uani 1 1 d . . . . .
C8 C 0.4135(2) 0.8132(2) 0.54194(15) 0.0535(4) Uani 1 1 d . . . . .
H8A H 0.362339 0.909895 0.512920 0.080 Uiso 1 1 calc R U . . .
H8B H 0.335018 0.808616 0.600340 0.080 Uiso 1 1 calc R U . . .
H8C H 0.445324 0.722790 0.500535 0.080 Uiso 1 1 calc R U . . .
C9 C 0.9675(2) 0.7623(2) 0.80422(11) 0.0490(4) Uani 1 1 d . . . . .
H9 H 0.875637 0.834571 0.849492 0.059 Uiso 1 1 calc R U . . .
C10 C 1.0994(3) 0.6469(3) 0.83150(13) 0.0562(5) Uani 1 1 d . . . . .
H10 H 1.096416 0.642597 0.894584 0.067 Uiso 1 1 calc R U . . .
C11 C 1.2351(2) 0.5384(2) 0.76449(13) 0.0526(4) Uani 1 1 d . . . . .
H11 H 1.323181 0.459599 0.782280 0.063 Uiso 1 1 calc R U . . .
C12 C 1.2391(2) 0.5477(2) 0.67117(12) 0.0438(4) Uani 1 1 d . . . . .
H12 H 1.331839 0.475119 0.626509 0.053 Uiso 1 1 calc R U . . .
C13 C 0.99093(18) 0.80555(18) 0.34660(10) 0.0363(3) Uani 1 1 d . . . . .
H13A H 1.035117 0.886536 0.335025 0.044 Uiso 1 1 calc R U . . .
H13B H 0.872231 0.856952 0.380511 0.044 Uiso 1 1 calc R U . . .
C14 C 1.01442(19) 0.7291(2) 0.25393(11) 0.0416(3) Uani 1 1 d . . . . .
H14A H 0.963047 0.653633 0.265541 0.050 Uiso 1 1 calc R U . . .
H14B H 0.959108 0.810633 0.215816 0.050 Uiso 1 1 calc R U . . .
C15 C 1.2869(2) 0.52854(19) 0.26234(11) 0.0416(3) Uani 1 1 d . . . . .
H15A H 1.406100 0.480940 0.229214 0.050 Uiso 1 1 calc R U . . .
H15B H 1.248219 0.443659 0.274443 0.050 Uiso 1 1 calc R U . . .
C16 C 1.25843(18) 0.6085(2) 0.35493(10) 0.0399(3) Uani 1 1 d . . . . .
H16A H 1.314966 0.529939 0.393927 0.048 Uiso 1 1 calc R U . . .
H16B H 1.304278 0.688287 0.343647 0.048 Uiso 1 1 calc R U . . .
C17 C 1.2225(3) 0.5660(3) 0.11098(12) 0.0567(5) Uani 1 1 d . . . . .
H17A H 1.183129 0.482806 0.123210 0.085 Uiso 1 1 calc R U . . .
H17B H 1.339928 0.520978 0.076837 0.085 Uiso 1 1 calc R U . . .
H17C H 1.161359 0.643564 0.074215 0.085 Uiso 1 1 calc R U . . .
C18 C 0.41320(19) 0.11909(19) 0.90369(9) 0.0368(3) Uani 1 1 d . . . . .
C20 C 0.2217(3) -0.0416(3) 0.93807(14) 0.0581(5) Uani 1 1 d . . . . .
H20 H 0.159153 -0.102354 0.948706 0.070 Uiso 1 1 calc R U . . .
C22 C 0.51623(19) 0.21659(18) 0.88469(9) 0.0370(3) Uani 1 1 d . . . . .
C19 C 0.2399(2) 0.1949(2) 0.93458(14) 0.0538(4) Uani 1 1 d . . . . .
H19 H 0.189625 0.305592 0.944499 0.065 Uiso 1 1 calc R U . . .
C21 C 0.3944(3) -0.1180(2) 0.90961(14) 0.0575(5) Uani 1 1 d . . . . .
H21 H 0.444680 -0.229101 0.903791 0.069 Uiso 1 1 calc R U . . .
H3A H 1.246(3) 0.720(2) 0.1869(14) 0.054(5) Uiso 1 1 d . . . . .
H4A H 0.756(2) 0.968(2) 0.7374(14) 0.050(5) Uiso 1 1 d . . . . .
N1 N 1.13964(15) 0.66738(15) 0.54259(8) 0.0352(3) Uani 1 1 d . . . . .
N2 N 1.07806(14) 0.68437(15) 0.40335(8) 0.0349(3) Uani 1 1 d . . . . .
N3 N 1.19620(16) 0.64463(15) 0.20181(8) 0.0364(3) Uani 1 1 d . . . . .
N4 N 0.83763(17) 0.89684(15) 0.68542(9) 0.0391(3) Uani 1 1 d . . . . .
N5 N 0.49188(19) -0.03916(18) 0.89018(11) 0.0501(4) Uani 1 1 d . . . . .
N6 N 0.1420(2) 0.1168(2) 0.95071(14) 0.0656(5) Uani 1 1 d . . . . .
O1 O 0.66695(15) 0.14802(14) 0.83384(8) 0.0492(3) Uani 1 1 d . . . . .
O2 O 0.44646(16) 0.35555(14) 0.91802(9) 0.0517(3) Uani 1 1 d . . . . .
S1 S 0.54849(5) 0.91009(5) 0.66052(3) 0.04234(14) 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 C12 1.397(2) . ?
C1 C2 1.406(2) . ?
C1 N1 1.4105(18) . ?
C2 C9 1.389(2) . ?
C2 N4 1.417(2) . ?
C3 C4 1.3691(19) . ?
C3 N4 1.3900(18) . ?
C3 S1 1.7308(14) . ?
C4 C6 1.4316(19) . ?
C4 C5 1.4708(18) . ?
C5 N1 1.2812(18) . ?
C5 N2 1.3916(17) . ?
C6 C7 1.354(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.497(2) . ?
C7 S1 1.7312(17) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N2 1.4604(18) . ?
C13 C14 1.509(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N3 1.4902(19) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.492(2) . ?
C15 C16 1.510(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.4635(18) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N3 1.4857(19) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N5 1.330(2) . ?
C18 C19 1.383(2) . ?
C18 C22 1.512(2) . ?
C20 N6 1.331(3) . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C22 O2 1.2305(19) . ?
C22 O1 1.2645(18) . ?
C19 N6 1.328(2) . ?
C19 H19 0.9300 . ?
C21 N5 1.328(2) . ?
C21 H21 0.9300 . ?
N3 H3A 0.96(2) . ?
N4 H4A 0.95(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
C12 C1 C2 117.50(14) . . ?
C12 C1 N1 115.42(13) . . ?
C2 C1 N1 126.63(13) . . ?
C9 C2 C1 120.10(15) . . ?
C9 C2 N4 118.55(14) . . ?
C1 C2 N4 121.26(13) . . ?
C4 C3 N4 126.45(13) . . ?
C4 C3 S1 111.32(11) . . ?
N4 C3 S1 122.20(11) . . ?
C3 C4 C6 111.73(12) . . ?
C3 C4 C5 122.29(12) . . ?
C6 C4 C5 125.93(12) . . ?
N1 C5 N2 117.48(12) . . ?
N1 C5 C4 127.21(12) . . ?
N2 C5 C4 115.19(11) . . ?
C7 C6 C4 114.21(13) . . ?
C7 C6 H6 122.9 . . ?
C4 C6 H6 122.9 . . ?
C6 C7 C8 128.75(16) . . ?
C6 C7 S1 110.52(11) . . ?
C8 C7 S1 120.73(13) . . ?
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 . . ?
C10 C9 C2 120.84(17) . . ?
C10 C9 H9 119.6 . . ?
C2 C9 H9 119.6 . . ?
C11 C10 C9 119.66(16) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 119.54(17) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C1 122.36(16) . . ?
C11 C12 H12 118.8 . . ?
C1 C12 H12 118.8 . . ?
N2 C13 C14 109.90(12) . . ?
N2 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
N2 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N3 C14 C13 110.75(12) . . ?
N3 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N3 C15 C16 111.45(12) . . ?
N3 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
N3 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
N2 C16 C15 109.15(12) . . ?
N2 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
N2 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N5 C18 C19 121.11(15) . . ?
N5 C18 C22 119.00(14) . . ?
C19 C18 C22 119.89(15) . . ?
N6 C20 C21 121.68(17) . . ?
N6 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
O2 C22 O1 125.66(15) . . ?
O2 C22 C18 117.82(14) . . ?
O1 C22 C18 116.50(13) . . ?
N6 C19 C18 122.97(18) . . ?
N6 C19 H19 118.5 . . ?
C18 C19 H19 118.5 . . ?
N5 C21 C20 122.56(18) . . ?
N5 C21 H21 118.7 . . ?
C20 C21 H21 118.7 . . ?
C5 N1 C1 124.15(12) . . ?
C5 N2 C13 120.72(12) . . ?
C5 N2 C16 118.23(11) . . ?
C13 N2 C16 110.73(11) . . ?
C17 N3 C14 111.71(13) . . ?
C17 N3 C15 111.62(13) . . ?
C14 N3 C15 110.46(11) . . ?
C17 N3 H3A 107.0(12) . . ?
C14 N3 H3A 109.6(12) . . ?
C15 N3 H3A 106.3(12) . . ?
C3 N4 C2 116.79(12) . . ?
C3 N4 H4A 111.6(12) . . ?
C2 N4 H4A 113.8(12) . . ?
C21 N5 C18 116.06(16) . . ?
C19 N6 C20 115.54(17) . . ?
C3 S1 C7 92.19(7) . . ?

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
C12 C1 C2 C9 -0.2(2) . . . . ?
N1 C1 C2 C9 -172.04(14) . . . . ?
C12 C1 C2 N4 176.42(13) . . . . ?
N1 C1 C2 N4 4.6(2) . . . . ?
N4 C3 C4 C6 177.49(13) . . . . ?
S1 C3 C4 C6 -0.67(15) . . . . ?
N4 C3 C4 C5 -4.8(2) . . . . ?
S1 C3 C4 C5 177.06(10) . . . . ?
C3 C4 C5 N1 33.4(2) . . . . ?
C6 C4 C5 N1 -149.17(15) . . . . ?
C3 C4 C5 N2 -150.63(13) . . . . ?
C6 C4 C5 N2 26.76(19) . . . . ?
C3 C4 C6 C7 1.75(18) . . . . ?
C5 C4 C6 C7 -175.88(13) . . . . ?
C4 C6 C7 C8 178.40(16) . . . . ?
C4 C6 C7 S1 -1.99(16) . . . . ?
C1 C2 C9 C10 0.2(2) . . . . ?
N4 C2 C9 C10 -176.44(15) . . . . ?
C2 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 C1 -1.0(3) . . . . ?
C2 C1 C12 C11 0.6(2) . . . . ?
N1 C1 C12 C11 173.34(14) . . . . ?
N2 C13 C14 N3 -57.48(16) . . . . ?
N3 C15 C16 N2 57.29(16) . . . . ?
N5 C18 C22 O2 -163.06(15) . . . . ?
C19 C18 C22 O2 17.0(2) . . . . ?
N5 C18 C22 O1 18.3(2) . . . . ?
C19 C18 C22 O1 -161.63(15) . . . . ?
N5 C18 C19 N6 -1.4(3) . . . . ?
C22 C18 C19 N6 178.58(17) . . . . ?
N6 C20 C21 N5 -2.2(3) . . . . ?
N2 C5 N1 C1 -171.22(12) . . . . ?
C4 C5 N1 C1 4.6(2) . . . . ?
C12 C1 N1 C5 148.39(14) . . . . ?
C2 C1 N1 C5 -39.6(2) . . . . ?
N1 C5 N2 C13 -137.61(14) . . . . ?
C4 C5 N2 C13 46.04(17) . . . . ?
N1 C5 N2 C16 4.23(19) . . . . ?
C4 C5 N2 C16 -172.12(12) . . . . ?
C14 C13 N2 C5 -154.44(12) . . . . ?
C14 C13 N2 C16 61.15(15) . . . . ?
C15 C16 N2 C5 153.95(13) . . . . ?
C15 C16 N2 C13 -60.65(16) . . . . ?
C13 C14 N3 C17 179.04(14) . . . . ?
C13 C14 N3 C15 54.16(16) . . . . ?
C16 C15 N3 C17 -179.43(13) . . . . ?
C16 C15 N3 C14 -54.51(16) . . . . ?
C4 C3 N4 C2 -51.4(2) . . . . ?
S1 C3 N4 C2 126.54(12) . . . . ?
C9 C2 N4 C3 -130.72(15) . . . . ?
C1 C2 N4 C3 52.64(19) . . . . ?
C20 C21 N5 C18 2.8(3) . . . . ?
C19 C18 N5 C21 -1.1(2) . . . . ?
C22 C18 N5 C21 178.92(15) . . . . ?
C18 C19 N6 C20 2.1(3) . . . . ?
C21 C20 N6 C19 -0.3(3) . . . . ?
C4 C3 S1 C7 -0.36(11) . . . . ?
N4 C3 S1 C7 -178.61(12) . . . . ?
C6 C7 S1 C3 1.34(12) . . . . ?
C8 C7 S1 C3 -179.01(14) . . . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.141

####################################################################### 
# 
# 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_OLN_246THBA_EtOH_EtOAc
_database_code_depnum_ccdc_archive 'CCDC 1919073'
loop_
_audit_author_name
_audit_author_address
'Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 N4 O5 S'
_chemical_formula_sum            'C24 H26 N4 O5 S'
_chemical_formula_weight         482.55

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                   9.5404(7)
_cell_length_b                   13.9656(9)
_cell_length_c                   18.1238(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.142(3)
_cell_angle_gamma                90
_cell_volume                     2360.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.65

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   0.996
_exptl_transmission_factor_max   0.997
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.011
_exptl_crystal_size_min          0.009
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31994
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.626
_diffrn_reflns_theta_max         28.158
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5722
_reflns_number_gt                4079
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0665P)²+0.4496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5722
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.80240(6) 0.32756(4) 0.65004(3) 0.04578(16) Uani 1 1 d . . . . .
O1 O 0.51746(15) 0.79789(12) 0.30613(8) 0.0569(4) Uani 1 1 d . . . . .
O2 O 0.51304(14) 0.85980(10) 0.41800(7) 0.0502(4) Uani 1 1 d . . . . .
O3 O 0.29309(18) 0.80410(11) 0.20109(8) 0.0535(4) Uani 1 1 d . . . . .
O4 O -0.09798(16) 0.99069(12) 0.24216(9) 0.0572(4) Uani 1 1 d . . . . .
O5 O 0.32277(16) 0.98451(11) 0.42908(7) 0.0502(4) Uani 1 1 d . . . . .
N1 N 0.78170(16) 0.78855(10) 0.45196(8) 0.0349(3) Uani 1 1 d . . . . .
N2 N 0.76964(15) 0.58365(10) 0.46107(8) 0.0330(3) Uani 1 1 d . . . . .
N3 N 0.74145(15) 0.43732(10) 0.40167(8) 0.0326(3) Uani 1 1 d . . . . .
N4 N 0.65406(16) 0.30052(12) 0.50454(9) 0.0393(4) Uani 1 1 d . . . . .
C1 C 0.8297(2) 0.72474(12) 0.39609(10) 0.0375(4) Uani 1 1 d . . . . .
H1A H 0.931680 0.712674 0.412252 0.045 Uiso 1 1 calc R U . . .
H1B H 0.813904 0.756648 0.347506 0.045 Uiso 1 1 calc R U . . .
C00J C 0.45646(19) 0.84665(13) 0.34786(10) 0.0387(4) Uani 1 1 d . . . . .
C2 C 0.7503(2) 0.63093(12) 0.38781(9) 0.0356(4) Uani 1 1 d . . . . .
H2A H 0.649106 0.642138 0.367873 0.043 Uiso 1 1 calc R U . . .
H2B H 0.786299 0.590092 0.352656 0.043 Uiso 1 1 calc R U . . .
C3 C 0.7951(2) 0.73828(13) 0.52609(10) 0.0407(4) Uani 1 1 d . . . . .
H3A H 0.755490 0.778265 0.560417 0.049 Uiso 1 1 calc R U . . .
H3B H 0.895625 0.727407 0.548171 0.049 Uiso 1 1 calc R U . . .
C4 C 0.7169(2) 0.64369(13) 0.51575(10) 0.0385(4) Uani 1 1 d . . . . .
H4A H 0.730825 0.610668 0.563830 0.046 Uiso 1 1 calc R U . . .
H4B H 0.615020 0.654962 0.498191 0.046 Uiso 1 1 calc R U . . .
C5 C 0.76826(16) 0.48525(12) 0.46431(9) 0.0297(4) Uani 1 1 d . . . . .
C6 C 0.76475(17) 0.33738(12) 0.39835(9) 0.0314(4) Uani 1 1 d . . . . .
C7 C 0.82561(19) 0.30454(13) 0.33941(10) 0.0374(4) Uani 1 1 d . . . . .
H7 H 0.854888 0.348862 0.307443 0.045 Uiso 1 1 calc R U . . .
C8 C 0.8437(2) 0.20769(14) 0.32719(11) 0.0417(4) Uani 1 1 d . . . . .
H8 H 0.886235 0.187570 0.288171 0.050 Uiso 1 1 calc R U . . .
C9 C 0.7980(2) 0.14185(14) 0.37323(11) 0.0442(5) Uani 1 1 d . . . . .
H9 H 0.808590 0.076745 0.365079 0.053 Uiso 1 1 calc R U . . .
C10 C 0.7363(2) 0.17232(13) 0.43186(11) 0.0414(4) Uani 1 1 d . . . . .
H10 H 0.705977 0.127305 0.462965 0.050 Uiso 1 1 calc R U . . .
C11 C 0.71905(17) 0.26910(13) 0.44475(10) 0.0341(4) Uani 1 1 d . . . . .
C12 C 0.74448(18) 0.35898(13) 0.55678(10) 0.0345(4) Uani 1 1 d . . . . .
C13 C 0.9122(2) 0.42693(13) 0.66784(10) 0.0393(4) Uani 1 1 d . . . . .
C14 C 0.90327(18) 0.47992(13) 0.60486(10) 0.0354(4) Uani 1 1 d . . . . .
H14 H 0.955823 0.535739 0.603495 0.042 Uiso 1 1 calc R U . . .
C15 C 0.80573(17) 0.44266(12) 0.54028(9) 0.0314(4) Uani 1 1 d . . . . .
C16 C 1.0036(2) 0.44047(17) 0.74491(11) 0.0551(5) Uani 1 1 d . . . . .
H16A H 1.073465 0.390121 0.755186 0.083 Uiso 1 1 calc R U . . .
H16B H 0.944411 0.438804 0.781687 0.083 Uiso 1 1 calc R U . . .
H16C H 1.051500 0.501190 0.747351 0.083 Uiso 1 1 calc R U . . .
C17 C 0.8611(2) 0.88053(14) 0.45996(13) 0.0538(5) Uani 1 1 d . . . . .
H17A H 0.960862 0.868702 0.480428 0.081 Uiso 1 1 calc R U . . .
H17B H 0.823399 0.922060 0.493261 0.081 Uiso 1 1 calc R U . . .
H17C H 0.850571 0.910366 0.411386 0.081 Uiso 1 1 calc R U . . .
C18 C 0.31452(18) 0.88898(12) 0.31781(9) 0.0323(4) Uani 1 1 d . . . . .
C19 C 0.2364(2) 0.86378(12) 0.24555(9) 0.0352(4) Uani 1 1 d . . . . .
C20 C 0.09882(19) 0.89662(13) 0.21881(9) 0.0381(4) Uani 1 1 d . . . . .
H20 H 0.047711 0.878093 0.171464 0.046 Uiso 1 1 calc R U . . .
C21 C 0.03766(19) 0.95778(14) 0.26364(10) 0.0386(4) Uani 1 1 d . . . . .
C22 C 0.1134(2) 0.98737(14) 0.33365(10) 0.0425(4) Uani 1 1 d . . . . .
H22 H 0.072331 1.029974 0.362410 0.051 Uiso 1 1 calc R U . . .
C23 C 0.25028(18) 0.95307(13) 0.36034(9) 0.0348(4) Uani 1 1 d . . . . .
H1C H 0.680(3) 0.8052(16) 0.4345(12) 0.061(7) Uiso 1 1 d . . . . .
H3C H 0.375(3) 0.7889(19) 0.2286(15) 0.071(8) Uiso 1 1 d . . . . .
H4C H 0.619(2) 0.2544(15) 0.5244(11) 0.045(6) Uiso 1 1 d . . . . .
H4D H -0.131(3) 0.9724(19) 0.2007(15) 0.076(9) Uiso 1 1 d . . . . .
H5C H 0.413(3) 0.948(2) 0.4405(16) 0.096(9) 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
S1 C12 1.7210(18) . ?
S1 C13 1.728(2) . ?
O1 C00J 1.249(2) . ?
O2 C00J 1.285(2) . ?
O3 C19 1.349(2) . ?
O3 H3C 0.86(3) . ?
O4 C21 1.351(2) . ?
O4 H4D 0.80(3) . ?
O5 C23 1.364(2) . ?
O5 H5C 0.98(3) . ?
N1 C17 1.483(2) . ?
N1 C1 1.491(2) . ?
N1 C3 1.497(2) . ?
N1 H1C 0.99(2) . ?
N2 C5 1.376(2) . ?
N2 C2 1.459(2) . ?
N2 C4 1.466(2) . ?
N3 C5 1.296(2) . ?
N3 C6 1.417(2) . ?
N4 C12 1.401(2) . ?
N4 C11 1.426(2) . ?
N4 H4C 0.84(2) . ?
C1 C2 1.505(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C00J C18 1.473(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.509(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C15 1.473(2) . ?
C6 C7 1.396(2) . ?
C6 C11 1.400(2) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9300 . ?
C12 C15 1.367(2) . ?
C13 C14 1.348(2) . ?
C13 C16 1.495(3) . ?
C14 C15 1.431(2) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.403(2) . ?
C18 C19 1.409(2) . ?
C19 C20 1.378(2) . ?
C20 C21 1.389(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(2) . ?
C22 C23 1.380(2) . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C13 92.03(9) . . ?
C19 O3 H3C 103.7(17) . . ?
C21 O4 H4D 109(2) . . ?
C23 O5 H5C 106.1(17) . . ?
C17 N1 C1 111.13(15) . . ?
C17 N1 C3 111.89(15) . . ?
C1 N1 C3 110.39(13) . . ?
C17 N1 H1C 106.1(13) . . ?
C1 N1 H1C 110.3(13) . . ?
C3 N1 H1C 106.9(13) . . ?
C5 N2 C2 119.35(14) . . ?
C5 N2 C4 122.34(14) . . ?
C2 N2 C4 111.15(13) . . ?
C5 N3 C6 122.83(14) . . ?
C12 N4 C11 112.85(14) . . ?
C12 N4 H4C 113.6(14) . . ?
C11 N4 H4C 111.3(14) . . ?
N1 C1 C2 111.60(14) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
O1 C00J O2 121.64(16) . . ?
O1 C00J C18 120.28(16) . . ?
O2 C00J C18 118.06(16) . . ?
N2 C2 C1 109.79(14) . . ?
N2 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 C4 110.62(15) . . ?
N1 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N2 C4 C3 110.71(14) . . ?
N2 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N3 C5 N2 118.71(14) . . ?
N3 C5 C15 125.07(15) . . ?
N2 C5 C15 116.14(14) . . ?
C7 C6 C11 117.90(16) . . ?
C7 C6 N3 116.76(15) . . ?
C11 C6 N3 125.03(15) . . ?
C8 C7 C6 121.87(17) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C9 C8 C7 119.36(18) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.05(17) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.84(17) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 119.97(17) . . ?
C10 C11 N4 120.89(16) . . ?
C6 C11 N4 119.14(16) . . ?
C15 C12 N4 125.51(16) . . ?
C15 C12 S1 111.65(13) . . ?
N4 C12 S1 122.68(13) . . ?
C14 C13 C16 129.97(19) . . ?
C14 C13 S1 110.79(14) . . ?
C16 C13 S1 119.18(15) . . ?
C13 C14 C15 114.03(16) . . ?
C13 C14 H14 123.0 . . ?
C15 C14 H14 123.0 . . ?
C12 C15 C14 111.48(15) . . ?
C12 C15 C5 121.23(15) . . ?
C14 C15 C5 127.28(15) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 117.59(15) . . ?
C23 C18 C00J 121.77(16) . . ?
C19 C18 C00J 120.60(16) . . ?
O3 C19 C20 117.86(16) . . ?
O3 C19 C18 120.63(16) . . ?
C20 C19 C18 121.49(16) . . ?
C19 C20 C21 119.01(16) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
O4 C21 C22 116.49(16) . . ?
O4 C21 C20 122.37(16) . . ?
C22 C21 C20 121.14(16) . . ?
C23 C22 C21 119.39(17) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
O5 C23 C22 117.98(16) . . ?
O5 C23 C18 120.72(15) . . ?
C22 C23 C18 121.29(16) . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_OLN_GA
_database_code_depnum_ccdc_archive 'CCDC 1919075'
loop_
_audit_author_name
_audit_author_address
'Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H30 N4 O7 S'
_chemical_formula_sum            'C24 H30 N4 O7 S'
_chemical_formula_weight         518.58

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                   11.9730(5)
_cell_length_b                   18.2134(7)
_cell_length_c                   11.9964(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.699(2)
_cell_angle_gamma                90
_cell_volume                     2598.18(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7764
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      20.95

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   0.964
_exptl_transmission_factor_max   0.978
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41430
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.045
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5318
_reflns_number_gt                3865
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+0.9640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5318
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1613
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_restrained_S_all      1.208
_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
S1 S 0.34245(8) 0.46421(5) 0.14150(6) 0.0617(3) Uani 1 1 d . . . . .
O1 O 0.15256(16) 0.30909(9) 0.88696(14) 0.0452(5) Uani 1 1 d . . . . .
O2 O 0.13159(17) 0.33799(9) 0.70699(14) 0.0496(5) Uani 1 1 d . . . . .
O3 O 0.0181(2) 0.04639(11) 0.89094(16) 0.0603(6) Uani 1 1 d . . . . .
O4 O 0.0173(2) -0.00196(11) 0.68148(19) 0.0605(6) Uani 1 1 d . . . . .
O5 O 0.06196(18) 0.08977(10) 0.51226(15) 0.0500(5) Uani 1 1 d . . . . .
O6 O 0.3792(3) 0.30037(15) 0.9826(2) 0.0671(7) Uani 1 1 d . . . . .
O7 O 0.9475(3) 0.10490(16) 0.0774(2) 0.0729(7) Uani 1 1 d . . . . .
N1 N 0.2797(2) 0.44688(13) 0.73961(19) 0.0488(6) Uani 1 1 d . . . . .
N2 N 0.3784(2) 0.40675(13) 0.54304(18) 0.0497(6) Uani 1 1 d . . . . .
N3 N 0.5083(2) 0.34085(12) 0.45950(19) 0.0490(6) Uani 1 1 d . . . . .
N4 N 0.4326(2) 0.33407(14) 0.2226(2) 0.0541(7) Uani 1 1 d . . . . .
C1 C 0.3942(3) 0.41559(18) 0.7464(2) 0.0557(8) Uani 1 1 d . . . . .
H1A H 0.409057 0.387469 0.815188 0.067 Uiso 1 1 calc R U . . .
H1B H 0.448450 0.455280 0.749340 0.067 Uiso 1 1 calc R U . . .
C2 C 0.4094(3) 0.36658(16) 0.6478(2) 0.0540(8) Uani 1 1 d . . . . .
H2A H 0.487148 0.350798 0.651924 0.065 Uiso 1 1 calc R U . . .
H2B H 0.362499 0.323286 0.649791 0.065 Uiso 1 1 calc R U . . .
C3 C 0.2625(3) 0.43216(16) 0.5359(2) 0.0500(7) Uani 1 1 d . . . . .
H3A H 0.212564 0.390590 0.540625 0.060 Uiso 1 1 calc R U . . .
H3B H 0.241940 0.456430 0.464524 0.060 Uiso 1 1 calc R U . . .
C4 C 0.2501(3) 0.48449(15) 0.6299(2) 0.0532(7) Uani 1 1 d . . . . .
H4A H 0.299150 0.526411 0.624523 0.064 Uiso 1 1 calc R U . . .
H4B H 0.173208 0.502128 0.624533 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4323(2) 0.39151(14) 0.4504(2) 0.0425(6) Uani 1 1 d . . . . .
C6 C 0.5823(2) 0.32880(14) 0.3777(2) 0.0473(7) Uani 1 1 d . . . . .
C7 C 0.6945(3) 0.31700(16) 0.4157(3) 0.0583(8) Uani 1 1 d . . . . .
H7 H 0.718407 0.320281 0.492103 0.070 Uiso 1 1 calc R U . . .
C8 C 0.7716(3) 0.30048(18) 0.3425(4) 0.0715(10) Uani 1 1 d . . . . .
H8 H 0.846914 0.293961 0.369596 0.086 Uiso 1 1 calc R U . . .
C9 C 0.7371(3) 0.29361(18) 0.2292(4) 0.0737(10) Uani 1 1 d . . . . .
H9 H 0.788690 0.281530 0.179907 0.088 Uiso 1 1 calc R U . . .
C10 C 0.6262(3) 0.30474(17) 0.1899(3) 0.0632(9) Uani 1 1 d . . . . .
H10 H 0.603052 0.300563 0.113421 0.076 Uiso 1 1 calc R U . . .
C11 C 0.5483(3) 0.32206(14) 0.2621(2) 0.0488(7) Uani 1 1 d . . . . .
C12 C 0.3944(2) 0.40458(15) 0.2452(2) 0.0463(7) Uani 1 1 d . . . . .
C13 C 0.3244(3) 0.53271(16) 0.2376(3) 0.0590(8) Uani 1 1 d . . . . .
C14 C 0.3595(3) 0.51003(15) 0.3426(2) 0.0504(7) Uani 1 1 d . . . . .
H14 H 0.358253 0.539960 0.405275 0.060 Uiso 1 1 calc R U . . .
C15 C 0.3988(2) 0.43588(14) 0.3494(2) 0.0433(6) Uani 1 1 d . . . . .
C16 C 0.2756(4) 0.6059(2) 0.1989(3) 0.0896(12) Uani 1 1 d . . . . .
H16A H 0.321710 0.627820 0.147687 0.134 Uiso 1 1 calc R U . . .
H16B H 0.273135 0.637555 0.262614 0.134 Uiso 1 1 calc R U . . .
H16C H 0.200822 0.598992 0.161939 0.134 Uiso 1 1 calc R U . . .
C17 C 0.2674(3) 0.4961(2) 0.8360(3) 0.0751(11) Uani 1 1 d . . . . .
H17A H 0.321451 0.535110 0.837417 0.113 Uiso 1 1 calc R U . . .
H17B H 0.279901 0.468600 0.904579 0.113 Uiso 1 1 calc R U . . .
H17C H 0.192909 0.516385 0.828284 0.113 Uiso 1 1 calc R U . . .
C18 C 0.09674(19) 0.21525(12) 0.75458(18) 0.0304(5) Uani 1 1 d . . . . .
C19 C 0.0725(2) 0.16721(13) 0.83782(19) 0.0359(6) Uani 1 1 d . . . . .
H19 H 0.075341 0.183335 0.911653 0.043 Uiso 1 1 calc R U . . .
C20 C 0.0441(2) 0.09565(14) 0.8113(2) 0.0417(6) Uani 1 1 d . . . . .
C21 C 0.0426(2) 0.07023(13) 0.7017(2) 0.0397(6) Uani 1 1 d . . . . .
C22 C 0.0668(2) 0.11869(13) 0.61857(19) 0.0370(6) Uani 1 1 d . . . . .
C23 C 0.0929(2) 0.19090(13) 0.64447(19) 0.0355(6) Uani 1 1 d . . . . .
H23 H 0.107937 0.223313 0.588195 0.043 Uiso 1 1 calc R U . . .
C24 C 0.1287(2) 0.29251(12) 0.78533(19) 0.0323(5) Uani 1 1 d . . . . .
H1 H 0.233(2) 0.4149(17) 0.740(2) 0.050(9) Uiso 1 1 d . . . . .
H3 H 0.004(4) 0.069(3) 0.952(4) 0.120(17) Uiso 1 1 d . . . . .
H4 H 0.020(3) -0.012(2) 0.619(3) 0.075(12) Uiso 1 1 d . . . . .
H5 H 0.090(3) 0.1223(19) 0.473(3) 0.064(10) Uiso 1 1 d . . . . .
H6A H 0.409(4) 0.267(3) 0.966(3) 0.091(16) Uiso 1 1 d . . . . .
H6B H 0.311(4) 0.297(2) 0.961(4) 0.092(16) Uiso 1 1 d . . . . .
H7A H 0.931(5) 0.064(3) 0.109(4) 0.14(2) Uiso 1 1 d . . . . .
H7B H 1.004(3) 0.124(2) 0.121(3) 0.073(12) Uiso 1 1 d . . . . .
H4CC H 0.416(3) 0.3211(18) 0.156(3) 0.063(10) 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
S1 C12 1.713(3) . ?
S1 C13 1.729(3) . ?
O1 C24 1.256(3) . ?
O2 C24 1.256(3) . ?
O3 C20 1.372(3) . ?
O3 H3 0.87(5) . ?
O4 C21 1.365(3) . ?
O4 H4 0.77(4) . ?
O5 C22 1.375(3) . ?
O5 H5 0.85(3) . ?
O6 H6A 0.75(4) . ?
O6 H6B 0.83(4) . ?
O7 H7A 0.86(6) . ?
O7 H7B 0.88(4) . ?
N1 C1 1.478(4) . ?
N1 C17 1.483(4) . ?
N1 C4 1.489(4) . ?
N1 H1 0.81(3) . ?
N2 C5 1.377(3) . ?
N2 C3 1.456(4) . ?
N2 C2 1.464(3) . ?
N3 C5 1.292(3) . ?
N3 C6 1.414(4) . ?
N4 C12 1.401(4) . ?
N4 C11 1.427(4) . ?
N4 H4CC 0.84(3) . ?
C1 C2 1.510(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.497(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C15 1.473(4) . ?
C6 C7 1.384(4) . ?
C6 C11 1.404(4) . ?
C7 C8 1.379(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9300 . ?
C12 C15 1.369(4) . ?
C13 C14 1.346(4) . ?
C13 C16 1.507(5) . ?
C14 C15 1.429(4) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.384(3) . ?
C18 C23 1.389(3) . ?
C18 C24 1.493(3) . ?
C19 C20 1.375(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.392(3) . ?
C21 C22 1.388(3) . ?
C22 C23 1.379(3) . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C13 92.09(14) . . ?
C20 O3 H3 110(3) . . ?
C21 O4 H4 112(3) . . ?
C22 O5 H5 106(2) . . ?
H6A O6 H6B 109(4) . . ?
H7A O7 H7B 107(4) . . ?
C1 N1 C17 111.5(3) . . ?
C1 N1 C4 110.5(2) . . ?
C17 N1 C4 112.1(2) . . ?
C1 N1 H1 111(2) . . ?
C17 N1 H1 108(2) . . ?
C4 N1 H1 104(2) . . ?
C5 N2 C3 123.4(2) . . ?
C5 N2 C2 119.7(2) . . ?
C3 N2 C2 110.7(2) . . ?
C5 N3 C6 123.0(2) . . ?
C12 N4 C11 113.8(2) . . ?
C12 N4 H4CC 113(2) . . ?
C11 N4 H4CC 113(2) . . ?
N1 C1 C2 112.4(2) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
N2 C2 C1 109.6(2) . . ?
N2 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N2 C3 C4 109.6(2) . . ?
N2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N1 C4 C3 109.8(2) . . ?
N1 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N3 C5 N2 117.9(2) . . ?
N3 C5 C15 125.6(2) . . ?
N2 C5 C15 116.4(2) . . ?
C7 C6 C11 118.1(3) . . ?
C7 C6 N3 117.3(3) . . ?
C11 C6 N3 124.4(3) . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C6 120.0(3) . . ?
C10 C11 N4 121.8(3) . . ?
C6 C11 N4 118.2(3) . . ?
C15 C12 N4 125.4(3) . . ?
C15 C12 S1 111.8(2) . . ?
N4 C12 S1 122.7(2) . . ?
C14 C13 C16 128.8(3) . . ?
C14 C13 S1 110.7(2) . . ?
C16 C13 S1 120.5(3) . . ?
C13 C14 C15 114.1(3) . . ?
C13 C14 H14 123.0 . . ?
C15 C14 H14 123.0 . . ?
C12 C15 C14 111.4(2) . . ?
C12 C15 C5 120.0(2) . . ?
C14 C15 C5 128.4(2) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 119.9(2) . . ?
C19 C18 C24 119.1(2) . . ?
C23 C18 C24 121.0(2) . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
O3 C20 C19 122.0(2) . . ?
O3 C20 C21 117.4(2) . . ?
C19 C20 C21 120.6(2) . . ?
O4 C21 C22 123.1(2) . . ?
O4 C21 C20 117.8(2) . . ?
C22 C21 C20 119.1(2) . . ?
O5 C22 C23 123.9(2) . . ?
O5 C22 C21 115.7(2) . . ?
C23 C22 C21 120.4(2) . . ?
C22 C23 C18 120.0(2) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
O2 C24 O1 123.0(2) . . ?
O2 C24 C18 117.7(2) . . ?
O1 C24 C18 119.3(2) . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_OLN-SPA-MeCN
_database_code_depnum_ccdc_archive 'CCDC 1919074'
loop_
_audit_author_name
_audit_author_address
'Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_OLN-SPA-MeCN        
;
PROBLEM: Short Inter D...A Contact  O1       ..O9       .       2.39 Ang.
RESPONSE: Disordered water H atoms. Hence H atoms have not been assigned from Fourier map 
;
# Added during the CSD deposition process: Tuesday 28 May 2019 08:40 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 N4 O9 S'
_chemical_formula_sum            'C28 H32 N4 O9 S'
_chemical_formula_weight         600.63

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                   9.9166(10)
_cell_length_b                   13.3673(14)
_cell_length_c                   23.035(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.163(5)
_cell_angle_gamma                90
_cell_volume                     3029.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5290
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      26.04

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22206
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.765
_diffrn_reflns_theta_max         26.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6198
_reflns_number_gt                3871
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1660P)²+1.3083P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6198
_refine_ls_number_parameters     395
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2804
_refine_ls_wR_factor_gt          0.2347
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 1.2710(3) 0.0305(2) 0.11225(15) 0.0477(8) Uani 1 1 d . . . . .
C2 C 1.2672(4) -0.0304(3) 0.16178(15) 0.0526(9) Uani 1 1 d . . . . .
C3 C 1.0319(4) -0.0674(3) 0.15107(15) 0.0487(8) Uani 1 1 d . . . . .
H3AA H 0.534(7) 0.295(5) 0.151(3) 0.13(2) Uiso 1 1 d . . . . .
H3 H 0.746(5) 0.328(4) 0.017(2) 0.096(16) Uiso 1 1 d . . . . .
C4 C 0.9814(3) -0.0217(2) 0.10009(13) 0.0404(7) Uani 1 1 d . . . . .
C5 C 1.0388(3) 0.0732(2) 0.08269(13) 0.0397(7) Uani 1 1 d . . . . .
C6 C 0.8712(3) -0.0759(2) 0.06936(15) 0.0464(8) Uani 1 1 d . . . . .
H6 H 0.826088 -0.054713 0.033640 0.056 Uiso 1 1 calc R U . . .
C7 C 0.8372(4) -0.1608(3) 0.09631(17) 0.0562(9) Uani 1 1 d . . . . .
C8 C 0.7288(5) -0.2349(3) 0.0772(2) 0.0837(14) Uani 1 1 d . . . . .
H8A H 0.679812 -0.214052 0.040633 0.126 Uiso 1 1 calc R U . . .
H8B H 0.667343 -0.239381 0.106201 0.126 Uiso 1 1 calc R U . . .
H8C H 0.769176 -0.299209 0.072497 0.126 Uiso 1 1 calc R U . . .
C9 C 1.3824(5) -0.0821(3) 0.18481(19) 0.0687(11) Uani 1 1 d . . . . .
H9 H 1.379362 -0.122044 0.217659 0.082 Uiso 1 1 calc R U . . .
C10 C 1.5008(4) -0.0755(4) 0.1603(2) 0.0781(13) Uani 1 1 d . . . . .
H10 H 1.577439 -0.110156 0.176841 0.094 Uiso 1 1 calc R U . . .
C11 C 1.5065(4) -0.0180(3) 0.1114(2) 0.0760(13) Uani 1 1 d . . . . .
H11 H 1.586091 -0.014746 0.094024 0.091 Uiso 1 1 calc R U . . .
C12 C 1.3928(4) 0.0352(3) 0.08816(19) 0.0602(10) Uani 1 1 d . . . . .
H12 H 1.397826 0.075228 0.055479 0.072 Uiso 1 1 calc R U . . .
C13 C 0.8113(3) 0.1547(2) 0.07132(15) 0.0462(8) Uani 1 1 d . . . . .
H13A H 0.814520 0.207324 0.100424 0.055 Uiso 1 1 calc R U . . .
H13B H 0.781751 0.093601 0.088656 0.055 Uiso 1 1 calc R U . . .
C14 C 0.7122(3) 0.1824(2) 0.01911(16) 0.0509(8) Uani 1 1 d . . . . .
H14A H 0.704808 0.127857 -0.008893 0.061 Uiso 1 1 calc R U . . .
H14B H 0.623259 0.193549 0.031258 0.061 Uiso 1 1 calc R U . . .
C15 C 0.9007(4) 0.2628(3) -0.02229(15) 0.0527(9) Uani 1 1 d . . . . .
H15A H 0.931475 0.325760 -0.036949 0.063 Uiso 1 1 calc R U . . .
H15B H 0.903045 0.212942 -0.052743 0.063 Uiso 1 1 calc R U . . .
C16 C 0.9954(3) 0.2319(2) 0.03062(16) 0.0482(8) Uani 1 1 d . . . . .
H16A H 1.086133 0.222312 0.020050 0.058 Uiso 1 1 calc R U . . .
H16B H 0.999323 0.283954 0.060138 0.058 Uiso 1 1 calc R U . . .
C17 C 0.6647(5) 0.3015(4) -0.0624(2) 0.0807(13) Uani 1 1 d . . . . .
H17A H 0.698339 0.360219 -0.079828 0.121 Uiso 1 1 calc R U . . .
H17B H 0.575637 0.314730 -0.051949 0.121 Uiso 1 1 calc R U . . .
H17C H 0.660074 0.247191 -0.089781 0.121 Uiso 1 1 calc R U . . .
C18 C 0.5047(6) 0.0869(3) 0.30047(17) 0.0775(15) Uani 1 1 d . . . . .
C19 C 0.6399(6) 0.0854(3) 0.28728(19) 0.0738(12) Uani 1 1 d . . . . .
H19 H 0.704677 0.046163 0.309394 0.089 Uiso 1 1 calc R U . . .
C20 C 0.6757(5) 0.1412(3) 0.24230(18) 0.0694(11) Uani 1 1 d . . . . .
C21 C 0.5792(5) 0.1998(3) 0.20916(16) 0.0616(10) Uani 1 1 d . . . . .
C22 C 0.4467(5) 0.2049(3) 0.22196(17) 0.0620(10) Uani 1 1 d . . . . .
C23 C 0.4084(5) 0.1480(3) 0.26799(18) 0.0714(13) Uani 1 1 d . . . . .
H23 H 0.319601 0.150597 0.277024 0.086 Uiso 1 1 calc R U . . .
C24 C 0.4730(7) 0.0210(4) 0.3477(2) 0.1004(19) Uani 1 1 d . . . . .
H24 H 0.545642 -0.018009 0.363992 0.120 Uiso 1 1 calc R U . . .
C25 C 0.3686(8) 0.0080(4) 0.3695(3) 0.112(2) Uani 1 1 d . . . . .
H25 H 0.293612 0.046667 0.355412 0.135 Uiso 1 1 calc R U . . .
C26 C 0.3511(8) -0.0672(4) 0.4184(3) 0.0987(19) Uani 1 1 d . . . . .
C27 C 0.9060(6) 0.0862(4) 0.2578(3) 0.1056(18) Uani 1 1 d . . . . .
H27A H 0.882935 0.016661 0.252953 0.158 Uiso 1 1 calc R U . . .
H27B H 0.913563 0.103324 0.298544 0.158 Uiso 1 1 calc R U . . .
H27C H 0.991223 0.098486 0.243354 0.158 Uiso 1 1 calc R U . . .
C28 C 0.2283(5) 0.2821(4) 0.1950(2) 0.0931(16) Uani 1 1 d . . . . .
H28A H 0.186475 0.329113 0.166785 0.140 Uiso 1 1 calc R U . . .
H28B H 0.224272 0.307483 0.233726 0.140 Uiso 1 1 calc R U . . .
H28C H 0.181083 0.219403 0.190434 0.140 Uiso 1 1 calc R U . . .
H4 H 1.153(5) -0.071(3) 0.2250(14) 0.098(16) Uiso 1 1 d D . . . .
N1 N 1.1663(3) 0.0966(2) 0.08859(12) 0.0454(7) Uani 1 1 d . . . . .
N2 N 0.9474(2) 0.13992(19) 0.05373(11) 0.0411(6) Uani 1 1 d . . . . .
N3 N 0.7579(3) 0.2744(2) -0.00891(12) 0.0475(7) Uani 1 1 d . . . . .
N4 N 1.1458(3) -0.0359(3) 0.18844(13) 0.0593(8) Uani 1 1 d D . . . .
O1 O 0.4528(6) -0.1260(4) 0.4361(2) 0.1237(15) Uani 1 1 d . . . . .
O2 O 0.2485(5) -0.0696(3) 0.4366(2) 0.1302(18) Uani 1 1 d . . . . .
O3 O 0.6194(4) 0.2523(3) 0.16359(15) 0.0845(10) Uani 1 1 d . . . . .
O4 O 0.8033(3) 0.1452(3) 0.22615(15) 0.0924(10) Uani 1 1 d . . . . .
O5 O 0.3661(3) 0.2680(2) 0.18616(14) 0.0800(9) Uani 1 1 d . . . . .
O6 O 0.0995(4) 0.8559(3) 0.29667(16) 0.1107(13) Uani 1 1 d . . . . .
O7 O 0.2228(10) 0.0628(6) 0.5370(3) 0.233(4) Uani 1 1 d . . . . .
O8 O 0.9708(14) -0.0033(6) 0.3996(4) 0.290(5) Uani 1 1 d . . . . .
O9 O 0.3239(19) 0.1955(13) 0.5606(5) 0.414(10) Uani 1 1 d . . . . .
S1 S 0.94454(12) -0.17697(7) 0.16140(4) 0.0655(4) 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 C12 1.392(5) . ?
C1 C2 1.406(5) . ?
C1 N1 1.419(4) . ?
C2 C9 1.383(5) . ?
C2 N4 1.420(5) . ?
C3 C4 1.362(5) . ?
C3 N4 1.397(5) . ?
C3 S1 1.733(4) . ?
C4 C6 1.424(5) . ?
C4 C5 1.467(4) . ?
C5 N1 1.293(4) . ?
C5 N2 1.382(4) . ?
C6 C7 1.356(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.488(6) . ?
C7 S1 1.741(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.367(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N2 1.469(4) . ?
C13 C14 1.501(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N3 1.486(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.495(4) . ?
C15 C16 1.501(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.444(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N3 1.489(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.401(7) . ?
C18 C19 1.412(7) . ?
C18 C24 1.464(6) . ?
C19 C20 1.359(6) . ?
C19 H19 0.9300 . ?
C20 O4 1.364(5) . ?
C20 C21 1.389(6) . ?
C21 O3 1.363(4) . ?
C21 C22 1.384(6) . ?
C22 O5 1.365(5) . ?
C22 C23 1.396(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.218(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.536(8) . ?
C25 H25 0.9300 . ?
C26 O2 1.148(7) . ?
C26 O1 1.303(8) . ?
C27 O4 1.416(6) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 O5 1.419(5) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
N3 H3 0.95(5) . ?
N4 H4 0.960(19) . ?
O3 H3AA 1.04(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C1 C2 117.5(3) . . ?
C12 C1 N1 116.7(3) . . ?
C2 C1 N1 125.4(3) . . ?
C9 C2 C1 119.7(4) . . ?
C9 C2 N4 120.9(4) . . ?
C1 C2 N4 119.4(3) . . ?
C4 C3 N4 125.3(3) . . ?
C4 C3 S1 111.2(3) . . ?
N4 C3 S1 123.3(3) . . ?
C3 C4 C6 112.2(3) . . ?
C3 C4 C5 120.7(3) . . ?
C6 C4 C5 127.1(3) . . ?
N1 C5 N2 118.0(3) . . ?
N1 C5 C4 126.0(3) . . ?
N2 C5 C4 115.9(3) . . ?
C7 C6 C4 114.7(3) . . ?
C7 C6 H6 122.7 . . ?
C4 C6 H6 122.7 . . ?
C6 C7 C8 129.3(4) . . ?
C6 C7 S1 109.8(3) . . ?
C8 C7 S1 120.9(3) . . ?
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 . . ?
C10 C9 C2 121.4(4) . . ?
C10 C9 H9 119.3 . . ?
C2 C9 H9 119.3 . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 119.4(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C1 121.9(4) . . ?
C11 C12 H12 119.1 . . ?
C1 C12 H12 119.1 . . ?
N2 C13 C14 110.1(3) . . ?
N2 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N2 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.2 . . ?
N3 C14 C13 110.4(3) . . ?
N3 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
N3 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N3 C15 C16 112.0(3) . . ?
N3 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N3 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N2 C16 C15 109.4(3) . . ?
N2 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
N2 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 119.8(4) . . ?
C23 C18 C24 123.5(5) . . ?
C19 C18 C24 116.7(5) . . ?
C20 C19 C18 120.1(5) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 O4 124.6(4) . . ?
C19 C20 C21 120.1(4) . . ?
O4 C20 C21 115.3(3) . . ?
O3 C21 C22 121.0(4) . . ?
O3 C21 C20 117.7(4) . . ?
C22 C21 C20 121.2(3) . . ?
O5 C22 C21 113.7(3) . . ?
O5 C22 C23 127.0(4) . . ?
C21 C22 C23 119.4(4) . . ?
C22 C23 C18 119.4(4) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?
C25 C24 C18 131.7(7) . . ?
C25 C24 H24 114.2 . . ?
C18 C24 H24 114.2 . . ?
C24 C25 C26 125.1(7) . . ?
C24 C25 H25 117.4 . . ?
C26 C25 H25 117.4 . . ?
O2 C26 O1 123.7(6) . . ?
O2 C26 C25 118.2(7) . . ?
O1 C26 C25 118.0(6) . . ?
O4 C27 H27A 109.5 . . ?
O4 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O4 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O5 C28 H28A 109.5 . . ?
O5 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O5 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C5 N1 C1 123.3(3) . . ?
C5 N2 C16 120.1(2) . . ?
C5 N2 C13 121.5(2) . . ?
C16 N2 C13 110.1(2) . . ?
C14 N3 C17 111.7(3) . . ?
C14 N3 C15 110.6(3) . . ?
C17 N3 C15 111.2(3) . . ?
C14 N3 H3 107(3) . . ?
C17 N3 H3 103(3) . . ?
C15 N3 H3 113(3) . . ?
C3 N4 C2 114.4(3) . . ?
C3 N4 H4 111(3) . . ?
C2 N4 H4 116(3) . . ?
C21 O3 H3AA 101(3) . . ?
C20 O4 C27 118.1(4) . . ?
C22 O5 C28 119.8(4) . . ?
C3 S1 C7 92.23(17) . . ?

_refine_diff_density_max         0.703
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.095

