# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_SR_252_rpt1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1995006'
loop_
_audit_author_name
_audit_author_address
'Muhammad Usman Anwar'
;University of Nizwa
Oman
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-05-19 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         'C10 H12 N4 O3 S'
_chemical_formula_sum            'C10 H12 N4 O3 S'
_chemical_formula_weight         268.30

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                   12.4131(9)
_cell_length_b                   7.2670(7)
_cell_length_c                   13.5080(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.147(2)
_cell_angle_gamma                90
_cell_volume                     1120.41(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5677
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      26.42

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.296
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6207
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16132
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.056
_diffrn_reflns_theta_max         26.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2289
_reflns_number_gt                1811
_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 2014/5 (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)+(0.0589P)²+1.2354P] 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         2289
_refine_ls_number_parameters     176
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.87217(5) 0.12783(11) 0.46179(5) 0.0376(2) Uani 1 1 d . . . . .
O1 O 0.62328(15) 0.1952(3) 0.66371(12) 0.0357(5) Uani 1 1 d . . . . .
O2 O 0.45679(15) 0.3027(3) 0.28951(13) 0.0388(5) Uani 1 1 d D . . . .
H1C H 0.467(3) 0.288(5) 0.2339(18) 0.047 Uiso 1 1 d D U . . .
O3 O -0.08270(15) 0.3215(3) 0.26588(14) 0.0399(5) Uani 1 1 d D . . . .
H3O H -0.106(3) 0.281(4) 0.311(2) 0.048 Uiso 1 1 d D U . . .
N1 N 0.72483(17) 0.1634(3) 0.55820(15) 0.0263(5) Uani 1 1 d D . . . .
H1A H 0.7836(19) 0.147(4) 0.6156(16) 0.032 Uiso 1 1 d D U . . .
N2 N 0.64500(17) 0.2136(3) 0.37728(15) 0.0289(5) Uani 1 1 d D . . . .
H2A H 0.653(2) 0.222(4) 0.3169(16) 0.035 Uiso 1 1 d D U . . .
N3 N 0.38816(16) 0.2848(3) 0.57215(15) 0.0247(4) Uani 1 1 d . . . . .
N4 N 0.22813(16) 0.3749(3) 0.44546(15) 0.0269(5) Uani 1 1 d . . . . .
C1 C 0.74006(19) 0.1703(3) 0.46494(18) 0.0255(5) Uani 1 1 d . . . . .
C2 C 0.61995(19) 0.2020(3) 0.57099(18) 0.0244(5) Uani 1 1 d . . . . .
C3 C 0.53454(19) 0.2569(3) 0.37647(17) 0.0257(5) Uani 1 1 d . . . . .
C4 C 0.52298(18) 0.2467(3) 0.47628(17) 0.0228(5) Uani 1 1 d . . . . .
C5 C 0.41045(19) 0.2916(3) 0.47902(17) 0.0229(5) Uani 1 1 d . . . . .
C6 C 0.30908(19) 0.3489(3) 0.40000(18) 0.0267(5) Uani 1 1 d . . . . .
H6 H 0.296365 0.367284 0.328126 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2775(2) 0.3361(3) 0.55033(18) 0.0260(5) Uani 1 1 d . . . . .
C8 C 0.2219(2) 0.3513(4) 0.6286(2) 0.0381(6) Uani 1 1 d . . . . .
H8A H 0.168766 0.453698 0.609725 0.057 Uiso 1 1 calc R U . . .
H8B H 0.281179 0.369864 0.699449 0.057 Uiso 1 1 calc R U . . .
H8C H 0.179605 0.240212 0.627580 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1054(2) 0.4263(4) 0.3858(2) 0.0346(6) Uani 1 1 d . . . . .
H9A H 0.101844 0.537139 0.344609 0.041 Uiso 1 1 calc R U . . .
H9B H 0.069488 0.453024 0.436334 0.041 Uiso 1 1 calc R U . . .
C10 C 0.0383(2) 0.2776(4) 0.3116(2) 0.0411(7) Uani 1 1 d . . . . .
H10A H 0.066896 0.262180 0.254784 0.049 Uiso 1 1 calc R U . . .
H10B H 0.049882 0.162462 0.350805 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.686(2) . ?
O1 C2 1.238(3) . ?
O2 C3 1.237(3) . ?
O2 H1C 0.819(18) . ?
O3 C10 1.418(3) . ?
O3 H3O 0.832(18) . ?
N1 C1 1.346(3) . ?
N1 C2 1.407(3) . ?
N1 H1A 0.838(17) . ?
N2 C1 1.340(3) . ?
N2 C3 1.403(3) . ?
N2 H2A 0.862(17) . ?
N3 C7 1.340(3) . ?
N3 C5 1.391(3) . ?
N4 C7 1.334(3) . ?
N4 C6 1.381(3) . ?
N4 C9 1.465(3) . ?
C2 C4 1.407(3) . ?
C3 C4 1.413(3) . ?
C4 C5 1.449(3) . ?
C5 C6 1.356(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.477(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.487(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
C3 O2 H1C 119(2) . . ?
C10 O3 H3O 103(2) . . ?
C1 N1 C2 125.77(19) . . ?
C1 N1 H1A 118.7(19) . . ?
C2 N1 H1A 115.1(19) . . ?
C1 N2 C3 125.33(19) . . ?
C1 N2 H2A 117.7(19) . . ?
C3 N2 H2A 116.9(19) . . ?
C7 N3 C5 110.03(18) . . ?
C7 N4 C6 109.42(19) . . ?
C7 N4 C9 125.6(2) . . ?
C6 N4 C9 124.9(2) . . ?
N2 C1 N1 115.9(2) . . ?
N2 C1 S1 123.25(17) . . ?
N1 C1 S1 120.84(17) . . ?
O1 C2 C4 127.3(2) . . ?
O1 C2 N1 116.9(2) . . ?
C4 C2 N1 115.86(19) . . ?
O2 C3 N2 117.6(2) . . ?
O2 C3 C4 125.9(2) . . ?
N2 C3 C4 116.50(19) . . ?
C2 C4 C3 120.6(2) . . ?
C2 C4 C5 121.15(19) . . ?
C3 C4 C5 118.23(19) . . ?
C6 C5 N3 105.65(19) . . ?
C6 C5 C4 130.9(2) . . ?
N3 C5 C4 123.47(19) . . ?
C5 C6 N4 107.70(19) . . ?
C5 C6 H6 126.1 . . ?
N4 C6 H6 126.1 . . ?
N4 C7 N3 107.2(2) . . ?
N4 C7 C8 126.6(2) . . ?
N3 C7 C8 126.2(2) . . ?
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 . . ?
N4 C9 C10 111.8(2) . . ?
N4 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N4 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
O3 C10 C9 110.3(2) . . ?
O3 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
O3 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?

_refine_diff_density_max         0.734
_refine_diff_density_min         -0.508
_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_SR287_rpt2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1995009'
loop_
_audit_author_name
_audit_author_address
'Muhammad Usman Anwar'
;University of Nizwa
Oman
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-05-19 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         'C20 H24 N4 O6'
_chemical_formula_sum            'C20 H24 N4 O6'
_chemical_formula_weight         416.43

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'

_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                   12.1408(6)
_cell_length_b                   11.8095(6)
_cell_length_c                   14.8569(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.558(2)
_cell_angle_gamma                90
_cell_volume                     2019.37(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      26.43

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36034
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.135
_diffrn_reflns_theta_max         26.440
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4131
_reflns_number_gt                3290
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0916P)²+1.3500P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4131
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1630
_refine_ls_wR_factor_gt          0.1397
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.29197(14) 0.68123(17) 0.19674(12) 0.0571(5) Uani 1 1 d . . . . .
O2 O 0.44657(14) 0.57289(13) 0.20698(11) 0.0481(4) Uani 1 1 d . . . . .
O3 O 0.72102(14) 0.41030(14) 0.56695(10) 0.0486(4) Uani 1 1 d . . . . .
O4 O 0.99838(12) 0.68258(13) 0.65085(10) 0.0405(4) Uani 1 1 d . . . . .
O5 O 0.84554(14) 0.59671(12) 0.33691(10) 0.0400(4) Uani 1 1 d D . . . .
H5A H 0.864(2) 0.6492(18) 0.3035(17) 0.048 Uiso 1 1 d D U . . .
O6 O 0.54043(16) 0.26332(16) 0.50327(16) 0.0677(6) Uani 1 1 d . . . . .
H6A H 0.600(3) 0.317(2) 0.518(3) 0.102 Uiso 1 1 calc R U . . .
N1 N 0.58351(13) 0.41665(12) 0.34417(10) 0.0265(4) Uani 1 1 d . . . . .
N2 N 0.63333(14) 0.27553(13) 0.27386(11) 0.0317(4) Uani 1 1 d . . . . .
N3 N 0.92124(13) 0.63973(12) 0.49376(11) 0.0290(4) Uani 1 1 d . . . . .
N4 N 0.85870(14) 0.54719(14) 0.60824(11) 0.0314(4) Uani 1 1 d . . . . .
C1 C 0.30457(17) 0.59072(16) 0.05750(14) 0.0331(4) Uani 1 1 d . . . . .
C2 C 0.2084(2) 0.64683(19) -0.00197(17) 0.0465(5) Uani 1 1 d . . . . .
H2A H 0.170598 0.701238 0.022680 0.056 Uiso 1 1 calc R U . . .
C3 C 0.1690(2) 0.6220(2) -0.09750(18) 0.0558(6) Uani 1 1 d . . . . .
H3 H 0.104587 0.659750 -0.137179 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2243(2) 0.5416(2) -0.13451(16) 0.0506(6) Uani 1 1 d . . . . .
H4 H 0.196982 0.525008 -0.199025 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3200(2) 0.4857(2) -0.07649(17) 0.0472(5) Uani 1 1 d . . . . .
H5 H 0.357380 0.431653 -0.101865 0.057 Uiso 1 1 calc R U . . .
C6 C 0.36062(18) 0.50977(18) 0.01965(15) 0.0395(5) Uani 1 1 d . . . . .
H6 H 0.425292 0.471905 0.058888 0.047 Uiso 1 1 calc R U . . .
C7 C 0.34441(17) 0.62089(17) 0.15982(14) 0.0351(4) Uani 1 1 d . . . . .
C8 C 0.5007(2) 0.60581(19) 0.30462(16) 0.0497(6) Uani 1 1 d . . . . .
H8A H 0.453797 0.663089 0.321924 0.060 Uiso 1 1 calc R U . . .
H8B H 0.576679 0.637955 0.312379 0.060 Uiso 1 1 calc R U . . .
C9 C 0.51298(17) 0.50456(18) 0.36839(14) 0.0370(5) Uani 1 1 d . . . . .
H9A H 0.549016 0.527499 0.433899 0.044 Uiso 1 1 calc R U . . .
H9B H 0.436623 0.474365 0.362240 0.044 Uiso 1 1 calc R U . . .
C10 C 0.54257(16) 0.33010(16) 0.28505(13) 0.0294(4) Uani 1 1 d . . . . .
C11 C 0.41904(18) 0.2967(2) 0.24260(17) 0.0458(5) Uani 1 1 d . . . . .
H11A H 0.376228 0.357981 0.205025 0.069 Uiso 1 1 calc R U . . .
H11B H 0.386972 0.279038 0.292242 0.069 Uiso 1 1 calc R U . . .
H11C H 0.413980 0.231300 0.203056 0.069 Uiso 1 1 calc R U . . .
C12 C 0.73424(16) 0.32759(16) 0.32806(13) 0.0306(4) Uani 1 1 d . . . . .
H12 H 0.809385 0.305599 0.332650 0.037 Uiso 1 1 calc R U . . .
C13 C 0.70497(15) 0.41611(14) 0.37334(12) 0.0255(4) Uani 1 1 d . . . . .
C14 C 0.77742(15) 0.49472(14) 0.44485(12) 0.0260(4) Uani 1 1 d . . . . .
C15 C 0.78128(16) 0.47898(16) 0.53976(13) 0.0303(4) Uani 1 1 d . . . . .
C16 C 0.8683(2) 0.5336(2) 0.70862(14) 0.0455(5) Uani 1 1 d . . . . .
H16A H 0.814378 0.476920 0.714530 0.068 Uiso 1 1 calc R U . . .
H16B H 0.850939 0.604292 0.733045 0.068 Uiso 1 1 calc R U . . .
H16C H 0.945939 0.510762 0.743953 0.068 Uiso 1 1 calc R U . . .
C17 C 0.93054(15) 0.62634(15) 0.58816(13) 0.0284(4) Uani 1 1 d . . . . .
C18 C 0.99303(19) 0.72647(18) 0.46985(16) 0.0411(5) Uani 1 1 d . . . . .
H18A H 1.042607 0.691863 0.438654 0.062 Uiso 1 1 calc R U . . .
H18B H 1.039738 0.763231 0.526851 0.062 Uiso 1 1 calc R U . . .
H18C H 0.943949 0.781334 0.428315 0.062 Uiso 1 1 calc R U . . .
C19 C 0.84591(15) 0.57638(14) 0.41936(12) 0.0260(4) Uani 1 1 d . . . . .
C20 C 0.5875(4) 0.1562(3) 0.5061(4) 0.1029(14) Uani 1 1 d . . . . .
H20A H 0.529369 0.105544 0.468000 0.154 Uiso 1 1 calc R U . . .
H20B H 0.613936 0.129607 0.570469 0.154 Uiso 1 1 calc R U . . .
H20C H 0.651765 0.159132 0.481695 0.154 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.198(2) . ?
O2 C7 1.341(2) . ?
O2 C8 1.442(3) . ?
O3 C15 1.243(2) . ?
O4 C17 1.224(2) . ?
O5 C19 1.247(2) . ?
O5 H5A 0.868(17) . ?
O6 C20 1.383(4) . ?
O6 H6A 0.93(4) . ?
N1 C10 1.336(2) . ?
N1 C13 1.399(2) . ?
N1 C9 1.462(2) . ?
N2 C10 1.332(2) . ?
N2 C12 1.378(2) . ?
N3 C17 1.380(2) . ?
N3 C19 1.405(2) . ?
N3 C18 1.460(2) . ?
N4 C17 1.374(2) . ?
N4 C15 1.400(2) . ?
N4 C16 1.467(2) . ?
C1 C2 1.388(3) . ?
C1 C6 1.392(3) . ?
C1 C7 1.484(3) . ?
C2 C3 1.377(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.503(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.484(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.350(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.473(2) . ?
C14 C19 1.402(2) . ?
C14 C15 1.408(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C8 117.47(16) . . ?
C19 O5 H5A 141.2(17) . . ?
C20 O6 H6A 109.5 . . ?
C10 N1 C13 109.58(15) . . ?
C10 N1 C9 125.50(16) . . ?
C13 N1 C9 124.71(15) . . ?
C10 N2 C12 109.15(15) . . ?
C17 N3 C19 124.11(15) . . ?
C17 N3 C18 117.75(15) . . ?
C19 N3 C18 118.14(15) . . ?
C17 N4 C15 124.01(15) . . ?
C17 N4 C16 116.38(16) . . ?
C15 N4 C16 119.59(16) . . ?
C2 C1 C6 119.4(2) . . ?
C2 C1 C7 118.12(18) . . ?
C6 C1 C7 122.47(18) . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1 C7 O2 123.4(2) . . ?
O1 C7 C1 124.33(19) . . ?
O2 C7 C1 112.30(17) . . ?
O2 C8 C9 109.97(18) . . ?
O2 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
O2 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N1 C9 C8 110.99(17) . . ?
N1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 N1 107.63(16) . . ?
N2 C10 C11 125.64(17) . . ?
N1 C10 C11 126.68(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N2 108.09(16) . . ?
C13 C12 H12 126.0 . . ?
N2 C12 H12 126.0 . . ?
C12 C13 N1 105.53(15) . . ?
C12 C13 C14 130.98(16) . . ?
N1 C13 C14 123.33(15) . . ?
C19 C14 C15 121.85(16) . . ?
C19 C14 C13 120.54(15) . . ?
C15 C14 C13 117.45(15) . . ?
O3 C15 N4 117.91(17) . . ?
O3 C15 C14 125.18(17) . . ?
N4 C15 C14 116.90(16) . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 N4 121.57(17) . . ?
O4 C17 N3 121.92(17) . . ?
N4 C17 N3 116.51(15) . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 C14 125.51(16) . . ?
O5 C19 N3 117.92(16) . . ?
C14 C19 N3 116.57(15) . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.636
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.051

