# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_HphenureaClO4
_database_code_depnum_ccdc_archive 'CCDC 2171843'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 N3 O, Cl O4'
_chemical_formula_sum            'C13 H14 Cl N3 O5'
_chemical_formula_weight         327.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.6033(11)
_cell_length_b                   9.1856(9)
_cell_length_c                   30.910(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3010.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3205
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.50
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0870 before and 0.0541 after correction.
The Ratio of minimum to maximum transmission is 0.9057.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6753
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            20497
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.329
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1762
_reflns_number_total             2666
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0650
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1146P)²+1.4143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1792
_refine_ls_wR_factor_ref         0.2044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N2-H2 = N1-H1
 0.858 with sigma of 0.02
 Cl1-O5 \\sim Cl1-O5A
 with sigma of 0.02
 Cl1-O3 \\sim Cl1-O3A
 with sigma of 0.02
 Cl1-O2 \\sim Cl1-O2A
 with sigma of 0.02
 Cl1-O4 \\sim Cl1-O4A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O3) = Uanis(O4A)
Uanis(O2A) = Uanis(O4)
Uanis(O3A) = Uanis(O2)
Uanis(O5) = Uanis(O5A)
4. Others
 Sof(O4A)=Sof(O2A)=Sof(O3A)=Sof(O5A)=1-FVAR(1)
 Sof(O4)=Sof(O2)=Sof(O3)=Sof(O5)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5), C3(H3A), C10(H10), C1(H1A), C13(H13), C2(H2A), C6(H6),
 C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   direct
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
Cl1 Cl 0.41310(11) 0.42292(12) 0.55813(4) 0.0706(4) Uani 1 1 d D . . . .
O1 O 0.7234(2) 0.5520(2) 0.66793(8) 0.0491(7) Uani 1 1 d . . . . .
N1 N 0.6463(3) 0.7831(3) 0.67273(10) 0.0463(7) Uani 1 1 d D . . . .
N2 N 0.8398(3) 0.7404(3) 0.64355(10) 0.0520(8) Uani 1 1 d D . . . .
C4 C 0.5272(3) 0.7515(3) 0.69048(11) 0.0439(8) Uani 1 1 d . . . . .
C7 C 0.7357(3) 0.6843(3) 0.66189(10) 0.0434(8) Uani 1 1 d . . . . .
C9 C 0.9489(3) 0.5474(3) 0.60189(11) 0.0465(9) Uani 1 1 d . . . . .
O4 O 0.3520(7) 0.4020(7) 0.59920(18) 0.0853(17) Uani 0.762(5) 1 d D . P A 1
C8 C 0.9519(3) 0.6546(4) 0.63871(12) 0.0496(9) Uani 1 1 d . . . . .
H8A H 0.966432 0.601705 0.665405 0.060 Uiso 1 1 calc R U . . .
H8B H 1.022849 0.719792 0.634466 0.060 Uiso 1 1 calc R U . . .
N3 N 0.9560(5) 0.3423(4) 0.53904(13) 0.0801(12) Uani 1 1 d . . . . .
H3 H 0.958755 0.277576 0.518949 0.096 Uiso 1 1 calc R U . . .
C5 C 0.4809(4) 0.8412(4) 0.72272(12) 0.0536(9) Uani 1 1 d . . . . .
H5 H 0.530178 0.917198 0.733189 0.064 Uiso 1 1 calc R U . . .
C3 C 0.4548(4) 0.6378(4) 0.67577(13) 0.0566(10) Uani 1 1 d . . . . .
H3A H 0.484829 0.577365 0.653938 0.068 Uiso 1 1 calc R U . . .
C10 C 0.8478(4) 0.5289(4) 0.57454(13) 0.0598(10) Uani 1 1 d . . . . .
H10 H 0.776766 0.587555 0.577490 0.072 Uiso 1 1 calc R U . . .
C1 C 0.2903(4) 0.7039(5) 0.72499(15) 0.0747(12) Uani 1 1 d . . . . .
H1A H 0.210411 0.687933 0.736467 0.090 Uiso 1 1 calc R U . . .
C13 C 1.0533(4) 0.4590(5) 0.59615(15) 0.0666(11) Uani 1 1 d . . . . .
H13 H 1.123134 0.470012 0.614052 0.080 Uiso 1 1 calc R U . . .
C2 C 0.3370(4) 0.6134(5) 0.69356(14) 0.0679(11) Uani 1 1 d . . . . .
H2A H 0.288985 0.534856 0.684114 0.081 Uiso 1 1 calc R U . . .
C6 C 0.3621(4) 0.8182(5) 0.73937(14) 0.0688(12) Uani 1 1 d . . . . .
H6 H 0.330468 0.880427 0.760473 0.083 Uiso 1 1 calc R U . . .
C11 C 0.8515(5) 0.4243(5) 0.54295(14) 0.0741(13) Uani 1 1 d . . . . .
H11 H 0.783111 0.410307 0.524577 0.089 Uiso 1 1 calc R U . . .
C12 C 1.0545(5) 0.3572(5) 0.56483(18) 0.0839(15) Uani 1 1 d . . . . .
H12 H 1.124553 0.297410 0.561359 0.101 Uiso 1 1 calc R U . . .
O2 O 0.3608(6) 0.5411(6) 0.5374(2) 0.1255(19) Uani 0.762(5) 1 d D . P A 1
O3 O 0.5393(5) 0.4631(11) 0.5698(2) 0.159(3) Uani 0.762(5) 1 d D . P A 1
H1 H 0.673(3) 0.870(2) 0.6702(11) 0.051(10) Uiso 1 1 d D . . . .
H2 H 0.850(4) 0.832(2) 0.6426(12) 0.062(12) Uiso 1 1 d D . . . .
O5 O 0.4120(14) 0.2984(7) 0.5352(3) 0.229(6) Uani 0.762(5) 1 d D . P A 1
O4A O 0.4944(19) 0.548(3) 0.5553(8) 0.159(3) Uani 0.238(5) 1 d D . P A 2
O2A O 0.341(3) 0.353(3) 0.5890(7) 0.0853(17) Uani 0.238(5) 1 d D . P A 2
O3A O 0.3390(19) 0.387(2) 0.5200(6) 0.1255(19) Uani 0.238(5) 1 d D . P A 2
O5A O 0.507(3) 0.331(2) 0.5434(11) 0.229(6) Uani 0.238(5) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 O4 1.438(6) . ?
Cl1 O2 1.378(5) . ?
Cl1 O3 1.435(6) . ?
Cl1 O5 1.345(5) . ?
Cl1 O4A 1.441(17) . ?
Cl1 O2A 1.378(18) . ?
Cl1 O3A 1.454(15) . ?
Cl1 O5A 1.378(19) . ?
O1 C7 1.237(4) . ?
N1 C4 1.407(4) . ?
N1 C7 1.354(4) . ?
N1 H1 0.851(19) . ?
N2 C7 1.344(4) . ?
N2 C8 1.434(4) . ?
N2 H2 0.848(19) . ?
C4 C5 1.383(5) . ?
C4 C3 1.374(5) . ?
C9 C8 1.506(5) . ?
C9 C10 1.376(5) . ?
C9 C13 1.385(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N3 H3 0.8600 . ?
N3 C11 1.345(6) . ?
N3 C12 1.321(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(5) . ?
C3 H3A 0.9300 . ?
C3 C2 1.382(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(6) . ?
C1 H1A 0.9300 . ?
C1 C2 1.371(6) . ?
C1 C6 1.371(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.346(6) . ?
C2 H2A 0.9300 . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 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
O2 Cl1 O4 109.6(4) . . ?
O2 Cl1 O3 106.9(4) . . ?
O3 Cl1 O4 103.4(4) . . ?
O5 Cl1 O4 110.3(4) . . ?
O5 Cl1 O2 114.9(6) . . ?
O5 Cl1 O3 111.1(7) . . ?
O4A Cl1 O3A 117.2(13) . . ?
O2A Cl1 O4A 138.1(14) . . ?
O2A Cl1 O3A 98.9(14) . . ?
O5A Cl1 O4A 92.1(15) . . ?
O5A Cl1 O2A 110.1(17) . . ?
O5A Cl1 O3A 89.0(18) . . ?
C4 N1 H1 122(3) . . ?
C7 N1 C4 125.9(3) . . ?
C7 N1 H1 112(3) . . ?
C7 N2 C8 121.0(3) . . ?
C7 N2 H2 120(3) . . ?
C8 N2 H2 116(3) . . ?
C5 C4 N1 118.5(3) . . ?
C3 C4 N1 122.0(3) . . ?
C3 C4 C5 119.5(4) . . ?
O1 C7 N1 123.2(3) . . ?
O1 C7 N2 121.8(3) . . ?
N2 C7 N1 115.0(3) . . ?
C10 C9 C8 124.2(3) . . ?
C10 C9 C13 118.2(3) . . ?
C13 C9 C8 117.6(3) . . ?
N2 C8 C9 114.9(3) . . ?
N2 C8 H8A 108.6 . . ?
N2 C8 H8B 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.5 . . ?
C11 N3 H3 118.7 . . ?
C12 N3 H3 118.7 . . ?
C12 N3 C11 122.6(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C3 H3A 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C2 C3 H3A 120.1 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 119.9 . . ?
C2 C1 H1A 120.2 . . ?
C6 C1 H1A 120.2 . . ?
C6 C1 C2 119.6(4) . . ?
C9 C13 H13 119.8 . . ?
C12 C13 C9 120.5(4) . . ?
C12 C13 H13 119.8 . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 C3 120.6(4) . . ?
C1 C2 H2A 119.7 . . ?
C5 C6 H6 119.9 . . ?
C1 C6 C5 120.3(4) . . ?
C1 C6 H6 119.9 . . ?
N3 C11 C10 118.7(4) . . ?
N3 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
N3 C12 C13 119.9(4) . . ?
N3 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?

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
N1 C4 C5 C6 176.7(3) . . . . ?
N1 C4 C3 C2 -178.4(3) . . . . ?
C4 N1 C7 O1 -2.5(5) . . . . ?
C4 N1 C7 N2 177.0(3) . . . . ?
C4 C5 C6 C1 1.8(6) . . . . ?
C4 C3 C2 C1 1.7(6) . . . . ?
C7 N1 C4 C5 140.1(3) . . . . ?
C7 N1 C4 C3 -42.0(5) . . . . ?
C7 N2 C8 C9 77.7(4) . . . . ?
C9 C10 C11 N3 -0.8(6) . . . . ?
C9 C13 C12 N3 0.7(7) . . . . ?
C8 N2 C7 O1 -13.7(5) . . . . ?
C8 N2 C7 N1 166.8(3) . . . . ?
C8 C9 C10 C11 -177.3(4) . . . . ?
C8 C9 C13 C12 177.5(4) . . . . ?
C5 C4 C3 C2 -0.5(5) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C10 C9 C8 N2 -0.5(5) . . . . ?
C10 C9 C13 C12 -0.6(6) . . . . ?
C13 C9 C8 N2 -178.6(3) . . . . ?
C13 C9 C10 C11 0.7(6) . . . . ?
C2 C1 C6 C5 -0.7(6) . . . . ?
C6 C1 C2 C3 -1.1(7) . . . . ?
C11 N3 C12 C13 -0.9(8) . . . . ?
C12 N3 C11 C10 1.0(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_HphenthioureaNO3
_database_code_depnum_ccdc_archive 'CCDC 2171845'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 N3 S, N O3'
_chemical_formula_sum            'C13 H14 N4 O3 S'
_chemical_formula_weight         306.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.5055(9)
_cell_length_b                   8.4091(7)
_cell_length_c                   14.4045(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.059(3)
_cell_angle_gamma                90
_cell_volume                     1392.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4026
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0913 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.9165.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6834
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12150
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         2.805
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1890
_reflns_number_total             2460
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+0.9160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1121
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C10(H10), C13(H13), C3(H3A), C11(H11), C5(H5),
 C12(H12), C6(H6), C2(H2A), C1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.06834(6) 0.43327(8) 0.25579(5) 0.0524(2) Uani 1 1 d . . . . .
N1 N 0.23272(17) 0.5997(2) 0.16821(13) 0.0416(5) Uani 1 1 d . . . . .
H1 H 0.282736 0.675322 0.174238 0.050 Uiso 1 1 calc R U . . .
N2 N 0.19772(17) 0.6764(2) 0.31356(13) 0.0441(5) Uani 1 1 d . . . . .
H2 H 0.249594 0.747236 0.303323 0.053 Uiso 1 1 calc R U . . .
O1 O 0.39490(17) 0.1867(3) 0.75293(15) 0.0758(6) Uani 1 1 d . . . . .
N4 N 0.50166(19) 0.2045(3) 0.75596(17) 0.0518(6) Uani 1 1 d . . . . .
N3 N 0.30635(19) 0.3754(3) 0.60633(15) 0.0522(6) Uani 1 1 d . . . . .
H3 H 0.338180 0.314840 0.648080 0.063 Uiso 1 1 calc R U . . .
C4 C 0.2308(2) 0.5243(3) 0.08094(16) 0.0380(5) Uani 1 1 d . . . . .
C7 C 0.16950(19) 0.5739(3) 0.24458(15) 0.0369(5) Uani 1 1 d . . . . .
C9 C 0.2054(2) 0.5672(3) 0.47363(16) 0.0384(5) Uani 1 1 d . . . . .
O3 O 0.54607(19) 0.2583(3) 0.68647(19) 0.0982(8) Uani 1 1 d . . . . .
C10 C 0.1541(2) 0.5419(3) 0.55827(17) 0.0459(6) Uani 1 1 d . . . . .
H10 H 0.084178 0.591816 0.570645 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3101(2) 0.4924(3) 0.45853(18) 0.0465(6) Uani 1 1 d . . . . .
H13 H 0.346856 0.506173 0.402636 0.056 Uiso 1 1 calc R U . . .
C3 C 0.1371(2) 0.4418(3) 0.04238(17) 0.0454(6) Uani 1 1 d . . . . .
H3A H 0.069779 0.429559 0.075526 0.055 Uiso 1 1 calc R U . . .
C8 C 0.1469(2) 0.6750(3) 0.40301(16) 0.0433(6) Uani 1 1 d . . . . .
H8A H 0.066105 0.643171 0.395117 0.052 Uiso 1 1 calc R U . . .
H8B H 0.148085 0.782533 0.427385 0.052 Uiso 1 1 calc R U . . .
O2 O 0.5613(2) 0.1713(3) 0.8245(2) 0.1056(10) Uani 1 1 d . . . . .
C11 C 0.2051(2) 0.4450(3) 0.62286(19) 0.0527(7) Uani 1 1 d . . . . .
H11 H 0.169467 0.427000 0.678826 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3295(2) 0.5432(3) 0.02890(18) 0.0515(7) Uani 1 1 d . . . . .
H5 H 0.393160 0.599306 0.053392 0.062 Uiso 1 1 calc R U . . .
C12 C 0.3593(2) 0.3975(3) 0.5269(2) 0.0518(7) Uani 1 1 d . . . . .
H12 H 0.430249 0.348181 0.517489 0.062 Uiso 1 1 calc R U . . .
C6 C 0.3328(3) 0.4784(4) -0.0594(2) 0.0622(8) Uani 1 1 d . . . . .
H6 H 0.398743 0.492167 -0.094057 0.075 Uiso 1 1 calc R U . . .
C2 C 0.1436(3) 0.3775(3) -0.04572(18) 0.0541(7) Uani 1 1 d . . . . .
H2A H 0.080352 0.321438 -0.070896 0.065 Uiso 1 1 calc R U . . .
C1 C 0.2403(3) 0.3942(4) -0.09631(19) 0.0607(8) Uani 1 1 d . . . . .
H1A H 0.243571 0.349121 -0.155127 0.073 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 C7 1.671(2) . ?
N1 H1 0.8600 . ?
N1 C4 1.407(3) . ?
N1 C7 1.358(3) . ?
N2 H2 0.8600 . ?
N2 C7 1.346(3) . ?
N2 C8 1.434(3) . ?
O1 N4 1.237(3) . ?
N4 O3 1.227(3) . ?
N4 O2 1.215(3) . ?
N3 H3 0.8600 . ?
N3 C11 1.332(3) . ?
N3 C12 1.328(3) . ?
C4 C3 1.381(3) . ?
C4 C5 1.392(3) . ?
C9 C10 1.390(3) . ?
C9 C13 1.383(3) . ?
C9 C8 1.504(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.355(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.374(4) . ?
C3 H3A 0.9300 . ?
C3 C2 1.384(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 H11 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C6 C1 1.370(4) . ?
C2 H2A 0.9300 . ?
C2 C1 1.358(4) . ?
C1 H1A 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
C4 N1 H1 114.4 . . ?
C7 N1 H1 114.4 . . ?
C7 N1 C4 131.3(2) . . ?
C7 N2 H2 117.9 . . ?
C7 N2 C8 124.3(2) . . ?
C8 N2 H2 117.9 . . ?
O3 N4 O1 117.3(2) . . ?
O2 N4 O1 122.2(3) . . ?
O2 N4 O3 120.5(3) . . ?
C11 N3 H3 119.2 . . ?
C12 N3 H3 119.2 . . ?
C12 N3 C11 121.6(2) . . ?
C3 C4 N1 124.9(2) . . ?
C3 C4 C5 118.7(2) . . ?
C5 C4 N1 116.3(2) . . ?
N1 C7 S1 125.92(18) . . ?
N2 C7 S1 122.13(17) . . ?
N2 C7 N1 111.9(2) . . ?
C10 C9 C8 119.5(2) . . ?
C13 C9 C10 117.9(2) . . ?
C13 C9 C8 122.6(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C13 H13 120.3 . . ?
C12 C13 C9 119.3(2) . . ?
C12 C13 H13 120.3 . . ?
C4 C3 H3A 120.1 . . ?
C4 C3 C2 119.8(2) . . ?
C2 C3 H3A 120.1 . . ?
N2 C8 C9 115.19(19) . . ?
N2 C8 H8A 108.5 . . ?
N2 C8 H8B 108.5 . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
N3 C11 C10 120.1(2) . . ?
N3 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
N3 C12 C13 120.6(2) . . ?
N3 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C5 C6 H6 119.6 . . ?
C1 C6 C5 120.8(3) . . ?
C1 C6 H6 119.6 . . ?
C3 C2 H2A 119.2 . . ?
C1 C2 C3 121.6(3) . . ?
C1 C2 H2A 119.2 . . ?
C6 C1 H1A 120.5 . . ?
C2 C1 C6 119.0(3) . . ?
C2 C1 H1A 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C3 C2 177.6(2) . . . . ?
N1 C4 C5 C6 -177.4(2) . . . . ?
C4 N1 C7 S1 1.6(4) . . . . ?
C4 N1 C7 N2 -178.7(2) . . . . ?
C4 C3 C2 C1 -0.5(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C7 N1 C4 C3 23.4(4) . . . . ?
C7 N1 C4 C5 -160.1(2) . . . . ?
C7 N2 C8 C9 87.3(3) . . . . ?
C9 C10 C11 N3 1.3(4) . . . . ?
C9 C13 C12 N3 1.0(4) . . . . ?
C10 C9 C13 C12 -0.3(4) . . . . ?
C10 C9 C8 N2 -171.8(2) . . . . ?
C13 C9 C10 C11 -0.9(4) . . . . ?
C13 C9 C8 N2 9.0(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C3 C2 C1 C6 -0.7(4) . . . . ?
C8 N2 C7 S1 1.1(3) . . . . ?
C8 N2 C7 N1 -178.6(2) . . . . ?
C8 C9 C10 C11 179.9(2) . . . . ?
C8 C9 C13 C12 179.0(2) . . . . ?
C11 N3 C12 C13 -0.6(4) . . . . ?
C5 C4 C3 C2 1.2(4) . . . . ?
C5 C6 C1 C2 1.3(4) . . . . ?
C12 N3 C11 C10 -0.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_HnaphureaClO4H2O
_database_code_depnum_ccdc_archive 'CCDC 2171846'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 N3 O, Cl O4, H2 O'
_chemical_formula_sum            'C17 H18 Cl N3 O6'
_chemical_formula_weight         395.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.886(3)
_cell_length_b                   8.2613(18)
_cell_length_c                   20.140(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.990(6)
_cell_angle_gamma                90
_cell_volume                     1789.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9517
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.53
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1709 before and 0.1056 after correction.
The Ratio of minimum to maximum transmission is 0.8118.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.6051
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25145
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         2.563
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2554
_reflns_number_total             3124
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0877P)²+2.1745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Cl1-O5 \\sim Cl1-O5A
 with sigma of 0.02
 Cl1-O4 \\sim Cl1-O4A
 with sigma of 0.02
 Cl1-O2 \\sim Cl1-O2A
 with sigma of 0.02
 Cl1-O3 \\sim Cl1-O3A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O3A) = Uanis(O3)
Uanis(O5A) = Uanis(O5)
Uanis(O2) = Uanis(O2A)
Uanis(O4A) = Uanis(O4)
4. Others
 Sof(O3A)=Sof(O5A)=Sof(O2A)=Sof(O4A)=1-FVAR(1)
 Sof(O5)=Sof(O4)=Sof(O2)=Sof(O3)=FVAR(1)
5.a Free rotating group:
 O6(H6A,H6B)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C2(H2A), C3(H3A), C7(H7), C10(H10), C17(H17),
 C14(H14), C15(H15), C9(H9), C8(H8), C4(H4), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.20702(8) 0.38292(11) 0.12674(4) 0.0571(3) Uani 1 1 d . . . A 2
O1 O 0.60517(18) 0.2972(2) 0.27046(10) 0.0440(5) Uani 1 1 d . . . . .
N1 N 0.4642(2) 0.4807(3) 0.29953(12) 0.0430(6) Uani 1 1 d . . . . .
H1 H 0.421666 0.564915 0.285188 0.052 Uiso 1 1 calc R U . . .
N2 N 0.5403(3) 0.5071(3) 0.20152(13) 0.0480(7) Uani 1 1 d . . . . .
H2 H 0.500106 0.597070 0.197359 0.058 Uiso 1 1 calc R U . . .
N3 N 0.9436(3) 0.7001(4) 0.13971(16) 0.0603(8) Uani 1 1 d . . . . .
H3 H 1.012844 0.748820 0.137979 0.072 Uiso 1 1 calc R U . . .
C13 C 0.7252(3) 0.5437(3) 0.14580(15) 0.0418(7) Uani 1 1 d . . . . .
O6 O 0.1536(3) 0.8842(4) 0.15662(19) 0.0846(9) Uani 1 1 d G . . . .
H6A H 0.223783 0.859938 0.179294 0.127 Uiso 1 1 d G U . . .
H6B H 0.159508 0.984432 0.147977 0.127 Uiso 1 1 d G U . . .
C5 C 0.3177(3) 0.4263(4) 0.45295(15) 0.0436(7) Uani 1 1 d . . . . .
C6 C 0.3350(3) 0.4752(3) 0.38730(14) 0.0374(6) Uani 1 1 d . . . . .
C11 C 0.5403(2) 0.4205(3) 0.25781(14) 0.0370(6) Uani 1 1 d . . . . .
C1 C 0.4461(3) 0.4228(3) 0.36319(14) 0.0371(6) Uani 1 1 d . . . . .
C12 C 0.6043(3) 0.4564(4) 0.14770(16) 0.0468(7) Uani 1 1 d . . . . .
H12A H 0.550134 0.473608 0.105273 0.056 Uiso 1 1 calc R U . . .
H12B H 0.620931 0.341263 0.152111 0.056 Uiso 1 1 calc R U . . .
C2 C 0.5304(3) 0.3277(4) 0.40246(15) 0.0447(7) Uani 1 1 d . . . . .
H2A H 0.602870 0.296148 0.386983 0.054 Uiso 1 1 calc R U . . .
C3 C 0.5084(3) 0.2770(4) 0.46623(16) 0.0516(8) Uani 1 1 d . . . . .
H3A H 0.565581 0.209346 0.491764 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2418(3) 0.5710(4) 0.34911(16) 0.0450(7) Uani 1 1 d . . . . .
H7 H 0.249274 0.599035 0.305199 0.054 Uiso 1 1 calc R U . . .
C10 C 0.2109(3) 0.4833(4) 0.47846(18) 0.0562(9) Uani 1 1 d . . . . .
H10 H 0.199305 0.453974 0.521634 0.067 Uiso 1 1 calc R U . . .
C17 C 0.7843(3) 0.5310(4) 0.08939(17) 0.0523(8) Uani 1 1 d . . . . .
H17 H 0.749346 0.468040 0.053020 0.063 Uiso 1 1 calc R U . . .
C14 C 0.7812(3) 0.6384(4) 0.19849(16) 0.0512(8) Uani 1 1 d . . . . .
H14 H 0.744407 0.649379 0.236922 0.061 Uiso 1 1 calc R U . . .
C15 C 0.8905(3) 0.7161(5) 0.19436(18) 0.0588(9) Uani 1 1 d . . . . .
H15 H 0.927704 0.780166 0.229846 0.071 Uiso 1 1 calc R U . . .
C9 C 0.1257(3) 0.5795(5) 0.4412(2) 0.0612(9) Uani 1 1 d . . . . .
H9 H 0.057153 0.616491 0.459095 0.073 Uiso 1 1 calc R U . . .
C8 C 0.1405(3) 0.6230(4) 0.37601(19) 0.0548(8) Uani 1 1 d . . . . .
H8 H 0.081166 0.687920 0.350552 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4055(3) 0.3248(4) 0.49130(16) 0.0535(8) Uani 1 1 d . . . . .
H4 H 0.392953 0.290571 0.533723 0.064 Uiso 1 1 calc R U . . .
O5 O 0.1829(6) 0.4714(6) 0.1831(2) 0.1099(19) Uani 0.835(5) 1 d . . P B 1
C16 C 0.8930(3) 0.6109(5) 0.08756(19) 0.0603(9) Uani 1 1 d . . . . .
H16 H 0.932011 0.603015 0.049773 0.072 Uiso 1 1 calc R U . . .
O4 O 0.1028(4) 0.3563(8) 0.0778(3) 0.133(2) Uani 0.835(5) 1 d . . P B 1
O2 O 0.2694(8) 0.2349(6) 0.1450(3) 0.135(3) Uani 0.835(5) 1 d . . P B 1
O3 O 0.2841(5) 0.4779(6) 0.0899(3) 0.1219(18) Uani 0.835(5) 1 d . . P B 1
O3A O 0.281(3) 0.505(4) 0.1388(17) 0.1219(18) Uani 0.165(5) 1 d . . P A 2
O5A O 0.116(3) 0.400(3) 0.1720(12) 0.1099(19) Uani 0.165(5) 1 d . . P A 2
O2A O 0.316(5) 0.309(3) 0.1416(16) 0.135(3) Uani 0.165(5) 1 d . . P A 2
O4A O 0.173(2) 0.451(4) 0.0665(14) 0.133(2) Uani 0.165(5) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 O3A 1.29(3) . ?
Cl1 O5A 1.45(3) . ?
Cl1 O2A 1.33(4) . ?
Cl1 O4A 1.34(3) . ?
O1 C11 1.243(3) . ?
N1 H1 0.8600 . ?
N1 C11 1.363(4) . ?
N1 C1 1.411(4) . ?
N2 H2 0.8600 . ?
N2 C11 1.340(4) . ?
N2 C12 1.440(4) . ?
N3 H3 0.8600 . ?
N3 C15 1.328(5) . ?
N3 C16 1.330(5) . ?
C13 C12 1.505(4) . ?
C13 C17 1.394(4) . ?
C13 C14 1.382(4) . ?
O6 H6A 0.8507 . ?
O6 H6B 0.8503 . ?
C5 C6 1.423(4) . ?
C5 C10 1.423(5) . ?
C5 C4 1.407(5) . ?
C6 C1 1.438(4) . ?
C6 C7 1.416(4) . ?
C1 C2 1.363(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C2 H2A 0.9300 . ?
C2 C3 1.406(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.358(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.356(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.361(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.365(5) . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.394(5) . ?
C8 H8 0.9300 . ?
C4 H4 0.9300 . ?
C16 H16 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
O3A Cl1 O5A 105.8(17) . . ?
O3A Cl1 O2A 79(2) . . ?
O3A Cl1 O4A 85.3(18) . . ?
O2A Cl1 O5A 125.2(17) . . ?
O2A Cl1 O4A 120.8(18) . . ?
O4A Cl1 O5A 114.0(16) . . ?
C11 N1 H1 115.8 . . ?
C11 N1 C1 128.4(2) . . ?
C1 N1 H1 115.8 . . ?
C11 N2 H2 118.5 . . ?
C11 N2 C12 123.1(3) . . ?
C12 N2 H2 118.5 . . ?
C15 N3 H3 119.0 . . ?
C15 N3 C16 122.0(3) . . ?
C16 N3 H3 119.0 . . ?
C17 C13 C12 120.1(3) . . ?
C14 C13 C12 122.3(3) . . ?
C14 C13 C17 117.6(3) . . ?
H6A O6 H6B 104.4 . . ?
C10 C5 C6 118.4(3) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 C10 121.5(3) . . ?
C5 C6 C1 118.0(3) . . ?
C7 C6 C5 118.4(3) . . ?
C7 C6 C1 123.6(3) . . ?
O1 C11 N1 123.6(3) . . ?
O1 C11 N2 122.4(3) . . ?
N2 C11 N1 114.0(2) . . ?
N1 C1 C6 116.7(2) . . ?
C2 C1 N1 123.1(3) . . ?
C2 C1 C6 120.2(3) . . ?
N2 C12 C13 114.1(3) . . ?
N2 C12 H12A 108.7 . . ?
N2 C12 H12B 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C1 C2 H2A 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2A 119.8 . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3A 119.3 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?
C5 C10 H10 119.3 . . ?
C9 C10 C5 121.4(3) . . ?
C9 C10 H10 119.3 . . ?
C13 C17 H17 120.0 . . ?
C16 C17 C13 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
N3 C15 C14 120.0(3) . . ?
N3 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.1 . . ?
N3 C16 C17 120.1(3) . . ?
N3 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?

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
N1 C1 C2 C3 178.4(3) . . . . ?
C13 C17 C16 N3 0.5(5) . . . . ?
C13 C14 C15 N3 -0.3(5) . . . . ?
C5 C6 C1 N1 -176.5(2) . . . . ?
C5 C6 C1 C2 0.8(4) . . . . ?
C5 C6 C7 C8 3.5(4) . . . . ?
C5 C10 C9 C8 0.9(5) . . . . ?
C6 C5 C10 C9 1.2(5) . . . . ?
C6 C5 C4 C3 1.7(5) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
C6 C7 C8 C9 -1.5(5) . . . . ?
C11 N1 C1 C6 -161.3(3) . . . . ?
C11 N1 C1 C2 21.5(5) . . . . ?
C11 N2 C12 C13 -102.8(3) . . . . ?
C1 N1 C11 O1 2.0(5) . . . . ?
C1 N1 C11 N2 -177.5(3) . . . . ?
C1 C6 C7 C8 -177.1(3) . . . . ?
C1 C2 C3 C4 -2.0(5) . . . . ?
C12 N2 C11 O1 6.8(4) . . . . ?
C12 N2 C11 N1 -173.7(3) . . . . ?
C12 C13 C17 C16 179.6(3) . . . . ?
C12 C13 C14 C15 -179.6(3) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C7 C6 C1 N1 4.2(4) . . . . ?
C7 C6 C1 C2 -178.6(3) . . . . ?
C10 C5 C6 C1 177.2(3) . . . . ?
C10 C5 C6 C7 -3.4(4) . . . . ?
C10 C5 C4 C3 -177.8(3) . . . . ?
C10 C9 C8 C7 -0.8(5) . . . . ?
C17 C13 C12 N2 -167.2(3) . . . . ?
C17 C13 C14 C15 0.1(5) . . . . ?
C14 C13 C12 N2 12.6(4) . . . . ?
C14 C13 C17 C16 -0.2(5) . . . . ?
C15 N3 C16 C17 -0.7(5) . . . . ?
C4 C5 C6 C1 -2.3(4) . . . . ?
C4 C5 C6 C7 177.1(3) . . . . ?
C4 C5 C10 C9 -179.2(3) . . . . ?
C16 N3 C15 C14 0.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_naphureaH2O
_database_code_depnum_ccdc_archive 'CCDC 2171849'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N3 O, H2 O'
_chemical_formula_sum            'C17 H17 N3 O2'
_chemical_formula_weight         295.33

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   43.205(6)
_cell_length_b                   7.7050(11)
_cell_length_c                   4.5617(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1518.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      24.65

_exptl_crystal_description       Rod
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   0.4828
_exptl_transmission_factor_max   0.7451
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1709 before and 0.1056 after correction.
The Ratio of minimum to maximum transmission is 0.8118.
The λ/2 correction factor is Not present.
;
_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            34761
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         1.885
_diffrn_reflns_theta_max         24.684
_diffrn_reflns_theta_full        24.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2570
_reflns_number_gt                1986
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.990

_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-2019/1 (Sheldrick, 2019)'
_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)+(0.1000P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_abs_structure_details 
;
 Flack x determined using 621 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2570
_refine_ls_number_parameters     215
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.2288
_refine_ls_wR_factor_gt          0.2066
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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
O1 O 0.36874(12) 0.3853(8) 0.6943(11) 0.0536(17) Uani 1 1 d . . . . .
O2 O 0.26777(18) 0.4751(9) 0.9528(16) 0.0613(18) Uani 1 1 d . . . . .
N1 N 0.39320(16) 0.4427(9) 0.2683(16) 0.0431(17) Uani 1 1 d . . . . .
N2 N 0.34609(15) 0.3102(9) 0.2726(16) 0.0438(17) Uani 1 1 d . . . . .
C11 C 0.36941(18) 0.3785(9) 0.4245(16) 0.0355(18) Uani 1 1 d . . . . .
C6 C 0.42612(16) 0.6982(9) 0.3096(15) 0.0361(18) Uani 1 1 d . . . . .
C1 C 0.41929(16) 0.5242(9) 0.3916(16) 0.0363(18) Uani 1 1 d . . . . .
N3 N 0.30642(19) -0.2358(10) 0.796(2) 0.070(2) Uani 1 1 d . . . . .
C5 C 0.45280(17) 0.7780(10) 0.4296(16) 0.0398(19) Uani 1 1 d . . . . .
C13 C 0.31460(16) 0.0930(10) 0.5471(17) 0.0399(18) Uani 1 1 d . . . . .
C2 C 0.43777(18) 0.4392(10) 0.5858(18) 0.0449(19) Uani 1 1 d . . . . .
H2 H 0.433048 0.325215 0.635996 0.054 Uiso 1 1 calc R U . . .
C3 C 0.46359(18) 0.5183(11) 0.712(2) 0.051(2) Uani 1 1 d . . . . .
H3 H 0.475737 0.458806 0.846677 0.061 Uiso 1 1 calc R U . . .
C12 C 0.31681(17) 0.2700(10) 0.4140(17) 0.046(2) Uani 1 1 d . . . . .
H12A H 0.300398 0.282162 0.270323 0.056 Uiso 1 1 calc R U . . .
H12B H 0.313148 0.355239 0.566553 0.056 Uiso 1 1 calc R U . . .
C4 C 0.47064(17) 0.6828(12) 0.6338(18) 0.053(2) Uani 1 1 d . . . . .
H4 H 0.487881 0.735331 0.717626 0.064 Uiso 1 1 calc R U . . .
C7 C 0.40769(19) 0.7959(10) 0.1176(17) 0.050(2) Uani 1 1 d . . . . .
H7 H 0.390006 0.746086 0.037404 0.060 Uiso 1 1 calc R U . . .
C10 C 0.4598(2) 0.9492(11) 0.351(2) 0.057(2) Uani 1 1 d . . . . .
H10 H 0.477244 1.002388 0.429952 0.068 Uiso 1 1 calc R U . . .
C17 C 0.28925(19) 0.0552(11) 0.723(2) 0.057(2) Uani 1 1 d . . . . .
H17 H 0.274347 0.139250 0.761513 0.069 Uiso 1 1 calc R U . . .
C14 C 0.3358(2) -0.0361(12) 0.510(2) 0.059(2) Uani 1 1 d . . . . .
H14 H 0.353572 -0.016422 0.399493 0.071 Uiso 1 1 calc R U . . .
C8 C 0.4152(2) 0.9637(11) 0.046(2) 0.062(2) Uani 1 1 d . . . . .
H8 H 0.402777 1.027313 -0.081010 0.074 Uiso 1 1 calc R U . . .
C15 C 0.3308(2) -0.1971(12) 0.638(3) 0.069(3) Uani 1 1 d . . . . .
H15 H 0.345667 -0.282856 0.610271 0.083 Uiso 1 1 calc R U . . .
C9 C 0.4418(3) 1.0374(12) 0.166(2) 0.073(3) Uani 1 1 d . . . . .
H9 H 0.447158 1.150514 0.115605 0.087 Uiso 1 1 calc R U . . .
C16 C 0.2866(2) -0.1079(13) 0.839(3) 0.071(3) Uani 1 1 d . . . . .
H16 H 0.269508 -0.130397 0.957535 0.085 Uiso 1 1 calc R U . . .
H1A H 0.3922(19) 0.440(11) 0.10(2) 0.05(3) Uiso 1 1 d . . . . .
H2A H 0.3467(18) 0.312(10) 0.08(2) 0.05(2) Uiso 1 1 d . . . . .
H2C H 0.258(2) 0.484(12) 0.80(3) 0.08(4) Uiso 1 1 d . . . . .
H2D H 0.281(2) 0.552(13) 0.90(2) 0.07(3) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.232(8) . ?
N1 C11 1.345(10) . ?
N1 C1 1.408(10) . ?
N2 C11 1.331(10) . ?
N2 C12 1.453(10) . ?
C6 C7 1.403(10) . ?
C6 C5 1.417(10) . ?
C6 C1 1.422(10) . ?
C1 C2 1.361(10) . ?
N3 C15 1.312(12) . ?
N3 C16 1.320(12) . ?
C5 C10 1.399(11) . ?
C5 C4 1.414(11) . ?
C13 C14 1.364(11) . ?
C13 C17 1.389(11) . ?
C13 C12 1.496(11) . ?
C2 C3 1.395(11) . ?
C3 C4 1.351(12) . ?
C7 C8 1.373(12) . ?
C10 C9 1.334(13) . ?
C17 C16 1.369(13) . ?
C14 C15 1.389(13) . ?
C8 C9 1.393(14) . ?

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
C11 N1 C1 124.4(7) . . ?
C11 N2 C12 120.8(7) . . ?
O1 C11 N2 121.3(7) . . ?
O1 C11 N1 122.1(7) . . ?
N2 C11 N1 116.6(7) . . ?
C7 C6 C5 118.0(7) . . ?
C7 C6 C1 123.5(7) . . ?
C5 C6 C1 118.5(7) . . ?
C2 C1 N1 121.0(7) . . ?
C2 C1 C6 120.2(7) . . ?
N1 C1 C6 118.8(7) . . ?
C15 N3 C16 115.7(8) . . ?
C10 C5 C4 122.7(7) . . ?
C10 C5 C6 119.1(8) . . ?
C4 C5 C6 118.2(7) . . ?
C14 C13 C17 116.7(8) . . ?
C14 C13 C12 124.9(7) . . ?
C17 C13 C12 118.4(7) . . ?
C1 C2 C3 121.8(7) . . ?
C4 C3 C2 118.8(8) . . ?
N2 C12 C13 115.5(6) . . ?
C3 C4 C5 122.5(7) . . ?
C8 C7 C6 121.3(8) . . ?
C9 C10 C5 121.1(8) . . ?
C16 C17 C13 118.9(8) . . ?
C13 C14 C15 119.6(8) . . ?
C7 C8 C9 119.1(9) . . ?
N3 C15 C14 124.1(9) . . ?
C10 C9 C8 121.4(8) . . ?
N3 C16 C17 125.0(9) . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_HnaphureaNO3
_database_code_depnum_ccdc_archive 'CCDC 2171847'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 N3 O, N O3'
_chemical_formula_sum            'C17 H16 N4 O4'
_chemical_formula_weight         340.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.1546(10)
_cell_length_b                   13.0529(9)
_cell_length_c                   16.4184(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3247.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9828
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1709 before and 0.1056 after correction.
The Ratio of minimum to maximum transmission is 0.8118.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   0.7419
_exptl_transmission_factor_min   0.6816
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            44922
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        23.490
_diffrn_reflns_theta_max         23.490
_diffrn_reflns_theta_min         2.404
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1862
_reflns_number_total             2397
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.258
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0669
_refine_ls_restrained_S_all      1.258
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0160P)²+4.5494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1314
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C14(H14), C7(H7), C15(H15), C4(H4), C2(H2A), C10(H10),
 C3(H3A), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62369(15) 0.88828(19) 0.33358(15) 0.0483(7) Uani 1 1 d . . . . .
O2 O 0.64820(17) 0.6066(2) 0.51824(15) 0.0577(7) Uani 1 1 d . . . . .
N2 N 0.72303(18) 0.8202(2) 0.42022(17) 0.0406(7) Uani 1 1 d . . . . .
N4 N 0.7208(2) 0.6090(2) 0.55468(18) 0.0471(8) Uani 1 1 d . . . . .
N3 N 0.98266(18) 0.9211(2) 0.25956(19) 0.0421(7) Uani 1 1 d . . . . .
N1 N 0.60924(19) 0.7222(2) 0.3747(2) 0.0476(8) Uani 1 1 d . . . . .
O3 O 0.78397(18) 0.6557(2) 0.52494(18) 0.0730(9) Uani 1 1 d . . . . .
O4 O 0.72776(19) 0.5632(3) 0.61934(17) 0.0852(10) Uani 1 1 d . . . . .
C11 C 0.6499(2) 0.8146(3) 0.3736(2) 0.0371(8) Uani 1 1 d . . . . .
C13 C 0.8475(2) 0.9215(2) 0.3693(2) 0.0351(8) Uani 1 1 d . . . . .
C17 C 0.8311(2) 0.9207(3) 0.2860(2) 0.0419(9) Uani 1 1 d . . . . .
H17 H 0.773310 0.920420 0.266976 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5335(2) 0.6813(2) 0.2464(2) 0.0364(8) Uani 1 1 d . . . . .
C16 C 0.8998(2) 0.9203(3) 0.2321(2) 0.0439(9) Uani 1 1 d . . . . .
H16 H 0.888809 0.919528 0.176397 0.053 Uiso 1 1 calc R U . . .
C1 C 0.5297(2) 0.7010(2) 0.3310(2) 0.0403(9) Uani 1 1 d . . . . .
C12 C 0.7727(2) 0.9145(3) 0.4293(2) 0.0421(9) Uani 1 1 d . . . . .
H12A H 0.796117 0.918298 0.484198 0.051 Uiso 1 1 calc R U . . .
H12B H 0.733388 0.972377 0.421542 0.051 Uiso 1 1 calc R U . . .
C14 C 0.9344(2) 0.9253(3) 0.3947(2) 0.0429(9) Uani 1 1 d . . . . .
H14 H 0.947547 0.928504 0.449987 0.051 Uiso 1 1 calc R U . . .
C5 C 0.4544(2) 0.6546(3) 0.2050(2) 0.0421(9) Uani 1 1 d . . . . .
C7 C 0.6126(2) 0.6858(3) 0.2005(2) 0.0469(9) Uani 1 1 d . . . . .
H7 H 0.665183 0.703305 0.226136 0.056 Uiso 1 1 calc R U . . .
C15 C 1.0012(2) 0.9245(3) 0.3383(2) 0.0467(10) Uani 1 1 d . . . . .
H15 H 1.059721 0.926279 0.355446 0.056 Uiso 1 1 calc R U . . .
C4 C 0.3753(2) 0.6476(3) 0.2499(3) 0.0559(11) Uani 1 1 d . . . . .
H4 H 0.323238 0.630094 0.223265 0.067 Uiso 1 1 calc R U . . .
C2 C 0.4513(2) 0.6934(3) 0.3719(2) 0.0530(10) Uani 1 1 d . . . . .
H2A H 0.449464 0.706673 0.427532 0.064 Uiso 1 1 calc R U . . .
C10 C 0.4576(3) 0.6341(3) 0.1207(2) 0.0578(11) Uani 1 1 d . . . . .
H10 H 0.405997 0.616940 0.093237 0.069 Uiso 1 1 calc R U . . .
C3 C 0.3738(2) 0.6658(3) 0.3309(3) 0.0630(12) Uani 1 1 d . . . . .
H3A H 0.321144 0.659942 0.359539 0.076 Uiso 1 1 calc R U . . .
C8 C 0.6126(3) 0.6650(3) 0.1195(2) 0.0613(11) Uani 1 1 d . . . . .
H8 H 0.665185 0.668124 0.090442 0.074 Uiso 1 1 calc R U . . .
C9 C 0.5347(3) 0.6390(3) 0.0794(2) 0.0655(12) Uani 1 1 d . . . . .
H9 H 0.535750 0.624959 0.023867 0.079 Uiso 1 1 calc R U . . .
H1 H 0.621(2) 0.681(3) 0.414(2) 0.057(12) Uiso 1 1 d . . . . .
H2 H 0.741(2) 0.766(3) 0.4456(19) 0.040(10) Uiso 1 1 d . . . . .
H3 H 1.034(3) 0.912(3) 0.218(3) 0.095(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.231(4) . ?
O2 N4 1.252(4) . ?
N2 C11 1.348(4) . ?
N2 C12 1.450(4) . ?
N2 H2 0.86(3) . ?
N4 O3 1.236(4) . ?
N4 O4 1.223(4) . ?
N3 C16 1.334(4) . ?
N3 C15 1.324(4) . ?
N3 H3 1.03(4) . ?
N1 C11 1.355(4) . ?
N1 C1 1.430(4) . ?
N1 H1 0.87(4) . ?
C13 C17 1.390(4) . ?
C13 C12 1.505(4) . ?
C13 C14 1.382(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.367(4) . ?
C6 C1 1.414(5) . ?
C6 C5 1.421(4) . ?
C6 C7 1.417(5) . ?
C16 H16 0.9300 . ?
C1 C2 1.368(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C15 1.373(5) . ?
C5 C4 1.410(5) . ?
C5 C10 1.410(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.356(5) . ?
C15 H15 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.351(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.401(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.353(5) . ?
C3 H3A 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.394(5) . ?
C9 H9 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
C11 N2 C12 122.1(3) . . ?
C11 N2 H2 119(2) . . ?
C12 N2 H2 119(2) . . ?
O3 N4 O2 120.2(3) . . ?
O4 N4 O2 118.6(3) . . ?
O4 N4 O3 121.1(3) . . ?
C16 N3 H3 119(2) . . ?
C15 N3 C16 122.0(3) . . ?
C15 N3 H3 119(2) . . ?
C11 N1 C1 123.4(3) . . ?
C11 N1 H1 118(2) . . ?
C1 N1 H1 116(2) . . ?
O1 C11 N2 121.8(3) . . ?
O1 C11 N1 123.7(3) . . ?
N2 C11 N1 114.5(3) . . ?
C17 C13 C12 120.6(3) . . ?
C14 C13 C17 117.9(3) . . ?
C14 C13 C12 121.5(3) . . ?
C13 C17 H17 120.0 . . ?
C16 C17 C13 120.1(3) . . ?
C16 C17 H17 120.0 . . ?
C1 C6 C5 118.7(3) . . ?
C1 C6 C7 123.4(3) . . ?
C7 C6 C5 118.0(3) . . ?
N3 C16 C17 119.9(3) . . ?
N3 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C6 C1 N1 119.5(3) . . ?
C2 C1 N1 120.0(3) . . ?
C2 C1 C6 120.3(3) . . ?
N2 C12 C13 112.0(3) . . ?
N2 C12 H12A 109.2 . . ?
N2 C12 H12B 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C4 C5 C6 118.9(3) . . ?
C10 C5 C6 119.1(3) . . ?
C10 C5 C4 121.9(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?
N3 C15 C14 120.1(3) . . ?
N3 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4 119.5 . . ?
C1 C2 H2A 119.7 . . ?
C1 C2 C3 120.7(4) . . ?
C3 C2 H2A 119.7 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.8(4) . . ?
C9 C10 H10 119.6 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(4) . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?

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
N1 C1 C2 C3 -175.7(3) . . . . ?
C11 N2 C12 C13 -93.8(4) . . . . ?
C11 N1 C1 C6 78.8(4) . . . . ?
C11 N1 C1 C2 -105.3(4) . . . . ?
C13 C17 C16 N3 -0.2(5) . . . . ?
C13 C14 C15 N3 0.7(5) . . . . ?
C17 C13 C12 N2 60.6(4) . . . . ?
C17 C13 C14 C15 -2.3(5) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
C6 C5 C4 C3 0.1(6) . . . . ?
C6 C5 C10 C9 0.3(6) . . . . ?
C6 C7 C8 C9 0.3(6) . . . . ?
C16 N3 C15 C14 1.2(5) . . . . ?
C1 N1 C11 O1 -1.8(5) . . . . ?
C1 N1 C11 N2 178.5(3) . . . . ?
C1 C6 C5 C4 -0.8(5) . . . . ?
C1 C6 C5 C10 -179.5(3) . . . . ?
C1 C6 C7 C8 179.2(3) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C12 N2 C11 O1 3.1(5) . . . . ?
C12 N2 C11 N1 -177.1(3) . . . . ?
C12 C13 C17 C16 -175.7(3) . . . . ?
C12 C13 C14 C15 175.5(3) . . . . ?
C14 C13 C17 C16 2.1(5) . . . . ?
C14 C13 C12 N2 -117.1(3) . . . . ?
C5 C6 C1 N1 176.5(3) . . . . ?
C5 C6 C1 C2 0.7(5) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C5 C4 C3 C2 0.8(6) . . . . ?
C5 C10 C9 C8 -0.3(6) . . . . ?
C7 C6 C1 N1 -3.0(5) . . . . ?
C7 C6 C1 C2 -178.8(3) . . . . ?
C7 C6 C5 C4 178.7(3) . . . . ?
C7 C6 C5 C10 0.0(5) . . . . ?
C7 C8 C9 C10 0.0(7) . . . . ?
C15 N3 C16 C17 -1.5(5) . . . . ?
C4 C5 C10 C9 -178.4(4) . . . . ?
C10 C5 C4 C3 178.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_HnaphthioureaClO4
_database_code_depnum_ccdc_archive 'CCDC 2171850'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 N3 S, Cl O4'
_chemical_formula_sum            'C17 H16 Cl N3 O4 S'
_chemical_formula_weight         393.84
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.241(2)
_cell_length_b                   17.685(5)
_cell_length_c                   25.201(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3672.9(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9203
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1709 before and 0.1056 after correction.
The Ratio of minimum to maximum transmission is 0.8118.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.6509
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            49810
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.303
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2744
_reflns_number_total             3225
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0640
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0683P)²+5.7964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1666
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 Cl1-O3 \\sim Cl1-O3A
 with sigma of 0.02
 Cl1-O4 \\sim Cl1-O4A
 with sigma of 0.02
 Cl1-O2 \\sim Cl1-O2A
 with sigma of 0.02
 Cl1-O1 \\sim Cl1-O1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O3) = Uanis(O3A)
Uanis(O1A) = Uanis(O1)
Uanis(O4) = Uanis(O4A)
Uanis(O2) = Uanis(O2A)
4. Others
 Sof(O3A)=Sof(O4A)=Sof(O2A)=Sof(O1A)=1-FVAR(1)
 Sof(O3)=Sof(O4)=Sof(O2)=Sof(O1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), N3(H3), C7(H7), C2(H2A), C17(H17), C14(H14), C15(H15), C4(H4),
  C16(H16), C10(H10), C3(H3A), C9(H9), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.65892(10) 0.55268(5) 0.26914(3) 0.0425(3) Uani 1 1 d . . . . .
Cl1 Cl 0.80492(13) 0.86824(6) 0.49510(4) 0.0580(3) Uani 1 1 d . . . A 2
N2 N 0.6675(3) 0.45799(15) 0.35067(11) 0.0427(7) Uani 1 1 d . . . . .
H2 H 0.622798 0.425028 0.371067 0.051 Uiso 1 1 calc R U . . .
N1 N 0.4231(3) 0.46968(15) 0.30781(11) 0.0434(7) Uani 1 1 d . . . . .
H1 H 0.372245 0.486265 0.280377 0.052 Uiso 1 1 calc R U . . .
N3 N 0.8986(4) 0.69776(19) 0.41988(13) 0.0627(9) Uani 1 1 d . . . . .
H3 H 0.910682 0.742962 0.431830 0.075 Uiso 1 1 calc R U . . .
C1 C 0.3310(4) 0.42426(18) 0.34378(13) 0.0395(7) Uani 1 1 d . . . . .
C11 C 0.5791(4) 0.48931(16) 0.31190(11) 0.0349(7) Uani 1 1 d . . . . .
C6 C 0.2683(4) 0.35443(18) 0.32588(13) 0.0403(8) Uani 1 1 d . . . . .
C13 C 0.8580(4) 0.55623(18) 0.38097(12) 0.0379(7) Uani 1 1 d . . . . .
C12 C 0.8358(4) 0.47783(19) 0.35937(14) 0.0447(8) Uani 1 1 d . . . . .
H12A H 0.893974 0.473656 0.326045 0.054 Uiso 1 1 calc R U . . .
H12B H 0.883192 0.441905 0.383983 0.054 Uiso 1 1 calc R U . . .
C7 C 0.3008(5) 0.3248(2) 0.27486(16) 0.0569(10) Uani 1 1 d . . . . .
H7 H 0.366825 0.351625 0.251607 0.068 Uiso 1 1 calc R U . . .
C5 C 0.1674(4) 0.3127(2) 0.36072(16) 0.0503(9) Uani 1 1 d . . . . .
C2 C 0.2980(4) 0.4507(2) 0.39356(14) 0.0509(9) Uani 1 1 d . . . . .
H2A H 0.340657 0.496721 0.404693 0.061 Uiso 1 1 calc R U . . .
C17 C 0.9879(5) 0.5994(2) 0.36579(15) 0.0603(11) Uani 1 1 d . . . . .
H17 H 1.063428 0.580235 0.341914 0.072 Uiso 1 1 calc R U . . .
C14 C 0.7506(5) 0.5861(2) 0.41739(13) 0.0498(9) Uani 1 1 d . . . . .
H14 H 0.663071 0.557454 0.429111 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7728(5) 0.6573(2) 0.43613(15) 0.0573(10) Uani 1 1 d . . . . .
H15 H 0.699787 0.677723 0.460357 0.069 Uiso 1 1 calc R U . . .
C4 C 0.1372(5) 0.3413(3) 0.41204(17) 0.0614(11) Uani 1 1 d . . . . .
H4 H 0.073089 0.313645 0.435371 0.074 Uiso 1 1 calc R U . . .
C16 C 1.0065(6) 0.6708(3) 0.38574(18) 0.0755(13) Uani 1 1 d . . . . .
H16 H 1.094458 0.700241 0.375422 0.091 Uiso 1 1 calc R U . . .
C10 C 0.1019(5) 0.2433(2) 0.3424(2) 0.0723(13) Uani 1 1 d . . . . .
H10 H 0.034108 0.215563 0.364565 0.087 Uiso 1 1 calc R U . . .
C3 C 0.1997(5) 0.4082(3) 0.42788(15) 0.0629(11) Uani 1 1 d . . . . .
H3A H 0.177356 0.426187 0.461772 0.076 Uiso 1 1 calc R U . . .
O3 O 0.8863(9) 0.8543(5) 0.4459(4) 0.111(3) Uani 0.790(4) 1 d . . P B 1
O4 O 0.6976(6) 0.8041(3) 0.50456(19) 0.0990(15) Uani 0.790(4) 1 d . . P B 1
C9 C 0.1354(6) 0.2170(2) 0.2940(3) 0.0861(16) Uani 1 1 d . . . . .
H9 H 0.091005 0.171251 0.283044 0.103 Uiso 1 1 calc R U . . .
C8 C 0.2367(6) 0.2575(3) 0.2594(2) 0.0786(14) Uani 1 1 d . . . . .
H8 H 0.260032 0.238275 0.225931 0.094 Uiso 1 1 calc R U . . .
O2 O 0.7004(10) 0.9322(3) 0.4898(2) 0.122(2) Uani 0.790(4) 1 d . . P B 1
O1 O 0.8948(7) 0.8737(3) 0.5409(2) 0.122(2) Uani 0.790(4) 1 d . . P B 1
O3A O 0.813(5) 0.849(2) 0.4428(18) 0.111(3) Uani 0.210(4) 1 d . . P A 2
O4A O 0.913(2) 0.8146(10) 0.5126(8) 0.0990(15) Uani 0.210(4) 1 d . . P A 2
O2A O 0.664(5) 0.8945(13) 0.5016(11) 0.122(2) Uani 0.210(4) 1 d . . P A 2
O1A O 0.917(3) 0.9395(13) 0.5003(8) 0.122(2) Uani 0.210(4) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C11 1.688(3) . ?
Cl1 O3A 1.37(4) . ?
Cl1 O4A 1.37(2) . ?
Cl1 O2A 1.26(3) . ?
Cl1 O1A 1.57(2) . ?
N2 H2 0.8600 . ?
N2 C11 1.338(4) . ?
N2 C12 1.448(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.429(4) . ?
N1 C11 1.336(4) . ?
N3 H3 0.8600 . ?
N3 C15 1.324(5) . ?
N3 C16 1.326(5) . ?
C1 C6 1.413(5) . ?
C1 C2 1.366(5) . ?
C6 C7 1.414(5) . ?
C6 C5 1.416(5) . ?
C13 C12 1.501(5) . ?
C13 C17 1.370(5) . ?
C13 C14 1.380(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.358(6) . ?
C5 C4 1.411(6) . ?
C5 C10 1.419(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.404(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.366(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.358(5) . ?
C15 H15 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.349(6) . ?
C16 H16 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.334(7) . ?
C3 H3A 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.404(7) . ?
C8 H8 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
O3A Cl1 O4A 96(2) . . ?
O3A Cl1 O1A 104.9(15) . . ?
O4A Cl1 O1A 98.5(10) . . ?
O2A Cl1 O3A 105(2) . . ?
O2A Cl1 O4A 144.0(14) . . ?
O2A Cl1 O1A 103.6(15) . . ?
C11 N2 H2 118.9 . . ?
C11 N2 C12 122.1(3) . . ?
C12 N2 H2 118.9 . . ?
C1 N1 H1 116.3 . . ?
C11 N1 H1 116.3 . . ?
C11 N1 C1 127.4(3) . . ?
C15 N3 H3 119.0 . . ?
C15 N3 C16 122.1(3) . . ?
C16 N3 H3 119.0 . . ?
C6 C1 N1 118.9(3) . . ?
C2 C1 N1 119.7(3) . . ?
C2 C1 C6 121.3(3) . . ?
N2 C11 S1 121.9(2) . . ?
N1 C11 S1 119.9(2) . . ?
N1 C11 N2 118.2(3) . . ?
C1 C6 C7 123.0(3) . . ?
C1 C6 C5 118.2(3) . . ?
C7 C6 C5 118.8(3) . . ?
C17 C13 C12 120.6(3) . . ?
C17 C13 C14 118.2(3) . . ?
C14 C13 C12 121.1(3) . . ?
N2 C12 C13 113.3(3) . . ?
N2 C12 H12A 108.9 . . ?
N2 C12 H12B 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C5 C10 118.2(4) . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 C10 122.8(4) . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.8(4) . . ?
C3 C2 H2A 120.1 . . ?
C13 C17 H17 120.0 . . ?
C16 C17 C13 120.0(4) . . ?
C16 C17 H17 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
N3 C15 C14 119.9(4) . . ?
N3 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 H4 119.4 . . ?
N3 C16 C17 119.7(4) . . ?
N3 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C5 C10 H10 119.3 . . ?
C9 C10 C5 121.4(4) . . ?
C9 C10 H10 119.3 . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3A 119.8 . . ?
C10 C9 H9 119.6 . . ?
C10 C9 C8 120.9(4) . . ?
C8 C9 H9 119.6 . . ?
C7 C8 C9 120.0(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?

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
N1 C1 C6 C7 4.2(5) . . . . ?
N1 C1 C6 C5 -175.4(3) . . . . ?
N1 C1 C2 C3 176.3(3) . . . . ?
C1 N1 C11 S1 -172.1(3) . . . . ?
C1 N1 C11 N2 7.3(5) . . . . ?
C1 C6 C7 C8 -179.6(4) . . . . ?
C1 C6 C5 C4 -1.6(5) . . . . ?
C1 C6 C5 C10 178.8(3) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C11 N2 C12 C13 70.4(4) . . . . ?
C11 N1 C1 C6 -116.5(4) . . . . ?
C11 N1 C1 C2 66.9(5) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C6 C7 C8 C9 0.8(7) . . . . ?
C6 C5 C4 C3 1.5(5) . . . . ?
C6 C5 C10 C9 0.9(6) . . . . ?
C13 C17 C16 N3 0.2(7) . . . . ?
C13 C14 C15 N3 -0.8(6) . . . . ?
C12 N2 C11 S1 1.7(4) . . . . ?
C12 N2 C11 N1 -177.7(3) . . . . ?
C12 C13 C17 C16 179.9(4) . . . . ?
C12 C13 C14 C15 -179.6(3) . . . . ?
C7 C6 C5 C4 178.8(3) . . . . ?
C7 C6 C5 C10 -0.8(5) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C5 C4 C3 C2 -0.6(6) . . . . ?
C5 C10 C9 C8 -0.2(7) . . . . ?
C2 C1 C6 C7 -179.4(3) . . . . ?
C2 C1 C6 C5 1.0(5) . . . . ?
C17 C13 C12 N2 -144.1(3) . . . . ?
C17 C13 C14 C15 1.8(5) . . . . ?
C14 C13 C12 N2 37.3(4) . . . . ?
C14 C13 C17 C16 -1.5(6) . . . . ?
C15 N3 C16 C17 0.9(7) . . . . ?
C4 C5 C10 C9 -178.6(4) . . . . ?
C16 N3 C15 C14 -0.6(6) . . . . ?
C10 C5 C4 C3 -179.0(4) . . . . ?
C10 C9 C8 C7 -0.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_HphenthioureaClO4
_database_code_depnum_ccdc_archive 'CCDC 2172477'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 N3 S, Cl O4'
_chemical_formula_sum            'C13 H14 Cl N3 O4 S'
_chemical_formula_weight         343.78

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'
Cl Cl 0.1484 0.1585 '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           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   18.620(3)
_cell_length_b                   5.4988(8)
_cell_length_c                   30.636(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.337(8)
_cell_angle_gamma                90
_cell_volume                     3117.6(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.59

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   0.7030
_exptl_transmission_factor_max   0.7453
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.400
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0913 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.9165.
The λ/2 correction factor is Not present.
;
_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            36194
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.338
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2750
_reflns_number_gt                2062
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0010P)²+30.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2750
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0810
_refine_ls_wR_factor_ref         0.1649
_refine_ls_wR_factor_gt          0.1397
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.20910(8) 1.3264(3) 0.81465(4) 0.0603(4) Uani 1 1 d . . . . .
N1 N 0.3142(2) 1.0432(8) 0.79297(13) 0.0513(11) Uani 1 1 d . . . . .
H1A H 0.299180 1.091267 0.766843 0.062 Uiso 1 1 d R U . . .
N2 N 0.2951(2) 1.0327(9) 0.86523(13) 0.0543(12) Uani 1 1 d . . . . .
H2A H 0.324826 0.912415 0.867925 0.065 Uiso 1 1 d R U . . .
N3 N 0.0697(3) 0.8472(11) 0.93631(17) 0.0755(15) Uani 1 1 d . . . . .
H3A H 0.029090 0.793061 0.943176 0.091 Uiso 1 1 d R U . . .
C1 C 0.4948(3) 0.5873(11) 0.8006(2) 0.0641(16) Uani 1 1 d . . . . .
H1 H 0.534901 0.485742 0.802008 0.077 Uiso 1 1 calc R U . . .
C2 C 0.4344(3) 0.5337(10) 0.7724(2) 0.0650(16) Uani 1 1 d . . . . .
H2 H 0.433655 0.397073 0.754477 0.078 Uiso 1 1 calc R U . . .
C3 C 0.3744(3) 0.6843(10) 0.77077(18) 0.0562(14) Uani 1 1 d . . . . .
H3 H 0.333314 0.648341 0.751789 0.067 Uiso 1 1 calc R U . . .
C4 C 0.3756(3) 0.8866(9) 0.79715(15) 0.0433(12) Uani 1 1 d . . . . .
C5 C 0.4368(3) 0.9416(10) 0.82490(17) 0.0524(13) Uani 1 1 d . . . . .
H5 H 0.438205 1.080281 0.842365 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4961(3) 0.7893(11) 0.82660(19) 0.0614(15) Uani 1 1 d . . . . .
H6 H 0.537218 0.824598 0.845602 0.074 Uiso 1 1 calc R U . . .
C7 C 0.2772(3) 1.1240(9) 0.82518(16) 0.0458(12) Uani 1 1 d . . . . .
C8 C 0.2676(3) 1.1238(11) 0.90436(15) 0.0546(14) Uani 1 1 d . . . . .
H8A H 0.262404 1.298802 0.901641 0.066 Uiso 1 1 calc R U . . .
H8B H 0.303351 1.092091 0.929223 0.066 Uiso 1 1 calc R U . . .
C9 C 0.1971(3) 1.0199(9) 0.91422(15) 0.0454(12) Uani 1 1 d . . . . .
C10 C 0.1647(3) 0.8225(10) 0.89265(17) 0.0581(14) Uani 1 1 d . . . . .
H10 H 0.186235 0.746867 0.870255 0.070 Uiso 1 1 calc R U . . .
C11 C 0.1002(4) 0.7384(12) 0.9046(2) 0.0721(17) Uani 1 1 d . . . . .
H11 H 0.077948 0.604520 0.890346 0.086 Uiso 1 1 calc R U . . .
C12 C 0.0996(3) 1.0367(14) 0.9578(2) 0.0771(19) Uani 1 1 d . . . . .
H12 H 0.076986 1.108666 0.980088 0.093 Uiso 1 1 calc R U . . .
C13 C 0.1631(3) 1.1255(11) 0.94734(17) 0.0588(15) Uani 1 1 d . . . . .
H13 H 0.184119 1.258607 0.962529 0.071 Uiso 1 1 calc R U . . .
Cl1 Cl 0.40561(8) 0.5824(3) 0.94533(5) 0.0645(4) Uani 1 1 d . . . . .
O1 O 0.3553(4) 0.5611(14) 0.9747(2) 0.180(4) Uani 1 1 d . . . . .
O2 O 0.4461(4) 0.7854(15) 0.9536(3) 0.196(4) Uani 1 1 d . . . . .
O3 O 0.3680(4) 0.5975(13) 0.9043(2) 0.169(3) Uani 1 1 d . . . . .
O4 O 0.4391(4) 0.3683(17) 0.9459(4) 0.240(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.691(5) . ?
N1 C7 1.340(6) . ?
N1 C4 1.427(6) . ?
N1 H1A 0.8597 . ?
N2 C7 1.334(6) . ?
N2 C8 1.444(6) . ?
N2 H2A 0.8600 . ?
N3 C11 1.321(7) . ?
N3 C12 1.323(8) . ?
N3 H3A 0.8599 . ?
C1 C6 1.365(8) . ?
C1 C2 1.372(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(7) . ?
C5 C6 1.382(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.493(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.375(7) . ?
C9 C13 1.382(7) . ?
C10 C11 1.375(8) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.350(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
Cl1 O4 1.332(7) . ?
Cl1 O2 1.355(7) . ?
Cl1 O1 1.372(6) . ?
Cl1 O3 1.373(6) . ?

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 N1 C4 127.3(4) . . ?
C7 N1 H1A 116.3 . . ?
C4 N1 H1A 116.4 . . ?
C7 N2 C8 123.9(4) . . ?
C7 N2 H2A 118.1 . . ?
C8 N2 H2A 118.0 . . ?
C11 N3 C12 122.0(6) . . ?
C11 N3 H3A 119.0 . . ?
C12 N3 H3A 119.0 . . ?
C6 C1 C2 120.2(5) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C2 C3 119.7(6) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 N1 118.4(5) . . ?
C5 C4 N1 121.5(5) . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 120.6(6) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N2 C7 N1 117.2(4) . . ?
N2 C7 S1 122.0(4) . . ?
N1 C7 S1 120.9(4) . . ?
N2 C8 C9 115.8(4) . . ?
N2 C8 H8A 108.3 . . ?
C9 C8 H8A 108.3 . . ?
N2 C8 H8B 108.3 . . ?
C9 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C13 118.2(5) . . ?
C10 C9 C8 123.6(5) . . ?
C13 C9 C8 118.2(5) . . ?
C11 C10 C9 119.2(5) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N3 C11 C10 120.2(6) . . ?
N3 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
N3 C12 C13 120.0(6) . . ?
N3 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C9 120.4(6) . . ?
C12 C13 H13 119.8 . . ?
C9 C13 H13 119.8 . . ?
O4 Cl1 O2 118.4(6) . . ?
O4 Cl1 O1 105.6(6) . . ?
O2 Cl1 O1 110.7(5) . . ?
O4 Cl1 O3 104.8(6) . . ?
O2 Cl1 O3 109.8(5) . . ?
O1 Cl1 O3 106.8(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.7(9) . . . . ?
C1 C2 C3 C4 0.2(8) . . . . ?
C2 C3 C4 C5 0.8(8) . . . . ?
C2 C3 C4 N1 177.0(5) . . . . ?
C7 N1 C4 C3 128.7(5) . . . . ?
C7 N1 C4 C5 -55.1(7) . . . . ?
C3 C4 C5 C6 -1.3(8) . . . . ?
N1 C4 C5 C6 -177.5(5) . . . . ?
C2 C1 C6 C5 0.1(8) . . . . ?
C4 C5 C6 C1 0.9(8) . . . . ?
C8 N2 C7 N1 171.2(5) . . . . ?
C8 N2 C7 S1 -10.7(7) . . . . ?
C4 N1 C7 N2 -6.5(8) . . . . ?
C4 N1 C7 S1 175.4(4) . . . . ?
C7 N2 C8 C9 86.2(7) . . . . ?
N2 C8 C9 C10 10.6(7) . . . . ?
N2 C8 C9 C13 -170.6(5) . . . . ?
C13 C9 C10 C11 0.2(8) . . . . ?
C8 C9 C10 C11 179.0(5) . . . . ?
C12 N3 C11 C10 -0.6(10) . . . . ?
C9 C10 C11 N3 0.3(9) . . . . ?
C11 N3 C12 C13 0.4(10) . . . . ?
N3 C12 C13 C9 0.1(10) . . . . ?
C10 C9 C13 C12 -0.4(8) . . . . ?
C8 C9 C13 C12 -179.3(5) . . . . ?

_refine_diff_density_max         0.706
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_Naphthiourea
_database_code_depnum_ccdc_archive 'CCDC 2173492'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N3 S'
_chemical_formula_sum            'C17 H15 N3 S'
_chemical_formula_weight         293.38

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'
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                   9.4256(6)
_cell_length_b                   9.7491(6)
_cell_length_c                   17.9657(12)
_cell_angle_alpha                85.658(2)
_cell_angle_beta                 85.018(2)
_cell_angle_gamma                69.168(2)
_cell_volume                     1535.35(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.22

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   0.7016
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0954 before and 0.0493 after correction.
The Ratio of minimum to maximum transmission is 0.9412.
The λ/2 correction factor is Not present.
;
_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            35054
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.238
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5374
_reflns_number_gt                4443
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²+0.9171P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         5374
_refine_ls_number_parameters     395
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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 0.54190(6) 0.19432(7) 0.51529(4) 0.05857(19) Uani 1 1 d . . . . .
S2 S 0.61144(8) 1.04931(7) 0.89420(4) 0.0668(2) Uani 1 1 d . . . . .
N2 N 0.2740(2) 0.36351(18) 0.57582(10) 0.0446(4) Uani 1 1 d D . . . .
N1 N 0.3188(2) 0.1171(2) 0.58101(12) 0.0544(5) Uani 1 1 d . . . . .
N5 N 0.5673(2) 0.8656(2) 0.80408(11) 0.0568(5) Uani 1 1 d . . . . .
N6 N 0.9793(3) 0.5295(2) 0.64390(14) 0.0701(6) Uani 1 1 d . . . . .
N4 N 0.4874(3) 0.8468(2) 0.92574(12) 0.0616(6) Uani 1 1 d . . . . .
C13 C 0.3487(3) 0.5614(2) 0.61829(12) 0.0464(5) Uani 1 1 d . . . . .
C11 C 0.3679(2) 0.2292(2) 0.55988(11) 0.0426(5) Uani 1 1 d . . . . .
C12 C 0.3024(3) 0.4984(2) 0.55443(12) 0.0478(5) Uani 1 1 d . . . . .
H12A H 0.211033 0.570585 0.535125 0.057 Uiso 1 1 calc R U . . .
H12B H 0.382178 0.479301 0.514535 0.057 Uiso 1 1 calc R U . . .
C6 C 0.1309(2) 0.1586(2) 0.68829(13) 0.0503(6) Uani 1 1 d . . . . .
N3 N 0.4431(3) 0.6822(3) 0.73217(13) 0.0771(7) Uani 1 1 d . . . . .
C18 C 0.4589(3) 0.7130(2) 0.91756(12) 0.0550(6) Uani 1 1 d . . . . .
C23 C 0.3081(3) 0.7166(2) 0.92243(12) 0.0519(6) Uani 1 1 d . . . . .
C28 C 0.5533(2) 0.9125(2) 0.87251(13) 0.0482(5) Uani 1 1 d . . . . .
C1 C 0.1683(2) 0.1339(2) 0.61152(13) 0.0484(5) Uani 1 1 d . . . . .
C30 C 0.7659(2) 0.7801(2) 0.70544(12) 0.0471(5) Uani 1 1 d . . . . .
C17 C 0.2597(3) 0.6954(2) 0.64550(14) 0.0619(6) Uani 1 1 d . . . . .
H17 H 0.166303 0.748140 0.626151 0.074 Uiso 1 1 calc R U . . .
C14 C 0.4845(3) 0.4889(3) 0.65021(14) 0.0626(7) Uani 1 1 d . . . . .
H14 H 0.547183 0.397091 0.634296 0.075 Uiso 1 1 calc R U . . .
C7 C 0.2346(3) 0.1696(3) 0.73814(15) 0.0644(7) Uani 1 1 d . . . . .
H7 H 0.332917 0.161363 0.720641 0.077 Uiso 1 1 calc R U . . .
C34 C 0.7674(3) 0.7512(3) 0.63237(14) 0.0674(7) Uani 1 1 d . . . . .
H34 H 0.696117 0.815607 0.601499 0.081 Uiso 1 1 calc R U . . .
C33 C 0.8750(3) 0.6261(3) 0.60453(16) 0.0748(8) Uani 1 1 d . . . . .
H33 H 0.873678 0.609016 0.554418 0.090 Uiso 1 1 calc R U . . .
C5 C -0.0188(3) 0.1718(3) 0.71669(17) 0.0670(7) Uani 1 1 d . . . . .
C19 C 0.5777(3) 0.5851(3) 0.90706(14) 0.0666(7) Uani 1 1 d . . . . .
H19 H 0.676946 0.584317 0.904467 0.080 Uiso 1 1 calc R U . . .
C29 C 0.6468(3) 0.9120(3) 0.74012(14) 0.0668(7) Uani 1 1 d . . . . .
H29A H 0.694824 0.977096 0.755791 0.080 Uiso 1 1 calc R U . . .
H29B H 0.574851 0.965542 0.703426 0.080 Uiso 1 1 calc R U . . .
C24 C 0.1811(3) 0.8477(3) 0.93234(14) 0.0633(7) Uani 1 1 d . . . . .
H24 H 0.196128 0.936350 0.935099 0.076 Uiso 1 1 calc R U . . .
C31 C 0.8754(3) 0.6811(3) 0.74691(14) 0.0709(7) Uani 1 1 d . . . . .
H31 H 0.880376 0.696067 0.796981 0.085 Uiso 1 1 calc R U . . .
C16 C 0.3117(4) 0.7504(3) 0.70216(16) 0.0753(8) Uani 1 1 d . . . . .
H16 H 0.250208 0.840875 0.720150 0.090 Uiso 1 1 calc R U . . .
C22 C 0.2811(3) 0.5838(3) 0.91665(14) 0.0632(7) Uani 1 1 d . . . . .
C2 C 0.0650(3) 0.1221(3) 0.56663(17) 0.0682(7) Uani 1 1 d . . . . .
H2A H 0.092729 0.104863 0.516311 0.082 Uiso 1 1 calc R U . . .
C15 C 0.5270(4) 0.5530(3) 0.70599(16) 0.0781(8) Uani 1 1 d . . . . .
H15 H 0.619968 0.502699 0.726350 0.094 Uiso 1 1 calc R U . . .
C20 C 0.5504(4) 0.4534(3) 0.90008(16) 0.0798(9) Uani 1 1 d . . . . .
H20 H 0.631735 0.366296 0.892177 0.096 Uiso 1 1 calc R U . . .
C32 C 0.9783(3) 0.5589(3) 0.71392(18) 0.0824(9) Uani 1 1 d . . . . .
H32 H 1.051807 0.493085 0.743234 0.099 Uiso 1 1 calc R U . . .
C3 C -0.0815(3) 0.1354(3) 0.5942(2) 0.0893(10) Uani 1 1 d . . . . .
H3 H -0.150899 0.127556 0.562561 0.107 Uiso 1 1 calc R U . . .
C21 C 0.4075(4) 0.4535(3) 0.90483(16) 0.0806(9) Uani 1 1 d . . . . .
H21 H 0.391234 0.365908 0.900249 0.097 Uiso 1 1 calc R U . . .
C4 C -0.1222(3) 0.1597(3) 0.6670(2) 0.0890(11) Uani 1 1 d . . . . .
H4 H -0.220477 0.168823 0.685134 0.107 Uiso 1 1 calc R U . . .
C27 C 0.1301(4) 0.5865(4) 0.92436(17) 0.0833(9) Uani 1 1 d . . . . .
H27 H 0.111577 0.499333 0.922151 0.100 Uiso 1 1 calc R U . . .
C26 C 0.0117(4) 0.7131(4) 0.93490(18) 0.0875(9) Uani 1 1 d . . . . .
H26 H -0.087128 0.712466 0.940203 0.105 Uiso 1 1 calc R U . . .
C25 C 0.0374(3) 0.8448(4) 0.93785(17) 0.0793(8) Uani 1 1 d . . . . .
H25 H -0.044851 0.931915 0.943667 0.095 Uiso 1 1 calc R U . . .
C8 C 0.1895(5) 0.1925(3) 0.81235(18) 0.0921(10) Uani 1 1 d . . . . .
H8 H 0.257545 0.199055 0.845210 0.111 Uiso 1 1 calc R U . . .
C10 C -0.0584(5) 0.1963(4) 0.7930(2) 0.1035(12) Uani 1 1 d . . . . .
H10 H -0.156179 0.205842 0.812055 0.124 Uiso 1 1 calc R U . . .
C9 C 0.0413(6) 0.2060(4) 0.8385(2) 0.1132(14) Uani 1 1 d . . . . .
H9 H 0.011743 0.222153 0.888772 0.136 Uiso 1 1 calc R U . . .
H1 H 0.369(3) 0.039(3) 0.5622(12) 0.050(7) Uiso 1 1 d . . . . .
H2 H 0.188(2) 0.376(2) 0.5989(11) 0.050(7) Uiso 1 1 d D . . . .
H4A H 0.467(3) 0.882(3) 0.9670(14) 0.054(7) Uiso 1 1 d . . . . .
H5 H 0.529(3) 0.807(3) 0.7960(13) 0.050(7) 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 C11 1.692(2) . ?
S2 C28 1.694(2) . ?
N2 C11 1.330(3) . ?
N2 C12 1.451(3) . ?
N2 H2 0.846(15) . ?
N1 C11 1.349(3) . ?
N1 C1 1.434(3) . ?
N1 H1 0.82(2) . ?
N5 C28 1.323(3) . ?
N5 C29 1.449(3) . ?
N5 H5 0.80(2) . ?
N6 C33 1.310(4) . ?
N6 C32 1.310(4) . ?
N4 C28 1.340(3) . ?
N4 C18 1.443(3) . ?
N4 H4A 0.82(2) . ?
C13 C14 1.374(3) . ?
C13 C17 1.377(3) . ?
C13 C12 1.506(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 C1 1.411(3) . ?
C6 C7 1.417(3) . ?
C6 C5 1.423(3) . ?
N3 C16 1.320(4) . ?
N3 C15 1.323(3) . ?
C18 C19 1.360(3) . ?
C18 C23 1.404(3) . ?
C23 C24 1.417(3) . ?
C23 C22 1.419(3) . ?
C1 C2 1.357(3) . ?
C30 C34 1.361(3) . ?
C30 C31 1.367(3) . ?
C30 C29 1.508(3) . ?
C17 C16 1.385(4) . ?
C17 H17 0.9300 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C7 C8 1.374(4) . ?
C7 H7 0.9300 . ?
C34 C33 1.375(3) . ?
C34 H34 0.9300 . ?
C33 H33 0.9300 . ?
C5 C10 1.404(5) . ?
C5 C4 1.418(4) . ?
C19 C20 1.413(4) . ?
C19 H19 0.9300 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C24 C25 1.359(4) . ?
C24 H24 0.9300 . ?
C31 C32 1.377(4) . ?
C31 H31 0.9300 . ?
C16 H16 0.9300 . ?
C22 C27 1.409(4) . ?
C22 C21 1.414(4) . ?
C2 C3 1.390(4) . ?
C2 H2A 0.9300 . ?
C15 H15 0.9300 . ?
C20 C21 1.342(4) . ?
C20 H20 0.9300 . ?
C32 H32 0.9300 . ?
C3 C4 1.344(5) . ?
C3 H3 0.9300 . ?
C21 H21 0.9300 . ?
C4 H4 0.9300 . ?
C27 C26 1.351(4) . ?
C27 H27 0.9300 . ?
C26 C25 1.394(4) . ?
C26 H26 0.9300 . ?
C25 H25 0.9300 . ?
C8 C9 1.398(5) . ?
C8 H8 0.9300 . ?
C10 C9 1.330(5) . ?
C10 H10 0.9300 . ?
C9 H9 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
C11 N2 C12 125.21(18) . . ?
C11 N2 H2 120.3(15) . . ?
C12 N2 H2 114.5(15) . . ?
C11 N1 C1 124.71(18) . . ?
C11 N1 H1 114.3(16) . . ?
C1 N1 H1 117.8(16) . . ?
C28 N5 C29 125.4(2) . . ?
C28 N5 H5 119.2(17) . . ?
C29 N5 H5 115.4(17) . . ?
C33 N6 C32 115.8(2) . . ?
C28 N4 C18 124.99(19) . . ?
C28 N4 H4A 117.8(17) . . ?
C18 N4 H4A 117.1(17) . . ?
C14 C13 C17 117.3(2) . . ?
C14 C13 C12 121.02(19) . . ?
C17 C13 C12 121.6(2) . . ?
N2 C11 N1 116.90(18) . . ?
N2 C11 S1 123.45(16) . . ?
N1 C11 S1 119.65(15) . . ?
N2 C12 C13 113.04(18) . . ?
N2 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
N2 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C1 C6 C7 123.5(2) . . ?
C1 C6 C5 117.7(2) . . ?
C7 C6 C5 118.8(2) . . ?
C16 N3 C15 116.6(2) . . ?
C19 C18 C23 121.0(2) . . ?
C19 C18 N4 119.8(2) . . ?
C23 C18 N4 119.1(2) . . ?
C18 C23 C24 122.9(2) . . ?
C18 C23 C22 118.8(2) . . ?
C24 C23 C22 118.3(2) . . ?
N5 C28 N4 116.5(2) . . ?
N5 C28 S2 123.40(19) . . ?
N4 C28 S2 120.09(16) . . ?
C2 C1 C6 121.0(2) . . ?
C2 C1 N1 119.6(2) . . ?
C6 C1 N1 119.4(2) . . ?
C34 C30 C31 116.7(2) . . ?
C34 C30 C29 122.1(2) . . ?
C31 C30 C29 121.2(2) . . ?
C13 C17 C16 118.9(3) . . ?
C13 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C30 C34 C33 119.5(2) . . ?
C30 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
N6 C33 C34 124.4(3) . . ?
N6 C33 H33 117.8 . . ?
C34 C33 H33 117.8 . . ?
C10 C5 C4 122.5(3) . . ?
C10 C5 C6 118.6(3) . . ?
C4 C5 C6 118.8(3) . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
N5 C29 C30 110.15(19) . . ?
N5 C29 H29A 109.6 . . ?
C30 C29 H29A 109.6 . . ?
N5 C29 H29B 109.6 . . ?
C30 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C30 C31 C32 119.5(2) . . ?
C30 C31 H31 120.3 . . ?
C32 C31 H31 120.3 . . ?
N3 C16 C17 124.0(2) . . ?
N3 C16 H16 118.0 . . ?
C17 C16 H16 118.0 . . ?
C27 C22 C21 122.7(3) . . ?
C27 C22 C23 118.8(3) . . ?
C21 C22 C23 118.4(3) . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
N3 C15 C14 123.7(3) . . ?
N3 C15 H15 118.2 . . ?
C14 C15 H15 118.2 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
N6 C32 C31 124.2(3) . . ?
N6 C32 H32 117.9 . . ?
C31 C32 H32 117.9 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C20 C21 C22 121.4(3) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C26 C27 C22 121.3(3) . . ?
C26 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?
C27 C26 C25 120.1(3) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C24 C25 C26 121.0(3) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C9 C10 C5 121.3(4) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
C10 C9 C8 121.4(4) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N2 C11 N1 -176.6(2) . . . . ?
C12 N2 C11 S1 3.4(3) . . . . ?
C1 N1 C11 N2 7.2(3) . . . . ?
C1 N1 C11 S1 -172.78(18) . . . . ?
C11 N2 C12 C13 -103.6(2) . . . . ?
C14 C13 C12 N2 66.4(3) . . . . ?
C17 C13 C12 N2 -115.7(2) . . . . ?
C28 N4 C18 C19 64.7(4) . . . . ?
C28 N4 C18 C23 -116.9(3) . . . . ?
C19 C18 C23 C24 -179.1(2) . . . . ?
N4 C18 C23 C24 2.4(3) . . . . ?
C19 C18 C23 C22 0.4(3) . . . . ?
N4 C18 C23 C22 -178.1(2) . . . . ?
C29 N5 C28 N4 -174.1(2) . . . . ?
C29 N5 C28 S2 6.8(3) . . . . ?
C18 N4 C28 N5 12.8(4) . . . . ?
C18 N4 C28 S2 -168.0(2) . . . . ?
C7 C6 C1 C2 179.0(2) . . . . ?
C5 C6 C1 C2 -0.5(3) . . . . ?
C7 C6 C1 N1 0.7(3) . . . . ?
C5 C6 C1 N1 -178.83(19) . . . . ?
C11 N1 C1 C2 99.5(3) . . . . ?
C11 N1 C1 C6 -82.1(3) . . . . ?
C14 C13 C17 C16 0.8(4) . . . . ?
C12 C13 C17 C16 -177.2(2) . . . . ?
C17 C13 C14 C15 -1.4(4) . . . . ?
C12 C13 C14 C15 176.7(2) . . . . ?
C1 C6 C7 C8 -179.4(2) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C31 C30 C34 C33 0.7(4) . . . . ?
C29 C30 C34 C33 -177.4(3) . . . . ?
C32 N6 C33 C34 -0.9(4) . . . . ?
C30 C34 C33 N6 0.1(5) . . . . ?
C1 C6 C5 C10 179.9(2) . . . . ?
C7 C6 C5 C10 0.4(3) . . . . ?
C1 C6 C5 C4 0.0(3) . . . . ?
C7 C6 C5 C4 -179.5(2) . . . . ?
C23 C18 C19 C20 0.7(4) . . . . ?
N4 C18 C19 C20 179.1(2) . . . . ?
C28 N5 C29 C30 124.9(3) . . . . ?
C34 C30 C29 N5 122.8(3) . . . . ?
C31 C30 C29 N5 -55.2(3) . . . . ?
C18 C23 C24 C25 -179.0(2) . . . . ?
C22 C23 C24 C25 1.5(4) . . . . ?
C34 C30 C31 C32 -0.8(4) . . . . ?
C29 C30 C31 C32 177.3(3) . . . . ?
C15 N3 C16 C17 -0.8(4) . . . . ?
C13 C17 C16 N3 0.2(4) . . . . ?
C18 C23 C22 C27 177.6(2) . . . . ?
C24 C23 C22 C27 -2.8(4) . . . . ?
C18 C23 C22 C21 -1.1(3) . . . . ?
C24 C23 C22 C21 178.4(2) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
N1 C1 C2 C3 179.0(2) . . . . ?
C16 N3 C15 C14 0.2(5) . . . . ?
C13 C14 C15 N3 0.9(5) . . . . ?
C18 C19 C20 C21 -0.9(4) . . . . ?
C33 N6 C32 C31 0.8(5) . . . . ?
C30 C31 C32 N6 0.0(5) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C19 C20 C21 C22 0.1(5) . . . . ?
C27 C22 C21 C20 -177.8(3) . . . . ?
C23 C22 C21 C20 0.9(4) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C10 C5 C4 C3 -179.6(3) . . . . ?
C6 C5 C4 C3 0.3(4) . . . . ?
C21 C22 C27 C26 -179.4(3) . . . . ?
C23 C22 C27 C26 1.9(4) . . . . ?
C22 C27 C26 C25 0.4(5) . . . . ?
C23 C24 C25 C26 0.9(4) . . . . ?
C27 C26 C25 C24 -1.9(5) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C4 C5 C10 C9 179.5(3) . . . . ?
C6 C5 C10 C9 -0.5(5) . . . . ?
C5 C10 C9 C8 0.1(6) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_Phenthiourea
_database_code_depnum_ccdc_archive 'CCDC 2171848'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C13 H13 N3 S'
_chemical_formula_sum            'C13 H13 N3 S'
_chemical_formula_weight         243.334
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   5.9160(4)
_cell_length_b                   22.1005(16)
_cell_length_c                   9.9693(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.216(6)
_cell_angle_gamma                90
_cell_volume                     1282.79(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1396
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.7700
_cell_measurement_theta_min      2.7900
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             512.756
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.9991
_diffrn_reflns_Laue_measured_fraction_max 0.9991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5590
_diffrn_reflns_point_group_measured_fraction_full 0.9991
_diffrn_reflns_point_group_measured_fraction_max 0.9991
_diffrn_reflns_theta_full        25.0400
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.78
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2760
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     63.00  95.00   1.00   15.99    --   20.92 178.00   0.00   32
  2  ω     17.00  78.00   1.00   15.99    --   20.92  19.00  30.00   61
  3  ω    -31.00  94.00   1.00   15.99    --   20.92   0.00 150.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0372042000
_diffrn_orient_matrix_UB_12      -0.0055842000
_diffrn_orient_matrix_UB_13      -0.0626887000
_diffrn_orient_matrix_UB_21      -0.0530986000
_diffrn_orient_matrix_UB_22      0.0272143000
_diffrn_orient_matrix_UB_23      -0.0269191000
_diffrn_orient_matrix_UB_31      0.1031623000
_diffrn_orient_matrix_UB_32      0.0160808000
_diffrn_orient_matrix_UB_33      0.0238137000
_diffrn_oxdiff_ac4_digest_frames 
;
018f431063bf0bd2cf55f4b2de3b1d431600027e87d
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1630
_reflns_number_total             2256
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2109
_refine_diff_density_min         -0.2403
_refine_diff_density_rms         0.0529
_refine_ls_d_res_high            0.8396
_refine_ls_d_res_low             7.3367
_refine_ls_goodness_of_fit_ref   1.0614
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.0614
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+0.2268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0949
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2a), C1(H1a), C6(H6), C5(H5), C13(H13), C12(H12), C11(H11),
 C10(H10)
;
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_refinement_flags_posn
S1 S 0.28162(11) 0.04785(3) 0.62342(6) 0.0640(2) Uani 1.000000 .
N1 N 0.1279(4) 0.05441(9) 0.35927(18) 0.0558(5) Uani 1.000000 .
N2 N 0.4580(3) 0.10793(8) 0.43527(19) 0.0504(5) Uani 1.000000 .
C4 C 0.1146(3) 0.06738(9) 0.21755(19) 0.0457(5) Uani 1.000000 .
C3 C -0.0826(4) 0.09312(11) 0.1479(2) 0.0630(6) Uani 1.000000 .
H3 H -0.2009(4) 0.10346(11) 0.1938(2) 0.0756(8) Uiso 1.000000 R
C2 C -0.1056(4) 0.10372(12) 0.0097(2) 0.0766(8) Uani 1.000000 .
H2a H -0.2395(4) 0.12122(12) -0.0374(2) 0.0919(9) Uiso 1.000000 R
C1 C 0.0672(4) 0.08861(12) -0.0583(2) 0.0693(7) Uani 1.000000 .
H1a H 0.0512(4) 0.09578(12) -0.1514(2) 0.0832(8) Uiso 1.000000 R
C6 C 0.2625(4) 0.06309(11) 0.0104(2) 0.0653(6) Uani 1.000000 .
H6 H 0.3808(4) 0.05310(11) -0.0358(2) 0.0784(8) Uiso 1.000000 R
C5 C 0.2868(4) 0.05187(10) 0.1485(2) 0.0581(6) Uani 1.000000 .
H5 H 0.4201(4) 0.03378(10) 0.1947(2) 0.0698(7) Uiso 1.000000 R
C7 C 0.2925(4) 0.07112(9) 0.4632(2) 0.0477(5) Uani 1.000000 .
C8 C 0.6500(4) 0.12774(10) 0.5357(2) 0.0568(6) Uani 1.000000 .
H8a H 0.6850(4) 0.09654(10) 0.6047(2) 0.0682(7) Uiso 1.000000 R
H8b H 0.7829(4) 0.13211(10) 0.4919(2) 0.0682(7) Uiso 1.000000 R
C9 C 0.6118(4) 0.18672(9) 0.6051(2) 0.0485(5) Uani 1.000000 .
C13 C 0.7845(4) 0.21174(12) 0.6985(3) 0.0756(7) Uani 1.000000 .
H13 H 0.9265(4) 0.19261(12) 0.7191(3) 0.0908(9) Uiso 1.000000 R
C12 C 0.7470(6) 0.26530(13) 0.7617(3) 0.0948(10) Uani 1.000000 .
H12 H 0.8671(6) 0.28069(13) 0.8256(3) 0.1137(12) Uiso 1.000000 R
N3 N 0.5538(4) 0.29641(9) 0.7386(2) 0.0767(6) Uani 1.000000 .
C11 C 0.3907(5) 0.27313(12) 0.6467(3) 0.0773(8) Uani 1.000000 .
H11 H 0.2529(5) 0.29420(12) 0.6254(3) 0.0928(9) Uiso 1.000000 R
C10 C 0.4110(4) 0.21919(11) 0.5795(3) 0.0747(8) Uani 1.000000 .
H10 H 0.2876(4) 0.20480(11) 0.5166(3) 0.0896(9) Uiso 1.000000 R
H2 H 0.455(3) 0.1243(10) 0.351(2) 0.067(7) Uiso 1.000000 .
H1 H 0.022(4) 0.0308(10) 0.375(2) 0.064(7) Uiso 1.000000 .


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 C7 1.690(2) . ?
N1 C4 1.430(2) . ?
N1 C7 1.342(3) . ?
N1 H1 0.85(2) . ?
N2 C7 1.340(3) . ?
N2 C8 1.442(3) . ?
N2 H2 0.91(2) . ?
C4 C3 1.371(3) . ?
C4 C5 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.381(3) . ?
C2 H2a 0.9300 . ?
C2 C1 1.365(3) . ?
C1 H1a 0.9300 . ?
C1 C6 1.357(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.381(3) . ?
C5 H5 0.9300 . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C8 C9 1.511(3) . ?
C9 C13 1.371(3) . ?
C9 C10 1.373(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.377(4) . ?
C12 H12 0.9300 . ?
C12 N3 1.319(3) . ?
N3 C11 1.312(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.383(3) . ?
C10 H10 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
C7 N1 C4 127.83(19) . . ?
H1 N1 C4 113.1(15) . . ?
H1 N1 C7 118.9(15) . . ?
C8 N2 C7 123.67(19) . . ?
H2 N2 C7 122.4(13) . . ?
H2 N2 C8 113.9(13) . . ?
C3 C4 N1 118.46(18) . . ?
C5 C4 N1 122.0(2) . . ?
C5 C4 C3 119.42(19) . . ?
H3 C3 C4 119.99(12) . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 119.99(15) . . ?
H2a C2 C3 119.86(15) . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2a 119.86(15) . . ?
H1a C1 C2 120.09(15) . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 H1a 120.09(13) . . ?
H6 C6 C1 119.78(13) . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.78(14) . . ?
C6 C5 C4 120.0(2) . . ?
H5 C5 C4 119.99(13) . . ?
H5 C5 C6 119.99(14) . . ?
N1 C7 S1 120.15(16) . . ?
N2 C7 S1 122.21(17) . . ?
N2 C7 N1 117.61(19) . . ?
H8a C8 N2 108.61(12) . . ?
H8b C8 N2 108.61(11) . . ?
H8b C8 H8a 107.6 . . ?
C9 C8 N2 114.61(18) . . ?
C9 C8 H8a 108.61(11) . . ?
C9 C8 H8b 108.61(11) . . ?
C13 C9 C8 120.3(2) . . ?
C10 C9 C8 124.1(2) . . ?
C10 C9 C13 115.6(2) . . ?
H13 C13 C9 120.12(14) . . ?
C12 C13 C9 119.8(2) . . ?
C12 C13 H13 120.12(17) . . ?
H12 C12 C13 117.52(17) . . ?
N3 C12 C13 125.0(3) . . ?
N3 C12 H12 117.52(15) . . ?
C11 N3 C12 115.2(2) . . ?
H11 C11 N3 117.98(15) . . ?
C10 C11 N3 124.0(3) . . ?
C10 C11 H11 117.98(16) . . ?
C11 C10 C9 120.5(2) . . ?
H10 C10 C9 119.76(14) . . ?
H10 C10 C11 119.76(16) . . ?

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
S1 C7 N1 C4 -176.93(15) . . . . ?
S1 C7 N2 C8 4.5(2) . . . . ?
N1 C4 C3 C2 -177.0(2) . . . . ?
N1 C4 C5 C6 177.4(2) . . . . ?
N1 C7 N2 C8 -177.63(18) . . . . ?
N2 C8 C9 C13 -177.3(2) . . . . ?
N2 C8 C9 C10 1.6(3) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C3 C2 C1 C6 -0.0(3) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C8 C9 C13 C12 -179.5(2) . . . . ?
C8 C9 C10 C11 -179.4(2) . . . . ?
C9 C13 C12 N3 -1.0(3) . . . . ?
C9 C10 C11 N3 -1.2(3) . . . . ?
C13 C12 N3 C11 -0.7(4) . . . . ?
C12 N3 C11 C10 1.7(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.788
_oxdiff_exptl_absorpt_empirical_full_min 0.612
