data_jhdbnap

# start Validation Reply Form
_vrf_PLAT430_jhdbnap
;
PROBLEM: Short Inter D...A Contact  O1       ..O1       .       2.77 Ang.  
RESPONSE: Cyclic hydrogen bonding between O1...H2(N2)...O1...H2(N2)
results in short interaction between O1 and O1 atoms.
;
# end Validation Reply Form










_audit_creation_date               2019-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H12 Cl2 N2 O S'
_chemical_formula_sum              'C18 H12 Cl2 N2 O S'
_chemical_formula_weight           375.26
_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        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     7.331(2)
_cell_length_b                     8.111(2)
_cell_length_c                     14.229(4)
_cell_angle_alpha                  92.899(3)
_cell_angle_beta                   101.046(3)
_cell_angle_gamma                  105.360(3)
_cell_volume                       796.2(4)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      5117
_cell_measurement_temperature      110.0
_cell_measurement_theta_max        27.478
_cell_measurement_theta_min        2.619
_shelx_estimated_absorpt_T_max     0.946
_shelx_estimated_absorpt_T_min     0.734
_exptl_absorpt_coefficient_mu      0.546
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6340
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.1198 before and 0.0455 after correction. The Ratio of minimum to maximum transmission is 0.8503. 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      1.565
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               384
_exptl_crystal_size_max            0.603
_exptl_crystal_size_mid            0.198
_exptl_crystal_size_min            0.102
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0360
_diffrn_reflns_av_unetI/netI       0.0381
_diffrn_reflns_Laue_measured_fraction_full  0.996
_diffrn_reflns_Laue_measured_fraction_max  0.982
_diffrn_reflns_limit_h_max         9
_diffrn_reflns_limit_h_min         -9
_diffrn_reflns_limit_k_max         10
_diffrn_reflns_limit_k_min         -10
_diffrn_reflns_limit_l_max         18
_diffrn_reflns_limit_l_min         -18
_diffrn_reflns_number              9336
_diffrn_reflns_point_group_measured_fraction_full  0.996
_diffrn_reflns_point_group_measured_fraction_max  0.982
_diffrn_reflns_theta_full          26.000
_diffrn_reflns_theta_max           27.506
_diffrn_reflns_theta_min           2.619
_diffrn_ambient_temperature        110.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.982
_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_special_details            ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3176
_reflns_number_total               3604
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.371
_refine_diff_density_min           -0.300
_refine_diff_density_rms           0.059
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.061
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       217
_refine_ls_number_reflns           3604
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0352
_refine_ls_R_factor_gt             0.0303
_refine_ls_restrained_S_all        1.061
_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)+(0.0300P)²+0.3509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0763
_refine_ls_wR_factor_ref           0.0791
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_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 0.10701(6) 0.33026(4) 0.15457(3) 0.01959(10) Uani 1 1 d . . . . .
 Cl2 Cl 0.26873(7) 0.96360(5) 0.04366(3) 0.03011(12) Uani 1 1 d . . . . .
 S1 S 0.47141(5) 0.19062(5) 0.45203(3) 0.01468(10) Uani 1 1 d . . . . .
 O1 O 0.08809(15) 0.55059(14) 0.42422(7) 0.0164(2) Uani 1 1 d . . . . .
 N1 N 0.28437(18) 0.40287(15) 0.37729(9) 0.0125(2) Uani 1 1 d . . . . .
 H1 H 0.366880 0.391592 0.336414 0.015 Uiso 1 1 d R . . . .
 N2 N 0.21595(18) 0.31564(15) 0.52270(8) 0.0129(3) Uani 1 1 d . . . . .
 H2 H 0.138379 0.382473 0.515542 0.015 Uiso 1 1 calc R . . . .
 C1 C 0.3151(2) 0.30536(18) 0.45425(10) 0.0118(3) Uani 1 1 d . . . . .
 C2 C 0.1809(2) 0.52058(18) 0.36645(10) 0.0117(3) Uani 1 1 d . . . . .
 C3 C 0.1974(2) 0.62049(18) 0.28113(10) 0.0118(3) Uani 1 1 d . . . . .
 C4 C 0.1719(2) 0.55123(18) 0.18630(10) 0.0127(3) Uani 1 1 d . . . . .
 C5 C 0.1901(2) 0.65565(19) 0.11256(11) 0.0156(3) Uani 1 1 d . . . . .
 H5 H 0.170457 0.607383 0.047937 0.019 Uiso 1 1 calc R . . . .
 C6 C 0.2374(2) 0.8320(2) 0.13522(11) 0.0164(3) Uani 1 1 d . . . . .
 C7 C 0.2629(2) 0.90537(19) 0.22811(11) 0.0170(3) Uani 1 1 d . . . . .
 H7 H 0.295305 1.026670 0.242114 0.020 Uiso 1 1 calc R . . . .
 C8 C 0.2404(2) 0.79882(19) 0.30041(10) 0.0144(3) Uani 1 1 d . . . . .
 H8 H 0.254478 0.847772 0.364370 0.017 Uiso 1 1 calc R . . . .
 C9 C 0.2261(2) 0.22634(19) 0.60681(10) 0.0125(3) Uani 1 1 d . . . . .
 C10 C 0.2689(2) 0.32459(18) 0.69807(10) 0.0120(3) Uani 1 1 d . . . . .
 C11 C 0.2685(2) 0.23536(19) 0.78168(10) 0.0149(3) Uani 1 1 d . . . . .
 C12 C 0.2275(2) 0.0539(2) 0.77191(11) 0.0174(3) Uani 1 1 d . . . . .
 H12 H 0.226112 -0.006105 0.827538 0.021 Uiso 1 1 calc R . . . .
 C13 C 0.1898(2) -0.03564(19) 0.68319(11) 0.0178(3) Uani 1 1 d . . . . .
 H13 H 0.163848 -0.157256 0.677702 0.021 Uiso 1 1 calc R . . . .
 C14 C 0.1890(2) 0.05051(19) 0.59983(11) 0.0149(3) Uani 1 1 d . . . . .
 H14 H 0.162775 -0.013099 0.538495 0.018 Uiso 1 1 calc R . . . .
 C15 C 0.3135(2) 0.50692(19) 0.70924(11) 0.0141(3) Uani 1 1 d . . . . .
 H15 H 0.312672 0.567773 0.653917 0.017 Uiso 1 1 calc R . . . .
 C16 C 0.3576(2) 0.5958(2) 0.79866(11) 0.0176(3) Uani 1 1 d . . . . .
 H16 H 0.389723 0.717829 0.805010 0.021 Uiso 1 1 calc R . . . .
 C17 C 0.3557(2) 0.5076(2) 0.88156(11) 0.0195(3) Uani 1 1 d . . . . .
 H17 H 0.385664 0.570257 0.943404 0.023 Uiso 1 1 calc R . . . .
 C18 C 0.3109(2) 0.3325(2) 0.87306(11) 0.0186(3) Uani 1 1 d . . . . .
 H18 H 0.307882 0.274405 0.929288 0.022 Uiso 1 1 calc R . . . .


_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 C4 1.7398(15) . ?
 Cl2 C6 1.7366(15) . ?
 S1 C1 1.6602(15) . ?
 O1 C2 1.2163(18) . ?
 N1 H1 0.9335 . ?
 N1 C1 1.4011(18) . ?
 N1 C2 1.3656(18) . ?
 N2 H2 0.8800 . ?
 N2 C1 1.3339(19) . ?
 N2 C9 1.4300(18) . ?
 C2 C3 1.4998(19) . ?
 C3 C4 1.394(2) . ?
 C3 C8 1.397(2) . ?
 C4 C5 1.386(2) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.385(2) . ?
 C6 C7 1.380(2) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.383(2) . ?
 C8 H8 0.9500 . ?
 C9 C10 1.424(2) . ?
 C9 C14 1.374(2) . ?
 C10 C11 1.4235(19) . ?
 C10 C15 1.421(2) . ?
 C11 C12 1.416(2) . ?
 C11 C18 1.421(2) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.366(2) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.407(2) . ?
 C14 H14 0.9500 . ?
 C15 H15 0.9500 . ?
 C15 C16 1.367(2) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.411(2) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.363(2) . ?
 C18 H18 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C1 N1 H1 108.5 . . ?
 C2 N1 H1 121.6 . . ?
 C2 N1 C1 129.01(12) . . ?
 C1 N2 H2 117.5 . . ?
 C1 N2 C9 124.99(12) . . ?
 C9 N2 H2 117.5 . . ?
 N1 C1 S1 117.30(11) . . ?
 N2 C1 S1 126.53(11) . . ?
 N2 C1 N1 116.17(12) . . ?
 O1 C2 N1 122.98(13) . . ?
 O1 C2 C3 121.06(13) . . ?
 N1 C2 C3 115.85(12) . . ?
 C4 C3 C2 125.95(13) . . ?
 C4 C3 C8 118.38(13) . . ?
 C8 C3 C2 115.67(12) . . ?
 C3 C4 Cl1 121.63(11) . . ?
 C5 C4 Cl1 117.08(11) . . ?
 C5 C4 C3 121.25(13) . . ?
 C4 C5 H5 120.8 . . ?
 C6 C5 C4 118.46(14) . . ?
 C6 C5 H5 120.8 . . ?
 C5 C6 Cl2 118.60(12) . . ?
 C7 C6 Cl2 119.39(12) . . ?
 C7 C6 C5 122.01(14) . . ?
 C6 C7 H7 120.7 . . ?
 C6 C7 C8 118.66(14) . . ?
 C8 C7 H7 120.7 . . ?
 C3 C8 H8 119.4 . . ?
 C7 C8 C3 121.22(14) . . ?
 C7 C8 H8 119.4 . . ?
 C10 C9 N2 117.94(13) . . ?
 C14 C9 N2 121.15(13) . . ?
 C14 C9 C10 120.87(13) . . ?
 C9 C10 C11 118.17(13) . . ?
 C15 C10 C9 122.98(13) . . ?
 C15 C10 C11 118.85(13) . . ?
 C12 C11 C10 119.55(14) . . ?
 C12 C11 C18 121.94(13) . . ?
 C18 C11 C10 118.51(14) . . ?
 C11 C12 H12 119.7 . . ?
 C13 C12 C11 120.53(13) . . ?
 C13 C12 H12 119.7 . . ?
 C12 C13 H13 119.7 . . ?
 C12 C13 C14 120.63(14) . . ?
 C14 C13 H13 119.7 . . ?
 C9 C14 C13 120.23(14) . . ?
 C9 C14 H14 119.9 . . ?
 C13 C14 H14 119.9 . . ?
 C10 C15 H15 119.6 . . ?
 C16 C15 C10 120.79(14) . . ?
 C16 C15 H15 119.6 . . ?
 C15 C16 H16 119.8 . . ?
 C15 C16 C17 120.46(15) . . ?
 C17 C16 H16 119.8 . . ?
 C16 C17 H17 119.9 . . ?
 C18 C17 C16 120.10(14) . . ?
 C18 C17 H17 119.9 . . ?
 C11 C18 H18 119.4 . . ?
 C17 C18 C11 121.27(14) . . ?
 C17 C18 H18 119.4 . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
  _geom_hbond_publ_flag
 N2 H2 O1 0.88 1.99 2.6809(16) 134.9 . yes
 N2 H2 O1 0.88 2.18 2.9257(17) 141.9 2_566 yes

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
 Cl1 C4 C5 C6 178.63(11) . . . . ?
 Cl2 C6 C7 C8 -179.00(12) . . . . ?
 O1 C2 C3 C4 -132.92(16) . . . . ?
 O1 C2 C3 C8 46.3(2) . . . . ?
 N1 C2 C3 C4 50.6(2) . . . . ?
 N1 C2 C3 C8 -130.13(14) . . . . ?
 N2 C9 C10 C11 176.55(12) . . . . ?
 N2 C9 C10 C15 -4.0(2) . . . . ?
 N2 C9 C14 C13 -176.66(13) . . . . ?
 C1 N1 C2 O1 -4.2(2) . . . . ?
 C1 N1 C2 C3 172.18(13) . . . . ?
 C1 N2 C9 C10 126.45(15) . . . . ?
 C1 N2 C9 C14 -55.8(2) . . . . ?
 C2 N1 C1 S1 -172.48(12) . . . . ?
 C2 N1 C1 N2 7.0(2) . . . . ?
 C2 C3 C4 Cl1 2.3(2) . . . . ?
 C2 C3 C4 C5 179.81(14) . . . . ?
 C2 C3 C8 C7 178.82(13) . . . . ?
 C3 C4 C5 C6 1.0(2) . . . . ?
 C4 C3 C8 C7 -1.9(2) . . . . ?
 C4 C5 C6 Cl2 177.76(11) . . . . ?
 C4 C5 C6 C7 -1.3(2) . . . . ?
 C5 C6 C7 C8 0.1(2) . . . . ?
 C6 C7 C8 C3 1.6(2) . . . . ?
 C8 C3 C4 Cl1 -176.98(11) . . . . ?
 C8 C3 C4 C5 0.6(2) . . . . ?
 C9 N2 C1 S1 -0.8(2) . . . . ?
 C9 N2 C1 N1 179.83(13) . . . . ?
 C9 C10 C11 C12 0.5(2) . . . . ?
 C9 C10 C11 C18 -179.89(13) . . . . ?
 C9 C10 C15 C16 -178.66(14) . . . . ?
 C10 C9 C14 C13 1.1(2) . . . . ?
 C10 C11 C12 C13 0.5(2) . . . . ?
 C10 C11 C18 C17 -1.6(2) . . . . ?
 C10 C15 C16 C17 -1.3(2) . . . . ?
 C11 C10 C15 C16 0.8(2) . . . . ?
 C11 C12 C13 C14 -0.7(2) . . . . ?
 C12 C11 C18 C17 178.06(15) . . . . ?
 C12 C13 C14 C9 -0.1(2) . . . . ?
 C14 C9 C10 C11 -1.2(2) . . . . ?
 C14 C9 C10 C15 178.20(14) . . . . ?
 C15 C10 C11 C12 -178.99(13) . . . . ?
 C15 C10 C11 C18 0.6(2) . . . . ?
 C15 C16 C17 C18 0.4(2) . . . . ?
 C16 C17 C18 C11 1.1(2) . . . . ?
 C18 C11 C12 C13 -179.15(14) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
