#------------------------------------------------------------------------------
#$Date: 2020-04-22 06:23:57 +0300 (Wed, 22 Apr 2020) $
#$Revision: 251007 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243360.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243360
loop_
_publ_author_name
'Izuogu, David Chukwuma'
'Asegbeloyin, Jonnie Niyi'
'Jotani, Mukesh M.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal
 structure, Hirshfeld surface analysis and computational study
;
_journal_coeditor_code           LH5956
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              697
_journal_page_last               702
_journal_paper_doi               10.1107/S2056989020005101
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C17 H16 N2 O3 S'
_chemical_formula_moiety         'C17 H16 N2 O3 S'
_chemical_formula_sum            'C17 H16 N2 O3 S'
_chemical_formula_weight         328.38
_chemical_name_systematic
;
2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                92.214(2)
_cell_angle_beta                 93.4230(10)
_cell_angle_gamma                114.2740(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9782(4)
_cell_length_b                   8.1711(5)
_cell_length_c                   12.6661(7)
_cell_measurement_reflns_used    5241
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.665
_cell_measurement_theta_min      2.741
_cell_volume                     749.55(7)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
APEX2 (Bruker, 2002)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11665
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.863
_diffrn_reflns_theta_min         1.614
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.386
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         5913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0479
_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)+(0.0579P)²+0.3671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                4625
_reflns_number_total             5913
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5956sup1.cif
_cod_data_source_block           I
_cod_database_code               2243360
_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.
;
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.52952(4) 0.91549(4) 0.73039(2) 0.00972(8) Uani d 1 . .
O O1 0.70758(13) 0.91524(14) 0.72487(8) 0.01414(19) Uani d 1 . .
O O2 0.51875(14) 1.07825(13) 0.76724(7) 0.01422(19) Uani d 1 . .
O O3 0.45530(14) 0.53580(14) 0.72961(7) 0.01357(19) Uani d 1 . .
N N1 0.42015(15) 0.76225(15) 0.82277(8) 0.0107(2) Uani d 1 . .
N N2 0.36966(17) 0.83676(16) 0.90820(9) 0.0138(2) Uani d 1 . .
C C1 0.38648(17) 0.82486(17) 0.61201(9) 0.0097(2) Uani d 1 . .
C C2 0.44783(17) 0.75451(17) 0.52613(10) 0.0103(2) Uani d 1 . .
C C3 0.32852(18) 0.69064(18) 0.43396(10) 0.0116(2) Uani d 1 . .
H H3 0.367189 0.643377 0.375142 0.014 Uiso calc 1 . .
C C4 0.15518(18) 0.69371(18) 0.42516(10) 0.0126(2) Uani d 1 . .
C C5 0.09886(18) 0.76139(19) 0.51177(10) 0.0133(2) Uani d 1 . .
H H5 -0.020289 0.761710 0.506665 0.016 Uiso calc 1 . .
C C6 0.21077(18) 0.82878(18) 0.60579(10) 0.0116(2) Uani d 1 . .
C C7 0.63166(18) 0.7437(2) 0.52408(11) 0.0141(2) Uani d 1 . .
H H7A 0.636640 0.683730 0.456594 0.021 Uiso calc 1 . .
H H7B 0.647194 0.675014 0.582699 0.021 Uiso calc 1 . .
H H7C 0.730720 0.865470 0.531622 0.021 Uiso calc 1 . .
C C8 0.0315(2) 0.6274(2) 0.32396(11) 0.0190(3) Uani d 1 . .
H H8A -0.094563 0.608096 0.337969 0.028 Uiso calc 1 . .
H H8B 0.032099 0.513741 0.296720 0.028 Uiso calc 1 . .
H H8C 0.076289 0.717057 0.271317 0.028 Uiso calc 1 . .
C C9 0.1341(2) 0.9043(2) 0.69211(11) 0.0190(3) Uani d 1 . .
H H9A 0.184991 1.035634 0.691039 0.028 Uiso calc 1 . .
H H9B 0.168371 0.871735 0.761207 0.028 Uiso calc 1 . .
H H9C -0.000599 0.854423 0.680026 0.028 Uiso calc 1 . .
C C10 0.40551(17) 0.58589(17) 0.80886(10) 0.0099(2) Uani d 1 . .
C C11 0.32443(17) 0.47264(18) 0.89581(10) 0.0106(2) Uani d 1 . .
C C12 0.30524(18) 0.29500(18) 0.89276(10) 0.0132(2) Uani d 1 . .
H H12 0.343082 0.246095 0.834285 0.016 Uiso calc 1 . .
C C13 0.23047(19) 0.19062(19) 0.97587(11) 0.0153(3) Uani d 1 . .
H H13 0.216814 0.069423 0.974185 0.018 Uiso calc 1 . .
C C14 0.17479(19) 0.2621(2) 1.06236(11) 0.0160(3) Uani d 1 . .
H H14 0.123129 0.189023 1.118763 0.019 Uiso calc 1 . .
C C15 0.19460(19) 0.4382(2) 1.06607(11) 0.0154(3) Uani d 1 . .
H H15 0.157015 0.486375 1.124986 0.018 Uiso calc 1 . .
C C16 0.27053(18) 0.54625(18) 0.98247(10) 0.0118(2) Uani d 1 . .
C C17 0.2996(2) 0.73194(19) 0.98264(10) 0.0145(2) Uani d 1 . .
H H17 0.264466 0.781298 1.042086 0.017 Uiso calc 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 118.39(6) ?
O1 S1 N1 . . 106.22(6) ?
O2 S1 N1 . . 104.37(6) ?
O1 S1 C1 . . 112.48(6) ?
O2 S1 C1 . . 110.28(6) ?
N1 S1 C1 . . 103.58(6) ?
N2 N1 C10 . . 126.97(11) ?
N2 N1 S1 . . 113.93(9) ?
C10 N1 S1 . . 118.89(8) ?
C17 N2 N1 . . 116.47(12) ?
C6 C1 C2 . . 121.56(11) ?
C6 C1 S1 . . 117.50(9) ?
C2 C1 S1 . . 120.94(10) ?
C3 C2 C1 . . 117.37(12) ?
C3 C2 C7 . . 116.62(11) ?
C1 C2 C7 . . 126.01(11) ?
C4 C3 C2 . . 122.42(12) ?
C4 C3 H3 . . 118.8 ?
C2 C3 H3 . . 118.8 ?
C5 C4 C3 . . 118.48(12) ?
C5 C4 C8 . . 120.39(12) ?
C3 C4 C8 . . 121.12(12) ?
C4 C5 C6 . . 122.33(12) ?
C4 C5 H5 . . 118.8 ?
C6 C5 H5 . . 118.8 ?
C5 C6 C1 . . 117.83(11) ?
C5 C6 C9 . . 116.57(12) ?
C1 C6 C9 . . 125.58(12) ?
C2 C7 H7A . . 109.5 ?
C2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C4 C8 H8A . . 109.5 ?
C4 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C4 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C6 C9 H9A . . 109.5 ?
C6 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C6 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O3 C10 N1 . . 120.86(12) ?
O3 C10 C11 . . 124.94(12) ?
N1 C10 C11 . . 114.19(11) ?
C12 C11 C16 . . 120.62(12) ?
C12 C11 C10 . . 120.00(11) ?
C16 C11 C10 . . 119.36(12) ?
C13 C12 C11 . . 119.31(12) ?
C13 C12 H12 . . 120.3 ?
C11 C12 H12 . . 120.3 ?
C12 C13 C14 . . 120.60(13) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C15 C14 C13 . . 120.31(13) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C16 . . 119.85(13) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C11 C16 C15 . . 119.30(13) ?
C11 C16 C17 . . 117.99(12) ?
C15 C16 C17 . . 122.69(12) ?
N2 C17 C16 . . 125.01(12) ?
N2 C17 H17 . . 117.5 ?
C16 C17 H17 . . 117.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4273(10) ?
S1 O2 . 1.4300(10) ?
S1 N1 . 1.7422(11) ?
S1 C1 . 1.7646(12) ?
O3 C10 . 1.2175(15) ?
N1 N2 . 1.3808(15) ?
N1 C10 . 1.4003(17) ?
N2 C17 . 1.2911(18) ?
C1 C6 . 1.4130(18) ?
C1 C2 . 1.4142(17) ?
C2 C3 . 1.3975(18) ?
C2 C7 . 1.5066(18) ?
C3 C4 . 1.3913(19) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3883(18) ?
C4 C8 . 1.5055(19) ?
C5 C6 . 1.3917(18) ?
C5 H5 . 0.9500 ?
C6 C9 . 1.5125(18) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.4694(18) ?
C11 C12 . 1.3943(19) ?
C11 C16 . 1.4034(18) ?
C12 C13 . 1.3847(19) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.400(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.380(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.4059(19) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.438(2) ?
C17 H17 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C12 H12 O2 1_545 0.95 2.49 3.3395(18) 149
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 N1 N2 . . . . 120.33(10) ?
O2 S1 N1 N2 . . . . -5.52(11) ?
C1 S1 N1 N2 . . . . -120.99(10) ?
O1 S1 N1 C10 . . . . -54.70(11) ?
O2 S1 N1 C10 . . . . 179.45(10) ?
C1 S1 N1 C10 . . . . 63.98(11) ?
C10 N1 N2 C17 . . . . -0.8(2) ?
S1 N1 N2 C17 . . . . -175.38(10) ?
O1 S1 C1 C6 . . . . -176.04(10) ?
O2 S1 C1 C6 . . . . -41.49(12) ?
N1 S1 C1 C6 . . . . 69.70(11) ?
O1 S1 C1 C2 . . . . 2.71(13) ?
O2 S1 C1 C2 . . . . 137.26(11) ?
N1 S1 C1 C2 . . . . -111.55(11) ?
C6 C1 C2 C3 . . . . 0.74(19) ?
S1 C1 C2 C3 . . . . -177.95(10) ?
C6 C1 C2 C7 . . . . 179.99(13) ?
S1 C1 C2 C7 . . . . 1.30(19) ?
C1 C2 C3 C4 . . . . -0.3(2) ?
C7 C2 C3 C4 . . . . -179.65(12) ?
C2 C3 C4 C5 . . . . -0.6(2) ?
C2 C3 C4 C8 . . . . 178.73(13) ?
C3 C4 C5 C6 . . . . 1.2(2) ?
C8 C4 C5 C6 . . . . -178.16(13) ?
C4 C5 C6 C1 . . . . -0.8(2) ?
C4 C5 C6 C9 . . . . 177.86(14) ?
C2 C1 C6 C5 . . . . -0.2(2) ?
S1 C1 C6 C5 . . . . 178.53(10) ?
C2 C1 C6 C9 . . . . -178.71(14) ?
S1 C1 C6 C9 . . . . 0.02(19) ?
N2 N1 C10 O3 . . . . -179.88(12) ?
S1 N1 C10 O3 . . . . -5.57(17) ?
N2 N1 C10 C11 . . . . 0.98(18) ?
S1 N1 C10 C11 . . . . 175.29(9) ?
O3 C10 C11 C12 . . . . 2.1(2) ?
N1 C10 C11 C12 . . . . -178.79(11) ?
O3 C10 C11 C16 . . . . -179.23(12) ?
N1 C10 C11 C16 . . . . -0.13(17) ?
C16 C11 C12 C13 . . . . 0.6(2) ?
C10 C11 C12 C13 . . . . 179.29(12) ?
C11 C12 C13 C14 . . . . -0.1(2) ?
C12 C13 C14 C15 . . . . -0.3(2) ?
C13 C14 C15 C16 . . . . 0.2(2) ?
C12 C11 C16 C15 . . . . -0.75(19) ?
C10 C11 C16 C15 . . . . -179.40(12) ?
C12 C11 C16 C17 . . . . 177.93(12) ?
C10 C11 C16 C17 . . . . -0.72(18) ?
C14 C15 C16 C11 . . . . 0.3(2) ?
C14 C15 C16 C17 . . . . -178.29(13) ?
N1 N2 C17 C16 . . . . -0.2(2) ?
C11 C16 C17 N2 . . . . 0.9(2) ?
C15 C16 C17 N2 . . . . 179.58(14) ?

_cod_database_fobs_code 2243360
