#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:43:10 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301803 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/97/2209750.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_2209750
loop_
_publ_author_name
'Demoin, Dustin Wayne'
'Pluth, Michael'
'Soo, Han Sen'
'Xu, Yue'
_publ_section_title
;
 Dimethoxyphosphinoyl phenyl ketone p-tolylsulfonylhydrazone
;
_journal_coeditor_code           BI2025
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3551
_journal_page_last               o3552
_journal_paper_doi               10.1107/S1600536806025451
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H19 N2 O5 P S'
_chemical_formula_moiety         'C16 H19 N2 O5 P S'
_chemical_formula_sum            'C16 H19 N2 O5 P S'
_chemical_formula_weight         382.36
_chemical_name_common
;
Dimethoxyphosphinoyl phenyl ketone p-tolylsulfonylhydrazone
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.514(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4692(19)
_cell_length_b                   10.889(3)
_cell_length_c                   9.690(2)
_cell_measurement_reflns_used    1816
_cell_measurement_temperature    166.0(10)
_cell_measurement_theta_max      21.4
_cell_measurement_theta_min      2.8
_cell_volume                     892.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2001)'
_diffrn_ambient_temperature      166.0(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4987
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         1.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.294
_refine_ls_abs_structure_details 'Flack (1983), 971 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2788
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0496P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0940
_reflns_number_gt                2383
_reflns_number_total             2788
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2025.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               2209750
_cod_database_fobs_code          2209750
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'
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_refinement_flags
_atom_site_occupancy
S S1 0.18365(10) 0.22114(8) 0.30113(8) 0.0228(2) Uani d . 1
P P1 0.01807(11) 0.42942(8) 0.74957(8) 0.0216(2) Uani d . 1
O O1 0.2054(3) 0.2524(2) 0.1594(2) 0.0300(6) Uani d . 1
O O2 0.0630(3) 0.1369(2) 0.3358(3) 0.0305(6) Uani d . 1
O O3 0.1586(3) 0.4799(3) 0.8444(2) 0.0304(6) Uani d . 1
O O4 -0.0025(3) 0.2898(2) 0.7806(2) 0.0308(6) Uani d . 1
O O5 -0.1307(3) 0.4935(2) 0.7600(2) 0.0297(6) Uani d . 1
N N1 0.1435(4) 0.3543(3) 0.3747(3) 0.0222(7) Uani d . 1
H H1 0.195(5) 0.403(4) 0.357(4) 0.027 Uiso d . 1
N N2 0.1013(3) 0.3451(3) 0.5098(3) 0.0202(6) Uani d . 1
C C1 0.8036(5) 0.0572(4) 0.5705(4) 0.0354(10) Uani d . 1
H H1A 0.7938 0.0534 0.6687 0.053 Uiso calc R 1
H H1B 0.8840 0.1156 0.5493 0.053 Uiso calc R 1
H H1C 0.8321 -0.0223 0.5367 0.053 Uiso calc R 1
C C2 0.6498(5) 0.0958(3) 0.5032(4) 0.0261(8) Uani d . 1
C C3 0.5072(5) 0.0699(3) 0.5630(4) 0.0284(9) Uani d . 1
H H3A 0.5078 0.0273 0.6461 0.034 Uiso calc R 1
C C4 0.3640(5) 0.1065(3) 0.5010(3) 0.0248(8) Uani d . 1
H H4A 0.2693 0.0890 0.5419 0.030 Uiso calc R 1
C C5 0.3650(4) 0.1701(3) 0.3761(3) 0.0235(8) Uani d . 1
C C6 0.5029(5) 0.1948(3) 0.3141(3) 0.0273(9) Uani d . 1
H H6A 0.5010 0.2357 0.2297 0.033 Uiso calc R 1
C C7 0.6459(5) 0.1589(4) 0.3767(4) 0.0317(9) Uani d . 1
H H7A 0.7399 0.1767 0.3347 0.038 Uiso calc R 1
C C8 0.0977(4) 0.4455(3) 0.5803(3) 0.0209(8) Uani d . 1
C C9 0.1337(4) 0.5716(3) 0.5305(3) 0.0221(8) Uani d . 1
C C10 0.0376(5) 0.6228(3) 0.4254(4) 0.0300(9) Uani d . 1
H H10A -0.0456 0.5778 0.3851 0.036 Uiso calc R 1
C C11 0.0667(5) 0.7410(4) 0.3814(4) 0.0389(11) Uani d . 1
H H11A 0.0025 0.7754 0.3113 0.047 Uiso calc R 1
C C12 0.1892(5) 0.8080(4) 0.4399(4) 0.0364(10) Uani d . 1
H H12A 0.2070 0.8879 0.4104 0.044 Uiso calc R 1
C C13 0.2857(5) 0.7570(4) 0.5421(4) 0.0368(10) Uani d . 1
H H13A 0.3703 0.8018 0.5804 0.044 Uiso calc R 1
C C14 0.2577(5) 0.6401(3) 0.5880(4) 0.0274(8) Uani d . 1
H H14A 0.3224 0.6066 0.6582 0.033 Uiso calc R 1
C C15 0.1320(6) 0.5189(4) 0.9853(4) 0.0402(11) Uani d . 1
H H15A 0.2176 0.5706 1.0178 0.060 Uiso calc R 1
H H15B 0.1264 0.4481 1.0438 0.060 Uiso calc R 1
H H15C 0.0346 0.5638 0.9870 0.060 Uiso calc R 1
C C16 0.1292(6) 0.2089(4) 0.8126(4) 0.0438(12) Uani d . 1
H H16A 0.0982 0.1256 0.7936 0.066 Uiso calc R 1
H H16B 0.1609 0.2169 0.9085 0.066 Uiso calc R 1
H H16C 0.2160 0.2305 0.7569 0.066 Uiso calc R 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'
P P 0.1023 0.0942 '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
_geom_angle_publ_flag
O2 S1 O1 120.14(16) n
O2 S1 N1 107.38(16) n
O1 S1 N1 103.99(15) n
O2 S1 C5 108.77(17) n
O1 S1 C5 108.88(16) n
N1 S1 C5 106.90(16) n
O5 P1 O4 110.56(16) n
O5 P1 O3 115.45(15) n
O4 P1 O3 108.46(15) n
O5 P1 C8 112.15(15) n
O4 P1 C8 108.56(15) n
O3 P1 C8 101.13(15) n
C15 O3 P1 120.4(3) n
C16 O4 P1 122.9(3) n
N2 N1 S1 114.3(2) n
N2 N1 H1 118(3) n
S1 N1 H1 114(3) n
C8 N2 N1 117.1(3) n
C2 C1 H1A 109.5 n
C2 C1 H1B 109.5 n
H1A C1 H1B 109.5 n
C2 C1 H1C 109.5 n
H1A C1 H1C 109.5 n
H1B C1 H1C 109.5 n
C3 C2 C7 118.4(4) n
C3 C2 C1 121.3(3) n
C7 C2 C1 120.4(4) n
C4 C3 C2 121.3(3) n
C4 C3 H3A 119.3 n
C2 C3 H3A 119.3 n
C3 C4 C5 118.7(4) n
C3 C4 H4A 120.7 n
C5 C4 H4A 120.7 n
C6 C5 C4 121.2(4) n
C6 C5 S1 120.3(3) n
C4 C5 S1 118.5(3) n
C5 C6 C7 120.0(3) n
C5 C6 H6A 120.0 n
C7 C6 H6A 120.0 n
C6 C7 C2 120.4(4) n
C6 C7 H7A 119.8 n
C2 C7 H7A 119.8 n
N2 C8 C9 126.8(3) n
N2 C8 P1 114.6(3) n
C9 C8 P1 118.2(2) n
C14 C9 C10 119.2(3) n
C14 C9 C8 121.9(3) n
C10 C9 C8 118.9(3) n
C11 C10 C9 119.5(4) n
C11 C10 H10A 120.3 n
C9 C10 H10A 120.3 n
C12 C11 C10 120.7(4) n
C12 C11 H11A 119.7 n
C10 C11 H11A 119.7 n
C11 C12 C13 119.9(4) n
C11 C12 H12A 120.0 n
C13 C12 H12A 120.0 n
C14 C13 C12 120.2(4) n
C14 C13 H13A 119.9 n
C12 C13 H13A 119.9 n
C13 C14 C9 120.5(4) n
C13 C14 H14A 119.7 n
C9 C14 H14A 119.7 n
O3 C15 H15A 109.5 n
O3 C15 H15B 109.5 n
H15A C15 H15B 109.5 n
O3 C15 H15C 109.5 n
H15A C15 H15C 109.5 n
H15B C15 H15C 109.5 n
O4 C16 H16A 109.5 n
O4 C16 H16B 109.5 n
H16A C16 H16B 109.5 n
O4 C16 H16C 109.5 n
H16A C16 H16C 109.5 n
H16B C16 H16C 109.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 1.424(3) n
S1 O1 1.435(2) n
S1 N1 1.658(3) n
S1 C5 1.760(4) n
P1 O5 1.448(3) n
P1 O4 1.561(3) n
P1 O3 1.571(3) n
P1 C8 1.809(3) n
O3 C15 1.457(4) n
O4 C16 1.444(5) n
N1 N2 1.376(4) n
N1 H1 0.71(4) n
N2 C8 1.290(4) n
C1 C2 1.492(5) n
C1 H1A 0.960 n
C1 H1B 0.960 n
C1 H1C 0.960 n
C2 C3 1.391(5) n
C2 C7 1.404(5) n
C3 C4 1.388(6) n
C3 H3A 0.930 n
C4 C5 1.395(5) n
C4 H4A 0.930 n
C5 C6 1.363(5) n
C6 C7 1.388(6) n
C6 H6A 0.930 n
C7 H7A 0.930 n
C8 C9 1.491(5) n
C9 C14 1.384(5) n
C9 C10 1.393(5) n
C10 C11 1.381(5) n
C10 H10A 0.930 n
C11 C12 1.371(6) n
C11 H11A 0.930 n
C12 C13 1.373(6) n
C12 H12A 0.930 n
C13 C14 1.372(5) n
C13 H13A 0.930 n
C14 H14A 0.930 n
C15 H15A 0.960 n
C15 H15B 0.960 n
C15 H15C 0.960 n
C16 H16A 0.960 n
C16 H16B 0.960 n
C16 H16C 0.960 n
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
_geom_hbond_publ_flag
N1 H1 O5 2_564 0.71(4) 2.11(4) 2.797(4) 162(4) 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_publ_flag
O5 P1 O3 C15 40.3(3) n
O4 P1 O3 C15 -84.4(3) n
C8 P1 O3 C15 161.6(3) n
O5 P1 O4 C16 -163.7(2) n
O3 P1 O4 C16 -36.2(3) n
C8 P1 O4 C16 72.9(3) n
O2 S1 N1 N2 45.1(3) n
O1 S1 N1 N2 173.4(3) n
C5 S1 N1 N2 -71.5(3) n
S1 N1 N2 C8 167.3(3) n
C7 C2 C3 C4 -0.8(5) n
C1 C2 C3 C4 179.6(4) n
C2 C3 C4 C5 0.2(5) n
C3 C4 C5 C6 1.0(5) n
C3 C4 C5 S1 -177.7(3) n
O2 S1 C5 C6 149.7(3) n
O1 S1 C5 C6 17.1(3) n
N1 S1 C5 C6 -94.6(3) n
O2 S1 C5 C4 -31.5(3) n
O1 S1 C5 C4 -164.1(3) n
N1 S1 C5 C4 84.1(3) n
C4 C5 C6 C7 -1.5(5) n
S1 C5 C6 C7 177.2(3) n
C5 C6 C7 C2 0.8(6) n
C3 C2 C7 C6 0.3(6) n
C1 C2 C7 C6 180.0(3) n
N1 N2 C8 C9 0.4(5) n
N1 N2 C8 P1 172.7(2) n
O5 P1 C8 N2 -113.0(3) n
O4 P1 C8 N2 9.4(3) n
O3 P1 C8 N2 123.4(3) n
O5 P1 C8 C9 60.0(3) n
O4 P1 C8 C9 -177.5(3) n
O3 P1 C8 C9 -63.6(3) n
N2 C8 C9 C14 -117.9(4) n
P1 C8 C9 C14 70.0(4) n
N2 C8 C9 C10 63.6(5) n
P1 C8 C9 C10 -108.5(3) n
C14 C9 C10 C11 -0.6(5) n
C8 C9 C10 C11 178.0(3) n
C9 C10 C11 C12 0.1(6) n
C10 C11 C12 C13 0.9(6) n
C11 C12 C13 C14 -1.4(6) n
C12 C13 C14 C9 1.0(6) n
C10 C9 C14 C13 0.0(5) n
C8 C9 C14 C13 -178.5(3) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21179046
2 PubChem 6370904
