#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/68/2216842.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_2216842
loop_
_publ_author_name
'Mague, Joel T.'
'Punji, Benudhar'
'Ganesamoorthy, Chelladurai'
'Balakrishna, Maravanji S.'
_publ_section_title
;
 O-2-Naphthyl diphenylthiophosphinate
;
_journal_coeditor_code           XU2358
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4644
_journal_page_last               o4644
_journal_paper_doi               10.1107/S1600536807056127
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C22 H17 O P S'
_chemical_formula_moiety         'C22 H17 O P S'
_chemical_formula_sum            'C22 H17 O P S'
_chemical_formula_weight         360.39
_chemical_melting_point          374.0(10)
_chemical_name_systematic
;
O-2-Naphthyl diphenylthiophosphinate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.8340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7701(3)
_cell_length_b                   19.1380(6)
_cell_length_c                   9.8933(3)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.36
_cell_measurement_theta_min      2.39
_cell_volume                     1779.66(10)
_computing_cell_refinement       'APEX2 (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2006)'
_computing_molecular_graphics    'APEX2 (Bruker, 2007)'
_computing_publication_material  'APEX2 (Bruker, 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            31295
_diffrn_reflns_theta_full        28.74
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_min         2.39
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.9660
_exptl_absorpt_correction_T_min  0.9082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.346
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0384P)²+0.8993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0837
_reflns_number_gt                4083
_reflns_number_total             4573
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2358.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '373-375' was changed to '374.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '373-375' was changed to '374.0(10)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1779.70(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2216842
_cod_database_fobs_code          2216842
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 -0.08033(3) 0.849586(17) 0.01116(3) 0.02282(9) Uani d . 1
P P1 0.10022(3) 0.816997(15) 0.12964(3) 0.01521(8) Uani d . 1
O O1 0.09681(9) 0.78019(5) 0.27593(9) 0.01828(17) Uani d . 1
C C1 0.02383(12) 0.71931(6) 0.29126(12) 0.0169(2) Uani d . 1
C C2 0.05707(13) 0.69478(7) 0.43088(13) 0.0201(2) Uani d . 1
H H2 0.1247 0.7189 0.5031 0.024 Uiso calc R 1
C C3 -0.00811(14) 0.63626(7) 0.46202(13) 0.0220(2) Uani d . 1
H H3 0.0156 0.6194 0.5559 0.026 Uiso calc R 1
C C4 -0.11095(13) 0.60028(6) 0.35561(13) 0.0202(2) Uani d . 1
C C5 -0.17985(15) 0.53896(7) 0.38492(15) 0.0258(3) Uani d . 1
H H5 -0.1578 0.5214 0.4782 0.031 Uiso calc R 1
C C6 -0.27766(15) 0.50503(7) 0.28000(16) 0.0293(3) Uani d . 1
H H6 -0.3230 0.4641 0.3008 0.035 Uiso calc R 1
C C7 -0.31155(14) 0.53064(7) 0.14100(16) 0.0276(3) Uani d . 1
H H7 -0.3793 0.5066 0.0688 0.033 Uiso calc R 1
C C8 -0.24774(13) 0.58994(7) 0.10886(14) 0.0221(2) Uani d . 1
H H8 -0.2724 0.6069 0.0150 0.026 Uiso calc R 1
C C9 -0.14487(12) 0.62608(6) 0.21541(13) 0.0178(2) Uani d . 1
C C10 -0.07381(12) 0.68640(6) 0.18446(12) 0.0175(2) Uani d . 1
H H10 -0.0938 0.7036 0.0910 0.021 Uiso calc R 1
C C11 0.19044(12) 0.75353(6) 0.04975(12) 0.0161(2) Uani d . 1
C C12 0.28582(13) 0.70621(6) 0.13399(13) 0.0194(2) Uani d . 1
H H12 0.2988 0.7058 0.2327 0.023 Uiso calc R 1
C C13 0.36164(14) 0.65980(7) 0.07347(15) 0.0240(3) Uani d . 1
H H13 0.4275 0.6282 0.1309 0.029 Uiso calc R 1
C C14 0.34077(15) 0.65982(7) -0.07084(15) 0.0257(3) Uani d . 1
H H14 0.3932 0.6285 -0.1120 0.031 Uiso calc R 1
C C15 0.24383(14) 0.70530(7) -0.15556(13) 0.0242(3) Uani d . 1
H H15 0.2283 0.7041 -0.2546 0.029 Uiso calc R 1
C C16 0.16905(13) 0.75275(7) -0.09583(12) 0.0197(2) Uani d . 1
H H16 0.1039 0.7844 -0.1538 0.024 Uiso calc R 1
C C17 0.22356(12) 0.88595(6) 0.20284(12) 0.0171(2) Uani d . 1
C C18 0.17919(14) 0.95549(7) 0.18510(13) 0.0217(2) Uani d . 1
H H18 0.0849 0.9665 0.1323 0.026 Uiso calc R 1
C C19 0.27334(16) 1.00869(7) 0.24487(14) 0.0261(3) Uani d . 1
H H19 0.2431 1.0560 0.2336 0.031 Uiso calc R 1
C C20 0.41147(15) 0.99270(7) 0.32104(14) 0.0260(3) Uani d . 1
H H20 0.4755 1.0292 0.3615 0.031 Uiso calc R 1
C C21 0.45647(14) 0.92363(7) 0.33830(14) 0.0251(3) Uani d . 1
H H21 0.5512 0.9130 0.3903 0.030 Uiso calc R 1
C C22 0.36292(13) 0.87011(7) 0.27945(13) 0.0211(2) Uani d . 1
H H22 0.3936 0.8228 0.2913 0.025 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'
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'
O O 0.0106 0.0060 '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
O1 P1 C17 97.71(5) y
O1 P1 C11 103.32(5) y
C17 P1 C11 108.43(5) y
O1 P1 S1 116.37(4) y
C17 P1 S1 114.00(4) y
C11 P1 S1 115.15(4) y
C1 O1 P1 126.61(8) y
C10 C1 O1 124.71(10) ?
C10 C1 C2 121.92(11) ?
O1 C1 C2 113.35(10) ?
C3 C2 C1 119.83(11) ?
C3 C2 H2 120.1 ?
C1 C2 H2 120.1 ?
C2 C3 C4 120.68(11) ?
C2 C3 H3 119.7 ?
C4 C3 H3 119.7 ?
C3 C4 C5 121.87(12) ?
C3 C4 C9 118.94(11) ?
C5 C4 C9 119.19(12) ?
C6 C5 C4 120.58(13) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C5 C6 C7 120.27(12) ?
C5 C6 H6 119.9 ?
C7 C6 H6 119.9 ?
C8 C7 C6 120.79(13) ?
C8 C7 H7 119.6 ?
C6 C7 H7 119.6 ?
C7 C8 C9 120.27(12) ?
C7 C8 H8 119.9 ?
C9 C8 H8 119.9 ?
C8 C9 C10 121.52(11) ?
C8 C9 C4 118.90(11) ?
C10 C9 C4 119.57(11) ?
C1 C10 C9 119.04(11) ?
C1 C10 H10 120.5 ?
C9 C10 H10 120.5 ?
C16 C11 C12 119.65(11) ?
C16 C11 P1 120.32(9) ?
C12 C11 P1 120.00(9) ?
C13 C12 C11 120.17(11) ?
C13 C12 H12 119.9 ?
C11 C12 H12 119.9 ?
C14 C13 C12 119.79(12) ?
C14 C13 H13 120.1 ?
C12 C13 H13 120.1 ?
C13 C14 C15 120.46(12) ?
C13 C14 H14 119.8 ?
C15 C14 H14 119.8 ?
C14 C15 C16 120.20(12) ?
C14 C15 H15 119.9 ?
C16 C15 H15 119.9 ?
C15 C16 C11 119.69(12) ?
C15 C16 H16 120.2 ?
C11 C16 H16 120.2 ?
C18 C17 C22 119.85(11) ?
C18 C17 P1 119.83(9) ?
C22 C17 P1 120.32(9) ?
C19 C18 C17 119.84(12) ?
C19 C18 H18 120.1 ?
C17 C18 H18 120.1 ?
C20 C19 C18 120.10(12) ?
C20 C19 H19 119.9 ?
C18 C19 H19 119.9 ?
C19 C20 C21 120.31(12) ?
C19 C20 H20 119.8 ?
C21 C20 H20 119.8 ?
C20 C21 C22 119.99(12) ?
C20 C21 H21 120.0 ?
C22 C21 H21 120.0 ?
C21 C22 C17 119.91(12) ?
C21 C22 H22 120.0 ?
C17 C22 H22 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 P1 1.9355(4) y
P1 O1 1.6182(9) ?
P1 C17 1.8004(12) ?
P1 C11 1.8048(12) ?
O1 C1 1.3957(14) ?
C1 C10 1.3685(16) ?
C1 C2 1.4103(16) ?
C2 C3 1.3645(18) ?
C2 H2 0.9500 ?
C3 C4 1.4194(18) ?
C3 H3 0.9500 ?
C4 C5 1.4217(18) ?
C4 C9 1.4236(17) ?
C5 C6 1.368(2) ?
C5 H5 0.9500 ?
C6 C7 1.412(2) ?
C6 H6 0.9500 ?
C7 C8 1.3732(18) ?
C7 H7 0.9500 ?
C8 C9 1.4218(17) ?
C8 H8 0.9500 ?
C9 C10 1.4229(16) ?
C10 H10 0.9500 ?
C11 C16 1.3979(16) ?
C11 C12 1.3996(16) ?
C12 C13 1.3923(17) ?
C12 H12 0.9500 ?
C13 C14 1.386(2) ?
C13 H13 0.9500 ?
C14 C15 1.387(2) ?
C14 H14 0.9500 ?
C15 C16 1.3941(18) ?
C15 H15 0.9500 ?
C16 H16 0.9500 ?
C17 C18 1.3959(17) ?
C17 C22 1.3990(16) ?
C18 C19 1.3912(18) ?
C18 H18 0.9500 ?
C19 C20 1.388(2) ?
C19 H19 0.9500 ?
C20 C21 1.389(2) ?
C20 H20 0.9500 ?
C21 C22 1.3904(17) ?
C21 H21 0.9500 ?
C22 H22 0.9500 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21120173
