#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/68/2216843.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_2216843
loop_
_publ_author_name
'Mague, Joel T.'
'Punji, Benudhar'
'Ganesamoorthy, Chelladurai'
'Balakrishna, Maravanji S.'
_publ_section_title
;
 O-2-Naphthyl diphenylselenophosphinate
;
_journal_coeditor_code           XU2359
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4645
_journal_page_last               o4645
_journal_paper_doi               10.1107/S1600536807056334
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C22 H17 O P Se'
_chemical_formula_moiety         'C22 H17 O P Se'
_chemical_formula_sum            'C22 H17 O P Se'
_chemical_formula_weight         407.29
_chemical_melting_point          392.0(10)
_chemical_name_systematic
;
O-2-Naphthyl diphenylselenophosphinate
;
_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                 105.6720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9490(8)
_cell_length_b                   19.044(2)
_cell_length_c                   9.9552(8)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.20
_cell_measurement_theta_min      2.38
_cell_volume                     1816.1(3)
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0247
_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            30965
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.162
_exptl_absorpt_correction_T_max  0.7269
_exptl_absorpt_correction_T_min  0.5450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.952
_refine_diff_density_min         -0.612
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0333
_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)+(0.0534P)²+0.981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                3896
_reflns_number_total             4675
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2359.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 '391-393' was changed to '392.0(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 '391-393' was changed to '392.0(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_sg_symbol_H-M      'P 21/n'
_cod_database_code               2216843
_cod_database_fobs_code          2216843
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
Se Se1 0.49213(2) 0.142334(11) 0.58260(2) 0.02478(8) Uani d . 1
P P1 0.36997(5) 0.18120(3) 0.39250(5) 0.01726(11) Uani d . 1
O O1 0.22562(14) 0.21964(7) 0.39571(14) 0.0206(3) Uani d . 1
C C1 0.21246(19) 0.27988(10) 0.4718(2) 0.0192(4) Uani d . 1
C C2 0.0736(2) 0.30497(12) 0.4418(2) 0.0229(4) Uani d . 1
H H2 0.0012 0.2816 0.3746 0.027 Uiso calc R 1
C C3 0.0441(2) 0.36264(11) 0.5095(2) 0.0258(4) Uani d . 1
H H3 -0.0489 0.3799 0.4879 0.031 Uiso calc R 1
C C4 0.1507(2) 0.39731(11) 0.6119(2) 0.0231(4) Uani d . 1
C C5 0.1234(2) 0.45743(12) 0.6846(3) 0.0309(5) Uani d . 1
H H5 0.0312 0.4756 0.6646 0.037 Uiso calc R 1
C C6 0.2283(3) 0.48944(13) 0.7830(3) 0.0352(5) Uani d . 1
H H6 0.2085 0.5295 0.8313 0.042 Uiso calc R 1
C C7 0.3657(3) 0.46325(12) 0.8133(2) 0.0321(5) Uani d . 1
H H7 0.4380 0.4859 0.8816 0.038 Uiso calc R 1
C C8 0.3961(2) 0.40536(11) 0.7450(2) 0.0252(4) Uani d . 1
H H8 0.4891 0.3882 0.7667 0.030 Uiso calc R 1
C C9 0.2897(2) 0.37103(11) 0.6423(2) 0.0208(4) Uani d . 1
C C10 0.3189(2) 0.31175(10) 0.5677(2) 0.0197(4) Uani d . 1
H H10 0.4117 0.2946 0.5846 0.024 Uiso calc R 1
C C11 0.45437(19) 0.24513(10) 0.30831(19) 0.0185(4) Uani d . 1
C C12 0.3740(2) 0.29457(11) 0.2174(2) 0.0219(4) Uani d . 1
H H12 0.2760 0.2965 0.2051 0.026 Uiso calc R 1
C C13 0.4370(2) 0.34104(12) 0.1447(2) 0.0276(4) Uani d . 1
H H13 0.3820 0.3740 0.0817 0.033 Uiso calc R 1
C C14 0.5804(2) 0.33876(12) 0.1649(2) 0.0293(5) Uani d . 1
H H14 0.6236 0.3701 0.1151 0.035 Uiso calc R 1
C C15 0.6610(2) 0.29102(12) 0.2574(2) 0.0279(5) Uani d . 1
H H15 0.7594 0.2907 0.2721 0.033 Uiso calc R 1
C C16 0.5994(2) 0.24347(11) 0.3291(2) 0.0228(4) Uani d . 1
H H16 0.6550 0.2103 0.3913 0.027 Uiso calc R 1
C C17 0.29536(19) 0.11402(10) 0.26658(19) 0.0187(4) Uani d . 1
C C18 0.3096(2) 0.04341(11) 0.3035(2) 0.0247(4) Uani d . 1
H H18 0.3610 0.0302 0.3949 0.030 Uiso calc R 1
C C19 0.2487(2) -0.00782(12) 0.2068(2) 0.0289(5) Uani d . 1
H H19 0.2576 -0.0560 0.2323 0.035 Uiso calc R 1
C C20 0.1746(2) 0.01165(12) 0.0725(2) 0.0280(5) Uani d . 1
H H20 0.1337 -0.0234 0.0062 0.034 Uiso calc R 1
C C21 0.1601(2) 0.08144(13) 0.0353(2) 0.0280(4) Uani d . 1
H H21 0.1089 0.0943 -0.0565 0.034 Uiso calc R 1
C C22 0.2201(2) 0.13322(11) 0.1311(2) 0.0234(4) Uani d . 1
H H22 0.2102 0.1813 0.1050 0.028 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'
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'
Se Se -0.0929 2.2259 '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 97.68(8) y
O1 P1 C11 103.29(8) y
C17 P1 C11 108.10(9) y
O1 P1 Se1 116.37(5) y
C17 P1 Se1 114.05(7) y
C11 P1 Se1 115.41(6) y
C1 O1 P1 126.43(12) y
C10 C1 O1 125.14(17) ?
C10 C1 C2 121.84(18) ?
O1 C1 C2 113.00(17) ?
C3 C2 C1 119.76(19) ?
C3 C2 H2 120.1 ?
C1 C2 H2 120.1 ?
C2 C3 C4 120.74(19) ?
C2 C3 H3 119.6 ?
C4 C3 H3 119.6 ?
C5 C4 C3 122.15(19) ?
C5 C4 C9 118.9(2) ?
C3 C4 C9 118.93(18) ?
C6 C5 C4 120.7(2) ?
C6 C5 H5 119.6 ?
C4 C5 H5 119.6 ?
C5 C6 C7 120.3(2) ?
C5 C6 H6 119.9 ?
C7 C6 H6 119.9 ?
C8 C7 C6 120.7(2) ?
C8 C7 H7 119.7 ?
C6 C7 H7 119.7 ?
C7 C8 C9 120.5(2) ?
C7 C8 H8 119.8 ?
C9 C8 H8 119.8 ?
C8 C9 C10 121.63(18) ?
C8 C9 C4 118.96(19) ?
C10 C9 C4 119.40(18) ?
C1 C10 C9 119.29(18) ?
C1 C10 H10 120.4 ?
C9 C10 H10 120.4 ?
C12 C11 C16 119.78(18) ?
C12 C11 P1 119.85(14) ?
C16 C11 P1 120.32(15) ?
C13 C12 C11 120.33(19) ?
C13 C12 H12 119.8 ?
C11 C12 H12 119.8 ?
C14 C13 C12 119.6(2) ?
C14 C13 H13 120.2 ?
C12 C13 H13 120.2 ?
C15 C14 C13 120.3(2) ?
C15 C14 H14 119.8 ?
C13 C14 H14 119.8 ?
C14 C15 C16 120.77(19) ?
C14 C15 H15 119.6 ?
C16 C15 H15 119.6 ?
C15 C16 C11 119.2(2) ?
C15 C16 H16 120.4 ?
C11 C16 H16 120.4 ?
C18 C17 C22 119.71(18) ?
C18 C17 P1 120.56(15) ?
C22 C17 P1 119.72(15) ?
C19 C18 C17 120.10(19) ?
C19 C18 H18 120.0 ?
C17 C18 H18 119.9 ?
C18 C19 C20 119.8(2) ?
C18 C19 H19 120.1 ?
C20 C19 H19 120.1 ?
C21 C20 C19 120.4(2) ?
C21 C20 H20 119.8 ?
C19 C20 H20 119.8 ?
C20 C21 C22 120.4(2) ?
C20 C21 H21 119.8 ?
C22 C21 H21 119.8 ?
C21 C22 C17 119.6(2) ?
C21 C22 H22 120.2 ?
C17 C22 H22 120.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Se1 P1 2.0890(5) y
P1 O1 1.6200(14) ?
P1 C17 1.805(2) ?
P1 C11 1.808(2) ?
O1 C1 1.400(2) ?
C1 C10 1.362(3) ?
C1 C2 1.416(3) ?
C2 C3 1.361(3) ?
C2 H2 0.9500 ?
C3 C4 1.420(3) ?
C3 H3 0.9500 ?
C4 C5 1.420(3) ?
C4 C9 1.424(3) ?
C5 C6 1.367(4) ?
C5 H5 0.9500 ?
C6 C7 1.409(3) ?
C6 H6 0.9500 ?
C7 C8 1.371(3) ?
C7 H7 0.9500 ?
C8 C9 1.417(3) ?
C8 H8 0.9500 ?
C9 C10 1.424(3) ?
C10 H10 0.9500 ?
C11 C12 1.398(3) ?
C11 C16 1.401(3) ?
C12 C13 1.395(3) ?
C12 H12 0.9500 ?
C13 C14 1.387(3) ?
C13 H13 0.9500 ?
C14 C15 1.385(3) ?
C14 H14 0.9500 ?
C15 C16 1.393(3) ?
C15 H15 0.9500 ?
C16 H16 0.9500 ?
C17 C18 1.391(3) ?
C17 C22 1.403(3) ?
C18 C19 1.390(3) ?
C18 H18 0.9500 ?
C19 C20 1.391(3) ?
C19 H19 0.9500 ?
C20 C21 1.377(3) ?
C20 H20 0.9500 ?
C21 C22 1.390(3) ?
C21 H21 0.9500 ?
C22 H22 0.9500 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655399
2 PubChem 139073887
