#------------------------------------------------------------------------------
#$Date: 2017-01-03 16:30:46 +0200 (Tue, 03 Jan 2017) $
#$Revision: 189762 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/22/4022226.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4022226
loop_
_publ_author_name
'Eric Mattmann'
'François Mercier'
'Louis Ricard'
'François Mathey'
_publ_contact_author
;
 Louis Ricard,
 Labo DCPH,
 Ecole Polytechnique
 Route de Saclay
 91128 Palaiseau
 France
;
_publ_contact_author_email       louis.ricard@polytechnique.fr
_publ_contact_author_fax         01-69-33-39-90
_publ_contact_author_phone       01-69-33-45-72
_publ_section_title
;
 Synthesis of New Tricyclic Phosphines and Phosphinites
 by Intramolecular Diels-Alder Reactions of Trivalent Phospholes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5422
_journal_page_last               5425
_journal_paper_doi               10.1021/jo025713+
_journal_volume                  67
_journal_year                    2002
_chemical_formula_sum            'C9 H13 O P S'
_chemical_formula_weight         200.22
_chemical_name_systematic
; 
 ? 
;
_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_date             03-04-02
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.619(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8411(4)
_cell_length_b                   7.2542(2)
_cell_length_c                   12.8170(5)
_cell_measurement_reflns_used    251
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      3.0
_cell_volume                     987.32(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4960
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.93
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.9573
_exptl_absorpt_correction_T_min  0.9172
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.836
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0998P)²+1.5286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1812
_refine_ls_wR_factor_ref         0.1923
_reflns_number_gt                2338
_reflns_number_total             2870
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo025713+_s2_1.cif
_cod_data_source_block           tricypos,_2(PS)
_cod_depositor_comments
;
 Changing the atom site type symbol of atom 'P1' from 'S' to 'P' and
 the atom site type symbol of atom 'S1' from 'P' to 'S' after consulting
 the original publication.

 Antanas Vaitkus,
 2017-01-03

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 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022226
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.77426(6) 0.02826(9) 0.47224(5) 0.0288(2) Uani 1 1 d .
S1 S 0.76327(8) -0.20605(10) 0.53902(6) 0.0352(2) Uani 1 1 d .
O1 O 0.8043(2) 0.0111(3) 0.35379(16) 0.0343(5) Uani 1 1 d .
C1 C 0.8793(2) 0.2192(3) 0.5224(2) 0.0264(5) Uani 1 1 d .
H1 H 0.9705 0.1873 0.5450 0.032 Uiso 1 1 calc R
C2 C 0.8166(2) 0.2951(3) 0.60824(19) 0.0231(5) Uani 1 1 d .
C3 C 0.6914(2) 0.2845(4) 0.57937(19) 0.0259(5) Uani 1 1 d .
C4 C 0.6517(3) 0.2075(4) 0.4672(2) 0.0286(5) Uani 1 1 d .
H4 H 0.5623 0.1652 0.4460 0.034 Uiso 1 1 calc R
C5 C 0.6966(3) 0.3512(4) 0.3927(2) 0.0330(6) Uani 1 1 d .
H5A H 0.6574 0.3273 0.3172 0.040 Uiso 1 1 calc R
H5B H 0.6752 0.4781 0.4114 0.040 Uiso 1 1 calc R
C6 C 0.8409(3) 0.3245(4) 0.4121(2) 0.0326(6) Uani 1 1 d .
H6 H 0.8878 0.4428 0.4103 0.039 Uiso 1 1 calc R
C7 C 0.8671(3) 0.1835(5) 0.3300(3) 0.0406(7) Uani 1 1 d .
H7A H 0.8318 0.2262 0.2567 0.049 Uiso 1 1 calc R
H7B H 0.9588 0.1638 0.3372 0.049 Uiso 1 1 calc R
C10 C 0.8934(3) 0.3699(5) 0.7095(2) 0.0387(7) Uani 1 1 d .
H10A H 0.9378 0.4811 0.6940 0.058 Uiso 1 1 calc R
H10B H 0.9548 0.2770 0.7422 0.058 Uiso 1 1 calc R
H10C H 0.8379 0.4006 0.7586 0.058 Uiso 1 1 calc R
C11 C 0.5952(3) 0.3493(5) 0.6396(3) 0.0405(7) Uani 1 1 d .
H11A H 0.6363 0.3777 0.7131 0.061 Uiso 1 1 calc R
H11B H 0.5322 0.2524 0.6395 0.061 Uiso 1 1 calc R
H11C H 0.5539 0.4603 0.6056 0.061 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0343(4) 0.0288(3) 0.0247(3) -0.0034(2) 0.0096(2) -0.0009(2)
S1 0.0493(5) 0.0220(3) 0.0359(4) 0.0009(3) 0.0127(3) -0.0037(3)
O1 0.0475(12) 0.0337(10) 0.0257(9) -0.0076(7) 0.0170(9) -0.0017(8)
C1 0.0267(12) 0.0272(12) 0.0271(12) -0.0029(9) 0.0099(9) 0.0008(9)
C2 0.0269(11) 0.0237(11) 0.0193(10) -0.0018(8) 0.0060(8) 0.0008(8)
C3 0.0263(11) 0.0322(12) 0.0201(10) 0.0025(9) 0.0068(9) 0.0054(9)
C4 0.0308(12) 0.0330(13) 0.0216(11) 0.0002(9) 0.0047(9) 0.0003(10)
C5 0.0411(15) 0.0327(13) 0.0238(12) 0.0038(10) 0.0037(10) -0.0021(11)
C6 0.0409(15) 0.0310(13) 0.0305(13) 0.0035(10) 0.0183(11) 0.0011(11)
C7 0.0519(18) 0.0427(16) 0.0328(14) 0.0001(12) 0.0216(13) 0.0005(13)
C10 0.0367(15) 0.0488(17) 0.0280(13) -0.0110(12) 0.0007(11) -0.0043(13)
C11 0.0328(14) 0.0561(19) 0.0357(15) -0.0015(14) 0.0140(12) 0.0119(13)
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'
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
O1 P1 C1 99.16(11)
O1 P1 C4 107.44(11)
C1 P1 C4 82.65(12)
O1 P1 S1 113.11(8)
C1 P1 S1 127.28(9)
C4 P1 S1 121.97(10)
C7 O1 P1 108.35(16)
C2 C1 C6 113.4(2)
C2 C1 P1 101.11(16)
C6 C1 P1 91.06(17)
C3 C2 C10 128.2(2)
C3 C2 C1 111.0(2)
C10 C2 C1 120.8(2)
C2 C3 C11 128.0(2)
C2 C3 C4 111.2(2)
C11 C3 C4 120.6(2)
C3 C4 C5 105.6(2)
C3 C4 P1 99.24(17)
C5 C4 P1 100.43(18)
C6 C5 C4 104.4(2)
C7 C6 C5 107.1(3)
C7 C6 C1 103.8(2)
C5 C6 C1 106.2(2)
O1 C7 C6 105.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.620(2)
P1 C1 1.826(3)
P1 C4 1.851(3)
P1 S1 1.9176(10)
O1 C7 1.484(4)
C1 C2 1.509(3)
C1 C6 1.586(4)
C2 C3 1.335(3)
C2 C10 1.496(4)
C3 C11 1.493(4)
C3 C4 1.522(4)
C4 C5 1.557(4)
C5 C6 1.547(4)
C6 C7 1.535(4)
