#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/59/4115906.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_4115906
loop_
_publ_author_name
'Sudha Kumaraswamy'
'C. Muthiah'
'K. C. Kumara Swamy'
_publ_section_title
;
 Characterization of Stereoisomers of Spirophosphoranes Bearing an
 Eight-Membered Ring: Implications on Apicophilicity in Trigonal
 Bipyramidal Phosphorus
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              964
_journal_page_last               965
_journal_paper_doi               10.1021/ja992304v
_journal_volume                  122
_journal_year                    2000
_chemical_formula_sum            'C38.5 H38 Cl5 O4 P S'
_chemical_formula_weight         804.97
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.49(3)
_cell_angle_beta                 79.47(3)
_cell_angle_gamma                85.56(5)
_cell_formula_units_Z            2
_cell_length_a                   11.656(6)
_cell_length_b                   12.354(9)
_cell_length_c                   13.738(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1925.3(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5805
_diffrn_reflns_theta_full        23.67
_diffrn_reflns_theta_max         23.67
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.512
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             834
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0753
_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)+(0.1592P)²+0.2979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1828
_refine_ls_wR_factor_ref         0.2435
_reflns_number_gt                3608
_reflns_number_total             5805
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja992304v_4.cif
_cod_data_source_block           compound7(Kumara_Swamy)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'triclinc' was replaced with
'triclinic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1592P)^2^+0.2979P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1592P)^2^+0.2979P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1925.4(18)
_cod_original_formula_sum        'C38.50 H38 Cl5 O4 P S'
_cod_database_code               4115906
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_calc_flag
_atom_site_refinement_flags
P P 0.30370(11) 0.71937(10) 0.68950(10) 0.0542(4) Uani 1 d .
S S 0.45162(12) 0.64539(11) 0.74896(11) 0.0693(5) Uani 1 d .
Cl1 Cl 0.12211(13) 0.38584(11) 0.73266(13) 0.0815(5) Uani 1 d .
Cl2 Cl -0.10922(14) 0.42110(12) 0.64364(15) 0.0924(6) Uani 1 d .
Cl3 Cl -0.18362(13) 0.64998(13) 0.54842(13) 0.0849(5) Uani 1 d .
Cl4 Cl -0.02495(12) 0.84758(11) 0.54055(11) 0.0737(5) Uani 1 d .
Cl5 Cl 0.2663(2) 0.3993(3) 1.16828(16) 0.1540(12) Uani 1 d .
O1 O 0.3980(3) 0.7696(3) 0.6001(3) 0.0594(9) Uani 1 d .
O2 O 0.2599(3) 0.7902(3) 0.7795(2) 0.0599(9) Uani 1 d .
O3 O 0.2506(3) 0.5971(2) 0.7018(3) 0.0581(9) Uani 1 d .
O4 O 0.1936(3) 0.7717(2) 0.6266(2) 0.0544(8) Uani 1 d .
C1 C 0.3781(4) 0.8502(4) 0.5204(4) 0.0578(12) Uani 1 d .
C2 C 0.3984(4) 0.8235(4) 0.4248(4) 0.0600(13) Uani 1 d .
C3 C 0.3780(5) 0.9079(5) 0.3530(4) 0.0691(14) Uani 1 d .
H3 H 0.3888 0.8930 0.2872 0.083 Uiso 1 calc R
C4 C 0.3424(5) 1.0131(4) 0.3728(4) 0.0689(14) Uani 1 d .
C5 C 0.3282(5) 1.0354(4) 0.4695(4) 0.0658(14) Uani 1 d .
H5 H 0.3065 1.1063 0.4841 0.079 Uiso 1 calc R
C6 C 0.3453(4) 0.9551(4) 0.5448(4) 0.0590(12) Uani 1 d .
C7 C 0.3284(5) 0.9816(4) 0.6515(4) 0.0660(13) Uani 1 d .
H7A H 0.3821 0.9340 0.6860 0.079 Uiso 1 calc R
H7B H 0.3499 1.0561 0.6502 0.079 Uiso 1 calc R
C8 C 0.2079(5) 0.9705(4) 0.7107(4) 0.0614(13) Uani 1 d .
C9 C 0.1227(5) 1.0543(4) 0.7015(4) 0.0663(14) Uani 1 d .
H9 H 0.1415 1.1168 0.6575 0.080 Uiso 1 calc R
C10 C 0.0123(5) 1.0478(4) 0.7550(4) 0.0687(14) Uani 1 d .
C11 C -0.0120(5) 0.9588(4) 0.8259(4) 0.0696(14) Uani 1 d .
H11 H -0.0862 0.9561 0.8647 0.084 Uiso 1 calc R
C12 C 0.0696(5) 0.8729(4) 0.8418(4) 0.0626(13) Uani 1 d .
C13 C 0.1753(4) 0.8798(4) 0.7771(4) 0.0582(12) Uani 1 d .
C14 C 0.4434(5) 0.7091(4) 0.3964(4) 0.0690(14) Uani 1 d .
C15 C 0.3701(6) 0.6187(5) 0.4554(5) 0.0829(16) Uani 1 d .
H15A H 0.3853 0.6070 0.5224 0.124 Uiso 1 calc R
H15B H 0.3898 0.5526 0.4248 0.124 Uiso 1 calc R
H15C H 0.2888 0.6392 0.4562 0.124 Uiso 1 calc R
C16 C 0.5676(5) 0.6881(5) 0.4187(7) 0.106(3) Uani 1 d .
H16A H 0.6176 0.7405 0.3773 0.159 Uiso 1 calc R
H16B H 0.5961 0.6156 0.4052 0.159 Uiso 1 calc R
H16C H 0.5670 0.6951 0.4876 0.159 Uiso 1 calc R
C17 C 0.4432(9) 0.7007(6) 0.2871(5) 0.124(3) Uani 1 d .
H17A H 0.3674 0.7240 0.2717 0.186 Uiso 1 calc R
H17B H 0.4613 0.6262 0.2742 0.186 Uiso 1 calc R
H17C H 0.5007 0.7465 0.2464 0.186 Uiso 1 calc R
C18 C 0.3236(7) 1.1018(5) 0.2899(5) 0.096(2) Uani 1 d .
H18A H 0.2452 1.1332 0.3034 0.144 Uiso 1 calc R
H18B H 0.3357 1.0712 0.2279 0.144 Uiso 1 calc R
H18C H 0.3779 1.1575 0.2858 0.144 Uiso 1 calc R
C19 C -0.0824(6) 1.1350(5) 0.7394(5) 0.0897(19) Uani 1 d .
H19A H -0.0606 1.2031 0.7553 0.135 Uiso 1 calc R
H19B H -0.1542 1.1144 0.7820 0.135 Uiso 1 calc R
H19C H -0.0928 1.1430 0.6711 0.135 Uiso 1 calc R
C20 C 0.0416(6) 0.7835(5) 0.9297(4) 0.0764(16) Uani 1 d .
C21 C 0.1335(7) 0.7823(6) 0.9970(5) 0.105(2) Uani 1 d .
H21A H 0.1136 0.7310 1.0555 0.157 Uiso 1 calc R
H21B H 0.1354 0.8540 1.0164 0.157 Uiso 1 calc R
H21C H 0.2089 0.7612 0.9614 0.157 Uiso 1 calc R
C22 C -0.0765(7) 0.8056(6) 0.9948(5) 0.103(2) Uani 1 d .
H22A H -0.1375 0.8051 0.9565 0.155 Uiso 1 calc R
H22B H -0.0783 0.8758 1.0181 0.155 Uiso 1 calc R
H22C H -0.0881 0.7500 1.0509 0.155 Uiso 1 calc R
C23 C 0.0422(7) 0.6700(5) 0.8968(6) 0.101(2) Uani 1 d .
H23A H 0.0183 0.6182 0.9540 0.151 Uiso 1 calc R
H23B H 0.1195 0.6491 0.8649 0.151 Uiso 1 calc R
H23C H -0.0110 0.6715 0.8509 0.151 Uiso 1 calc R
C24 C 0.1451(4) 0.5983(4) 0.6684(4) 0.0539(11) Uani 1 d .
C25 C 0.0792(4) 0.5103(4) 0.6768(4) 0.0568(12) Uani 1 d .
C26 C -0.0232(4) 0.5287(4) 0.6379(4) 0.0595(13) Uani 1 d .
C27 C -0.0573(4) 0.6305(4) 0.5970(4) 0.0566(12) Uani 1 d .
C28 C 0.0127(4) 0.7190(4) 0.5901(3) 0.0505(11) Uani 1 d .
C29 C 0.1136(4) 0.6984(4) 0.6271(3) 0.0476(10) Uani 1 d .
C30 C 0.3923(5) 0.5781(4) 0.8669(4) 0.0648(13) Uani 1 d .
C31 C 0.3420(5) 0.4783(4) 0.8767(4) 0.0730(15) Uani 1 d .
H31 H 0.3346 0.4475 0.8201 0.088 Uiso 1 calc R
C32 C 0.3033(5) 0.4250(6) 0.9690(5) 0.0866(18) Uani 1 d .
H32 H 0.2702 0.3578 0.9748 0.104 Uiso 1 calc R
C33 C 0.3127(6) 0.4693(7) 1.0519(5) 0.097(2) Uani 1 d .
C34 C 0.3633(7) 0.5680(7) 1.0431(6) 0.103(2) Uani 1 d .
H34 H 0.3710 0.5983 1.0999 0.124 Uiso 1 calc R
C35 C 0.4015(6) 0.6206(6) 0.9522(5) 0.0895(19) Uani 1 d .
H35 H 0.4351 0.6874 0.9472 0.107 Uiso 1 calc R
C36 C 0.418(3) 0.052(3) -0.0525(17) 0.290(13) Uani 1 d D
C37 C 0.584(4) 0.060(3) 0.046(2) 0.35(2) Uani 1 d D
C38 C 0.489(3) 0.1083(19) -0.0138(15) 0.282(13) Uani 1 d D
C39 C 0.348(2) 0.060(3) -0.096(2) 0.179(14) Uani 0.50 d PD
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'
Cl Cl 0.1484 0.1585 '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'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
O1 P O2 117.45(19) . .
O1 P O3 126.35(19) . .
O2 P O3 116.12(19) . .
O1 P O4 90.28(17) . .
O2 P O4 93.42(17) . .
O3 P O4 89.32(16) . .
O1 P S 84.59(13) . .
O2 P S 94.36(14) . .
O3 P S 88.82(13) . .
O4 P S 172.03(14) . .
C30 S P 104.66(18) . .
C1 O1 P 127.3(3) . .
C13 O2 P 124.2(3) . .
C24 O3 P 113.3(3) . .
C29 O4 P 112.8(3) . .
C2 C1 C6 123.8(5) . .
C2 C1 O1 119.6(4) . .
C6 C1 O1 116.5(5) . .
C1 C2 C3 115.0(5) . .
C1 C2 C14 124.0(5) . .
C3 C2 C14 120.9(5) . .
C4 C3 C2 123.9(6) . .
C3 C4 C5 118.1(5) . .
C3 C4 C18 120.9(6) . .
C5 C4 C18 121.0(5) . .
C6 C5 C4 121.1(5) . .
C5 C6 C1 118.0(5) . .
C5 C6 C7 120.2(5) . .
C1 C6 C7 121.8(4) . .
C8 C7 C6 116.0(4) . .
C13 C8 C9 116.6(5) . .
C13 C8 C7 123.2(5) . .
C9 C8 C7 120.3(5) . .
C10 C9 C8 122.0(5) . .
C9 C10 C11 118.5(5) . .
C9 C10 C19 121.9(5) . .
C11 C10 C19 119.6(6) . .
C10 C11 C12 122.9(5) . .
C13 C12 C11 115.0(5) . .
C13 C12 C20 124.8(5) . .
C11 C12 C20 120.1(5) . .
C12 C13 C8 124.4(5) . .
C12 C13 O2 119.4(4) . .
C8 C13 O2 116.2(5) . .
C17 C14 C15 106.4(6) . .
C17 C14 C16 110.1(6) . .
C15 C14 C16 107.9(5) . .
C17 C14 C2 111.8(5) . .
C15 C14 C2 112.9(5) . .
C16 C14 C2 107.7(5) . .
C22 C20 C21 106.1(5) . .
C22 C20 C23 107.8(6) . .
C21 C20 C23 109.0(6) . .
C22 C20 C12 112.5(5) . .
C21 C20 C12 108.3(5) . .
C23 C20 C12 112.9(5) . .
C29 C24 C25 123.1(4) . .
C29 C24 O3 111.9(4) . .
C25 C24 O3 124.9(4) . .
C24 C25 C26 115.9(4) . .
C24 C25 Cl1 121.0(4) . .
C26 C25 Cl1 123.1(4) . .
C27 C26 C25 121.6(4) . .
C27 C26 Cl2 119.9(4) . .
C25 C26 Cl2 118.6(4) . .
C26 C27 C28 120.7(4) . .
C26 C27 Cl3 120.3(4) . .
C28 C27 Cl3 118.9(4) . .
C29 C28 C27 116.5(4) . .
C29 C28 Cl4 120.5(4) . .
C27 C28 Cl4 123.0(4) . .
C24 C29 O4 112.0(4) . .
C24 C29 C28 122.1(4) . .
O4 C29 C28 125.8(4) . .
C35 C30 C31 117.8(6) . .
C35 C30 S 120.3(5) . .
C31 C30 S 121.7(4) . .
C32 C31 C30 120.5(6) . .
C33 C32 C31 120.3(7) . .
C32 C33 C34 119.7(7) . .
C32 C33 Cl5 119.8(7) . .
C34 C33 Cl5 120.4(6) . .
C35 C34 C33 119.9(7) . .
C34 C35 C30 121.7(7) . .
C39 C36 C38 143(4) . .
C39 C36 C37 90(3) . 2_655
C38 C36 C37 126(4) . 2_655
C36 C37 C38 107(4) 2_655 .
C36 C37 C39 38.1(18) 2_655 2_655
C38 C37 C39 145(3) . 2_655
C36 C38 C37 126(2) . .
C36 C39 C37 52(2) . 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P O1 1.585(4) .
P O2 1.594(4) .
P O3 1.653(3) .
P O4 1.716(3) .
P S 2.133(2) .
S C30 1.766(6) .
Cl1 C25 1.707(5) .
Cl2 C26 1.711(5) .
Cl3 C27 1.713(5) .
Cl4 C28 1.702(5) .
Cl5 C33 1.730(7) .
O1 C1 1.420(6) .
O2 C13 1.425(6) .
O3 C24 1.387(5) .
O4 C29 1.349(5) .
C1 C2 1.370(7) .
C1 C6 1.388(7) .
C2 C3 1.377(7) .
C2 C14 1.542(7) .
C3 C4 1.380(8) .
C4 C5 1.369(8) .
C4 C18 1.508(7) .
C5 C6 1.368(7) .
C6 C7 1.518(7) .
C7 C8 1.495(7) .
C8 C13 1.380(7) .
C8 C9 1.389(7) .
C9 C10 1.362(8) .
C10 C11 1.380(7) .
C10 C19 1.505(8) .
C11 C12 1.391(7) .
C12 C13 1.383(7) .
C12 C20 1.532(8) .
C14 C17 1.518(9) .
C14 C15 1.514(8) .
C14 C16 1.530(8) .
C20 C22 1.526(9) .
C20 C21 1.536(9) .
C20 C23 1.527(9) .
C24 C29 1.344(6) .
C24 C25 1.360(7) .
C25 C26 1.387(7) .
C26 C27 1.370(7) .
C27 C28 1.397(7) .
C28 C29 1.358(6) .
C30 C35 1.370(8) .
C30 C31 1.386(8) .
C31 C32 1.365(8) .
C32 C33 1.352(10) .
C33 C34 1.377(11) .
C34 C35 1.345(10) .
C36 C39 1.08(4) .
C36 C38 1.35(3) .
C36 C37 1.37(3) 2_655
C37 C36 1.37(3) 2_655
C37 C38 1.53(4) .
C37 C39 1.75(5) 2_655
C39 C37 1.75(5) 2_655
