#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/60/4116020.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_4116020
loop_
_publ_author_name
'Neil Burford'
'T. Stanley Cameron'
'Daren J. LeBlanc'
'Andrew D. Phillips'
'Thomas E. Concolino'
'Kin-Chung Lam'
'Arnold L. Rheingold'
_publ_contact_author_address
;  Department of Chemistry
   Dalhousie University
   Halifax, NS B3H 4J3
   CANADA
;
_publ_contact_author_email       burford@chem1.chem.dal.ca
_publ_contact_author_fax         '(902) 494-1310'
_publ_contact_author_name        'Neil Burford'
_publ_contact_author_phone       '(902) 494-3190'
_publ_section_title
;
 Iminophosphide Bonding Environments from Carbene Complexes of
 Iminophosphines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5413
_journal_page_last               5414
_journal_paper_doi               10.1021/ja000432+
_journal_volume                  122
_journal_year                    2000
_chemical_formula_sum            'C30 H49 F3 N3 O3 P S'
_chemical_formula_weight         619.75
_chemical_melting_point          424(1)
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.6688(2)
_cell_length_b                   15.2337(3)
_cell_length_c                   42.5078(6)
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     6908.6(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            23185
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.9814
_exptl_absorpt_correction_T_min  0.9369
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       plate
_exptl_crystal_F_000             2656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.1360
_refine_ls_R_factor_gt           0.0892
_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)+(0.0134P)²+23.7562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                3752
_reflns_number_total             5361
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0004322B_1.cif
_cod_data_source_block           burk_7b
_cod_database_code               4116020
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P P 0.71138(13) 0.02743(9) 0.14777(3) 0.0300(3) Uani 1 1 d .
O1 O 0.9420(5) -0.0310(3) 0.17989(11) 0.0770(15) Uani 1 1 d .
O2 O 0.9040(4) -0.1853(3) 0.17003(10) 0.0728(14) Uani 1 1 d .
O3 O 0.9843(4) -0.1369(3) 0.22098(8) 0.0498(11) Uani 1 1 d .
S S 0.97169(13) -0.12044(10) 0.18777(3) 0.0409(4) Uani 1 1 d .
F1 F 1.1723(4) -0.2146(3) 0.17801(10) 0.0966(16) Uani 1 1 d .
F2 F 1.2109(4) -0.0823(4) 0.18814(9) 0.1054(18) Uani 1 1 d .
F3 F 1.1426(3) -0.1175(3) 0.14295(8) 0.0678(11) Uani 1 1 d .
N1 N 0.7260(3) 0.1256(3) 0.20288(9) 0.0248(9) Uani 1 1 d .
N2 N 0.8496(4) 0.1844(2) 0.16797(9) 0.0250(9) Uani 1 1 d .
N3 N 0.7114(4) 0.0686(3) 0.11380(9) 0.0273(10) Uani 1 1 d .
C1 C 0.7671(4) 0.1189(3) 0.17282(10) 0.0223(11) Uani 1 1 d .
C2 C 0.7812(5) 0.1974(3) 0.21698(11) 0.0290(12) Uani 1 1 d .
C3 C 0.8604(5) 0.2338(3) 0.19533(11) 0.0263(12) Uani 1 1 d .
C4 C 0.6353(5) 0.0635(3) 0.21774(12) 0.0341(13) Uani 1 1 d .
H4A H 0.6107 0.0214 0.2011 0.041 Uiso 1 1 c R
C5 C 0.5164(5) 0.1109(5) 0.22741(15) 0.0635(19) Uani 1 1 d .
H5A H 0.4833 0.1432 0.2096 0.095 Uiso 1 1 c R
H5B H 0.5350 0.1515 0.2444 0.095 Uiso 1 1 c R
H5C H 0.4547 0.0685 0.2345 0.095 Uiso 1 1 c R
C6 C 0.6971(6) 0.0095(4) 0.24352(12) 0.0472(16) Uani 1 1 d .
H6A H 0.7727 -0.0176 0.2354 0.071 Uiso 1 1 c R
H6B H 0.6396 -0.0358 0.2506 0.071 Uiso 1 1 c R
H6C H 0.7184 0.0473 0.2611 0.071 Uiso 1 1 c R
C7 C 0.7531(5) 0.2330(3) 0.24926(11) 0.0392(14) Uani 1 1 d .
H7A H 0.8057 0.2837 0.2533 0.059 Uiso 1 1 c R
H7B H 0.7698 0.1882 0.2649 0.059 Uiso 1 1 c R
H7C H 0.6656 0.2502 0.2504 0.059 Uiso 1 1 c R
C8 C 0.9393(6) 0.3142(3) 0.19891(13) 0.0474(16) Uani 1 1 d .
H8A H 0.9298 0.3374 0.2200 0.071 Uiso 1 1 c R
H8B H 0.9129 0.3581 0.1838 0.071 Uiso 1 1 c R
H8C H 1.0266 0.2994 0.1953 0.071 Uiso 1 1 c R
C9 C 0.9181(5) 0.1981(3) 0.13790(11) 0.0334(13) Uani 1 1 d .
H9A H 0.8876 0.1525 0.1231 0.040 Uiso 1 1 c R
C10 C 1.0565(5) 0.1819(5) 0.14226(16) 0.068(2) Uani 1 1 d .
H10A H 1.0693 0.1238 0.1511 0.103 Uiso 1 1 c R
H10B H 1.0908 0.2256 0.1565 0.103 Uiso 1 1 c R
H10C H 1.0986 0.1859 0.1221 0.103 Uiso 1 1 c R
C11 C 0.8851(7) 0.2863(4) 0.12330(15) 0.066(2) Uani 1 1 d .
H11A H 0.7948 0.2913 0.1214 0.099 Uiso 1 1 c R
H11B H 0.9230 0.2907 0.1026 0.099 Uiso 1 1 c R
H11C H 0.9165 0.3332 0.1366 0.099 Uiso 1 1 c R
C12 C 0.6523(5) 0.0172(3) 0.08946(11) 0.0261(11) Uani 1 1 d .
C13 C 0.7256(5) -0.0342(3) 0.06842(10) 0.0257(11) Uani 1 1 d .
C14 C 0.6612(5) -0.0903(3) 0.04815(11) 0.0305(12) Uani 1 1 d .
H14A H 0.7082 -0.1264 0.0346 0.037 Uiso 1 1 c R
C15 C 0.5310(5) -0.0959(3) 0.04686(12) 0.0345(13) Uani 1 1 d .
C16 C 0.4645(5) -0.0374(3) 0.06516(12) 0.0362(13) Uani 1 1 d .
H16A H 0.3766 -0.0373 0.0634 0.043 Uiso 1 1 c R
C17 C 0.5196(5) 0.0216(3) 0.08610(11) 0.0308(12) Uani 1 1 d .
C18 C 0.8702(5) -0.0275(4) 0.06611(11) 0.0330(13) Uani 1 1 d .
C19 C 0.9053(5) 0.0691(4) 0.05887(14) 0.0509(16) Uani 1 1 d .
H19A H 0.8614 0.0883 0.0401 0.076 Uiso 1 1 c R
H19B H 0.9950 0.0735 0.0555 0.076 Uiso 1 1 c R
H19C H 0.8815 0.1060 0.0765 0.076 Uiso 1 1 c R
C20 C 0.9368(6) -0.0582(4) 0.09571(14) 0.0584(18) Uani 1 1 d .
H20A H 0.9054 -0.0257 0.1137 0.088 Uiso 1 1 c R
H20B H 1.0261 -0.0481 0.0936 0.088 Uiso 1 1 c R
H20C H 0.9214 -0.1203 0.0988 0.088 Uiso 1 1 c R
C21 C 0.9224(6) -0.0814(4) 0.03873(15) 0.0624(19) Uani 1 1 d .
H21A H 0.8822 -0.0632 0.0193 0.094 Uiso 1 1 c R
H21B H 0.9060 -0.1432 0.0424 0.094 Uiso 1 1 c R
H21C H 1.0121 -0.0719 0.0371 0.094 Uiso 1 1 c R
C22 C 0.4630(6) -0.1602(4) 0.02496(13) 0.0458(15) Uani 1 1 d .
C23 C 0.5555(8) -0.2178(5) 0.00620(19) 0.094(3) Uani 1 1 d .
H23A H 0.6064 -0.2517 0.0207 0.140 Uiso 1 1 c R
H23B H 0.6091 -0.1806 -0.0065 0.140 Uiso 1 1 c R
H23C H 0.5090 -0.2574 -0.0074 0.140 Uiso 1 1 c R
C24 C 0.3834(8) -0.1109(5) 0.00133(17) 0.093(3) Uani 1 1 d .
H24A H 0.3224 -0.0751 0.0124 0.140 Uiso 1 1 c R
H24B H 0.3401 -0.1525 -0.0121 0.140 Uiso 1 1 c R
H24C H 0.4366 -0.0735 -0.0114 0.140 Uiso 1 1 c R
C25 C 0.3824(8) -0.2226(5) 0.04418(16) 0.090(3) Uani 1 1 d .
H25A H 0.3224 -0.1891 0.0564 0.135 Uiso 1 1 c R
H25B H 0.4354 -0.2563 0.0582 0.135 Uiso 1 1 c R
H25C H 0.3381 -0.2621 0.0302 0.135 Uiso 1 1 c R
C26 C 0.4373(5) 0.0927(4) 0.10209(14) 0.0456(15) Uani 1 1 d .
C27 C 0.3095(6) 0.0999(5) 0.08474(16) 0.080(2) Uani 1 1 d .
H27A H 0.3238 0.1154 0.0629 0.121 Uiso 1 1 c R
H27B H 0.2587 0.1448 0.0947 0.121 Uiso 1 1 c R
H27C H 0.2662 0.0439 0.0858 0.121 Uiso 1 1 c R
C28 C 0.4980(7) 0.1843(4) 0.09985(18) 0.076(2) Uani 1 1 d .
H28A H 0.5163 0.1977 0.0780 0.113 Uiso 1 1 c R
H28B H 0.5752 0.1850 0.1119 0.113 Uiso 1 1 c R
H28C H 0.4408 0.2280 0.1082 0.113 Uiso 1 1 c R
C29 C 0.4050(6) 0.0705(5) 0.13648(15) 0.077(2) Uani 1 1 d .
H29A H 0.3647 0.0135 0.1374 0.116 Uiso 1 1 c R
H29B H 0.3488 0.1148 0.1448 0.116 Uiso 1 1 c R
H29C H 0.4813 0.0693 0.1489 0.116 Uiso 1 1 c R
C30 C 1.1313(6) -0.1316(4) 0.17333(14) 0.0490(16) Uani 1 1 d .
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'
F F 0.0171 0.0103 '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
N3 P C1 103.2(2)
N3 P O1 122.98(18)
C1 P O1 72.12(17)
S O1 P 125.2(3)
O2 S O1 114.8(3)
O2 S O3 116.2(3)
O1 S O3 114.4(3)
O2 S C30 103.2(3)
O1 S C30 102.5(3)
O3 S C30 103.1(3)
C1 N1 C2 109.3(4)
C1 N1 C4 124.1(4)
C2 N1 C4 126.5(4)
C1 N2 C3 109.1(4)
C1 N2 C9 123.8(4)
C3 N2 C9 127.1(4)
C12 N3 P 116.2(3)
N2 C1 N1 107.5(4)
N2 C1 P 132.8(3)
N1 C1 P 119.7(3)
C3 C2 N1 107.1(4)
C3 C2 C7 126.2(5)
N1 C2 C7 126.7(5)
C2 C3 N2 107.0(4)
C2 C3 C8 127.8(5)
N2 C3 C8 125.2(5)
N1 C4 C5 110.8(4)
N1 C4 C6 111.5(4)
C5 C4 C6 115.2(5)
N2 C9 C10 110.6(5)
N2 C9 C11 111.1(4)
C10 C9 C11 114.9(5)
C13 C12 C17 120.6(4)
C13 C12 N3 120.6(4)
C17 C12 N3 118.7(4)
C14 C13 C12 117.1(5)
C14 C13 C18 119.4(4)
C12 C13 C18 123.5(4)
C15 C14 C13 123.6(5)
C16 C15 C14 116.9(5)
C16 C15 C22 120.8(5)
C14 C15 C22 122.3(5)
C15 C16 C17 124.0(5)
C16 C17 C12 116.9(5)
C16 C17 C26 119.4(5)
C12 C17 C26 123.5(5)
C20 C18 C21 107.2(5)
C20 C18 C13 113.2(4)
C21 C18 C13 112.1(4)
C20 C18 C19 110.1(5)
C21 C18 C19 105.7(5)
C13 C18 C19 108.4(4)
C24 C22 C25 110.5(6)
C24 C22 C15 110.5(5)
C25 C22 C15 109.9(5)
C24 C22 C23 107.3(6)
C25 C22 C23 106.5(6)
C15 C22 C23 112.0(5)
C29 C26 C28 110.5(6)
C29 C26 C17 113.0(5)
C28 C26 C17 111.5(5)
C29 C26 C27 105.7(5)
C28 C26 C27 106.0(6)
C17 C26 C27 109.8(5)
F2 C30 F3 108.8(5)
F2 C30 F1 105.0(6)
F3 C30 F1 105.5(5)
F2 C30 S 113.3(4)
F3 C30 S 113.7(4)
F1 C30 S 109.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P N3 1.574(4)
P C1 1.852(5)
P O1 2.951(5)
O1 S 1.438(4)
O2 S 1.438(4)
O3 S 1.440(4)
S C30 1.818(6)
F1 C30 1.351(7)
F2 C30 1.297(7)
F3 C30 1.315(6)
N1 C1 1.355(5)
N1 C2 1.379(6)
N1 C4 1.493(6)
N2 C1 1.347(6)
N2 C3 1.390(6)
N2 C9 1.487(6)
N3 C12 1.442(6)
C2 C3 1.367(7)
C2 C7 1.506(7)
C3 C8 1.494(7)
C4 C5 1.517(7)
C4 C6 1.521(7)
C9 C10 1.509(8)
C9 C11 1.522(7)
C12 C13 1.422(7)
C12 C17 1.424(7)
C13 C14 1.395(7)
C13 C18 1.549(7)
C14 C15 1.393(7)
C15 C16 1.379(7)
C15 C22 1.534(7)
C16 C17 1.396(7)
C17 C26 1.551(7)
C18 C20 1.518(7)
C18 C21 1.529(7)
C18 C19 1.551(7)
C22 C24 1.515(8)
C22 C25 1.519(8)
C22 C23 1.543(9)
C26 C29 1.539(8)
C26 C28 1.542(9)
C26 C27 1.554(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660562
