#------------------------------------------------------------------------------
#$Date: 2016-03-25 08:53:21 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179710 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/13/7001379.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_7001379
loop_
_publ_author_name
'Ariyananda, Piyal W. G.'
'Kieber-Emmons, Matthew T.'
'Yap, Glenn P. A.'
'Riordan, Charles G.'
_publ_section_title
;
 Synthetic analogs for evaluating the influence of N--H⋯S
 hydrogen bonds on the formation of thioester in acetyl coenzyme a
 synthase
;
_journal_issue                   22
_journal_name_full               'Dalton Transactions'
_journal_page_first              4359
_journal_page_last               4369
_journal_paper_doi               10.1039/b901192g
_journal_year                    2009
_chemical_formula_sum            'C17 H27 F5 Ni P2 S'
_chemical_formula_weight         479.10
_chemical_name_common            'manuscript number B901192G'
_chemical_name_systematic
;
manuscript number B901192G
;
_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                 99.304(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.378(3)
_cell_length_b                   19.453(6)
_cell_length_c                   11.641(3)
_cell_measurement_reflns_used    1017
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.74
_cell_volume                     2095.7(11)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       ω
_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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28393
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.220
_exptl_absorpt_correction_T_max  0.8363
_exptl_absorpt_correction_T_min  0.6727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         5208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0245
_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)+(0.0430P)²+0.6041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0679
_reflns_number_gt                4915
_reflns_number_total             5208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b901192g.txt
_cod_data_source_block           char198
_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 
;
_cod_original_cell_volume        2095.9(10)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7001379
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.945218(16) 0.124682(8) 0.857841(12) 0.01711(6) Uani 1 1 d . . .
S1 S 1.00947(4) 0.042004(17) 0.74670(3) 0.02339(8) Uani 1 1 d . . .
P1 P 0.87964(3) 0.193851(16) 0.98080(3) 0.01748(7) Uani 1 1 d . . .
P2 P 1.14585(3) 0.110644(16) 0.98036(3) 0.01764(7) Uani 1 1 d . . .
F1 F 0.75831(12) -0.04860(5) 0.64443(8) 0.0443(3) Uani 1 1 d . . .
F2 F 0.60384(11) -0.04461(6) 0.42942(9) 0.0472(3) Uani 1 1 d . . .
F3 F 0.66531(10) 0.05022(5) 0.27228(7) 0.0386(2) Uani 1 1 d . . .
F4 F 0.88700(14) 0.14040(6) 0.33458(9) 0.0502(3) Uani 1 1 d . . .
F5 F 1.04213(11) 0.13688(5) 0.54822(8) 0.0421(2) Uani 1 1 d . . .
C1 C 0.76783(15) 0.15081(8) 0.75171(12) 0.0294(3) Uani 1 1 d . . .
H1A H 0.7105 0.1821 0.7919 0.044 Uiso 1 1 calc R . .
H1B H 0.7111 0.1095 0.7274 0.044 Uiso 1 1 calc R . .
H1C H 0.7937 0.1738 0.6831 0.044 Uiso 1 1 calc R . .
C2 C 0.79198(15) -0.00030(7) 0.57048(11) 0.0256(3) Uani 1 1 d . . .
C3 C 0.71116(15) 0.00079(7) 0.45977(12) 0.0281(3) Uani 1 1 d . . .
C4 C 0.74191(16) 0.04855(7) 0.38006(11) 0.0275(3) Uani 1 1 d . . .
C5 C 0.85373(17) 0.09427(7) 0.41228(12) 0.0293(3) Uani 1 1 d . . .
C6 C 0.93269(15) 0.09180(7) 0.52289(11) 0.0254(3) Uani 1 1 d . . .
C7 C 0.90479(14) 0.04490(6) 0.60673(10) 0.0205(2) Uani 1 1 d . . .
C8 C 1.02314(14) 0.20500(6) 1.10803(11) 0.0217(2) Uani 1 1 d . . .
H8A H 1.0841 0.2450 1.0957 0.026 Uiso 1 1 calc R . .
H8B H 0.9794 0.2136 1.1786 0.026 Uiso 1 1 calc R . .
C9 C 1.11603(14) 0.13989(7) 1.12466(10) 0.0229(2) Uani 1 1 d . . .
H9A H 1.0661 0.1037 1.1629 0.027 Uiso 1 1 calc R . .
H9B H 1.2097 0.1499 1.1744 0.027 Uiso 1 1 calc R . .
C10 C 0.83369(15) 0.28275(7) 0.93848(12) 0.0246(3) Uani 1 1 d . . .
H10A H 0.7389 0.2839 0.8868 0.030 Uiso 1 1 calc R . .
H10B H 0.8259 0.3103 1.0087 0.030 Uiso 1 1 calc R . .
C11 C 0.94895(17) 0.31420(8) 0.87524(15) 0.0375(4) Uani 1 1 d . . .
H11A H 0.9194 0.3607 0.8488 0.056 Uiso 1 1 calc R . .
H11B H 0.9601 0.2856 0.8079 0.056 Uiso 1 1 calc R . .
H11C H 1.0412 0.3164 0.9285 0.056 Uiso 1 1 calc R . .
C12 C 0.72688(14) 0.15929(7) 1.04278(11) 0.0228(2) Uani 1 1 d . . .
H12A H 0.6505 0.1457 0.9777 0.027 Uiso 1 1 calc R . .
H12B H 0.7595 0.1170 1.0866 0.027 Uiso 1 1 calc R . .
C13 C 0.65948(15) 0.20678(7) 1.12327(12) 0.0272(3) Uani 1 1 d . . .
H13A H 0.5868 0.1814 1.1580 0.041 Uiso 1 1 calc R . .
H13B H 0.6134 0.2458 1.0785 0.041 Uiso 1 1 calc R . .
H13C H 0.7348 0.2237 1.1850 0.041 Uiso 1 1 calc R . .
C14 C 1.23298(14) 0.02685(6) 1.00568(11) 0.0227(2) Uani 1 1 d . . .
H14A H 1.1629 -0.0056 1.0311 0.027 Uiso 1 1 calc R . .
H14B H 1.2562 0.0097 0.9308 0.027 Uiso 1 1 calc R . .
C15 C 1.37100(16) 0.02561(8) 1.09556(12) 0.0307(3) Uani 1 1 d . . .
H15A H 1.4080 -0.0215 1.1044 0.046 Uiso 1 1 calc R . .
H15B H 1.3498 0.0422 1.1705 0.046 Uiso 1 1 calc R . .
H15C H 1.4437 0.0554 1.0694 0.046 Uiso 1 1 calc R . .
C16 C 1.28825(14) 0.16808(7) 0.94520(12) 0.0273(3) Uani 1 1 d . . .
H16A H 1.2503 0.2156 0.9380 0.033 Uiso 1 1 calc R . .
H16B H 1.3704 0.1673 1.0104 0.033 Uiso 1 1 calc R . .
C17 C 1.34333(16) 0.14888(9) 0.83299(14) 0.0344(3) Uani 1 1 d . . .
H17A H 1.4165 0.1822 0.8181 0.052 Uiso 1 1 calc R . .
H17B H 1.2626 0.1493 0.7680 0.052 Uiso 1 1 calc R . .
H17C H 1.3862 0.1028 0.8409 0.052 Uiso 1 1 calc R . .
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'
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'
Ni Ni 0.3393 1.1124 '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
_geom_angle_publ_flag
C1 Ni1 P1 87.26(4) . . ?
C1 Ni1 P2 172.21(5) . . ?
P1 Ni1 P2 87.25(2) . . ?
C1 Ni1 S1 95.92(4) . . ?
P1 Ni1 S1 172.421(14) . . ?
P2 Ni1 S1 90.210(19) . . ?
C7 S1 Ni1 110.76(4) . . ?
C10 P1 C12 106.71(6) . . ?
C10 P1 C8 102.37(6) . . ?
C12 P1 C8 104.01(6) . . ?
C10 P1 Ni1 119.85(5) . . ?
C12 P1 Ni1 111.25(4) . . ?
C8 P1 Ni1 111.21(4) . . ?
C14 P2 C9 105.02(6) . . ?
C14 P2 C16 104.85(7) . . ?
C9 P2 C16 103.82(7) . . ?
C14 P2 Ni1 122.16(4) . . ?
C9 P2 Ni1 108.40(5) . . ?
C16 P2 Ni1 111.01(5) . . ?
F1 C2 C3 117.12(12) . . ?
F1 C2 C7 119.60(12) . . ?
C3 C2 C7 123.27(12) . . ?
F2 C3 C4 119.77(12) . . ?
F2 C3 C2 120.58(13) . . ?
C4 C3 C2 119.65(13) . . ?
F3 C4 C3 120.53(13) . . ?
F3 C4 C5 120.47(13) . . ?
C3 C4 C5 119.00(12) . . ?
F4 C5 C6 120.20(13) . . ?
F4 C5 C4 119.71(13) . . ?
C6 C5 C4 120.08(12) . . ?
F5 C6 C5 117.21(12) . . ?
F5 C6 C7 119.79(12) . . ?
C5 C6 C7 122.99(13) . . ?
C2 C7 C6 115.00(11) . . ?
C2 C7 S1 122.98(10) . . ?
C6 C7 S1 121.99(10) . . ?
C9 C8 P1 109.28(8) . . ?
C8 C9 P2 107.94(8) . . ?
C11 C10 P1 110.69(9) . . ?
C13 C12 P1 116.61(9) . . ?
C15 C14 P2 115.61(9) . . ?
C17 C16 P2 113.61(10) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C1 1.9717(14) . ?
Ni1 P1 2.1266(5) . ?
Ni1 P2 2.1867(6) . ?
Ni1 S1 2.2082(5) . ?
S1 C7 1.7620(13) . ?
P1 C10 1.8304(14) . ?
P1 C12 1.8329(13) . ?
P1 C8 1.8459(13) . ?
P2 C14 1.8259(13) . ?
P2 C9 1.8373(13) . ?
P2 C16 1.8375(14) . ?
F1 C2 1.3460(15) . ?
F2 C3 1.3427(16) . ?
F3 C4 1.3416(15) . ?
F4 C5 1.3460(16) . ?
F5 C6 1.3458(16) . ?
C2 C3 1.3857(18) . ?
C2 C7 1.3879(18) . ?
C3 C4 1.376(2) . ?
C4 C5 1.380(2) . ?
C5 C6 1.3786(19) . ?
C6 C7 1.3914(18) . ?
C8 C9 1.5318(18) . ?
C10 C11 1.5305(19) . ?
C12 C13 1.5240(18) . ?
C14 C15 1.5274(18) . ?
C16 C17 1.527(2) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Ni1 S1 C7 11.39(7) . . . . ?
P1 Ni1 S1 C7 125.88(11) . . . . ?
P2 Ni1 S1 C7 -163.80(5) . . . . ?
C1 Ni1 P1 C10 -52.58(7) . . . . ?
P2 Ni1 P1 C10 121.90(5) . . . . ?
S1 Ni1 P1 C10 -167.59(11) . . . . ?
C1 Ni1 P1 C12 72.79(7) . . . . ?
P2 Ni1 P1 C12 -112.73(5) . . . . ?
S1 Ni1 P1 C12 -42.22(12) . . . . ?
C1 Ni1 P1 C8 -171.77(7) . . . . ?
P2 Ni1 P1 C8 2.70(5) . . . . ?
S1 Ni1 P1 C8 73.22(12) . . . . ?
C1 Ni1 P2 C14 -174.3(3) . . . . ?
P1 Ni1 P2 C14 140.49(5) . . . . ?
S1 Ni1 P2 C14 -32.37(5) . . . . ?
C1 Ni1 P2 C9 63.5(3) . . . . ?
P1 Ni1 P2 C9 18.37(5) . . . . ?
S1 Ni1 P2 C9 -154.49(5) . . . . ?
C1 Ni1 P2 C16 -49.9(3) . . . . ?
P1 Ni1 P2 C16 -95.06(5) . . . . ?
S1 Ni1 P2 C16 92.09(5) . . . . ?
F1 C2 C3 F2 0.3(2) . . . . ?
C7 C2 C3 F2 179.52(13) . . . . ?
F1 C2 C3 C4 -179.24(13) . . . . ?
C7 C2 C3 C4 0.0(2) . . . . ?
F2 C3 C4 F3 0.1(2) . . . . ?
C2 C3 C4 F3 179.70(13) . . . . ?
F2 C3 C4 C5 -179.21(13) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
F3 C4 C5 F4 -0.7(2) . . . . ?
C3 C4 C5 F4 178.68(14) . . . . ?
F3 C4 C5 C6 -179.44(13) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
F4 C5 C6 F5 0.0(2) . . . . ?
C4 C5 C6 F5 178.72(13) . . . . ?
F4 C5 C6 C7 -179.29(13) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
F1 C2 C7 C6 178.66(12) . . . . ?
C3 C2 C7 C6 -0.5(2) . . . . ?
F1 C2 C7 S1 0.56(19) . . . . ?
C3 C2 C7 S1 -178.62(11) . . . . ?
F5 C6 C7 C2 -178.42(12) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
F5 C6 C7 S1 -0.30(18) . . . . ?
C5 C6 C7 S1 178.92(11) . . . . ?
Ni1 S1 C7 C2 -103.25(11) . . . . ?
Ni1 S1 C7 C6 78.78(11) . . . . ?
C10 P1 C8 C9 -157.03(9) . . . . ?
C12 P1 C8 C9 91.99(10) . . . . ?
Ni1 P1 C8 C9 -27.85(10) . . . . ?
P1 C8 C9 P2 41.48(11) . . . . ?
C14 P2 C9 C8 -171.75(9) . . . . ?
C16 P2 C9 C8 78.42(10) . . . . ?
Ni1 P2 C9 C8 -39.68(10) . . . . ?
C12 P1 C10 C11 -174.77(11) . . . . ?
C8 P1 C10 C11 76.28(12) . . . . ?
Ni1 P1 C10 C11 -47.29(12) . . . . ?
C10 P1 C12 C13 -41.73(12) . . . . ?
C8 P1 C12 C13 66.06(11) . . . . ?
Ni1 P1 C12 C13 -174.13(9) . . . . ?
C9 P2 C14 C15 -55.28(11) . . . . ?
C16 P2 C14 C15 53.81(11) . . . . ?
Ni1 P2 C14 C15 -178.97(8) . . . . ?
C14 P2 C16 C17 64.06(11) . . . . ?
C9 P2 C16 C17 174.02(10) . . . . ?
Ni1 P2 C16 C17 -69.71(11) . . . . ?
