#------------------------------------------------------------------------------
#$Date: 2016-03-25 08:53:21 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179710 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/13/7001380.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_7001380
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            'C22 H41 N Ni O P2 S'
_chemical_formula_weight         488.27
_chemical_name_common            'manuscript number B901192G'
_chemical_name_systematic
;
manuscript number B901192G
;
_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                   17.408(3)
_cell_length_b                   17.549(3)
_cell_length_c                   17.680(3)
_cell_measurement_reflns_used    1022
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      16.31
_cell_measurement_theta_min      2.30
_cell_volume                     5401.1(16)
_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      290(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.1890
_diffrn_reflns_av_sigmaI/netI    0.1000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            58983
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.926
_exptl_absorpt_correction_T_max  0.9578
_exptl_absorpt_correction_T_min  0.8790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         6733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.2300
_refine_ls_R_factor_gt           0.0798
_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)+(0.0703P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.2257
_reflns_number_gt                2259
_reflns_number_total             6733
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b901192g.txt
_cod_data_source_block           char201
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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        5401.1(15)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7001380
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.25205(5) 0.03073(4) 0.67703(4) 0.0664(3) Uani 1 1 d . . .
P1 P 0.29633(12) 0.03007(11) 0.56534(9) 0.0854(6) Uani 1 1 d . . .
P2 P 0.26727(14) -0.09321(10) 0.67873(10) 0.0953(7) Uani 1 1 d . . .
S1 S 0.21576(13) 0.02374(10) 0.79505(9) 0.0894(6) Uani 1 1 d . . .
N1 N 0.3065(4) 0.1546(3) 0.8592(3) 0.0823(17) Uani 1 1 d . . .
H1 H 0.316(4) 0.117(4) 0.830(4) 0.099 Uiso 1 1 d . . .
O1 O 0.3526(4) 0.2349(4) 0.9447(4) 0.176(3) Uani 1 1 d . . .
C1 C 0.2353(4) 0.1412(3) 0.6690(3) 0.089(2) Uani 1 1 d . . .
H1A H 0.2430 0.1571 0.6176 0.133 Uiso 1 1 calc R . .
H1B H 0.2709 0.1674 0.7013 0.133 Uiso 1 1 calc R . .
H1C H 0.1837 0.1531 0.6842 0.133 Uiso 1 1 calc R . .
C2 C 0.2270(4) 0.1657(4) 0.8653(3) 0.0752(18) Uani 1 1 d . . .
C3 C 0.1963(5) 0.2274(4) 0.9012(3) 0.084(2) Uani 1 1 d . . .
H3A H 0.2285 0.2639 0.9224 0.101 Uiso 1 1 calc R . .
C4 C 0.1186(6) 0.2358(5) 0.9061(4) 0.109(3) Uani 1 1 d . . .
H4A H 0.0987 0.2774 0.9319 0.130 Uiso 1 1 calc R . .
C5 C 0.0696(5) 0.1850(6) 0.8742(4) 0.113(3) Uani 1 1 d . . .
H5A H 0.0168 0.1929 0.8758 0.136 Uiso 1 1 calc R . .
C6 C 0.1000(5) 0.1212(5) 0.8393(4) 0.095(2) Uani 1 1 d . . .
H6A H 0.0668 0.0851 0.8188 0.114 Uiso 1 1 calc R . .
C7 C 0.1786(4) 0.1096(4) 0.8341(3) 0.0757(18) Uani 1 1 d . . .
C8 C 0.3633(5) 0.1890(5) 0.8956(5) 0.103(2) Uani 1 1 d . . .
C9 C 0.4444(5) 0.1694(5) 0.8736(5) 0.111(3) Uani 1 1 d . . .
C10 C 0.4934(7) 0.1724(10) 0.9409(7) 0.297(10) Uani 1 1 d . . .
H10A H 0.4910 0.1245 0.9670 0.445 Uiso 1 1 calc R . .
H10B H 0.4758 0.2123 0.9739 0.445 Uiso 1 1 calc R . .
H10C H 0.5455 0.1824 0.9261 0.445 Uiso 1 1 calc R . .
C11 C 0.4549(6) 0.0940(6) 0.8368(7) 0.190(5) Uani 1 1 d . . .
H11A H 0.4350 0.0548 0.8692 0.285 Uiso 1 1 calc R . .
H11B H 0.5086 0.0853 0.8280 0.285 Uiso 1 1 calc R . .
H11C H 0.4279 0.0933 0.7895 0.285 Uiso 1 1 calc R . .
C12 C 0.4731(7) 0.2273(7) 0.8188(8) 0.242(8) Uani 1 1 d . . .
H12A H 0.5273 0.2204 0.8113 0.364 Uiso 1 1 calc R . .
H12B H 0.4637 0.2775 0.8383 0.364 Uiso 1 1 calc R . .
H12C H 0.4469 0.2214 0.7714 0.364 Uiso 1 1 calc R . .
C13 C 0.3263(6) -0.0671(5) 0.5406(5) 0.150(4) Uani 1 1 d . . .
H13A H 0.3087 -0.0778 0.4896 0.180 Uiso 1 1 calc R . .
H13B H 0.3820 -0.0685 0.5398 0.180 Uiso 1 1 calc R . .
C14 C 0.3005(7) -0.1258(5) 0.5879(4) 0.156(4) Uani 1 1 d . . .
H14A H 0.3421 -0.1618 0.5956 0.187 Uiso 1 1 calc R . .
H14B H 0.2590 -0.1526 0.5629 0.187 Uiso 1 1 calc R . .
C15 C 0.2322(7) 0.0654(7) 0.4898(4) 0.154(4) Uani 1 1 d . . .
H15A H 0.2294 0.1205 0.4934 0.185 Uiso 1 1 calc R . .
H15B H 0.2550 0.0531 0.4413 0.185 Uiso 1 1 calc R . .
C16 C 0.1562(7) 0.0357(8) 0.4914(6) 0.198(6) Uani 1 1 d . . .
H16A H 0.1262 0.0593 0.4524 0.297 Uiso 1 1 calc R . .
H16B H 0.1334 0.0460 0.5398 0.297 Uiso 1 1 calc R . .
H16C H 0.1578 -0.0184 0.4831 0.297 Uiso 1 1 calc R . .
C17 C 0.3838(5) 0.0862(5) 0.5512(5) 0.134(3) Uani 1 1 d . . .
H17A H 0.3715 0.1393 0.5602 0.160 Uiso 1 1 calc R . .
H17B H 0.4209 0.0710 0.5892 0.160 Uiso 1 1 calc R . .
C18 C 0.4219(6) 0.0803(6) 0.4744(6) 0.177(5) Uani 1 1 d . . .
H18A H 0.4647 0.1147 0.4721 0.266 Uiso 1 1 calc R . .
H18B H 0.3854 0.0932 0.4357 0.266 Uiso 1 1 calc R . .
H18C H 0.4396 0.0291 0.4666 0.266 Uiso 1 1 calc R . .
C19 C 0.3339(8) -0.1330(5) 0.7468(5) 0.164(5) Uani 1 1 d . . .
H19A H 0.3137 -0.1249 0.7973 0.197 Uiso 1 1 calc R . .
H19B H 0.3375 -0.1875 0.7386 0.197 Uiso 1 1 calc R . .
C20 C 0.4129(8) -0.0993(7) 0.7425(8) 0.245(9) Uani 1 1 d . . .
H20B H 0.4450 -0.1222 0.7803 0.368 Uiso 1 1 calc R . .
H20C H 0.4100 -0.0453 0.7510 0.368 Uiso 1 1 calc R . .
H20D H 0.4342 -0.1087 0.6933 0.368 Uiso 1 1 calc R . .
C21 C 0.1807(8) -0.1514(5) 0.7006(7) 0.168(5) Uani 1 1 d . . .
H21A H 0.1934 -0.2049 0.6950 0.202 Uiso 1 1 calc R . .
H21B H 0.1660 -0.1428 0.7528 0.202 Uiso 1 1 calc R . .
C22 C 0.1159(9) -0.1335(8) 0.6519(8) 0.227(7) Uani 1 1 d . . .
H22B H 0.0726 -0.1642 0.6661 0.341 Uiso 1 1 calc R . .
H22C H 0.1293 -0.1439 0.6003 0.341 Uiso 1 1 calc R . .
H22D H 0.1029 -0.0806 0.6572 0.341 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'
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'
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 Ni P1 89.56(18) . . ?
C1 Ni S1 94.66(18) . . ?
P1 Ni S1 174.30(9) . . ?
C1 Ni P2 176.28(19) . . ?
P1 Ni P2 87.90(8) . . ?
S1 Ni P2 88.06(7) . . ?
C17 P1 C13 103.3(4) . . ?
C17 P1 C15 102.9(5) . . ?
C13 P1 C15 108.1(5) . . ?
C17 P1 Ni 115.3(3) . . ?
C13 P1 Ni 109.3(3) . . ?
C15 P1 Ni 116.9(3) . . ?
C14 P2 C19 105.3(5) . . ?
C14 P2 C21 105.7(5) . . ?
C19 P2 C21 99.8(6) . . ?
C14 P2 Ni 110.0(3) . . ?
C19 P2 Ni 118.0(4) . . ?
C21 P2 Ni 116.7(4) . . ?
C7 S1 Ni 115.4(2) . . ?
C8 N1 C2 129.5(6) . . ?
C3 C2 N1 122.2(7) . . ?
C3 C2 C7 120.3(7) . . ?
N1 C2 C7 117.5(6) . . ?
C4 C3 C2 120.2(7) . . ?
C5 C4 C3 121.8(8) . . ?
C4 C5 C6 118.5(8) . . ?
C5 C6 C7 121.6(8) . . ?
C6 C7 C2 117.5(6) . . ?
C6 C7 S1 120.6(6) . . ?
C2 C7 S1 121.9(6) . . ?
O1 C8 N1 122.9(8) . . ?
O1 C8 C9 119.1(8) . . ?
N1 C8 C9 118.0(7) . . ?
C10 C9 C11 108.4(10) . . ?
C10 C9 C12 108.0(10) . . ?
C11 C9 C12 106.4(9) . . ?
C10 C9 C8 109.1(8) . . ?
C11 C9 C8 115.6(8) . . ?
C12 C9 C8 109.1(8) . . ?
C14 C13 P1 116.7(6) . . ?
C13 C14 P2 113.7(6) . . ?
C16 C15 P1 115.1(8) . . ?
C18 C17 P1 116.7(7) . . ?
C20 C19 P2 113.7(8) . . ?
C22 C21 P2 112.8(9) . . ?
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
Ni C1 1.966(6) . ?
Ni P1 2.1198(17) . ?
Ni S1 2.1836(17) . ?
Ni P2 2.191(2) . ?
P1 C17 1.831(8) . ?
P1 C13 1.836(8) . ?
P1 C15 1.848(10) . ?
P2 C14 1.799(7) . ?
P2 C19 1.811(9) . ?
P2 C21 1.861(12) . ?
S1 C7 1.778(6) . ?
N1 C8 1.325(9) . ?
N1 C2 1.403(8) . ?
O1 C8 1.199(8) . ?
C2 C3 1.365(8) . ?
C2 C7 1.408(8) . ?
C3 C4 1.362(10) . ?
C4 C5 1.355(11) . ?
C5 C6 1.384(10) . ?
C6 C7 1.388(9) . ?
C8 C9 1.505(11) . ?
C9 C10 1.466(12) . ?
C9 C11 1.485(11) . ?
C9 C12 1.490(12) . ?
C13 C14 1.402(10) . ?
C15 C16 1.422(13) . ?
C17 C18 1.514(10) . ?
C19 C20 1.499(15) . ?
C21 C22 1.453(14) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.85(6) 2.48(7) 3.009(6) 122(6) .
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 Ni P1 C17 62.8(4) . . . . ?
S1 Ni P1 C17 -75.0(9) . . . . ?
P2 Ni P1 C17 -119.9(4) . . . . ?
C1 Ni P1 C13 178.6(4) . . . . ?
S1 Ni P1 C13 40.9(10) . . . . ?
P2 Ni P1 C13 -4.1(4) . . . . ?
C1 Ni P1 C15 -58.3(5) . . . . ?
S1 Ni P1 C15 164.0(9) . . . . ?
P2 Ni P1 C15 119.0(4) . . . . ?
C1 Ni P2 C14 43(3) . . . . ?
P1 Ni P2 C14 -3.8(4) . . . . ?
S1 Ni P2 C14 -179.7(4) . . . . ?
C1 Ni P2 C19 164(3) . . . . ?
P1 Ni P2 C19 117.0(5) . . . . ?
S1 Ni P2 C19 -58.9(5) . . . . ?
C1 Ni P2 C21 -77(3) . . . . ?
P1 Ni P2 C21 -124.2(4) . . . . ?
S1 Ni P2 C21 59.9(4) . . . . ?
C1 Ni S1 C7 5.7(4) . . . . ?
P1 Ni S1 C7 143.2(8) . . . . ?
P2 Ni S1 C7 -171.8(3) . . . . ?
C8 N1 C2 C3 13.8(11) . . . . ?
C8 N1 C2 C7 -164.9(7) . . . . ?
N1 C2 C3 C4 -179.8(6) . . . . ?
C7 C2 C3 C4 -1.1(10) . . . . ?
C2 C3 C4 C5 -1.7(12) . . . . ?
C3 C4 C5 C6 3.3(12) . . . . ?
C4 C5 C6 C7 -2.1(11) . . . . ?
C5 C6 C7 C2 -0.6(10) . . . . ?
C5 C6 C7 S1 175.4(5) . . . . ?
C3 C2 C7 C6 2.2(9) . . . . ?
N1 C2 C7 C6 -179.1(5) . . . . ?
C3 C2 C7 S1 -173.7(5) . . . . ?
N1 C2 C7 S1 5.0(8) . . . . ?
Ni S1 C7 C6 99.0(5) . . . . ?
Ni S1 C7 C2 -85.2(5) . . . . ?
C2 N1 C8 O1 4.0(14) . . . . ?
C2 N1 C8 C9 -175.7(7) . . . . ?
O1 C8 C9 C10 34.3(14) . . . . ?
N1 C8 C9 C10 -146.0(10) . . . . ?
O1 C8 C9 C11 156.8(10) . . . . ?
N1 C8 C9 C11 -23.5(12) . . . . ?
O1 C8 C9 C12 -83.4(12) . . . . ?
N1 C8 C9 C12 96.3(11) . . . . ?
C17 P1 C13 C14 137.4(9) . . . . ?
C15 P1 C13 C14 -114.0(10) . . . . ?
Ni P1 C13 C14 14.2(10) . . . . ?
P1 C13 C14 P2 -17.6(13) . . . . ?
C19 P2 C14 C13 -114.7(9) . . . . ?
C21 P2 C14 C13 140.3(10) . . . . ?
Ni P2 C14 C13 13.4(10) . . . . ?
C17 P1 C15 C16 -174.8(9) . . . . ?
C13 P1 C15 C16 76.3(10) . . . . ?
Ni P1 C15 C16 -47.4(10) . . . . ?
C13 P1 C17 C18 54.4(9) . . . . ?
C15 P1 C17 C18 -58.0(8) . . . . ?
Ni P1 C17 C18 173.6(6) . . . . ?
C14 P2 C19 C20 68.7(10) . . . . ?
C21 P2 C19 C20 178.1(9) . . . . ?
Ni P2 C19 C20 -54.5(9) . . . . ?
C14 P2 C21 C22 -69.2(11) . . . . ?
C19 P2 C21 C22 -178.3(10) . . . . ?
Ni P2 C21 C22 53.4(11) . . . . ?
