#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:47:42 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178701 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/12/4081241.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_4081241
loop_
_publ_author_name
'Almazahreh, Laith R.'
'Apfel, Ulf-Peter'
'Imhof, Wolfgang'
'Rudolph, Manfred'
'Görls, Helmar'
'Talarmin, Jean'
'Schollhammer, Philippe'
'El-khateeb, Mohammad'
'Weigand, Wolfgang'
_publ_section_title
;
 A Novel [FeFe] Hydrogenase Model with a (SCH2)2P═O Moiety
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              4523
_journal_paper_doi               10.1021/om4003544
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C8 H9 Cl2 O P'
_chemical_formula_sum            'C8 H9 Cl2 O P'
_chemical_formula_weight         223.02
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 102.665(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7410(4)
_cell_length_b                   7.3835(2)
_cell_length_c                   10.5054(3)
_cell_measurement_reflns_used    6073
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.21
_cell_volume                     964.23(5)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6073
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.071
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.221
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0645
_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)+(0.0585P)²+12.4247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2207
_refine_ls_wR_factor_ref         0.2216
_reflns_number_gt                2095
_reflns_number_total             2206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4003544_si_001.cif
_cod_data_source_block           FO4440
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4081241
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl1 Cl 1.27339(12) 0.5551(2) 0.15552(16) 0.0247(4) Uani 1 1 d .
Cl2 Cl 0.91611(11) 0.23448(19) 0.09849(14) 0.0190(4) Uani 1 1 d .
P1 P 1.14513(11) 0.21998(19) 0.09281(13) 0.0128(3) Uani 1 1 d .
O1 O 1.1220(3) 0.2333(6) -0.0527(4) 0.0172(8) Uani 1 1 d .
C1 C 1.2948(5) 0.0624(8) 0.2953(6) 0.0206(12) Uani 1 1 d .
H1A H 1.2520 0.1076 0.3518 0.025 Uiso 1 1 calc R
C2 C 1.3886(5) -0.0364(9) 0.3454(6) 0.0232(13) Uani 1 1 d .
H2A H 1.4094 -0.0597 0.4364 0.028 Uiso 1 1 calc R
C3 C 1.4512(5) -0.1002(8) 0.2625(7) 0.0233(13) Uani 1 1 d .
H3A H 1.5150 -0.1666 0.2971 0.028 Uiso 1 1 calc R
C4 C 1.4216(5) -0.0678(9) 0.1299(7) 0.0231(13) Uani 1 1 d .
H4A H 1.4649 -0.1125 0.0739 0.028 Uiso 1 1 calc R
C5 C 1.3285(5) 0.0297(8) 0.0779(6) 0.0183(11) Uani 1 1 d .
H5A H 1.3083 0.0527 -0.0132 0.022 Uiso 1 1 calc R
C6 C 1.2652(4) 0.0935(8) 0.1615(5) 0.0159(11) Uani 1 1 d .
C7 C 1.1559(4) 0.4389(7) 0.1739(5) 0.0144(10) Uani 1 1 d .
H7A H 1.0918 0.5129 0.1364 0.017 Uiso 1 1 calc R
H7B H 1.1581 0.4213 0.2679 0.017 Uiso 1 1 calc R
C8 C 1.0388(4) 0.1131(7) 0.1566(5) 0.0140(10) Uani 1 1 d .
H8A H 1.0301 -0.0146 0.1273 0.017 Uiso 1 1 calc R
H8B H 1.0575 0.1145 0.2531 0.017 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
Cl1 0.0184(7) 0.0176(7) 0.0381(9) -0.0015(6) 0.0063(6) -0.0057(5)
Cl2 0.0122(6) 0.0173(7) 0.0264(7) 0.0035(5) 0.0022(5) 0.0005(5)
P1 0.0140(7) 0.0132(7) 0.0111(6) 0.0004(5) 0.0025(5) -0.0011(5)
O1 0.019(2) 0.019(2) 0.0147(19) -0.0019(15) 0.0057(15) -0.0028(16)
C1 0.020(3) 0.021(3) 0.020(3) -0.002(2) 0.003(2) -0.002(2)
C2 0.019(3) 0.026(3) 0.021(3) 0.002(2) -0.003(2) -0.002(2)
C3 0.014(3) 0.015(3) 0.038(3) 0.001(3) 0.000(2) -0.001(2)
C4 0.018(3) 0.019(3) 0.035(3) 0.000(3) 0.013(3) 0.001(2)
C5 0.017(3) 0.018(3) 0.021(3) -0.001(2) 0.006(2) -0.002(2)
C6 0.017(3) 0.013(2) 0.017(3) -0.001(2) 0.003(2) -0.002(2)
C7 0.017(2) 0.010(2) 0.017(2) -0.0026(19) 0.005(2) -0.003(2)
C8 0.013(2) 0.013(2) 0.016(2) 0.003(2) 0.0032(19) -0.003(2)
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'
Cl Cl 0.1484 0.1585 '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 C6 113.8(3)
O1 P1 C8 114.2(2)
C6 P1 C8 105.2(3)
O1 P1 C7 113.5(2)
C6 P1 C7 107.6(3)
C8 P1 C7 101.5(3)
C6 C1 C2 119.1(6)
C6 C1 H1A 120.5
C2 C1 H1A 120.5
C3 C2 C1 120.1(6)
C3 C2 H2A 119.9
C1 C2 H2A 119.9
C4 C3 C2 120.4(6)
C4 C3 H3A 119.8
C2 C3 H3A 119.8
C3 C4 C5 120.4(6)
C3 C4 H4A 119.8
C5 C4 H4A 119.8
C4 C5 C6 119.1(6)
C4 C5 H5A 120.5
C6 C5 H5A 120.5
C1 C6 C5 120.9(5)
C1 C6 P1 120.6(4)
C5 C6 P1 118.6(4)
Cl1 C7 P1 111.0(3)
Cl1 C7 H7A 109.4
P1 C7 H7A 109.4
Cl1 C7 H7B 109.4
P1 C7 H7B 109.4
H7A C7 H7B 108.0
Cl2 C8 P1 108.8(3)
Cl2 C8 H8A 109.9
P1 C8 H8A 109.9
Cl2 C8 H8B 109.9
P1 C8 H8B 109.9
H8A C8 H8B 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C7 1.772(6)
Cl2 C8 1.789(5)
P1 O1 1.495(4)
P1 C6 1.802(6)
P1 C8 1.818(5)
P1 C7 1.819(5)
C1 C6 1.392(8)
C1 C2 1.401(8)
C1 H1A 0.9500
C2 C3 1.386(9)
C2 H2A 0.9500
C3 C4 1.382(9)
C3 H3A 0.9500
C4 C5 1.393(8)
C4 H4A 0.9500
C5 C6 1.398(8)
C5 H5A 0.9500
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
