#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/09/7050943.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_7050943
loop_
_publ_author_name
'Petr Štěpnička'
'Ivana Císařová'
_publ_section_title
;
 Hydrogen bonding and self-assembly in the crystal structures of
 ferrocenylmethanol derivatives having different phosphorus
 substituents on the ferrocene unit
;
_journal_issue                   10
_journal_name_full               'New J. Chem.'
_journal_page_first              1389
_journal_page_last               1396
_journal_paper_doi               10.1039/b204655p
_journal_volume                  26
_journal_year                    2002
_chemical_formula_sum            'C23 H21 Fe O P S'
_chemical_formula_weight         432.28
_chemical_name_systematic
; 
2-(diphenylthiophosphoryl)ferrocenylmethanol
;
_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.
_cell_angle_beta                 105.749(1)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   8.6792(1)
_cell_length_b                   17.6265(3)
_cell_length_c                   13.2883(2)
_cell_measurement_reflns_used    17834
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     1956.58(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Giacovazzo, 1994)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 0.110
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Enraf KappaCCD'
_diffrn_measurement_method
;
CCD
rotation scans to fill Ewald sphere
(262 frames; 2 deg omega rotation, 70 s exposure each)
;
_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  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8689
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.969
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0294
_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)+(0.0242P)²+1.5162P] where 
P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0712
_reflns_number_gt                4135
_reflns_number_total             4488
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b204655p.txt
_cod_data_source_block           ps670
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7050943
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.66485(3) -0.107391(12) 0.301945(17) 0.01924(7) Uani 1 1 d . . .
S S 0.89473(5) 0.11364(3) 0.35669(3) 0.02909(11) Uani 1 1 d . . .
P P 0.74113(5) 0.07487(2) 0.23090(3) 0.01680(9) Uani 1 1 d . . .
O O 1.12384(16) -0.02044(8) 0.28048(12) 0.0346(3) Uani 1 1 d . . .
H90 H 1.097(3) 0.0229(15) 0.2898(19) 0.049(7) Uiso 1 1 d . . .
C1 C 0.86314(19) -0.07991(9) 0.25561(13) 0.0212(3) Uani 1 1 d . . .
C2 C 0.73507(18) -0.02612(8) 0.21612(11) 0.0178(3) Uani 1 1 d . . .
C3 C 0.6000(2) -0.06784(9) 0.15277(12) 0.0228(3) Uani 1 1 d . . .
H3 H 0.5010 -0.0476 0.1180 0.027 Uiso 1 1 calc R . .
C4 C 0.6453(2) -0.14538(10) 0.15302(13) 0.0275(4) Uani 1 1 d . . .
H4 H 0.5808 -0.1847 0.1184 0.033 Uiso 1 1 calc R . .
C5 C 0.8054(2) -0.15250(9) 0.21486(13) 0.0255(3) Uani 1 1 d . . .
H5 H 0.8638 -0.1974 0.2270 0.031 Uiso 1 1 calc R . .
C6 C 0.7050(3) -0.08641(16) 0.45728(16) 0.0551(7) Uani 1 1 d . . .
H6 H 0.7865 -0.0561 0.4973 0.066 Uiso 1 1 calc R . .
C7 C 0.5499(4) -0.06199(12) 0.40294(18) 0.0543(7) Uani 1 1 d . . .
H7 H 0.5107 -0.0127 0.4008 0.065 Uiso 1 1 calc R . .
C8 C 0.4650(2) -0.12600(14) 0.35233(17) 0.0424(5) Uani 1 1 d . . .
H8 H 0.3600 -0.1267 0.3105 0.051 Uiso 1 1 calc R . .
C9 C 0.5682(3) -0.18781(11) 0.37696(16) 0.0374(5) Uani 1 1 d . . .
H9 H 0.5427 -0.2373 0.3542 0.045 Uiso 1 1 calc R . .
C10 C 0.7143(3) -0.16446(14) 0.44032(16) 0.0436(5) Uani 1 1 d . . .
H10 H 0.8032 -0.1951 0.4670 0.052 Uiso 1 1 calc R . .
C11 C 1.0260(2) -0.06545(10) 0.32757(14) 0.0272(4) Uani 1 1 d . . .
H11A H 1.0147 -0.0399 0.3898 0.033 Uiso 1 1 calc R . .
H11B H 1.0788 -0.1136 0.3490 0.033 Uiso 1 1 calc R . .
C12 C 0.78105(18) 0.11122(9) 0.11244(12) 0.0198(3) Uani 1 1 d . . .
C13 C 0.7764(2) 0.18980(10) 0.09731(15) 0.0308(4) Uani 1 1 d . . .
H13 H 0.7533 0.2217 0.1470 0.037 Uiso 1 1 calc R . .
C14 C 0.8063(2) 0.22020(12) 0.00848(17) 0.0390(5) Uani 1 1 d . . .
H14 H 0.8034 0.2725 -0.0014 0.047 Uiso 1 1 calc R . .
C15 C 0.8405(2) 0.17289(13) -0.06575(16) 0.0390(5) Uani 1 1 d . . .
H15 H 0.8600 0.1935 -0.1255 0.047 Uiso 1 1 calc R . .
C16 C 0.8457(2) 0.09507(12) -0.05160(14) 0.0324(4) Uani 1 1 d . . .
H16 H 0.8685 0.0635 -0.1018 0.039 Uiso 1 1 calc R . .
C17 C 0.81672(19) 0.06411(10) 0.03832(13) 0.0243(3) Uani 1 1 d . . .
H17 H 0.8213 0.0119 0.0484 0.029 Uiso 1 1 calc R . .
C18 C 0.53723(18) 0.10436(8) 0.21909(12) 0.0186(3) Uani 1 1 d . . .
C19 C 0.4910(2) 0.12908(9) 0.30613(13) 0.0239(3) Uani 1 1 d . . .
H19 H 0.5656 0.1315 0.3712 0.029 Uiso 1 1 calc R . .
C20 C 0.3328(2) 0.15018(9) 0.29515(15) 0.0302(4) Uani 1 1 d . . .
H20 H 0.3018 0.1665 0.3533 0.036 Uiso 1 1 calc R . .
C21 C 0.2212(2) 0.14708(10) 0.19864(16) 0.0315(4) Uani 1 1 d . . .
H21 H 0.1155 0.1609 0.1921 0.038 Uiso 1 1 calc R . .
C22 C 0.2670(2) 0.12331(10) 0.11163(16) 0.0297(4) Uani 1 1 d . . .
H22 H 0.1923 0.1215 0.0466 0.036 Uiso 1 1 calc R . .
C23 C 0.42416(19) 0.10230(9) 0.12157(13) 0.0228(3) Uani 1 1 d . . .
H23 H 0.4547 0.0867 0.0629 0.027 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'
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'
Fe Fe 0.3463 0.8444 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Fe C3 41.73(6) . . ?
C2 Fe C6 116.65(8) . . ?
C3 Fe C6 148.71(10) . . ?
C2 Fe C10 146.70(8) . . ?
C3 Fe C10 170.10(9) . . ?
C6 Fe C10 40.25(10) . . ?
C2 Fe C1 41.72(6) . . ?
C3 Fe C1 69.90(7) . . ?
C6 Fe C1 109.75(8) . . ?
C10 Fe C1 113.70(8) . . ?
C2 Fe C9 173.37(8) . . ?
C3 Fe C9 132.36(8) . . ?
C6 Fe C9 67.04(9) . . ?
C10 Fe C9 39.59(9) . . ?
C1 Fe C9 143.71(7) . . ?
C2 Fe C7 111.62(7) . . ?
C3 Fe C7 116.86(9) . . ?
C6 Fe C7 40.54(11) . . ?
C10 Fe C7 67.72(9) . . ?
C1 Fe C7 135.19(9) . . ?
C9 Fe C7 67.16(8) . . ?
C2 Fe C8 135.11(8) . . ?
C3 Fe C8 109.83(8) . . ?
C6 Fe C8 67.90(9) . . ?
C10 Fe C8 67.38(9) . . ?
C1 Fe C8 175.32(8) . . ?
C9 Fe C8 39.82(8) . . ?
C7 Fe C8 40.46(10) . . ?
C2 Fe C4 69.29(6) . . ?
C3 Fe C4 40.75(7) . . ?
C6 Fe C4 170.25(10) . . ?
C10 Fe C4 130.65(9) . . ?
C1 Fe C4 68.99(7) . . ?
C9 Fe C4 107.90(8) . . ?
C7 Fe C4 146.63(10) . . ?
C8 Fe C4 114.05(8) . . ?
C2 Fe C5 68.98(6) . . ?
C3 Fe C5 68.46(7) . . ?
C6 Fe C5 132.69(10) . . ?
C10 Fe C5 107.77(8) . . ?
C1 Fe C5 40.78(6) . . ?
C9 Fe C5 113.07(7) . . ?
C7 Fe C5 173.08(10) . . ?
C8 Fe C5 143.78(9) . . ?
C4 Fe C5 40.29(7) . . ?
C2 P C18 106.09(7) . . ?
C2 P C12 105.21(7) . . ?
C18 P C12 103.62(7) . . ?
C2 P S 115.72(5) . . ?
C18 P S 113.40(5) . . ?
C12 P S 111.77(5) . . ?
C5 C1 C2 107.11(14) . . ?
C5 C1 C11 124.63(15) . . ?
C2 C1 C11 128.25(14) . . ?
C5 C1 Fe 70.30(9) . . ?
C2 C1 Fe 68.69(8) . . ?
C11 C1 Fe 125.16(11) . . ?
C3 C2 C1 107.43(13) . . ?
C3 C2 P 124.41(12) . . ?
C1 C2 P 127.96(12) . . ?
C3 C2 Fe 69.36(9) . . ?
C1 C2 Fe 69.59(8) . . ?
P C2 Fe 130.24(8) . . ?
C4 C3 C2 107.93(15) . . ?
C4 C3 Fe 70.41(9) . . ?
C2 C3 Fe 68.91(9) . . ?
C5 C4 C3 108.30(15) . . ?
C5 C4 Fe 69.99(9) . . ?
C3 C4 Fe 68.84(9) . . ?
C4 C5 C1 109.22(14) . . ?
C4 C5 Fe 69.72(10) . . ?
C1 C5 Fe 68.91(9) . . ?
C10 C6 C7 107.8(2) . . ?
C10 C6 Fe 70.07(12) . . ?
C7 C6 Fe 70.06(12) . . ?
C6 C7 C8 107.54(19) . . ?
C6 C7 Fe 69.40(12) . . ?
C8 C7 Fe 70.05(11) . . ?
C9 C8 C7 107.1(2) . . ?
C9 C8 Fe 69.76(11) . . ?
C7 C8 Fe 69.48(12) . . ?
C10 C9 C8 109.63(19) . . ?
C10 C9 Fe 70.10(11) . . ?
C8 C9 Fe 70.42(11) . . ?
C9 C10 C6 107.9(2) . . ?
C9 C10 Fe 70.31(11) . . ?
C6 C10 Fe 69.68(12) . . ?
O C11 C1 112.70(14) . . ?
C17 C12 C13 119.63(15) . . ?
C17 C12 P 122.41(12) . . ?
C13 C12 P 117.95(13) . . ?
C14 C13 C12 120.11(18) . . ?
C13 C14 C15 120.04(18) . . ?
C16 C15 C14 120.41(17) . . ?
C15 C16 C17 119.77(18) . . ?
C12 C17 C16 120.03(16) . . ?
C19 C18 C23 119.35(15) . . ?
C19 C18 P 120.86(12) . . ?
C23 C18 P 119.79(12) . . ?
C20 C19 C18 119.65(16) . . ?
C21 C20 C19 120.65(16) . . ?
C20 C21 C22 119.88(16) . . ?
C23 C22 C21 119.99(17) . . ?
C22 C23 C18 120.47(16) . . ?
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
Fe C2 2.0252(15) . ?
Fe C3 2.0314(16) . ?
Fe C6 2.032(2) . ?
Fe C10 2.0369(19) . ?
Fe C1 2.0373(16) . ?
Fe C9 2.0395(18) . ?
Fe C7 2.0405(19) . ?
Fe C8 2.0480(19) . ?
Fe C4 2.0522(17) . ?
Fe C5 2.0558(16) . ?
S P 1.9567(6) . ?
P C2 1.7901(15) . ?
P C18 1.8100(16) . ?
P C12 1.8178(16) . ?
O C11 1.425(2) . ?
C1 C5 1.426(2) . ?
C1 C2 1.447(2) . ?
C1 C11 1.498(2) . ?
C2 C3 1.445(2) . ?
C3 C4 1.422(2) . ?
C4 C5 1.415(3) . ?
C6 C10 1.400(4) . ?
C6 C7 1.411(4) . ?
C7 C8 1.414(3) . ?
C8 C9 1.392(3) . ?
C9 C10 1.381(3) . ?
C12 C17 1.386(2) . ?
C12 C13 1.399(2) . ?
C13 C14 1.384(3) . ?
C14 C15 1.384(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.397(2) . ?
C18 C19 1.393(2) . ?
C18 C23 1.398(2) . ?
C19 C20 1.392(2) . ?
C20 C21 1.382(3) . ?
C21 C22 1.386(3) . ?
C22 C23 1.384(2) . ?
