#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/22/4022228.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_4022228
loop_
_publ_author_name
'Noriyasu Kataoka'
'Quinetta Shelby'
'James P. Stambuli'
'John F. Hartwig'
_publ_contact_author
;
    John F. Hartwig
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, 
CT 06520-8107
;
_publ_contact_author_email       ' John.Hartwig@yale.edu '
_publ_contact_author_fax         ' 203-432-6144 '
_publ_contact_author_phone       ' 203-432-3917 '
_publ_section_title
;
 Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines
 for Palladium-Catalyzed C-C, C-N, and C-O Bond-Forming Cross-Couplings
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5553
_journal_page_last               5566
_journal_paper_doi               10.1021/jo025732j
_journal_volume                  67
_journal_year                    2002
_chemical_formula_moiety         'C42 H43 Fe P '
_chemical_formula_sum            'C42 H43 Fe P'
_chemical_formula_weight         634.62
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             'Thu Jun 30 15:37:56 2000'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                88.715(2)
_cell_angle_beta                 78.692(2)
_cell_angle_gamma                79.560(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3484(3)
_cell_length_b                   12.5331(3)
_cell_length_c                   13.3058(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    183.2
_cell_measurement_theta_max      0.0
_cell_measurement_theta_min      0.0
_cell_volume                     1664.06(8)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_diffrn_ambient_temperature      183.2
_diffrn_measurement_device       unknown
_diffrn_measurement_method       'omega scans with profile analysis'
_diffrn_orient_matrix_UB_11      0.00000
_diffrn_orient_matrix_UB_12      0.00000
_diffrn_orient_matrix_UB_13      0.00000
_diffrn_orient_matrix_UB_21      0.00000
_diffrn_orient_matrix_UB_22      0.00000
_diffrn_orient_matrix_UB_23      0.00000
_diffrn_orient_matrix_UB_31      0.00000
_diffrn_orient_matrix_UB_32      0.00000
_diffrn_orient_matrix_UB_33      0.00000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoKalpha
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.00
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7626
_diffrn_reflns_theta_max         27.56
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       plate
_exptl_crystal_F_000             672.00
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.686
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         5135
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0409
_refine_ls_shift/esd_max         0.0015
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0403
_reflns_number_observed          5135
_reflns_number_total             7626
_reflns_observed_criterion       3.00
_cod_data_source_file            jo025732j_s2_1.cif
_cod_data_source_block           Ph4FcP(t-Bu)2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 87 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1       '
_cod_original_formula_sum        'C42 H43 Fe P '
_cod_database_code               4022228
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,   -y,   -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
Fe(1) 0.52098(3) 0.29811(2) 0.73249(2) 0.02394(9) Uani
P(1) 0.22348(6) 0.22914(4) 0.89799(4) 0.0263(2) Uani
C(1) 0.4035(2) 0.4121(2) 0.6602(2) 0.0253(6) Uani
C(2) 0.4919(2) 0.3391(2) 0.5861(2) 0.0253(6) Uani
C(3) 0.6263(2) 0.3448(2) 0.5955(2) 0.0261(6) Uani
C(4) 0.6204(2) 0.4218(2) 0.6764(2) 0.0252(6) Uani
C(5) 0.4795(2) 0.4638(2) 0.7162(2) 0.0255(6) Uani
C(6) 0.4483(2) 0.2724(2) 0.5128(2) 0.0263(6) Uani
C(7) 0.3348(3) 0.3130(2) 0.4734(2) 0.0332(7) Uani
C(8) 0.2876(3) 0.2519(2) 0.4085(2) 0.0414(8) Uani
C(9) 0.3554(3) 0.1495(2) 0.3795(2) 0.0466(9) Uani
C(10) 0.4688(3) 0.1077(2) 0.4170(2) 0.0444(9) Uani
C(11) 0.5151(3) 0.1683(2) 0.4838(2) 0.0350(7) Uani
C(12) 0.7477(2) 0.2881(2) 0.5238(2) 0.0304(7) Uani
C(13) 0.8552(3) 0.2222(2) 0.5566(2) 0.0371(8) Uani
C(14) 0.9625(3) 0.1681(2) 0.4853(2) 0.0484(9) Uani
C(15) 0.9637(3) 0.1799(3) 0.3817(2) 0.0527(9) Uani
C(16) 0.8610(3) 0.2461(2) 0.3487(2) 0.0473(9) Uani
C(17) 0.7538(3) 0.3001(2) 0.4186(2) 0.0367(8) Uani
C(18) 0.7352(2) 0.4560(2) 0.7104(2) 0.0277(6) Uani
C(19) 0.8491(2) 0.4701(2) 0.6394(2) 0.0335(7) Uani
C(20) 0.9539(3) 0.5074(2) 0.6694(2) 0.0446(9) Uani
C(21) 0.9470(3) 0.5313(2) 0.7709(2) 0.0483(10) Uani
C(22) 0.8362(3) 0.5174(2) 0.8423(2) 0.0410(8) Uani
C(23) 0.7313(3) 0.4792(2) 0.8132(2) 0.0342(7) Uani
C(24) 0.4161(2) 0.5535(2) 0.7911(2) 0.0256(6) Uani
C(25) 0.4629(3) 0.6508(2) 0.7842(2) 0.0319(7) Uani
C(26) 0.3947(3) 0.7387(2) 0.8464(2) 0.0357(8) Uani
C(27) 0.2796(3) 0.7307(2) 0.9144(2) 0.0359(7) Uani
C(28) 0.2315(3) 0.6344(2) 0.9226(2) 0.0375(8) Uani
C(29) 0.2999(3) 0.5461(2) 0.8610(2) 0.0333(7) Uani
C(30) 0.4025(2) 0.2141(2) 0.8414(2) 0.0240(6) Uani
C(31) 0.4891(2) 0.1424(2) 0.7646(2) 0.0292(7) Uani
C(32) 0.6229(3) 0.1497(2) 0.7644(2) 0.0355(7) Uani
C(33) 0.6235(3) 0.2268(2) 0.8392(2) 0.0335(8) Uani
C(34) 0.4895(2) 0.2677(2) 0.8855(2) 0.0289(7) Uani
C(35) 0.1436(2) 0.1677(2) 0.8018(2) 0.0321(7) Uani
C(36) 0.1772(3) 0.2283(3) 0.7019(2) 0.0473(10) Uani
C(37) -0.0088(3) 0.1974(3) 0.8387(2) 0.0488(10) Uani
C(38) 0.1801(4) 0.0459(2) 0.7801(3) 0.0483(10) Uani
C(39) 0.2349(2) 0.1315(2) 1.0094(2) 0.0331(7) Uani
C(40) 0.2928(5) 0.1865(3) 1.0871(2) 0.062(1) Uani
C(41) 0.0946(3) 0.1158(3) 1.0608(3) 0.057(1) Uani
C(42) 0.3235(4) 0.0212(3) 0.9820(3) 0.062(1) Uani
H(1) 0.308(2) 0.424(1) 0.671(1) 0.012(5) Uani
H(2) 0.293(2) 0.380(2) 0.492(2) 0.036(7) Uani
H(3) 0.211(2) 0.283(2) 0.383(2) 0.040(7) Uani
H(4) 0.332(2) 0.106(2) 0.333(2) 0.049(8) Uani
H(5) 0.519(2) 0.039(2) 0.400(2) 0.036(7) Uani
H(6) 0.596(2) 0.138(2) 0.510(2) 0.034(6) Uani
H(7) 0.852(2) 0.215(2) 0.631(2) 0.038(6) Uani
H(8) 1.032(3) 0.122(2) 0.509(2) 0.049(8) Uani
H(9) 1.036(3) 0.139(2) 0.339(2) 0.046(7) Uani
H(10) 0.864(2) 0.253(2) 0.275(2) 0.053(7) Uani
H(11) 0.682(2) 0.346(2) 0.396(2) 0.043(7) Uani
H(12) 0.859(2) 0.455(2) 0.570(2) 0.034(7) Uani
H(13) 1.028(2) 0.523(2) 0.622(2) 0.041(7) Uani
H(14) 1.016(2) 0.553(2) 0.790(2) 0.034(7) Uani
H(15) 0.824(2) 0.534(2) 0.911(2) 0.038(7) Uani
H(16) 0.654(2) 0.470(2) 0.864(2) 0.031(6) Uani
H(17) 0.532(2) 0.656(2) 0.740(2) 0.026(7) Uani
H(18) 0.429(2) 0.803(2) 0.841(2) 0.034(7) Uani
H(19) 0.235(2) 0.791(2) 0.959(2) 0.048(7) Uani
H(20) 0.155(2) 0.630(2) 0.965(2) 0.031(6) Uani
H(21) 0.265(2) 0.482(2) 0.867(2) 0.031(6) Uani
H(22) 0.460(2) 0.100(2) 0.721(2) 0.025(6) Uani
H(23) 0.696(2) 0.115(2) 0.721(2) 0.030(6) Uani
H(24) 0.691(2) 0.249(2) 0.853(2) 0.028(7) Uani
H(25) 0.462(2) 0.320(2) 0.931(2) 0.021(6) Uani
H(26) 0.147(2) 0.310(2) 0.717(2) 0.048(8) Uani
H(27) 0.271(3) 0.211(2) 0.672(2) 0.040(7) Uani
H(28) 0.123(3) 0.208(2) 0.653(2) 0.057(8) Uani
H(29) -0.036(3) 0.279(3) 0.845(2) 0.10(1) Uani
H(30) -0.052(3) 0.173(2) 0.787(2) 0.055(8) Uani
H(31) -0.042(3) 0.159(2) 0.896(2) 0.053(8) Uani
H(32) 0.149(2) 0.006(2) 0.837(2) 0.038(7) Uani
H(33) 0.132(3) 0.035(2) 0.722(2) 0.071(9) Uani
H(34) 0.278(3) 0.019(2) 0.761(2) 0.067(9) Uani
H(35) 0.231(3) 0.254(2) 1.104(2) 0.049(9) Uani
H(36) 0.293(3) 0.140(2) 1.144(2) 0.09(1) Uani
H(37) 0.393(4) 0.192(3) 1.054(3) 0.09(1) Uani
H(38) 0.056(3) 0.076(2) 1.017(2) 0.08(1) Uani
H(39) 0.034(3) 0.190(2) 1.075(2) 0.08(1) Uani
H(40) 0.099(3) 0.076(2) 1.125(2) 0.059(8) Uani
H(41) 0.297(4) -0.019(3) 0.937(3) 0.13(1) Uani
H(42) 0.410(4) 0.025(3) 0.946(3) 0.09(1) Uani
H(43) 0.325(3) -0.017(2) 1.046(2) 0.069(9) Uani
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 84 0.003 0.002 'International Tables'
H 0 86 0.000 0.000 'International Tables'
P 0 2 0.102 0.094 'International Tables'
Fe 0 2 0.346 0.844 'International Tables'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) Fe(1) C(2) 40.47(8) yes
C(1) Fe(1) C(3) 68.17(9) yes
C(1) Fe(1) C(4) 68.74(9) yes
C(1) Fe(1) C(5) 40.54(8) yes
C(1) Fe(1) C(30) 110.88(9) yes
C(1) Fe(1) C(31) 125.24(9) yes
C(1) Fe(1) C(32) 158.78(10) yes
C(1) Fe(1) C(33) 160.63(9) yes
C(1) Fe(1) C(34) 126.01(9) yes
C(2) Fe(1) C(3) 40.66(8) yes
C(2) Fe(1) C(4) 69.00(8) yes
C(2) Fe(1) C(5) 68.66(8) yes
C(2) Fe(1) C(30) 126.85(9) yes
C(2) Fe(1) C(31) 110.19(9) yes
C(2) Fe(1) C(32) 122.02(9) yes
C(2) Fe(1) C(33) 155.65(10) yes
C(2) Fe(1) C(34) 163.06(9) yes
C(3) Fe(1) C(4) 41.06(8) yes
C(3) Fe(1) C(5) 68.93(8) yes
C(3) Fe(1) C(30) 161.98(8) yes
C(3) Fe(1) C(31) 124.51(9) yes
C(3) Fe(1) C(32) 106.15(9) yes
C(3) Fe(1) C(33) 119.07(10) yes
C(3) Fe(1) C(34) 154.89(9) yes
C(4) Fe(1) C(5) 41.37(8) yes
C(4) Fe(1) C(30) 156.73(8) yes
C(4) Fe(1) C(31) 158.91(9) yes
C(4) Fe(1) C(32) 121.30(9) yes
C(4) Fe(1) C(33) 104.20(10) yes
C(4) Fe(1) C(34) 119.61(9) yes
C(5) Fe(1) C(30) 122.91(8) yes
C(5) Fe(1) C(31) 159.43(9) yes
C(5) Fe(1) C(32) 158.56(10) yes
C(5) Fe(1) C(33) 122.47(10) yes
C(5) Fe(1) C(34) 107.31(9) yes
C(30) Fe(1) C(31) 40.20(8) yes
C(30) Fe(1) C(32) 67.86(9) yes
C(30) Fe(1) C(33) 68.13(10) yes
C(30) Fe(1) C(34) 40.46(8) yes
C(31) Fe(1) C(32) 39.98(9) yes
C(31) Fe(1) C(33) 67.4(1) yes
C(31) Fe(1) C(34) 67.45(9) yes
C(32) Fe(1) C(33) 40.26(10) yes
C(32) Fe(1) C(34) 67.81(10) yes
C(33) Fe(1) C(34) 40.55(9) yes
C(30) P(1) C(35) 106.31(10) yes
C(30) P(1) C(39) 98.99(10) yes
C(35) P(1) C(39) 108.4(1) yes
Fe(1) C(1) C(2) 70.4(1) yes
Fe(1) C(1) C(5) 70.0(1) yes
C(2) C(1) C(5) 109.5(2) yes
Fe(1) C(2) C(1) 69.2(1) yes
Fe(1) C(2) C(3) 69.5(1) yes
Fe(1) C(2) C(6) 127.5(1) yes
C(1) C(2) C(3) 107.5(2) yes
C(1) C(2) C(6) 124.6(2) yes
C(3) C(2) C(6) 127.9(2) yes
Fe(1) C(3) C(2) 69.8(1) yes
Fe(1) C(3) C(4) 69.3(1) yes
Fe(1) C(3) C(12) 131.7(1) yes
C(2) C(3) C(4) 108.5(2) yes
C(2) C(3) C(12) 123.4(2) yes
C(4) C(3) C(12) 127.8(2) yes
Fe(1) C(4) C(3) 69.6(1) yes
Fe(1) C(4) C(5) 69.3(1) yes
Fe(1) C(4) C(18) 128.2(1) yes
C(3) C(4) C(5) 107.1(2) yes
C(3) C(4) C(18) 127.1(2) yes
C(5) C(4) C(18) 125.8(2) yes
Fe(1) C(5) C(1) 69.5(1) yes
Fe(1) C(5) C(4) 69.4(1) yes
Fe(1) C(5) C(24) 132.0(1) yes
C(1) C(5) C(4) 107.5(2) yes
C(1) C(5) C(24) 122.2(2) yes
C(4) C(5) C(24) 129.9(2) yes
C(2) C(6) C(7) 119.8(2) yes
C(2) C(6) C(11) 122.1(2) yes
C(7) C(6) C(11) 118.0(2) yes
C(6) C(7) C(8) 121.6(2) yes
C(7) C(8) C(9) 119.8(3) yes
C(8) C(9) C(10) 119.7(3) yes
C(9) C(10) C(11) 120.6(3) yes
C(6) C(11) C(10) 120.2(2) yes
C(3) C(12) C(13) 123.4(2) yes
C(3) C(12) C(17) 118.6(2) yes
C(13) C(12) C(17) 118.0(2) yes
C(12) C(13) C(14) 120.3(2) yes
C(13) C(14) C(15) 120.1(3) yes
C(14) C(15) C(16) 120.2(3) yes
C(15) C(16) C(17) 120.3(3) yes
C(12) C(17) C(16) 121.1(2) yes
C(4) C(18) C(19) 120.7(2) yes
C(4) C(18) C(23) 121.6(2) yes
C(19) C(18) C(23) 117.7(2) yes
C(18) C(19) C(20) 121.3(2) yes
C(19) C(20) C(21) 120.0(3) yes
C(20) C(21) C(22) 119.8(3) yes
C(21) C(22) C(23) 120.6(3) yes
C(18) C(23) C(22) 120.6(3) yes
C(5) C(24) C(25) 120.5(2) yes
C(5) C(24) C(29) 120.4(2) yes
C(25) C(24) C(29) 118.6(2) yes
C(24) C(25) C(26) 120.6(2) yes
C(25) C(26) C(27) 120.2(2) yes
C(26) C(27) C(28) 120.0(2) yes
C(27) C(28) C(29) 119.9(3) yes
C(24) C(29) C(28) 120.6(2) yes
Fe(1) C(30) P(1) 135.7(1) yes
Fe(1) C(30) C(31) 68.3(1) yes
Fe(1) C(30) C(34) 67.3(1) yes
P(1) C(30) C(31) 132.8(2) yes
P(1) C(30) C(34) 121.2(2) yes
C(31) C(30) C(34) 105.2(2) yes
Fe(1) C(31) C(30) 71.5(1) yes
Fe(1) C(31) C(32) 69.5(1) yes
C(30) C(31) C(32) 109.5(2) yes
Fe(1) C(32) C(31) 70.6(1) yes
Fe(1) C(32) C(33) 69.4(1) yes
C(31) C(32) C(33) 108.0(2) yes
Fe(1) C(33) C(32) 70.3(1) yes
Fe(1) C(33) C(34) 69.9(1) yes
C(32) C(33) C(34) 108.0(2) yes
Fe(1) C(34) C(30) 72.2(1) yes
Fe(1) C(34) C(33) 69.6(1) yes
C(30) C(34) C(33) 109.2(2) yes
P(1) C(35) C(36) 105.9(2) yes
P(1) C(35) C(37) 107.0(2) yes
P(1) C(35) C(38) 119.2(2) yes
C(36) C(35) C(37) 106.6(2) yes
C(36) C(35) C(38) 109.2(2) yes
C(37) C(35) C(38) 108.4(2) yes
P(1) C(39) C(40) 106.7(2) yes
P(1) C(39) C(41) 109.5(2) yes
P(1) C(39) C(42) 115.4(2) yes
C(40) C(39) C(41) 107.8(3) yes
C(40) C(39) C(42) 107.8(3) yes
C(41) C(39) C(42) 109.4(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Fe(1) C(1) 2.052(2) yes
Fe(1) C(2) 2.068(2) yes
Fe(1) C(3) 2.063(2) yes
Fe(1) C(4) 2.059(2) yes
Fe(1) C(5) 2.058(2) yes
Fe(1) C(30) 2.101(2) yes
Fe(1) C(31) 2.059(2) yes
Fe(1) C(32) 2.045(2) yes
Fe(1) C(33) 2.032(2) yes
Fe(1) C(34) 2.036(2) yes
P(1) C(30) 1.835(2) yes
P(1) C(35) 1.899(2) yes
P(1) C(39) 1.909(2) yes
C(1) C(2) 1.425(3) yes
C(1) C(5) 1.424(3) yes
C(2) C(3) 1.435(3) yes
C(2) C(6) 1.483(3) yes
C(3) C(4) 1.446(3) yes
C(3) C(12) 1.493(3) yes
C(4) C(5) 1.455(3) yes
C(4) C(18) 1.485(3) yes
C(5) C(24) 1.488(3) yes
C(6) C(7) 1.388(3) yes
C(6) C(11) 1.386(3) yes
C(7) C(8) 1.378(3) yes
C(8) C(9) 1.371(4) yes
C(9) C(10) 1.376(4) yes
C(10) C(11) 1.388(3) yes
C(12) C(13) 1.396(3) yes
C(12) C(17) 1.395(3) yes
C(13) C(14) 1.391(4) yes
C(14) C(15) 1.381(4) yes
C(15) C(16) 1.363(4) yes
C(16) C(17) 1.380(4) yes
C(18) C(19) 1.393(3) yes
C(18) C(23) 1.397(3) yes
C(19) C(20) 1.385(4) yes
C(20) C(21) 1.375(4) yes
C(21) C(22) 1.374(4) yes
C(22) C(23) 1.384(4) yes
C(24) C(25) 1.385(3) yes
C(24) C(29) 1.385(3) yes
C(25) C(26) 1.388(3) yes
C(26) C(27) 1.365(4) yes
C(27) C(28) 1.381(4) yes
C(28) C(29) 1.388(3) yes
C(30) C(31) 1.430(3) yes
C(30) C(34) 1.432(3) yes
C(31) C(32) 1.403(3) yes
C(32) C(33) 1.403(4) yes
C(33) C(34) 1.410(3) yes
C(35) C(36) 1.529(4) yes
C(35) C(37) 1.535(4) yes
C(35) C(38) 1.525(4) yes
C(39) C(40) 1.525(4) yes
C(39) C(41) 1.524(4) yes
C(39) C(42) 1.523(4) yes
