#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:32:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180144 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/41/7104193.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_7104193
loop_
_publ_author_name
'Pattacini, Roberto'
'Jie, Suyun'
'Braunstein, Pierre'
_publ_section_title
;
 Facile dichloromethane activation and phosphine methylation. Isolation
 of unprecedented zwitterionic organozinc and organocobalt
 intermediates.
;
_journal_issue                   8
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              890
_journal_page_last               892
_journal_paper_doi               10.1039/b817728g
_journal_volume                  34
_journal_year                    2009
_chemical_formula_moiety         'C38 H34 Cl4 P2 Zn2'
_chemical_formula_sum            'C38 H34 Cl4 P2 Zn2'
_chemical_formula_weight         825.13
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 104.530(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5489(7)
_cell_length_b                   13.7296(3)
_cell_length_c                   18.8997(8)
_cell_measurement_reflns_used    4830
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      0.998
_cell_volume                     3654.5(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12656
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.07
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.720
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.854
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         5318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0354
_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)+(0.0630P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1142
_reflns_number_gt                3964
_reflns_number_total             5318
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b817728g.txt
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7104193
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Zn1 Zn 0.729161(19) 0.199178(18) 0.073174(14) 0.02680(10) Uani 1 1 d . . .
C1 C 0.61492(16) 0.12522(16) 0.08778(14) 0.0298(5) Uani 1 1 d . . .
H1A H 0.6056 0.0701 0.0546 0.036 Uiso 1 1 calc R . .
H1B H 0.6326 0.0987 0.1369 0.036 Uiso 1 1 calc R . .
C2 C 0.51431(16) 0.30506(14) 0.10793(12) 0.0245(4) Uani 1 1 d . . .
C3 C 0.46057(18) 0.37944(16) 0.06777(14) 0.0342(5) Uani 1 1 d . . .
H3 H 0.4188 0.3664 0.0228 0.041 Uiso 1 1 calc R . .
C4 C 0.4701(2) 0.47371(17) 0.09570(16) 0.0438(7) Uani 1 1 d . . .
H4 H 0.4348 0.5239 0.0690 0.053 Uiso 1 1 calc R . .
C5 C 0.5311(2) 0.49332(18) 0.16218(16) 0.0404(6) Uani 1 1 d . . .
H5 H 0.5365 0.5566 0.1804 0.049 Uiso 1 1 calc R . .
C6 C 0.58442(19) 0.41965(18) 0.20217(15) 0.0374(6) Uani 1 1 d . . .
H6 H 0.6257 0.4332 0.2473 0.045 Uiso 1 1 calc R . .
C7 C 0.57651(18) 0.32581(17) 0.17511(13) 0.0316(5) Uani 1 1 d . . .
H7 H 0.6129 0.2763 0.2019 0.038 Uiso 1 1 calc R . .
C8 C 0.43294(16) 0.11787(15) 0.12826(12) 0.0247(4) Uani 1 1 d . . .
C9 C 0.44686(18) 0.01903(16) 0.14156(13) 0.0325(5) Uani 1 1 d . . .
H9 H 0.4951 -0.0134 0.1269 0.039 Uiso 1 1 calc R . .
C10 C 0.38866(19) -0.03125(18) 0.17673(15) 0.0412(6) Uani 1 1 d . . .
H10 H 0.3972 -0.0978 0.1850 0.049 Uiso 1 1 calc R . .
C11 C 0.3180(2) 0.01706(18) 0.19959(15) 0.0419(6) Uani 1 1 d . . .
H11 H 0.2796 -0.0169 0.2238 0.050 Uiso 1 1 calc R . .
C12 C 0.3042(2) 0.11471(18) 0.18678(16) 0.0406(6) Uani 1 1 d . . .
H12 H 0.2561 0.1468 0.2019 0.049 Uiso 1 1 calc R . .
C13 C 0.36152(19) 0.16618(17) 0.15125(15) 0.0349(6) Uani 1 1 d . . .
H13 H 0.3522 0.2326 0.1429 0.042 Uiso 1 1 calc R . .
C14 C 0.43841(16) 0.17792(15) -0.01733(12) 0.0252(5) Uani 1 1 d . . .
C15 C 0.47783(18) 0.22082(16) -0.07051(12) 0.0304(5) Uani 1 1 d . . .
H15 H 0.5368 0.2510 -0.0568 0.036 Uiso 1 1 calc R . .
C16 C 0.42864(19) 0.21799(16) -0.14322(13) 0.0320(5) Uani 1 1 d . . .
H16 H 0.4546 0.2468 -0.1783 0.038 Uiso 1 1 calc R . .
C17 C 0.34118(19) 0.17262(17) -0.16416(13) 0.0342(5) Uani 1 1 d . . .
H17 H 0.3081 0.1716 -0.2131 0.041 Uiso 1 1 calc R . .
C18 C 0.30257(18) 0.12844(17) -0.11188(14) 0.0350(5) Uani 1 1 d . . .
H18 H 0.2444 0.0966 -0.1261 0.042 Uiso 1 1 calc R . .
C19 C 0.35052(17) 0.13188(16) -0.03917(13) 0.0302(5) Uani 1 1 d . . .
H19 H 0.3240 0.1032 -0.0043 0.036 Uiso 1 1 calc R . .
Cl1 Cl 0.71526(4) 0.35923(4) 0.02759(3) 0.03061(14) Uani 1 1 d . . .
Cl2 Cl 0.84983(5) 0.18656(4) 0.17389(3) 0.03539(15) Uani 1 1 d . . .
P1 P 0.50382(4) 0.18068(4) 0.07706(3) 0.02323(13) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
P P 0.1023 0.0942 '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'
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 Zn1 Cl2 109.82(7) . . ?
C1 Zn1 Cl1 121.38(6) . . ?
Cl2 Zn1 Cl1 111.06(2) . . ?
C1 Zn1 Cl1 113.22(7) . 7_655 ?
Cl2 Zn1 Cl1 107.50(2) . 7_655 ?
Cl1 Zn1 Cl1 92.115(19) . 7_655 ?
P1 C1 Zn1 122.10(12) . . ?
P1 C1 H1A 106.8 . . ?
Zn1 C1 H1A 106.8 . . ?
P1 C1 H1B 106.8 . . ?
Zn1 C1 H1B 106.8 . . ?
H1A C1 H1B 106.7 . . ?
C3 C2 C7 119.7(2) . . ?
C3 C2 P1 122.00(18) . . ?
C7 C2 P1 118.25(17) . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 120.3(2) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C9 C8 C13 119.8(2) . . ?
C9 C8 P1 119.27(17) . . ?
C13 C8 P1 120.84(16) . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.7(2) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C19 C14 C15 119.2(2) . . ?
C19 C14 P1 121.41(17) . . ?
C15 C14 P1 119.41(18) . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.6(2) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
Zn1 Cl1 Zn1 87.885(19) . 7_655 ?
C1 P1 C2 111.99(11) . . ?
C1 P1 C14 110.40(11) . . ?
C2 P1 C14 108.81(10) . . ?
C1 P1 C8 111.46(10) . . ?
C2 P1 C8 107.08(10) . . ?
C14 P1 C8 106.91(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
Zn1 C1 2.025(2) . ?
Zn1 Cl2 2.2491(7) . ?
Zn1 Cl1 2.3505(6) . ?
Zn1 Cl1 2.3867(6) 7_655 ?
C1 P1 1.752(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.390(3) . ?
C2 C7 1.391(3) . ?
C2 P1 1.799(2) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.386(3) . ?
C8 C13 1.391(3) . ?
C8 P1 1.801(2) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.393(3) . ?
C14 C15 1.405(3) . ?
C14 P1 1.799(2) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
Cl1 Zn1 2.3867(6) 7_655 ?
