#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:32:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180144 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/41/7104189.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_7104189
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         'C19 H18 P, Cl3 H2 O Zn'
_chemical_formula_sum            'C19 H20 Cl3 O P Zn'
_chemical_formula_weight         467.04
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 94.549(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5221(5)
_cell_length_b                   8.8570(2)
_cell_length_c                   20.7669(9)
_cell_measurement_reflns_used    4604
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.024
_cell_measurement_theta_min      0.998
_cell_volume                     2112.60(14)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12513
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    1.622
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0506P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                3508
_reflns_number_total             4770
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b817728g.txt
_cod_data_source_block           (Ph3PMe)[ZnCl3(H2O)]
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7104189
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
Zn1 Zn 0.91678(2) 0.74372(2) 0.803799(13) 0.03098(11) Uani 1 1 d . . .
Cl1 Cl 0.97841(5) 0.53539(6) 0.85921(3) 0.03572(15) Uani 1 1 d . . .
Cl2 Cl 0.97850(5) 0.95955(6) 0.85450(3) 0.03388(15) Uani 1 1 d . . .
Cl3 Cl 0.72997(7) 0.74390(8) 0.77244(5) 0.0664(2) Uani 1 1 d . . .
O1 O 1.0213(2) 0.7482(2) 0.73029(10) 0.0494(6) Uani 1 1 d . . .
P1 P 0.75392(4) 0.14601(6) 0.99212(3) 0.02587(15) Uani 1 1 d . . .
C1 C 0.90198(18) 0.2067(2) 0.99130(11) 0.0299(5) Uani 1 1 d . . .
H1A H 0.9441 0.1797 1.0314 0.045 Uiso 1 1 calc R . .
H1B H 0.9042 0.3142 0.9858 0.045 Uiso 1 1 calc R . .
H1C H 0.9371 0.1586 0.9562 0.045 Uiso 1 1 calc R . .
C2 C 0.67823(18) 0.1812(2) 0.91495(10) 0.0297(5) Uani 1 1 d . . .
C3 C 0.5764(2) 0.1028(3) 0.89535(12) 0.0412(6) Uani 1 1 d . . .
H3 H 0.5486 0.0276 0.9214 0.049 Uiso 1 1 calc R . .
C4 C 0.5173(2) 0.1383(3) 0.83683(12) 0.0490(7) Uani 1 1 d . . .
H4 H 0.4490 0.0871 0.8237 0.059 Uiso 1 1 calc R . .
C5 C 0.5581(2) 0.2484(3) 0.79789(13) 0.0445(7) Uani 1 1 d . . .
H5 H 0.5178 0.2705 0.7584 0.053 Uiso 1 1 calc R . .
C6 C 0.6582(2) 0.3261(3) 0.81692(11) 0.0422(6) Uani 1 1 d . . .
H6 H 0.6851 0.4012 0.7906 0.051 Uiso 1 1 calc R . .
C7 C 0.7190(2) 0.2926(3) 0.87526(11) 0.0354(5) Uani 1 1 d . . .
H7 H 0.7872 0.3445 0.8880 0.042 Uiso 1 1 calc R . .
C8 C 0.75192(17) -0.0520(2) 1.00969(10) 0.0279(5) Uani 1 1 d . . .
C9 C 0.7497(2) -0.1032(2) 1.07292(11) 0.0375(6) Uani 1 1 d . . .
H9 H 0.7410 -0.0348 1.1062 0.045 Uiso 1 1 calc R . .
C10 C 0.7604(3) -0.2550(2) 1.08643(14) 0.0472(7) Uani 1 1 d . . .
H10 H 0.7577 -0.2893 1.1286 0.057 Uiso 1 1 calc R . .
C11 C 0.7749(2) -0.3551(3) 1.03760(14) 0.0493(7) Uani 1 1 d . . .
H11 H 0.7841 -0.4573 1.0470 0.059 Uiso 1 1 calc R . .
C12 C 0.7760(2) -0.3066(3) 0.97437(14) 0.0492(7) Uani 1 1 d . . .
H12 H 0.7848 -0.3760 0.9415 0.059 Uiso 1 1 calc R . .
C13 C 0.7641(2) -0.1551(2) 0.96014(12) 0.0388(6) Uani 1 1 d . . .
H13 H 0.7641 -0.1221 0.9176 0.047 Uiso 1 1 calc R . .
C14 C 0.6860(2) 0.24914(19) 1.05352(12) 0.0289(5) Uani 1 1 d . . .
C15 C 0.5738(2) 0.3065(3) 1.04273(12) 0.0397(6) Uani 1 1 d . . .
H15 H 0.5309 0.2894 1.0036 0.048 Uiso 1 1 calc R . .
C16 C 0.5267(2) 0.3892(3) 1.09071(13) 0.0521(7) Uani 1 1 d . . .
H16 H 0.4515 0.4273 1.0839 0.062 Uiso 1 1 calc R . .
C17 C 0.5904(2) 0.4155(3) 1.14866(13) 0.0498(7) Uani 1 1 d . . .
H17 H 0.5580 0.4718 1.1805 0.060 Uiso 1 1 calc R . .
C18 C 0.7014(2) 0.3594(2) 1.15985(11) 0.0401(6) Uani 1 1 d . . .
H18 H 0.7439 0.3782 1.1990 0.048 Uiso 1 1 calc R . .
C19 C 0.7497(2) 0.2752(2) 1.11276(12) 0.0327(5) Uani 1 1 d . . .
H19 H 0.8243 0.2358 1.1204 0.039 Uiso 1 1 calc R . .
H1O H 1.010(3) 0.679(4) 0.7061(15) 0.073(11) Uiso 1 1 d . . .
H2O H 1.005(3) 0.826(4) 0.7051(18) 0.114(15) Uiso 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'
Cl Cl 0.1484 0.1585 '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'
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'
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
O1 Zn1 Cl3 113.88(8) . . ?
O1 Zn1 Cl1 102.65(6) . . ?
Cl3 Zn1 Cl1 114.35(3) . . ?
O1 Zn1 Cl2 98.65(6) . . ?
Cl3 Zn1 Cl2 113.59(3) . . ?
Cl1 Zn1 Cl2 112.18(2) . . ?
Zn1 O1 H1O 113(2) . . ?
Zn1 O1 H2O 111(3) . . ?
H1O O1 H2O 102(4) . . ?
C2 P1 C1 109.65(11) . . ?
C2 P1 C8 109.84(10) . . ?
C1 P1 C8 108.87(10) . . ?
C2 P1 C14 109.76(11) . . ?
C1 P1 C14 108.86(11) . . ?
C8 P1 C14 109.85(9) . . ?
P1 C1 H1A 109.5 . . ?
P1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
P1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 119.7(2) . . ?
C7 C2 P1 119.36(17) . . ?
C3 C2 P1 120.87(17) . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.0(2) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C13 C8 C9 119.60(19) . . ?
C13 C8 P1 119.24(16) . . ?
C9 C8 P1 120.86(16) . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 119.7(2) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C15 C14 C19 119.8(2) . . ?
C15 C14 P1 121.52(19) . . ?
C19 C14 P1 118.66(18) . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.8(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 119.9(2) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
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 O1 2.019(2) . ?
Zn1 Cl3 2.1988(8) . ?
Zn1 Cl1 2.2591(6) . ?
Zn1 Cl2 2.2693(6) . ?
O1 H1O 0.80(3) . ?
O1 H2O 0.87(4) . ?
P1 C2 1.790(2) . ?
P1 C1 1.790(2) . ?
P1 C8 1.792(2) . ?
P1 C14 1.797(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.391(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.392(3) . ?
C8 C9 1.391(3) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.391(3) . ?
C14 C19 1.400(3) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
