#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:28:04 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179897 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/93/7019355.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_7019355
loop_
_publ_author_name
'Alhanash, Fatma B.'
'Barnes, Nicholas A.'
'Godfrey, Stephen M.'
'Hurst, Paul A.'
'Hutchinson, Adrian'
'Khan, Rana Z.'
'Pritchard, Robin G.'
_publ_section_title
;
 Structural isomerism in tris-tolyl halo-phosphonium and halo-arsonium
 tri-halides, [(CH(3)C(6)H(4))(3)EX][X(3)], (E = P, As; X = Br, I).
;
_journal_issue                   25
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7708
_journal_page_last               7728
_journal_paper_doi               10.1039/c2dt30235g
_journal_volume                  41
_journal_year                    2012
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H21 I4 P1'
_chemical_formula_sum            'C21 H21 I4 P'
_chemical_formula_weight         811.78
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-07-07T00:30:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.104(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4993(2)
_cell_length_b                   19.4335(5)
_cell_length_c                   12.6047(3)
_cell_measurement_reflns_used    5602
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_measurement_wavelength     0.71073
_cell_volume                     2482.99(10)
_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_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.577729E-1
_diffrn_orient_matrix_UB_12      -0.368744E-1
_diffrn_orient_matrix_UB_13      0.175174E-1
_diffrn_orient_matrix_UB_21      -0.516538E-1
_diffrn_orient_matrix_UB_22      0.355683E-1
_diffrn_orient_matrix_UB_23      0.283027E-1
_diffrn_orient_matrix_UB_31      -0.610452E-1
_diffrn_orient_matrix_UB_32      0.48014E-2
_diffrn_orient_matrix_UB_33      -0.751314E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15682
_diffrn_reflns_reduction_process
;
Scaled and merged with SORTAV
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    5.088
_exptl_absorpt_correction_T_max  0.4611
_exptl_absorpt_correction_T_min  0.4007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         3.092
_refine_diff_density_min         -1.792
_refine_diff_density_rms         0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.247
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.247
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²+26.0483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1877
_reflns_number_gt                3245
_reflns_number_total             4864
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2dt30235g.txt
_cod_data_source_block           rob3
_cod_database_code               7019355
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
C1 C 0.6701(10) 0.1852(6) 0.2243(8) 0.034(2) Uani 1 1 d .
C2 C 0.6993(12) 0.1149(6) 0.2341(9) 0.039(3) Uani 1 1 d .
H2 H 0.6485 0.0848 0.2662 0.047 Uiso 1 1 calc R
C3 C 0.8049(12) 0.0889(6) 0.1959(10) 0.042(3) Uani 1 1 d .
H3 H 0.8247 0.0412 0.2027 0.051 Uiso 1 1 calc R
C4 C 0.8794(11) 0.1316(6) 0.1492(9) 0.038(3) Uani 1 1 d .
C5 C 0.8488(11) 0.2006(7) 0.1396(9) 0.040(3) Uani 1 1 d .
H5 H 0.901 0.2304 0.1084 0.048 Uiso 1 1 calc R
C6 C 0.7456(11) 0.2276(6) 0.1736(9) 0.038(3) Uani 1 1 d .
H6 H 0.725 0.2751 0.163 0.045 Uiso 1 1 calc R
C7 C 0.9943(12) 0.1037(8) 0.1113(11) 0.051(3) Uani 1 1 d .
H7A H 1.0262 0.0613 0.1514 0.077 Uiso 1 1 calc R
H7B H 1.0655 0.1378 0.1256 0.077 Uiso 1 1 calc R
H7C H 0.9659 0.094 0.0324 0.077 Uiso 1 1 calc R
C8 C 0.4972(11) 0.1648(5) 0.3701(8) 0.033(2) Uani 1 1 d .
C9 C 0.3685(11) 0.1388(6) 0.3526(9) 0.037(3) Uani 1 1 d .
H9 H 0.3035 0.149 0.2866 0.045 Uiso 1 1 calc R
C10 C 0.3370(12) 0.0976(6) 0.4334(10) 0.043(3) Uani 1 1 d .
H10 H 0.2492 0.0812 0.4225 0.052 Uiso 1 1 calc R
C11 C 0.4312(11) 0.0801(6) 0.5290(9) 0.038(3) Uani 1 1 d .
C12 C 0.5599(11) 0.1060(6) 0.5438(9) 0.038(3) Uani 1 1 d .
H12 H 0.6253 0.0957 0.6096 0.046 Uiso 1 1 calc R
C13 C 0.5919(11) 0.1453(6) 0.4658(8) 0.034(2) Uani 1 1 d .
H13 H 0.6807 0.1599 0.4762 0.041 Uiso 1 1 calc R
C14 C 0.3968(13) 0.0380(6) 0.6162(9) 0.042(3) Uani 1 1 d .
H14A H 0.3372 0.0641 0.6493 0.062 Uiso 1 1 calc R
H14B H 0.4774 0.0265 0.6729 0.062 Uiso 1 1 calc R
H14C H 0.3531 -0.0045 0.5838 0.062 Uiso 1 1 calc R
C15 C 0.3951(10) 0.2320(5) 0.1578(8) 0.032(2) Uani 1 1 d .
C16 C 0.2972(12) 0.2799(6) 0.1642(9) 0.042(3) Uani 1 1 d .
H16 H 0.3078 0.3079 0.2278 0.05 Uiso 1 1 calc R
C17 C 0.1874(12) 0.2863(7) 0.0793(11) 0.049(3) Uani 1 1 d .
H17 H 0.1224 0.3193 0.084 0.059 Uiso 1 1 calc R
C18 C 0.1680(12) 0.2453(7) -0.0149(10) 0.049(3) Uani 1 1 d .
C19 C 0.2648(13) 0.1973(7) -0.0204(9) 0.051(3) Uani 1 1 d .
H19 H 0.2532 0.169 -0.0837 0.061 Uiso 1 1 calc R
C20 C 0.3757(12) 0.1905(6) 0.0635(8) 0.036(3) Uani 1 1 d .
H20 H 0.4405 0.1575 0.0584 0.043 Uiso 1 1 calc R
C21 C 0.0427(15) 0.2525(9) -0.1072(12) 0.069(4) Uani 1 1 d .
H21A H 0.0536 0.2898 -0.1565 0.104 Uiso 1 1 calc R
H21B H -0.0315 0.2631 -0.0762 0.104 Uiso 1 1 calc R
H21C H 0.0252 0.2093 -0.1485 0.104 Uiso 1 1 calc R
I1 I 0.60761(8) 0.33009(4) 0.34943(6) 0.0405(2) Uani 1 1 d .
I2 I 0.71382(8) 0.49926(4) 0.39275(7) 0.0479(3) Uani 1 1 d .
I3 I 0.5 0.5 0.5 0.0400(3) Uani 1 2 d S
I4 I 0 0 0.5 0.0553(4) Uani 1 2 d S
I5 I -0.05326(10) 0.07860(6) 0.68207(9) 0.0673(3) Uani 1 1 d .
P1 P 0.5369(3) 0.21878(14) 0.2704(2) 0.0314(6) 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
C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.474 1.812 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.102 0.094 '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
C2 C1 C6 118.4(10) .
C2 C1 P1 120.3(8) .
C6 C1 P1 121.3(9) .
C1 C2 C3 119.5(11) .
C1 C2 H2 120.2 .
C3 C2 H2 120.2 .
C4 C3 C2 121.1(11) .
C4 C3 H3 119.5 .
C2 C3 H3 119.5 .
C3 C4 C5 118.7(11) .
C3 C4 C7 120.7(11) .
C5 C4 C7 120.6(11) .
C6 C5 C4 122.1(11) .
C6 C5 H5 118.9 .
C4 C5 H5 118.9 .
C5 C6 C1 120.2(11) .
C5 C6 H6 119.9 .
C1 C6 H6 119.9 .
C4 C7 H7A 109.5 .
C4 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
C4 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
C13 C8 C9 118.3(10) .
C13 C8 P1 121.8(8) .
C9 C8 P1 119.8(8) .
C10 C9 C8 119.4(10) .
C10 C9 H9 120.3 .
C8 C9 H9 120.3 .
C11 C10 C9 121.4(11) .
C11 C10 H10 119.3 .
C9 C10 H10 119.3 .
C10 C11 C12 118.1(10) .
C10 C11 C14 121.4(11) .
C12 C11 C14 120.5(11) .
C13 C12 C11 121.1(11) .
C13 C12 H12 119.5 .
C11 C12 H12 119.5 .
C12 C13 C8 121.5(10) .
C12 C13 H13 119.2 .
C8 C13 H13 119.2 .
C11 C14 H14A 109.5 .
C11 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C11 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C16 C15 C20 118.8(10) .
C16 C15 P1 121.3(8) .
C20 C15 P1 119.8(8) .
C17 C16 C15 119.8(11) .
C17 C16 H16 120.1 .
C15 C16 H16 120.1 .
C16 C17 C18 121.5(12) .
C16 C17 H17 119.2 .
C18 C17 H17 119.2 .
C19 C18 C17 118.4(11) .
C19 C18 C21 121.4(12) .
C17 C18 C21 120.2(12) .
C20 C19 C18 120.9(12) .
C20 C19 H19 119.6 .
C18 C19 H19 119.6 .
C19 C20 C15 120.5(11) .
C19 C20 H20 119.7 .
C15 C20 H20 119.7 .
C18 C21 H21A 109.5 .
C18 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C18 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
I2 I3 I2 180 3_666
I5 I4 I5 180 3_556
C8 P1 C1 111.5(5) .
C8 P1 C15 110.3(5) .
C1 P1 C15 110.9(5) .
C8 P1 I1 110.0(4) .
C1 P1 I1 106.3(4) .
C15 P1 I1 107.6(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.400(16) .
C1 C6 1.408(15) .
C1 P1 1.772(11) .
C2 C3 1.411(16) .
C2 H2 0.95 .
C3 C4 1.374(16) .
C3 H3 0.95 .
C4 C5 1.376(17) .
C4 C7 1.509(15) .
C5 C6 1.370(16) .
C5 H5 0.95 .
C6 H6 0.95 .
C7 H7A 0.98 .
C7 H7B 0.98 .
C7 H7C 0.98 .
C8 C13 1.401(15) .
C8 C9 1.405(15) .
C8 P1 1.768(11) .
C9 C10 1.401(16) .
C9 H9 0.95 .
C10 C11 1.387(17) .
C10 H10 0.95 .
C11 C12 1.408(16) .
C11 C14 1.489(15) .
C12 C13 1.355(15) .
C12 H12 0.95 .
C13 H13 0.95 .
C14 H14A 0.98 .
C14 H14B 0.98 .
C14 H14C 0.98 .
C15 C16 1.406(16) .
C15 C20 1.406(15) .
C15 P1 1.788(10) .
C16 C17 1.359(17) .
C16 H16 0.95 .
C17 C18 1.399(19) .
C17 H17 0.95 .
C18 C19 1.395(19) .
C18 C21 1.519(17) .
C19 C20 1.360(16) .
C19 H19 0.95 .
C20 H20 0.95 .
C21 H21A 0.98 .
C21 H21B 0.98 .
C21 H21C 0.98 .
I1 P1 2.416(3) .
I2 I3 2.9067(8) .
I3 I2 2.9067(8) 3_666
I4 I5 2.9294(12) 3_556
I4 I5 2.9294(12) .
