#------------------------------------------------------------------------------
#$Date: 2019-11-08 02:22:27 +0200 (Fri, 08 Nov 2019) $
#$Revision: 224741 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/86/7058663.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_7058663
loop_
_publ_author_name
'Kobra, Khadijatul'
'Li, Yuxuan'
'Sachdeva, Rakesh'
'McMillen, Colin D.'
'Pennington, William T.'
_publ_section_title
;
 New polymorphism and structural sensitivity in triphenylmethylphosphonium
 trihalide salts
;
_journal_issue                   32
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12702
_journal_paper_doi               10.1039/C9NJ01846H
_journal_volume                  43
_journal_year                    2019
_chemical_formula_sum            'C19 H18 Br2.14 I0.86 P'
_chemical_formula_weight         557.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-04-09 deposited with the CCDC.    2019-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.654(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8305(8)
_cell_length_b                   15.5357(12)
_cell_length_c                   12.3762(9)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      3.11
_cell_volume                     2039.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24244
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.485
_diffrn_reflns_theta_min         3.609
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    5.625
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_description       tabular
_exptl_crystal_F_000             1070
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.042
_refine_diff_density_max         1.011
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0236P)²+3.9568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0638
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3092
_reflns_number_total             3771
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj01846h2.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 7058659--7058663.cif.'
_cod_database_code               7058663
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.492
_shelx_estimated_absorpt_t_max   0.798
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
I1 I 0.34527(2) 0.24253(2) 0.55699(2) 0.02490(10) Uani 0.864(5) 1 d . . P
Br1 Br 0.34527(2) 0.24253(2) 0.55699(2) 0.02490(10) Uani 0.136(5) 1 d . . P
Br2 Br 0.18976(5) 0.37973(3) 0.53808(5) 0.05912(18) Uani 1 1 d . . .
Br3 Br 0.50088(4) 0.10468(3) 0.57726(3) 0.03107(13) Uani 1 1 d . . .
P1 P 0.23249(9) 0.66415(6) 0.59943(7) 0.0213(2) Uani 1 1 d . . .
C1 C 0.1939(3) 0.7746(2) 0.6181(3) 0.0239(8) Uani 1 1 d . . .
C2 C 0.2821(4) 0.8387(2) 0.6136(3) 0.0293(9) Uani 1 1 d . . .
H2 H 0.365838 0.823535 0.609065 0.035 Uiso 1 1 calc R U .
C3 C 0.2484(4) 0.9244(3) 0.6157(3) 0.0383(10) Uani 1 1 d . . .
H3 H 0.308527 0.968152 0.611631 0.046 Uiso 1 1 calc R U .
C4 C 0.1270(4) 0.9462(3) 0.6238(3) 0.0393(11) Uani 1 1 d . . .
H4 H 0.104120 1.005125 0.626221 0.047 Uiso 1 1 calc R U .
C5 C 0.0392(4) 0.8833(3) 0.6285(4) 0.0431(11) Uani 1 1 d . . .
H5 H -0.044026 0.898917 0.634209 0.052 Uiso 1 1 calc R U .
C6 C 0.0712(4) 0.7973(3) 0.6249(3) 0.0322(9) Uani 1 1 d . . .
H6 H 0.009828 0.753953 0.627072 0.039 Uiso 1 1 calc R U .
C7 C 0.3914(3) 0.6423(2) 0.6671(3) 0.0235(8) Uani 1 1 d . . .
C8 C 0.4395(4) 0.6776(3) 0.7698(3) 0.0288(9) Uani 1 1 d . . .
H8 H 0.391123 0.717759 0.801662 0.035 Uiso 1 1 calc R U .
C9 C 0.5589(4) 0.6537(3) 0.8259(3) 0.0363(10) Uani 1 1 d . . .
H9 H 0.591807 0.677121 0.896761 0.044 Uiso 1 1 calc R U .
C10 C 0.6295(4) 0.5966(3) 0.7793(4) 0.0417(11) Uani 1 1 d . . .
H10 H 0.711581 0.581266 0.817760 0.050 Uiso 1 1 calc R U .
C11 C 0.5822(4) 0.5612(3) 0.6773(4) 0.0507(13) Uani 1 1 d . . .
H11 H 0.631103 0.521195 0.645755 0.061 Uiso 1 1 calc R U .
C12 C 0.4638(4) 0.5843(3) 0.6212(3) 0.0420(11) Uani 1 1 d . . .
H12 H 0.431386 0.560373 0.550505 0.050 Uiso 1 1 calc R U .
C13 C 0.2152(3) 0.6438(2) 0.4543(3) 0.0209(8) Uani 1 1 d . . .
C14 C 0.1255(4) 0.5870(3) 0.4000(3) 0.0299(9) Uani 1 1 d . . .
H14 H 0.073545 0.555943 0.439744 0.036 Uiso 1 1 calc R U .
C15 C 0.1121(4) 0.5756(3) 0.2872(3) 0.0367(10) Uani 1 1 d . . .
H15 H 0.051389 0.536030 0.249796 0.044 Uiso 1 1 calc R U .
C16 C 0.1855(4) 0.6208(3) 0.2292(3) 0.0343(10) Uani 1 1 d . . .
H16 H 0.175095 0.612785 0.151789 0.041 Uiso 1 1 calc R U .
C17 C 0.2749(4) 0.6782(3) 0.2831(3) 0.0361(10) Uani 1 1 d . . .
H17 H 0.325570 0.709778 0.242671 0.043 Uiso 1 1 calc R U .
C18 C 0.2904(4) 0.6896(3) 0.3958(3) 0.0315(9) Uani 1 1 d . . .
H18 H 0.352179 0.728496 0.433180 0.038 Uiso 1 1 calc R U .
C19 C 0.1303(4) 0.5958(2) 0.6572(3) 0.0279(9) Uani 1 1 d . . .
H19A H 0.042635 0.607003 0.620940 0.042 Uiso 1 1 calc R U .
H19B H 0.151052 0.535519 0.645957 0.042 Uiso 1 1 calc R U .
H19C H 0.141018 0.607434 0.736363 0.042 Uiso 1 1 calc R U .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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_3
Br2 I1 Br3 179.621(19) .
I1 Br2 C14 142.68(6) .
I1 Br3 Br3 134.15(2) 3_656
C19 P1 C7 108.40(18) .
C19 P1 C1 109.75(18) .
C7 P1 C1 110.44(17) .
C19 P1 C13 110.38(17) .
C7 P1 C13 109.37(16) .
C1 P1 C13 108.51(16) .
C2 C1 C6 119.6(3) .
C2 C1 P1 120.0(3) .
C6 C1 P1 120.0(3) .
C3 C2 C1 120.2(4) .
C3 C2 H2 119.9 .
C1 C2 H2 119.9 .
C4 C3 C2 119.8(4) .
C4 C3 H3 120.1 .
C2 C3 H3 120.1 .
C5 C4 C3 120.4(4) .
C5 C4 H4 119.8 .
C3 C4 H4 119.8 .
C4 C5 C6 120.4(4) .
C4 C5 H5 119.8 .
C6 C5 H5 119.8 .
C5 C6 C1 119.6(4) .
C5 C6 H6 120.2 .
C1 C6 H6 120.2 .
C8 C7 C12 119.6(3) .
C8 C7 P1 120.2(3) .
C12 C7 P1 120.1(3) .
C7 C8 C9 119.5(4) .
C7 C8 H8 120.3 .
C9 C8 H8 120.3 .
C10 C9 C8 120.3(4) .
C10 C9 H9 119.8 .
C8 C9 H9 119.8 .
C9 C10 C11 120.5(4) .
C9 C10 H10 119.8 .
C11 C10 H10 119.8 .
C12 C11 C10 119.6(4) .
C12 C11 H11 120.2 .
C10 C11 H11 120.2 .
C11 C12 C7 120.5(4) .
C11 C12 H12 119.7 .
C7 C12 H12 119.7 .
C14 C13 C18 120.1(3) .
C14 C13 P1 121.3(3) .
C18 C13 P1 118.5(3) .
C13 C14 C15 119.4(4) .
C13 C14 Br2 106.7(2) .
C15 C14 Br2 109.3(3) .
C13 C14 H14 120.3 .
C15 C14 H14 120.3 .
Br2 C14 H14 52.1 .
C16 C15 C14 120.7(4) .
C16 C15 H15 119.7 .
C14 C15 H15 119.7 .
C15 C16 C17 120.1(4) .
C15 C16 H16 119.9 .
C17 C16 H16 119.9 .
C18 C17 C16 119.9(4) .
C18 C17 H17 120.0 .
C16 C17 H17 120.1 .
C17 C18 C13 119.8(4) .
C17 C18 H18 120.1 .
C13 C18 H18 120.1 .
P1 C19 H19A 109.5 .
P1 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
P1 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Br2 2.6973(5) .
I1 Br3 2.7053(5) .
Br2 C14 3.645(4) .
Br3 Br3 3.7712(9) 3_656
P1 C19 1.784(4) .
P1 C7 1.788(4) .
P1 C1 1.792(4) .
P1 C13 1.795(3) .
C1 C2 1.388(5) .
C1 C6 1.394(5) .
C2 C3 1.383(6) .
C2 H2 0.9500 .
C3 C4 1.380(6) .
C3 H3 0.9500 .
C4 C5 1.373(6) .
C4 H4 0.9500 .
C5 C6 1.383(6) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.386(5) .
C7 C12 1.389(5) .
C8 C9 1.388(5) .
C8 H8 0.9500 .
C9 C10 1.373(6) .
C9 H9 0.9500 .
C10 C11 1.377(6) .
C10 H10 0.9500 .
C11 C12 1.377(6) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C14 1.382(5) .
C13 C18 1.389(5) .
C14 C15 1.386(5) .
C14 H14 0.9500 .
C15 C16 1.368(6) .
C15 H15 0.9500 .
C16 C17 1.385(6) .
C16 H16 0.9500 .
C17 C18 1.383(5) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
