#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/09/2230941.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230941
loop_
_publ_author_name
'Peulecke, Normen'
'Peitz, Stephan'
'Müller, Bernd H.'
'Spannenberg, Anke'
'Rosenthal, Uwe'
_publ_section_title
;
 (Isopropylamino)(methyl)diphenylphosphonium iodide
;
_journal_coeditor_code           YA2139
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1741
_journal_paper_doi               10.1107/S1600536811020332
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H21 N P +, I -'
_chemical_formula_moiety         'C16 H21 N P +, I -'
_chemical_formula_sum            'C16 H21 I N P'
_chemical_formula_weight         385.21
_chemical_name_systematic
;
(Isopropylamino)(methyl)diphenylphosphonium iodide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0
_cell_angle_beta                 93.492(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   9.0283(2)
_cell_length_b                   20.2810(6)
_cell_length_c                   9.2298(3)
_cell_measurement_reflns_used    9114
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.0
_cell_volume                     1686.87(8)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.013
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28937
_diffrn_reflns_theta_full        27.9
_diffrn_reflns_theta_max         27.9
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.98
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(X-SHAPE and X-RED32; Stoe & Cie, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.63
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.023
_refine_ls_R_factor_gt           0.019
_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)+(0.0324P)²+0.1321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.047
_refine_ls_wR_factor_ref         0.048
_reflns_number_gt                3604
_reflns_number_total             4035
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya2139.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230941
_cod_database_fobs_code          2230941
loop_
_symmetry_equiv_pos_as_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3442(2) 0.76211(8) 0.30748(19) 0.0309(3) Uani d . 1 1 . .
H H1B 0.4488 0.7578 0.2787 0.037 Uiso calc R 1 1 . .
C C2 0.3472(3) 0.78356(12) 0.4653(2) 0.0532(6) Uani d . 1 1 . .
H H2A 0.3970 0.8264 0.4762 0.080 Uiso calc R 1 1 . .
H H2B 0.4011 0.7508 0.5260 0.080 Uiso calc R 1 1 . .
H H2C 0.2454 0.7874 0.4955 0.080 Uiso calc R 1 1 . .
C C3 0.2667(2) 0.69656(9) 0.2829(2) 0.0404(4) Uani d . 1 1 . .
H H3A 0.1616 0.7012 0.3019 0.061 Uiso calc R 1 1 . .
H H3B 0.3127 0.6635 0.3487 0.061 Uiso calc R 1 1 . .
H H3C 0.2755 0.6825 0.1822 0.061 Uiso calc R 1 1 . .
C C4 0.36979(17) 0.94492(8) 0.24664(16) 0.0237(3) Uani d . 1 1 . .
C C5 0.4810(2) 0.99058(9) 0.22218(18) 0.0315(3) Uani d . 1 1 . .
H H5 0.5504 0.9820 0.1511 0.038 Uiso calc R 1 1 . .
C C6 0.4901(2) 1.04863(9) 0.3019(2) 0.0355(4) Uani d . 1 1 . .
H H6 0.5654 1.0800 0.2853 0.043 Uiso calc R 1 1 . .
C C7 0.3891(2) 1.06068(9) 0.40561(19) 0.0328(4) Uani d . 1 1 . .
H H7 0.3950 1.1006 0.4596 0.039 Uiso calc R 1 1 . .
C C8 0.28023(19) 1.01536(9) 0.43122(18) 0.0306(3) Uani d . 1 1 . .
H H8 0.2124 1.0239 0.5037 0.037 Uiso calc R 1 1 . .
C C9 0.26912(18) 0.95730(8) 0.35172(16) 0.0267(3) Uani d . 1 1 . .
H H9 0.1934 0.9262 0.3689 0.032 Uiso calc R 1 1 . .
C C10 0.23107(17) 0.89557(8) -0.02177(16) 0.0236(3) Uani d . 1 1 . .
C C11 0.1988(2) 0.84705(9) -0.12705(18) 0.0297(3) Uani d . 1 1 . .
H H11 0.2304 0.8029 -0.1107 0.036 Uiso calc R 1 1 . .
C C12 0.1206(2) 0.86407(10) -0.25494(18) 0.0344(4) Uani d . 1 1 . .
H H12 0.0985 0.8315 -0.3270 0.041 Uiso calc R 1 1 . .
C C13 0.0743(2) 0.92834(11) -0.27819(19) 0.0368(4) Uani d . 1 1 . .
H H13 0.0212 0.9397 -0.3667 0.044 Uiso calc R 1 1 . .
C C14 0.1045(2) 0.97639(10) -0.17426(19) 0.0359(4) Uani d . 1 1 . .
H H14 0.0716 1.0204 -0.1909 0.043 Uiso calc R 1 1 . .
C C15 0.18339(18) 0.95991(9) -0.04522(17) 0.0284(3) Uani d . 1 1 . .
H H15 0.2046 0.9926 0.0267 0.034 Uiso calc R 1 1 . .
N N1 0.26667(16) 0.81103(7) 0.21097(14) 0.0255(3) Uani d . 1 1 . .
P P1 0.34534(4) 0.87284(2) 0.13541(4) 0.02117(8) Uani d . 1 1 . .
I I1 -0.103895(11) 0.834024(5) 0.344262(11) 0.02825(4) Uani d . 1 1 . .
C C16 0.52126(19) 0.84672(9) 0.07819(19) 0.0300(3) Uani d . 1 1 . .
H H16A 0.5904 0.8409 0.1633 0.045 Uiso calc R 1 1 . .
H H16B 0.5603 0.8801 0.0139 0.045 Uiso calc R 1 1 . .
H H16C 0.5097 0.8048 0.0260 0.045 Uiso calc R 1 1 . .
H H1A 0.180(2) 0.8158(10) 0.223(2) 0.025(5) Uiso d . 1 1 . .
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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C3 . . 107.52(15) ?
N1 C1 C2 . . 111.42(15) ?
C3 C1 C2 . . 112.10(16) ?
N1 C1 H1B . . 108.6 ?
C3 C1 H1B . . 108.6 ?
C2 C1 H1B . . 108.6 ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C1 C3 H3A . . 109.5 ?
C1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C9 C4 C5 . . 120.01(15) ?
C9 C4 P1 . . 118.91(12) ?
C5 C4 P1 . . 120.91(13) ?
C6 C5 C4 . . 119.83(17) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C7 C6 C5 . . 119.77(17) ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C8 C7 C6 . . 120.56(16) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C7 C8 C9 . . 120.33(17) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
C8 C9 C4 . . 119.49(16) ?
C8 C9 H9 . . 120.3 ?
C4 C9 H9 . . 120.3 ?
C15 C10 C11 . . 120.21(15) ?
C15 C10 P1 . . 121.82(12) ?
C11 C10 P1 . . 117.82(13) ?
C12 C11 C10 . . 119.39(17) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C13 C12 C11 . . 120.15(17) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C14 . . 120.82(16) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C13 C14 C15 . . 119.58(18) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C10 C15 C14 . . 119.85(16) ?
C10 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C1 N1 P1 . . 125.03(12) ?
C1 N1 H1A . . 115.3(14) ?
P1 N1 H1A . . 115.0(14) ?
N1 P1 C16 . . 108.61(8) ?
N1 P1 C10 . . 107.60(7) ?
C16 P1 C10 . . 108.44(8) ?
N1 P1 C4 . . 115.25(7) ?
C16 P1 C4 . . 109.32(8) ?
C10 P1 C4 . . 107.41(7) ?
P1 C16 H16A . . 109.5 ?
P1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
P1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.481(2) ?
C1 C3 . 1.513(3) ?
C1 C2 . 1.519(3) ?
C1 H1B . 1.0000 ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2C . 0.9800 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C4 C9 . 1.392(2) ?
C4 C5 . 1.394(2) ?
C4 P1 . 1.7922(16) ?
C5 C6 . 1.388(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.383(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.377(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.388(2) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 C15 . 1.387(2) ?
C10 C11 . 1.401(2) ?
C10 P1 . 1.7886(15) ?
C11 C12 . 1.382(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.381(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.383(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.391(2) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
N1 P1 . 1.6195(15) ?
N1 H1A . 0.81(2) ?
P1 C16 . 1.7845(17) ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A I1 . 0.81(2) 2.88(2) 3.6641(15) 164.9(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656812
