#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/39/2003905.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_2003905
loop_
_publ_author_name
'Schödel, H.'
'Näther, C.'
'Bock, H.'
_publ_section_title
;
 Two Trimethylphenylphosphonium Iodides
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1841
_journal_page_last               1844
_journal_paper_doi               10.1107/S0108270194015052
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source        ethanol
_chemical_formula_sum            'C11 H19 I N P'
_chemical_formula_weight         323.14
_chemical_melting_point          531
_chemical_name_systematic
;
 Trimethyl(p-N,N-dimethylamino)phenylphosphoniumiodide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 91.30(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0330(10)
_cell_length_b                   8.0480(10)
_cell_length_c                   27.348(5)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.5
_cell_measurement_theta_min      10.5
_cell_volume                     1327.5(4)
_computing_cell_refinement       'DIF4 (Stoe & Cie, 1988a)'
_computing_data_collection       'DIF4 (Stoe & Cie, 1988a)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1988b)'
_computing_molecular_graphics    'SHELXTL/PC XP (Sheldrick, 1990)'
_computing_publication_material  'SHELXL93 CIFTAB'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_device       'Siemens-Stoe AED-2 four-circle'
_diffrn_measurement_method       ω-θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0144
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -05
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -034
_diffrn_reflns_number            3919
_diffrn_reflns_theta_max         26.52
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.500
_exptl_absorpt_correction_T_max  .53
_exptl_absorpt_correction_T_min  .41
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_description       'transparent block'
_exptl_crystal_F_000             640
_exptl_crystal_size_max          .54
_exptl_crystal_size_mid          .36
_exptl_crystal_size_min          .27
_refine_diff_density_max         .713
_refine_diff_density_min         -0.707
_refine_ls_extinction_coef       .0011(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.024
_refine_ls_goodness_of_fit_obs   1.081
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_restrained_S_obs      1.081
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_obs          .0213
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0290P)^2^ + 0.3450P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         .0555
_refine_ls_wR_factor_obs         .0508
_reflns_number_observed          2112
_reflns_number_total             2760
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jz1022.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2003905
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
I1 0.01682(10) 0.01410(10) 0.01703(10) 0.00076(6) 0.00402(6) 0.00144(6)
P1 0.0121(3) 0.0128(3) 0.0144(3) 0.0002(2) 0.0015(2) 0.0003(2)
N1 0.0192(10) 0.0235(10) 0.0143(10) 0.0052(9) 0.0006(8) 0.0027(8)
C1 0.0132(11) 0.0154(11) 0.0155(11) -0.0024(8) 0.0027(9) 0.0004(9)
C2 0.0166(12) 0.0150(11) 0.0228(13) 0.0023(9) -0.0004(10) 0.0008(9)
C3 0.0178(12) 0.0159(11) 0.0177(12) 0.0023(9) -0.0013(10) 0.0031(9)
C4 0.0172(11) 0.0140(10) 0.0149(11) -0.0039(9) 0.0004(9) 0.0008(9)
C5 0.0137(12) 0.0176(11) 0.0199(12) 0.0017(9) 0.0021(10) 0.0015(9)
C6 0.0152(12) 0.0161(11) 0.0200(13) 0.0021(9) 0.0003(10) 0.0037(9)
C7 0.0193(13) 0.0153(11) 0.0222(14) -0.0028(10) 0.0028(11) -0.0008(10)
C8 0.0221(14) 0.0170(11) 0.0197(14) 0.0063(10) 0.0046(11) -0.0012(9)
C9 0.0169(12) 0.0216(13) 0.0162(11) -0.0017(9) -0.0012(9) -0.0007(9)
C10 0.0250(14) 0.0250(12) 0.0175(12) 0.0016(11) 0.0008(11) 0.0056(10)
C11 0.0208(14) 0.0282(13) 0.0190(13) 0.0044(11) 0.0036(11) -0.0008(10)
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
I1 1 .31305(2) .74193(2) -.066027(5) .01593(7) Uani d . I
P1 1 .03771(10) .75084(6) .08052(2) .01311(13) Uani d . P
N1 1 -0.3177(4) .7794(3) .28335(7) .0190(4) Uani d . N
C1 1 -.0665(4) .7576(2) .14100(9) .0147(5) Uani d . C
C2 1 .0262(4) .6613(3) .17896(9) .0182(5) Uani d . C
H2 1 .1449(4) .5879(3) .17214(9) .019(7) Uiso calc R H
C3 1 -.0515(4) .6706(3) .22626(9) .0172(5) Uani d . C
H3 1 .0177(4) .6065(3) .25149(9) .029(8) Uiso calc R H
C4 1 -0.2326(4) .7744(3) .23723(9) .0154(5) Uani d . C
C5 1 -0.3234(4) .8731(3) .19891(9) .0171(5) Uani d . C
H5 1 -0.4431(4) .9460(3) .20533(9) .023(7) Uiso calc R H
C6 1 -0.2405(4) .8648(3) .15238(9) .0171(5) Uani d . C
H6 1 -0.3031(4) .9336(3) .12745(9) .019(7) Uiso calc R H
C7 1 .1977(4) .9331(3) .06816(10) .0189(5) Uani d . C
H7A 1 .2535(4) .9272(3) .03482(10) .032(5) Uiso calc R H
H7B 1 .3230(4) .9399(3) .09152(10) .032(5) Uiso calc R H
H7C 1 .1042(4) 1.0319(3) .07137(10) .032(5) Uiso calc R H
C8 1 .2104(4) .5727(3) .07349(10) .0195(5) Uani d . C
H8A 1 .2668(4) .5701(3) .04017(10) .021(4) Uiso calc R H
H8B 1 .1240(4) .4719(3) .07943(10) .021(4) Uiso calc R H
H8C 1 .3352(4) .5784(3) .09700(10) .021(4) Uiso calc R H
C9 1 -0.1867(4) .7432(3) .03677(9) .0183(5) Uani d . C
H9A 1 -0.1277(4) .7395(3) .00369(9) .025(5) Uiso calc R H
H9B 1 -0.2795(4) .8423(3) .04021(9) .025(5) Uiso calc R H
H9C 1 -0.2760(4) .6436(3) .04242(9) .025(5) Uiso calc R H
C10 1 -0.2044(4) .6942(3) .32375(9) .0225(5) Uani d . C
H10A 1 -0.2872(4) .7105(3) .35379(9) .033(5) Uiso calc R H
H10B 1 -.0545(4) .7395(3) .32816(9) .033(5) Uiso calc R H
H10C 1 -0.1954(4) .5752(3) .31646(9) .033(5) Uiso calc R H
C11 1 -0.5154(4) .8768(3) .29290(10) .0226(6) Uani d . C
H11A 1 -0.5526(4) .8664(3) .32746(10) .041(5) Uiso calc R H
H11B 1 -0.6392(4) .8358(3) .27244(10) .041(5) Uiso calc R H
H11C 1 -0.4876(4) .9938(3) .28521(10) .041(5) Uiso calc R H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' .0033 .0016
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' .0000 .0000
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' .0061 .0033
P P 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' .1023 .0942
I I 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' -0.4742 1.8119
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 P1 C8 110.10(10) yes
C1 P1 C9 110.10(10) yes
C8 P1 C9 109.60(10) yes
C1 P1 C7 110.70(10) yes
C8 P1 C7 108.60(10) yes
C9 P1 C7 107.80(10) yes
C4 N1 C11 120.4(2) yes
C4 N1 C10 120.3(2) yes
C11 N1 C10 119.3(2) yes
C6 C1 C2 117.7(2) yes
C6 C1 P1 120.5(2) yes
C2 C1 P1 121.8(2) yes
C3 C2 C1 121.6(2) yes
C2 C3 C4 120.6(2) yes
N1 C4 C3 121.3(2) yes
N1 C4 C5 121.1(2) yes
C3 C4 C5 117.6(2) yes
C6 C5 C4 120.9(2) yes
C5 C6 C1 121.6(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C1 1.784(2) yes
P1 C8 1.785(2) yes
P1 C9 1.788(2) yes
P1 C7 1.793(2) yes
N1 C4 1.373(3) yes
N1 C11 1.456(3) yes
N1 C10 1.457(3) yes
C1 C6 1.400(3) yes
C1 C2 1.401(3) yes
C2 C3 1.388(3) yes
C3 C4 1.413(3) yes
C4 C5 1.415(3) yes
C5 C6 1.379(3) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 P1 C1 C6 -166.7(2)
C9 P1 C1 C6 -45.7(2)
C7 P1 C1 C6 73.3(2)
C8 P1 C1 C2 15.5(2)
C9 P1 C1 C2 136.5(2)
C7 P1 C1 C2 -104.5(2)
C6 C1 C2 C3 0.3(3)
P1 C1 C2 C3 178.1(2)
C1 C2 C3 C4 2.1(4)
C11 N1 C4 C3 -174.9(2)
C10 N1 C4 C3 8.2(3)
C11 N1 C4 C5 5.0(3)
C10 N1 C4 C5 -171.9(2)
C2 C3 C4 N1 177.1(2)
C2 C3 C4 C5 -2.9(3)
N1 C4 C5 C6 -178.5(2)
C3 C4 C5 C6 1.4(3)
C4 C5 C6 C1 0.9(4)
C2 C1 C6 C5 -1.8(3)
P1 C1 C6 C5 -179.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21138765
