#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/14/2001499.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_2001499
loop_
_publ_author_name
'Pohl, E.'
'Gosink, H. J.'
'Herbst-Irmer, R.'
'Noltemeyer, M.'
'Roesky, H. W.'
'Sheldrick, G. M.'
_publ_section_title
;
 Structures of amino(triphenyl)phosphonium bromide and
 amino(triphenyl)phosphonium hexachloroantimonate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1280
_journal_page_last               1283
_journal_paper_doi               10.1107/S0108270192013180
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C18 H17 N1 P1, Br'
_chemical_formula_sum            'C18 H17 Br N P'
_chemical_formula_weight         358.21
_chemical_name_systematic
;
 Aminotriphenylphosphonium bromide
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9780(10)
_cell_length_b                   9.6280(10)
_cell_length_c                   15.530(2)
_cell_measurement_reflns_used    56
_cell_measurement_temperature    153.0(10)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     1641.5(3)
_computing_cell_refinement       'Stoe DIF4'
_computing_data_collection       'Stoe DIF4'
_computing_data_reduction        'Stoe REDU4'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 19??)'
_computing_publication_material  SHELXL-92
_computing_structure_refinement  'SHELXL-92 (Sheldrick, 1992)'
_computing_structure_solution    'SHELXS-92 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153.0(10)
_diffrn_measurement_device       'Stoe-Siemens AED four-circle'
_diffrn_measurement_method       'Profile data from 2θ/ω scans'
_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  0.0068
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3776
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         4.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.595
_exptl_absorpt_correction_T_max  0.783
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       Block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.230
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.016(7)
_refine_ls_extinction_coef       0.0050(3)
_refine_ls_extinction_method     SHELXL-92
_refine_ls_goodness_of_fit_all   1.102
_refine_ls_goodness_of_fit_obs   1.066
_refine_ls_hydrogen_treatment
;Coordinates of H atoms attached to N refined with distance restraints; those
 of
C-H H atoms not refined
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3701
_refine_ls_number_restraints     106
_refine_ls_restrained_S_all      1.095
_refine_ls_restrained_S_obs      1.049
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_obs          '0.0258 for F > 4\s(F)'
_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^) + (0.0241P)^2^ + 0.6395P] where
P=(F~o~^2^+2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.0598
_refine_ls_wR_factor_obs         '0.0547 for F > 4\s(F)'
_reflns_number_observed          3385
_reflns_number_total             3704
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            sh1034.cif
_cod_data_source_block           alge
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' 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 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' 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_database_code               2001499
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_label
_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_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
Br(1) 0.38157(2) 0.27359(2) 0.50000(2) 0.02694(9) Uani d . 1 . Br
P(1) 0.14371(4) 0.49898(7) 0.65684(4) 0.0173(2) Uani d . 1 . P
N(1) 0.1273(2) 0.3578(2) 0.60192(13) 0.0234(8) Uani d D 1 . N
H(1A) 0.185(2) 0.329(3) 0.5715(17) 0.031(6) Uiso d D 1 . H
H(1B) 0.058(2) 0.339(3) 0.5819(18) 0.031(6) Uiso d D 1 . H
C(11) 0.1653(2) 0.6551(2) 0.59526(13) 0.0209(9) Uani d . 1 . C
C(12) 0.2659(2) 0.6611(3) 0.5394(2) 0.0295(11) Uani d D 1 . C
H(12) 0.3171(6) 0.5838(9) 0.5328(2) 0.036(4) Uiso calc RD 1 . H
C(13) 0.2886(2) 0.7828(3) 0.4941(2) 0.0374(11) Uani d D 1 . C
H(13) 0.3568(8) 0.7880(3) 0.4576(5) 0.039(4) Uiso calc RD 1 . H
C(14) 0.2121(2) 0.8966(3) 0.5018(2) 0.0356(12) Uani d D 1 . C
H(14) 0.2281(3) 0.9781(10) 0.4706(4) 0.039(5) Uiso calc RD 1 . H
C(15) 0.1116(2) 0.8897(3) 0.5560(2) 0.0346(12) Uani d D 1 . C
H(15) 0.0591(7) 0.9666(9) 0.5612(2) 0.039(4) Uiso calc RD 1 . H
C(16) 0.0882(2) 0.7688(3) 0.6029(2) 0.0282(10) Uani d D 1 . C
H(16) 0.0203(8) 0.7644(3) 0.6396(4) 0.036(4) Uiso calc RD 1 . H
C(21) 0.0109(2) 0.5193(2) 0.72264(13) 0.0191(9) Uani d . 1 . C
C(22) 0.0224(2) 0.5529(3) 0.8098(2) 0.0261(10) Uani d D 1 . C
H(22) 0.0997(9) 0.5658(3) 0.8342(3) 0.036(4) Uiso calc RD 1 . H
C(23) -0.0819(2) 0.5672(3) 0.8600(2) 0.0336(12) Uani d D 1 . C
H(23) -0.0748(3) 0.5898(4) 0.9186(7) 0.039(4) Uiso calc RD 1 . H
C(24) -0.1958(2) 0.5483(3) 0.8241(2) 0.0303(11) Uani d D 1 . C
H(24) -0.2660(8) 0.5578(3) 0.8586(4) 0.039(5) Uiso calc RD 1 . H
C(25) -0.2077(2) 0.5154(3) 0.7374(2) 0.0253(9) Uani d D 1 . C
H(25) -0.2856(9) 0.5026(3) 0.7134(3) 0.039(4) Uiso calc RD 1 . H
C(26) -0.1045(2) 0.5011(3) 0.68582(14) 0.0210(9) Uani d D 1 . C
H(26) -0.1122(2) 0.4796(4) 0.6272(7) 0.036(4) Uiso calc RD 1 . H
C(31) 0.2764(2) 0.4780(2) 0.72269(13) 0.0187(9) Uani d . 1 . C
C(32) 0.3141(2) 0.3456(3) 0.7437(2) 0.0314(13) Uani d D 1 . C
H(32) 0.2720(5) 0.2682(9) 0.7220(3) 0.036(4) Uiso calc RD 1 . H
C(33) 0.4146(3) 0.3265(3) 0.7973(2) 0.0390(15) Uani d D 1 . C
H(33) 0.4408(4) 0.2364(11) 0.8113(2) 0.039(4) Uiso calc RD 1 . H
C(34) 0.4753(2) 0.4401(3) 0.8297(2) 0.0291(10) Uani d D 1 . C
H(34) 0.5433(8) 0.4270(3) 0.8658(4) 0.039(5) Uiso calc RD 1 . H
C(35) 0.4378(2) 0.5722(3) 0.8101(2) 0.0351(13) Uani d D 1 . C
H(35) 0.4788(5) 0.6489(9) 0.8335(3) 0.039(4) Uiso calc RD 1 . H
C(36) 0.3386(2) 0.5924(3) 0.7553(2) 0.0294(11) Uani d D 1 . C
H(36) 0.3139(4) 0.6829(11) 0.7406(2) 0.036(4) Uiso calc RD 1 . H
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'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 '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
N(1) P(1) C(21) . . 107.58(10) yes
N(1) P(1) C(31) . . 107.31(10) yes
C(21) P(1) C(31) . . 110.39(10) yes
N(1) P(1) C(11) . . 115.96(11) yes
C(21) P(1) C(11) . . 108.64(11) yes
C(31) P(1) C(11) . . 106.93(10) yes
P(1) N(1) H(1A) . . 120.(2) yes
P(1) N(1) H(1B) . . 118.(2) yes
H(1A) N(1) H(1B) . . 114.(3) yes
C(16) C(11) C(12) . . 119.9(2) ?
C(16) C(11) P(1) . . 122.3(2) ?
C(12) C(11) P(1) . . 117.8(2) ?
C(13) C(12) C(11) . . 119.2(3) ?
C(13) C(12) H(12) . . 120.4(2) ?
C(11) C(12) H(12) . . 120.38(15) ?
C(14) C(13) C(12) . . 120.9(3) ?
C(14) C(13) H(13) . . 119.5(2) ?
C(12) C(13) H(13) . . 119.5(2) ?
C(13) C(14) C(15) . . 119.8(3) ?
C(13) C(14) H(14) . . 120.1(2) ?
C(15) C(14) H(14) . . 120.1(2) ?
C(14) C(15) C(16) . . 120.1(3) ?
C(14) C(15) H(15) . . 120.0(2) ?
C(16) C(15) H(15) . . 120.0(2) ?
C(11) C(16) C(15) . . 120.1(2) ?
C(11) C(16) H(16) . . 119.96(14) ?
C(15) C(16) H(16) . . 120.0(2) ?
C(22) C(21) C(26) . . 120.4(2) ?
C(22) C(21) P(1) . . 120.3(2) ?
C(26) C(21) P(1) . . 119.3(2) ?
C(23) C(22) C(21) . . 119.4(2) ?
C(23) C(22) H(22) . . 120.30(14) ?
C(21) C(22) H(22) . . 120.30(13) ?
C(24) C(23) C(22) . . 120.4(2) ?
C(24) C(23) H(23) . . 119.82(14) ?
C(22) C(23) H(23) . . 119.82(14) ?
C(23) C(24) C(25) . . 120.4(2) ?
C(23) C(24) H(24) . . 119.78(14) ?
C(25) C(24) H(24) . . 119.78(14) ?
C(24) C(25) C(26) . . 120.2(2) ?
C(24) C(25) H(25) . . 119.91(14) ?
C(26) C(25) H(25) . . 119.91(13) ?
C(25) C(26) C(21) . . 119.2(2) ?
C(25) C(26) H(26) . . 120.39(13) ?
C(21) C(26) H(26) . . 120.39(12) ?
C(32) C(31) C(36) . . 119.9(2) ?
C(32) C(31) P(1) . . 118.9(2) ?
C(36) C(31) P(1) . . 121.2(2) ?
C(31) C(32) C(33) . . 120.0(2) ?
C(31) C(32) H(32) . . 119.99(13) ?
C(33) C(32) H(32) . . 120.0(2) ?
C(34) C(33) C(32) . . 119.8(3) ?
C(34) C(33) H(33) . . 120.1(2) ?
C(32) C(33) H(33) . . 120.1(2) ?
C(35) C(34) C(33) . . 120.7(2) ?
C(35) C(34) H(34) . . 119.66(14) ?
C(33) C(34) H(34) . . 119.7(2) ?
C(34) C(35) C(36) . . 120.0(2) ?
C(34) C(35) H(35) . . 120.02(14) ?
C(36) C(35) H(35) . . 120.0(2) ?
C(31) C(36) C(35) . . 119.6(2) ?
C(31) C(36) H(36) . . 120.18(14) ?
C(35) C(36) H(36) . . 120.2(2) ?
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
P(1) N(1) . 1.615(2) yes
P(1) C(21) . 1.791(2) yes
P(1) C(31) . 1.791(2) yes
P(1) C(11) . 1.797(2) yes
N(1) H(1A) . 0.84(2) yes
N(1) H(1B) . 0.84(2) yes
C(11) C(16) . 1.388(4) ?
C(11) C(12) . 1.406(3) ?
C(12) C(13) . 1.389(4) ?
C(12) H(12) . 0.939(11) ?
C(13) C(14) . 1.385(4) ?
C(13) H(13) . 0.941(11) ?
C(14) C(15) . 1.389(4) ?
C(14) H(14) . 0.939(11) ?
C(15) C(16) . 1.397(4) ?
C(15) H(15) . 0.942(11) ?
C(16) H(16) . 0.940(11) ?
C(21) C(22) . 1.397(3) ?
C(21) C(26) . 1.401(3) ?
C(22) C(23) . 1.392(3) ?
C(22) H(22) . 0.937(11) ?
C(23) C(24) . 1.381(4) ?
C(23) H(23) . 0.939(11) ?
C(24) C(25) . 1.389(3) ?
C(24) H(24) . 0.943(11) ?
C(25) C(26) . 1.395(3) ?
C(25) H(25) . 0.940(11) ?
C(26) H(26) . 0.937(11) ?
C(31) C(32) . 1.380(3) ?
C(31) C(36) . 1.392(3) ?
C(32) C(33) . 1.394(3) ?
C(32) H(32) . 0.939(11) ?
C(33) C(34) . 1.376(4) ?
C(33) H(33) . 0.939(11) ?
C(34) C(35) . 1.371(4) ?
C(34) H(34) . 0.942(11) ?
C(35) C(36) . 1.396(3) ?
C(35) H(35) . 0.938(11) ?
C(36) H(36) . 0.941(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 19933778
