#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:25:41 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179895 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/91/7019183.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_7019183
loop_
_publ_author_name
'Adamová, Gabriela'
'Gardas, Ramesh L.'
'Nieuwenhuyzen, Mark'
'Puga, Alberto V.'
'Rebelo, Luís Paulo N'
'Robertson, Allan J.'
'Seddon, Kenneth R.'
_publ_section_title
;
 Alkyltributylphosphonium chloride ionic liquids: synthesis,
 physicochemical properties and crystal structure.
;
_journal_issue                   27
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8316
_journal_page_last               8332
_journal_paper_doi               10.1039/c1dt10466g
_journal_volume                  41
_journal_year                    2012
_chemical_formula_sum            'C15 H34 Cl P'
_chemical_formula_weight         280.84
_chemical_name_systematic
;
?
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.331(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9996(5)
_cell_length_b                   13.4309(12)
_cell_length_c                   13.3481(10)
_cell_measurement_temperature    150(2)
_cell_volume                     1792.2(2)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7858
_diffrn_reflns_theta_full        56.65
_diffrn_reflns_theta_max         56.65
_diffrn_reflns_theta_min         4.42
_exptl_absorpt_coefficient_mu    2.565
_exptl_absorpt_correction_T_max  0.8825
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Multiscan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.041
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     302
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0821
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1629P)²+0.8109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2273
_refine_ls_wR_factor_ref         0.2539
_reflns_number_gt                1602
_reflns_number_total             2329
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10466g.txt
_cod_data_source_block           p10prr185
_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_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7019183
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.44536(17) -0.18973(10) 0.41073(9) 0.0680(6) Uani 1 1 d . . .
P1 P 0.60233(15) 0.09270(11) 0.31266(9) 0.0553(6) Uani 0.50 1 d PD A 1
C11 C 0.648(2) 0.0560(11) 0.1873(9) 0.044(7) Uiso 0.50 1 d PD A 1
H11A H 0.6065 0.1021 0.1380 0.053 Uiso 0.50 1 calc PR A 1
H11B H 0.7466 0.0609 0.1813 0.053 Uiso 0.50 1 calc PR A 1
C12 C 0.6035(16) -0.0510(10) 0.1634(9) 0.049(5) Uiso 0.50 1 d PD A 1
H12A H 0.6471 -0.0969 0.2121 0.059 Uiso 0.50 1 calc PR A 1
H12B H 0.5056 -0.0560 0.1720 0.059 Uiso 0.50 1 calc PR A 1
C13 C 0.6364(14) -0.0841(14) 0.0583(11) 0.048(5) Uiso 0.50 1 d PD A 1
H13A H 0.5783 -0.1400 0.0363 0.058 Uiso 0.50 1 calc PR A 1
H13B H 0.6260 -0.0285 0.0101 0.058 Uiso 0.50 1 calc PR A 1
C14 C 0.7808(13) -0.1167(12) 0.0678(12) 0.093(4) Uiso 0.50 1 d PD A 1
H14A H 0.8131 -0.1354 0.0017 0.140 Uiso 0.50 1 calc PR A 1
H14B H 0.7878 -0.1739 0.1131 0.140 Uiso 0.50 1 calc PR A 1
H14C H 0.8351 -0.0617 0.0948 0.140 Uiso 0.50 1 calc PR A 1
C21 C 0.6628(13) 0.2161(8) 0.3330(11) 0.042(5) Uiso 0.50 1 d PD A 1
H21A H 0.6039 0.2617 0.2941 0.050 Uiso 0.50 1 calc PR A 1
H21B H 0.6511 0.2319 0.4047 0.050 Uiso 0.50 1 calc PR A 1
C22 C 0.8048(12) 0.2409(9) 0.3081(11) 0.063(4) Uiso 0.50 1 d PD A 1
H22A H 0.8191 0.2251 0.2367 0.075 Uiso 0.50 1 calc PR A 1
H22B H 0.8659 0.1985 0.3489 0.075 Uiso 0.50 1 calc PR A 1
C23 C 0.8399(16) 0.3490(9) 0.3265(10) 0.078(4) Uiso 0.50 1 d PD A 1
H23A H 0.7768 0.3920 0.2882 0.094 Uiso 0.50 1 calc PR A 1
H23B H 0.9312 0.3623 0.3027 0.094 Uiso 0.50 1 calc PR A 1
C24 C 0.833(2) 0.3741(15) 0.4377(12) 0.122(6) Uiso 0.50 1 d PD A 1
H24A H 0.8534 0.4449 0.4476 0.184 Uiso 0.50 1 calc PR A 1
H24B H 0.8992 0.3339 0.4753 0.184 Uiso 0.50 1 calc PR A 1
H24C H 0.7436 0.3597 0.4616 0.184 Uiso 0.50 1 calc PR A 1
C31 C 0.4225(11) 0.0921(17) 0.3274(16) 0.070(9) Uiso 0.50 1 d PD A 1
H31A H 0.3917 0.0221 0.3237 0.084 Uiso 0.50 1 calc PR A 1
H31B H 0.4039 0.1164 0.3957 0.084 Uiso 0.50 1 calc PR A 1
C32 C 0.3391(16) 0.1515(15) 0.2550(14) 0.086(6) Uiso 0.50 1 d PD A 1
H32A H 0.3590 0.1289 0.1863 0.104 Uiso 0.50 1 calc PR A 1
H32B H 0.3668 0.2221 0.2603 0.104 Uiso 0.50 1 calc PR A 1
C33 C 0.1886(15) 0.1460(15) 0.2682(14) 0.099(7) Uiso 0.50 1 d PD A 1
H33A H 0.1435 0.1875 0.2174 0.149 Uiso 0.50 1 calc PR A 1
H33B H 0.1666 0.1702 0.3351 0.149 Uiso 0.50 1 calc PR A 1
H33C H 0.1588 0.0769 0.2606 0.149 Uiso 0.50 1 calc PR A 1
C41 C 0.6669(13) 0.0091(9) 0.4019(8) 0.043(4) Uiso 0.50 1 d PD A 1
H41A H 0.6717 0.0420 0.4683 0.052 Uiso 0.50 1 calc PR A 1
H41B H 0.6061 -0.0488 0.4069 0.052 Uiso 0.50 1 calc PR A 1
C42 C 0.8046(14) -0.0266(10) 0.3748(10) 0.055(4) Uiso 0.50 1 d PD A 1
H42A H 0.8682 0.0298 0.3774 0.066 Uiso 0.50 1 calc PR A 1
H42B H 0.8022 -0.0533 0.3056 0.066 Uiso 0.50 1 calc PR A 1
C43 C 0.8511(15) -0.1072(10) 0.4472(10) 0.070(4) Uiso 0.50 1 d PD A 1
H43A H 0.8567 -0.0789 0.5156 0.083 Uiso 0.50 1 calc PR A 1
H43B H 0.7839 -0.1612 0.4472 0.083 Uiso 0.50 1 calc PR A 1
C44 C 0.9836(19) -0.1500(17) 0.4221(17) 0.126(8) Uiso 0.50 1 d PD A 1
H44A H 1.0085 -0.2011 0.4715 0.189 Uiso 0.50 1 calc PR A 1
H44B H 1.0512 -0.0971 0.4232 0.189 Uiso 0.50 1 calc PR A 1
H44C H 0.9783 -0.1799 0.3552 0.189 Uiso 0.50 1 calc PR A 1
P1' P 0.60233(15) 0.09270(11) 0.31266(9) 0.0553(6) Uani 0.50 1 d P B 2
C11' C 0.626(2) 0.0540(13) 0.1855(10) 0.054(9) Uiso 0.50 1 d PD B 2
H11C H 0.5873 0.1056 0.1405 0.065 Uiso 0.50 1 calc PR B 2
H11D H 0.7234 0.0517 0.1737 0.065 Uiso 0.50 1 calc PR B 2
C12' C 0.5663(17) -0.0461(11) 0.1554(10) 0.058(5) Uiso 0.50 1 d PD B 2
H12C H 0.4710 -0.0371 0.1359 0.070 Uiso 0.50 1 calc PR B 2
H12D H 0.5709 -0.0919 0.2135 0.070 Uiso 0.50 1 calc PR B 2
C13' C 0.642(3) -0.093(2) 0.0664(18) 0.125(15) Uiso 0.50 1 d PD B 2
H13C H 0.6029 -0.1579 0.0497 0.187 Uiso 0.50 1 calc PR B 2
H13D H 0.7367 -0.1017 0.0855 0.187 Uiso 0.50 1 calc PR B 2
H13E H 0.6348 -0.0489 0.0080 0.187 Uiso 0.50 1 calc PR B 2
C21' C 0.6330(14) 0.2232(9) 0.3347(14) 0.063(6) Uiso 0.50 1 d PD B 2
H21C H 0.5943 0.2624 0.2783 0.076 Uiso 0.50 1 calc PR B 2
H21D H 0.5879 0.2439 0.3966 0.076 Uiso 0.50 1 calc PR B 2
C22' C 0.7841(13) 0.2458(10) 0.3455(12) 0.074(5) Uiso 0.50 1 d PD B 2
H22C H 0.8241 0.2020 0.3978 0.089 Uiso 0.50 1 calc PR B 2
H22D H 0.8276 0.2306 0.2814 0.089 Uiso 0.50 1 calc PR B 2
C23' C 0.8112(13) 0.3537(10) 0.3732(15) 0.085(4) Uiso 0.50 1 d PD B 2
H23C H 0.7778 0.3970 0.3180 0.102 Uiso 0.50 1 calc PR B 2
H23D H 0.7605 0.3705 0.4338 0.102 Uiso 0.50 1 calc PR B 2
C24' C 0.9561(16) 0.3757(16) 0.3929(16) 0.139(7) Uiso 0.50 1 d PD B 2
H24D H 0.9673 0.4467 0.4077 0.209 Uiso 0.50 1 calc PR B 2
H24E H 1.0073 0.3584 0.3337 0.209 Uiso 0.50 1 calc PR B 2
H24F H 0.9885 0.3364 0.4503 0.209 Uiso 0.50 1 calc PR B 2
C31' C 0.4296(10) 0.0759(16) 0.3340(12) 0.053(7) Uiso 0.50 1 d PD B 2
H31C H 0.4112 0.0038 0.3409 0.063 Uiso 0.50 1 calc PR B 2
H31D H 0.4073 0.1083 0.3981 0.063 Uiso 0.50 1 calc PR B 2
C32' C 0.3388(11) 0.1183(11) 0.2506(9) 0.047(4) Uiso 0.50 1 d PD B 2
H32C H 0.3571 0.0833 0.1871 0.056 Uiso 0.50 1 calc PR B 2
H32D H 0.3601 0.1896 0.2411 0.056 Uiso 0.50 1 calc PR B 2
C33' C 0.1898(11) 0.1079(13) 0.2736(10) 0.065(4) Uiso 0.50 1 d PD B 2
H33C H 0.1712 0.0378 0.2918 0.078 Uiso 0.50 1 calc PR B 2
H33D H 0.1695 0.1499 0.3323 0.078 Uiso 0.50 1 calc PR B 2
C34' C 0.1009(15) 0.1367(13) 0.1894(11) 0.108(5) Uiso 0.50 1 d PD B 2
H34C H 0.0078 0.1345 0.2105 0.161 Uiso 0.50 1 calc PR B 2
H34D H 0.1129 0.0904 0.1335 0.161 Uiso 0.50 1 calc PR B 2
H34E H 0.1229 0.2044 0.1678 0.161 Uiso 0.50 1 calc PR B 2
C41' C 0.7046(13) 0.0109(10) 0.3969(9) 0.051(5) Uiso 0.50 1 d PD B 2
H41C H 0.7130 0.0453 0.4623 0.061 Uiso 0.50 1 calc PR B 2
H41D H 0.6515 -0.0502 0.4081 0.061 Uiso 0.50 1 calc PR B 2
C42' C 0.8450(13) -0.0226(10) 0.3692(10) 0.056(4) Uiso 0.50 1 d PD B 2
H42C H 0.8411 -0.0539 0.3020 0.068 Uiso 0.50 1 calc PR B 2
H42D H 0.9040 0.0364 0.3656 0.068 Uiso 0.50 1 calc PR B 2
C43' C 0.9039(14) -0.0953(9) 0.4433(10) 0.063(4) Uiso 0.50 1 d PD B 2
H43C H 0.8431 -0.1531 0.4496 0.075 Uiso 0.50 1 calc PR B 2
H43D H 0.9128 -0.0631 0.5099 0.075 Uiso 0.50 1 calc PR B 2
C44' C 1.0391(18) -0.1310(16) 0.4111(16) 0.118(7) Uiso 0.50 1 d PD B 2
H44D H 1.0744 -0.1794 0.4598 0.176 Uiso 0.50 1 calc PR B 2
H44E H 1.1004 -0.0742 0.4075 0.176 Uiso 0.50 1 calc PR B 2
H44F H 1.0305 -0.1625 0.3451 0.176 Uiso 0.50 1 calc PR B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C41 P1 C21 112.0(7)
C41 P1 C31 105.9(7)
C21 P1 C31 108.7(9)
C41 P1 C11 110.9(8)
C21 P1 C11 107.5(7)
C31 P1 C11 111.9(10)
C12 C11 P1 111.5(9)
C13 C12 C11 113.4(10)
C14 C13 C12 103.6(11)
C22 C21 P1 119.4(9)
C21 C22 C23 113.2(10)
C22 C23 C24 110.9(12)
C32 C31 P1 117.9(12)
C31 C32 C33 116.0(13)
C42 C41 P1 111.4(8)
C41 C42 C43 110.0(10)
C44 C43 C42 113.2(12)
C11' C12' C13' 111.3(14)
C23' C22' C21' 112.3(10)
C24' C23' C22' 113.4(12)
C31' C32' C33' 112.5(9)
C34' C33' C32' 113.3(11)
C43' C42' C41' 112.4(10)
C42' C43' C44' 111.1(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C41 1.750(9)
P1 C21 1.783(9)
P1 C31 1.814(11)
P1 C11 1.814(10)
C11 C12 1.537(12)
C12 C13 1.515(11)
C13 C14 1.511(14)
C21 C22 1.503(12)
C22 C23 1.512(12)
C23 C24 1.524(13)
C31 C32 1.493(13)
C32 C33 1.521(13)
C41 C42 1.510(12)
C42 C43 1.517(11)
C43 C44 1.489(14)
C11' C12' 1.522(13)
C12' C13' 1.558(14)
C21' C22' 1.544(13)
C22' C23' 1.519(12)
C23' C24' 1.496(13)
C31' C32' 1.531(12)
C32' C33' 1.535(11)
C33' C34' 1.469(13)
C41' C42' 1.528(12)
C42' C43' 1.501(11)
C43' C44' 1.507(14)
