#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/61/2236195.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_2236195
loop_
_publ_author_name
'Reiss, Guido J.'
'Jörgens, Stefan'
_publ_section_title
;
 (Dimethylphosphoryl)methanaminium chloride
;
_journal_coeditor_code           FJ2594
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2899
_journal_page_last               o2900
_journal_paper_doi               10.1107/S1600536812037890
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C3 H11 N O P +, Cl -'
_chemical_formula_moiety         'C3 H11 N O P +, Cl -'
_chemical_formula_sum            'C3 H11 Cl N O P'
_chemical_formula_weight         143.55
_chemical_name_systematic
;
(Dimethylphosphoryl)methanaminium chloride
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.057(4)
_cell_angle_beta                 87.691(3)
_cell_angle_gamma                89.016(4)
_cell_formula_units_Z            2
_cell_length_a                   5.2965(2)
_cell_length_b                   7.7030(4)
_cell_length_c                   8.8035(3)
_cell_measurement_reflns_used    3569
_cell_measurement_temperature    106.0(10)
_cell_measurement_theta_max      32.6283
_cell_measurement_theta_min      3.3426
_cell_volume                     356.92(3)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      106.0(10)
_diffrn_detector_area_resol_mean 16.2711
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur diffractometer, Eos'
_diffrn_measurement_method       '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  0.0121
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3785
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.35
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             152
_exptl_crystal_size_max          0.920
_exptl_crystal_size_mid          0.782
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.336
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         2076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0206
_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)+(0.0120P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0493
_reflns_number_gt                1968
_reflns_number_total             2076
_reflns_threshold_expression     I>2sigma(I)
_iucr_refine_instructions_details
;
TITL EXP_260_106 IN P-1
CELL  0.71073  5.29655  7.70299  8.80351 84.05680 87.69100 89.01630
ZERR 2  0.00020  0.00044  0.00032  0.00380  0.00300  0.00380
LATT 1
SFAC C H N O P CL
UNIT 6 22 2 2 2 2
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
OMIT -2 60
PLAN 30
FMAP 2
L.S. 7
EQIV $1 x-1, y, z
EQIV $2 -x+1, -y, -z+1
HTAB N1 Cl1
HTAB N1 Cl1_$1
HTAB N1 O1_$2
BOND $H
CONF
ACTA
WGHT    0.012000    0.200000
EXTI    0.010526
FVAR      13.89926
CL1   6    0.830502   -0.229553    0.161346    11.00000    0.00959    0.01727 =
         0.01736   -0.00544   -0.00150   -0.00039
P1    5    0.489268    0.254179    0.289159    11.00000    0.00887    0.00949 =
         0.01037    0.00029   -0.00141    0.00077
O1    4    0.658909    0.183503    0.413455    11.00000    0.01260    0.01677 =
         0.01117    0.00123   -0.00296    0.00075
N1    3    0.315930   -0.081709    0.285829    11.00000    0.00983    0.01101 =
         0.01141   -0.00124   -0.00201   -0.00049
H1    2    0.465694   -0.105629    0.234098    11.00000    0.02192
H2    2    0.192546   -0.141866    0.256006    11.00000    0.02525
H3    2    0.337897   -0.112094    0.387118    11.00000    0.02447
C1    1    0.237388    0.104554    0.260125    11.00000    0.00834    0.01195 =
         0.01470    0.00083   -0.00172    0.00068
H1a   2    0.098960    0.122554    0.327013    11.00000    0.01587
H1b   2    0.184905    0.127736    0.155498    11.00000    0.02038
C2    1    0.323492    0.449949    0.326894    11.00000    0.01915    0.01411 =
         0.02967   -0.00560   -0.00383    0.00466
AFIX 137
H2a   2    0.442331    0.541685    0.331966    11.00000    0.03528
H2b   2    0.229507    0.430625    0.422528    11.00000    0.03209
H2c   2    0.209536    0.482758    0.246470    11.00000    0.02819
AFIX   0
C3    1    0.654415    0.295198    0.108794    11.00000    0.01310    0.02239 =
         0.01167    0.00254   -0.00093   -0.00355
AFIX 137
H3a    2    0.742556    0.191024    0.084633    11.00000    0.02749
H3b   2    0.773557    0.386847    0.113428    11.00000    0.02985
H3c   2    0.536039    0.329807    0.031222    11.00000    0.01876
AFIX   0
HKLF 4
END
;
_cod_data_source_file            fj2594.cif
_cod_data_source_block           I
_cod_original_cell_volume        356.93(3)
_cod_database_code               2236195
_cod_database_fobs_code          2236195
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl Cl1 0.83052(4) -0.22956(3) 0.16135(3) 0.01445(7) Uani d . 1 1
P P1 0.48926(5) 0.25417(3) 0.28914(3) 0.00963(7) Uani d . 1 1
O O1 0.65884(14) 0.18353(10) 0.41347(8) 0.01364(15) Uani d . 1 1
N N1 0.31590(16) -0.08170(11) 0.28582(10) 0.01068(16) Uani d . 1 1
H H1 0.465(3) -0.105(2) 0.2342(17) 0.024(4) Uiso d . 1 1
H H2 0.192(3) -0.142(2) 0.2566(18) 0.023(4) Uiso d . 1 1
H H3 0.338(3) -0.112(2) 0.3865(19) 0.025(4) Uiso d . 1 1
C C1 0.23746(18) 0.10462(13) 0.26016(12) 0.01177(18) Uani d . 1 1
H H1A 0.099(3) 0.1224(18) 0.3275(16) 0.017(3) Uiso d . 1 1
H H1B 0.185(3) 0.128(2) 0.1563(18) 0.022(4) Uiso d . 1 1
C C2 0.3235(2) 0.45000(15) 0.32696(15) 0.0207(2) Uani d . 1 1
H H2A 0.4425 0.5416 0.3322 0.036(5) Uiso calc R 1 1
H H2B 0.2293 0.4306 0.4225 0.031(4) Uiso calc R 1 1
H H2C 0.2098 0.4830 0.2465 0.029(4) Uiso calc R 1 1
C C3 0.6544(2) 0.29523(15) 0.10879(12) 0.0159(2) Uani d . 1 1
H H3A 0.7423 0.1910 0.0845 0.028(4) Uiso calc R 1 1
H H3B 0.7737 0.3868 0.1135 0.030(4) Uiso calc R 1 1
H H3C 0.5361 0.3300 0.0312 0.020(4) Uiso calc R 1 1
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
Cl1 0.00962(11) 0.01729(12) 0.01731(13) -0.00050(8) -0.00147(8) -0.00548(9)
P1 0.00893(12) 0.00947(12) 0.01030(12) 0.00069(8) -0.00136(8) 0.00023(8)
O1 0.0127(3) 0.0166(4) 0.0112(3) 0.0006(3) -0.0029(3) 0.0011(3)
N1 0.0099(4) 0.0110(4) 0.0113(4) -0.0007(3) -0.0019(3) -0.0013(3)
C1 0.0085(4) 0.0118(4) 0.0146(5) 0.0006(3) -0.0016(3) 0.0008(3)
C2 0.0192(5) 0.0141(5) 0.0296(6) 0.0047(4) -0.0037(4) -0.0056(4)
C3 0.0131(5) 0.0222(5) 0.0117(5) -0.0035(4) -0.0010(4) 0.0025(4)
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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
O1 P1 C3 112.50(5)
O1 P1 C2 114.00(5)
C3 P1 C2 107.74(6)
O1 P1 C1 112.45(4)
C3 P1 C1 105.97(5)
C2 P1 C1 103.48(5)
C1 N1 H1 112.4(9)
C1 N1 H2 106.4(10)
H1 N1 H2 111.5(14)
C1 N1 H3 109.8(10)
H1 N1 H3 107.6(13)
H2 N1 H3 109.1(14)
N1 C1 P1 113.12(7)
N1 C1 H1A 107.9(9)
P1 C1 H1A 109.8(9)
N1 C1 H1B 108.5(9)
P1 C1 H1B 108.3(9)
H1A C1 H1B 109.1(13)
P1 C2 H2A 109.5
P1 C2 H2B 109.5
H2A C2 H2B 109.5
P1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
P1 C3 H3A 109.5
P1 C3 H3B 109.5
H3A C3 H3B 109.5
P1 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4966(7)
P1 C3 1.7832(11)
P1 C2 1.7866(11)
P1 C1 1.8199(10)
N1 C1 1.4844(13)
N1 H1 0.921(16)
N1 H2 0.872(16)
N1 H3 0.905(16)
C1 H1A 0.941(15)
C1 H1B 0.965(15)
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
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 H1 Cl1 . 0.921(16) 2.245(16) 3.1367(9) 162.8(13)
N1 H2 Cl1 1_455 0.872(16) 2.262(16) 3.1134(9) 165.3(14)
N1 H3 O1 2_656 0.905(16) 1.791(16) 2.6900(12) 172.4(15)
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
O1 P1 C1 N1 -34.32(9)
C3 P1 C1 N1 88.97(8)
C2 P1 C1 N1 -157.80(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658055
