#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:43:03 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234486 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/50/7125072.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_7125072
loop_
_publ_author_name
'Jost, Maximilian'
'Finger, Lars H.'
'Sundermeyer, Jörg'
'von Hänisch, Carsten'
_publ_section_title
;
 Simple access to ionic liquids and organic salts containing the
 phosphaethynolate (PCO(-)) and Zintl (Sb11(3-)) anions.
;
_journal_issue                   78
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11646
_journal_page_last               11648
_journal_paper_doi               10.1039/c6cc06620h
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C4 H12 N, C O P'
_chemical_formula_sum            'C5 H12 N O P'
_chemical_formula_weight         133.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-01-27 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.184(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9410(5)
_cell_length_b                   7.4092(6)
_cell_length_c                   8.8324(8)
_cell_measurement_reflns_used    2211
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.34
_cell_volume                     383.80(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_structure_solution    'ShelXS (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4874
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.135
_diffrn_reflns_theta_min         2.336
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       plate
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0326P)²+0.1491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                807
_reflns_number_total             921
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc06620h2.cif
_cod_data_source_block           compound6
_cod_database_code               7125072
_shelxl_version_number           2014-3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2.a Riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_file
;
TITL shelx C m R = New: P21/m
CELL 0.71073 5.941 7.4092 8.8324 90 99.184 90
ZERR 2 0.0005 0.0006 0.0008 0 0.004 0
LATT 1
SYMM -X,0.5+Y,-Z
SFAC C H N O P
UNIT 10 24 2 2 2

L.S. 15
PLAN  20
TEMP -173.15
BOND $H
CONF
fmap 2
acta 50.0
MERG 2
REM <olex2.extras>
REM <HklSrc "%.\\mj82a.hkl">
REM </olex2.extras>

WGHT    0.032600    0.149100
FVAR       1.46154
N1    3    0.456405    0.750000    0.753343    10.50000    0.01440    0.01259 =
         0.01401    0.00000    0.00097    0.00000
C1    1    0.604362    0.585460    0.759240    11.00000    0.01918    0.01374 =
         0.02059   -0.00105    0.00190    0.00321
AFIX 137
H1A   2    0.714800    0.586290    0.854361    11.00000   -1.50000
H1B   2    0.685774    0.585476    0.671085    11.00000   -1.50000
H1C   2    0.509243    0.477044    0.756130    11.00000   -1.50000
AFIX   0
C2    1    0.331565    0.750000    0.888015    10.50000    0.02188    0.02125 =
         0.02019    0.00000    0.00834    0.00000
AFIX   3
H2A   2    0.438255    0.750000    0.973075    10.50000   -1.50000
H2B   2    0.238545    0.855800    0.882085    11.00000   -1.50000
AFIX   0
C3    1    0.287643    0.750000    0.607820    10.50000    0.02031    0.02218 =
         0.01946    0.00000   -0.00499    0.00000
AFIX   3
H3A   2    0.187693    0.858300    0.608770    11.00000   -1.50000
H3B   2    0.369493    0.750000    0.523770    10.50000   -1.50000
AFIX   0
P1    5    0.952842    0.750000    0.166555    10.50000    0.01899    0.01889 =
         0.01839    0.00000    0.00415    0.00000
O1    4    0.763233    0.750000    0.437623    10.50000    0.02905    0.04005 =
         0.01830    0.00000    0.00729    0.00000
C4    1    0.846045    0.750000    0.321915    10.50000    0.01498    0.01466 =
         0.01912    0.00000   -0.00242    0.00000
HKLF 4 1 0 0 -1 0 -0.5 0 -0.5 0 0

REM  shelx C m R = New: P21/m
REM R1 =  0.0303 for     807 Fo > 4sig(Fo)  and  0.0376 for all     921 data
REM     47 parameters refined using      0 restraints

END

WGHT      0.0326      0.1491

REM Highest difference peak  0.378,  deepest hole -0.160,  1-sigma level  0.049
Q1    1   0.8157  0.7500  0.2230  10.50000  0.05    0.38
Q2    1   0.3965  0.7500  0.8137  10.50000  0.05    0.36
Q3    1   0.3780  0.7500  0.6868  10.50000  0.05    0.34
Q4    1   0.9709  0.7500  0.2738  10.50000  0.05    0.31
Q5    1   0.5304  0.8293  0.7546  11.00000  0.05    0.28
Q6    1   0.7888  0.7500  0.1019  10.50000  0.05    0.20
Q7    1   0.8773  0.7500  0.3581  10.50000  0.05    0.20
Q8    1   1.1175  0.7500  0.2142  10.50000  0.05    0.18
Q9    1   1.0946  0.7500  0.1217  10.50000  0.05    0.18
Q10   1   0.9194  0.7500  0.0522  10.50000  0.05    0.17
Q11   1   0.6407  0.5840  0.6936  11.00000  0.05    0.15
Q12   1   0.4402  0.7500  1.0529  10.50000  0.05    0.15
Q13   1   0.8454  0.8120  0.4363  11.00000  0.05    0.14
Q14   1   0.6869  0.7500  0.3910  10.50000  0.05    0.14
Q15   1   0.9565  0.7500  0.4987  10.50000  0.05    0.14
Q16   1   0.7443  0.7500  0.4831  10.50000  0.05    0.14
Q17   1   1.1205  0.7500  0.3419  10.50000  0.05    0.13
Q18   1   0.8646  0.7500  0.5707  10.50000  0.05    0.13
Q19   1   0.4514  0.7500  0.4685  10.50000  0.05    0.13
Q20   1   0.6459  0.5881  0.8277  11.00000  0.05    0.13
;
_shelx_res_checksum              11807
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N 0.4564(2) 0.7500 0.75334(16) 0.0138(3) Uani 1 2 d S T P
C1 C 0.6044(2) 0.58546(16) 0.75924(15) 0.0180(3) Uani 1 1 d . . .
H1A H 0.7148 0.5863 0.8544 0.027 Uiso 1 1 calc GR . .
H1B H 0.6858 0.5855 0.6711 0.027 Uiso 1 1 calc GR . .
H1C H 0.5092 0.4770 0.7561 0.027 Uiso 1 1 calc GR . .
C2 C 0.3316(3) 0.7500 0.8880(2) 0.0206(4) Uani 1 2 d S T P
H2A H 0.4383 0.7500 0.9731 0.031 Uiso 1 2 d RS T P
H2B H 0.2385 0.8558 0.8821 0.031 Uiso 1 1 d R . .
C3 C 0.2876(3) 0.7500 0.6078(2) 0.0215(4) Uani 1 2 d S T P
H3A H 0.1877 0.8583 0.6088 0.032 Uiso 1 1 d R . .
H3B H 0.3695 0.7500 0.5238 0.032 Uiso 1 2 d RS T P
P1 P 0.95284(8) 0.7500 0.16655(6) 0.01863(16) Uani 1 2 d S T P
O1 O 0.7632(2) 0.7500 0.43762(15) 0.0287(3) Uani 1 2 d S T P
C4 C 0.8460(3) 0.7500 0.3219(2) 0.0168(4) Uani 1 2 d S T P
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0144(7) 0.0126(7) 0.0140(8) 0.000 0.0010(6) 0.000
C1 0.0192(6) 0.0137(6) 0.0206(7) -0.0011(5) 0.0019(5) 0.0032(5)
C2 0.0219(9) 0.0212(9) 0.0202(9) 0.000 0.0083(8) 0.000
C3 0.0203(9) 0.0222(10) 0.0195(9) 0.000 -0.0050(8) 0.000
P1 0.0190(3) 0.0189(3) 0.0184(3) 0.000 0.00415(19) 0.000
O1 0.0290(8) 0.0401(9) 0.0183(7) 0.000 0.0073(6) 0.000
C4 0.0150(8) 0.0147(8) 0.0191(9) 0.000 -0.0024(7) 0.000
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C1 N1 C1 108.84(13) 4_575
C2 N1 C1 109.52(9) .
C2 N1 C1 109.52(9) 4_575
C3 N1 C1 109.76(9) .
C3 N1 C1 109.76(9) 4_575
C3 N1 C2 109.43(14) .
N1 C1 H1A 109.5 .
N1 C1 H1B 109.5 .
N1 C1 H1C 109.5 .
H1A C1 H1B 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
N1 C2 H2A 106.9 .
N1 C2 H2B 108.2 .
H2A C2 H2B 111.6 .
N1 C3 H3A 108.1 .
N1 C3 H3B 108.3 .
H3A C3 H3B 112.7 .
O1 C4 P1 179.22(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.4990(14) 4_575
N1 C1 1.4990(14) .
N1 C2 1.499(2) .
N1 C3 1.499(2) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 H2A 0.9023 .
C2 H2B 0.9557 .
C3 H3A 0.9991 .
C3 H3B 0.9502 .
P1 C4 1.6011(19) .
O1 C4 1.203(2) .
