#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:32:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180144 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/41/7104177.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_7104177
loop_
_publ_author_name
'Schmid, Dirk'
'Loscher, Sebastian'
'Gudat, Dietrich'
'Bubrin, Denis'
'Hartenbach, Ingo'
'Schleid, Thomas'
'Benko, Zoltán'
'Nyulászi, László'
_publ_section_title
;
 Benzo-1,3,2-diazaphospholide and benzo-1,3,2-diazaphospholium: an
 isoelectronic aromatic anion-cation pair.
;
_journal_issue                   7
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              830
_journal_page_last               832
_journal_paper_doi               10.1039/b817046k
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C7 H6 F3 N2 O3 P S'
_chemical_formula_weight         286.17
_chemical_name_common
'Benzo-1,3,2H-Diazaphospholenium Trifluormethane sulfonate'
_chemical_name_systematic
;
?
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.374(4)
_cell_angle_beta                 112.907(4)
_cell_angle_gamma                92.534(4)
_cell_formula_units_Z            4
_cell_length_a                   9.9377(7)
_cell_length_b                   11.2028(8)
_cell_length_c                   11.6347(8)
_cell_measurement_reflns_used    10799
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      1.02
_cell_volume                     1053.91(13)
_computing_cell_refinement       'DENZO (W. Minor & Z. Otwinowski)'
_computing_data_collection       'Nonius Collect Software'
_computing_data_reduction        'DENZO (W. Minor & Z. Otwinowski)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'four-circle, ccd detector'
_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  0.1513
_diffrn_reflns_av_sigmaI/netI    0.1427
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15230
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  0.9529
_exptl_absorpt_correction_T_min  0.7698
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'HABITUS (W. Herrendorf)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath-shaped
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.0638
_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)+(0.0620P)²+0.1748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1576
_reflns_number_gt                2912
_reflns_number_total             5077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b817046k.txt
_cod_data_source_block           c:\crystal\x-red32\dsnov07
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7104177
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.03365(13) 0.77066(12) 0.16846(13) 0.0203(3) Uani 1 1 d . . .
N2 N 0.0586(4) 0.8365(4) 0.0738(4) 0.0172(8) Uani 1 1 d . . .
H2A H 0.0025 0.8031 -0.0154 0.021 Uiso 1 1 calc R . .
C3 C 0.1779(5) 0.9508(4) 0.1491(5) 0.0150(9) Uani 1 1 d . . .
C4 C 0.2488(4) 0.9798(4) 0.2900(4) 0.0134(9) Uani 1 1 d . . .
N5 N 0.1771(4) 0.8860(4) 0.3098(4) 0.0172(8) Uani 1 1 d . . .
H5A H 0.2061 0.8885 0.3909 0.021 Uiso 1 1 calc R . .
C6 C 0.3723(5) 1.0884(5) 0.3886(5) 0.0203(10) Uani 1 1 d . . .
H6A H 0.4191 1.1074 0.4828 0.024 Uiso 1 1 calc R . .
C7 C 0.4239(5) 1.1683(5) 0.3413(5) 0.0230(11) Uani 1 1 d . . .
H7A H 0.5064 1.2420 0.4046 0.028 Uiso 1 1 calc R . .
C8 C 0.3524(5) 1.1379(5) 0.2000(6) 0.0250(11) Uani 1 1 d . . .
H8A H 0.3892 1.1924 0.1711 0.030 Uiso 1 1 calc R . .
C9 C 0.2282(5) 1.0299(4) 0.0999(5) 0.0157(9) Uani 1 1 d . . .
H9A H 0.1812 1.0111 0.0058 0.019 Uiso 1 1 calc R . .
S1 S 0.22643(11) 0.51630(11) -0.79935(11) 0.0139(2) Uani 1 1 d . . .
O1 O 0.2150(3) 0.6135(3) -0.6761(3) 0.0168(7) Uani 1 1 d . . .
O2 O 0.1690(3) 0.3780(3) -0.8368(3) 0.0207(7) Uani 1 1 d . . .
O3 O 0.1839(4) 0.5483(4) -0.9139(3) 0.0273(8) Uani 1 1 d . . .
C1 C 0.4289(5) 0.5321(5) -0.7370(5) 0.0196(10) Uani 1 1 d . . .
F1 F 0.4999(3) 0.6558(3) -0.6971(3) 0.0304(7) Uani 1 1 d . . .
F2 F 0.4852(3) 0.5087(3) -0.6259(3) 0.0326(7) Uani 1 1 d . . .
F3 F 0.4580(3) 0.4455(3) -0.8366(3) 0.0316(7) Uani 1 1 d . . .
P11 P 0.11381(12) 0.29664(12) -0.62425(12) 0.0153(3) Uani 1 1 d . . .
N12 N 0.1632(4) 0.4620(4) -0.5520(4) 0.0131(8) Uani 1 1 d . . .
H12A H 0.1716 0.5034 -0.5976 0.016 Uiso 1 1 calc R . .
C13 C 0.1905(4) 0.5301(4) -0.4117(4) 0.0114(9) Uani 1 1 d . . .
C14 C 0.1686(4) 0.4355(4) -0.3657(4) 0.0118(9) Uani 1 1 d . . .
N15 N 0.1273(4) 0.3055(4) -0.4751(4) 0.0135(8) Uani 1 1 d . . .
H15A H 0.1100 0.2349 -0.4658 0.016 Uiso 1 1 calc R . .
C16 C 0.1898(4) 0.4800(4) -0.2277(4) 0.0146(9) Uani 1 1 d . . .
H16A H 0.1741 0.4190 -0.1964 0.017 Uiso 1 1 calc R . .
C17 C 0.2343(5) 0.6156(5) -0.1399(5) 0.0183(10) Uani 1 1 d . . .
H17A H 0.2507 0.6467 -0.0469 0.022 Uiso 1 1 calc R . .
C18 C 0.2563(5) 0.7103(5) -0.1850(5) 0.0167(10) Uani 1 1 d . . .
H18A H 0.2862 0.8022 -0.1221 0.020 Uiso 1 1 calc R . .
C19 C 0.2337(4) 0.6677(4) -0.3230(5) 0.0148(9) Uani 1 1 d . . .
H19A H 0.2472 0.7293 -0.3543 0.018 Uiso 1 1 calc R . .
S2 S 0.81531(11) 0.98130(11) 0.32822(11) 0.0131(2) Uani 1 1 d . . .
O4 O 0.8595(3) 0.8765(3) 0.3655(3) 0.0201(7) Uani 1 1 d . . .
O5 O 0.7767(3) 1.0858(3) 0.4246(3) 0.0197(7) Uani 1 1 d . . .
O6 O 0.9074(3) 1.0297(3) 0.2792(3) 0.0207(7) Uani 1 1 d . . .
C2 C 0.6354(5) 0.8922(5) 0.1700(5) 0.0205(10) Uani 1 1 d . . .
F4 F 0.5826(3) 0.9742(3) 0.1155(3) 0.0271(7) Uani 1 1 d . . .
F5 F 0.6518(3) 0.7878(3) 0.0738(3) 0.0363(8) Uani 1 1 d . . .
F6 F 0.5328(3) 0.8498(3) 0.2002(3) 0.0355(8) Uani 1 1 d . . .
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'
P P 0.1023 0.0942 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 P1 N2 90.56(18) . . ?
C3 N2 P1 114.9(3) . . ?
C4 C3 N2 109.6(4) . . ?
C4 C3 C9 121.5(4) . . ?
N2 C3 C9 128.9(4) . . ?
C6 C4 N5 128.7(4) . . ?
C6 C4 C3 121.6(4) . . ?
N5 C4 C3 109.7(4) . . ?
C4 N5 P1 115.3(3) . . ?
C4 C6 C7 117.6(4) . . ?
C8 C7 C6 120.2(4) . . ?
C9 C8 C7 122.9(4) . . ?
C8 C9 C3 116.1(4) . . ?
O3 S1 O2 116.0(2) . . ?
O3 S1 O1 115.3(2) . . ?
O2 S1 O1 112.88(18) . . ?
O3 S1 C1 103.9(2) . . ?
O2 S1 C1 103.1(2) . . ?
O1 S1 C1 103.4(2) . . ?
F3 C1 F1 108.5(4) . . ?
F3 C1 F2 108.4(4) . . ?
F1 C1 F2 107.8(4) . . ?
F3 C1 S1 110.9(3) . . ?
F1 C1 S1 110.8(3) . . ?
F2 C1 S1 110.4(3) . . ?
N12 P11 N15 90.87(18) . . ?
C13 N12 P11 115.1(3) . . ?
C19 C13 N12 128.7(4) . . ?
C19 C13 C14 121.9(4) . . ?
N12 C13 C14 109.4(4) . . ?
N15 C14 C16 130.2(4) . . ?
N15 C14 C13 109.8(4) . . ?
C16 C14 C13 120.0(4) . . ?
C14 N15 P11 114.8(3) . . ?
C17 C16 C14 118.0(4) . . ?
C16 C17 C18 122.2(4) . . ?
C19 C18 C17 120.5(4) . . ?
C13 C19 C18 117.3(4) . . ?
O5 S2 O6 114.41(19) . . ?
O5 S2 O4 115.47(19) . . ?
O6 S2 O4 115.0(2) . . ?
O5 S2 C2 103.5(2) . . ?
O6 S2 C2 103.3(2) . . ?
O4 S2 C2 102.8(2) . . ?
F5 C2 F6 109.0(4) . . ?
F5 C2 F4 108.4(4) . . ?
F6 C2 F4 107.5(4) . . ?
F5 C2 S2 110.4(3) . . ?
F6 C2 S2 110.9(3) . . ?
F4 C2 S2 110.6(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N5 1.632(4) . ?
P1 N2 1.638(4) . ?
N2 C3 1.394(5) . ?
C3 C4 1.390(6) . ?
C3 C9 1.401(6) . ?
C4 C6 1.386(6) . ?
C4 N5 1.388(5) . ?
C6 C7 1.397(6) . ?
C7 C8 1.390(7) . ?
C8 C9 1.389(6) . ?
S1 O3 1.432(3) . ?
S1 O2 1.445(3) . ?
S1 O1 1.450(3) . ?
S1 C1 1.826(5) . ?
C1 F3 1.314(6) . ?
C1 F1 1.327(5) . ?
C1 F2 1.336(5) . ?
P11 N12 1.641(4) . ?
P11 N15 1.648(4) . ?
N12 C13 1.389(5) . ?
C13 C19 1.381(6) . ?
C13 C14 1.412(5) . ?
C14 N15 1.386(5) . ?
C14 C16 1.392(6) . ?
C16 C17 1.362(6) . ?
C17 C18 1.406(6) . ?
C18 C19 1.390(6) . ?
S2 O5 1.438(3) . ?
S2 O6 1.440(3) . ?
S2 O4 1.441(3) . ?
S2 C2 1.829(4) . ?
C2 F5 1.314(6) . ?
C2 F6 1.328(5) . ?
C2 F4 1.336(5) . ?
