#------------------------------------------------------------------------------
#$Date: 2020-05-17 02:29:50 +0300 (Sun, 17 May 2020) $
#$Revision: 252119 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038375.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_4038375
loop_
_publ_author_name
'Schoemaker, Robin'
'Schwedtmann, Kai'
'Hennersdorf, Felix'
'Bauzá, Antonio'
'Frontera, Antonio'
'Weigand, Jan J.'
_publ_section_title
;
 Toward N,P-Doped π-Extended PAHs: A One-Pot Synthesis to Diannulated
 1,4,2-Diazaphospholium Triflate Salts.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00577
_journal_year                    2020
_chemical_formula_moiety         'C10 H8 N2 P, C F3 O3 S'
_chemical_formula_sum            'C11 H8 F3 N2 O3 P S'
_chemical_formula_weight         336.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                95.055(3)
_cell_angle_beta                 99.126(3)
_cell_angle_gamma                109.450(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2241(5)
_cell_length_b                   9.0577(7)
_cell_length_c                   10.9162(8)
_cell_measurement_reflns_used    3662
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.107
_cell_measurement_theta_min      2.841
_cell_volume                     657.34(9)
_computing_cell_refinement       '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, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8822
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.123
_diffrn_reflns_theta_min         1.911
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0332 before and 0.0287 after correction.
The Ratio of minimum to maximum transmission is 0.9315.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0468P)²+0.2272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3277
_reflns_number_total             3836
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00577_si_001.cif
_cod_data_source_block           jjw0327
_cod_original_cell_volume        657.34(8)
_cod_database_code               4038375
_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.
;
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.925
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C5(H5), C11(H11), C3(H3), C10(H10), C4(H4)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-03-11
_olex2_date_sample_submission    2015-03-11
_olex2_submission_original_sample_id jjw0327
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.64664(5) 0.81512(4) 0.22408(3) 0.01636(9) Uani 1 1 d . . . . .
P1 P 0.13914(6) 0.70132(4) 0.54878(3) 0.02044(10) Uani 1 1 d . . . . .
F1 F 0.90224(14) 0.66513(12) 0.23563(10) 0.0313(2) Uani 1 1 d . . . . .
F2 F 0.65694(16) 0.56795(12) 0.32841(11) 0.0378(3) Uani 1 1 d . . . . .
F3 F 0.60861(16) 0.52888(12) 0.12711(11) 0.0401(3) Uani 1 1 d . . . . .
O3 O 0.77513(16) 0.91822(13) 0.33514(10) 0.0250(2) Uani 1 1 d . . . . .
O2 O 0.69844(18) 0.86458(14) 0.10808(10) 0.0296(3) Uani 1 1 d . . . . .
O1 O 0.43584(16) 0.75991(13) 0.22544(11) 0.0256(2) Uani 1 1 d . . . . .
N1 N 0.25962(17) 0.75729(13) 0.79309(11) 0.0172(2) Uani 1 1 d . . . . .
N2 N 0.39033(18) 0.79755(13) 0.61951(11) 0.0179(2) Uani 1 1 d . . . . .
C7 C 0.43180(19) 0.81954(14) 0.74730(11) 0.0134(2) Uani 1 1 d . . . . .
C6 C 0.2519(2) 0.76068(16) 0.91981(13) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.3676 0.8091 0.9810 0.023 Uiso 1 1 calc R . . . .
C8 C 0.6263(2) 0.89257(16) 0.81689(12) 0.0170(3) Uani 1 1 d . . . . .
H8 H 0.6519 0.9053 0.9041 0.020 Uiso 1 1 calc R . . . .
C1 C 0.0908(2) 0.68789(15) 0.69875(13) 0.0173(3) Uani 1 1 d . . . . .
C12 C 0.7076(2) 0.63572(17) 0.22902(14) 0.0216(3) Uani 1 1 d . . . . .
C9 C 0.7786(2) 0.94513(17) 0.75300(13) 0.0197(3) Uani 1 1 d . . . . .
H9 H 0.9098 0.9951 0.7970 0.024 Uiso 1 1 calc R . . . .
C5 C 0.0733(2) 0.69229(18) 0.95234(15) 0.0239(3) Uani 1 1 d . . . . .
H5 H 0.0654 0.6945 1.0367 0.029 Uiso 1 1 calc R . . . .
C11 C 0.5457(2) 0.85074(16) 0.55584(13) 0.0195(3) Uani 1 1 d . . . . .
H11 H 0.5188 0.8365 0.4686 0.023 Uiso 1 1 calc R . . . .
C3 C -0.0941(2) 0.61477(18) 0.73501(16) 0.0247(3) Uani 1 1 d . . . . .
H3 H -0.2100 0.5650 0.6742 0.030 Uiso 1 1 calc R . . . .
C10 C 0.7369(2) 0.92352(17) 0.62042(14) 0.0205(3) Uani 1 1 d . . . . .
H10 H 0.8406 0.9592 0.5773 0.025 Uiso 1 1 calc R . . . .
C4 C -0.1022(2) 0.61725(18) 0.85846(16) 0.0266(3) Uani 1 1 d . . . . .
H4 H -0.2241 0.5692 0.8817 0.032 Uiso 1 1 calc R . . . .
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'
F F 0.0171 0.0103 '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'
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
O3 S1 O2 114.27(7) . . ?
O3 S1 O1 115.51(7) . . ?
O3 S1 C12 103.27(7) . . ?
O2 S1 C12 103.03(7) . . ?
O1 S1 O2 115.26(7) . . ?
O1 S1 C12 103.03(7) . . ?
C1 P1 N2 87.08(6) . . ?
C7 N1 C6 124.70(12) . . ?
C7 N1 C1 112.73(11) . . ?
C1 N1 C6 122.56(12) . . ?
C7 N2 P1 115.69(9) . . ?
C7 N2 C11 119.25(12) . . ?
C11 N2 P1 125.05(10) . . ?
N1 C7 C8 127.05(12) . . ?
N2 C7 N1 110.72(11) . . ?
N2 C7 C8 122.21(12) . . ?
N1 C6 H6 120.6 . . ?
C5 C6 N1 118.82(14) . . ?
C5 C6 H6 120.6 . . ?
C7 C8 H8 121.0 . . ?
C9 C8 C7 118.04(12) . . ?
C9 C8 H8 121.0 . . ?
N1 C1 P1 113.75(10) . . ?
N1 C1 C3 117.61(13) . . ?
C3 C1 P1 128.63(11) . . ?
F1 C12 S1 111.90(10) . . ?
F1 C12 F2 107.67(12) . . ?
F1 C12 F3 107.64(12) . . ?
F2 C12 S1 111.03(10) . . ?
F2 C12 F3 107.12(12) . . ?
F3 C12 S1 111.26(10) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.13(13) . . ?
C10 C9 H9 119.9 . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.28(14) . . ?
C4 C5 H5 119.9 . . ?
N2 C11 H11 119.9 . . ?
C10 C11 N2 120.23(13) . . ?
C10 C11 H11 119.9 . . ?
C1 C3 H3 120.0 . . ?
C4 C3 C1 120.02(14) . . ?
C4 C3 H3 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.13(13) . . ?
C11 C10 H10 119.9 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.68(14) . . ?
C3 C4 H4 119.7 . . ?
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
S1 O3 1.4387(11) . ?
S1 O2 1.4433(11) . ?
S1 O1 1.4389(11) . ?
S1 C12 1.8224(15) . ?
P1 N2 1.7413(13) . ?
P1 C1 1.7333(14) . ?
F1 C12 1.3300(17) . ?
F2 C12 1.3348(17) . ?
F3 C12 1.3351(17) . ?
N1 C7 1.3765(16) . ?
N1 C6 1.3912(17) . ?
N1 C1 1.3855(18) . ?
N2 C7 1.3617(16) . ?
N2 C11 1.3859(18) . ?
C7 C8 1.3936(18) . ?
C6 H6 0.9300 . ?
C6 C5 1.352(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.3704(19) . ?
C1 C3 1.4160(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.413(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.418(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.357(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(2) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 N2 C7 N1 0.50(14) . . . . ?
P1 N2 C7 C8 179.02(10) . . . . ?
P1 N2 C11 C10 -179.51(11) . . . . ?
P1 C1 C3 C4 -179.66(12) . . . . ?
O3 S1 C12 F1 -55.84(12) . . . . ?
O3 S1 C12 F2 64.50(12) . . . . ?
O3 S1 C12 F3 -176.30(10) . . . . ?
O2 S1 C12 F1 63.37(12) . . . . ?
O2 S1 C12 F2 -176.29(10) . . . . ?
O2 S1 C12 F3 -57.08(12) . . . . ?
O1 S1 C12 F1 -176.42(10) . . . . ?
O1 S1 C12 F2 -56.08(12) . . . . ?
O1 S1 C12 F3 63.13(12) . . . . ?
N1 C7 C8 C9 179.14(13) . . . . ?
N1 C6 C5 C4 0.6(2) . . . . ?
N1 C1 C3 C4 1.4(2) . . . . ?
N2 P1 C1 N1 1.33(10) . . . . ?
N2 P1 C1 C3 -177.67(14) . . . . ?
N2 C7 C8 C9 0.9(2) . . . . ?
N2 C11 C10 C9 0.1(2) . . . . ?
C7 N1 C6 C5 -178.68(13) . . . . ?
C7 N1 C1 P1 -1.36(15) . . . . ?
C7 N1 C1 C3 177.76(12) . . . . ?
C7 N2 C11 C10 0.2(2) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C6 N1 C7 N2 179.96(12) . . . . ?
C6 N1 C7 C8 1.5(2) . . . . ?
C6 N1 C1 P1 179.21(10) . . . . ?
C6 N1 C1 C3 -1.67(19) . . . . ?
C6 C5 C4 C3 -0.9(2) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C1 P1 N2 C7 -1.05(10) . . . . ?
C1 P1 N2 C11 178.65(12) . . . . ?
C1 N1 C7 N2 0.54(16) . . . . ?
C1 N1 C7 C8 -177.89(13) . . . . ?
C1 N1 C6 C5 0.7(2) . . . . ?
C1 C3 C4 C5 -0.1(2) . . . . ?
C11 N2 C7 N1 -179.21(11) . . . . ?
C11 N2 C7 C8 -0.69(19) . . . . ?
