#------------------------------------------------------------------------------
#$Date: 2020-05-17 02:28:52 +0300 (Sun, 17 May 2020) $
#$Revision: 252116 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038372.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_4038372
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         'C7 H4 Cl2 N P S'
_chemical_formula_sum            'C7 H4 Cl2 N P S'
_chemical_formula_weight         236.04
_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   difmap
_audit_creation_date             2017-02-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                91.2912(19)
_cell_angle_beta                 107.150(2)
_cell_angle_gamma                108.239(2)
_cell_formula_units_Z            2
_cell_length_a                   6.71538(17)
_cell_length_b                   6.98592(18)
_cell_length_c                   10.6276(2)
_cell_measurement_reflns_used    2960
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.3340
_cell_measurement_theta_min      4.3590
_cell_volume                     448.83(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -58.00  28.00   0.50    0.50    --  -38.50  57.00   0.00  172
  2  ω    -29.00  -2.00   0.50    0.50    --  -38.50 125.00-150.00   54
  3  ω    -68.00 -35.00   0.50    0.50    --  -38.50 125.00-150.00   66
  4  ω     16.00 113.00   0.50    0.50    --   42.50  57.00-150.00  194
  5  ω    141.00 176.00   0.50    2.00    --  111.00  61.00-180.00   70
  6  ω    113.00 171.00   0.50    2.00    --  111.00  15.00-180.00  116
  7  ω    104.00 133.00   0.50    2.00    --  111.00 -77.00-150.00   58
  8  ω    101.00 133.00   0.50    2.00    --  111.00 -45.00-150.00   64
  9  ω     89.00 177.00   0.50    2.00    --  111.00  30.00-120.00  176
 10  ω     85.00 112.00   0.50    2.00    --  111.00  61.00-180.00   54
 11  ω     66.00  92.00   0.50    2.00    --  111.00  15.00-180.00   52
 12  ω     41.00 100.00   0.50    2.00    --  111.00 -45.00-150.00  118
 13  ω     79.00 106.00   0.50    2.00    --  111.00 -94.00-180.00   54
 14  ω     84.00 111.00   0.50    2.00    --  111.00-125.00-180.00   54
 15  ω     53.00  81.00   0.50    2.00    --  111.00 -77.00-150.00   56
 16  ω     41.00  66.00   0.50    2.00    --  111.00-125.00-180.00   50
 17  ω     39.00  78.00   0.50    2.00    --  111.00 -77.00-180.00   78
 18  ω     47.00 121.00   0.50    2.00    --  111.00-125.00 -60.00  148
 19  ω     43.00 139.00   0.50    2.00    --  111.00 -61.00  30.00  192
 20  ω    153.00 178.00   0.50    2.00    --  111.00  15.00 120.00   50
 21  ω    140.00 172.00   0.50    2.00    --  111.00  45.00  90.00   64
 22  ω    109.00 136.00   0.50    2.00    --  111.00  45.00  90.00   54
 23  ω     76.00 101.00   0.50    2.00    --  111.00  15.00 120.00   50
 24  ω     32.00 105.00   0.50    2.00    --  111.00 -94.00  30.00  146
 25  ω     46.00 102.00   0.50    2.00    --  111.00-125.00  30.00  112
 26  ω    -60.00  33.00   0.50    0.50    --  -38.50  77.00  90.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0114612000
_diffrn_orient_matrix_UB_12      -0.0805301000
_diffrn_orient_matrix_UB_13      -0.1390097000
_diffrn_orient_matrix_UB_21      -0.1743750000
_diffrn_orient_matrix_UB_22      0.0993140000
_diffrn_orient_matrix_UB_23      -0.0637334000
_diffrn_orient_matrix_UB_31      0.1853860000
_diffrn_orient_matrix_UB_32      0.1960624000
_diffrn_orient_matrix_UB_33      -0.0017118000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3556
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.555
_diffrn_reflns_theta_min         4.389
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0223
_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)+(0.0375P)²+0.1374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1796
_reflns_number_total             1850
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00577_si_010.cif
_cod_data_source_block           jjw0611
_cod_database_code               4038372
_chemical_oxdiff_formula         'C14 H8 Cl4 N2 P2 S2 '
_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.
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.863
_oxdiff_exptl_absorpt_empirical_full_min 0.777
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
Cl1 Cl 0.74026(5) 0.92976(5) 0.03758(3) 0.01925(10) Uani 1 1 d . . . . .
Cl2 Cl 0.77755(6) 0.49350(5) 0.07457(3) 0.01985(10) Uani 1 1 d . . . . .
S1 S 0.57774(5) 0.81218(5) 0.29360(3) 0.01503(10) Uani 1 1 d . . . . .
P1 P 0.93931(5) 0.79226(5) 0.16083(3) 0.01577(10) Uani 1 1 d . . . . .
N1 N 0.94548(19) 0.74555(17) 0.41063(12) 0.0154(2) Uani 1 1 d . . . . .
C1 C 0.8271(2) 0.7807(2) 0.29825(14) 0.0146(3) Uani 1 1 d . . . . .
C2 C 0.6328(2) 0.7710(2) 0.45845(13) 0.0144(3) Uani 1 1 d . . . . .
C3 C 0.8376(2) 0.7381(2) 0.50445(14) 0.0140(3) Uani 1 1 d . . . . .
C4 C 0.9176(2) 0.7018(2) 0.63587(14) 0.0164(3) Uani 1 1 d . . . . .
H4 H 1.058(3) 0.678(3) 0.6670(19) 0.017(4) Uiso 1 1 d . . . . .
C5 C 0.7912(2) 0.7000(2) 0.71808(14) 0.0176(3) Uani 1 1 d . . . . .
H5 H 0.841(3) 0.674(3) 0.808(2) 0.018(4) Uiso 1 1 d . . . . .
C6 C 0.5866(2) 0.7326(2) 0.67096(14) 0.0173(3) Uani 1 1 d . . . . .
H6 H 0.506(4) 0.731(3) 0.729(2) 0.027(5) Uiso 1 1 d . . . . .
C7 C 0.5040(2) 0.7674(2) 0.54120(15) 0.0161(3) Uani 1 1 d . . . . .
H7 H 0.369(3) 0.786(3) 0.508(2) 0.022(5) Uiso 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 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0288
0 0 -1 0.0288
3 -3 -4 0.0380
-3 3 4 0.0380
-3 -1 2 0.0814
3 1 -2 0.0814
-2 4 -3 0.0532
0 -4 3 0.0916
4 -1 2 0.0652
-4 3 -1 0.0636
-2 2 6 0.0344
2 -2 4 0.0487
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
C2 S1 C1 88.40(7) . . ?
Cl1 P1 Cl2 99.727(19) . . ?
C1 P1 Cl1 98.26(5) . . ?
C1 P1 Cl2 98.23(4) . . ?
C1 N1 C3 109.84(11) . . ?
S1 C1 P1 126.38(8) . . ?
N1 C1 S1 117.08(10) . . ?
N1 C1 P1 116.54(10) . . ?
C3 C2 S1 109.89(10) . . ?
C7 C2 S1 128.56(11) . . ?
C7 C2 C3 121.55(13) . . ?
N1 C3 C2 114.79(12) . . ?
N1 C3 C4 125.02(12) . . ?
C4 C3 C2 120.20(13) . . ?
C3 C4 H4 119.9(11) . . ?
C5 C4 C3 118.30(13) . . ?
C5 C4 H4 121.8(11) . . ?
C4 C5 H5 120.1(11) . . ?
C4 C5 C6 121.02(13) . . ?
C6 C5 H5 118.9(11) . . ?
C5 C6 H6 118.9(13) . . ?
C7 C6 C5 121.57(13) . . ?
C7 C6 H6 119.5(13) . . ?
C2 C7 H7 120.0(13) . . ?
C6 C7 C2 117.36(13) . . ?
C6 C7 H7 122.6(13) . . ?
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
Cl1 P1 2.0623(5) . ?
Cl2 P1 2.0697(5) . ?
S1 C1 1.7427(13) . ?
S1 C2 1.7310(14) . ?
P1 C1 1.8231(14) . ?
N1 C1 1.3015(18) . ?
N1 C3 1.3881(18) . ?
C2 C3 1.4101(19) . ?
C2 C7 1.3998(19) . ?
C3 C4 1.4008(19) . ?
C4 H4 0.97(2) . ?
C4 C5 1.384(2) . ?
C5 H5 0.95(2) . ?
C5 C6 1.409(2) . ?
C6 H6 0.93(2) . ?
C6 C7 1.385(2) . ?
C7 H7 0.92(2) . ?
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
Cl1 P1 C1 S1 15.67(9) . . . . ?
Cl1 P1 C1 N1 -164.29(10) . . . . ?
Cl2 P1 C1 S1 -85.49(9) . . . . ?
Cl2 P1 C1 N1 94.56(10) . . . . ?
S1 C2 C3 N1 -0.09(15) . . . . ?
S1 C2 C3 C4 179.82(10) . . . . ?
S1 C2 C7 C6 -179.46(11) . . . . ?
N1 C3 C4 C5 179.67(12) . . . . ?
C1 S1 C2 C3 0.48(10) . . . . ?
C1 S1 C2 C7 -179.36(13) . . . . ?
C1 N1 C3 C2 -0.53(17) . . . . ?
C1 N1 C3 C4 179.56(13) . . . . ?
C2 S1 C1 P1 179.19(9) . . . . ?
C2 S1 C1 N1 -0.86(11) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 N1 C1 S1 0.94(15) . . . . ?
C3 N1 C1 P1 -179.10(9) . . . . ?
C3 C2 C7 C6 0.7(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C2 -0.6(2) . . . . ?
C7 C2 C3 N1 179.77(12) . . . . ?
C7 C2 C3 C4 -0.3(2) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0006 -0.0015 0.9997 -0.1389 -0.0640 -0.0019
-0.0006 0.0015 -0.9997 0.1389 0.0640 0.0019
2.9946 -2.9966 -4.0077 0.7641 -0.5644 -0.0255
-2.9946 2.9966 4.0077 -0.7641 0.5644 0.0255
-2.9976 -0.9960 1.9960 -0.1629 0.2966 -0.7544
2.9976 0.9960 -1.9960 0.1629 -0.2966 0.7544
-1.9991 4.0042 -2.9873 0.1157 0.9367 0.4196
0.0002 -4.0003 2.9871 -0.0931 -0.5877 -0.7894
3.9987 -1.0099 1.9970 -0.2421 -0.9249 0.5399
-3.9972 3.0062 -0.9912 -0.0585 1.0588 -0.1499
-1.9943 1.9926 6.0043 -0.9723 0.1630 0.0107
2.0006 -2.0079 3.9932 -0.4163 -0.8028 -0.0296
