#------------------------------------------------------------------------------
#$Date: 2019-11-17 07:07:30 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228576 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/25/7122595.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_7122595
loop_
_publ_author_name
'Begum, Imtiaz'
'Schnakenburg, Gregor'
'Kelemen, Zsolt'
'Nyulászi, László'
'Boeré, René T'
'Streubel, Rainer'
_publ_section_title
;
 Expanding the chemistry of ring-fused 1,4-diphosphinines by stable mono
 anion formation.
;
_journal_issue                   96
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13555
_journal_page_last               13558
_journal_paper_doi               10.1039/c8cc08158a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C12 H14 Cl2 N2 P2 S4'
_chemical_formula_sum            'C12 H14 Cl2 N2 P2 S4'
_chemical_formula_weight         447.33
_chemical_name_systematic        IB-266
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-07 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                84.231(6)
_cell_angle_beta                 88.651(6)
_cell_angle_gamma                88.674(6)
_cell_formula_units_Z            1
_cell_length_a                   6.5353(5)
_cell_length_b                   6.6119(4)
_cell_length_c                   10.7915(9)
_cell_measurement_reflns_used    1487
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.5750
_cell_measurement_theta_min      3.1360
_cell_volume                     463.72(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35t (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,17:45:29)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35t (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,17:45:29)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35t (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,17:45:29)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   21.00  177.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000    0.0000  102.0000 156
;
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_orient_matrix_UB_11      0.0516861000
_diffrn_orient_matrix_UB_12      0.0460480000
_diffrn_orient_matrix_UB_13      0.0465895000
_diffrn_orient_matrix_UB_21      0.0588733000
_diffrn_orient_matrix_UB_22      -0.0906156000
_diffrn_orient_matrix_UB_23      0.0137213000
_diffrn_orient_matrix_UB_31      0.0751922000
_diffrn_orient_matrix_UB_32      0.0360427000
_diffrn_orient_matrix_UB_33      -0.0448036000
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3033
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_min         3.097
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35t (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,17:45:29)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       plank
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         3033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0329
_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)+(0.0525P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2210
_reflns_number_total             3033
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc08158a2.cif
_cod_data_source_block           5379
_cod_depositor_comments
'Adding full bibliography for 7122593--7122597.cif.'
_cod_database_code               7122595
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H13 Cl2 N2 P2 S4'
_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   0.868
_shelx_estimated_absorpt_t_min   0.760
_diffrn_oxdiff_twin_integration_method simultaneous
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9038(7)
 0.0962(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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
Cl1 Cl 0.12097(14) 0.14330(14) 0.84566(10) 0.0183(3) Uani 1 1 d .
S1 S 0.41184(14) 0.76044(14) 1.01796(9) 0.0133(3) Uani 1 1 d .
S2 S 0.67528(15) 0.83665(16) 0.78823(11) 0.0215(3) Uani 1 1 d .
P1 P -0.04384(15) 0.41973(15) 0.84197(9) 0.0124(3) Uani 1 1 d .
N1 N 0.3154(5) 0.6367(5) 0.8127(3) 0.0122(7) Uani 1 1 d .
C1 C 0.1596(5) 0.5715(5) 0.8968(3) 0.0107(8) Uani 1 1 d .
C2 C 0.1873(5) 0.6271(6) 1.0121(4) 0.0124(8) Uani 1 1 d .
C3 C 0.4660(6) 0.7391(6) 0.8627(4) 0.0155(8) Uani 1 1 d .
C4 C 0.3185(6) 0.6016(6) 0.6803(4) 0.0163(8) Uani 1 1 d .
H4A H 0.2573 0.4685 0.6712 0.020 Uiso 1 1 calc R
H4B H 0.4621 0.5968 0.6493 0.020 Uiso 1 1 calc R
C5 C 0.2006(7) 0.7679(6) 0.6019(4) 0.0229(10) Uani 1 1 d .
H5A H 0.0556 0.7694 0.6306 0.027 Uiso 1 1 calc R
H5B H 0.2584 0.9017 0.6133 0.027 Uiso 1 1 calc R
C6 C 0.2118(8) 0.7339(8) 0.4644(4) 0.0364(12) Uani 1 1 d .
H6A H 0.1252 0.8358 0.4172 0.055 Uiso 1 1 calc GR
H6B H 0.1636 0.5976 0.4538 0.055 Uiso 1 1 calc GR
H6C H 0.3537 0.7465 0.4337 0.055 Uiso 1 1 calc GR
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'
Cl Cl 0.1484 0.1585 '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'
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
C3 S1 C2 91.63(19) . .
C1 P1 Cl1 97.47(12) . .
C2 P1 Cl1 99.08(13) 2_567 .
C2 P1 C1 98.32(17) 2_567 .
C1 N1 C4 123.7(3) . .
C3 N1 C1 114.4(3) . .
C3 N1 C4 121.9(3) . .
N1 C1 P1 118.3(3) . .
C2 C1 P1 128.9(3) . .
C2 C1 N1 112.8(4) . .
S1 C2 P1 116.1(2) . 2_567
C1 C2 S1 111.0(3) . .
C1 C2 P1 132.8(3) . 2_567
S2 C3 S1 123.2(3) . .
N1 C3 S1 110.1(3) . .
N1 C3 S2 126.7(3) . .
N1 C4 H4A 109.3 . .
N1 C4 H4B 109.3 . .
N1 C4 C5 111.7(3) . .
H4A C4 H4B 107.9 . .
C5 C4 H4A 109.3 . .
C5 C4 H4B 109.3 . .
C4 C5 H5A 109.4 . .
C4 C5 H5B 109.4 . .
H5A C5 H5B 108.0 . .
C6 C5 C4 111.2(3) . .
C6 C5 H5A 109.4 . .
C6 C5 H5B 109.4 . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6B 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 P1 2.0973(13) .
S1 C2 1.735(4) .
S1 C3 1.723(4) .
S2 C3 1.679(4) .
P1 C1 1.828(4) .
P1 C2 1.817(4) 2_567
N1 C1 1.394(4) .
N1 C3 1.359(5) .
N1 C4 1.470(5) .
C1 C2 1.350(5) .
C2 P1 1.817(4) 2_567
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C4 C5 1.524(6) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C5 C6 1.523(6) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.8873 3465 1002
2 0.1127 3444 1002
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9038(7)
2 0.0962(7)
