#------------------------------------------------------------------------------
#$Date: 2019-11-17 04:59:05 +0200 (Sun, 17 Nov 2019) $
#$Revision: 227998 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/11/7121137.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_7121137
loop_
_publ_author_name
'Koner, Abhishek'
'Kelemen, Zsolt'
'Schnakenburg, Gregor'
'Nyulászi, László'
'Streubel, Rainer'
_publ_section_title
;
 1,4-Additions of tricyclic 1,4-diphosphinines - a novel system to study
 σ-bond activation and π-π dispersion interactions.
;
_journal_issue                   10
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1182
_journal_page_last               1184
_journal_paper_doi               10.1039/c7cc09349g
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C34 H46 N4 P2 S4'
_chemical_formula_sum            'C34 H46 N4 P2 S4'
_chemical_formula_weight         700.93
_chemical_name_systematic        ABK-465
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-12-05 deposited with the CCDC.
2018-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.230(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.465(3)
_cell_length_b                   13.1095(18)
_cell_length_c                   15.633(2)
_cell_measurement_reflns_used    7641
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.49
_cell_volume                     3683.8(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            50325
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         1.133
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4664
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1032 before and 0.0734 after correction. The Ratio of minimum to maximum transmission is 0.6253. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         8895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0466
_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)+(0.0246P)²+2.5985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7330
_reflns_number_total             8895
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cc09349g2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 7121136--7121139.cif.'
_cod_database_code               7121137
_shelx_shelxl_version_number     2014/7
_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   0.982
_shelx_estimated_absorpt_t_min   0.936
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C3'(H3'A,H3'B), C4'(H4'A,H4'B), C5'(H5'A,H5'B), C8'(H8'A,H8'B), C9'(H9'A,H9'B),
  C10'(H10D,H10E)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C13'(H13'), C14'(H14'),
 C15'(H15'), C16'(H16'), C17'(H17')
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C10(H10A,H10B,H10C), C6'(H6'A,H6'B,H6'C), C11'(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S1 S 0.37667(3) 0.74732(4) 0.68349(4) 0.02173(13) Uani 1 1 d .
S2 S 0.56217(3) 0.69865(4) 0.41702(3) 0.01606(12) Uani 1 1 d .
P P 0.47408(3) 0.58761(4) 0.40227(3) 0.01195(11) Uani 1 1 d .
N1 N 0.41650(10) 0.67519(12) 0.53587(10) 0.0126(3) Uani 1 1 d .
N2 N 0.44690(9) 0.57390(12) 0.64845(10) 0.0125(3) Uani 1 1 d .
C1 C 0.45431(11) 0.59345(14) 0.50992(12) 0.0114(4) Uani 1 1 d .
C2 C 0.41299(12) 0.66472(15) 0.62206(13) 0.0140(4) Uani 1 1 d .
C3 C 0.38307(12) 0.76050(15) 0.47972(13) 0.0155(4) Uani 1 1 d .
H3A H 0.4173 0.7817 0.4427 0.019 Uiso 1 1 calc R
H3B H 0.3769 0.8191 0.5173 0.019 Uiso 1 1 calc R
C4 C 0.30786(12) 0.73372(16) 0.42056(14) 0.0203(5) Uani 1 1 d .
H4A H 0.3145 0.6788 0.3796 0.024 Uiso 1 1 calc R
H4B H 0.2746 0.7077 0.4571 0.024 Uiso 1 1 calc R
C5 C 0.27170(13) 0.82517(18) 0.36813(15) 0.0244(5) Uani 1 1 d .
H5A H 0.3073 0.8556 0.3368 0.029 Uiso 1 1 calc R
H5B H 0.2605 0.8772 0.4092 0.029 Uiso 1 1 calc R
C6 C 0.20038(15) 0.7983(2) 0.30175(17) 0.0416(7) Uani 1 1 d .
H6A H 0.1652 0.7669 0.3322 0.062 Uiso 1 1 calc GR
H6B H 0.2116 0.7504 0.2585 0.062 Uiso 1 1 calc GR
H6C H 0.1784 0.8605 0.2718 0.062 Uiso 1 1 calc GR
C7 C 0.45442(12) 0.53086(16) 0.73693(12) 0.0141(4) Uani 1 1 d .
H7A H 0.4458 0.4563 0.7320 0.017 Uiso 1 1 calc R
H7B H 0.4157 0.5608 0.7639 0.017 Uiso 1 1 calc R
C8 C 0.53063(12) 0.55072(15) 0.79664(12) 0.0136(4) Uani 1 1 d .
H8A H 0.5691 0.5154 0.7727 0.016 Uiso 1 1 calc R
H8B H 0.5413 0.6248 0.7978 0.016 Uiso 1 1 calc R
C9 C 0.53463(12) 0.51361(16) 0.88982(12) 0.0167(4) Uani 1 1 d .
H9A H 0.5211 0.4405 0.8882 0.020 Uiso 1 1 calc R
H9B H 0.4981 0.5518 0.9149 0.020 Uiso 1 1 calc R
C10 C 0.61209(12) 0.52771(16) 0.94883(14) 0.0195(5) Uani 1 1 d .
H10A H 0.6117 0.5066 1.0089 0.029 Uiso 1 1 calc GR
H10B H 0.6265 0.5997 0.9489 0.029 Uiso 1 1 calc GR
H10C H 0.6479 0.4860 0.9267 0.029 Uiso 1 1 calc GR
C11 C 0.52595(11) 0.47027(14) 0.41917(12) 0.0110(4) Uani 1 1 d .
C12 C 0.61041(12) 0.68294(15) 0.52873(13) 0.0141(4) Uani 1 1 d .
C13 C 0.59269(12) 0.74733(15) 0.59219(13) 0.0161(4) Uani 1 1 d .
H13 H 0.5567 0.7997 0.5752 0.019 Uiso 1 1 calc R
C14 C 0.62773(13) 0.73467(16) 0.68000(14) 0.0194(5) Uani 1 1 d .
H14 H 0.6156 0.7781 0.7233 0.023 Uiso 1 1 calc R
C15 C 0.68062(13) 0.65848(17) 0.70455(14) 0.0206(5) Uani 1 1 d .
H15 H 0.7043 0.6495 0.7648 0.025 Uiso 1 1 calc R
C16 C 0.69910(12) 0.59542(16) 0.64149(14) 0.0195(5) Uani 1 1 d .
H16 H 0.7357 0.5439 0.6586 0.023 Uiso 1 1 calc R
C17 C 0.66402(12) 0.60747(16) 0.55310(13) 0.0167(4) Uani 1 1 d .
H17 H 0.6767 0.5644 0.5099 0.020 Uiso 1 1 calc R
S1' S 0.00014(4) 0.15640(4) 0.66319(3) 0.02171(13) Uani 1 1 d .
S2' S -0.09547(3) 0.60592(4) 0.62406(3) 0.01330(11) Uani 1 1 d .
P' P 0.01514(3) 0.57034(4) 0.60806(3) 0.01006(11) Uani 1 1 d .
N1' N 0.00799(9) 0.36350(12) 0.64677(10) 0.0118(3) Uani 1 1 d .
N2' N 0.01272(10) 0.71716(12) 0.47806(10) 0.0117(3) Uani 1 1 d .
C1' C 0.00546(11) 0.43674(14) 0.58130(12) 0.0100(4) Uani 1 1 d .
C2' C -0.00189(12) 0.26803(15) 0.61082(12) 0.0139(4) Uani 1 1 d .
C3' C 0.02882(12) 0.38257(15) 0.74177(12) 0.0136(4) Uani 1 1 d .
H3'A H 0.0052 0.3307 0.7726 0.016 Uiso 1 1 calc R
H3'B H 0.0103 0.4505 0.7544 0.016 Uiso 1 1 calc R
C4' C 0.11303(12) 0.37841(16) 0.77572(12) 0.0150(4) Uani 1 1 d .
H4'A H 0.1363 0.4297 0.7440 0.018 Uiso 1 1 calc R
H4'B H 0.1311 0.3103 0.7628 0.018 Uiso 1 1 calc R
C5' C 0.13764(12) 0.39861(16) 0.87438(13) 0.0172(4) Uani 1 1 d .
H5'A H 0.1251 0.4697 0.8868 0.021 Uiso 1 1 calc R
H5'B H 0.1104 0.3525 0.9061 0.021 Uiso 1 1 calc R
C6' C 0.22109(13) 0.38186(19) 0.90757(15) 0.0265(5) Uani 1 1 d .
H6'A H 0.2356 0.3981 0.9704 0.040 Uiso 1 1 calc GR
H6'B H 0.2481 0.4263 0.8752 0.040 Uiso 1 1 calc GR
H6'C H 0.2331 0.3105 0.8985 0.040 Uiso 1 1 calc GR
C7' C 0.00814(11) 0.61424(14) 0.49689(12) 0.0100(4) Uani 1 1 d .
C8' C 0.03021(12) 0.80060(15) 0.54200(13) 0.0141(4) Uani 1 1 d .
H8'A H 0.0173 0.7793 0.5974 0.017 Uiso 1 1 calc R
H8'B H -0.0008 0.8605 0.5191 0.017 Uiso 1 1 calc R
C9' C 0.11144(12) 0.83117(16) 0.56122(14) 0.0189(5) Uani 1 1 d .
H9'A H 0.1253 0.8497 0.5057 0.023 Uiso 1 1 calc R
H9'B H 0.1427 0.7727 0.5875 0.023 Uiso 1 1 calc R
C10' C 0.12573(14) 0.92143(18) 0.62418(16) 0.0284(6) Uani 1 1 d .
H10D H 0.0900 0.9765 0.6009 0.034 Uiso 1 1 calc R
H10E H 0.1169 0.9000 0.6817 0.034 Uiso 1 1 calc R
C11' C 0.20413(17) 0.9627(2) 0.6375(2) 0.0486(8) Uani 1 1 d .
H11A H 0.2099 1.0220 0.6766 0.073 Uiso 1 1 calc GR
H11B H 0.2135 0.9830 0.5807 0.073 Uiso 1 1 calc GR
H11C H 0.2397 0.9097 0.6639 0.073 Uiso 1 1 calc GR
C12' C -0.15338(11) 0.57054(16) 0.52079(12) 0.0141(4) Uani 1 1 d .
C13' C -0.17858(12) 0.64593(17) 0.45806(13) 0.0177(4) Uani 1 1 d .
H13' H -0.1629 0.7146 0.4693 0.021 Uiso 1 1 calc R
C14' C -0.22695(13) 0.61997(19) 0.37871(14) 0.0233(5) Uani 1 1 d .
H14' H -0.2448 0.6713 0.3362 0.028 Uiso 1 1 calc R
C15' C -0.24901(13) 0.51970(19) 0.36165(14) 0.0240(5) Uani 1 1 d .
H15' H -0.2816 0.5024 0.3072 0.029 Uiso 1 1 calc R
C16' C -0.22379(13) 0.44441(18) 0.42367(14) 0.0220(5) Uani 1 1 d .
H16' H -0.2389 0.3756 0.4116 0.026 Uiso 1 1 calc R
C17' C -0.17636(12) 0.46969(16) 0.50360(14) 0.0168(4) Uani 1 1 d .
H17' H -0.1596 0.4183 0.5464 0.020 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'
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
C12 S2 P 102.86(7) . .
C1 P S2 100.40(7) . .
C11 P S2 101.44(7) . .
C11 P C1 96.54(9) . .
C1 N1 C3 125.72(16) . .
C2 N1 C1 110.47(16) . .
C2 N1 C3 123.80(17) . .
C2 N2 C7 123.86(17) . .
C2 N2 C11 110.65(16) . 3_666
C11 N2 C7 125.48(16) 3_666 .
N1 C1 P 121.85(14) . .
C11 C1 P 131.03(15) 3_666 .
C11 C1 N1 107.02(16) 3_666 .
N1 C2 S1 127.62(15) . .
N2 C2 S1 127.12(15) . .
N2 C2 N1 105.25(17) . .
N1 C3 C4 112.81(17) . .
C5 C4 C3 111.91(18) . .
C4 C5 C6 113.0(2) . .
N2 C7 C8 112.71(17) . .
C9 C8 C7 111.58(17) . .
C8 C9 C10 111.94(18) . .
N2 C11 P 121.00(14) 3_666 .
C1 C11 P 132.42(15) 3_666 .
C1 C11 N2 106.56(17) 3_666 3_666
C13 C12 S2 118.71(16) . .
C17 C12 S2 121.07(16) . .
C17 C12 C13 120.21(19) . .
C14 C13 C12 119.9(2) . .
C13 C14 C15 119.9(2) . .
C16 C15 C14 120.3(2) . .
C15 C16 C17 120.2(2) . .
C12 C17 C16 119.52(19) . .
C12' S2' P' 103.04(7) . .
C1' P' S2' 100.98(7) . .
C1' P' C7' 96.02(8) . .
C7' P' S2' 100.42(7) . .
C1' N1' C3' 125.56(16) . .
C2' N1' C1' 110.44(15) . .
C2' N1' C3' 123.46(16) . .
C2' N2' C7' 110.53(16) 3_566 .
C2' N2' C8' 122.89(16) 3_566 .
C7' N2' C8' 126.51(16) . .
N1' C1' P' 120.92(13) . .
C7' C1' P' 132.27(14) 3_566 .
C7' C1' N1' 106.74(16) 3_566 .
N1' C2' S1' 127.86(15) . .
N1' C2' N2' 105.17(16) . 3_566
N2' C2' S1' 126.96(15) 3_566 .
N1' C3' C4' 110.88(16) . .
C3' C4' C5' 112.91(17) . .
C6' C5' C4' 111.25(18) . .
N2' C7' P' 121.28(14) . .
C1' C7' P' 131.55(15) 3_566 .
C1' C7' N2' 107.08(16) 3_566 .
N2' C8' C9' 112.71(17) . .
C8' C9' C10' 110.55(18) . .
C11' C10' C9' 112.7(2) . .
C13' C12' S2' 119.15(16) . .
C13' C12' C17' 119.86(19) . .
C17' C12' S2' 120.93(16) . .
C14' C13' C12' 119.7(2) . .
C15' C14' C13' 120.2(2) . .
C14' C15' C16' 120.3(2) . .
C15' C16' C17' 120.0(2) . .
C16' C17' C12' 120.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.685(2) .
S2 P 2.1555(8) .
S2 C12 1.781(2) .
P C1 1.803(2) .
P C11 1.799(2) .
N1 C1 1.389(2) .
N1 C2 1.371(2) .
N1 C3 1.468(2) .
N2 C2 1.364(3) .
N2 C7 1.471(2) .
N2 C11 1.395(2) 3_666
C1 C11 1.369(3) 3_666
C3 C4 1.523(3) .
C4 C5 1.518(3) .
C5 C6 1.520(3) .
C7 C8 1.523(3) .
C8 C9 1.521(3) .
C9 C10 1.525(3) .
C11 N2 1.395(2) 3_666
C11 C1 1.369(3) 3_666
C12 C13 1.397(3) .
C12 C17 1.390(3) .
C13 C14 1.387(3) .
C14 C15 1.388(3) .
C15 C16 1.388(3) .
C16 C17 1.394(3) .
S1' C2' 1.673(2) .
S2' P' 2.1646(8) .
S2' C12' 1.782(2) .
P' C1' 1.800(2) .
P' C7' 1.8071(19) .
N1' C1' 1.396(2) .
N1' C2' 1.367(2) .
N1' C3' 1.468(2) .
N2' C2' 1.372(2) 3_566
N2' C7' 1.388(2) .
N2' C8' 1.467(2) .
C1' C7' 1.365(3) 3_566
C2' N2' 1.372(2) 3_566
C3' C4' 1.525(3) .
C4' C5' 1.528(3) .
C5' C6' 1.525(3) .
C7' C1' 1.365(3) 3_566
C8' C9' 1.515(3) .
C9' C10' 1.523(3) .
C10' C11' 1.514(4) .
C12' C13' 1.395(3) .
C12' C17' 1.396(3) .
C13' C14' 1.395(3) .
C14' C15' 1.384(3) .
C15' C16' 1.387(3) .
C16' C17' 1.392(3) .
