#------------------------------------------------------------------------------
#$Date: 2017-05-06 01:08:43 +0300 (Sat, 06 May 2017) $
#$Revision: 196439 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/23/7042372.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_7042372
loop_
_publ_author_name
'Reuter, K.'
'Maas, R. G. M.'
'Reuter, A.'
'Kilgenstein, F.'
'Asfaha, Y.'
'von Hänisch, C'
_publ_section_title
;
 Synthesis of heteroatomic bridged paracyclophanes.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4530
_journal_page_last               4541
_journal_paper_doi               10.1039/c7dt00321h
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C18 H33 P Si2'
_chemical_formula_sum            'C18 H33 P Si2'
_chemical_formula_weight         336.59
_chemical_name_systematic
;
 ?
;
_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   mixed
_audit_creation_date             2016-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-01-13 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                103.979(4)
_cell_angle_beta                 94.721(4)
_cell_angle_gamma                109.762(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2321(10)
_cell_length_b                   9.5654(10)
_cell_length_c                   12.1031(12)
_cell_measurement_reflns_used    10277
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.6520
_cell_measurement_theta_min      3.8694
_cell_volume                     960.21(18)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10277
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.318
_diffrn_reflns_theta_min         2.362
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.045
_exptl_transmission_factor_max   0.988
_exptl_transmission_factor_min   0.980
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0437
_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)+(0.0450P)²+1.0765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2905
_reflns_number_total             3496
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt00321h1.cif
_cod_data_source_block           kr164p-1
_cod_depositor_comments
'Adding full bibliography for 7042367--7042376.cif.'
_cod_original_cell_volume        960.21(17)
_cod_database_code               7042372
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 P1-H1A
 1.3 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C1(H1), C7(H7), C16(H16), C0AA(H0AA)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C14(H14), C15(H15)
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,
 H17B,H17C), C18(H18A,H18B,H18C), C2AA(H2AA,H2AB,H2AC), C1AA(H1AA,H1AB,H1AC)
;
_shelx_shelxl_version_number     2014/7
_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
C1 C 0.1991(3) 0.6664(3) 0.8202(2) 0.0138(5) Uani 1 1 d .
H1 H 0.2227 0.7712 0.8750 0.017 Uiso 1 1 calc R
C2 C 0.1283(3) 0.5463(3) 0.8846(2) 0.0207(6) Uani 1 1 d .
H2A H 0.0264 0.5482 0.9003 0.031 Uiso 1 1 calc GR
H2B H 0.1985 0.5715 0.9578 0.031 Uiso 1 1 calc GR
H2C H 0.1148 0.4428 0.8367 0.031 Uiso 1 1 calc GR
C3 C 0.0779(3) 0.6463(3) 0.7171(2) 0.0207(6) Uani 1 1 d .
H3A H 0.0504 0.5436 0.6620 0.031 Uiso 1 1 calc GR
H3B H 0.1220 0.7264 0.6787 0.031 Uiso 1 1 calc GR
H3C H -0.0161 0.6560 0.7446 0.031 Uiso 1 1 calc GR
C4 C 0.3513(3) 0.4878(3) 0.6492(2) 0.0116(5) Uani 1 1 d .
C5 C 0.3604(3) 0.3501(3) 0.6647(2) 0.0141(5) Uani 1 1 d .
H5 H 0.3846 0.3445 0.7409 0.017 Uiso 1 1 calc R
C6 C 0.3107(3) 0.4875(3) 0.5347(2) 0.0139(5) Uani 1 1 d .
H6 H 0.3009 0.5776 0.5206 0.017 Uiso 1 1 calc R
C7 C 0.5090(3) 0.6442(3) 0.9055(2) 0.0141(5) Uani 1 1 d .
H7 H 0.4437 0.5462 0.9211 0.017 Uiso 1 1 calc R
C8 C 0.6656(3) 0.6286(3) 0.8877(2) 0.0196(6) Uani 1 1 d .
H8A H 0.7387 0.7265 0.8806 0.029 Uiso 1 1 calc GR
H8B H 0.6496 0.5453 0.8170 0.029 Uiso 1 1 calc GR
H8C H 0.7087 0.6041 0.9541 0.029 Uiso 1 1 calc GR
C9 C 0.5309(3) 0.7750(3) 1.0150(2) 0.0225(6) Uani 1 1 d .
H9A H 0.5809 0.7560 1.0815 0.034 Uiso 1 1 calc GR
H9B H 0.4287 0.7785 1.0282 0.034 Uiso 1 1 calc GR
H9C H 0.5971 0.8742 1.0054 0.034 Uiso 1 1 calc GR
C13 C 0.2973(3) 0.2223(3) 0.4575(2) 0.0119(5) Uani 1 1 d .
C14 C 0.2848(3) 0.3592(3) 0.4420(2) 0.0141(5) Uani 1 1 d .
H14 H 0.2578 0.3637 0.3658 0.017 Uiso 1 1 calc R
C15 C 0.3348(3) 0.2217(3) 0.5714(2) 0.0148(5) Uani 1 1 d .
H15 H 0.3430 0.1309 0.5855 0.018 Uiso 1 1 calc R
C16 C 0.7324(3) 1.1179(3) 0.6161(2) 0.0132(5) Uani 1 1 d .
H16 H 0.6417 1.0808 0.5512 0.016 Uiso 1 1 calc R
C17 C 0.7139(3) 1.2523(3) 0.7059(2) 0.0178(5) Uani 1 1 d .
H17A H 0.8049 1.2991 0.7688 0.027 Uiso 1 1 calc GR
H17B H 0.6188 1.2127 0.7374 0.027 Uiso 1 1 calc GR
H17C H 0.7063 1.3305 0.6688 0.027 Uiso 1 1 calc GR
C18 C 0.8797(3) 1.1793(3) 0.5643(2) 0.0197(6) Uani 1 1 d .
H18A H 0.8658 1.2483 0.5198 0.030 Uiso 1 1 calc GR
H18B H 0.8968 1.0919 0.5132 0.030 Uiso 1 1 calc GR
H18C H 0.9705 1.2367 0.6269 0.030 Uiso 1 1 calc GR
Si1 Si 0.39059(7) 0.66123(7) 0.77683(6) 0.01055(17) Uani 1 1 d .
Si2 Si 0.71837(7) 0.94405(7) 0.66954(6) 0.01082(17) Uani 1 1 d .
P1 P 0.47979(8) 0.87996(8) 0.72157(7) 0.0238(2) Uani 1 1 d D
C0AA C 0.8857(3) 0.9810(3) 0.7886(2) 0.0141(5) Uani 1 1 d .
H0AA H 0.8688 0.8788 0.8035 0.017 Uiso 1 1 calc R
C2AA C 0.8875(3) 1.0915(3) 0.9040(2) 0.0224(6) Uani 1 1 d .
H2AA H 0.9131 1.1963 0.8961 0.034 Uiso 1 1 calc GR
H2AB H 0.9664 1.0923 0.9638 0.034 Uiso 1 1 calc GR
H2AC H 0.7843 1.0565 0.9260 0.034 Uiso 1 1 calc GR
C1AA C 1.0471(3) 1.0323(3) 0.7529(2) 0.0229(6) Uani 1 1 d .
H1AA H 1.0427 0.9634 0.6771 0.034 Uiso 1 1 calc GR
H1AB H 1.1249 1.0273 0.8105 0.034 Uiso 1 1 calc GR
H1AC H 1.0766 1.1390 0.7482 0.034 Uiso 1 1 calc GR
H1A H 0.510(4) 0.971(3) 0.8239(13) 0.044(9) Uiso 1 1 d 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
C2 C1 H1 107.2 . .
C2 C1 Si1 112.37(16) . .
C3 C1 H1 107.2 . .
C3 C1 C2 109.9(2) . .
C3 C1 Si1 112.69(16) . .
Si1 C1 H1 107.2 . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2B 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C1 C3 H3A 109.5 . .
C1 C3 H3B 109.5 . .
C1 C3 H3C 109.5 . .
H3A C3 H3B 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C5 C4 C6 116.5(2) . .
C5 C4 Si1 120.79(18) . .
C6 C4 Si1 122.67(17) . .
C4 C5 H5 119.2 . .
C15 C5 C4 121.7(2) . .
C15 C5 H5 119.2 . .
C4 C6 H6 119.2 . .
C14 C6 C4 121.6(2) . .
C14 C6 H6 119.2 . .
C8 C7 H7 105.9 . .
C8 C7 C9 110.5(2) . .
C8 C7 Si1 116.24(17) . .
C9 C7 H7 105.9 . .
C9 C7 Si1 111.50(16) . .
Si1 C7 H7 105.9 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C14 C13 Si2 121.37(18) . 2_666
C15 C13 C14 116.6(2) . .
C15 C13 Si2 121.85(17) . 2_666
C6 C14 C13 121.8(2) . .
C6 C14 H14 119.1 . .
C13 C14 H14 119.1 . .
C5 C15 C13 121.8(2) . .
C5 C15 H15 119.1 . .
C13 C15 H15 119.1 . .
C17 C16 H16 106.0 . .
C17 C16 C18 109.90(19) . .
C17 C16 Si2 114.21(16) . .
C18 C16 H16 106.0 . .
C18 C16 Si2 114.11(16) . .
Si2 C16 H16 106.0 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C16 C18 H18A 109.5 . .
C16 C18 H18B 109.5 . .
C16 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C1 Si1 C7 107.04(11) . .
C1 Si1 P1 101.52(8) . .
C4 Si1 C1 109.95(10) . .
C4 Si1 C7 109.48(10) . .
C4 Si1 P1 109.55(8) . .
C7 Si1 P1 118.82(8) . .
C13 Si2 C16 108.67(11) 2_666 .
C13 Si2 P1 105.60(7) 2_666 .
C13 Si2 C0AA 110.57(10) 2_666 .
C16 Si2 P1 102.37(8) . .
C16 Si2 C0AA 114.39(11) . .
C0AA Si2 P1 114.56(8) . .
Si1 P1 Si2 117.60(4) . .
Si1 P1 H1A 94.5(15) . .
Si2 P1 H1A 101.8(15) . .
Si2 C0AA H0AA 106.0 . .
C2AA C0AA Si2 114.22(17) . .
C2AA C0AA H0AA 106.0 . .
C2AA C0AA C1AA 110.5(2) . .
C1AA C0AA Si2 113.44(17) . .
C1AA C0AA H0AA 106.0 . .
C0AA C2AA H2AA 109.5 . .
C0AA C2AA H2AB 109.5 . .
C0AA C2AA H2AC 109.5 . .
H2AA C2AA H2AB 109.5 . .
H2AA C2AA H2AC 109.5 . .
H2AB C2AA H2AC 109.5 . .
C0AA C1AA H1AA 109.5 . .
C0AA C1AA H1AB 109.5 . .
C0AA C1AA H1AC 109.5 . .
H1AA C1AA H1AB 109.5 . .
H1AA C1AA H1AC 109.5 . .
H1AB C1AA H1AC 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 1.0000 .
C1 C2 1.537(3) .
C1 C3 1.535(3) .
C1 Si1 1.898(2) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 C5 1.403(3) .
C4 C6 1.404(3) .
C4 Si1 1.880(2) .
C5 H5 0.9500 .
C5 C15 1.389(3) .
C6 H6 0.9500 .
C6 C14 1.383(3) .
C7 H7 1.0000 .
C7 C8 1.530(3) .
C7 C9 1.532(3) .
C7 Si1 1.900(2) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C13 C14 1.408(3) .
C13 C15 1.395(3) .
C13 Si2 1.882(2) 2_666
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 H16 1.0000 .
C16 C17 1.538(3) .
C16 C18 1.539(3) .
C16 Si2 1.894(2) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
Si1 P1 2.2593(9) .
Si2 C13 1.882(2) 2_666
Si2 P1 2.2640(9) .
Si2 C0AA 1.899(2) .
P1 H1A 1.275(10) .
C0AA H0AA 1.0000 .
C0AA C2AA 1.529(3) .
C0AA C1AA 1.537(3) .
C2AA H2AA 0.9800 .
C2AA H2AB 0.9800 .
C2AA H2AC 0.9800 .
C1AA H1AA 0.9800 .
C1AA H1AB 0.9800 .
C1AA H1AC 0.9800 .
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_4
C2 C1 Si1 C4 75.5(2) . .
C2 C1 Si1 C7 -43.4(2) . .
C2 C1 Si1 P1 -168.61(16) . .
C3 C1 Si1 C4 -49.34(19) . .
C3 C1 Si1 C7 -168.18(16) . .
C3 C1 Si1 P1 66.58(17) . .
C4 C5 C15 C13 -0.6(4) . .
C4 C6 C14 C13 0.1(4) . .
C5 C4 C6 C14 -1.5(3) . .
C5 C4 Si1 C1 -96.7(2) . .
C5 C4 Si1 C7 20.6(2) . .
C5 C4 Si1 P1 152.56(17) . .
C6 C4 C5 C15 1.7(3) . .
C6 C4 Si1 C1 82.9(2) . .
C6 C4 Si1 C7 -159.80(18) . .
C6 C4 Si1 P1 -27.9(2) . .
C8 C7 Si1 C1 176.60(17) . .
C8 C7 Si1 C4 57.47(19) . .
C8 C7 Si1 P1 -69.38(19) . .
C9 C7 Si1 C1 -55.46(19) . .
C9 C7 Si1 C4 -174.60(16) . .
C9 C7 Si1 P1 58.56(18) . .
C13 Si2 C0AA C2AA -168.42(17) 2_666 .
C13 Si2 C0AA C1AA 63.77(19) 2_666 .
C14 C13 C15 C5 -0.8(3) . .
C15 C13 C14 C6 1.0(3) . .
C16 Si2 C0AA C2AA 68.5(2) . .
C16 Si2 C0AA C1AA -59.3(2) . .
C17 C16 Si2 C13 168.81(16) . 2_666
C17 C16 Si2 P1 57.42(18) . .
C17 C16 Si2 C0AA -67.11(19) . .
C18 C16 Si2 C13 -63.6(2) . 2_666
C18 C16 Si2 P1 -174.99(16) . .
C18 C16 Si2 C0AA 60.5(2) . .
Si1 C4 C5 C15 -178.70(18) . .
Si1 C4 C6 C14 178.94(18) . .
Si2 C13 C14 C6 -173.80(17) 2_666 .
Si2 C13 C15 C5 174.00(18) 2_666 .
P1 Si2 C0AA C2AA -49.26(19) . .
P1 Si2 C0AA C1AA -177.06(15) . .
