#------------------------------------------------------------------------------
#$Date: 2024-07-05 18:26:26 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/84/7248459.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_7248459
loop_
_publ_author_name
'Paska, Bartłomiej'
'Cichowicz, Grzegorz'
'Rzepiński, Patryk'
'Cyrański, Michał Ksawery'
'Dobrzycki, Łukasz'
'Boese, Roland'
_publ_section_title
;
 Structural chemistry of decalins and perfluorodecalins
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              2474
_journal_page_last               2490
_journal_paper_doi               10.1039/D3CE01117H
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C10 H18'
_chemical_formula_weight         138.24
_chemical_melting_point          229
_chemical_name_systematic        'cis-Decalin (LT form refined in triclinic SG)'
_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_update_record
;
2023-11-05 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                113.5061(11)
_cell_angle_beta                 90.1124(13)
_cell_angle_gamma                112.8047(12)
_cell_formula_units_Z            4
_cell_length_a                   8.2775(4)
_cell_length_b                   10.5829(4)
_cell_length_c                   11.9879(5)
_cell_measurement_reflns_used    5745
_cell_measurement_temperature    140.(2)
_cell_measurement_theta_max      25.3378
_cell_measurement_theta_min      2.7165
_cell_volume                     872.36(7)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi scans'
_diffrn_radiation_monochromator  TRIUMPH
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            10556
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.32
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.053
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylindrical
_exptl_crystal_F_000             312
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0424
_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)+(0.0473P)²+0.2516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                2473
_reflns_number_total             2863
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01117h2.cif
_cod_data_source_block           c_Dec_k180K_140K_cd_aP
_cod_depositor_comments
'Adding full bibliography for 7248441--7248493.cif.'
_cod_database_code               7248459
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1A 0.7471(3) 0.2006(3) 0.5626(2) 0.0284(5) Uani d . . . 1 . .
H H1A 0.6381 0.1318 0.58 0.034 Uiso calc U . R 1 . .
C C2A 0.7703(3) 0.3633(3) 0.64139(19) 0.0324(5) Uani d . . . 1 . .
H H2A1 0.7838 0.3841 0.7299 0.039 Uiso calc U . R 1 . .
H H2A2 0.8803 0.4355 0.6297 0.039 Uiso calc U . R 1 . .
C C3A 0.6118(4) 0.3885(3) 0.6070(2) 0.0414(6) Uani d . . . 1 . .
H H3A1 0.634 0.4959 0.6568 0.05 Uiso calc U . R 1 . .
H H3A2 0.5036 0.3236 0.6266 0.05 Uiso calc U . R 1 . .
C C4A 0.5805(4) 0.3503(3) 0.4694(2) 0.0421(6) Uani d . . . 1 . .
H H4A1 0.4725 0.3615 0.4485 0.05 Uiso calc U . R 1 . .
H H4A2 0.6832 0.4226 0.4516 0.05 Uiso calc U . R 1 . .
C C5A 0.5571(3) 0.1885(3) 0.3897(2) 0.0341(6) Uani d . . . 1 . .
H H5A1 0.5457 0.1699 0.3017 0.041 Uiso calc U . R 1 . .
H H5A2 0.445 0.1164 0.3995 0.041 Uiso calc U . R 1 . .
C C6A 0.7119(3) 0.1569(3) 0.42255(19) 0.0284(5) Uani d . . . 1 . .
H H6A 0.6746 0.0447 0.3776 0.034 Uiso calc U . R 1 . .
C C7A 0.8836(4) 0.2349(3) 0.3818(2) 0.0397(6) Uani d . . . 1 . .
H H7A1 0.8596 0.2002 0.2911 0.048 Uiso calc U . R 1 . .
H H7A2 0.9212 0.3463 0.4221 0.048 Uiso calc U . R 1 . .
C C8A 1.0332(4) 0.2003(4) 0.4148(3) 0.0550(8) Uani d . . . 1 . .
H H8A1 1.1428 0.2568 0.3908 0.066 Uiso calc U . R 1 . .
H H8A2 1.001 0.0903 0.3677 0.066 Uiso calc U . R 1 . .
C C9A 1.0704(3) 0.2445(3) 0.5535(2) 0.0495(7) Uani d . . . 1 . .
H H9A1 1.1624 0.2135 0.5709 0.059 Uiso calc U . R 1 . .
H H9A2 1.1171 0.3564 0.6004 0.059 Uiso calc U . R 1 . .
C C10A 0.9027(3) 0.1693(3) 0.5960(2) 0.0387(6) Uani d . . . 1 . .
H H10A 0.929 0.2065 0.6869 0.046 Uiso calc U . R 1 . .
H H10B 0.8663 0.0581 0.5577 0.046 Uiso calc U . R 1 . .
C C1B 0.5442(3) 0.8010(2) 0.93683(19) 0.0256(5) Uani d . . . 1 A 2
H H1B 0.4988 0.8686 0.9215 0.031 Uiso calc U . R 1 A 2
C C2B 0.4093(3) 0.6359(2) 0.85772(18) 0.0298(5) Uani d . . . 1 A 2
H H2B1 0.3984 0.6156 0.7693 0.036 Uiso calc U . R 1 A 2
H H2B2 0.4529 0.5657 0.8682 0.036 Uiso calc U . R 1 A 2
C C3B 0.2268(3) 0.6064(3) 0.8948(2) 0.0402(6) Uani d . . . 1 A 2
H H3B1 0.1441 0.4983 0.8451 0.048 Uiso calc U . R 1 A 2
H H3B2 0.1781 0.6697 0.8769 0.048 Uiso calc U . R 1 A 2
C C4B 0.2394(3) 0.6434(3) 1.03227(18) 0.0394(6) Uani d . . . 1 A 2
H H4B1 0.2751 0.5723 1.0484 0.047 Uiso calc U . R 1 A 2
H H4B2 0.1208 0.6296 1.055 0.047 Uiso calc U . R 1 A 2
C C5B 0.3753(3) 0.8072(3) 1.1123(2) 0.0343(6) Uani d . . . 1 A 2
H H5B1 0.3308 0.8782 1.1045 0.041 Uiso calc U . R 1 A 2
H H5B2 0.3867 0.8251 1.2002 0.041 Uiso calc U . R 1 A 2
C C6B 0.5583(3) 0.8412(2) 1.07605(19) 0.0269(5) Uani d . . . 1 A 2
H H6B 0.6305 0.9536 1.1215 0.032 Uiso calc U . R 1 A 2
C C7B 0.6592(4) 0.7657(3) 1.1146(2) 0.0370(6) Uani d . . . 1 A 2
H H7B1 0.6727 0.7998 1.2053 0.044 Uiso calc U . R 1 A 2
H H7B2 0.5889 0.6539 1.0742 0.044 Uiso calc U . R 1 A 2
C C8B 0.8431(4) 0.8051(4) 1.0788(3) 0.0450(7) Uani d . . . 1 A 2
H H8B1 0.9019 0.7508 1.1012 0.054 Uiso calc U . R 1 A 2
H H8B2 0.9176 0.9157 1.1256 0.054 Uiso calc U . R 1 A 2
C C9B 0.8290(3) 0.7612(3) 0.9401(2) 0.0422(6) Uani d . . . 1 A 2
H H9B1 0.9502 0.7944 0.9202 0.051 Uiso calc U . R 1 A 2
H H9B2 0.7666 0.6492 0.8934 0.051 Uiso calc U . R 1 A 2
C C10B 0.7276(3) 0.8345(3) 0.9007(2) 0.0352(6) Uani d . . . 1 A 2
H H10C 0.7995 0.946 0.9388 0.042 Uiso calc U . R 1 A 2
H H10D 0.713 0.7978 0.8097 0.042 Uiso calc U . R 1 A 2
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A C1A C10A . . 113.4(2) ?
C2A C1A C6A . . 111.87(18) ?
C10A C1A C6A . . 110.76(19) ?
C2A C1A H1A . . 106.8 ?
C10A C1A H1A . . 106.8 ?
C6A C1A H1A . . 106.8 ?
C3A C2A C1A . . 111.6(2) ?
C3A C2A H2A1 . . 109.3 ?
C1A C2A H2A1 . . 109.3 ?
C3A C2A H2A2 . . 109.3 ?
C1A C2A H2A2 . . 109.3 ?
H2A1 C2A H2A2 . . 108.0 ?
C2A C3A C4A . . 111.1(2) ?
C2A C3A H3A1 . . 109.4 ?
C4A C3A H3A1 . . 109.4 ?
C2A C3A H3A2 . . 109.4 ?
C4A C3A H3A2 . . 109.4 ?
H3A1 C3A H3A2 . . 108.0 ?
C5A C4A C3A . . 110.96(19) ?
C5A C4A H4A1 . . 109.4 ?
C3A C4A H4A1 . . 109.4 ?
C5A C4A H4A2 . . 109.4 ?
C3A C4A H4A2 . . 109.4 ?
H4A1 C4A H4A2 . . 108.0 ?
C4A C5A C6A . . 113.2(2) ?
C4A C5A H5A1 . . 108.9 ?
C6A C5A H5A1 . . 108.9 ?
C4A C5A H5A2 . . 108.9 ?
C6A C5A H5A2 . . 108.9 ?
H5A1 C5A H5A2 . . 107.8 ?
C5A C6A C7A . . 113.4(2) ?
C5A C6A C1A . . 110.61(19) ?
C7A C6A C1A . . 110.74(18) ?
C5A C6A H6A . . 107.3 ?
C7A C6A H6A . . 107.3 ?
C1A C6A H6A . . 107.3 ?
C8A C7A C6A . . 111.9(2) ?
C8A C7A H7A1 . . 109.2 ?
C6A C7A H7A1 . . 109.2 ?
C8A C7A H7A2 . . 109.2 ?
C6A C7A H7A2 . . 109.2 ?
H7A1 C7A H7A2 . . 107.9 ?
C7A C8A C9A . . 111.6(2) ?
C7A C8A H8A1 . . 109.3 ?
C9A C8A H8A1 . . 109.3 ?
C7A C8A H8A2 . . 109.3 ?
C9A C8A H8A2 . . 109.3 ?
H8A1 C8A H8A2 . . 108.0 ?
C10A C9A C8A . . 111.0(2) ?
C10A C9A H9A1 . . 109.4 ?
C8A C9A H9A1 . . 109.4 ?
C10A C9A H9A2 . . 109.4 ?
C8A C9A H9A2 . . 109.4 ?
H9A1 C9A H9A2 . . 108.0 ?
C9A C10A C1A . . 112.93(19) ?
C9A C10A H10A . . 109.0 ?
C1A C10A H10A . . 109.0 ?
C9A C10A H10B . . 109.0 ?
C1A C10A H10B . . 109.0 ?
H10A C10A H10B . . 107.8 ?
C10B C1B C2B . . 112.3(2) ?
C10B C1B C6B . . 110.65(18) ?
C2B C1B C6B . . 111.47(17) ?
C10B C1B H1B . . 107.4 ?
C2B C1B H1B . . 107.4 ?
C6B C1B H1B . . 107.4 ?
C3B C2B C1B . . 111.1(2) ?
C3B C2B H2B1 . . 109.4 ?
C1B C2B H2B1 . . 109.4 ?
C3B C2B H2B2 . . 109.4 ?
C1B C2B H2B2 . . 109.4 ?
H2B1 C2B H2B2 . . 108.0 ?
C2B C3B C4B . . 111.0(2) ?
C2B C3B H3B1 . . 109.4 ?
C4B C3B H3B1 . . 109.4 ?
C2B C3B H3B2 . . 109.4 ?
C4B C3B H3B2 . . 109.4 ?
H3B1 C3B H3B2 . . 108.0 ?
C3B C4B C5B . . 111.14(19) ?
C3B C4B H4B1 . . 109.4 ?
C5B C4B H4B1 . . 109.4 ?
C3B C4B H4B2 . . 109.4 ?
C5B C4B H4B2 . . 109.4 ?
H4B1 C4B H4B2 . . 108.0 ?
C6B C5B C4B . . 112.6(2) ?
C6B C5B H5B1 . . 109.1 ?
C4B C5B H5B1 . . 109.1 ?
C6B C5B H5B2 . . 109.1 ?
C4B C5B H5B2 . . 109.1 ?
H5B1 C5B H5B2 . . 107.8 ?
C5B C6B C7B . . 113.23(18) ?
C5B C6B C1B . . 110.79(18) ?
C7B C6B C1B . . 111.77(19) ?
C5B C6B H6B . . 106.9 ?
C7B C6B H6B . . 106.9 ?
C1B C6B H6B . . 106.9 ?
C8B C7B C6B . . 111.50(19) ?
C8B C7B H7B1 . . 109.3 ?
C6B C7B H7B1 . . 109.3 ?
C8B C7B H7B2 . . 109.3 ?
C6B C7B H7B2 . . 109.3 ?
H7B1 C7B H7B2 . . 108.0 ?
C7B C8B C9B . . 111.1(2) ?
C7B C8B H8B1 . . 109.4 ?
C9B C8B H8B1 . . 109.4 ?
C7B C8B H8B2 . . 109.4 ?
C9B C8B H8B2 . . 109.4 ?
H8B1 C8B H8B2 . . 108.0 ?
C10B C9B C8B . . 110.8(2) ?
C10B C9B H9B1 . . 109.5 ?
C8B C9B H9B1 . . 109.5 ?
C10B C9B H9B2 . . 109.5 ?
C8B C9B H9B2 . . 109.5 ?
H9B1 C9B H9B2 . . 108.1 ?
C1B C10B C9B . . 113.70(17) ?
C1B C10B H10C . . 108.8 ?
C9B C10B H10C . . 108.8 ?
C1B C10B H10D . . 108.8 ?
C9B C10B H10D . . 108.8 ?
H10C C10B H10D . . 107.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1A C2A . 1.529(3) ?
C1A C10A . 1.538(3) ?
C1A C6A . 1.547(3) ?
C1A H1A . 1.0 ?
C2A C3A . 1.523(4) ?
C2A H2A1 . 0.99 ?
C2A H2A2 . 0.99 ?
C3A C4A . 1.529(3) ?
C3A H3A1 . 0.99 ?
C3A H3A2 . 0.99 ?
C4A C5A . 1.523(3) ?
C4A H4A1 . 0.99 ?
C4A H4A2 . 0.99 ?
C5A C6A . 1.531(3) ?
C5A H5A1 . 0.99 ?
C5A H5A2 . 0.99 ?
C6A C7A . 1.535(3) ?
C6A H6A . 1.0 ?
C7A C8A . 1.513(4) ?
C7A H7A1 . 0.99 ?
C7A H7A2 . 0.99 ?
C8A C9A . 1.531(4) ?
C8A H8A1 . 0.99 ?
C8A H8A2 . 0.99 ?
C9A C10A . 1.513(4) ?
C9A H9A1 . 0.99 ?
C9A H9A2 . 0.99 ?
C10A H10A . 0.99 ?
C10A H10B . 0.99 ?
C1B C10B . 1.525(3) ?
C1B C2B . 1.536(3) ?
C1B C6B . 1.541(3) ?
C1B H1B . 1.0 ?
C2B C3B . 1.524(3) ?
C2B H2B1 . 0.99 ?
C2B H2B2 . 0.99 ?
C3B C4B . 1.528(3) ?
C3B H3B1 . 0.99 ?
C3B H3B2 . 0.99 ?
C4B C5B . 1.533(3) ?
C4B H4B1 . 0.99 ?
C4B H4B2 . 0.99 ?
C5B C6B . 1.523(3) ?
C5B H5B1 . 0.99 ?
C5B H5B2 . 0.99 ?
C6B C7B . 1.537(3) ?
C6B H6B . 1.0 ?
C7B C8B . 1.526(4) ?
C7B H7B1 . 0.99 ?
C7B H7B2 . 0.99 ?
C8B C9B . 1.528(3) ?
C8B H8B1 . 0.99 ?
C8B H8B2 . 0.99 ?
C9B C10B . 1.525(4) ?
C9B H9B1 . 0.99 ?
C9B H9B2 . 0.99 ?
C10B H10C . 0.99 ?
C10B H10D . 0.99 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10A C1A C2A C3A . . . . -178.90(18) ?
C6A C1A C2A C3A . . . . 55.0(2) ?
C1A C2A C3A C4A . . . . -56.3(3) ?
C2A C3A C4A C5A . . . . 55.6(3) ?
C3A C4A C5A C6A . . . . -54.7(3) ?
C4A C5A C6A C7A . . . . -72.3(2) ?
C4A C5A C6A C1A . . . . 52.7(3) ?
C2A C1A C6A C5A . . . . -52.4(3) ?
C10A C1A C6A C5A . . . . -179.9(2) ?
C2A C1A C6A C7A . . . . 74.2(3) ?
C10A C1A C6A C7A . . . . -53.3(3) ?
C5A C6A C7A C8A . . . . -179.6(2) ?
C1A C6A C7A C8A . . . . 55.4(3) ?
C6A C7A C8A C9A . . . . -56.1(3) ?
C7A C8A C9A C10A . . . . 54.9(3) ?
C8A C9A C10A C1A . . . . -54.3(3) ?
C2A C1A C10A C9A . . . . -72.9(2) ?
C6A C1A C10A C9A . . . . 53.8(3) ?
C10B C1B C2B C3B . . . . -179.27(17) ?
C6B C1B C2B C3B . . . . 55.9(2) ?
C1B C2B C3B C4B . . . . -56.5(3) ?
C2B C3B C4B C5B . . . . 55.5(3) ?
C3B C4B C5B C6B . . . . -54.6(3) ?
C4B C5B C6B C7B . . . . -72.9(2) ?
C4B C5B C6B C1B . . . . 53.6(3) ?
C10B C1B C6B C5B . . . . -179.7(2) ?
C2B C1B C6B C5B . . . . -54.0(3) ?
C10B C1B C6B C7B . . . . -52.5(2) ?
C2B C1B C6B C7B . . . . 73.3(2) ?
C5B C6B C7B C8B . . . . -178.9(2) ?
C1B C6B C7B C8B . . . . 55.1(3) ?
C6B C7B C8B C9B . . . . -56.3(3) ?
C7B C8B C9B C10B . . . . 55.2(3) ?
C2B C1B C10B C9B . . . . -72.5(2) ?
C6B C1B C10B C9B . . . . 52.8(3) ?
C8B C9B C10B C1B . . . . -54.4(3) ?
