#------------------------------------------------------------------------------
#$Date: 2024-07-05 18:26:26 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/84/7248456.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_7248456
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                113.5057(12)
_cell_angle_beta                 90.1279(14)
_cell_angle_gamma                112.7902(12)
_cell_formula_units_Z            4
_cell_length_a                   8.2770(4)
_cell_length_b                   10.5807(4)
_cell_length_c                   11.9867(5)
_cell_measurement_reflns_used    5788
_cell_measurement_temperature    140.(2)
_cell_measurement_theta_max      25.3652
_cell_measurement_theta_min      2.7164
_cell_volume                     872.11(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 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'π scans'
_diffrn_radiation_monochromator  TRIUMPH
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0129
_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            10639
_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       dylindrical
_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         0.201
_refine_diff_density_min         -0.148
_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     182
_refine_ls_number_reflns         2871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0417
_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)+(0.0448P)²+0.2607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                2486
_reflns_number_total             2871
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01117h2.cif
_cod_data_source_block           c_Dec_k180K_140K_hu_aP
_cod_depositor_comments
'Adding full bibliography for 7248441--7248493.cif.'
_cod_database_code               7248456
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 0.7469(3) 0.2004(2) 0.56259(19) 0.0283(5) Uani d . . . 1 . .
H H1A 0.6382 0.1315 0.5802 0.034 Uiso calc U . R 1 . .
C C2A 0.7704(3) 0.3632(2) 0.64123(18) 0.0323(5) Uani d . . . 1 . .
H H2A1 0.7845 0.3845 0.7298 0.039 Uiso calc U . R 1 . .
H H2A2 0.8802 0.4353 0.6291 0.039 Uiso calc U . R 1 . .
C C3A 0.6115(4) 0.3883(3) 0.6071(2) 0.0416(6) Uani d . . . 1 . .
H H3A1 0.6337 0.4958 0.6569 0.05 Uiso calc U . R 1 . .
H H3A2 0.5036 0.3236 0.627 0.05 Uiso calc U . R 1 . .
C C4A 0.5794(4) 0.3498(3) 0.46933(19) 0.0424(6) Uani d . . . 1 . .
H H4A1 0.4708 0.3602 0.4485 0.051 Uiso calc U . R 1 . .
H H4A2 0.6814 0.4224 0.4514 0.051 Uiso calc U . R 1 . .
C C5A 0.5571(3) 0.1881(3) 0.3897(2) 0.0342(5) Uani d . . . 1 . .
H H5A1 0.5459 0.1696 0.3017 0.041 Uiso calc U . R 1 . .
H H5A2 0.4451 0.1156 0.3992 0.041 Uiso calc U . R 1 . .
C C6A 0.7118(3) 0.1569(2) 0.42262(18) 0.0282(5) Uani d . . . 1 . .
H H6A 0.6746 0.0447 0.3776 0.034 Uiso calc U . R 1 . .
C C7A 0.8831(3) 0.2350(3) 0.3816(2) 0.0395(6) Uani d . . . 1 . .
H H7A1 0.8589 0.2003 0.2909 0.047 Uiso calc U . R 1 . .
H H7A2 0.9207 0.3464 0.4219 0.047 Uiso calc U . R 1 . .
C C8A 1.0330(3) 0.2003(4) 0.4147(2) 0.0555(8) Uani d . . . 1 . .
H H8A1 1.1424 0.2566 0.3905 0.067 Uiso calc U . R 1 . .
H H8A2 1.0006 0.0902 0.3677 0.067 Uiso calc U . R 1 . .
C C9A 1.0703(3) 0.2449(3) 0.5535(2) 0.0495(7) Uani d . . . 1 . .
H H9A1 1.1626 0.2141 0.571 0.059 Uiso calc U . R 1 . .
H H9A2 1.1167 0.3568 0.6002 0.059 Uiso calc U . R 1 . .
C C10A 0.9033(3) 0.1697(3) 0.5958(2) 0.0388(6) Uani d . . . 1 . .
H H10A 0.9297 0.2068 0.6867 0.047 Uiso calc U . R 1 . .
H H10B 0.8672 0.0585 0.5575 0.047 Uiso calc U . R 1 . .
C C1B 0.5442(3) 0.8008(2) 0.93683(18) 0.0255(5) Uani d . . . 1 . .
H H1B 0.4986 0.8684 0.9215 0.031 Uiso calc U . R 1 . .
C C2B 0.4091(3) 0.6359(2) 0.85760(18) 0.0300(5) Uani d . . . 1 . .
H H2B1 0.398 0.6158 0.7693 0.036 Uiso calc U . R 1 . .
H H2B2 0.4528 0.5655 0.8677 0.036 Uiso calc U . R 1 . .
C C3B 0.2271(3) 0.6062(3) 0.89477(19) 0.0402(6) Uani d . . . 1 . .
H H3B1 0.1445 0.498 0.8451 0.048 Uiso calc U . R 1 . .
H H3B2 0.1781 0.6694 0.8771 0.048 Uiso calc U . R 1 . .
C C4B 0.2403(3) 0.6432(2) 1.03230(18) 0.0388(6) Uani d . . . 1 . .
H H4B1 0.2769 0.5724 1.0482 0.047 Uiso calc U . R 1 . .
H H4B2 0.1217 0.6286 1.0552 0.047 Uiso calc U . R 1 . .
C C5B 0.3753(3) 0.8073(3) 1.1125(2) 0.0340(5) Uani d . . . 1 . .
H H5B1 0.3304 0.878 1.1045 0.041 Uiso calc U . R 1 . .
H H5B2 0.3867 0.8252 1.2004 0.041 Uiso calc U . R 1 . .
C C6B 0.5584(3) 0.8414(2) 1.07618(18) 0.0269(5) Uani d . . . 1 . .
H H6B 0.6305 0.9539 1.1215 0.032 Uiso calc U . R 1 . .
C C7B 0.6600(3) 0.7662(3) 1.11464(19) 0.0360(6) Uani d . . . 1 . .
H H7B1 0.6737 0.8003 1.2054 0.043 Uiso calc U . R 1 . .
H H7B2 0.5899 0.6544 1.0743 0.043 Uiso calc U . R 1 . .
C C8B 0.8436(3) 0.8055(3) 1.0788(2) 0.0445(6) Uani d . . . 1 . .
H H8B1 0.9023 0.751 1.101 0.053 Uiso calc U . R 1 . .
H H8B2 0.9181 0.9161 1.1256 0.053 Uiso calc U . R 1 . .
C C9B 0.8295(3) 0.7617(3) 0.9400(2) 0.0416(6) Uani d . . . 1 . .
H H9B1 0.9506 0.7952 0.9202 0.05 Uiso calc U . R 1 . .
H H9B2 0.7674 0.6497 0.8932 0.05 Uiso calc U . R 1 . .
C C10B 0.7274(3) 0.8349(3) 0.90060(19) 0.0346(5) Uani d . . . 1 . .
H H10C 0.799 0.9465 0.9388 0.042 Uiso calc U . R 1 . .
H H10D 0.7127 0.7983 0.8096 0.042 Uiso calc U . R 1 . .
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 . . 113.21(19) ?
C2A C1A C6A . . 111.73(17) ?
C10A C1A C6A . . 110.70(18) ?
C2A C1A H1A . . 106.9 ?
C10A C1A H1A . . 106.9 ?
C6A C1A H1A . . 106.9 ?
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 . . 113.4(2) ?
C4A C5A H5A1 . . 108.9 ?
C6A C5A H5A1 . . 108.9 ?
C4A C5A H5A2 . . 108.9 ?
C6A C5A H5A2 . . 108.9 ?
H5A1 C5A H5A2 . . 107.7 ?
C5A C6A C7A . . 113.24(19) ?
C5A C6A C1A . . 110.72(18) ?
C7A C6A C1A . . 110.86(17) ?
C5A C6A H6A . . 107.2 ?
C7A C6A H6A . . 107.2 ?
C1A C6A H6A . . 107.2 ?
C8A C7A C6A . . 111.8(2) ?
C8A C7A H7A1 . . 109.3 ?
C6A C7A H7A1 . . 109.3 ?
C8A C7A H7A2 . . 109.3 ?
C6A C7A H7A2 . . 109.3 ?
H7A1 C7A H7A2 . . 107.9 ?
C7A C8A C9A . . 111.5(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 . . 110.97(19) ?
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 . . 113.13(18) ?
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 . . 112.49(18) ?
C10B C1B C6B . . 110.74(17) ?
C2B C1B C6B . . 111.64(16) ?
C10B C1B H1B . . 107.2 ?
C2B C1B H1B . . 107.2 ?
C6B C1B H1B . . 107.2 ?
C3B C2B C1B . . 111.20(19) ?
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 . . 110.97(19) ?
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 . . 111.25(18) ?
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 . . 112.34(19) ?
C6B C5B H5B1 . . 109.1 ?
C4B C5B H5B1 . . 109.1 ?
C6B C5B H5B2 . . 109.1 ?
C4B C5B H5B2 . . 109.1 ?
H5B1 C5B H5B2 . . 107.9 ?
C5B C6B C7B . . 113.37(17) ?
C5B C6B C1B . . 110.81(17) ?
C7B C6B C1B . . 111.58(18) ?
C5B C6B H6B . . 106.9 ?
C7B C6B H6B . . 106.9 ?
C1B C6B H6B . . 106.9 ?
C8B C7B C6B . . 111.70(18) ?
C8B C7B H7B1 . . 109.3 ?
C6B C7B H7B1 . . 109.3 ?
C8B C7B H7B2 . . 109.3 ?
C6B C7B H7B2 . . 109.3 ?
H7B1 C7B H7B2 . . 107.9 ?
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 . . 113.57(16) ?
C1B C10B H10C . . 108.9 ?
C9B C10B H10C . . 108.9 ?
C1B C10B H10D . . 108.9 ?
C9B C10B H10D . . 108.9 ?
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 . 1.530(3) ?
C1A C10A . 1.538(3) ?
C1A C6A . 1.546(3) ?
C1A H1A . 1.0 ?
C2A C3A . 1.523(3) ?
C2A H2A1 . 0.99 ?
C2A H2A2 . 0.99 ?
C3A C4A . 1.530(3) ?
C3A H3A1 . 0.99 ?
C3A H3A2 . 0.99 ?
C4A C5A . 1.524(3) ?
C4A H4A1 . 0.99 ?
C4A H4A2 . 0.99 ?
C5A C6A . 1.528(3) ?
C5A H5A1 . 0.99 ?
C5A H5A2 . 0.99 ?
C6A C7A . 1.535(3) ?
C6A H6A . 1.0 ?
C7A C8A . 1.516(4) ?
C7A H7A1 . 0.99 ?
C7A H7A2 . 0.99 ?
C8A C9A . 1.531(3) ?
C8A H8A1 . 0.99 ?
C8A H8A2 . 0.99 ?
C9A C10A . 1.508(3) ?
C9A H9A1 . 0.99 ?
C9A H9A2 . 0.99 ?
C10A H10A . 0.99 ?
C10A H10B . 0.99 ?
C1B C10B . 1.524(3) ?
C1B C2B . 1.536(3) ?
C1B C6B . 1.541(3) ?
C1B H1B . 1.0 ?
C2B C3B . 1.521(3) ?
C2B H2B1 . 0.99 ?
C2B H2B2 . 0.99 ?
C3B C4B . 1.528(3) ?
C3B H3B1 . 0.99 ?
C3B H3B2 . 0.99 ?
C4B C5B . 1.532(3) ?
C4B H4B1 . 0.99 ?
C4B H4B2 . 0.99 ?
C5B C6B . 1.524(3) ?
C5B H5B1 . 0.99 ?
C5B H5B2 . 0.99 ?
C6B C7B . 1.537(3) ?
C6B H6B . 1.0 ?
C7B C8B . 1.524(4) ?
C7B H7B1 . 0.99 ?
C7B H7B2 . 0.99 ?
C8B C9B . 1.529(3) ?
C8B H8B1 . 0.99 ?
C8B H8B2 . 0.99 ?
C9B C10B . 1.528(3) ?
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 . . . . -178.99(17) ?
C6A C1A C2A C3A . . . . 55.2(2) ?
C1A C2A C3A C4A . . . . -56.4(2) ?
C2A C3A C4A C5A . . . . 55.3(3) ?
C3A C4A C5A C6A . . . . -54.3(3) ?
C4A C5A C6A C7A . . . . -72.5(2) ?
C4A C5A C6A C1A . . . . 52.7(2) ?
C2A C1A C6A C5A . . . . -52.6(2) ?
C10A C1A C6A C5A . . . . -179.71(19) ?
C2A C1A C6A C7A . . . . 74.0(2) ?
C10A C1A C6A C7A . . . . -53.2(3) ?
C5A C6A C7A C8A . . . . -179.5(2) ?
C1A C6A C7A C8A . . . . 55.4(3) ?
C6A C7A C8A C9A . . . . -56.3(3) ?
C7A C8A C9A C10A . . . . 55.1(3) ?
C8A C9A C10A C1A . . . . -54.4(3) ?
C2A C1A C10A C9A . . . . -72.6(2) ?
C6A C1A C10A C9A . . . . 53.7(3) ?
C10B C1B C2B C3B . . . . -179.19(16) ?
C6B C1B C2B C3B . . . . 55.6(2) ?
C1B C2B C3B C4B . . . . -56.4(2) ?
C2B C3B C4B C5B . . . . 55.8(3) ?
C3B C4B C5B C6B . . . . -54.9(3) ?
C4B C5B C6B C7B . . . . -72.8(2) ?
C4B C5B C6B C1B . . . . 53.6(2) ?
C10B C1B C6B C5B . . . . -179.95(18) ?
C2B C1B C6B C5B . . . . -53.8(2) ?
C10B C1B C6B C7B . . . . -52.6(2) ?
C2B C1B C6B C7B . . . . 73.6(2) ?
C5B C6B C7B C8B . . . . -178.9(2) ?
C1B C6B C7B C8B . . . . 55.1(2) ?
C6B C7B C8B C9B . . . . -56.2(3) ?
C7B C8B C9B C10B . . . . 55.0(3) ?
C2B C1B C10B C9B . . . . -72.7(2) ?
C6B C1B C10B C9B . . . . 53.0(2) ?
C8B C9B C10B C1B . . . . -54.4(3) ?
