#------------------------------------------------------------------------------
#$Date: 2024-07-05 18:26:26 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/84/7248458.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_7248458
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                113.554(2)
_cell_angle_beta                 90.201(3)
_cell_angle_gamma                112.704(2)
_cell_formula_units_Z            4
_cell_length_a                   8.2665(7)
_cell_length_b                   10.5475(7)
_cell_length_c                   11.9704(9)
_cell_measurement_reflns_used    5874
_cell_measurement_temperature    120.(2)
_cell_measurement_theta_max      25.3545
_cell_measurement_theta_min      2.7188
_cell_volume                     867.12(12)
_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      120.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0150
_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            10269
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.27
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.059
_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         0.176
_refine_diff_density_min         -0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0422
_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)+(0.0338P)²+0.3364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                2514
_reflns_number_total             2823
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01117h2.cif
_cod_data_source_block           c_Dec_k180K_120K_hu_aP
_cod_depositor_comments
'Adding full bibliography for 7248441--7248493.cif.'
_cod_database_code               7248458
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 0.7492(3) 0.2000(2) 0.56193(18) 0.0244(5) Uani d . . . 1 . .
H H1A 0.6415 0.1304 0.5798 0.029 Uiso calc U . R 1 . .
C C2A 0.7708(3) 0.3631(2) 0.64099(18) 0.0272(5) Uani d . . . 1 . .
H H2A1 0.8796 0.4359 0.6285 0.033 Uiso calc U . R 1 . .
H H2A2 0.7864 0.3846 0.7297 0.033 Uiso calc U . R 1 . .
C C3A 0.6093(3) 0.3872(3) 0.60774(19) 0.0348(5) Uani d . . . 1 . .
H H3A1 0.5024 0.3219 0.6281 0.042 Uiso calc U . R 1 . .
H H3A2 0.6308 0.4949 0.6577 0.042 Uiso calc U . R 1 . .
C C4A 0.5749(3) 0.3482(3) 0.46996(19) 0.0345(5) Uani d . . . 1 . .
H H4A1 0.4651 0.3577 0.4498 0.041 Uiso calc U . R 1 . .
H H4A2 0.6756 0.4216 0.4516 0.041 Uiso calc U . R 1 . .
C C5A 0.5539(3) 0.1863(3) 0.38955(19) 0.0294(5) Uani d . . . 1 . .
H H5A1 0.5414 0.1678 0.3014 0.035 Uiso calc U . R 1 . .
H H5A2 0.4429 0.113 0.3994 0.035 Uiso calc U . R 1 . .
C C6A 0.7117(3) 0.1563(2) 0.42189(17) 0.0246(5) Uani d . . . 1 . .
H H6A 0.676 0.044 0.3765 0.03 Uiso calc U . R 1 . .
C C7A 0.8800(3) 0.2359(3) 0.38044(19) 0.0346(6) Uani d . . . 1 . .
H H7A1 0.9157 0.3473 0.4211 0.042 Uiso calc U . R 1 . .
H H7A2 0.8543 0.201 0.2896 0.042 Uiso calc U . R 1 . .
C C8A 1.0339(3) 0.2030(3) 0.4126(2) 0.0472(7) Uani d . . . 1 . .
H H8A1 1.1421 0.2608 0.3883 0.057 Uiso calc U . R 1 . .
H H8A2 1.0033 0.093 0.3652 0.057 Uiso calc U . R 1 . .
C C9A 1.0730(3) 0.2478(3) 0.5517(2) 0.0428(6) Uani d . . . 1 . .
H H9A1 1.1674 0.2186 0.5688 0.051 Uiso calc U . R 1 . .
H H9A2 1.1173 0.3598 0.5987 0.051 Uiso calc U . R 1 . .
C C10A 0.9074(3) 0.1700(3) 0.59408(19) 0.0339(5) Uani d . . . 1 . .
H H10A 0.9346 0.2065 0.685 0.041 Uiso calc U . R 1 . .
H H10B 0.8728 0.0587 0.5548 0.041 Uiso calc U . R 1 . .
C C1B 0.5429(3) 0.8011(2) 0.93670(17) 0.0222(4) Uani d . . . 1 . .
H H1B 0.4952 0.8682 0.9222 0.027 Uiso calc U . R 1 . .
C C2B 0.4103(3) 0.6356(2) 0.85708(17) 0.0257(5) Uani d . . . 1 . .
H H2B1 0.3975 0.6161 0.7687 0.031 Uiso calc U . R 1 . .
H H2B2 0.4566 0.5659 0.8661 0.031 Uiso calc U . R 1 . .
C C3B 0.2286(3) 0.6035(3) 0.89550(19) 0.0328(5) Uani d . . . 1 . .
H H3B1 0.147 0.4947 0.8456 0.039 Uiso calc U . R 1 . .
H H3B2 0.1772 0.6662 0.8788 0.039 Uiso calc U . R 1 . .
C C4B 0.2444(3) 0.6398(2) 1.03332(18) 0.0322(5) Uani d . . . 1 . .
H H4B1 0.2838 0.5696 1.0484 0.039 Uiso calc U . R 1 . .
H H4B2 0.1259 0.6236 1.057 0.039 Uiso calc U . R 1 . .
C C5B 0.3778(3) 0.8049(3) 1.11356(18) 0.0282(5) Uani d . . . 1 . .
H H5B1 0.3305 0.8749 1.1061 0.034 Uiso calc U . R 1 . .
H H5B2 0.3908 0.8229 1.2015 0.034 Uiso calc U . R 1 . .
C C6B 0.5602(3) 0.8414(2) 1.07648(17) 0.0230(4) Uani d . . . 1 . .
H H6B 0.6312 0.9543 1.1222 0.028 Uiso calc U . R 1 . .
C C7B 0.6655(3) 0.7663(3) 1.11321(18) 0.0292(5) Uani d . . . 1 . .
H H7B1 0.6804 0.7997 1.204 0.035 Uiso calc U . R 1 . .
H H7B2 0.5965 0.654 1.0722 0.035 Uiso calc U . R 1 . .
C C8B 0.8475(3) 0.8074(3) 1.0767(2) 0.0351(5) Uani d . . . 1 . .
H H8B1 0.9083 0.7533 1.098 0.042 Uiso calc U . R 1 . .
H H8B2 0.9212 0.9185 1.1239 0.042 Uiso calc U . R 1 . .
C C9B 0.8310(3) 0.7641(3) 0.93775(19) 0.0329(5) Uani d . . . 1 . .
H H9B1 0.7698 0.6517 0.8906 0.039 Uiso calc U . R 1 . .
H H9B2 0.9517 0.7987 0.9172 0.039 Uiso calc U . R 1 . .
C C10B 0.7258(3) 0.8369(3) 0.89953(18) 0.0286(5) Uani d . . . 1 . .
H H10C 0.7963 0.949 0.9381 0.034 Uiso calc U . R 1 . .
H H10D 0.71 0.8006 0.8084 0.034 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 . . 113.54(18) ?
C2A C1A C6A . . 111.57(16) ?
C10A C1A C6A . . 110.71(17) ?
C2A C1A H1A . . 106.9 ?
C10A C1A H1A . . 106.9 ?
C6A C1A H1A . . 106.9 ?
C1A C2A C3A . . 111.84(19) ?
C1A C2A H2A1 . . 109.2 ?
C3A C2A H2A1 . . 109.2 ?
C1A C2A H2A2 . . 109.2 ?
C3A C2A H2A2 . . 109.2 ?
H2A1 C2A H2A2 . . 107.9 ?
C4A C3A C2A . . 111.08(18) ?
C4A C3A H3A1 . . 109.4 ?
C2A C3A H3A1 . . 109.4 ?
C4A C3A H3A2 . . 109.4 ?
C2A C3A H3A2 . . 109.4 ?
H3A1 C3A H3A2 . . 108.0 ?
C5A C4A C3A . . 111.06(18) ?
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 . . 113.30(19) ?
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 ?
C7A C6A C5A . . 112.88(18) ?
C7A C6A C1A . . 110.91(16) ?
C5A C6A C1A . . 110.82(17) ?
C7A C6A H6A . . 107.3 ?
C5A C6A H6A . . 107.3 ?
C1A C6A H6A . . 107.3 ?
C6A C7A C8A . . 111.79(19) ?
C6A C7A H7A1 . . 109.3 ?
C8A C7A H7A1 . . 109.3 ?
C6A C7A H7A2 . . 109.3 ?
C8A C7A H7A2 . . 109.3 ?
H7A1 C7A H7A2 . . 107.9 ?
C7A C8A C9A . . 111.32(19) ?
C7A C8A H8A1 . . 109.4 ?
C9A C8A H8A1 . . 109.4 ?
C7A C8A H8A2 . . 109.4 ?
C9A C8A H8A2 . . 109.4 ?
H8A1 C8A H8A2 . . 108.0 ?
C10A C9A C8A . . 110.90(18) ?
C10A C9A H9A1 . . 109.5 ?
C8A C9A H9A1 . . 109.5 ?
C10A C9A H9A2 . . 109.5 ?
C8A C9A H9A2 . . 109.5 ?
H9A1 C9A H9A2 . . 108.0 ?
C9A C10A C1A . . 112.73(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 . . 112.11(18) ?
C10B C1B C6B . . 110.46(16) ?
C2B C1B C6B . . 111.90(16) ?
C10B C1B H1B . . 107.4 ?
C2B C1B H1B . . 107.4 ?
C6B C1B H1B . . 107.4 ?
C3B C2B C1B . . 110.95(18) ?
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 . . 110.98(17) ?
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 . . 111.09(17) ?
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 . . 112.40(18) ?
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 C1B . . 110.52(16) ?
C5B C6B C7B . . 113.47(16) ?
C1B C6B C7B . . 111.49(16) ?
C5B C6B H6B . . 107.0 ?
C1B C6B H6B . . 107.0 ?
C7B C6B H6B . . 107.0 ?
C8B C7B C6B . . 111.89(17) ?
C8B C7B H7B1 . . 109.2 ?
C6B C7B H7B1 . . 109.2 ?
C8B C7B H7B2 . . 109.2 ?
C6B C7B H7B2 . . 109.2 ?
H7B1 C7B H7B2 . . 107.9 ?
C7B C8B C9B . . 110.96(18) ?
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 ?
C8B C9B C10B . . 110.94(18) ?
C8B C9B H9B1 . . 109.5 ?
C10B C9B H9B1 . . 109.5 ?
C8B C9B H9B2 . . 109.5 ?
C10B C9B H9B2 . . 109.5 ?
H9B1 C9B H9B2 . . 108.0 ?
C1B C10B C9B . . 113.60(16) ?
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 . 1.532(3) ?
C1A C10A . 1.540(3) ?
C1A C6A . 1.545(3) ?
C1A H1A . 1.0 ?
C2A C3A . 1.532(3) ?
C2A H2A1 . 0.99 ?
C2A H2A2 . 0.99 ?
C3A C4A . 1.528(3) ?
C3A H3A1 . 0.99 ?
C3A H3A2 . 0.99 ?
C4A C5A . 1.526(3) ?
C4A H4A1 . 0.99 ?
C4A H4A2 . 0.99 ?
C5A C6A . 1.538(3) ?
C5A H5A1 . 0.99 ?
C5A H5A2 . 0.99 ?
C6A C7A . 1.524(3) ?
C6A H6A . 1.0 ?
C7A C8A . 1.526(4) ?
C7A H7A1 . 0.99 ?
C7A H7A2 . 0.99 ?
C8A C9A . 1.532(3) ?
C8A H8A1 . 0.99 ?
C8A H8A2 . 0.99 ?
C9A C10A . 1.509(3) ?
C9A H9A1 . 0.99 ?
C9A H9A2 . 0.99 ?
C10A H10A . 0.99 ?
C10A H10B . 0.99 ?
C1B C10B . 1.524(3) ?
C1B C2B . 1.531(3) ?
C1B C6B . 1.544(2) ?
C1B H1B . 1.0 ?
C2B C3B . 1.522(3) ?
C2B H2B1 . 0.99 ?
C2B H2B2 . 0.99 ?
C3B C4B . 1.530(3) ?
C3B H3B1 . 0.99 ?
C3B H3B2 . 0.99 ?
C4B C5B . 1.531(3) ?
C4B H4B1 . 0.99 ?
C4B H4B2 . 0.99 ?
C5B C6B . 1.520(3) ?
C5B H5B1 . 0.99 ?
C5B H5B2 . 0.99 ?
C6B C7B . 1.545(3) ?
C6B H6B . 1.0 ?
C7B C8B . 1.515(3) ?
C7B H7B1 . 0.99 ?
C7B H7B2 . 0.99 ?
C8B C9B . 1.529(3) ?
C8B H8B1 . 0.99 ?
C8B H8B2 . 0.99 ?
C9B C10B . 1.533(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 . . . . -178.92(16) ?
C6A C1A C2A C3A . . . . 55.1(2) ?
C1A C2A C3A C4A . . . . -56.3(2) ?
C2A C3A C4A C5A . . . . 55.1(3) ?
C3A C4A C5A C6A . . . . -54.2(3) ?
C4A C5A C6A C7A . . . . -72.5(2) ?
C4A C5A C6A C1A . . . . 52.6(2) ?
C2A C1A C6A C7A . . . . 73.8(2) ?
C10A C1A C6A C7A . . . . -53.7(2) ?
C2A C1A C6A C5A . . . . -52.4(2) ?
C10A C1A C6A C5A . . . . -179.93(18) ?
C5A C6A C7A C8A . . . . -179.51(19) ?
C1A C6A C7A C8A . . . . 55.4(3) ?
C6A C7A C8A C9A . . . . -56.1(3) ?
C7A C8A C9A C10A . . . . 55.2(3) ?
C8A C9A C10A C1A . . . . -54.9(3) ?
C2A C1A C10A C9A . . . . -72.1(2) ?
C6A C1A C10A C9A . . . . 54.3(2) ?
C10B C1B C2B C3B . . . . -179.52(16) ?
C6B C1B C2B C3B . . . . 55.7(2) ?
C1B C2B C3B C4B . . . . -56.4(2) ?
C2B C3B C4B C5B . . . . 55.9(3) ?
C3B C4B C5B C6B . . . . -55.2(2) ?
C4B C5B C6B C1B . . . . 53.8(2) ?
C4B C5B C6B C7B . . . . -72.3(2) ?
C10B C1B C6B C5B . . . . -179.72(18) ?
C2B C1B C6B C5B . . . . -54.1(2) ?
C10B C1B C6B C7B . . . . -52.5(2) ?
C2B C1B C6B C7B . . . . 73.1(2) ?
C5B C6B C7B C8B . . . . -179.0(2) ?
C1B C6B C7B C8B . . . . 55.4(2) ?
C6B C7B C8B C9B . . . . -56.4(3) ?
C7B C8B C9B C10B . . . . 55.1(3) ?
C2B C1B C10B C9B . . . . -72.6(2) ?
C6B C1B C10B C9B . . . . 52.9(2) ?
C8B C9B C10B C1B . . . . -54.4(2) ?
