#------------------------------------------------------------------------------
#$Date: 2024-04-19 00:47:03 +0200 (Fri 19 de Apr de 2024) $
#$Revision: 291276 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/84/7248461.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_7248461
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_name_full               CrystEngComm
_journal_paper_doi               10.1039/D3CE01117H
_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                113.547(3)
_cell_angle_beta                 90.225(3)
_cell_angle_gamma                112.687(3)
_cell_formula_units_Z            4
_cell_length_a                   8.2602(9)
_cell_length_b                   10.5243(9)
_cell_length_c                   11.9532(12)
_cell_measurement_reflns_used    5831
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      25.3688
_cell_measurement_theta_min      2.7207
_cell_volume                     863.42(15)
_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      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0178
_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            9821
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_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  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.063
_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         0.186
_refine_diff_density_min         -0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0423
_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)+(0.0308P)²+0.3970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                2463
_reflns_number_total             2761
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01117h2.cif
_cod_data_source_block           c_Dec_k180K_100K_cd_aP
_cod_database_code               7248461
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 0.7499(3) 0.1997(2) 0.56171(18) 0.0216(5) Uani d . . . 1 . .
H H1A 0.6429 0.1296 0.5799 0.026 Uiso calc U . R 1 . .
C C2A 0.7708(3) 0.3632(3) 0.64127(18) 0.0245(5) Uani d . . . 1 . .
H H2A1 0.7872 0.3847 0.7301 0.029 Uiso calc U . R 1 . .
H H2A2 0.879 0.4365 0.6285 0.029 Uiso calc U . R 1 . .
C C3A 0.6079(3) 0.3866(3) 0.60855(19) 0.0301(5) Uani d . . . 1 . .
H H3A1 0.5017 0.3208 0.6293 0.036 Uiso calc U . R 1 . .
H H3A2 0.629 0.4944 0.6588 0.036 Uiso calc U . R 1 . .
C C4A 0.5719(3) 0.3474(3) 0.47033(18) 0.0296(5) Uani d . . . 1 . .
H H4A1 0.4613 0.3563 0.4506 0.035 Uiso calc U . R 1 . .
H H4A2 0.6718 0.4212 0.4516 0.035 Uiso calc U . R 1 . .
C C5A 0.5517(3) 0.1851(3) 0.38950(19) 0.0259(5) Uani d . . . 1 . .
H H5A1 0.5383 0.1664 0.3013 0.031 Uiso calc U . R 1 . .
H H5A2 0.4413 0.1112 0.3997 0.031 Uiso calc U . R 1 . .
C C6A 0.7112(3) 0.1557(2) 0.42141(17) 0.0215(4) Uani d . . . 1 . .
H H6A 0.6764 0.0434 0.3757 0.026 Uiso calc U . R 1 . .
C C7A 0.8784(3) 0.2367(3) 0.37960(19) 0.0307(5) Uani d . . . 1 . .
H H7A1 0.9132 0.3482 0.4205 0.037 Uiso calc U . R 1 . .
H H7A2 0.8521 0.2018 0.2887 0.037 Uiso calc U . R 1 . .
C C8A 1.0336(3) 0.2046(3) 0.4114(2) 0.0407(6) Uani d . . . 1 . .
H H8A1 1.1411 0.2626 0.3864 0.049 Uiso calc U . R 1 . .
H H8A2 1.0034 0.0943 0.3639 0.049 Uiso calc U . R 1 . .
C C9A 1.0746(3) 0.2498(3) 0.5505(2) 0.0378(6) Uani d . . . 1 . .
H H9A1 1.1701 0.2213 0.5671 0.045 Uiso calc U . R 1 . .
H H9A2 1.1182 0.362 0.5976 0.045 Uiso calc U . R 1 . .
C C10A 0.9095(3) 0.1707(3) 0.59347(18) 0.0297(5) Uani d . . . 1 . .
H H10A 0.9374 0.2073 0.6845 0.036 Uiso calc U . R 1 . .
H H10B 0.8758 0.0593 0.554 0.036 Uiso calc U . R 1 . .
C C1B 0.5425(3) 0.8012(2) 0.93664(17) 0.0199(4) Uani d . . . 1 . .
H H1B 0.4939 0.8683 0.9227 0.024 Uiso calc U . R 1 . .
C C2B 0.4100(3) 0.6355(2) 0.85727(17) 0.0224(5) Uani d . . . 1 . .
H H2B1 0.3966 0.616 0.7688 0.027 Uiso calc U . R 1 . .
H H2B2 0.4571 0.5659 0.8661 0.027 Uiso calc U . R 1 . .
C C3B 0.2289(3) 0.6025(3) 0.89588(18) 0.0280(5) Uani d . . . 1 . .
H H3B1 0.1476 0.4934 0.8458 0.034 Uiso calc U . R 1 . .
H H3B2 0.1766 0.6652 0.8797 0.034 Uiso calc U . R 1 . .
C C4B 0.2462(3) 0.6385(3) 1.03399(17) 0.0273(5) Uani d . . . 1 . .
H H4B1 0.1278 0.6215 1.0582 0.033 Uiso calc U . R 1 . .
H H4B2 0.2871 0.5686 1.0486 0.033 Uiso calc U . R 1 . .
C C5B 0.3787(3) 0.8041(3) 1.11404(18) 0.0246(5) Uani d . . . 1 . .
H H5B1 0.3306 0.8737 1.1064 0.03 Uiso calc U . R 1 . .
H H5B2 0.392 0.8224 1.2022 0.03 Uiso calc U . R 1 . .
C C6B 0.5610(3) 0.8411(2) 1.07669(17) 0.0209(4) Uani d . . . 1 . .
H H6B 0.6317 0.9543 1.1226 0.025 Uiso calc U . R 1 . .
C C7B 0.6672(3) 0.7661(3) 1.11298(18) 0.0245(5) Uani d . . . 1 . .
H H7B1 0.6825 0.7995 1.2039 0.029 Uiso calc U . R 1 . .
H H7B2 0.5985 0.6536 1.0718 0.029 Uiso calc U . R 1 . .
C C8B 0.8496(3) 0.8080(3) 1.0760(2) 0.0299(5) Uani d . . . 1 . .
H H8B1 0.9107 0.7534 1.0965 0.036 Uiso calc U . R 1 . .
H H8B2 0.9233 0.9192 1.1236 0.036 Uiso calc U . R 1 . .
C C9B 0.8314(3) 0.7653(3) 0.93667(18) 0.0277(5) Uani d . . . 1 . .
H H9B1 0.7705 0.6527 0.8892 0.033 Uiso calc U . R 1 . .
H H9B2 0.9518 0.8004 0.9157 0.033 Uiso calc U . R 1 . .
C C10B 0.7250(3) 0.8379(3) 0.89906(18) 0.0250(5) Uani d . . . 1 . .
H H10C 0.7951 0.9503 0.9378 0.03 Uiso calc U . R 1 . .
H H10D 0.7086 0.8018 0.8078 0.03 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 . . 113.44(18) ?
C2A C1A C6A . . 111.60(16) ?
C10A C1A C6A . . 110.73(17) ?
C2A C1A H1A . . 106.9 ?
C10A C1A H1A . . 106.9 ?
C6A C1A H1A . . 106.9 ?
C3A C2A C1A . . 111.84(18) ?
C3A C2A H2A1 . . 109.2 ?
C1A C2A H2A1 . . 109.2 ?
C3A C2A H2A2 . . 109.2 ?
C1A C2A H2A2 . . 109.2 ?
H2A1 C2A H2A2 . . 107.9 ?
C4A C3A C2A . . 111.17(17) ?
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 . . 110.98(17) ?
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 . . 113.31(18) ?
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 . . 112.69(17) ?
C7A C6A C1A . . 110.92(16) ?
C5A C6A C1A . . 110.81(16) ?
C7A C6A H6A . . 107.4 ?
C5A C6A H6A . . 107.4 ?
C1A C6A H6A . . 107.4 ?
C6A C7A C8A . . 111.57(19) ?
C6A C7A H7A1 . . 109.3 ?
C8A C7A H7A1 . . 109.3 ?
C6A C7A H7A2 . . 109.3 ?
C8A C7A H7A2 . . 109.3 ?
H7A1 C7A H7A2 . . 108.0 ?
C7A C8A C9A . . 111.50(18) ?
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 . . 110.69(18) ?
C10A C9A H9A1 . . 109.5 ?
C8A C9A H9A1 . . 109.5 ?
C10A C9A H9A2 . . 109.5 ?
C8A C9A H9A2 . . 109.5 ?
H9A1 C9A H9A2 . . 108.1 ?
C9A C10A C1A . . 112.65(17) ?
C9A C10A H10A . . 109.1 ?
C1A C10A H10A . . 109.1 ?
C9A C10A H10B . . 109.1 ?
C1A C10A H10B . . 109.1 ?
H10A C10A H10B . . 107.8 ?
C10B C1B C2B . . 112.30(17) ?
C10B C1B C6B . . 110.37(16) ?
C2B C1B C6B . . 111.75(16) ?
C10B C1B H1B . . 107.4 ?
C2B C1B H1B . . 107.4 ?
C6B C1B H1B . . 107.4 ?
C3B C2B C1B . . 111.18(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 . . 110.74(17) ?
C2B C3B H3B1 . . 109.5 ?
C4B C3B H3B1 . . 109.5 ?
C2B C3B H3B2 . . 109.5 ?
C4B C3B H3B2 . . 109.5 ?
H3B1 C3B H3B2 . . 108.1 ?
C5B C4B C3B . . 110.99(17) ?
C5B C4B H4B1 . . 109.4 ?
C3B C4B H4B1 . . 109.4 ?
C5B C4B H4B2 . . 109.4 ?
C3B C4B H4B2 . . 109.4 ?
H4B1 C4B H4B2 . . 108.0 ?
C6B C5B C4B . . 112.29(17) ?
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 . . 113.55(16) ?
C5B C6B C1B . . 110.32(16) ?
C7B C6B C1B . . 111.68(16) ?
C5B C6B H6B . . 107.0 ?
C7B C6B H6B . . 107.0 ?
C1B C6B H6B . . 107.0 ?
C8B C7B C6B . . 111.91(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 . . 110.69(17) ?
C7B C8B H8B1 . . 109.5 ?
C9B C8B H8B1 . . 109.5 ?
C7B C8B H8B2 . . 109.5 ?
C9B C8B H8B2 . . 109.5 ?
H8B1 C8B H8B2 . . 108.1 ?
C8B C9B C10B . . 111.24(18) ?
C8B C9B H9B1 . . 109.4 ?
C10B C9B H9B1 . . 109.4 ?
C8B C9B H9B2 . . 109.4 ?
C10B C9B H9B2 . . 109.4 ?
H9B1 C9B H9B2 . . 108.0 ?
C1B C10B C9B . . 113.58(16) ?
C1B C10B H10C . . 108.9 ?
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 . 1.535(3) ?
C1A C10A . 1.542(3) ?
C1A C6A . 1.546(3) ?
C1A H1A . 1.0 ?
C2A C3A . 1.534(3) ?
C2A H2A1 . 0.99 ?
C2A H2A2 . 0.99 ?
C3A C4A . 1.531(3) ?
C3A H3A1 . 0.99 ?
C3A H3A2 . 0.99 ?
C4A C5A . 1.530(3) ?
C4A H4A1 . 0.99 ?
C4A H4A2 . 0.99 ?
C5A C6A . 1.543(3) ?
C5A H5A1 . 0.99 ?
C5A H5A2 . 0.99 ?
C6A C7A . 1.523(3) ?
C6A H6A . 1.0 ?
C7A C8A . 1.528(3) ?
C7A H7A1 . 0.99 ?
C7A H7A2 . 0.99 ?
C8A C9A . 1.531(3) ?
C8A H8A1 . 0.99 ?
C8A H8A2 . 0.99 ?
C9A C10A . 1.513(3) ?
C9A H9A1 . 0.99 ?
C9A H9A2 . 0.99 ?
C10A H10A . 0.99 ?
C10A H10B . 0.99 ?
C1B C10B . 1.523(3) ?
C1B C2B . 1.528(3) ?
C1B C6B . 1.546(2) ?
C1B H1B . 1.0 ?
C2B C3B . 1.518(3) ?
C2B H2B1 . 0.99 ?
C2B H2B2 . 0.99 ?
C3B C4B . 1.532(3) ?
C3B H3B1 . 0.99 ?
C3B H3B2 . 0.99 ?
C4B C5B . 1.529(3) ?
C4B H4B1 . 0.99 ?
C4B H4B2 . 0.99 ?
C5B C6B . 1.520(3) ?
C5B H5B1 . 0.99 ?
C5B H5B2 . 0.99 ?
C6B C7B . 1.544(3) ?
C6B H6B . 1.0 ?
C7B C8B . 1.519(3) ?
C7B H7B1 . 0.99 ?
C7B H7B2 . 0.99 ?
C8B C9B . 1.532(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 . . . . -178.94(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 . . . . -54.1(2) ?
C4A C5A C6A C7A . . . . -72.3(2) ?
C4A C5A C6A C1A . . . . 52.7(2) ?
C2A C1A C6A C7A . . . . 73.5(2) ?
C10A C1A C6A C7A . . . . -53.9(2) ?
C2A C1A C6A C5A . . . . -52.5(2) ?
C10A C1A C6A C5A . . . . -179.87(18) ?
C5A C6A C7A C8A . . . . -179.53(19) ?
C1A C6A C7A C8A . . . . 55.6(2) ?
C6A C7A C8A C9A . . . . -56.4(3) ?
C7A C8A C9A C10A . . . . 55.4(3) ?
C8A C9A C10A C1A . . . . -54.8(3) ?
C2A C1A C10A C9A . . . . -72.0(2) ?
C6A C1A C10A C9A . . . . 54.3(2) ?
C10B C1B C2B C3B . . . . -179.45(16) ?
C6B C1B C2B C3B . . . . 55.9(2) ?
C1B C2B C3B C4B . . . . -56.5(2) ?
C2B C3B C4B C5B . . . . 56.1(2) ?
C3B C4B C5B C6B . . . . -55.8(2) ?
C4B C5B C6B C7B . . . . -72.0(2) ?
C4B C5B C6B C1B . . . . 54.2(2) ?
C10B C1B C6B C5B . . . . -179.91(18) ?
C2B C1B C6B C5B . . . . -54.2(2) ?
C10B C1B C6B C7B . . . . -52.6(2) ?
C2B C1B C6B C7B . . . . 73.1(2) ?
C5B C6B C7B C8B . . . . -179.04(19) ?
C1B C6B C7B C8B . . . . 55.4(2) ?
C6B C7B C8B C9B . . . . -56.1(2) ?
C7B C8B C9B C10B . . . . 54.9(3) ?
C2B C1B C10B C9B . . . . -72.5(2) ?
C6B C1B C10B C9B . . . . 52.9(2) ?
C8B C9B C10B C1B . . . . -54.5(2) ?
