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#$Date: 2023-04-03 10:32:47 +0300 (Mon, 03 Apr 2023) $
#$Revision: 282200 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106993.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_8106993
loop_
_publ_author_name
'Zhao, Chen-Liang'
'Zhang, Jing-Jie'
'Zhang, Qi-Long'
'Pan, Lu-Tai'
_publ_section_title
;
 Crystal structure of
 5,5,9,13-tetramethyltetracyclo[10·2·1·01,10·04,9]pentadecane-3,7,14-triol,
 C20H34O4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              745
_journal_page_last               746
_journal_paper_doi               10.1515/ncrs-2015-0254
_journal_volume                  231
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H34 O4'
_chemical_formula_weight         338.47
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.222(2)
_cell_length_b                   13.705(5)
_cell_length_c                   21.903(8)
_cell_measurement_reflns_used    1740
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.75
_cell_volume                     1867.7(11)
_computing_cell_refinement       'APEX2 (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX II CCD Area Detector'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_sigmaI/netI    0.0803
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9546
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_correction_T_min  0.9807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(3)
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0679P)²+0.5277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1736
_reflns_number_gt                2029
_reflns_number_total             3247
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0254_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1867.9(12)
_cod_original_sg_symbol_Hall     'P2ac2ab '
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               8106993
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5839(7) 0.3796(3) 0.72382(17) 0.0481(10) Uani 1 1 d . . .
H1A H 0.4362 0.3985 0.7316 0.058 Uiso 1 1 calc R . .
H1B H 0.5821 0.3134 0.7081 0.058 Uiso 1 1 calc R . .
C2 C 0.7050(7) 0.3803(3) 0.78364(17) 0.0485(11) Uani 1 1 d . . .
H2 H 0.8499 0.3541 0.7774 0.058 Uiso 1 1 calc R . .
C3 C 0.7201(8) 0.4826(3) 0.80864(18) 0.0522(11) Uani 1 1 d . . .
H3A H 0.8063 0.4808 0.8455 0.063 Uiso 1 1 calc R . .
H3B H 0.5768 0.5036 0.8201 0.063 Uiso 1 1 calc R . .
C4 C 0.8163(7) 0.5595(3) 0.76545(17) 0.0443(10) Uani 1 1 d . . .
C5 C 0.6986(6) 0.5524(3) 0.70237(16) 0.0389(9) Uani 1 1 d . . .
H5 H 0.5505 0.5725 0.7109 0.047 Uiso 1 1 calc R . .
C6 C 0.7750(7) 0.6222(3) 0.65253(17) 0.0429(10) Uani 1 1 d . . .
H6 H 0.9070 0.5953 0.6349 0.051 Uiso 1 1 calc R . .
C7 C 0.6068(7) 0.6280(3) 0.60169(18) 0.0477(10) Uani 1 1 d . . .
H7A H 0.4751 0.6544 0.6187 0.057 Uiso 1 1 calc R . .
H7B H 0.6573 0.6734 0.5709 0.057 Uiso 1 1 calc R . .
C8 C 0.5562(6) 0.5321(3) 0.57128(17) 0.0413(10) Uani 1 1 d . . .
C9 C 0.5135(6) 0.4526(3) 0.62052(17) 0.0406(10) Uani 1 1 d . . .
H9 H 0.3788 0.4730 0.6399 0.049 Uiso 1 1 calc R . .
C10 C 0.6773(6) 0.4475(3) 0.67423(17) 0.0400(9) Uani 1 1 d . . .
C11 C 0.4580(7) 0.3523(3) 0.58987(19) 0.0529(12) Uani 1 1 d . . .
H11A H 0.4838 0.3007 0.6193 0.063 Uiso 1 1 calc R . .
H11B H 0.3059 0.3516 0.5801 0.063 Uiso 1 1 calc R . .
C12 C 0.5845(9) 0.3292(3) 0.5318(2) 0.0622(13) Uani 1 1 d . . .
H12A H 0.5151 0.2760 0.5102 0.075 Uiso 1 1 calc R . .
H12B H 0.7284 0.3082 0.5427 0.075 Uiso 1 1 calc R . .
C13 C 0.5987(8) 0.4188(3) 0.4895(2) 0.0611(13) Uani 1 1 d . . .
H13 H 0.6663 0.4027 0.4504 0.073 Uiso 1 1 calc R . .
C14 C 0.7205(7) 0.4989(3) 0.52309(18) 0.0519(11) Uani 1 1 d . . .
H14A H 0.7585 0.5519 0.4958 0.062 Uiso 1 1 calc R . .
H14B H 0.8499 0.4737 0.5421 0.062 Uiso 1 1 calc R . .
C15 C 0.3505(6) 0.5407(3) 0.53054(17) 0.0443(10) Uani 1 1 d . . .
H15 H 0.2227 0.5247 0.5547 0.053 Uiso 1 1 calc R . .
C16 C 0.3818(7) 0.4650(3) 0.48092(18) 0.0525(11) Uani 1 1 d . . .
C17 C 0.2434(9) 0.4478(4) 0.4371(2) 0.0776(16) Uani 1 1 d . . .
H17A H 0.2756 0.4026 0.4068 0.093 Uiso 1 1 calc R . .
H17B H 0.1129 0.4809 0.4363 0.093 Uiso 1 1 calc R . .
C18 C 0.7658(9) 0.6570(3) 0.79713(19) 0.0664(14) Uani 1 1 d . . .
H18A H 0.6130 0.6644 0.8009 0.100 Uiso 1 1 calc R . .
H18B H 0.8229 0.7097 0.7733 0.100 Uiso 1 1 calc R . .
H18C H 0.8300 0.6576 0.8370 0.100 Uiso 1 1 calc R . .
C19 C 1.0618(7) 0.5521(4) 0.7610(2) 0.0670(14) Uani 1 1 d . . .
H19A H 1.1004 0.4915 0.7419 0.101 Uiso 1 1 calc R . .
H19B H 1.1228 0.5547 0.8012 0.101 Uiso 1 1 calc R . .
H19C H 1.1158 0.6054 0.7371 0.101 Uiso 1 1 calc R . .
C20 C 0.8956(7) 0.4021(3) 0.65438(19) 0.0528(11) Uani 1 1 d . . .
H20A H 0.9605 0.4423 0.6236 0.079 Uiso 1 1 calc R . .
H20B H 0.8715 0.3379 0.6382 0.079 Uiso 1 1 calc R . .
H20C H 0.9894 0.3979 0.6891 0.079 Uiso 1 1 calc R . .
O1 O 0.8209(5) 0.72007(18) 0.67282(11) 0.0520(8) Uani 1 1 d . . .
H1 H 0.7462 0.7588 0.6538 0.078 Uiso 1 1 calc R . .
O2 O 0.5883(6) 0.3182(2) 0.82505(13) 0.0695(10) Uani 1 1 d . . .
H2A H 0.6496 0.3172 0.8582 0.104 Uiso 1 1 calc R . .
O1W O 1.1064(6) 0.7747(2) 0.57952(16) 0.0611(9) Uiso 1 1 d . . .
H1D H 1.1352 0.8031 0.5473 0.45(10) Uiso 1 1 d R . .
H1C H 1.0352 0.7753 0.6050 0.17(3) Uiso 1 1 d R . .
O3 O 0.3258(5) 0.6357(2) 0.50351(12) 0.0576(9) Uani 1 1 d . . .
H3 H 0.3006 0.6298 0.4670 0.086 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 '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 C10 114.7(3) . .
C2 C1 H1A 108.6 . .
C10 C1 H1A 108.6 . .
C2 C1 H1B 108.6 . .
C10 C1 H1B 108.6 . .
H1A C1 H1B 107.6 . .
O2 C2 C3 110.6(3) . .
O2 C2 C1 106.9(3) . .
C3 C2 C1 110.6(3) . .
O2 C2 H2 109.6 . .
C3 C2 H2 109.6 . .
C1 C2 H2 109.6 . .
C2 C3 C4 116.0(3) . .
C2 C3 H3A 108.3 . .
C4 C3 H3A 108.3 . .
C2 C3 H3B 108.3 . .
C4 C3 H3B 108.3 . .
H3A C3 H3B 107.4 . .
C19 C4 C3 112.5(4) . .
C19 C4 C18 106.8(4) . .
C3 C4 C18 103.8(3) . .
C19 C4 C5 113.9(4) . .
C3 C4 C5 108.6(3) . .
C18 C4 C5 110.8(3) . .
C6 C5 C4 116.5(3) . .
C6 C5 C10 108.6(3) . .
C4 C5 C10 116.2(3) . .
C6 C5 H5 104.7 . .
C4 C5 H5 104.7 . .
C10 C5 H5 104.7 . .
O1 C6 C5 115.1(3) . .
O1 C6 C7 108.2(3) . .
C5 C6 C7 109.9(3) . .
O1 C6 H6 107.8 . .
C5 C6 H6 107.8 . .
C7 C6 H6 107.8 . .
C8 C7 C6 114.8(3) . .
C8 C7 H7A 108.6 . .
C6 C7 H7A 108.6 . .
C8 C7 H7B 108.6 . .
C6 C7 H7B 108.6 . .
H7A C7 H7B 107.5 . .
C7 C8 C14 115.0(3) . .
C7 C8 C9 109.9(3) . .
C14 C8 C9 112.4(3) . .
C7 C8 C15 110.9(3) . .
C14 C8 C15 100.1(3) . .
C9 C8 C15 108.0(3) . .
C8 C9 C10 116.3(3) . .
C8 C9 C11 110.8(3) . .
C10 C9 C11 115.3(3) . .
C8 C9 H9 104.2 . .
C10 C9 H9 104.2 . .
C11 C9 H9 104.2 . .
C1 C10 C20 106.5(3) . .
C1 C10 C9 108.2(3) . .
C20 C10 C9 112.2(3) . .
C1 C10 C5 107.9(3) . .
C20 C10 C5 113.7(3) . .
C9 C10 C5 108.1(3) . .
C12 C11 C9 115.1(3) . .
C12 C11 H11A 108.5 . .
C9 C11 H11A 108.5 . .
C12 C11 H11B 108.5 . .
C9 C11 H11B 108.5 . .
H11A C11 H11B 107.5 . .
C11 C12 C13 111.4(4) . .
C11 C12 H12A 109.4 . .
C13 C12 H12A 109.4 . .
C11 C12 H12B 109.4 . .
C13 C12 H12B 109.4 . .
H12A C12 H12B 108.0 . .
C16 C13 C14 101.8(4) . .
C16 C13 C12 111.1(4) . .
C14 C13 C12 108.2(4) . .
C16 C13 H13 111.8 . .
C14 C13 H13 111.8 . .
C12 C13 H13 111.8 . .
C13 C14 C8 102.4(3) . .
C13 C14 H14A 111.3 . .
C8 C14 H14A 111.3 . .
C13 C14 H14B 111.3 . .
C8 C14 H14B 111.3 . .
H14A C14 H14B 109.2 . .
O3 C15 C16 109.8(3) . .
O3 C15 C8 113.0(3) . .
C16 C15 C8 104.6(3) . .
O3 C15 H15 109.8 . .
C16 C15 H15 109.8 . .
C8 C15 H15 109.8 . .
C17 C16 C13 127.3(4) . .
C17 C16 C15 124.3(4) . .
C13 C16 C15 108.3(3) . .
C16 C17 H17A 120.0 . .
C16 C17 H17B 120.0 . .
H17A C17 H17B 120.0 . .
C4 C18 H18A 109.5 . .
C4 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C4 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C4 C19 H19A 109.5 . .
C4 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C4 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C10 C20 H20A 109.5 . .
C10 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C10 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C6 O1 H1 109.5 . .
C2 O2 H2A 109.5 . .
H1D O1W H1C 143.2 . .
C15 O3 H3 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.512(5) .
C1 C10 1.544(5) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 O2 1.440(5) .
C2 C3 1.508(6) .
C2 H2 0.9800 .
C3 C4 1.537(6) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C19 1.534(6) .
C4 C18 1.538(6) .
C4 C5 1.567(5) .
C5 C6 1.527(5) .
C5 C10 1.571(5) .
C5 H5 0.9800 .
C6 O1 1.441(4) .
C6 C7 1.530(6) .
C6 H6 0.9800 .
C7 C8 1.506(5) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C14 1.538(5) .
C8 C9 1.556(5) .
C8 C15 1.565(5) .
C9 C10 1.558(5) .
C9 C11 1.568(5) .
C9 H9 0.9800 .
C10 C20 1.556(5) .
C11 C12 1.529(6) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.541(6) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C16 1.502(6) .
C13 C14 1.523(6) .
C13 H13 0.9800 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 O3 1.438(5) .
C15 C16 1.516(5) .
C15 H15 0.9800 .
C16 C17 1.310(6) .
C17 H17A 0.9300 .
C17 H17B 0.9300 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
O1 H1 0.8200 .
O2 H2A 0.8200 .
O1W H1D 0.8247 .
O1W H1C 0.7129 .
O3 H3 0.8200 .
