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#$Date: 2022-06-23 10:17:49 +0300 (Thu, 23 Jun 2022) $
#$Revision: 276165 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105459.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_8105459
loop_
_publ_author_name
'Zhai, Shengxian'
'Yu, Youzhu'
'Niu, Yongsheng'
'Han, Chuchu'
_publ_section_title
;
 Crystal structure of (4aS,5S,6aS,6a1S, 10aS)-4a,5,6a,6a
 1,9,10-hexahydro-7H-4,5-methanocyclobuta[4,5]naphtho[8a,1-b]pyran-6(2H)-one,
 C15H16O2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1335
_journal_page_last               1337
_journal_paper_doi               10.1515/ncrs-2020-0304
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C15 H16 O2'
_chemical_formula_sum            'C15 H16 O2'
_chemical_formula_weight         228.28
_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
_cell_angle_alpha                92.790(7)
_cell_angle_beta                 100.516(7)
_cell_angle_gamma                106.105(6)
_cell_formula_units_Z            2
_cell_length_a                   5.6034(7)
_cell_length_b                   8.7105(11)
_cell_length_c                   12.5661(16)
_cell_measurement_reflns_used    3876
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      3.87
_cell_volume                     576.15(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5634
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.503
_diffrn_reflns_theta_min         3.866
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0476
_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)+(0.0716P)²+0.1386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1348
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2588
_reflns_number_total             2869
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0304_suppl.cif
_cod_data_source_block           2_a
_cod_database_code               8105459
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C10(H10), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C15(H15A,H15B), C12(H12A,H12B), C3(H3A,H3B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C4(H4)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5765(2) 0.28624(13) 0.82412(9) 0.0285(2) Uani 1 1 d . . . . .
C2 C 0.5558(3) 0.26267(16) 0.94308(9) 0.0391(3) Uani 1 1 d . . . . .
H2A H 0.5755 0.3660 0.9817 0.047 Uiso 1 1 calc R . . . .
H2B H 0.6937 0.2231 0.9772 0.047 Uiso 1 1 calc R . . . .
C3 C 0.3021(3) 0.14482(18) 0.95458(11) 0.0467(3) Uani 1 1 d . . . . .
H3A H 0.3258 0.1014 1.0241 0.056 Uiso 1 1 calc R . . . .
H3B H 0.1780 0.2034 0.9547 0.056 Uiso 1 1 calc R . . . .
C4 C 0.1998(3) 0.00867(16) 0.86580(12) 0.0446(3) Uani 1 1 d . . . . .
H4 H 0.0476 -0.0689 0.8658 0.053 Uiso 1 1 calc R . . . .
C5 C 0.3241(2) -0.00193(14) 0.78757(11) 0.0384(3) Uani 1 1 d . . . . .
C6 C 0.2710(3) -0.08108(16) 0.67263(12) 0.0494(3) Uani 1 1 d . . . . .
H6A H 0.0979 -0.0989 0.6335 0.059 Uiso 1 1 calc R . . . .
H6B H 0.3238 -0.1777 0.6668 0.059 Uiso 1 1 calc R . . . .
C7 C 0.4652(2) 0.07387(15) 0.64600(10) 0.0388(3) Uani 1 1 d . . . . .
H7 H 0.5952 0.0493 0.6112 0.047 Uiso 1 1 calc R . . . .
C8 C 0.5586(2) 0.12234(13) 0.77144(9) 0.0320(2) Uani 1 1 d . . . . .
H8 H 0.7116 0.0909 0.7989 0.038 Uiso 1 1 calc R . . . .
C9 C 0.3424(3) 0.18610(16) 0.58708(10) 0.0424(3) Uani 1 1 d . . . . .
C10 C 0.2093(2) 0.27689(16) 0.64884(10) 0.0372(3) Uani 1 1 d . . . . .
H10 H 0.0339 0.2155 0.6488 0.045 Uiso 1 1 calc R . . . .
C11 C 0.3650(2) 0.35065(13) 0.76518(9) 0.0300(2) Uani 1 1 d . . . . .
H11 H 0.2509 0.3617 0.8137 0.036 Uiso 1 1 calc R . . . .
C12 C 0.2343(3) 0.45022(18) 0.61695(12) 0.0487(3) Uani 1 1 d . . . . .
H12A H 0.2835 0.4689 0.5475 0.058 Uiso 1 1 calc R . . . .
H12B H 0.0897 0.4882 0.6230 0.058 Uiso 1 1 calc R . . . .
C13 C 0.4513(3) 0.50382(15) 0.71406(11) 0.0406(3) Uani 1 1 d . . . . .
C14 C 0.6835(3) 0.60222(16) 0.73953(13) 0.0502(3) Uani 1 1 d . . . . .
H14 H 0.7365 0.6923 0.7034 0.060 Uiso 1 1 calc R . . . .
C15 C 0.8560(3) 0.55846(15) 0.83100(12) 0.0469(3) Uani 1 1 d . . . . .
H15A H 1.0308 0.6164 0.8307 0.056 Uiso 1 1 calc R . . . .
H15B H 0.8185 0.5895 0.8998 0.056 Uiso 1 1 calc R . . . .
O1 O 0.3476(3) 0.20177(19) 0.49237(9) 0.0831(5) Uani 1 1 d . . . . .
O2 O 0.82422(15) 0.38882(10) 0.82021(7) 0.0375(2) Uani 1 1 d . . . . .
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
C15 O2 C1 116.23(9) . .
C5 C8 H8 111.1 . .
C5 C8 C1 110.98(9) . .
C5 C8 C7 88.14(9) . .
C1 C8 H8 111.1 . .
C1 C8 C7 122.27(10) . .
C7 C8 H8 111.1 . .
C13 C11 H11 110.4 . .
C13 C11 C10 85.84(9) . .
C13 C11 C1 115.84(10) . .
C10 C11 H11 110.4 . .
C1 C11 H11 110.4 . .
C1 C11 C10 121.77(9) . .
H2A C2 H2B 107.7 . .
C1 C2 H2A 108.9 . .
C1 C2 H2B 108.9 . .
C1 C2 C3 113.47(10) . .
C3 C2 H2A 108.9 . .
C3 C2 H2B 108.9 . .
C11 C13 C12 92.92(10) . .
C14 C13 C11 123.76(12) . .
C14 C13 C12 138.92(14) . .
C11 C10 H10 112.9 . .
C9 C10 C11 113.27(9) . .
C9 C10 H10 112.9 . .
C9 C10 C12 113.79(11) . .
C12 C10 C11 88.88(9) . .
C12 C10 H10 112.9 . .
C8 C5 C6 92.49(10) . .
C4 C5 C8 125.45(12) . .
C4 C5 C6 138.57(13) . .
O2 C1 C8 106.41(8) . .
O2 C1 C11 111.78(9) . .
O2 C1 C2 109.95(9) . .
C8 C1 C11 111.08(9) . .
C8 C1 C2 105.58(9) . .
C11 C1 C2 111.73(9) . .
O1 C9 C10 121.15(14) . .
O1 C9 C7 120.92(14) . .
C7 C9 C10 117.92(11) . .
C8 C7 H7 112.8 . .
C8 C7 C6 87.92(9) . .
C9 C7 C8 114.41(10) . .
C9 C7 H7 112.8 . .
C9 C7 C6 113.80(11) . .
C6 C7 H7 112.8 . .
C13 C14 H14 122.5 . .
C13 C14 C15 115.07(13) . .
C15 C14 H14 122.5 . .
O2 C15 C14 110.55(10) . .
O2 C15 H15A 109.5 . .
O2 C15 H15B 109.5 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 108.1 . .
C5 C4 H4 119.8 . .
C5 C4 C3 120.42(12) . .
C3 C4 H4 119.8 . .
C13 C12 C10 85.99(9) . .
C13 C12 H12A 114.3 . .
C13 C12 H12B 114.3 . .
C10 C12 H12A 114.3 . .
C10 C12 H12B 114.3 . .
H12A C12 H12B 111.5 . .
C2 C3 H3A 108.9 . .
C2 C3 H3B 108.9 . .
C4 C3 C2 113.46(11) . .
C4 C3 H3A 108.9 . .
C4 C3 H3B 108.9 . .
H3A C3 H3B 107.7 . .
C5 C6 C7 87.61(9) . .
C5 C6 H6A 114.1 . .
C5 C6 H6B 114.1 . .
C7 C6 H6A 114.1 . .
C7 C6 H6B 114.1 . .
H6A C6 H6B 111.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C1 1.4385(13) .
O2 C15 1.4351(15) .
O1 C9 1.2093(17) .
C8 H8 0.9800 .
C8 C5 1.5064(16) .
C8 C1 1.5136(15) .
C8 C7 1.5646(16) .
C11 H11 0.9800 .
C11 C13 1.5051(16) .
C11 C10 1.5630(16) .
C11 C1 1.5350(14) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C1 1.5395(16) .
C2 C3 1.541(2) .
C13 C14 1.316(2) .
C13 C12 1.5078(19) .
C10 H10 0.9800 .
C10 C9 1.5042(19) .
C10 C12 1.5563(19) .
C5 C4 1.3178(19) .
C5 C6 1.5107(19) .
C9 C7 1.495(2) .
C7 H7 0.9800 .
C7 C6 1.5749(19) .
C14 H14 0.9300 .
C14 C15 1.497(2) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C4 H4 0.9300 .
C4 C3 1.497(2) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C9 C7 C8 152.02(15) . . . .
O1 C9 C7 C6 -108.96(17) . . . .
C8 C5 C4 C3 -6.0(2) . . . .
C8 C5 C6 C7 -14.99(10) . . . .
C8 C7 C6 C5 14.41(9) . . . .
C11 C13 C14 C15 -4.7(2) . . . .
C11 C13 C12 C10 -19.34(10) . . . .
C11 C10 C9 O1 -136.04(15) . . . .
C11 C10 C9 C7 44.81(15) . . . .
C11 C10 C12 C13 18.58(10) . . . .
C13 C11 C10 C9 96.90(11) . . . .
C13 C11 C10 C12 -18.62(9) . . . .
C13 C11 C1 O2 0.72(13) . . . .
C13 C11 C1 C8 -117.97(11) . . . .
C13 C11 C1 C2 124.41(11) . . . .
C13 C14 C15 O2 42.81(18) . . . .
C10 C11 C13 C14 -141.12(14) . . . .
C10 C11 C13 C12 19.26(10) . . . .
C10 C11 C1 O2 102.55(11) . . . .
C10 C11 C1 C8 -16.14(14) . . . .
C10 C11 C1 C2 -133.76(11) . . . .
C10 C9 C7 C8 -28.83(16) . . . .
C10 C9 C7 C6 70.19(14) . . . .
C5 C8 C1 O2 170.54(9) . . . .
C5 C8 C1 C11 -67.59(12) . . . .
C5 C8 C1 C2 53.71(12) . . . .
C5 C8 C7 C9 100.83(11) . . . .
C5 C8 C7 C6 -14.45(9) . . . .
C5 C4 C3 C2 -0.18(18) . . . .
C1 O2 C15 C14 -61.88(15) . . . .
C1 C8 C5 C4 -23.12(17) . . . .
C1 C8 C5 C6 139.12(10) . . . .
C1 C8 C7 C9 -12.94(16) . . . .
C1 C8 C7 C6 -128.23(11) . . . .
C1 C11 C13 C14 -17.67(18) . . . .
C1 C11 C13 C12 142.71(10) . . . .
C1 C11 C10 C9 -21.06(15) . . . .
C1 C11 C10 C12 -136.58(11) . . . .
C1 C2 C3 C4 35.13(15) . . . .
C9 C10 C12 C13 -96.46(12) . . . .
C9 C7 C6 C5 -101.44(11) . . . .
C7 C8 C5 C4 -147.16(13) . . . .
C7 C8 C5 C6 15.08(10) . . . .
C7 C8 C1 O2 -87.86(12) . . . .
C7 C8 C1 C11 34.01(14) . . . .
C7 C8 C1 C2 155.31(10) . . . .
C14 C13 C12 C10 135.52(18) . . . .
C15 O2 C1 C8 159.74(10) . . . .
C15 O2 C1 C11 38.31(13) . . . .
C15 O2 C1 C2 -86.38(12) . . . .
C4 C5 C6 C7 142.95(17) . . . .
C12 C13 C14 C15 -154.05(16) . . . .
C12 C10 C9 O1 -36.47(19) . . . .
C12 C10 C9 C7 144.39(12) . . . .
C3 C2 C1 O2 -176.08(10) . . . .
C3 C2 C1 C8 -61.68(12) . . . .
C3 C2 C1 C11 59.20(13) . . . .
C6 C5 C4 C3 -158.57(15) . . . .
