#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:55:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178450 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/71/4027190.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_4027190
loop_
_publ_author_name
'Jelena Veljković'
'Lidija Uzelac'
'Krešimir Molčanov'
'Kata Mlinarić-Majerski'
'Marijeta Kralj'
'Peter Wan'
'Nikola Basarić'
_publ_section_title
;
 Sterically Congested Adamantylnaphthalene Quinone Methides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4596
_journal_page_last               4610
_journal_paper_doi               10.1021/jo3002479
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H20 O1'
_chemical_formula_sum            'C20 H20 O'
_chemical_formula_weight         276.36
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2b'
_symmetry_space_group_name_H-M   'P b c 21'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2012-01-23T13:13:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6033(6)
_cell_length_b                   13.7896(8)
_cell_length_c                   11.3522(6)
_cell_measurement_reflns_used    1926
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.4669
_cell_measurement_theta_min      3.2022
_cell_volume                     1503.32(15)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
        (compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
        (compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
        (compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'CCD, ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4156
_diffrn_reflns_theta_full        76.66
_diffrn_reflns_theta_max         76.66
_diffrn_reflns_theta_min         4.6
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.154
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.3
_refine_diff_density_min         -0.264
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.9(11)
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_gt           0.0867
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1526P)²+0.4018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2807
_reflns_number_gt                1633
_reflns_number_total             2311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3002479_si_002.cif
_cod_data_source_block           nikola-qm-1,2
_cod_database_code               4027190
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, 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_calc_flag
_atom_site_refinement_flags
C15 C 0.6195(5) 0.1128(4) 0.1373(5) 0.0689(12) Uani 1 d .
C11 C 0.7932(5) 0.0955(3) -0.0251(4) 0.0577(10) Uani 1 d .
C20 C 0.7215(5) 0.1559(4) 0.0647(5) 0.0660(12) Uani 1 d .
C12 C 0.7089(5) 0.0119(4) -0.0711(5) 0.0654(11) Uani 1 d .
O1 O 0.7150(4) -0.0197(4) -0.1709(4) 0.0915(14) Uani 1 d .
C3 C 1.0321(6) 0.1662(4) 0.0139(5) 0.0743(14) Uani 1 d .
H3 H 0.9834 0.2039 0.0744 0.089 Uiso 1 calc R
C2 C 0.9304(5) 0.1039(3) -0.0517(4) 0.0582(10) Uani 1 d .
C1 C 1.0052(6) 0.0445(5) -0.1439(5) 0.0822(16) Uani 1 d .
H1 H 0.9387 0.0032 -0.1861 0.099 Uiso 1 calc R
C16 C 0.5559(6) 0.1684(5) 0.2274(6) 0.0869(17) Uani 1 d .
H16 H 0.4886 0.1403 0.2754 0.104 Uiso 1 calc R
C10 C 1.1424(6) 0.1010(6) 0.0714(6) 0.100(2) Uani 1 d .
H10A H 1.2074 0.1406 0.1156 0.12 Uiso 1 calc R
H10B H 1.0976 0.0566 0.1258 0.12 Uiso 1 calc R
C14 C 0.5760(5) 0.0140(5) 0.1130(6) 0.0774(15) Uani 1 d .
H14 H 0.5178 -0.0174 0.1663 0.093 Uiso 1 calc R
C19 C 0.7481(6) 0.2537(5) 0.0794(7) 0.0816(16) Uani 1 d .
H19 H 0.8096 0.2844 0.0283 0.098 Uiso 1 calc R
C6 C 1.2916(6) 0.1118(5) -0.1063(6) 0.0804(15) Uani 1 d .
H6A H 1.3586 0.1518 -0.0649 0.097 Uiso 1 calc R
H6B H 1.3408 0.0743 -0.1654 0.097 Uiso 1 calc R
C5 C 1.1834(7) 0.1750(6) -0.1645(6) 0.0939(19) Uani 1 d .
H5 H 1.2291 0.2187 -0.2205 0.113 Uiso 1 calc R
C13 C 0.6174(6) -0.0330(5) 0.0163(6) 0.0792(15) Uani 1 d .
H13 H 0.5871 -0.0963 0.0041 0.095 Uiso 1 calc R
C7 C 1.2197(6) 0.0445(5) -0.0207(8) 0.094(2) Uani 1 d .
H7 H 1.2895 0.0034 0.0177 0.113 Uiso 1 calc R
C9 C 1.0777(8) 0.1128(7) -0.2296(6) 0.112(3) Uani 1 d .
H9A H 1.1244 0.0754 -0.2902 0.134 Uiso 1 calc R
H9B H 1.0093 0.1541 -0.2674 0.134 Uiso 1 calc R
C8 C 1.1159(7) -0.0184(5) -0.0824(10) 0.106(3) Uani 1 d .
H8A H 1.0712 -0.061 -0.0258 0.127 Uiso 1 calc R
H8B H 1.163 -0.0584 -0.1402 0.127 Uiso 1 calc R
C4 C 1.1073(7) 0.2346(5) -0.0717(10) 0.108(3) Uani 1 d .
H4A H 1.0404 0.2771 -0.1094 0.13 Uiso 1 calc R
H4B H 1.1734 0.2745 -0.0288 0.13 Uiso 1 calc R
C17 C 0.5926(7) 0.2628(6) 0.2443(7) 0.100(2) Uani 1 d .
H17 H 0.5554 0.2976 0.3071 0.12 Uiso 1 calc R
C18 C 0.6856(7) 0.3069(5) 0.1679(7) 0.097(2) Uani 1 d .
H18 H 0.7059 0.3725 0.1761 0.116 Uiso 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C20 C15 C16 119.5(5)
C20 C15 C14 118.9(5)
C16 C15 C14 121.4(5)
C2 C11 C20 123.7(4)
C2 C11 C12 120.8(4)
C20 C11 C12 114.8(4)
C19 C20 C15 117.9(5)
C19 C20 C11 123.0(4)
C15 C20 C11 119.1(5)
O1 C12 C13 120.6(5)
O1 C12 C11 125.0(5)
C13 C12 C11 114.4(5)
C2 C3 C10 109.0(5)
C2 C3 C4 110.1(6)
C10 C3 C4 107.7(5)
C2 C3 H3 110
C10 C3 H3 110
C4 C3 H3 110
C11 C2 C3 124.8(4)
C11 C2 C1 124.7(4)
C3 C2 C1 110.2(4)
C2 C1 C9 108.9(5)
C2 C1 C8 108.7(6)
C9 C1 C8 108.8(6)
C2 C1 H1 110.1
C9 C1 H1 110.1
C8 C1 H1 110.1
C17 C16 C15 120.5(6)
C17 C16 H16 119.8
C15 C16 H16 119.8
C7 C10 C3 110.5(5)
C7 C10 H10A 109.6
C3 C10 H10A 109.6
C7 C10 H10B 109.6
C3 C10 H10B 109.6
H10A C10 H10B 108.1
C13 C14 C15 121.8(5)
C13 C14 H14 119.1
C15 C14 H14 119.1
C18 C19 C20 121.7(6)
C18 C19 H19 119.2
C20 C19 H19 119.2
C5 C6 C7 108.8(5)
C5 C6 H6A 109.9
C7 C6 H6A 109.9
C5 C6 H6B 109.9
C7 C6 H6B 109.9
H6A C6 H6B 108.3
C6 C5 C9 110.3(7)
C6 C5 C4 109.8(6)
C9 C5 C4 108.7(5)
C6 C5 H5 109.3
C9 C5 H5 109.3
C4 C5 H5 109.3
C14 C13 C12 122.0(5)
C14 C13 H13 119
C12 C13 H13 119
C8 C7 C10 107.3(6)
C8 C7 C6 111.1(7)
C10 C7 C6 110.8(6)
C8 C7 H7 109.2
C10 C7 H7 109.2
C6 C7 H7 109.2
C5 C9 C1 110.1(5)
C5 C9 H9A 109.6
C1 C9 H9A 109.6
C5 C9 H9B 109.6
C1 C9 H9B 109.6
H9A C9 H9B 108.2
C7 C8 C1 110.2(5)
C7 C8 H8A 109.6
C1 C8 H8A 109.6
C7 C8 H8B 109.6
C1 C8 H8B 109.6
H8A C8 H8B 108.1
C5 C4 C3 109.4(5)
C5 C4 H4A 109.8
C3 C4 H4A 109.8
C5 C4 H4B 109.8
C3 C4 H4B 109.8
H4A C4 H4B 108.2
C16 C17 C18 119.8(6)
C16 C17 H17 120.1
C18 C17 H17 120.1
C19 C18 C17 120.2(7)
C19 C18 H18 119.9
C17 C18 H18 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C15 C20 1.412(6)
C15 C16 1.417(8)
C15 C14 1.451(8)
C11 C2 1.357(6)
C11 C20 1.486(7)
C11 C12 1.503(6)
C20 C19 1.382(8)
C12 O1 1.215(7)
C12 C13 1.463(8)
C3 C2 1.499(7)
C3 C10 1.535(9)
C3 C4 1.535(10)
C3 H3 0.98
C2 C1 1.510(6)
C1 C9 1.523(9)
C1 C8 1.539(10)
C1 H1 0.98
C16 C17 1.362(10)
C16 H16 0.93
C10 C7 1.500(11)
C10 H10A 0.97
C10 H10B 0.97
C14 C13 1.336(9)
C14 H14 0.93
C19 C18 1.381(9)
C19 H19 0.93
C6 C5 1.508(9)
C6 C7 1.511(9)
C6 H6A 0.97
C6 H6B 0.97
C5 C9 1.520(10)
C5 C4 1.523(12)
C5 H5 0.98
C13 H13 0.93
C7 C8 1.496(11)
C7 H7 0.98
C9 H9A 0.97
C9 H9B 0.97
C8 H8A 0.97
C8 H8B 0.97
C4 H4A 0.97
C4 H4B 0.97
C17 C18 1.385(10)
C17 H17 0.93
C18 H18 0.93
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
C16 C15 C20 C19 -4.6(8)
C14 C15 C20 C19 171.6(5)
C16 C15 C20 C11 176.6(5)
C14 C15 C20 C11 -7.1(7)
C2 C11 C20 C19 39.6(8)
C12 C11 C20 C19 -150.3(5)
C2 C11 C20 C15 -141.7(5)
C12 C11 C20 C15 28.4(6)
C2 C11 C12 O1 -42.7(8)
C20 C11 C12 O1 146.9(5)
C2 C11 C12 C13 135.6(5)
C20 C11 C12 C13 -34.8(6)
C20 C11 C2 C3 7.4(7)
C12 C11 C2 C3 -162.2(5)
C20 C11 C2 C1 -179.0(5)
C12 C11 C2 C1 11.4(7)
C10 C3 C2 C11 115.9(5)
C4 C3 C2 C11 -126.1(5)
C10 C3 C2 C1 -58.5(6)
C4 C3 C2 C1 59.5(6)
C11 C2 C1 C9 125.8(5)
C3 C2 C1 C9 -59.8(6)
C11 C2 C1 C8 -115.8(6)
C3 C2 C1 C8 58.6(6)
C20 C15 C16 C17 0.0(9)
C14 C15 C16 C17 -176.2(6)
C2 C3 C10 C7 60.5(6)
C4 C3 C10 C7 -58.9(7)
C20 C15 C14 C13 -8.0(8)
C16 C15 C14 C13 168.1(5)
C15 C20 C19 C18 4.9(9)
C11 C20 C19 C18 -176.3(6)
C7 C6 C5 C9 -59.5(7)
C7 C6 C5 C4 60.3(8)
C15 C14 C13 C12 0.0(9)
O1 C12 C13 C14 -159.8(6)
C11 C12 C13 C14 21.8(8)
C3 C10 C7 C8 -61.8(7)
C3 C10 C7 C6 59.7(7)
C5 C6 C7 C8 59.8(8)
C5 C6 C7 C10 -59.4(7)
C6 C5 C9 C1 59.9(7)
C4 C5 C9 C1 -60.5(8)
C2 C1 C9 C5 60.5(7)
C8 C1 C9 C5 -57.7(8)
C10 C7 C8 C1 61.9(8)
C6 C7 C8 C1 -59.3(8)
C2 C1 C8 C7 -60.9(8)
C9 C1 C8 C7 57.6(9)
C6 C5 C4 C3 -61.7(8)
C9 C5 C4 C3 59.0(8)
C2 C3 C4 C5 -59.1(7)
C10 C3 C4 C5 59.6(8)
C15 C16 C17 C18 4.5(11)
C20 C19 C18 C17 -0.5(11)
C16 C17 C18 C19 -4.3(11)
