#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227919.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_2227919
loop_
_publ_author_name
'Mohammad, Akhtar'
'Shah, Muhammad Raza'
'Anis, Itrat'
'McKee, Vickie'
'Frese, Josef W. A.'
_publ_section_title
;
 7-[2-(3-Furyl)ethyl]-7,8-dimethyl-3,5,6,6a,7,8,9,10-octahydro-1H-naphtho[1,8a-c]furan-3-one
;
_journal_coeditor_code           PV2325
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2529
_journal_paper_doi               10.1107/S1600536810035373
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H26 O3'
_chemical_formula_moiety         'C20 H26 O3'
_chemical_formula_sum            'C20 H26 O3'
_chemical_formula_weight         314.41
_chemical_name_systematic
;
7-[2-(3-Furyl)ethyl]-7,8-dimethyl-3,5,6,6a,7,8,9,10-octahydro-1H-
naphtho[1,8a-c]furan-3-one
;
_space_group_IT_number           19
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1343(8)
_cell_length_b                   11.8752(10)
_cell_length_c                   15.5255(13)
_cell_measurement_reflns_used    4592
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.62
_cell_volume                     1684.1(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'APEX2 (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement
;SHELXL97 (Sheldrick, 20088b) and
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_solution
;SHELXS97 (Sheldrick, 20088b) and OLEX2
(Dolomanov et al., 2009)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17210
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.1493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                2124
_reflns_number_total             2378
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2325.cif
_cod_data_source_block           I
_cod_database_code               2227919
_cod_database_fobs_code          2227919
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_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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7909(2) 0.60429(16) 0.47103(12) 0.0302(4) Uani d . 1 . .
H H1 0.7308 0.5466 0.4945 0.036 Uiso calc R 1 . .
O O1 0.90632(16) 0.65328(12) 0.51339(8) 0.0364(3) Uani d . 1 . .
C C2 0.9617(2) 0.73164(17) 0.45834(13) 0.0363(4) Uani d . 1 . .
H H2 1.0422 0.7795 0.4710 0.044 Uiso calc R 1 . .
C C3 0.8874(2) 0.73222(16) 0.38386(13) 0.0313(4) Uani d . 1 . .
H H3 0.9060 0.7787 0.3353 0.038 Uiso calc R 1 . .
C C4 0.77393(19) 0.64889(14) 0.39168(11) 0.0243(3) Uani d . 1 . .
C C5 0.6611(2) 0.61806(14) 0.32528(11) 0.0263(4) Uani d . 1 . .
H H5A 0.5867 0.5685 0.3520 0.032 Uiso calc R 1 . .
H H5B 0.7089 0.5754 0.2783 0.032 Uiso calc R 1 . .
C C6 0.58507(19) 0.72228(13) 0.28730(11) 0.0232(3) Uani d . 1 . .
H H6A 0.6615 0.7716 0.2624 0.028 Uiso calc R 1 . .
H H6B 0.5391 0.7642 0.3353 0.028 Uiso calc R 1 . .
C C7 0.46681(18) 0.70275(13) 0.21744(10) 0.0205(3) Uani d . 1 . .
C C8 0.4031(2) 0.82001(13) 0.19732(12) 0.0274(4) Uani d . 1 . .
H H8A 0.3394 0.8439 0.2447 0.041 Uiso calc R 1 . .
H H8B 0.3461 0.8165 0.1439 0.041 Uiso calc R 1 . .
H H8C 0.4831 0.8742 0.1905 0.041 Uiso calc R 1 . .
C C9 0.53645(18) 0.64730(14) 0.13577(10) 0.0223(3) Uani d . 1 . .
H H9 0.5889 0.5781 0.1557 0.027 Uiso calc R 1 . .
C C10 0.6498(2) 0.72123(16) 0.09011(12) 0.0310(4) Uani d . 1 . .
H H10A 0.6954 0.6784 0.0432 0.047 Uiso calc R 1 . .
H H10B 0.7252 0.7444 0.1314 0.047 Uiso calc R 1 . .
H H10C 0.6015 0.7881 0.0665 0.047 Uiso calc R 1 . .
C C11 0.42124(19) 0.60881(15) 0.06978(10) 0.0260(4) Uani d . 1 . .
H H11A 0.3736 0.6761 0.0447 0.031 Uiso calc R 1 . .
H H11B 0.4713 0.5683 0.0225 0.031 Uiso calc R 1 . .
C C12 0.30336(19) 0.53222(15) 0.10773(10) 0.0256(4) Uani d . 1 . .
H H12A 0.3482 0.4606 0.1268 0.031 Uiso calc R 1 . .
H H12B 0.2295 0.5147 0.0630 0.031 Uiso calc R 1 . .
C C13 0.22816(18) 0.59026(14) 0.18497(10) 0.0219(3) Uani d . 1 . .
C C14 0.34897(18) 0.61938(13) 0.25089(10) 0.0194(3) Uani d . 1 . .
H H14 0.4034 0.5471 0.2589 0.023 Uiso calc R 1 . .
C C15 0.2826(2) 0.64366(14) 0.33993(10) 0.0237(3) Uani d . 1 . .
H H15A 0.3606 0.6675 0.3803 0.028 Uiso calc R 1 . .
H H15B 0.2101 0.7053 0.3355 0.028 Uiso calc R 1 . .
C C16 0.2082(2) 0.53662(15) 0.37365(11) 0.0280(4) Uani d . 1 . .
H H16A 0.2832 0.4784 0.3853 0.034 Uiso calc R 1 . .
H H16B 0.1571 0.5535 0.4284 0.034 Uiso calc R 1 . .
C C17 0.1000(2) 0.49250(14) 0.30904(12) 0.0281(4) Uani d . 1 . .
H H17 0.0218 0.4459 0.3279 0.034 Uiso calc R 1 . .
C C18 0.11187(19) 0.51761(15) 0.22587(11) 0.0257(4) Uani d . 1 . .
C C19 -0.0169(2) 0.52032(18) 0.16805(12) 0.0330(4) Uani d . 1 . .
O O4 -0.11876(15) 0.45656(14) 0.15980(10) 0.0450(4) Uani d . 1 . .
O O5 -0.00711(14) 0.61773(13) 0.12226(9) 0.0390(3) Uani d . 1 . .
C C20 0.12289(19) 0.68107(16) 0.14996(12) 0.0298(4) Uani d . 1 . .
H H20A 0.0974 0.7361 0.1955 0.036 Uiso calc R 1 . .
H H20B 0.1674 0.7218 0.1009 0.036 Uiso calc 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 0.0000 '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 0.0000 '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
C4 C1 O1 . . 111.05(17) ?
C4 C1 H1 . . 124.5 ?
O1 C1 H1 . . 124.5 ?
C2 O1 C1 . . 105.92(15) ?
C3 C2 O1 . . 110.93(18) ?
C3 C2 H2 . . 124.5 ?
O1 C2 H2 . . 124.5 ?
C2 C3 C4 . . 106.76(18) ?
C2 C3 H3 . . 126.6 ?
C4 C3 H3 . . 126.6 ?
C1 C4 C3 . . 105.33(16) ?
C1 C4 C5 . . 127.53(17) ?
C3 C4 C5 . . 127.14(16) ?
C4 C5 C6 . . 112.14(14) ?
C4 C5 H5A . . 109.2 ?
C6 C5 H5A . . 109.2 ?
C4 C5 H5B . . 109.2 ?
C6 C5 H5B . . 109.2 ?
H5A C5 H5B . . 107.9 ?
C5 C6 C7 . . 117.61(13) ?
C5 C6 H6A . . 107.9 ?
C7 C6 H6A . . 107.9 ?
C5 C6 H6B . . 107.9 ?
C7 C6 H6B . . 107.9 ?
H6A C6 H6B . . 107.2 ?
C8 C7 C6 . . 105.68(13) ?
C8 C7 C14 . . 112.47(13) ?
C6 C7 C14 . . 110.19(12) ?
C8 C7 C9 . . 111.70(13) ?
C6 C7 C9 . . 110.32(13) ?
C14 C7 C9 . . 106.55(12) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C11 . . 108.94(14) ?
C10 C9 C7 . . 114.14(14) ?
C11 C9 C7 . . 112.76(13) ?
C10 C9 H9 . . 106.9 ?
C11 C9 H9 . . 106.9 ?
C7 C9 H9 . . 106.9 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 C9 . . 113.72(13) ?
C12 C11 H11A . . 108.8 ?
C9 C11 H11A . . 108.8 ?
C12 C11 H11B . . 108.8 ?
C9 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
C11 C12 C13 . . 110.32(14) ?
C11 C12 H12A . . 109.6 ?
C13 C12 H12A . . 109.6 ?
C11 C12 H12B . . 109.6 ?
C13 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
C18 C13 C20 . . 96.26(13) ?
C18 C13 C14 . . 110.63(13) ?
C20 C13 C14 . . 121.47(14) ?
C18 C13 C12 . . 112.63(14) ?
C20 C13 C12 . . 108.38(14) ?
C14 C13 C12 . . 107.26(13) ?
C15 C14 C13 . . 110.88(13) ?
C15 C14 C7 . . 117.05(13) ?
C13 C14 C7 . . 114.63(13) ?
C15 C14 H14 . . 104.2 ?
C13 C14 H14 . . 104.2 ?
C7 C14 H14 . . 104.2 ?
C16 C15 C14 . . 109.05(13) ?
C16 C15 H15A . . 109.9 ?
C14 C15 H15A . . 109.9 ?
C16 C15 H15B . . 109.9 ?
C14 C15 H15B . . 109.9 ?
H15A C15 H15B . . 108.3 ?
C17 C16 C15 . . 110.66(14) ?
C17 C16 H16A . . 109.5 ?
C15 C16 H16A . . 109.5 ?
C17 C16 H16B . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 108.1 ?
C18 C17 C16 . . 121.11(16) ?
C18 C17 H17 . . 119.4 ?
C16 C17 H17 . . 119.4 ?
C17 C18 C19 . . 121.95(17) ?
C17 C18 C13 . . 126.47(16) ?
C19 C18 C13 . . 106.96(15) ?
O4 C19 O5 . . 121.90(18) ?
O4 C19 C18 . . 131.6(2) ?
O5 C19 C18 . . 106.47(15) ?
C19 O5 C20 . . 109.57(14) ?
O5 C20 C13 . . 104.40(14) ?
O5 C20 H20A . . 110.9 ?
C13 C20 H20A . . 110.9 ?
O5 C20 H20B . . 110.9 ?
C13 C20 H20B . . 110.9 ?
H20A C20 H20B . . 108.9 ?
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
C1 C4 . 1.350(3) ?
C1 O1 . 1.372(2) ?
C1 H1 . 0.9500 ?
O1 C2 . 1.361(3) ?
C2 C3 . 1.341(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.438(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.503(2) ?
C5 C6 . 1.537(2) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.548(2) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.541(2) ?
C7 C14 . 1.552(2) ?
C7 C9 . 1.564(2) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.532(2) ?
C9 C11 . 1.538(2) ?
C9 H9 . 1.0000 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.528(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.544(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C18 . 1.509(2) ?
C13 C20 . 1.544(2) ?
C13 C14 . 1.544(2) ?
C14 C15 . 1.537(2) ?
C14 H14 . 1.0000 ?
C15 C16 . 1.534(2) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C17 . 1.502(3) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.330(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.480(2) ?
C19 O4 . 1.207(2) ?
C19 O5 . 1.361(3) ?
O5 C20 . 1.470(2) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
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
C4 C1 O1 C2 . . . . 0.5(2) ?
C1 O1 C2 C3 . . . . -0.8(2) ?
O1 C2 C3 C4 . . . . 0.8(2) ?
O1 C1 C4 C3 . . . . -0.1(2) ?
O1 C1 C4 C5 . . . . 179.74(15) ?
C2 C3 C4 C1 . . . . -0.4(2) ?
C2 C3 C4 C5 . . . . 179.75(17) ?
C1 C4 C5 C6 . . . . 131.66(19) ?
C3 C4 C5 C6 . . . . -48.6(2) ?
C4 C5 C6 C7 . . . . 179.56(14) ?
C5 C6 C7 C8 . . . . 175.77(15) ?
C5 C6 C7 C14 . . . . 54.02(18) ?
C5 C6 C7 C9 . . . . -63.35(18) ?
C8 C7 C9 C10 . . . . 53.24(19) ?
C6 C7 C9 C10 . . . . -63.98(17) ?
C14 C7 C9 C10 . . . . 176.42(14) ?
C8 C7 C9 C11 . . . . -71.78(18) ?
C6 C7 C9 C11 . . . . 171.00(13) ?
C14 C7 C9 C11 . . . . 51.41(16) ?
C10 C9 C11 C12 . . . . 178.88(14) ?
C7 C9 C11 C12 . . . . -53.32(19) ?
C9 C11 C12 C13 . . . . 55.58(19) ?
C11 C12 C13 C18 . . . . -179.20(14) ?
C11 C12 C13 C20 . . . . 75.54(17) ?
C11 C12 C13 C14 . . . . -57.24(17) ?
C18 C13 C14 C15 . . . . -39.51(18) ?
C20 C13 C14 C15 . . . . 72.02(19) ?
C12 C13 C14 C15 . . . . -162.72(13) ?
C18 C13 C14 C7 . . . . -174.78(13) ?
C20 C13 C14 C7 . . . . -63.25(19) ?
C12 C13 C14 C7 . . . . 62.01(17) ?
C8 C7 C14 C15 . . . . -67.88(18) ?
C6 C7 C14 C15 . . . . 49.74(18) ?
C9 C7 C14 C15 . . . . 169.42(13) ?
C8 C7 C14 C13 . . . . 64.53(18) ?
C6 C7 C14 C13 . . . . -177.85(13) ?
C9 C7 C14 C13 . . . . -58.16(16) ?
C13 C14 C15 C16 . . . . 63.59(17) ?
C7 C14 C15 C16 . . . . -162.32(14) ?
C14 C15 C16 C17 . . . . -53.83(19) ?
C15 C16 C17 C18 . . . . 23.3(2) ?
C16 C17 C18 C19 . . . . -152.89(18) ?
C16 C17 C18 C13 . . . . -0.2(3) ?
C20 C13 C18 C17 . . . . -118.6(2) ?
C14 C13 C18 C17 . . . . 8.4(3) ?
C12 C13 C18 C17 . . . . 128.46(19) ?
C20 C13 C18 C19 . . . . 37.37(17) ?
C14 C13 C18 C19 . . . . 164.41(14) ?
C12 C13 C18 C19 . . . . -75.55(18) ?
C17 C18 C19 O4 . . . . -44.6(3) ?
C13 C18 C19 O4 . . . . 158.06(19) ?
C17 C18 C19 O5 . . . . 132.85(18) ?
C13 C18 C19 O5 . . . . -24.47(19) ?
O4 C19 O5 C20 . . . . 176.28(17) ?
C18 C19 O5 C20 . . . . -1.49(19) ?
C19 O5 C20 C13 . . . . 25.98(18) ?
C18 C13 C20 O5 . . . . -37.35(15) ?
C14 C13 C20 O5 . . . . -156.21(14) ?
C12 C13 C20 O5 . . . . 79.04(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28488923
