#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/49/2014928.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2014928
loop_
_publ_author_name
'Wojciechowski, Jakub'
'Krawczyk, Henryk'
'Śliwiński, Marcin'
'Wolf, Wojciech M.'
_publ_section_title
;X-ray investigations of bicyclic α-methylene-δ-valerolactones. III.
 trans-(4aR,8aR)-4a-Methoxy-3-methyleneperhydrochromen-2-one
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o351
_journal_page_last               o353
_journal_paper_doi               10.1107/S0108270105010607
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C11 H16 O3'
_chemical_formula_moiety         'C11 H16 O3'
_chemical_formula_sum            'C11 H16 O3'
_chemical_formula_weight         196.24
_chemical_melting_point          397
_chemical_name_systematic
;
(4aR,8aR)-4a-Methoxy-3-methyleneperhydrochromen-2-one
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1555(2)
_cell_length_b                   12.3990(2)
_cell_length_c                   13.3019(2)
_cell_measurement_reflns_used    4441
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6
_cell_measurement_theta_min      3.3
_cell_volume                     1015.23(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.95
_diffrn_measured_fraction_theta_max 0.95
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5162
_diffrn_reflns_theta_full        70.74
_diffrn_reflns_theta_max         70.74
_diffrn_reflns_theta_min         4.88
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.8954
_exptl_absorpt_correction_T_min  0.7951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SHELXTL; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.137
_refine_ls_abs_structure_details 'Flack (1983), with 720 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0045(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Bruker, 2003)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0295
_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)+(0.049P)²+0.0969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                1793
_reflns_number_total             1816
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq1200.cif
_cod_data_source_block           I
_cod_database_code               2014928
_cod_database_fobs_code          2014928
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_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
_atom_site_type_symbol
O1 -0.15801(17) 0.58118(8) -0.04022(7) 0.0501(3) Uani d . 1 . . O
O2 -0.12023(16) 0.43031(7) 0.11624(7) 0.0449(2) Uani d . 1 . . O
O3 -0.4441(2) 0.67943(10) -0.01049(10) 0.0680(4) Uani d . 1 . . O
C1 0.0480(2) 0.53461(11) -0.01040(10) 0.0426(3) Uani d . 1 . . C
H11 0.161(3) 0.5889(14) -0.0245(12) 0.045(4) Uiso d . 1 . . H
C2 -0.2772(2) 0.64159(11) 0.02220(11) 0.0475(3) Uani d . 1 . . C
C3 -0.2046(2) 0.65591(10) 0.12862(11) 0.0465(3) Uani d . 1 . . C
C4 -0.3376(4) 0.70628(15) 0.19026(15) 0.0654(5) Uani d . 1 . . C
H42 -0.480(4) 0.733(2) 0.1699(18) 0.092(8) Uiso d . 1 . . H
H41 -0.309(3) 0.7139(15) 0.2594(16) 0.063(5) Uiso d . 1 . . H
C5 0.0115(3) 0.61033(12) 0.15846(10) 0.0467(3) Uani d . 1 . . C
H51 0.131(3) 0.6604(14) 0.1373(12) 0.050(4) Uiso d . 1 . . H
H52 0.023(3) 0.6017(16) 0.2326(15) 0.066(5) Uiso d . 1 . . H
C6 0.0537(2) 0.50583(10) 0.10142(9) 0.0392(3) Uani d . 1 . . C
C7 0.2744(3) 0.45541(12) 0.12449(11) 0.0480(3) Uani d . 1 . . C
H71 0.389(3) 0.5051(13) 0.1136(11) 0.047(4) Uiso d . 1 . . H
H72 0.278(3) 0.4355(14) 0.1958(13) 0.056(5) Uiso d . 1 . . H
C8 0.3210(3) 0.35796(13) 0.05820(12) 0.0553(4) Uani d . 1 . . C
H81 0.213(3) 0.2995(14) 0.0748(11) 0.049(4) Uiso d . 1 . . H
H82 0.470(3) 0.3294(16) 0.0729(14) 0.060(5) Uiso d . 1 . . H
C9 0.3071(3) 0.38754(15) -0.05291(13) 0.0623(4) Uani d . 1 . . C
H91 0.434(3) 0.4406(17) -0.0687(15) 0.067(5) Uiso d . 1 . . H
H92 0.326(3) 0.3235(18) -0.0949(15) 0.073(6) Uiso d . 1 . . H
C10 0.0871(3) 0.43784(13) -0.07732(10) 0.0533(4) Uani d . 1 . . C
H101 0.078(3) 0.4604(14) -0.1482(14) 0.059(5) Uiso d . 1 . . H
H102 -0.036(3) 0.3874(15) -0.0651(13) 0.053(4) Uiso d . 1 . . H
C11 -0.1582(3) 0.39879(14) 0.21747(11) 0.0598(4) Uani d . 1 . . C
H111 -0.0256 0.3723 0.2463 0.093(7) Uiso calc R 1 . . H
H112 -0.2663 0.3430 0.2191 0.106(8) Uiso calc R 1 . . H
H113 -0.2083 0.4598 0.2553 0.128(10) Uiso calc R 1 . . H
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 0.0000 0.0000 '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
_geom_angle_publ_flag
C4 C3 C2 117.42(16) y
C4 C3 C5 124.46(16) y
C2 C3 C5 118.11(12) y
C11 O2 C6 115.59(11) n
O3 C2 O1 117.37(14) n
O3 C2 C3 123.21(15) n
O1 C2 C3 119.38(12) n
C2 O1 C1 122.23(11) n
O1 C1 C10 107.10(12) n
O1 C1 C6 112.27(11) n
C10 C1 C6 112.54(11) n
O1 C1 H11 107.1(9) n
C10 C1 H11 108.4(9) n
C6 C1 H11 109.2(9) n
C3 C4 H42 123.2(15) n
C3 C4 H41 122.7(12) n
H42 C4 H41 113.8(18) n
C3 C5 C6 109.88(11) n
C3 C5 H51 110.2(10) n
C6 C5 H51 105.1(10) n
C3 C5 H52 111.4(11) n
C6 C5 H52 113.0(11) n
H51 C5 H52 107.0(15) n
O2 C6 C5 111.04(11) n
O2 C6 C7 111.64(10) n
C5 C6 C7 113.57(11) n
O2 C6 C1 105.58(10) n
C5 C6 C1 106.37(10) n
C7 C6 C1 108.13(11) n
C8 C7 C6 112.10(12) n
C8 C7 H71 106.8(10) n
C6 C7 H71 111.3(10) n
C8 C7 H72 110.8(11) n
C6 C7 H72 108.6(11) n
H71 C7 H72 107.1(14) n
C7 C8 C9 111.08(14) n
C7 C8 H81 108.6(9) n
C9 C8 H81 110.4(9) n
C7 C8 H82 109.9(11) n
C9 C8 H82 109.0(11) n
H81 C8 H82 107.8(15) n
C8 C9 C10 110.74(14) n
C8 C9 H91 107.7(11) n
C10 C9 H91 111.3(11) n
C8 C9 H92 110.6(12) n
C10 C9 H92 108.3(12) n
H91 C9 H92 108.2(16) n
C1 C10 C9 109.88(14) n
C1 C10 H101 109.2(10) n
C9 C10 H101 111.7(11) n
C1 C10 H102 106.3(10) n
C9 C10 H102 112.6(10) n
H101 C10 H102 107.0(15) n
O2 C11 H111 109.5 n
O2 C11 H112 109.5 n
H111 C11 H112 109.5 n
O2 C11 H113 109.5 n
H111 C11 H113 109.5 n
H112 C11 H113 109.5 n
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
O1 C2 . 1.3374(18) y
O1 C1 . 1.4490(17) y
O3 C2 . 1.2105(19) y
C2 C3 . 1.495(2) y
C3 C4 . 1.316(2) y
O2 C11 . 1.4214(16) n
O2 C6 . 1.4359(16) n
C1 C10 . 1.513(2) n
C1 C6 . 1.5300(16) n
C6 C7 . 1.527(2) n
C7 C8 . 1.523(2) n
C3 C5 . 1.499(2) n
C9 C10 . 1.526(3) n
C8 C9 . 1.525(2) n
C5 C6 . 1.5238(18) n
C4 H42 . 0.98(3) n
C4 H41 . 0.94(2) n
C5 H51 . 1.005(18) n
C5 H52 . 0.99(2) n
C1 H11 . 0.986(17) n
C7 H71 . 0.945(17) n
C7 H72 . 0.981(17) n
C8 H81 . 1.009(18) n
C8 H82 . 1.00(2) n
C9 H91 . 1.04(2) n
C9 H92 . 0.98(2) n
C10 H101 . 0.985(19) n
C10 H102 . 0.995(18) n
C11 H111 . 0.9600 n
C11 H112 . 0.9600 n
C11 H113 . 0.9600 n
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
C3 O3 3.035(2) 1_555 4_565 y
C2 O3 3.025(2) 1_555 4_565 y
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H11 O3 1_655 0.986(17) 2.683(16) 3.605(2) 156.0(10)
C5 H51 O3 4_565 1.005(18) 2.646(17) 3.278(2) 121.0(10)
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_publ_flag
C2 O1 C1 C6 32.16(16) y
O1 C1 C6 C5 -58.90(14) y
C1 O1 C2 C3 -4.28(18) y
O1 C2 C3 C5 5.81(18) y
C2 C3 C5 C6 -34.72(16) y
C3 C5 C6 C1 59.24(15) y
C1 O1 C2 O3 178.00(13) n
O3 C2 C3 C4 4.6(2) n
C11 O2 C6 C5 -60.00(15) n
C11 O2 C6 C7 67.85(15) n
C11 O2 C6 C1 -174.88(12) n
C10 C1 C6 O2 -61.78(15) n
C10 C1 C6 C7 57.84(16) n
O2 C6 C7 C8 59.57(15) n
C1 C6 C7 C8 -56.15(15) n
C6 C7 C8 C9 56.40(19) n
C7 C8 C9 C10 -55.4(2) n
C6 C1 C10 C9 -58.58(17) n
C8 C9 C10 C1 56.06(19) n
O1 C2 C3 C4 -173.00(14) n
O3 C2 C3 C5 -176.61(14) n
O1 C1 C10 C9 177.56(11) n
C5 C6 C7 C8 -173.95(13) n
C10 C1 C6 C5 -179.84(13) n
C3 C5 C6 O2 -55.14(14) n
C3 C5 C6 C7 178.06(11) n
C3 C5 C6 C1 59.24(15) n
O1 C1 C6 O2 59.16(13) n
C4 C3 C5 C6 144.00(15) n
C2 O1 C1 C10 156.18(12) n
O1 C1 C6 C7 178.78(11) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9724947
