#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/94/2219415.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_2219415
loop_
_publ_author_name
'Kitamura, Chitoshi'
'Kawase, Takeshi'
_publ_section_title
;
 3-(5,6,7,8-Tetrahydro-2-naphthyl)isobenzofuran-1(3H)-one
;
_journal_coeditor_code           PK2111
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1696
_journal_paper_doi               10.1107/S1600536808024598
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H16 O2'
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31
_chemical_name_systematic
;
3-(5,6,7,8-Tetrahydro-2-naphthyl)isobenzofuran-1(3H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 109.0970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2950(11)
_cell_length_b                   15.8251(10)
_cell_length_c                   7.8092(10)
_cell_measurement_reflns_used    4161
_cell_measurement_temperature    223
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.0448
_cell_volume                     1319.0(2)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2001)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2001)'
_computing_data_reduction        'WinGX (Farrugia, 1999)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type
;
Rigaku/MSC Mercury CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating-anode X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5765
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(NUMABS; Higashi, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.1
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1123P)²+0.367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                2502
_reflns_number_total             2955
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2111.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2219415
_cod_database_fobs_code          2219415
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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 1.02994(10) 0.24031(7) 0.24158(14) 0.0297(2) Uani d . 1 . .
C C2 0.88406(10) 0.15608(7) 0.31444(13) 0.0275(2) Uani d . 1 . .
H H2 0.8899 0.1481 0.4427 0.033 Uiso calc R 1 . .
C C3 0.97929(9) 0.10068(7) 0.27234(12) 0.0253(2) Uani d . 1 . .
C C4 0.99036(10) 0.01332(7) 0.27188(13) 0.0298(2) Uani d . 1 . .
H H4 0.9325 -0.0218 0.3009 0.036 Uiso calc R 1 . .
C C5 1.08967(11) -0.02030(7) 0.22709(14) 0.0333(3) Uani d . 1 . .
H H5 1.0999 -0.0793 0.2274 0.04 Uiso calc R 1 . .
C C6 1.17465(11) 0.03146(8) 0.18158(14) 0.0349(3) Uani d . 1 . .
H H6 1.241 0.0069 0.1514 0.042 Uiso calc R 1 . .
C C7 1.16291(10) 0.11850(7) 0.18020(14) 0.0314(2) Uani d . 1 . .
H H7 1.2193 0.1537 0.1481 0.038 Uiso calc R 1 . .
C C8 1.06447(10) 0.15181(7) 0.22818(12) 0.0261(2) Uani d . 1 . .
C C9 0.71587(10) 0.15338(7) 0.00822(13) 0.0268(2) Uani d . 1 . .
H H9 0.7772 0.1683 -0.0437 0.032 Uiso calc R 1 . .
C C10 0.75057(10) 0.14339(6) 0.19540(13) 0.0254(2) Uani d . 1 . .
C C11 0.65959(11) 0.12144(7) 0.27084(14) 0.0309(2) Uani d . 1 . .
H H11 0.6811 0.1149 0.397 0.037 Uiso calc R 1 . .
C C12 0.53701(11) 0.10919(8) 0.16038(14) 0.0333(3) Uani d . 1 . .
H H12 0.4763 0.0939 0.2131 0.04 Uiso calc R 1 . .
C C13 0.50144(10) 0.11891(6) -0.02704(13) 0.0272(2) Uani d . 1 B .
C C14 0.36564(10) 0.10711(8) -0.14102(15) 0.0368(3) Uani d D 1 . .
H H14A 0.3166 0.1534 -0.1148 0.044 Uiso calc R 1 A 1
H H14B 0.3353 0.0543 -0.1046 0.044 Uiso calc R 1 A 1
C C15A 0.34138(19) 0.10439(13) -0.3451(2) 0.0362(5) Uani d P 0.838(4) B 1
H H15A 0.3638 0.0486 -0.3796 0.043 Uiso calc PR 0.838(4) B 1
H H15B 0.2522 0.1141 -0.4099 0.043 Uiso calc PR 0.838(4) B 1
C C16A 0.41910(14) 0.17205(11) -0.39664(18) 0.0363(5) Uani d P 0.838(4) B 1
H H16A 0.3992 0.2275 -0.3573 0.044 Uiso calc PR 0.838(4) B 1
H H16B 0.3988 0.1734 -0.5286 0.044 Uiso calc PR 0.838(4) B 1
C C15B 0.3475(11) 0.1453(9) -0.3284(11) 0.070(5) Uani d PD 0.162(4) B 2
H H15C 0.2625 0.1325 -0.4085 0.084 Uiso calc PR 0.162(4) B 2
H H15D 0.3555 0.2068 -0.3169 0.084 Uiso calc PR 0.162(4) B 2
C C16B 0.4407(7) 0.1126(8) -0.4145(10) 0.056(3) Uani d PD 0.162(4) B 2
H H16C 0.4475 0.0509 -0.4059 0.068 Uiso calc PR 0.162(4) B 2
H H16D 0.4168 0.1292 -0.5422 0.068 Uiso calc PR 0.162(4) B 2
C C17 0.55921(11) 0.15332(8) -0.30668(14) 0.0347(3) Uani d D 1 . .
H H17A 0.5809 0.1019 -0.3597 0.042 Uiso calc R 1 B 1
H H17B 0.6084 0.2 -0.3311 0.042 Uiso calc R 1 B 1
C C18 0.59290(10) 0.14175(6) -0.10368(13) 0.0257(2) Uani d . 1 B .
O O1 0.92438(7) 0.24194(5) 0.29001(10) 0.0330(2) Uani d . 1 . .
O O2 1.07896(8) 0.30458(5) 0.21603(11) 0.0418(2) Uani d . 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 0.0016 '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 0.0106 0.006 '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
O2 C1 O1 121.36(10)
O2 C1 C8 130.29(11)
O1 C1 C8 108.35(9)
O1 C2 C10 109.57(8)
O1 C2 C3 103.71(8)
C10 C2 C3 115.52(8)
O1 C2 H2 109.3
C10 C2 H2 109.3
C3 C2 H2 109.3
C8 C3 C4 120.72(10)
C8 C3 C2 108.57(9)
C4 C3 C2 130.71(10)
C5 C4 C3 117.65(10)
C5 C4 H4 121.2
C3 C4 H4 121.2
C4 C5 C6 121.37(10)
C4 C5 H5 119.3
C6 C5 H5 119.3
C7 C6 C5 120.99(10)
C7 C6 H6 119.5
C5 C6 H6 119.5
C6 C7 C8 117.33(10)
C6 C7 H7 121.3
C8 C7 H7 121.3
C3 C8 C7 121.91(10)
C3 C8 C1 108.52(9)
C7 C8 C1 129.57(10)
C18 C9 C10 121.66(9)
C18 C9 H9 119.2
C10 C9 H9 119.2
C11 C10 C9 118.78(9)
C11 C10 C2 120.25(9)
C9 C10 C2 120.97(9)
C12 C11 C10 119.99(9)
C12 C11 H11 120
C10 C11 H11 120
C11 C12 C13 121.65(10)
C11 C12 H12 119.2
C13 C12 H12 119.2
C12 C13 C18 118.55(9)
C12 C13 C14 119.53(9)
C18 C13 C14 121.90(9)
C13 C14 C15A 114.77(11)
C13 C14 C15B 107.8(5)
C13 C14 H14A 108.6
C15A C14 H14A 108.6
C15B C14 H14A 89.8
C13 C14 H14B 108.6
C15A C14 H14B 108.6
C15B C14 H14B 131.5
H14A C14 H14B 107.6
C16A C15A C14 109.54(14)
C16A C15A H15A 109.8
C14 C15A H15A 109.8
C16A C15A H15B 109.8
C14 C15A H15B 109.8
H15A C15A H15B 108.2
C15A C16A C17 109.93(13)
C15A C16A H16A 109.7
C17 C16A H16A 109.7
C15A C16A H16B 109.7
C17 C16A H16B 109.7
H16A C16A H16B 108.2
C16B C15B C14 113.2(8)
C16B C15B H15C 108.9
C14 C15B H15C 108.9
C16B C15B H15D 108.9
C14 C15B H15D 108.9
H15C C15B H15D 107.7
C17 C16B C15B 103.3(8)
C17 C16B H16C 111.1
C15B C16B H16C 111.1
C17 C16B H16D 111.1
C15B C16B H16D 111.1
H16C C16B H16D 109.1
C16B C17 C18 114.5(4)
C18 C17 C16A 111.74(10)
C16B C17 H17A 72.7
C18 C17 H17A 109.3
C16A C17 H17A 109.3
C16B C17 H17B 133.2
C18 C17 H17B 109.3
C16A C17 H17B 109.3
H17A C17 H17B 107.9
C9 C18 C13 119.38(9)
C9 C18 C17 119.92(9)
C13 C18 C17 120.69(9)
C1 O1 C2 110.84(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.2054(13)
C1 O1 1.3639(14)
C1 C8 1.4668(15)
C2 O1 1.4651(13)
C2 C10 1.5037(14)
C2 C3 1.5050(14)
C2 H2 0.99
C3 C8 1.3844(14)
C3 C4 1.3881(15)
C4 C5 1.3858(15)
C4 H4 0.94
C5 C6 1.3935(17)
C5 H5 0.94
C6 C7 1.3834(16)
C6 H6 0.94
C7 C8 1.3882(15)
C7 H7 0.94
C9 C18 1.3901(15)
C9 C10 1.3930(14)
C9 H9 0.94
C10 C11 1.3856(14)
C11 C12 1.3846(16)
C11 H11 0.94
C12 C13 1.3937(14)
C12 H12 0.94
C13 C18 1.4002(14)
C13 C14 1.5122(15)
C14 C15A 1.527(2)
C14 C15B 1.534(9)
C14 H14A 0.98
C14 H14B 0.98
C15A C16A 1.520(2)
C15A H15A 0.98
C15A H15B 0.98
C16A C17 1.5357(19)
C16A H16A 0.98
C16A H16B 0.98
C15B C16B 1.514(9)
C15B H15C 0.98
C15B H15D 0.98
C16B C17 1.476(7)
C16B H16C 0.98
C16B H16D 0.98
C17 C18 1.5155(14)
C17 H17A 0.98
C17 H17B 0.98
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
O1 C2 C3 C8 -0.12(10)
C10 C2 C3 C8 119.79(9)
O1 C2 C3 C4 -179.84(9)
C10 C2 C3 C4 -59.94(14)
C8 C3 C4 C5 0.44(14)
C2 C3 C4 C5 -179.87(10)
C3 C4 C5 C6 -0.87(15)
C4 C5 C6 C7 0.23(16)
C5 C6 C7 C8 0.84(15)
C4 C3 C8 C7 0.66(14)
C2 C3 C8 C7 -179.10(9)
C4 C3 C8 C1 -179.57(8)
C2 C3 C8 C1 0.67(10)
C6 C7 C8 C3 -1.29(14)
C6 C7 C8 C1 178.99(10)
O2 C1 C8 C3 179.48(11)
O1 C1 C8 C3 -1.02(10)
O2 C1 C8 C7 -0.77(18)
O1 C1 C8 C7 178.73(10)
C18 C9 C10 C11 -0.10(15)
C18 C9 C10 C2 179.91(9)
O1 C2 C10 C11 -121.44(10)
C3 C2 C10 C11 121.92(11)
O1 C2 C10 C9 58.55(12)
C3 C2 C10 C9 -58.09(13)
C9 C10 C11 C12 0.51(16)
C2 C10 C11 C12 -179.50(10)
C10 C11 C12 C13 -0.44(17)
C11 C12 C13 C18 -0.07(17)
C11 C12 C13 C14 -178.35(11)
C12 C13 C14 C15A -170.05(12)
C18 C13 C14 C15A 11.73(17)
C12 C13 C14 C15B 164.3(5)
C18 C13 C14 C15B -13.9(5)
C13 C14 C15A C16A -42.2(2)
C15B C14 C15A C16A 36.6(10)
C14 C15A C16A C17 63.7(2)
C13 C14 C15B C16B 52.2(11)
C15A C14 C15B C16B -58.4(9)
C14 C15B C16B C17 -72.0(13)
C15B C16B C17 C18 52.0(9)
C15B C16B C17 C16A -42.7(6)
C15A C16A C17 C16B 48.9(5)
C15A C16A C17 C18 -53.52(17)
C10 C9 C18 C13 -0.41(15)
C10 C9 C18 C17 179.96(10)
C12 C13 C18 C9 0.49(15)
C14 C13 C18 C9 178.72(10)
C12 C13 C18 C17 -179.89(10)
C14 C13 C18 C17 -1.65(16)
C16B C17 C18 C9 160.3(5)
C16A C17 C18 C9 -157.81(11)
C16B C17 C18 C13 -19.3(5)
C16A C17 C18 C13 22.56(15)
O2 C1 O1 C2 -179.49(9)
C8 C1 O1 C2 0.95(10)
C10 C2 O1 C1 -124.41(9)
C3 C2 O1 C1 -0.53(10)
