##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2018/3'
_journal_date_recd_electronic     2020-02-27
_journal_date_accepted     2020-03-01
_journal_name_full     'IUCrData'
_journal_year     2020
_journal_volume     5
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314620002886
_journal_coeditor_code     HB4340
_publ_contact_author_name     'Alan J. Lough'
_publ_contact_author_address
;
Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6,
Canada
;
_publ_contact_author_email     'alan.lough@utoronto.ca'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '(416) 978-6275'
_publ_section_title
;
1,2,3,5-Tetrahydronaphtho[2,1-c]oxepine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Lough, Alan J.' .
;
Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6,
Canada
;
    'Pounder, Austin' .
;
Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1
Canada
;
    'Wicks, Christopher' .
;
Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1
Canada
;
    'Tam, William' .
;
Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1
Canada
;
_publ_section_synopsis
;
In the title compound, the seven-membered ring is in a psuedo-chair
conformation. In the crystal, molecules are linked by weak C---H...O hydrogen
bonds forming layers parallel to (010). In addition, there are weak π--π
stacking interactions between inversion-related naphthalene ring systems.
;
_chemical_name_systematic
;
1,2,3,5-Tetrahydronaphtho[2,1-c]oxepine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H14 O'
_chemical_formula_sum     'C14 H14 O'
_chemical_formula_iupac     'C14 H14 O'
_chemical_formula_weight     198.25
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.4559(3)
_cell_length_b     12.8405(4)
_cell_length_c     8.9638(3)
_cell_angle_alpha     90
_cell_angle_beta     111.4450(10)
_cell_angle_gamma     90
_cell_volume     1013.02(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9948
_cell_measurement_theta_min     2.31
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     150(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.370
_exptl_crystal_size_mid     0.260
_exptl_crystal_size_min     0.250
_exptl_crystal_density_diffrn     1.300
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     424
_exptl_absorpt_coefficient_mu     0.080
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.7233
_exptl_absorpt_correction_T_max     0.7456
_diffrn_ambient_temperature     150(2)
_diffrn_source     'selaed tube with Bruker Triumph monochromator'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker Kappa APEX DUO CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     21543
_diffrn_reflns_av_R_equivalents     0.0211
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_theta_min     2.314
_diffrn_reflns_theta_max     27.582
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_refine_special_details     ?
_reflns_number_total     2347
_reflns_number_gt     2055
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0413
_refine_ls_R_factor_gt     0.0350
_refine_ls_wR_factor_gt     0.0930
_refine_ls_wR_factor_ref     0.0996
_refine_ls_goodness_of_fit_ref     1.065
_refine_ls_restrained_S_all     1.065
_refine_ls_number_reflns     2347
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0520P)²+0.3073P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.296
_refine_diff_density_min     -0.198
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_cell_refinement
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 1.00150(8) 0.34280(6) 0.72056(9) 0.02263(19) Uani d 1 . .
    C C1 0.77678(11) 0.44489(7) 0.56216(11) 0.0171(2) Uani d 1 . .
    C C2 0.65678(11) 0.37620(7) 0.53419(11) 0.0163(2) Uani d 1 . .
    C C3 0.66501(11) 0.29413(8) 0.65822(12) 0.0209(2) Uani d 1 . .
    H H3A 0.5679(16) 0.2539(11) 0.6272(16) 0.029(3) Uiso d 1 . .
    H H3B 0.6758(16) 0.3299(11) 0.7608(17) 0.031(3) Uiso d 1 . .
    C C4 0.79563(12) 0.21581(8) 0.68926(13) 0.0235(2) Uani d 1 . .
    H H4A 0.7759(16) 0.1550(11) 0.7461(16) 0.029(3) Uiso d 1 . .
    H H4B 0.7980(16) 0.1911(12) 0.5840(18) 0.035(4) Uiso d 1 . .
    C C5 0.95069(12) 0.25805(9) 0.79119(14) 0.0254(2) Uani d 1 . .
    H H5A 0.9486(16) 0.2824(11) 0.8993(18) 0.033(4) Uiso d 1 . .
    H H5B 1.0304(15) 0.2034(10) 0.8079(16) 0.025(3) Uiso d 1 . .
    C C6 0.91744(11) 0.43684(8) 0.71202(13) 0.0214(2) Uani d 1 . .
    H H6A 0.9889(14) 0.4953(11) 0.7133(14) 0.023(3) Uiso d 1 . .
    H H6B 0.8913(15) 0.4415(10) 0.8106(17) 0.028(3) Uiso d 1 . .
    C C7 0.77109(12) 0.52380(7) 0.45040(12) 0.0194(2) Uani d 1 . .
    H H7A 0.8559(16) 0.5724(11) 0.4711(16) 0.029(3) Uiso d 1 . .
    C C8 0.64771(12) 0.53392(7) 0.31122(12) 0.0198(2) Uani d 1 . .
    H H8A 0.6454(15) 0.5891(11) 0.2355(16) 0.027(3) Uiso d 1 . .
    C C9 0.52464(11) 0.46395(7) 0.27548(11) 0.0172(2) Uani d 1 . .
    C C10 0.39883(12) 0.47042(8) 0.12770(12) 0.0218(2) Uani d 1 . .
    H H10A 0.4011(15) 0.5267(11) 0.0541(16) 0.026(3) Uiso d 1 . .
    C C11 0.28267(12) 0.40005(9) 0.08940(13) 0.0248(2) Uani d 1 . .
    H H11A 0.1987(17) 0.4037(11) -0.0128(19) 0.036(4) Uiso d 1 . .
    C C12 0.28495(12) 0.32073(9) 0.19878(13) 0.0236(2) Uani d 1 . .
    H H12A 0.2036(16) 0.2691(11) 0.1702(16) 0.031(3) Uiso d 1 . .
    C C13 0.40269(11) 0.31364(8) 0.34385(12) 0.0201(2) Uani d 1 . .
    H H13A 0.4012(15) 0.2577(11) 0.4170(16) 0.027(3) Uiso d 1 . .
    C C14 0.52804(10) 0.38377(7) 0.38733(11) 0.0157(2) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C5 . 1.4277(13) ?
    O1 C6 . 1.4323(12) ?
    C1 C2 . 1.3858(13) ?
    C1 C7 . 1.4120(14) ?
    C1 C6 . 1.5092(13) ?
    C2 C14 . 1.4327(13) ?
    C2 C3 . 1.5131(13) ?
    C3 C4 . 1.5372(14) ?
    C3 H3A . 1.000(14) ?
    C3 H3B . 0.999(14) ?
    C4 C5 . 1.5163(15) ?
    C4 H4A . 0.987(14) ?
    C4 H4B . 1.004(15) ?
    C5 H5A . 1.025(15) ?
    C5 H5B . 1.000(13) ?
    C6 H6A . 1.007(13) ?
    C6 H6B . 1.003(14) ?
    C7 C8 . 1.3675(14) ?
    C7 H7A . 0.979(14) ?
    C8 C9 . 1.4112(14) ?
    C8 H8A . 0.975(14) ?
    C9 C10 . 1.4229(13) ?
    C9 C14 . 1.4292(13) ?
    C10 C11 . 1.3657(16) ?
    C10 H10A . 0.984(14) ?
    C11 C12 . 1.4084(16) ?
    C11 H11A . 0.969(15) ?
    C12 C13 . 1.3712(15) ?
    C12 H12A . 0.976(14) ?
    C13 C14 . 1.4248(13) ?
    C13 H13A . 0.977(14) ?
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
    C5 O1 C6 . . 113.34(8) ?
    C2 C1 C7 . . 120.80(9) ?
    C2 C1 C6 . . 120.95(9) ?
    C7 C1 C6 . . 118.24(9) ?
    C1 C2 C14 . . 119.18(9) ?
    C1 C2 C3 . . 119.45(9) ?
    C14 C2 C3 . . 121.38(8) ?
    C2 C3 C4 . . 114.25(8) ?
    C2 C3 H3A . . 111.1(8) ?
    C4 C3 H3A . . 107.9(8) ?
    C2 C3 H3B . . 108.5(8) ?
    C4 C3 H3B . . 109.2(8) ?
    H3A C3 H3B . . 105.5(11) ?
    C5 C4 C3 . . 114.27(9) ?
    C5 C4 H4A . . 107.2(8) ?
    C3 C4 H4A . . 108.7(8) ?
    C5 C4 H4B . . 109.3(8) ?
    C3 C4 H4B . . 109.2(8) ?
    H4A C4 H4B . . 108.0(12) ?
    O1 C5 C4 . . 114.42(9) ?
    O1 C5 H5A . . 108.2(8) ?
    C4 C5 H5A . . 109.3(8) ?
    O1 C5 H5B . . 104.1(8) ?
    C4 C5 H5B . . 110.4(8) ?
    H5A C5 H5B . . 110.3(11) ?
    O1 C6 C1 . . 113.36(8) ?
    O1 C6 H6A . . 105.7(7) ?
    C1 C6 H6A . . 109.2(7) ?
    O1 C6 H6B . . 108.3(8) ?
    C1 C6 H6B . . 111.0(8) ?
    H6A C6 H6B . . 109.0(10) ?
    C8 C7 C1 . . 120.93(9) ?
    C8 C7 H7A . . 118.6(8) ?
    C1 C7 H7A . . 120.5(8) ?
    C7 C8 C9 . . 120.28(9) ?
    C7 C8 H8A . . 119.9(8) ?
    C9 C8 H8A . . 119.8(8) ?
    C8 C9 C10 . . 120.90(9) ?
    C8 C9 C14 . . 119.61(9) ?
    C10 C9 C14 . . 119.47(9) ?
    C11 C10 C9 . . 121.14(10) ?
    C11 C10 H10A . . 122.0(8) ?
    C9 C10 H10A . . 116.8(8) ?
    C10 C11 C12 . . 119.82(10) ?
    C10 C11 H11A . . 120.8(9) ?
    C12 C11 H11A . . 119.4(9) ?
    C13 C12 C11 . . 120.57(10) ?
    C13 C12 H12A . . 119.5(8) ?
    C11 C12 H12A . . 119.9(8) ?
    C12 C13 C14 . . 121.55(10) ?
    C12 C13 H13A . . 118.7(8) ?
    C14 C13 H13A . . 119.7(8) ?
    C13 C14 C9 . . 117.41(9) ?
    C13 C14 C2 . . 123.42(9) ?
    C9 C14 C2 . . 119.15(8) ?
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
    C7 C1 C2 C14 . . . . 2.09(14) ?
    C6 C1 C2 C14 . . . . -177.41(8) ?
    C7 C1 C2 C3 . . . . -178.58(9) ?
    C6 C1 C2 C3 . . . . 1.92(14) ?
    C1 C2 C3 C4 . . . . -62.32(12) ?
    C14 C2 C3 C4 . . . . 117.00(10) ?
    C2 C3 C4 C5 . . . . 76.33(12) ?
    C6 O1 C5 C4 . . . . 69.71(12) ?
    C3 C4 C5 O1 . . . . -63.49(12) ?
    C5 O1 C6 C1 . . . . -87.27(10) ?
    C2 C1 C6 O1 . . . . 65.29(12) ?
    C7 C1 C6 O1 . . . . -114.22(10) ?
    C2 C1 C7 C8 . . . . -0.56(15) ?
    C6 C1 C7 C8 . . . . 178.95(9) ?
    C1 C7 C8 C9 . . . . -1.23(15) ?
    C7 C8 C9 C10 . . . . -176.95(9) ?
    C7 C8 C9 C14 . . . . 1.43(14) ?
    C8 C9 C10 C11 . . . . 177.03(9) ?
    C14 C9 C10 C11 . . . . -1.35(15) ?
    C9 C10 C11 C12 . . . . 1.34(15) ?
    C10 C11 C12 C13 . . . . 0.19(16) ?
    C11 C12 C13 C14 . . . . -1.72(15) ?
    C12 C13 C14 C9 . . . . 1.66(14) ?
    C12 C13 C14 C2 . . . . -176.93(9) ?
    C8 C9 C14 C13 . . . . -178.54(9) ?
    C10 C9 C14 C13 . . . . -0.14(13) ?
    C8 C9 C14 C2 . . . . 0.11(13) ?
    C10 C9 C14 C2 . . . . 178.51(8) ?
    C1 C2 C14 C13 . . . . 176.72(9) ?
    C3 C2 C14 C13 . . . . -2.60(14) ?
    C1 C2 C14 C9 . . . . -1.84(13) ?
    C3 C2 C14 C9 . . . . 178.83(8) ?
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
    _geom_hbond_publ_flag
    C11 H11A O1 1_454 0.970(16) 2.558(16) 3.4803(14) 159.0(11) yes
    C12 H12A O1 4_465 0.976(15) 2.560(15) 3.4661(14) 154.5(11) yes
_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_min     0.971
_shelx_estimated_absorpt_T_max     0.980
