data_14
_audit_creation_date               2020-03-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number       '2018/3'
loop_
  _audit_author_name
  _audit_author_email
  _audit_author_address
 'Sarlah, D.' sarlah@illinois.edu
;
University of Illinois at Urbana-Champaign
Department of Chemistry
600 S. Mathews Ave
Urbana
61801
USA
;
 'Shved, A.S.' shvedalx@illinois.edu
;
University of Illinois at Urbana-Champaign
Department of Chemistry
600 S. Mathews Ave
Urbana
61801
USA
;

_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          benzo[d]oxepine
_chemical_formula_moiety           'C10 H8 O'
_chemical_formula_sum              'C10 H8 O'
_chemical_formula_weight           144.16
_chemical_melting_point            ?
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'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_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                     7.8858(2)
_cell_length_b                     6.0451(2)
_cell_length_c                     8.4347(3)
_cell_angle_alpha                  90
_cell_angle_beta                   114.3054(10)
_cell_angle_gamma                  90
_cell_volume                       366.45(2)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      6743
_cell_measurement_temperature      100.0
_cell_measurement_theta_max        28.243
_cell_measurement_theta_min        4.289
_shelx_estimated_absorpt_T_max     0.988
_shelx_estimated_absorpt_T_min     0.956
_exptl_absorpt_coefficient_mu      0.083
_exptl_absorpt_correction_T_max    0.7457
_exptl_absorpt_correction_T_min    0.7092
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1154 before and 0.0378 after correction. The Ratio of minimum to maximum transmission is 0.9511. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear yellow'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_primary      yellow
_exptl_crystal_density_diffrn      1.307
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               152
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 2.00 3.00 -2.00 0.0860
 -2.00 -3.00 2.00 0.1090
 3.00 1.00 3.00 0.1960
 -3.00 0.00 -2.00 0.2450
 4.00 -3.00 -4.00 0.0710
 -4.00 3.00 4.00 0.0670
 -3.00 -4.00 -1.00 0.1690
 1.00 -4.00 -1.00 0.0880
 -4.00 0.00 -1.00 0.2320
 -4.00 1.00 4.00 0.0960
 3.00 2.00 -3.00 0.0850
 -3.00 -2.00 3.00 0.1140

_exptl_crystal_recrystallization_method 
 'Crystallized from methanol by slow evaporation'
_exptl_crystal_size_max            0.541
_exptl_crystal_size_mid            0.227
_exptl_crystal_size_min            0.142
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0175
_diffrn_reflns_av_unetI/netI       0.0113
_diffrn_reflns_Laue_measured_fraction_full  0.989
_diffrn_reflns_Laue_measured_fraction_max  0.992
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         8
_diffrn_reflns_limit_k_min         -8
_diffrn_reflns_limit_l_max         11
_diffrn_reflns_limit_l_min         -11
_diffrn_reflns_number              8457
_diffrn_reflns_point_group_measured_fraction_full  0.989
_diffrn_reflns_point_group_measured_fraction_max  0.992
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.270
_diffrn_reflns_theta_min           4.289
_diffrn_ambient_temperature        100.0
_diffrn_detector                   'Bruker Photon II area detector'
_diffrn_detector_area_resol_mean   ?
_diffrn_detector_type              'charge integrated pixel array'
_diffrn_measured_fraction_theta_full  0.989
_diffrn_measured_fraction_theta_max  0.992
_diffrn_measurement_device         'kappa diffractometer'
_diffrn_measurement_device_type    'Bruker D8 Venture/Photon II'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_monochromator    'multilayer mirrors'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'microfocus sealed X-ray tube'
_diffrn_source_current             1.0
_diffrn_source_power               0.05
_diffrn_source_target              Mo
_diffrn_source_type                'Incoatec I\ms'
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  870
_reflns_number_total               901
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'XS  (Sheldrick, 2008)'
_refine_diff_density_max           0.193
_refine_diff_density_min           -0.156
_refine_diff_density_rms           0.034
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.166
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       88
_refine_ls_number_reflns           901
_refine_ls_number_restraints       86
_refine_ls_R_factor_all            0.0430
_refine_ls_R_factor_gt             0.0421
_refine_ls_restrained_S_all        1.140
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0469P)²+0.1052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1120
_refine_ls_wR_factor_ref           0.1126
_refine_special_details           
 'Due to whole molecule disorder around inversion centers, pseudosymmetric relationship between C5/C10 and C3/C8 prevented from independent refinement of ADPs. They were constrained to be identical. All bond lengths in arene ring, as well as symmetry-related distances in oxepin ring were restrained to similar distances using SADI 0.01. Free refinement of C2-C3 and C10-C11 showed poor stability and occasionally resulted in bond lengths as short as 1.265 A. It was therefore restrained to be as close to the mean of 1.317 A, as found in 15 oxepine structures (CCDC, Mogul search)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C3-C2 = C10-C11
 1.317 with sigma of 0.02
 O1-C2 \\sim O1-C11
 with sigma of 0.01
 C3-C2 \\sim C10-C11
 with sigma of 0.01
 C5-C4 \\sim C9-C4 \\sim C9-C8 \\sim C8-C7 \\sim C7-C6 \\sim C6-C5
 with sigma of 0.01
 C4-C3 \\sim C9-C10
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(C5)
Uanis(C3) = Uanis(C8)
4. Rigid body (RIGU) restrains
 O1, C2, C3, C4, C5, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O1(0.5) C2(0.5) H2(0.5) C3(0.5) H3(0.5) C4(0.5) C5(0.5) H5(0.5)
 C6(0.5) H6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) C10(0.5) H10(0.5)
 C11(0.5) H11(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       direct
_atom_sites_solution_secondary     ?
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_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O 0.1635(2) 0.4336(3) 0.1462(2) 0.0435(5) Uani 0.5 1 d D . P A -1
 C2 C 0.1518(6) 0.6003(6) 0.2513(6) 0.0325(8) Uani 0.5 1 d D . P A -1
 H2 H 0.035002 0.673975 0.205813 0.039 Uiso 0.5 1 calc R U P A -1
 C3 C 0.2682(12) 0.680(2) 0.4018(14) 0.0245(10) Uani 0.5 1 d D . P A -1
 H3 H 0.221150 0.797901 0.446029 0.029 Uiso 0.5 1 calc R U P A -1
 C4 C 0.4612(13) 0.613(2) 0.5128(13) 0.0223(14) Uani 0.5 1 d D . P A -1
 C5 C 0.5723(17) 0.743(3) 0.6525(18) 0.0282(7) Uani 0.5 1 d D . P A -1
 H5 H 0.524889 0.880041 0.672017 0.034 Uiso 0.5 1 calc R U P A -1
 C6 C 0.7517(5) 0.6789(6) 0.7652(5) 0.0301(7) Uani 0.5 1 d D . P A -1
 H6 H 0.824401 0.773974 0.858047 0.036 Uiso 0.5 1 calc R U P A -1
 C7 C 0.8245(6) 0.4809(6) 0.7441(5) 0.0308(7) Uani 0.5 1 d D . P A -1
 H7 H 0.946988 0.437273 0.819925 0.037 Uiso 0.5 1 calc R U P A -1
 C8 C 0.7122(12) 0.346(2) 0.6075(13) 0.0245(10) Uani 0.5 1 d D . P A -1
 H8 H 0.758084 0.205661 0.593116 0.029 Uiso 0.5 1 calc R U P A -1
 C9 C 0.5346(11) 0.410(2) 0.4908(12) 0.0211(15) Uani 0.5 1 d D . P A -1
 C10 C 0.4339(17) 0.241(3) 0.3572(18) 0.0282(7) Uani 0.5 1 d D . P A -1
 H10 H 0.491598 0.099962 0.376979 0.034 Uiso 0.5 1 calc R U P A -1
 C11 C 0.2774(6) 0.2550(6) 0.2157(6) 0.0313(8) Uani 0.5 1 d D . P A -1
 H11 H 0.237648 0.120965 0.152300 0.038 Uiso 0.5 1 calc R U P A -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_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 C2 1.371(4) . ?
 O1 C11 1.372(4) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.313(7) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.477(8) . ?
 C4 C5 1.388(8) . ?
 C4 C9 1.400(4) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.396(8) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.371(4) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.392(7) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.395(7) . ?
 C9 C10 1.485(9) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.320(7) . ?
 C11 H11 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C2 O1 C11 120.6(3) . . ?
 O1 C2 H2 113.3 . . ?
 C3 C2 O1 133.4(5) . . ?
 C3 C2 H2 113.3 . . ?
 C2 C3 H3 115.0 . . ?
 C2 C3 C4 129.9(8) . . ?
 C4 C3 H3 115.0 . . ?
 C5 C4 C3 120.6(8) . . ?
 C5 C4 C9 117.2(6) . . ?
 C9 C4 C3 121.9(6) . . ?
 C4 C5 H5 119.0 . . ?
 C4 C5 C6 122.0(10) . . ?
 C6 C5 H5 119.0 . . ?
 C5 C6 H6 119.5 . . ?
 C7 C6 C5 121.1(7) . . ?
 C7 C6 H6 119.5 . . ?
 C6 C7 H7 121.3 . . ?
 C6 C7 C8 117.4(5) . . ?
 C8 C7 H7 121.3 . . ?
 C7 C8 H8 118.9 . . ?
 C7 C8 C9 122.3(8) . . ?
 C9 C8 H8 118.9 . . ?
 C4 C9 C10 125.5(5) . . ?
 C8 C9 C4 120.0(6) . . ?
 C8 C9 C10 114.4(7) . . ?
 C9 C10 H10 114.7 . . ?
 C11 C10 C9 130.7(10) . . ?
 C11 C10 H10 114.7 . . ?
 O1 C11 H11 115.1 . . ?
 C10 C11 O1 129.8(8) . . ?
 C10 C11 H11 115.1 . . ?

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_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 O1 C2 C3 C4 1(2) . . . . ?
 C2 O1 C11 C10 -29.1(14) . . . . ?
 C2 C3 C4 C5 168.5(17) . . . . ?
 C2 C3 C4 C9 -17(2) . . . . ?
 C3 C4 C5 C6 176.5(15) . . . . ?
 C3 C4 C9 C8 -174.8(19) . . . . ?
 C3 C4 C9 C10 0.6(13) . . . . ?
 C4 C5 C6 C7 -1(2) . . . . ?
 C4 C9 C10 C11 14(3) . . . . ?
 C5 C4 C9 C8 0.4(13) . . . . ?
 C5 C4 C9 C10 176(2) . . . . ?
 C5 C6 C7 C8 -0.6(14) . . . . ?
 C6 C7 C8 C9 2.4(17) . . . . ?
 C7 C8 C9 C4 -2.3(17) . . . . ?
 C7 C8 C9 C10 -178.2(14) . . . . ?
 C8 C9 C10 C11 -169.9(18) . . . . ?
 C9 C4 C5 C6 1(2) . . . . ?
 C9 C10 C11 O1 2(3) . . . . ?
 C11 O1 C2 C3 28.4(12) . . . . ?

_olex2_date_sample_data_collection  2019-04-08
_olex2_date_sample_submission      2019-04-05
_olex2_exptl_crystal_mounting_method 
 'Mounted using Krytox oil on a Cryo-Loop with (5 -2 1) face roughly perpendicular to the spindle axis'
_olex2_submission_original_sample_id  D64U
_olex2_submission_special_instructions  'No special instructions were received'
