#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:14:45 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263822 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157885.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_7157885
loop_
_publ_author_name
'Chang, Meng-Yang'
'Tsai, Min-Chen'
_publ_section_title
;
 Synthesis of benzofused cyclobutaoxepanones via intramolecular
 annulation of o-cinnamyl chalcones.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2254
_journal_page_last               2268
_journal_paper_doi               10.1039/d1ob00058f
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C26 H24 O4'
_chemical_formula_weight         400.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2019-07-25 deposited with the CCDC.	2021-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                92.823(2)
_cell_angle_beta                 108.693(2)
_cell_angle_gamma                109.839(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4174(5)
_cell_length_b                   10.5047(5)
_cell_length_c                   11.7070(6)
_cell_measurement_reflns_used    8284
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3517
_cell_measurement_theta_min      2.4633
_cell_volume                     1015.58(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23935
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_min         1.866
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lump
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0361
_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)+(0.0409P)²+0.4300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3553
_reflns_number_total             4180
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00058f2.cif
_cod_data_source_block           mo_190608LT_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157884--7157887.cif.
;
_cod_database_code               7157885
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 -0.16568(12) -0.06699(10) 0.24219(10) 0.0284(2) Uani 1 1 d . . . . .
O2 O 0.27615(11) 0.14713(9) 0.11257(8) 0.0199(2) Uani 1 1 d . . . . .
O3 O 0.36246(11) 0.68541(9) -0.09233(8) 0.0196(2) Uani 1 1 d . . . . .
O4 O 0.02804(10) 0.30710(9) -0.08098(8) 0.0194(2) Uani 1 1 d . . . . .
C1 C -0.2730(2) -0.05415(16) 0.30007(17) 0.0390(4) Uani 1 1 d . . . . .
H24 H -0.2105 0.0049 0.3807 0.059 Uiso 1 1 calc R U . . .
H3 H -0.3376 -0.1453 0.3100 0.059 Uiso 1 1 calc R U . . .
H1 H -0.3449 -0.0132 0.2495 0.059 Uiso 1 1 calc R U . . .
C2 C -0.06198(15) 0.05254(13) 0.22551(12) 0.0190(3) Uani 1 1 d . . . . .
C3 C -0.06525(15) 0.18111(13) 0.25153(12) 0.0182(3) Uani 1 1 d . . . . .
H4 H -0.1415 0.1921 0.2841 0.022 Uiso 1 1 calc R U . . .
C4 C 0.04620(15) 0.29465(12) 0.22884(11) 0.0154(3) Uani 1 1 d . . . . .
H5 H 0.0444 0.3832 0.2466 0.018 Uiso 1 1 calc R U . . .
C5 C 0.15875(14) 0.28268(12) 0.18151(11) 0.0140(2) Uani 1 1 d . . . . .
C6 C 0.28781(14) 0.40487(12) 0.16657(11) 0.0135(2) Uani 1 1 d . . . . .
H10 H 0.3943 0.4073 0.2231 0.016 Uiso 1 1 calc R U . . .
C7 C 0.30665(14) 0.43374(12) 0.04166(11) 0.0137(2) Uani 1 1 d . . . . .
H23 H 0.3948 0.4084 0.0298 0.016 Uiso 1 1 calc R U . . .
C8 C 0.15938(14) 0.38924(12) -0.07349(11) 0.0145(2) Uani 1 1 d . . . . .
C9 C 0.18253(15) 0.44433(13) -0.18567(11) 0.0159(3) Uani 1 1 d . . . . .
C10 C 0.27827(15) 0.57832(13) -0.18933(12) 0.0167(3) Uani 1 1 d . . . . .
C11 C 0.29100(16) 0.61365(14) -0.30034(12) 0.0204(3) Uani 1 1 d . . . . .
H18 H 0.3566 0.7045 -0.3020 0.025 Uiso 1 1 calc R U . . .
C12 C 0.20951(16) 0.51813(15) -0.40754(12) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.2191 0.5434 -0.4823 0.027 Uiso 1 1 calc R U . . .
C13 C 0.15931(15) 0.15017(12) 0.15691(11) 0.0155(3) Uani 1 1 d . . . . .
C14 C 0.29193(17) 0.01833(13) 0.09298(13) 0.0220(3) Uani 1 1 d . . . . .
H6 H 0.3164 -0.0159 0.1705 0.033 Uiso 1 1 calc R U . . .
H8 H 0.3798 0.0303 0.0619 0.033 Uiso 1 1 calc R U . . .
H7 H 0.1905 -0.0480 0.0331 0.033 Uiso 1 1 calc R U . . .
C15 C 0.05056(16) 0.03588(13) 0.17793(12) 0.0188(3) Uani 1 1 d . . . . .
H9 H 0.0521 -0.0528 0.1603 0.023 Uiso 1 1 calc R U . . .
C16 C 0.36705(15) 0.59017(12) 0.09381(11) 0.0146(2) Uani 1 1 d . . . . .
H17 H 0.4875 0.6310 0.1339 0.018 Uiso 1 1 calc R U . . .
C17 C 0.28509(14) 0.54997(12) 0.18985(11) 0.0135(2) Uani 1 1 d . . . . .
H16 H 0.1709 0.5443 0.1549 0.016 Uiso 1 1 calc R U . . .
C18 C 0.36543(14) 0.63789(12) 0.31526(11) 0.0141(2) Uani 1 1 d . . . . .
C19 C 0.50036(16) 0.62795(13) 0.40232(12) 0.0189(3) Uani 1 1 d . . . . .
H15 H 0.5392 0.5596 0.3847 0.023 Uiso 1 1 calc R U . . .
C20 C 0.57926(17) 0.71658(14) 0.51475(12) 0.0225(3) Uani 1 1 d . . . . .
H14 H 0.6720 0.7093 0.5730 0.027 Uiso 1 1 calc R U . . .
C21 C 0.52242(17) 0.81531(13) 0.54165(12) 0.0232(3) Uani 1 1 d . . . . .
H13 H 0.5760 0.8760 0.6184 0.028 Uiso 1 1 calc R U . . .
C22 C 0.38689(17) 0.82535(13) 0.45618(13) 0.0230(3) Uani 1 1 d . . . . .
H12 H 0.3469 0.8923 0.4748 0.028 Uiso 1 1 calc R U . . .
C23 C 0.30961(15) 0.73783(13) 0.34356(12) 0.0181(3) Uani 1 1 d . . . . .
H11 H 0.2177 0.7461 0.2851 0.022 Uiso 1 1 calc R U . . .
C24 C 0.30670(16) 0.67860(13) 0.00878(11) 0.0178(3) Uani 1 1 d . . . . .
H22 H 0.1870 0.6408 -0.0230 0.021 Uiso 1 1 calc R U . . .
H21 H 0.3444 0.7726 0.0550 0.021 Uiso 1 1 calc R U . . .
C25 C 0.10072(15) 0.34971(14) -0.29663(12) 0.0195(3) Uani 1 1 d . . . . .
H20 H 0.0345 0.2585 -0.2964 0.023 Uiso 1 1 calc R U . . .
C26 C 0.11369(16) 0.38520(15) -0.40582(12) 0.0224(3) Uani 1 1 d . . . . .
H19 H 0.0574 0.3191 -0.4793 0.027 Uiso 1 1 calc R U . . .
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'
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 C1 116.82(11) . . ?
C13 O2 C14 117.60(10) . . ?
C10 O3 C24 117.10(10) . . ?
O1 C1 H24 109.5 . . ?
O1 C1 H3 109.5 . . ?
H24 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H24 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O1 C2 C3 124.28(12) . . ?
O1 C2 C15 114.75(11) . . ?
C3 C2 C15 120.96(11) . . ?
C2 C3 C4 118.54(11) . . ?
C2 C3 H4 120.7 . . ?
C4 C3 H4 120.7 . . ?
C5 C4 C3 122.35(11) . . ?
C5 C4 H5 118.8 . . ?
C3 C4 H5 118.8 . . ?
C4 C5 C13 117.54(11) . . ?
C4 C5 C6 122.79(11) . . ?
C13 C5 C6 119.42(11) . . ?
C5 C6 C17 119.66(10) . . ?
C5 C6 C7 124.66(10) . . ?
C17 C6 C7 88.86(9) . . ?
C5 C6 H10 107.2 . . ?
C17 C6 H10 107.2 . . ?
C7 C6 H10 107.2 . . ?
C8 C7 C6 119.85(10) . . ?
C8 C7 C16 111.91(10) . . ?
C6 C7 C16 87.41(9) . . ?
C8 C7 H23 111.8 . . ?
C6 C7 H23 111.8 . . ?
C16 C7 H23 111.8 . . ?
O4 C8 C7 123.22(11) . . ?
O4 C8 C9 119.86(11) . . ?
C7 C8 C9 116.80(10) . . ?
C10 C9 C25 117.57(11) . . ?
C10 C9 C8 126.56(11) . . ?
C25 C9 C8 115.86(11) . . ?
O3 C10 C11 113.73(11) . . ?
O3 C10 C9 126.17(11) . . ?
C11 C10 C9 120.08(12) . . ?
C12 C11 C10 120.87(12) . . ?
C12 C11 H18 119.6 . . ?
C10 C11 H18 119.6 . . ?
C11 C12 C26 119.88(12) . . ?
C11 C12 H2 120.1 . . ?
C26 C12 H2 120.1 . . ?
O2 C13 C15 124.39(11) . . ?
O2 C13 C5 114.06(10) . . ?
C15 C13 C5 121.54(11) . . ?
O2 C14 H6 109.5 . . ?
O2 C14 H8 109.5 . . ?
H6 C14 H8 109.5 . . ?
O2 C14 H7 109.5 . . ?
H6 C14 H7 109.5 . . ?
H8 C14 H7 109.5 . . ?
C13 C15 C2 119.06(11) . . ?
C13 C15 H9 120.5 . . ?
C2 C15 H9 120.5 . . ?
C24 C16 C17 115.96(10) . . ?
C24 C16 C7 117.31(10) . . ?
C17 C16 C7 88.42(9) . . ?
C24 C16 H17 111.1 . . ?
C17 C16 H17 111.1 . . ?
C7 C16 H17 111.1 . . ?
C18 C17 C6 121.92(10) . . ?
C18 C17 C16 117.97(10) . . ?
C6 C17 C16 88.19(8) . . ?
C18 C17 H16 109.0 . . ?
C6 C17 H16 109.0 . . ?
C16 C17 H16 109.0 . . ?
C19 C18 C23 118.53(11) . . ?
C19 C18 C17 121.93(11) . . ?
C23 C18 C17 119.44(11) . . ?
C20 C19 C18 120.94(12) . . ?
C20 C19 H15 119.5 . . ?
C18 C19 H15 119.5 . . ?
C21 C20 C19 119.90(12) . . ?
C21 C20 H14 120.1 . . ?
C19 C20 H14 120.1 . . ?
C20 C21 C22 119.76(12) . . ?
C20 C21 H13 120.1 . . ?
C22 C21 H13 120.1 . . ?
C21 C22 C23 120.19(12) . . ?
C21 C22 H12 119.9 . . ?
C23 C22 H12 119.9 . . ?
C22 C23 C18 120.67(12) . . ?
C22 C23 H11 119.7 . . ?
C18 C23 H11 119.7 . . ?
O3 C24 C16 111.84(10) . . ?
O3 C24 H22 109.2 . . ?
C16 C24 H22 109.2 . . ?
O3 C24 H21 109.2 . . ?
C16 C24 H21 109.2 . . ?
H22 C24 H21 107.9 . . ?
C26 C25 C9 122.07(12) . . ?
C26 C25 H20 119.0 . . ?
C9 C25 H20 119.0 . . ?
C25 C26 C12 119.53(12) . . ?
C25 C26 H19 120.2 . . ?
C12 C26 H19 120.2 . . ?
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 1.3720(15) . ?
O1 C1 1.4217(18) . ?
O2 C13 1.3673(15) . ?
O2 C14 1.4259(14) . ?
O3 C10 1.3694(15) . ?
O3 C24 1.4364(15) . ?
O4 C8 1.2168(15) . ?
C1 H24 0.9800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.3826(18) . ?
C2 C15 1.3996(18) . ?
C3 C4 1.3983(17) . ?
C3 H4 0.9500 . ?
C4 C5 1.3807(17) . ?
C4 H5 0.9500 . ?
C5 C13 1.4096(16) . ?
C5 C6 1.5016(16) . ?
C6 C17 1.5453(16) . ?
C6 C7 1.5606(16) . ?
C6 H10 1.0000 . ?
C7 C8 1.5029(17) . ?
C7 C16 1.5623(16) . ?
C7 H23 1.0000 . ?
C8 C9 1.5100(17) . ?
C9 C10 1.4019(18) . ?
C9 C25 1.4073(18) . ?
C10 C11 1.3993(18) . ?
C11 C12 1.381(2) . ?
C11 H18 0.9500 . ?
C12 C26 1.387(2) . ?
C12 H2 0.9500 . ?
C13 C15 1.3808(18) . ?
C14 H6 0.9800 . ?
C14 H8 0.9800 . ?
C14 H7 0.9800 . ?
C15 H9 0.9500 . ?
C16 C24 1.5045(17) . ?
C16 C17 1.5557(16) . ?
C16 H17 1.0000 . ?
C17 C18 1.5036(17) . ?
C17 H16 1.0000 . ?
C18 C19 1.3909(18) . ?
C18 C23 1.3930(17) . ?
C19 C20 1.3907(19) . ?
C19 H15 0.9500 . ?
C20 C21 1.3834(19) . ?
C20 H14 0.9500 . ?
C21 C22 1.387(2) . ?
C21 H13 0.9500 . ?
C22 C23 1.3873(18) . ?
C22 H12 0.9500 . ?
C23 H11 0.9500 . ?
C24 H22 0.9900 . ?
C24 H21 0.9900 . ?
C25 C26 1.3799(19) . ?
C25 H20 0.9500 . ?
C26 H19 0.9500 . ?
