#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/48/4034889.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_4034889
loop_
_publ_author_name
'Chang, Meng-Yang'
'Hsiao, Yu-Ting'
'Lai, Kai-Hsiang'
_publ_section_title
;
 mCPBA-Mediated Intramolecular Oxidative Annulation of ortho-Crotyl or
 Cinnamyl Arylaldehydes: Synthesis of Benzofused Five-, Six-, and
 Seven-Membered Oxacycles.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14110
_journal_page_last               14119
_journal_paper_doi               10.1021/acs.joc.8b02146
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 91.367(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8432(2)
_cell_length_b                   18.7402(7)
_cell_length_c                   11.7029(4)
_cell_measurement_reflns_used    4078
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3570
_cell_measurement_theta_min      2.7851
_cell_volume                     1500.39(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12349
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         2.052
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0421
_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)+(0.0481P)²+0.6250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2510
_reflns_number_total             3084
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b02146_si_002.cif
_cod_data_source_block           180414lt_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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034889
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O1 O 0.72075(16) 0.09768(7) 0.33890(10) 0.0318(3) Uani 1 1 d . .
O2 O -0.00751(15) 0.16618(6) 0.02069(9) 0.0235(3) Uani 1 1 d . .
O3 O 0.41090(16) 0.13001(6) 0.45030(9) 0.0282(3) Uani 1 1 d . .
O4 O 0.32944(17) 0.14287(7) -0.21238(10) 0.0343(3) Uani 1 1 d . .
H13 H 0.457(3) 0.1265(12) -0.2219(18) 0.052 Uiso 1 1 d . U
C1 C 0.8481(2) 0.05200(9) 0.27706(15) 0.0327(4) Uani 1 1 d . .
H11 H 0.7701 0.0184 0.2308 0.049 Uiso 1 1 calc R U
H10 H 0.9322 0.0254 0.3310 0.049 Uiso 1 1 calc R U
H1 H 0.9294 0.0809 0.2270 0.049 Uiso 1 1 calc R U
C2 C 0.5727(2) 0.12941(8) 0.27654(13) 0.0229(3) Uani 1 1 d . .
C3 C 0.5786(2) 0.14305(8) 0.16062(13) 0.0232(3) Uani 1 1 d . .
H12 H 0.6933 0.1317 0.1201 0.028 Uiso 1 1 calc R U
C4 C 0.4188(2) 0.17317(8) 0.10217(13) 0.0209(3) Uani 1 1 d . .
C5 C 0.4251(2) 0.18528(9) -0.02492(13) 0.0243(3) Uani 1 1 d . .
H16 H 0.5590 0.1752 -0.0507 0.029 Uiso 1 1 calc R U
H15 H 0.3973 0.2362 -0.0408 0.029 Uiso 1 1 calc R U
C6 C 0.2807(2) 0.13963(8) -0.09464(12) 0.0215(3) Uani 1 1 d . .
H14 H 0.2873 0.0891 -0.0675 0.026 Uiso 1 1 calc R U
C7 C 0.0685(2) 0.16638(8) -0.09173(13) 0.0221(3) Uani 1 1 d . .
H19 H 0.0640 0.2163 -0.1218 0.026 Uiso 1 1 calc R U
C8 C -0.0675(2) 0.12072(8) -0.16439(13) 0.0207(3) Uani 1 1 d . .
C9 C -0.1077(2) 0.13871(8) -0.27739(13) 0.0232(3) Uani 1 1 d . .
H3 H -0.0496 0.1801 -0.3089 0.028 Uiso 1 1 calc R U
C10 C -0.2318(2) 0.09706(9) -0.34516(14) 0.0262(4) Uani 1 1 d . .
H20 H -0.2573 0.1099 -0.4226 0.031 Uiso 1 1 calc R U
C11 C -0.3182(2) 0.03693(9) -0.30024(14) 0.0273(4) Uani 1 1 d . .
H2 H -0.4038 0.0086 -0.3464 0.033 Uiso 1 1 calc R U
C12 C -0.1544(2) 0.06001(8) -0.11980(13) 0.0245(3) Uani 1 1 d . .
H5 H -0.1283 0.0470 -0.0425 0.029 Uiso 1 1 calc R U
C13 C -0.2790(2) 0.01820(9) -0.18706(14) 0.0277(4) Uani 1 1 d . .
H4 H -0.3375 -0.0232 -0.1557 0.033 Uiso 1 1 calc R U
C14 C 0.0744(2) 0.21800(8) 0.09871(13) 0.0231(3) Uani 1 1 d . .
H6 H -0.0255 0.2318 0.1544 0.028 Uiso 1 1 calc R U
H18 H 0.1111 0.2613 0.0557 0.028 Uiso 1 1 calc R U
C15 C 0.2513(2) 0.18943(8) 0.16186(13) 0.0204(3) Uani 1 1 d . .
C16 C 0.2462(2) 0.17673(8) 0.27908(13) 0.0218(3) Uani 1 1 d . .
H17 H 0.1325 0.1888 0.3199 0.026 Uiso 1 1 calc R U
C17 C 0.4047(2) 0.14672(8) 0.33676(12) 0.0213(3) Uani 1 1 d . .
C18 C 0.2365(3) 0.14092(12) 0.51201(14) 0.0389(5) Uani 1 1 d . .
H7 H 0.2049 0.1919 0.5128 0.058 Uiso 1 1 calc R U
H8 H 0.2559 0.1239 0.5906 0.058 Uiso 1 1 calc R U
H9 H 0.1289 0.1145 0.4750 0.058 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
C2 O1 C1 116.23(12)
C7 O2 C14 116.04(11)
C17 O3 C18 116.98(12)
C6 O4 H13 110.0(13)
O1 C1 H11 109.5
O1 C1 H10 109.5
H11 C1 H10 109.5
O1 C1 H1 109.5
H11 C1 H1 109.5
H10 C1 H1 109.5
O1 C2 C3 124.38(14)
O1 C2 C17 115.97(14)
C3 C2 C17 119.63(14)
C2 C3 C4 121.00(14)
C2 C3 H12 119.5
C4 C3 H12 119.5
C15 C4 C3 119.24(14)
C15 C4 C5 120.43(14)
C3 C4 C5 120.29(13)
C4 C5 C6 114.18(12)
C4 C5 H16 108.7
C6 C5 H16 108.7
C4 C5 H15 108.7
C6 C5 H15 108.7
H16 C5 H15 107.6
O4 C6 C5 109.21(12)
O4 C6 C7 104.48(12)
C5 C6 C7 113.85(12)
O4 C6 H14 109.7
C5 C6 H14 109.7
C7 C6 H14 109.7
O2 C7 C8 106.52(12)
O2 C7 C6 112.64(12)
C8 C7 C6 111.85(12)
O2 C7 H19 108.6
C8 C7 H19 108.6
C6 C7 H19 108.6
C9 C8 C12 118.69(14)
C9 C8 C7 120.31(14)
C12 C8 C7 121.00(14)
C8 C9 C10 120.87(15)
C8 C9 H3 119.6
C10 C9 H3 119.6
C11 C10 C9 120.16(15)
C11 C10 H20 119.9
C9 C10 H20 119.9
C10 C11 C13 119.59(15)
C10 C11 H2 120.2
C13 C11 H2 120.2
C13 C12 C8 120.73(14)
C13 C12 H5 119.6
C8 C12 H5 119.6
C12 C13 C11 119.96(15)
C12 C13 H4 120.0
C11 C13 H4 120.0
O2 C14 C15 111.66(12)
O2 C14 H6 109.3
C15 C14 H6 109.3
O2 C14 H18 109.3
C15 C14 H18 109.3
H6 C14 H18 107.9
C4 C15 C16 119.85(14)
C4 C15 C14 119.70(13)
C16 C15 C14 120.41(13)
C17 C16 C15 120.79(14)
C17 C16 H17 119.6
C15 C16 H17 119.6
O3 C17 C16 125.05(13)
O3 C17 C2 115.44(13)
C16 C17 C2 119.48(14)
O3 C18 H7 109.5
O3 C18 H8 109.5
H7 C18 H8 109.5
O3 C18 H9 109.5
H7 C18 H9 109.5
H8 C18 H9 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3700(19)
O1 C1 1.431(2)
O2 C7 1.4262(17)
O2 C14 1.4374(18)
O3 C17 1.3648(18)
O3 C18 1.4241(19)
O4 C6 1.4266(18)
O4 H13 0.94(2)
C1 H11 0.9800
C1 H10 0.9800
C1 H1 0.9800
C2 C3 1.382(2)
C2 C17 1.401(2)
C3 C4 1.396(2)
C3 H12 0.9500
C4 C15 1.390(2)
C4 C5 1.506(2)
C5 C6 1.528(2)
C5 H16 0.9900
C5 H15 0.9900
C6 C7 1.538(2)
C6 H14 1.0000
C7 C8 1.511(2)
C7 H19 1.0000
C8 C9 1.386(2)
C8 C12 1.391(2)
C9 C10 1.388(2)
C9 H3 0.9500
C10 C11 1.382(2)
C10 H20 0.9500
C11 C13 1.390(2)
C11 H2 0.9500
C12 C13 1.389(2)
C12 H5 0.9500
C13 H4 0.9500
C14 C15 1.502(2)
C14 H6 0.9900
C14 H18 0.9900
C15 C16 1.394(2)
C16 C17 1.383(2)
C16 H17 0.9500
C18 H7 0.9800
C18 H8 0.9800
C18 H9 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328732
