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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/31/4033137.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_4033137
loop_
_publ_author_name
'Riedel, Sibylle'
'Maichle-Mössmer, Cäcilia'
'Maier, Martin E.'
_publ_section_title
;
 Intramolecular Diels-Alder Reactions of Tethered Enoate Substituted
 Furans Induced by Dialkylaluminum Chloride.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12798
_journal_page_last               12805
_journal_paper_doi               10.1021/acs.joc.7b02117
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C13 H20 O3'
_chemical_formula_weight         224.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1885(12)
_cell_length_b                   8.975(2)
_cell_length_c                   25.944(6)
_cell_measurement_reflns_used    124
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      4.801
_cell_volume                     1208.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker COSMO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-13 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            8190
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         2.401
_diffrn_source                   'ImuS-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       column
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 924 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0405
_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)+(0.0419P)²+0.2419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2583
_reflns_number_total             2957
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02117_si_002.cif
_cod_data_source_block           mo_sr112nl_0m_naphthalene_22_endo
_cod_depositor_comments
'Adding full bibliography for 4033135--4033140.cif.'
_cod_original_cell_volume        1208.2(5)
_cod_database_code               4033137
_shelx_shelxl_version_number     2014/7
_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   0.987
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.1238(4) 0.5715(2) 0.15501(7) 0.0185(4) Uani 1 1 d . .
H1 H -0.0236 0.6263 0.1710 0.022 Uiso 1 1 calc R U
O1 O 0.0958(3) 0.73186(16) 0.02136(5) 0.0243(3) Uani 1 1 d . .
H1A H -0.0343 0.7500 0.0031 0.036 Uiso 1 1 calc R U
C2 C 0.3438(4) 0.5660(2) 0.19466(7) 0.0259(5) Uani 1 1 d . .
H2A H 0.5014 0.5282 0.1776 0.031 Uiso 1 1 calc R U
H2B H 0.3798 0.6683 0.2069 0.031 Uiso 1 1 calc R U
O2 O 0.0623(3) 0.89521(18) 0.14100(7) 0.0402(4) Uani 1 1 d . .
C3 C 0.2835(5) 0.4677(3) 0.24086(8) 0.0307(5) Uani 1 1 d . .
H3A H 0.4353 0.4638 0.2639 0.037 Uiso 1 1 calc R U
H3B H 0.1380 0.5111 0.2605 0.037 Uiso 1 1 calc R U
O3 O 0.4484(3) 0.88216(16) 0.10291(6) 0.0280(4) Uani 1 1 d . .
C4 C 0.2141(5) 0.3113(2) 0.22363(8) 0.0263(5) Uani 1 1 d . .
H4A H 0.1710 0.2499 0.2541 0.032 Uiso 1 1 calc R U
H4B H 0.3641 0.2653 0.2062 0.032 Uiso 1 1 calc R U
C5 C -0.0161(4) 0.3142(2) 0.18663(8) 0.0274(5) Uani 1 1 d . .
H5A H -0.0490 0.2120 0.1738 0.033 Uiso 1 1 calc R U
H5B H -0.1714 0.3478 0.2055 0.033 Uiso 1 1 calc R U
C6 C 0.0306(4) 0.4168(2) 0.14126(7) 0.0199(4) Uani 1 1 d . .
C7 C -0.0123(4) 0.3737(2) 0.09307(7) 0.0227(4) Uani 1 1 d . .
H7 H -0.0732 0.2751 0.0877 0.027 Uiso 1 1 calc R U
C8 C 0.0289(4) 0.4704(2) 0.04626(7) 0.0215(4) Uani 1 1 d . .
H8 H -0.1193 0.4537 0.0223 0.026 Uiso 1 1 calc R U
C9 C 0.0252(4) 0.6344(2) 0.06260(7) 0.0184(4) Uani 1 1 d . .
H9 H -0.1530 0.6604 0.0742 0.022 Uiso 1 1 calc R U
C10 C 0.2108(4) 0.6599(2) 0.10732(7) 0.0168(4) Uani 1 1 d . .
H10 H 0.3859 0.6244 0.0969 0.020 Uiso 1 1 calc R U
C11 C 0.2774(5) 0.4244(2) 0.01790(8) 0.0295(5) Uani 1 1 d . .
H11A H 0.2615 0.3212 0.0060 0.044 Uiso 1 1 calc R U
H11B H 0.4244 0.4325 0.0414 0.044 Uiso 1 1 calc R U
H11C H 0.3045 0.4901 -0.0118 0.044 Uiso 1 1 calc R U
C12 C 0.2261(4) 0.8245(2) 0.11931(7) 0.0214(4) Uani 1 1 d . .
C13 C 0.4837(5) 1.0395(2) 0.11188(9) 0.0364(6) Uani 1 1 d . .
H13A H 0.6650 1.0656 0.1065 0.055 Uiso 1 1 calc R U
H13B H 0.4343 1.0634 0.1474 0.055 Uiso 1 1 calc R U
H13C H 0.3756 1.0962 0.0879 0.055 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
C6 C1 C2 111.42(16)
C6 C1 C10 112.20(15)
C2 C1 C10 109.72(16)
C6 C1 H1 107.8
C2 C1 H1 107.8
C10 C1 H1 107.8
C9 O1 H1A 109.5
C3 C2 C1 113.19(18)
C3 C2 H2A 108.9
C1 C2 H2A 108.9
C3 C2 H2B 108.9
C1 C2 H2B 108.9
H2A C2 H2B 107.8
C4 C3 C2 110.69(16)
C4 C3 H3A 109.5
C2 C3 H3A 109.5
C4 C3 H3B 109.5
C2 C3 H3B 109.5
H3A C3 H3B 108.1
C12 O3 C13 115.98(18)
C3 C4 C5 110.74(18)
C3 C4 H4A 109.5
C5 C4 H4A 109.5
C3 C4 H4B 109.5
C5 C4 H4B 109.5
H4A C4 H4B 108.1
C6 C5 C4 111.87(17)
C6 C5 H5A 109.2
C4 C5 H5A 109.2
C6 C5 H5B 109.2
C4 C5 H5B 109.2
H5A C5 H5B 107.9
C7 C6 C1 122.88(16)
C7 C6 C5 121.90(18)
C1 C6 C5 115.21(16)
C6 C7 C8 124.56(18)
C6 C7 H7 117.7
C8 C7 H7 117.7
C7 C8 C9 109.17(15)
C7 C8 C11 110.42(18)
C9 C8 C11 113.59(17)
C7 C8 H8 107.8
C9 C8 H8 107.8
C11 C8 H8 107.8
O1 C9 C10 108.38(15)
O1 C9 C8 112.19(15)
C10 C9 C8 110.31(15)
O1 C9 H9 108.6
C10 C9 H9 108.6
C8 C9 H9 108.6
C12 C10 C9 109.67(16)
C12 C10 C1 110.74(15)
C9 C10 C1 110.43(15)
C12 C10 H10 108.6
C9 C10 H10 108.6
C1 C10 H10 108.6
C8 C11 H11A 109.5
C8 C11 H11B 109.5
H11A C11 H11B 109.5
C8 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O2 C12 O3 123.82(19)
O2 C12 C10 125.1(2)
O3 C12 C10 111.04(18)
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.513(3)
C1 C2 1.537(3)
C1 C10 1.538(2)
C1 H1 1.0000
O1 C9 1.430(2)
O1 H1A 0.8400
C2 C3 1.520(3)
C2 H2A 0.9900
C2 H2B 0.9900
O2 C12 1.201(3)
C3 C4 1.517(3)
C3 H3A 0.9900
C3 H3B 0.9900
O3 C12 1.334(3)
O3 C13 1.443(2)
C4 C5 1.533(3)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.514(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.327(3)
C7 C8 1.508(3)
C7 H7 0.9500
C8 C9 1.532(3)
C8 C11 1.541(3)
C8 H8 1.0000
C9 C10 1.525(3)
C9 H9 1.0000
C10 C12 1.512(3)
C10 H10 1.0000
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095690
