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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/4/03/51/4035143.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_4035143
loop_
_publ_author_name
'Kaufman, Riley H.'
'Law, Chunyin M.'
'Simanis, Justin A.'
'Woodall, Erica L.'
'Zwick, 3rd, Christian R'
'Wedler, Henry B.'
'Wendelboe, Paul'
'Hamaker, Christopher G.'
'Goodell, John R.'
'Tantillo, Dean J.'
'Mitchell, T. Andrew'
_publ_section_title
;
 Oxidopyrylium-Alkene [5 + 2] Cycloaddition Conjugate Addition Cascade
 (C³) Sequences: Scope, Limitation, and Computational
 Investigations.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9818
_journal_page_last               9838
_journal_paper_doi               10.1021/acs.joc.8b01322
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C9 H10 O3'
_chemical_formula_sum            'C9 H10 O3'
_chemical_formula_weight         166.17
_chemical_name_common            'Marshal Law/Mitchell ether from acetone'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 108.147(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.9246(7)
_cell_length_b                   7.3318(3)
_cell_length_c                   12.7929(6)
_cell_measurement_reflns_used    8345
_cell_measurement_temperature    101.(2)
_cell_measurement_theta_max      26.7940
_cell_measurement_theta_min      2.5328
_cell_volume                     1508.48(11)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      101.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22013
_diffrn_reflns_theta_full        26.82
_diffrn_reflns_theta_max         26.82
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0402P)²+1.8243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                1460
_reflns_number_total             1621
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01322_si_003.cif
_cod_data_source_block           5c
_cod_database_code               4035143
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
O O1 0.36522(6) 0.16165(12) 1.07745(7) 0.0180(2) Uani d . . 1
O O2 0.45601(5) 0.17265(11) 0.87501(6) 0.0140(2) Uani d . . 1
O O3 0.38399(6) 0.59206(12) 0.94047(7) 0.0197(2) Uani d . . 1
C C1 0.38692(7) 0.48260(17) 0.76708(10) 0.0165(3) Uani d . . 1
H H1 0.382269 0.599557 0.733746 0.02 Uiso calc U R 1
C C2 0.39371(7) 0.46453(16) 0.88443(9) 0.0131(2) Uani d . . 1
C C3 0.40426(7) 0.26926(16) 0.92627(9) 0.0117(2) Uani d . . 1
C C4 0.31865(7) 0.16904(16) 0.88496(9) 0.0134(2) Uani d . . 1
H H9 0.271306 0.257206 0.869229 0.016 Uiso calc U R 1
C C5 0.32308(8) 0.05017(17) 0.98470(10) 0.0186(3) Uani d . . 1
H H10 0.266659 0.017553 0.986111 0.022 Uiso calc U R 1
H H2 0.354647 -0.063213 0.983873 0.022 Uiso calc U R 1
C C6 0.32161(8) 0.07228(18) 0.77957(10) 0.0179(3) Uani d . . 1
H H8 0.272366 0.102984 0.716303 0.021 Uiso calc U R 1
H H3 0.324855 -0.061751 0.789341 0.021 Uiso calc U R 1
C C7 0.40222(7) 0.14940(17) 0.76386(9) 0.0154(3) Uani d . . 1
H H7 0.426634 0.061667 0.722539 0.018 Uiso calc U R 1
C C8 0.43375(7) 0.24264(17) 1.05068(9) 0.0154(3) Uani d . . 1
H H4 0.482894 0.161415 1.073028 0.018 Uiso calc U R 1
H H5 0.448897 0.361197 1.088692 0.018 Uiso calc U R 1
C C9 0.38740(7) 0.33215(18) 0.70836(10) 0.0171(3) Uani d . . 1
H H6 0.378354 0.34088 0.631423 0.021 Uiso calc U R 1
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
C5 O1 C8 105.59(9)
C3 O2 C7 102.81(8)
C9 C1 C2 119.06(11)
C9 C1 H1 120.5
C2 C1 H1 120.5
O3 C2 C1 123.16(11)
O3 C2 C3 122.53(10)
C1 C2 C3 113.98(10)
O2 C3 C2 109.02(9)
O2 C3 C8 111.48(9)
C2 C3 C8 116.91(9)
O2 C3 C4 104.31(9)
C2 C3 C4 109.21(9)
C8 C3 C4 105.09(9)
C5 C4 C6 117.55(10)
C5 C4 C3 100.76(9)
C6 C4 C3 103.50(9)
C5 C4 H9 111.4
C6 C4 H9 111.4
C3 C4 H9 111.4
O1 C5 C4 104.37(9)
O1 C5 H10 110.9
C4 C5 H10 110.9
O1 C5 H2 110.9
C4 C5 H2 110.9
H10 C5 H2 108.9
C4 C6 C7 102.48(9)
C4 C6 H8 111.3
C7 C6 H8 111.3
C4 C6 H3 111.3
C7 C6 H3 111.3
H8 C6 H3 109.2
O2 C7 C9 108.82(9)
O2 C7 C6 103.12(9)
C9 C7 C6 111.32(10)
O2 C7 H7 111.1
C9 C7 H7 111.1
C6 C7 H7 111.1
O1 C8 C3 106.01(9)
O1 C8 H4 110.5
C3 C8 H4 110.5
O1 C8 H5 110.5
C3 C8 H5 110.5
H4 C8 H5 108.7
C1 C9 C7 120.04(10)
C1 C9 H6 120.0
C7 C9 H6 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.4344(15)
O1 C8 1.4362(14)
O2 C3 1.4341(13)
O2 C7 1.4398(14)
O3 C2 1.2201(14)
C1 C9 1.3360(18)
C1 C2 1.4755(16)
C1 H1 0.95
C2 C3 1.5194(16)
C3 C8 1.5250(15)
C3 C4 1.5625(16)
C4 C5 1.5277(16)
C4 C6 1.5380(16)
C4 H9 1.0
C5 H10 0.99
C5 H2 0.99
C6 C7 1.5467(16)
C6 H8 0.99
C6 H3 0.99
C7 C9 1.5005(17)
C7 H7 1.0
C8 H4 0.99
C8 H5 0.99
C9 H6 0.95
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
C1 H1 O1 6_565 0.95 2.61 3.5026(15) 157.7
C7 H7 O1 6 1.00 2.45 3.2171(14) 133.0
C9 H6 O3 6_565 0.95 2.52 3.4546(15) 166.9
C1 H1 O1 6_565 0.95 2.61 3.5026(15) 157.7
C7 H7 O1 6 1.00 2.45 3.2171(14) 133.0
C9 H6 O3 6_565 0.95 2.52 3.4546(15) 166.9
C1 H1 O1 6_565 0.95 2.61 3.5026(15) 157.7
C7 H7 O1 6 1.00 2.45 3.2171(14) 133.0
C9 H6 O3 6_565 0.95 2.52 3.4546(15) 166.9
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
C9 C1 C2 O3 -171.10(12)
C9 C1 C2 C3 2.40(16)
C7 O2 C3 C2 -72.49(10)
C7 O2 C3 C8 156.96(10)
C7 O2 C3 C4 44.06(10)
O3 C2 C3 O2 -149.28(11)
C1 C2 C3 O2 37.18(13)
O3 C2 C3 C8 -21.75(16)
C1 C2 C3 C8 164.72(10)
O3 C2 C3 C4 97.34(13)
C1 C2 C3 C4 -76.20(12)
O2 C3 C4 C5 100.65(10)
C2 C3 C4 C5 -142.92(9)
C8 C3 C4 C5 -16.74(11)
O2 C3 C4 C6 -21.34(11)
C2 C3 C4 C6 95.08(10)
C8 C3 C4 C6 -138.73(10)
C8 O1 C5 C4 -44.23(12)
C6 C4 C5 O1 148.16(10)
C3 C4 C5 O1 36.62(11)
C5 C4 C6 C7 -117.62(11)
C3 C4 C6 C7 -7.63(12)
C3 O2 C7 C9 68.91(11)
C3 O2 C7 C6 -49.38(11)
C4 C6 C7 O2 34.24(12)
C4 C6 C7 C9 -82.29(11)
C5 O1 C8 C3 32.45(12)
O2 C3 C8 O1 -120.76(10)
C2 C3 C8 O1 112.91(11)
C4 C3 C8 O1 -8.36(12)
C2 C1 C9 C7 -5.34(17)
O2 C7 C9 C1 -31.07(15)
C6 C7 C9 C1 81.92(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328943
