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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/4/03/51/4035147.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_4035147
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         'C17 H16 O3'
_chemical_formula_sum            'C17 H16 O3'
_chemical_formula_weight         268.30
_chemical_name_common            'CML-II-141 from acetone'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.855(3)
_cell_length_b                   7.9583(15)
_cell_length_c                   18.760(3)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.7344
_cell_measurement_theta_min      2.1791
_cell_volume                     2665.7(8)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.848
_diffrn_measured_fraction_theta_max 0.848
_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  0.0238
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6095
_diffrn_reflns_theta_full        26.62
_diffrn_reflns_theta_max         26.62
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0358
_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)+(0.0441P)²+1.0588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                1980
_reflns_number_total             2368
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01322_si_003.cif
_cod_data_source_block           6f
_cod_database_code               4035147
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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 0.92322(6) 0.59124(12) 0.58033(5) 0.0186(3) Uani d . . 1
O O2 0.95932(7) 0.22358(14) 0.73672(5) 0.0285(3) Uani d . . 1
O O3 0.73209(7) 0.50076(12) 0.56653(5) 0.0206(3) Uani d . . 1
C C1 0.83160(9) 0.66087(19) 0.33258(8) 0.0222(4) Uani d . . 1
H H1 0.823487 0.699473 0.285287 0.027 Uiso calc U R 1
C C2 0.84125(9) 0.49007(18) 0.34584(7) 0.0202(4) Uani d . . 1
H H16 0.839834 0.412922 0.307219 0.024 Uiso calc U R 1
C C3 0.85301(8) 0.43005(18) 0.41511(7) 0.0152(3) Uani d . . 1
C C4 0.85508(8) 0.54570(17) 0.47135(7) 0.0143(3) Uani d . . 1
C C5 0.86611(9) 0.48794(16) 0.54760(7) 0.0142(3) Uani d . . 1
C C6 0.89365(9) 0.30140(16) 0.55820(7) 0.0137(3) Uani d . . 1
H H13 0.851401 0.232488 0.57744 0.016 Uiso calc U R 1
C C7 0.95435(9) 0.32110(18) 0.61679(7) 0.0163(3) Uani d . . 1
H H7 1.004153 0.318792 0.592427 0.02 Uiso calc U R 1
C C8 0.95564(9) 0.18602(18) 0.67377(7) 0.0185(3) Uani d . . 1
C C9 0.95385(11) 0.00531(19) 0.64989(8) 0.0275(4) Uani d . . 1
H H5 0.964536 -0.068107 0.690573 0.041 Uiso calc U R 1
H H6 0.991696 -0.012329 0.612796 0.041 Uiso calc U R 1
H H2 0.904163 -0.021167 0.630749 0.041 Uiso calc U R 1
C C10 0.86533(9) 0.24489(17) 0.42901(7) 0.0174(3) Uani d . . 1
H H4 0.883944 0.18993 0.385103 0.021 Uiso calc U R 1
H H3 0.817254 0.191471 0.442328 0.021 Uiso calc U R 1
C C11 0.92219(9) 0.22094(17) 0.48915(7) 0.0157(3) Uani d . . 1
H H15 0.970471 0.272885 0.475455 0.019 Uiso calc U R 1
H H14 0.930827 0.099455 0.496979 0.019 Uiso calc U R 1
C C12 0.94231(9) 0.50202(18) 0.64477(7) 0.0191(4) Uani d . . 1
H H10 0.989117 0.547806 0.666666 0.023 Uiso calc U R 1
C C13 0.87716(10) 0.51379(18) 0.69565(8) 0.0238(4) Uani d . . 1
H H9 0.885583 0.515187 0.745649 0.029 Uiso calc U R 1
C C14 0.80781(10) 0.52220(19) 0.67003(8) 0.0238(4) Uani d . . 1
H H8 0.766729 0.537608 0.701545 0.029 Uiso calc U R 1
C C15 0.79472(10) 0.50754(16) 0.59251(7) 0.0163(3) Uani d . . 1
C C16 0.84546(9) 0.71768(18) 0.45795(8) 0.0182(3) Uani d . . 1
H H12 0.846866 0.795492 0.496332 0.022 Uiso calc U R 1
C C17 0.83387(9) 0.77496(18) 0.38884(8) 0.0213(4) Uani d . . 1
H H11 0.827516 0.891624 0.379989 0.026 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
C12 O1 C5 104.03(10)
C2 C1 C17 119.83(13)
C2 C1 H1 120.1
C17 C1 H1 120.1
C1 C2 C3 121.15(13)
C1 C2 H16 119.4
C3 C2 H16 119.4
C2 C3 C4 118.61(13)
C2 C3 C10 120.94(12)
C4 C3 C10 120.43(12)
C3 C4 C16 120.21(13)
C3 C4 C5 121.01(12)
C16 C4 C5 118.77(12)
O1 C5 C4 108.66(11)
O1 C5 C15 107.13(11)
C4 C5 C15 112.27(12)
O1 C5 C6 105.18(11)
C4 C5 C6 116.44(11)
C15 C5 C6 106.58(11)
C11 C6 C7 114.13(12)
C11 C6 C5 112.99(10)
C7 C6 C5 102.24(10)
C11 C6 H13 109.1
C7 C6 H13 109.1
C5 C6 H13 109.1
C8 C7 C12 115.00(11)
C8 C7 C6 116.00(12)
C12 C7 C6 103.73(11)
C8 C7 H7 107.2
C12 C7 H7 107.2
C6 C7 H7 107.2
O2 C8 C9 121.53(13)
O2 C8 C7 120.64(13)
C9 C8 C7 117.82(12)
C8 C9 H5 109.5
C8 C9 H6 109.5
H5 C9 H6 109.5
C8 C9 H2 109.5
H5 C9 H2 109.5
H6 C9 H2 109.5
C3 C10 C11 110.18(12)
C3 C10 H4 109.6
C11 C10 H4 109.6
C3 C10 H3 109.6
C11 C10 H3 109.6
H4 C10 H3 108.1
C10 C11 C6 110.53(12)
C10 C11 H15 109.5
C6 C11 H15 109.5
C10 C11 H14 109.5
C6 C11 H14 109.5
H15 C11 H14 108.1
O1 C12 C13 108.52(12)
O1 C12 C7 101.91(10)
C13 C12 C7 112.32(12)
O1 C12 H10 111.2
C13 C12 H10 111.2
C7 C12 H10 111.2
C14 C13 C12 119.52(13)
C14 C13 H9 120.2
C12 C13 H9 120.2
C13 C14 C15 119.93(14)
C13 C14 H8 120.0
C15 C14 H8 120.0
O3 C15 C14 122.76(14)
O3 C15 C5 122.46(12)
C14 C15 C5 114.61(14)
C17 C16 C4 120.37(13)
C17 C16 H12 119.8
C4 C16 H12 119.8
C16 C17 C1 119.83(13)
C16 C17 H11 120.1
C1 C17 H11 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.4428(16)
O1 C5 1.4465(17)
O2 C8 1.2200(17)
O3 C15 1.2209(19)
C1 C2 1.393(2)
C1 C17 1.393(2)
C1 H1 0.95
C2 C3 1.4002(19)
C2 H16 0.95
C3 C4 1.4006(19)
C3 C10 1.5126(19)
C4 C16 1.4021(19)
C4 C5 1.5154(18)
C5 C15 1.536(2)
C5 C6 1.5764(18)
C6 C11 1.5323(18)
C6 C7 1.551(2)
C6 H13 1.0
C7 C8 1.5162(19)
C7 C12 1.5475(19)
C7 H7 1.0
C8 C9 1.507(2)
C9 H5 0.98
C9 H6 0.98
C9 H2 0.98
C10 C11 1.530(2)
C10 H4 0.99
C10 H3 0.99
C11 H15 0.99
C11 H14 0.99
C12 C13 1.508(2)
C12 H10 1.0
C13 C14 1.330(2)
C13 H9 0.95
C14 C15 1.478(2)
C14 H8 0.95
C16 C17 1.390(2)
C16 H12 0.95
C17 H11 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
C6 H13 O3 6_755 1.00 2.38 3.2847(18) 150.0
C9 H5 O2 3_746 0.98 2.54 3.4576(19) 155.7
C12 H10 O2 3_756 1.00 2.47 3.3370(18) 145.1
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
C17 C1 C2 C3 0.2(2)
C1 C2 C3 C4 -0.1(2)
C1 C2 C3 C10 -178.51(15)
C2 C3 C4 C16 0.0(2)
C10 C3 C4 C16 178.43(14)
C2 C3 C4 C5 178.80(14)
C10 C3 C4 C5 -2.8(2)
C12 O1 C5 C4 -166.38(11)
C12 O1 C5 C15 72.11(13)
C12 O1 C5 C6 -41.03(13)
C3 C4 C5 O1 132.35(14)
C16 C4 C5 O1 -48.88(18)
C3 C4 C5 C15 -109.35(15)
C16 C4 C5 C15 69.43(17)
C3 C4 C5 C6 13.9(2)
C16 C4 C5 C6 -167.33(13)
O1 C5 C6 C11 -106.99(13)
C4 C5 C6 C11 13.34(18)
C15 C5 C6 C11 139.48(12)
O1 C5 C6 C7 16.13(13)
C4 C5 C6 C7 136.47(13)
C15 C5 C6 C7 -97.40(12)
C11 C6 C7 C8 -98.10(14)
C5 C6 C7 C8 139.55(12)
C11 C6 C7 C12 134.81(12)
C5 C6 C7 C12 12.46(13)
C12 C7 C8 O2 -11.5(2)
C6 C7 C8 O2 -132.73(15)
C12 C7 C8 C9 169.76(14)
C6 C7 C8 C9 48.52(19)
C2 C3 C10 C11 143.74(14)
C4 C3 C10 C11 -34.62(19)
C3 C10 C11 C6 60.65(15)
C7 C6 C11 C10 -166.24(11)
C5 C6 C11 C10 -49.98(16)
C5 O1 C12 C13 -69.85(13)
C5 O1 C12 C7 48.83(14)
C8 C7 C12 O1 -164.85(12)
C6 C7 C12 O1 -37.13(14)
C8 C7 C12 C13 -48.91(18)
C6 C7 C12 C13 78.81(14)
O1 C12 C13 C14 31.44(18)
C7 C12 C13 C14 -80.45(17)
C12 C13 C14 C15 4.4(2)
C13 C14 C15 O3 173.94(14)
C13 C14 C15 C5 -1.6(2)
O1 C5 C15 O3 147.76(12)
C4 C5 C15 O3 28.55(18)
C6 C5 C15 O3 -100.06(14)
O1 C5 C15 C14 -36.67(15)
C4 C5 C15 C14 -155.88(12)
C6 C5 C15 C14 75.51(14)
C3 C4 C16 C17 -0.1(2)
C5 C4 C16 C17 -178.86(14)
C4 C16 C17 C1 0.2(2)
C2 C1 C17 C16 -0.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328949
