#------------------------------------------------------------------------------
#$Date: 2023-11-06 08:47:24 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287300 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/00/1570040.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_1570040
loop_
_publ_author_name
'Goyal, Karan'
'Kukier, Garrett A.'
'Chen, Xiangyang'
'Turlik, Aneta'
'Houk, K. N.'
'Sarpong, Richmond'
_publ_section_title
;
 Rearrangement of a carboxy-substituted spiro[4.4]nonatriene to annulated
 fulvenes through a Pd(ii)-mediated 1,5-vinyl shift.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              11809
_journal_page_last               11817
_journal_paper_doi               10.1039/d3sc03222a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C12 H12 O4'
_chemical_formula_sum            'C12 H12 O4'
_chemical_formula_weight         220.22
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-03-02 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.1660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   17.1400(2)
_cell_length_b                   8.09620(10)
_cell_length_c                   31.5007(4)
_cell_measurement_reflns_used    17270
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.4400
_cell_measurement_theta_min      5.3660
_cell_volume                     4219.07(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            26165
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        74.000
_diffrn_reflns_theta_max         74.480
_diffrn_reflns_theta_min         5.348
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 30% ethyl acetate in hexanes'
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0423
_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)+(0.0667P)²+2.6239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3926
_reflns_number_total             4271
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc03222a1.cif
_cod_data_source_block           KGoyal001_Sarpong
_cod_depositor_comments
'Adding full bibliography for 1570039--1570041.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1570040
_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   0.738
_shelx_estimated_absorpt_t_max   0.902
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_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
C1 C 0.39911(7) 0.54525(15) 0.49032(4) 0.0200(2) Uani 1 1 d . . . . .
C2 C 0.37703(7) 0.41761(15) 0.51814(4) 0.0197(2) Uani 1 1 d . . . . .
C3 C 0.34508(7) 0.45471(15) 0.55751(4) 0.0190(2) Uani 1 1 d . . . . .
C4 C 0.26572(7) 0.56156(15) 0.54588(4) 0.0214(3) Uani 1 1 d . . . . .
H4A H 0.2500 0.5905 0.5142 0.026 Uiso 1 1 calc R U . . .
H4B H 0.2206 0.5014 0.5531 0.026 Uiso 1 1 calc R U . . .
C5 C 0.28729(8) 0.71342(15) 0.57380(4) 0.0231(3) Uani 1 1 d . . . . .
H5 H 0.2509 0.8023 0.5733 0.028 Uiso 1 1 calc R U . . .
C6 C 0.36210(8) 0.71107(15) 0.59918(4) 0.0226(3) Uani 1 1 d . . . . .
H6 H 0.3851 0.7981 0.6187 0.027 Uiso 1 1 calc R U . . .
C7 C 0.40688(8) 0.55588(15) 0.59394(4) 0.0209(3) Uani 1 1 d . . . . .
H7A H 0.4224 0.4934 0.6219 0.025 Uiso 1 1 calc R U . . .
H7B H 0.4562 0.5819 0.5845 0.025 Uiso 1 1 calc R U . . .
C8 C 0.33261(7) 0.28181(15) 0.57236(4) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.30010(8) 0.25005(16) 0.61062(4) 0.0224(3) Uani 1 1 d . . . . .
C10 C 0.25870(10) 0.04386(18) 0.65301(5) 0.0332(3) Uani 1 1 d . . . . .
H10A H 0.2088 0.1056 0.6512 0.050 Uiso 1 1 calc R U . . .
H10B H 0.2986 0.0708 0.6806 0.050 Uiso 1 1 calc R U . . .
H10C H 0.2472 -0.0749 0.6521 0.050 Uiso 1 1 calc R U . . .
C11 C 0.35537(8) 0.16773(15) 0.54668(4) 0.0221(3) Uani 1 1 d . . . . .
H11 H 0.3539 0.0514 0.5503 0.026 Uiso 1 1 calc R U . . .
C12 C 0.38257(8) 0.25299(15) 0.51250(4) 0.0214(3) Uani 1 1 d . . . . .
H12 H 0.4012 0.2014 0.4899 0.026 Uiso 1 1 calc R U . . .
C13 C 0.42957(7) 0.87964(15) 0.41093(4) 0.0206(2) Uani 1 1 d . . . . .
C14 C 0.42727(7) 1.00859(15) 0.37794(4) 0.0202(3) Uani 1 1 d . . . . .
C15 C 0.41594(7) 0.97378(15) 0.32956(4) 0.0201(3) Uani 1 1 d . . . . .
C16 C 0.33506(8) 0.87891(16) 0.30869(4) 0.0259(3) Uani 1 1 d . . . . .
H16A H 0.3059 0.8536 0.3312 0.031 Uiso 1 1 calc R U . . .
H16B H 0.2993 0.9447 0.2849 0.031 Uiso 1 1 calc R U . . .
C17 C 0.36191(10) 0.72343(17) 0.29078(5) 0.0328(3) Uani 1 1 d . . . . .
H17 H 0.3257 0.6395 0.2766 0.039 Uiso 1 1 calc R U . . .
C18 C 0.44059(10) 0.71523(17) 0.29680(5) 0.0328(3) Uani 1 1 d . . . . .
H18 H 0.4669 0.6246 0.2873 0.039 Uiso 1 1 calc R U . . .
C19 C 0.48473(8) 0.86278(16) 0.32005(4) 0.0255(3) Uani 1 1 d . . . . .
H19A H 0.5137 0.9216 0.3012 0.031 Uiso 1 1 calc R U . . .
H19B H 0.5241 0.8300 0.3478 0.031 Uiso 1 1 calc R U . . .
C20 C 0.41556(7) 1.14743(15) 0.31223(4) 0.0204(3) Uani 1 1 d . . . . .
C21 C 0.40410(7) 1.18299(15) 0.26500(4) 0.0211(3) Uani 1 1 d . . . . .
C22 C 0.38791(9) 1.38988(18) 0.21072(4) 0.0282(3) Uani 1 1 d . . . . .
H22A H 0.3398 1.3339 0.1928 0.042 Uiso 1 1 calc R U . . .
H22B H 0.4354 1.3562 0.2010 0.042 Uiso 1 1 calc R U . . .
H22C H 0.3807 1.5097 0.2074 0.042 Uiso 1 1 calc R U . . .
C23 C 0.42485(8) 1.25959(16) 0.34484(4) 0.0222(3) Uani 1 1 d . . . . .
H23 H 0.4265 1.3760 0.3415 0.027 Uiso 1 1 calc R U . . .
C24 C 0.43189(8) 1.17222(16) 0.38605(4) 0.0233(3) Uani 1 1 d . . . . .
H24 H 0.4386 1.2223 0.4141 0.028 Uiso 1 1 calc R U . . .
O1 O 0.41617(6) 0.49285(12) 0.45459(3) 0.0265(2) Uani 1 1 d . . . . .
O2 O 0.40047(6) 0.69390(11) 0.50082(3) 0.0246(2) Uani 1 1 d . . . . .
O3 O 0.28404(7) 0.35687(12) 0.63378(3) 0.0331(2) Uani 1 1 d . . . . .
O4 O 0.29043(6) 0.08795(12) 0.61644(3) 0.0286(2) Uani 1 1 d . . . . .
O5 O 0.43519(6) 0.93064(12) 0.45096(3) 0.0256(2) Uani 1 1 d . . . . .
O6 O 0.42548(6) 0.73081(12) 0.40022(3) 0.0276(2) Uani 1 1 d . . . . .
O7 O 0.39885(7) 1.07870(12) 0.23709(3) 0.0333(2) Uani 1 1 d . . . . .
O8 O 0.39946(6) 1.34548(12) 0.25640(3) 0.0281(2) Uani 1 1 d . . . . .
H1 H 0.4249(17) 0.582(4) 0.4364(10) 0.077(8) Uiso 1 1 d . . . . .
H5A H 0.4319(16) 0.845(4) 0.4710(9) 0.067(7) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
O2 C1 O1 123.33(11) . . ?
O2 C1 C2 120.76(11) . . ?
O1 C1 C2 115.91(11) . . ?
C12 C2 C1 125.33(11) . . ?
C12 C2 C3 110.91(11) . . ?
C1 C2 C3 123.75(11) . . ?
C8 C3 C2 100.44(9) . . ?
C8 C3 C4 113.50(10) . . ?
C2 C3 C4 113.29(10) . . ?
C8 C3 C7 112.33(10) . . ?
C2 C3 C7 112.51(10) . . ?
C4 C3 C7 105.07(9) . . ?
C5 C4 C3 104.41(10) . . ?
C6 C5 C4 113.20(11) . . ?
C5 C6 C7 112.82(11) . . ?
C6 C7 C3 104.45(10) . . ?
C11 C8 C9 126.83(11) . . ?
C11 C8 C3 111.24(11) . . ?
C9 C8 C3 121.93(11) . . ?
O3 C9 O4 124.17(12) . . ?
O3 C9 C8 124.21(12) . . ?
O4 C9 C8 111.62(11) . . ?
C8 C11 C12 108.51(11) . . ?
C2 C12 C11 108.89(11) . . ?
O6 C13 O5 123.42(11) . . ?
O6 C13 C14 120.43(11) . . ?
O5 C13 C14 116.14(11) . . ?
C24 C14 C13 125.18(12) . . ?
C24 C14 C15 111.11(11) . . ?
C13 C14 C15 123.67(11) . . ?
C20 C15 C14 100.28(10) . . ?
C20 C15 C16 112.63(10) . . ?
C14 C15 C16 112.32(10) . . ?
C20 C15 C19 113.35(10) . . ?
C14 C15 C19 113.18(10) . . ?
C16 C15 C19 105.34(10) . . ?
C17 C16 C15 104.11(11) . . ?
C18 C17 C16 113.11(13) . . ?
C17 C18 C19 113.47(12) . . ?
C18 C19 C15 103.93(11) . . ?
C23 C20 C21 126.43(11) . . ?
C23 C20 C15 111.33(11) . . ?
C21 C20 C15 122.22(11) . . ?
O7 C21 O8 123.42(12) . . ?
O7 C21 C20 124.27(12) . . ?
O8 C21 C20 112.31(11) . . ?
C20 C23 C24 108.53(11) . . ?
C14 C24 C23 108.76(11) . . ?
C9 O4 C10 115.95(11) . . ?
C21 O8 C22 115.48(10) . . ?
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
C1 O2 1.2467(16) . ?
C1 O1 1.3057(15) . ?
C1 C2 1.4670(17) . ?
C2 C12 1.3512(17) . ?
C2 C3 1.5112(16) . ?
C3 C8 1.5087(16) . ?
C3 C4 1.5722(17) . ?
C3 C7 1.5730(16) . ?
C4 C5 1.5007(17) . ?
C5 C6 1.3218(19) . ?
C6 C7 1.5038(17) . ?
C8 C11 1.3507(18) . ?
C8 C9 1.4768(17) . ?
C9 O3 1.2087(17) . ?
C9 O4 1.3415(16) . ?
C10 O4 1.4414(16) . ?
C11 C12 1.4545(17) . ?
C13 O6 1.2483(16) . ?
C13 O5 1.3062(16) . ?
C13 C14 1.4663(17) . ?
C14 C24 1.3476(18) . ?
C14 C15 1.5116(16) . ?
C15 C20 1.5076(16) . ?
C15 C16 1.5707(17) . ?
C15 C19 1.5725(17) . ?
C16 C17 1.5000(19) . ?
C17 C18 1.313(2) . ?
C18 C19 1.499(2) . ?
C20 C23 1.3488(18) . ?
C20 C21 1.4774(17) . ?
C21 O7 1.2052(17) . ?
C21 O8 1.3414(16) . ?
C22 O8 1.4457(15) . ?
C23 C24 1.4556(17) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C12 -172.00(12) . . . . ?
O1 C1 C2 C12 8.47(19) . . . . ?
O2 C1 C2 C3 7.68(19) . . . . ?
O1 C1 C2 C3 -171.85(11) . . . . ?
C12 C2 C3 C8 -0.83(14) . . . . ?
C1 C2 C3 C8 179.46(11) . . . . ?
C12 C2 C3 C4 -122.20(12) . . . . ?
C1 C2 C3 C4 58.08(15) . . . . ?
C12 C2 C3 C7 118.81(12) . . . . ?
C1 C2 C3 C7 -60.91(15) . . . . ?
C8 C3 C4 C5 125.23(11) . . . . ?
C2 C3 C4 C5 -121.06(11) . . . . ?
C7 C3 C4 C5 2.14(12) . . . . ?
C3 C4 C5 C6 -1.19(14) . . . . ?
C4 C5 C6 C7 -0.38(16) . . . . ?
C5 C6 C7 C3 1.76(14) . . . . ?
C8 C3 C7 C6 -126.17(11) . . . . ?
C2 C3 C7 C6 121.36(11) . . . . ?
C4 C3 C7 C6 -2.33(12) . . . . ?
C2 C3 C8 C11 1.33(14) . . . . ?
C4 C3 C8 C11 122.56(12) . . . . ?
C7 C3 C8 C11 -118.44(12) . . . . ?
C2 C3 C8 C9 -179.17(11) . . . . ?
C4 C3 C8 C9 -57.95(15) . . . . ?
C7 C3 C8 C9 61.06(15) . . . . ?
C11 C8 C9 O3 176.48(14) . . . . ?
C3 C8 C9 O3 -2.9(2) . . . . ?
C11 C8 C9 O4 -3.66(19) . . . . ?
C3 C8 C9 O4 176.93(11) . . . . ?
C9 C8 C11 C12 179.18(12) . . . . ?
C3 C8 C11 C12 -1.36(15) . . . . ?
C1 C2 C12 C11 179.81(12) . . . . ?
C3 C2 C12 C11 0.10(15) . . . . ?
C8 C11 C12 C2 0.79(15) . . . . ?
O6 C13 C14 C24 -179.46(13) . . . . ?
O5 C13 C14 C24 1.21(19) . . . . ?
O6 C13 C14 C15 3.10(19) . . . . ?
O5 C13 C14 C15 -176.24(11) . . . . ?
C24 C14 C15 C20 0.32(13) . . . . ?
C13 C14 C15 C20 178.08(11) . . . . ?
C24 C14 C15 C16 -119.50(12) . . . . ?
C13 C14 C15 C16 58.27(15) . . . . ?
C24 C14 C15 C19 121.37(12) . . . . ?
C13 C14 C15 C19 -60.86(15) . . . . ?
C20 C15 C16 C17 125.94(11) . . . . ?
C14 C15 C16 C17 -121.72(12) . . . . ?
C19 C15 C16 C17 1.91(13) . . . . ?
C15 C16 C17 C18 -1.26(16) . . . . ?
C16 C17 C18 C19 0.00(18) . . . . ?
C17 C18 C19 C15 1.26(16) . . . . ?
C20 C15 C19 C18 -125.48(11) . . . . ?
C14 C15 C19 C18 121.18(12) . . . . ?
C16 C15 C19 C18 -1.90(13) . . . . ?
C14 C15 C20 C23 -0.09(13) . . . . ?
C16 C15 C20 C23 119.51(12) . . . . ?
C19 C15 C20 C23 -121.02(12) . . . . ?
C14 C15 C20 C21 -178.63(10) . . . . ?
C16 C15 C20 C21 -59.03(15) . . . . ?
C19 C15 C20 C21 60.44(15) . . . . ?
C23 C20 C21 O7 177.28(13) . . . . ?
C15 C20 C21 O7 -4.4(2) . . . . ?
C23 C20 C21 O8 -3.24(18) . . . . ?
C15 C20 C21 O8 175.07(11) . . . . ?
C21 C20 C23 C24 178.31(12) . . . . ?
C15 C20 C23 C24 -0.15(15) . . . . ?
C13 C14 C24 C23 -178.15(12) . . . . ?
C15 C14 C24 C23 -0.43(15) . . . . ?
C20 C23 C24 C14 0.36(15) . . . . ?
O3 C9 O4 C10 0.0(2) . . . . ?
C8 C9 O4 C10 -179.85(12) . . . . ?
O7 C21 O8 C22 -0.29(19) . . . . ?
C20 C21 O8 C22 -179.78(11) . . . . ?
