#------------------------------------------------------------------------------
#$Date: 2023-08-05 11:33:07 +0200 (Sat 05 de Aug de 2023) $
#$Revision: 285523 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/94/7159474.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_7159474
loop_
_publ_author_name
'Fadeev, Alexander A.'
'Kotora, Martin'
_publ_section_title
;
 Catalytic vs. uncatalyzed [2 + 2] photocycloadditions of quinones
 with alkynes.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6174
_journal_page_last               6179
_journal_paper_doi               10.1039/d3ob00636k
_journal_volume                  21
_journal_year                    2023
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C16 H14 O3'
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-02-07 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.9100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4042(4)
_cell_length_b                   8.1827(2)
_cell_length_c                   12.1889(4)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4815
_cell_measurement_theta_min      2.9960
_cell_volume                     1218.71(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0063
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            76544
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.996
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.179
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0350
_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)+(0.0397P)²+0.6323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2723
_reflns_number_total             2792
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00636k2.cif
_cod_data_source_block           mo_fa0529_kotora
_cod_depositor_comments
'Adding full bibliography for 7159473--7159474.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159474
_shelx_shelxl_version_number     2018/3
_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   0.979
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.12841(7) 0.29874(10) 0.51549(7) 0.02613(19) Uani 1 1 d . . . . .
O2 O 0.30668(6) 0.57227(10) 0.19705(6) 0.02218(18) Uani 1 1 d . . . . .
O3 O 0.09451(6) 0.65594(9) 0.21577(6) 0.01660(16) Uani 1 1 d . . . . .
C1 C 0.27598(8) 0.54365(12) 0.28475(8) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.17217(8) 0.62470(12) 0.31161(8) 0.01382(19) Uani 1 1 d . . . . .
C3 C 0.12621(8) 0.54640(13) 0.41293(8) 0.0159(2) Uani 1 1 d . . . . .
H3 H 0.0483(12) 0.5355(17) 0.3989(11) 0.024 Uiso 1 1 d . U . . .
C4 C 0.17785(8) 0.39332(13) 0.46521(8) 0.0167(2) Uani 1 1 d . . . . .
C5 C 0.29520(8) 0.36477(12) 0.45687(8) 0.0168(2) Uani 1 1 d . . . . .
C6 C 0.35861(9) 0.26112(13) 0.53327(9) 0.0218(2) Uani 1 1 d . . . . .
H6 H 0.328327 0.214261 0.592491 0.026 Uiso 1 1 calc R U . . .
C7 C 0.46587(10) 0.22671(14) 0.52253(10) 0.0264(3) Uani 1 1 d . . . . .
H7 H 0.509180 0.157523 0.575202 0.032 Uiso 1 1 calc R U . . .
C8 C 0.51033(9) 0.29286(14) 0.43518(10) 0.0262(2) Uani 1 1 d . . . . .
H8 H 0.583415 0.267411 0.427633 0.031 Uiso 1 1 calc R U . . .
C9 C 0.44807(9) 0.39593(14) 0.35909(9) 0.0213(2) Uani 1 1 d . . . . .
H9 H 0.478626 0.440859 0.299432 0.026 Uiso 1 1 calc R U . . .
C10 C 0.34031(8) 0.43413(12) 0.36979(8) 0.0162(2) Uani 1 1 d . . . . .
C11 C 0.19796(8) 0.77493(12) 0.38579(8) 0.0156(2) Uani 1 1 d . . . . .
C12 C 0.16565(8) 0.70406(13) 0.47330(8) 0.0184(2) Uani 1 1 d . . . . .
H12 H 0.160266 0.739273 0.547765 0.022 Uiso 1 1 d R U . . .
C13 C 0.23814(9) 0.93823(13) 0.36485(9) 0.0196(2) Uani 1 1 d . . . . .
H13 H 0.256641 1.001523 0.430649 0.023 Uiso 1 1 d R U . . .
C14 C 0.19193(9) 1.02688(14) 0.25780(9) 0.0226(2) Uani 1 1 d . . . . .
H14A H 0.139169 0.966588 0.206224 0.027 Uiso 1 1 d R U . . .
H14B H 0.179869 1.141388 0.264724 0.027 Uiso 1 1 d R U . . .
C15 C 0.30788(9) 0.97044(14) 0.27660(10) 0.0244(2) Uani 1 1 d . . . . .
H15B H 0.367539 1.052089 0.295451 0.029 Uiso 1 1 d R U . . .
H15A H 0.323439 0.876689 0.234651 0.029 Uiso 1 1 d R U . . .
C16 C 0.05563(9) 0.51049(13) 0.15556(9) 0.0211(2) Uani 1 1 d . . . . .
H16A H -0.007996 0.537281 0.098898 0.032 Uiso 1 1 calc R U . . .
H16B H 0.034594 0.429646 0.207323 0.032 Uiso 1 1 calc R U . . .
H16C H 0.113793 0.465360 0.119411 0.032 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O3 C16 113.33(8) . . ?
O2 C1 C10 120.96(9) . . ?
O2 C1 C2 120.35(9) . . ?
C10 C1 C2 118.66(8) . . ?
O3 C2 C11 112.95(8) . . ?
O3 C2 C1 112.49(8) . . ?
C11 C2 C1 112.13(8) . . ?
O3 C2 C3 115.81(8) . . ?
C11 C2 C3 86.03(7) . . ?
C1 C2 C3 114.85(8) . . ?
C4 C3 C12 115.10(8) . . ?
C4 C3 C2 119.04(8) . . ?
C12 C3 C2 84.56(7) . . ?
C4 C3 H3 110.1(9) . . ?
C12 C3 H3 113.3(8) . . ?
C2 C3 H3 112.8(8) . . ?
O1 C4 C5 121.06(10) . . ?
O1 C4 C3 122.03(9) . . ?
C5 C4 C3 116.86(8) . . ?
C6 C5 C10 119.86(10) . . ?
C6 C5 C4 119.51(9) . . ?
C10 C5 C4 120.55(9) . . ?
C7 C6 C5 119.93(10) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.41(10) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.04(10) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.28(10) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 119.46(10) . . ?
C9 C10 C1 118.28(9) . . ?
C5 C10 C1 122.22(9) . . ?
C12 C11 C13 133.94(9) . . ?
C12 C11 C2 93.57(8) . . ?
C13 C11 C2 132.42(9) . . ?
C11 C12 C3 95.60(8) . . ?
C11 C12 H12 134.5 . . ?
C3 C12 H12 129.7 . . ?
C11 C13 C15 122.40(9) . . ?
C11 C13 C14 119.80(9) . . ?
C15 C13 C14 58.89(7) . . ?
C11 C13 H13 113.0 . . ?
C15 C13 H13 114.9 . . ?
C14 C13 H13 117.8 . . ?
C15 C14 C13 60.50(7) . . ?
C15 C14 H14A 118.1 . . ?
C13 C14 H14A 115.5 . . ?
C15 C14 H14B 116.9 . . ?
C13 C14 H14B 115.8 . . ?
H14A C14 H14B 117.5 . . ?
C14 C15 C13 60.61(7) . . ?
C14 C15 H15B 119.2 . . ?
C13 C15 H15B 116.5 . . ?
C14 C15 H15A 116.3 . . ?
C13 C15 H15A 115.5 . . ?
H15B C15 H15A 116.8 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
O1 C4 1.2166(13) . ?
O2 C1 1.2176(12) . ?
O3 C2 1.4038(11) . ?
O3 C16 1.4373(12) . ?
C1 C10 1.4931(14) . ?
C1 C2 1.5330(13) . ?
C2 C11 1.5269(13) . ?
C2 C3 1.5822(13) . ?
C3 C4 1.4983(14) . ?
C3 C12 1.5236(14) . ?
C3 H3 0.956(14) . ?
C4 C5 1.4948(14) . ?
C5 C6 1.3975(14) . ?
C5 C10 1.4022(14) . ?
C6 C7 1.3881(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3903(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3861(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4005(14) . ?
C9 H9 0.9500 . ?
C11 C12 1.3349(14) . ?
C11 C13 1.4638(14) . ?
C12 H12 0.9655 . ?
C13 C15 1.5150(15) . ?
C13 C14 1.5165(15) . ?
C13 H13 0.9491 . ?
C14 C15 1.4902(15) . ?
C14 H14A 0.9620 . ?
C14 H14B 0.9549 . ?
C15 H15B 0.9941 . ?
C15 H15A 0.9598 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
