#------------------------------------------------------------------------------
#$Date: 2020-04-02 02:44:09 +0300 (Thu, 02 Apr 2020) $
#$Revision: 249942 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038164.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_4038164
loop_
_publ_author_name
'Zhao, Xuchen'
'Song, Changqing'
'Rainier, Jon Douglas'
_publ_section_title
;
 Photoelectrocyclization Reactions of Conjugated Cycloalkenones. Scope and
 Reactivity.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00197
_journal_year                    2020
_chemical_formula_moiety         'C19 H18 O'
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33
_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   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 101.674(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7467(13)
_cell_length_b                   6.3268(5)
_cell_length_c                   13.5922(11)
_cell_measurement_reflns_used    9272
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      36.43
_cell_measurement_theta_min      3.06
_cell_volume                     1326.13(19)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '/w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38002
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.630
_diffrn_reflns_theta_min         2.642
_diffrn_source                   'Fine-focused sealed tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.7171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       'RECTANGULAR BLOCK'
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         6129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0366
_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)+(0.0621P)²+0.3509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5312
_reflns_number_total             6129
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00197_si_002.cif
_cod_data_source_block           20180918JR_PM
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038164
_shelx_shelxl_version_number     2017/1
_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   0.959
_shelx_estimated_absorpt_t_max   0.984
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 0.41823(3) 0.16062(9) 0.79654(4) 0.01797(11) Uani 1 1 d . . . . .
C1 C 0.38637(4) 0.19268(10) 0.70830(4) 0.01076(10) Uani 1 1 d . . . . .
C2 C 0.41382(4) 0.07265(10) 0.62484(5) 0.01341(11) Uani 1 1 d . . . . .
H2A H 0.363660 -0.005788 0.586000 0.016 Uiso 1 1 calc R U . . .
H2AB H 0.459258 -0.031067 0.653295 0.016 Uiso 1 1 calc R U . . .
C3 C 0.44918(5) 0.22621(13) 0.55493(6) 0.02060(14) Uani 1 1 d . . . . .
H3A H 0.509750 0.263231 0.586026 0.025 Uiso 1 1 calc R U . . .
H3AB H 0.449933 0.153668 0.490575 0.025 Uiso 1 1 calc R U . . .
C4 C 0.39595(4) 0.43098(10) 0.53309(5) 0.01209(10) Uani 1 1 d . . . . .
H4A H 0.428181 0.549101 0.571379 0.015 Uiso 1 1 calc R U . . .
H4AB H 0.387557 0.465010 0.460669 0.015 Uiso 1 1 calc R U . . .
C5 C 0.30758(4) 0.40786(9) 0.56220(4) 0.00903(9) Uani 1 1 d . . . . .
H5 H 0.280096 0.278215 0.527495 0.011 Uiso 1 1 calc R U . . .
C6 C 0.24425(4) 0.58675(9) 0.53155(4) 0.00981(10) Uani 1 1 d . . . . .
C7 C 0.25552(4) 0.74456(10) 0.46376(5) 0.01269(10) Uani 1 1 d . . . . .
H7 H 0.305690 0.743143 0.434970 0.015 Uiso 1 1 calc R U . . .
C8 C 0.19404(5) 0.90472(10) 0.43757(5) 0.01565(12) Uani 1 1 d . . . . .
H8 H 0.201674 1.009148 0.389894 0.019 Uiso 1 1 calc R U . . .
C9 C 0.12157(5) 0.91083(11) 0.48156(5) 0.01717(12) Uani 1 1 d . . . . .
H9 H 0.080492 1.021884 0.465548 0.021 Uiso 1 1 calc R U . . .
C10 C 0.10949(4) 0.75367(11) 0.54910(5) 0.01537(11) Uani 1 1 d . . . . .
H10 H 0.060098 0.758642 0.579236 0.018 Uiso 1 1 calc R U . . .
C11 C 0.16922(4) 0.58835(9) 0.57317(4) 0.01088(10) Uani 1 1 d . . . . .
C12 C 0.15672(4) 0.41557(9) 0.64224(4) 0.01068(10) Uani 1 1 d . . . . .
C13 C 0.07374(4) 0.36078(11) 0.65599(5) 0.01407(11) Uani 1 1 d . . . . .
H13 H 0.024700 0.434473 0.619735 0.017 Uiso 1 1 calc R U . . .
C14 C 0.06190(4) 0.20010(11) 0.72193(5) 0.01588(12) Uani 1 1 d . . . . .
H14 H 0.005227 0.164995 0.730623 0.019 Uiso 1 1 calc R U . . .
C15 C 0.13336(4) 0.09132(11) 0.77495(5) 0.01486(11) Uani 1 1 d . . . . .
H15 H 0.125694 -0.017467 0.820538 0.018 Uiso 1 1 calc R U . . .
C16 C 0.21643(4) 0.14215(10) 0.76113(5) 0.01208(10) Uani 1 1 d . . . . .
H16 H 0.265026 0.067054 0.797496 0.015 Uiso 1 1 calc R U . . .
C17 C 0.22912(4) 0.30163(9) 0.69467(4) 0.00939(9) Uani 1 1 d . . . . .
C18 C 0.31821(4) 0.36731(9) 0.67680(4) 0.00887(9) Uani 1 1 d . . . . .
C19 C 0.34913(4) 0.56502(10) 0.74063(5) 0.01274(10) Uani 1 1 d . . . . .
H19A H 0.403948 0.614937 0.725371 0.019 Uiso 1 1 calc R U . . .
H19B H 0.357756 0.529005 0.812092 0.019 Uiso 1 1 calc R U . . .
H19C H 0.305313 0.676605 0.724951 0.019 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
O1 C1 C2 122.38(6) . . ?
O1 C1 C18 121.17(6) . . ?
C2 C1 C18 116.39(5) . . ?
C1 C2 C3 110.05(5) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2AB 109.7 . . ?
C3 C2 H2AB 109.7 . . ?
H2A C2 H2AB 108.2 . . ?
C4 C3 C2 113.54(5) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3AB 108.9 . . ?
C2 C3 H3AB 108.9 . . ?
H3A C3 H3AB 107.7 . . ?
C5 C4 C3 111.00(5) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4AB 109.4 . . ?
C3 C4 H4AB 109.4 . . ?
H4A C4 H4AB 108.0 . . ?
C6 C5 C4 116.21(5) . . ?
C6 C5 C18 109.35(5) . . ?
C4 C5 C18 110.87(5) . . ?
C6 C5 H5 106.6 . . ?
C4 C5 H5 106.6 . . ?
C18 C5 H5 106.6 . . ?
C7 C6 C11 119.29(5) . . ?
C7 C6 C5 123.63(5) . . ?
C11 C6 C5 117.07(5) . . ?
C6 C7 C8 120.90(6) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 119.79(6) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 119.78(6) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.83(6) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 119.31(6) . . ?
C10 C11 C12 122.05(6) . . ?
C6 C11 C12 118.64(5) . . ?
C13 C12 C17 119.05(5) . . ?
C13 C12 C11 121.00(5) . . ?
C17 C12 C11 119.95(5) . . ?
C14 C13 C12 121.10(6) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 119.71(6) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.90(6) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.96(6) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C12 119.25(5) . . ?
C16 C17 C18 123.75(5) . . ?
C12 C17 C18 116.98(5) . . ?
C17 C18 C1 111.80(5) . . ?
C17 C18 C19 109.03(5) . . ?
C1 C18 C19 107.60(5) . . ?
C17 C18 C5 106.73(4) . . ?
C1 C18 C5 108.96(5) . . ?
C19 C18 C5 112.79(5) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 C1 1.2198(8) . ?
C1 C2 1.4995(9) . ?
C1 C18 1.5396(8) . ?
C2 C3 1.5398(10) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.5390(10) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.5288(8) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C6 1.5102(8) . ?
C5 C18 1.5539(8) . ?
C5 H5 1.0000 . ?
C6 C7 1.3942(8) . ?
C6 C11 1.4093(9) . ?
C7 C8 1.3968(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.3919(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.3923(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.4005(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.4799(9) . ?
C12 C13 1.4005(9) . ?
C12 C17 1.4137(8) . ?
C13 C14 1.3924(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.3896(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.3962(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.3954(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.5289(8) . ?
C18 C19 1.5439(8) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
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
O1 C1 C2 C3 -120.28(7) . . . . ?
C18 C1 C2 C3 57.03(7) . . . . ?
C1 C2 C3 C4 -41.36(8) . . . . ?
C2 C3 C4 C5 -15.47(8) . . . . ?
C3 C4 C5 C6 -171.92(5) . . . . ?
C3 C4 C5 C18 62.41(7) . . . . ?
C4 C5 C6 C7 12.81(8) . . . . ?
C18 C5 C6 C7 139.23(6) . . . . ?
C4 C5 C6 C11 -168.57(5) . . . . ?
C18 C5 C6 C11 -42.15(7) . . . . ?
C11 C6 C7 C8 0.69(9) . . . . ?
C5 C6 C7 C8 179.29(6) . . . . ?
C6 C7 C8 C9 1.73(10) . . . . ?
C7 C8 C9 C10 -1.93(10) . . . . ?
C8 C9 C10 C11 -0.29(10) . . . . ?
C9 C10 C11 C6 2.70(10) . . . . ?
C9 C10 C11 C12 -178.08(6) . . . . ?
C7 C6 C11 C10 -2.88(9) . . . . ?
C5 C6 C11 C10 178.44(6) . . . . ?
C7 C6 C11 C12 177.87(5) . . . . ?
C5 C6 C11 C12 -0.81(8) . . . . ?
C10 C11 C12 C13 25.10(9) . . . . ?
C6 C11 C12 C13 -155.67(6) . . . . ?
C10 C11 C12 C17 -155.58(6) . . . . ?
C6 C11 C12 C17 23.64(8) . . . . ?
C17 C12 C13 C14 1.52(10) . . . . ?
C11 C12 C13 C14 -179.16(6) . . . . ?
C12 C13 C14 C15 -0.19(11) . . . . ?
C13 C14 C15 C16 -0.64(11) . . . . ?
C14 C15 C16 C17 0.11(10) . . . . ?
C15 C16 C17 C12 1.22(9) . . . . ?
C15 C16 C17 C18 179.24(6) . . . . ?
C13 C12 C17 C16 -2.01(9) . . . . ?
C11 C12 C17 C16 178.66(5) . . . . ?
C13 C12 C17 C18 179.84(5) . . . . ?
C11 C12 C17 C18 0.51(8) . . . . ?
C16 C17 C18 C1 20.71(8) . . . . ?
C12 C17 C18 C1 -161.23(5) . . . . ?
C16 C17 C18 C19 -98.13(7) . . . . ?
C12 C17 C18 C19 79.93(6) . . . . ?
C16 C17 C18 C5 139.76(6) . . . . ?
C12 C17 C18 C5 -42.18(7) . . . . ?
O1 C1 C18 C17 -76.49(7) . . . . ?
C2 C1 C18 C17 106.17(6) . . . . ?
O1 C1 C18 C19 43.20(8) . . . . ?
C2 C1 C18 C19 -134.14(5) . . . . ?
O1 C1 C18 C5 165.79(6) . . . . ?
C2 C1 C18 C5 -11.55(7) . . . . ?
C6 C5 C18 C17 62.03(6) . . . . ?
C4 C5 C18 C17 -168.56(5) . . . . ?
C6 C5 C18 C1 -177.09(5) . . . . ?
C4 C5 C18 C1 -47.68(6) . . . . ?
C6 C5 C18 C19 -57.69(6) . . . . ?
C4 C5 C18 C19 71.73(6) . . . . ?
