#------------------------------------------------------------------------------
#$Date: 2020-04-02 02:44:33 +0300 (Thu, 02 Apr 2020) $
#$Revision: 249943 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038165.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_4038165
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         'C17 H14 O2'
_chemical_formula_sum            'C17 H14 O2'
_chemical_formula_weight         250.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90.785(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.775(2)
_cell_length_b                   6.3219(10)
_cell_length_c                   15.637(3)
_cell_measurement_reflns_used    1840
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.60
_cell_volume                     1262.8(4)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14355
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.723
_diffrn_reflns_theta_min         2.605
_diffrn_source                   'Fine-focused sealed tube'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       Rod
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0688
_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)+(0.0591P)²+1.3307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1679
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2065
_reflns_number_total             3273
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00197_si_003.cif
_cod_data_source_block           20180918JR_0m
_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_cell_volume        1262.7(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038165
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.61665(12) 0.5270(3) 0.34156(11) 0.0226(4) Uani 1 1 d . . . . .
H1 H 0.672637 0.567769 0.319343 0.034 Uiso 1 1 calc R U . . .
O2 O 0.69446(14) 0.2007(3) 0.21103(13) 0.0335(5) Uani 1 1 d . . . . .
C1 C 0.55669(18) 0.4047(4) 0.27974(16) 0.0206(5) Uani 1 1 d . . . . .
C2 C 0.62734(18) 0.2135(4) 0.26494(17) 0.0240(6) Uani 1 1 d . . . . .
C3 C 0.6049(2) 0.0534(4) 0.3339(2) 0.0319(7) Uani 1 1 d . . . . .
H3A H 0.668803 0.025629 0.368731 0.038 Uiso 1 1 calc R U . . .
H3AB H 0.580860 -0.081546 0.308266 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5193(2) 0.1487(4) 0.38944(18) 0.0278(6) Uani 1 1 d . . . . .
H4A H 0.549486 0.221152 0.440186 0.033 Uiso 1 1 calc R U . . .
H4AB H 0.469416 0.039044 0.408471 0.033 Uiso 1 1 calc R U . . .
C5 C 0.46609(18) 0.3069(4) 0.32826(16) 0.0223(5) Uani 1 1 d . . . . .
H5 H 0.423790 0.222763 0.286088 0.027 Uiso 1 1 calc R U . . .
C6 C 0.39578(17) 0.4764(4) 0.36260(16) 0.0210(5) Uani 1 1 d . . . . .
C7 C 0.35145(19) 0.4703(5) 0.44348(16) 0.0275(6) Uani 1 1 d . . . . .
H7 H 0.368038 0.357095 0.481240 0.033 Uiso 1 1 calc R U . . .
C8 C 0.28346(19) 0.6277(5) 0.46936(17) 0.0284(6) Uani 1 1 d . . . . .
H8 H 0.254109 0.622127 0.524810 0.034 Uiso 1 1 calc R U . . .
C9 C 0.25817(18) 0.7922(4) 0.41513(17) 0.0255(6) Uani 1 1 d . . . . .
H9 H 0.210144 0.897975 0.432539 0.031 Uiso 1 1 calc R U . . .
C10 C 0.30316(17) 0.8027(4) 0.33496(16) 0.0205(5) Uani 1 1 d . . . . .
H10 H 0.286255 0.917509 0.298105 0.025 Uiso 1 1 calc R U . . .
C11 C 0.37276(16) 0.6475(4) 0.30751(15) 0.0172(5) Uani 1 1 d . . . . .
C12 C 0.42526(17) 0.6606(4) 0.22320(15) 0.0163(5) Uani 1 1 d . . . . .
C13 C 0.38702(19) 0.7928(4) 0.15842(16) 0.0250(6) Uani 1 1 d . . . . .
H13 H 0.324528 0.870834 0.167154 0.030 Uiso 1 1 calc R U . . .
C14 C 0.4387(2) 0.8115(5) 0.08189(17) 0.0295(6) Uani 1 1 d . . . . .
H14 H 0.412247 0.904080 0.038891 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5289(2) 0.6964(4) 0.06740(17) 0.0278(6) Uani 1 1 d . . . . .
H15 H 0.564241 0.709596 0.014626 0.033 Uiso 1 1 calc R U . . .
C16 C 0.56714(18) 0.5619(4) 0.13021(17) 0.0248(6) Uani 1 1 d . . . . .
H16 H 0.629042 0.482884 0.120322 0.030 Uiso 1 1 calc R U . . .
C17 C 0.51610(17) 0.5413(4) 0.20748(15) 0.0176(5) Uani 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 0.0033 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
C1 O1 H1 109.5 . . ?
O1 C1 C17 111.58(19) . . ?
O1 C1 C5 106.4(2) . . ?
C17 C1 C5 110.47(19) . . ?
O1 C1 C2 102.42(18) . . ?
C17 C1 C2 122.5(2) . . ?
C5 C1 C2 102.03(19) . . ?
O2 C2 C3 126.5(2) . . ?
O2 C2 C1 125.6(2) . . ?
C3 C2 C1 107.7(2) . . ?
C2 C3 C4 106.6(2) . . ?
C2 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
C2 C3 H3AB 110.4 . . ?
C4 C3 H3AB 110.4 . . ?
H3A C3 H3AB 108.6 . . ?
C3 C4 C5 102.5(2) . . ?
C3 C4 H4A 111.3 . . ?
C5 C4 H4A 111.3 . . ?
C3 C4 H4AB 111.3 . . ?
C5 C4 H4AB 111.3 . . ?
H4A C4 H4AB 109.2 . . ?
C6 C5 C1 110.5(2) . . ?
C6 C5 C4 120.2(2) . . ?
C1 C5 C4 104.01(19) . . ?
C6 C5 H5 107.1 . . ?
C1 C5 H5 107.1 . . ?
C4 C5 H5 107.1 . . ?
C7 C6 C11 119.4(2) . . ?
C7 C6 C5 123.9(2) . . ?
C11 C6 C5 116.7(2) . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 121.2(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C6 118.6(2) . . ?
C10 C11 C12 122.0(2) . . ?
C6 C11 C12 119.3(2) . . ?
C13 C12 C17 118.3(2) . . ?
C13 C12 C11 121.2(2) . . ?
C17 C12 C11 120.4(2) . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 120.0(2) . . ?
C16 C17 C1 123.1(2) . . ?
C12 C17 C1 116.8(2) . . ?
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 1.448(3) . ?
O1 H1 0.8400 . ?
O2 C2 1.213(3) . ?
C1 C17 1.508(3) . ?
C1 C5 1.524(3) . ?
C1 C2 1.528(3) . ?
C2 C3 1.510(4) . ?
C3 C4 1.530(4) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.536(3) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C6 1.502(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.393(3) . ?
C6 C11 1.412(3) . ?
C7 C8 1.385(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.490(3) . ?
C12 C13 1.396(3) . ?
C12 C17 1.408(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
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 O2 -90.1(3) . . . . ?
C17 C1 C2 O2 35.8(4) . . . . ?
C5 C1 C2 O2 159.8(2) . . . . ?
O1 C1 C2 C3 85.0(2) . . . . ?
C17 C1 C2 C3 -149.1(2) . . . . ?
C5 C1 C2 C3 -25.0(3) . . . . ?
O2 C2 C3 C4 175.9(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 23.6(3) . . . . ?
O1 C1 C5 C6 63.2(2) . . . . ?
C17 C1 C5 C6 -58.1(3) . . . . ?
C2 C1 C5 C6 170.20(19) . . . . ?
O1 C1 C5 C4 -67.1(2) . . . . ?
C17 C1 C5 C4 171.6(2) . . . . ?
C2 C1 C5 C4 39.9(2) . . . . ?
C3 C4 C5 C6 -163.9(2) . . . . ?
C3 C4 C5 C1 -39.7(2) . . . . ?
C1 C5 C6 C7 -139.2(2) . . . . ?
C4 C5 C6 C7 -18.1(3) . . . . ?
C1 C5 C6 C11 42.3(3) . . . . ?
C4 C5 C6 C11 163.4(2) . . . . ?
C11 C6 C7 C8 1.5(4) . . . . ?
C5 C6 C7 C8 -177.0(2) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 -1.6(4) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C9 C10 C11 C6 0.9(3) . . . . ?
C9 C10 C11 C12 -177.4(2) . . . . ?
C7 C6 C11 C10 -2.1(3) . . . . ?
C5 C6 C11 C10 176.5(2) . . . . ?
C7 C6 C11 C12 176.3(2) . . . . ?
C5 C6 C11 C12 -5.1(3) . . . . ?
C10 C11 C12 C13 -18.0(3) . . . . ?
C6 C11 C12 C13 163.7(2) . . . . ?
C10 C11 C12 C17 161.1(2) . . . . ?
C6 C11 C12 C17 -17.3(3) . . . . ?
C17 C12 C13 C14 -2.1(4) . . . . ?
C11 C12 C13 C14 177.0(2) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C12 -1.1(4) . . . . ?
C15 C16 C17 C1 -177.2(2) . . . . ?
C13 C12 C17 C16 2.1(3) . . . . ?
C11 C12 C17 C16 -177.0(2) . . . . ?
C13 C12 C17 C1 178.5(2) . . . . ?
C11 C12 C17 C1 -0.6(3) . . . . ?
O1 C1 C17 C16 95.9(3) . . . . ?
C5 C1 C17 C16 -145.9(2) . . . . ?
C2 C1 C17 C16 -25.8(4) . . . . ?
O1 C1 C17 C12 -80.4(3) . . . . ?
C5 C1 C17 C12 37.8(3) . . . . ?
C2 C1 C17 C12 157.9(2) . . . . ?
