#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:11:38 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/26/7242614.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_7242614
loop_
_publ_author_name
'Li, Wenjing'
'Li, Shun'
'Luo, Lihua'
'Ge, Yicen'
'Xu, Jiaqi'
'Zheng, Xueli'
'Yuan, Maolin'
'Li, Ruixiang'
'Chen, Hua'
'Fu, Haiyan'
_publ_section_title
;
 Visible-light-initiated catalyst-free oxidative cleavage of
 (Z)-triaryl-substituted alkenes containing pyridyl motif under ambient
 conditions
;
_journal_issue                   10
_journal_name_full               'Green Chemistry'
_journal_page_first              3649
_journal_page_last               3655
_journal_paper_doi               10.1039/D1GC00716E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C18 H13 N O'
_chemical_formula_weight         259.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-01-13 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                93.473(7)
_cell_angle_beta                 98.583(7)
_cell_angle_gamma                109.416(8)
_cell_formula_units_Z            2
_cell_length_a                   7.1154(7)
_cell_length_b                   9.6387(8)
_cell_length_c                   10.8333(9)
_cell_measurement_temperature    293(2)
_cell_volume                     688.03(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5657
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.086
_exptl_absorpt_coefficient_mu    0.078
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0502
_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)+(0.0578P)²+0.0615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1315
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1992
_reflns_number_total             2806
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1gc00716e2.cif
_cod_data_source_block           200821_s2_lwj
_cod_depositor_comments          'Adding full bibliography for 7242614.cif.'
_cod_database_code               7242614
_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   0.973
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.1878(2) 0.78294(14) 0.44800(11) 0.0416(3) Uani 1 1 d . . . . .
C5 C 0.2754(2) 0.75734(17) 0.55856(15) 0.0411(4) Uani 1 1 d . . . . .
C13 C 0.1431(2) 0.71237(17) 0.65356(14) 0.0398(4) Uani 1 1 d . . . . .
C6 C 0.2094(3) 0.86674(19) 0.24237(15) 0.0484(4) Uani 1 1 d . . . . .
C18 C -0.0596(2) 0.62474(18) 0.61712(15) 0.0460(4) Uani 1 1 d . . . . .
H18 H -0.1135 0.5947 0.5322 0.055 Uiso 1 1 calc R U . . .
C7 C -0.0134(3) 0.80557(18) 0.19781(14) 0.0427(4) Uani 1 1 d . . . . .
C1 C 0.3058(3) 0.82889(17) 0.36220(14) 0.0436(4) Uani 1 1 d . . . . .
O1 O 0.31792(19) 0.95024(16) 0.18090(12) 0.0715(4) Uani 1 1 d . . . . .
C8 C -0.1314(3) 0.66351(18) 0.21519(15) 0.0465(4) Uani 1 1 d . . . . .
H8 H -0.0738 0.6062 0.2632 0.056 Uiso 1 1 calc R U . . .
C14 C 0.2188(3) 0.7581(2) 0.78120(15) 0.0500(4) Uani 1 1 d . . . . .
H14 H 0.3541 0.8170 0.8074 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4790(3) 0.7728(2) 0.58331(16) 0.0505(4) Uani 1 1 d . . . . .
H4 H 0.5351 0.7523 0.6601 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5972(3) 0.8186(2) 0.49384(17) 0.0555(5) Uani 1 1 d . . . . .
H3 H 0.7334 0.8286 0.5089 0.067 Uiso 1 1 calc R U . . .
C2 C 0.5102(3) 0.8495(2) 0.38171(16) 0.0512(5) Uani 1 1 d . . . . .
H2 H 0.5872 0.8834 0.3203 0.061 Uiso 1 1 calc R U . . .
C9 C -0.3341(3) 0.6073(2) 0.16130(16) 0.0528(5) Uani 1 1 d . . . . .
H9 H -0.4120 0.5114 0.1716 0.063 Uiso 1 1 calc R U . . .
C15 C 0.0953(3) 0.7171(2) 0.86901(16) 0.0577(5) Uani 1 1 d . . . . .
H15 H 0.1472 0.7490 0.9539 0.069 Uiso 1 1 calc R U . . .
C16 C -0.1040(3) 0.6292(2) 0.83162(18) 0.0588(5) Uani 1 1 d . . . . .
H16 H -0.1869 0.6015 0.8912 0.071 Uiso 1 1 calc R U . . .
C12 C -0.1039(3) 0.8897(2) 0.12735(15) 0.0532(5) Uani 1 1 d . . . . .
H12 H -0.0264 0.9849 0.1149 0.064 Uiso 1 1 calc R U . . .
C10 C -0.4216(3) 0.6924(2) 0.09237(17) 0.0587(5) Uani 1 1 d . . . . .
H10 H -0.5586 0.6543 0.0570 0.070 Uiso 1 1 calc R U . . .
C17 C -0.1818(3) 0.5818(2) 0.70563(18) 0.0552(5) Uani 1 1 d . . . . .
H17 H -0.3165 0.5211 0.6805 0.066 Uiso 1 1 calc R U . . .
C11 C -0.3067(3) 0.8339(2) 0.07572(17) 0.0607(5) Uani 1 1 d . . . . .
H11 H -0.3660 0.8917 0.0296 0.073 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'
N N 0.0061 0.0033 '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
C5 N1 C1 117.51(14) . . ?
N1 C5 C4 121.91(14) . . ?
N1 C5 C13 116.37(14) . . ?
C4 C5 C13 121.71(14) . . ?
C18 C13 C14 118.45(15) . . ?
C18 C13 C5 120.72(14) . . ?
C14 C13 C5 120.83(15) . . ?
O1 C6 C7 119.85(15) . . ?
O1 C6 C1 118.63(16) . . ?
C7 C6 C1 121.52(13) . . ?
C17 C18 C13 120.64(16) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C8 C7 C12 118.83(16) . . ?
C8 C7 C6 122.58(15) . . ?
C12 C7 C6 118.39(15) . . ?
N1 C1 C2 123.51(14) . . ?
N1 C1 C6 117.03(15) . . ?
C2 C1 C6 119.39(14) . . ?
C9 C8 C7 120.04(16) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C15 C14 C13 120.67(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C3 C4 C5 119.76(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C2 C3 C4 118.75(17) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C2 C1 118.51(15) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C10 C9 C8 120.39(17) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C16 C15 C14 120.17(17) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.10(16) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C11 C12 C7 120.82(17) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C9 C10 C11 120.05(18) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C18 C17 C16 119.96(17) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C12 C11 C10 119.87(17) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
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
N1 C5 1.3414(19) . ?
N1 C1 1.3420(19) . ?
C5 C4 1.388(2) . ?
C5 C13 1.485(2) . ?
C13 C18 1.389(2) . ?
C13 C14 1.394(2) . ?
C6 O1 1.2219(18) . ?
C6 C7 1.486(2) . ?
C6 C1 1.499(2) . ?
C18 C17 1.380(2) . ?
C18 H18 0.9300 . ?
C7 C8 1.389(2) . ?
C7 C12 1.389(2) . ?
C1 C2 1.382(2) . ?
C8 C9 1.381(2) . ?
C8 H8 0.9300 . ?
C14 C15 1.378(2) . ?
C14 H14 0.9300 . ?
C4 C3 1.375(2) . ?
C4 H4 0.9300 . ?
C3 C2 1.374(2) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C9 C10 1.376(2) . ?
C9 H9 0.9300 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C12 C11 1.375(3) . ?
C12 H12 0.9300 . ?
C10 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C17 H17 0.9300 . ?
C11 H11 0.9300 . ?
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
C1 N1 C5 C4 -2.0(2) . . . . ?
C1 N1 C5 C13 177.66(14) . . . . ?
N1 C5 C13 C18 34.7(2) . . . . ?
C4 C5 C13 C18 -145.67(17) . . . . ?
N1 C5 C13 C14 -144.72(16) . . . . ?
C4 C5 C13 C14 34.9(2) . . . . ?
C14 C13 C18 C17 -1.2(2) . . . . ?
C5 C13 C18 C17 179.36(15) . . . . ?
O1 C6 C7 C8 144.86(18) . . . . ?
C1 C6 C7 C8 -35.3(2) . . . . ?
O1 C6 C7 C12 -29.8(3) . . . . ?
C1 C6 C7 C12 149.94(16) . . . . ?
C5 N1 C1 C2 0.6(2) . . . . ?
C5 N1 C1 C6 -176.08(14) . . . . ?
O1 C6 C1 N1 157.26(17) . . . . ?
C7 C6 C1 N1 -22.5(2) . . . . ?
O1 C6 C1 C2 -19.6(3) . . . . ?
C7 C6 C1 C2 160.63(16) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
C6 C7 C8 C9 -173.71(15) . . . . ?
C18 C13 C14 C15 0.1(3) . . . . ?
C5 C13 C14 C15 179.52(15) . . . . ?
N1 C5 C4 C3 1.4(3) . . . . ?
C13 C5 C4 C3 -178.21(15) . . . . ?
C5 C4 C3 C2 0.6(3) . . . . ?
C4 C3 C2 C1 -1.9(3) . . . . ?
N1 C1 C2 C3 1.3(3) . . . . ?
C6 C1 C2 C3 177.93(16) . . . . ?
C7 C8 C9 C10 -1.4(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
C6 C7 C12 C11 175.04(16) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C13 C18 C17 C16 1.6(3) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C7 C12 C11 C10 -0.8(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
