#------------------------------------------------------------------------------
#$Date: 2021-12-01 00:56:04 +0200 (Wed, 01 Dec 2021) $
#$Revision: 270945 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/93/7129331.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_7129331
loop_
_publ_author_name
'Xia, Dong'
'Duan, Xin-Fang'
_publ_section_title
;
 Tandem vinyl radical Minisci-type annulation on pyridines: one-pot
 expeditious access to azaindenones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06204B
_journal_year                    2021
_chemical_formula_sum            'C25 H22 N2 O'
_chemical_formula_weight         366.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc28wrmk
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-09-25 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.1929(4)
_cell_length_b                   12.0792(3)
_cell_length_c                   7.0699(2)
_cell_measurement_temperature    100(2)
_cell_volume                     1895.25(8)
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.957
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6734
_diffrn_reflns_point_group_measured_fraction_full 0.809
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.416
_diffrn_reflns_theta_min         3.659
_exptl_absorpt_coefficient_mu    0.615
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             776
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 881 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0363
_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)+(0.0532P)²+0.2806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.462
_reflns_Friedel_fraction_full    0.582
_reflns_Friedel_fraction_max     0.525
_reflns_number_gt                2902
_reflns_number_total             3021
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06204b2.cif
_cod_data_source_block           20210815a_auto
_cod_database_code               7129331
_shelx_shelxl_version_number     2018/1
_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, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
O28 O 0.74787(6) 0.20891(10) 0.5060(3) 0.0278(3) Uani 1 1 d . . . . .
N1 N 0.73499(7) 0.60010(11) 0.4907(3) 0.0191(3) Uani 1 1 d . . . . .
C9 C 0.79482(8) 0.62442(14) 0.4961(4) 0.0202(4) Uani 1 1 d . . . . .
N16 N 0.87784(10) 0.89384(15) 0.5623(4) 0.0386(5) Uani 1 1 d . . . . .
C2 C 0.72092(8) 0.49392(14) 0.4953(3) 0.0182(4) Uani 1 1 d . . . . .
C5 C 0.72736(8) 0.30211(14) 0.5059(4) 0.0209(4) Uani 1 1 d . . . . .
C15 C 0.55519(9) 0.48812(16) 0.3643(3) 0.0221(4) Uani 1 1 d . . . . .
H15 H 0.555470 0.418661 0.301336 0.027 Uiso 1 1 calc R U . . .
C3 C 0.65829(8) 0.44753(13) 0.4922(3) 0.0183(4) Uani 1 1 d . . . . .
C18 C 0.80859(9) 0.74481(14) 0.4968(4) 0.0215(4) Uani 1 1 d . . . . .
C6 C 0.76247(8) 0.40755(14) 0.5032(4) 0.0201(4) Uani 1 1 d . . . . .
C7 C 0.82284(8) 0.43115(15) 0.5039(4) 0.0215(4) Uani 1 1 d . . . . .
H7 H 0.852255 0.374040 0.506551 0.026 Uiso 1 1 calc R U . . .
C10 C 0.60503(8) 0.51966(14) 0.4740(3) 0.0187(4) Uani 1 1 d . . . . .
C26 C 0.55651(10) 0.10247(17) 0.3245(4) 0.0255(5) Uani 1 1 d . . . . .
H26A H 0.517392 0.141539 0.333291 0.031 Uiso 1 1 calc R U . . .
H26B H 0.556921 0.059819 0.204924 0.031 Uiso 1 1 calc R U . . .
C4 C 0.66163(8) 0.33527(14) 0.5033(3) 0.0201(4) Uani 1 1 d . . . . .
C19 C 0.76477(10) 0.82118(16) 0.4442(3) 0.0260(5) Uani 1 1 d . . . . .
H19 H 0.726159 0.796693 0.403984 0.031 Uiso 1 1 calc R U . . .
C23 C 0.61813(9) 0.16949(17) 0.6764(3) 0.0230(5) Uani 1 1 d . . . . .
H23A H 0.656726 0.128952 0.664685 0.028 Uiso 1 1 calc R U . . .
H23B H 0.618668 0.210819 0.797272 0.028 Uiso 1 1 calc R U . . .
C11 C 0.60375(9) 0.62350(15) 0.5628(3) 0.0209(4) Uani 1 1 d . . . . .
H11 H 0.637362 0.647198 0.635465 0.025 Uiso 1 1 calc R U . . .
C14 C 0.50550(10) 0.55712(18) 0.3468(4) 0.0268(5) Uani 1 1 d . . . . .
H14 H 0.471900 0.534562 0.272976 0.032 Uiso 1 1 calc R U . . .
C12 C 0.55382(9) 0.69195(15) 0.5453(3) 0.0251(5) Uani 1 1 d . . . . .
H12 H 0.553194 0.761555 0.607790 0.030 Uiso 1 1 calc R U . . .
C8 C 0.83936(8) 0.54309(14) 0.5007(3) 0.0210(4) Uani 1 1 d . . . . .
H8 H 0.880707 0.563455 0.501644 0.025 Uiso 1 1 calc R U . . .
C20 C 0.77789(11) 0.93315(17) 0.4508(3) 0.0294(5) Uani 1 1 d . . . . .
H20 H 0.748714 0.986770 0.415106 0.035 Uiso 1 1 calc R U . . .
C27 C 0.60778(10) 0.18729(17) 0.3224(4) 0.0243(5) Uani 1 1 d . . . . .
H27A H 0.601245 0.240225 0.217520 0.029 Uiso 1 1 calc R U . . .
H27B H 0.646440 0.148684 0.299478 0.029 Uiso 1 1 calc R U . . .
C24 C 0.56559(10) 0.08675(17) 0.6769(4) 0.0256(5) Uani 1 1 d . . . . .
H24A H 0.570670 0.034050 0.782928 0.031 Uiso 1 1 calc R U . . .
H24B H 0.527219 0.127018 0.696068 0.031 Uiso 1 1 calc R U . . .
C25 C 0.56302(9) 0.02331(15) 0.4913(4) 0.0276(5) Uani 1 1 d . . . . .
H25A H 0.528397 -0.028355 0.493510 0.033 Uiso 1 1 calc R U . . .
H25B H 0.600279 -0.020871 0.476231 0.033 Uiso 1 1 calc R U . . .
C22 C 0.61158(8) 0.25128(14) 0.5104(3) 0.0206(4) Uani 1 1 d . . . . .
H22 H 0.572801 0.292221 0.527580 0.025 Uiso 1 1 calc R U . . .
C21 C 0.83453(10) 0.96476(16) 0.5107(4) 0.0313(5) Uani 1 1 d . . . . .
H21 H 0.843322 1.041682 0.515562 0.038 Uiso 1 1 calc R U . . .
C13 C 0.50497(9) 0.65930(18) 0.4373(4) 0.0275(5) Uani 1 1 d . . . . .
H13 H 0.471045 0.706721 0.424964 0.033 Uiso 1 1 calc R U . . .
C17 C 0.86428(10) 0.78570(17) 0.5546(4) 0.0321(5) Uani 1 1 d . . . . .
H17 H 0.894431 0.734013 0.590585 0.039 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 0.0181 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'
N N 0.0311 0.0180 '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
C2 N1 C9 116.09(15) . . ?
N1 C9 C8 122.72(15) . . ?
N1 C9 C18 114.33(16) . . ?
C8 C9 C18 122.95(16) . . ?
C21 N16 C17 116.8(2) . . ?
N1 C2 C6 124.87(16) . . ?
N1 C2 C3 125.60(15) . . ?
C6 C2 C3 109.53(14) . . ?
O28 C5 C6 126.52(17) . . ?
O28 C5 C4 127.37(17) . . ?
C6 C5 C4 106.09(14) . . ?
C14 C15 C10 120.84(19) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C4 C3 C10 129.64(16) . . ?
C4 C3 C2 108.74(15) . . ?
C10 C3 C2 121.60(15) . . ?
C19 C18 C17 117.63(17) . . ?
C19 C18 C9 120.29(17) . . ?
C17 C18 C9 122.05(18) . . ?
C7 C6 C2 119.44(16) . . ?
C7 C6 C5 133.46(16) . . ?
C2 C6 C5 107.09(15) . . ?
C6 C7 C8 117.18(16) . . ?
C6 C7 H7 121.4 . . ?
C8 C7 H7 121.4 . . ?
C11 C10 C15 118.28(17) . . ?
C11 C10 C3 120.38(17) . . ?
C15 C10 C3 121.31(17) . . ?
C25 C26 C27 110.88(19) . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C3 C4 C22 129.32(16) . . ?
C3 C4 C5 108.49(15) . . ?
C22 C4 C5 122.19(15) . . ?
C20 C19 C18 119.5(2) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C24 C23 C22 110.33(17) . . ?
C24 C23 H23A 109.6 . . ?
C22 C23 H23A 109.6 . . ?
C24 C23 H23B 109.6 . . ?
C22 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C12 C11 C10 120.59(19) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C13 C12 C11 120.33(19) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C9 C8 C7 119.66(16) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C21 C20 C19 118.2(2) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C26 C27 C22 111.62(19) . . ?
C26 C27 H27A 109.3 . . ?
C22 C27 H27A 109.3 . . ?
C26 C27 H27B 109.3 . . ?
C22 C27 H27B 109.3 . . ?
H27A C27 H27B 108.0 . . ?
C25 C24 C23 110.76(18) . . ?
C25 C24 H24A 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 C26 110.79(15) . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C4 C22 C27 110.49(19) . . ?
C4 C22 C23 112.83(18) . . ?
C27 C22 C23 109.91(15) . . ?
C4 C22 H22 107.8 . . ?
C27 C22 H22 107.8 . . ?
C23 C22 H22 107.8 . . ?
N16 C21 C20 124.10(18) . . ?
N16 C21 H21 118.0 . . ?
C20 C21 H21 118.0 . . ?
C12 C13 C14 120.03(19) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
N16 C17 C18 123.8(2) . . ?
N16 C17 H17 118.1 . . ?
C18 C17 H17 118.1 . . ?
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
O28 C5 1.214(2) . ?
N1 C2 1.320(2) . ?
N1 C9 1.360(2) . ?
C9 C8 1.394(3) . ?
C9 C18 1.486(2) . ?
N16 C21 1.338(3) . ?
N16 C17 1.342(3) . ?
C2 C6 1.393(2) . ?
C2 C3 1.499(2) . ?
C5 C6 1.493(2) . ?
C5 C4 1.513(3) . ?
C15 C14 1.388(3) . ?
C15 C10 1.404(3) . ?
C15 H15 0.9500 . ?
C3 C4 1.360(2) . ?
C3 C10 1.474(2) . ?
C18 C19 1.391(3) . ?
C18 C17 1.392(3) . ?
C6 C7 1.370(3) . ?
C7 C8 1.401(3) . ?
C7 H7 0.9500 . ?
C10 C11 1.403(3) . ?
C26 C25 1.525(3) . ?
C26 C27 1.531(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C4 C22 1.505(2) . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C23 C24 1.536(3) . ?
C23 C22 1.541(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C14 C13 1.390(3) . ?
C14 H14 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C8 H8 0.9500 . ?
C20 C21 1.380(3) . ?
C20 H20 0.9500 . ?
C27 C22 1.540(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C24 C25 1.520(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C22 H22 1.0000 . ?
C21 H21 0.9500 . ?
C13 H13 0.9500 . ?
C17 H17 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
C2 N1 C9 C8 1.8(3) . . . . ?
C2 N1 C9 C18 -178.2(2) . . . . ?
C9 N1 C2 C6 -0.7(4) . . . . ?
C9 N1 C2 C3 179.6(2) . . . . ?
N1 C2 C3 C4 -178.6(2) . . . . ?
C6 C2 C3 C4 1.6(3) . . . . ?
N1 C2 C3 C10 3.0(4) . . . . ?
C6 C2 C3 C10 -176.8(2) . . . . ?
N1 C9 C18 C19 -16.5(3) . . . . ?
C8 C9 C18 C19 163.6(2) . . . . ?
N1 C9 C18 C17 161.5(2) . . . . ?
C8 C9 C18 C17 -18.4(4) . . . . ?
N1 C2 C6 C7 -0.9(4) . . . . ?
C3 C2 C6 C7 178.9(2) . . . . ?
N1 C2 C6 C5 -179.9(2) . . . . ?
C3 C2 C6 C5 -0.1(3) . . . . ?
O28 C5 C6 C7 -1.5(5) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
O28 C5 C6 C2 177.3(3) . . . . ?
C4 C5 C6 C2 -1.2(3) . . . . ?
C2 C6 C7 C8 1.3(4) . . . . ?
C5 C6 C7 C8 -179.9(3) . . . . ?
C14 C15 C10 C11 -1.1(3) . . . . ?
C14 C15 C10 C3 -179.4(2) . . . . ?
C4 C3 C10 C11 145.0(2) . . . . ?
C2 C3 C10 C11 -37.0(3) . . . . ?
C4 C3 C10 C15 -36.7(3) . . . . ?
C2 C3 C10 C15 141.3(2) . . . . ?
C10 C3 C4 C22 -3.5(4) . . . . ?
C2 C3 C4 C22 178.2(2) . . . . ?
C10 C3 C4 C5 175.9(2) . . . . ?
C2 C3 C4 C5 -2.4(3) . . . . ?
O28 C5 C4 C3 -176.3(3) . . . . ?
C6 C5 C4 C3 2.3(3) . . . . ?
O28 C5 C4 C22 3.2(4) . . . . ?
C6 C5 C4 C22 -178.3(2) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C9 C18 C19 C20 178.2(2) . . . . ?
C15 C10 C11 C12 1.3(3) . . . . ?
C3 C10 C11 C12 179.68(19) . . . . ?
C10 C15 C14 C13 0.5(3) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
N1 C9 C8 C7 -1.3(4) . . . . ?
C18 C9 C8 C7 178.6(2) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C25 C26 C27 C22 -55.7(2) . . . . ?
C22 C23 C24 C25 58.3(2) . . . . ?
C23 C24 C25 C26 -58.0(2) . . . . ?
C27 C26 C25 C24 56.4(2) . . . . ?
C3 C4 C22 C27 108.2(3) . . . . ?
C5 C4 C22 C27 -71.2(3) . . . . ?
C3 C4 C22 C23 -128.3(3) . . . . ?
C5 C4 C22 C23 52.3(3) . . . . ?
C26 C27 C22 C4 -179.07(17) . . . . ?
C26 C27 C22 C23 55.8(2) . . . . ?
C24 C23 C22 C4 179.54(17) . . . . ?
C24 C23 C22 C27 -56.7(2) . . . . ?
C17 N16 C21 C20 -0.1(4) . . . . ?
C19 C20 C21 N16 0.3(4) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C15 C14 C13 C12 -0.2(3) . . . . ?
C21 N16 C17 C18 0.0(4) . . . . ?
C19 C18 C17 N16 0.1(4) . . . . ?
C9 C18 C17 N16 -178.0(3) . . . . ?
