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#$Date: 2022-05-18 00:52:54 +0300 (Wed, 18 May 2022) $
#$Revision: 275490 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/01/7130107.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_7130107
loop_
_publ_author_name
'Wang, Shuxia'
'Sun, Lei'
'Gao, Minghui'
'Jiang, Qin'
'Hu, Weiming'
'Liu, Yaya'
'Tao, Chuanzhou'
_publ_section_title
;
 Copper-catalyzed C2 alkenylation of pyridine-N-oxides with alkynes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00851C
_journal_year                    2022
_chemical_formula_sum            'C20 H17 N'
_chemical_formula_weight         271.35
_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-2016/6
_audit_update_record
;
2022-01-26 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.82(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.15(4)
_cell_length_b                   9.86(3)
_cell_length_c                   15.05(5)
_cell_measurement_reflns_used    1015
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.34
_cell_measurement_theta_min      2.51
_cell_volume                     1575(9)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1188
_diffrn_reflns_av_unetI/netI     0.1503
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9081
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         25.241
_diffrn_reflns_theta_min         1.919
_exptl_absorpt_coefficient_mu    0.066
_exptl_crystal_colour            colourlss
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1875
_refine_ls_R_factor_gt           0.0982
_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)+(0.1200P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2427
_refine_ls_wR_factor_ref         0.3096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1222
_reflns_number_total             2833
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00851c2.cif
_cod_data_source_block           TAO0604_0m
_cod_original_cell_volume        1574(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7130107
_shelx_shelxl_version_number     2016/6
_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   0.992
_shelx_estimated_absorpt_t_max   0.995
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
N1 N 0.7336(4) 0.6221(4) 0.6150(2) 0.0708(11) Uani 1 1 d . . . . .
C1 C 0.6516(4) 0.5753(4) 0.6584(3) 0.0674(12) Uani 1 1 d . . . . .
C2 C 0.6910(5) 0.4855(5) 0.7343(3) 0.0804(14) Uani 1 1 d . . . . .
H2 H 0.633895 0.454536 0.763620 0.097 Uiso 1 1 calc R U . . .
C3 C 0.8148(5) 0.4434(6) 0.7651(4) 0.0980(17) Uani 1 1 d . . . . .
H3 H 0.842031 0.384510 0.815598 0.118 Uiso 1 1 calc R U . . .
C4 C 0.8971(5) 0.4892(5) 0.7206(4) 0.0930(16) Uani 1 1 d . . . . .
H4 H 0.980574 0.460695 0.740178 0.112 Uiso 1 1 calc R U . . .
C5 C 0.8548(5) 0.5799(5) 0.6450(3) 0.0745(13) Uani 1 1 d . . . . .
C6 C 0.9396(5) 0.6332(6) 0.5914(4) 0.1062(19) Uani 1 1 d . . . . .
H6A H 1.017820 0.584256 0.609629 0.159 Uiso 1 1 calc R U . . .
H6B H 0.955792 0.727926 0.604739 0.159 Uiso 1 1 calc R U . . .
H6C H 0.899111 0.621374 0.525665 0.159 Uiso 1 1 calc R U . . .
C7 C 0.5197(4) 0.6265(4) 0.6259(3) 0.0632(11) Uani 1 1 d . . . . .
C8 C 0.4258(4) 0.5520(5) 0.6612(3) 0.0667(12) Uani 1 1 d . . . . .
C9 C 0.3797(5) 0.6122(5) 0.7277(3) 0.0794(14) Uani 1 1 d . . . . .
H9 H 0.404505 0.699886 0.747831 0.095 Uiso 1 1 calc R U . . .
C10 C 0.2975(5) 0.5435(7) 0.7642(4) 0.0969(17) Uani 1 1 d . . . . .
H10 H 0.267237 0.585682 0.808347 0.116 Uiso 1 1 calc R U . . .
C11 C 0.2608(5) 0.4157(7) 0.7364(4) 0.0963(17) Uani 1 1 d . . . . .
H11 H 0.206912 0.369605 0.762461 0.116 Uiso 1 1 calc R U . . .
C12 C 0.3029(5) 0.3532(6) 0.6694(4) 0.0973(17) Uani 1 1 d . . . . .
H12 H 0.276516 0.265735 0.649705 0.117 Uiso 1 1 calc R U . . .
C13 C 0.3846(5) 0.4215(5) 0.6317(3) 0.0815(14) Uani 1 1 d . . . . .
H13 H 0.412245 0.379613 0.586164 0.098 Uiso 1 1 calc R U . . .
C14 C 0.4914(4) 0.7417(5) 0.5746(3) 0.0697(12) Uani 1 1 d . . . . .
H14 H 0.558566 0.784567 0.561684 0.084 Uiso 1 1 calc R U . . .
C15 C 0.3673(5) 0.8075(5) 0.5365(3) 0.0674(12) Uani 1 1 d . . . . .
C16 C 0.3611(5) 0.9503(5) 0.5355(3) 0.0793(14) Uani 1 1 d . . . . .
H16 H 0.434463 1.000423 0.560043 0.095 Uiso 1 1 calc R U . . .
C17 C 0.2472(6) 1.0171(6) 0.4984(3) 0.0925(16) Uani 1 1 d . . . . .
H17 H 0.244853 1.111415 0.499376 0.111 Uiso 1 1 calc R U . . .
C18 C 0.1381(6) 0.9453(7) 0.4603(4) 0.0967(17) Uani 1 1 d . . . . .
H18 H 0.061913 0.990559 0.435529 0.116 Uiso 1 1 calc R U . . .
C19 C 0.1424(5) 0.8049(7) 0.4590(3) 0.0966(17) Uani 1 1 d . . . . .
H19 H 0.068879 0.755699 0.432644 0.116 Uiso 1 1 calc R U . . .
C20 C 0.2550(5) 0.7376(6) 0.4967(3) 0.0841(15) Uani 1 1 d . . . . .
H20 H 0.256024 0.643300 0.495560 0.101 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'
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 119.1(4) . . ?
N1 C1 C2 121.1(5) . . ?
N1 C1 C7 118.0(4) . . ?
C2 C1 C7 120.9(4) . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.7(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 121.2(4) . . ?
N1 C5 C6 116.0(5) . . ?
C4 C5 C6 122.8(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C14 C7 C1 120.3(4) . . ?
C14 C7 C8 123.1(4) . . ?
C1 C7 C8 116.3(4) . . ?
C9 C8 C13 117.7(4) . . ?
C9 C8 C7 119.8(5) . . ?
C13 C8 C7 122.5(4) . . ?
C10 C9 C8 121.0(5) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.2(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 119.7(6) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C8 120.8(5) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C7 C14 C15 128.1(4) . . ?
C7 C14 H14 116.0 . . ?
C15 C14 H14 116.0 . . ?
C20 C15 C16 117.0(5) . . ?
C20 C15 C14 124.2(5) . . ?
C16 C15 C14 118.7(5) . . ?
C17 C16 C15 121.0(5) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.6(6) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.4(5) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 120.4(6) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C15 121.6(6) . . ?
C19 C20 H20 119.2 . . ?
C15 C20 H20 119.2 . . ?
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
N1 C5 1.352(7) . ?
N1 C1 1.357(6) . ?
C1 C2 1.405(7) . ?
C1 C7 1.488(8) . ?
C2 C3 1.378(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.513(7) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C14 1.355(7) . ?
C7 C8 1.502(7) . ?
C8 C9 1.390(6) . ?
C8 C13 1.392(7) . ?
C9 C10 1.381(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.352(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.476(7) . ?
C14 H14 0.9300 . ?
C15 C20 1.393(7) . ?
C15 C16 1.408(8) . ?
C16 C17 1.387(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(8) . ?
C19 H19 0.9300 . ?
C20 H20 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
C5 N1 C1 C2 0.7(6) . . . . ?
C5 N1 C1 C7 178.2(4) . . . . ?
N1 C1 C2 C3 -0.3(7) . . . . ?
C7 C1 C2 C3 -177.7(5) . . . . ?
C1 C2 C3 C4 -0.5(8) . . . . ?
C2 C3 C4 C5 0.9(8) . . . . ?
C1 N1 C5 C4 -0.3(7) . . . . ?
C1 N1 C5 C6 178.3(4) . . . . ?
C3 C4 C5 N1 -0.5(8) . . . . ?
C3 C4 C5 C6 -179.0(5) . . . . ?
N1 C1 C7 C14 -18.2(6) . . . . ?
C2 C1 C7 C14 159.2(4) . . . . ?
N1 C1 C7 C8 167.7(3) . . . . ?
C2 C1 C7 C8 -14.9(6) . . . . ?
C14 C7 C8 C9 -66.5(6) . . . . ?
C1 C7 C8 C9 107.5(5) . . . . ?
C14 C7 C8 C13 115.4(5) . . . . ?
C1 C7 C8 C13 -70.7(6) . . . . ?
C13 C8 C9 C10 1.1(7) . . . . ?
C7 C8 C9 C10 -177.2(5) . . . . ?
C8 C9 C10 C11 0.4(8) . . . . ?
C9 C10 C11 C12 -1.4(9) . . . . ?
C10 C11 C12 C13 0.9(8) . . . . ?
C11 C12 C13 C8 0.6(8) . . . . ?
C9 C8 C13 C12 -1.6(7) . . . . ?
C7 C8 C13 C12 176.6(4) . . . . ?
C1 C7 C14 C15 -180.0(4) . . . . ?
C8 C7 C14 C15 -6.3(7) . . . . ?
C7 C14 C15 C20 -40.7(7) . . . . ?
C7 C14 C15 C16 142.6(5) . . . . ?
C20 C15 C16 C17 1.5(6) . . . . ?
C14 C15 C16 C17 178.4(4) . . . . ?
C15 C16 C17 C18 -1.1(7) . . . . ?
C16 C17 C18 C19 0.0(7) . . . . ?
C17 C18 C19 C20 0.8(7) . . . . ?
C18 C19 C20 C15 -0.3(7) . . . . ?
C16 C15 C20 C19 -0.8(6) . . . . ?
C14 C15 C20 C19 -177.5(4) . . . . ?
