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#$Date: 2022-06-01 00:55:28 +0300 (Wed, 01 Jun 2022) $
#$Revision: 275703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/01/7130162.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_7130162
loop_
_publ_author_name
'Cao, Shujun'
'Yuan, Weidong'
'Li, Yun'
'Teng, Xinjie'
'Si, Huaxing'
'Chen, Rongshun'
'Zhu, Yingguang'
_publ_section_title
;
 Photoredox/copper cocatalyzed domino cyclization of oxime esters with
 TMSCN: access to antifungal active tetrasubstituted pyrazines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02480B
_journal_year                    2022
_chemical_formula_moiety         'C19 H16 N4'
_chemical_formula_sum            'C19 H16 N4'
_chemical_formula_weight         300.36
_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-2018/3
_audit_update_record
;
2021-08-04 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                80.485(4)
_cell_angle_beta                 88.980(5)
_cell_angle_gamma                82.009(5)
_cell_formula_units_Z            2
_cell_length_a                   6.3310(9)
_cell_length_b                   9.7410(13)
_cell_length_c                   13.1586(19)
_cell_measurement_reflns_used    3615
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.44
_cell_volume                     792.55(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10488
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.437
_diffrn_source.source            'Ius 2.0'
_diffrn_source.type              microfocus
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0499
_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)+(0.0631P)²+0.1625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1791
_reflns_number_total             2766
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02480b2.cif
_cod_data_source_block           CSJ06_86_1_a
_cod_database_code               7130162
_shelx_shelxl_version_number     2018/3
_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   0.985
_shelx_estimated_absorpt_t_max   0.996
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
C1 C -0.3080(4) 0.7084(3) 0.5161(2) 0.0826(8) Uani 1 1 d . . . . .
H1 H -0.419913 0.701690 0.562555 0.099 Uiso 1 1 calc R U . . .
C2 C -0.2761(4) 0.6215(3) 0.4451(2) 0.0935(9) Uani 1 1 d . . . . .
H2 H -0.364566 0.553217 0.443607 0.112 Uiso 1 1 calc R U . . .
C3 C -0.1127(4) 0.6343(3) 0.37498(19) 0.0841(8) Uani 1 1 d . . . . .
H3 H -0.092998 0.574166 0.326585 0.101 Uiso 1 1 calc R U . . .
C4 C 0.0212(3) 0.7331(2) 0.37469(16) 0.0522(5) Uani 1 1 d . . . . .
C5 C -0.0120(4) 0.8168(2) 0.4486(2) 0.0813(8) Uani 1 1 d . . . . .
H5 H 0.077967 0.883793 0.451716 0.098 Uiso 1 1 calc R U . . .
C6 C -0.1749(5) 0.8049(3) 0.5184(2) 0.1009(10) Uani 1 1 d . . . . .
H6 H -0.193780 0.863662 0.567775 0.121 Uiso 1 1 calc R U . . .
C7 C 0.1968(3) 0.7533(2) 0.29675(18) 0.0629(6) Uani 1 1 d . . . . .
H7A H 0.141251 0.824713 0.239616 0.076 Uiso 1 1 calc R U . . .
H7B H 0.310767 0.788612 0.328520 0.076 Uiso 1 1 calc R U . . .
C8 C 0.2890(3) 0.6241(2) 0.25497(17) 0.0567(6) Uani 1 1 d . . . . .
H8A H 0.179236 0.594766 0.216210 0.068 Uiso 1 1 calc R U . . .
H8B H 0.330659 0.549288 0.312242 0.068 Uiso 1 1 calc R U . . .
C9 C 0.4799(3) 0.64329(19) 0.18620(15) 0.0470(5) Uani 1 1 d . . . . .
C10 C 0.6131(3) 0.53015(19) 0.15592(14) 0.0440(5) Uani 1 1 d . . . . .
C11 C 0.5835(3) 0.3812(2) 0.19224(15) 0.0464(5) Uani 1 1 d . . . . .
C12 C 0.3968(4) 0.3297(2) 0.17371(17) 0.0600(6) Uani 1 1 d . . . . .
H12 H 0.284741 0.389534 0.138478 0.072 Uiso 1 1 calc R U . . .
C13 C 0.3761(4) 0.1905(3) 0.2072(2) 0.0716(7) Uani 1 1 d . . . . .
H13 H 0.252534 0.155836 0.192369 0.086 Uiso 1 1 calc R U . . .
C14 C 0.5371(5) 0.1035(3) 0.2620(2) 0.0780(8) Uani 1 1 d . . . . .
H14 H 0.521120 0.010287 0.286120 0.094 Uiso 1 1 calc R U . . .
C15 C 0.7222(4) 0.1527(2) 0.2818(2) 0.0781(7) Uani 1 1 d . . . . .
H15 H 0.831648 0.092975 0.319131 0.094 Uiso 1 1 calc R U . . .
C16 C 0.7456(4) 0.2909(2) 0.24624(18) 0.0632(6) Uani 1 1 d . . . . .
H16 H 0.872278 0.323590 0.258779 0.076 Uiso 1 1 calc R U . . .
C17 C 0.8294(3) 0.68000(19) 0.06696(14) 0.0457(5) Uani 1 1 d . . . . .
C18 C 0.6946(3) 0.79116(19) 0.09831(15) 0.0508(5) Uani 1 1 d . . . . .
C19 C 0.7376(3) 0.9330(2) 0.06796(19) 0.0645(7) Uani 1 1 d . . . . .
N1 N 0.5240(3) 0.77288(16) 0.15742(13) 0.0549(5) Uani 1 1 d . . . . .
N2 N 0.7845(2) 0.54851(15) 0.09660(12) 0.0459(4) Uani 1 1 d . . . . .
N3 N 0.7781(4) 1.0432(2) 0.04223(19) 0.0905(8) Uani 1 1 d . . . . .
N4 N 1.0027(3) 0.69723(17) 0.00882(13) 0.0586(5) Uani 1 1 d . . . . .
H4A H 1.081130 0.625357 -0.008367 0.070 Uiso 1 1 calc R U . . .
H4B H 1.035433 0.780159 -0.011316 0.070 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
C6 C1 C2 119.1(2) . . ?
C6 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 116.72(19) . . ?
C5 C4 C7 120.12(19) . . ?
C3 C4 C7 123.1(2) . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C4 115.15(17) . . ?
C8 C7 H7A 108.5 . . ?
C4 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C4 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 114.06(16) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N1 C9 C10 119.85(16) . . ?
N1 C9 C8 117.45(17) . . ?
C10 C9 C8 122.65(16) . . ?
N2 C10 C9 122.01(16) . . ?
N2 C10 C11 115.13(16) . . ?
C9 C10 C11 122.75(16) . . ?
C16 C11 C12 118.59(19) . . ?
C16 C11 C10 119.38(17) . . ?
C12 C11 C10 122.03(19) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N4 C17 N2 117.91(17) . . ?
N4 C17 C18 123.42(16) . . ?
N2 C17 C18 118.67(16) . . ?
N1 C18 C17 123.03(16) . . ?
N1 C18 C19 116.80(17) . . ?
C17 C18 C19 120.17(17) . . ?
N3 C19 C18 177.5(2) . . ?
C9 N1 C18 118.12(16) . . ?
C10 N2 C17 118.31(16) . . ?
C17 N4 H4A 120.0 . . ?
C17 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
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
C1 C6 1.350(4) . ?
C1 C2 1.356(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(3) . ?
C4 C7 1.510(3) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.497(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.511(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.323(2) . ?
C9 C10 1.400(3) . ?
C10 N2 1.340(2) . ?
C10 C11 1.487(2) . ?
C11 C16 1.379(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N4 1.340(2) . ?
C17 N2 1.344(2) . ?
C17 C18 1.396(3) . ?
C18 N1 1.335(2) . ?
C18 C19 1.436(3) . ?
C19 N3 1.133(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4B N3 0.86 2.20 3.025(2) 161.0 2_775 yes
N4 H4A N2 0.86 2.27 3.099(2) 161.8 2_765 yes
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
C6 C1 C2 C3 -1.5(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C2 C3 C4 C7 -177.8(2) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C7 C4 C5 C6 177.6(3) . . . . ?
C2 C1 C6 C5 1.3(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C5 C4 C7 C8 151.8(2) . . . . ?
C3 C4 C7 C8 -29.2(3) . . . . ?
C4 C7 C8 C9 -173.66(18) . . . . ?
C7 C8 C9 N1 -10.3(3) . . . . ?
C7 C8 C9 C10 167.3(2) . . . . ?
N1 C9 C10 N2 -1.1(3) . . . . ?
C8 C9 C10 N2 -178.61(18) . . . . ?
N1 C9 C10 C11 174.96(18) . . . . ?
C8 C9 C10 C11 -2.6(3) . . . . ?
N2 C10 C11 C16 56.1(2) . . . . ?
C9 C10 C11 C16 -120.2(2) . . . . ?
N2 C10 C11 C12 -124.1(2) . . . . ?
C9 C10 C11 C12 59.7(3) . . . . ?
C16 C11 C12 C13 -1.1(3) . . . . ?
C10 C11 C12 C13 179.00(18) . . . . ?
C11 C12 C13 C14 2.3(3) . . . . ?
C12 C13 C14 C15 -1.8(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C11 1.1(4) . . . . ?
C12 C11 C16 C15 -0.5(3) . . . . ?
C10 C11 C16 C15 179.3(2) . . . . ?
N4 C17 C18 N1 -179.04(19) . . . . ?
N2 C17 C18 N1 0.7(3) . . . . ?
N4 C17 C18 C19 0.3(3) . . . . ?
N2 C17 C18 C19 -179.92(19) . . . . ?
C10 C9 N1 C18 1.1(3) . . . . ?
C8 C9 N1 C18 178.71(18) . . . . ?
C17 C18 N1 C9 -0.9(3) . . . . ?
C19 C18 N1 C9 179.71(19) . . . . ?
C9 C10 N2 C17 0.9(3) . . . . ?
C11 C10 N2 C17 -175.45(16) . . . . ?
N4 C17 N2 C10 179.11(17) . . . . ?
C18 C17 N2 C10 -0.7(3) . . . . ?
