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#$Date: 2020-02-08 00:23:29 +0200 (Sat, 08 Feb 2020) $
#$Revision: 247951 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/73/4517389.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_4517389
loop_
_publ_author_name
'Ohmatsu, Kohsuke'
'Suzuki, Ryuhei'
'Furukawa, Yukino'
'Sato, Makoto'
'Ooi, Takashi'
_publ_section_title
;
 Zwitterionic 1,2,3-Triazolium Amidate as a Catalyst for Photoinduced
 Hydrogen-Atom Transfer Radical Alkylation
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2627
_journal_paper_doi               10.1021/acscatal.9b04491
_journal_year                    2020
_chemical_formula_sum            'C16 H14 N4 O'
_chemical_formula_weight         278.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 94.256(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.451(7)
_cell_length_b                   7.875(2)
_cell_length_c                   13.315(4)
_cell_measurement_reflns_used    2760
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     2765.9(13)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9227
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         3.077
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0342
_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)+(0.0460P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1882
_reflns_number_total             2565
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs9b04491_si_001.cif
_cod_data_source_block           ydkr
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4517389
_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.
;
_shelx_estimated_absorpt_t_min   0.991
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.08978(5) 0.08973(16) 0.49232(10) 0.0244(3) Uani 1 1 d . .
C2 C 0.11164(5) 0.00281(18) 0.57471(10) 0.0317(3) Uani 1 1 d . .
H1 H 0.095366 -0.001786 0.635898 0.038 Uiso 1 1 calc R U
C3 C 0.15774(6) -0.07745(19) 0.56626(12) 0.0373(4) Uani 1 1 d . .
H2 H 0.173349 -0.137273 0.622247 0.045 Uiso 1 1 calc R U
C4 C 0.18110(6) -0.07112(19) 0.47729(12) 0.0384(4) Uani 1 1 d . .
H3 H 0.212859 -0.125573 0.472228 0.046 Uiso 1 1 calc R U
C5 C 0.15833(5) 0.0144(2) 0.39540(12) 0.0388(4) Uani 1 1 d . .
H4 H 0.174359 0.017220 0.333894 0.047 Uiso 1 1 calc R U
C6 C 0.11225(5) 0.09632(18) 0.40217(11) 0.0314(3) Uani 1 1 d . .
H5 H 0.096555 0.155542 0.346040 0.038 Uiso 1 1 calc R U
C7 C -0.05157(5) 0.3081(2) 0.65273(10) 0.0345(4) Uani 1 1 d . .
H6 H -0.044861 0.224849 0.706783 0.052 Uiso 1 1 calc R U
H7 H -0.087210 0.300812 0.627133 0.052 Uiso 1 1 calc R U
H8 H -0.044414 0.422528 0.678998 0.052 Uiso 1 1 calc R U
C8 C -0.02928(5) 0.31524(16) 0.47203(9) 0.0219(3) Uani 1 1 d . .
C9 C 0.01163(5) 0.24853(16) 0.42571(9) 0.0228(3) Uani 1 1 d . .
H9 H 0.017194 0.253011 0.356086 0.027 Uiso 1 1 calc R U
C10 C -0.08728(5) 0.40213(16) 0.34719(9) 0.0224(3) Uani 1 1 d . .
C11 C -0.13678(5) 0.49272(17) 0.32080(9) 0.0233(3) Uani 1 1 d . .
C12 C -0.16268(5) 0.57646(18) 0.39361(11) 0.0322(3) Uani 1 1 d . .
H10 H -0.149660 0.575284 0.462045 0.039 Uiso 1 1 calc R U
C13 C -0.20753(6) 0.6616(2) 0.36597(13) 0.0412(4) Uani 1 1 d . .
H11 H -0.224855 0.719318 0.415827 0.049 Uiso 1 1 calc R U
C14 C -0.22726(5) 0.66355(19) 0.26739(12) 0.0389(4) Uani 1 1 d . .
H12 H -0.257708 0.723626 0.249122 0.047 Uiso 1 1 calc R U
C15 C -0.20242(5) 0.57738(19) 0.19519(12) 0.0358(4) Uani 1 1 d . .
H13 H -0.216185 0.575942 0.127232 0.043 Uiso 1 1 calc R U
C16 C -0.15747(5) 0.49315(18) 0.22186(10) 0.0291(3) Uani 1 1 d . .
H14 H -0.140527 0.434772 0.171714 0.035 Uiso 1 1 calc R U
N1 N 0.04208(4) 0.17560(13) 0.50014(8) 0.0229(3) Uani 1 1 d . .
N2 N 0.02402(4) 0.18851(14) 0.59018(8) 0.0260(3) Uani 1 1 d . .
N3 N -0.01924(4) 0.27262(14) 0.57144(8) 0.0245(3) Uani 1 1 d . .
N4 N -0.07221(4) 0.40344(14) 0.44560(8) 0.0237(3) Uani 1 1 d . .
O1 O -0.06507(3) 0.33244(12) 0.27857(6) 0.0300(2) 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'
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
C6 C1 C2 121.82(13)
C6 C1 N1 118.75(12)
C2 C1 N1 119.43(12)
C1 C2 C3 118.69(14)
C4 C3 C2 120.48(14)
C3 C4 C5 119.97(14)
C4 C5 C6 120.60(15)
C1 C6 C5 118.44(13)
N4 C8 N3 118.32(11)
N4 C8 C9 138.12(12)
N3 C8 C9 103.56(11)
N1 C9 C8 106.00(11)
O1 C10 N4 126.60(12)
O1 C10 C11 118.96(11)
N4 C10 C11 114.43(11)
C16 C11 C12 118.64(12)
C16 C11 C10 119.73(12)
C12 C11 C10 121.63(12)
C13 C12 C11 119.91(14)
C14 C13 C12 120.95(14)
C13 C14 C15 119.45(14)
C14 C15 C16 120.02(14)
C15 C16 C11 121.00(14)
N2 N1 C9 113.17(11)
N2 N1 C1 118.47(10)
C9 N1 C1 128.36(11)
N1 N2 N3 103.36(10)
N2 N3 C8 113.90(11)
N2 N3 C7 120.07(11)
C8 N3 C7 126.01(11)
C10 N4 C8 115.61(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3793(19)
C1 C2 1.3827(19)
C1 N1 1.4422(17)
C2 C3 1.385(2)
C3 C4 1.377(2)
C4 C5 1.381(2)
C5 C6 1.388(2)
C7 N3 1.4555(16)
C8 N4 1.3551(17)
C8 N3 1.3723(16)
C8 C9 1.3880(17)
C9 N1 1.3573(16)
C10 O1 1.2492(15)
C10 N4 1.3412(16)
C10 C11 1.5095(18)
C11 C16 1.3885(18)
C11 C12 1.3937(18)
C12 C13 1.388(2)
C13 C14 1.376(2)
C14 C15 1.382(2)
C15 C16 1.3845(19)
N1 N2 1.3270(14)
N2 N3 1.3295(15)
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
C6 C1 C2 C3 0.9(2)
N1 C1 C2 C3 -179.31(12)
C1 C2 C3 C4 -0.3(2)
C2 C3 C4 C5 -0.6(2)
C3 C4 C5 C6 0.8(2)
C2 C1 C6 C5 -0.7(2)
N1 C1 C6 C5 179.55(12)
C4 C5 C6 C1 -0.2(2)
N4 C8 C9 N1 179.06(14)
N3 C8 C9 N1 -0.75(13)
O1 C10 C11 C16 1.81(19)
N4 C10 C11 C16 -177.02(12)
O1 C10 C11 C12 -178.37(12)
N4 C10 C11 C12 2.80(18)
C16 C11 C12 C13 -1.6(2)
C10 C11 C12 C13 178.55(13)
C11 C12 C13 C14 0.6(2)
C12 C13 C14 C15 1.0(2)
C13 C14 C15 C16 -1.4(2)
C14 C15 C16 C11 0.4(2)
C12 C11 C16 C15 1.2(2)
C10 C11 C16 C15 -179.00(12)
C8 C9 N1 N2 0.53(14)
C8 C9 N1 C1 -179.39(11)
C6 C1 N1 N2 -171.04(12)
C2 C1 N1 N2 9.21(18)
C6 C1 N1 C9 8.9(2)
C2 C1 N1 C9 -170.88(12)
C9 N1 N2 N3 -0.05(14)
C1 N1 N2 N3 179.87(10)
N1 N2 N3 C8 -0.47(14)
N1 N2 N3 C7 178.21(11)
N4 C8 N3 N2 -179.07(11)
C9 C8 N3 N2 0.78(14)
N4 C8 N3 C7 2.34(19)
C9 C8 N3 C7 -177.81(12)
O1 C10 N4 C8 -2.12(19)
C11 C10 N4 C8 176.61(11)
N3 C8 N4 C10 -162.66(11)
C9 C8 N4 C10 17.6(2)
