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#$Date: 2020-02-08 00:23:47 +0200 (Sat, 08 Feb 2020) $
#$Revision: 247952 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/73/4517390.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_4517390
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 H15 Cl N4 O'
_chemical_formula_weight         314.77
_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                 92.386(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.465(9)
_cell_length_b                   11.018(7)
_cell_length_c                   22.209(15)
_cell_measurement_reflns_used    4559
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      3.00
_cell_volume                     3048(4)
_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 0.988
_diffrn_measured_fraction_theta_max 0.987
_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  0.0951
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9363
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         3.036
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       prism
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0446
_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)+(0.0469P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2060
_reflns_number_total             2803
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs9b04491_si_002.cif
_cod_data_source_block           HClsalt
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4517390
_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   0.927
_shelx_estimated_absorpt_t_max   0.950
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
N1 N 0.65389(13) 0.17939(15) 0.14486(7) 0.0249(4) Uani 1 1 d . .
N2 N 0.55900(14) 0.13356(15) 0.12870(8) 0.0285(4) Uani 1 1 d . .
N3 N 0.53679(13) 0.18294(16) 0.07519(7) 0.0264(4) Uani 1 1 d . .
N4 N 0.60801(13) 0.32296(15) 0.00410(7) 0.0262(4) Uani 1 1 d . .
H1 H 0.566535 0.295921 -0.026008 0.031 Uiso 1 1 calc R U
C1 C 0.70229(17) 0.14315(18) 0.20242(9) 0.0258(5) Uani 1 1 d . .
C2 C 0.64475(18) 0.0650(2) 0.23841(10) 0.0370(6) Uani 1 1 d . .
H2 H 0.577374 0.033286 0.224388 0.044 Uiso 1 1 calc R U
C3 C 0.6873(2) 0.0344(2) 0.29476(11) 0.0409(6) Uani 1 1 d . .
H3 H 0.648565 -0.017300 0.320335 0.049 Uiso 1 1 calc R U
C4 C 0.7867(2) 0.0795(2) 0.31379(10) 0.0386(6) Uani 1 1 d . .
H4 H 0.815536 0.059492 0.352784 0.046 Uiso 1 1 calc R U
C5 C 0.8445(2) 0.1537(2) 0.27642(10) 0.0375(6) Uani 1 1 d . .
H5 H 0.913566 0.182041 0.289577 0.045 Uiso 1 1 calc R U
C6 C 0.80236(17) 0.18687(19) 0.22012(9) 0.0298(5) Uani 1 1 d . .
H6 H 0.841230 0.238191 0.194454 0.036 Uiso 1 1 calc R U
C7 C 0.61612(16) 0.25926(18) 0.05771(9) 0.0239(5) Uani 1 1 d . .
C8 C 0.69275(16) 0.25677(19) 0.10317(9) 0.0259(5) Uani 1 1 d . .
H7 H 0.758925 0.299647 0.105355 0.031 Uiso 1 1 calc R U
C9 C 0.43389(18) 0.1532(2) 0.04463(10) 0.0376(6) Uani 1 1 d . .
H8 H 0.406498 0.077038 0.060859 0.056 Uiso 1 1 calc R U
H9 H 0.443898 0.144009 0.001329 0.056 Uiso 1 1 calc R U
H10 H 0.382356 0.218522 0.051222 0.056 Uiso 1 1 calc R U
C10 C 0.66513(16) 0.42893(19) -0.00198(10) 0.0270(5) Uani 1 1 d . .
C11 C 0.65102(17) 0.49262(17) -0.06119(9) 0.0260(5) Uani 1 1 d . .
C12 C 0.73867(18) 0.55885(19) -0.08056(10) 0.0317(5) Uani 1 1 d . .
H11 H 0.803542 0.560008 -0.056547 0.038 Uiso 1 1 calc R U
C13 C 0.7324(2) 0.6227(2) -0.13407(10) 0.0390(6) Uani 1 1 d . .
H12 H 0.793160 0.665428 -0.147502 0.047 Uiso 1 1 calc R U
C14 C 0.6369(2) 0.6236(2) -0.16784(10) 0.0388(6) Uani 1 1 d . .
H13 H 0.631376 0.668808 -0.204270 0.047 Uiso 1 1 calc R U
C15 C 0.54932(19) 0.5591(2) -0.14893(10) 0.0354(5) Uani 1 1 d . .
H14 H 0.483921 0.560636 -0.172465 0.042 Uiso 1 1 calc R U
C16 C 0.55587(17) 0.49206(19) -0.09583(10) 0.0295(5) Uani 1 1 d . .
H15 H 0.495946 0.446481 -0.083469 0.035 Uiso 1 1 calc R U
Cl1 Cl 0.97414(4) 0.32636(5) 0.10581(2) 0.03266(17) Uani 1 1 d . .
O1 O 0.72312(14) 0.46821(15) 0.03851(7) 0.0425(4) 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'
Cl Cl 0.1484 0.1585 '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
N2 N1 C8 113.19(17)
N2 N1 C1 118.04(17)
C8 N1 C1 128.77(17)
N1 N2 N3 103.76(16)
N2 N3 C7 112.37(17)
N2 N3 C9 118.05(17)
C7 N3 C9 129.55(18)
C10 N4 C7 119.69(17)
C6 C1 C2 122.2(2)
C6 C1 N1 119.63(19)
C2 C1 N1 118.14(19)
C3 C2 C1 118.9(2)
C2 C3 C4 119.6(2)
C3 C4 C5 120.6(2)
C6 C5 C4 120.5(2)
C1 C6 C5 118.0(2)
C8 C7 N3 105.70(18)
C8 C7 N4 132.32(19)
N3 C7 N4 121.96(18)
C7 C8 N1 104.97(18)
O1 C10 N4 121.7(2)
O1 C10 C11 122.05(19)
N4 C10 C11 116.23(18)
C16 C11 C12 119.6(2)
C16 C11 C10 123.56(19)
C12 C11 C10 116.84(19)
C13 C12 C11 121.0(2)
C12 C13 C14 119.2(2)
C13 C14 C15 120.3(2)
C14 C15 C16 120.7(2)
C11 C16 C15 119.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.322(2)
N1 C8 1.363(3)
N1 C1 1.447(3)
N2 N3 1.326(2)
N3 C7 1.367(3)
N3 C9 1.463(3)
N4 C10 1.377(3)
N4 C7 1.382(3)
C1 C6 1.379(3)
C1 C2 1.394(3)
C2 C3 1.380(3)
C3 C4 1.384(3)
C4 C5 1.388(3)
C5 C6 1.385(3)
C7 C8 1.361(3)
C10 O1 1.210(2)
C10 C11 1.494(3)
C11 C16 1.387(3)
C11 C12 1.397(3)
C12 C13 1.380(3)
C13 C14 1.380(3)
C14 C15 1.383(3)
C15 C16 1.391(3)
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
C8 N1 N2 N3 0.1(2)
C1 N1 N2 N3 180.00(16)
N1 N2 N3 C7 -0.2(2)
N1 N2 N3 C9 -178.44(17)
N2 N1 C1 C6 178.46(18)
C8 N1 C1 C6 -1.6(3)
N2 N1 C1 C2 -2.0(3)
C8 N1 C1 C2 177.9(2)
C6 C1 C2 C3 2.8(3)
N1 C1 C2 C3 -176.72(19)
C1 C2 C3 C4 -1.4(3)
C2 C3 C4 C5 -0.9(4)
C3 C4 C5 C6 1.9(4)
C2 C1 C6 C5 -1.8(3)
N1 C1 C6 C5 177.71(18)
C4 C5 C6 C1 -0.5(3)
N2 N3 C7 C8 0.3(2)
C9 N3 C7 C8 178.2(2)
N2 N3 C7 N4 -178.19(17)
C9 N3 C7 N4 -0.2(3)
C10 N4 C7 C8 -22.5(3)
C10 N4 C7 N3 155.47(19)
N3 C7 C8 N1 -0.2(2)
N4 C7 C8 N1 178.0(2)
N2 N1 C8 C7 0.1(2)
C1 N1 C8 C7 -179.84(18)
C7 N4 C10 O1 0.3(3)
C7 N4 C10 C11 -179.49(17)
O1 C10 C11 C16 -146.8(2)
N4 C10 C11 C16 32.9(3)
O1 C10 C11 C12 31.0(3)
N4 C10 C11 C12 -149.27(19)
C16 C11 C12 C13 -0.8(3)
C10 C11 C12 C13 -178.68(19)
C11 C12 C13 C14 1.9(3)
C12 C13 C14 C15 -1.5(3)
C13 C14 C15 C16 -0.2(4)
C12 C11 C16 C15 -0.9(3)
C10 C11 C16 C15 176.87(19)
C14 C15 C16 C11 1.4(3)
