#------------------------------------------------------------------------------
#$Date: 2023-01-06 11:41:16 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280176 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/57/7245764.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_7245764
loop_
_publ_author_name
'Li, Sifeng'
'Wang, Taimin'
'Li, Xingchen'
'Fang, Lijing'
'Zhai, Hongbin'
'Cheng, Bin'
_publ_section_title
;
 Switchable electrooxidative N-methyl amines: access to C3-aminomethylated
 and C3-arylmethylated imidazo[1,2-a] pyridines
;
_journal_issue                   24
_journal_name_full               'Green Chemistry'
_journal_page_first              9482
_journal_page_last               9488
_journal_paper_doi               10.1039/D2GC03464F
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C21 H19 N3'
_chemical_formula_sum            'C21 H19 N3'
_chemical_formula_weight         313.39
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-31 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                115.055(14)
_cell_angle_beta                 99.780(14)
_cell_angle_gamma                98.016(15)
_cell_formula_units_Z            2
_cell_length_a                   8.365(4)
_cell_length_b                   10.655(5)
_cell_length_c                   10.809(5)
_cell_measurement_reflns_used    3982
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      27.689
_cell_measurement_theta_min      2.881
_cell_volume                     835.6(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.994
_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  0.0552
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13642
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.151
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1175 before and 0.0804 after correction.
The Ratio of minimum to maximum transmission is 0.8530.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0470
_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)+(0.0563P)²+0.1179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2783
_reflns_number_total             3805
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc03464f2.cif
_cod_data_source_block           1132_lsf_0m
_cod_depositor_comments
'Adding full bibliography for 7245762--7245764.cif.'
_cod_database_code               7245764
_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_max   0.957
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
N1 N 0.69513(16) 0.38191(12) 0.43107(13) 0.0537(3) Uani 1 1 d . . . . .
N2 N 0.37712(15) 0.13875(12) 0.28414(12) 0.0486(3) Uani 1 1 d . . . . .
N3 N 0.23128(15) 0.11535(13) 0.07826(13) 0.0526(3) Uani 1 1 d . . . . .
C00G C 0.3613(2) 0.2818(2) -0.06069(19) 0.0696(5) Uani 1 1 d . . . . .
H00G H 0.260692 0.296707 -0.038392 0.084 Uiso 1 1 calc R U . . .
C1 C 0.8533(2) 0.55122(17) 0.66903(17) 0.0613(4) Uani 1 1 d . . . . .
H1 H 0.813377 0.623403 0.656630 0.074 Uiso 1 1 calc R U . . .
C2 C 0.9566(2) 0.5830(2) 0.79756(18) 0.0694(5) Uani 1 1 d . . . . .
H2 H 0.983519 0.675732 0.870336 0.083 Uiso 1 1 calc R U . . .
C3 C 1.0200(2) 0.4805(2) 0.81991(18) 0.0687(5) Uani 1 1 d . . . . .
H3 H 1.090599 0.502649 0.906411 0.082 Uiso 1 1 calc R U . . .
C4 C 0.9769(2) 0.3444(2) 0.71151(19) 0.0663(4) Uani 1 1 d . . . . .
H4 H 1.018381 0.273504 0.725353 0.080 Uiso 1 1 calc R U . . .
C5 C 0.87334(19) 0.31011(17) 0.58236(17) 0.0580(4) Uani 1 1 d . . . . .
H5 H 0.846930 0.216770 0.510864 0.070 Uiso 1 1 calc R U . . .
C6 C 0.80725(16) 0.41294(15) 0.55678(15) 0.0459(3) Uani 1 1 d . . . . .
C7 C 0.6608(2) 0.49890(18) 0.40247(19) 0.0689(5) Uani 1 1 d . . . . .
H7A H 0.583198 0.461066 0.311736 0.103 Uiso 1 1 calc R U . . .
H7B H 0.762829 0.553100 0.402824 0.103 Uiso 1 1 calc R U . . .
H7C H 0.613751 0.559538 0.474036 0.103 Uiso 1 1 calc R U . . .
C8 C 0.67179(19) 0.24869(17) 0.30222(16) 0.0561(4) Uani 1 1 d . . . . .
H8A H 0.716314 0.180547 0.326737 0.067 Uiso 1 1 calc R U . . .
H8B H 0.733329 0.266929 0.240806 0.067 Uiso 1 1 calc R U . . .
C9 C 0.49183(18) 0.18658(15) 0.22541(15) 0.0476(3) Uani 1 1 d . . . . .
C10 C 0.39825(18) 0.17148(15) 0.10000(15) 0.0479(3) Uani 1 1 d . . . . .
C11 C 0.22052(18) 0.09576(15) 0.19034(15) 0.0501(3) Uani 1 1 d . . . . .
C12 C 0.0804(2) 0.04216(17) 0.22587(18) 0.0602(4) Uani 1 1 d . . . . .
H12 H -0.025397 0.011171 0.164570 0.072 Uiso 1 1 calc R U . . .
C13 C 0.1023(2) 0.03652(18) 0.35078(19) 0.0674(5) Uani 1 1 d . . . . .
H13 H 0.010544 0.002116 0.375185 0.081 Uiso 1 1 calc R U . . .
C14 C 0.2622(3) 0.08216(18) 0.44365(18) 0.0673(5) Uani 1 1 d . . . . .
H14 H 0.274826 0.078083 0.528939 0.081 Uiso 1 1 calc R U . . .
C15 C 0.3977(2) 0.13190(16) 0.41008(16) 0.0591(4) Uani 1 1 d . . . . .
H15 H 0.503276 0.161059 0.471261 0.071 Uiso 1 1 calc R U . . .
C16 C 0.45522(18) 0.21344(15) -0.00240(14) 0.0487(3) Uani 1 1 d . . . . .
C17 C 0.6026(2) 0.18942(16) -0.04115(15) 0.0558(4) Uani 1 1 d . . . . .
H17 H 0.666362 0.141999 -0.004909 0.067 Uiso 1 1 calc R U . . .
C18 C 0.6557(2) 0.23510(18) -0.13291(17) 0.0630(4) Uani 1 1 d . . . . .
H18 H 0.754440 0.217876 -0.157993 0.076 Uiso 1 1 calc R U . . .
C19 C 0.5635(2) 0.3057(2) -0.18705(18) 0.0710(5) Uani 1 1 d . . . . .
H19 H 0.600528 0.338201 -0.247045 0.085 Uiso 1 1 calc R U . . .
C20 C 0.4156(3) 0.3279(3) -0.1517(2) 0.0826(6) Uani 1 1 d . . . . .
H20 H 0.351788 0.374270 -0.189274 0.099 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 N1 C7 119.06(12) . . ?
C6 N1 C8 121.70(12) . . ?
C7 N1 C8 112.97(13) . . ?
C9 N2 C11 107.22(12) . . ?
C15 N2 C9 131.04(13) . . ?
C15 N2 C11 121.73(13) . . ?
C11 N3 C10 105.44(12) . . ?
C16 C00G H00G 119.7 . . ?
C20 C00G H00G 119.7 . . ?
C20 C00G C16 120.67(17) . . ?
C2 C1 H1 119.2 . . ?
C2 C1 C6 121.61(16) . . ?
C6 C1 H1 119.2 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.17(17) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.26(16) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.54(16) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.30(15) . . ?
C6 C5 H5 119.4 . . ?
N1 C6 C1 120.44(13) . . ?
N1 C6 C5 123.36(13) . . ?
C5 C6 C1 116.12(14) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
N1 C8 C9 111.47(13) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
N2 C9 C8 121.59(13) . . ?
C10 C9 N2 104.86(13) . . ?
C10 C9 C8 133.38(13) . . ?
N3 C10 C16 120.17(12) . . ?
C9 C10 N3 111.62(13) . . ?
C9 C10 C16 128.14(13) . . ?
N2 C11 C12 118.54(14) . . ?
N3 C11 N2 110.86(13) . . ?
N3 C11 C12 130.59(14) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.14(16) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.78(16) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.68(16) . . ?
C15 C14 H14 119.7 . . ?
N2 C15 H15 120.4 . . ?
C14 C15 N2 119.11(16) . . ?
C14 C15 H15 120.4 . . ?
C00G C16 C10 119.54(14) . . ?
C00G C16 C17 118.08(14) . . ?
C17 C16 C10 122.36(13) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.92(15) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.34(16) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.36(16) . . ?
C20 C19 H19 120.3 . . ?
C00G C20 H20 119.7 . . ?
C19 C20 C00G 120.59(17) . . ?
C19 C20 H20 119.7 . . ?
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 C6 1.3912(18) . ?
N1 C7 1.4587(19) . ?
N1 C8 1.466(2) . ?
N2 C9 1.3885(18) . ?
N2 C11 1.3935(19) . ?
N2 C15 1.3770(19) . ?
N3 C10 1.378(2) . ?
N3 C11 1.3286(19) . ?
C00G H00G 0.9300 . ?
C00G C16 1.387(2) . ?
C00G C20 1.384(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(2) . ?
C1 C6 1.400(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.492(2) . ?
C9 C10 1.377(2) . ?
C10 C16 1.480(2) . ?
C11 C12 1.414(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.359(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.408(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.354(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.391(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(3) . ?
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
N1 C8 C9 N2 -64.59(18) . . . . ?
N1 C8 C9 C10 109.80(19) . . . . ?
N2 C9 C10 N3 -0.53(16) . . . . ?
N2 C9 C10 C16 176.42(13) . . . . ?
N2 C11 C12 C13 1.1(2) . . . . ?
N3 C10 C16 C00G 40.6(2) . . . . ?
N3 C10 C16 C17 -140.72(15) . . . . ?
N3 C11 C12 C13 -178.07(15) . . . . ?
C00G C16 C17 C18 1.4(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C1 C6 N1 176.16(15) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 N1 -176.33(15) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C6 N1 C8 C9 138.30(14) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C7 N1 C6 C1 16.3(2) . . . . ?
C7 N1 C6 C5 -167.10(15) . . . . ?
C7 N1 C8 C9 -69.85(17) . . . . ?
C8 N1 C6 C1 166.52(14) . . . . ?
C8 N1 C6 C5 -16.9(2) . . . . ?
C8 C9 C10 N3 -175.59(15) . . . . ?
C8 C9 C10 C16 1.4(3) . . . . ?
C9 N2 C11 N3 -0.60(16) . . . . ?
C9 N2 C11 C12 -179.92(13) . . . . ?
C9 N2 C15 C14 178.81(15) . . . . ?
C9 C10 C16 C00G -136.16(17) . . . . ?
C9 C10 C16 C17 42.6(2) . . . . ?
C10 N3 C11 N2 0.27(16) . . . . ?
C10 N3 C11 C12 179.48(15) . . . . ?
C10 C16 C17 C18 -177.39(14) . . . . ?
C11 N2 C9 C8 176.45(13) . . . . ?
C11 N2 C9 C10 0.66(15) . . . . ?
C11 N2 C15 C14 0.0(2) . . . . ?
C11 N3 C10 C9 0.17(16) . . . . ?
C11 N3 C10 C16 -177.05(13) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 N2 0.6(2) . . . . ?
C15 N2 C9 C8 -2.5(2) . . . . ?
C15 N2 C9 C10 -178.31(14) . . . . ?
C15 N2 C11 N3 178.49(13) . . . . ?
C15 N2 C11 C12 -0.8(2) . . . . ?
C16 C00G C20 C19 0.6(3) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C17 C18 C19 C20 -1.4(3) . . . . ?
C18 C19 C20 C00G 1.0(3) . . . . ?
C20 C00G C16 C10 177.04(17) . . . . ?
C20 C00G C16 C17 -1.7(3) . . . . ?
