#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:32:14 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290220 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247899.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_7247899
loop_
_publ_author_name
'Charpe, Vaibhav Pramod'
'Gupta, Mahima'
'Hwang, Kuo Chu'
_publ_section_title
;
 Visible light-mediated copper catalyzed regioselective diamination of
 terminal alkynes at room temperature: a facile synthesis of substituted
 imidazo[1,2-α]pyridines
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              1329
_journal_page_last               1337
_journal_paper_doi               10.1039/D3GC04062C
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C21 H12 F2 N2'
_chemical_formula_weight         330.33
_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-2014/6
_audit_update_record
;
2023-08-07 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.180(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4478(6)
_cell_length_b                   17.5319(7)
_cell_length_c                   12.9774(4)
_cell_measurement_reflns_used    3181
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.6191
_cell_measurement_theta_min      2.8155
_cell_volume                     3245.0(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0305
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12325
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_min         1.841
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.9055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0463
_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)+(0.0605P)²+1.2434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2370
_reflns_number_total             3321
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc04062c2.cif
_cod_data_source_block           170613LT_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7247899--7247903.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7247899
_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.
;
_shelxl_version_number           2014/6
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.14485(14) -0.03143(8) 1.04522(16) 0.1383(7) Uani 1 1 d . . . . .
F2 F 0.11889(10) 0.16425(8) 0.29189(10) 0.0967(5) Uani 1 1 d . . . . .
N1 N 0.12007(9) 0.45583(8) 0.59912(9) 0.0436(3) Uani 1 1 d . . . . .
N2 N 0.12378(12) 0.43397(9) 0.77025(10) 0.0597(4) Uani 1 1 d . . . . .
C1 C 0.12045(14) 0.21661(11) 0.36954(14) 0.0629(5) Uani 1 1 d . . . . .
C2 C 0.17879(13) 0.27776(11) 0.37097(13) 0.0574(5) Uani 1 1 d . . . . .
H12 H 0.2175 0.2838 0.3188 0.069 Uiso 1 1 calc R U . . .
C3 C 0.18048(12) 0.33102(10) 0.45009(12) 0.0494(4) Uani 1 1 d . . . . .
H11 H 0.2210 0.3739 0.4524 0.059 Uiso 1 1 calc R U . . .
C4 C 0.12340(11) 0.32244(9) 0.52629(11) 0.0450(4) Uani 1 1 d . . . . .
C5 C 0.12399(11) 0.37749(9) 0.61162(11) 0.0445(4) Uani 1 1 d . . . . .
C6 C 0.12596(12) 0.36631(10) 0.71749(12) 0.0512(4) Uani 1 1 d . . . . .
C7 C 0.13227(13) 0.29526(11) 0.77171(12) 0.0548(4) Uani 1 1 d . . . . .
C8 C 0.13739(13) 0.23678(11) 0.81942(13) 0.0557(5) Uani 1 1 d . . . . .
C9 C 0.14095(12) 0.16681(10) 0.87689(14) 0.0543(4) Uani 1 1 d . . . . .
C10 C 0.12473(17) 0.09773(13) 0.82682(19) 0.0831(7) Uani 1 1 d . . . . .
H9 H 0.1120 0.0959 0.7527 0.100 Uiso 1 1 calc R U . . .
C11 C 0.1269(2) 0.03039(13) 0.8846(3) 0.1019(9) Uani 1 1 d . . . . .
H8 H 0.1164 -0.0176 0.8506 0.122 Uiso 1 1 calc R U . . .
C12 C 0.14431(18) 0.03496(13) 0.9902(2) 0.0871(7) Uani 1 1 d . . . . .
C13 C 0.06600(12) 0.25868(10) 0.52201(14) 0.0559(5) Uani 1 1 d . . . . .
H2 H 0.0271 0.2518 0.5738 0.067 Uiso 1 1 calc R U . . .
C14 C 0.06438(14) 0.20498(12) 0.44367(16) 0.0671(5) Uani 1 1 d . . . . .
H1 H 0.0254 0.1612 0.4414 0.081 Uiso 1 1 calc R U . . .
C15 C 0.11347(11) 0.50165(10) 0.51164(11) 0.0470(4) Uani 1 1 d . . . . .
H3 H 0.1133 0.4795 0.4448 0.056 Uiso 1 1 calc R U . . .
C16 C 0.10733(12) 0.57765(10) 0.52147(13) 0.0517(4) Uani 1 1 d . . . . .
H4 H 0.1038 0.6091 0.4613 0.062 Uiso 1 1 calc R U . . .
C17 C 0.10600(14) 0.61132(11) 0.61954(14) 0.0607(5) Uani 1 1 d . . . . .
H5 H 0.1014 0.6651 0.6253 0.073 Uiso 1 1 calc R U . . .
C18 C 0.11136(15) 0.56688(11) 0.70592(14) 0.0635(5) Uani 1 1 d . . . . .
H10 H 0.1099 0.5896 0.7721 0.076 Uiso 1 1 calc R U . . .
C19 C 0.11900(12) 0.48751(10) 0.69763(11) 0.0516(4) Uani 1 1 d . . . . .
C20 C 0.16232(15) 0.10080(13) 1.04192(18) 0.0740(6) Uani 1 1 d . . . . .
H7 H 0.1758 0.1015 1.1160 0.089 Uiso 1 1 calc R U . . .
C21 C 0.16098(13) 0.16746(11) 0.98545(14) 0.0600(5) Uani 1 1 d . . . . .
H6 H 0.1739 0.2145 1.0211 0.072 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'
F F 0.0171 0.0103 '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
C15 N1 C5 132.06(13) . . ?
C15 N1 C19 120.78(14) . . ?
C5 N1 C19 107.09(12) . . ?
C19 N2 C6 105.09(13) . . ?
F2 C1 C2 118.57(18) . . ?
F2 C1 C14 118.59(19) . . ?
C2 C1 C14 122.84(17) . . ?
C1 C2 C3 118.58(16) . . ?
C1 C2 H12 120.7 . . ?
C3 C2 H12 120.7 . . ?
C2 C3 C4 120.72(17) . . ?
C2 C3 H11 119.6 . . ?
C4 C3 H11 119.6 . . ?
C13 C4 C3 118.44(15) . . ?
C13 C4 C5 119.44(14) . . ?
C3 C4 C5 122.11(15) . . ?
N1 C5 C6 104.54(14) . . ?
N1 C5 C4 124.70(13) . . ?
C6 C5 C4 130.74(15) . . ?
N2 C6 C5 111.99(15) . . ?
N2 C6 C7 120.89(14) . . ?
C5 C6 C7 127.09(16) . . ?
C8 C7 C6 178.30(18) . . ?
C7 C8 C9 178.48(19) . . ?
C10 C9 C21 118.49(18) . . ?
C10 C9 C8 121.23(18) . . ?
C21 C9 C8 120.28(17) . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H9 119.9 . . ?
C11 C10 H9 119.9 . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H8 120.7 . . ?
C10 C11 H8 120.7 . . ?
C20 C12 C11 123.2(2) . . ?
C20 C12 F1 119.3(3) . . ?
C11 C12 F1 117.6(3) . . ?
C14 C13 C4 121.18(16) . . ?
C14 C13 H2 119.4 . . ?
C4 C13 H2 119.4 . . ?
C1 C14 C13 118.23(18) . . ?
C1 C14 H1 120.9 . . ?
C13 C14 H1 120.9 . . ?
C16 C15 N1 119.73(14) . . ?
C16 C15 H3 120.1 . . ?
N1 C15 H3 120.1 . . ?
C15 C16 C17 120.88(15) . . ?
C15 C16 H4 119.6 . . ?
C17 C16 H4 119.6 . . ?
C18 C17 C16 119.97(18) . . ?
C18 C17 H5 120.0 . . ?
C16 C17 H5 120.0 . . ?
C17 C18 C19 120.09(16) . . ?
C17 C18 H10 120.0 . . ?
C19 C18 H10 120.0 . . ?
N2 C19 N1 111.27(15) . . ?
N2 C19 C18 130.17(15) . . ?
N1 C19 C18 118.54(15) . . ?
C12 C20 C21 118.7(2) . . ?
C12 C20 H7 120.7 . . ?
C21 C20 H7 120.7 . . ?
C20 C21 C9 120.9(2) . . ?
C20 C21 H6 119.5 . . ?
C9 C21 H6 119.5 . . ?
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
F1 C12 1.365(2) . ?
F2 C1 1.361(2) . ?
N1 C15 1.3815(19) . ?
N1 C5 1.383(2) . ?
N1 C19 1.3962(19) . ?
N2 C19 1.324(2) . ?
N2 C6 1.373(2) . ?
C1 C2 1.362(3) . ?
C1 C14 1.368(3) . ?
C2 C3 1.385(2) . ?
C2 H12 0.9500 . ?
C3 C4 1.393(2) . ?
C3 H11 0.9500 . ?
C4 C13 1.388(2) . ?
C4 C5 1.468(2) . ?
C5 C6 1.384(2) . ?
C6 C7 1.426(2) . ?
C7 C8 1.194(2) . ?
C8 C9 1.432(2) . ?
C9 C10 1.377(3) . ?
C9 C21 1.392(3) . ?
C10 C11 1.396(3) . ?
C10 H9 0.9500 . ?
C11 C12 1.356(4) . ?
C11 H8 0.9500 . ?
C12 C20 1.339(3) . ?
C13 C14 1.383(2) . ?
C13 H2 0.9500 . ?
C14 H1 0.9500 . ?
C15 C16 1.343(2) . ?
C15 H3 0.9500 . ?
C16 C17 1.406(2) . ?
C16 H4 0.9500 . ?
C17 C18 1.357(3) . ?
C17 H5 0.9500 . ?
C18 C19 1.401(3) . ?
C18 H10 0.9500 . ?
C20 C21 1.378(3) . ?
C20 H7 0.9500 . ?
C21 H6 0.9500 . ?
