#------------------------------------------------------------------------------
#$Date: 2019-09-20 06:25:54 +0300 (Fri, 20 Sep 2019) $
#$Revision: 218569 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/39/7233987.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_7233987
loop_
_publ_author_name
'Sivappa, Rasapalli'
'Sammeta, Vamshikrishna Reddy'
'Huang, Yanchang'
'Golen, James A.'
'Savinov, Sergey N.'
_publ_section_title
;
 Facile synthesis of 3-substituted imidazo[1,2-a]pyridines through
 formimidamide chemistry
;
_journal_issue                   51
_journal_name_full               'RSC Advances'
_journal_page_first              29659
_journal_paper_doi               10.1039/C9RA05841A
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C14 H9 F3 N2'
_chemical_formula_weight         262.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2019-05-31 deposited with the CCDC.    2019-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.316(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7552(7)
_cell_length_b                   9.5594(8)
_cell_length_c                   12.4421(10)
_cell_measurement_reflns_used    9094
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.70
_cell_measurement_theta_min      2.98
_cell_volume                     1159.97(16)
_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-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            42264
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.729
_diffrn_reflns_theta_min         2.984
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.215(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0553
_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)+(0.0676P)²+0.9899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1469
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2013
_reflns_number_total             2203
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra05841a2.cif
_cod_data_source_block           UMD1749e_a
_cod_database_code               7233987
_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   0.959
_shelx_estimated_absorpt_t_max   0.966
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F1 F 0.41355(17) 0.3883(2) 0.43520(14) 0.0703(6) Uani 1 1 d . .
F2 F 0.3007(2) 0.54780(16) 0.35279(13) 0.0698(6) Uani 1 1 d . .
F3 F 0.22248(18) 0.34113(18) 0.35950(12) 0.0639(5) Uani 1 1 d . .
N1 N 0.33277(16) 0.15555(17) 0.60562(12) 0.0275(4) Uani 1 1 d . .
N2 N 0.18991(18) -0.01447(18) 0.55002(16) 0.0368(5) Uani 1 1 d . .
C1 C 0.4541(2) 0.2107(2) 0.64519(16) 0.0340(5) Uani 1 1 d . .
H1 H 0.4631 0.3085 0.6569 0.041 Uiso 1 1 calc R U
C2 C 0.5601(2) 0.1237(2) 0.66714(18) 0.0395(5) Uani 1 1 d . .
H2 H 0.6446 0.1606 0.6940 0.047 Uiso 1 1 calc R U
C3 C 0.5462(2) -0.0223(2) 0.65041(17) 0.0386(5) Uani 1 1 d . .
H3 H 0.6217 -0.0824 0.6658 0.046 Uiso 1 1 calc R U
C4 C 0.4266(2) -0.0769(2) 0.61269(17) 0.0346(5) Uani 1 1 d . .
H4 H 0.4177 -0.1750 0.6024 0.041 Uiso 1 1 calc R U
C5 C 0.3145(2) 0.0129(2) 0.58857(15) 0.0296(5) Uani 1 1 d . .
C6 C 0.1270(2) 0.1132(2) 0.54277(19) 0.0363(5) Uani 1 1 d . .
H6 H 0.0353 0.1262 0.5174 0.044 Uiso 1 1 calc R U
C7 C 0.2107(2) 0.2193(2) 0.57602(16) 0.0307(5) Uani 1 1 d . .
C8 C 0.18379(19) 0.3700(2) 0.59343(16) 0.0297(5) Uani 1 1 d . .
C9 C 0.2171(2) 0.4746(2) 0.51954(16) 0.0312(5) Uani 1 1 d . .
C10 C 0.1865(2) 0.6139(2) 0.54047(18) 0.0360(5) Uani 1 1 d . .
H10 H 0.2081 0.6837 0.4893 0.043 Uiso 1 1 calc R U
C11 C 0.1251(2) 0.6514(2) 0.63467(19) 0.0419(6) Uani 1 1 d . .
H11 H 0.1070 0.7471 0.6492 0.050 Uiso 1 1 calc R U
C12 C 0.0896(2) 0.5494(2) 0.70862(19) 0.0433(6) Uani 1 1 d . .
H12 H 0.0456 0.5744 0.7732 0.052 Uiso 1 1 calc R U
C13 C 0.1189(2) 0.4115(2) 0.68698(18) 0.0369(5) Uani 1 1 d . .
H13 H 0.0940 0.3420 0.7376 0.044 Uiso 1 1 calc R U
C14 C 0.2868(2) 0.4378(2) 0.41729(18) 0.0372(5) 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'
F F 0.0171 0.0103 '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
C1 N1 C7 130.96(17)
C1 N1 C5 122.42(17)
C7 N1 C5 106.62(16)
C5 N2 C6 104.74(17)
C2 C1 N1 118.99(19)
C2 C1 H1 120.5
N1 C1 H1 120.5
C1 C2 C3 120.4(2)
C1 C2 H2 119.8
C3 C2 H2 119.8
C4 C3 C2 120.7(2)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 119.65(19)
C3 C4 H4 120.2
C5 C4 H4 120.2
N2 C5 N1 111.25(17)
N2 C5 C4 130.92(19)
N1 C5 C4 117.82(18)
C7 C6 N2 112.35(18)
C7 C6 H6 123.8
N2 C6 H6 123.8
C6 C7 N1 105.04(17)
C6 C7 C8 131.49(19)
N1 C7 C8 123.06(17)
C13 C8 C9 117.48(19)
C13 C8 C7 118.92(18)
C9 C8 C7 123.59(19)
C10 C9 C8 120.39(19)
C10 C9 C14 119.20(19)
C8 C9 C14 120.41(18)
C11 C10 C9 120.6(2)
C11 C10 H10 119.7
C9 C10 H10 119.7
C10 C11 C12 120.1(2)
C10 C11 H11 120.0
C12 C11 H11 120.0
C13 C12 C11 119.1(2)
C13 C12 H12 120.5
C11 C12 H12 120.5
C12 C13 C8 122.4(2)
C12 C13 H13 118.8
C8 C13 H13 118.8
F3 C14 F2 106.1(2)
F3 C14 F1 105.62(19)
F2 C14 F1 105.86(19)
F3 C14 C9 114.04(18)
F2 C14 C9 112.37(18)
F1 C14 C9 112.17(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C14 1.337(3)
F2 C14 1.332(3)
F3 C14 1.321(3)
N1 C1 1.376(3)
N1 C7 1.380(2)
N1 C5 1.391(2)
N2 C5 1.323(3)
N2 C6 1.368(3)
C1 C2 1.351(3)
C1 H1 0.9500
C2 C3 1.417(3)
C2 H2 0.9500
C3 C4 1.353(3)
C3 H3 0.9500
C4 C5 1.417(3)
C4 H4 0.9500
C6 C7 1.361(3)
C6 H6 0.9500
C7 C8 1.481(3)
C8 C13 1.395(3)
C8 C9 1.402(3)
C9 C10 1.390(3)
C9 C14 1.498(3)
C10 C11 1.376(3)
C10 H10 0.9500
C11 C12 1.390(3)
C11 H11 0.9500
C12 C13 1.377(3)
C12 H12 0.9500
C13 H13 0.9500
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
C7 N1 C1 C2 -179.4(2)
C5 N1 C1 C2 0.8(3)
N1 C1 C2 C3 -0.5(3)
C1 C2 C3 C4 -0.3(3)
C2 C3 C4 C5 0.7(3)
C6 N2 C5 N1 -0.3(2)
C6 N2 C5 C4 -179.6(2)
C1 N1 C5 N2 -179.83(17)
C7 N1 C5 N2 0.3(2)
C1 N1 C5 C4 -0.4(3)
C7 N1 C5 C4 179.76(17)
C3 C4 C5 N2 178.9(2)
C3 C4 C5 N1 -0.4(3)
C5 N2 C6 C7 0.1(3)
N2 C6 C7 N1 0.1(2)
N2 C6 C7 C8 -172.5(2)
C1 N1 C7 C6 179.93(19)
C5 N1 C7 C6 -0.3(2)
C1 N1 C7 C8 -6.6(3)
C5 N1 C7 C8 173.17(18)
C6 C7 C8 C13 78.1(3)
N1 C7 C8 C13 -93.5(2)
C6 C7 C8 C9 -100.4(3)
N1 C7 C8 C9 88.1(3)
C13 C8 C9 C10 0.3(3)
C7 C8 C9 C10 178.82(19)
C13 C8 C9 C14 -179.94(18)
C7 C8 C9 C14 -1.5(3)
C8 C9 C10 C11 1.1(3)
C14 C9 C10 C11 -178.6(2)
C9 C10 C11 C12 -1.9(4)
C10 C11 C12 C13 1.2(4)
C11 C12 C13 C8 0.3(4)
C9 C8 C13 C12 -1.0(3)
C7 C8 C13 C12 -179.6(2)
C10 C9 C14 F3 -126.3(2)
C8 C9 C14 F3 54.0(3)
C10 C9 C14 F2 -5.4(3)
C8 C9 C14 F2 174.87(19)
C10 C9 C14 F1 113.7(2)
C8 C9 C14 F1 -66.0(3)
