#------------------------------------------------------------------------------
#$Date: 2019-11-23 22:15:22 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235319 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/62/7236253.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_7236253
loop_
_publ_author_name
'Chen, Zhengwang'
'Wen, Yuelu'
'Luo, Guotian'
'Ye, Min'
'Wang, Qinghao'
_publ_section_title
;
 Transition-metal-free C--C bond cleavage and formation: efficient
 synthesis of 2,3-diarylimidazo[1,2-α]pyridines from 2-aminopyridines and
 alkynoates
;
_journal_issue                   89
_journal_name_full               'RSC Advances'
_journal_page_first              86464
_journal_paper_doi               10.1039/C6RA19291B
_journal_volume                  6
_journal_year                    2016
_chemical_formula_sum            'C19 H14 N2'
_chemical_formula_weight         270.32
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-12-08 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9203(2)
_cell_length_b                   10.4738(3)
_cell_length_c                   16.8627(6)
_cell_measurement_reflns_used    1591
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.30
_cell_measurement_theta_min      3.22
_cell_volume                     1398.86(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7630
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   5(6)
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0838
_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
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.4254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                1804
_reflns_number_total             2489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra19291b2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               7236253
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.4718(3) 0.3528(2) 0.19567(16) 0.0420(7) Uani 1 1 d .
N2 N 0.7067(4) 0.4297(3) 0.14013(16) 0.0482(7) Uani 1 1 d .
C14 C 0.8831(4) 0.4782(3) 0.25667(19) 0.0424(8) Uani 1 1 d .
C5 C 0.3055(4) 0.3109(3) 0.1953(2) 0.0501(9) Uani 1 1 d .
H5 H 0.2491 0.2948 0.2427 0.060 Uiso 1 1 calc R
C7 C 0.7236(4) 0.4305(3) 0.22187(19) 0.0411(8) Uani 1 1 d .
C9 C 0.4644(5) 0.2476(3) 0.3668(2) 0.0503(9) Uani 1 1 d .
H9 H 0.4525 0.1807 0.3310 0.060 Uiso 1 1 calc R
C6 C 0.5811(4) 0.3836(3) 0.25832(19) 0.0401(8) Uani 1 1 d .
C3 C 0.3093(5) 0.3198(4) 0.0540(2) 0.0631(11) Uani 1 1 d .
H3 H 0.2529 0.3066 0.0063 0.076 Uiso 1 1 calc R
C15 C 0.9447(4) 0.4373(3) 0.3300(2) 0.0496(9) Uani 1 1 d .
H15 H 0.8849 0.3774 0.3594 0.060 Uiso 1 1 calc R
C1 C 0.5555(4) 0.3829(3) 0.1257(2) 0.0429(8) Uani 1 1 d .
C8 C 0.5339(4) 0.3630(3) 0.34178(19) 0.0432(8) Uani 1 1 d .
C13 C 0.5581(4) 0.4594(3) 0.3978(2) 0.0463(8) Uani 1 1 d .
H13 H 0.6064 0.5364 0.3825 0.056 Uiso 1 1 calc R
C2 C 0.4717(5) 0.3646(3) 0.0527(2) 0.0575(10) Uani 1 1 d .
H2 H 0.5254 0.3824 0.0050 0.069 Uiso 1 1 calc R
C18 C 1.1258(5) 0.6151(3) 0.2434(2) 0.0623(11) Uani 1 1 d .
H18 H 1.1864 0.6751 0.2144 0.075 Uiso 1 1 calc R
C4 C 0.2269(5) 0.2938(4) 0.1248(2) 0.0594(10) Uani 1 1 d .
H4 H 0.1162 0.2642 0.1238 0.071 Uiso 1 1 calc R
C19 C 0.9761(4) 0.5666(3) 0.2137(2) 0.0545(9) Uani 1 1 d .
H19 H 0.9374 0.5935 0.1644 0.065 Uiso 1 1 calc R
C10 C 0.4134(5) 0.2320(4) 0.4442(2) 0.0615(10) Uani 1 1 d .
H10 H 0.3635 0.1558 0.4601 0.074 Uiso 1 1 calc R
C16 C 1.0955(5) 0.4863(3) 0.3586(2) 0.0564(10) Uani 1 1 d .
H16 H 1.1364 0.4588 0.4075 0.068 Uiso 1 1 calc R
C17 C 1.1850(5) 0.5747(4) 0.3159(3) 0.0624(10) Uani 1 1 d .
H17 H 1.2855 0.6073 0.3359 0.075 Uiso 1 1 calc R
C12 C 0.5109(5) 0.4411(4) 0.4753(2) 0.0575(10) Uani 1 1 d .
H12 H 0.5300 0.5052 0.5124 0.069 Uiso 1 1 calc R
C11 C 0.4360(5) 0.3294(4) 0.4984(2) 0.0640(11) Uani 1 1 d .
H11 H 0.4004 0.3191 0.5506 0.077 Uiso 1 1 calc R
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
C5 N1 C1 121.4(3)
C5 N1 C6 131.4(3)
C1 N1 C6 107.0(3)
C1 N2 C7 105.9(3)
C19 C14 C15 118.8(3)
C19 C14 C7 118.1(3)
C15 C14 C7 123.1(3)
C4 C5 N1 118.8(3)
C4 C5 H5 120.6
N1 C5 H5 120.6
C6 C7 N2 111.3(3)
C6 C7 C14 130.1(3)
N2 C7 C14 118.6(3)
C10 C9 C8 120.4(3)
C10 C9 H9 119.8
C8 C9 H9 119.8
C7 C6 N1 104.6(3)
C7 C6 C8 133.5(3)
N1 C6 C8 121.9(3)
C2 C3 C4 121.5(4)
C2 C3 H3 119.3
C4 C3 H3 119.3
C16 C15 C14 119.7(3)
C16 C15 H15 120.1
C14 C15 H15 120.1
N2 C1 N1 111.2(3)
N2 C1 C2 129.8(3)
N1 C1 C2 119.0(3)
C9 C8 C13 118.5(3)
C9 C8 C6 121.2(3)
C13 C8 C6 120.4(3)
C12 C13 C8 120.4(3)
C12 C13 H13 119.8
C8 C13 H13 119.8
C3 C2 C1 118.4(4)
C3 C2 H2 120.8
C1 C2 H2 120.8
C17 C18 C19 120.0(4)
C17 C18 H18 120.0
C19 C18 H18 120.0
C5 C4 C3 120.9(4)
C5 C4 H4 119.5
C3 C4 H4 119.5
C18 C19 C14 120.7(4)
C18 C19 H19 119.7
C14 C19 H19 119.7
C9 C10 C11 120.1(3)
C9 C10 H10 119.9
C11 C10 H10 119.9
C17 C16 C15 120.8(4)
C17 C16 H16 119.6
C15 C16 H16 119.6
C16 C17 C18 119.9(3)
C16 C17 H17 120.0
C18 C17 H17 120.0
C11 C12 C13 120.6(4)
C11 C12 H12 119.7
C13 C12 H12 119.7
C12 C11 C10 119.9(4)
C12 C11 H11 120.0
C10 C11 H11 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.388(4)
N1 C1 1.390(4)
N1 C6 1.404(4)
N2 C1 1.316(4)
N2 C7 1.385(4)
C14 C19 1.387(4)
C14 C15 1.397(4)
C14 C7 1.480(5)
C5 C4 1.354(5)
C5 H5 0.9300
C7 C6 1.375(4)
C9 C10 1.376(5)
C9 C8 1.394(4)
C9 H9 0.9300
C6 C8 1.472(4)
C3 C2 1.369(5)
C3 C4 1.387(5)
C3 H3 0.9300
C15 C16 1.387(5)
C15 H15 0.9300
C1 C2 1.411(5)
C8 C13 1.396(4)
C13 C12 1.373(5)
C13 H13 0.9300
C2 H2 0.9300
C18 C17 1.376(5)
C18 C19 1.384(5)
C18 H18 0.9300
C4 H4 0.9300
C19 H19 0.9300
C10 C11 1.381(5)
C10 H10 0.9300
C16 C17 1.370(5)
C16 H16 0.9300
C17 H17 0.9300
C12 C11 1.368(5)
C12 H12 0.9300
C11 H11 0.9300
