#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/43/7214386.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_7214386
loop_
_publ_author_name
'Mutai, Toshiki'
'Shono, Hideaki'
'Shigemitsu, Yasuhiro'
'Araki, Koji'
_publ_section_title
;
 Three-color polymorph-dependent luminescence: crystallographic analysis
 and theoretical study on excited-state intramolecular proton transfer
 (ESIPT) luminescence of cyano-substituted imidazo[1,2-a]pyridine
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              3890
_journal_paper_doi               10.1039/c3ce42627k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C14 H9 N3 O'
_chemical_formula_sum            'C14 H9 N3 O'
_chemical_formula_weight         235.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.1960(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8196(10)
_cell_length_b                   11.356(3)
_cell_length_c                   25.246(7)
_cell_measurement_reflns_used    8368
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1093.4(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.1100
_diffrn_reflns_av_sigmaI/netI    0.1177
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8368
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0591
_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)+(0.0512P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                1750
_reflns_number_total             2479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce42627k2.cif
_cod_data_source_block           2_R
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1093.3(5)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7214386
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.8386(3) 0.67462(11) 0.18329(5) 0.0193(3) Uani 1 1 d
C15 C 0.3369(4) 0.39160(15) 0.26091(7) 0.0133(4) Uani 1 1 d
N2 N 0.5872(4) 0.57286(12) 0.26631(6) 0.0136(4) Uani 1 1 d
N3 N 0.0138(4) 0.33779(15) 0.48696(7) 0.0265(4) Uani 1 1 d
C1 C 0.4941(4) 0.47939(14) 0.23296(7) 0.0120(4) Uani 1 1 d
N4 N 0.3317(4) 0.43148(12) 0.31237(5) 0.0117(3) Uani 1 1 d
C3 C 0.2113(4) 0.37844(15) 0.35660(7) 0.0133(4) Uani 1 1 d
C4 C 0.2426(4) 0.43790(16) 0.40354(7) 0.0144(4) Uani 1 1 d
C5 C 0.3973(4) 0.55213(16) 0.40721(7) 0.0153(4) Uani 1 1 d
C6 C 0.5155(5) 0.60371(16) 0.36301(7) 0.0149(4) Uani 1 1 d
C7 C 0.4872(4) 0.54343(15) 0.31408(7) 0.0123(4) Uani 1 1 d
C8 C 0.1149(5) 0.38181(15) 0.45001(7) 0.0175(4) Uani 1 1 d
C9 C 0.5710(4) 0.48087(15) 0.17693(7) 0.0134(4) Uani 1 1 d
C10 C 0.7360(4) 0.57843(15) 0.15411(7) 0.0143(4) Uani 1 1 d
C11 C 0.7991(5) 0.57862(17) 0.10035(7) 0.0185(4) Uani 1 1 d
C12 C 0.7055(5) 0.48320(17) 0.06898(8) 0.0199(4) Uani 1 1 d
C13 C 0.5453(5) 0.38488(17) 0.09059(7) 0.0196(5) Uani 1 1 d
C14 C 0.4790(5) 0.38579(16) 0.14393(7) 0.0165(4) Uani 1 1 d
H1 H 0.231(4) 0.3159(15) 0.2504(6) 0.006(4) Uiso 1 1 d
H2 H 0.096(4) 0.3019(16) 0.3505(7) 0.012(5) Uiso 1 1 d
H3 H 0.415(5) 0.5906(17) 0.4411(7) 0.024(5) Uiso 1 1 d
H4 H 0.627(5) 0.6770(18) 0.3632(7) 0.023(5) Uiso 1 1 d
H5 H 0.912(5) 0.6484(18) 0.0850(7) 0.029(6) Uiso 1 1 d
H6 H 0.757(5) 0.4857(16) 0.0311(8) 0.022(5) Uiso 1 1 d
H7 H 0.478(5) 0.3180(17) 0.0675(7) 0.024(5) Uiso 1 1 d
H8 H 0.365(4) 0.3154(17) 0.1608(7) 0.017(5) Uiso 1 1 d
H9 H 0.790(6) 0.6595(19) 0.2190(9) 0.039(7) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N4 C15 C1 105.96(15)
C7 N2 C1 106.34(14)
C15 C1 N2 110.27(15)
C15 C1 C9 128.39(16)
N2 C1 C9 121.32(15)
C3 N4 C15 130.35(15)
C3 N4 C7 122.27(14)
C15 N4 C7 107.37(14)
C4 C3 N4 118.25(17)
C3 C4 C5 121.52(16)
C3 C4 C8 118.07(17)
C5 C4 C8 120.40(16)
C6 C5 C4 119.60(17)
C5 C6 C7 119.79(18)
N2 C7 N4 110.06(15)
N2 C7 C6 131.38(17)
N4 C7 C6 118.56(16)
N3 C8 C4 179.7(2)
C14 C9 C10 117.78(17)
C14 C9 C1 120.74(16)
C10 C9 C1 121.47(15)
O1 C10 C11 117.75(16)
O1 C10 C9 121.97(16)
C11 C10 C9 120.28(17)
C12 C11 C10 120.39(17)
C11 C12 C13 120.60(18)
C14 C13 C12 118.77(18)
C13 C14 C9 122.18(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.363(2)
C15 N4 1.377(2)
C15 C1 1.378(2)
N2 C7 1.328(2)
N2 C1 1.389(2)
N3 C8 1.144(2)
C1 C9 1.461(2)
N4 C3 1.371(2)
N4 C7 1.403(2)
C3 C4 1.363(2)
C4 C5 1.426(3)
C4 C8 1.444(2)
C5 C6 1.359(2)
C6 C7 1.411(2)
C9 C14 1.397(2)
C9 C10 1.413(2)
C10 C11 1.392(2)
C11 C12 1.377(3)
C12 C13 1.399(3)
C13 C14 1.384(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
N4 C15 C1 N2 0.18(19)
N4 C15 C1 C9 178.67(15)
C7 N2 C1 C15 -0.33(18)
C7 N2 C1 C9 -178.95(14)
C1 C15 N4 C3 -178.65(15)
C1 C15 N4 C7 0.04(18)
C15 N4 C3 C4 179.11(16)
C7 N4 C3 C4 0.6(2)
N4 C3 C4 C5 -0.3(3)
N4 C3 C4 C8 179.88(14)
C3 C4 C5 C6 0.3(3)
C8 C4 C5 C6 -179.87(16)
C4 C5 C6 C7 -0.6(3)
C1 N2 C7 N4 0.36(18)
C1 N2 C7 C6 179.72(18)
C3 N4 C7 N2 178.56(14)
C15 N4 C7 N2 -0.25(18)
C3 N4 C7 C6 -0.9(2)
C15 N4 C7 C6 -179.71(15)
C5 C6 C7 N2 -178.44(17)
C5 C6 C7 N4 0.9(2)
C3 C4 C8 N3 -169(100)
C5 C4 C8 N3 11(51)
C15 C1 C9 C14 1.0(3)
N2 C1 C9 C14 179.38(15)
C15 C1 C9 C10 -179.79(17)
N2 C1 C9 C10 -1.4(2)
C14 C9 C10 O1 -179.29(15)
C1 C9 C10 O1 1.5(2)
C14 C9 C10 C11 0.6(2)
C1 C9 C10 C11 -178.56(15)
O1 C10 C11 C12 179.13(16)
C9 C10 C11 C12 -0.8(3)
C10 C11 C12 C13 0.1(3)
C11 C12 C13 C14 0.7(3)
C12 C13 C14 C9 -0.9(3)
C10 C9 C14 C13 0.2(3)
C1 C9 C14 C13 179.41(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71614809
