#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/63/1516385.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_1516385
loop_
_publ_author_name
'Chen, Chyi-Lin'
'Lin, Chun-Wei'
'Hsieh, Cheng-Chih'
'Lai, Chin-Hung'
'Lee, Gene-Hsiang'
'Wang, Chih-Chieh'
'Chou, Pi-Tai'
_publ_section_title
;
 Dual excited-state intramolecular proton transfer reaction in
 3-hydroxy-2-(pyridin-2-yl)-4H-chromen-4-one.
;
_journal_issue                   1
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              205
_journal_page_last               214
_journal_paper_doi               10.1021/jp809072a
_journal_volume                  113
_journal_year                    2009
_chemical_formula_sum            'C14 H9 N O3'
_chemical_formula_weight         239.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.8483(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4213(3)
_cell_length_b                   12.9119(4)
_cell_length_c                   7.4058(2)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.00
_cell_volume                     1076.04(5)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'NONIUS COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω 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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7518
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9670
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.053(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0546
_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)+(0.0915P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1506
_reflns_number_gt                1656
_reflns_number_total             2461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp809072a_si_001.cif
_cod_data_source_block           ic13091
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/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 

The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1516385
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.15406(8) 0.33476(7) 0.33457(13) 0.0332(3) Uani 1 1 d .
O2 O 0.10188(9) 0.05736(7) 0.35615(15) 0.0404(3) Uani 1 1 d .
H2 H 0.0318(19) 0.0766(15) 0.393(3) 0.072(6) Uiso 1 1 d .
O3 O 0.32102(9) 0.06183(8) 0.25926(15) 0.0451(3) Uani 1 1 d .
N1 N -0.07348(10) 0.16553(9) 0.43490(15) 0.0332(3) Uani 1 1 d .
C1 C 0.26521(12) 0.33610(11) 0.28935(18) 0.0311(3) Uani 1 1 d .
C2 C 0.31376(13) 0.43362(11) 0.2721(2) 0.0395(4) Uani 1 1 d .
H2A H 0.2702 0.4943 0.2904 0.047 Uiso 1 1 calc R
C3 C 0.42566(13) 0.44098(12) 0.2283(2) 0.0426(4) Uani 1 1 d .
H3 H 0.4601 0.5072 0.2173 0.051 Uiso 1 1 calc R
C4 C 0.48901(13) 0.35144(13) 0.1997(2) 0.0412(4) Uani 1 1 d .
H4 H 0.5663 0.3571 0.1695 0.049 Uiso 1 1 calc R
C5 C 0.44005(13) 0.25569(11) 0.2152(2) 0.0378(4) Uani 1 1 d .
H5 H 0.4835 0.1954 0.1944 0.045 Uiso 1 1 calc R
C6 C 0.32629(12) 0.24574(10) 0.26155(19) 0.0313(3) Uani 1 1 d .
C7 C 0.27203(12) 0.14457(11) 0.28234(19) 0.0341(4) Uani 1 1 d .
C8 C 0.15402(12) 0.14925(10) 0.33367(18) 0.0306(3) Uani 1 1 d .
C9 C 0.10060(12) 0.24142(10) 0.35566(18) 0.0292(3) Uani 1 1 d .
C10 C -0.01812(12) 0.25429(10) 0.40144(18) 0.0294(3) Uani 1 1 d .
C11 C -0.07175(12) 0.35110(11) 0.40661(19) 0.0341(4) Uani 1 1 d .
H11 H -0.0305 0.4126 0.3854 0.041 Uiso 1 1 calc R
C12 C -0.18626(13) 0.35544(12) 0.44322(19) 0.0385(4) Uani 1 1 d .
H12 H -0.2261 0.4200 0.4432 0.046 Uiso 1 1 calc R
C13 C -0.24222(13) 0.26478(12) 0.47982(19) 0.0381(4) Uani 1 1 d .
H13 H -0.3205 0.2664 0.5073 0.046 Uiso 1 1 calc R
C14 C -0.18264(12) 0.17173(12) 0.47592(19) 0.0371(4) Uani 1 1 d .
H14 H -0.2209 0.1098 0.5035 0.044 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0337(5) 0.0278(5) 0.0396(6) -0.0006(4) 0.0107(4) -0.0005(4)
O2 0.0394(6) 0.0266(6) 0.0560(7) 0.0005(4) 0.0099(5) 0.0005(4)
O3 0.0393(6) 0.0368(6) 0.0590(7) -0.0049(5) 0.0081(5) 0.0086(4)
N1 0.0332(6) 0.0344(7) 0.0316(6) 0.0020(5) 0.0045(5) -0.0004(5)
C1 0.0299(7) 0.0359(8) 0.0280(7) -0.0012(5) 0.0060(5) -0.0002(5)
C2 0.0444(8) 0.0336(8) 0.0426(8) -0.0030(6) 0.0132(6) -0.0020(6)
C3 0.0422(8) 0.0424(9) 0.0447(9) -0.0021(7) 0.0115(7) -0.0101(7)
C4 0.0318(7) 0.0530(10) 0.0396(8) 0.0014(7) 0.0087(6) -0.0019(6)
C5 0.0324(7) 0.0453(9) 0.0351(8) -0.0009(6) 0.0047(6) 0.0068(6)
C6 0.0305(7) 0.0357(8) 0.0263(7) -0.0009(5) 0.0009(5) 0.0018(5)
C7 0.0338(7) 0.0350(8) 0.0318(8) -0.0020(6) 0.0012(6) 0.0068(6)
C8 0.0309(7) 0.0278(7) 0.0315(7) 0.0001(5) 0.0006(6) 0.0001(5)
C9 0.0322(7) 0.0273(7) 0.0273(7) 0.0009(5) 0.0030(6) -0.0005(5)
C10 0.0316(7) 0.0312(8) 0.0247(7) 0.0002(5) 0.0032(5) 0.0026(5)
C11 0.0376(8) 0.0328(8) 0.0322(7) 0.0003(6) 0.0074(6) 0.0006(6)
C12 0.0406(8) 0.0415(9) 0.0341(8) 0.0017(6) 0.0085(6) 0.0119(6)
C13 0.0315(7) 0.0508(9) 0.0329(8) 0.0037(6) 0.0076(6) 0.0039(6)
C14 0.0348(7) 0.0434(8) 0.0329(8) 0.0033(6) 0.0056(6) -0.0019(6)
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
C1 O1 C9 119.27(10)
C14 N1 C10 118.36(12)
O1 C1 C2 115.82(12)
O1 C1 C6 122.35(12)
C2 C1 C6 121.83(13)
C3 C2 C1 119.06(13)
C2 C3 C4 120.28(14)
C5 C4 C3 120.28(13)
C4 C5 C6 120.71(13)
C1 C6 C5 117.83(13)
C1 C6 C7 119.99(13)
C5 C6 C7 122.18(12)
O3 C7 C8 122.18(13)
O3 C7 C6 123.26(13)
C8 C7 C6 114.56(11)
O2 C8 C9 122.53(13)
O2 C8 C7 116.17(11)
C9 C8 C7 121.30(12)
C8 C9 O1 122.52(13)
C8 C9 C10 125.45(12)
O1 C9 C10 112.02(11)
N1 C10 C11 122.20(13)
N1 C10 C9 115.31(11)
C11 C10 C9 122.48(12)
C12 C11 C10 118.46(13)
C11 C12 C13 119.27(13)
C12 C13 C14 119.06(13)
N1 C14 C13 122.58(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3673(17)
O1 C9 1.3719(16)
O2 C8 1.3505(16)
O3 C7 1.2315(16)
N1 C14 1.3351(17)
N1 C10 1.3521(17)
C1 C2 1.3905(19)
C1 C6 1.3927(19)
C2 C3 1.3747(19)
C3 C4 1.399(2)
C4 C5 1.370(2)
C5 C6 1.4054(19)
C6 C7 1.465(2)
C7 C8 1.463(2)
C8 C9 1.3598(19)
C9 C10 1.462(2)
C10 C11 1.3955(19)
C11 C12 1.3814(19)
C12 C13 1.383(2)
C13 C14 1.384(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 136494865
