#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/38/7233886.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_7233886
loop_
_publ_author_name
'Kunchala Dhanunjayarao'
'Vanga Mukundam'
'Krishnan Venkatasubbaiah'
_publ_section_title
;
 A highly selective ratiometric detection of F- based on excited-state
 intramolecular proton-transfer (imidazole) materials
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              8599
_journal_page_last               8606
_journal_paper_doi               10.1039/C4TC01711K
_journal_volume                  2
_journal_year                    2014
_chemical_formula_moiety         'C28 H22 N2 O'
_chemical_formula_sum            'C28 H22 N2 O'
_chemical_formula_weight         402.48
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                89.314(2)
_cell_angle_beta                 76.447(2)
_cell_angle_gamma                86.532(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0790(3)
_cell_length_b                   10.2068(3)
_cell_length_c                   10.6405(3)
_cell_measurement_reflns_used    1932
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.53
_cell_measurement_theta_min      2.51
_cell_volume                     1062.20(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18495
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         6183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1240
_refine_ls_R_factor_gt           0.0608
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0950P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1882
_reflns_number_gt                3231
_reflns_number_total             6183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000002.cif
_cod_data_source_block           PCOD1000002
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7233886
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C16 C 0.0046(2) 1.0287(2) 0.2963(2) 0.0718(7) Uani 1 1 d . . .
H16A H 0.0339 1.0330 0.2039 0.108 Uiso 1 1 calc R . .
H16B H -0.0152 1.1159 0.3311 0.108 Uiso 1 1 calc R . .
H16C H -0.0761 0.9801 0.3197 0.108 Uiso 1 1 calc R . .
N2 N 0.45477(14) 0.76758(14) 0.45698(14) 0.0386(4) Uani 1 1 d . . .
N1 N 0.66546(15) 0.68037(14) 0.42740(14) 0.0422(4) Uani 1 1 d . . .
O1 O 0.84781(14) 0.69358(17) 0.21604(15) 0.0687(5) Uani 1 1 d . . .
H1 H 0.8144 0.6736 0.2912 0.103 Uiso 1 1 calc R . .
C13 C 0.11639(19) 0.96134(19) 0.35017(18) 0.0479(5) Uani 1 1 d . . .
C12 C 0.1245(2) 0.8264(2) 0.3645(2) 0.0527(5) Uani 1 1 d . . .
H12 H 0.0564 0.7776 0.3459 0.063 Uiso 1 1 calc R . .
C11 C 0.23161(19) 0.76253(17) 0.40587(19) 0.0464(5) Uani 1 1 d . . .
H11 H 0.2352 0.6718 0.4155 0.056 Uiso 1 1 calc R . .
C10 C 0.33282(16) 0.83454(16) 0.43261(16) 0.0368(4) Uani 1 1 d . . .
C3 C 0.46978(18) 0.72111(16) 0.57699(17) 0.0388(4) Uani 1 1 d . . .
C2 C 0.60133(18) 0.66704(16) 0.55604(17) 0.0400(4) Uani 1 1 d . . .
C23 C 0.67818(19) 0.60481(16) 0.64557(17) 0.0419(4) Uani 1 1 d . . .
C28 C 0.6154(2) 0.54673(19) 0.76117(19) 0.0529(5) Uani 1 1 d . . .
H28 H 0.5205 0.5466 0.7855 0.063 Uiso 1 1 calc R . .
C27 C 0.6938(3) 0.4887(2) 0.8408(2) 0.0626(6) Uani 1 1 d . . .
H27 H 0.6508 0.4507 0.9184 0.075 Uiso 1 1 calc R . .
C26 C 0.8338(3) 0.4872(2) 0.8059(2) 0.0620(6) Uani 1 1 d . . .
H26 H 0.8855 0.4479 0.8594 0.074 Uiso 1 1 calc R . .
C14 C 0.2159(2) 1.03126(19) 0.3851(2) 0.0509(5) Uani 1 1 d . . .
H14 H 0.2102 1.1224 0.3805 0.061 Uiso 1 1 calc R . .
C15 C 0.32303(19) 0.96906(17) 0.42652(18) 0.0437(4) Uani 1 1 d . . .
H15 H 0.3883 1.0179 0.4502 0.052 Uiso 1 1 calc R . .
C1 C 0.57607(17) 0.73923(16) 0.36838(17) 0.0389(4) Uani 1 1 d . . .
C25 C 0.8970(2) 0.54379(19) 0.6922(2) 0.0571(6) Uani 1 1 d . . .
H25 H 0.9919 0.5434 0.6685 0.068 Uiso 1 1 calc R . .
C24 C 0.8201(2) 0.60160(17) 0.6123(2) 0.0490(5) Uani 1 1 d . . .
H24 H 0.8642 0.6391 0.5349 0.059 Uiso 1 1 calc R . .
C4 C 0.36044(18) 0.73919(17) 0.69592(17) 0.0387(4) Uani 1 1 d . . .
C5 C 0.2737(2) 0.64028(19) 0.7423(2) 0.0543(5) Uani 1 1 d . . .
H5 H 0.2801 0.5633 0.6949 0.065 Uiso 1 1 calc R . .
C6 C 0.1780(2) 0.6548(2) 0.8579(2) 0.0643(6) Uani 1 1 d . . .
H6 H 0.1213 0.5872 0.8886 0.077 Uiso 1 1 calc R . .
C7 C 0.1659(2) 0.7684(2) 0.9281(2) 0.0602(6) Uani 1 1 d . . .
H7 H 0.1023 0.7774 1.0068 0.072 Uiso 1 1 calc R . .
C8 C 0.2481(2) 0.8686(2) 0.8817(2) 0.0611(6) Uani 1 1 d . . .
H8 H 0.2387 0.9465 0.9282 0.073 Uiso 1 1 calc R . .
C9 C 0.3446(2) 0.85435(19) 0.7664(2) 0.0532(5) Uani 1 1 d . . .
H9 H 0.3997 0.9231 0.7356 0.064 Uiso 1 1 calc R . .
C17 C 0.61060(18) 0.76505(17) 0.22888(17) 0.0408(4) Uani 1 1 d . . .
C18 C 0.5167(2) 0.8086(2) 0.15813(19) 0.0572(5) Uani 1 1 d . . .
H18 H 0.4257 0.8250 0.2011 0.069 Uiso 1 1 calc R . .
C19 C 0.5540(2) 0.8282(2) 0.0267(2) 0.0637(6) Uani 1 1 d . . .
H19 H 0.4888 0.8580 -0.0176 0.076 Uiso 1 1 calc R . .
C20 C 0.6874(2) 0.8039(2) -0.0389(2) 0.0620(6) Uani 1 1 d . . .
H20 H 0.7131 0.8171 -0.1277 0.074 Uiso 1 1 calc R . .
C21 C 0.7820(2) 0.7602(2) 0.0271(2) 0.0613(6) Uani 1 1 d . . .
H21 H 0.8724 0.7440 -0.0178 0.074 Uiso 1 1 calc R . .
C22 C 0.74704(19) 0.73941(18) 0.15927(19) 0.0474(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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C13 C16 H16A 109.5 . .
C13 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C13 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C1 N2 C3 107.79(14) . .
C1 N2 C10 126.91(14) . .
C3 N2 C10 125.30(14) . .
C1 N1 C2 107.77(14) . .
C22 O1 H1 109.5 . .
C12 C13 C14 117.53(17) . .
C12 C13 C16 120.87(19) . .
C14 C13 C16 121.59(19) . .
C13 C12 C11 121.44(18) . .
C13 C12 H12 119.3 . .
C11 C12 H12 119.3 . .
C10 C11 C12 119.36(17) . .
C10 C11 H11 120.3 . .
C12 C11 H11 120.3 . .
C15 C10 C11 120.29(16) . .
C15 C10 N2 119.95(15) . .
C11 C10 N2 119.58(15) . .
C2 C3 N2 105.63(15) . .
C2 C3 C4 131.81(16) . .
N2 C3 C4 122.49(15) . .
C3 C2 N1 109.29(15) . .
C3 C2 C23 131.28(17) . .
N1 C2 C23 119.41(15) . .
C28 C23 C24 117.96(17) . .
C28 C23 C2 123.10(17) . .
C24 C23 C2 118.93(17) . .
C23 C28 C27 120.3(2) . .
C23 C28 H28 119.9 . .
C27 C28 H28 119.9 . .
C26 C27 C28 120.6(2) . .
C26 C27 H27 119.7 . .
C28 C27 H27 119.7 . .
C25 C26 C27 119.72(19) . .
C25 C26 H26 120.1 . .
C27 C26 H26 120.1 . .
C15 C14 C13 121.61(17) . .
C15 C14 H14 119.2 . .
C13 C14 H14 119.2 . .
C10 C15 C14 119.55(17) . .
C10 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
N1 C1 N2 109.50(15) . .
N1 C1 C17 121.78(16) . .
N2 C1 C17 128.71(15) . .
C26 C25 C24 120.1(2) . .
C26 C25 H25 119.9 . .
C24 C25 H25 119.9 . .
C25 C24 C23 121.31(19) . .
C25 C24 H24 119.3 . .
C23 C24 H24 119.3 . .
C9 C4 C5 118.14(18) . .
C9 C4 C3 120.65(16) . .
C5 C4 C3 121.18(17) . .
C6 C5 C4 120.7(2) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C7 C6 C5 120.4(2) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C8 C7 C6 119.7(2) . .
C8 C7 H7 120.2 . .
C6 C7 H7 120.2 . .
C7 C8 C9 120.2(2) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
C8 C9 C4 120.84(19) . .
C8 C9 H9 119.6 . .
C4 C9 H9 119.6 . .
C18 C17 C22 116.90(17) . .
C18 C17 C1 124.53(17) . .
C22 C17 C1 118.53(16) . .
C19 C18 C17 122.2(2) . .
C19 C18 H18 118.9 . .
C17 C18 H18 118.9 . .
C20 C19 C18 119.9(2) . .
C20 C19 H19 120.0 . .
C18 C19 H19 120.0 . .
C21 C20 C19 119.5(2) . .
C21 C20 H20 120.2 . .
C19 C20 H20 120.2 . .
C20 C21 C22 121.6(2) . .
C20 C21 H21 119.2 . .
C22 C21 H21 119.2 . .
O1 C22 C21 117.37(18) . .
O1 C22 C17 122.82(17) . .
C21 C22 C17 119.81(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C16 C13 1.506(3) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
N2 C1 1.375(2) .
N2 C3 1.395(2) .
N2 C10 1.445(2) .
N1 C1 1.326(2) .
N1 C2 1.379(2) .
O1 C22 1.356(2) .
O1 H1 0.8200 .
C13 C12 1.383(3) .
C13 C14 1.386(3) .
C12 C11 1.384(2) .
C12 H12 0.9300 .
C11 C10 1.376(2) .
C11 H11 0.9300 .
C10 C15 1.372(2) .
C3 C2 1.374(2) .
C3 C4 1.476(2) .
C2 C23 1.477(2) .
C23 C28 1.389(3) .
C23 C24 1.389(3) .
C28 C27 1.392(3) .
C28 H28 0.9300 .
C27 C26 1.372(3) .
C27 H27 0.9300 .
C26 C25 1.368(3) .
C26 H26 0.9300 .
C14 C15 1.377(3) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C1 C17 1.468(2) .
C25 C24 1.383(3) .
C25 H25 0.9300 .
C24 H24 0.9300 .
C4 C9 1.382(3) .
C4 C5 1.386(2) .
C5 C6 1.377(3) .
C5 H5 0.9300 .
C6 C7 1.370(3) .
C6 H6 0.9300 .
C7 C8 1.368(3) .
C7 H7 0.9300 .
C8 C9 1.379(3) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C17 C18 1.391(2) .
C17 C22 1.411(3) .
C18 C19 1.376(3) .
C18 H18 0.9300 .
C19 C20 1.371(3) .
C19 H19 0.9300 .
C20 C21 1.362(3) .
C20 H20 0.9300 .
C21 C22 1.385(3) .
C21 H21 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 135869142
