#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:37:56 +0100 (Tue 04 de Mar de 2025) $
#$Revision: 298172 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/98/7249867.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_7249867
loop_
_publ_author_name
'Ravi, Sasikala'
'Priyadharsan, R. Rameshbabu'
'Karthikeyan, Subramanian'
'Pannipara, Mehboobali'
'Al-Sehemi, Abdullah G.'
'Moon, Dohyun'
'Anthony, Savarimuthu Philip'
_publ_section_title
;
 Crystallization solvent-induced fluorescence tuning by subtle
 conformational change in a conformationally flexible fluorophore
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1420
_journal_page_last               1426
_journal_paper_doi               10.1039/D4CE01197J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-11-28 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.71(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.005(2)
_cell_length_b                   11.349(2)
_cell_length_c                   10.792(2)
_cell_measurement_reflns_used    42895
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      30.000
_cell_measurement_theta_min      0.361
_cell_volume                     1439.8(5)
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_collection
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Rayonix SX165 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.630
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14776
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        22.210
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.536
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.119(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0447
_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)+(0.0611P)²+0.2816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3346
_reflns_number_total             3948
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01197j2.cif
_cod_data_source_block           SPA992
_cod_depositor_comments
'Adding full bibliography for 7249862--7249868.cif.'
_cod_original_cell_volume        1439.7(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249867
_shelx_shelxl_version_number     2019/3
_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   0.991
_shelx_estimated_absorpt_t_max   0.995
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.01459(8) 0.27112(8) 0.39773(12) 0.0541(3) Uani 1 1 d . . . . .
N1 N 0.31032(7) 0.74110(7) 0.54952(10) 0.0343(2) Uani 1 1 d . . . . .
C1 C 0.28406(8) 0.85782(8) 0.50486(10) 0.0289(2) Uani 1 1 d . . . . .
C2 C 0.18036(9) 0.90748(9) 0.51318(11) 0.0339(2) Uani 1 1 d . . . . .
H2 H 0.127742 0.864404 0.548732 0.041 Uiso 1 1 calc R U . . .
C3 C 0.15459(9) 1.02057(10) 0.46899(12) 0.0371(3) Uani 1 1 d . . . . .
H3 H 0.083990 1.053945 0.474031 0.045 Uiso 1 1 calc R U . . .
C4 C 0.23132(10) 1.08470(9) 0.41772(11) 0.0380(3) Uani 1 1 d . . . . .
H4 H 0.213178 1.161439 0.387456 0.046 Uiso 1 1 calc R U . . .
C5 C 0.33496(10) 1.03574(10) 0.41099(12) 0.0394(3) Uani 1 1 d . . . . .
H5 H 0.387970 1.079820 0.377102 0.047 Uiso 1 1 calc R U . . .
C6 C 0.36161(9) 0.92238(10) 0.45364(11) 0.0346(2) Uani 1 1 d . . . . .
H6 H 0.432135 0.889208 0.447911 0.042 Uiso 1 1 calc R U . . .
C7 C 0.41795(8) 0.72048(9) 0.62910(10) 0.0298(2) Uani 1 1 d . . . . .
C8 C 0.48851(10) 0.63328(10) 0.59962(13) 0.0399(3) Uani 1 1 d . . . . .
H8 H 0.463804 0.585564 0.528124 0.048 Uiso 1 1 calc R U . . .
C9 C 0.59497(10) 0.61562(12) 0.67425(15) 0.0486(3) Uani 1 1 d . . . . .
H9 H 0.642252 0.555863 0.653550 0.058 Uiso 1 1 calc R U . . .
C10 C 0.63199(10) 0.68500(13) 0.77853(13) 0.0495(3) Uani 1 1 d . . . . .
H10 H 0.704585 0.673188 0.829272 0.059 Uiso 1 1 calc R U . . .
C11 C 0.56224(11) 0.77177(14) 0.80821(12) 0.0492(3) Uani 1 1 d . . . . .
H11 H 0.587475 0.819419 0.879644 0.059 Uiso 1 1 calc R U . . .
C12 C 0.45488(10) 0.79004(11) 0.73403(12) 0.0398(3) Uani 1 1 d . . . . .
H12 H 0.407603 0.849552 0.755265 0.048 Uiso 1 1 calc R U . . .
C13 C 0.24009(8) 0.64773(8) 0.49919(10) 0.0291(2) Uani 1 1 d . . . . .
C14 C 0.23796(9) 0.54439(9) 0.56968(11) 0.0336(2) Uani 1 1 d . . . . .
H14 H 0.284641 0.537839 0.650606 0.040 Uiso 1 1 calc R U . . .
C15 C 0.16802(9) 0.45265(9) 0.52114(12) 0.0343(2) Uani 1 1 d . . . . .
H15 H 0.167575 0.383514 0.569003 0.041 Uiso 1 1 calc R U . . .
C16 C 0.09797(9) 0.46090(9) 0.40213(11) 0.0331(2) Uani 1 1 d . . . . .
C17 C 0.09971(9) 0.56362(9) 0.33314(11) 0.0355(2) Uani 1 1 d . . . . .
H17 H 0.051819 0.570430 0.252941 0.043 Uiso 1 1 calc R U . . .
C18 C 0.17032(9) 0.65591(9) 0.37991(11) 0.0338(2) Uani 1 1 d . . . . .
H18 H 0.171303 0.724383 0.331148 0.041 Uiso 1 1 calc R U . . .
C19 C 0.02154(10) 0.36581(10) 0.34892(14) 0.0437(3) Uani 1 1 d . . . . .
H19 H -0.026443 0.379342 0.269868 0.052 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 '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
_geom_angle_publ_flag
C13 N1 C7 121.01(8) . . ?
C13 N1 C1 120.06(8) . . ?
C7 N1 C1 118.08(8) . . ?
C6 C1 C2 119.75(10) . . ?
C6 C1 N1 120.47(9) . . ?
C2 C1 N1 119.78(9) . . ?
C3 C2 C1 119.75(10) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.60(10) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.56(10) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.56(10) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.77(10) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C12 C7 C8 119.33(10) . . ?
C12 C7 N1 120.31(10) . . ?
C8 C7 N1 120.31(10) . . ?
C9 C8 C7 120.55(12) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.20(13) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.49(11) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.79(12) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 119.65(12) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C18 C13 N1 120.91(9) . . ?
C18 C13 C14 119.01(9) . . ?
N1 C13 C14 120.08(10) . . ?
C15 C14 C13 120.33(10) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.70(10) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 118.78(9) . . ?
C17 C16 C19 119.24(11) . . ?
C15 C16 C19 121.97(10) . . ?
C18 C17 C16 121.21(11) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 119.96(10) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O1 C19 C16 125.54(13) . . ?
O1 C19 H19 117.2 . . ?
C16 C19 H19 117.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.2072(15) . ?
N1 C13 1.3938(13) . ?
N1 C7 1.4182(13) . ?
N1 C1 1.4230(13) . ?
C1 C6 1.3850(15) . ?
C1 C2 1.3859(14) . ?
C2 C3 1.3822(15) . ?
C2 H2 0.9400 . ?
C3 C4 1.3753(17) . ?
C3 H3 0.9400 . ?
C4 C5 1.3779(17) . ?
C4 H4 0.9400 . ?
C5 C6 1.3818(16) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.3778(16) . ?
C7 C8 1.3811(15) . ?
C8 C9 1.3800(17) . ?
C8 H8 0.9400 . ?
C9 C10 1.371(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.372(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.3878(18) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.3890(16) . ?
C13 C14 1.4010(14) . ?
C14 C15 1.3728(15) . ?
C14 H14 0.9400 . ?
C15 C16 1.3882(17) . ?
C15 H15 0.9400 . ?
C16 C17 1.3856(15) . ?
C16 C19 1.4568(15) . ?
C17 C18 1.3772(14) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O1 0.94 2.45 3.3799(15) 168.5 3_566 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C1 C6 -121.98(12) . . . . ?
C7 N1 C1 C6 47.55(15) . . . . ?
C13 N1 C1 C2 58.31(15) . . . . ?
C7 N1 C1 C2 -132.16(11) . . . . ?
C6 C1 C2 C3 0.73(17) . . . . ?
N1 C1 C2 C3 -179.56(10) . . . . ?
C1 C2 C3 C4 -0.52(18) . . . . ?
C2 C3 C4 C5 -0.30(18) . . . . ?
C3 C4 C5 C6 0.91(18) . . . . ?
C4 C5 C6 C1 -0.70(18) . . . . ?
C2 C1 C6 C5 -0.12(17) . . . . ?
N1 C1 C6 C5 -179.83(10) . . . . ?
C13 N1 C7 C12 -139.68(11) . . . . ?
C1 N1 C7 C12 50.90(15) . . . . ?
C13 N1 C7 C8 42.70(16) . . . . ?
C1 N1 C7 C8 -126.73(12) . . . . ?
C12 C7 C8 C9 0.03(18) . . . . ?
N1 C7 C8 C9 177.68(11) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C8 C7 C12 C11 0.17(18) . . . . ?
N1 C7 C12 C11 -177.48(11) . . . . ?
C10 C11 C12 C7 -0.19(19) . . . . ?
C7 N1 C13 C18 -146.25(11) . . . . ?
C1 N1 C13 C18 22.97(16) . . . . ?
C7 N1 C13 C14 34.63(16) . . . . ?
C1 N1 C13 C14 -156.15(10) . . . . ?
C18 C13 C14 C15 0.15(17) . . . . ?
N1 C13 C14 C15 179.28(10) . . . . ?
C13 C14 C15 C16 -0.38(17) . . . . ?
C14 C15 C16 C17 -0.11(17) . . . . ?
C14 C15 C16 C19 -179.01(11) . . . . ?
C15 C16 C17 C18 0.85(17) . . . . ?
C19 C16 C17 C18 179.78(11) . . . . ?
C16 C17 C18 C13 -1.09(18) . . . . ?
N1 C13 C18 C17 -178.55(10) . . . . ?
C14 C13 C18 C17 0.58(17) . . . . ?
C17 C16 C19 O1 177.64(13) . . . . ?
C15 C16 C19 O1 -3.5(2) . . . . ?
