#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:22:40 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281464 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/60/7246006.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_7246006
loop_
_publ_author_name
'Gayathri, Parthasarathy'
'Ravi, Sasikala'
'Karthikeyan, Subramanian'
'Pannipara, Mehboobali'
'Al-Sehemi, Abdullah G.'
'Moon, Dohyun'
'Anthony, Savarimuthu Philip'
_publ_section_title
;
 Hexagon and network structured organic geometrical isomers with distinct
 intramolecular H-bonding and stimuli-induced self-reversible fluorescence
 switching
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              460
_journal_page_last               466
_journal_paper_doi               10.1039/D2CE01361D
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35
_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-2018/3
_audit_update_record
;
2022-09-13 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.15(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3490(17)
_cell_length_b                   16.722(3)
_cell_length_c                   11.913(2)
_cell_measurement_reflns_used    54663
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      33.548
_cell_measurement_theta_min      0.361
_cell_volume                     1656.5(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.630
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15431
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        22.210
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.865
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.062
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0545
_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)+(0.0856P)²+0.3546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1594
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3730
_reflns_number_total             4182
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01361d2.cif
_cod_data_source_block           SPA711
_cod_depositor_comments
'Adding full bibliography for 7246005--7246006.cif.'
_cod_original_cell_volume        1656.5(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7246006
_shelx_shelxl_version_number     2018/3
_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   0.996
_shelx_estimated_absorpt_t_max   0.996
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 0.33516(13) 0.26933(7) 0.48481(8) 0.0435(3) Uani 1 1 d . . . . .
H1 H 0.281074 0.276240 0.539151 0.065 Uiso 1 1 calc R U . . .
O2 O -0.02170(12) 0.63311(5) 0.66624(9) 0.0400(3) Uani 1 1 d . . . . .
H2O2 H -0.093844 0.646509 0.706023 0.060 Uiso 1 1 calc R U . . .
N1 N 0.26730(13) 0.19503(6) 0.71850(9) 0.0286(2) Uani 1 1 d . . . . .
N2 N 0.24420(13) 0.27529(6) 0.68654(9) 0.0304(2) Uani 1 1 d . . . . .
C1 C 0.48484(16) 0.24538(7) 0.52259(10) 0.0308(3) Uani 1 1 d . . . . .
C2 C 0.6121(2) 0.27121(8) 0.46289(12) 0.0412(3) Uani 1 1 d . . . . .
H2 H 0.590197 0.303845 0.399098 0.049 Uiso 1 1 calc R U . . .
C3 C 0.7677(2) 0.25001(10) 0.49533(14) 0.0482(4) Uani 1 1 d . . . . .
H3 H 0.851580 0.268582 0.454599 0.058 Uiso 1 1 calc R U . . .
C4 C 0.80134(19) 0.20107(11) 0.58842(14) 0.0495(4) Uani 1 1 d . . . . .
H4 H 0.908150 0.187031 0.611870 0.059 Uiso 1 1 calc R U . . .
C5 C 0.67645(17) 0.17303(9) 0.64656(12) 0.0391(3) Uani 1 1 d . . . . .
H5 H 0.699766 0.138520 0.708148 0.047 Uiso 1 1 calc R U . . .
C6 C 0.51667(15) 0.19459(7) 0.61627(9) 0.0277(3) Uani 1 1 d . . . . .
C7 C 0.39149(14) 0.15989(7) 0.68378(9) 0.0268(2) Uani 1 1 d . . . . .
C8 C 0.40938(16) 0.07472(7) 0.71908(10) 0.0301(3) Uani 1 1 d . . . . .
C9 C 0.4357(3) 0.01715(8) 0.63920(13) 0.0558(5) Uani 1 1 d . . . . .
H9 H 0.454066 0.032862 0.565684 0.067 Uiso 1 1 calc R U . . .
C10 C 0.4353(3) -0.06343(9) 0.66662(16) 0.0636(6) Uani 1 1 d . . . . .
H10 H 0.450010 -0.102103 0.611210 0.076 Uiso 1 1 calc R U . . .
C11 C 0.4132(2) -0.08692(8) 0.77535(14) 0.0476(4) Uani 1 1 d . . . . .
H11 H 0.413577 -0.141497 0.794245 0.057 Uiso 1 1 calc R U . . .
C12 C 0.39051(17) -0.02994(8) 0.85592(12) 0.0377(3) Uani 1 1 d . . . . .
H12 H 0.377298 -0.045834 0.930215 0.045 Uiso 1 1 calc R U . . .
C13 C 0.38701(15) 0.05069(7) 0.82840(10) 0.0305(3) Uani 1 1 d . . . . .
H13 H 0.369530 0.089092 0.883615 0.037 Uiso 1 1 calc R U . . .
C14 C 0.16794(15) 0.31679(7) 0.75490(11) 0.0318(3) Uani 1 1 d . . . . .
H14 H 0.138219 0.292542 0.821126 0.038 Uiso 1 1 calc R U . . .
C15 C 0.12593(15) 0.40004(7) 0.73342(11) 0.0318(3) Uani 1 1 d . . . . .
C16 C 0.16929(17) 0.44123(8) 0.63838(12) 0.0380(3) Uani 1 1 d . . . . .
H16 H 0.232053 0.415485 0.587549 0.046 Uiso 1 1 calc R U . . .
C17 C 0.12084(17) 0.51913(8) 0.61863(12) 0.0377(3) Uani 1 1 d . . . . .
H17 H 0.151213 0.546342 0.554830 0.045 Uiso 1 1 calc R U . . .
C18 C 0.02685(14) 0.55766(7) 0.69314(11) 0.0311(3) Uani 1 1 d . . . . .
C19 C -0.01222(17) 0.51868(8) 0.78998(11) 0.0353(3) Uani 1 1 d . . . . .
H19 H -0.071475 0.545332 0.842068 0.042 Uiso 1 1 calc R U . . .
C20 C 0.03663(17) 0.44025(8) 0.80943(11) 0.0356(3) Uani 1 1 d . . . . .
H20 H 0.009262 0.413813 0.874669 0.043 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
C1 O1 H1 109.5 . . ?
C18 O2 H2O2 109.5 . . ?
C7 N1 N2 116.28(9) . . ?
C14 N2 N1 114.15(10) . . ?
O1 C1 C2 117.46(11) . . ?
O1 C1 C6 123.09(12) . . ?
C2 C1 C6 119.42(12) . . ?
C3 C2 C1 121.43(13) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.86(13) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.50(14) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.86(13) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 117.90(11) . . ?
C5 C6 C7 117.32(11) . . ?
C1 C6 C7 124.75(11) . . ?
N1 C7 C8 114.06(10) . . ?
N1 C7 C6 128.09(10) . . ?
C8 C7 C6 117.84(10) . . ?
C9 C8 C13 119.03(11) . . ?
C9 C8 C7 119.27(11) . . ?
C13 C8 C7 121.48(10) . . ?
C8 C9 C10 120.64(13) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.03(14) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 119.67(13) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.58(12) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.01(12) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
N2 C14 C15 122.19(11) . . ?
N2 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C20 C15 C16 118.65(11) . . ?
C20 C15 C14 118.81(11) . . ?
C16 C15 C14 122.54(11) . . ?
C17 C16 C15 120.65(12) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.10(12) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
O2 C18 C19 123.08(11) . . ?
O2 C18 C17 116.95(11) . . ?
C19 C18 C17 119.97(11) . . ?
C20 C19 C18 119.67(11) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C15 120.88(12) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
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 C1 1.3504(17) . ?
O1 H1 0.8300 . ?
O2 C18 1.3549(15) . ?
O2 H2O2 0.8300 . ?
N1 C7 1.2917(15) . ?
N1 N2 1.4038(13) . ?
N2 C14 1.2819(16) . ?
C1 C2 1.3987(19) . ?
C1 C6 1.4086(16) . ?
C2 C3 1.369(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.3844(19) . ?
C4 H4 0.9400 . ?
C5 C6 1.3976(19) . ?
C5 H5 0.9400 . ?
C6 C7 1.4923(16) . ?
C7 C8 1.4887(15) . ?
C8 C9 1.3850(17) . ?
C8 C13 1.3915(16) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.377(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.3872(17) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C14 C15 1.4528(16) . ?
C14 H14 0.9400 . ?
C15 C20 1.3961(17) . ?
C15 C16 1.4004(18) . ?
C16 C17 1.3780(18) . ?
C16 H16 0.9400 . ?
C17 C18 1.3942(18) . ?
C17 H17 0.9400 . ?
C18 C19 1.3892(18) . ?
C19 C20 1.3866(18) . ?
C19 H19 0.9400 . ?
C20 H20 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
O1 H1 N1 0.83 2.54 3.1462(15) 130.5 . yes
O1 H1 N2 0.83 1.81 2.5865(15) 155.2 . yes
O2 H2O2 N1 0.83 1.95 2.7691(15) 169.5 2_556 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
C7 N1 N2 C14 -152.74(12) . . . . ?
O1 C1 C2 C3 179.83(14) . . . . ?
C6 C1 C2 C3 -1.8(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -2.0(3) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C5 C6 C7 179.13(14) . . . . ?
O1 C1 C6 C5 179.17(12) . . . . ?
C2 C1 C6 C5 0.92(18) . . . . ?
O1 C1 C6 C7 1.16(19) . . . . ?
C2 C1 C6 C7 -177.09(11) . . . . ?
N2 N1 C7 C8 -179.43(10) . . . . ?
N2 N1 C7 C6 1.83(18) . . . . ?
C5 C6 C7 N1 138.85(14) . . . . ?
C1 C6 C7 N1 -43.13(19) . . . . ?
C5 C6 C7 C8 -39.84(15) . . . . ?
C1 C6 C7 C8 138.18(12) . . . . ?
N1 C7 C8 C9 130.60(16) . . . . ?
C6 C7 C8 C9 -50.52(19) . . . . ?
N1 C7 C8 C13 -43.98(17) . . . . ?
C6 C7 C8 C13 134.90(13) . . . . ?
C13 C8 C9 C10 1.8(3) . . . . ?
C7 C8 C9 C10 -172.87(18) . . . . ?
C8 C9 C10 C11 -1.9(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C11 C12 C13 C8 -1.2(2) . . . . ?
C9 C8 C13 C12 -0.3(2) . . . . ?
C7 C8 C13 C12 174.29(12) . . . . ?
N1 N2 C14 C15 -177.05(11) . . . . ?
N2 C14 C15 C20 177.22(13) . . . . ?
N2 C14 C15 C16 -1.7(2) . . . . ?
C20 C15 C16 C17 -1.8(2) . . . . ?
C14 C15 C16 C17 177.09(13) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 O2 -177.49(13) . . . . ?
C16 C17 C18 C19 2.8(2) . . . . ?
O2 C18 C19 C20 177.44(13) . . . . ?
C17 C18 C19 C20 -2.9(2) . . . . ?
C18 C19 C20 C15 0.6(2) . . . . ?
C16 C15 C20 C19 1.8(2) . . . . ?
C14 C15 C20 C19 -177.21(13) . . . . ?
