#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:07:39 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286160 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/26/7062600.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_7062600
loop_
_publ_author_name
'Kumar M, Naveen'
'Lyngkhoi, Deikrisha Lyngdoh'
'Gaikwad, Sudhakar'
'Samanta, Debabrata'
'Khatua, Snehadrinarayan'
'Pramanik, Susnata'
_publ_section_title
;
 The effect of substituents on the aggregation-induced emission of
 9,10-phenanthraquinone-hydrazones
;
_journal_issue                   32
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15066
_journal_page_last               15075
_journal_paper_doi               10.1039/D3NJ02198J
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33
_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
;
2023-07-08 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.468(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1687(11)
_cell_length_b                   15.6842(10)
_cell_length_c                   6.4380(4)
_cell_measurement_reflns_used    3485
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      30.662
_cell_measurement_theta_min      2.937
_cell_volume                     1501.08(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon III detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            32645
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.937
_diffrn_source                   'I\^A?S DIAMOND microfocus Mo tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0511
_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)+(0.0364P)²+0.5758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2103
_reflns_number_total             2622
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj02198j2.cif
_cod_data_source_block           compound1
_cod_depositor_comments
'Adding full bibliography for 7062600--7062602.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7062600
_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   0.980
_shelx_estimated_absorpt_t_max   0.989
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
C1 C 0.77219(14) 0.58099(11) 0.1998(3) 0.0477(5) Uani 1 1 d . . . . .
C2 C 0.84276(16) 0.62126(13) 0.1339(3) 0.0595(6) Uani 1 1 d . . . . .
H2 H 0.900906 0.616099 0.212907 0.071 Uiso 1 1 calc R U . . .
C3 C 0.82685(18) 0.66914(14) -0.0492(4) 0.0697(7) Uani 1 1 d . . . . .
H3 H 0.874365 0.696547 -0.093056 0.084 Uiso 1 1 calc R U . . .
C4 C 0.74133(19) 0.67659(15) -0.1671(4) 0.0737(7) Uani 1 1 d . . . . .
H4 H 0.730604 0.709212 -0.290228 0.088 Uiso 1 1 calc R U . . .
C5 C 0.67175(18) 0.63548(15) -0.1019(3) 0.0703(7) Uani 1 1 d . . . . .
H5 H 0.613834 0.640158 -0.182423 0.084 Uiso 1 1 calc R U . . .
C6 C 0.68624(15) 0.58727(13) 0.0813(3) 0.0577(5) Uani 1 1 d . . . . .
H6 H 0.638662 0.559488 0.123960 0.069 Uiso 1 1 calc R U . . .
C7 C 0.74667(12) 0.45258(11) 0.6415(3) 0.0423(4) Uani 1 1 d . . . . .
C8 C 0.83663(13) 0.44590(11) 0.7674(3) 0.0438(4) Uani 1 1 d . . . . .
C9 C 0.84916(12) 0.40077(11) 0.9711(3) 0.0421(4) Uani 1 1 d . . . . .
C10 C 0.93543(13) 0.39687(12) 1.0967(3) 0.0513(5) Uani 1 1 d . . . . .
H10 H 0.983272 0.422074 1.049098 0.062 Uiso 1 1 calc R U . . .
C11 C 0.95049(14) 0.35645(13) 1.2888(3) 0.0575(5) Uani 1 1 d . . . . .
H11 H 1.008203 0.354137 1.371290 0.069 Uiso 1 1 calc R U . . .
C12 C 0.87932(14) 0.31907(12) 1.3595(3) 0.0546(5) Uani 1 1 d . . . . .
H12 H 0.889296 0.291560 1.490051 0.066 Uiso 1 1 calc R U . . .
C13 C 0.79417(13) 0.32230(11) 1.2384(3) 0.0480(5) Uani 1 1 d . . . . .
H13 H 0.747182 0.296606 1.288308 0.058 Uiso 1 1 calc R U . . .
C14 C 0.77612(12) 0.36337(10) 1.0411(3) 0.0415(4) Uani 1 1 d . . . . .
C15 C 0.68534(12) 0.36720(11) 0.9076(3) 0.0426(4) Uani 1 1 d . . . . .
C16 C 0.61182(13) 0.32702(12) 0.9674(3) 0.0547(5) Uani 1 1 d . . . . .
H16 H 0.620537 0.297036 1.094472 0.066 Uiso 1 1 calc R U . . .
C17 C 0.52720(14) 0.33078(14) 0.8430(4) 0.0633(6) Uani 1 1 d . . . . .
H17 H 0.479306 0.303835 0.886392 0.076 Uiso 1 1 calc R U . . .
C18 C 0.51336(14) 0.37464(14) 0.6536(4) 0.0631(6) Uani 1 1 d . . . . .
H18 H 0.455937 0.377866 0.569893 0.076 Uiso 1 1 calc R U . . .
C19 C 0.58429(13) 0.41351(13) 0.5885(3) 0.0553(5) Uani 1 1 d . . . . .
H19 H 0.574456 0.442090 0.459406 0.066 Uiso 1 1 calc R U . . .
C20 C 0.67100(12) 0.41093(11) 0.7127(3) 0.0434(4) Uani 1 1 d . . . . .
N1 N 0.79134(11) 0.53349(10) 0.3882(2) 0.0502(4) Uani 1 1 d . . . . .
H1 H 0.846019 0.528808 0.455970 0.060 Uiso 1 1 calc R U . . .
N2 N 0.72621(10) 0.49608(9) 0.4620(2) 0.0463(4) Uani 1 1 d . . . . .
O1 O 0.90291(9) 0.47785(9) 0.7076(2) 0.0602(4) 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
_geom_angle_publ_flag
C6 C1 C2 120.23(18) . . ?
C6 C1 N1 121.82(17) . . ?
C2 C1 N1 117.95(19) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N2 C7 C8 123.89(16) . . ?
N2 C7 C20 116.00(17) . . ?
C8 C7 C20 120.10(15) . . ?
O1 C8 C7 121.70(16) . . ?
O1 C8 C9 119.92(17) . . ?
C7 C8 C9 118.38(15) . . ?
C10 C9 C14 120.29(16) . . ?
C10 C9 C8 118.56(16) . . ?
C14 C9 C8 121.15(17) . . ?
C11 C10 C9 120.84(18) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.55(19) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.41(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.65(17) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C9 117.27(17) . . ?
C13 C14 C15 122.61(16) . . ?
C9 C14 C15 120.12(15) . . ?
C16 C15 C20 118.28(18) . . ?
C16 C15 C14 121.67(16) . . ?
C20 C15 C14 120.04(16) . . ?
C17 C16 C15 121.61(18) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 119.83(19) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 121.23(19) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 119.00(17) . . ?
C19 C20 C7 120.88(16) . . ?
C15 C20 C7 120.12(17) . . ?
N2 N1 C1 120.48(17) . . ?
N2 N1 H1 119.8 . . ?
C1 N1 H1 119.8 . . ?
N1 N2 C7 118.81(16) . . ?
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
C1 C6 1.377(3) . ?
C1 C2 1.380(3) . ?
C1 N1 1.404(2) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.325(2) . ?
C7 C8 1.446(3) . ?
C7 C20 1.471(2) . ?
C8 O1 1.251(2) . ?
C8 C9 1.469(2) . ?
C9 C10 1.396(3) . ?
C9 C14 1.405(2) . ?
C10 C11 1.368(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.402(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.472(3) . ?
C15 C16 1.400(2) . ?
C15 C20 1.409(2) . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.397(3) . ?
C19 H19 0.9300 . ?
N1 N2 1.316(2) . ?
N1 H1 0.8600 . ?
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
N1 H1 O1 0.86 1.86 2.543(2) 135.5 . 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
C6 C1 C2 C3 1.1(3) . . . . ?
N1 C1 C2 C3 -179.45(17) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
N1 C1 C6 C5 179.57(17) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
N2 C7 C8 O1 -3.8(3) . . . . ?
C20 C7 C8 O1 177.30(16) . . . . ?
N2 C7 C8 C9 175.67(15) . . . . ?
C20 C7 C8 C9 -3.2(2) . . . . ?
O1 C8 C9 C10 1.8(2) . . . . ?
C7 C8 C9 C10 -177.69(16) . . . . ?
O1 C8 C9 C14 -179.22(16) . . . . ?
C7 C8 C9 C14 1.3(2) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
C8 C9 C10 C11 179.25(17) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C9 0.5(3) . . . . ?
C12 C13 C14 C15 179.61(17) . . . . ?
C10 C9 C14 C13 -0.5(2) . . . . ?
C8 C9 C14 C13 -179.41(15) . . . . ?
C10 C9 C14 C15 -179.65(16) . . . . ?
C8 C9 C14 C15 1.4(2) . . . . ?
C13 C14 C15 C16 -2.4(3) . . . . ?
C9 C14 C15 C16 176.77(16) . . . . ?
C13 C14 C15 C20 178.69(16) . . . . ?
C9 C14 C15 C20 -2.2(2) . . . . ?
C20 C15 C16 C17 -1.2(3) . . . . ?
C14 C15 C16 C17 179.87(18) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C18 C19 C20 C15 0.2(3) . . . . ?
C18 C19 C20 C7 179.86(18) . . . . ?
C16 C15 C20 C19 0.9(3) . . . . ?
C14 C15 C20 C19 179.84(16) . . . . ?
C16 C15 C20 C7 -178.76(16) . . . . ?
C14 C15 C20 C7 0.2(2) . . . . ?
N2 C7 C20 C19 3.9(2) . . . . ?
C8 C7 C20 C19 -177.12(17) . . . . ?
N2 C7 C20 C15 -176.47(15) . . . . ?
C8 C7 C20 C15 2.5(2) . . . . ?
C6 C1 N1 N2 -2.8(3) . . . . ?
C2 C1 N1 N2 177.79(16) . . . . ?
C1 N1 N2 C7 -179.25(15) . . . . ?
C8 C7 N2 N1 2.3(2) . . . . ?
C20 C7 N2 N1 -178.78(15) . . . . ?
