#------------------------------------------------------------------------------
#$Date: 2023-01-12 03:47:35 +0200 (Thu, 12 Jan 2023) $
#$Revision: 280295 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/61/7246120.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_7246120
loop_
_publ_author_name
'Kakimoto, Yuna'
'Ikemura, Ryoya'
'Imai, Yoshitane'
'Tohnai, Norimitsu'
'Yamazaki, Shoko'
'Nakata, Eiji'
'Takashima, Hiroshi'
_publ_section_title
;
 Circularly polarised luminescence from excimer emission of anthracene
 derivatives complexed with γ-cyclodextrin in the solid state
;
_journal_issue                   3
_journal_name_full               'RSC Advances'
_journal_page_first              1914
_journal_page_last               1922
_journal_paper_doi               10.1039/D2RA07971B
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-02-03 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                111.862(2)
_cell_angle_beta                 93.627(2)
_cell_angle_gamma                103.670(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9450(2)
_cell_length_b                   9.2434(2)
_cell_length_c                   10.47923(19)
_cell_measurement_reflns_used    5739
_cell_measurement_temperature    296
_cell_measurement_theta_max      73.91
_cell_measurement_theta_min      4.60
_cell_volume                     770.29(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7062
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        74.170
_diffrn_reflns_theta_max         74.170
_diffrn_reflns_theta_min         4.612
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            pALEYELLOW
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pRISM
_exptl_crystal_F_000             324.00
_exptl_crystal_size_max          7.000
_exptl_crystal_size_mid          0.700
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.337
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3007
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1573
_reflns_number_gt                2823
_reflns_number_total             3007
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d2ra07971b2.cif
_cod_data_source_block           xcalibur_CCDC1
_cod_database_code               7246120
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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
O1 O 0.34842(9) 0.63534(10) 0.32861(9) 0.0299(2) Uani 1 1 d . . .
O2 O 0.26190(9) 0.55152(10) 0.49313(9) 0.0305(3) Uani 1 1 d . . .
O3 O 0.18172(9) 0.93212(10) 0.62931(8) 0.0310(3) Uani 1 1 d . . .
N1 N 0.01398(10) 0.68858(11) 0.49391(10) 0.0242(3) Uani 1 1 d . . .
H1 H -0.0727 0.6179 0.4841 0.029 Uiso 1 1 calc R . .
C1 C -0.22628(13) 0.91361(14) 0.62937(13) 0.0284(3) Uani 1 1 d . . .
H1A H -0.1709 0.9178 0.5581 0.034 Uiso 1 1 calc R . .
C2 C -0.36291(14) 0.95419(15) 0.63479(15) 0.0356(3) Uani 1 1 d . . .
H2 H -0.3991 0.9870 0.5678 0.043 Uiso 1 1 calc R . .
C3 C -0.45104(14) 0.94720(16) 0.74123(16) 0.0386(3) Uani 1 1 d . . .
H3 H -0.5456 0.9728 0.7424 0.046 Uiso 1 1 calc R . .
C4 C -0.39757(14) 0.90320(15) 0.84156(14) 0.0339(3) Uani 1 1 d . . .
H4 H -0.4560 0.8997 0.9112 0.041 Uiso 1 1 calc R . .
C5 C -0.25332(13) 0.86217(13) 0.84220(13) 0.0265(3) Uani 1 1 d . . .
C6 C -0.16674(12) 0.86482(13) 0.73122(12) 0.0234(3) Uani 1 1 d . . .
C7 C -0.02648(12) 0.82145(12) 0.72931(11) 0.0215(3) Uani 1 1 d . . .
C8 C 0.03171(13) 0.77829(12) 0.83323(11) 0.0224(3) Uani 1 1 d . . .
C9 C -0.05451(13) 0.77829(13) 0.94448(12) 0.0247(3) Uani 1 1 d . . .
C10 C -0.19503(13) 0.81957(14) 0.94525(12) 0.0283(3) Uani 1 1 d . . .
H10 H -0.2513 0.8185 1.0167 0.034 Uiso 1 1 calc R . .
C11 C 0.17482(13) 0.73360(13) 0.83341(12) 0.0255(3) Uani 1 1 d . . .
H11 H 0.2319 0.7317 0.7619 0.031 Uiso 1 1 calc R . .
C12 C 0.22771(14) 0.69419(14) 0.93672(13) 0.0297(3) Uani 1 1 d . . .
H12 H 0.3209 0.6659 0.9352 0.036 Uiso 1 1 calc R . .
C13 C 0.14306(15) 0.69532(15) 1.04745(13) 0.0330(3) Uani 1 1 d . . .
H13 H 0.1811 0.6681 1.1175 0.040 Uiso 1 1 calc R . .
C14 C 0.00694(15) 0.73609(14) 1.05078(13) 0.0312(3) Uani 1 1 d . . .
H14 H -0.0475 0.7366 1.1236 0.037 Uiso 1 1 calc R . .
C15 C 0.06616(11) 0.82150(13) 0.61400(11) 0.0221(3) Uani 1 1 d . . .
C16 C 0.10363(12) 0.66454(13) 0.38129(11) 0.0247(3) Uani 1 1 d . . .
H16A H 0.1374 0.7652 0.3683 0.030 Uiso 1 1 calc R . .
H16B H 0.0377 0.5829 0.2956 0.030 Uiso 1 1 calc R . .
C17 C 0.24536(12) 0.61112(13) 0.40987(11) 0.0242(3) Uani 1 1 d . . .
C18 C 0.48766(14) 0.58043(14) 0.33993(14) 0.0331(3) Uani 1 1 d . . .
H18A H 0.4601 0.4628 0.3026 0.040 Uiso 1 1 calc R . .
H18B H 0.5367 0.6228 0.4367 0.040 Uiso 1 1 calc R . .
C19 C 0.59643(16) 0.64373(19) 0.25706(17) 0.0463(4) Uani 1 1 d . . .
H19A H 0.6176 0.7596 0.2915 0.056 Uiso 1 1 calc R . .
H19B H 0.5488 0.5959 0.1606 0.056 Uiso 1 1 calc R . .
H19C H 0.6923 0.6161 0.2661 0.056 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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
C17 O1 C18 116.43(9) . . ?
C15 N1 C16 120.09(8) . . ?
C15 N1 H1 120.0 . . ?
C16 N1 H1 120.0 . . ?
C2 C1 C6 120.98(12) . . ?
C2 C1 H1A 119.5 . . ?
C6 C1 H1A 119.5 . . ?
C1 C2 C3 120.86(13) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.10(11) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.31(12) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C10 C5 C4 122.28(11) . . ?
C10 C5 C6 119.49(11) . . ?
C4 C5 C6 118.23(11) . . ?
C7 C6 C1 122.85(11) . . ?
C7 C6 C5 118.67(11) . . ?
C1 C6 C5 118.47(10) . . ?
C8 C7 C6 121.65(10) . . ?
C8 C7 C15 118.34(10) . . ?
C6 C7 C15 120.01(10) . . ?
C7 C8 C11 122.60(10) . . ?
C7 C8 C9 119.19(11) . . ?
C11 C8 C9 118.21(10) . . ?
C10 C9 C14 122.24(11) . . ?
C10 C9 C8 119.07(11) . . ?
C14 C9 C8 118.69(11) . . ?
C5 C10 C9 121.92(11) . . ?
C5 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 C11 C8 120.70(11) . . ?
C12 C11 H11 119.6 . . ?
C8 C11 H11 119.6 . . ?
C11 C12 C13 121.14(11) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 120.00(11) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 121.25(11) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
O3 C15 N1 122.61(10) . . ?
O3 C15 C7 122.58(10) . . ?
N1 C15 C7 114.79(8) . . ?
N1 C16 C17 111.96(9) . . ?
N1 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N1 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
O2 C17 O1 124.32(10) . . ?
O2 C17 C16 124.97(9) . . ?
O1 C17 C16 110.70(9) . . ?
O1 C18 C19 106.55(11) . . ?
O1 C18 H18A 110.4 . . ?
C19 C18 H18A 110.4 . . ?
O1 C18 H18B 110.4 . . ?
C19 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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 C17 1.3299(13) . ?
O1 C18 1.4656(14) . ?
O2 C17 1.2111(13) . ?
O3 C15 1.2235(12) . ?
N1 C15 1.3470(14) . ?
N1 C16 1.4470(12) . ?
N1 H1 0.8600 . ?
C1 C2 1.3591(17) . ?
C1 C6 1.4235(16) . ?
C1 H1A 0.9300 . ?
C2 C3 1.418(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.4286(16) . ?
C4 H4 0.9300 . ?
C5 C10 1.3912(18) . ?
C5 C6 1.4420(16) . ?
C6 C7 1.4035(15) . ?
C7 C8 1.4022(15) . ?
C7 C15 1.5079(14) . ?
C8 C11 1.4350(15) . ?
C8 C9 1.4380(15) . ?
C9 C10 1.3969(17) . ?
C9 C14 1.4292(17) . ?
C10 H10 0.9300 . ?
C11 C12 1.3561(16) . ?
C11 H11 0.9300 . ?
C12 C13 1.4233(17) . ?
C12 H12 0.9300 . ?
C13 C14 1.3558(19) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C16 C17 1.5162(15) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C19 1.5031(17) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O2 . . 2_566 2.9516(12) 0.860 2.109 166.3 no
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 -0.76(19) . . . . ?
C1 C2 C3 C4 1.57(19) . . . . ?
C2 C3 C4 C5 -0.42(19) . . . . ?
C3 C4 C5 C10 178.84(11) . . . . ?
C3 C4 C5 C6 -1.44(17) . . . . ?
C2 C1 C6 C7 179.80(10) . . . . ?
C2 C1 C6 C5 -1.12(17) . . . . ?
C10 C5 C6 C7 1.03(16) . . . . ?
C4 C5 C6 C7 -178.70(9) . . . . ?
C10 C5 C6 C1 -178.09(9) . . . . ?
C4 C5 C6 C1 2.18(16) . . . . ?
C1 C6 C7 C8 178.15(9) . . . . ?
C5 C6 C7 C8 -0.93(16) . . . . ?
C1 C6 C7 C15 -1.46(16) . . . . ?
C5 C6 C7 C15 179.46(9) . . . . ?
C6 C7 C8 C11 -179.97(9) . . . . ?
C15 C7 C8 C11 -0.35(16) . . . . ?
C6 C7 C8 C9 0.06(16) . . . . ?
C15 C7 C8 C9 179.68(8) . . . . ?
C7 C8 C9 C10 0.71(16) . . . . ?
C11 C8 C9 C10 -179.25(9) . . . . ?
C7 C8 C9 C14 -179.22(9) . . . . ?
C11 C8 C9 C14 0.82(16) . . . . ?
C4 C5 C10 C9 179.45(10) . . . . ?
C6 C5 C10 C9 -0.26(17) . . . . ?
C14 C9 C10 C5 179.31(9) . . . . ?
C8 C9 C10 C5 -0.61(17) . . . . ?
C7 C8 C11 C12 179.36(9) . . . . ?
C9 C8 C11 C12 -0.68(17) . . . . ?
C8 C11 C12 C13 0.23(18) . . . . ?
C11 C12 C13 C14 0.09(18) . . . . ?
C12 C13 C14 C9 0.07(18) . . . . ?
C10 C9 C14 C13 179.54(10) . . . . ?
C8 C9 C14 C13 -0.53(17) . . . . ?
C16 N1 C15 O3 6.18(16) . . . . ?
C16 N1 C15 C7 -172.33(9) . . . . ?
C8 C7 C15 O3 -78.76(13) . . . . ?
C6 C7 C15 O3 100.87(12) . . . . ?
C8 C7 C15 N1 99.74(11) . . . . ?
C6 C7 C15 N1 -80.63(12) . . . . ?
C15 N1 C16 C17 75.31(12) . . . . ?
C18 O1 C17 O2 1.95(16) . . . . ?
C18 O1 C17 C16 -176.70(8) . . . . ?
N1 C16 C17 O2 19.57(15) . . . . ?
N1 C16 C17 O1 -161.79(9) . . . . ?
C17 O1 C18 C19 -171.24(10) . . . . ?
