#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:27:46 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286198 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/96/1569618.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_1569618
loop_
_publ_author_name
'De, Sagnik'
'Das, Gopal'
_publ_section_title
;
 Surfactant-induced disaggregation of a quinoxaline AIEgen scaffold:
 aggregation aptitude in the solid and solution states.
;
_journal_issue                   32
_journal_name_full               'Soft matter'
_journal_page_first              6116
_journal_page_last               6121
_journal_paper_doi               10.1039/d3sm00638g
_journal_volume                  19
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C21 H14 N2 O2'
_chemical_formula_sum            'C21 H14 N2 O2'
_chemical_formula_weight         326.34
_chemical_name_common            L2
_chemical_name_systematic        L2
_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
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-03-13 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                100.887(17)
_cell_angle_beta                 93.957(16)
_cell_angle_gamma                98.408(15)
_cell_formula_units_Z            2
_cell_length_a                   6.4465(10)
_cell_length_b                   10.691(2)
_cell_length_c                   12.369(2)
_cell_measurement_reflns_used    1027
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9920
_cell_measurement_theta_min      3.2180
_cell_volume                     824.0(2)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.1409
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6370
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.712
_diffrn_reflns_theta_min         2.317
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Golden
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.2001
_refine_ls_R_factor_gt           0.0778
_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)+(0.0893P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.2537
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1455
_reflns_number_total             3715
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sm00638g2.cif
_cod_data_source_block           L2
_cod_depositor_comments
'Adding full bibliography for 1569618--1569621.cif.'
_cod_database_code               1569618
_shelxl_version_number           2019/1
_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.
;
loop_
_space_group_symop_operation_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_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
O24 O 0.1401(4) 0.0209(3) 0.89061(19) 0.0727(10) Uani 1 1 d . . . . .
H24 H 0.033224 -0.013591 0.912377 0.109 Uiso 1 1 calc R U . . .
O25 O 0.2178(4) 0.1005(3) 1.07181(18) 0.0658(9) Uani 1 1 d . . . . .
N2 N 1.0413(5) 0.3444(3) 0.8869(2) 0.0519(9) Uani 1 1 d . . . . .
N9 N 0.7683(4) 0.1809(3) 0.7132(2) 0.0520(9) Uani 1 1 d . . . . .
C1 C 1.0849(5) 0.3317(3) 0.7827(2) 0.0455(9) Uani 1 1 d . . . . .
C3 C 0.8584(5) 0.2755(3) 0.9074(2) 0.0475(10) Uani 1 1 d . . . . .
C4 C 0.8025(6) 0.2864(4) 1.0165(3) 0.0558(11) Uani 1 1 d . . . . .
H4 H 0.894661 0.337102 1.074759 0.067 Uiso 1 1 calc R U . . .
C5 C 0.6152(6) 0.2237(4) 1.0377(3) 0.0556(11) Uani 1 1 d . . . . .
H5 H 0.581420 0.230105 1.110180 0.067 Uiso 1 1 calc R U . . .
C6 C 0.4726(5) 0.1492(3) 0.9500(3) 0.0480(10) Uani 1 1 d . . . . .
C7 C 0.5228(6) 0.1339(3) 0.8432(3) 0.0511(10) Uani 1 1 d . . . . .
H7 H 0.428901 0.082040 0.786325 0.061 Uiso 1 1 calc R U . . .
C8 C 0.7176(6) 0.1972(3) 0.8195(2) 0.0472(10) Uani 1 1 d . . . . .
C10 C 0.9478(5) 0.2438(3) 0.6939(2) 0.0497(10) Uani 1 1 d . . . . .
C11 C 1.2775(6) 0.4166(3) 0.7628(3) 0.0485(10) Uani 1 1 d . . . . .
C12 C 1.4500(6) 0.4441(3) 0.8429(3) 0.0542(11) Uani 1 1 d . . . . .
H12 H 1.441880 0.409666 0.906482 0.065 Uiso 1 1 calc R U . . .
C13 C 1.6336(6) 0.5223(4) 0.8286(3) 0.0697(12) Uani 1 1 d . . . . .
H13 H 1.748617 0.538567 0.881792 0.084 Uiso 1 1 calc R U . . .
C14 C 1.6458(7) 0.5754(4) 0.7372(4) 0.0809(16) Uani 1 1 d . . . . .
H14 H 1.770215 0.626100 0.727118 0.097 Uiso 1 1 calc R U . . .
C15 C 1.4748(8) 0.5541(4) 0.6599(3) 0.0869(17) Uani 1 1 d . . . . .
H15 H 1.481923 0.592938 0.598762 0.104 Uiso 1 1 calc R U . . .
C16 C 1.2913(7) 0.4749(4) 0.6727(3) 0.0747(15) Uani 1 1 d . . . . .
H16 H 1.176186 0.461031 0.619770 0.090 Uiso 1 1 calc R U . . .
C17 C 1.0067(6) 0.2117(4) 0.5785(2) 0.0542(11) Uani 1 1 d . . . . .
C18 C 1.1937(6) 0.1703(4) 0.5557(3) 0.0629(12) Uani 1 1 d . . . . .
H18 H 1.292815 0.168801 0.613529 0.075 Uiso 1 1 calc R U . . .
C19 C 1.2364(8) 0.1308(4) 0.4477(3) 0.0789(15) Uani 1 1 d . . . . .
H19 H 1.361765 0.100606 0.433091 0.095 Uiso 1 1 calc R U . . .
C20 C 1.0929(10) 0.1363(5) 0.3620(3) 0.0880(19) Uani 1 1 d . . . . .
H20 H 1.122921 0.111720 0.289262 0.106 Uiso 1 1 calc R U . . .
C21 C 0.9074(9) 0.1776(5) 0.3830(3) 0.0912(18) Uani 1 1 d . . . . .
H21 H 0.811007 0.180922 0.324489 0.109 Uiso 1 1 calc R U . . .
C22 C 0.8605(7) 0.2149(4) 0.4917(3) 0.0757(15) Uani 1 1 d . . . . .
H22 H 0.732346 0.241714 0.505800 0.091 Uiso 1 1 calc R U . . .
C23 C 0.2652(6) 0.0856(4) 0.9738(3) 0.0519(10) 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
C23 O24 H24 109.5 . . ?
C1 N2 C3 117.6(3) . . ?
C10 N9 C8 118.2(3) . . ?
N2 C1 C10 121.4(3) . . ?
N2 C1 C11 115.8(3) . . ?
C10 C1 C11 122.7(3) . . ?
N2 C3 C4 120.1(3) . . ?
N2 C3 C8 120.7(3) . . ?
C4 C3 C8 119.1(3) . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 C23 119.5(3) . . ?
C5 C6 C23 119.5(3) . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
N9 C8 C7 119.8(3) . . ?
N9 C8 C3 121.0(3) . . ?
C7 C8 C3 119.1(3) . . ?
N9 C10 C1 120.9(3) . . ?
N9 C10 C17 116.0(3) . . ?
C1 C10 C17 123.0(3) . . ?
C16 C11 C12 118.0(3) . . ?
C16 C11 C1 123.8(3) . . ?
C12 C11 C1 118.1(3) . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.8(4) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C22 119.3(3) . . ?
C18 C17 C10 122.0(4) . . ?
C22 C17 C10 118.5(4) . . ?
C17 C18 C19 120.8(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 119.8(5) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 120.3(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.5(4) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.4(5) . . ?
C17 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
O25 C23 O24 123.5(3) . . ?
O25 C23 C6 119.7(3) . . ?
O24 C23 C6 116.8(3) . . ?
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
O24 C23 1.281(4) . ?
O24 H24 0.8200 . ?
O25 C23 1.257(3) . ?
N2 C1 1.324(4) . ?
N2 C3 1.362(4) . ?
N9 C10 1.312(4) . ?
N9 C8 1.362(4) . ?
C1 C10 1.451(4) . ?
C1 C11 1.491(4) . ?
C3 C4 1.409(4) . ?
C3 C8 1.417(4) . ?
C4 C5 1.359(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(4) . ?
C6 C23 1.483(4) . ?
C7 C8 1.414(4) . ?
C7 H7 0.9300 . ?
C10 C17 1.492(4) . ?
C11 C16 1.378(5) . ?
C11 C12 1.396(5) . ?
C12 C13 1.388(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.359(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.373(6) . ?
C17 C22 1.388(5) . ?
C18 C19 1.382(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.359(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.396(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
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
C3 N2 C1 C10 -2.5(6) . . . . ?
C3 N2 C1 C11 175.3(3) . . . . ?
C1 N2 C3 C4 -179.2(4) . . . . ?
C1 N2 C3 C8 -2.3(6) . . . . ?
N2 C3 C4 C5 176.4(4) . . . . ?
C8 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 -1.4(7) . . . . ?
C4 C5 C6 C7 2.8(6) . . . . ?
C4 C5 C6 C23 -177.5(4) . . . . ?
C5 C6 C7 C8 -2.1(6) . . . . ?
C23 C6 C7 C8 178.2(4) . . . . ?
C10 N9 C8 C7 178.2(4) . . . . ?
C10 N9 C8 C3 -2.6(6) . . . . ?
C6 C7 C8 N9 179.4(4) . . . . ?
C6 C7 C8 C3 0.1(6) . . . . ?
N2 C3 C8 N9 5.0(6) . . . . ?
C4 C3 C8 N9 -178.0(3) . . . . ?
N2 C3 C8 C7 -175.8(4) . . . . ?
C4 C3 C8 C7 1.2(6) . . . . ?
C8 N9 C10 C1 -2.1(6) . . . . ?
C8 N9 C10 C17 173.5(3) . . . . ?
N2 C1 C10 N9 4.9(6) . . . . ?
C11 C1 C10 N9 -172.7(4) . . . . ?
N2 C1 C10 C17 -170.4(4) . . . . ?
C11 C1 C10 C17 12.0(6) . . . . ?
N2 C1 C11 C16 -141.2(4) . . . . ?
C10 C1 C11 C16 36.6(6) . . . . ?
N2 C1 C11 C12 35.3(5) . . . . ?
C10 C1 C11 C12 -147.0(4) . . . . ?
C16 C11 C12 C13 -3.5(6) . . . . ?
C1 C11 C12 C13 179.9(3) . . . . ?
C11 C12 C13 C14 1.4(6) . . . . ?
C12 C13 C14 C15 1.5(7) . . . . ?
C13 C14 C15 C16 -2.2(8) . . . . ?
C12 C11 C16 C15 2.8(6) . . . . ?
C1 C11 C16 C15 179.2(4) . . . . ?
C14 C15 C16 C11 0.0(7) . . . . ?
N9 C10 C17 C18 -123.7(4) . . . . ?
C1 C10 C17 C18 51.9(5) . . . . ?
N9 C10 C17 C22 51.5(5) . . . . ?
C1 C10 C17 C22 -133.0(4) . . . . ?
C22 C17 C18 C19 -0.6(5) . . . . ?
C10 C17 C18 C19 174.5(3) . . . . ?
C17 C18 C19 C20 1.8(6) . . . . ?
C18 C19 C20 C21 -1.5(7) . . . . ?
C19 C20 C21 C22 0.1(7) . . . . ?
C18 C17 C22 C21 -0.8(6) . . . . ?
C10 C17 C22 C21 -176.1(3) . . . . ?
C20 C21 C22 C17 1.1(7) . . . . ?
C7 C6 C23 O25 -179.3(4) . . . . ?
C5 C6 C23 O25 1.1(6) . . . . ?
C7 C6 C23 O24 -1.6(6) . . . . ?
C5 C6 C23 O24 178.7(4) . . . . ?
