Quinoxaline-based azamacrocycles: synthesis, AIE behavior and acidochromism.
Kharlamova, Alisa D.; Ermakova, Elizaveta V.; Abel, Anton S.; Gontcharenko, Victoria E.; Cheprakov, Andrei V.; Averin, Alexei D.; Beletskaya, Irina P.; Andraud, Chantal; Bretonnière, Yann; Bessmertnykh-Lemeune, Alla; Organic & biomolecular chemistry 22 (2024) 5181–5192; doi:10.1039/d4ob00558a

data_7159963
_publ_section_title
;
 Quinoxaline-based azamacrocycles: synthesis, AIE behavior and
 acidochromism.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5181
_journal_page_last               5192
_journal_paper_doi               10.1039/d4ob00558a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C28 H30 N4 O3'
_chemical_formula_sum            'C28 H30 N4 O3'
_chemical_formula_weight         470.56
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-19
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-08 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.3910(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6697(5)
_cell_length_b                   10.2676(4)
_cell_length_c                   18.2714(7)
_cell_measurement_reflns_used    6978
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.36
_cell_volume                     2419.01(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            39741
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.585
_diffrn_reflns_theta_min         1.579
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.6478
_exptl_absorpt_correction_T_min  0.5912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1715 before and 0.0574 after correction.
The Ratio of minimum to maximum transmission is 0.9126.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         7421
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0908P)^2^+0.5551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1669
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5697
_reflns_number_total             7421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00558a2.cif
_cod_data_source_block           q
_cod_depositor_comments          'Adding full bibliography for 7159963.cif.'
_cod_database_code               7159963
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C4-C3
 1.52 with sigma of 0.01
 O2-C4
 1.43 with sigma of 0.02
 O2-C5 = O2-C30
 1.43 with sigma of 0.01
 C6-C5 \\sim C30-C29
 with sigma of 0.02
 O2-C5 \\sim O2-C30
 with sigma of 0.02
 O2-C4 \\sim O2-C30
 with sigma of 0.02
 O2-C30 \\sim O2-C5
 with sigma of 0.02
3. Others
 Fixed Sof: C5(0.7) H5A(0.7) H5B(0.7) C6(0.7) H6A(0.7) H6B(0.7) C29(0.3)
 H29A(0.3) H29B(0.3) C30(0.3) H30A(0.3) H30B(0.3)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C2(H2A,H2B), C7(H7A,H7B), C3(H3A,H3B), C4(H4A,H4B),
 C5(H5A,H5B), C6(H6A,H6B), C29(H29A,H29B), C30(H30A,H30B)
4.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C14(H14), C12(H12), C17(H17), C10(H10), C28(H28), C20(H20),
 C18(H18), C11(H11), C26(H26), C27(H27), C19(H19)
;
_shelx_res_checksum              85805
_olex2_submission_special_instructions 'No special instructions were received'