Unexpected synthesis, delayed emission and solid-state acidochromism of novel 2,7-naphthyridine derivatives obtained from 2-(3,5-diaryl-4H-pyran-4-ylidene)malononitrile
Jiang, Yitian; Liu, Miaochang; Wang, Mengzhu; Lei, yunxiang; Ding, Qiuping; Wu, Huayue; Huang, Xiaobo; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01336C

data_7158889
_publ_section_title
;
 Unexpected synthesis, delayed emission and solid-state acidochromism of
 novel 2,7-naphthyridine derivatives obtained from
 2-(3,5-diaryl-4H-pyran-4-ylidene)malononitrile
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01336C
_journal_year                    2022
_chemical_formula_sum            'C34 H24 N2 O'
_chemical_formula_weight         476.55
_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-2013
_audit_update_record
;
2022-05-19 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.914(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.271(3)
_cell_length_b                   19.1087(18)
_cell_length_c                   9.0450(9)
_cell_measurement_reflns_used    1932
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.774
_cell_measurement_theta_min      4.998
_cell_volume                     5212.8(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1164
_diffrn_reflns_av_unetI/netI     0.1819
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23606
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.499
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         9146
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.2503
_refine_ls_R_factor_gt           0.0825
_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^)+(0.0666P)^2^+0.9597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.2425
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3007
_reflns_number_total             9146
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01336c2.cif
_cod_data_source_block           ddz21124
_cod_depositor_comments
;

2024-10-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C68 H48 N4 O2'
_cod_original_formula_weight         953.10
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158889
_shelx_estimated_absorpt_t_min   0.990
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2013-4
_shelx_res_checksum              13054