Pyrazolo-fused 4-azafluorenones as key reagents for the synthesis of fluorescent dicyanovinylidene-substituted derivatives
Orrego-Hernández, Jessica; Lizarazo, Carolina; Cobo, Justo; Portilla, Jaime; RSC Advances 9 (2019) 27318–; doi:10.1039/C9RA04682H

data_7233594
_publ_section_title
;
 Pyrazolo-fused 4-azafluorenones as key reagents for the synthesis of
 fluorescent dicyanovinylidene-substituted derivatives
;
_journal_issue                   47
_journal_name_full               'RSC Advances'
_journal_page_first              27318
_journal_paper_doi               10.1039/C9RA04682H
_journal_volume                  9
_journal_year                    2019
_chemical_compound_source        'synthetized by authors'
_chemical_formula_moiety         'C30 H19 N5 O'
_chemical_formula_sum            'C30 H19 N5 O'
_chemical_formula_weight         465.5
_chemical_melting_point          518.0(10)
_chemical_name_systematic
2-(4-(4-Methoxyphenyl)-3-methyl-1-phenylindeno[1,2-b]pyrazolo[4,3-e]pyridin-5(1H)-ylidene)malononitrile'
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_date             2019-08-13T08:39:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-08-13 deposited with the CCDC.    2019-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.052(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.878(7)
_cell_length_b                   12.149(6)
_cell_length_c                   27.262(12)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.345
_cell_measurement_wavelength     0.71073
_cell_volume                     4900(4)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 v2016.1--0 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'mercury 3.10.3'
_computing_publication_material  'wingx v2018.2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector_type            'CMOS Photon 100'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            70587
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        27.496
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.248
_diffrn_source_type
'INCOATEC high brilliance microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.09
_refine_ls_R_factor_gt           0.0628
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+12.4144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1339
_reflns_Friedel_coverage         0
_reflns_number_gt                4245
_reflns_number_total             5639
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra04682h2.cif
_cod_data_source_block           1_a_sq
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7233594
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.986
_shelx_shelxl_version_number     2018/3
_platon_squeeze_void_probe_radius 1.20