Synthesis of a visibly emissive 9-nitro-2,3-dihydro-1H-pyrimido[1,2-a]quinoxalin-5-amine scaffold with large stokes shift and live cell imaging
Kanungo, Ajay; Patra, Dipendu; Mukherjee, Sanghamitra; Mahata, Tridib; Maulik, Prakas R.; Dutta, Sanjay; RSC Adv. 5 (2015) 70958–; doi:10.1039/C5RA12960E

data_7221835
_publ_section_title
;
 Synthesis of a visibly emissive
 9-nitro-2,3-dihydro-1H-pyrimido[1,2-a]quinoxalin-5-amine scaffold with
 large stokes shift and live cell imaging
;
_journal_issue                   87
_journal_name_full               'RSC Adv.'
_journal_page_first              70958
_journal_paper_doi               10.1039/C5RA12960E
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C25 H26 N6 O5'
_chemical_formula_sum            'C25 H26 N6 O5'
_chemical_formula_weight         490.52
_chemical_name_common            5e
_chemical_name_systematic
'(E)-methyl 2-(4-benzyl-1-(3-(dimethylamino)propyl)-8-nitro-3- oxo-3,4-dihydropyrazino[2,3-b]quinoxalin-2(1H)-ylidene)acetate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-08-04
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.07.23 svn.r3196 for OlexSys, GUI svn.r5077)
;
_audit_update_record
;
2015-08-06 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                76.719(7)
_cell_angle_beta                 87.487(6)
_cell_angle_gamma                80.980(6)
_cell_formula_units_Z            2
_cell_length_a                   5.8603(5)
_cell_length_b                   11.0162(13)
_cell_length_c                   19.371(2)
_cell_measurement_reflns_used    3410
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.17
_cell_measurement_theta_min      2.41
_cell_volume                     1202.0(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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  0.0638
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23939
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         1.080
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1233 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.8961.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform, methanol'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.1671
_refine_ls_R_factor_gt           0.0558
_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/[\s^2^(Fo^2^)+(0.0824P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2157
_reflns_number_total             5490
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra12960e2.cif
_cod_data_source_block           sd_ak2786bl2_1058069
_cod_database_code               7221835
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C11(H11A,H11B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C5(H5), C8(H8), C7(H7), C13(H13), C17(H17), C14(H14), C16(H16),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              68627
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'