A domino green method for the rapid synthesis of novel fused isoquinoline derivatives via Knoevenagel/Michael/cyclisation reactions on aqueous media and their photophysical properties
Meshram, Harshadas Mitaram; N, satish kumar; L, Chandrasekhara Rao; Nanubolu, Jagadeesh Babu; RSC Adv.  (2015) –; doi:10.1039/C5RA15948B

data_7223074
_publ_section_title
;
 A domino green method for the rapid synthesis of novel fused isoquinoline
 derivatives via Knoevenagel/Michael/cyclisation reactions on aqueous
 media and their photophysical properties
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA15948B
_journal_year                    2015
_chemical_formula_moiety         'C20 H13 Br N3, C2 F3 O2, C2 H F3 O2'
_chemical_formula_sum            'C24 H14 Br F6 N3 O4'
_chemical_formula_weight         602.29
_chemical_name_systematic
'1:2 salt of 2-(4-bromophenyl)-4-imino-4,1b-dihydro-1H-pyrido[2,1-a]isoquinoline-3-carbonitrile and trifluoroacetic acid'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-05-05 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.6100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8210(7)
_cell_length_b                   15.0720(9)
_cell_length_c                   14.4847(9)
_cell_measurement_reflns_used    6825
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.52
_cell_measurement_theta_min      2.27
_cell_volume                     2431.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23026
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    1.774
_exptl_absorpt_correction_T_max  0.8288
_exptl_absorpt_correction_T_min  0.6006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Trifluroacetic acid'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+2.6979P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                3110
_reflns_number_total             4277
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra15948b2.cif
_cod_data_source_block           aw78m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               7223074