Efficient synthesis of some new antiproliferative N-fused indoles and isoquinolines via 1,3-dipolar cycloaddition reaction in an ionic liquid
Sutariya, Tushar R.; Labana, Balvantsingh M.; Parmar, Narsidas J.; Kant, Rajni; Gupta, Vivek K.; Plata, Gabriela B.; Padrón, José M.; New J. Chem. 39 (2015) 2657–; doi:10.1039/C4NJ02308K

data_7054636
_publ_section_title
;
 Efficient synthesis of some new antiproliferative N-fused indoles and
 isoquinolines via 1,3-dipolar cycloaddition reaction in an ionic liquid
;
_journal_issue                   4
_journal_name_full               'New J. Chem.'
_journal_page_first              2657
_journal_paper_doi               10.1039/C4NJ02308K
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C23 H23 Cl N2 O2'
_chemical_formula_sum            'C23 H23 Cl N2 O2'
_chemical_formula_weight         394.88
_chemical_name_systematic
;
 Ethyl(2R,3aR,10bR)-1-benzyl-10-chloro-1,2,3,3a,4,10b-hexadydropyrrolo-
[2'3':3,4]pyrrolo[1,2-a]indole-2-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-09-13 deposited with the CCDC.
2015-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                81.614(5)
_cell_angle_beta                 81.335(6)
_cell_angle_gamma                89.456(5)
_cell_formula_units_Z            2
_cell_length_a                   9.2721(7)
_cell_length_b                   10.3272(6)
_cell_length_c                   10.7817(7)
_cell_measurement_reflns_used    1820
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7300
_cell_measurement_theta_min      3.8450
_cell_volume                     1009.62(12)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  PLATON(Spek,2009)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1049
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7318
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3954
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0569
_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^)+(0.0494P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1606
_reflns_number_gt                1914
_reflns_number_total             3954
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj02308k2.cif
_cod_data_source_block           iabne1
_cod_depositor_comments
'Adding full bibliography for 7054636--7054637.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7054636