Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines featuring an intramolecular radical-oxidative cyclization of polysubstituted pyrroles, and evaluation of their cytotoxic activity.
Reyes-Gutiérrez, Paul E; Camacho, José R; Ramírez-Apan, Maria Teresa; Osornio, Yazmin M.; Martínez, Roberto; Organic & biomolecular chemistry 8 (2010) 4374–4382; doi:10.1039/c004399k

data_7153379
_publ_section_title
;
 Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines featuring an
 intramolecular radical-oxidative cyclization of polysubstituted pyrroles,
 and evaluation of their cytotoxic activity.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4374
_journal_page_last               4382
_journal_paper_doi               10.1039/c004399k
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C36 H45 N3 O5'
_chemical_formula_sum            'C36 H45 N3 O5'
_chemical_formula_weight         599.75
_chemical_name_common
;
Etil 2-(3-((4-Ciclohexilmetil)-1-piperazinil)-carbonil)-
fenil)-8,9-dimetoxi-3-metil-5,6-dihidropirrolo(2,1-a)-isoquinolin-1-
carboxilato
;
_chemical_name_systematic
;
Etil 2-(3-{[4-Ciclohexilmetil)-1-piperazinil]-carbonil}-fenil)-8,9-
dimetoxi-3-metil-5,6-dihidropirrolo[2,1-a]-isoquinolin-1-carboxilato
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.122(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.400(1)
_cell_length_b                   11.217(1)
_cell_length_c                   27.800(2)
_cell_measurement_reflns_used    4656
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.57
_cell_measurement_theta_min      2.34
_cell_volume                     3224.6(5)
_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'
_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'
_computing_data_reduction        'SAINT V 6.23C (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL V 6.12 (Sheldrick, 2000)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 0.661
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart Apex CCD diffractometer'
_diffrn_measurement_method       \w-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  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            26547
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         1.47
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square-pyram
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.162
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         5912
_refine_ls_number_restraints     264
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+1.0814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1587
_reflns_number_gt                3654
_reflns_number_total             5912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c004399k.txt
_cod_data_source_block           293MAR05
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7153379