A versatile synthesis of pyrazolo[3,4-c]isoquinoline derivatives by reaction of 4-aryl-5-aminopyrazoles with aryl/heteroaryl aldehydes: the effect of the heterocycle on the reaction pathways.
Bogza, Sergei L.; Kobrakov, Konstantin I.; Malienko, Anna A.; Perepichka, Igor F.; Sujkov, Sergei Yu; Bryce, Martin R.; Lyubchik, Svetlana B.; Batsanov, Andrei S.; Bogdan, Natalya M.; Organic & biomolecular chemistry 3 (2005) 932–940; doi:10.1039/b417002d

data_7150057
_publ_section_title
;
 A versatile synthesis of pyrazolo[3,4-c]isoquinoline derivatives by
 reaction of 4-aryl-5-aminopyrazoles with aryl/heteroaryl aldehydes:
 the effect of the heterocycle on the reaction pathways.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              932
_journal_page_last               940
_journal_paper_doi               10.1039/b417002d
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C35 H34 N4 O2'
_chemical_formula_sum            'C35 H34 N4 O2'
_chemical_formula_weight         542.66
_chemical_melting_point          473.4(3)
_chemical_name_common
;5-(4-(dimethylamino)phenyl)-7,8-dimethoxypyrazolo(3,4-
c)isoquinoline
;
_chemical_name_systematic
;
5-{4-(dimethylamino)phenyl}-
7,8-dimethoxypyrazolo[3,4-c]isoquinoline
;
_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
_cell_angle_alpha                64.13(2)
_cell_angle_beta                 73.04(2)
_cell_angle_gamma                81.00(2)
_cell_formula_units_Z            2
_cell_length_a                   8.944(4)
_cell_length_b                   12.945(5)
_cell_length_c                   13.918(7)
_cell_measurement_reflns_used    421
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      20.79
_cell_measurement_theta_min      10.13
_cell_volume                     1386.1(11)
_computing_cell_refinement       'SMART version 5.625 (Bruker, 2001)'
_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT version 6.28A (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL version 5.10 (Bruker, 1997)'
_computing_publication_material  'SHELXTL version 5.10 (Bruker, 1997)'
_computing_structure_refinement  'SHELXTL version 6.12 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL version 6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEX CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source
'60W microfocus Bede Microsource with glass polycapillary optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_sigmaI/netI    0.1520
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10374
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.835
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.835
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0099P)^2^P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                2568
_reflns_number_total             5074
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b417002d.txt
_cod_data_source_block           (10Cd)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '200--200.5 \% C' was changed to
'473.4(3)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        1386.1(12)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150057