#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/00/7150057.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150057
loop_
_publ_author_name
'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.'
_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 & 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       'ω 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/[σ²(Fo²)+(0.0099P)²P] where P=(Fo²+2Fc²)/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>2σ(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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8299(2) 0.44709(15) 0.56955(13) 0.0237(5) Uani 1 1 d . . .
O2 O 0.7850(2) 0.42841(15) 0.40565(13) 0.0238(5) Uani 1 1 d . . .
N1 N 0.1638(3) 0.22023(18) 0.71685(16) 0.0198(5) Uani 1 1 d . . .
N2 N 0.0853(3) 0.21062(18) 0.90192(16) 0.0198(5) Uani 1 1 d . . .
N3 N 0.1495(3) 0.23273(18) 0.96949(16) 0.0210(5) Uani 1 1 d . . .
N4 N 0.1847(3) 0.13706(18) 0.29479(16) 0.0208(5) Uani 1 1 d . . .
C1 C 0.6929(3) 0.4000(2) 0.5907(2) 0.0186(6) Uani 1 1 d . . .
C2 C 0.6680(3) 0.3879(2) 0.4999(2) 0.0186(6) Uani 1 1 d . . .
C3 C 0.5350(3) 0.3403(2) 0.5115(2) 0.0181(6) Uani 1 1 d . . .
H3 H 0.5193 0.3331 0.4501 0.022 Uiso 1 1 d R . .
C4 C 0.4191(3) 0.3004(2) 0.6135(2) 0.0174(6) Uani 1 1 d . . .
C5 C 0.4438(3) 0.3161(2) 0.70259(19) 0.0180(6) Uani 1 1 d . . .
C6 C 0.5817(3) 0.3652(2) 0.6891(2) 0.0181(6) Uani 1 1 d . . .
H6 H 0.5981 0.3748 0.7492 0.022 Uiso 1 1 d R . .
C7 C 0.3197(3) 0.2810(2) 0.80076(19) 0.0179(6) Uani 1 1 d . . .
C8 C 0.1889(3) 0.2392(2) 0.7992(2) 0.0180(6) Uani 1 1 d . . .
C9 C 0.2815(3) 0.2473(2) 0.6267(2) 0.0186(6) Uani 1 1 d . . .
C10 C 0.2876(3) 0.2754(2) 0.9100(2) 0.0189(6) Uani 1 1 d . . .
C11 C -0.0586(3) 0.1548(2) 0.9464(2) 0.0189(6) Uani 1 1 d . . .
C12 C -0.1114(3) 0.0969(2) 1.0602(2) 0.0215(7) Uani 1 1 d . . .
H12 H -0.0506 0.0938 1.1071 0.026 Uiso 1 1 d R . .
C13 C -0.2523(3) 0.0437(2) 1.1043(2) 0.0257(7) Uani 1 1 d . . .
H13 H -0.2885 0.0043 1.1820 0.031 Uiso 1 1 d R . .
C14 C -0.3420(3) 0.0468(2) 1.0376(2) 0.0254(7) Uani 1 1 d . . .
H14 H -0.4395 0.0103 1.0690 0.030 Uiso 1 1 d R . .
C15 C -0.2880(3) 0.1032(2) 0.9244(2) 0.0245(7) Uani 1 1 d . . .
H15 H -0.3487 0.1051 0.8779 0.029 Uiso 1 1 d R . .
C16 C -0.1474(3) 0.1569(2) 0.8787(2) 0.0225(7) Uani 1 1 d . . .
H16 H -0.1110 0.1951 0.8008 0.027 Uiso 1 1 d R . .
C17 C 0.3838(3) 0.3113(2) 0.96244(19) 0.0204(7) Uani 1 1 d . . .
H171 H 0.4940 0.2860 0.9414 0.027 Uiso 1 1 d R . .
H172 H 0.3464 0.2716 1.0436 0.027 Uiso 1 1 d R . .
C18 C 0.8598(3) 0.4678(2) 0.6552(2) 0.0262(7) Uani 1 1 d . . .
H181 H 0.7853 0.5267 0.6694 0.035(5) Uiso 1 1 d R . .
H182 H 0.9664 0.4944 0.6320 0.035(5) Uiso 1 1 d R . .
H183 H 0.8484 0.3965 0.7227 0.035(5) Uiso 1 1 d R . .
C19 C 0.7650(3) 0.4192(2) 0.3117(2) 0.0258(7) Uani 1 1 d . . .
H191 H 0.7562 0.3382 0.3288 0.024(4) Uiso 1 1 d R . .
H192 H 0.8554 0.4507 0.2492 0.024(4) Uiso 1 1 d R . .
H193 H 0.6698 0.4623 0.2925 0.024(4) Uiso 1 1 d R . .
C20 C 0.2588(3) 0.2189(2) 0.53944(19) 0.0181(6) Uani 1 1 d . . .
C21 C 0.3720(3) 0.1574(2) 0.4900(2) 0.0210(6) Uani 1 1 d . . .
H21 H 0.4686 0.1356 0.5102 0.025 Uiso 1 1 d R . .
C22 C 0.3460(3) 0.1274(2) 0.41262(19) 0.0210(7) Uani 1 1 d . . .
H22 H 0.4245 0.0842 0.3817 0.025 Uiso 1 1 d R . .
C23 C 0.2077(3) 0.1594(2) 0.37818(19) 0.0204(7) Uani 1 1 d . . .
C24 C 0.0933(3) 0.2183(2) 0.4305(2) 0.0206(6) Uani 1 1 d . . .
H24 H -0.0042 0.2394 0.4115 0.025 Uiso 1 1 d R . .
C25 C 0.1196(3) 0.2462(2) 0.50937(19) 0.0196(6) Uani 1 1 d . . .
H25 H 0.0391 0.2855 0.5437 0.024 Uiso 1 1 d R . .
C26 C 0.3767(3) 0.4397(2) 0.93011(19) 0.0191(6) Uani 1 1 d . . .
C27 C 0.5098(3) 0.5038(2) 0.87536(19) 0.0227(7) Uani 1 1 d . . .
H27 H 0.6077 0.4667 0.8581 0.027 Uiso 1 1 d R . .
C28 C 0.5029(4) 0.6218(2) 0.8452(2) 0.0280(7) Uani 1 1 d . . .
H28 H 0.5951 0.6647 0.8070 0.034 Uiso 1 1 d R . .
C29 C 0.3611(4) 0.6764(2) 0.8709(2) 0.0315(8) Uani 1 1 d . . .
H29 H 0.3556 0.7570 0.8498 0.038 Uiso 1 1 d R . .
C30 C 0.2283(4) 0.6134(2) 0.9275(2) 0.0319(8) Uani 1 1 d . . .
H30 H 0.1314 0.6505 0.9470 0.038 Uiso 1 1 d R . .
C31 C 0.2353(3) 0.4954(2) 0.9561(2) 0.0250(7) Uani 1 1 d . . .
H31 H 0.1428 0.4528 0.9937 0.030 Uiso 1 1 d R . .
C32 C 0.2908(3) 0.0591(2) 0.2547(2) 0.0256(7) Uani 1 1 d . . .
H321 H 0.3995 0.0806 0.2391 0.033 Uiso 1 1 d R . .
H322 H 0.2726 0.0690 0.1843 0.033 Uiso 1 1 d R . .
C33 C 0.2741(4) -0.0672(2) 0.3345(2) 0.0331(8) Uani 1 1 d . . .
H331 H 0.2861 -0.0775 0.4059 0.041(5) Uiso 1 1 d R . .
H332 H 0.3549 -0.1135 0.3046 0.041(5) Uiso 1 1 d R . .
H333 H 0.1706 -0.0919 0.3442 0.041(5) Uiso 1 1 d R . .
C34 C 0.0408(3) 0.1729(2) 0.2592(2) 0.0242(7) Uani 1 1 d . . .
H341 H 0.0617 0.1791 0.1831 0.032 Uiso 1 1 d R . .
H342 H 0.0090 0.2506 0.2570 0.032 Uiso 1 1 d R . .
C35 C -0.0951(4) 0.0940(2) 0.3311(2) 0.0335(8) Uani 1 1 d . . .
H351 H -0.0712 0.0198 0.3259 0.040(5) Uiso 1 1 d R . .
H352 H -0.1897 0.1292 0.3058 0.040(5) Uiso 1 1 d R . .
H353 H -0.1122 0.0822 0.4080 0.040(5) Uiso 1 1 d R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C18 117.8(2) . . ?
C2 O2 C19 116.5(2) . . ?
C9 N1 C8 114.6(2) . . ?
N3 N2 C8 109.8(2) . . ?
N3 N2 C11 119.4(2) . . ?
C8 N2 C11 130.5(2) . . ?
C10 N3 N2 106.6(2) . . ?
C23 N4 C34 121.2(2) . . ?
C23 N4 C32 120.6(2) . . ?
C34 N4 C32 117.2(2) . . ?
O1 C1 C6 125.7(2) . . ?
O1 C1 C2 114.5(2) . . ?
C6 C1 C2 119.8(3) . . ?
C3 C2 O2 125.8(2) . . ?
C3 C2 C1 119.9(2) . . ?
O2 C2 C1 114.3(2) . . ?
C2 C3 C4 121.7(2) . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 C9 120.6(2) . . ?
C3 C4 C9 121.7(2) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 C7 124.8(2) . . ?
C4 C5 C7 115.3(2) . . ?
C1 C6 C5 121.1(2) . . ?
C8 C7 C5 117.8(2) . . ?
C8 C7 C10 104.6(2) . . ?
C5 C7 C10 137.6(2) . . ?
N1 C8 C7 128.1(2) . . ?
N1 C8 N2 123.8(2) . . ?
C7 C8 N2 107.9(2) . . ?
N1 C9 C4 123.1(2) . . ?
N1 C9 C20 114.7(2) . . ?
C4 C9 C20 122.2(2) . . ?
N3 C10 C7 111.2(2) . . ?
N3 C10 C17 118.3(2) . . ?
C7 C10 C17 130.5(2) . . ?
C16 C11 C12 119.7(3) . . ?
C16 C11 N2 121.3(2) . . ?
C12 C11 N2 119.0(2) . . ?
C13 C12 C11 119.5(3) . . ?
C12 C13 C14 121.1(3) . . ?
C13 C14 C15 119.2(3) . . ?
C16 C15 C14 120.6(3) . . ?
C15 C16 C11 119.9(2) . . ?
C10 C17 C26 113.7(2) . . ?
C25 C20 C21 117.2(2) . . ?
C25 C20 C9 120.5(2) . . ?
C21 C20 C9 122.1(3) . . ?
C22 C21 C20 121.3(3) . . ?
C21 C22 C23 121.7(2) . . ?
N4 C23 C22 122.3(2) . . ?
N4 C23 C24 121.3(3) . . ?
C22 C23 C24 116.4(2) . . ?
C25 C24 C23 121.3(3) . . ?
C20 C25 C24 122.0(2) . . ?
C27 C26 C31 118.5(3) . . ?
C27 C26 C17 121.3(2) . . ?
C31 C26 C17 120.2(2) . . ?
C26 C27 C28 121.2(3) . . ?
C29 C28 C27 119.7(3) . . ?
C30 C29 C28 119.7(3) . . ?
C29 C30 C31 120.3(3) . . ?
C26 C31 C30 120.5(3) . . ?
N4 C32 C33 114.2(2) . . ?
N4 C34 C35 115.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.351(3) . ?
O1 C18 1.432(3) . ?
O2 C2 1.364(3) . ?
O2 C19 1.427(3) . ?
N1 C9 1.329(3) . ?
N1 C8 1.356(3) . ?
N2 N3 1.377(3) . ?
N2 C8 1.383(3) . ?
N2 C11 1.413(3) . ?
N3 C10 1.317(3) . ?
N4 C23 1.387(3) . ?
N4 C34 1.449(3) . ?
N4 C32 1.454(3) . ?
C1 C6 1.369(3) . ?
C1 C2 1.422(3) . ?
C2 C3 1.360(3) . ?
C3 C4 1.423(3) . ?
C4 C5 1.421(3) . ?
C4 C9 1.429(4) . ?
C5 C6 1.403(4) . ?
C5 C7 1.427(3) . ?
C7 C8 1.372(4) . ?
C7 C10 1.434(3) . ?
C9 C20 1.487(3) . ?
C10 C17 1.508(3) . ?
C11 C16 1.388(4) . ?
C11 C12 1.390(3) . ?
C12 C13 1.375(4) . ?
C13 C14 1.378(4) . ?
C14 C15 1.382(3) . ?
C15 C16 1.375(4) . ?
C17 C26 1.516(3) . ?
C20 C25 1.374(4) . ?
C20 C21 1.397(3) . ?
C21 C22 1.380(3) . ?
C22 C23 1.394(4) . ?
C23 C24 1.402(3) . ?
C24 C25 1.383(3) . ?
C26 C27 1.383(4) . ?
C26 C31 1.387(4) . ?
C27 C28 1.393(3) . ?
C28 C29 1.382(4) . ?
C29 C30 1.376(4) . ?
C30 C31 1.396(4) . ?
C32 C33 1.524(4) . ?
C34 C35 1.520(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O1 C1 C2 176.7(2) . . . . ?
O1 C1 C2 C19 -2.0(5) . . . . ?
N3 C10 C17 C26 -100.4(3) . . . . ?
C10 C17 C26 C31 61.8(3) . . . . ?
N1 C9 C20 C25 46.1(3) . . . . ?
C28 C29 N4 C32 12.5(4) . . . . ?
C23 N4 C32 C33 72.6(3) . . . . ?
C33 C32 N4 C34 -96.4(3) . . . . ?
C32 N4 C34 C35 87.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1668477
