#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/00/7150056.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_7150056
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         'C19 H17 N3 O2,C2 H3 N'
_chemical_formula_sum            'C21 H20 N4 O2'
_chemical_formula_weight         360.41
_chemical_melting_point          439.4(3)
_chemical_name_common
;1-methyl-3-phenyl-7,8-dimethoxypyrazolo(3,4-c)isoquinoline,
acetonitile solvate
;
_chemical_name_systematic
;
1-methyl-3-phenyl-7,8-dimethoxypyrazolo[3,4-c]isoquinoline,
acetonitile solvate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.16(2)
_cell_angle_beta                 105.87(2)
_cell_angle_gamma                95.86(1)
_cell_formula_units_Z            2
_cell_length_a                   7.086(1)
_cell_length_b                   10.791(3)
_cell_length_c                   12.850(2)
_cell_measurement_reflns_used    917
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      12.0
_cell_volume                     901.2(3)
_computing_cell_refinement       'SMART version 5.049 (Bruker, 1997)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1997)'
_computing_data_reduction        'SAINT version 5.00 (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL version 5.10 (Bruker, 1997)'
_computing_publication_material  'SHELXTL version 5.10 (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       'ω 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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10258
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9490
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'XPREP (SHELXTL), R(int)=0.039 before correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       trapetzoid
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0404
_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/[σ²(Fo²)+(0.0523P)²+0.1401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                2988
_reflns_number_total             4128
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b417002d.txt
_cod_data_source_block           (11D)
_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 '166--166.5 \% C' was changed to
'439.4(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_sg_symbol_H-M      P-1
_cod_database_code               7150056
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 0.26383(15) 0.80985(9) 0.41678(8) 0.0246(2) Uani 1 1 d . . .
O2 O 0.25986(15) 0.62183(9) 0.25037(8) 0.0251(2) Uani 1 1 d . . .
N1 N 0.24487(17) 0.28036(11) 0.56571(10) 0.0202(3) Uani 1 1 d . . .
N2 N 0.23851(17) 0.37579(10) 0.75689(9) 0.0193(3) Uani 1 1 d . . .
N3 N 0.23686(17) 0.49667(10) 0.82351(10) 0.0204(3) Uani 1 1 d . . .
N4 N 0.3137(2) 1.12121(14) 0.22088(13) 0.0411(4) Uani 1 1 d . . .
C1 C 0.2588(2) 0.69227(13) 0.43823(12) 0.0200(3) Uani 1 1 d . . .
C2 C 0.25868(19) 0.58726(13) 0.34553(11) 0.0202(3) Uani 1 1 d . . .
C3 C 0.25811(19) 0.46446(13) 0.35749(12) 0.0195(3) Uani 1 1 d . . .
H3 H 0.265(2) 0.3938(15) 0.2973(13) 0.022(4) Uiso 1 1 d . . .
C4 C 0.25252(19) 0.44106(13) 0.46066(11) 0.0184(3) Uani 1 1 d . . .
C5 C 0.24965(18) 0.54479(12) 0.55177(11) 0.0182(3) Uani 1 1 d . . .
C6 C 0.25491(19) 0.67144(13) 0.53888(12) 0.0192(3) Uani 1 1 d . . .
H6 H 0.261(2) 0.7444(14) 0.6013(13) 0.020(4) Uiso 1 1 d . . .
C7 C 0.24434(19) 0.51134(12) 0.65145(11) 0.0177(3) Uani 1 1 d . . .
C8 C 0.24208(19) 0.38179(13) 0.65144(11) 0.0185(3) Uani 1 1 d . . .
C9 C 0.25027(19) 0.31329(13) 0.47384(12) 0.0199(3) Uani 1 1 d . . .
H9 H 0.253(2) 0.2440(13) 0.4089(12) 0.014(3) Uiso 1 1 d . . .
C10 C 0.23892(19) 0.57750(13) 0.76064(11) 0.0191(3) Uani 1 1 d . . .
C11 C 0.2412(2) 0.26979(13) 0.80391(12) 0.0197(3) Uani 1 1 d . . .
C12 C 0.3011(2) 0.29575(14) 0.92108(12) 0.0242(3) Uani 1 1 d . . .
H12 H 0.348(2) 0.3868(16) 0.9691(14) 0.031(4) Uiso 1 1 d . . .
C13 C 0.2971(2) 0.19338(14) 0.96854(13) 0.0277(3) Uani 1 1 d . . .
H13 H 0.338(2) 0.2134(16) 1.0490(15) 0.035(5) Uiso 1 1 d . . .
C14 C 0.2382(2) 0.06618(15) 0.90100(14) 0.0283(3) Uani 1 1 d . . .
H14 H 0.239(2) -0.0046(16) 0.9350(14) 0.033(4) Uiso 1 1 d . . .
C15 C 0.1823(2) 0.04155(14) 0.78454(13) 0.0274(3) Uani 1 1 d . . .
H15 H 0.142(2) -0.0478(16) 0.7338(14) 0.035(4) Uiso 1 1 d . . .
C16 C 0.1820(2) 0.14217(13) 0.73534(13) 0.0234(3) Uani 1 1 d . . .
H16 H 0.140(2) 0.1247(14) 0.6541(14) 0.027(4) Uiso 1 1 d . . .
C17 C 0.2282(2) 0.71667(13) 0.80839(13) 0.0230(3) Uani 1 1 d . . .
H171 H 0.344(2) 0.7779(15) 0.8058(13) 0.031(4) Uiso 1 1 d . . .
H172 H 0.234(2) 0.7359(15) 0.8905(15) 0.032(4) Uiso 1 1 d . . .
H173 H 0.104(3) 0.7377(15) 0.7662(14) 0.036(5) Uiso 1 1 d . . .
C18 C 0.2627(3) 0.91857(15) 0.50626(14) 0.0275(3) Uani 1 1 d . . .
H181 H 0.384(2) 0.9360(15) 0.5744(14) 0.029(4) Uiso 1 1 d . . .
H182 H 0.137(2) 0.9046(15) 0.5276(14) 0.028(4) Uiso 1 1 d . . .
H183 H 0.269(2) 0.9938(15) 0.4765(13) 0.027(4) Uiso 1 1 d . . .
C19 C 0.2463(2) 0.51938(16) 0.15274(13) 0.0262(3) Uani 1 1 d . . .
H191 H 0.370(2) 0.4750(15) 0.1663(13) 0.032(4) Uiso 1 1 d . . .
H192 H 0.123(3) 0.4571(16) 0.1282(14) 0.033(4) Uiso 1 1 d . . .
H193 H 0.249(2) 0.5605(15) 0.0943(14) 0.031(4) Uiso 1 1 d . . .
C20 C 0.2950(2) 1.01055(16) 0.19631(13) 0.0286(3) Uani 1 1 d . . .
C21 C 0.2716(3) 0.86967(17) 0.16571(18) 0.0373(4) Uani 1 1 d . . .
H211 H 0.372(3) 0.843(2) 0.1306(18) 0.065(6) Uiso 1 1 d . . .
H212 H 0.141(3) 0.832(2) 0.1105(18) 0.064(6) Uiso 1 1 d . . .
H213 H 0.292(4) 0.839(2) 0.231(2) 0.090(8) Uiso 1 1 d . . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 1.00 0.0700
0.00 1.00 -1.00 0.0700
0.00 0.00 1.00 0.0600
0.00 0.00 -1.00 0.0600
-1.00 0.00 1.00 0.2800
1.00 0.00 1.00 0.2800
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 116.81(11) . . ?
C2 O2 C19 116.84(11) . . ?
C9 N1 C8 113.45(12) . . ?
N3 N2 C8 110.67(11) . . ?
N3 N2 C11 118.61(11) . . ?
C8 N2 C11 130.70(12) . . ?
C10 N3 N2 106.34(11) . . ?
O1 C1 C6 124.90(13) . . ?
O1 C1 C2 114.28(12) . . ?
C6 C1 C2 120.82(13) . . ?
O2 C2 C3 125.76(12) . . ?
O2 C2 C1 114.45(12) . . ?
C3 C2 C1 119.78(13) . . ?
C2 C3 C4 120.11(13) . . ?
C2 C3 H3 120.7(9) . . ?
C4 C3 H3 119.2(9) . . ?
C5 C4 C3 120.01(12) . . ?
C5 C4 C9 119.37(12) . . ?
C3 C4 C9 120.62(12) . . ?
C4 C5 C6 119.16(13) . . ?
C4 C5 C7 115.68(12) . . ?
C6 C5 C7 125.15(12) . . ?
C1 C6 C5 120.10(13) . . ?
C1 C6 H6 119.4(9) . . ?
C5 C6 H6 120.5(9) . . ?
C8 C7 C5 118.34(12) . . ?
C8 C7 C10 105.06(12) . . ?
C5 C7 C10 136.60(12) . . ?
N1 C8 N2 125.83(12) . . ?
N1 C8 C7 127.38(13) . . ?
N2 C8 C7 106.78(12) . . ?
N1 C9 C4 125.78(13) . . ?
N1 C9 H9 117.2(8) . . ?
C4 C9 H9 117.0(8) . . ?
N3 C10 C7 111.14(12) . . ?
N3 C10 C17 119.06(13) . . ?
C7 C10 C17 129.76(12) . . ?
C16 C11 C12 120.21(13) . . ?
C16 C11 N2 121.13(13) . . ?
C12 C11 N2 118.65(12) . . ?
C13 C12 C11 119.44(14) . . ?
C13 C12 H12 121.0(9) . . ?
C11 C12 H12 119.5(10) . . ?
C14 C13 C12 120.73(15) . . ?
C14 C13 H13 121.2(10) . . ?
C12 C13 H13 118.0(10) . . ?
C13 C14 C15 119.26(14) . . ?
C13 C14 H14 120.1(10) . . ?
C15 C14 H14 120.7(10) . . ?
C16 C15 C14 121.00(14) . . ?
C16 C15 H15 117.5(10) . . ?
C14 C15 H15 121.5(10) . . ?
C15 C16 C11 119.35(14) . . ?
C15 C16 H16 120.8(9) . . ?
C11 C16 H16 119.9(9) . . ?
C10 C17 H171 111.9(9) . . ?
C10 C17 H172 111.2(9) . . ?
H171 C17 H172 106.5(13) . . ?
C10 C17 H173 110.5(10) . . ?
H171 C17 H173 108.2(13) . . ?
H172 C17 H173 108.3(13) . . ?
O1 C18 H181 112.2(9) . . ?
O1 C18 H182 110.2(9) . . ?
H181 C18 H182 110.5(13) . . ?
O1 C18 H183 105.5(9) . . ?
H181 C18 H183 107.2(13) . . ?
H182 C18 H183 111.2(12) . . ?
O2 C19 H191 110.9(9) . . ?
O2 C19 H192 111.9(10) . . ?
H191 C19 H192 111.8(13) . . ?
O2 C19 H193 105.9(10) . . ?
H191 C19 H193 107.0(13) . . ?
H192 C19 H193 109.1(13) . . ?
N4 C20 C21 179.67(18) . . ?
C20 C21 H211 109.3(12) . . ?
C20 C21 H212 109.4(12) . . ?
H211 C21 H212 107.8(18) . . ?
C20 C21 H213 111.1(15) . . ?
H211 C21 H213 106.8(19) . . ?
H212 C21 H213 112(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 1.3618(16) . ?
O1 C18 1.4302(18) . ?
O2 C2 1.3647(16) . ?
O2 C19 1.4280(18) . ?
N1 C9 1.3223(18) . ?
N1 C8 1.3559(18) . ?
N2 N3 1.3772(16) . ?
N2 C8 1.3793(17) . ?
N2 C11 1.4178(17) . ?
N3 C10 1.3275(18) . ?
N4 C20 1.142(2) . ?
C1 C6 1.373(2) . ?
C1 C2 1.429(2) . ?
C2 C3 1.3706(19) . ?
C3 C4 1.4189(19) . ?
C3 H3 0.961(16) . ?
C4 C5 1.4144(19) . ?
C4 C9 1.4287(19) . ?
C5 C6 1.4144(19) . ?
C5 C7 1.4221(19) . ?
C6 H6 0.965(15) . ?
C7 C8 1.3964(19) . ?
C7 C10 1.4229(19) . ?
C9 H9 0.981(14) . ?
C10 C17 1.495(2) . ?
C11 C16 1.391(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.388(2) . ?
C12 H12 0.991(17) . ?
C13 C14 1.383(2) . ?
C13 H13 0.956(18) . ?
C14 C15 1.388(2) . ?
C14 H14 0.968(17) . ?
C15 C16 1.384(2) . ?
C15 H15 0.985(17) . ?
C16 H16 0.968(16) . ?
C17 H171 1.011(17) . ?
C17 H172 1.013(17) . ?
C17 H173 0.981(17) . ?
C18 H181 1.009(17) . ?
C18 H182 1.011(17) . ?
C18 H183 0.980(16) . ?
C19 H191 1.034(16) . ?
C19 H192 0.971(17) . ?
C19 H193 0.965(17) . ?
C20 C21 1.454(2) . ?
C21 H211 0.98(2) . ?
C21 H212 0.98(2) . ?
C21 H213 0.95(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C21 H213 O1 0.95(3) 2.54(3) 3.455(2) 160(2) .
C21 H213 O2 0.95(3) 2.41(3) 3.126(2) 131(2) .
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 179.55(12) . . . . ?
O1 C1 C2 O2 -1.17(17) . . . . ?
C1 C2 O2 C19 -175.93(12) . . . . ?
N3 N2 C11 C12 -18.87(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141310
