#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:57:29 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230671 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/60/7156036.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_7156036
loop_
_publ_author_name
'Miliutina, Mariia'
'Janke, Julia'
'Hassan, Sidra'
'Zaib, Sumera'
'Iqbal, Jamshed'
'Lecka, Joanna'
'Sévigny, Jean'
'Villinger, Alexander'
'Friedrich, Aleksej'
'Lochbrunner, Stefan'
'Langer, Peter'
_publ_section_title
;
 A domino reaction of 3-chlorochromones with aminoheterocycles. Synthesis
 of pyrazolopyridines and benzofuropyridines and their optical and
 ecto-5'-nucleotidase inhibitory effects.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              717
_journal_page_last               732
_journal_paper_doi               10.1039/c7ob02729j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C19 H14 Cl N3 O'
_chemical_formula_sum            'C19 H14 Cl N3 O'
_chemical_formula_weight         335.78
_chemical_name_systematic
2-(5-Chloro-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6-yl)phenol
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-06-02 deposited with the CCDC.
2017-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.364(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6542(8)
_cell_length_b                   6.7364(4)
_cell_length_c                   18.7735(12)
_cell_measurement_reflns_used    1580
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      41.692
_cell_measurement_theta_min      4.460
_cell_volume                     1556.99(17)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_sigmaI/netI    0.0890
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16946
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.7857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.99
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0623
_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)+(0.0408P)²+0.9274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                2134
_reflns_number_total             3568
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c7ob02729j2.cif
_cod_data_source_block           is_mm251
_cod_depositor_comments
'Adding full bibliography for 7156036--7156039.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7156036
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Cl1 Cl 0.42858(6) 0.82456(14) 0.55848(4) 0.0347(2) Uani 1 1 d .
N1 N 0.12690(19) 0.7533(3) 0.58788(12) 0.0190(5) Uani 1 1 d .
N2 N -0.03645(19) 0.7330(4) 0.48937(13) 0.0221(6) Uani 1 1 d .
N3 N -0.0598(2) 0.7423(4) 0.41385(13) 0.0259(6) Uani 1 1 d .
O1 O 0.2163(2) 0.4666(3) 0.70484(13) 0.0365(6) Uani 1 1 d .
C1 C 0.2349(2) 0.7822(4) 0.60018(15) 0.0205(6) Uani 1 1 d .
C2 C 0.2878(2) 0.8095(4) 0.54209(15) 0.0214(6) Uani 1 1 d .
C3 C 0.2305(2) 0.8121(4) 0.47000(15) 0.0232(7) Uani 1 1 d .
H3 H 0.2659 0.8289 0.4310 0.028 Uiso 1 1 calc R
C4 C 0.1194(2) 0.7891(4) 0.45730(15) 0.0211(7) Uani 1 1 d .
C5 C 0.0315(3) 0.7769(4) 0.39424(16) 0.0246(7) Uani 1 1 d .
C6 C 0.0732(2) 0.7597(4) 0.51731(15) 0.0193(6) Uani 1 1 d .
C7 C 0.0364(3) 0.7956(5) 0.31572(15) 0.0354(9) Uani 1 1 d .
H7A H -0.0360 0.7726 0.2843 0.053 Uiso 1 1 calc R
H7B H 0.0873 0.6973 0.3045 0.053 Uiso 1 1 calc R
H7C H 0.0611 0.9293 0.3068 0.053 Uiso 1 1 calc R
C8 C 0.2954(2) 0.7805(4) 0.67831(15) 0.0214(7) Uani 1 1 d .
C9 C 0.3663(2) 0.9347(5) 0.70590(17) 0.0295(8) Uani 1 1 d .
H9 H 0.3733 1.0430 0.6749 0.035 Uiso 1 1 calc R
C10 C 0.4268(3) 0.9340(5) 0.77754(17) 0.0341(8) Uani 1 1 d .
H10 H 0.4747 1.0406 0.7955 0.041 Uiso 1 1 calc R
C11 C 0.4166(3) 0.7759(5) 0.82253(16) 0.0319(8) Uani 1 1 d .
H11 H 0.4590 0.7725 0.8714 0.038 Uiso 1 1 calc R
C12 C 0.3452(2) 0.6230(5) 0.79678(16) 0.0289(8) Uani 1 1 d .
H12 H 0.3382 0.5158 0.8282 0.035 Uiso 1 1 calc R
C13 C 0.2833(2) 0.6253(5) 0.72481(15) 0.0240(7) Uani 1 1 d .
C14 C -0.1238(2) 0.7100(4) 0.52459(16) 0.0219(7) Uani 1 1 d .
C15 C -0.2294(2) 0.6982(4) 0.48090(17) 0.0257(7) Uani 1 1 d .
H15 H -0.2417 0.7049 0.4291 0.031 Uiso 1 1 calc R
C16 C -0.3156(3) 0.6765(5) 0.51408(18) 0.0323(8) Uani 1 1 d .
H16 H -0.3874 0.6670 0.4846 0.039 Uiso 1 1 calc R
C17 C -0.2989(3) 0.6685(5) 0.58930(18) 0.0317(8) Uani 1 1 d .
H17 H -0.3586 0.6536 0.6116 0.038 Uiso 1 1 calc R
C18 C -0.1941(3) 0.6824(5) 0.63198(17) 0.0307(8) Uani 1 1 d .
H18 H -0.1822 0.6777 0.6838 0.037 Uiso 1 1 calc R
C19 C -0.1066(2) 0.7030(5) 0.59992(16) 0.0261(7) Uani 1 1 d .
H19 H -0.0350 0.7123 0.6296 0.031 Uiso 1 1 calc R
H1 H 0.172(3) 0.477(6) 0.664(2) 0.077(15) 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'
Cl Cl 0.1484 0.1585 '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
C6 N1 C1 115.3(2)
C6 N2 N3 110.1(2)
C6 N2 C14 131.3(2)
N3 N2 C14 118.5(2)
C5 N3 N2 107.6(2)
C13 O1 H1 116(3)
N1 C1 C2 121.9(2)
N1 C1 C8 116.0(3)
C2 C1 C8 122.1(3)
C3 C2 C1 121.4(3)
C3 C2 Cl1 117.2(2)
C1 C2 Cl1 121.2(2)
C4 C3 C2 116.9(3)
C4 C3 H3 121.6
C2 C3 H3 121.6
C3 C4 C6 118.4(3)
C3 C4 C5 135.9(3)
C6 C4 C5 105.6(3)
N3 C5 C4 110.2(3)
N3 C5 C7 122.1(3)
C4 C5 C7 127.7(3)
N1 C6 N2 127.4(3)
N1 C6 C4 126.1(3)
N2 C6 C4 106.5(2)
C5 C7 H7A 109.5
C5 C7 H7B 109.5
H7A C7 H7B 109.5
C5 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 118.8(3)
C9 C8 C1 120.1(3)
C13 C8 C1 121.1(3)
C10 C9 C8 121.5(3)
C10 C9 H9 119.2
C8 C9 H9 119.2
C11 C10 C9 119.1(3)
C11 C10 H10 120.4
C9 C10 H10 120.4
C12 C11 C10 120.4(3)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C13 120.4(3)
C11 C12 H12 119.8
C13 C12 H12 119.8
O1 C13 C8 124.6(3)
O1 C13 C12 115.6(3)
C8 C13 C12 119.7(3)
C19 C14 C15 120.1(3)
C19 C14 N2 121.6(3)
C15 C14 N2 118.3(3)
C16 C15 C14 119.2(3)
C16 C15 H15 120.4
C14 C15 H15 120.4
C17 C16 C15 121.0(3)
C17 C16 H16 119.5
C15 C16 H16 119.5
C16 C17 C18 119.3(3)
C16 C17 H17 120.3
C18 C17 H17 120.3
C17 C18 C19 120.7(3)
C17 C18 H18 119.7
C19 C18 H18 119.7
C14 C19 C18 119.7(3)
C14 C19 H19 120.1
C18 C19 H19 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.739(3)
N1 C6 1.343(3)
N1 C1 1.346(4)
N2 C6 1.377(3)
N2 N3 1.381(3)
N2 C14 1.421(4)
N3 C5 1.312(4)
O1 C13 1.362(4)
O1 H1 0.84(4)
C1 C2 1.418(4)
C1 C8 1.490(4)
C2 C3 1.380(4)
C3 C4 1.380(4)
C3 H3 0.9500
C4 C6 1.398(4)
C4 C5 1.427(4)
C5 C7 1.495(4)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.392(4)
C8 C13 1.393(4)
C9 C10 1.385(4)
C9 H9 0.9500
C10 C11 1.384(5)
C10 H10 0.9500
C11 C12 1.382(4)
C11 H11 0.9500
C12 C13 1.397(4)
C12 H12 0.9500
C14 C19 1.381(4)
C14 C15 1.399(4)
C15 C16 1.383(4)
C15 H15 0.9500
C16 C17 1.380(4)
C16 H16 0.9500
C17 C18 1.384(4)
C17 H17 0.9500
C18 C19 1.385(4)
C18 H18 0.9500
C19 H19 0.9500
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
C6 N2 N3 C5 -1.0(3)
C14 N2 N3 C5 175.8(2)
C6 N1 C1 C2 -2.4(4)
C6 N1 C1 C8 178.5(2)
N1 C1 C2 C3 1.4(4)
C8 C1 C2 C3 -179.5(3)
N1 C1 C2 Cl1 -174.2(2)
C8 C1 C2 Cl1 4.8(4)
C1 C2 C3 C4 0.7(4)
Cl1 C2 C3 C4 176.5(2)
C2 C3 C4 C6 -1.7(4)
C2 C3 C4 C5 -177.8(3)
N2 N3 C5 C4 0.7(3)
N2 N3 C5 C7 179.8(3)
C3 C4 C5 N3 176.1(3)
C6 C4 C5 N3 -0.3(3)
C3 C4 C5 C7 -2.9(6)
C6 C4 C5 C7 -179.3(3)
C1 N1 C6 N2 179.2(3)
C1 N1 C6 C4 1.3(4)
N3 N2 C6 N1 -177.4(3)
C14 N2 C6 N1 6.4(5)
N3 N2 C6 C4 0.8(3)
C14 N2 C6 C4 -175.4(3)
C3 C4 C6 N1 0.7(4)
C5 C4 C6 N1 177.9(3)
C3 C4 C6 N2 -177.5(3)
C5 C4 C6 N2 -0.3(3)
N1 C1 C8 C9 -129.4(3)
C2 C1 C8 C9 51.6(4)
N1 C1 C8 C13 51.2(4)
C2 C1 C8 C13 -127.9(3)
C13 C8 C9 C10 1.8(5)
C1 C8 C9 C10 -177.6(3)
C8 C9 C10 C11 0.2(5)
C9 C10 C11 C12 -1.4(5)
C10 C11 C12 C13 0.6(5)
C9 C8 C13 O1 179.6(3)
C1 C8 C13 O1 -1.0(5)
C9 C8 C13 C12 -2.6(5)
C1 C8 C13 C12 176.8(3)
C11 C12 C13 O1 179.4(3)
C11 C12 C13 C8 1.4(5)
C6 N2 C14 C19 -2.9(5)
N3 N2 C14 C19 -178.9(3)
C6 N2 C14 C15 175.9(3)
N3 N2 C14 C15 -0.1(4)
C19 C14 C15 C16 -0.9(4)
N2 C14 C15 C16 -179.8(3)
C14 C15 C16 C17 0.7(5)
C15 C16 C17 C18 0.0(5)
C16 C17 C18 C19 -0.4(5)
C15 C14 C19 C18 0.6(4)
N2 C14 C19 C18 179.4(3)
C17 C18 C19 C14 0.1(5)
