One-Pot Synthesis of Densely Substituted Pyrazolo[3,4-b]-4,7-dihydropyridines.
Rao, H. Surya Prakash; Adigopula, Lakshmi Narayana; Ramadas, Krishna; ACS combinatorial science 19 (2017) 279–285; doi:10.1021/acscombsci.6b00156

data_4514150
_publ_section_title
;
 One-Pot Synthesis of Densely Substituted
 Pyrazolo[3,4-b]-4,7-dihydropyridines.
;
_journal_issue                   5
_journal_name_full               'ACS combinatorial science'
_journal_page_first              279
_journal_page_last               285
_journal_paper_doi               10.1021/acscombsci.6b00156
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C19 H17.65 N5 O3, C19 H18.29 N5 O3'
_chemical_formula_sum            'C38 H35.94 N10 O6'
_chemical_formula_weight         728.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                86.351(7)
_cell_angle_beta                 72.539(8)
_cell_angle_gamma                78.203(7)
_cell_formula_units_Z            2
_cell_length_a                   11.3633(9)
_cell_length_b                   12.4790(10)
_cell_length_c                   16.6341(17)
_cell_measurement_reflns_used    3677
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.1159
_cell_measurement_theta_min      3.8290
_cell_volume                     2202.5(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21029
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.180
_diffrn_reflns_theta_min         3.837
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_description       plate
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.197
_refine_ls_extinction_coef       0.077(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.492
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         9939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.492
_refine_ls_R_factor_all          0.2104
_refine_ls_R_factor_gt           0.1598
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4485
_refine_ls_wR_factor_ref         0.4731
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4977
_reflns_number_total             9939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co6b00156_si_002.cif
_cod_data_source_block           hsp-aln-i-313_sqd
_cod_database_code               4514150
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(H31)=Sof(H50A)=Sof(H50B)=Sof(O3)=Sof(H3)=Sof(O4)=Sof(H4A)=1-FVAR(1)
 Sof(H45)=Sof(O47)=Sof(O48)=Sof(H51)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C19(H19), C24(H24)
3.b Secondary CH2 refined with riding coordinates:
 C50(H50A,H50B)
3.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N7(H7), N10(H10), N12(H12), N13(H13), N15(H15), N18(H18), C31(H31),
 C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41),
  C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C51(H51), C53(H53),
 C54(H54), C55(H55), C56(H56)
3.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C33(H33A,H33B,H33C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4A)
;
_shelx_res_checksum              67257
_shelx_hkl_checksum              38256
_platon_squeeze_void_probe_radius 1.20