Multicomponent Dipolar Cycloaddition Strategy: Combinatorial Synthesis of Novel Spiro-Tethered Pyrazolo[3,4-b]quinoline Hybrid Heterocycles.
Sumesh, Remani Vasudevan; Muthu, Muthumani; Almansour, Abdulrahman I.; Suresh Kumar, Raju; Arumugam, Natarajan; Athimoolam, S.; Jeya Yasmi Prabha, E. Arockia; Kumar, Raju Ranjith; ACS combinatorial science 18 (2016) 262–270; doi:10.1021/acscombsci.6b00003

data_4513898
_publ_section_title
;
 Multicomponent Dipolar Cycloaddition Strategy: Combinatorial Synthesis of
 Novel Spiro-Tethered Pyrazolo[3,4-b]quinoline Hybrid Heterocycles.
;
_journal_issue                   5
_journal_name_full               'ACS combinatorial science'
_journal_page_first              262
_journal_page_last               270
_journal_paper_doi               10.1021/acscombsci.6b00003
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C17 H15 N3 O'
_chemical_formula_sum            'C17 H15 N3 O'
_chemical_formula_weight         277.32
_chemical_melting_point          101
_chemical_name_common
;
3-methyl-1-phenyl-1,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one
;
_chemical_name_systematic
;
3-Methyl-1-phenyl-1,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 99.3660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   13.6926(10)
_cell_length_b                   18.4002(13)
_cell_length_c                   22.7816(17)
_cell_measurement_reflns_used    2622
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.45
_cell_measurement_theta_min      2.56
_cell_volume                     5663.2(7)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            53873
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.430
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     779
_refine_ls_number_reflns         9971
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1026P)^2^+1.7264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6185
_reflns_number_total             9971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co6b00003_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               4513898
_shelxl_version_number           2014-3
_shelx_res_checksum              15228
_shelx_hkl_checksum              4338