Substituent-Oriented Synthesis of Substituted Pyrazoles/Chromeno[3,2- c]pyrazoles via Sequential Reactions of Chromones/3-Chlorochromones and Tosylhydrazones.
Dai, Tianzi; Li, Qunyi; Zhang, Xiaofei; Yang, Chunhao; The Journal of organic chemistry 84 (2019) 5913–5921; doi:10.1021/acs.joc.9b00282

data_4034381
_publ_section_title
;
 Substituent-Oriented Synthesis of Substituted Pyrazoles/Chromeno[3,2-
 c]pyrazoles via Sequential Reactions of Chromones/3-Chlorochromones and
 Tosylhydrazones.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5913
_journal_page_last               5921
_journal_paper_doi               10.1021/acs.joc.9b00282
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C16 H10 N2 O2'
_chemical_formula_sum            'C16 H10 N2 O2'
_chemical_formula_weight         262.26
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   37.313(3)
_cell_length_b                   37.313(3)
_cell_length_c                   4.8514(5)
_cell_measurement_reflns_used    2642
_cell_measurement_temperature    297
_cell_measurement_theta_max      63.621
_cell_measurement_theta_min      2.368
_cell_volume                     5849.5(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.01
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6587
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        63.863
_diffrn_reflns_theta_max         63.863
_diffrn_reflns_theta_min         2.368
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.3928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1104 before and 0.0739 after correction. The Ratio of minimum to maximum transmission is 0.5221. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       needle
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_platon_squeeze_details
;
TITL 20181002-d1015_0m_a.res in R-3
CELL   37.3140   37.3140    4.8514     90.00     90.00    120.00
SPGR R-3
C101 1.000 1.000 0.500 !       1.65 eA-3
C102 1.001 0.999 0.127 !       1.35 eA-3
Q103 0.619 0.983 0.927 !       0.53 eA-3
Q104 0.957 0.968 0.131 !       0.51 eA-3
;
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0808
_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^)+(0.0920P)^2^+9.0727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1945
_refine_ls_wR_factor_ref         0.2233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1229
_reflns_number_total             2111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00282_si_003.cif
_cod_data_source_block           20181002-d1015_0m_sq
_cod_original_cell_volume        5849.6(12)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4034381
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C15(H15), C12(H12), C14(H14), C13(H13), C1(H1), C5(H5), C4(H4),
 C3(H3), C2(H2A)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'