Synthesis of pyrazolo[5,1-a]isoquinolines through copper-catalyzed regioselective bicyclization of N-propargylic sulfonylhydrazones
Tang, Hai-Tao; Zeng, Jia-Hao; Chen, Jun-Jia; Zhou, Yun-Bing; Li, Ren-Hao; Zhan, Zhuang-Ping; Organic Chemistry Frontiers 4 (2017) 1513–; doi:10.1039/C7QO00249A

data_1553779
_publ_section_title
;
 Synthesis of pyrazolo[5,1-a]isoquinolines through copper-catalyzed
 regioselective bicyclization of N-propargylic sulfonylhydrazones
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1513
_journal_paper_doi               10.1039/C7QO00249A
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C21 H16 N2 O3'
_chemical_formula_sum            'C21 H16 N2 O3'
_chemical_formula_weight         344.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-03-21 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0348(7)
_cell_length_b                   21.2718(12)
_cell_length_c                   7.2221(6)
_cell_measurement_reflns_used    1090
_cell_measurement_temperature    184.3(3)
_cell_measurement_theta_max      28.5310
_cell_measurement_theta_min      3.5100
_cell_volume                     1695.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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      184.3(3)
_diffrn_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -47.00   -2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   57.0000  150.0000 45

  2 omega  -16.00   40.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   38.0000  -30.0000 56

  3 omega  -50.00   27.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   77.0000 -180.0000 77

  4 omega  -38.00   38.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   52.0000   48.0000 76
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0368903000
_diffrn_orient_matrix_UB_12      -0.0272179000
_diffrn_orient_matrix_UB_13      0.0063556000
_diffrn_orient_matrix_UB_21      -0.0162701000
_diffrn_orient_matrix_UB_22      0.0034709000
_diffrn_orient_matrix_UB_23      -0.0944466000
_diffrn_orient_matrix_UB_31      0.0500242000
_diffrn_orient_matrix_UB_32      -0.0189791000
_diffrn_orient_matrix_UB_33      -0.0261397000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6362
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.415
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 771 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0610
_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^)+(0.0534P)^2^+0.2789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    0.826
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                2472
_reflns_number_total             2770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00249a2.cif
_cod_data_source_block           tht160623-1
_cod_database_code               1553779
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00J(H00B,H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00Q(H00E,H00F,H00J)
;
_shelx_res_checksum              60409
_shelx_hkl_checksum              37115
_olex2_submission_special_instructions 'No special instructions were received'