Coumarin-3-formylpyrazoles as 3-carbon synthons in cyclocondensation for the synthesis of spiro-fused pentacyclic spirooxindoles.
Lei, Chuan-Wen; Zhang, Chuan-Bao; Wang, Zhen-Hua; Xie, Ke-Xin; Zhao, Jian-Qiang; Zhou, Ming-Qiang; Zhang, Xiao-Mei; Xu, Xiao-Ying; Yuan, Wei-Cheng; Organic & biomolecular chemistry 18 (2020) 845–850; doi:10.1039/c9ob02434d

data_7157277
_publ_section_title
;
 Coumarin-3-formylpyrazoles as 3-carbon synthons in cyclocondensation for
 the synthesis of spiro-fused pentacyclic spirooxindoles.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              845
_journal_page_last               850
_journal_paper_doi               10.1039/c9ob02434d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C19 H13 N O5'
_chemical_formula_sum            'C19 H13 N O5'
_chemical_formula_weight         335.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-17 deposited with the CCDC.	2019-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9043(5)
_cell_length_b                   10.8551(4)
_cell_length_c                   20.2244(7)
_cell_measurement_reflns_used    2471
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9870
_cell_measurement_theta_min      4.3550
_cell_volume                     3052.52(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -87.00  -47.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -150.0000 40

  2 omega  -51.00  -24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -30.0000 27

  3 omega  -66.00  -33.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 33

  4 omega   65.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 42

  5 omega   64.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 46

  6 omega   74.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 25

  7 omega   14.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -180.0000 90

  8 omega   74.00  102.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 28

  9 omega   40.00   70.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 30

 10 omega   39.00   85.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 46

 11 omega   92.00  176.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 84

 12 omega   37.00   62.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 25

 13 omega   37.00  115.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 78

 14 omega  118.00  148.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1039207000
_diffrn_orient_matrix_UB_12      -0.0132264000
_diffrn_orient_matrix_UB_13      -0.0253913000
_diffrn_orient_matrix_UB_21      -0.0382795000
_diffrn_orient_matrix_UB_22      -0.0442659000
_diffrn_orient_matrix_UB_23      -0.0673740000
_diffrn_orient_matrix_UB_31      -0.0022746000
_diffrn_orient_matrix_UB_32      0.1343017000
_diffrn_orient_matrix_UB_33      -0.0247815000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7243
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.372
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       prism
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.00145(16)
_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   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0638P)^2^+0.4398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2235
_reflns_number_total             2722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02434d2.cif
_cod_data_source_block           20190231
_cod_depositor_comments          'Adding full bibliography for 7157277.cif.'
_cod_database_code               7157277
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C28H31ON5
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.849
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C15(H15), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'