Copper acetate catalysed C–C bond formation en route to the synthesis of spiro indanedione cyclopropylpyrazolones
Penjarla, Thirupathi Reddy; Shukla, Adarash Kumar; Hazra, Rituparna; Roy, Durba; Kundarapu, Maheshwar; Dixit, Mudit; Bhattacharya, Anupam; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D1OB02351A

data_7158645
_publ_section_title
;
 Copper acetate catalysed C--C bond formation en route to the synthesis of
 spiro indanedione cyclopropylpyrazolones
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB02351A
_journal_year                    2022
_chemical_formula_moiety         'C26 H18 N2 O3'
_chemical_formula_sum            'C26 H18 N2 O3'
_chemical_formula_weight         406.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-24 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                97.421(2)
_cell_angle_beta                 95.373(2)
_cell_angle_gamma                101.685(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4393(2)
_cell_length_b                   8.56590(10)
_cell_length_c                   14.2744(4)
_cell_measurement_reflns_used    6208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.0150
_cell_measurement_theta_min      5.3750
_cell_volume                     994.40(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -32.00   1.00   0.50    1.44    --    0.00  82.00  60.00   66
  2  \w    -20.00  16.00   0.50    1.44    --    0.00 -57.00  30.00   72
  3  \w    -85.00 -49.00   0.50    1.44    --    0.00 -57.00  30.00   72
  4  \w      8.00  75.00   0.50    1.44    --    0.00  82.00  60.00  134
  5  \w    -20.00  29.00   0.50    1.44    --    0.00 -82.00   0.00   98
  6  \w    -84.00 -29.00   0.50    1.44    --    0.00 -82.00   0.00  110
  7  \w     38.00 106.00   0.50    5.75    --  107.20 -61.00 -60.00  136
  8  \w     82.00 159.00   0.50    5.75    --  107.20  15.00   0.00  154
  9  \w     40.00 135.00   0.50    5.75    --  107.20 -82.00-180.00  190
 10  \w     18.00  78.00   0.50    5.75    --  107.20 -77.00 120.00  120
 11  \w     98.00 197.00   0.50    5.75    --  107.20  30.00  30.00  198
 12  \w     62.00 132.00   0.50    5.75    --  107.20 -82.00 -90.00  140
 13  \w    125.00 151.00   0.50    5.75    --  107.20  45.00 -90.00   52
 14  \w    170.00 196.00   0.50    5.75    --  107.20  45.00 -90.00   52
 15  \w     89.00 196.00   0.50    5.75    --  107.20  30.00  60.00  214
 16  \w     85.00 136.00   0.50    5.75    --  107.20 -82.00  60.00  102
 17  \w     35.00  79.00   0.50    5.75    --  107.20 -82.00  60.00   88
 18  \w     37.00  88.00   0.50    5.75    --  107.20 -45.00  30.00  102
 19  \w     19.00 134.00   0.50    5.75    --  107.20 -15.00  60.00  230
 20  \w     84.00 110.00   0.50    5.75    --  107.20 -82.00-150.00   52
 21  \w     23.00 130.00   0.50    5.75    --  107.20 -61.00-180.00  214
 22  \w     79.00 104.00   0.50    5.75    --  107.20 -82.00 -60.00   50
 23  \w     35.00 120.00   0.50    5.75    --  107.20 -82.00 -12.21  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0180244000
_diffrn_orient_matrix_UB_12      -0.0004748000
_diffrn_orient_matrix_UB_13      0.1063733000
_diffrn_orient_matrix_UB_21      -0.1869533000
_diffrn_orient_matrix_UB_22      -0.0435085000
_diffrn_orient_matrix_UB_23      -0.0240404000
_diffrn_orient_matrix_UB_31      0.0030706000
_diffrn_orient_matrix_UB_32      -0.1806454000
_diffrn_orient_matrix_UB_33      -0.0116276000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10645
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.841
_diffrn_reflns_theta_min         5.335
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0514P)^2^+1.2273P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1588
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3766
_reflns_number_total             4180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02351a2.cif
_cod_data_source_block           exp_793_tp-abc-002a
_cod_original_cell_volume        994.39(4)
_cod_database_code               7158645
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C7C(H7C)
2.b Aromatic/amide H refined with riding coordinates:
 C14C(H14C), C20C(H20C), C1C(H1C), C21C(H21C), C11C(H11C), C5C(H5C),
 C24C(H24C), C4C(H4C), C2C(H2C), C22C(H22C), C3C(H3C), C13C(H13C), C12C(H12C),
 C23C(H23C)
2.c Idealised Me refined as rotating group:
 C(HA,HB,HC)
;
_shelx_res_checksum              44730
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.910
_oxdiff_exptl_absorpt_empirical_full_min 0.691