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_7158646
_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 H17 Cl N2 O3'
_chemical_formula_sum            'C26 H17 Cl N2 O3'
_chemical_formula_weight         440.88
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-04 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.647(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8370(2)
_cell_length_b                   10.83450(10)
_cell_length_c                   16.2470(2)
_cell_measurement_reflns_used    7441
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.1860
_cell_measurement_theta_min      5.0200
_cell_volume                     2085.44(5)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_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    -44.00   1.00   0.50    1.55    --    0.00 -37.00-180.00   90
  2  \w    -30.00  59.00   0.50    1.55    --    0.00  77.00 -60.00  178
  3  \w    -80.00   7.00   0.50    1.55    --    0.00 -37.00 -90.00  174
  4  \w     21.00 138.00   0.50    6.20    --  107.20 -82.00 -30.00  234
  5  \w    101.00 127.00   0.50    6.20    --  107.20 -82.00 150.00   52
  6  \w     37.00 113.00   0.50    6.20    --  107.20 -82.00-180.00  152
  7  \w     54.00 124.00   0.50    6.20    --  107.20 -82.00-120.00  140
  8  \w     22.00  55.00   0.50    6.20    --  107.20 -30.00 -60.00   66
  9  \w     89.00 195.00   0.50    6.20    --  107.20  30.00 -90.00  212
 10  \w     30.00  82.00   0.50    6.20    --  107.20 -82.00 150.00  104
 11  \w     18.00 129.00   0.50    6.20    --  107.20 -61.00  30.00  222
 12  \w    108.00 194.00   0.50    6.20    --  107.20  45.00 150.00  172
;
_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      0.0613255000
_diffrn_orient_matrix_UB_12      -0.0279544000
_diffrn_orient_matrix_UB_13      -0.0628692000
_diffrn_orient_matrix_UB_21      0.0066435000
_diffrn_orient_matrix_UB_22      -0.1375127000
_diffrn_orient_matrix_UB_23      0.0256494000
_diffrn_orient_matrix_UB_31      -0.1144523000
_diffrn_orient_matrix_UB_32      -0.0230480000
_diffrn_orient_matrix_UB_33      -0.0770943000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13423
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.974
_diffrn_reflns_theta_min         5.036
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.889
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77365
_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            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.9611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4054
_reflns_number_total             4437
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02351a2.cif
_cod_data_source_block           exp-880_tp-19b
_cod_depositor_comments
;

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11.56 H7.56 Cl0.44 N0.89 O1.33'
_cod_original_formula_weight         195.94
_cod_original_formula_moiety         '0.44(C26 H17 Cl N2 O3)'
_cod_original_formula_units_Z            9
_cod_database_code               7158646
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.834
_reflns_odcompleteness_completeness 99.93
_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:
 C10C(H10C)
2.b Aromatic/amide H refined with riding coordinates:
 C3C(H3C), C4C(H4C), C5C(H5C), C6C(H6C), C14C(H14C), C15C(H15C), C17C(H17C),
 C18C(H18C), C22C(H22C), C23C(H23C), C24C(H24C), C25C(H25C), C26C(H26C)
2.c Idealised Me refined as rotating group:
 C20C(H20A,H20B,H20C)
;
_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 1.806
_oxdiff_exptl_absorpt_empirical_full_min 0.746