#------------------------------------------------------------------------------
#$Date: 2022-04-20 04:06:07 +0300 (Wed, 20 Apr 2022) $
#$Revision: 274599 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158645.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158645
loop_
_publ_author_name
'Penjarla, Thirupathi Reddy'
'Shukla, Adarash Kumar'
'Hazra, Rituparna'
'Roy, Durba'
'Kundarapu, Maheshwar'
'Dixit, Mudit'
'Bhattacharya, Anupam'
_publ_section_title
;
 Copper acetate catalysed C--C bond formation en route to the synthesis of
 spiro indanedione cyclopropylpyrazolones
;
_journal_name_full               'Organic & 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00   1.00   0.50    1.44    --    0.00  82.00  60.00   66
  2  ω    -20.00  16.00   0.50    1.44    --    0.00 -57.00  30.00   72
  3  ω    -85.00 -49.00   0.50    1.44    --    0.00 -57.00  30.00   72
  4  ω      8.00  75.00   0.50    1.44    --    0.00  82.00  60.00  134
  5  ω    -20.00  29.00   0.50    1.44    --    0.00 -82.00   0.00   98
  6  ω    -84.00 -29.00   0.50    1.44    --    0.00 -82.00   0.00  110
  7  ω     38.00 106.00   0.50    5.75    --  107.20 -61.00 -60.00  136
  8  ω     82.00 159.00   0.50    5.75    --  107.20  15.00   0.00  154
  9  ω     40.00 135.00   0.50    5.75    --  107.20 -82.00-180.00  190
 10  ω     18.00  78.00   0.50    5.75    --  107.20 -77.00 120.00  120
 11  ω     98.00 197.00   0.50    5.75    --  107.20  30.00  30.00  198
 12  ω     62.00 132.00   0.50    5.75    --  107.20 -82.00 -90.00  140
 13  ω    125.00 151.00   0.50    5.75    --  107.20  45.00 -90.00   52
 14  ω    170.00 196.00   0.50    5.75    --  107.20  45.00 -90.00   52
 15  ω     89.00 196.00   0.50    5.75    --  107.20  30.00  60.00  214
 16  ω     85.00 136.00   0.50    5.75    --  107.20 -82.00  60.00  102
 17  ω     35.00  79.00   0.50    5.75    --  107.20 -82.00  60.00   88
 18  ω     37.00  88.00   0.50    5.75    --  107.20 -45.00  30.00  102
 19  ω     19.00 134.00   0.50    5.75    --  107.20 -15.00  60.00  230
 20  ω     84.00 110.00   0.50    5.75    --  107.20 -82.00-150.00   52
 21  ω     23.00 130.00   0.50    5.75    --  107.20 -61.00-180.00  214
 22  ω     79.00 104.00   0.50    5.75    --  107.20 -82.00 -60.00   50
 23  ω     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       'ω 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/[σ²(Fo²)+(0.0514P)²+1.2273P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1O O -0.3141(2) 0.0039(2) 0.21425(12) 0.0333(4) Uani 1 1 d . . . . .
N2N N 0.2222(2) 0.3797(2) 0.35272(12) 0.0228(4) Uani 1 1 d . . . . .
O2O O 0.1213(2) 0.1781(2) 0.04201(11) 0.0311(4) Uani 1 1 d . . . . .
N1N N 0.1009(2) 0.3156(2) 0.40644(13) 0.0233(4) Uani 1 1 d . . . . .
O3O O 0.3228(2) 0.2964(2) 0.21358(12) 0.0362(4) Uani 1 1 d . . . . .
C19C C 0.3350(3) 0.5251(2) 0.39358(15) 0.0235(4) Uani 1 1 d . . . . .
C18C C 0.0125(3) 0.1845(2) 0.35803(15) 0.0221(4) Uani 1 1 d . . . . .
C16C C -0.0023(3) 0.1743(3) 0.07924(15) 0.0248(4) Uani 1 1 d . . . . .
C C -0.1201(3) 0.0914(3) 0.40387(16) 0.0266(5) Uani 1 1 d . . . . .
HA H -0.116248 0.141924 0.468361 0.040 Uiso 1 1 calc GR . . . .
HB H -0.105366 -0.016902 0.403505 0.040 Uiso 1 1 calc GR . . . .
HC H -0.223816 0.089301 0.369256 0.040 Uiso 1 1 calc GR . . . .
C14C C -0.1699(3) 0.3199(3) -0.02977(16) 0.0325(5) Uani 1 1 d . . . . .
H14C H -0.083391 0.359621 -0.062071 0.039 Uiso 1 1 calc R . . . .
C20C C 0.3399(3) 0.5828(3) 0.48964(16) 0.0263(5) Uani 1 1 d . . . . .
H20C H 0.270441 0.526821 0.526803 0.032 Uiso 1 1 calc R . . . .
C9C C -0.2263(3) 0.0782(3) 0.16510(15) 0.0255(4) Uani 1 1 d . . . . .
C10C C -0.2801(3) 0.1682(3) 0.09020(15) 0.0259(5) Uani 1 1 d . . . . .
C6C C -0.0156(3) -0.1701(2) 0.23359(15) 0.0233(4) Uani 1 1 d . . . . .
C1C C 0.0501(3) -0.2168(3) 0.31568(16) 0.0269(5) Uani 1 1 d . . . . .
H1C H 0.140502 -0.149422 0.352976 0.032 Uiso 1 1 calc R . . . .
C17C C 0.0710(3) 0.1490(2) 0.26418(15) 0.0234(4) Uani 1 1 d . . . . .
C25C C 0.2220(3) 0.2817(3) 0.26918(15) 0.0246(4) Uani 1 1 d . . . . .
C8C C -0.0437(3) 0.0959(2) 0.16611(15) 0.0231(4) Uani 1 1 d . . . . .
C21C C 0.4498(3) 0.7250(3) 0.52956(17) 0.0293(5) Uani 1 1 d . . . . .
H21C H 0.453706 0.764004 0.593822 0.035 Uiso 1 1 calc R . . . .
C15C C -0.1500(3) 0.2284(3) 0.04286(15) 0.0262(5) Uani 1 1 d . . . . .
C11C C -0.4354(3) 0.1944(3) 0.06682(17) 0.0305(5) Uani 1 1 d . . . . .
H11C H -0.522617 0.152048 0.097889 0.037 Uiso 1 1 calc R . . . .
C5C C -0.1464(3) -0.2752(3) 0.17657(15) 0.0262(5) Uani 1 1 d . . . . .
H5C H -0.189597 -0.246076 0.120698 0.031 Uiso 1 1 calc R . . . .
C24C C 0.4383(3) 0.6085(3) 0.33777(17) 0.0320(5) Uani 1 1 d . . . . .
H24C H 0.434769 0.569731 0.273491 0.038 Uiso 1 1 calc R . . . .
C4C C -0.2135(3) -0.4236(3) 0.20231(16) 0.0295(5) Uani 1 1 d . . . . .
H4C H -0.300659 -0.493545 0.163618 0.035 Uiso 1 1 calc R . . . .
C2C C -0.0186(3) -0.3636(3) 0.34242(16) 0.0291(5) Uani 1 1 d . . . . .
H2C H 0.023652 -0.392668 0.398538 0.035 Uiso 1 1 calc R . . . .
C22C C 0.5535(3) 0.8092(3) 0.47464(19) 0.0335(5) Uani 1 1 d . . . . .
H22C H 0.626671 0.904303 0.501759 0.040 Uiso 1 1 calc R . . . .
C3C C -0.1500(3) -0.4665(3) 0.28543(16) 0.0285(5) Uani 1 1 d . . . . .
H3C H -0.195553 -0.564856 0.303269 0.034 Uiso 1 1 calc R . . . .
C13C C -0.3235(4) 0.3493(3) -0.05190(18) 0.0392(6) Uani 1 1 d . . . . .
H13C H -0.339738 0.412029 -0.098975 0.047 Uiso 1 1 calc R . . . .
C12C C -0.4544(3) 0.2866(3) -0.00492(18) 0.0375(6) Uani 1 1 d . . . . .
H12C H -0.556420 0.307047 -0.022045 0.045 Uiso 1 1 calc R . . . .
C23C C 0.5472(3) 0.7506(3) 0.37920(19) 0.0372(6) Uani 1 1 d . . . . .
H23C H 0.616674 0.806864 0.342183 0.045 Uiso 1 1 calc R . . . .
C7C C 0.0579(3) -0.0127(2) 0.20372(14) 0.0227(4) Uani 1 1 d . . . . .
H7C H 0.153211 -0.017643 0.170114 0.027 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1N N2N C19C 118.13(17) . . ?
C25C N2N N1N 112.78(16) . . ?
C25C N2N C19C 128.84(17) . . ?
C18C N1N N2N 108.87(17) . . ?
C20C C19C N2N 119.25(18) . . ?
C24C C19C N2N 120.20(19) . . ?
C24C C19C C20C 120.55(19) . . ?
N1N C18C C 117.93(19) . . ?
N1N C18C C17C 110.86(18) . . ?
C17C C18C C 131.11(18) . . ?
O2O C16C C8C 126.3(2) . . ?
O2O C16C C15C 126.7(2) . . ?
C15C C16C C8C 106.64(18) . . ?
C13C C14C C15C 117.5(2) . . ?
C19C C20C C21C 119.3(2) . . ?
O1O C9C C10C 125.7(2) . . ?
O1O C9C C8C 127.5(2) . . ?
C10C C9C C8C 106.77(17) . . ?
C15C C10C C9C 110.39(19) . . ?
C15C C10C C11C 121.8(2) . . ?
C11C C10C C9C 127.9(2) . . ?
C1C C6C C5C 119.05(19) . . ?
C1C C6C C7C 120.89(19) . . ?
C5C C6C C7C 119.99(19) . . ?
C6C C1C C2C 120.4(2) . . ?
C18C C17C C25C 103.04(17) . . ?
C18C C17C C8C 124.44(18) . . ?
C18C C17C C7C 128.76(18) . . ?
C25C C17C C8C 117.99(17) . . ?
C7C C17C C25C 120.16(18) . . ?
C7C C17C C8C 57.97(13) . . ?
N2N C25C C17C 103.98(17) . . ?
O3O C25C N2N 127.52(19) . . ?
O3O C25C C17C 128.5(2) . . ?
C16C C8C C17C 120.98(17) . . ?
C9C C8C C16C 105.17(18) . . ?
C9C C8C C17C 119.36(17) . . ?
C7C C8C C16C 120.42(18) . . ?
C7C C8C C9C 126.82(18) . . ?
C7C C8C C17C 58.63(13) . . ?
C22C C21C C20C 120.7(2) . . ?
C14C C15C C16C 129.1(2) . . ?
C10C C15C C16C 109.86(19) . . ?
C10C C15C C14C 121.0(2) . . ?
C12C C11C C10C 117.1(2) . . ?
C6C C5C C4C 120.6(2) . . ?
C19C C24C C23C 119.2(2) . . ?
C3C C4C C5C 119.7(2) . . ?
C3C C2C C1C 120.0(2) . . ?
C23C C22C C21C 119.4(2) . . ?
C4C C3C C2C 120.2(2) . . ?
C14C C13C C12C 121.3(2) . . ?
C11C C12C C13C 121.4(2) . . ?
C22C C23C C24C 120.9(2) . . ?
C6C C7C C17C 123.32(18) . . ?
C6C C7C C8C 122.60(18) . . ?
C8C C7C C17C 63.40(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1O C9C 1.212(3) . ?
N2N N1N 1.402(2) . ?
N2N C19C 1.423(3) . ?
N2N C25C 1.366(3) . ?
O2O C16C 1.211(3) . ?
N1N C18C 1.288(3) . ?
O3O C25C 1.216(3) . ?
C19C C20C 1.390(3) . ?
C19C C24C 1.389(3) . ?
C18C C 1.492(3) . ?
C18C C17C 1.487(3) . ?
C16C C8C 1.520(3) . ?
C16C C15C 1.488(3) . ?
C14C C15C 1.396(3) . ?
C14C C13C 1.385(4) . ?
C20C C21C 1.390(3) . ?
C9C C10C 1.485(3) . ?
C9C C8C 1.517(3) . ?
C10C C15C 1.388(3) . ?
C10C C11C 1.392(3) . ?
C6C C1C 1.389(3) . ?
C6C C5C 1.390(3) . ?
C6C C7C 1.498(3) . ?
C1C C2C 1.391(3) . ?
C17C C25C 1.516(3) . ?
C17C C8C 1.583(3) . ?
C17C C7C 1.512(3) . ?
C8C C7C 1.501(3) . ?
C21C C22C 1.386(3) . ?
C11C C12C 1.388(4) . ?
C5C C4C 1.393(3) . ?
C24C C23C 1.391(3) . ?
C4C C3C 1.380(3) . ?
C2C C3C 1.385(3) . ?
C22C C23C 1.382(4) . ?
C13C C12C 1.396(4) . ?
