#------------------------------------------------------------------------------
#$Date: 2022-04-20 03:06:07 +0200 (Wed 20 de Apr de 2022) $
#$Revision: 274599 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/86/7158646.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_7158646
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         '0.44(C26 H17 Cl N2 O3)'
_chemical_formula_sum            'C11.56 H7.56 Cl0.44 N0.89 O1.33'
_chemical_formula_weight         195.94
_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            9
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00   1.00   0.50    1.55    --    0.00 -37.00-180.00   90
  2  ω    -30.00  59.00   0.50    1.55    --    0.00  77.00 -60.00  178
  3  ω    -80.00   7.00   0.50    1.55    --    0.00 -37.00 -90.00  174
  4  ω     21.00 138.00   0.50    6.20    --  107.20 -82.00 -30.00  234
  5  ω    101.00 127.00   0.50    6.20    --  107.20 -82.00 150.00   52
  6  ω     37.00 113.00   0.50    6.20    --  107.20 -82.00-180.00  152
  7  ω     54.00 124.00   0.50    6.20    --  107.20 -82.00-120.00  140
  8  ω     22.00  55.00   0.50    6.20    --  107.20 -30.00 -60.00   66
  9  ω     89.00 195.00   0.50    6.20    --  107.20  30.00 -90.00  212
 10  ω     30.00  82.00   0.50    6.20    --  107.20 -82.00 150.00  104
 11  ω     18.00 129.00   0.50    6.20    --  107.20 -61.00  30.00  222
 12  ω    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       'ω 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/[σ²(Fo²)+(0.0523P)²+0.9611P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            d1ob02351a2.cif
_cod_data_source_block           exp-880_tp-19b
_cod_database_code               7158646
_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.
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cl1C Cl 0.55775(4) -0.14754(4) 0.74194(3) 0.03959(14) Uani 1 1 d . . . . .
O1C O 0.97213(8) 0.40478(10) 0.56215(7) 0.0245(2) Uani 1 1 d . . . . .
O2C O 0.67409(9) 0.66869(10) 0.39360(7) 0.0269(2) Uani 1 1 d . . . . .
O3C O 0.81797(9) 0.20906(10) 0.53184(7) 0.0261(2) Uani 1 1 d . . . . .
N1N N 0.63931(10) 0.25471(12) 0.52762(8) 0.0242(3) Uani 1 1 d . . . . .
N2N N 0.54770(10) 0.32845(13) 0.47509(8) 0.0250(3) Uani 1 1 d . . . . .
C1C C 0.90174(11) 0.48571(13) 0.54375(9) 0.0195(3) Uani 1 1 d . . . . .
C2C C 0.91137(12) 0.60626(14) 0.58901(9) 0.0208(3) Uani 1 1 d . . . . .
C3C C 0.99436(13) 0.64687(15) 0.66858(10) 0.0257(3) Uani 1 1 d . . . . .
H3C H 1.050424 0.593764 0.704371 0.031 Uiso 1 1 calc R . . . .
C4C C 0.99068(13) 0.76919(17) 0.69274(11) 0.0309(4) Uani 1 1 d . . . . .
H4C H 1.044546 0.798306 0.745955 0.037 Uiso 1 1 calc R . . . .
C5C C 0.90757(14) 0.84886(16) 0.63849(11) 0.0317(4) Uani 1 1 d . . . . .
H5C H 0.908464 0.931056 0.655248 0.038 Uiso 1 1 calc R . . . .
C6C C 0.82354(13) 0.80853(15) 0.56010(10) 0.0267(3) Uani 1 1 d . . . . .
H6C H 0.767136 0.861572 0.524669 0.032 Uiso 1 1 calc R . . . .
C7C C 0.82677(12) 0.68570(14) 0.53642(9) 0.0211(3) Uani 1 1 d . . . . .
C8C C 0.75104(12) 0.62170(13) 0.45494(9) 0.0201(3) Uani 1 1 d . . . . .
C9C C 0.79072(11) 0.48906(13) 0.46277(9) 0.0184(3) Uani 1 1 d . . . . .
C10C C 0.76830(11) 0.40192(13) 0.38640(9) 0.0181(3) Uani 1 1 d . . . . .
H10C H 0.829162 0.341481 0.398273 0.022 Uiso 1 1 calc R . . . .
C11C C 0.70216(12) 0.38094(13) 0.44435(9) 0.0193(3) Uani 1 1 d . . . . .
C12C C 0.73288(12) 0.27195(13) 0.50717(9) 0.0206(3) Uani 1 1 d . . . . .
C13C C 0.61979(13) 0.15919(14) 0.57966(10) 0.0233(3) Uani 1 1 d . . . . .
C14C C 0.51038(14) 0.13176(17) 0.57044(12) 0.0319(4) Uani 1 1 d . . . . .
H14C H 0.450193 0.176547 0.530724 0.038 Uiso 1 1 calc R . . . .
C15C C 0.49066(14) 0.03776(18) 0.62028(12) 0.0350(4) Uani 1 1 d . . . . .
H15C H 0.417396 0.019809 0.614708 0.042 Uiso 1 1 calc R . . . .
C16C C 0.58039(14) -0.02921(15) 0.67835(11) 0.0286(3) Uani 1 1 d . . . . .
C17C C 0.68948(15) -0.00145(17) 0.68893(12) 0.0359(4) Uani 1 1 d . . . . .
H17C H 0.749379 -0.046412 0.728830 0.043 Uiso 1 1 calc R . . . .
C18C C 0.70991(14) 0.09360(17) 0.64004(12) 0.0356(4) Uani 1 1 d . . . . .
H18C H 0.783529 0.113396 0.647589 0.043 Uiso 1 1 calc R . . . .
C19C C 0.58039(12) 0.40087(14) 0.42683(9) 0.0215(3) Uani 1 1 d . . . . .
C20C C 0.49547(13) 0.48346(16) 0.36175(10) 0.0276(3) Uani 1 1 d . . . . .
H20A H 0.420943 0.457561 0.354563 0.041 Uiso 1 1 calc GR . . . .
H20B H 0.503097 0.479227 0.305309 0.041 Uiso 1 1 calc GR . . . .
H20C H 0.507639 0.566809 0.383425 0.041 Uiso 1 1 calc GR . . . .
C21C C 0.71808(11) 0.43915(13) 0.28997(9) 0.0183(3) Uani 1 1 d . . . . .
C22C C 0.76089(12) 0.54032(13) 0.26030(9) 0.0210(3) Uani 1 1 d . . . . .
H22C H 0.815475 0.590259 0.301058 0.025 Uiso 1 1 calc R . . . .
C23C C 0.72179(12) 0.56654(14) 0.16947(9) 0.0233(3) Uani 1 1 d . . . . .
H23C H 0.750964 0.633685 0.149730 0.028 Uiso 1 1 calc R . . . .
C24C C 0.63958(12) 0.49317(15) 0.10818(9) 0.0249(3) Uani 1 1 d . . . . .
H24C H 0.613099 0.511975 0.047719 0.030 Uiso 1 1 calc R . . . .
C25C C 0.59697(13) 0.39188(15) 0.13711(10) 0.0256(3) Uani 1 1 d . . . . .
H25C H 0.542374 0.342116 0.096204 0.031 Uiso 1 1 calc R . . . .
C26C C 0.63656(12) 0.36524(14) 0.22789(10) 0.0225(3) Uani 1 1 d . . . . .
H26C H 0.608192 0.297171 0.247333 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'
Cl Cl 0.3639 0.7018 '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
N2N N1N C13C 118.56(12) . . ?
C12C N1N N2N 112.33(12) . . ?
C12C N1N C13C 127.85(13) . . ?
C19C N2N N1N 108.86(12) . . ?
O1C C1C C2C 127.19(13) . . ?
O1C C1C C9C 126.27(13) . . ?
C2C C1C C9C 106.22(11) . . ?
C3C C2C C1C 128.87(14) . . ?
C7C C2C C1C 110.16(12) . . ?
C7C C2C C3C 120.79(14) . . ?
C2C C3C H3C 121.1 . . ?
C4C C3C C2C 117.84(14) . . ?
C4C C3C H3C 121.1 . . ?
C3C C4C H4C 119.5 . . ?
C3C C4C C5C 120.96(14) . . ?
C5C C4C H4C 119.5 . . ?
C4C C5C H5C 119.3 . . ?
C6C C5C C4C 121.49(15) . . ?
C6C C5C H5C 119.3 . . ?
C5C C6C H6C 121.3 . . ?
C5C C6C C7C 117.43(15) . . ?
C7C C6C H6C 121.3 . . ?
C2C C7C C8C 110.38(13) . . ?
C6C C7C C2C 121.44(13) . . ?
C6C C7C C8C 128.11(13) . . ?
O2C C8C C7C 125.84(14) . . ?
O2C C8C C9C 127.52(13) . . ?
C7C C8C C9C 106.62(11) . . ?
C1C C9C C11C 120.81(11) . . ?
C8C C9C C1C 105.54(11) . . ?
C8C C9C C11C 119.62(12) . . ?
C10C C9C C1C 121.23(12) . . ?
C10C C9C C8C 125.33(12) . . ?
C10C C9C C11C 58.67(9) . . ?
C9C C10C H10C 112.0 . . ?
C9C C10C C11C 63.39(9) . . ?
C9C C10C C21C 124.33(12) . . ?
C11C C10C H10C 112.0 . . ?
C21C C10C H10C 112.0 . . ?
C21C C10C C11C 124.96(12) . . ?
C10C C11C C9C 57.94(9) . . ?
C10C C11C C12C 118.45(12) . . ?
C12C C11C C9C 118.06(11) . . ?
C19C C11C C9C 123.61(12) . . ?
C19C C11C C10C 131.23(12) . . ?
C19C C11C C12C 102.93(12) . . ?
O3C C12C N1N 126.90(14) . . ?
O3C C12C C11C 128.90(13) . . ?
N1N C12C C11C 104.13(12) . . ?
C14C C13C N1N 119.75(14) . . ?
C14C C13C C18C 120.00(15) . . ?
C18C C13C N1N 120.25(14) . . ?
C13C C14C H14C 120.0 . . ?
C15C C14C C13C 120.05(15) . . ?
C15C C14C H14C 120.0 . . ?
C14C C15C H15C 120.2 . . ?
C16C C15C C14C 119.61(15) . . ?
C16C C15C H15C 120.2 . . ?
C15C C16C Cl1C 120.45(13) . . ?
C17C C16C Cl1C 118.77(13) . . ?
C17C C16C C15C 120.75(15) . . ?
C16C C17C H17C 120.0 . . ?
C16C C17C C18C 119.90(16) . . ?
C18C C17C H17C 120.0 . . ?
C13C C18C H18C 120.2 . . ?
C17C C18C C13C 119.65(15) . . ?
C17C C18C H18C 120.2 . . ?
N2N C19C C11C 111.00(13) . . ?
N2N C19C C20C 118.49(13) . . ?
C20C C19C C11C 130.43(13) . . ?
C19C C20C H20A 109.5 . . ?
C19C C20C H20B 109.5 . . ?
C19C C20C H20C 109.5 . . ?
H20A C20C H20B 109.5 . . ?
H20A C20C H20C 109.5 . . ?
H20B C20C H20C 109.5 . . ?
C22C C21C C10C 120.29(12) . . ?
C22C C21C C26C 119.23(13) . . ?
C26C C21C C10C 120.13(13) . . ?
C21C C22C H22C 120.1 . . ?
C21C C22C C23C 119.86(13) . . ?
C23C C22C H22C 120.1 . . ?
C22C C23C H23C 119.8 . . ?
C24C C23C C22C 120.49(14) . . ?
C24C C23C H23C 119.8 . . ?
C23C C24C H24C 120.0 . . ?
C25C C24C C23C 120.01(13) . . ?
C25C C24C H24C 120.0 . . ?
C24C C25C H25C 120.3 . . ?
C24C C25C C26C 119.49(14) . . ?
C26C C25C H25C 120.3 . . ?
C21C C26C H26C 119.5 . . ?
C25C C26C C21C 120.90(14) . . ?
C25C C26C H26C 119.5 . . ?
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
Cl1C C16C 1.7398(16) . ?
O1C C1C 1.2109(18) . ?
O2C C8C 1.2124(17) . ?
O3C C12C 1.2169(18) . ?
N1N N2N 1.4060(17) . ?
N1N C12C 1.3768(19) . ?
N1N C13C 1.4183(19) . ?
N2N C19C 1.288(2) . ?
C1C C2C 1.481(2) . ?
C1C C9C 1.5230(18) . ?
C2C C3C 1.393(2) . ?
C2C C7C 1.391(2) . ?
C3C H3C 0.9300 . ?
C3C C4C 1.388(2) . ?
C4C H4C 0.9300 . ?
C4C C5C 1.391(2) . ?
C5C H5C 0.9300 . ?
C5C C6C 1.385(2) . ?
C6C H6C 0.9300 . ?
C6C C7C 1.390(2) . ?
C7C C8C 1.4790(19) . ?
C8C C9C 1.5135(19) . ?
C9C C10C 1.4963(19) . ?
C9C C11C 1.5786(19) . ?
C10C H10C 0.9800 . ?
C10C C11C 1.5081(19) . ?
C10C C21C 1.5017(18) . ?
C11C C12C 1.5106(19) . ?
C11C C19C 1.4928(19) . ?
C13C C14C 1.386(2) . ?
C13C C18C 1.390(2) . ?
C14C H14C 0.9300 . ?
C14C C15C 1.384(2) . ?
C15C H15C 0.9300 . ?
C15C C16C 1.381(2) . ?
C16C C17C 1.377(2) . ?
C17C H17C 0.9300 . ?
C17C C18C 1.386(2) . ?
C18C H18C 0.9300 . ?
C19C C20C 1.490(2) . ?
C20C H20A 0.9600 . ?
C20C H20B 0.9600 . ?
C20C H20C 0.9600 . ?
C21C C22C 1.393(2) . ?
C21C C26C 1.3931(19) . ?
C22C H22C 0.9300 . ?
C22C C23C 1.3928(19) . ?
C23C H23C 0.9300 . ?
C23C C24C 1.388(2) . ?
C24C H24C 0.9300 . ?
C24C C25C 1.386(2) . ?
C25C H25C 0.9300 . ?
C25C C26C 1.393(2) . ?
C26C H26C 0.9300 . ?
