#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:26:31 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266154 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158010.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_7158010
loop_
_publ_author_name
'Pirovano, Valentina'
'Brambilla, Elisa'
'Riva, Marika'
'Leoni, Sara'
'Rizzato, Silvia'
'Garanzini, Davide'
'Abbiati, Giorgio'
'Rossi, Elisabetta'
_publ_section_title
;
 Stereoselective synthesis of 2-spirocyclopropyl-indolin-3-ones through
 cyclopropanation of aza-aurones with tosylhydrazones.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3925
_journal_page_last               3931
_journal_paper_doi               10.1039/d1ob00076d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C27 H19 N O3'
_chemical_formula_sum            'C27 H19 N O3'
_chemical_formula_weight         405.43
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2021-01-12 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.272(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.301(2)
_cell_length_b                   6.870(1)
_cell_length_c                   29.971(6)
_cell_measurement_reflns_used    2826
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.4
_cell_measurement_theta_min      2.3
_cell_measurement_wavelength     0.71073
_cell_volume                     2103.9(7)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution
'SIR 2014: C. Giacovazzo et all., J. Appl. Cryst.(2015) 48, 306'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CCD_plate
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker apex II ccd diffractometer'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12735
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        22.70
_diffrn_reflns_theta_max         22.70
_diffrn_reflns_theta_min         1.37
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.6373
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs 2.01 (Bruker AXS, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.2801
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     289
_refine_ls_number_reflns         2824
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0643P)²+1.2343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1491
_reflns_Friedel_coverage         0
_reflns_number_gt                2001
_reflns_number_total             2824
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00076d2.cif
_cod_data_source_block           3n
_cod_depositor_comments          'Adding full bibliography for 7158010.cif.'
_cod_original_cell_volume        2103.8(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158010
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.7731(2) 0.5050(4) 0.95371(8) 0.0529(7) Uani 1 1 d . . . . .
O1 O 0.5041(2) 0.2611(3) 0.89321(7) 0.0621(6) Uani 1 1 d . . . . .
O2 O 0.9110(3) 0.7191(4) 0.92865(9) 0.0936(9) Uani 1 1 d . . . . .
O3 O 0.8819(5) 0.7602(9) 1.00480(16) 0.197(2) Uani 1 1 d D . . . .
C1 C 0.7025(3) 0.4471(4) 0.90995(9) 0.0465(7) Uani 1 1 d . . . . .
C2 C 0.5851(3) 0.3383(4) 0.92053(10) 0.0471(7) Uani 1 1 d . . . . .
C3 C 0.5955(3) 0.3263(4) 0.96917(10) 0.0476(8) Uani 1 1 d . . . . .
C4 C 0.7097(3) 0.4157(5) 0.98782(10) 0.0536(8) Uani 1 1 d . . . . .
C5 C 0.7481(4) 0.4017(6) 1.03393(11) 0.0733(10) Uani 1 1 d . . . . .
H5 H 0.827273 0.453535 1.047019 0.088 Uiso 1 1 calc R U . . .
C6 C 0.6650(5) 0.3085(6) 1.05953(12) 0.0839(12) Uani 1 1 d . . . . .
H6 H 0.688928 0.300076 1.09045 0.101 Uiso 1 1 calc R U . . .
C7 C 0.5492(5) 0.2281(5) 1.04149(13) 0.0803(12) Uani 1 1 d . . . . .
H7 H 0.494376 0.170011 1.059983 0.096 Uiso 1 1 calc R U . . .
C8 C 0.5140(4) 0.2337(5) 0.99544(12) 0.0629(9) Uani 1 1 d . . . . .
H8 H 0.43665 0.175993 0.982437 0.075 Uiso 1 1 calc R U . . .
C9 C 0.7634(3) 0.3697(5) 0.86950(10) 0.0498(8) Uani 1 1 d . . . . .
C10 C 0.7012(3) 0.5650(5) 0.86652(10) 0.0512(8) Uani 1 1 d . . . . .
C11 C 0.9055(3) 0.3325(5) 0.86988(9) 0.0535(8) Uani 1 1 d . . . . .
C12 C 0.9538(3) 0.1541(6) 0.88444(11) 0.0712(10) Uani 1 1 d . . . . .
H12 H 0.898268 0.063375 0.89515 0.085 Uiso 1 1 calc R U . . .
C13 C 1.0829(5) 0.1079(9) 0.88340(15) 0.1052(16) Uani 1 1 d . . . . .
H13 H 1.113567 -0.01431 0.893049 0.126 Uiso 1 1 calc R U . . .
C14 C 1.1663(5) 0.2384(12) 0.86845(17) 0.118(2) Uani 1 1 d . . . . .
H14 H 1.254092 0.207317 0.868369 0.142 Uiso 1 1 calc R U . . .
C15 C 1.1196(4) 0.4165(10) 0.85349(14) 0.1016(16) Uani 1 1 d . . . . .
H15 H 1.175946 0.505932 0.842743 0.122 Uiso 1 1 calc R U . . .
C16 C 0.9894(3) 0.4647(6) 0.85419(11) 0.0742(10) Uani 1 1 d . . . . .
H16 H 0.958591 0.586267 0.844088 0.089 Uiso 1 1 calc R U . . .
C17 C 0.5766(3) 0.6178(5) 0.83844(10) 0.0531(8) Uani 1 1 d . . . . .
C18 C 0.5093(3) 0.4961(5) 0.80837(10) 0.0590(9) Uani 1 1 d . . . . .
H18 H 0.542802 0.373068 0.803793 0.071 Uiso 1 1 calc R U . . .
C19 C 0.3871(3) 0.5535(6) 0.78342(10) 0.0624(9) Uani 1 1 d . . . . .
C20 C 0.3403(4) 0.7426(6) 0.79037(11) 0.0710(10) Uani 1 1 d . . . . .
C21 C 0.4134(4) 0.8682(6) 0.81988(13) 0.0803(11) Uani 1 1 d . . . . .
H21 H 0.383719 0.994141 0.823711 0.096 Uiso 1 1 calc R U . . .
C22 C 0.5289(4) 0.8080(5) 0.84334(11) 0.0663(10) Uani 1 1 d . . . . .
H22 H 0.576816 0.894108 0.862913 0.08 Uiso 1 1 calc R U . . .
C23 C 0.3145(4) 0.4258(7) 0.75399(12) 0.0861(12) Uani 1 1 d . . . . .
H23 H 0.346561 0.302195 0.748986 0.103 Uiso 1 1 calc R U . . .
C24 C 0.1949(4) 0.4837(10) 0.73237(13) 0.1095(17) Uani 1 1 d . . . . .
H24 H 0.145757 0.398238 0.712976 0.131 Uiso 1 1 calc R U . . .
C25 C 0.1467(5) 0.6702(11) 0.73933(16) 0.1148(19) Uani 1 1 d . . . . .
H25 H 0.065566 0.706338 0.724472 0.138 Uiso 1 1 calc R U . . .
C26 C 0.2147(5) 0.7983(9) 0.76689(15) 0.1049(16) Uani 1 1 d . . . . .
H26 H 0.181158 0.921901 0.770845 0.126 Uiso 1 1 calc R U . . .
C27 C 0.8578(3) 0.6586(6) 0.95969(12) 0.0703(10) Uani 1 1 d . . . . .
H9 H 0.712(3) 0.270(5) 0.8569(12) 0.084 Uiso 1 1 d . U . . .
H10 H 0.761(3) 0.669(5) 0.8715(11) 0.084 Uiso 1 1 d . U . . .
H3O H 0.954(3) 0.714(6) 1.0247(13) 0.105 Uiso 1 1 d D U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C27 N1 C4 125.7(3) . . ?
C27 N1 C1 124.1(3) . . ?
C4 N1 C1 107.8(2) . . ?
N1 C1 C2 105.6(2) . . ?
N1 C1 C9 126.5(2) . . ?
C2 C1 C9 114.8(2) . . ?
N1 C1 C10 124.4(2) . . ?
C2 C1 C10 121.8(2) . . ?
C9 C1 C10 58.03(19) . . ?
O1 C2 C3 127.6(3) . . ?
O1 C2 C1 125.6(3) . . ?
C3 C2 C1 106.5(3) . . ?
C8 C3 C4 121.6(3) . . ?
C8 C3 C2 128.9(3) . . ?
C4 C3 C2 109.4(3) . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 N1 110.3(3) . . ?
C5 C4 N1 130.2(3) . . ?
C6 C5 C4 117.8(4) . . ?
C7 C6 C5 122.8(4) . . ?
C6 C7 C8 119.4(4) . . ?
C3 C8 C7 118.8(4) . . ?
C11 C9 C10 125.0(3) . . ?
C11 C9 C1 123.8(3) . . ?
C10 C9 C1 61.1(2) . . ?
C9 C10 C17 126.1(3) . . ?
C9 C10 C1 60.9(2) . . ?
C17 C10 C1 121.6(3) . . ?
C12 C11 C16 118.6(3) . . ?
C12 C11 C9 118.3(3) . . ?
C16 C11 C9 123.0(3) . . ?
C13 C12 C11 120.9(4) . . ?
C14 C13 C12 120.7(5) . . ?
C13 C14 C15 119.2(4) . . ?
C14 C15 C16 120.6(5) . . ?
C11 C16 C15 119.9(4) . . ?
C18 C17 C22 119.0(3) . . ?
C18 C17 C10 124.0(3) . . ?
C22 C17 C10 117.0(3) . . ?
C17 C18 C19 121.3(3) . . ?
C23 C19 C20 120.5(4) . . ?
C23 C19 C18 121.5(4) . . ?
C20 C19 C18 118.0(3) . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 C26 121.8(4) . . ?
C19 C20 C26 118.3(4) . . ?
C22 C21 C20 120.5(4) . . ?
C21 C22 C17 121.3(4) . . ?
C24 C23 C19 119.5(5) . . ?
C23 C24 C25 120.5(5) . . ?
C26 C25 C24 121.7(5) . . ?
C25 C26 C20 119.5(5) . . ?
O2 C27 N1 120.5(3) . . ?
O2 C27 O3 119.2(4) . . ?
N1 C27 O3 120.2(4) . . ?
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
N1 C27 1.367(4) . ?
N1 C4 1.420(4) . ?
N1 C1 1.472(4) . ?
O1 C2 1.214(3) . ?
O2 C27 1.212(4) . ?
O3 C27 1.514(6) . ?
C1 C2 1.489(4) . ?
C1 C9 1.529(4) . ?
C1 C10 1.531(4) . ?
C2 C3 1.451(4) . ?
C3 C8 1.377(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.392(4) . ?
C5 C6 1.378(5) . ?
C6 C7 1.363(5) . ?
C7 C8 1.382(5) . ?
C9 C11 1.484(4) . ?
C9 C10 1.484(4) . ?
C10 C17 1.488(4) . ?
C11 C12 1.373(5) . ?
C11 C16 1.377(5) . ?
C12 C13 1.371(5) . ?
C13 C14 1.357(7) . ?
C14 C15 1.369(7) . ?
C15 C16 1.385(5) . ?
C17 C18 1.354(4) . ?
C17 C22 1.411(5) . ?
C18 C19 1.436(4) . ?
C19 C23 1.393(5) . ?
C19 C20 1.410(5) . ?
C20 C21 1.388(5) . ?
C20 C26 1.444(5) . ?
C21 C22 1.366(5) . ?
C23 C24 1.376(6) . ?
C24 C25 1.399(7) . ?
C25 C26 1.341(7) . ?
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_details
O3 H3o 0.9 0 'generated by SHELX DFIX'
