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#$Date: 2022-03-31 00:55:50 +0300 (Thu, 31 Mar 2022) $
#$Revision: 274131 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/99/7129907.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_7129907
loop_
_publ_author_name
'Solanke, Pooja R.'
'Cinsani, Radhika'
'Nayani, Kiranmai'
'Mainkar, Prathama S.'
'Chandrasekhar, Srivari'
_publ_section_title
;
 Quaternary Carbon Construction through Piancatelli Rearrangement: Easy
 Access to Spirocyclopentenones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00050D
_journal_year                    2022
_chemical_formula_moiety         'C20 H14 N2 O2'
_chemical_formula_sum            'C20 H14 N2 O2'
_chemical_formula_weight         314.33
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-08-21 deposited with the CCDC.	2022-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                102.836(3)
_cell_angle_beta                 101.585(8)
_cell_angle_gamma                99.182(9)
_cell_formula_units_Z            2
_cell_length_a                   6.5740(7)
_cell_length_b                   8.6042(6)
_cell_length_c                   14.8471(8)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.97
_cell_measurement_theta_min      2.68
_cell_volume                     783.60(12)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10367
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_min         2.485
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0717P)²+0.0353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2187
_reflns_number_total             3214
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00050d2.cif
_cod_data_source_block           KB14_0m
_cod_original_cell_volume        783.60(11)
_cod_database_code               7129907
_shelx_shelxl_version_number     2018/3
_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_min   0.978
_shelx_estimated_absorpt_t_max   0.986
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
C1 C 0.5694(3) 0.1579(2) 0.75140(13) 0.0385(4) Uani 1 1 d . . . . .
C2 C 0.3969(3) 0.0215(2) 0.71892(14) 0.0418(5) Uani 1 1 d . . . . .
C3 C 0.2422(4) -0.0043(2) 0.76841(16) 0.0530(6) Uani 1 1 d . . . . .
H3 H 0.131059 -0.095566 0.746123 0.064 Uiso 1 1 calc R U . . .
C4 C 0.2604(4) 0.1107(3) 0.85160(17) 0.0634(7) Uani 1 1 d . . . . .
H4 H 0.158817 0.096938 0.886261 0.076 Uiso 1 1 calc R U . . .
C5 C 0.4266(4) 0.2476(3) 0.88571(16) 0.0638(7) Uani 1 1 d . . . . .
H5 H 0.433125 0.323530 0.942182 0.077 Uiso 1 1 calc R U . . .
C6 C 0.5820(4) 0.2724(2) 0.83696(14) 0.0524(6) Uani 1 1 d . . . . .
H6 H 0.693256 0.363610 0.860512 0.063 Uiso 1 1 calc R U . . .
C7 C 0.6966(3) 0.14149(19) 0.68270(13) 0.0371(4) Uani 1 1 d . . . . .
C8 C 0.5995(3) 0.0008(2) 0.61474(14) 0.0436(5) Uani 1 1 d . . . . .
H8 H 0.648610 -0.040681 0.561751 0.052 Uiso 1 1 calc R U . . .
C9 C 0.9007(3) 0.2520(2) 0.68713(13) 0.0380(4) Uani 1 1 d . . . . .
H9 H 0.994364 0.265945 0.749975 0.046 Uiso 1 1 calc R U . . .
C10 C 0.8901(3) 0.42696(18) 0.67556(12) 0.0305(4) Uani 1 1 d . . . . .
C11 C 1.0648(3) 0.4623(2) 0.62280(14) 0.0402(4) Uani 1 1 d . . . . .
C12 C 1.1123(3) 0.3060(2) 0.58117(17) 0.0530(5) Uani 1 1 d . . . . .
H12 H 1.195580 0.289399 0.537571 0.064 Uiso 1 1 calc R U . . .
C13 C 1.0190(3) 0.1917(2) 0.61494(15) 0.0481(5) Uani 1 1 d . . . . .
H13 H 1.026155 0.082691 0.595452 0.058 Uiso 1 1 calc R U . . .
C14 C 0.9020(3) 0.55925(19) 0.76240(12) 0.0332(4) Uani 1 1 d . . . . .
C15 C 0.7300(3) 0.63198(19) 0.74468(12) 0.0352(4) Uani 1 1 d . . . . .
C16 C 0.6823(3) 0.43128(18) 0.60730(12) 0.0294(4) Uani 1 1 d . . . . .
C17 C 1.0452(4) 0.6115(2) 0.85002(14) 0.0504(5) Uani 1 1 d . . . . .
H17 H 1.162473 0.564808 0.862795 0.061 Uiso 1 1 calc R U . . .
C18 C 1.0099(4) 0.7361(3) 0.91914(15) 0.0645(7) Uani 1 1 d . . . . .
H18 H 1.104539 0.772862 0.978883 0.077 Uiso 1 1 calc R U . . .
C19 C 0.8383(5) 0.8050(3) 0.90035(15) 0.0636(7) Uani 1 1 d . . . . .
H19 H 0.817895 0.887641 0.947790 0.076 Uiso 1 1 calc R U . . .
C20 C 0.6939(4) 0.7549(2) 0.81242(15) 0.0541(6) Uani 1 1 d . . . . .
H20 H 0.577448 0.802356 0.799660 0.065 Uiso 1 1 calc R U . . .
O1 O 1.1447(2) 0.59678(16) 0.61941(11) 0.0548(4) Uani 1 1 d . . . . .
O2 O 0.6029(2) 0.34207(14) 0.52805(9) 0.0393(3) Uani 1 1 d . . . . .
N1 N 0.4194(3) -0.07146(19) 0.63495(13) 0.0471(4) Uani 1 1 d . . . . .
H1N H 0.340(4) -0.167(3) 0.5993(15) 0.061(7) Uiso 1 1 d . . . . .
N2 N 0.6065(3) 0.55655(17) 0.65166(11) 0.0387(4) Uani 1 1 d . . . . .
H2N H 0.492(3) 0.587(2) 0.6222(15) 0.058 Uiso 1 1 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 0.0000 0.0000 '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 0.0060 '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
C6 C1 C2 118.13(18) . . ?
C6 C1 C7 134.96(18) . . ?
C2 C1 C7 106.90(16) . . ?
N1 C2 C3 129.88(19) . . ?
N1 C2 C1 107.22(17) . . ?
C3 C2 C1 122.89(19) . . ?
C4 C3 C2 117.1(2) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C8 C7 C1 106.19(17) . . ?
C8 C7 C9 126.48(18) . . ?
C1 C7 C9 127.27(17) . . ?
C7 C8 N1 110.64(18) . . ?
C7 C8 H8 124.7 . . ?
N1 C8 H8 124.7 . . ?
C7 C9 C13 116.09(16) . . ?
C7 C9 C10 117.42(14) . . ?
C13 C9 C10 102.18(14) . . ?
C7 C9 H9 106.8 . . ?
C13 C9 H9 106.8 . . ?
C10 C9 H9 106.8 . . ?
C14 C10 C16 102.75(13) . . ?
C14 C10 C11 114.54(14) . . ?
C16 C10 C11 104.87(13) . . ?
C14 C10 C9 118.40(13) . . ?
C16 C10 C9 112.80(13) . . ?
C11 C10 C9 102.99(13) . . ?
O1 C11 C12 128.33(18) . . ?
O1 C11 C10 124.52(17) . . ?
C12 C11 C10 107.15(15) . . ?
C13 C12 C11 109.55(18) . . ?
C13 C12 H12 125.2 . . ?
C11 C12 H12 125.2 . . ?
C12 C13 C9 114.50(17) . . ?
C12 C13 H13 122.7 . . ?
C9 C13 H13 122.7 . . ?
C17 C14 C15 119.83(17) . . ?
C17 C14 C10 131.44(16) . . ?
C15 C14 C10 108.73(15) . . ?
C20 C15 C14 122.30(18) . . ?
C20 C15 N2 128.58(18) . . ?
C14 C15 N2 109.10(15) . . ?
O2 C16 N2 126.14(16) . . ?
O2 C16 C10 126.90(15) . . ?
N2 C16 C10 106.95(14) . . ?
C14 C17 C18 118.2(2) . . ?
C14 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 121.5(2) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C15 C20 C19 117.2(2) . . ?
C15 C20 H20 121.4 . . ?
C19 C20 H20 121.4 . . ?
C8 N1 C2 109.04(17) . . ?
C8 N1 H1N 122.4(15) . . ?
C2 N1 H1N 128.5(15) . . ?
C16 N2 C15 112.34(15) . . ?
C16 N2 H2N 121.9(13) . . ?
C15 N2 H2N 125.8(13) . . ?
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
C1 C6 1.403(3) . ?
C1 C2 1.414(3) . ?
C1 C7 1.441(3) . ?
C2 N1 1.373(2) . ?
C2 C3 1.387(3) . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.358(3) . ?
C7 C9 1.496(2) . ?
C8 N1 1.367(3) . ?
C8 H8 0.9300 . ?
C9 C13 1.496(3) . ?
C9 C10 1.563(2) . ?
C9 H9 0.9800 . ?
C10 C14 1.498(2) . ?
C10 C16 1.540(2) . ?
C10 C11 1.543(2) . ?
C11 O1 1.208(2) . ?
C11 C12 1.460(3) . ?
C12 C13 1.321(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C17 1.376(2) . ?
C14 C15 1.385(2) . ?
C15 C20 1.375(2) . ?
C15 N2 1.404(2) . ?
C16 O2 1.213(2) . ?
C16 N2 1.353(2) . ?
C17 C18 1.394(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 H1N 0.89(2) . ?
N2 H2N 0.90(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1 0.89(2) 2.34(2) 3.059(2) 138.6(19) 1_445 yes
N1 H1N O2 0.89(2) 2.28(2) 2.923(2) 129.6(19) 2_656 yes
N2 H2N O1 0.90(2) 2.29(2) 3.065(2) 144.1(18) 1_455 yes
N2 H2N O2 0.90(2) 2.43(2) 3.1173(19) 133.5(18) 2_666 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 N1 179.95(16) . . . . ?
C7 C1 C2 N1 -0.19(19) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C7 C1 C2 C3 179.15(16) . . . . ?
N1 C2 C3 C4 179.98(19) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C7 C1 C6 C5 -179.82(19) . . . . ?
C6 C1 C7 C8 179.5(2) . . . . ?
C2 C1 C7 C8 -0.32(19) . . . . ?
C6 C1 C7 C9 2.3(3) . . . . ?
C2 C1 C7 C9 -177.57(15) . . . . ?
C1 C7 C8 N1 0.7(2) . . . . ?
C9 C7 C8 N1 178.00(15) . . . . ?
C8 C7 C9 C13 -6.8(3) . . . . ?
C1 C7 C9 C13 169.96(16) . . . . ?
C8 C7 C9 C10 114.5(2) . . . . ?
C1 C7 C9 C10 -68.8(2) . . . . ?
C7 C9 C10 C14 86.4(2) . . . . ?
C13 C9 C10 C14 -145.40(16) . . . . ?
C7 C9 C10 C16 -33.6(2) . . . . ?
C13 C9 C10 C16 94.65(17) . . . . ?
C7 C9 C10 C11 -146.09(16) . . . . ?
C13 C9 C10 C11 -17.86(17) . . . . ?
C14 C10 C11 O1 -31.6(2) . . . . ?
C16 C10 C11 O1 80.3(2) . . . . ?
C9 C10 C11 O1 -161.51(19) . . . . ?
C14 C10 C11 C12 147.63(16) . . . . ?
C16 C10 C11 C12 -100.52(16) . . . . ?
C9 C10 C11 C12 17.70(19) . . . . ?
O1 C11 C12 C13 168.8(2) . . . . ?
C10 C11 C12 C13 -10.4(2) . . . . ?
C11 C12 C13 C9 -2.2(3) . . . . ?
C7 C9 C13 C12 142.44(18) . . . . ?
C10 C9 C13 C12 13.4(2) . . . . ?
C16 C10 C14 C17 176.77(18) . . . . ?
C11 C10 C14 C17 -70.1(2) . . . . ?
C9 C10 C14 C17 51.7(3) . . . . ?
C16 C10 C14 C15 -1.85(16) . . . . ?
C11 C10 C14 C15 111.26(16) . . . . ?
C9 C10 C14 C15 -126.88(16) . . . . ?
C17 C14 C15 C20 -0.8(3) . . . . ?
C10 C14 C15 C20 177.99(16) . . . . ?
C17 C14 C15 N2 -179.13(16) . . . . ?
C10 C14 C15 N2 -0.32(19) . . . . ?
C14 C10 C16 O2 -177.91(15) . . . . ?
C11 C10 C16 O2 62.0(2) . . . . ?
C9 C10 C16 O2 -49.3(2) . . . . ?
C14 C10 C16 N2 3.44(16) . . . . ?
C11 C10 C16 N2 -116.60(15) . . . . ?
C9 C10 C16 N2 132.06(15) . . . . ?
C15 C14 C17 C18 0.8(3) . . . . ?
C10 C14 C17 C18 -177.72(18) . . . . ?
C14 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C14 C15 C20 C19 0.3(3) . . . . ?
N2 C15 C20 C19 178.23(18) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C7 C8 N1 C2 -0.9(2) . . . . ?
C3 C2 N1 C8 -178.64(19) . . . . ?
C1 C2 N1 C8 0.6(2) . . . . ?
O2 C16 N2 C15 177.42(15) . . . . ?
C10 C16 N2 C15 -3.92(19) . . . . ?
C20 C15 N2 C16 -175.38(18) . . . . ?
C14 C15 N2 C16 2.8(2) . . . . ?
