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#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/45/4024579.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_4024579
loop_
_publ_author_name
'Nugzar Ghavtadze'
'Roland Fröhlich'
'Ernst-Ulrich Würthwein'
_publ_section_title
;
Acid-Mediated Electrocyclic Domino Transformations of 5,5-Disubstituted
1-Amino-1-azapenta-1,4-dien-3-ones into Dihydrospiroindenepyrazole and
Dihydroindenodiazepine Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4584
_journal_page_last               4591
_journal_paper_doi               10.1021/jo900270e
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C16 H15 F3 N2 O'
_chemical_formula_weight         308.30
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.026(1)
_cell_length_b                   16.043(5)
_cell_length_c                   26.047(4)
_cell_measurement_reflns_used    16
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      23.90
_cell_measurement_theta_min      20.94
_cell_volume                     2936.0(11)
_computing_cell_refinement       'Express (Nonius B.V., 1994)'
_computing_data_collection       'Express (Nonius B.V., 1994)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3489
_diffrn_reflns_theta_full        74.27
_diffrn_reflns_theta_max         74.27
_diffrn_reflns_theta_min         3.39
_diffrn_standards_decay_%        2.6
_diffrn_standards_interval_count 250
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.979
_exptl_absorpt_correction_T_max  0.9527
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'based on ψ scan data'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.00049(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc2^λ3^/sin(2θ)]-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ2^(Fo2^)+(0.1057P)2^+0.0000P] where P=(Fo2+2Fc2)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1809
_reflns_number_gt                1786
_reflns_number_total             2986
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900270e_si_004.cif
_cod_data_source_block           wue3776
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4024579
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5579(4) 0.1241(2) 0.28337(10) 0.0474(7) Uani 1 1 d . . .
H1 H 0.6033 0.1629 0.2592 0.057 Uiso 1 1 calc R . .
C2 C 0.5841(4) 0.0392(2) 0.27647(11) 0.0534(8) Uani 1 1 d . . .
H2 H 0.6494 0.0205 0.2472 0.064 Uiso 1 1 calc R . .
C3 C 0.5181(4) -0.0179(2) 0.31087(11) 0.0508(8) Uani 1 1 d . . .
H3 H 0.5374 -0.0751 0.3047 0.061 Uiso 1 1 calc R . .
C4 C 0.4210(4) 0.00787(17) 0.35567(10) 0.0424(6) Uani 1 1 d . . .
H4 H 0.3765 -0.0313 0.3797 0.051 Uiso 1 1 calc R . .
C5 C 0.3935(4) 0.09161(17) 0.36307(9) 0.0345(6) Uani 1 1 d . . .
C6 C 0.4616(3) 0.14989(16) 0.32753(9) 0.0340(6) Uani 1 1 d . . .
C7 C 0.4115(4) 0.23339(17) 0.34701(9) 0.0377(6) Uani 1 1 d . . .
C8 C 0.3179(4) 0.22727(16) 0.39106(10) 0.0365(6) Uani 1 1 d . . .
H8 H 0.2738 0.2728 0.4104 0.044 Uiso 1 1 calc R . .
C9 C 0.2919(3) 0.13615(16) 0.40597(9) 0.0320(6) Uani 1 1 d . . .
C10 C 0.0777(4) 0.11651(16) 0.41097(10) 0.0366(6) Uani 1 1 d . . .
N11 N 0.0194(3) 0.11702(14) 0.45725(8) 0.0410(6) Uani 1 1 d . . .
N12 N 0.1753(3) 0.13770(13) 0.48857(8) 0.0368(5) Uani 1 1 d . . .
C13 C 0.1744(4) 0.1080(2) 0.54130(10) 0.0492(8) Uani 1 1 d . . .
H13A H 0.1842 0.0471 0.5424 0.059 Uiso 1 1 calc R . .
H13B H 0.0573 0.1250 0.5589 0.059 Uiso 1 1 calc R . .
C14 C 0.3456(5) 0.1478(2) 0.56590(10) 0.0541(8) Uani 1 1 d . . .
H14A H 0.3302 0.2085 0.5654 0.065 Uiso 1 1 calc R . .
H14B H 0.3535 0.1301 0.6018 0.065 Uiso 1 1 calc R . .
O15 O 0.5175(3) 0.12638(13) 0.54037(7) 0.0472(5) Uani 1 1 d . . .
C16 C 0.5164(4) 0.15272(18) 0.48775(9) 0.0403(6) Uani 1 1 d . . .
H16A H 0.6347 0.1355 0.4709 0.048 Uiso 1 1 calc R . .
H16B H 0.5071 0.2136 0.4859 0.048 Uiso 1 1 calc R . .
C17 C 0.3485(3) 0.11342(15) 0.46135(9) 0.0309(5) Uani 1 1 d . . .
H17 H 0.3618 0.0521 0.4636 0.037 Uiso 1 1 calc R . .
C18 C 0.4632(5) 0.3107(2) 0.32003(10) 0.0510(8) Uani 1 1 d . . .
F1 F 0.3917(4) 0.31595(15) 0.27372(8) 0.1034(10) Uani 1 1 d . . .
F2 F 0.6521(3) 0.31770(14) 0.31392(8) 0.0812(7) Uani 1 1 d . . .
F3 F 0.4142(4) 0.37963(11) 0.34593(8) 0.0794(7) Uani 1 1 d . . .
C19 C -0.0519(4) 0.1051(2) 0.36578(12) 0.0553(8) Uani 1 1 d . . .
H19A H -0.1813 0.0969 0.3777 0.083 Uiso 1 1 calc R . .
H19B H -0.0117 0.0569 0.3462 0.083 Uiso 1 1 calc R . .
H19C H -0.0466 0.1543 0.3442 0.083 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'
F F 0.0727 0.0534 '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
C2 C1 C6 117.5(3) . . ?
C3 C2 C1 122.1(3) . . ?
C2 C3 C4 120.6(3) . . ?
C5 C4 C3 118.1(3) . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 C9 129.5(2) . . ?
C6 C5 C9 109.6(2) . . ?
C1 C6 C5 120.8(3) . . ?
C1 C6 C7 131.9(2) . . ?
C5 C6 C7 107.3(2) . . ?
C8 C7 C18 126.7(3) . . ?
C8 C7 C6 110.4(2) . . ?
C18 C7 C6 122.9(2) . . ?
C7 C8 C9 110.6(2) . . ?
C5 C9 C8 102.08(19) . . ?
C5 C9 C10 115.3(2) . . ?
C8 C9 C10 109.6(2) . . ?
C5 C9 C17 117.4(2) . . ?
C8 C9 C17 115.8(2) . . ?
C10 C9 C17 97.14(18) . . ?
N11 C10 C19 123.3(2) . . ?
N11 C10 C9 113.1(2) . . ?
C19 C10 C9 123.4(2) . . ?
C10 N11 N12 107.5(2) . . ?
N11 N12 C13 117.9(2) . . ?
N11 N12 C17 107.72(19) . . ?
C13 N12 C17 112.0(2) . . ?
N12 C13 C14 105.1(2) . . ?
O15 C14 C13 112.2(2) . . ?
C14 O15 C16 111.8(2) . . ?
O15 C16 C17 108.5(2) . . ?
N12 C17 C16 108.6(2) . . ?
N12 C17 C9 100.16(19) . . ?
C16 C17 C9 122.1(2) . . ?
F1 C18 F3 108.2(3) . . ?
F1 C18 F2 105.4(3) . . ?
F3 C18 F2 104.2(3) . . ?
F1 C18 C7 113.5(3) . . ?
F3 C18 C7 113.1(2) . . ?
F2 C18 C7 111.8(3) . . ?
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 C2 1.386(5) . ?
C1 C6 1.397(4) . ?
C2 C3 1.363(5) . ?
C3 C4 1.414(4) . ?
C4 C5 1.371(4) . ?
C5 C6 1.400(4) . ?
C5 C9 1.506(3) . ?
C6 C7 1.475(4) . ?
C7 C8 1.326(4) . ?
C7 C18 1.472(4) . ?
C8 C9 1.523(3) . ?
C9 C10 1.543(3) . ?
C9 C17 1.540(3) . ?
C10 N11 1.273(3) . ?
C10 C19 1.499(4) . ?
N11 N12 1.406(3) . ?
N12 C13 1.454(3) . ?
N12 C17 1.461(3) . ?
C13 C14 1.505(4) . ?
C14 O15 1.421(3) . ?
O15 C16 1.434(3) . ?
C16 C17 1.504(4) . ?
C18 F1 1.309(3) . ?
C18 F3 1.340(4) . ?
C18 F2 1.342(4) . ?
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 C3 0.5(4) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C3 C4 C5 C9 178.3(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C1 C6 C7 179.3(3) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C9 C5 C6 C1 -178.6(2) . . . . ?
C4 C5 C6 C7 -179.2(2) . . . . ?
C9 C5 C6 C7 1.7(3) . . . . ?
C1 C6 C7 C8 179.7(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C1 C6 C7 C18 -0.8(4) . . . . ?
C5 C6 C7 C18 179.0(2) . . . . ?
C18 C7 C8 C9 179.7(3) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C4 C5 C9 C8 178.9(3) . . . . ?
C6 C5 C9 C8 -2.0(3) . . . . ?
C4 C5 C9 C10 -62.4(4) . . . . ?
C6 C5 C9 C10 116.7(2) . . . . ?
C4 C5 C9 C17 51.2(4) . . . . ?
C6 C5 C9 C17 -129.7(2) . . . . ?
C7 C8 C9 C5 1.7(3) . . . . ?
C7 C8 C9 C10 -121.0(2) . . . . ?
C7 C8 C9 C17 130.5(2) . . . . ?
C5 C9 C10 N11 146.1(2) . . . . ?
C8 C9 C10 N11 -99.5(3) . . . . ?
C17 C9 C10 N11 21.2(3) . . . . ?
C5 C9 C10 C19 -38.8(4) . . . . ?
C8 C9 C10 C19 75.7(3) . . . . ?
C17 C9 C10 C19 -163.7(3) . . . . ?
C19 C10 N11 N12 -173.9(3) . . . . ?
C9 C10 N11 N12 1.2(3) . . . . ?
C10 N11 N12 C13 -153.4(2) . . . . ?
C10 N11 N12 C17 -25.4(3) . . . . ?
N11 N12 C13 C14 -173.8(2) . . . . ?
C17 N12 C13 C14 60.3(3) . . . . ?
N12 C13 C14 O15 -58.7(3) . . . . ?
C13 C14 O15 C16 60.3(3) . . . . ?
C14 O15 C16 C17 -57.8(3) . . . . ?
N11 N12 C17 C16 166.7(2) . . . . ?
C13 N12 C17 C16 -62.1(3) . . . . ?
N11 N12 C17 C9 37.6(2) . . . . ?
C13 N12 C17 C9 168.8(2) . . . . ?
O15 C16 C17 N12 57.5(3) . . . . ?
O15 C16 C17 C9 173.1(2) . . . . ?
C5 C9 C17 N12 -156.3(2) . . . . ?
C8 C9 C17 N12 83.0(2) . . . . ?
C10 C9 C17 N12 -32.8(2) . . . . ?
C5 C9 C17 C16 84.0(3) . . . . ?
C8 C9 C17 C16 -36.8(3) . . . . ?
C10 C9 C17 C16 -152.6(2) . . . . ?
C8 C7 C18 F1 -120.5(3) . . . . ?
C6 C7 C18 F1 60.1(4) . . . . ?
C8 C7 C18 F3 3.3(4) . . . . ?
C6 C7 C18 F3 -176.1(2) . . . . ?
C8 C7 C18 F2 120.5(3) . . . . ?
C6 C7 C18 F2 -58.9(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091151
