#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/45/4024580.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_4024580
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            'C14 H13 F3 N2'
_chemical_formula_weight         266.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 123.22(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.159(1)
_cell_length_b                   8.921(1)
_cell_length_c                   16.079(1)
_cell_measurement_reflns_used    5007
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     2539.1(3)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ 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  0.031
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17000
_diffrn_reflns_theta_full        67.79
_diffrn_reflns_theta_max         67.79
_diffrn_reflns_theta_min         6.58
_exptl_absorpt_coefficient_mu    0.979
_exptl_absorpt_correction_T_max  0.8283
_exptl_absorpt_correction_T_min  0.6403
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0484
_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)+(0.0675P)²+1.4657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1298
_reflns_number_gt                2130
_reflns_number_total             2230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900270e_si_005.cif
_cod_data_source_block           wue3672
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4024580
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.21804(9) 0.5128(2) -0.02417(13) 0.0565(4) Uani 1 1 d . . .
H1A H 0.2184 0.5517 -0.0776 0.068 Uiso 1 1 calc R . .
C2 C 0.28073(9) 0.43821(18) 0.06049(12) 0.0491(4) Uani 1 1 d . . .
C3 C 0.35059(9) 0.41566(18) 0.07502(12) 0.0492(4) Uani 1 1 d . . .
C4 C 0.36514(11) 0.4445(2) -0.00535(14) 0.0612(5) Uani 1 1 d . . .
H4A H 0.4027 0.3757 0.0018 0.092 Uiso 1 1 calc R . .
H4B H 0.3828 0.5454 0.0002 0.092 Uiso 1 1 calc R . .
H4C H 0.3192 0.4309 -0.0693 0.092 Uiso 1 1 calc R . .
N5 N 0.41161(8) 0.36723(17) 0.16077(11) 0.0534(4) Uani 1 1 d . . .
H5 H 0.4513(12) 0.341(2) 0.1630(14) 0.055(5) Uiso 1 1 d . . .
N6 N 0.42162(7) 0.36072(16) 0.25527(10) 0.0527(4) Uani 1 1 d . . .
C6 C 0.25448(9) 0.39420(17) 0.12391(12) 0.0472(4) Uani 1 1 d . . .
C7 C 0.36930(10) 0.2555(2) 0.25894(14) 0.0587(4) Uani 1 1 d . . .
H7A H 0.3898 0.2299 0.3278 0.070 Uiso 1 1 calc R . .
H7B H 0.3670 0.1640 0.2247 0.070 Uiso 1 1 calc R . .
C8 C 0.29002(9) 0.31397(18) 0.21346(13) 0.0519(4) Uani 1 1 d . . .
C9 C 0.24977(11) 0.2910(2) 0.25741(14) 0.0611(5) Uani 1 1 d . . .
H9A H 0.2727 0.2409 0.3179 0.073 Uiso 1 1 calc R . .
C10 C 0.17547(11) 0.3417(2) 0.21259(15) 0.0633(5) Uani 1 1 d . . .
H10A H 0.1500 0.3245 0.2439 0.076 Uiso 1 1 calc R . .
C11 C 0.13927(10) 0.41650(19) 0.12312(14) 0.0570(4) Uani 1 1 d . . .
H11A H 0.0895 0.4483 0.0933 0.068 Uiso 1 1 calc R . .
C12 C 0.17889(9) 0.44369(18) 0.07805(13) 0.0500(4) Uani 1 1 d . . .
C13 C 0.15818(9) 0.5176(2) -0.01399(13) 0.0547(4) Uani 1 1 d . . .
C14 C 0.08386(10) 0.5844(3) -0.08492(15) 0.0688(5) Uani 1 1 d . . .
C15 C 0.42067(11) 0.5111(2) 0.29144(15) 0.0622(5) Uani 1 1 d . . .
H15A H 0.4594 0.5713 0.2942 0.093 Uiso 1 1 calc R . .
H15B H 0.4297 0.5038 0.3567 0.093 Uiso 1 1 calc R . .
H15C H 0.3723 0.5566 0.2471 0.093 Uiso 1 1 calc R . .
F1 F 0.08075(8) 0.6595(2) -0.15823(11) 0.1171(7) Uani 1 1 d . . .
F2 F 0.06124(8) 0.68123(17) -0.04185(12) 0.1011(5) Uani 1 1 d . . .
F3 F 0.02802(6) 0.48318(18) -0.12682(11) 0.1028(5) Uani 1 1 d . . .
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'
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
C13 C1 C2 109.63(15) . . ?
C3 C2 C1 125.02(16) . . ?
C3 C2 C6 128.77(15) . . ?
C1 C2 C6 106.20(14) . . ?
N5 C3 C2 124.00(15) . . ?
N5 C3 C4 113.74(14) . . ?
C2 C3 C4 122.26(15) . . ?
C3 N5 N6 127.54(14) . . ?
N5 N6 C15 111.20(14) . . ?
N5 N6 C7 113.22(13) . . ?
C15 N6 C7 113.09(14) . . ?
C8 C6 C12 120.77(15) . . ?
C8 C6 C2 131.36(15) . . ?
C12 C6 C2 107.84(14) . . ?
N6 C7 C8 114.80(14) . . ?
C9 C8 C6 117.69(16) . . ?
C9 C8 C7 122.12(16) . . ?
C6 C8 C7 120.19(14) . . ?
C8 C9 C10 121.36(17) . . ?
C11 C10 C9 121.37(16) . . ?
C10 C11 C12 118.53(17) . . ?
C11 C12 C6 120.22(16) . . ?
C11 C12 C13 132.53(16) . . ?
C6 C12 C13 107.26(14) . . ?
C1 C13 C12 109.06(15) . . ?
C1 C13 C14 126.04(17) . . ?
C12 C13 C14 124.89(16) . . ?
F1 C14 F3 107.03(18) . . ?
F1 C14 F2 105.95(19) . . ?
F3 C14 F2 103.10(16) . . ?
F1 C14 C13 113.92(16) . . ?
F3 C14 C13 112.98(18) . . ?
F2 C14 C13 113.01(17) . . ?
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 C13 1.364(2) . ?
C1 C2 1.441(2) . ?
C2 C3 1.379(2) . ?
C2 C6 1.457(2) . ?
C3 N5 1.343(2) . ?
C3 C4 1.506(2) . ?
N5 N6 1.416(2) . ?
N6 C15 1.467(2) . ?
N6 C7 1.477(2) . ?
C6 C8 1.402(2) . ?
C6 C12 1.416(2) . ?
C7 C8 1.509(2) . ?
C8 C9 1.388(2) . ?
C9 C10 1.398(3) . ?
C10 C11 1.376(3) . ?
C11 C12 1.397(2) . ?
C12 C13 1.451(3) . ?
C13 C14 1.471(3) . ?
C14 F1 1.325(2) . ?
C14 F3 1.339(2) . ?
C14 F2 1.348(3) . ?
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
C13 C1 C2 C3 -179.07(16) . . . . ?
C13 C1 C2 C6 1.0(2) . . . . ?
C1 C2 C3 N5 169.22(16) . . . . ?
C6 C2 C3 N5 -10.9(3) . . . . ?
C1 C2 C3 C4 -10.5(3) . . . . ?
C6 C2 C3 C4 169.41(16) . . . . ?
C2 C3 N5 N6 -14.4(3) . . . . ?
C4 C3 N5 N6 165.34(15) . . . . ?
C3 N5 N6 C15 -64.2(2) . . . . ?
C3 N5 N6 C7 64.4(2) . . . . ?
C3 C2 C6 C8 -2.6(3) . . . . ?
C1 C2 C6 C8 177.30(17) . . . . ?
C3 C2 C6 C12 179.30(16) . . . . ?
C1 C2 C6 C12 -0.79(18) . . . . ?
N5 N6 C7 C8 -78.06(18) . . . . ?
C15 N6 C7 C8 49.6(2) . . . . ?
C12 C6 C8 C9 -2.9(2) . . . . ?
C2 C6 C8 C9 179.26(17) . . . . ?
C12 C6 C8 C7 177.05(15) . . . . ?
C2 C6 C8 C7 -0.8(3) . . . . ?
N6 C7 C8 C9 -138.23(17) . . . . ?
N6 C7 C8 C6 41.9(2) . . . . ?
C6 C8 C9 C10 2.1(3) . . . . ?
C7 C8 C9 C10 -177.85(17) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C10 C11 C12 C6 0.3(2) . . . . ?
C10 C11 C12 C13 179.98(17) . . . . ?
C8 C6 C12 C11 1.7(2) . . . . ?
C2 C6 C12 C11 -179.94(14) . . . . ?
C8 C6 C12 C13 -178.03(14) . . . . ?
C2 C6 C12 C13 0.30(18) . . . . ?
C2 C1 C13 C12 -0.8(2) . . . . ?
C2 C1 C13 C14 -179.96(18) . . . . ?
C11 C12 C13 C1 -179.39(18) . . . . ?
C6 C12 C13 C1 0.33(19) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C6 C12 C13 C14 179.46(17) . . . . ?
C1 C13 C14 F1 -7.8(3) . . . . ?
C12 C13 C14 F1 173.20(18) . . . . ?
C1 C13 C14 F3 114.6(2) . . . . ?
C12 C13 C14 F3 -64.4(3) . . . . ?
C1 C13 C14 F2 -128.8(2) . . . . ?
C12 C13 C14 F2 52.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658964
