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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/4/02/45/4024576.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.
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data_4024576
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            'C10 H19 N2 O5 P'
_chemical_formula_weight         278.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 96.56(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.691(1)
_cell_length_b                   10.311(1)
_cell_length_c                   17.038(1)
_cell_measurement_reflns_used    3090
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      38.38
_cell_measurement_theta_min      0.41
_cell_volume                     1342.3(2)
_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      198(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11459
_diffrn_reflns_theta_full        28.12
_diffrn_reflns_theta_max         28.12
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_correction_T_min  0.9369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995 & 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0532P)²+0.2773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                2086
_reflns_number_total             3212
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900270e_si_001.cif
_cod_data_source_block           wue3774
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4024576
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.49308(16) 1.29838(15) 0.10631(9) 0.0448(4) Uani 1 1 d . . .
C2 C 0.4757(3) 1.2676(2) 0.18642(13) 0.0504(6) Uani 1 1 d . . .
H2A H 0.4030 1.3346 0.2086 0.061 Uiso 1 1 calc R . .
H2B H 0.5928 1.2687 0.2174 0.061 Uiso 1 1 calc R . .
C3 C 0.3928(2) 1.1361(2) 0.19413(13) 0.0425(5) Uani 1 1 d . . .
H3A H 0.4672 1.0680 0.1741 0.051 Uiso 1 1 calc R . .
H3B H 0.3816 1.1177 0.2504 0.051 Uiso 1 1 calc R . .
N4 N 0.21891(17) 1.13568(15) 0.14813(9) 0.0285(4) Uani 1 1 d . . .
C5 C 0.2374(2) 1.1672(2) 0.06533(11) 0.0351(5) Uani 1 1 d . . .
H5A H 0.1207 1.1695 0.0341 0.042 Uiso 1 1 calc R . .
H5B H 0.3083 1.0997 0.0426 0.042 Uiso 1 1 calc R . .
C6 C 0.3252(2) 1.2971(2) 0.06155(13) 0.0414(5) Uani 1 1 d . . .
H6A H 0.3378 1.3182 0.0058 0.050 Uiso 1 1 calc R . .
H6B H 0.2508 1.3646 0.0821 0.050 Uiso 1 1 calc R . .
N7 N 0.13491(18) 1.01892(15) 0.16171(8) 0.0272(4) Uani 1 1 d . . .
C8 C -0.0275(2) 1.00528(18) 0.13474(10) 0.0267(4) Uani 1 1 d . . .
C9 C -0.1457(2) 1.1026(2) 0.09128(13) 0.0392(5) Uani 1 1 d . . .
H9A H -0.1064 1.1902 0.1070 0.059 Uiso 1 1 calc R . .
H9B H -0.2655 1.0897 0.1040 0.059 Uiso 1 1 calc R . .
H9C H -0.1427 1.0919 0.0343 0.059 Uiso 1 1 calc R . .
C10 C -0.1077(2) 0.87969(19) 0.15533(11) 0.0286(4) Uani 1 1 d . . .
O11 O -0.26036(16) 0.85629(14) 0.13159(8) 0.0415(4) Uani 1 1 d . . .
C12 C 0.0023(2) 0.78297(19) 0.20567(11) 0.0317(4) Uani 1 1 d . A .
H12A H -0.0673 0.7491 0.2466 0.038 Uiso 1 1 calc R . .
H12B H 0.1051 0.8286 0.2331 0.038 Uiso 1 1 calc R . .
P13 P 0.07762(7) 0.64925(5) 0.15216(3) 0.04005(19) Uani 1 1 d . . .
O14 O 0.18576(17) 0.55794(14) 0.20231(8) 0.0459(4) Uani 1 1 d . A .
O15 O 0.1661(2) 0.70820(16) 0.08135(8) 0.0535(4) Uani 1 1 d . A .
C17 C 0.3506(3) 0.7346(3) 0.09043(16) 0.0766(9) Uani 1 1 d . . .
H17A H 0.3883 0.7546 0.0387 0.115 Uiso 1 1 calc R A .
H17B H 0.4142 0.6584 0.1129 0.115 Uiso 1 1 calc R . .
H17C H 0.3751 0.8089 0.1259 0.115 Uiso 1 1 calc R . .
O16A O -0.1181(7) 0.5945(4) 0.1233(6) 0.0378(18) Uani 0.494(16) 1 d P A 1
C18A C -0.1288(14) 0.4624(10) 0.0924(7) 0.0443(19) Uani 0.494(16) 1 d P A 1
H18A H -0.0869 0.4607 0.0402 0.066 Uiso 0.494(16) 1 calc PR A 1
H18B H -0.2506 0.4329 0.0879 0.066 Uiso 0.494(16) 1 calc PR A 1
H18C H -0.0562 0.4050 0.1284 0.066 Uiso 0.494(16) 1 calc PR A 1
O16B O -0.0640(10) 0.5933(4) 0.0874(5) 0.0386(18) Uani 0.506(16) 1 d P A 2
C18B C -0.1769(15) 0.4956(11) 0.1095(7) 0.054(2) Uani 0.506(16) 1 d P A 2
H18D H -0.1087 0.4300 0.1412 0.082 Uiso 0.506(16) 1 calc PR A 2
H18E H -0.2374 0.4550 0.0620 0.082 Uiso 0.506(16) 1 calc PR A 2
H18F H -0.2633 0.5340 0.1407 0.082 Uiso 0.506(16) 1 calc PR A 2
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'
P P 0.1023 0.0942 '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 O1 C2 109.49(14) . . ?
O1 C2 C3 111.73(18) . . ?
N4 C3 C2 108.86(17) . . ?
N7 N4 C5 116.51(14) . . ?
N7 N4 C3 108.87(14) . . ?
C5 N4 C3 109.19(14) . . ?
N4 C5 C6 109.32(16) . . ?
O1 C6 C5 111.67(17) . . ?
C8 N7 N4 118.84(15) . . ?
N7 C8 C9 127.87(17) . . ?
N7 C8 C10 114.85(16) . . ?
C9 C8 C10 117.11(15) . . ?
O11 C10 C8 120.04(17) . . ?
O11 C10 C12 120.84(17) . . ?
C8 C10 C12 119.12(15) . . ?
C10 C12 P13 114.42(13) . . ?
O14 P13 O16B 118.44(16) . . ?
O14 P13 O15 115.40(9) . . ?
O16B P13 O15 85.9(4) . . ?
O14 P13 O16A 113.4(2) . . ?
O15 P13 O16A 111.6(4) . . ?
O14 P13 C12 113.21(9) . . ?
O16B P13 C12 113.8(3) . . ?
O15 P13 C12 106.68(9) . . ?
O16A P13 C12 94.6(3) . . ?
C17 O15 P13 119.97(14) . . ?
C18A O16A P13 116.4(7) . . ?
C18B O16B P13 118.3(8) . . ?
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
O1 C6 1.422(2) . ?
O1 C2 1.422(3) . ?
C2 C3 1.511(3) . ?
C3 N4 1.471(2) . ?
N4 N7 1.398(2) . ?
N4 C5 1.470(2) . ?
C5 C6 1.505(3) . ?
N7 C8 1.289(2) . ?
C8 C9 1.493(3) . ?
C8 C10 1.493(3) . ?
C10 O11 1.222(2) . ?
C10 C12 1.510(3) . ?
C12 P13 1.786(2) . ?
P13 O14 1.4649(14) . ?
P13 O16B 1.569(3) . ?
P13 O15 1.5736(17) . ?
P13 O16A 1.630(4) . ?
O15 C17 1.435(3) . ?
O16A C18A 1.459(12) . ?
O16B C18B 1.409(13) . ?
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 O1 C2 C3 59.0(2) . . . . ?
O1 C2 C3 N4 -59.1(2) . . . . ?
C2 C3 N4 N7 -173.98(16) . . . . ?
C2 C3 N4 C5 57.8(2) . . . . ?
N7 N4 C5 C6 178.29(14) . . . . ?
C3 N4 C5 C6 -57.9(2) . . . . ?
C2 O1 C6 C5 -58.8(2) . . . . ?
N4 C5 C6 O1 58.9(2) . . . . ?
C5 N4 N7 C8 -64.5(2) . . . . ?
C3 N4 N7 C8 171.51(16) . . . . ?
N4 N7 C8 C9 -2.3(3) . . . . ?
N4 N7 C8 C10 -177.39(14) . . . . ?
N7 C8 C10 O11 -178.86(17) . . . . ?
C9 C8 C10 O11 5.5(3) . . . . ?
N7 C8 C10 C12 1.2(2) . . . . ?
C9 C8 C10 C12 -174.48(17) . . . . ?
O11 C10 C12 P13 76.8(2) . . . . ?
C8 C10 C12 P13 -103.21(17) . . . . ?
C10 C12 P13 O14 179.27(12) . . . . ?
C10 C12 P13 O16B -41.7(3) . . . . ?
C10 C12 P13 O15 51.26(15) . . . . ?
C10 C12 P13 O16A -62.9(4) . . . . ?
O14 P13 O15 C17 -34.7(2) . . . . ?
O16B P13 O15 C17 -154.3(3) . . . . ?
O16A P13 O15 C17 -166.0(3) . . . . ?
C12 P13 O15 C17 92.0(2) . . . . ?
O14 P13 O16A C18A -47.0(11) . . . . ?
O16B P13 O16A C18A 60.0(9) . . . . ?
O15 P13 O16A C18A 85.4(10) . . . . ?
C12 P13 O16A C18A -164.7(10) . . . . ?
O14 P13 O16B C18B 48.3(14) . . . . ?
O15 P13 O16B C18B 165.1(12) . . . . ?
O16A P13 O16B C18B -38.4(10) . . . . ?
C12 P13 O16B C18B -88.4(11) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 44196482
