#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150938.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_7150938
loop_
_publ_author_name
'Bentabed-Ababsa, Ghenia'
'Derdour, Aicha'
'Roisnel, Thierry'
'Sáez, Jose A.'
'Domingo, Luis R.'
'Mongin, Florence'
_publ_section_title
;
 Polar [3 + 2] cycloaddition of ketones with electrophilically
 activated carbonyl ylides. Synthesis of spirocyclic dioxolane
 indolinones
;
_journal_issue                   17
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3144
_journal_page_last               3157
_journal_paper_doi               10.1039/b804856h
_journal_volume                  6
_journal_year                    2008
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H13 Cl1 N2 O4'
_chemical_formula_sum            'C15 H13 Cl N2 O4'
_chemical_formula_weight         320.72
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                111.597(3)
_cell_angle_beta                 96.849(3)
_cell_angle_gamma                103.339(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5107(5)
_cell_length_b                   10.4161(8)
_cell_length_c                   10.9534(7)
_cell_measurement_reflns_used    6940
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.2
_cell_measurement_wavelength     0.71073
_cell_volume                     755.26(9)
_computing_cell_refinement       'Bruker SMART, 2006'
_computing_data_collection       'Bruker SMART, 2006'
_computing_data_reduction        'Bruker SAINT, 2006'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14105
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.41
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0456P)²+0.4513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                3060
_reflns_number_total             3361
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b804856h.txt
_cod_data_source_block           4a
_cod_original_cell_volume        755.25(9)
_cod_database_code               7150938
loop_
_symmetry_equiv_pos_as_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0846(2) 0.5981(2) 0.77586(18) 0.0170(4) Uani 1 d . . .
H1 H -0.0315 0.6291 0.7706 0.02 Uiso 1 calc R . .
C2 C 0.2292(2) 0.68738(19) 0.64153(18) 0.0147(4) Uani 1 d . . .
C3 C 0.3532(2) 0.77260(19) 0.79057(18) 0.0153(4) Uani 1 d . . .
C4 C 0.0528(2) 0.47281(19) 0.81453(18) 0.0164(4) Uani 1 d . . .
C5 C -0.1273(3) 0.4064(2) 0.82030(18) 0.0179(4) Uani 1 d . . .
H5 H -0.2257 0.4465 0.8073 0.021 Uiso 1 calc R . .
C6 C -0.1656(3) 0.2821(2) 0.84481(19) 0.0206(4) Uani 1 d . . .
H6 H -0.2889 0.2368 0.8485 0.025 Uiso 1 calc R . .
C7 C -0.0189(3) 0.2255(2) 0.86383(19) 0.0200(4) Uani 1 d . . .
C8 C 0.1634(3) 0.2923(2) 0.8628(2) 0.0221(4) Uani 1 d . . .
H8 H 0.2625 0.2541 0.8795 0.027 Uiso 1 calc R . .
C9 C 0.1988(3) 0.4158(2) 0.8370(2) 0.0212(4) Uani 1 d . . .
H9 H 0.3225 0.4617 0.8347 0.025 Uiso 1 calc R . .
C10 C 0.3447(2) 0.6508(2) 0.53473(18) 0.0172(4) Uani 1 d . . .
C11 C 0.5967(3) 0.7542(2) 0.4558(2) 0.0246(4) Uani 1 d . . .
H11A H 0.5243 0.7108 0.3612 0.03 Uiso 1 calc R . .
H11B H 0.6694 0.6898 0.4675 0.03 Uiso 1 calc R . .
C12 C 0.7273(3) 0.9022(3) 0.4888(2) 0.0341(5) Uani 1 d . . .
H12A H 0.8149 0.8939 0.4288 0.051 Uiso 1 calc R . .
H12B H 0.798 0.9441 0.5826 0.051 Uiso 1 calc R . .
H12C H 0.6538 0.9648 0.4765 0.051 Uiso 1 calc R . .
C13 C 0.0939(3) 0.7654(2) 0.60749(19) 0.0193(4) Uani 1 d . . .
H13A H 0.0209 0.7883 0.6768 0.029 Uiso 1 calc R . .
H13B H 0.0086 0.7027 0.5196 0.029 Uiso 1 calc R . .
H13C H 0.1656 0.855 0.6043 0.029 Uiso 1 calc R . .
C14 C 0.3920(2) 0.9316(2) 0.83750(18) 0.0172(4) Uani 1 d . . .
C15 C 0.5355(3) 0.7386(2) 0.80553(18) 0.0185(4) Uani 1 d . . .
N1 N 0.4207(2) 1.05389(18) 0.87010(17) 0.0228(4) Uani 1 d . . .
N2 N 0.6716(2) 0.70845(19) 0.81814(18) 0.0279(4) Uani 1 d . . .
O1 O 0.24401(18) 0.72012(14) 0.86801(13) 0.0186(3) Uani 1 d . . .
O2 O 0.13551(17) 0.55738(13) 0.64947(12) 0.0161(3) Uani 1 d . . .
O3 O 0.32175(19) 0.53206(15) 0.45091(14) 0.0239(3) Uani 1 d . . .
O4 O 0.46976(18) 0.77285(14) 0.54830(13) 0.0219(3) Uani 1 d . . .
Cl1 Cl -0.06573(7) 0.06710(5) 0.89026(5) 0.02613(16) Uani 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
O2 C1 O1 104.47(13) . . ?
O2 C1 C4 109.04(14) . . ?
O1 C1 C4 112.45(15) . . ?
O2 C1 H1 110.2 . . ?
O1 C1 H1 110.2 . . ?
C4 C1 H1 110.2 . . ?
O2 C2 C10 107.93(14) . . ?
O2 C2 C13 112.68(14) . . ?
C10 C2 C13 110.36(15) . . ?
O2 C2 C3 99.45(14) . . ?
C10 C2 C3 113.49(14) . . ?
C13 C2 C3 112.46(14) . . ?
O1 C3 C14 111.00(14) . . ?
O1 C3 C15 108.29(15) . . ?
C14 C3 C15 109.04(15) . . ?
O1 C3 C2 103.95(14) . . ?
C14 C3 C2 112.17(15) . . ?
C15 C3 C2 112.25(14) . . ?
C5 C4 C9 119.51(18) . . ?
C5 C4 C1 119.34(16) . . ?
C9 C4 C1 121.03(17) . . ?
C4 C5 C6 121.02(17) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 118.39(18) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C8 C7 C6 121.76(18) . . ?
C8 C7 Cl1 119.24(15) . . ?
C6 C7 Cl1 119.00(15) . . ?
C7 C8 C9 119.00(17) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C8 C9 C4 120.26(18) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
O3 C10 O4 126.30(17) . . ?
O3 C10 C2 124.64(17) . . ?
O4 C10 C2 109.03(15) . . ?
O4 C11 C12 107.18(16) . . ?
O4 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O4 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C3 178.1(2) . . ?
N2 C15 C3 177.5(2) . . ?
C3 O1 C1 108.23(13) . . ?
C2 O2 C1 106.26(13) . . ?
C10 O4 C11 115.39(14) . . ?
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 O2 1.418(2) . ?
C1 O1 1.460(2) . ?
C1 C4 1.492(3) . ?
C1 H1 1 . ?
C2 O2 1.414(2) . ?
C2 C10 1.527(2) . ?
C2 C13 1.532(2) . ?
C2 C3 1.584(2) . ?
C3 O1 1.411(2) . ?
C3 C14 1.486(3) . ?
C3 C15 1.497(2) . ?
C4 C5 1.390(3) . ?
C4 C9 1.400(3) . ?
C5 C6 1.391(3) . ?
C5 H5 0.95 . ?
C6 C7 1.393(3) . ?
C6 H6 0.95 . ?
C7 C8 1.389(3) . ?
C7 Cl1 1.743(2) . ?
C8 C9 1.390(3) . ?
C8 H8 0.95 . ?
C9 H9 0.95 . ?
C10 O3 1.196(2) . ?
C10 O4 1.341(2) . ?
C11 O4 1.465(2) . ?
C11 C12 1.509(3) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 N1 1.147(2) . ?
C15 N2 1.144(2) . ?
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
O2 C2 C3 O1 -30.51(15) . . . . ?
C10 C2 C3 O1 -144.88(15) . . . . ?
C13 C2 C3 O1 88.95(17) . . . . ?
O2 C2 C3 C14 -150.51(14) . . . . ?
C10 C2 C3 C14 95.12(17) . . . . ?
C13 C2 C3 C14 -31.1(2) . . . . ?
O2 C2 C3 C15 86.30(17) . . . . ?
C10 C2 C3 C15 -28.1(2) . . . . ?
C13 C2 C3 C15 -154.24(16) . . . . ?
O2 C1 C4 C5 -113.03(17) . . . . ?
O1 C1 C4 C5 131.59(17) . . . . ?
O2 C1 C4 C9 63.1(2) . . . . ?
O1 C1 C4 C9 -52.3(2) . . . . ?
C9 C4 C5 C6 -1.6(3) . . . . ?
C1 C4 C5 C6 174.55(16) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
C5 C6 C7 Cl1 -178.33(14) . . . . ?
C6 C7 C8 C9 -2.5(3) . . . . ?
Cl1 C7 C8 C9 177.80(15) . . . . ?
C7 C8 C9 C4 0.9(3) . . . . ?
C5 C4 C9 C8 1.0(3) . . . . ?
C1 C4 C9 C8 -175.03(17) . . . . ?
O2 C2 C10 O3 17.2(2) . . . . ?
C13 C2 C10 O3 -106.3(2) . . . . ?
C3 C2 C10 O3 126.44(19) . . . . ?
O2 C2 C10 O4 -164.66(14) . . . . ?
C13 C2 C10 O4 71.81(18) . . . . ?
C3 C2 C10 O4 -55.46(19) . . . . ?
O1 C3 C14 N1 -135(5) . . . . ?
C15 C3 C14 N1 106(5) . . . . ?
C2 C3 C14 N1 -19(6) . . . . ?
O1 C3 C15 N2 24(5) . . . . ?
C14 C3 C15 N2 145(5) . . . . ?
C2 C3 C15 N2 -90(5) . . . . ?
C14 C3 O1 C1 129.45(15) . . . . ?
C15 C3 O1 C1 -110.87(15) . . . . ?
C2 C3 O1 C1 8.66(17) . . . . ?
O2 C1 O1 C3 16.53(17) . . . . ?
C4 C1 O1 C3 134.64(15) . . . . ?
C10 C2 O2 C1 160.42(13) . . . . ?
C13 C2 O2 C1 -77.47(17) . . . . ?
C3 C2 O2 C1 41.83(15) . . . . ?
O1 C1 O2 C2 -38.33(16) . . . . ?
C4 C1 O2 C2 -158.75(14) . . . . ?
O3 C10 O4 C11 -4.3(3) . . . . ?
C2 C10 O4 C11 177.61(15) . . . . ?
C12 C11 O4 C10 -178.92(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25938380
2 PubChem 139190304
