#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150946.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_7150946
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         'C18 H10 Cl1 N3 O3'
_chemical_formula_sum            'C18 H10 Cl N3 O3'
_chemical_formula_weight         351.74
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90
_cell_angle_beta                 98.668(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4743(11)
_cell_length_b                   10.6042(12)
_cell_length_c                   13.0970(14)
_cell_measurement_reflns_used    8461
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.63
_cell_measurement_wavelength     0.71073
_cell_volume                     1575.4(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0398
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15693
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.858
_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    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0332P)²+1.0054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0895
_reflns_number_gt                3325
_reflns_number_total             3596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b804856h.txt
_cod_data_source_block           11a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7150946
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.46610(12) 0.21139(13) 0.63969(11) 0.0145(3) Uani 1 d . . .
H1 H 0.5072 0.235 0.5803 0.017 Uiso 1 calc R . .
C2 C 0.59863(11) 0.13187(12) 0.77724(10) 0.0126(3) Uani 1 d . . .
C3 C 0.59728(11) 0.28156(12) 0.77284(10) 0.0136(3) Uani 1 d . . .
C4 C 0.55183(12) 0.08726(12) 0.87750(10) 0.0141(3) Uani 1 d . . .
C5 C 0.79927(12) 0.06278(13) 0.72107(11) 0.0170(3) Uani 1 d . . .
H5 H 0.7817 0.0934 0.6523 0.02 Uiso 1 calc R . .
C6 C 0.90760(12) 0.00517(13) 0.75699(12) 0.0187(3) Uani 1 d . . .
H6 H 0.964 -0.0053 0.7115 0.022 Uiso 1 calc R . .
C7 C 0.93348(12) -0.03682(13) 0.85831(12) 0.0199(3) Uani 1 d . . .
H7 H 1.0085 -0.073 0.8815 0.024 Uiso 1 calc R . .
C8 C 0.85190(12) -0.02712(13) 0.92704(11) 0.0173(3) Uani 1 d . . .
H8 H 0.8699 -0.0554 0.9964 0.021 Uiso 1 calc R . .
C9 C 0.71882(11) 0.07343(12) 0.78932(11) 0.0138(3) Uani 1 d . . .
C10 C 0.74400(11) 0.02542(12) 0.88958(11) 0.0141(3) Uani 1 d . . .
C11 C 0.33718(12) 0.19485(12) 0.60323(11) 0.0150(3) Uani 1 d . . .
C12 C 0.29529(12) 0.19657(13) 0.49794(11) 0.0167(3) Uani 1 d . . .
H12 H 0.3489 0.2065 0.4498 0.02 Uiso 1 calc R . .
C13 C 0.17517(13) 0.18387(14) 0.46265(12) 0.0198(3) Uani 1 d . . .
H13 H 0.146 0.1849 0.3908 0.024 Uiso 1 calc R . .
C14 C 0.09914(12) 0.16966(13) 0.53461(12) 0.0198(3) Uani 1 d . . .
C15 C 0.13960(13) 0.16538(14) 0.63990(12) 0.0204(3) Uani 1 d . . .
H15 H 0.0858 0.1545 0.6877 0.024 Uiso 1 calc R . .
C16 C 0.25951(12) 0.17723(13) 0.67451(12) 0.0181(3) Uani 1 d . . .
H16 H 0.2886 0.1734 0.7463 0.022 Uiso 1 calc R . .
C17 C 0.61295(12) 0.33929(12) 0.87698(11) 0.0158(3) Uani 1 d . . .
C18 C 0.69135(12) 0.33246(13) 0.71619(11) 0.0163(3) Uani 1 d . . .
N1 N 0.64384(10) 0.03619(11) 0.94004(9) 0.0144(2) Uani 1 d . . .
HN1 H 0.6352(19) -0.001(2) 0.9986(18) 0.05 Uiso 1 d . . .
N2 N 0.63247(12) 0.37613(12) 0.95976(10) 0.0231(3) Uani 1 d . . .
N3 N 0.76022(11) 0.37477(13) 0.67170(11) 0.0241(3) Uani 1 d . . .
O1 O 0.48442(8) 0.30783(9) 0.71822(7) 0.0148(2) Uani 1 d . . .
O2 O 0.51819(8) 0.09948(9) 0.68868(7) 0.0153(2) Uani 1 d . . .
O3 O 0.45053(8) 0.09902(9) 0.89364(8) 0.0177(2) Uani 1 d . . .
Cl1 Cl -0.05211(3) 0.16213(4) 0.49145(3) 0.02768(12) 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 105.14(10) . . ?
O2 C1 C11 111.78(11) . . ?
O1 C1 C11 109.98(11) . . ?
O2 C1 H1 109.9 . . ?
O1 C1 H1 109.9 . . ?
C11 C1 H1 109.9 . . ?
O2 C2 C9 117.62(11) . . ?
O2 C2 C4 110.57(10) . . ?
C9 C2 C4 102.30(10) . . ?
O2 C2 C3 102.23(10) . . ?
C9 C2 C3 114.90(11) . . ?
C4 C2 C3 109.26(10) . . ?
O1 C3 C17 111.12(11) . . ?
O1 C3 C18 110.65(11) . . ?
C17 C3 C18 108.08(11) . . ?
O1 C3 C2 102.66(10) . . ?
C17 C3 C2 112.37(11) . . ?
C18 C3 C2 111.95(11) . . ?
O3 C4 N1 128.00(13) . . ?
O3 C4 C2 124.85(12) . . ?
N1 C4 C2 107.15(11) . . ?
C9 C5 C6 117.61(13) . . ?
C9 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C7 C6 C5 120.78(13) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.64(13) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C10 C8 C7 116.97(13) . . ?
C10 C8 H8 121.5 . . ?
C7 C8 H8 121.5 . . ?
C5 C9 C10 120.93(12) . . ?
C5 C9 C2 131.22(13) . . ?
C10 C9 C2 107.85(11) . . ?
C8 C10 C9 121.94(13) . . ?
C8 C10 N1 128.02(13) . . ?
C9 C10 N1 110.01(12) . . ?
C12 C11 C16 120.30(13) . . ?
C12 C11 C1 119.53(12) . . ?
C16 C11 C1 120.17(13) . . ?
C11 C12 C13 120.32(13) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 118.54(14) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C13 C14 C15 121.93(13) . . ?
C13 C14 Cl1 118.83(12) . . ?
C15 C14 Cl1 119.21(12) . . ?
C14 C15 C16 119.22(14) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C11 119.65(14) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
N2 C17 C3 174.04(15) . . ?
N3 C18 C3 177.45(15) . . ?
C4 N1 C10 111.45(12) . . ?
C4 N1 HN1 121.8(14) . . ?
C10 N1 HN1 125.2(14) . . ?
C3 O1 C1 104.21(10) . . ?
C2 O2 C1 110.04(10) . . ?
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 1.4358(16) . ?
C1 O1 1.4431(16) . ?
C1 C11 1.4947(18) . ?
C1 H1 1 . ?
C2 O2 1.4116(15) . ?
C2 C9 1.4984(18) . ?
C2 C4 1.5649(18) . ?
C2 C3 1.5883(18) . ?
C3 O1 1.4097(15) . ?
C3 C17 1.4811(19) . ?
C3 C18 1.4995(19) . ?
C4 O3 1.2188(16) . ?
C4 N1 1.3484(17) . ?
C5 C9 1.3829(19) . ?
C5 C6 1.4012(19) . ?
C5 H5 0.95 . ?
C6 C7 1.389(2) . ?
C6 H6 0.95 . ?
C7 C8 1.397(2) . ?
C7 H7 0.95 . ?
C8 C10 1.3787(18) . ?
C8 H8 0.95 . ?
C9 C10 1.3974(19) . ?
C10 N1 1.4140(17) . ?
C11 C12 1.390(2) . ?
C11 C16 1.397(2) . ?
C12 C13 1.3926(19) . ?
C12 H12 0.95 . ?
C13 C14 1.386(2) . ?
C13 H13 0.95 . ?
C14 C15 1.388(2) . ?
C14 Cl1 1.7443(14) . ?
C15 C16 1.3880(19) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 N2 1.1423(19) . ?
C18 N3 1.1419(19) . ?
N1 HN1 0.88(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 26.66(12) . . . . ?
C9 C2 C3 O1 155.23(11) . . . . ?
C4 C2 C3 O1 -90.50(12) . . . . ?
O2 C2 C3 C17 146.12(11) . . . . ?
C9 C2 C3 C17 -85.31(14) . . . . ?
C4 C2 C3 C17 28.96(14) . . . . ?
O2 C2 C3 C18 -92.03(12) . . . . ?
C9 C2 C3 C18 36.53(16) . . . . ?
C4 C2 C3 C18 150.80(11) . . . . ?
O2 C2 C4 O3 -43.65(17) . . . . ?
C9 C2 C4 O3 -169.71(13) . . . . ?
C3 C2 C4 O3 68.11(16) . . . . ?
O2 C2 C4 N1 136.88(11) . . . . ?
C9 C2 C4 N1 10.82(13) . . . . ?
C3 C2 C4 N1 -111.36(12) . . . . ?
C9 C5 C6 C7 -1.4(2) . . . . ?
C5 C6 C7 C8 2.1(2) . . . . ?
C6 C7 C8 C10 0.4(2) . . . . ?
C6 C5 C9 C10 -1.6(2) . . . . ?
C6 C5 C9 C2 178.12(13) . . . . ?
O2 C2 C9 C5 48.8(2) . . . . ?
C4 C2 C9 C5 170.14(14) . . . . ?
C3 C2 C9 C5 -71.60(18) . . . . ?
O2 C2 C9 C10 -131.45(12) . . . . ?
C4 C2 C9 C10 -10.13(13) . . . . ?
C3 C2 C9 C10 108.13(13) . . . . ?
C7 C8 C10 C9 -3.5(2) . . . . ?
C7 C8 C10 N1 174.24(13) . . . . ?
C5 C9 C10 C8 4.2(2) . . . . ?
C2 C9 C10 C8 -175.60(12) . . . . ?
C5 C9 C10 N1 -173.91(12) . . . . ?
C2 C9 C10 N1 6.33(15) . . . . ?
O2 C1 C11 C12 -114.07(14) . . . . ?
O1 C1 C11 C12 129.54(13) . . . . ?
O2 C1 C11 C16 65.65(16) . . . . ?
O1 C1 C11 C16 -50.74(16) . . . . ?
C16 C11 C12 C13 1.6(2) . . . . ?
C1 C11 C12 C13 -178.69(12) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C13 C14 C15 -1.3(2) . . . . ?
C12 C13 C14 Cl1 176.63(11) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
Cl1 C14 C15 C16 -177.05(11) . . . . ?
C14 C15 C16 C11 0.8(2) . . . . ?
C12 C11 C16 C15 -2.0(2) . . . . ?
C1 C11 C16 C15 178.27(13) . . . . ?
O1 C3 C17 N2 157.1(14) . . . . ?
C18 C3 C17 N2 -81.4(14) . . . . ?
C2 C3 C17 N2 42.7(15) . . . . ?
O1 C3 C18 N3 32(4) . . . . ?
C17 C3 C18 N3 -90(4) . . . . ?
C2 C3 C18 N3 146(4) . . . . ?
O3 C4 N1 C10 172.86(13) . . . . ?
C2 C4 N1 C10 -7.69(14) . . . . ?
C8 C10 N1 C4 -176.82(13) . . . . ?
C9 C10 N1 C4 1.10(15) . . . . ?
C17 C3 O1 C1 -159.18(11) . . . . ?
C18 C3 O1 C1 80.75(13) . . . . ?
C2 C3 O1 C1 -38.86(12) . . . . ?
O2 C1 O1 C3 37.44(12) . . . . ?
C11 C1 O1 C3 157.93(11) . . . . ?
C9 C2 O2 C1 -130.87(12) . . . . ?
C4 C2 O2 C1 112.18(11) . . . . ?
C3 C2 O2 C1 -4.04(13) . . . . ?
O1 C1 O2 C2 -19.57(13) . . . . ?
C11 C1 O2 C2 -138.86(11) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190309
