#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:14:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180295 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150948.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_7150948
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         'C19 H12 Cl1 N3 O4'
_chemical_formula_sum            'C19 H12 Cl N3 O4'
_chemical_formula_weight         381.77
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 98.387(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1149(11)
_cell_length_b                   18.630(3)
_cell_length_c                   13.388(2)
_cell_measurement_reflns_used    3618
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.67
_cell_measurement_wavelength     0.71073
_cell_volume                     1755.6(5)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0482
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18548
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.883
_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    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.468
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1051P)²+2.5426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1876
_refine_ls_wR_factor_ref         0.2032
_reflns_number_gt                3013
_reflns_number_total             4026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b804856h.txt
_cod_data_source_block           18b
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7150948
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4805(5) 0.01226(18) 0.7383(3) 0.0324(7) Uani 1 d . . .
H1 H 0.5915 -0.0207 0.7382 0.039 Uiso 1 calc R . .
C2 C 0.5714(4) 0.07535(14) 0.8821(2) 0.0197(6) Uani 1 d . . .
C3 C 0.5918(4) 0.12578(15) 0.7884(2) 0.0201(6) Uani 1 d . . .
C4 C 0.7667(4) 0.04111(15) 0.9239(2) 0.0221(6) Uani 1 d . . .
C5 C 0.3500(4) 0.14334(15) 0.9886(2) 0.0225(6) Uani 1 d . . .
H5 H 0.2427 0.1447 0.9372 0.027 Uiso 1 calc R . .
C6 C 0.3454(4) 0.17358(16) 1.0827(2) 0.0267(6) Uani 1 d . . .
C7 C 0.5018(4) 0.17310(16) 1.1575(2) 0.0257(6) Uani 1 d . . .
H7 H 0.4944 0.1959 1.2203 0.031 Uiso 1 calc R . .
C8 C 0.6687(4) 0.13972(15) 1.1417(2) 0.0234(6) Uani 1 d . . .
H8 H 0.7767 0.1388 1.1926 0.028 Uiso 1 calc R . .
C9 C 0.5174(4) 0.11132(14) 0.9730(2) 0.0198(6) Uani 1 d . . .
C10 C 0.6719(4) 0.10814(14) 1.0496(2) 0.0202(6) Uani 1 d . . .
C11 C 0.3052(5) -0.01681(18) 0.6746(2) 0.0315(7) Uani 1 d . . .
C12 C 0.1277(5) 0.0053(2) 0.6852(3) 0.0384(8) Uani 1 d . . .
H12 H 0.1122 0.044 0.7295 0.046 Uiso 1 calc R . .
C13 C -0.0256(5) -0.0261(2) 0.6345(3) 0.0430(9) Uani 1 d . . .
H13 H -0.1482 -0.0085 0.6418 0.052 Uiso 1 calc R . .
C14 C -0.0100(5) -0.08237(19) 0.5734(3) 0.0370(8) Uani 1 d . . .
C15 C 0.1649(6) -0.10743(18) 0.5557(3) 0.0408(9) Uani 1 d . . .
H15 H 0.1758 -0.1457 0.5101 0.049 Uiso 1 calc R . .
C16 C 0.3302(5) -0.0727(2) 0.6099(3) 0.0387(8) Uani 1 d . . .
H16 H 0.4542 -0.088 0.6013 0.046 Uiso 1 calc R . .
C17 C -0.1661(5) -0.1749(2) 0.4648(3) 0.0462(9) Uani 1 d . . .
H17A H -0.1153 -0.1612 0.4033 0.069 Uiso 1 calc R . .
H17B H -0.2932 -0.1954 0.4466 0.069 Uiso 1 calc R . .
H17C H -0.0822 -0.2105 0.5022 0.069 Uiso 1 calc R . .
C18 C 0.4739(4) 0.19107(16) 0.7896(2) 0.0237(6) Uani 1 d . . .
C19 C 0.7903(4) 0.14792(16) 0.7863(2) 0.0242(6) Uani 1 d . . .
N1 N 0.8175(3) 0.06684(13) 1.01727(19) 0.0223(5) Uani 1 d . . .
HN1 H 0.908(6) 0.053(2) 1.051(3) 0.05 Uiso 1 d . . .
N2 N 0.3823(4) 0.24086(16) 0.7922(2) 0.0362(7) Uani 1 d . . .
N3 N 0.9444(4) 0.16431(16) 0.7884(2) 0.0356(7) Uani 1 d . . .
O1 O 0.5218(3) 0.08456(12) 0.70332(15) 0.0305(5) Uani 1 d . . .
O2 O 0.4405(3) 0.02443(10) 0.83711(14) 0.0219(4) Uani 1 d . . .
O3 O 0.8522(3) -0.00107(12) 0.87770(15) 0.0273(5) Uani 1 d . . .
O4 O -0.1770(4) -0.11302(16) 0.5262(2) 0.0497(7) Uani 1 d . . .
Cl1 Cl 0.13552(10) 0.21292(5) 1.10636(7) 0.0415(3) 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 103.2(2) . . ?
O2 C1 C11 109.0(3) . . ?
O1 C1 C11 109.6(3) . . ?
O2 C1 H1 111.6 . . ?
O1 C1 H1 111.6 . . ?
C11 C1 H1 111.6 . . ?
O2 C2 C9 114.9(2) . . ?
O2 C2 C4 112.3(2) . . ?
C9 C2 C4 102.3(2) . . ?
O2 C2 C3 101.1(2) . . ?
C9 C2 C3 116.3(2) . . ?
C4 C2 C3 110.2(2) . . ?
O1 C3 C19 111.4(2) . . ?
O1 C3 C18 108.9(2) . . ?
C19 C3 C18 108.5(2) . . ?
O1 C3 C2 104.7(2) . . ?
C19 C3 C2 112.2(2) . . ?
C18 C3 C2 111.1(2) . . ?
O3 C4 N1 128.2(3) . . ?
O3 C4 C2 124.6(3) . . ?
N1 C4 C2 107.1(2) . . ?
C9 C5 C6 116.8(3) . . ?
C9 C5 H5 121.6 . . ?
C6 C5 H5 121.6 . . ?
C7 C6 C5 122.2(3) . . ?
C7 C6 Cl1 119.5(2) . . ?
C5 C6 Cl1 118.3(2) . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C10 C8 C7 117.3(3) . . ?
C10 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
C5 C9 C10 121.1(3) . . ?
C5 C9 C2 130.7(3) . . ?
C10 C9 C2 108.3(2) . . ?
C8 C10 C9 122.0(3) . . ?
C8 C10 N1 128.4(3) . . ?
C9 C10 N1 109.6(2) . . ?
C12 C11 C16 120.1(3) . . ?
C12 C11 C1 122.6(3) . . ?
C16 C11 C1 117.0(3) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 121.6(3) . . ?
C13 C14 O4 117.2(3) . . ?
C15 C14 O4 121.2(3) . . ?
C14 C15 C16 116.8(3) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 H15 121.6 . . ?
C11 C16 C15 118.9(3) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C3 178.8(3) . . ?
N3 C19 C3 177.4(3) . . ?
C4 N1 C10 111.8(2) . . ?
C4 N1 HN1 121(3) . . ?
C10 N1 HN1 126(3) . . ?
C3 O1 C1 107.8(2) . . ?
C2 O2 C1 107.4(2) . . ?
C14 O4 C17 118.8(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 O2 1.411(4) . ?
C1 O1 1.470(4) . ?
C1 C11 1.506(4) . ?
C1 H1 1 . ?
C2 O2 1.402(3) . ?
C2 C9 1.488(4) . ?
C2 C4 1.557(4) . ?
C2 C3 1.590(4) . ?
C3 O1 1.404(3) . ?
C3 C19 1.476(4) . ?
C3 C18 1.479(4) . ?
C4 O3 1.217(3) . ?
C4 N1 1.338(4) . ?
C5 C9 1.375(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.95 . ?
C6 C7 1.385(4) . ?
C6 Cl1 1.734(3) . ?
C7 C8 1.384(4) . ?
C7 H7 0.95 . ?
C8 C10 1.370(4) . ?
C8 H8 0.95 . ?
C9 C10 1.390(4) . ?
C10 N1 1.409(3) . ?
C11 C12 1.356(5) . ?
C11 C16 1.382(5) . ?
C12 C13 1.333(5) . ?
C12 H12 0.95 . ?
C13 C14 1.344(5) . ?
C13 H13 0.95 . ?
C14 C15 1.381(5) . ?
C14 O4 1.384(4) . ?
C15 C16 1.442(5) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 O4 1.425(5) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 N2 1.137(4) . ?
C19 N3 1.134(4) . ?
N1 HN1 0.77(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
O2 C2 C3 O1 -18.0(2) . . . . ?
C9 C2 C3 O1 -143.2(2) . . . . ?
C4 C2 C3 O1 100.9(2) . . . . ?
O2 C2 C3 C19 -139.0(2) . . . . ?
C9 C2 C3 C19 95.8(3) . . . . ?
C4 C2 C3 C19 -20.0(3) . . . . ?
O2 C2 C3 C18 99.4(2) . . . . ?
C9 C2 C3 C18 -25.8(3) . . . . ?
C4 C2 C3 C18 -141.6(2) . . . . ?
O2 C2 C4 O3 46.9(4) . . . . ?
C9 C2 C4 O3 170.6(3) . . . . ?
C3 C2 C4 O3 -65.0(3) . . . . ?
O2 C2 C4 N1 -133.1(2) . . . . ?
C9 C2 C4 N1 -9.3(3) . . . . ?
C3 C2 C4 N1 115.0(2) . . . . ?
C9 C5 C6 C7 1.1(4) . . . . ?
C9 C5 C6 Cl1 -178.7(2) . . . . ?
C5 C6 C7 C8 -2.2(5) . . . . ?
Cl1 C6 C7 C8 177.6(2) . . . . ?
C6 C7 C8 C10 0.4(4) . . . . ?
C6 C5 C9 C10 1.7(4) . . . . ?
C6 C5 C9 C2 -178.9(3) . . . . ?
O2 C2 C9 C5 -48.9(4) . . . . ?
C4 C2 C9 C5 -170.9(3) . . . . ?
C3 C2 C9 C5 68.9(4) . . . . ?
O2 C2 C9 C10 130.5(2) . . . . ?
C4 C2 C9 C10 8.5(3) . . . . ?
C3 C2 C9 C10 -111.7(3) . . . . ?
C7 C8 C10 C9 2.4(4) . . . . ?
C7 C8 C10 N1 -175.1(3) . . . . ?
C5 C9 C10 C8 -3.5(4) . . . . ?
C2 C9 C10 C8 177.0(3) . . . . ?
C5 C9 C10 N1 174.4(2) . . . . ?
C2 C9 C10 N1 -5.1(3) . . . . ?
O2 C1 C11 C12 36.4(4) . . . . ?
O1 C1 C11 C12 -75.9(4) . . . . ?
O2 C1 C11 C16 -137.6(3) . . . . ?
O1 C1 C11 C16 110.1(3) . . . . ?
C16 C11 C12 C13 0.3(5) . . . . ?
C1 C11 C12 C13 -173.5(3) . . . . ?
C11 C12 C13 C14 2.0(6) . . . . ?
C12 C13 C14 C15 -3.8(6) . . . . ?
C12 C13 C14 O4 178.0(3) . . . . ?
C13 C14 C15 C16 3.0(5) . . . . ?
O4 C14 C15 C16 -178.9(3) . . . . ?
C12 C11 C16 C15 -1.0(5) . . . . ?
C1 C11 C16 C15 173.2(3) . . . . ?
C14 C15 C16 C11 -0.6(5) . . . . ?
O1 C3 C18 N2 118(16) . . . . ?
C19 C3 C18 N2 -120(16) . . . . ?
C2 C3 C18 N2 3(16) . . . . ?
O1 C3 C19 N3 -137(7) . . . . ?
C18 C3 C19 N3 104(7) . . . . ?
C2 C3 C19 N3 -20(7) . . . . ?
O3 C4 N1 C10 -173.1(3) . . . . ?
C2 C4 N1 C10 6.8(3) . . . . ?
C8 C10 N1 C4 176.4(3) . . . . ?
C9 C10 N1 C4 -1.3(3) . . . . ?
C19 C3 O1 C1 115.9(3) . . . . ?
C18 C3 O1 C1 -124.6(2) . . . . ?
C2 C3 O1 C1 -5.7(3) . . . . ?
O2 C1 O1 C3 27.5(3) . . . . ?
C11 C1 O1 C3 143.5(3) . . . . ?
C9 C2 O2 C1 162.3(2) . . . . ?
C4 C2 O2 C1 -81.3(3) . . . . ?
C3 C2 O2 C1 36.2(3) . . . . ?
O1 C1 O2 C2 -40.9(3) . . . . ?
C11 C1 O2 C2 -157.4(2) . . . . ?
C13 C14 O4 C17 -177.0(3) . . . . ?
C15 C14 O4 C17 4.8(5) . . . . ?
