#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:14:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180295 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150940.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_7150940
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 O3'
_chemical_formula_sum            'C19 H12 Cl N3 O3'
_chemical_formula_weight         365.77
_chemical_name_systematic
;
?
;
_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                76.326(5)
_cell_angle_beta                 69.235(4)
_cell_angle_gamma                87.179(4)
_cell_formula_units_Z            2
_cell_length_a                   9.1044(8)
_cell_length_b                   9.8097(8)
_cell_length_c                   10.3197(9)
_cell_measurement_reflns_used    4879
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.6
_cell_measurement_wavelength     0.71073
_cell_volume                     836.76(13)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0363
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11773
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.847
_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    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0415
_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)+(0.0694P)²+0.2316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                3188
_reflns_number_total             3795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b804856h.txt
_cod_data_source_block           7b
_cod_original_cell_volume        836.76(12)
_cod_database_code               7150940
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 0.78680(17) 0.33098(17) 0.00998(16) 0.0206(3) Uani 1 d . . .
H1 H 0.8408 0.4188 0.0065 0.025 Uiso 1 calc R . .
C2 C 0.52848(16) 0.33251(15) 0.15513(15) 0.0168(3) Uani 1 d . . .
C3 C 0.60607(16) 0.19894(16) 0.22042(16) 0.0178(3) Uani 1 d . . .
C4 C 0.53131(18) 0.44992(16) 0.23317(16) 0.0197(3) Uani 1 d . . .
C5 C 0.27992(17) 0.24117(16) 0.12223(16) 0.0193(3) Uani 1 d . . .
H5 H 0.3364 0.1889 0.0546 0.023 Uiso 1 calc R . .
C6 C 0.11527(18) 0.24428(17) 0.16870(18) 0.0230(3) Uani 1 d . . .
H6 H 0.0592 0.1934 0.1322 0.028 Uiso 1 calc R . .
C7 C 0.03343(18) 0.32085(18) 0.26740(18) 0.0254(4) Uani 1 d . . .
H7 H -0.0781 0.3203 0.2983 0.03 Uiso 1 calc R . .
C8 C 0.11162(18) 0.39906(17) 0.32254(17) 0.0233(3) Uani 1 d . . .
H8 H 0.0555 0.452 0.3896 0.028 Uiso 1 calc R . .
C9 C 0.35748(16) 0.31646(15) 0.17787(16) 0.0167(3) Uani 1 d . . .
C10 C 0.27383(17) 0.39590(16) 0.27522(16) 0.0181(3) Uani 1 d . . .
C11 C 0.88071(17) 0.27001(16) -0.11419(16) 0.0202(3) Uani 1 d . . .
C12 C 0.80785(18) 0.18461(17) -0.16646(17) 0.0222(3) Uani 1 d . . .
H12 H 0.6969 0.1696 -0.1279 0.027 Uiso 1 calc R . .
C13 C 0.89799(18) 0.12161(17) -0.27499(17) 0.0228(3) Uani 1 d . . .
H13 H 0.8492 0.0646 -0.3121 0.027 Uiso 1 calc R . .
C14 C 1.06077(18) 0.14330(17) -0.32854(17) 0.0220(3) Uani 1 d . . .
C15 C 1.13513(18) 0.22822(17) -0.27875(17) 0.0235(3) Uani 1 d . . .
H15 H 1.2462 0.2421 -0.3168 0.028 Uiso 1 calc R . .
C16 C 1.04361(18) 0.29285(17) -0.17172(17) 0.0223(3) Uani 1 d . . .
H16 H 1.0925 0.3529 -0.1377 0.027 Uiso 1 calc R . .
C17 C 0.3334(2) 0.56513(18) 0.40595(19) 0.0275(4) Uani 1 d . . .
H17A H 0.2185 0.5641 0.4485 0.041 Uiso 0.5 calc PR . .
H17B H 0.3734 0.6608 0.3532 0.041 Uiso 0.5 calc PR . .
H17C H 0.3775 0.5335 0.4815 0.041 Uiso 0.5 calc PR . .
H17D H 0.4278 0.6081 0.407 0.041 Uiso 0.5 calc PR . .
H17E H 0.2729 0.5115 0.5022 0.041 Uiso 0.5 calc PR . .
H17F H 0.2688 0.6388 0.374 0.041 Uiso 0.5 calc PR . .
C18 C 0.57329(17) 0.18443(16) 0.37478(16) 0.0193(3) Uani 1 d . . .
C19 C 0.55526(17) 0.06815(16) 0.19498(16) 0.0193(3) Uani 1 d . . .
N1 N 0.37925(15) 0.47136(14) 0.30870(14) 0.0196(3) Uani 1 d . . .
N2 N 0.54438(16) 0.18005(15) 0.49265(15) 0.0261(3) Uani 1 d . . .
N3 N 0.52253(17) -0.03042(15) 0.16850(16) 0.0270(3) Uani 1 d . . .
O1 O 0.76825(12) 0.22752(12) 0.14397(11) 0.0219(3) Uani 1 d . . .
O2 O 0.63157(12) 0.35939(11) 0.01104(11) 0.0191(2) Uani 1 d . . .
O3 O 0.64960(13) 0.50597(12) 0.23059(13) 0.0264(3) Uani 1 d . . .
Cl3 Cl 1.17315(5) 0.05779(4) -0.45924(4) 0.02926(14) 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 105.70(11) . . ?
O2 C1 C11 111.24(12) . . ?
O1 C1 C11 109.53(13) . . ?
O2 C1 H1 110.1 . . ?
O1 C1 H1 110.1 . . ?
C11 C1 H1 110.1 . . ?
O2 C2 C9 115.33(12) . . ?
O2 C2 C4 114.48(12) . . ?
C9 C2 C4 103.08(11) . . ?
O2 C2 C3 99.80(11) . . ?
C9 C2 C3 116.31(12) . . ?
C4 C2 C3 108.15(11) . . ?
O1 C3 C18 109.57(12) . . ?
O1 C3 C19 110.01(12) . . ?
C18 C3 C19 110.66(13) . . ?
O1 C3 C2 103.03(12) . . ?
C18 C3 C2 111.87(12) . . ?
C19 C3 C2 111.44(12) . . ?
O3 C4 N1 127.46(14) . . ?
O3 C4 C2 125.47(14) . . ?
N1 C4 C2 106.99(12) . . ?
C9 C5 C6 117.99(14) . . ?
C9 C5 H5 121 . . ?
C6 C5 H5 121 . . ?
C7 C6 C5 120.76(14) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.48(14) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C10 C8 C7 117.20(14) . . ?
C10 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
C5 C9 C10 120.75(13) . . ?
C5 C9 C2 131.74(13) . . ?
C10 C9 C2 107.51(12) . . ?
C8 C10 C9 121.78(14) . . ?
C8 C10 N1 127.88(14) . . ?
C9 C10 N1 110.29(12) . . ?
C16 C11 C12 119.97(14) . . ?
C16 C11 C1 119.14(13) . . ?
C12 C11 C1 120.79(13) . . ?
C13 C12 C11 119.94(14) . . ?
C13 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
C12 C13 C14 119.08(14) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 121.84(14) . . ?
C15 C14 Cl3 119.49(12) . . ?
C13 C14 Cl3 118.65(12) . . ?
C14 C15 C16 118.65(14) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C11 120.48(14) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C17 H17D 109.5 . . ?
H17A C17 H17D 141.1 . . ?
H17B C17 H17D 56.3 . . ?
H17C C17 H17D 56.3 . . ?
N1 C17 H17E 109.5 . . ?
H17A C17 H17E 56.3 . . ?
H17B C17 H17E 141.1 . . ?
H17C C17 H17E 56.3 . . ?
H17D C17 H17E 109.5 . . ?
N1 C17 H17F 109.5 . . ?
H17A C17 H17F 56.3 . . ?
H17B C17 H17F 56.3 . . ?
H17C C17 H17F 141.1 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
N2 C18 C3 176.33(16) . . ?
N3 C19 C3 176.35(16) . . ?
C4 N1 C10 111.09(12) . . ?
C4 N1 C17 123.57(13) . . ?
C10 N1 C17 125.29(13) . . ?
C3 O1 C1 108.24(11) . . ?
C2 O2 C1 107.98(11) . . ?
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 1.4237(18) . ?
C1 O1 1.4691(19) . ?
C1 C11 1.505(2) . ?
C1 H1 1 . ?
C2 O2 1.4180(17) . ?
C2 C9 1.5004(19) . ?
C2 C4 1.559(2) . ?
C2 C3 1.581(2) . ?
C3 O1 1.4112(17) . ?
C3 C18 1.486(2) . ?
C3 C19 1.494(2) . ?
C4 O3 1.2222(18) . ?
C4 N1 1.3609(19) . ?
C5 C9 1.383(2) . ?
C5 C6 1.404(2) . ?
C5 H5 0.95 . ?
C6 C7 1.388(2) . ?
C6 H6 0.95 . ?
C7 C8 1.402(2) . ?
C7 H7 0.95 . ?
C8 C10 1.383(2) . ?
C8 H8 0.95 . ?
C9 C10 1.402(2) . ?
C10 N1 1.4194(19) . ?
C11 C16 1.396(2) . ?
C11 C12 1.398(2) . ?
C12 C13 1.391(2) . ?
C12 H12 0.95 . ?
C13 C14 1.393(2) . ?
C13 H13 0.95 . ?
C14 C15 1.386(2) . ?
C14 Cl3 1.7441(15) . ?
C15 C16 1.394(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 N1 1.4592(19) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C17 H17D 0.98 . ?
C17 H17E 0.98 . ?
C17 H17F 0.98 . ?
C18 N2 1.140(2) . ?
C19 N3 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 36.06(13) . . . . ?
C9 C2 C3 O1 160.80(12) . . . . ?
C4 C2 C3 O1 -83.88(13) . . . . ?
O2 C2 C3 C18 153.67(11) . . . . ?
C9 C2 C3 C18 -81.60(15) . . . . ?
C4 C2 C3 C18 33.73(16) . . . . ?
O2 C2 C3 C19 -81.85(13) . . . . ?
C9 C2 C3 C19 42.88(16) . . . . ?
C4 C2 C3 C19 158.21(12) . . . . ?
O2 C2 C4 O3 -46.8(2) . . . . ?
C9 C2 C4 O3 -172.82(15) . . . . ?
C3 C2 C4 O3 63.47(19) . . . . ?
O2 C2 C4 N1 136.26(13) . . . . ?
C9 C2 C4 N1 10.22(15) . . . . ?
C3 C2 C4 N1 -113.49(13) . . . . ?
C9 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C6 C7 C8 C10 -0.5(2) . . . . ?
C6 C5 C9 C10 -1.4(2) . . . . ?
C6 C5 C9 C2 178.09(15) . . . . ?
O2 C2 C9 C5 46.1(2) . . . . ?
C4 C2 C9 C5 171.63(16) . . . . ?
C3 C2 C9 C5 -70.2(2) . . . . ?
O2 C2 C9 C10 -134.28(13) . . . . ?
C4 C2 C9 C10 -8.79(15) . . . . ?
C3 C2 C9 C10 109.35(14) . . . . ?
C7 C8 C10 C9 -0.9(2) . . . . ?
C7 C8 C10 N1 176.29(15) . . . . ?
C5 C9 C10 C8 1.9(2) . . . . ?
C2 C9 C10 C8 -177.70(14) . . . . ?
C5 C9 C10 N1 -175.73(13) . . . . ?
C2 C9 C10 N1 4.62(17) . . . . ?
O2 C1 C11 C16 151.39(14) . . . . ?
O1 C1 C11 C16 -92.13(17) . . . . ?
O2 C1 C11 C12 -32.4(2) . . . . ?
O1 C1 C11 C12 84.12(17) . . . . ?
C16 C11 C12 C13 0.5(2) . . . . ?
C1 C11 C12 C13 -175.70(15) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C12 C13 C14 Cl3 177.31(13) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
Cl3 C14 C15 C16 -178.40(12) . . . . ?
C14 C15 C16 C11 1.3(2) . . . . ?
C12 C11 C16 C15 -1.6(2) . . . . ?
C1 C11 C16 C15 174.64(15) . . . . ?
O1 C3 C18 N2 108(2) . . . . ?
C19 C3 C18 N2 -130(2) . . . . ?
C2 C3 C18 N2 -6(3) . . . . ?
O1 C3 C19 N3 -29(3) . . . . ?
C18 C3 C19 N3 -151(2) . . . . ?
C2 C3 C19 N3 84(2) . . . . ?
O3 C4 N1 C10 175.12(16) . . . . ?
C2 C4 N1 C10 -7.99(17) . . . . ?
O3 C4 N1 C17 -2.3(3) . . . . ?
C2 C4 N1 C17 174.56(14) . . . . ?
C8 C10 N1 C4 -175.13(15) . . . . ?
C9 C10 N1 C4 2.36(18) . . . . ?
C8 C10 N1 C17 2.3(3) . . . . ?
C9 C10 N1 C17 179.75(14) . . . . ?
C18 C3 O1 C1 -140.85(12) . . . . ?
C19 C3 O1 C1 97.29(14) . . . . ?
C2 C3 O1 C1 -21.63(14) . . . . ?
O2 C1 O1 C3 -0.69(15) . . . . ?
C11 C1 O1 C3 -120.62(13) . . . . ?
C9 C2 O2 C1 -163.17(12) . . . . ?
C4 C2 O2 C1 77.45(14) . . . . ?
C3 C2 O2 C1 -37.77(13) . . . . ?
O1 C1 O2 C2 26.09(14) . . . . ?
C11 C1 O2 C2 144.89(12) . . . . ?
