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#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025614.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_4025614
loop_
_publ_author_name
'Marcus Angelin'
'Martin Rahm'
'Andreas Fischer'
'Tore Brinck'
'Olof Ramström'
_publ_contact_author_address
;
Organic Chemistry
School of Chemical Science and Engineering
Royal Institute of Technology (KTH)
100 44 Stockholm
Sweden
;
_publ_contact_author_email       ramstrom@kth.se
_publ_contact_author_name        'Olof Ramström'
_publ_contact_author_phone       '+46(0)8 790-6915'
_publ_section_title
;
 Diastereoselective One-Pot Tandem Synthesis of 3-Substituted
 Isoindolinones: A Mechanistic Investigation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5882
_journal_page_last               5887
_journal_paper_doi               10.1021/jo100868z
_journal_volume                  75
_journal_year                    2010
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C10 H10 N2 O4'
_chemical_formula_sum            'C10 H10 N2 O4'
_chemical_formula_weight         222.2
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2010-01-25 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.11(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.626(2)
_cell_length_b                   5.8228(12)
_cell_length_c                   16.673(4)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    299
_cell_measurement_theta_max      20.7
_cell_measurement_theta_min      4.0
_cell_volume                     1000.5(4)
_computing_cell_refinement       Dirax
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      299
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.129
_diffrn_reflns_av_sigmaI/netI    0.097
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10068
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         4.7
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.142
_refine_ls_R_factor_gt           0.055
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0439P)²+0.1631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.093
_refine_ls_wR_factor_ref         0.116
_reflns_number_gt                982
_reflns_number_total             1846
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo100868z_si_004.cif
_cod_data_source_block           ramstroem090624
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025614
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7306(3) 0.4616(5) 0.42678(16) 0.0355(7) Uani 1 1 d . . .
C2 C 0.7265(3) 0.4397(5) 0.50898(15) 0.0336(7) Uani 1 1 d . . .
C3 C 0.8011(3) 0.5741(6) 0.57007(18) 0.0554(9) Uani 1 1 d . . .
C4 C 0.8814(4) 0.7327(7) 0.5477(2) 0.0880(14) Uani 1 1 d . . .
C5 C 0.8884(4) 0.7493(8) 0.4663(2) 0.0928(15) Uani 1 1 d . . .
C6 C 0.8134(3) 0.6161(6) 0.40489(18) 0.0602(10) Uani 1 1 d . . .
C7 C 0.6353(3) 0.2548(5) 0.51469(17) 0.0339(7) Uani 1 1 d . . .
C8 C 0.6310(2) 0.3043(5) 0.37440(15) 0.0304(7) Uani 1 1 d . . .
C9 C 0.5180(3) 0.4386(5) 0.31842(16) 0.0335(7) Uani 1 1 d . . .
C10 C 0.4160(3) 0.2895(6) 0.2645(2) 0.0451(8) Uani 1 1 d . . .
N1 N 0.5834(2) 0.1823(4) 0.43720(13) 0.0354(6) Uani 1 1 d . . .
N2 N 0.5715(2) 0.5947(4) 0.26310(14) 0.0399(6) Uani 1 1 d . . .
O1 O 0.61098(18) 0.1758(3) 0.57851(11) 0.0438(6) Uani 1 1 d . . .
O2 O 0.3169(2) 0.4385(4) 0.22220(15) 0.0692(8) Uani 1 1 d . . .
O3 O 0.6270(2) 0.5089(4) 0.21499(12) 0.0590(7) Uani 1 1 d . . .
O4 O 0.5581(2) 0.8010(4) 0.26936(14) 0.0697(8) Uani 1 1 d . . .
H3 H 0.7971 0.5580 0.6249 0.067 Uiso 1 1 calc R . .
H4 H 0.9313 0.8293 0.5873 0.106 Uiso 1 1 calc R . .
H5 H 0.9458 0.8541 0.4525 0.111 Uiso 1 1 calc R . .
H6 H 0.8188 0.6305 0.3503 0.072 Uiso 1 1 calc R . .
H8 H 0.664(2) 0.196(4) 0.3409(15) 0.036 Uiso 1 1 d . . .
H9 H 0.482(2) 0.538(5) 0.3527(16) 0.040 Uiso 1 1 d . . .
H10A H 0.380(3) 0.190(5) 0.3013(17) 0.054 Uiso 1 1 d . . .
H10B H 0.456(3) 0.208(5) 0.2278(17) 0.054 Uiso 1 1 d . . .
H1 H 0.526(3) 0.071(5) 0.4276(16) 0.042 Uiso 1 1 d . . .
H2 H 0.271(4) 0.367(7) 0.185(2) 0.104 Uiso 1 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 0.0000 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'
loop_
_diffrn_radiation_wavelength
0.71073
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 C1 C2 120.0(3) . . ?
C6 C1 C8 130.6(2) . . ?
C2 C1 C8 109.3(2) . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 C7 129.9(3) . . ?
C1 C2 C7 108.1(2) . . ?
C4 C3 C2 117.9(3) . . ?
C3 C4 C5 120.1(3) . . ?
C6 C5 C4 122.2(3) . . ?
C1 C6 C5 117.8(3) . . ?
O1 C7 N1 125.8(2) . . ?
O1 C7 C2 127.2(2) . . ?
N1 C7 C2 107.0(2) . . ?
N1 C8 C1 101.4(2) . . ?
N1 C8 C9 109.1(2) . . ?
C1 C8 C9 112.1(2) . . ?
N2 C9 C10 107.9(2) . . ?
N2 C9 C8 108.8(2) . . ?
C10 C9 C8 114.3(2) . . ?
O2 C10 C9 106.6(3) . . ?
C7 N1 C8 113.9(2) . . ?
O3 N2 O4 123.3(3) . . ?
O3 N2 C9 118.3(2) . . ?
O4 N2 C9 118.4(2) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
N1 C8 H8 109.7(15) . . ?
C1 C8 H8 115.6(15) . . ?
C9 C8 H8 108.7(15) . . ?
N2 C9 H9 105.5(15) . . ?
C10 C9 H9 111.8(16) . . ?
C8 C9 H9 108.2(15) . . ?
O2 C10 H10A 108.4(17) . . ?
C9 C10 H10A 107.4(17) . . ?
O2 C10 H10B 112.4(18) . . ?
C9 C10 H10B 107.3(17) . . ?
H10A C10 H10B 114(3) . . ?
C7 N1 H1 120.9(18) . . ?
C8 N1 H1 125.2(18) . . ?
C10 O2 H2 108(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 C6 1.369(4) . ?
C1 C2 1.388(3) . ?
C1 C8 1.507(4) . ?
C2 C3 1.373(4) . ?
C2 C7 1.467(4) . ?
C3 C4 1.370(4) . ?
C4 C5 1.380(5) . ?
C5 C6 1.374(4) . ?
C7 O1 1.242(3) . ?
C7 N1 1.344(3) . ?
C8 N1 1.454(3) . ?
C8 C9 1.543(4) . ?
C9 N2 1.502(3) . ?
C9 C10 1.504(4) . ?
C10 O2 1.414(4) . ?
N2 O3 1.212(3) . ?
N2 O4 1.217(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 H8 0.96(3) . ?
C9 H9 0.96(3) . ?
C10 H10A 0.99(3) . ?
C10 H10B 0.95(3) . ?
N1 H1 0.88(3) . ?
O2 H2 0.81(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.88(3) 2.03(3) 2.902(3) 172(3) 3_656
O2 H2 O1 0.81(4) 2.15(4) 2.903(3) 155(4) 4_565
