#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025613.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_4025613
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_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         'C11 H12 N2 O3'
_chemical_formula_sum            'C11 H12 N2 O3'
_chemical_formula_weight         220.228
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           148
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2010-02-01 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   35.530(5)
_cell_length_b                   35.530(5)
_cell_length_c                   5.4355(7)
_cell_measurement_reflns_used    44
_cell_measurement_temperature    299
_cell_measurement_theta_max      16.8
_cell_measurement_theta_min      3.4
_cell_volume                     5942.4(14)
_computing_cell_refinement       Dirax
_computing_data_collection       KappaCCD
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      299
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.081
_diffrn_reflns_av_sigmaI/netI    0.037
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            20055
_diffrn_reflns_theta_full        22.5
_diffrn_reflns_theta_max         22.5
_diffrn_reflns_theta_min         4.59
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2088
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1662
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.11
_refine_ls_R_factor_all          0.127
_refine_ls_R_factor_gt           0.095
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1468P)²+24.5817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.251
_refine_ls_wR_factor_ref         0.283
_reflns_number_gt                1186
_reflns_number_total             1662
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo100868z_si_003.cif
_cod_data_source_block           091005
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4025613
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.29658(15) 0.02733(15) -0.1163(9) 0.0517(13) Uani 1 1 d . . .
C2 C 0.27456(17) -0.00779(16) 0.0353(10) 0.0585(14) Uani 1 1 d . . .
C3 C 0.25046(18) -0.00633(17) 0.2304(10) 0.0602(15) Uani 1 1 d . . .
C4 C 0.24691(18) 0.03011(17) 0.2755(9) 0.0597(15) Uani 1 1 d . . .
C5 C 0.26885(16) 0.06515(14) 0.1217(9) 0.0495(13) Uani 1 1 d . . .
C6 C 0.29335(15) 0.06388(15) -0.0694(8) 0.0471(12) Uani 1 1 d . . .
C7 C 0.31343(16) 0.10611(15) -0.1992(10) 0.0525(13) Uani 1 1 d . B .
C8 C 0.27054(19) 0.10850(16) 0.1234(9) 0.0630(16) Uani 1 1 d . B .
C9 C 0.2269(3) 0.1064(2) 0.1019(13) 0.087(2) Uani 1 1 d D . .
C10A C 0.2382(5) 0.1553(5) 0.161(4) 0.076(5) Uani 0.50 1 d PD B 1
C11A C 0.1959(6) 0.1560(7) 0.176(5) 0.143(9) Uani 0.50 1 d PD B 1
C10B C 0.2206(6) 0.1434(5) 0.031(2) 0.077(5) Uani 0.50 1 d PD B 2
C11B C 0.2320(10) 0.1709(5) 0.260(3) 0.113(8) Uani 0.50 1 d PD B 2
N1 N 0.30051(15) 0.13078(13) -0.0781(9) 0.0697(15) Uani 1 1 d . . .
N2 N 0.2044(3) 0.0792(4) -0.1300(16) 0.132(3) Uani 1 1 d D B .
O1 O 0.33736(12) 0.11754(11) -0.3803(7) 0.0652(12) Uani 1 1 d . . .
O2 O 0.1745(4) 0.0445(4) -0.086(2) 0.224(5) Uani 1 1 d D . .
O3 O 0.2157(3) 0.0942(5) -0.3155(15) 0.234(6) Uani 1 1 d D . .
H1 H 0.3133 0.0266 -0.2473 0.062 Uiso 1 1 calc R . .
H2 H 0.2758 -0.0332 0.0065 0.070 Uiso 1 1 calc R . .
H3 H 0.2363 -0.0305 0.3341 0.072 Uiso 1 1 calc R . .
H4 H 0.2302 0.0309 0.4061 0.072 Uiso 1 1 calc R . .
H8 H 0.2846 0.1237 0.2771 0.076 Uiso 1 1 calc R . .
H9 H 0.2094 0.0886 0.2418 0.104 Uiso 1 1 calc R A 1
H10A H 0.2652 0.1766 0.0805 0.100 Uiso 0.50 1 d PR B 1
H10B H 0.2148 0.1465 0.0409 0.100 Uiso 0.50 1 d PR B 1
H11A H 0.1870 0.1379 0.3213 0.215 Uiso 0.50 1 d PR B 1
H11B H 0.1729 0.1617 0.1280 0.215 Uiso 0.50 1 d PR B 1
H11C H 0.2221 0.1833 0.2109 0.215 Uiso 0.50 1 d PR B 1
H10C H 0.2212 0.1568 -0.1263 0.092 Uiso 0.50 1 d PR B 2
H10D H 0.1938 0.1343 0.1237 0.092 Uiso 0.50 1 d PR B 2
H11D H 0.2258 0.1617 0.4293 0.169 Uiso 0.50 1 d PR B 2
H11E H 0.2451 0.2023 0.2516 0.169 Uiso 0.50 1 d PR B 2
H11F H 0.2518 0.1623 0.1928 0.169 Uiso 0.50 1 d PR B 2
H1N H 0.3041 0.1553 -0.1149 0.084 Uiso 1 1 d R B .
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
C2 C1 C6 117.6(5) . . ?
C1 C2 C3 121.0(5) . . ?
C4 C3 C2 121.3(5) . . ?
C5 C4 C3 117.5(5) . . ?
C6 C5 C4 121.1(5) . . ?
C6 C5 C8 109.6(4) . . ?
C4 C5 C8 129.3(5) . . ?
C5 C6 C1 121.5(4) . . ?
C5 C6 C7 108.9(4) . . ?
C1 C6 C7 129.6(4) . . ?
O1 C7 N1 125.6(4) . . ?
O1 C7 C6 128.5(5) . . ?
N1 C7 C6 105.9(4) . . ?
N1 C8 C5 101.2(4) . . ?
N1 C8 C9 114.7(5) . . ?
C5 C8 C9 115.5(5) . . ?
C8 C9 N2 106.8(5) . . ?
C7 N1 C8 114.3(4) . . ?
O3 N2 O2 127.0(14) . . ?
O3 N2 C9 119.6(11) . . ?
O2 N2 C9 113.3(9) . . ?
C2 C1 H1 121.2 . . ?
C6 C1 H1 121.2 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
N1 C8 H8 108.4 . . ?
C5 C8 H8 108.4 . . ?
C9 C8 H8 108.4 . . ?
C8 C9 H9 105.8 . . ?
N2 C9 H9 105.8 . . ?
C7 N1 H1N 129.1 . . ?
C8 N1 H1N 115.8 . . ?
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 C2 1.368(7) . ?
C1 C6 1.383(7) . ?
C2 C3 1.372(7) . ?
C3 C4 1.384(8) . ?
C4 C5 1.373(7) . ?
C5 C6 1.363(7) . ?
C5 C8 1.511(7) . ?
C6 C7 1.479(7) . ?
C7 O1 1.223(6) . ?
C7 N1 1.347(8) . ?
C8 N1 1.455(7) . ?
C8 C9 1.519(13) . ?
C9 C10B 1.476(13) . ?
C9 N2 1.538(10) . ?
C9 C10A 1.591(14) . ?
C10 C11A 1.506(16) . ?
C10 C11B 1.502(14) . ?
N2 O3 1.112(9) . ?
N2 O2 1.170(10) . ?
C1 H1 0.93 . ?
C2 H2 0.93 . ?
C3 H3 0.93 . ?
C4 H4 0.93 . ?
C8 H8 0.98 . ?
C9 H9 0.98 . ?
C10A H10A 0.97 . ?
C10A H10B 0.97 . ?
C11A H11A 0.96 . ?
C11A H11B 0.96 . ?
C11A H11C 0.96 . ?
C10B H10C 0.97 . ?
C10B H10D 0.97 . ?
C11B H11D 0.96 . ?
C11B H11E 0.96 . ?
C11B H11F 0.96 . ?
N1 H1N 0.84 . ?
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 H1N O1 0.83 2.09 2.892(5) 160 13_554
