# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2007
data_global
_journal_coden_Cambridge 0182
_publ_contact_author_name 'Olof Ramstrom'
_publ_contact_author_address
;
Royal Institute of Technology (KTH)
Department of Chemistry
S-100 44 Stockholm
Sweden
;
_publ_contact_author_email ramstrom@kth.se
_publ_contact_author_fax '+46 8 791 2333'
_publ_contact_author_phone '+46 8 790 6915'
_publ_contact_letter
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;
_publ_requested_journal 'Chem. Commun.'
#
loop_
_publ_author_name
_publ_author_address
'Angelin, Marcus'
;
Royal Institute of Technology (KTH)
Department of Chemistry
S-100 44 Stockholm
Sweden
;
'Vongvilai, Pornrapee'
;
Royal Institute of Technology (KTH)
Department of Chemistry
S-100 44 Stockholm
Sweden
;
'Fischer, Andreas'
;
Royal Institute of Technology (KTH)
Department of Chemistry
S-100 44 Stockholm
Sweden
;
'Ramstrom, Olof'
;
Royal Institute of Technology (KTH)
Department of Chemistry
S-100 44 Stockholm
Sweden
;
_publ_section_title
;
Tandem Driven Dynamic Combinatorial Resolution via
Henry - Iminolactone Rearrangement
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 665392'
_chemical_compound_source 'Local laboratory'
_exptl_crystal_description Needle
_exptl_crystal_colour Colourless
_cell_measurement_temperature 299
_refine_ls_hydrogen_treatment constr
_diffrn_measurement_device 'Bruler-Nonius KappaCCD'
_computing_data_collection KappaCCD
_computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 20
loop_
_diffrn_radiation_wavelength
0.71073
_diffrn_radiation_wavelength_id all
_cell_formula_units_Z 4
_exptl_crystal_density_diffrn 1.442
_exptl_crystal_density_method 'not measured'
_exptl_special_details
;
?
;
_chemical_formula_weight 206.20
_diffrn_radiation_type ' MoK\a'
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'
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_cell_setting monoclinic
_chemical_formula_moiety 'C10 H10 N2 O3'
_chemical_formula_sum 'C10 H10 N2 O3 '
_chemical_name_systematic
;
?
;
_cell_length_a 5.5118(7)
_cell_length_b 10.8225(9)
_cell_length_c 16.149(2)
_cell_angle_alpha 90.00
_cell_angle_beta 99.653(8)
_cell_angle_gamma 90.00
_cell_volume 949.65(19)
_diffrn_reflns_number 12286
_diffrn_reflns_av_R_equivalents 0.0454
_diffrn_reflns_av_sigmaI/netI 0.0260
_diffrn_reflns_theta_max 26.4
_diffrn_reflns_theta_min 4.6
_diffrn_reflns_theta_full 26.4
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_cell_measurement_reflns_used 77
_cell_measurement_theta_min 4.3
_cell_measurement_theta_max 20.6
_diffrn_measurement_method '\f & \w'
_computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_structure_solution
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_crystal_size_min 0.21
_exptl_crystal_size_mid 0.27
_exptl_crystal_size_max 0.51
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'
_exptl_absorpt_coefficient_mu 0.109
_reflns_number_total 1923
_reflns_number_gt 1577
_reflns_threshold_expression I>2\s(I)
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0196P)^2^+1.7204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 1923
_refine_ls_number_parameters 137
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0796
_refine_ls_R_factor_gt 0.0648
_refine_ls_wR_factor_ref 0.1426
_refine_ls_wR_factor_gt 0.1355
_refine_ls_goodness_of_fit_ref 1.161
_refine_ls_restrained_S_all 1.161
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
N2 N 0.7011(4) 0.0325(2) 0.76516(13) 0.0300(6) Uani 1 1 d . . .
O1 O 0.7959(3) 0.04943(19) 1.07531(11) 0.0314(5) Uani 1 1 d . . .
C8 C 0.6783(5) 0.1893(2) 0.87460(15) 0.0231(6) Uani 1 1 d . . .
N1 N 0.8023(4) 0.1051(2) 0.93789(13) 0.0266(5) Uani 1 1 d . . .
O3 O 0.9026(4) 0.0719(2) 0.75588(14) 0.0461(6) Uani 1 1 d . . .
C10 C 0.4040(5) 0.1970(3) 0.73000(16) 0.0316(7) Uani 1 1 d . . .
C7 C 0.5119(5) 0.2593(2) 0.92341(15) 0.0257(6) Uani 1 1 d . . .
C3 C 0.3950(6) 0.2503(3) 1.06128(17) 0.0371(7) Uani 1 1 d . . .
C2 C 0.5314(5) 0.2083(2) 1.00299(16) 0.0248(6) Uani 1 1 d . . .
O2 O 0.6275(5) -0.0711(2) 0.74508(15) 0.0532(7) Uani 1 1 d . . .
C9 C 0.5296(5) 0.1176(2) 0.80159(15) 0.0242(6) Uani 1 1 d . . .
C1 C 0.7221(5) 0.1114(2) 1.01222(15) 0.0241(6) Uani 1 1 d . . .
C6 C 0.3584(7) 0.3575(3) 0.90102(19) 0.0499(10) Uani 1 1 d . . .
C5 C 0.2219(10) 0.4002(5) 0.9590(2) 0.0877(19) Uani 1 1 d . . .
C4 C 0.2380(9) 0.3458(4) 1.0383(2) 0.0772(16) Uani 1 1 d . . .
H8 H 0.7861 0.2461 0.8531 0.028 Uiso 1 1 d R . .
H1 H 0.9231 0.0612 0.9246 0.032 Uiso 1 1 d R . .
H10A H 0.2924 0.2529 0.7505 0.038 Uiso 1 1 d R . .
H10B H 0.3146 0.1455 0.6869 0.038 Uiso 1 1 d R . .
H10C H 0.5259 0.2433 0.7071 0.038 Uiso 1 1 d R . .
H3 H 0.4142 0.2126 1.1159 0.045 Uiso 1 1 d R . .
H9 H 0.4034 0.0710 0.8219 0.029 Uiso 1 1 d R . .
H6 H 0.3539 0.3946 0.8467 0.060 Uiso 1 1 d R . .
H5 H 0.1072 0.4668 0.9454 0.105 Uiso 1 1 d R . .
H4 H 0.1361 0.3769 1.0764 0.093 Uiso 1 1 d R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0374(14) 0.0350(14) 0.0181(11) -0.0002(10) 0.0060(9) 0.0087(11)
O1 0.0339(11) 0.0411(12) 0.0200(9) 0.0100(8) 0.0072(8) 0.0128(9)
C8 0.0248(13) 0.0271(13) 0.0177(12) 0.0032(10) 0.0042(10) 0.0017(11)
N1 0.0263(11) 0.0358(13) 0.0185(10) 0.0038(9) 0.0063(8) 0.0104(10)
O3 0.0390(13) 0.0604(16) 0.0446(13) -0.0011(11) 0.0237(10) 0.0071(11)
C10 0.0311(15) 0.0427(17) 0.0202(13) 0.0019(12) 0.0016(11) 0.0041(13)
C7 0.0321(14) 0.0257(13) 0.0194(12) -0.0004(10) 0.0043(10) 0.0048(11)
C3 0.0462(18) 0.0461(18) 0.0199(13) 0.0039(12) 0.0081(12) 0.0194(15)
C2 0.0280(13) 0.0265(13) 0.0196(12) -0.0010(10) 0.0029(10) 0.0038(11)
O2 0.0672(16) 0.0386(14) 0.0545(15) -0.0207(11) 0.0120(12) 0.0033(12)
C9 0.0251(13) 0.0278(14) 0.0211(12) 0.0005(10) 0.0082(10) 0.0016(11)
C1 0.0228(13) 0.0296(14) 0.0202(12) 0.0011(11) 0.0048(10) 0.0016(11)
C6 0.078(2) 0.050(2) 0.0234(14) 0.0073(13) 0.0121(15) 0.0361(19)
C5 0.138(4) 0.095(3) 0.0358(19) 0.022(2) 0.031(2) 0.094(3)
C4 0.112(3) 0.098(3) 0.0289(17) 0.0131(19) 0.031(2) 0.078(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
N2 O2 1.218(3) . ?
N2 O3 1.222(3) . ?
N2 C9 1.508(3) . ?
O1 C1 1.229(3) . ?
C8 N1 1.451(3) . ?
C8 C7 1.509(3) . ?
C8 C9 1.528(3) . ?
N1 C1 1.347(3) . ?
C10 C9 1.511(4) . ?
C7 C6 1.369(4) . ?
C7 C2 1.384(4) . ?
C3 C4 1.360(5) . ?
C3 C2 1.375(4) . ?
C2 C1 1.475(4) . ?
C6 C5 1.374(5) . ?
C5 C4 1.397(5) . ?
C8 H8 0.9600 . ?
N1 H1 0.8737 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9599 . ?
C10 H10C 0.9600 . ?
C3 H3 0.9601 . ?
C9 H9 0.9600 . ?
C6 H6 0.9600 . ?
C5 H5 0.9600 . ?
C4 H4 0.9602 . ?
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 N2 O3 124.0(3) . . ?
O2 N2 C9 117.6(2) . . ?
O3 N2 C9 118.4(2) . . ?
N1 C8 C7 101.82(19) . . ?
N1 C8 C9 110.6(2) . . ?
C7 C8 C9 111.2(2) . . ?
C1 N1 C8 114.1(2) . . ?
C6 C7 C2 120.2(2) . . ?
C6 C7 C8 131.0(2) . . ?
C2 C7 C8 108.9(2) . . ?
C4 C3 C2 117.5(3) . . ?
C3 C2 C7 122.3(2) . . ?
C3 C2 C1 128.9(2) . . ?
C7 C2 C1 108.7(2) . . ?
N2 C9 C10 106.7(2) . . ?
N2 C9 C8 108.6(2) . . ?
C10 C9 C8 114.6(2) . . ?
O1 C1 N1 126.6(2) . . ?
O1 C1 C2 127.1(2) . . ?
N1 C1 C2 106.3(2) . . ?
C7 C6 C5 117.8(3) . . ?
C6 C5 C4 121.5(3) . . ?
C3 C4 C5 120.7(3) . . ?
N1 C8 H8 114.2 . . ?
C7 C8 H8 109.5 . . ?
C9 C8 H8 109.4 . . ?
C1 N1 H1 128.6 . . ?
C8 N1 H1 117.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.3 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C3 H3 122.7 . . ?
C2 C3 H3 119.8 . . ?
N2 C9 H9 110.4 . . ?
C10 C9 H9 107.1 . . ?
C8 C9 H9 109.3 . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 123.2 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 117.7 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 118.9 . . ?
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max 0.301
_refine_diff_density_min -0.338
_refine_diff_density_rms 0.056
_publ_section_references
;
Mackay, S., Gilmore, C. J., Edwards, C., Stewart, N. & Shankland, K. (1999).
MAXUS Computer Program for the Solution and Refinement of Crystal
Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University
of Glasgow.
Johnson, C. K. (1976). ORTEPII. A Fortran Thermal-Ellipsoid Plot
Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge,
Tennessee, USA.
Otwinowski, Z. & Minor, W. (1997). In Methods in Enzymology, 276, edited
by C.W. Carter, Jr. & R.M. Sweet pp. 307--326, New York:Academic Press.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C.,
Guagliardi, A., Moliterni, A. G. G. & Spagna, R. (1999). J. Appl.
Cryst. 32, 115--119.
Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal
Structures. University of G\"ottingen, Germany.
;
# Formatted by publCIF