# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004


data_global

_journal_coden_Cambridge         182

_publ_requested_journal          'Chem. Commun.'

_publ_contact_author_name        'Prof Peter Kundig'
_publ_contact_author_address     
;
Organic Chemistry
University of Geneva
30 Quai Ernest Ansermet
1211 Geneva 4
SWITZERLAND
;

_publ_contact_author_email       PETER.KUNDIG@CHIORG.UNIGE.CH

loop_
_publ_author_name
_publ_author_address

'E. Peter Kundig'
;    Department of Organic Chemistry
University of Geneva
30, quai E. Ansermet
CH - 1212 Geneva 4
Switzerland
;
'Thierry Lomberget'
;    Department of Organic Chemistry
University of Geneva
30, quai E. Ansermet
CH - 1212 Geneva 4
Switzerland
;
'Ryan Bragg'
;    Department of Organic Chemistry
University of Geneva
30, quai E. Ansermet
CH - 1212 Geneva 4
Switzerland
;
'Cyril Poulard'
;    Department of Organic Chemistry
University of Geneva
30, quai E. Ansermet
CH - 1212 Geneva 4
Switzerland
;
'Gerald Bernardinelli'
;    Laboratoiry of X-ray Crystallography
University of Geneva
24, quai E. Ansermet
CH - 1211 Geneva 4
Switzerland
;

_publ_section_title              
;
Synthesis and Reactivity of [Cr(CO3)(\h^6^5,8-naphtoquinone)]. Preparation
of Enantiopure Planar Chiral Complexes via Asymmetric Acylation.
;


data_LOMBA
_database_code_depnum_ccdc_archive 'CCDC 235092'

#--- (C10H6O2)Cr(CO)3 --------------------------compound 1 -----------------

_audit_creation_date             2003-09-25
_audit_creation_method           from_xtal_archive_file_using_CIFIO
_audit_update_record             2004-03-12
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.0.1

#---------------------------------------------------------------------------

_chemical_formula_moiety         'C13 H6 Cr O5'
_chemical_formula_sum            'C13 H6 Cr O5'
_chemical_formula_weight         294.2

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,-y,-z
_cell_length_a                   7.1180(8)
_cell_length_b                   7.6777(9)
_cell_length_c                   10.9461(14)
_cell_angle_alpha                87.055(15)
_cell_angle_beta                 73.479(14)
_cell_angle_gamma                86.175(14)
_cell_volume                     571.90(13)
_cell_formula_units_Z            2
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      not_measured
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_cell_measurement_reflns_used    5241
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      28.1
_cell_measurement_temperature    200
_exptl_absorpt_coefficient_mu    1.013
_exptl_crystal_F_000             296
_exptl_crystal_description       prism
_exptl_crystal_size_max          .24
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .06
_exptl_crystal_colour            dark-violet

_diffrn_measurement_device_type  'Stoe Ipds'
_diffrn_measurement_method       \f
_diffrn_detector_area_resol_mean 6
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'XRED; Stoe & Cie, 1999'
_exptl_absorpt_correction_T_min  .8447
_exptl_absorpt_correction_T_max  .9436
_diffrn_reflns_number            7602
_reflns_number_total             2787
_reflns_number_gt                1788
_reflns_threshold_expression     'refl observed if Fo > 3.99 \s(Fo)'
_diffrn_reflns_theta_max         28.2
_diffrn_measured_fraction_theta_max .99
_diffrn_reflns_theta_full        28.2
_diffrn_measured_fraction_theta_full .99
_diffrn_reflns_av_R_equivalents  .041
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_decay_%        0

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           .043
_refine_ls_wR_factor_ref         .041
_refine_ls_goodness_of_fit_ref   1.55(2)
_refine_ls_number_reflns         1809
_refine_ls_number_parameters     190
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     \w=1/[\s^2^(Fo)+0.00015(Fo^2^)]
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_shift/su_max          .00015
_refine_diff_density_max         .574
_refine_diff_density_min         -1.636
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details none

_computing_data_collection       'EXPOSE (Stoe & Cie, 1999)'
_computing_cell_refinement       'CELL (Stoe & Cie, 1999)'
_computing_data_reduction        'XRED (Stoe & Cie, 1999)'
_computing_structure_solution    SIR97
_computing_structure_refinement  xtal_CRYLSQ
_computing_molecular_graphics    xtal_gx3
_computing_publication_material  xtal_CIFIO

loop_
_atom_type_symbol
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .002 .002
H Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 0 0
O Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .008 .006
Cr Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .284 .624

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
Cr .43152(8) .11420(8) .26603(5) .0273(4) 1.00000 Uani
O1 .2344(4) .3468(4) -.0049(3) .055(3) 1.00000 Uani
O2 .2338(4) .5587(4) .4534(3) .0459(19) 1.00000 Uani
O3 .1682(4) .0747(4) .5341(3) .052(3) 1.00000 Uani
O4 .6154(4) -.2464(4) .2947(3) .050(3) 1.00000 Uani
O5 .1203(4) -.0367(4) .1731(3) .0422(18) 1.00000 Uani
C1 .4061(5) .3994(4) .2718(3) .030(3) 1.00000 Uani
C2 .5625(5) .3407(5) .3232(4) .036(3) 1.00000 Uani
C3 .7146(5) .2309(5) .2531(4) .040(3) 1.00000 Uani
C4 .7162(5) .1795(5) .1300(4) .040(3) 1.00000 Uani
C5 .5662(5) .2390(5) .0779(4) .036(3) 1.00000 Uani
C6 .4073(5) .3477(5) .1493(3) .030(3) 1.00000 Uani
C7 .2395(5) .3993(5) .0977(4) .035(3) 1.00000 Uani
C8 .0817(5) .5143(5) .1743(4) .036(3) 1.00000 Uani
C9 .0802(5) .5642(5) .2892(4) .037(3) 1.00000 Uani
C10 .2379(5) .5103(5) .3481(4) .033(3) 1.00000 Uani
C11 .2699(5) .0888(5) .4317(4) .036(3) 1.00000 Uani
C12 .5448(5) -.1107(5) .2839(4) .037(3) 1.00000 Uani
C13 .2402(5) .0188(5) .2097(4) .033(3) 1.00000 Uani
H2 .553(6) .383(6) .409(4) .05000 1.00000 Uiso
H3 .809(6) .185(6) .298(4) .05000 1.00000 Uiso
H4 .815(6) .107(6) .089(4) .05000 1.00000 Uiso
H5 .555(6) .207(6) .008(5) .05000 1.00000 Uiso
H8 -.026(6) .552(6) .131(4) .05000 1.00000 Uiso
H9 -.019(6) .633(6) .337(4) .05000 1.00000 Uiso

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cr .0270(3) .0266(3) .0298(3) .00164(17) -.01058(18) -.00231(18)
O1 .0653(17) .067(3) .0370(15) .0211(14) -.0270(13) -.0105(13)
O2 .0460(14) .0510(18) .0428(15) .0003(11) -.0140(11) -.0152(12)
O3 .0552(16) .065(2) .0325(15) -.0098(13) -.0064(12) .0004(12)
O4 .0542(15) .0285(16) .0727(19) .0086(11) -.0281(14) -.0026(13)
O5 .0370(12) .0430(16) .0535(15) -.0039(10) -.0220(11) -.0111(12)
C1 .0312(15) .0225(17) .0369(17) -.0041(12) -.0107(13) .0018(13)
C2 .0341(16) .031(2) .047(2) -.0067(13) -.0195(15) -.0023(15)
C3 .0274(16) .038(3) .056(3) -.0050(13) -.0168(15) .0019(17)
C4 .0272(16) .043(3) .044(3) .0022(14) -.0001(14) .0011(16)
C5 .0378(17) .037(3) .0278(17) .0007(14) -.0036(14) .0016(14)
C6 .0336(15) .0273(18) .0302(16) -.0024(12) -.0101(13) .0058(13)
C7 .0420(17) .033(2) .0312(17) .0005(13) -.0143(14) .0046(14)
C8 .0347(16) .035(2) .0393(19) .0030(13) -.0147(14) .0041(15)
C9 .0348(17) .034(3) .041(2) .0055(14) -.0091(14) -.0011(15)
C10 .0371(16) .0309(19) .0338(18) -.0044(13) -.0124(13) -.0016(14)
C11 .0391(17) .034(3) .040(3) -.0028(14) -.0165(16) -.0037(15)
C12 .0361(17) .035(3) .0429(19) -.0039(14) -.0151(15) -.0049(15)
C13 .0348(17) .0303(19) .0321(17) .0066(13) -.0066(13) -.0021(13)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
Cr C1 . . 2.188(4)
Cr C2 . . 2.224(4)
Cr C3 . . 2.224(4)
Cr C4 . . 2.218(3)
Cr C5 . . 2.208(4)
Cr C6 . . 2.174(4)
Cr C11 . . 1.860(4)
Cr C12 . . 1.881(4)
Cr C13 . . 1.851(4)
O1 C7 . . 1.223(5)
O2 C10 . . 1.222(5)
O3 C11 . . 1.153(4)
O4 C12 . . 1.142(5)
O5 C13 . . 1.154(5)
C1 C2 . . 1.422(5)
C1 C6 . . 1.416(5)
C1 C10 . . 1.491(4)
C2 C3 . . 1.394(5)
C2 H2 . . .99(5)
C3 C4 . . 1.420(6)
C3 H3 . . .98(5)
C4 C5 . . 1.389(6)
C4 H4 . . .90(4)
C5 C6 . . 1.423(5)
C5 H5 . . .84(5)
C6 C7 . . 1.483(5)
C7 C8 . . 1.467(5)
C8 C9 . . 1.330(6)
C8 H8 . . 1.03(5)
C9 C10 . . 1.473(6)
C9 H9 . . .91(4)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
C11 Cr C12 . . . 88.76(15)
C11 Cr C13 . . . 88.30(15)
C12 Cr C13 . . . 90.08(16)
C2 C1 C6 . . . 119.7(3)
C2 C1 C10 . . . 120.3(4)
C6 C1 C10 . . . 120.0(3)
C1 C2 C3 . . . 119.7(4)
C1 C2 H2 . . . 115(3)
C3 C2 H2 . . . 125(3)
C2 C3 C4 . . . 120.5(4)
C2 C3 H3 . . . 115(3)
C4 C3 H3 . . . 124(3)
C3 C4 C5 . . . 120.2(3)
C3 C4 H4 . . . 118(4)
C5 C4 H4 . . . 122(4)
C4 C5 C6 . . . 120.1(4)
C4 C5 H5 . . . 124(3)
C6 C5 H5 . . . 116(3)
C1 C6 C5 . . . 119.7(4)
C1 C6 C7 . . . 120.3(3)
C5 C6 C7 . . . 119.9(3)
O1 C7 C6 . . . 120.6(3)
O1 C7 C8 . . . 121.8(4)
C6 C7 C8 . . . 117.5(4)
C7 C8 C9 . . . 122.4(4)
C7 C8 H8 . . . 114(3)
C9 C8 H8 . . . 124(3)
C8 C9 C10 . . . 122.6(3)
C8 C9 H9 . . . 122(4)
C10 C9 H9 . . . 115(4)
O2 C10 C1 . . . 121.4(4)
O2 C10 C9 . . . 121.4(3)
C1 C10 C9 . . . 117.2(3)
Cr C11 O3 . . . 179.1(4)
Cr C12 O4 . . . 179.2(3)
Cr C13 O5 . . . 178.3(3)

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . . . . -.8(5)
C6 C1 C2 H2 . . . . 179(3)
C10 C1 C2 C3 . . . . 177.2(3)
C10 C1 C2 H2 . . . . -3(3)
C2 C1 C6 C5 . . . . -.7(5)
C2 C1 C6 C7 . . . . 176.4(3)
C10 C1 C6 C5 . . . . -178.7(3)
C10 C1 C6 C7 . . . . -1.6(5)
C2 C1 C10 O2 . . . . 2.9(5)
C2 C1 C10 C9 . . . . -179.2(3)
C6 C1 C10 O2 . . . . -179.1(3)
C6 C1 C10 C9 . . . . -1.2(5)
C1 C2 C3 C4 . . . . 1.0(5)
C1 C2 C3 H3 . . . . -173(3)
H2 C2 C3 C4 . . . . -179(3)
H2 C2 C3 H3 . . . . 7(4)
C2 C3 C4 C5 . . . . .3(6)
C2 C3 C4 H4 . . . . -179(3)
H3 C3 C4 C5 . . . . 174(3)
H3 C3 C4 H4 . . . . -5(5)
C3 C4 C5 C6 . . . . -1.8(6)
C3 C4 C5 H5 . . . . -175(4)
H4 C4 C5 C6 . . . . 177(4)
H4 C4 C5 H5 . . . . 4(5)
C4 C5 C6 C1 . . . . 2.0(5)
C4 C5 C6 C7 . . . . -175.1(4)
H5 C5 C6 C1 . . . . 176(4)
H5 C5 C6 C7 . . . . -1(4)
C1 C6 C7 O1 . . . . -175.8(4)
C1 C6 C7 C8 . . . . 4.1(5)
C5 C6 C7 O1 . . . . 1.3(5)
C5 C6 C7 C8 . . . . -178.8(3)
O1 C7 C8 C9 . . . . 176.1(4)
O1 C7 C8 H8 . . . . -4(3)
C6 C7 C8 C9 . . . . -3.8(5)
C6 C7 C8 H8 . . . . 176(3)
C7 C8 C9 C10 . . . . .9(6)
C7 C8 C9 H9 . . . . -178(4)
H8 C8 C9 C10 . . . . -179(3)
H8 C8 C9 H9 . . . . 1(5)
C8 C9 C10 O2 . . . . 179.5(4)
C8 C9 C10 C1 . . . . 1.7(5)
H9 C9 C10 O2 . . . . -1(3)
H9 C9 C10 C1 . . . . -179(3)

#==end===================================================================