# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
#TrackingRef 'Gesamtcif.cif'

_audit_creation_method           'manual editing of form.cif'

_publ_contact_author_phone       '049 228 73-2317'
_publ_contact_author_fax         '049 228 73-2567'
_publ_contact_author_email       guetschow@uni-bonn.de

loop_
_publ_author_name
_publ_author_address
P.A.Ottersbach
; Pharmaceutical Institute I
Rheinische Friedrich-Wilhelms-University of Bonn
An der Immenburg 4
D-53121 Bonn
Germany
;
G.Schnakenburg
; Institute of Inorganic Chemistry
Rheinische Friedrich-Wilhelms-University of Bonn
Gerhard-Domagk-Str. 1
D-53121 Bonn
Germany
;
M.Gutschow
; Pharmaceutical Institute I
Rheinische Friedrich-Wilhelms-University of Bonn
An der Immenburg 4
D-53121 Bonn
Germany
;

_chemical_name_systematic        
;
Induction of Chirality: Experimental Investigations on
Atropisomerism in Azadipeptides
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

data_Greg1405f
_database_code_depnum_ccdc_archive 'CCDC 837002'
#TrackingRef 'Gesamtcif.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 N4 O4'
_chemical_formula_sum            'C13 H18 N4 O4'
_chemical_formula_weight         294.31

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4949(12)
_cell_length_b                   7.7324(8)
_cell_length_c                   14.7304(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.741(4)
_cell_angle_gamma                90.00
_cell_volume                     1421.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4907
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      29.64

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9675
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_process_details   'SADABS 2008/1'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing \f and \w scans'
_diffrn_detector_area_resol_mean 8.33333
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_diffrn_reflns_number            15892
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3426
_reflns_number_gt                2750
_reflns_threshold_expression     I>2sigma(I)

_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^)+(0.0451P)^2^+0.5683P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3426
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C -0.17584(10) 0.66702(17) 0.37605(8) 0.0189(3) Uani 1 1 d . . .
C2 C -0.20199(11) 0.85194(19) 0.23997(9) 0.0237(3) Uani 1 1 d . . .
H2A H -0.2194 0.7437 0.2080 0.036 Uiso 1 1 calc R . .
H2B H -0.1541 0.9213 0.2038 0.036 Uiso 1 1 calc R . .
H2C H -0.2680 0.9168 0.2489 0.036 Uiso 1 1 calc R . .
C3 C -0.16024(11) 1.08709(18) 0.41117(9) 0.0243(3) Uani 1 1 d . . .
H3A H -0.1132 1.1669 0.4459 0.036 Uiso 1 1 calc R . .
H3B H -0.2122 1.0366 0.4513 0.036 Uiso 1 1 calc R . .
H3C H -0.1984 1.1501 0.3618 0.036 Uiso 1 1 calc R . .
C4 C 0.01145(10) 0.96477(17) 0.36426(8) 0.0181(3) Uani 1 1 d . . .
C5 C 0.06275(10) 0.81855(18) 0.31147(9) 0.0211(3) Uani 1 1 d . . .
H5A H 0.0430 0.7064 0.3384 0.025 Uiso 1 1 calc R . .
H5B H 0.0334 0.8205 0.2478 0.025 Uiso 1 1 calc R . .
C6 C 0.23912(10) 0.73146(16) 0.36769(8) 0.0178(3) Uani 1 1 d . . .
C7 C 0.41915(11) 0.63460(18) 0.39833(8) 0.0208(3) Uani 1 1 d . . .
H7A H 0.4774 0.6057 0.3577 0.025 Uiso 1 1 calc R . .
H7B H 0.3820 0.5258 0.4131 0.025 Uiso 1 1 calc R . .
C8 C 0.46679(10) 0.71260(17) 0.48437(8) 0.0189(3) Uani 1 1 d . . .
C9 C 0.56726(11) 0.78980(17) 0.48559(9) 0.0213(3) Uani 1 1 d . . .
H9 H 0.6053 0.7953 0.4314 0.026 Uiso 1 1 calc R . .
C10 C 0.61245(11) 0.85908(18) 0.56563(9) 0.0227(3) Uani 1 1 d . . .
H10 H 0.6816 0.9103 0.5661 0.027 Uiso 1 1 calc R . .
C11 C 0.55655(11) 0.85343(18) 0.64508(9) 0.0231(3) Uani 1 1 d . . .
H11 H 0.5867 0.9032 0.6994 0.028 Uiso 1 1 calc R . .
C12 C 0.45702(11) 0.77520(18) 0.64465(9) 0.0232(3) Uani 1 1 d . . .
H12 H 0.4192 0.7700 0.6990 0.028 Uiso 1 1 calc R . .
C13 C 0.41205(11) 0.70407(18) 0.56479(9) 0.0207(3) Uani 1 1 d . . .
H13 H 0.3439 0.6496 0.5650 0.025 Uiso 1 1 calc R . .
N1 N -0.13782(11) 0.65624(17) 0.46258(8) 0.0243(3) Uani 1 1 d . . .
HN1A H -0.1575(14) 0.571(3) 0.4943(12) 0.033(5) Uiso 1 1 d . . .
HN1B H -0.1072(14) 0.741(3) 0.4922(12) 0.032(5) Uiso 1 1 d . . .
N2 N -0.14918(9) 0.81327(14) 0.32803(7) 0.0191(2) Uani 1 1 d . . .
N3 N -0.09596(9) 0.94921(14) 0.37294(7) 0.0181(2) Uani 1 1 d . . .
N4 N 0.17759(9) 0.83091(16) 0.31167(8) 0.0212(2) Uani 1 1 d . . .
HN4 H 0.2054(13) 0.895(2) 0.2717(11) 0.026(4) Uiso 1 1 d . . .
O1 O -0.22876(8) 0.55151(12) 0.33704(6) 0.0244(2) Uani 1 1 d . . .
O2 O 0.06270(8) 1.08623(13) 0.39632(6) 0.0249(2) Uani 1 1 d . . .
O3 O 0.20511(8) 0.63415(12) 0.42486(6) 0.0225(2) Uani 1 1 d . . .
O4 O 0.34323(7) 0.75076(12) 0.35067(6) 0.0194(2) Uani 1 1 d . . .

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
C1 0.0205(6) 0.0184(6) 0.0180(6) -0.0013(5) 0.0049(5) -0.0006(5)
C2 0.0273(7) 0.0255(7) 0.0180(6) 0.0035(5) -0.0026(5) 0.0004(6)
C3 0.0291(7) 0.0197(7) 0.0247(6) -0.0009(5) 0.0086(5) 0.0029(6)
C4 0.0228(6) 0.0174(6) 0.0141(5) 0.0022(5) 0.0006(5) -0.0010(5)
C5 0.0212(6) 0.0198(6) 0.0222(6) -0.0013(5) 0.0011(5) 0.0004(5)
C6 0.0245(7) 0.0146(6) 0.0146(5) -0.0033(5) 0.0024(5) -0.0007(5)
C7 0.0233(7) 0.0213(7) 0.0177(6) 0.0003(5) 0.0003(5) 0.0056(5)
C8 0.0232(6) 0.0160(6) 0.0176(6) 0.0013(5) 0.0011(5) 0.0047(5)
C9 0.0242(7) 0.0205(7) 0.0194(6) 0.0036(5) 0.0054(5) 0.0029(5)
C10 0.0205(6) 0.0208(7) 0.0268(7) 0.0012(5) 0.0012(5) -0.0008(5)
C11 0.0294(7) 0.0199(7) 0.0198(6) -0.0018(5) -0.0017(5) 0.0010(5)
C12 0.0267(7) 0.0259(7) 0.0173(6) 0.0001(5) 0.0050(5) 0.0026(6)
C13 0.0212(6) 0.0208(7) 0.0201(6) 0.0011(5) 0.0018(5) 0.0012(5)
N1 0.0385(7) 0.0175(6) 0.0168(5) 0.0022(5) 0.0010(5) -0.0077(5)
N2 0.0223(6) 0.0178(5) 0.0172(5) 0.0004(4) -0.0006(4) -0.0037(4)
N3 0.0221(6) 0.0145(5) 0.0179(5) -0.0020(4) 0.0021(4) -0.0010(4)
N4 0.0202(6) 0.0228(6) 0.0206(5) 0.0064(5) 0.0033(4) 0.0007(5)
O1 0.0310(5) 0.0216(5) 0.0210(5) -0.0043(4) 0.0048(4) -0.0076(4)
O2 0.0290(5) 0.0221(5) 0.0237(5) -0.0041(4) 0.0030(4) -0.0080(4)
O3 0.0295(5) 0.0203(5) 0.0178(4) 0.0028(4) 0.0030(4) -0.0035(4)
O4 0.0210(5) 0.0200(5) 0.0174(4) 0.0028(3) 0.0009(3) 0.0022(4)

_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
C1 O1 1.2365(16) . ?
C1 N1 1.3413(17) . ?
C1 N2 1.3831(17) . ?
C2 N2 1.4580(16) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N3 1.4636(16) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O2 1.2191(16) . ?
C4 N3 1.3595(17) . ?
C4 C5 1.5303(18) . ?
C5 N4 1.4378(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O3 1.2207(15) . ?
C6 N4 1.3427(17) . ?
C6 O4 1.3448(16) . ?
C7 O4 1.4614(15) . ?
C7 C8 1.5007(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3895(19) . ?
C8 C13 1.3975(18) . ?
C9 C10 1.3901(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.3918(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3924(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N1 HN1A 0.851(19) . ?
N1 HN1B 0.864(19) . ?
N2 N3 1.3938(15) . ?
N4 HN4 0.856(17) . ?

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
O1 C1 N1 123.64(12) . . ?
O1 C1 N2 119.31(11) . . ?
N1 C1 N2 116.99(12) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 N3 122.30(12) . . ?
O2 C4 C5 122.75(12) . . ?
N3 C4 C5 114.95(11) . . ?
N4 C5 C4 113.08(11) . . ?
N4 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
N4 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
O3 C6 N4 124.68(12) . . ?
O3 C6 O4 124.67(12) . . ?
N4 C6 O4 110.63(11) . . ?
O4 C7 C8 112.39(10) . . ?
O4 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
O4 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C13 119.20(12) . . ?
C9 C8 C7 120.34(11) . . ?
C13 C8 C7 120.43(12) . . ?
C8 C9 C10 120.43(12) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 120.09(13) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 119.82(12) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.21(12) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.23(12) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C1 N1 HN1A 118.1(12) . . ?
C1 N1 HN1B 124.1(12) . . ?
HN1A N1 HN1B 116.1(16) . . ?
C1 N2 N3 119.67(10) . . ?
C1 N2 C2 120.86(11) . . ?
N3 N2 C2 116.94(10) . . ?
C4 N3 N2 118.22(10) . . ?
C4 N3 C3 122.28(11) . . ?
N2 N3 C3 118.28(11) . . ?
C6 N4 C5 120.35(11) . . ?
C6 N4 HN4 121.0(11) . . ?
C5 N4 HN4 118.3(11) . . ?
C6 O4 C7 116.97(10) . . ?

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 C4 C5 N4 5.79(17) . . . . ?
N3 C4 C5 N4 -174.15(11) . . . . ?
O4 C7 C8 C9 -98.29(14) . . . . ?
O4 C7 C8 C13 83.57(15) . . . . ?
C13 C8 C9 C10 -0.6(2) . . . . ?
C7 C8 C9 C10 -178.72(12) . . . . ?
C8 C9 C10 C11 -0.8(2) . . . . ?
C9 C10 C11 C12 1.5(2) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?
C11 C12 C13 C8 -0.6(2) . . . . ?
C9 C8 C13 C12 1.2(2) . . . . ?
C7 C8 C13 C12 179.40(12) . . . . ?
O1 C1 N2 N3 175.61(11) . . . . ?
N1 C1 N2 N3 -7.28(17) . . . . ?
O1 C1 N2 C2 14.21(19) . . . . ?
N1 C1 N2 C2 -168.68(12) . . . . ?
O2 C4 N3 N2 175.06(11) . . . . ?
C5 C4 N3 N2 -5.00(15) . . . . ?
O2 C4 N3 C3 7.91(18) . . . . ?
C5 C4 N3 C3 -172.15(11) . . . . ?
C1 N2 N3 C4 101.25(14) . . . . ?
C2 N2 N3 C4 -96.63(13) . . . . ?
C1 N2 N3 C3 -91.08(14) . . . . ?
C2 N2 N3 C3 71.04(14) . . . . ?
O3 C6 N4 C5 -4.7(2) . . . . ?
O4 C6 N4 C5 173.86(11) . . . . ?
C4 C5 N4 C6 101.20(14) . . . . ?
O3 C6 O4 C7 6.05(17) . . . . ?
N4 C6 O4 C7 -172.48(10) . . . . ?
C8 C7 O4 C6 -94.35(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046

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

data_Greg1588f
_database_code_depnum_ccdc_archive 'CCDC 837003'
#TrackingRef 'Gesamtcif.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N4 O4'
_chemical_formula_sum            'C12 H16 N4 O4'
_chemical_formula_weight         280.29

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'

_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                   4.8613(5)
_cell_length_b                   11.6939(16)
_cell_length_c                   11.7674(16)
_cell_angle_alpha                99.755(7)
_cell_angle_beta                 94.085(7)
_cell_angle_gamma                90.661(8)
_cell_volume                     657.41(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    905
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      24.33

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.9378
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_process_details   'SADABS 2008/1'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing \f and \w scans'
_diffrn_detector_area_resol_mean 8.33333
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_diffrn_reflns_number            4690
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2358
_reflns_number_gt                1551
_reflns_threshold_expression     >2sigma(I)

_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^)+(0.0799P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2358
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1538
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_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
C1 C 0.3015(6) 0.2746(3) 0.6544(3) 0.0193(7) Uani 1 1 d . . .
C2 C 0.4590(6) 0.1754(3) 0.6313(3) 0.0227(7) Uani 1 1 d . . .
H2A H 0.4514 0.1173 0.6786 0.027 Uiso 1 1 calc R . .
C3 C 0.6266(6) 0.1615(3) 0.5397(3) 0.0267(8) Uani 1 1 d . . .
H3A H 0.7339 0.0940 0.5246 0.032 Uiso 1 1 calc R . .
C4 C 0.6382(7) 0.2450(3) 0.4705(3) 0.0291(8) Uani 1 1 d . . .
H4A H 0.7547 0.2356 0.4082 0.035 Uiso 1 1 calc R . .
C5 C 0.4796(7) 0.3429(3) 0.4919(3) 0.0285(8) Uani 1 1 d . . .
H5A H 0.4857 0.4001 0.4435 0.034 Uiso 1 1 calc R . .
C6 C 0.3115(6) 0.3580(3) 0.5837(3) 0.0255(8) Uani 1 1 d . . .
H6A H 0.2034 0.4254 0.5981 0.031 Uiso 1 1 calc R . .
C7 C 0.1314(6) 0.2911(3) 0.7568(3) 0.0222(7) Uani 1 1 d . . .
H7A H -0.0231 0.3433 0.7451 0.027 Uiso 1 1 calc R . .
H7B H 0.0544 0.2156 0.7687 0.027 Uiso 1 1 calc R . .
C8 C 0.2027(6) 0.3598(3) 0.9582(3) 0.0184(7) Uani 1 1 d . . .
C9 C 0.3061(6) 0.4151(3) 1.1639(3) 0.0203(7) Uani 1 1 d . . .
H9A H 0.2056 0.4887 1.1696 0.024 Uiso 1 1 calc R . .
H9B H 0.4721 0.4287 1.2187 0.024 Uiso 1 1 calc R . .
C10 C 0.1235(6) 0.3239(3) 1.1995(3) 0.0187(7) Uani 1 1 d . . .
C11 C -0.1834(6) 0.0714(3) 1.1139(3) 0.0191(7) Uani 1 1 d . . .
C12 C 0.1430(6) 0.0727(3) 1.2859(3) 0.0247(8) Uani 1 1 d . . .
H12A H 0.0200 0.0093 1.2974 0.037 Uiso 1 1 calc R . .
H12B H 0.1493 0.1343 1.3539 0.037 Uiso 1 1 calc R . .
H12C H 0.3289 0.0433 1.2749 0.037 Uiso 1 1 calc R . .
N1 N 0.3922(5) 0.3838(2) 1.0476(2) 0.0178(6) Uani 1 1 d . . .
HN1A H 0.5688 0.3806 1.0358 0.021 Uiso 1 1 calc R . .
N2 N 0.1843(5) 0.2128(2) 1.1571(2) 0.0199(6) Uani 1 1 d . . .
HN2A H 0.3191 0.1997 1.1109 0.024 Uiso 1 1 calc R . .
N3 N 0.0406(5) 0.1191(2) 1.1844(2) 0.0229(6) Uani 1 1 d . . .
N4 N -0.2697(6) 0.1271(3) 1.0264(2) 0.0215(6) Uani 1 1 d . . .
HN4A H -0.180(7) 0.188(3) 1.008(3) 0.030(10) Uiso 1 1 d . . .
HN4B H -0.382(8) 0.086(3) 0.971(3) 0.046(12) Uiso 1 1 d . . .
O1 O 0.3159(4) 0.34229(18) 0.85632(17) 0.0221(5) Uani 1 1 d . . .
O2 O -0.0470(4) 0.35280(18) 0.96845(17) 0.0201(5) Uani 1 1 d . . .
O3 O -0.0657(4) 0.34925(19) 1.26178(18) 0.0257(6) Uani 1 1 d . . .
O4 O -0.3014(4) -0.01629(18) 1.13411(18) 0.0243(5) Uani 1 1 d . . .

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
C1 0.0131(15) 0.0249(17) 0.0192(17) 0.0015(13) 0.0018(12) 0.0000(12)
C2 0.0218(16) 0.0250(18) 0.0224(17) 0.0066(14) 0.0029(14) 0.0038(13)
C3 0.0198(17) 0.034(2) 0.0257(18) 0.0012(15) 0.0058(14) 0.0055(14)
C4 0.0246(18) 0.040(2) 0.0210(18) -0.0004(15) 0.0039(14) -0.0079(15)
C5 0.039(2) 0.0263(19) 0.0211(18) 0.0064(14) 0.0019(15) -0.0062(15)
C6 0.0259(17) 0.0253(18) 0.0237(18) -0.0001(14) -0.0004(14) 0.0032(14)
C7 0.0152(15) 0.0284(18) 0.0211(17) -0.0005(13) -0.0007(13) 0.0032(13)
C8 0.0166(16) 0.0182(16) 0.0216(17) 0.0047(13) 0.0061(13) 0.0042(12)
C9 0.0210(16) 0.0219(17) 0.0173(16) 0.0002(13) 0.0030(13) 0.0030(13)
C10 0.0146(15) 0.0273(18) 0.0144(16) 0.0036(13) 0.0008(12) 0.0035(13)
C11 0.0136(15) 0.0214(17) 0.0219(17) 0.0011(13) 0.0038(13) 0.0056(13)
C12 0.0184(16) 0.0330(19) 0.0252(18) 0.0113(15) 0.0036(13) 0.0036(14)
N1 0.0100(12) 0.0265(15) 0.0175(14) 0.0047(11) 0.0022(10) 0.0037(10)
N2 0.0145(13) 0.0235(15) 0.0232(15) 0.0060(11) 0.0066(11) 0.0035(10)
N3 0.0186(13) 0.0234(15) 0.0283(15) 0.0112(12) -0.0021(11) -0.0010(11)
N4 0.0189(14) 0.0231(16) 0.0233(16) 0.0061(13) 0.0017(12) 0.0000(12)
O1 0.0140(10) 0.0331(13) 0.0186(12) 0.0011(9) 0.0044(9) 0.0013(9)
O2 0.0094(10) 0.0280(12) 0.0243(12) 0.0066(9) 0.0047(8) 0.0050(8)
O3 0.0191(11) 0.0350(14) 0.0248(12) 0.0063(10) 0.0103(10) 0.0067(9)
O4 0.0196(11) 0.0249(13) 0.0298(13) 0.0087(10) 0.0023(9) -0.0023(9)

_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
C1 C6 1.387(4) . ?
C1 C2 1.396(4) . ?
C1 C7 1.496(4) . ?
C2 C3 1.386(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.377(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.390(4) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 O1 1.462(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O2 1.232(3) . ?
C8 N1 1.338(4) . ?
C8 O1 1.340(3) . ?
C9 N1 1.448(4) . ?
C9 C10 1.511(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O3 1.224(3) . ?
C10 N2 1.354(4) . ?
C11 O4 1.235(4) . ?
C11 N4 1.354(4) . ?
C11 N3 1.373(4) . ?
C12 N3 1.452(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 HN1A 0.8800 . ?
N2 N3 1.388(3) . ?
N2 HN2A 0.8800 . ?
N4 HN4A 0.89(4) . ?
N4 HN4B 0.89(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
C6 C1 C2 119.3(3) . . ?
C6 C1 C7 121.1(3) . . ?
C2 C1 C7 119.6(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C1 C6 C5 120.0(3) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
O1 C7 C1 106.5(2) . . ?
O1 C7 H7A 110.4 . . ?
C1 C7 H7A 110.4 . . ?
O1 C7 H7B 110.4 . . ?
C1 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
O2 C8 N1 123.8(3) . . ?
O2 C8 O1 123.9(3) . . ?
N1 C8 O1 112.3(2) . . ?
N1 C9 C10 113.5(3) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
O3 C10 N2 122.8(3) . . ?
O3 C10 C9 122.2(3) . . ?
N2 C10 C9 115.0(3) . . ?
O4 C11 N4 123.1(3) . . ?
O4 C11 N3 119.9(3) . . ?
N4 C11 N3 117.0(3) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 N1 C9 119.9(2) . . ?
C8 N1 HN1A 120.0 . . ?
C9 N1 HN1A 120.0 . . ?
C10 N2 N3 122.1(2) . . ?
C10 N2 HN2A 119.0 . . ?
N3 N2 HN2A 119.0 . . ?
C11 N3 N2 119.8(2) . . ?
C11 N3 C12 122.7(3) . . ?
N2 N3 C12 117.5(2) . . ?
C11 N4 HN4A 124(2) . . ?
C11 N4 HN4B 115(2) . . ?
HN4A N4 HN4B 117(3) . . ?
C8 O1 C7 115.5(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
C6 C1 C2 C3 0.9(5) . . . . ?
C7 C1 C2 C3 -177.3(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C7 C1 C6 C5 177.4(3) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C6 C1 C7 O1 -94.2(3) . . . . ?
C2 C1 C7 O1 84.0(3) . . . . ?
N1 C9 C10 O3 -144.6(3) . . . . ?
N1 C9 C10 N2 35.2(4) . . . . ?
O2 C8 N1 C9 -6.4(4) . . . . ?
O1 C8 N1 C9 174.7(2) . . . . ?
C10 C9 N1 C8 57.8(4) . . . . ?
O3 C10 N2 N3 -2.0(4) . . . . ?
C9 C10 N2 N3 178.2(2) . . . . ?
O4 C11 N3 N2 175.7(2) . . . . ?
N4 C11 N3 N2 -6.6(4) . . . . ?
O4 C11 N3 C12 -2.0(4) . . . . ?
N4 C11 N3 C12 175.7(3) . . . . ?
C10 N2 N3 C11 92.5(4) . . . . ?
C10 N2 N3 C12 -89.7(3) . . . . ?
O2 C8 O1 C7 -11.8(4) . . . . ?
N1 C8 O1 C7 167.1(2) . . . . ?
C1 C7 O1 C8 -177.6(2) . . . . ?

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 HN1A O2 0.88 2.09 2.950(3) 166 1_655
N2 HN2A N4 0.88 2.40 3.246(3) 163 1_655
N4 HN4A O2 0.89(4) 2.16(4) 3.042(4) 168(3) .
N4 HN4B O4 0.89(4) 1.98(4) 2.853(4) 167(3) 2_457

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.070

#END---------------------------------------------------------------------------