# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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data_6n
_database_code_depnum_ccdc_archive 'CCDC 873380'
#TrackingRef 'data_6n.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(3-benzyl-2-ethyl-7-methoxy-9H-pyrido[2,3-b]indole)
;
_chemical_name_common            carboline
_chemical_melting_point          212(2)
_chemical_formula_moiety         'C21 H20 N2 O'
_chemical_formula_sum            'C21 H20 N2 O'
_chemical_formula_weight         316.39

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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7251(10)
_cell_length_b                   12.062(2)
_cell_length_c                   12.371(2)
_cell_angle_alpha                82.492(3)
_cell_angle_beta                 80.563(3)
_cell_angle_gamma                81.462(3)
_cell_volume                     828.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    25
_cell_measurement_reflns_used    1694
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      25
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8026
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_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         1.68
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2912
_reflns_number_gt                2307
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0470P)^2^+0.1056P] 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         2912
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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 0.1149(4) -0.06226(18) 0.85640(17) 0.0511(5) Uani 1 1 d . . .
C2 C 0.0041(4) 0.00003(19) 0.76981(18) 0.0537(6) Uani 1 1 d . . .
C3 C 0.0546(4) 0.10899(19) 0.73606(18) 0.0580(6) Uani 1 1 d . . .
H3 H -0.0184 0.1523 0.6800 0.070 Uiso 1 1 calc R . .
C4 C 0.2824(5) 0.35993(19) 0.70820(19) 0.0644(7) Uani 1 1 d . . .
H4 H 0.1773 0.3703 0.6568 0.077 Uiso 1 1 calc R . .
C5 C 0.4092(5) 0.44472(19) 0.7186(2) 0.0650(7) Uani 1 1 d . . .
H5 H 0.3881 0.5131 0.6747 0.078 Uiso 1 1 calc R . .
C6 C 0.5694(4) 0.42963(19) 0.7945(2) 0.0595(6) Uani 1 1 d . . .
C7 C 0.6036(4) 0.32977(18) 0.86199(19) 0.0577(6) Uani 1 1 d . . .
H7 H 0.7108 0.3197 0.9125 0.069 Uiso 1 1 calc R . .
C8 C 0.4716(4) 0.24478(18) 0.85161(17) 0.0504(5) Uani 1 1 d . . .
C9 C 0.3117(4) 0.25803(18) 0.77502(17) 0.0525(6) Uani 1 1 d . . .
C10 C 0.2132(4) 0.15320(18) 0.78570(17) 0.0516(5) Uani 1 1 d . . .
C11 C 0.3165(4) 0.08258(18) 0.86982(16) 0.0474(5) Uani 1 1 d . . .
C12 C 0.0745(4) -0.18128(18) 0.89811(19) 0.0580(6) Uani 1 1 d . . .
H12A H -0.0701 -0.1968 0.8748 0.070 Uiso 1 1 calc R . .
H12B H 0.0513 -0.1896 0.9781 0.070 Uiso 1 1 calc R . .
C13 C 0.2813(4) -0.26657(19) 0.8566(2) 0.0646(7) Uani 1 1 d . . .
H13A H 0.2951 -0.2638 0.7780 0.097 Uiso 1 1 calc R . .
H13B H 0.2532 -0.3408 0.8899 0.097 Uiso 1 1 calc R . .
H13C H 0.4264 -0.2491 0.8758 0.097 Uiso 1 1 calc R . .
C14 C -0.1606(4) -0.0501(2) 0.71129(19) 0.0632(6) Uani 1 1 d . . .
H14A H -0.2801 -0.0828 0.7660 0.076 Uiso 1 1 calc R . .
H14B H -0.2429 0.0100 0.6660 0.076 Uiso 1 1 calc R . .
C15 C -0.0358(4) -0.1397(2) 0.63921(18) 0.0560(6) Uani 1 1 d . . .
C16 C 0.1815(4) -0.1279(2) 0.5741(2) 0.0689(7) Uani 1 1 d . . .
H16 H 0.2523 -0.0633 0.5737 0.083 Uiso 1 1 calc R . .
C17 C 0.2941(5) -0.2105(3) 0.5100(2) 0.0782(8) Uani 1 1 d . . .
H17 H 0.4412 -0.2017 0.4675 0.094 Uiso 1 1 calc R . .
C18 C 0.1917(6) -0.3057(3) 0.5083(2) 0.0820(8) Uani 1 1 d . . .
H18 H 0.2675 -0.3609 0.4639 0.098 Uiso 1 1 calc R . .
C19 C -0.0221(6) -0.3187(2) 0.5719(2) 0.0833(8) Uani 1 1 d . . .
H19 H -0.0918 -0.3836 0.5720 0.100 Uiso 1 1 calc R . .
C20 C -0.1352(5) -0.2361(2) 0.6361(2) 0.0698(7) Uani 1 1 d . . .
H20 H -0.2823 -0.2456 0.6785 0.084 Uiso 1 1 calc R . .
C21 C 0.8221(5) 0.5189(2) 0.8817(2) 0.0821(8) Uani 1 1 d . . .
H21A H 0.7203 0.5113 0.9514 0.123 Uiso 1 1 calc R . .
H21B H 0.8898 0.5883 0.8737 0.123 Uiso 1 1 calc R . .
H21C H 0.9479 0.4567 0.8786 0.123 Uiso 1 1 calc R . .
H22 H 0.558(4) 0.1112(18) 0.9628(19) 0.061(7) Uiso 1 1 d . . .
N1 N 0.2720(3) -0.02179(14) 0.90620(14) 0.0509(5) Uani 1 1 d . . .
N2 N 0.4724(3) 0.13837(15) 0.90866(16) 0.0529(5) Uani 1 1 d . . .
O1 O 0.6871(3) 0.51978(13) 0.79556(15) 0.0783(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 0.0493(13) 0.0521(13) 0.0498(13) -0.0116(10) 0.0001(10) -0.0032(10)
C2 0.0509(13) 0.0548(14) 0.0548(13) -0.0106(11) -0.0078(11) -0.0003(11)
C3 0.0623(15) 0.0593(15) 0.0512(13) -0.0055(11) -0.0173(11) 0.0058(12)
C4 0.0800(17) 0.0547(15) 0.0570(15) -0.0024(12) -0.0179(13) 0.0020(13)
C5 0.0820(17) 0.0441(14) 0.0630(15) 0.0046(11) -0.0092(14) -0.0003(13)
C6 0.0652(15) 0.0472(14) 0.0622(15) -0.0076(11) 0.0013(12) -0.0048(12)
C7 0.0590(14) 0.0531(14) 0.0603(15) -0.0070(12) -0.0090(12) -0.0039(11)
C8 0.0530(13) 0.0446(13) 0.0506(13) -0.0051(10) -0.0067(10) 0.0022(10)
C9 0.0569(13) 0.0469(13) 0.0503(13) -0.0055(10) -0.0066(11) 0.0034(10)
C10 0.0585(14) 0.0485(13) 0.0457(12) -0.0077(10) -0.0082(11) 0.0024(11)
C11 0.0494(13) 0.0458(13) 0.0450(12) -0.0085(10) -0.0052(10) 0.0010(10)
C12 0.0539(14) 0.0593(15) 0.0612(14) -0.0051(12) -0.0076(11) -0.0109(11)
C13 0.0693(16) 0.0546(14) 0.0682(16) -0.0076(12) -0.0074(13) -0.0053(12)
C14 0.0541(14) 0.0710(16) 0.0644(15) -0.0082(12) -0.0133(12) -0.0025(12)
C15 0.0534(14) 0.0679(16) 0.0491(13) -0.0062(11) -0.0158(11) -0.0065(12)
C16 0.0647(16) 0.0810(18) 0.0618(15) -0.0098(14) -0.0075(13) -0.0125(14)
C17 0.0685(17) 0.105(2) 0.0569(16) -0.0110(16) -0.0044(13) -0.0013(17)
C18 0.101(2) 0.084(2) 0.0591(17) -0.0172(15) -0.0187(16) 0.0117(18)
C19 0.105(2) 0.077(2) 0.0729(18) -0.0173(15) -0.0155(18) -0.0172(17)
C20 0.0697(16) 0.0776(18) 0.0655(16) -0.0126(14) -0.0089(13) -0.0173(14)
C21 0.0817(19) 0.0658(18) 0.103(2) -0.0141(15) -0.0118(17) -0.0211(15)
N1 0.0543(11) 0.0471(11) 0.0511(11) -0.0065(8) -0.0087(9) -0.0041(8)
N2 0.0587(12) 0.0486(11) 0.0528(11) -0.0009(9) -0.0172(10) -0.0058(9)
O1 0.0900(13) 0.0550(11) 0.0908(13) 0.0007(9) -0.0151(11) -0.0182(10)

_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 N1 1.348(3) . ?
C1 C2 1.409(3) . ?
C1 C12 1.499(3) . ?
C2 C3 1.384(3) . ?
C2 C14 1.512(3) . ?
C3 C10 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(3) . ?
C4 C9 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 O1 1.364(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.391(3) . ?
C7 H7 0.9300 . ?
C8 N2 1.381(3) . ?
C8 C9 1.401(3) . ?
C9 C10 1.441(3) . ?
C10 C11 1.407(3) . ?
C11 N1 1.327(3) . ?
C11 N2 1.373(3) . ?
C12 C13 1.516(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.512(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.376(3) . ?
C15 C16 1.382(3) . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.361(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O1 1.414(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N2 H22 0.90(2) . ?

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
N1 C1 C2 123.2(2) . . ?
N1 C1 C12 114.22(19) . . ?
C2 C1 C12 122.6(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 C14 119.7(2) . . ?
C1 C2 C14 121.9(2) . . ?
C10 C3 C2 119.9(2) . . ?
C10 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C9 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C9 C4 H4 120.2 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
O1 C6 C7 123.7(2) . . ?
O1 C6 C5 114.9(2) . . ?
C7 C6 C5 121.4(2) . . ?
C6 C7 C8 117.4(2) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
N2 C8 C7 128.8(2) . . ?
N2 C8 C9 109.2(2) . . ?
C7 C8 C9 122.0(2) . . ?
C4 C9 C8 118.9(2) . . ?
C4 C9 C10 134.6(2) . . ?
C8 C9 C10 106.52(18) . . ?
C3 C10 C11 116.8(2) . . ?
C3 C10 C9 136.9(2) . . ?
C11 C10 C9 106.37(19) . . ?
N1 C11 N2 124.97(19) . . ?
N1 C11 C10 125.7(2) . . ?
N2 C11 C10 109.3(2) . . ?
C1 C12 C13 112.45(18) . . ?
C1 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C1 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C2 114.23(18) . . ?
C15 C14 H14A 108.7 . . ?
C2 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C2 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C20 C15 C16 117.6(2) . . ?
C20 C15 C14 121.0(2) . . ?
C16 C15 C14 121.5(2) . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.4(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 121.5(3) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 N1 C1 116.01(18) . . ?
C11 N2 C8 108.59(19) . . ?
C11 N2 H22 126.0(14) . . ?
C8 N2 H22 125.4(14) . . ?
C6 O1 C21 118.46(19) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.030


data_8
_database_code_depnum_ccdc_archive 'CCDC 873381'
#TrackingRef 'data_8.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(2-[2-Cyano-2-(2-nitrophenyl)]ethylcyclohex-2-en-1-one)
;
_chemical_name_common            ?
_chemical_melting_point          78(2)
_chemical_formula_moiety         'C15 H14 N2 O3'
_chemical_formula_sum            'C15 H14 N2 O3'
_chemical_formula_weight         270.28

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   'P2(1)/c '

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                   7.9981(14)
_cell_length_b                   10.3530(18)
_cell_length_c                   16.174(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.804(3)
_cell_angle_gamma                90.00
_cell_volume                     1337.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    25
_cell_measurement_reflns_used    4745
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.67

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_process_details   SADABAS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      25
_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 SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12501
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2355
_reflns_number_gt                2099
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0870P)^2^+0.9701P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2355
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1589
_refine_ls_wR_factor_gt          0.1535
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_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
O1 O 0.2003(2) 0.2807(2) 0.58808(11) 0.0685(5) Uani 1 1 d . . .
N1 N 0.8780(3) 0.2706(2) 0.43990(16) 0.0708(7) Uani 1 1 d . . .
C1 C 0.3660(3) 0.4421(2) 0.31092(12) 0.0413(5) Uani 1 1 d . . .
O2 O 0.2673(2) 0.41727(15) 0.49510(10) 0.0541(4) Uani 1 1 d . . .
N2 N 0.2571(2) 0.30746(18) 0.52152(11) 0.0443(5) Uani 1 1 d . . .
C2 C 0.3205(3) 0.5695(2) 0.34426(14) 0.0491(6) Uani 1 1 d . . .
O3 O 0.4235(2) 0.63907(17) 0.37880(13) 0.0697(6) Uani 1 1 d . . .
H3A H 0.0865 0.5844 0.3853 0.095 Uiso 1 1 calc R . .
H3B H 0.1347 0.7011 0.3299 0.095 Uiso 1 1 calc R . .
C3 C 0.1402(4) 0.6078(3) 0.3349(2) 0.0794(9) Uani 1 1 d . . .
H4A H 0.0677 0.6022 0.2169 0.117 Uiso 1 1 calc R . .
H4B H -0.0725 0.5620 0.2757 0.117 Uiso 1 1 calc R . .
C4 C 0.0455(4) 0.5522(4) 0.2658(3) 0.0971(12) Uani 1 1 d . . .
H5A H 0.0483 0.4002 0.1896 0.083 Uiso 1 1 calc R . .
H5B H 0.0034 0.3632 0.2798 0.083 Uiso 1 1 calc R . .
C5 C 0.0767(3) 0.4160(3) 0.24773(19) 0.0690(8) Uani 1 1 d . . .
H6 H 0.2866 0.2960 0.2451 0.066 Uiso 1 1 calc R . .
C6 C 0.2532(3) 0.3748(2) 0.26634(15) 0.0549(6) Uani 1 1 d . . .
H7A H 0.6178 0.4664 0.3275 0.057 Uiso 1 1 calc R . .
H7B H 0.5696 0.3322 0.2884 0.057 Uiso 1 1 calc R . .
C7 C 0.5407(3) 0.3944(2) 0.33018(13) 0.0474(5) Uani 1 1 d . . .
H8 H 0.5313 0.3928 0.4587 0.048 Uiso 1 1 calc R . .
C8 C 0.5626(2) 0.33032(19) 0.41669(13) 0.0396(5) Uani 1 1 d . . .
C9 C 0.4548(2) 0.21015(19) 0.42385(12) 0.0380(5) Uani 1 1 d . . .
C10 C 0.3145(2) 0.19970(19) 0.47113(12) 0.0384(5) Uani 1 1 d . . .
H11 H 0.1309 0.0832 0.5079 0.061 Uiso 1 1 calc R . .
C11 C 0.2236(3) 0.0870(2) 0.47544(15) 0.0509(6) Uani 1 1 d . . .
H12 H 0.2078 -0.0952 0.4334 0.069 Uiso 1 1 calc R . .
C12 C 0.2702(3) -0.0196(2) 0.43173(15) 0.0577(6) Uani 1 1 d . . .
H13 H 0.4432 -0.0865 0.3569 0.068 Uiso 1 1 calc R . .
C13 C 0.4095(3) -0.0139(2) 0.38556(15) 0.0564(6) Uani 1 1 d . . .
H14 H 0.5931 0.1012 0.3498 0.059 Uiso 1 1 calc R . .
C14 C 0.4995(3) 0.0990(2) 0.38164(14) 0.0492(6) Uani 1 1 d . . .
C15 C 0.7404(3) 0.2966(2) 0.43138(14) 0.0484(6) 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
O1 0.0704(12) 0.0842(13) 0.0531(10) -0.0001(9) 0.0241(9) 0.0014(10)
N1 0.0438(12) 0.0766(16) 0.0915(17) 0.0128(13) 0.0001(11) 0.0083(11)
C1 0.0467(11) 0.0375(11) 0.0396(10) 0.0064(8) 0.0017(9) 0.0006(9)
O2 0.0573(10) 0.0414(9) 0.0640(10) -0.0038(7) 0.0080(8) 0.0069(7)
N2 0.0370(9) 0.0508(11) 0.0453(10) -0.0019(8) 0.0035(8) 0.0025(8)
C2 0.0559(13) 0.0387(12) 0.0515(13) 0.0014(9) -0.0103(10) 0.0020(10)
O3 0.0682(11) 0.0467(10) 0.0918(14) -0.0098(9) -0.0214(10) -0.0051(8)
C3 0.0690(18) 0.0662(18) 0.100(2) -0.0278(16) -0.0269(16) 0.0284(14)
C4 0.0546(17) 0.094(2) 0.140(3) -0.039(2) -0.0275(19) 0.0169(16)
C5 0.0615(16) 0.0674(17) 0.0760(18) -0.0117(14) -0.0181(13) -0.0035(13)
C6 0.0655(15) 0.0426(13) 0.0560(14) -0.0077(10) -0.0031(11) 0.0046(11)
C7 0.0479(12) 0.0464(12) 0.0484(12) 0.0085(9) 0.0086(9) 0.0042(10)
C8 0.0380(10) 0.0389(11) 0.0422(11) -0.0001(8) 0.0037(8) 0.0030(8)
C9 0.0411(11) 0.0363(10) 0.0360(10) 0.0013(8) -0.0029(8) 0.0039(8)
C10 0.0376(10) 0.0385(11) 0.0386(10) 0.0029(8) -0.0023(8) 0.0023(8)
C11 0.0456(12) 0.0494(13) 0.0571(13) 0.0092(10) -0.0028(10) -0.0060(10)
C12 0.0710(16) 0.0391(13) 0.0612(15) 0.0050(10) -0.0141(12) -0.0118(11)
C13 0.0796(17) 0.0382(12) 0.0505(13) -0.0075(10) -0.0082(12) 0.0037(11)
C14 0.0584(14) 0.0440(12) 0.0454(12) -0.0044(9) 0.0037(10) 0.0065(10)
C15 0.0454(13) 0.0466(13) 0.0532(13) 0.0056(10) 0.0022(10) 0.0005(10)

_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 O1 1.221(2) . ?
N2 O2 1.219(2) . ?
C1 C2 1.477(3) . ?
C1 C6 1.325(3) . ?
C1 C7 1.500(3) . ?
C2 O3 1.211(3) . ?
C2 C3 1.496(4) . ?
C3 C4 1.439(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.464(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.491(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9800 . ?
C8 C7 1.551(3) . ?
C9 C8 1.521(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.393(3) . ?
C10 N2 1.469(3) . ?
C10 C11 1.379(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.372(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.373(4) . ?
C13 C14 1.375(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.135(3) . ?
C15 C8 1.472(3) . ?

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 N2 C10 117.17(19) . . ?
O2 N2 O1 123.74(19) . . ?
O2 N2 C10 119.08(17) . . ?
O3 C2 C1 121.7(2) . . ?
O3 C2 C3 121.3(2) . . ?
N1 C15 C8 177.7(3) . . ?
C1 C2 C3 117.0(2) . . ?
C1 C6 C5 124.9(2) . . ?
C1 C6 H6 117.5 . . ?
C1 C7 C8 113.04(17) . . ?
C1 C7 H7A 109.0 . . ?
C1 C7 H7B 109.0 . . ?
C2 C1 C7 117.53(19) . . ?
C2 C3 H3B 108.3 . . ?
C2 C3 H3A 108.3 . . ?
C3 C4 C5 116.9(3) . . ?
C3 C4 H4A 108.1 . . ?
C3 C4 H4B 108.1 . . ?
C4 C3 C2 116.1(2) . . ?
C4 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
C4 C5 C6 113.8(2) . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C5 C4 H4A 108.1 . . ?
C5 C4 H4B 108.1 . . ?
C5 C6 H6 117.5 . . ?
C6 C1 C2 119.6(2) . . ?
C6 C1 C7 122.9(2) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C7 C8 H8 108.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C9 C8 H8 108.8 . . ?
C9 C8 C7 112.27(17) . . ?
C9 C10 N2 121.88(18) . . ?
C9 C14 H14 118.9 . . ?
C10 C9 C8 125.46(18) . . ?
C10 C11 H11 120.1 . . ?
C11 C10 C9 122.3(2) . . ?
C11 C10 N2 115.79(19) . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C13 C12 H12 120.2 . . ?
C13 C14 C9 122.1(2) . . ?
C13 C14 H14 118.9 . . ?
C14 C9 C10 115.95(19) . . ?
C14 C9 C8 118.58(19) . . ?
C14 C13 H13 119.9 . . ?
C15 C8 H8 108.8 . . ?
C15 C8 C7 108.23(17) . . ?
C15 C8 C9 109.87(17) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.053