# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
B.Spingler
S.Schnidrig
T.Todorova
F.Wild
_publ_contact_author_name        'Bernhard Spingler'
_publ_contact_author_email       spingler@aci.uzh.ch

# Attachment '- sts300909.cif'

data_sts300909
_database_code_depnum_ccdc_archive 'CCDC 800843'
#TrackingRef '- sts300909.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N O2'
_chemical_formula_weight         201.22

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'
O O 0.0106 0.0060 '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'

_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                   7.5975(5)
_cell_length_b                   12.2026(7)
_cell_length_c                   12.8137(8)
_cell_angle_alpha                61.607(6)
_cell_angle_beta                 77.247(5)
_cell_angle_gamma                78.353(5)
_cell_volume                     1012.74(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    2605
_cell_measurement_theta_min      2.7631
_cell_measurement_theta_max      32.8164

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8558
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur Ruby'
_diffrn_measurement_method       '\o oscillation scan'
_diffrn_detector_area_resol_mean 10.4498
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11480
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.1183
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         29.13
_reflns_number_total             5457
_reflns_number_gt                2329
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis RED (Oxford, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford, 2007)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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^)+(0.0314P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5457
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_restrained_S_all      0.810
_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
C2 C 0.2350(3) 0.37098(17) 0.70410(15) 0.0402(5) Uani 1 1 d . . .
H2 H 0.1963 0.3534 0.7857 0.048 Uiso 1 1 calc R . .
C3 C 0.1785(2) 0.49134(16) 0.61593(15) 0.0306(4) Uani 1 1 d . . .
C4 C 0.2301(2) 0.51740(15) 0.49844(15) 0.0312(4) Uani 1 1 d . . .
H4 H 0.1920 0.5968 0.4372 0.037 Uiso 1 1 calc R . .
C5 C 0.3404(2) 0.42599(16) 0.46815(15) 0.0288(4) Uani 1 1 d . . .
C6 C 0.4018(2) 0.44701(17) 0.34863(15) 0.0380(5) Uani 1 1 d . . .
H6 H 0.3674 0.5252 0.2845 0.046 Uiso 1 1 calc R . .
C7 C 0.5101(3) 0.35587(18) 0.32475(17) 0.0420(5) Uani 1 1 d . . .
H7 H 0.5511 0.3706 0.2440 0.050 Uiso 1 1 calc R . .
C8 C 0.5612(2) 0.23999(18) 0.41918(17) 0.0427(5) Uani 1 1 d . . .
H8 H 0.6366 0.1769 0.4015 0.051 Uiso 1 1 calc R . .
C9 C 0.5050(2) 0.21655(17) 0.53522(17) 0.0399(5) Uani 1 1 d . . .
H9 H 0.5413 0.1378 0.5979 0.048 Uiso 1 1 calc R . .
C10 C 0.3925(2) 0.30924(16) 0.56275(15) 0.0323(4) Uani 1 1 d . . .
C12 C 0.0683(2) 0.58384(17) 0.65541(17) 0.0332(5) Uani 1 1 d . . .
C15 C -0.0805(2) 0.79006(16) 0.59032(15) 0.0354(5) Uani 1 1 d . . .
H15A H -0.0136 0.8099 0.6362 0.043 Uiso 1 1 calc R . .
H15B H -0.1982 0.7626 0.6394 0.043 Uiso 1 1 calc R . .
C16 C -0.1110(3) 0.90314(16) 0.47390(15) 0.0441(5) Uani 1 1 d . . .
H16C H -0.1715 0.8811 0.4275 0.066 Uiso 1 1 calc R . .
H16B H 0.0061 0.9323 0.4282 0.066 Uiso 1 1 calc R . .
H16A H -0.1875 0.9699 0.4900 0.066 Uiso 1 1 calc R . .
C22 C 0.7647(2) 0.14425(16) -0.19995(15) 0.0395(5) Uani 1 1 d . . .
H22 H 0.7595 0.1657 -0.2809 0.047 Uiso 1 1 calc R . .
C23 C 0.7371(2) 0.01976(15) -0.11242(15) 0.0304(4) Uani 1 1 d . . .
C24 C 0.7410(2) -0.01130(15) 0.00424(15) 0.0307(4) Uani 1 1 d . . .
H24 H 0.7200 -0.0933 0.0652 0.037 Uiso 1 1 calc R . .
C25 C 0.7760(2) 0.07843(15) 0.03438(14) 0.0299(4) Uani 1 1 d . . .
C26 C 0.7872(2) 0.05224(16) 0.15239(15) 0.0365(5) Uani 1 1 d . . .
H26 H 0.7659 -0.0283 0.2163 0.044 Uiso 1 1 calc R . .
C27 C 0.8283(2) 0.14123(17) 0.17573(16) 0.0408(5) Uani 1 1 d . . .
H27 H 0.8376 0.1220 0.2555 0.049 Uiso 1 1 calc R . .
C28 C 0.8570(2) 0.26105(17) 0.08264(17) 0.0381(5) Uani 1 1 d . . .
H28 H 0.8849 0.3225 0.1001 0.046 Uiso 1 1 calc R . .
C29 C 0.8454(2) 0.29043(16) -0.03225(16) 0.0376(5) Uani 1 1 d . . .
H29 H 0.8644 0.3722 -0.0944 0.045 Uiso 1 1 calc R . .
C30 C 0.8051(2) 0.19923(15) -0.05951(15) 0.0318(4) Uani 1 1 d . . .
C32 C 0.7121(2) -0.07056(16) -0.15321(16) 0.0326(4) Uani 1 1 d . . .
C35 C 0.6685(3) -0.27968(15) -0.09287(15) 0.0375(5) Uani 1 1 d . . .
H35A H 0.7747 -0.2873 -0.1507 0.045 Uiso 1 1 calc R . .
H35B H 0.5572 -0.2585 -0.1300 0.045 Uiso 1 1 calc R . .
C36 C 0.6587(3) -0.40017(15) 0.02069(15) 0.0460(5) Uani 1 1 d . . .
H36A H 0.7698 -0.4203 0.0562 0.069 Uiso 1 1 calc R . .
H36B H 0.6463 -0.4677 0.0028 0.069 Uiso 1 1 calc R . .
H36C H 0.5535 -0.3912 0.0773 0.069 Uiso 1 1 calc R . .
O13 O 0.02477(17) 0.56547(11) 0.75851(10) 0.0435(4) Uani 1 1 d . . .
O14 O 0.02439(16) 0.69215(11) 0.56194(10) 0.0354(3) Uani 1 1 d . . .
O33 O 0.71686(17) -0.04632(11) -0.25663(10) 0.0435(4) Uani 1 1 d . . .
O34 O 0.68547(15) -0.18336(10) -0.06128(9) 0.0343(3) Uani 1 1 d . . .
N1 N 0.3368(2) 0.28166(14) 0.68186(13) 0.0408(4) Uani 1 1 d . . .
N21 N 0.7970(2) 0.23229(13) -0.17723(12) 0.0403(4) 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
C2 0.0514(15) 0.0324(12) 0.0305(11) -0.0095(10) -0.0069(9) -0.0027(11)
C3 0.0316(11) 0.0234(10) 0.0351(11) -0.0104(9) -0.0078(8) -0.0035(9)
C4 0.0318(12) 0.0230(10) 0.0343(11) -0.0066(9) -0.0102(8) -0.0044(9)
C5 0.0303(11) 0.0229(10) 0.0326(10) -0.0101(9) -0.0073(8) -0.0049(9)
C6 0.0449(13) 0.0315(12) 0.0333(11) -0.0101(9) -0.0058(9) -0.0070(10)
C7 0.0461(14) 0.0384(12) 0.0407(12) -0.0192(11) -0.0005(10) -0.0058(11)
C8 0.0383(13) 0.0354(13) 0.0532(14) -0.0231(11) -0.0031(10) 0.0029(10)
C9 0.0414(13) 0.0265(11) 0.0437(12) -0.0088(10) -0.0121(10) 0.0012(10)
C10 0.0311(12) 0.0255(11) 0.0361(11) -0.0102(9) -0.0071(9) -0.0019(9)
C12 0.0362(12) 0.0271(11) 0.0337(11) -0.0094(9) -0.0063(9) -0.0079(9)
C15 0.0393(12) 0.0270(11) 0.0390(11) -0.0160(9) -0.0054(9) 0.0009(9)
C16 0.0571(15) 0.0272(11) 0.0418(12) -0.0096(10) -0.0127(10) -0.0013(10)
C22 0.0488(14) 0.0335(12) 0.0290(11) -0.0075(9) -0.0072(9) -0.0052(10)
C23 0.0282(11) 0.0234(10) 0.0331(11) -0.0094(9) -0.0025(8) -0.0001(8)
C24 0.0250(11) 0.0246(10) 0.0345(11) -0.0095(9) -0.0002(8) -0.0003(9)
C25 0.0249(11) 0.0264(10) 0.0326(10) -0.0113(9) -0.0023(8) 0.0015(9)
C26 0.0387(12) 0.0307(11) 0.0336(11) -0.0117(9) -0.0036(9) 0.0002(9)
C27 0.0426(13) 0.0403(12) 0.0387(12) -0.0197(10) -0.0062(9) 0.0020(10)
C28 0.0334(12) 0.0330(12) 0.0503(12) -0.0232(10) -0.0060(9) 0.0023(9)
C29 0.0339(12) 0.0279(11) 0.0456(12) -0.0135(10) -0.0032(9) -0.0028(9)
C30 0.0287(11) 0.0262(11) 0.0332(11) -0.0094(9) -0.0036(8) 0.0003(9)
C32 0.0295(11) 0.0269(11) 0.0339(11) -0.0093(9) -0.0048(8) 0.0012(9)
C35 0.0448(13) 0.0311(11) 0.0406(11) -0.0181(10) -0.0097(9) -0.0039(10)
C36 0.0576(15) 0.0277(11) 0.0494(13) -0.0135(10) -0.0104(10) -0.0052(11)
O13 0.0570(10) 0.0344(8) 0.0291(8) -0.0097(6) -0.0042(6) 0.0017(7)
O14 0.0463(9) 0.0233(7) 0.0311(7) -0.0091(6) -0.0071(6) 0.0008(6)
O33 0.0614(10) 0.0336(8) 0.0303(8) -0.0091(6) -0.0110(6) -0.0036(7)
O34 0.0432(8) 0.0245(7) 0.0326(7) -0.0110(6) -0.0038(6) -0.0047(6)
N1 0.0480(12) 0.0283(9) 0.0366(10) -0.0088(8) -0.0076(8) 0.0018(8)
N21 0.0531(12) 0.0245(9) 0.0364(9) -0.0065(8) -0.0101(8) -0.0053(8)

_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
C2 N1 1.313(2) . ?
C2 C3 1.414(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(2) . ?
C3 C12 1.485(2) . ?
C4 C5 1.410(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.410(2) . ?
C5 C10 1.413(2) . ?
C6 C7 1.360(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.356(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.411(2) . ?
C9 H9 0.9500 . ?
C10 N1 1.381(2) . ?
C12 O13 1.2085(18) . ?
C12 O14 1.336(2) . ?
C15 O14 1.4475(18) . ?
C15 C16 1.500(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16C 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16A 0.9800 . ?
C22 N21 1.3170(19) . ?
C22 C23 1.419(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.362(2) . ?
C23 C32 1.483(2) . ?
C24 C25 1.409(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.408(2) . ?
C25 C30 1.413(2) . ?
C26 C27 1.361(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.401(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.359(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.417(2) . ?
C29 H29 0.9500 . ?
C30 N21 1.376(2) . ?
C32 O33 1.2064(18) . ?
C32 O34 1.3372(18) . ?
C35 O34 1.4487(16) . ?
C35 C36 1.499(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

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 C2 C3 125.05(17) . . ?
N1 C2 H2 117.5 . . ?
C3 C2 H2 117.5 . . ?
C4 C3 C2 118.23(17) . . ?
C4 C3 C12 123.10(17) . . ?
C2 C3 C12 118.66(16) . . ?
C3 C4 C5 119.69(17) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 122.89(17) . . ?
C4 C5 C10 117.84(16) . . ?
C6 C5 C10 119.27(17) . . ?
C7 C6 C5 120.32(19) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.14(18) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 121.17(19) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.97(19) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
N1 C10 C9 118.34(17) . . ?
N1 C10 C5 122.52(17) . . ?
C9 C10 C5 119.14(16) . . ?
O13 C12 O14 123.58(18) . . ?
O13 C12 C3 124.99(18) . . ?
O14 C12 C3 111.43(15) . . ?
O14 C15 C16 107.37(13) . . ?
O14 C15 H15A 110.2 . . ?
C16 C15 H15A 110.2 . . ?
O14 C15 H15B 110.2 . . ?
C16 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
C15 C16 H16C 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
N21 C22 C23 124.84(16) . . ?
N21 C22 H22 117.6 . . ?
C23 C22 H22 117.6 . . ?
C24 C23 C22 118.06(15) . . ?
C24 C23 C32 123.55(15) . . ?
C22 C23 C32 118.36(16) . . ?
C23 C24 C25 119.87(15) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 123.10(15) . . ?
C26 C25 C30 119.07(14) . . ?
C24 C25 C30 117.82(15) . . ?
C27 C26 C25 120.59(16) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 120.33(17) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 120.86(16) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 120.09(16) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
N21 C30 C25 122.68(14) . . ?
N21 C30 C29 118.27(15) . . ?
C25 C30 C29 119.06(15) . . ?
O33 C32 O34 123.75(15) . . ?
O33 C32 C23 124.46(16) . . ?
O34 C32 C23 111.79(15) . . ?
O34 C35 C36 107.14(13) . . ?
O34 C35 H35A 110.3 . . ?
C36 C35 H35A 110.3 . . ?
O34 C35 H35B 110.3 . . ?
C36 C35 H35B 110.3 . . ?
H35A C35 H35B 108.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C12 O14 C15 116.01(13) . . ?
C32 O34 C35 115.76(13) . . ?
C2 N1 C10 116.64(16) . . ?
C22 N21 C30 116.71(15) . . ?

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
N1 C2 C3 C4 1.1(3) . . . . ?
N1 C2 C3 C12 -178.00(15) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C12 C3 C4 C5 177.67(14) . . . . ?
C3 C4 C5 C6 -178.81(15) . . . . ?
C3 C4 C5 C10 0.3(2) . . . . ?
C4 C5 C6 C7 179.09(16) . . . . ?
C10 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 N1 179.49(15) . . . . ?
C8 C9 C10 C5 -0.2(2) . . . . ?
C4 C5 C10 N1 1.3(2) . . . . ?
C6 C5 C10 N1 -179.60(14) . . . . ?
C4 C5 C10 C9 -179.07(14) . . . . ?
C6 C5 C10 C9 0.1(2) . . . . ?
C4 C3 C12 O13 -177.59(17) . . . . ?
C2 C3 C12 O13 1.5(2) . . . . ?
C4 C3 C12 O14 1.6(2) . . . . ?
C2 C3 C12 O14 -179.37(15) . . . . ?
N21 C22 C23 C24 1.2(3) . . . . ?
N21 C22 C23 C32 -176.71(17) . . . . ?
C22 C23 C24 C25 -1.5(3) . . . . ?
C32 C23 C24 C25 176.26(16) . . . . ?
C23 C24 C25 C26 -178.16(17) . . . . ?
C23 C24 C25 C30 0.4(2) . . . . ?
C24 C25 C26 C27 177.49(17) . . . . ?
C30 C25 C26 C27 -1.0(3) . . . . ?
C25 C26 C27 C28 1.1(3) . . . . ?
C26 C27 C28 C29 -0.4(3) . . . . ?
C27 C28 C29 C30 -0.4(3) . . . . ?
C26 C25 C30 N21 179.88(16) . . . . ?
C24 C25 C30 N21 1.3(3) . . . . ?
C26 C25 C30 C29 0.2(2) . . . . ?
C24 C25 C30 C29 -178.37(16) . . . . ?
C28 C29 C30 N21 -179.18(17) . . . . ?
C28 C29 C30 C25 0.5(3) . . . . ?
C24 C23 C32 O33 -176.32(18) . . . . ?
C22 C23 C32 O33 1.5(3) . . . . ?
C24 C23 C32 O34 2.9(2) . . . . ?
C22 C23 C32 O34 -179.28(15) . . . . ?
O13 C12 O14 C15 0.3(2) . . . . ?
C3 C12 O14 C15 -178.88(12) . . . . ?
C16 C15 O14 C12 178.72(14) . . . . ?
O33 C32 O34 C35 2.2(3) . . . . ?
C23 C32 O34 C35 -177.10(14) . . . . ?
C36 C35 O34 C32 174.40(15) . . . . ?
C3 C2 N1 C10 0.4(3) . . . . ?
C9 C10 N1 C2 178.76(15) . . . . ?
C5 C10 N1 C2 -1.6(2) . . . . ?
C23 C22 N21 C30 0.4(3) . . . . ?
C25 C30 N21 C22 -1.6(3) . . . . ?
C29 C30 N21 C22 178.02(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.038


data_bs071011
_database_code_depnum_ccdc_archive 'CCDC 849680'
#TrackingRef '- bs071011.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N4 O4'
_chemical_formula_weight         430.46

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   P21/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                   9.3329(2)
_cell_length_b                   12.7049(3)
_cell_length_c                   9.1195(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.085(2)
_cell_angle_gamma                90.00
_cell_volume                     1070.59(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    7141
_cell_measurement_theta_min      2.7202
_cell_measurement_theta_max      32.6893

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7360
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur Ruby CCD'
_diffrn_measurement_method       '\o oscillation scan'
_diffrn_detector_area_resol_mean 10.4498
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14471
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         32.76
_reflns_number_total             3660
_reflns_number_gt                3116
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis^Pro^ (Oxford, 2007)'
_computing_cell_refinement       'CrysAlis^Pro^ (Oxford, 2007)'
_computing_data_reduction        'CrysAlis^Pro^ (Oxford, 2007)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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^)+(0.0636P)^2^+0.2695P] 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         3660
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1294
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C2 C 0.99316(10) 0.05717(7) 0.99545(10) 0.02022(18) Uani 1 1 d . . .
C3 C 0.87413(10) 0.12662(7) 0.96459(10) 0.02056(18) Uani 1 1 d . . .
C4 C 0.93251(10) 0.23153(7) 0.97222(11) 0.02191(19) Uani 1 1 d . . .
C5 C 1.08023(11) 0.22206(7) 1.00530(12) 0.0264(2) Uani 1 1 d . . .
H5A H 1.1474 0.2786 1.0164 0.032 Uiso 1 1 calc R . .
C6 C 0.86144(11) 0.33569(7) 0.95676(11) 0.02233(19) Uani 1 1 d . . .
C7 C 0.76356(12) 0.36880(8) 1.04920(12) 0.0288(2) Uani 1 1 d . . .
H7A H 0.7342 0.3222 1.1209 0.035 Uiso 1 1 calc R . .
C8 C 0.70941(13) 0.47041(9) 1.03554(14) 0.0331(2) Uani 1 1 d . . .
H8A H 0.6428 0.4914 1.0997 0.040 Uiso 1 1 calc R . .
C10 C 0.83949(15) 0.50847(9) 0.84998(13) 0.0360(3) Uani 1 1 d . . .
H10A H 0.8670 0.5569 0.7796 0.043 Uiso 1 1 calc R . .
C11 C 0.90010(13) 0.40842(8) 0.85516(12) 0.0297(2) Uani 1 1 d . . .
H11A H 0.9671 0.3899 0.7901 0.036 Uiso 1 1 calc R . .
C12 C 0.72112(10) 0.09986(8) 0.92322(11) 0.02343(19) Uani 1 1 d . . .
C15 C 0.48603(12) 0.16686(9) 0.83969(15) 0.0356(3) Uani 1 1 d . . .
H15A H 0.4437 0.1294 0.9186 0.043 Uiso 1 1 calc R . .
H15B H 0.4705 0.1237 0.7485 0.043 Uiso 1 1 calc R . .
C16 C 0.41703(15) 0.27249(11) 0.8120(2) 0.0500(4) Uani 1 1 d . . .
H16A H 0.4291 0.3131 0.9043 0.075 Uiso 1 1 calc R . .
H16B H 0.3137 0.2636 0.7765 0.075 Uiso 1 1 calc R . .
H16C H 0.4631 0.3100 0.7372 0.075 Uiso 1 1 calc R . .
N1 N 1.11417(9) 0.11770(6) 1.01945(10) 0.02520(19) Uani 1 1 d . . .
H1A H 1.2027 0.0929 1.0412 0.030 Uiso 1 1 calc R . .
N9 N 0.74520(12) 0.54089(7) 0.93747(12) 0.0353(2) Uani 1 1 d . . .
O13 O 0.66724(9) 0.01199(6) 0.91840(12) 0.0378(2) Uani 1 1 d . . .
O14 O 0.64014(8) 0.18467(6) 0.88512(9) 0.02837(18) 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
C2 0.0205(4) 0.0154(4) 0.0249(4) -0.0007(3) 0.0034(3) 0.0009(3)
C3 0.0216(4) 0.0163(4) 0.0238(4) 0.0000(3) 0.0030(3) 0.0011(3)
C4 0.0242(4) 0.0154(4) 0.0260(4) 0.0001(3) 0.0029(3) 0.0014(3)
C5 0.0242(4) 0.0149(4) 0.0396(5) -0.0003(4) 0.0031(4) 0.0005(3)
C6 0.0250(4) 0.0158(4) 0.0252(4) 0.0000(3) 0.0001(3) 0.0016(3)
C7 0.0334(5) 0.0196(4) 0.0346(5) 0.0004(4) 0.0094(4) 0.0027(4)
C8 0.0356(6) 0.0227(5) 0.0418(6) -0.0038(4) 0.0081(5) 0.0070(4)
C10 0.0507(7) 0.0220(5) 0.0350(6) 0.0081(4) 0.0047(5) 0.0069(4)
C11 0.0384(6) 0.0229(5) 0.0286(5) 0.0037(4) 0.0071(4) 0.0048(4)
C12 0.0215(4) 0.0188(4) 0.0298(5) 0.0002(3) 0.0027(3) 0.0029(3)
C15 0.0210(5) 0.0291(5) 0.0544(7) -0.0011(5) -0.0024(4) 0.0032(4)
C16 0.0318(6) 0.0366(7) 0.0771(10) 0.0018(7) -0.0078(6) 0.0136(5)
N1 0.0202(4) 0.0154(4) 0.0394(5) -0.0005(3) 0.0023(3) 0.0011(3)
N9 0.0423(5) 0.0208(4) 0.0412(5) 0.0019(4) 0.0002(4) 0.0090(4)
O13 0.0226(4) 0.0198(4) 0.0692(6) 0.0027(4) 0.0001(4) -0.0005(3)
O14 0.0206(3) 0.0199(3) 0.0427(4) 0.0002(3) -0.0023(3) 0.0038(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
C2 N1 1.3584(12) . ?
C2 C3 1.4156(12) . ?
C2 C2 1.4596(18) 3_757 ?
C3 C4 1.4379(13) . ?
C3 C12 1.4649(13) . ?
C4 C5 1.3745(14) . ?
C4 C6 1.4780(13) . ?
C5 N1 1.3651(12) . ?
C6 C11 1.3916(14) . ?
C6 C7 1.3924(14) . ?
C7 C8 1.3855(15) . ?
C8 N9 1.3406(16) . ?
C10 N9 1.3335(17) . ?
C10 C11 1.3894(15) . ?
C12 O13 1.2227(12) . ?
C12 O14 1.3338(11) . ?
C15 O14 1.4574(13) . ?
C15 C16 1.4946(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
N1 C2 C3 106.89(8) . . ?
N1 C2 C2 119.35(10) . 3_757 ?
C3 C2 C2 133.76(11) . 3_757 ?
C2 C3 C4 106.66(8) . . ?
C2 C3 C12 128.01(8) . . ?
C4 C3 C12 125.22(8) . . ?
C5 C4 C3 106.92(8) . . ?
C5 C4 C6 121.47(9) . . ?
C3 C4 C6 131.56(9) . . ?
N1 C5 C4 108.54(8) . . ?
C11 C6 C7 117.14(9) . . ?
C11 C6 C4 120.21(9) . . ?
C7 C6 C4 122.45(9) . . ?
C8 C7 C6 119.28(10) . . ?
N9 C8 C7 124.08(11) . . ?
N9 C10 C11 124.20(11) . . ?
C10 C11 C6 119.19(10) . . ?
O13 C12 O14 120.88(9) . . ?
O13 C12 C3 127.03(9) . . ?
O14 C12 C3 112.07(8) . . ?
O14 C15 C16 107.04(10) . . ?
C2 N1 C5 110.98(8) . . ?
C10 N9 C8 116.11(10) . . ?
C12 O14 C15 116.67(8) . . ?

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
N1 C2 C3 C4 -0.12(10) . . . . ?
C2 C2 C3 C4 -179.90(13) 3_757 . . . ?
N1 C2 C3 C12 176.29(9) . . . . ?
C2 C2 C3 C12 -3.5(2) 3_757 . . . ?
C2 C3 C4 C5 0.43(11) . . . . ?
C12 C3 C4 C5 -176.11(9) . . . . ?
C2 C3 C4 C6 -177.01(10) . . . . ?
C12 C3 C4 C6 6.46(17) . . . . ?
C3 C4 C5 N1 -0.58(12) . . . . ?
C6 C4 C5 N1 177.17(9) . . . . ?
C5 C4 C6 C11 56.72(14) . . . . ?
C3 C4 C6 C11 -126.15(12) . . . . ?
C5 C4 C6 C7 -117.89(12) . . . . ?
C3 C4 C6 C7 59.23(15) . . . . ?
C11 C6 C7 C8 0.40(16) . . . . ?
C4 C6 C7 C8 175.17(10) . . . . ?
C6 C7 C8 N9 0.01(18) . . . . ?
N9 C10 C11 C6 0.25(19) . . . . ?
C7 C6 C11 C10 -0.51(16) . . . . ?
C4 C6 C11 C10 -175.41(10) . . . . ?
C2 C3 C12 O13 5.80(18) . . . . ?
C4 C3 C12 O13 -178.41(10) . . . . ?
C2 C3 C12 O14 -172.58(9) . . . . ?
C4 C3 C12 O14 3.21(14) . . . . ?
C3 C2 N1 C5 -0.24(11) . . . . ?
C2 C2 N1 C5 179.58(11) 3_757 . . . ?
C4 C5 N1 C2 0.52(12) . . . . ?
C11 C10 N9 C8 0.16(19) . . . . ?
C7 C8 N9 C10 -0.29(18) . . . . ?
O13 C12 O14 C15 0.61(15) . . . . ?
C3 C12 O14 C15 179.10(9) . . . . ?
C16 C15 O14 C12 176.46(11) . . . . ?

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 H1A O13 0.88 1.81 2.6216(11) 153.2 3_757

_diffrn_measured_fraction_theta_max 0.925
_diffrn_reflns_theta_full        30.44
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.047