# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Alessia Bacchi'
'Giulia Cantoni'
'Mauro Carcelli'
'Tiziana Chiodo'
'Cecilia De Filippo'
'Silvio Pipolo'

_publ_contact_author_name        'Alessia Bacchi'
_publ_contact_author_email       ALESSIA.BACCHI@UNIPR.IT

_publ_section_title              
;
A discussion on the solid state organization of
4-pyridil imino compounds and on the cocrystallization between their
molecular precursors
;

# Attachment 'bacchi.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 712725'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -4.2923 7.6849 '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                   10.8998(5)
_cell_length_b                   11.4338(4)
_cell_length_c                   17.9406(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.393(5)
_cell_angle_gamma                90.00
_cell_volume                     2233.92(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      6
_cell_measurement_theta_max      16

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens AED diffractometer'
_diffrn_measurement_method       'θ/2θ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         1
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4453
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_sigmaI/netI    0.0082
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.06
_diffrn_reflns_theta_max         70.03
_reflns_number_total             4234
_reflns_number_gt                3638
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0622P)²+0.4061P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0067(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4234
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
N1 N 0.14242(14) -0.31795(13) 0.62988(8) 0.0709(4) Uani 1 1 d . . .
N2 N 0.28338(12) -0.61091(11) 0.44627(6) 0.0585(3) Uani 1 1 d . . .
N3 N -0.42195(13) -0.75679(13) 1.10931(7) 0.0694(4) Uani 1 1 d . . .
N4 N -0.18913(12) -0.47398(12) 0.95695(7) 0.0624(3) Uani 1 1 d . . .
O1 O 0.43788(12) -0.88148(9) 0.20920(6) 0.0684(3) Uani 1 1 d . . .
H1O H 0.4839 -0.8443 0.1831 0.103 Uiso 1 1 calc R . .
O2 O 0.02763(13) -0.20022(10) 0.74162(6) 0.0740(4) Uani 1 1 d . . .
H2O H 0.0667 -0.2403 0.7130 0.111 Uiso 1 1 calc R . .
C1 C 0.07912(18) -0.30235(17) 0.56570(10) 0.0770(5) Uani 1 1 d . . .
H1A H 0.0177 -0.2459 0.5639 0.092 Uiso 1 1 calc R . .
C2 C 0.09924(16) -0.36495(16) 0.50182(9) 0.0705(4) Uani 1 1 d . . .
H2A H 0.0527 -0.3499 0.4583 0.085 Uiso 1 1 calc R . .
C3 C 0.18910(13) -0.45023(13) 0.50288(8) 0.0533(3) Uani 1 1 d . . .
C4 C 0.25609(16) -0.46533(15) 0.56906(8) 0.0644(4) Uani 1 1 d . . .
H4 H 0.3187 -0.5206 0.5724 0.077 Uiso 1 1 calc R . .
C5 C 0.23020(17) -0.39853(17) 0.63016(9) 0.0712(5) Uani 1 1 d . . .
H5 H 0.2767 -0.4104 0.6741 0.085 Uiso 1 1 calc R . .
C6 C 0.21447(13) -0.52269(13) 0.43577(8) 0.0539(3) Uani 1 1 d . . .
C7 C 0.15490(19) -0.48772(18) 0.36244(9) 0.0817(6) Uani 1 1 d . . .
H7A H 0.1689 -0.5472 0.3260 0.123 Uiso 1 1 calc R . .
H7B H 0.1894 -0.4151 0.3464 0.123 Uiso 1 1 calc R . .
H7C H 0.0682 -0.4784 0.3679 0.123 Uiso 1 1 calc R . .
C8 C 0.31995(13) -0.67835(13) 0.38403(7) 0.0528(3) Uani 1 1 d . . .
C9 C 0.40221(15) -0.63325(14) 0.33513(8) 0.0621(4) Uani 1 1 d . . .
H9 H 0.4305 -0.5570 0.3415 0.074 Uiso 1 1 calc R . .
C10 C 0.44317(15) -0.69953(14) 0.27685(8) 0.0593(4) Uani 1 1 d . . .
H10 H 0.4991 -0.6680 0.2447 0.071 Uiso 1 1 calc R . .
C11 C 0.40135(13) -0.81247(13) 0.26619(7) 0.0528(3) Uani 1 1 d . . .
C12 C 0.32032(15) -0.85826(14) 0.31566(8) 0.0604(4) Uani 1 1 d . . .
H12 H 0.2920 -0.9345 0.3093 0.073 Uiso 1 1 calc R . .
C13 C 0.28080(14) -0.79239(14) 0.37444(8) 0.0593(4) Uani 1 1 d . . .
H13 H 0.2275 -0.8250 0.4078 0.071 Uiso 1 1 calc R . .
C14 C -0.31960(17) -0.69461(17) 1.11983(9) 0.0701(4) Uani 1 1 d . . .
H14 H -0.2779 -0.6997 1.1660 0.084 Uiso 1 1 calc R . .
C15 C -0.27166(15) -0.62354(15) 1.06681(8) 0.0656(4) Uani 1 1 d . . .
H15 H -0.1993 -0.5825 1.0774 0.079 Uiso 1 1 calc R . .
C16 C -0.33117(13) -0.61301(13) 0.99750(8) 0.0553(3) Uani 1 1 d . . .
C17 C -0.43613(16) -0.67816(18) 0.98591(10) 0.0776(5) Uani 1 1 d . . .
H17 H -0.4792 -0.6752 0.9401 0.093 Uiso 1 1 calc R . .
C18 C -0.47754(18) -0.74777(19) 1.04218(10) 0.0838(6) Uani 1 1 d . . .
H18 H -0.5487 -0.7911 1.0327 0.101 Uiso 1 1 calc R . .
C19 C -0.28061(14) -0.53763(13) 0.93812(8) 0.0562(4) Uani 1 1 d . . .
C20 C -0.3397(2) -0.5443(2) 0.86119(10) 0.0920(7) Uani 1 1 d . . .
H20A H -0.2967 -0.4940 0.8283 0.138 Uiso 1 1 calc R . .
H20B H -0.4238 -0.5199 0.8627 0.138 Uiso 1 1 calc R . .
H20C H -0.3363 -0.6234 0.8434 0.138 Uiso 1 1 calc R . .
C21 C -0.13364(13) -0.40455(14) 0.90146(8) 0.0552(4) Uani 1 1 d . . .
C22 C -0.04894(15) -0.45334(14) 0.85558(8) 0.0620(4) Uani 1 1 d . . .
H22 H -0.0287 -0.5320 0.8609 0.074 Uiso 1 1 calc R . .
C23 C 0.00620(14) -0.38709(13) 0.80189(8) 0.0583(4) Uani 1 1 d . . .
H23 H 0.0637 -0.4211 0.7717 0.070 Uiso 1 1 calc R . .
C24 C -0.02397(14) -0.27072(13) 0.79314(7) 0.0541(3) Uani 1 1 d . . .
C25 C -0.10774(15) -0.22143(14) 0.83941(9) 0.0632(4) Uani 1 1 d . . .
H25 H -0.1283 -0.1429 0.8340 0.076 Uiso 1 1 calc R . .
C26 C -0.16129(15) -0.28728(15) 0.89365(9) 0.0639(4) Uani 1 1 d . . .
H26 H -0.2163 -0.2525 0.9251 0.077 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0845(9) 0.0709(9) 0.0590(8) -0.0119(7) 0.0219(7) -0.0104(8)
N2 0.0684(8) 0.0604(7) 0.0469(6) 0.0008(5) 0.0068(5) 0.0087(6)
N3 0.0773(9) 0.0752(9) 0.0571(8) -0.0026(6) 0.0197(6) -0.0138(7)
N4 0.0664(7) 0.0710(8) 0.0501(7) -0.0005(6) 0.0046(5) -0.0169(7)
O1 0.0890(8) 0.0592(6) 0.0585(6) -0.0082(5) 0.0218(5) -0.0018(6)
O2 0.1066(10) 0.0590(6) 0.0583(6) -0.0026(5) 0.0265(6) -0.0133(6)
C1 0.0795(11) 0.0769(11) 0.0756(11) -0.0162(9) 0.0137(9) 0.0110(9)
C2 0.0747(10) 0.0756(11) 0.0609(9) -0.0101(8) -0.0001(8) 0.0120(9)
C3 0.0583(8) 0.0539(8) 0.0482(7) -0.0013(6) 0.0073(6) -0.0045(6)
C4 0.0740(10) 0.0674(9) 0.0519(8) -0.0019(7) 0.0034(7) 0.0039(8)
C5 0.0864(12) 0.0780(11) 0.0495(8) -0.0053(8) 0.0058(8) -0.0061(10)
C6 0.0594(8) 0.0552(8) 0.0471(7) -0.0013(6) 0.0029(6) 0.0004(7)
C7 0.1034(14) 0.0847(12) 0.0555(9) -0.0107(9) -0.0144(9) 0.0309(11)
C8 0.0585(8) 0.0562(8) 0.0440(7) 0.0028(6) 0.0040(6) 0.0074(6)
C9 0.0781(10) 0.0499(8) 0.0591(8) -0.0020(7) 0.0136(7) -0.0043(7)
C10 0.0680(9) 0.0578(8) 0.0534(8) 0.0032(7) 0.0162(7) -0.0043(7)
C11 0.0602(8) 0.0528(8) 0.0455(7) 0.0009(6) 0.0039(6) 0.0045(6)
C12 0.0705(9) 0.0537(8) 0.0576(8) -0.0006(7) 0.0089(7) -0.0082(7)
C13 0.0625(8) 0.0638(9) 0.0524(8) 0.0045(7) 0.0122(6) -0.0044(7)
C14 0.0789(11) 0.0826(11) 0.0491(8) 0.0004(8) 0.0059(7) -0.0113(9)
C15 0.0670(9) 0.0768(10) 0.0529(8) -0.0003(7) 0.0020(7) -0.0171(8)
C16 0.0558(8) 0.0587(8) 0.0517(8) -0.0023(6) 0.0057(6) -0.0051(6)
C17 0.0722(11) 0.0983(13) 0.0616(9) 0.0105(9) -0.0056(8) -0.0283(10)
C18 0.0749(11) 0.1060(15) 0.0706(11) 0.0077(10) 0.0049(9) -0.0355(11)
C19 0.0571(8) 0.0593(8) 0.0522(8) 0.0018(6) 0.0007(6) -0.0064(7)
C20 0.0952(13) 0.1124(16) 0.0664(11) 0.0258(11) -0.0208(9) -0.0430(12)
C21 0.0572(8) 0.0623(9) 0.0461(7) -0.0029(6) 0.0014(6) -0.0134(7)
C22 0.0752(10) 0.0520(8) 0.0593(8) -0.0004(7) 0.0078(7) -0.0017(7)
C23 0.0658(9) 0.0599(9) 0.0497(7) -0.0064(6) 0.0094(6) -0.0003(7)
C24 0.0643(8) 0.0551(8) 0.0431(7) -0.0048(6) 0.0034(6) -0.0116(7)
C25 0.0750(10) 0.0524(8) 0.0630(9) -0.0042(7) 0.0112(7) -0.0016(7)
C26 0.0643(9) 0.0670(10) 0.0614(9) -0.0077(7) 0.0147(7) -0.0034(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
N1 C5 1.328(2) . ?
N1 C1 1.329(2) . ?
N2 C6 1.2671(19) . ?
N2 C8 1.4274(18) . ?
N3 C18 1.329(2) . ?
N3 C14 1.330(2) . ?
N4 C19 1.2688(19) . ?
N4 C21 1.4273(18) . ?
O1 C11 1.3639(17) . ?
O2 C24 1.3652(17) . ?
C1 C2 1.377(2) . ?
C2 C3 1.382(2) . ?
C3 C4 1.379(2) . ?
C3 C6 1.4966(19) . ?
C4 C5 1.375(2) . ?
C6 C7 1.497(2) . ?
C8 C9 1.380(2) . ?
C8 C13 1.380(2) . ?
C9 C10 1.381(2) . ?
C10 C11 1.380(2) . ?
C11 C12 1.381(2) . ?
C12 C13 1.379(2) . ?
C14 C15 1.371(2) . ?
C15 C16 1.383(2) . ?
C16 C17 1.374(2) . ?
C16 C19 1.494(2) . ?
C17 C18 1.376(2) . ?
C19 C20 1.500(2) . ?
C21 C22 1.380(2) . ?
C21 C26 1.380(2) . ?
C22 C23 1.382(2) . ?
C23 C24 1.378(2) . ?
C24 C25 1.380(2) . ?
C25 C26 1.379(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
C5 N1 C1 116.36(14) . . ?
C6 N2 C8 119.79(12) . . ?
C18 N3 C14 115.79(14) . . ?
C19 N4 C21 118.98(12) . . ?
N1 C1 C2 123.81(17) . . ?
C1 C2 C3 119.54(16) . . ?
C4 C3 C2 116.74(14) . . ?
C4 C3 C6 120.97(14) . . ?
C2 C3 C6 122.29(13) . . ?
C5 C4 C3 119.88(16) . . ?
N1 C5 C4 123.66(16) . . ?
N2 C6 C3 116.70(12) . . ?
N2 C6 C7 125.16(13) . . ?
C3 C6 C7 118.12(13) . . ?
C9 C8 C13 118.64(13) . . ?
C9 C8 N2 120.36(14) . . ?
C13 C8 N2 120.85(13) . . ?
C8 C9 C10 121.03(14) . . ?
C11 C10 C9 120.21(14) . . ?
O1 C11 C10 122.69(13) . . ?
O1 C11 C12 118.49(13) . . ?
C10 C11 C12 118.82(13) . . ?
C13 C12 C11 120.85(14) . . ?
C12 C13 C8 120.41(13) . . ?
N3 C14 C15 124.07(15) . . ?
C14 C15 C16 119.81(15) . . ?
C17 C16 C15 116.43(14) . . ?
C17 C16 C19 122.33(14) . . ?
C15 C16 C19 121.21(13) . . ?
C16 C17 C18 119.94(16) . . ?
N3 C18 C17 123.94(16) . . ?
N4 C19 C16 116.77(13) . . ?
N4 C19 C20 125.20(14) . . ?
C16 C19 C20 118.03(13) . . ?
C22 C21 C26 118.74(14) . . ?
C22 C21 N4 120.31(14) . . ?
C26 C21 N4 120.93(14) . . ?
C21 C22 C23 121.02(15) . . ?
C24 C23 C22 119.99(14) . . ?
O2 C24 C23 122.97(13) . . ?
O2 C24 C25 117.89(14) . . ?
C23 C24 C25 119.12(14) . . ?
C26 C25 C24 120.78(15) . . ?
C25 C26 C21 120.33(14) . . ?

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
O1 H1O N3 0.82 1.98 2.7942(17) 172.4 1_654
O2 H2O N1 0.82 1.95 2.7578(17) 168.8 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        70.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.031

#===END

data_2
_database_code_depnum_ccdc_archive 'CCDC 712726'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   p21ab

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

_cell_length_a                   7.7618(6)
_cell_length_b                   22.981(3)
_cell_length_c                   5.6539(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1008.51(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    26
_cell_measurement_theta_min      6
_cell_measurement_theta_max      16

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens AED diffractometer'
_diffrn_measurement_method       'θ/2θ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         1
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1918
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         69.99
_reflns_number_total             1037
_reflns_number_gt                726
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0540P)²+0.0000P] where P=(Fo²+2Fc²)/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         1037
_refine_ls_number_parameters     137
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.957
_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
O1 O 0.8929(5) 0.31897(9) 0.0766(4) 0.0902(8) Uani 1 1 d . . .
H1O H 0.8785 0.2937 -0.0239 0.135 Uiso 1 1 calc R . .
N1 N 0.8641(5) 0.73165(10) -0.7423(5) 0.0808(8) Uani 1 1 d . . .
N2 N 0.8331(4) 0.53541(11) -0.3540(5) 0.0747(8) Uani 1 1 d . . .
C1 C 0.9474(6) 0.73345(14) -0.5366(6) 0.0850(12) Uani 1 1 d . . .
H1 H 0.9983 0.7684 -0.4922 0.102 Uiso 1 1 calc R . .
C2 C 0.9629(5) 0.68663(13) -0.3852(6) 0.0806(11) Uani 1 1 d . . .
H2 H 1.0257 0.6903 -0.2458 0.097 Uiso 1 1 calc R . .
C3 C 0.8852(5) 0.63455(13) -0.4410(6) 0.0692(9) Uani 1 1 d . . .
C4 C 0.7918(5) 0.63268(14) -0.6530(6) 0.0750(9) Uani 1 1 d . . .
H4 H 0.7345 0.5989 -0.6979 0.090 Uiso 1 1 calc R . .
C5 C 0.7862(5) 0.68130(13) -0.7933(7) 0.0802(10) Uani 1 1 d . . .
H5 H 0.7239 0.6791 -0.9336 0.096 Uiso 1 1 calc R . .
C6 C 0.9033(5) 0.58210(13) -0.2938(6) 0.0729(9) Uani 1 1 d . . .
H6 H 0.9674 0.5837 -0.1550 0.087 Uiso 1 1 calc R . .
C7 C 0.8504(5) 0.48256(13) -0.2286(6) 0.0662(8) Uani 1 1 d . . .
C8 C 0.9314(5) 0.47478(14) -0.0091(6) 0.0768(10) Uani 1 1 d . . .
H8 H 0.9776 0.5066 0.0703 0.092 Uiso 1 1 calc R . .
C9 C 0.9427(5) 0.42015(14) 0.0884(6) 0.0766(10) Uani 1 1 d . . .
H9 H 0.9972 0.4154 0.2336 0.092 Uiso 1 1 calc R . .
C10 C 0.8749(5) 0.37231(13) -0.0246(6) 0.0703(9) Uani 1 1 d . . .
C11 C 0.7914(5) 0.38011(14) -0.2393(6) 0.0787(10) Uani 1 1 d . . .
H11 H 0.7435 0.3484 -0.3177 0.094 Uiso 1 1 calc R . .
C12 C 0.7800(5) 0.43456(13) -0.3351(6) 0.0751(10) Uani 1 1 d . . .
H12 H 0.7222 0.4392 -0.4779 0.090 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.116(2) 0.0800(14) 0.0749(14) 0.0089(11) -0.0053(18) -0.0020(17)
N1 0.094(2) 0.0691(15) 0.0798(18) -0.0062(15) 0.0137(19) 0.0014(17)
N2 0.078(2) 0.0686(15) 0.0773(17) -0.0089(14) -0.0019(16) 0.0013(15)
C1 0.103(3) 0.066(2) 0.086(2) -0.0158(18) 0.024(2) -0.014(2)
C2 0.087(3) 0.081(2) 0.073(2) -0.0118(18) 0.011(2) -0.008(2)
C3 0.071(2) 0.0678(18) 0.0688(18) -0.0080(15) 0.0135(19) 0.0021(18)
C4 0.077(2) 0.0621(17) 0.086(2) -0.0090(18) 0.003(2) -0.0012(17)
C5 0.086(3) 0.075(2) 0.080(2) -0.0069(17) 0.004(2) 0.002(2)
C6 0.078(2) 0.0787(19) 0.0623(18) -0.0071(16) 0.0054(19) -0.001(2)
C7 0.0685(19) 0.0652(16) 0.0650(18) -0.0077(15) -0.0004(17) 0.0016(15)
C8 0.088(3) 0.077(2) 0.0655(19) -0.0157(16) -0.009(2) -0.001(2)
C9 0.086(3) 0.086(2) 0.0584(17) -0.0043(17) -0.0093(19) 0.005(2)
C10 0.075(3) 0.0730(19) 0.0626(18) -0.0005(16) 0.0049(19) 0.0029(19)
C11 0.089(3) 0.0720(18) 0.075(2) -0.0073(17) -0.017(2) -0.007(2)
C12 0.084(3) 0.0742(19) 0.0668(19) -0.0032(16) -0.0150(19) -0.0009(19)

_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
O1 C10 1.360(3) . ?
N1 C1 1.331(5) . ?
N1 C5 1.337(4) . ?
N2 C6 1.251(4) . ?
N2 C7 1.413(4) . ?
C1 C2 1.380(5) . ?
C2 C3 1.377(4) . ?
C3 C4 1.402(5) . ?
C3 C6 1.471(4) . ?
C4 C5 1.371(4) . ?
C7 C12 1.370(4) . ?
C7 C8 1.403(5) . ?
C8 C9 1.374(4) . ?
C9 C10 1.376(4) . ?
C10 C11 1.388(4) . ?
C11 C12 1.366(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
C1 N1 C5 115.8(3) . . ?
C6 N2 C7 124.0(3) . . ?
N1 C1 C2 124.1(3) . . ?
C3 C2 C1 119.8(3) . . ?
C2 C3 C4 116.7(3) . . ?
C2 C3 C6 122.7(3) . . ?
C4 C3 C6 120.5(3) . . ?
C5 C4 C3 119.1(3) . . ?
N1 C5 C4 124.5(4) . . ?
N2 C6 C3 120.5(3) . . ?
C12 C7 C8 117.7(3) . . ?
C12 C7 N2 115.7(3) . . ?
C8 C7 N2 126.6(3) . . ?
C9 C8 C7 120.0(3) . . ?
C8 C9 C10 121.3(3) . . ?
O1 C10 C9 119.0(3) . . ?
O1 C10 C11 122.2(3) . . ?
C9 C10 C11 118.8(3) . . ?
C12 C11 C10 119.7(3) . . ?
C11 C12 C7 122.5(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        69.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.033

#===END

data_3
_database_code_depnum_ccdc_archive 'CCDC 712727'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 N2 O'
_chemical_formula_weight         350.40

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                   6.452(5)
_cell_length_b                   18.073(13)
_cell_length_c                   16.549(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.52(3)
_cell_angle_gamma                90.00
_cell_volume                     1819(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    800
_cell_measurement_theta_min      4
_cell_measurement_theta_max      18

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.763395
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS procedure'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'SMART diffractometer'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 8.2
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15389
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         23.29
_reflns_number_total             2623
_reflns_number_gt                2116
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0701P)²+1.3650P] where P=(Fo²+2Fc²)/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         2623
_refine_ls_number_parameters     245
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1648
_refine_ls_wR_factor_gt          0.1551
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.088
_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
N1 N 2.2383(3) -0.77882(13) 1.02241(15) 0.0522(6) Uani 1 1 d U . .
N2 N 1.4465(4) -0.77438(16) 0.83513(18) 0.0724(8) Uani 1 1 d U . .
O1 O 0.5849(3) -0.80577(10) 0.60964(14) 0.0608(6) Uani 1 1 d U . .
H1O H 0.5296 -0.7648 0.5960 0.091 Uiso 1 1 calc R . .
C1 C 2.1860(5) -0.83741(17) 0.97134(19) 0.0604(8) Uani 1 1 d U . .
H1 H 2.2968 -0.8713 0.9744 0.072 Uiso 1 1 calc R . .
C2 C 1.9818(5) -0.85154(19) 0.91479(19) 0.0630(8) Uani 1 1 d U . .
H2 H 1.9560 -0.8942 0.8814 0.076 Uiso 1 1 calc R . .
C3 C 1.8166(5) -0.80307(18) 0.90754(18) 0.0601(8) Uani 1 1 d U . .
C4 C 1.8619(4) -0.74154(19) 0.9606(2) 0.0665(9) Uani 1 1 d U . .
H4 H 1.7521 -0.7075 0.9584 0.080 Uiso 1 1 calc R . .
C5 C 2.0777(5) -0.73153(17) 1.0180(2) 0.0596(8) Uani 1 1 d U . .
H5 H 2.1083 -0.6905 1.0539 0.072 Uiso 1 1 calc R . .
C6 C 1.5920(5) -0.81740(19) 0.8426(2) 0.0668(8) Uani 1 1 d U . .
H6 H 1.5672 -0.8596 0.8085 0.080 Uiso 1 1 calc R . .
C7 C 1.2300(4) -0.78781(17) 0.77316(18) 0.0555(7) Uani 1 1 d U . .
C8 C 1.1398(4) -0.85549(17) 0.74026(18) 0.0545(7) Uani 1 1 d U . .
H8 H 1.2268 -0.8977 0.7551 0.065 Uiso 1 1 calc R . .
C9 C 0.9215(4) -0.86248(14) 0.68532(16) 0.0455(6) Uani 1 1 d U . .
C10 C 0.7944(4) -0.79796(14) 0.66433(16) 0.0446(6) Uani 1 1 d U . .
C11 C 0.8835(4) -0.72907(15) 0.69548(16) 0.0463(6) Uani 1 1 d U . .
C12 C 1.1000(4) -0.72581(16) 0.75044(18) 0.0543(7) Uani 1 1 d U . .
H12 H 1.1588 -0.6802 0.7726 0.065 Uiso 1 1 calc R . .
C13 C 0.7600(4) -0.65867(15) 0.66995(17) 0.0486(7) Uani 1 1 d U . .
C14 C 0.5865(5) -0.63942(18) 0.6975(2) 0.0635(8) Uani 1 1 d U . .
H14 H 0.5400 -0.6723 0.7312 0.076 Uiso 1 1 calc R . .
C15 C 0.4822(6) -0.5723(2) 0.6755(2) 0.0775(10) Uani 1 1 d U . .
H15 H 0.3663 -0.5599 0.6945 0.093 Uiso 1 1 calc R . .
C16 C 0.5488(7) -0.5237(2) 0.6258(3) 0.0841(11) Uani 1 1 d U . .
H16 H 0.4783 -0.4783 0.6110 0.101 Uiso 1 1 calc R . .
C17 C 0.7190(7) -0.54193(19) 0.5978(3) 0.0850(11) Uani 1 1 d U . .
H17 H 0.7634 -0.5090 0.5636 0.102 Uiso 1 1 calc R . .
C18 C 0.8248(5) -0.60864(17) 0.6200(2) 0.0670(8) Uani 1 1 d U . .
H18 H 0.9415 -0.6203 0.6012 0.080 Uiso 1 1 calc R . .
C19 C 0.8368(4) -0.93571(15) 0.64994(18) 0.0489(7) Uani 1 1 d U . .
C20 C 0.9666(5) -0.98180(18) 0.6204(3) 0.0759(10) Uani 1 1 d U . .
H20 H 1.1051 -0.9657 0.6223 0.091 Uiso 1 1 calc R . .
C21 C 0.8963(6) -1.0505(2) 0.5884(3) 0.0894(12) Uani 1 1 d U . .
H21 H 0.9877 -1.0804 0.5693 0.107 Uiso 1 1 calc R . .
C22 C 0.6930(6) -1.07595(18) 0.5842(2) 0.0710(9) Uani 1 1 d U . .
H22 H 0.6455 -1.1227 0.5622 0.085 Uiso 1 1 calc R . .
C23 C 0.5613(5) -1.03136(18) 0.6127(2) 0.0669(9) Uani 1 1 d U . .
H23 H 0.4230 -1.0480 0.6104 0.080 Uiso 1 1 calc R . .
C24 C 0.6307(4) -0.96219(16) 0.6450(2) 0.0589(8) Uani 1 1 d U . .
H24 H 0.5382 -0.9326 0.6638 0.071 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0344(12) 0.0570(14) 0.0548(14) 0.0005(11) 0.0010(10) -0.0025(10)
N2 0.0478(14) 0.0828(19) 0.0811(19) 0.0231(15) 0.0141(13) 0.0042(14)
O1 0.0337(10) 0.0494(11) 0.0769(14) -0.0029(10) -0.0112(9) 0.0029(8)
C1 0.0466(16) 0.0663(19) 0.0636(19) -0.0046(16) 0.0124(14) -0.0035(14)
C2 0.0485(17) 0.076(2) 0.0569(18) -0.0052(16) 0.0081(14) -0.0117(15)
C3 0.0469(16) 0.077(2) 0.0434(16) 0.0108(15) -0.0022(13) -0.0223(15)
C4 0.0378(15) 0.075(2) 0.083(2) 0.0246(17) 0.0160(15) 0.0162(14)
C5 0.0475(16) 0.0591(18) 0.0653(19) -0.0021(15) 0.0095(14) -0.0004(14)
C6 0.066(2) 0.063(2) 0.071(2) 0.0077(16) 0.0226(16) -0.0010(16)
C7 0.0297(13) 0.0733(19) 0.0509(16) 0.0101(14) -0.0031(11) -0.0117(13)
C8 0.0332(14) 0.0644(18) 0.0594(17) 0.0174(14) 0.0067(12) 0.0074(12)
C9 0.0325(13) 0.0509(15) 0.0486(15) 0.0076(12) 0.0078(11) 0.0010(11)
C10 0.0285(12) 0.0539(15) 0.0440(14) 0.0028(12) 0.0025(10) -0.0006(11)
C11 0.0339(13) 0.0546(16) 0.0448(15) 0.0010(12) 0.0060(11) -0.0048(11)
C12 0.0409(14) 0.0602(17) 0.0516(16) 0.0040(14) 0.0018(12) -0.0103(13)
C13 0.0422(14) 0.0478(15) 0.0480(15) -0.0047(12) 0.0045(12) -0.0056(12)
C14 0.0539(18) 0.068(2) 0.067(2) 0.0010(16) 0.0182(15) 0.0032(15)
C15 0.069(2) 0.075(2) 0.082(2) -0.0134(19) 0.0160(18) 0.0160(18)
C16 0.092(3) 0.051(2) 0.089(3) -0.0078(18) 0.004(2) 0.0140(18)
C17 0.097(3) 0.052(2) 0.099(3) 0.0132(19) 0.024(2) -0.0031(19)
C18 0.068(2) 0.0577(19) 0.076(2) 0.0042(16) 0.0258(17) -0.0040(15)
C19 0.0384(14) 0.0497(15) 0.0531(16) 0.0099(12) 0.0078(12) 0.0062(12)
C20 0.0518(18) 0.0585(19) 0.121(3) -0.0059(19) 0.0331(19) 0.0027(15)
C21 0.075(2) 0.062(2) 0.138(4) -0.016(2) 0.045(2) 0.0069(18)
C22 0.076(2) 0.0491(18) 0.079(2) -0.0013(16) 0.0142(18) -0.0022(15)
C23 0.0525(17) 0.063(2) 0.080(2) -0.0002(16) 0.0154(16) -0.0093(15)
C24 0.0458(16) 0.0585(18) 0.071(2) -0.0029(15) 0.0177(14) -0.0023(13)

_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
N1 C1 1.326(4) . ?
N1 C5 1.326(4) . ?
N2 C6 1.193(4) . ?
N2 C7 1.451(4) . ?
O1 C10 1.360(3) . ?
C1 C2 1.361(4) . ?
C2 C3 1.354(4) . ?
C3 C4 1.386(5) . ?
C3 C6 1.510(4) . ?
C4 C5 1.410(4) . ?
C7 C12 1.375(4) . ?
C7 C8 1.385(4) . ?
C8 C9 1.404(4) . ?
C9 C10 1.401(4) . ?
C9 C19 1.476(4) . ?
C10 C11 1.396(4) . ?
C11 C12 1.390(4) . ?
C11 C13 1.486(4) . ?
C13 C18 1.380(4) . ?
C13 C14 1.387(4) . ?
C14 C15 1.377(5) . ?
C15 C16 1.366(5) . ?
C16 C17 1.368(5) . ?
C17 C18 1.374(5) . ?
C19 C20 1.381(4) . ?
C19 C24 1.390(4) . ?
C20 C21 1.366(5) . ?
C21 C22 1.370(5) . ?
C22 C23 1.365(5) . ?
C23 C24 1.374(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
C1 N1 C5 116.8(2) . . ?
C6 N2 C7 120.2(3) . . ?
N1 C1 C2 124.7(3) . . ?
C3 C2 C1 119.5(3) . . ?
C2 C3 C4 118.0(3) . . ?
C2 C3 C6 119.5(3) . . ?
C4 C3 C6 122.5(3) . . ?
C3 C4 C5 118.8(3) . . ?
N1 C5 C4 122.1(3) . . ?
N2 C6 C3 119.7(3) . . ?
C12 C7 C8 118.3(2) . . ?
C12 C7 N2 114.4(3) . . ?
C8 C7 N2 127.2(3) . . ?
C7 C8 C9 122.2(3) . . ?
C10 C9 C8 117.6(2) . . ?
C10 C9 C19 122.7(2) . . ?
C8 C9 C19 119.7(2) . . ?
O1 C10 C11 122.2(2) . . ?
O1 C10 C9 116.6(2) . . ?
C11 C10 C9 121.1(2) . . ?
C12 C11 C10 118.6(2) . . ?
C12 C11 C13 118.4(2) . . ?
C10 C11 C13 122.9(2) . . ?
C7 C12 C11 122.2(3) . . ?
C18 C13 C14 118.1(3) . . ?
C18 C13 C11 119.4(3) . . ?
C14 C13 C11 122.4(3) . . ?
C15 C14 C13 120.8(3) . . ?
C16 C15 C14 120.1(3) . . ?
C15 C16 C17 119.9(3) . . ?
C16 C17 C18 120.2(4) . . ?
C17 C18 C13 120.9(3) . . ?
C20 C19 C24 116.9(3) . . ?
C20 C19 C9 119.5(2) . . ?
C24 C19 C9 123.5(2) . . ?
C21 C20 C19 121.5(3) . . ?
C20 C21 C22 120.9(3) . . ?
C23 C22 C21 118.7(3) . . ?
C22 C23 C24 120.8(3) . . ?
C23 C24 C19 121.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        23.29
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.786
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.043

#===END

data_4
_database_code_depnum_ccdc_archive 'CCDC 712728'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25

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                   11.737(2)
_cell_length_b                   7.473(2)
_cell_length_c                   13.759(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.814(4)
_cell_angle_gamma                90.00
_cell_volume                     1104.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    800
_cell_measurement_theta_min      4
_cell_measurement_theta_max      18

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5981
_exptl_absorpt_correction_T_max  0.7443
_exptl_absorpt_process_details   'SADABS procedure'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'APEX diffractometer'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 8.2
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5973
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         18.91
_reflns_number_total             879
_reflns_number_gt                713
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0598P)²+1.3511P] where P=(Fo²+2Fc²)/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         879
_refine_ls_number_parameters     146
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1370
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.002
_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
N1 N -0.4393(4) 0.2994(5) -0.3087(3) 0.0630(12) Uani 1 1 d U . .
N2 N -0.0572(5) 0.2649(6) 0.0310(4) 0.0803(14) Uani 1 1 d U . .
O1 O 0.3739(4) 0.3347(5) 0.4856(3) 0.1218(18) Uani 1 1 d U . .
H1O H 0.4374 0.3200 0.5395 0.183 Uiso 1 1 calc R . .
C1 C -0.3266(5) 0.3642(6) -0.2841(4) 0.0637(14) Uani 1 1 d U . .
H1 H -0.3093 0.4198 -0.3371 0.076 Uiso 1 1 calc R . .
C2 C -0.2330(4) 0.3532(6) -0.1833(4) 0.0628(14) Uani 1 1 d U . .
H2 H -0.1541 0.3988 -0.1688 0.075 Uiso 1 1 calc R . .
C3 C -0.2595(5) 0.2732(6) -0.1050(4) 0.0590(14) Uani 1 1 d U . .
C4 C -0.3766(5) 0.2108(7) -0.1307(4) 0.0692(15) Uani 1 1 d U . .
H4 H -0.3983 0.1587 -0.0792 0.083 Uiso 1 1 calc R . .
C5 C -0.4609(4) 0.2252(7) -0.2315(5) 0.0658(15) Uani 1 1 d U . .
H5 H -0.5401 0.1793 -0.2476 0.079 Uiso 1 1 calc R . .
C6 C -0.1631(6) 0.2450(7) 0.0097(5) 0.0800(17) Uani 1 1 d U . .
H6 H -0.1896 0.2119 0.0624 0.096 Uiso 1 1 calc R . .
C7 C 0.0302(4) 0.2375(6) 0.1418(4) 0.0548(13) Uani 1 1 d U . .
C8 C 0.1393(5) 0.1558(6) 0.1550(4) 0.0604(14) Uani 1 1 d U . .
H8 H 0.1526 0.1164 0.0963 0.072 Uiso 1 1 calc R . .
C9 C 0.2292(4) 0.1321(6) 0.2553(4) 0.0581(13) Uani 1 1 d U . .
H9 H 0.3022 0.0725 0.2639 0.070 Uiso 1 1 calc R . .
C10 C 0.2146(4) 0.1941(6) 0.3436(4) 0.0543(13) Uani 1 1 d U . .
C11 C 0.1044(5) 0.2783(6) 0.3281(4) 0.0613(14) Uani 1 1 d U . .
H11 H 0.0924 0.3219 0.3866 0.074 Uiso 1 1 calc R . .
C12 C 0.0119(4) 0.2995(6) 0.2287(4) 0.0592(14) Uani 1 1 d U . .
H12 H -0.0625 0.3552 0.2200 0.071 Uiso 1 1 calc R . .
C13 C 0.3155(5) 0.1746(7) 0.4529(4) 0.0882(18) Uani 1 1 d U . .
H13A H 0.2799 0.1351 0.5017 0.106 Uiso 1 1 calc R . .
H13B H 0.3752 0.0853 0.4522 0.106 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.058(3) 0.060(3) 0.051(3) 0.002(2) 0.000(2) 0.003(2)
N2 0.071(3) 0.068(3) 0.089(3) -0.018(2) 0.019(3) -0.008(3)
O1 0.136(4) 0.079(3) 0.072(3) 0.008(2) -0.039(2) -0.025(3)
C1 0.078(4) 0.059(3) 0.057(3) 0.007(3) 0.030(3) 0.000(3)
C2 0.039(3) 0.061(3) 0.077(4) -0.014(3) 0.012(3) -0.007(2)
C3 0.062(4) 0.058(3) 0.038(3) -0.003(2) 0.000(3) 0.015(3)
C4 0.077(4) 0.067(4) 0.062(4) 0.009(3) 0.027(3) 0.004(3)
C5 0.044(3) 0.063(3) 0.083(4) -0.001(3) 0.018(3) -0.002(3)
C6 0.078(4) 0.070(4) 0.096(4) -0.005(3) 0.039(4) 0.004(3)
C7 0.057(3) 0.051(3) 0.039(3) -0.003(2) 0.000(3) -0.004(2)
C8 0.065(3) 0.063(3) 0.050(3) -0.005(3) 0.020(3) 0.005(3)
C9 0.047(3) 0.056(3) 0.066(3) 0.001(3) 0.017(3) 0.002(2)
C10 0.051(3) 0.049(3) 0.045(3) 0.000(2) 0.001(3) -0.004(2)
C11 0.073(4) 0.065(3) 0.043(3) -0.005(2) 0.020(3) 0.007(3)
C12 0.043(3) 0.060(3) 0.067(3) 0.001(3) 0.014(3) 0.008(2)
C13 0.093(4) 0.065(4) 0.063(3) 0.002(3) -0.014(3) -0.003(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
N1 C5 1.310(6) . ?
N1 C1 1.319(6) . ?
N2 C6 1.165(6) . ?
N2 C7 1.468(6) . ?
O1 C13 1.362(6) . ?
C1 C2 1.381(6) . ?
C2 C3 1.373(6) . ?
C3 C4 1.356(6) . ?
C3 C6 1.541(7) . ?
C4 C5 1.344(7) . ?
C7 C8 1.363(6) . ?
C7 C12 1.378(6) . ?
C8 C9 1.368(6) . ?
C9 C10 1.374(6) . ?
C10 C11 1.376(6) . ?
C10 C13 1.499(6) . ?
C11 C12 1.369(6) . ?

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
C5 N1 C1 116.7(4) . . ?
C6 N2 C7 118.1(5) . . ?
N1 C1 C2 123.0(4) . . ?
C3 C2 C1 118.2(4) . . ?
C4 C3 C2 118.2(4) . . ?
C4 C3 C6 117.9(5) . . ?
C2 C3 C6 123.9(5) . . ?
C5 C4 C3 119.2(5) . . ?
N1 C5 C4 124.6(5) . . ?
N2 C6 C3 120.5(6) . . ?
C8 C7 C12 120.1(4) . . ?
C8 C7 N2 115.2(4) . . ?
C12 C7 N2 124.5(5) . . ?
C7 C8 C9 119.5(4) . . ?
C8 C9 C10 121.8(4) . . ?
C9 C10 C11 117.6(4) . . ?
C9 C10 C13 121.6(5) . . ?
C11 C10 C13 120.8(5) . . ?
C12 C11 C10 121.6(4) . . ?
C11 C12 C7 119.3(4) . . ?
O1 C13 C10 109.5(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        18.91
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034

#===END

data_5
_database_code_depnum_ccdc_archive 'CCDC 712729'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.29

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           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                   10.913(4)
_cell_length_b                   8.774(3)
_cell_length_c                   14.000(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.55(2)
_cell_angle_gamma                90.00
_cell_volume                     1321.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      6
_cell_measurement_theta_max      16

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Siemens AED diffractometer'
_diffrn_measurement_method       'θ/2θ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         1
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7474
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         30.05
_reflns_number_total             3863
_reflns_number_gt                2365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0805P)²+0.0000P] where P=(Fo²+2Fc²)/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         3863
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1276
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
N1 N 0.68183(10) 0.64746(14) -0.16592(8) 0.0565(3) Uani 1 1 d . . .
N2 N 1.23542(13) 0.8962(2) 0.36960(10) 0.0684(4) Uani 1 1 d . . .
O1 O 0.44795(11) 0.71807(16) -0.49995(8) 0.0876(4) Uani 1 1 d . . .
O2 O 0.83993(8) 0.66399(12) 0.01614(6) 0.0580(3) Uani 1 1 d . . .
H2O H 0.7940 0.6573 -0.0363 0.087 Uiso 1 1 calc R . .
C1 C 0.71052(12) 0.70567(16) -0.24756(11) 0.0568(4) Uani 1 1 d . . .
H1 H 0.7884 0.7499 -0.2450 0.068 Uiso 1 1 calc R . .
C2 C 0.63174(12) 0.70412(15) -0.33517(10) 0.0505(3) Uani 1 1 d . . .
H2 H 0.6555 0.7480 -0.3897 0.061 Uiso 1 1 calc R . .
C3 C 0.51594(10) 0.63568(13) -0.34046(9) 0.0403(3) Uani 1 1 d . . .
C4 C 0.48642(11) 0.57215(16) -0.25697(10) 0.0495(3) Uani 1 1 d . . .
H4 H 0.4106 0.5233 -0.2579 0.059 Uiso 1 1 calc R . .
C5 C 0.57123(13) 0.58204(17) -0.17177(10) 0.0574(4) Uani 1 1 d . . .
H5 H 0.5495 0.5406 -0.1158 0.069 Uiso 1 1 calc R . .
C6 C 0.42744(11) 0.63505(16) -0.43545(10) 0.0502(3) Uani 1 1 d . . .
C7 C 0.31818(12) 0.53110(18) -0.44799(12) 0.0624(4) Uani 1 1 d . . .
H7A H 0.2733 0.5403 -0.5128 0.094 Uiso 1 1 calc R . .
H7B H 0.2648 0.5581 -0.4027 0.094 Uiso 1 1 calc R . .
H7C H 0.3460 0.4279 -0.4366 0.094 Uiso 1 1 calc R . .
C8 C 1.16641(10) 0.85183(15) 0.28200(9) 0.0456(3) Uani 1 1 d . . .
C9 C 1.06585(11) 0.93953(15) 0.23815(10) 0.0510(3) Uani 1 1 d . . .
H9 H 1.0433 1.0263 0.2692 0.061 Uiso 1 1 calc R . .
C10 C 0.99956(11) 0.89872(15) 0.14903(10) 0.0501(3) Uani 1 1 d . . .
H10 H 0.9325 0.9586 0.1216 0.060 Uiso 1 1 calc R . .
C11 C 1.02974(10) 0.77141(14) 0.09917(9) 0.0440(3) Uani 1 1 d . . .
C12 C 1.12979(11) 0.68513(14) 0.14321(10) 0.0476(3) Uani 1 1 d . . .
H12 H 1.1524 0.5989 0.1116 0.057 Uiso 1 1 calc R . .
C13 C 1.19711(11) 0.72324(14) 0.23270(9) 0.0472(3) Uani 1 1 d . . .
H13 H 1.2635 0.6624 0.2602 0.057 Uiso 1 1 calc R . .
C14 C 0.95513(12) 0.72861(18) 0.00269(9) 0.0567(4) Uani 1 1 d . . .
H14A H 0.9403 0.8184 -0.0380 0.068 Uiso 1 1 calc R . .
H14B H 1.0012 0.6557 -0.0295 0.068 Uiso 1 1 calc R . .
H2NB H 1.2050(14) 0.970(2) 0.4018(12) 0.066(5) Uiso 1 1 d . . .
H2NA H 1.2901(17) 0.835(2) 0.4007(13) 0.080(6) Uiso 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
N1 0.0513(6) 0.0623(7) 0.0507(7) -0.0093(6) -0.0066(5) 0.0062(5)
N2 0.0606(8) 0.0877(10) 0.0517(7) -0.0178(7) -0.0061(6) 0.0090(7)
O1 0.0794(7) 0.1164(10) 0.0596(7) 0.0351(7) -0.0105(6) -0.0116(7)
O2 0.0495(5) 0.0749(6) 0.0448(5) 0.0017(5) -0.0064(4) -0.0117(5)
C1 0.0418(6) 0.0615(8) 0.0644(9) -0.0122(7) 0.0011(6) -0.0094(6)
C2 0.0504(7) 0.0516(7) 0.0494(7) -0.0011(6) 0.0081(6) -0.0087(6)
C3 0.0375(6) 0.0402(6) 0.0420(6) -0.0019(5) 0.0031(5) 0.0031(4)
C4 0.0396(6) 0.0586(8) 0.0496(7) 0.0035(6) 0.0050(5) -0.0031(5)
C5 0.0547(7) 0.0727(9) 0.0433(7) 0.0044(7) 0.0040(6) 0.0032(7)
C6 0.0457(7) 0.0571(7) 0.0453(7) -0.0016(6) -0.0002(5) 0.0080(6)
C7 0.0493(7) 0.0729(9) 0.0601(8) -0.0169(8) -0.0055(6) -0.0024(7)
C8 0.0388(6) 0.0550(7) 0.0424(7) -0.0008(6) 0.0046(5) -0.0053(5)
C9 0.0438(6) 0.0514(7) 0.0576(8) -0.0102(6) 0.0079(6) 0.0046(5)
C10 0.0373(6) 0.0537(7) 0.0569(8) 0.0034(6) 0.0008(5) 0.0062(5)
C11 0.0391(6) 0.0502(7) 0.0419(6) 0.0025(5) 0.0043(5) -0.0072(5)
C12 0.0479(6) 0.0402(6) 0.0535(8) -0.0043(6) 0.0053(5) -0.0012(5)
C13 0.0419(6) 0.0439(6) 0.0529(7) 0.0052(6) -0.0008(5) 0.0034(5)
C14 0.0517(7) 0.0749(9) 0.0419(7) 0.0008(7) 0.0033(6) -0.0098(6)

_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
N1 C5 1.3267(19) . ?
N1 C1 1.3357(19) . ?
N2 C8 1.3842(18) . ?
O1 C6 1.2096(17) . ?
O2 C14 1.4199(16) . ?
C1 C2 1.3762(18) . ?
C2 C3 1.3900(17) . ?
C3 C4 1.3805(19) . ?
C3 C6 1.5083(18) . ?
C4 C5 1.3858(19) . ?
C6 C7 1.488(2) . ?
C8 C13 1.3922(18) . ?
C8 C9 1.3963(18) . ?
C9 C10 1.382(2) . ?
C10 C11 1.3856(19) . ?
C11 C12 1.3863(18) . ?
C11 C14 1.5045(18) . ?
C12 C13 1.3842(18) . ?

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
C5 N1 C1 116.92(11) . . ?
N1 C1 C2 123.94(12) . . ?
C1 C2 C3 118.67(12) . . ?
C4 C3 C2 117.85(12) . . ?
C4 C3 C6 122.67(11) . . ?
C2 C3 C6 119.48(12) . . ?
C3 C4 C5 119.16(12) . . ?
N1 C5 C4 123.43(13) . . ?
O1 C6 C7 121.66(13) . . ?
O1 C6 C3 119.03(12) . . ?
C7 C6 C3 119.31(12) . . ?
N2 C8 C13 121.78(13) . . ?
N2 C8 C9 120.47(13) . . ?
C13 C8 C9 117.70(11) . . ?
C10 C9 C8 120.65(12) . . ?
C9 C10 C11 122.09(12) . . ?
C10 C11 C12 116.85(11) . . ?
C10 C11 C14 121.00(12) . . ?
C12 C11 C14 122.14(12) . . ?
C13 C12 C11 122.09(12) . . ?
C12 C13 C8 120.62(11) . . ?
O2 C14 C11 109.87(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
O2 H2O N1 0.82 2.01 2.8346(17) 178.3 .
N2 H2NB O2 0.883(18) 2.157(19) 3.032(2) 171.0(14) 2_755
N2 H2NA O1 0.863(18) 2.273(19) 3.123(2) 168.4(16) 1_656

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.05
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.053

#===END

data_7
_database_code_depnum_ccdc_archive 'CCDC 712730'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31

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   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                   11.3071(14)
_cell_length_b                   17.413(2)
_cell_length_c                   7.2568(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.005(2)
_cell_angle_gamma                90.00
_cell_volume                     1402.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    800
_cell_measurement_theta_min      4
_cell_measurement_theta_max      18

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.762934
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS procedure'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'SMART diffractometer'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 8.2
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13177
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         24.77
_reflns_number_total             2409
_reflns_number_gt                1811
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0631P)²+0.1091P] where P=(Fo²+2Fc²)/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         2409
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
N1 N -0.08173(15) -0.82356(9) 0.93342(17) 0.0492(4) Uani 1 1 d . . .
O1 O 0.07365(9) -0.88425(7) 0.25851(14) 0.0505(3) Uani 1 1 d . . .
H1O H 0.0189 -0.8762 0.1688 0.076 Uiso 1 1 calc R . .
C1 C 0.03234(13) -0.87274(8) 0.42269(19) 0.0388(3) Uani 1 1 d . . .
C2 C 0.11532(12) -0.84587(8) 0.57910(19) 0.0391(3) Uani 1 1 d . . .
C3 C 0.07401(13) -0.82851(8) 0.74383(19) 0.0407(3) Uani 1 1 d . . .
H3 H 0.1281 -0.8096 0.8466 0.049 Uiso 1 1 calc R . .
C4 C -0.04612(13) -0.83883(8) 0.75828(19) 0.0396(3) Uani 1 1 d . . .
C5 C -0.12548(13) -0.86848(8) 0.6053(2) 0.0408(3) Uani 1 1 d . . .
H5 H -0.2051 -0.8773 0.6153 0.049 Uiso 1 1 calc R . .
C6 C -0.08885(12) -0.88558(8) 0.43573(19) 0.0383(3) Uani 1 1 d . . .
C7 C 0.24639(13) -0.83787(9) 0.57632(19) 0.0443(4) Uani 1 1 d . . .
C8 C 0.30999(15) -0.89646(10) 0.5059(2) 0.0568(4) Uani 1 1 d . . .
H8 H 0.2695 -0.9401 0.4536 0.068 Uiso 1 1 calc R . .
C9 C 0.43343(17) -0.88974(13) 0.5137(3) 0.0724(6) Uani 1 1 d . . .
H9 H 0.4752 -0.9289 0.4668 0.087 Uiso 1 1 calc R . .
C10 C 0.49412(17) -0.82501(15) 0.5912(3) 0.0771(6) Uani 1 1 d . . .
H10 H 0.5768 -0.8209 0.5973 0.093 Uiso 1 1 calc R . .
C11 C 0.43292(17) -0.76714(14) 0.6588(3) 0.0724(6) Uani 1 1 d . . .
H11 H 0.4740 -0.7234 0.7091 0.087 Uiso 1 1 calc R . .
C12 C 0.30988(15) -0.77320(11) 0.6530(2) 0.0546(4) Uani 1 1 d . . .
H12 H 0.2694 -0.7337 0.7008 0.066 Uiso 1 1 calc R . .
C13 C -0.17828(13) -0.91521(8) 0.2722(2) 0.0411(4) Uani 1 1 d . . .
C14 C -0.15394(15) -0.97994(9) 0.1725(2) 0.0494(4) Uani 1 1 d . . .
H14 H -0.0813 -1.0058 0.2093 0.059 Uiso 1 1 calc R . .
C15 C -0.23657(16) -1.00625(10) 0.0193(3) 0.0616(5) Uani 1 1 d . . .
H15 H -0.2190 -1.0494 -0.0462 0.074 Uiso 1 1 calc R . .
C16 C -0.34493(17) -0.96845(13) -0.0361(3) 0.0711(6) Uani 1 1 d . . .
H16 H -0.4003 -0.9861 -0.1389 0.085 Uiso 1 1 calc R . .
C17 C -0.37095(16) -0.90472(12) 0.0605(3) 0.0716(6) Uani 1 1 d . . .
H17 H -0.4439 -0.8793 0.0228 0.086 Uiso 1 1 calc R . .
C18 C -0.28867(14) -0.87824(11) 0.2144(2) 0.0556(4) Uani 1 1 d . . .
H18 H -0.3073 -0.8354 0.2797 0.067 Uiso 1 1 calc R . .
H1NB H -0.1600(19) -0.8332(11) 0.930(3) 0.073(6) Uiso 1 1 d . . .
H1NA H -0.0633(17) -0.7755(12) 0.972(3) 0.074(6) Uiso 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
N1 0.0591(9) 0.0544(9) 0.0374(7) -0.0035(6) 0.0176(6) -0.0030(7)
O1 0.0462(6) 0.0728(7) 0.0342(5) -0.0046(5) 0.0123(4) 0.0015(5)
C1 0.0442(8) 0.0402(8) 0.0334(7) 0.0018(6) 0.0112(6) 0.0033(6)
C2 0.0422(8) 0.0395(8) 0.0355(7) 0.0043(6) 0.0073(6) 0.0012(6)
C3 0.0480(8) 0.0397(8) 0.0332(7) 0.0006(6) 0.0049(6) -0.0018(6)
C4 0.0516(9) 0.0367(8) 0.0325(7) 0.0027(6) 0.0129(6) 0.0025(6)
C5 0.0410(8) 0.0438(8) 0.0395(8) 0.0028(6) 0.0124(6) 0.0003(6)
C6 0.0428(8) 0.0379(8) 0.0348(7) 0.0008(6) 0.0091(6) 0.0003(6)
C7 0.0445(8) 0.0556(9) 0.0328(7) 0.0062(7) 0.0073(6) 0.0006(7)
C8 0.0525(10) 0.0614(11) 0.0566(10) 0.0042(8) 0.0107(8) 0.0084(8)
C9 0.0541(11) 0.0961(15) 0.0693(13) 0.0127(11) 0.0176(9) 0.0219(11)
C10 0.0426(10) 0.132(2) 0.0558(11) 0.0081(12) 0.0074(8) -0.0050(12)
C11 0.0581(11) 0.1127(17) 0.0466(10) -0.0085(10) 0.0102(8) -0.0283(11)
C12 0.0518(9) 0.0749(12) 0.0378(8) -0.0062(8) 0.0103(7) -0.0119(8)
C13 0.0429(8) 0.0467(8) 0.0353(7) 0.0018(6) 0.0112(6) -0.0037(6)
C14 0.0538(9) 0.0447(9) 0.0483(9) -0.0025(7) 0.0067(7) 0.0001(7)
C15 0.0718(12) 0.0564(10) 0.0548(10) -0.0127(8) 0.0076(9) -0.0042(9)
C16 0.0624(12) 0.0910(15) 0.0545(11) -0.0176(10) -0.0028(9) -0.0107(10)
C17 0.0485(10) 0.1012(16) 0.0608(12) -0.0120(11) -0.0003(9) 0.0119(10)
C18 0.0485(9) 0.0707(11) 0.0476(9) -0.0109(8) 0.0090(7) 0.0080(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
N1 C4 1.4295(18) . ?
O1 C1 1.3749(17) . ?
C1 C2 1.407(2) . ?
C1 C6 1.409(2) . ?
C2 C3 1.397(2) . ?
C2 C7 1.493(2) . ?
C3 C4 1.394(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.403(2) . ?
C6 C13 1.496(2) . ?
C7 C12 1.393(2) . ?
C7 C8 1.400(2) . ?
C8 C9 1.391(2) . ?
C9 C10 1.382(3) . ?
C10 C11 1.366(3) . ?
C11 C12 1.388(2) . ?
C13 C18 1.396(2) . ?
C13 C14 1.395(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.381(3) . ?
C16 C17 1.374(3) . ?
C17 C18 1.388(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
O1 C1 C2 117.57(12) . . ?
O1 C1 C6 122.05(12) . . ?
C2 C1 C6 120.37(12) . . ?
C3 C2 C1 118.79(13) . . ?
C3 C2 C7 119.11(12) . . ?
C1 C2 C7 122.07(12) . . ?
C4 C3 C2 121.76(13) . . ?
C5 C4 C3 118.59(13) . . ?
C5 C4 N1 122.14(13) . . ?
C3 C4 N1 119.13(13) . . ?
C4 C5 C6 121.79(13) . . ?
C5 C6 C1 118.61(13) . . ?
C5 C6 C13 120.04(12) . . ?
C1 C6 C13 121.34(12) . . ?
C12 C7 C8 118.26(15) . . ?
C12 C7 C2 120.49(14) . . ?
C8 C7 C2 121.16(14) . . ?
C9 C8 C7 120.34(17) . . ?
C10 C9 C8 120.12(19) . . ?
C11 C10 C9 120.11(17) . . ?
C10 C11 C12 120.44(19) . . ?
C11 C12 C7 120.73(17) . . ?
C18 C13 C14 118.05(14) . . ?
C18 C13 C6 120.64(13) . . ?
C14 C13 C6 121.31(13) . . ?
C15 C14 C13 120.90(15) . . ?
C16 C15 C14 120.03(17) . . ?
C17 C16 C15 120.05(16) . . ?
C16 C17 C18 120.17(17) . . ?
C17 C18 C13 120.81(16) . . ?

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
O1 H1O N1 0.82 2.08 2.8612(18) 160.2 1_554

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.77
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.030

#===END

data_8
_database_code_depnum_ccdc_archive 'CCDC 712731'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H9 N O'
_chemical_formula_weight         123.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   pna21

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

_cell_length_a                   15.0879(7)
_cell_length_b                   7.4306(3)
_cell_length_c                   5.77510(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     647.46(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      6
_cell_measurement_theta_max      16

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens AED diffractometer'
_diffrn_measurement_method       'θ/2θ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         1
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            677
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0104
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         5.87
_diffrn_reflns_theta_max         70.02
_reflns_number_total             677
_reflns_number_gt                617
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0973P)²+0.0143P] where P=(Fo²+2Fc²)/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         677
_refine_ls_number_parameters     91
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.074
_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
N1 N 0.34884(16) 0.3279(3) -0.1853(6) 0.0559(6) Uani 1 1 d . . .
O1 O 0.72145(11) 0.0235(2) 0.1786(7) 0.0707(7) Uani 1 1 d . . .
H1 H 0.7006 -0.0761 0.2070 0.106 Uiso 1 1 calc R . .
C1 C 0.67053(16) 0.1585(3) 0.2947(7) 0.0610(8) Uani 1 1 d . . .
H1A H 0.7061 0.2665 0.3099 0.073 Uiso 1 1 calc R . .
H1B H 0.6563 0.1166 0.4494 0.073 Uiso 1 1 calc R . .
C2 C 0.58576(15) 0.2044(3) 0.1696(5) 0.0446(7) Uani 1 1 d . . .
C3 C 0.58768(16) 0.2884(3) -0.0457(5) 0.0489(7) Uani 1 1 d . . .
H3 H 0.6420 0.3156 -0.1132 0.059 Uiso 1 1 calc R . .
C4 C 0.51088(16) 0.3321(3) -0.1602(5) 0.0471(7) Uani 1 1 d . . .
H4 H 0.5139 0.3888 -0.3035 0.056 Uiso 1 1 calc R . .
C5 C 0.42862(15) 0.2925(3) -0.0645(5) 0.0431(6) Uani 1 1 d . . .
C6 C 0.42609(15) 0.2099(3) 0.1525(4) 0.0445(7) Uani 1 1 d . . .
H6 H 0.3718 0.1837 0.2207 0.053 Uiso 1 1 calc R . .
C7 C 0.50363(15) 0.1667(3) 0.2667(5) 0.0444(6) Uani 1 1 d . . .
H7 H 0.5008 0.1114 0.4110 0.053 Uiso 1 1 calc R . .
H1NA H 0.358(2) 0.407(6) -0.301(11) 0.109(13) Uiso 1 1 d . . .
H1NB H 0.308(2) 0.368(5) -0.108(8) 0.076(11) Uiso 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
N1 0.0559(12) 0.0490(11) 0.0629(14) 0.0042(12) -0.0069(12) 0.0040(9)
O1 0.0495(9) 0.0569(10) 0.1058(17) 0.0117(13) 0.0130(11) 0.0047(8)
C1 0.0495(13) 0.0554(14) 0.078(2) -0.0036(16) -0.0106(14) -0.0026(10)
C2 0.0461(12) 0.0382(10) 0.0497(16) -0.0067(13) -0.0003(11) -0.0003(8)
C3 0.0484(12) 0.0452(12) 0.0529(19) -0.0051(14) 0.0108(11) -0.0061(9)
C4 0.0615(14) 0.0385(11) 0.0412(16) -0.0004(12) 0.0055(11) -0.0049(9)
C5 0.0504(12) 0.0321(10) 0.0469(15) -0.0058(13) -0.0003(11) 0.0010(8)
C6 0.0454(12) 0.0418(11) 0.0464(16) -0.0006(12) 0.0081(10) -0.0028(8)
C7 0.0527(12) 0.0408(11) 0.0397(15) -0.0001(12) 0.0023(9) -0.0008(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
N1 C5 1.416(3) . ?
O1 C1 1.430(4) . ?
C1 C2 1.508(4) . ?
C2 C7 1.389(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.373(4) . ?
C4 C5 1.390(3) . ?
C5 C6 1.396(3) . ?
C6 C7 1.381(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
O1 C1 C2 112.9(3) . . ?
C7 C2 C3 118.0(2) . . ?
C7 C2 C1 121.2(3) . . ?
C3 C2 C1 120.8(2) . . ?
C4 C3 C2 121.3(2) . . ?
C3 C4 C5 120.8(3) . . ?
C4 C5 C6 118.3(2) . . ?
C4 C5 N1 121.6(3) . . ?
C6 C5 N1 120.0(2) . . ?
C7 C6 C5 120.5(2) . . ?
C6 C7 C2 121.1(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        70.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.043


