# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl[2]

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N3 O3'
_chemical_formula_weight         325.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   5.5440(18)
_cell_length_b                   23.166(8)
_cell_length_c                   12.365(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.769(4)
_cell_angle_gamma                90.00
_cell_volume                     1548.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    108(2)
_cell_measurement_reflns_used    5114
_cell_measurement_theta_min      1.8145
_cell_measurement_theta_max      31.3688

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7933
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   Crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      108(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn 724 CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7067
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0716
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2638
_reflns_number_gt                1957
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1253P)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         2638
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.2225
_refine_ls_wR_factor_gt          0.1700
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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 1.1552(4) 0.04299(9) 0.43998(18) 0.0262(6) Uani 1 1 d . . .
O2 O 0.7122(4) 0.19960(10) 0.50425(18) 0.0268(6) Uani 1 1 d . . .
O3 O 0.2711(4) 0.07278(11) -0.02550(17) 0.0309(6) Uani 1 1 d . . .
N1 N 1.9381(5) 0.04494(12) 0.7440(2) 0.0294(7) Uani 1 1 d . . .
H1A H 2.0595 0.0533 0.8008 0.035 Uiso 1 1 calc R . .
H1B H 1.9453 0.0134 0.7051 0.035 Uiso 1 1 calc R . .
N5 N 0.9302(4) 0.12010(11) 0.4760(2) 0.0197(6) Uani 1 1 d . . .
N6 N 0.5268(4) 0.11216(11) 0.1884(2) 0.0205(6) Uani 1 1 d . . .
C19 C 1.7385(5) 0.08080(14) 0.7164(2) 0.0207(7) Uani 1 1 d . . .
C20 C 1.5416(5) 0.06628(13) 0.6247(2) 0.0179(7) Uani 1 1 d . . .
H20 H 1.5516 0.0318 0.5842 0.021 Uiso 1 1 calc R . .
C21 C 1.3399(5) 0.10106(13) 0.5944(2) 0.0195(7) Uani 1 1 d . . .
C22 C 1.3170(5) 0.15242(13) 0.6531(2) 0.0190(7) Uani 1 1 d . . .
C23 C 1.7187(6) 0.13062(14) 0.7748(2) 0.0222(7) Uani 1 1 d . . .
H23 H 1.8469 0.1402 0.8369 0.027 Uiso 1 1 calc R . .
C24 C 1.5130(5) 0.16779(14) 0.7449(2) 0.0194(7) Uani 1 1 d . . .
C25 C 1.4902(6) 0.21998(14) 0.8002(3) 0.0263(8) Uani 1 1 d . . .
H25 H 1.6196 0.2313 0.8605 0.032 Uiso 1 1 calc R . .
C26 C 1.2869(6) 0.25486(15) 0.7697(3) 0.0284(8) Uani 1 1 d . . .
H26 H 1.2761 0.2896 0.8092 0.034 Uiso 1 1 calc R . .
C27 C 1.0947(6) 0.23930(14) 0.6800(3) 0.0242(7) Uani 1 1 d . . .
H27 H 0.9546 0.2637 0.6584 0.029 Uiso 1 1 calc R . .
C28 C 1.1094(5) 0.18871(13) 0.6237(2) 0.0197(7) Uani 1 1 d . . .
C29 C 0.9021(6) 0.17166(13) 0.5318(2) 0.0203(7) Uani 1 1 d . . .
C30 C 1.1394(5) 0.08524(13) 0.4991(2) 0.0198(7) Uani 1 1 d . . .
C31 C 0.7243(5) 0.10171(14) 0.3861(2) 0.0202(7) Uani 1 1 d . . .
H31A H 0.5665 0.1151 0.4024 0.024 Uiso 1 1 calc R . .
H31B H 0.7201 0.0590 0.3827 0.024 Uiso 1 1 calc R . .
C32 C 0.7476(5) 0.12547(14) 0.2741(2) 0.0196(7) Uani 1 1 d . . .
H32A H 0.7709 0.1678 0.2795 0.024 Uiso 1 1 calc R . .
H32B H 0.8948 0.1085 0.2533 0.024 Uiso 1 1 calc R . .
C33 C 0.5226(5) 0.14552(15) 0.0874(2) 0.0248(8) Uani 1 1 d . . .
H33A H 0.6680 0.1354 0.0571 0.030 Uiso 1 1 calc R . .
H33B H 0.5311 0.1873 0.1050 0.030 Uiso 1 1 calc R . .
C34 C 0.2896(6) 0.13281(15) 0.0028(3) 0.0303(8) Uani 1 1 d . . .
H34A H 0.1449 0.1443 0.0326 0.036 Uiso 1 1 calc R . .
H34B H 0.2872 0.1559 -0.0648 0.036 Uiso 1 1 calc R . .
C35 C 0.2777(6) 0.03901(15) 0.0726(3) 0.0294(8) Uani 1 1 d . . .
H35A H 0.2697 -0.0025 0.0531 0.035 Uiso 1 1 calc R . .
H35B H 0.1316 0.0484 0.1031 0.035 Uiso 1 1 calc R . .
C36 C 0.5105(6) 0.05065(14) 0.1597(3) 0.0246(8) Uani 1 1 d . . .
H36A H 0.5091 0.0274 0.2267 0.030 Uiso 1 1 calc R . .
H36B H 0.6568 0.0392 0.1311 0.030 Uiso 1 1 calc R . .


_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 C30 1.236(4) . ?
O2 C29 1.219(4) . ?
O3 C34 1.432(4) . ?
O3 C35 1.437(4) . ?
N1 C19 1.365(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N5 C30 1.390(4) . ?
N5 C29 1.405(4) . ?
N5 C31 1.469(4) . ?
N6 C32 1.464(4) . ?
N6 C33 1.464(4) . ?
N6 C36 1.467(4) . ?
C19 C23 1.379(4) . ?
C19 C20 1.430(4) . ?
C20 C21 1.362(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.415(4) . ?
C21 C30 1.476(4) . ?
C22 C28 1.407(4) . ?
C22 C24 1.432(4) . ?
C23 C24 1.411(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.408(4) . ?
C25 C26 1.370(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.404(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.375(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.480(4) . ?
C31 C32 1.522(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.501(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.511(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

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
C34 O3 C35 109.6(2) . . ?
C19 N1 H1A 120.0 . . ?
C19 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C30 N5 C29 124.8(3) . . ?
C30 N5 C31 117.4(3) . . ?
C29 N5 C31 117.8(2) . . ?
C32 N6 C33 111.1(2) . . ?
C32 N6 C36 112.2(2) . . ?
C33 N6 C36 108.5(2) . . ?
N1 C19 C23 122.2(3) . . ?
N1 C19 C20 119.3(3) . . ?
C23 C19 C20 118.5(3) . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 C30 120.0(3) . . ?
C22 C21 C30 118.8(3) . . ?
C28 C22 C21 122.1(3) . . ?
C28 C22 C24 119.4(3) . . ?
C21 C22 C24 118.5(3) . . ?
C19 C23 C24 121.8(3) . . ?
C19 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C25 C24 C23 123.4(3) . . ?
C25 C24 C22 117.7(3) . . ?
C23 C24 C22 118.9(3) . . ?
C26 C25 C24 122.0(3) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C25 C26 C27 120.0(3) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 119.9(3) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C22 121.0(3) . . ?
C27 C28 C29 119.6(3) . . ?
C22 C28 C29 119.4(3) . . ?
O2 C29 N5 119.8(3) . . ?
O2 C29 C28 123.3(3) . . ?
N5 C29 C28 116.9(3) . . ?
O1 C30 N5 120.2(3) . . ?
O1 C30 C21 122.0(3) . . ?
N5 C30 C21 117.8(3) . . ?
N5 C31 C32 112.0(2) . . ?
N5 C31 H31A 109.2 . . ?
C32 C31 H31A 109.2 . . ?
N5 C31 H31B 109.2 . . ?
C32 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
N6 C32 C31 110.9(2) . . ?
N6 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
N6 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.0 . . ?
N6 C33 C34 109.9(3) . . ?
N6 C33 H33A 109.7 . . ?
C34 C33 H33A 109.7 . . ?
N6 C33 H33B 109.7 . . ?
C34 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
O3 C34 C33 111.4(3) . . ?
O3 C34 H34A 109.4 . . ?
C33 C34 H34A 109.4 . . ?
O3 C34 H34B 109.4 . . ?
C33 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
O3 C35 C36 111.2(3) . . ?
O3 C35 H35A 109.4 . . ?
C36 C35 H35A 109.4 . . ?
O3 C35 H35B 109.4 . . ?
C36 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
N6 C36 C35 110.1(3) . . ?
N6 C36 H36A 109.6 . . ?
C35 C36 H36A 109.6 . . ?
N6 C36 H36B 109.6 . . ?
C35 C36 H36B 109.6 . . ?
H36A C36 H36B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C19 C20 C21 -179.8(3) . . . . ?
C23 C19 C20 C21 0.8(4) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C19 C20 C21 C30 179.8(3) . . . . ?
C20 C21 C22 C28 -179.5(3) . . . . ?
C30 C21 C22 C28 0.1(4) . . . . ?
C20 C21 C22 C24 0.9(4) . . . . ?
C30 C21 C22 C24 -179.5(3) . . . . ?
N1 C19 C23 C24 179.3(3) . . . . ?
C20 C19 C23 C24 -1.4(4) . . . . ?
C19 C23 C24 C25 -177.8(3) . . . . ?
C19 C23 C24 C22 1.7(4) . . . . ?
C28 C22 C24 C25 -1.5(4) . . . . ?
C21 C22 C24 C25 178.1(3) . . . . ?
C28 C22 C24 C23 179.0(3) . . . . ?
C21 C22 C24 C23 -1.4(4) . . . . ?
C23 C24 C25 C26 -179.4(3) . . . . ?
C22 C24 C25 C26 1.1(5) . . . . ?
C24 C25 C26 C27 -0.7(5) . . . . ?
C25 C26 C27 C28 0.7(5) . . . . ?
C26 C27 C28 C22 -1.1(5) . . . . ?
C26 C27 C28 C29 177.9(3) . . . . ?
C21 C22 C28 C27 -178.0(3) . . . . ?
C24 C22 C28 C27 1.5(5) . . . . ?
C21 C22 C28 C29 2.9(4) . . . . ?
C24 C22 C28 C29 -177.5(3) . . . . ?
C30 N5 C29 O2 179.0(3) . . . . ?
C31 N5 C29 O2 -0.7(4) . . . . ?
C30 N5 C29 C28 -1.7(4) . . . . ?
C31 N5 C29 C28 178.7(2) . . . . ?
C27 C28 C29 O2 -2.0(5) . . . . ?
C22 C28 C29 O2 177.1(3) . . . . ?
C27 C28 C29 N5 178.7(3) . . . . ?
C22 C28 C29 N5 -2.2(4) . . . . ?
C29 N5 C30 O1 -174.4(3) . . . . ?
C31 N5 C30 O1 5.3(4) . . . . ?
C29 N5 C30 C21 4.6(4) . . . . ?
C31 N5 C30 C21 -175.7(2) . . . . ?
C20 C21 C30 O1 -5.1(5) . . . . ?
C22 C21 C30 O1 175.2(3) . . . . ?
C20 C21 C30 N5 175.8(3) . . . . ?
C22 C21 C30 N5 -3.8(4) . . . . ?
C30 N5 C31 C32 -89.3(3) . . . . ?
C29 N5 C31 C32 90.4(3) . . . . ?
C33 N6 C32 C31 167.2(3) . . . . ?
C36 N6 C32 C31 -71.2(3) . . . . ?
N5 C31 C32 N6 -173.5(2) . . . . ?
C32 N6 C33 C34 -177.7(3) . . . . ?
C36 N6 C33 C34 58.6(3) . . . . ?
C35 O3 C34 C33 58.3(3) . . . . ?
N6 C33 C34 O3 -59.7(4) . . . . ?
C34 O3 C35 C36 -57.5(3) . . . . ?
C32 N6 C36 C35 179.0(2) . . . . ?
C33 N6 C36 C35 -58.0(3) . . . . ?
O3 C35 C36 N6 58.3(4) . . . . ?

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 O3 0.88 2.25 3.102(3) 161.7 1_756
N1 H1B O1 0.88 2.19 3.013(4) 155.4 3_856

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.117
_database_code_depnum_ccdc_archive 'CCDC 970628'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl[1]

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N3 O2'
_chemical_formula_weight         323.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.962(2)
_cell_length_b                   14.046(5)
_cell_length_c                   16.346(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.843(4)
_cell_angle_gamma                90.00
_cell_volume                     1590.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    108(2)
_cell_measurement_reflns_used    4274
_cell_measurement_theta_min      1.8654
_cell_measurement_theta_max      31.3572

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7695
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   Crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      108(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn 724 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12869
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2792
_reflns_number_gt                2506
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0365P)²+0.8025P] 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         2792
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_restrained_S_all      1.202
_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 0.1966(2) 0.27740(11) 0.28492(9) 0.0267(4) Uani 1 1 d . . .
O2 O -0.3513(2) 0.42559(11) 0.34780(9) 0.0242(4) Uani 1 1 d . . .
N1 N -0.0748(2) 0.35464(13) 0.31649(10) 0.0198(4) Uani 1 1 d . . .
N2 N -0.2708(3) 0.46803(13) 0.65868(11) 0.0244(4) Uani 1 1 d . . .
H1Y H -0.2300 0.4675 0.7114 0.029 Uiso 1 1 calc R . .
H1X H -0.3836 0.4932 0.6418 0.029 Uiso 1 1 calc R . .
N3 N 0.0447(2) 0.48000(13) 0.17570(10) 0.0200(4) Uani 1 1 d . . .
C1 C 0.4334(3) 0.27903(16) 0.53319(14) 0.0240(5) Uani 1 1 d . . .
H1 H 0.5586 0.2546 0.5496 0.029 Uiso 1 1 calc R . .
C2 C 0.3238(3) 0.31398(15) 0.59179(14) 0.0235(5) Uani 1 1 d . . .
H2 H 0.3738 0.3129 0.6481 0.028 Uiso 1 1 calc R . .
C3 C 0.1368(3) 0.35160(15) 0.56923(13) 0.0208(5) Uani 1 1 d . . .
C4 C 0.0674(3) 0.35189(15) 0.48428(13) 0.0184(5) Uani 1 1 d . . .
C5 C 0.3634(3) 0.27877(15) 0.44959(14) 0.0229(5) Uani 1 1 d . . .
H5 H 0.4407 0.2543 0.4098 0.028 Uiso 1 1 calc R . .
C6 C 0.1815(3) 0.31432(15) 0.42556(13) 0.0195(5) Uani 1 1 d . . .
C7 C -0.1166(3) 0.39143(15) 0.46036(13) 0.0184(5) Uani 1 1 d . . .
C8 C -0.2250(3) 0.43009(15) 0.51765(13) 0.0195(5) Uani 1 1 d . . .
H8 H -0.3469 0.4576 0.5000 0.023 Uiso 1 1 calc R . .
C9 C -0.1588(3) 0.42982(15) 0.60303(13) 0.0204(5) Uani 1 1 d . . .
C10 C 0.0200(3) 0.38944(15) 0.62688(13) 0.0206(5) Uani 1 1 d . . .
H10 H 0.0650 0.3872 0.6837 0.025 Uiso 1 1 calc R . .
C11 C -0.1917(3) 0.39358(15) 0.37257(13) 0.0193(5) Uani 1 1 d . . .
C12 C 0.1076(3) 0.31363(15) 0.33764(13) 0.0210(5) Uani 1 1 d . . .
C13 C 0.1548(3) 0.41627(16) 0.12614(13) 0.0221(5) Uani 1 1 d . . .
H13A H 0.0875 0.4106 0.0700 0.026 Uiso 1 1 calc R . .
H13B H 0.1625 0.3521 0.1512 0.026 Uiso 1 1 calc R . .
C14 C 0.3567(3) 0.45484(16) 0.12138(14) 0.0238(5) Uani 1 1 d . . .
H14A H 0.4285 0.4114 0.0878 0.029 Uiso 1 1 calc R . .
H14B H 0.4259 0.4573 0.1773 0.029 Uiso 1 1 calc R . .
C15 C 0.3516(3) 0.55379(16) 0.08375(14) 0.0274(5) Uani 1 1 d . . .
H15A H 0.3005 0.5501 0.0251 0.033 Uiso 1 1 calc R . .
H15B H 0.4841 0.5800 0.0869 0.033 Uiso 1 1 calc R . .
C16 C 0.2239(3) 0.61948(16) 0.12938(14) 0.0293(5) Uani 1 1 d . . .
H16A H 0.2879 0.6327 0.1851 0.035 Uiso 1 1 calc R . .
H16B H 0.2066 0.6808 0.0996 0.035 Uiso 1 1 calc R . .
C17 C 0.0273(3) 0.57442(16) 0.13641(14) 0.0249(5) Uani 1 1 d . . .
H17A H -0.0494 0.6167 0.1691 0.030 Uiso 1 1 calc R . .
H17B H -0.0426 0.5680 0.0808 0.030 Uiso 1 1 calc R . .
C18 C -0.1503(3) 0.44244(16) 0.18303(13) 0.0224(5) Uani 1 1 d . . .
H18A H -0.2163 0.4334 0.1270 0.027 Uiso 1 1 calc R . .
H18B H -0.2239 0.4909 0.2108 0.027 Uiso 1 1 calc R . .
C19 C -0.1580(3) 0.34913(16) 0.22967(12) 0.0226(5) Uani 1 1 d . . .
H19A H -0.2943 0.3285 0.2280 0.027 Uiso 1 1 calc R . .
H19B H -0.0874 0.3000 0.2013 0.027 Uiso 1 1 calc R . .


_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 C12 1.223(3) . ?
O2 C11 1.229(2) . ?
N1 C11 1.397(3) . ?
N1 C12 1.405(3) . ?
N1 C19 1.479(3) . ?
N2 C9 1.367(3) . ?
N2 H1Y 0.8800 . ?
N2 H1X 0.8800 . ?
N3 C18 1.473(3) . ?
N3 C17 1.473(3) . ?
N3 C13 1.473(3) . ?
C1 C2 1.375(3) . ?
C1 C5 1.403(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.418(3) . ?
C2 H2 0.9500 . ?
C3 C10 1.410(3) . ?
C3 C4 1.423(3) . ?
C4 C6 1.409(3) . ?
C4 C7 1.414(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 C12 1.476(3) . ?
C7 C8 1.373(3) . ?
C7 C11 1.477(3) . ?
C8 C9 1.425(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C10 H10 0.9500 . ?
C13 C14 1.516(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.519(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.527(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.523(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.520(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

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
C11 N1 C12 124.80(18) . . ?
C11 N1 C19 116.92(17) . . ?
C12 N1 C19 118.05(17) . . ?
C9 N2 H1Y 120.0 . . ?
C9 N2 H1X 120.0 . . ?
H1Y N2 H1X 120.0 . . ?
C18 N3 C17 108.79(16) . . ?
C18 N3 C13 111.24(17) . . ?
C17 N3 C13 109.38(16) . . ?
C2 C1 C5 121.1(2) . . ?
C2 C1 H1 119.4 . . ?
C5 C1 H1 119.4 . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C10 C3 C2 122.9(2) . . ?
C10 C3 C4 119.29(19) . . ?
C2 C3 C4 117.8(2) . . ?
C6 C4 C7 121.08(19) . . ?
C6 C4 C3 120.29(19) . . ?
C7 C4 C3 118.63(19) . . ?
C6 C5 C1 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C1 C5 H5 120.2 . . ?
C5 C6 C4 120.4(2) . . ?
C5 C6 C12 119.56(19) . . ?
C4 C6 C12 120.03(19) . . ?
C8 C7 C4 120.80(19) . . ?
C8 C7 C11 119.33(19) . . ?
C4 C7 C11 119.86(19) . . ?
C7 C8 C9 121.4(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
N2 C9 C10 122.00(19) . . ?
N2 C9 C8 120.09(19) . . ?
C10 C9 C8 117.91(19) . . ?
C9 C10 C3 121.9(2) . . ?
C9 C10 H10 119.1 . . ?
C3 C10 H10 119.1 . . ?
O2 C11 N1 119.63(19) . . ?
O2 C11 C7 123.13(19) . . ?
N1 C11 C7 117.22(18) . . ?
O1 C12 N1 120.5(2) . . ?
O1 C12 C6 122.50(19) . . ?
N1 C12 C6 116.97(18) . . ?
N3 C13 C14 110.36(17) . . ?
N3 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N3 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 111.35(18) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 110.24(18) . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 110.97(19) . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N3 C17 C16 111.84(18) . . ?
N3 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
N3 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
N3 C18 C19 115.45(17) . . ?
N3 C18 H18A 108.4 . . ?
C19 C18 H18A 108.4 . . ?
N3 C18 H18B 108.4 . . ?
C19 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
N1 C19 C18 113.93(18) . . ?
N1 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
N1 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?

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
C5 C1 C2 C3 -0.5(3) . . . . ?
C1 C2 C3 C10 -179.1(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C10 C3 C4 C6 -179.9(2) . . . . ?
C2 C3 C4 C6 1.0(3) . . . . ?
C10 C3 C4 C7 0.8(3) . . . . ?
C2 C3 C4 C7 -178.33(19) . . . . ?
C2 C1 C5 C6 0.1(3) . . . . ?
C1 C5 C6 C4 0.9(3) . . . . ?
C1 C5 C6 C12 -179.72(19) . . . . ?
C7 C4 C6 C5 177.88(19) . . . . ?
C3 C4 C6 C5 -1.4(3) . . . . ?
C7 C4 C6 C12 -1.5(3) . . . . ?
C3 C4 C6 C12 179.17(19) . . . . ?
C6 C4 C7 C8 -178.35(19) . . . . ?
C3 C4 C7 C8 1.0(3) . . . . ?
C6 C4 C7 C11 0.1(3) . . . . ?
C3 C4 C7 C11 179.41(19) . . . . ?
C4 C7 C8 C9 -1.5(3) . . . . ?
C11 C7 C8 C9 -179.95(19) . . . . ?
C7 C8 C9 N2 -179.4(2) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
N2 C9 C10 C3 -178.8(2) . . . . ?
C8 C9 C10 C3 1.5(3) . . . . ?
C2 C3 C10 C9 177.0(2) . . . . ?
C4 C3 C10 C9 -2.1(3) . . . . ?
C12 N1 C11 O2 -178.16(19) . . . . ?
C19 N1 C11 O2 -3.7(3) . . . . ?
C12 N1 C11 C7 0.2(3) . . . . ?
C19 N1 C11 C7 174.65(18) . . . . ?
C8 C7 C11 O2 -2.6(3) . . . . ?
C4 C7 C11 O2 178.9(2) . . . . ?
C8 C7 C11 N1 179.07(19) . . . . ?
C4 C7 C11 N1 0.6(3) . . . . ?
C11 N1 C12 O1 176.77(19) . . . . ?
C19 N1 C12 O1 2.4(3) . . . . ?
C11 N1 C12 C6 -1.6(3) . . . . ?
C19 N1 C12 C6 -175.97(18) . . . . ?
C5 C6 C12 O1 4.5(3) . . . . ?
C4 C6 C12 O1 -176.1(2) . . . . ?
C5 C6 C12 N1 -177.20(19) . . . . ?
C4 C6 C12 N1 2.2(3) . . . . ?
C18 N3 C13 C14 -178.42(17) . . . . ?
C17 N3 C13 C14 61.4(2) . . . . ?
N3 C13 C14 C15 -58.8(2) . . . . ?
C13 C14 C15 C16 53.2(2) . . . . ?
C14 C15 C16 C17 -51.1(3) . . . . ?
C18 N3 C17 C16 178.02(17) . . . . ?
C13 N3 C17 C16 -60.3(2) . . . . ?
C15 C16 C17 N3 55.5(2) . . . . ?
C17 N3 C18 C19 -174.54(17) . . . . ?
C13 N3 C18 C19 64.9(2) . . . . ?
C11 N1 C19 C18 80.2(2) . . . . ?
C12 N1 C19 C18 -105.0(2) . . . . ?
N3 C18 C19 N1 61.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1X O2 0.88 2.19 3.018(2) 156.4 3_466
N2 H1Y N3 0.88 2.26 3.078(3) 153.6 3_566

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 970629'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N3 O2'
_chemical_formula_weight         309.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.6599(17)
_cell_length_b                   21.310(5)
_cell_length_c                   11.054(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.174(4)
_cell_angle_gamma                90.00
_cell_volume                     1548.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    118(2)
_cell_measurement_reflns_used    3289
_cell_measurement_theta_min      1.8639
_cell_measurement_theta_max      31.2862

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7695
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   Crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      118(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn 724 CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12422
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2692
_reflns_number_gt                2202
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1073P)²+0.1417P] 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         2692
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1973
_refine_ls_wR_factor_gt          0.1641
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_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 0.6954(3) 0.04191(8) 0.95694(15) 0.0293(5) Uani 1 1 d . . .
O2 O 0.1260(2) 0.04022(7) 0.67119(14) 0.0245(4) Uani 1 1 d . . .
N1 N 0.4920(3) 0.18203(9) 0.82748(17) 0.0255(5) Uani 1 1 d . . .
N2 N 0.4107(3) 0.04112(9) 0.81305(16) 0.0204(5) Uani 1 1 d . . .
N6 N 0.2563(3) -0.11841(9) 0.35063(18) 0.0282(5) Uani 1 1 d . . .
H6A H 0.3069 -0.1472 0.3071 0.034 Uiso 1 1 calc R . .
H6B H 0.1335 -0.1035 0.3258 0.034 Uiso 1 1 calc R . .
C19 C 0.6752(5) 0.27464(13) 0.8024(3) 0.0426(8) Uani 1 1 d . . .
H19A H 0.6627 0.3206 0.8115 0.051 Uiso 1 1 calc R . .
H19B H 0.7606 0.2659 0.7387 0.051 Uiso 1 1 calc R . .
C20 C 0.4668(5) 0.24417(12) 0.7700(2) 0.0338(7) Uani 1 1 d . . .
H20A H 0.3620 0.2688 0.8032 0.041 Uiso 1 1 calc R . .
H20B H 0.4273 0.2405 0.6801 0.041 Uiso 1 1 calc R . .
C21 C 0.7658(5) 0.24403(14) 0.9250(3) 0.0451(8) Uani 1 1 d . . .
H21A H 0.8967 0.2233 0.9188 0.054 Uiso 1 1 calc R . .
H21B H 0.7887 0.2758 0.9912 0.054 Uiso 1 1 calc R . .
C22 C 0.6073(4) 0.19597(12) 0.9499(2) 0.0332(7) Uani 1 1 d . . .
H22A H 0.6733 0.1577 0.9882 0.040 Uiso 1 1 calc R . .
H22B H 0.5172 0.2137 1.0043 0.040 Uiso 1 1 calc R . .
C23 C 0.2969(4) 0.15239(11) 0.8309(2) 0.0256(6) Uani 1 1 d . . .
H23A H 0.2206 0.1506 0.7464 0.031 Uiso 1 1 calc R . .
H23B H 0.2182 0.1789 0.8800 0.031 Uiso 1 1 calc R . .
C24 C 0.3107(4) 0.08671(11) 0.8841(2) 0.0242(6) Uani 1 1 d . . .
H24A H 0.3868 0.0885 0.9686 0.029 Uiso 1 1 calc R . .
H24B H 0.1717 0.0716 0.8890 0.029 Uiso 1 1 calc R . .
C25 C 0.6066(4) 0.02013(11) 0.8610(2) 0.0222(5) Uani 1 1 d . . .
C26 C 0.2965(3) 0.01924(10) 0.7044(2) 0.0202(5) Uani 1 1 d . . .
C27 C 0.3896(3) -0.02892(10) 0.63519(19) 0.0190(5) Uani 1 1 d . . .
C28 C 0.5868(3) -0.05107(10) 0.67996(19) 0.0193(5) Uani 1 1 d . . .
C29 C 0.6963(3) -0.02855(10) 0.7913(2) 0.0207(5) Uani 1 1 d . . .
C30 C 0.8875(4) -0.05135(11) 0.8346(2) 0.0238(6) Uani 1 1 d . . .
H30 H 0.9600 -0.0363 0.9101 0.029 Uiso 1 1 calc R . .
C31 C 0.9757(4) -0.09676(11) 0.7676(2) 0.0256(6) Uani 1 1 d . . .
H31 H 1.1076 -0.1124 0.7981 0.031 Uiso 1 1 calc R . .
C32 C 0.8730(4) -0.11874(11) 0.6584(2) 0.0240(6) Uani 1 1 d . . .
H32 H 0.9358 -0.1491 0.6137 0.029 Uiso 1 1 calc R . .
C33 C 0.6746(3) -0.09696(10) 0.61101(19) 0.0197(5) Uani 1 1 d . . .
C34 C 0.5626(4) -0.11868(10) 0.5001(2) 0.0211(5) Uani 1 1 d . . .
H34 H 0.6214 -0.1491 0.4537 0.025 Uiso 1 1 calc R . .
C35 C 0.2833(3) -0.05123(10) 0.5270(2) 0.0206(5) Uani 1 1 d . . .
H35 H 0.1502 -0.0359 0.4986 0.025 Uiso 1 1 calc R . .
C36 C 0.3690(3) -0.09675(11) 0.4572(2) 0.0208(5) Uani 1 1 d . . .


_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 C25 1.220(3) . ?
O2 C26 1.221(3) . ?
N1 C23 1.451(3) . ?
N1 C20 1.467(3) . ?
N1 C22 1.475(3) . ?
N2 C26 1.395(3) . ?
N2 C25 1.401(3) . ?
N2 C24 1.473(3) . ?
N6 C36 1.372(3) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
C19 C20 1.523(4) . ?
C19 C21 1.538(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.527(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.516(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C29 1.475(3) . ?
C26 C27 1.475(3) . ?
C27 C35 1.374(3) . ?
C27 C28 1.409(3) . ?
C28 C29 1.411(3) . ?
C28 C33 1.422(3) . ?
C29 C30 1.376(3) . ?
C30 C31 1.403(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.371(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.420(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.408(3) . ?
C34 C36 1.382(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.415(3) . ?
C35 H35 0.9500 . ?

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
C23 N1 C20 111.3(2) . . ?
C23 N1 C22 113.64(19) . . ?
C20 N1 C22 102.86(19) . . ?
C26 N2 C25 124.5(2) . . ?
C26 N2 C24 116.63(19) . . ?
C25 N2 C24 118.78(18) . . ?
C36 N6 H6A 120.0 . . ?
C36 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C20 C19 C21 104.0(2) . . ?
C20 C19 H19A 111.0 . . ?
C21 C19 H19A 111.0 . . ?
C20 C19 H19B 111.0 . . ?
C21 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
N1 C20 C19 104.2(2) . . ?
N1 C20 H20A 110.9 . . ?
C19 C20 H20A 110.9 . . ?
N1 C20 H20B 110.9 . . ?
C19 C20 H20B 110.9 . . ?
H20A C20 H20B 108.9 . . ?
C22 C21 C19 105.0(2) . . ?
C22 C21 H21A 110.8 . . ?
C19 C21 H21A 110.8 . . ?
C22 C21 H21B 110.8 . . ?
C19 C21 H21B 110.8 . . ?
H21A C21 H21B 108.8 . . ?
N1 C22 C21 104.1(2) . . ?
N1 C22 H22A 110.9 . . ?
C21 C22 H22A 110.9 . . ?
N1 C22 H22B 110.9 . . ?
C21 C22 H22B 110.9 . . ?
H22A C22 H22B 109.0 . . ?
N1 C23 C24 114.4(2) . . ?
N1 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
N1 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
N2 C24 C23 114.01(19) . . ?
N2 C24 H24A 108.8 . . ?
C23 C24 H24A 108.8 . . ?
N2 C24 H24B 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.6 . . ?
O1 C25 N2 120.1(2) . . ?
O1 C25 C29 122.7(2) . . ?
N2 C25 C29 117.2(2) . . ?
O2 C26 N2 119.3(2) . . ?
O2 C26 C27 123.1(2) . . ?
N2 C26 C27 117.5(2) . . ?
C35 C27 C28 120.8(2) . . ?
C35 C27 C26 119.4(2) . . ?
C28 C27 C26 119.8(2) . . ?
C27 C28 C29 121.1(2) . . ?
C27 C28 C33 118.8(2) . . ?
C29 C28 C33 120.1(2) . . ?
C30 C29 C28 120.3(2) . . ?
C30 C29 C25 119.8(2) . . ?
C28 C29 C25 119.9(2) . . ?
C29 C30 C31 120.1(2) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C32 C31 C30 120.6(2) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C31 C32 C33 121.2(2) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C34 C33 C32 123.2(2) . . ?
C34 C33 C28 119.1(2) . . ?
C32 C33 C28 117.7(2) . . ?
C36 C34 C33 121.6(2) . . ?
C36 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C27 C35 C36 121.0(2) . . ?
C27 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
N6 C36 C34 122.2(2) . . ?
N6 C36 C35 119.1(2) . . ?
C34 C36 C35 118.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C23 N1 C20 C19 166.21(19) . . . . ?
C22 N1 C20 C19 44.2(2) . . . . ?
C21 C19 C20 N1 -28.6(3) . . . . ?
C20 C19 C21 C22 2.9(3) . . . . ?
C23 N1 C22 C21 -162.4(2) . . . . ?
C20 N1 C22 C21 -42.0(2) . . . . ?
C19 C21 C22 N1 23.5(3) . . . . ?
C20 N1 C23 C24 177.46(19) . . . . ?
C22 N1 C23 C24 -67.0(3) . . . . ?
C26 N2 C24 C23 -75.9(3) . . . . ?
C25 N2 C24 C23 107.6(2) . . . . ?
N1 C23 C24 N2 -63.0(3) . . . . ?
C26 N2 C25 O1 -179.9(2) . . . . ?
C24 N2 C25 O1 -3.7(3) . . . . ?
C26 N2 C25 C29 -0.1(3) . . . . ?
C24 N2 C25 C29 176.09(19) . . . . ?
C25 N2 C26 O2 179.2(2) . . . . ?
C24 N2 C26 O2 2.9(3) . . . . ?
C25 N2 C26 C27 -0.5(3) . . . . ?
C24 N2 C26 C27 -176.84(18) . . . . ?
O2 C26 C27 C35 1.0(3) . . . . ?
N2 C26 C27 C35 -179.24(19) . . . . ?
O2 C26 C27 C28 -179.6(2) . . . . ?
N2 C26 C27 C28 0.2(3) . . . . ?
C35 C27 C28 C29 -179.71(19) . . . . ?
C26 C27 C28 C29 0.9(3) . . . . ?
C35 C27 C28 C33 0.1(3) . . . . ?
C26 C27 C28 C33 -179.27(19) . . . . ?
C27 C28 C29 C30 179.0(2) . . . . ?
C33 C28 C29 C30 -0.8(3) . . . . ?
C27 C28 C29 C25 -1.6(3) . . . . ?
C33 C28 C29 C25 178.6(2) . . . . ?
O1 C25 C29 C30 0.4(4) . . . . ?
N2 C25 C29 C30 -179.4(2) . . . . ?
O1 C25 C29 C28 -179.0(2) . . . . ?
N2 C25 C29 C28 1.2(3) . . . . ?
C28 C29 C30 C31 0.7(3) . . . . ?
C25 C29 C30 C31 -178.7(2) . . . . ?
C29 C30 C31 C32 0.2(4) . . . . ?
C30 C31 C32 C33 -0.8(4) . . . . ?
C31 C32 C33 C34 -179.3(2) . . . . ?
C31 C32 C33 C28 0.7(3) . . . . ?
C27 C28 C33 C34 0.2(3) . . . . ?
C29 C28 C33 C34 -179.9(2) . . . . ?
C27 C28 C33 C32 -179.7(2) . . . . ?
C29 C28 C33 C32 0.2(3) . . . . ?
C32 C33 C34 C36 179.5(2) . . . . ?
C28 C33 C34 C36 -0.4(3) . . . . ?
C28 C27 C35 C36 -0.4(3) . . . . ?
C26 C27 C35 C36 179.1(2) . . . . ?
C33 C34 C36 N6 -178.6(2) . . . . ?
C33 C34 C36 C35 0.2(3) . . . . ?
C27 C35 C36 N6 179.0(2) . . . . ?
C27 C35 C36 C34 0.2(3) . . . . ?

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
N6 H6A N1 0.88 2.28 3.094(3) 154.2 3_656
N6 H6B O2 0.88 2.20 3.020(3) 155.8 3_556

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.145
_database_code_depnum_ccdc_archive 'CCDC 970630'
