# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 4-hydroxy-3[1-(3,4,5-trimethoxy-benzylimino)-ethyl]chromen-2-one 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N O6'
_chemical_formula_sum            'C21 H21 N O6'
_chemical_formula_weight         383.39

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   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   4.6927(3)
_cell_length_b                   13.1132(10)
_cell_length_c                   14.7084(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.090(6)
_cell_angle_gamma                90.00
_cell_volume                     905.10(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2915
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      26.49

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 16.0328
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7997
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         26.49
_reflns_number_total             3657
_reflns_number_gt                2490
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2006)'
_computing_publication_material  'PLATON (Spek, 2006)'

_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)+(0.0206P)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     SHELXL
_refine_ls_extinction_coef       0.0089(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3657
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0564
_refine_ls_wR_factor_gt          0.0536
_refine_ls_goodness_of_fit_ref   0.800
_refine_ls_restrained_S_all      0.800
_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 0.6999(3) -0.20376(10) 0.90868(10) 0.0217(4) Uani 1 1 d . . .
O2 O 0.4345(3) -0.14688(11) 1.01908(10) 0.0270(4) Uani 1 1 d . . .
O4 O 0.4067(3) 0.00819(10) 0.72751(9) 0.0204(4) Uani 1 1 d . . .
O35 O 0.3551(3) 0.47205(10) 0.70512(10) 0.0206(4) Uani 1 1 d . . .
O36 O 0.0729(3) 0.41891(10) 0.55537(10) 0.0201(4) Uani 1 1 d . . .
O37 O -0.3090(3) 0.26810(10) 0.55626(10) 0.0223(4) Uani 1 1 d . . .
N1 N 0.1140(3) 0.08861(13) 0.85289(12) 0.0164(4) Uani 1 1 d . . .
C2 C 0.4989(4) -0.13478(17) 0.94024(16) 0.0200(5) Uani 1 1 d . . .
C3 C 0.3941(4) -0.05759(16) 0.87785(15) 0.0165(5) Uani 1 1 d . . .
C4 C 0.4894(4) -0.05590(15) 0.78521(15) 0.0155(5) Uani 1 1 d . . .
C5 C 0.7970(4) -0.13963(17) 0.66801(15) 0.0216(5) Uani 1 1 d . . .
H5 H 0.7288 -0.0930 0.6236 0.026 Uiso 1 1 calc R . .
C6 C 0.9959(4) -0.21232(17) 0.64390(15) 0.0241(5) Uani 1 1 d . . .
H6 H 1.0631 -0.2159 0.5831 0.029 Uiso 1 1 calc R . .
C7 C 1.0977(4) -0.28035(17) 0.70885(15) 0.0227(5) Uani 1 1 d . . .
H7 H 1.2353 -0.3301 0.6923 0.027 Uiso 1 1 calc R . .
C8 C 0.9994(4) -0.27591(17) 0.79747(15) 0.0211(5) Uani 1 1 d . . .
H8 H 1.0704 -0.3217 0.8421 0.025 Uiso 1 1 calc R . .
C9 C 0.7961(4) -0.20366(16) 0.82013(14) 0.0175(5) Uani 1 1 d . . .
C10 C 0.6946(4) -0.13405(16) 0.75738(14) 0.0164(5) Uani 1 1 d . . .
C31 C 0.1989(4) 0.01850(16) 0.91060(14) 0.0155(5) Uani 1 1 d . . .
C32 C -0.0615(4) 0.18028(16) 0.87232(15) 0.0207(5) Uani 1 1 d . . .
H32A H 0.0115 0.2159 0.9269 0.025 Uiso 1 1 calc R . .
H32B H -0.2620 0.1605 0.8834 0.025 Uiso 1 1 calc R . .
C33 C -0.0422(4) 0.24882(15) 0.79038(14) 0.0157(5) Uani 1 1 d . . .
C34 C 0.1498(4) 0.32993(15) 0.79093(14) 0.0164(5) Uani 1 1 d . . .
H34 H 0.2592 0.3449 0.8437 0.020 Uiso 1 1 calc R . .
C35 C 0.1782(4) 0.38898(15) 0.71200(14) 0.0162(5) Uani 1 1 d . . .
C36 C 0.0242(4) 0.36579(16) 0.63435(14) 0.0146(5) Uani 1 1 d . . .
C37 C -0.1678(4) 0.28437(16) 0.63587(14) 0.0163(5) Uani 1 1 d . . .
C38 C -0.2022(4) 0.22621(16) 0.71419(14) 0.0171(5) Uani 1 1 d . . .
H38 H -0.3346 0.1714 0.7152 0.021 Uiso 1 1 calc R . .
C351 C 0.5187(4) 0.49705(17) 0.78360(14) 0.0238(6) Uani 1 1 d . . .
H35A H 0.3904 0.5131 0.8341 0.036 Uiso 1 1 calc R . .
H35B H 0.6390 0.5563 0.7705 0.036 Uiso 1 1 calc R . .
H35C H 0.6393 0.4389 0.8002 0.036 Uiso 1 1 calc R . .
C361 C -0.1425(4) 0.49303(17) 0.53505(15) 0.0259(6) Uani 1 1 d . . .
H36A H -0.3310 0.4614 0.5401 0.039 Uiso 1 1 calc R . .
H36B H -0.1154 0.5185 0.4730 0.039 Uiso 1 1 calc R . .
H36C H -0.1282 0.5498 0.5781 0.039 Uiso 1 1 calc R . .
C371 C -0.4915(4) 0.18136(16) 0.55101(15) 0.0237(6) Uani 1 1 d . . .
H37A H -0.3795 0.1192 0.5609 0.036 Uiso 1 1 calc R . .
H37B H -0.5809 0.1787 0.4908 0.036 Uiso 1 1 calc R . .
H37C H -0.6394 0.1865 0.5977 0.036 Uiso 1 1 calc R . .
C311 C 0.0881(4) 0.02356(17) 1.00510(14) 0.0239(6) Uani 1 1 d . . .
H31A H -0.0817 0.0671 1.0066 0.036 Uiso 1 1 calc R . .
H31B H 0.2347 0.0521 1.0452 0.036 Uiso 1 1 calc R . .
H31C H 0.0381 -0.0452 1.0258 0.036 Uiso 1 1 calc R . .
H1 H 0.198(4) 0.0813(15) 0.7913(14) 0.021(6) Uiso 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 C9 1.379(2) . ?
O1 C2 1.387(2) . ?
O2 C2 1.209(2) . ?
O4 C4 1.255(2) . ?
O35 C35 1.374(2) . ?
O35 C351 1.424(2) . ?
O36 C36 1.374(2) . ?
O36 C361 1.433(2) . ?
O37 C37 1.361(2) . ?
O37 C371 1.426(2) . ?
N1 C31 1.313(3) . ?
N1 C32 1.485(3) . ?
N1 H1 0.99(2) . ?
C2 C3 1.452(3) . ?
C3 C4 1.435(3) . ?
C3 C31 1.438(3) . ?
C4 C10 1.465(3) . ?
C5 C6 1.381(3) . ?
C5 C10 1.402(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C31 C311 1.486(3) . ?
C32 C33 1.506(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C38 1.380(3) . ?
C33 C34 1.394(3) . ?
C34 C35 1.402(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.384(3) . ?
C36 C37 1.397(3) . ?
C37 C38 1.391(3) . ?
C38 H38 0.9500 . ?
C351 H35A 0.9800 . ?
C351 H35B 0.9800 . ?
C351 H35C 0.9800 . ?
C361 H36A 0.9800 . ?
C361 H36B 0.9800 . ?
C361 H36C 0.9800 . ?
C371 H37A 0.9800 . ?
C371 H37B 0.9800 . ?
C371 H37C 0.9800 . ?
C311 H31A 0.9800 . ?
C311 H31B 0.9800 . ?
C311 H31C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C2 122.61(17) . . ?
C35 O35 C351 116.62(16) . . ?
C36 O36 C361 113.70(15) . . ?
C37 O37 C371 117.60(16) . . ?
C31 N1 C32 127.61(19) . . ?
C31 N1 H1 113.8(12) . . ?
C32 N1 H1 118.3(12) . . ?
O2 C2 O1 113.99(19) . . ?
O2 C2 C3 127.8(2) . . ?
O1 C2 C3 118.23(19) . . ?
C4 C3 C31 120.46(18) . . ?
C4 C3 C2 120.35(18) . . ?
C31 C3 C2 119.18(19) . . ?
O4 C4 C3 123.77(19) . . ?
O4 C4 C10 118.81(19) . . ?
C3 C4 C10 117.42(18) . . ?
C6 C5 C10 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.1(2) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
O1 C9 C10 121.23(18) . . ?
O1 C9 C8 116.93(19) . . ?
C10 C9 C8 121.8(2) . . ?
C9 C10 C5 118.3(2) . . ?
C9 C10 C4 120.08(19) . . ?
C5 C10 C4 121.65(19) . . ?
N1 C31 C3 117.53(19) . . ?
N1 C31 C311 117.84(19) . . ?
C3 C31 C311 124.63(19) . . ?
N1 C32 C33 107.15(17) . . ?
N1 C32 H32A 110.3 . . ?
C33 C32 H32A 110.3 . . ?
N1 C32 H32B 110.3 . . ?
C33 C32 H32B 110.3 . . ?
H32A C32 H32B 108.5 . . ?
C38 C33 C34 121.30(19) . . ?
C38 C33 C32 119.22(18) . . ?
C34 C33 C32 119.36(19) . . ?
C33 C34 C35 118.61(19) . . ?
C33 C34 H34 120.7 . . ?
C35 C34 H34 120.7 . . ?
O35 C35 C36 115.36(17) . . ?
O35 C35 C34 123.87(18) . . ?
C36 C35 C34 120.77(18) . . ?
O36 C36 C35 119.92(18) . . ?
O36 C36 C37 120.60(18) . . ?
C35 C36 C37 119.37(19) . . ?
O37 C37 C38 124.70(18) . . ?
O37 C37 C36 114.78(17) . . ?
C38 C37 C36 120.52(18) . . ?
C33 C38 C37 119.40(19) . . ?
C33 C38 H38 120.3 . . ?
C37 C38 H38 120.3 . . ?
O35 C351 H35A 109.5 . . ?
O35 C351 H35B 109.5 . . ?
H35A C351 H35B 109.5 . . ?
O35 C351 H35C 109.5 . . ?
H35A C351 H35C 109.5 . . ?
H35B C351 H35C 109.5 . . ?
O36 C361 H36A 109.5 . . ?
O36 C361 H36B 109.5 . . ?
H36A C361 H36B 109.5 . . ?
O36 C361 H36C 109.5 . . ?
H36A C361 H36C 109.5 . . ?
H36B C361 H36C 109.5 . . ?
O37 C371 H37A 109.5 . . ?
O37 C371 H37B 109.5 . . ?
H37A C371 H37B 109.5 . . ?
O37 C371 H37C 109.5 . . ?
H37A C371 H37C 109.5 . . ?
H37B C371 H37C 109.5 . . ?
C31 C311 H31A 109.5 . . ?
C31 C311 H31B 109.5 . . ?
H31A C311 H31B 109.5 . . ?
C31 C311 H31C 109.5 . . ?
H31A C311 H31C 109.5 . . ?
H31B C311 H31C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 990515'
#######################################################################
#
#                 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        
; 
4-hydroxy-3-[phenyl-(3,4,5-tromethoxy-bezylimino)-methyl]
chromen-2-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H23 N O6'
_chemical_formula_sum            'C26 H23 N O6'
_chemical_formula_weight         445.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4149(3)
_cell_length_b                   15.5812(3)
_cell_length_c                   15.0592(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 126.999(2)
_cell_angle_gamma                90.00
_cell_volume                     2139.09(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4874
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.099
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 16.0328
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14059
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3760
_reflns_number_gt                2595
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2006)'
_computing_publication_material  'PLATON (Spek, 2006)'

_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)+(0.0407P)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         3760
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_restrained_S_all      0.861
_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 0.07201(10) 0.42910(7) -0.37452(8) 0.0268(3) Uani 1 1 d . . .
O2 O -0.10464(11) 0.35363(7) -0.39636(8) 0.0354(3) Uani 1 1 d . . .
O4 O 0.36529(10) 0.36376(6) -0.04658(8) 0.0259(3) Uani 1 1 d . . .
O35 O 0.00488(11) 0.45457(7) 0.14694(9) 0.0439(3) Uani 1 1 d . . .
O37 O 0.46251(10) 0.32542(7) 0.39422(9) 0.0360(3) Uani 1 1 d . . .
N1 N 0.16881(14) 0.26906(8) -0.06426(10) 0.0248(3) Uani 1 1 d . . .
C2 C 0.02101(16) 0.37590(10) -0.32965(12) 0.0233(4) Uani 1 1 d . . .
C3 C 0.12229(14) 0.35391(9) -0.21297(11) 0.0182(3) Uani 1 1 d . . .
C4 C 0.27173(15) 0.38264(9) -0.14724(12) 0.0200(3) Uani 1 1 d . . .
C5 C 0.45961(15) 0.46704(9) -0.14572(12) 0.0241(4) Uani 1 1 d . . .
H5 H 0.5300 0.4551 -0.0688 0.029 Uiso 1 1 calc R . .
C6 C 0.49975(16) 0.51399(10) -0.20082(13) 0.0277(4) Uani 1 1 d . . .
H6 H 0.5977 0.5339 -0.1623 0.033 Uiso 1 1 calc R . .
C7 C 0.39649(16) 0.53213(10) -0.31290(13) 0.0299(4) Uani 1 1 d . . .
H7 H 0.4250 0.5637 -0.3510 0.036 Uiso 1 1 calc R . .
C8 C 0.25300(16) 0.50505(10) -0.37003(12) 0.0280(4) Uani 1 1 d . . .
H8 H 0.1819 0.5190 -0.4463 0.034 Uiso 1 1 calc R . .
C9 C 0.21538(14) 0.45696(9) -0.31325(12) 0.0217(3) Uani 1 1 d . . .
C10 C 0.31605(14) 0.43678(9) -0.20209(11) 0.0180(3) Uani 1 1 d . . .
C31 C 0.07253(15) 0.29974(9) -0.16536(12) 0.0200(3) Uani 1 1 d . . .
C311 C -0.08529(15) 0.27821(9) -0.22312(11) 0.0197(3) Uani 1 1 d . . .
C312 C -0.13663(16) 0.19555(10) -0.26050(12) 0.0258(4) Uani 1 1 d . . .
H312 H -0.0720 0.1521 -0.2517 0.031 Uiso 1 1 calc R . .
C313 C -0.28200(16) 0.17676(11) -0.31049(12) 0.0295(4) Uani 1 1 d . . .
H313 H -0.3178 0.1204 -0.3374 0.035 Uiso 1 1 calc R . .
C314 C -0.37548(16) 0.23880(11) -0.32167(12) 0.0308(4) Uani 1 1 d . . .
H314 H -0.4752 0.2252 -0.3555 0.037 Uiso 1 1 calc R . .
C315 C -0.32444(16) 0.32086(11) -0.28381(13) 0.0330(4) Uani 1 1 d . . .
H315 H -0.3888 0.3637 -0.2909 0.040 Uiso 1 1 calc R . .
C316 C -0.17955(15) 0.34097(10) -0.23547(12) 0.0272(4) Uani 1 1 d . . .
H316 H -0.1450 0.3978 -0.2108 0.033 Uiso 1 1 calc R . .
C32 C 0.14140(16) 0.22083(10) 0.00513(12) 0.0264(4) Uani 1 1 d . . .
H32A H 0.2047 0.1692 0.0355 0.032 Uiso 1 1 calc R . .
H32B H 0.0379 0.2017 -0.0406 0.032 Uiso 1 1 calc R . .
C33 C 0.17307(15) 0.27640(9) 0.09936(12) 0.0222(3) Uani 1 1 d . A .
C34 C 0.06874(15) 0.33635(10) 0.07778(12) 0.0251(4) Uani 1 1 d . . .
H34 H -0.0233 0.3389 0.0063 0.030 Uiso 1 1 calc R . .
C35 C 0.09898(16) 0.39217(10) 0.16015(13) 0.0307(4) Uani 1 1 d . A .
C36 C 0.23359(18) 0.38805(11) 0.26518(14) 0.0439(5) Uani 1 1 d . . .
C37 C 0.33611(15) 0.32585(10) 0.28793(13) 0.0271(4) Uani 1 1 d . A .
C38 C 0.30628(15) 0.27082(10) 0.20432(12) 0.0227(4) Uani 1 1 d . . .
H38 H 0.3769 0.2294 0.2188 0.027 Uiso 1 1 calc R A .
C371 C 0.57625(15) 0.26694(10) 0.41979(13) 0.0321(4) Uani 1 1 d . . .
H37A H 0.6004 0.2763 0.3681 0.048 Uiso 1 1 calc R . .
H37B H 0.5423 0.2078 0.4126 0.048 Uiso 1 1 calc R . .
H37C H 0.6637 0.2768 0.4961 0.048 Uiso 1 1 calc R . .
C351 C -0.13587(16) 0.45854(11) 0.04143(14) 0.0395(5) Uani 1 1 d . . .
H35A H -0.1871 0.4038 0.0266 0.059 Uiso 1 1 calc R . .
H35B H -0.1238 0.4695 -0.0167 0.059 Uiso 1 1 calc R . .
H35C H -0.1934 0.5050 0.0420 0.059 Uiso 1 1 calc R . .
O36A O 0.2845(2) 0.46046(14) 0.32853(18) 0.0258(9) Uani 0.533(5) 1 d P A 1
C36A C 0.2629(6) 0.4478(3) 0.4107(4) 0.0395(13) Uani 0.533(5) 1 d P A 1
H36A H 0.3241 0.4000 0.4590 0.059 Uiso 0.533(5) 1 calc PR A 1
H36B H 0.1595 0.4345 0.3748 0.059 Uiso 0.533(5) 1 calc PR A 1
H36C H 0.2901 0.5001 0.4553 0.059 Uiso 0.533(5) 1 calc PR A 1
O36B O 0.2352(4) 0.4279(2) 0.3590(3) 0.0275(10) Uani 0.467(5) 1 d P A 2
C36B C 0.3597(4) 0.4842(2) 0.4256(3) 0.0283(12) Uani 0.467(5) 1 d P A 2
H36D H 0.3976 0.4995 0.3841 0.043 Uiso 0.467(5) 1 calc PR A 2
H36E H 0.4365 0.4549 0.4946 0.043 Uiso 0.467(5) 1 calc PR A 2
H36F H 0.3297 0.5363 0.4434 0.043 Uiso 0.467(5) 1 calc PR A 2
H1 H 0.2632(18) 0.2918(10) -0.0299(14) 0.043(5) Uiso 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 C9 1.3786(16) . ?
O1 C2 1.3986(17) . ?
O2 C2 1.2052(16) . ?
O4 C4 1.2556(16) . ?
O35 C35 1.3717(18) . ?
O35 C351 1.4273(17) . ?
O37 C37 1.3653(17) . ?
O37 C371 1.4361(17) . ?
N1 C31 1.3193(18) . ?
N1 C32 1.4654(18) . ?
N1 H1 0.940(17) . ?
C2 C3 1.4479(19) . ?
C3 C31 1.428(2) . ?
C3 C4 1.4346(18) . ?
C4 C10 1.467(2) . ?
C5 C6 1.375(2) . ?
C5 C10 1.3979(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3806(19) . ?
C31 C311 1.4929(19) . ?
C311 C316 1.381(2) . ?
C311 C312 1.386(2) . ?
C312 C313 1.379(2) . ?
C312 H312 0.9500 . ?
C313 C314 1.373(2) . ?
C313 H313 0.9500 . ?
C314 C315 1.378(2) . ?
C314 H314 0.9500 . ?
C315 C316 1.384(2) . ?
C315 H315 0.9500 . ?
C316 H316 0.9500 . ?
C32 C33 1.509(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C38 1.3876(19) . ?
C33 C34 1.389(2) . ?
C34 C35 1.378(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.393(2) . ?
C36 O36A 1.361(3) . ?
C36 C37 1.394(2) . ?
C36 O36B 1.534(4) . ?
C37 C38 1.386(2) . ?
C38 H38 0.9500 . ?
C371 H37A 0.9800 . ?
C371 H37B 0.9800 . ?
C371 H37C 0.9800 . ?
C351 H35A 0.9800 . ?
C351 H35B 0.9800 . ?
C351 H35C 0.9800 . ?
O36A C36A 1.414(6) . ?
C36A H36A 0.9800 . ?
C36A H36B 0.9800 . ?
C36A H36C 0.9800 . ?
O36B C36B 1.442(6) . ?
C36B H36D 0.9800 . ?
C36B H36E 0.9800 . ?
C36B H36F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C2 122.33(11) . . ?
C35 O35 C351 116.79(12) . . ?
C37 O37 C371 117.68(12) . . ?
C31 N1 C32 128.44(13) . . ?
C31 N1 H1 112.4(10) . . ?
C32 N1 H1 117.9(10) . . ?
O2 C2 O1 113.61(12) . . ?
O2 C2 C3 128.61(14) . . ?
O1 C2 C3 117.78(12) . . ?
C31 C3 C4 120.34(12) . . ?
C31 C3 C2 118.74(12) . . ?
C4 C3 C2 120.86(13) . . ?
O4 C4 C3 123.66(14) . . ?
O4 C4 C10 118.91(13) . . ?
C3 C4 C10 117.43(12) . . ?
C6 C5 C10 120.50(14) . . ?
C6 C5 H5 119.8 . . ?
C10 C5 H5 119.8 . . ?
C5 C6 C7 119.67(14) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 121.13(15) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 118.23(14) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
O1 C9 C10 121.76(13) . . ?
O1 C9 C8 116.18(13) . . ?
C10 C9 C8 122.04(13) . . ?
C9 C10 C5 118.40(14) . . ?
C9 C10 C4 119.74(12) . . ?
C5 C10 C4 121.83(13) . . ?
N1 C31 C3 119.13(13) . . ?
N1 C31 C311 117.77(13) . . ?
C3 C31 C311 123.06(12) . . ?
C316 C311 C312 119.90(13) . . ?
C316 C311 C31 119.24(13) . . ?
C312 C311 C31 120.82(13) . . ?
C313 C312 C311 119.64(14) . . ?
C313 C312 H312 120.2 . . ?
C311 C312 H312 120.2 . . ?
C314 C313 C312 120.55(15) . . ?
C314 C313 H313 119.7 . . ?
C312 C313 H313 119.7 . . ?
C313 C314 C315 119.91(14) . . ?
C313 C314 H314 120.0 . . ?
C315 C314 H314 120.0 . . ?
C314 C315 C316 120.11(15) . . ?
C314 C315 H315 119.9 . . ?
C316 C315 H315 119.9 . . ?
C311 C316 C315 119.87(14) . . ?
C311 C316 H316 120.1 . . ?
C315 C316 H316 120.1 . . ?
N1 C32 C33 110.07(12) . . ?
N1 C32 H32A 109.6 . . ?
C33 C32 H32A 109.6 . . ?
N1 C32 H32B 109.6 . . ?
C33 C32 H32B 109.6 . . ?
H32A C32 H32B 108.2 . . ?
C38 C33 C34 120.40(14) . . ?
C38 C33 C32 120.89(13) . . ?
C34 C33 C32 118.64(13) . . ?
C35 C34 C33 119.91(13) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
O35 C35 C34 124.53(13) . . ?
O35 C35 C36 115.44(14) . . ?
C34 C35 C36 120.03(14) . . ?
O36A C36 C35 118.13(16) . . ?
O36A C36 C37 117.55(15) . . ?
C35 C36 C37 120.01(15) . . ?
O36A C36 O36B 41.89(15) . . ?
C35 C36 O36B 114.87(18) . . ?
C37 C36 O36B 120.83(18) . . ?
O37 C37 C38 124.79(13) . . ?
O37 C37 C36 115.47(14) . . ?
C38 C37 C36 119.73(14) . . ?
C37 C38 C33 119.86(14) . . ?
C37 C38 H38 120.1 . . ?
C33 C38 H38 120.1 . . ?
O37 C371 H37A 109.5 . . ?
O37 C371 H37B 109.5 . . ?
H37A C371 H37B 109.5 . . ?
O37 C371 H37C 109.5 . . ?
H37A C371 H37C 109.5 . . ?
H37B C371 H37C 109.5 . . ?
O35 C351 H35A 109.5 . . ?
O35 C351 H35B 109.5 . . ?
H35A C351 H35B 109.5 . . ?
O35 C351 H35C 109.5 . . ?
H35A C351 H35C 109.5 . . ?
H35B C351 H35C 109.5 . . ?
C36 O36A C36A 105.8(3) . . ?
C36B O36B C36 110.3(3) . . ?
O36B C36B H36D 109.5 . . ?
O36B C36B H36E 109.5 . . ?
H36D C36B H36E 109.5 . . ?
O36B C36B H36F 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.033

_database_code_depnum_ccdc_archive 'CCDC 990516'
#######################################################################
#
#                 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        
; 
  4-hydroxy-3-[(2-imidazol-1-yl-ethylimino)-methyl]-chromen-2-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N3 O3'
_chemical_formula_sum            'C16 H15 N3 O3'
_chemical_formula_weight         297.31

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.166(3)
_cell_length_b                   17.642(3)
_cell_length_c                   10.775(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.06(2)
_cell_angle_gamma                90.00
_cell_volume                     1382.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    54389
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      21.72

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.097
_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      100(2)
_diffrn_radiation_wavelength     0.60000
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_measurement_device_type  'Huber diffractometer'
_diffrn_detector_type            'MarCCD detector'
_diffrn_measurement_method       'φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54389
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0092
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         21.72
_reflns_number_total             2668
_reflns_number_gt                2528
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'MarCCD (Paulmann & Morgenroth, 2006)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2006)'
_computing_publication_material  'PLATON (Spek, 2006)'

_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)+(0.0584P)²+0.5869P] 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         2668
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.15568(12) -0.06919(5) -0.17849(9) 0.0202(2) Uani 1 1 d . . .
O2 O 0.13596(12) -0.06689(5) 0.01851(10) 0.0233(2) Uani 1 1 d . . .
O4 O 0.40822(11) 0.13969(5) -0.10287(9) 0.0186(2) Uani 1 1 d . . .
N1 N 0.37247(13) 0.14369(6) 0.13985(10) 0.0158(2) Uani 1 1 d . . .
N2 N -0.07944(12) 0.26576(5) 0.17319(9) 0.0131(2) Uani 1 1 d . . .
N3 N -0.37254(13) 0.26799(6) 0.13319(10) 0.0169(2) Uani 1 1 d . . .
C2 C 0.18780(15) -0.03277(6) -0.05535(12) 0.0173(2) Uani 1 1 d . . .
C3 C 0.27694(15) 0.04105(6) -0.02864(12) 0.0154(2) Uani 1 1 d . . .
C4 C 0.33272(14) 0.07624(6) -0.12461(12) 0.0145(2) Uani 1 1 d . . .
C5 C 0.33613(15) 0.06052(7) -0.35661(12) 0.0179(3) Uani 1 1 d . . .
H5 H 0.3930 0.1087 -0.3454 0.022 Uiso 1 1 calc R . .
C6 C 0.29729(16) 0.01790(7) -0.47493(13) 0.0216(3) Uani 1 1 d . . .
H6 H 0.3274 0.0370 -0.5444 0.026 Uiso 1 1 calc R . .
C7 C 0.21362(17) -0.05334(7) -0.49217(13) 0.0236(3) Uani 1 1 d . . .
H7 H 0.1878 -0.0824 -0.5732 0.028 Uiso 1 1 calc R . .
C8 C 0.16815(16) -0.08173(7) -0.39150(13) 0.0220(3) Uani 1 1 d . . .
H8 H 0.1116 -0.1300 -0.4029 0.026 Uiso 1 1 calc R . .
C9 C 0.20698(15) -0.03802(6) -0.27314(12) 0.0160(2) Uani 1 1 d . . .
C10 C 0.29194(14) 0.03282(6) -0.25326(12) 0.0146(2) Uani 1 1 d . . .
C31 C 0.29978(15) 0.07679(6) 0.09512(12) 0.0160(2) Uani 1 1 d . . .
H31 H 0.2584 0.0497 0.1518 0.019 Uiso 1 1 calc R . .
C32 C 0.39337(15) 0.17690(7) 0.27267(12) 0.0179(3) Uani 1 1 d . . .
H32B H 0.4611 0.2254 0.2890 0.022 Uiso 1 1 calc R . .
H32A H 0.4684 0.1421 0.3499 0.022 Uiso 1 1 calc R . .
C33 C 0.21046(15) 0.19151(6) 0.27572(12) 0.0153(2) Uani 1 1 d . . .
H33A H 0.1459 0.1427 0.2657 0.018 Uiso 1 1 calc R . .
H33B H 0.2352 0.2135 0.3671 0.018 Uiso 1 1 calc R . .
C34 C 0.08588(15) 0.24533(7) 0.15989(12) 0.0161(2) Uani 1 1 d . . .
H34B H 0.1552 0.2919 0.1632 0.019 Uiso 1 1 calc R . .
H34A H 0.0491 0.2208 0.0684 0.019 Uiso 1 1 calc R . .
C35 C -0.25386(15) 0.24076(6) 0.09212(11) 0.0149(2) Uani 1 1 d . . .
H35 H -0.2867 0.2076 0.0150 0.018 Uiso 1 1 calc R . .
C36 C -0.26742(16) 0.31290(6) 0.24757(12) 0.0156(2) Uani 1 1 d . . .
H36 H -0.3143 0.3404 0.3003 0.019 Uiso 1 1 calc R . .
C37 C -0.08712(15) 0.31212(6) 0.27413(11) 0.0143(2) Uani 1 1 d . . .
H37 H 0.0124 0.3380 0.3468 0.017 Uiso 1 1 calc R . .
H1 H 0.422(2) 0.1713(10) 0.0902(18) 0.035(4) Uiso 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 C9 1.3809(15) . ?
O1 C2 1.3875(15) . ?
O2 C2 1.2171(15) . ?
O4 C4 1.2477(14) . ?
N1 C31 1.3103(16) . ?
N1 C32 1.4827(15) . ?
N1 H1 0.937(18) . ?
N2 C35 1.3617(15) . ?
N2 C37 1.3849(14) . ?
N2 C34 1.4660(15) . ?
N3 C35 1.3252(15) . ?
N3 C36 1.3859(15) . ?
C2 C3 1.4554(16) . ?
C3 C31 1.4088(17) . ?
C3 C4 1.4459(16) . ?
C4 C10 1.4829(16) . ?
C5 C6 1.3869(17) . ?
C5 C10 1.4053(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4020(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3977(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3978(16) . ?
C31 H31 0.9500 . ?
C32 C33 1.5308(16) . ?
C32 H32B 0.9900 . ?
C32 H32A 0.9900 . ?
C33 C34 1.5293(16) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34B 0.9900 . ?
C34 H34A 0.9900 . ?
C35 H35 0.9500 . ?
C36 C37 1.3661(17) . ?
C36 H36 0.9500 . ?
C37 H37 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
C9 O1 C2 122.21(9) . . ?
C31 N1 C32 123.01(10) . . ?
C31 N1 H1 119.9(11) . . ?
C32 N1 H1 117.0(11) . . ?
C35 N2 C37 106.69(9) . . ?
C35 N2 C34 126.77(10) . . ?
C37 N2 C34 126.50(9) . . ?
C35 N3 C36 104.65(10) . . ?
O2 C2 O1 115.19(11) . . ?
O2 C2 C3 127.21(11) . . ?
O1 C2 C3 117.60(10) . . ?
C31 C3 C4 122.39(11) . . ?
C31 C3 C2 115.25(10) . . ?
C4 C3 C2 122.33(10) . . ?
O4 C4 C3 122.72(10) . . ?
O4 C4 C10 121.36(10) . . ?
C3 C4 C10 115.91(10) . . ?
C6 C5 C10 120.41(11) . . ?
C6 C5 H5 119.8 . . ?
C10 C5 H5 119.8 . . ?
C5 C6 C7 120.11(12) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.45(11) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 118.88(11) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
O1 C9 C8 115.79(11) . . ?
O1 C9 C10 122.61(10) . . ?
C8 C9 C10 121.60(11) . . ?
C9 C10 C5 118.55(11) . . ?
C9 C10 C4 119.33(10) . . ?
C5 C10 C4 122.13(10) . . ?
N1 C31 C3 126.44(11) . . ?
N1 C31 H31 116.8 . . ?
C3 C31 H31 116.8 . . ?
N1 C32 C33 113.72(9) . . ?
N1 C32 H32B 108.8 . . ?
C33 C32 H32B 108.8 . . ?
N1 C32 H32A 108.8 . . ?
C33 C32 H32A 108.8 . . ?
H32B C32 H32A 107.7 . . ?
C34 C33 C32 112.35(9) . . ?
C34 C33 H33A 109.1 . . ?
C32 C33 H33A 109.1 . . ?
C34 C33 H33B 109.1 . . ?
C32 C33 H33B 109.1 . . ?
H33A C33 H33B 107.9 . . ?
N2 C34 C33 111.91(9) . . ?
N2 C34 H34B 109.2 . . ?
C33 C34 H34B 109.2 . . ?
N2 C34 H34A 109.2 . . ?
C33 C34 H34A 109.2 . . ?
H34B C34 H34A 107.9 . . ?
N3 C35 N2 112.26(10) . . ?
N3 C35 H35 123.9 . . ?
N2 C35 H35 123.9 . . ?
C37 C36 N3 110.67(10) . . ?
C37 C36 H36 124.7 . . ?
N3 C36 H36 124.7 . . ?
C36 C37 N2 105.72(10) . . ?
C36 C37 H37 127.1 . . ?
N2 C37 H37 127.1 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        21.72
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 990517'
