# 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_gehen_twin1_hklf5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H13 N3 O'
_chemical_formula_weight         167.21

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   7.4126(6)
_cell_length_b                   7.6720(6)
_cell_length_c                   8.1731(6)
_cell_angle_alpha                88.391(6)
_cell_angle_beta                 83.564(6)
_cell_angle_gamma                80.059(6)
_cell_volume                     454.92(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6731
_cell_measurement_theta_min      7.9650
_cell_measurement_theta_max      75.3380

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             180
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80018
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;

_exptl_special_details           
;
 The crystal was a non-merohedral twin by 180 degree rotation about
 (a*-c*). The untwinning routines merge equivalent reflections, so
 that R(int) is meaningless and the number of reflections should be
 interpreted with caution.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.3543
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3650
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0081
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.45
_diffrn_reflns_theta_max         75.82
_reflns_number_total             3650
_reflns_number_gt                3328
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_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.

 The twin scale factor refined to 0.499(3).

 The NH hydrogens were refined freely. Methyl groups were refined as
 ideally disordered hexagons of half-occupied hydrogen atoms. Other
 hydrogens were included using a riding model starting from calculated
 positions.
;

_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)+(0.0638P)²+0.0585P] 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         3650
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.096
_refine_ls_shift/su_mean         0.003

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
N11 N 0.26677(9) 0.57334(9) 0.41213(8) 0.02384(17) Uani 1 1 d . . .
C12 C 0.31101(11) 0.40650(11) 0.35586(10) 0.02496(19) Uani 1 1 d . . .
C13 C 0.30386(11) 0.25995(11) 0.45917(11) 0.0277(2) Uani 1 1 d . . .
H13 H 0.3354 0.1436 0.4161 0.033 Uiso 1 1 calc R . .
C14 C 0.25026(11) 0.28636(12) 0.62519(11) 0.0298(2) Uani 1 1 d . . .
H14 H 0.2446 0.1884 0.6982 0.036 Uiso 1 1 calc R . .
C15 C 0.20485(11) 0.45785(13) 0.68373(10) 0.0300(2) Uani 1 1 d . . .
H15 H 0.1675 0.4789 0.7975 0.036 Uiso 1 1 calc R . .
C16 C 0.21455(11) 0.59904(11) 0.57403(10) 0.02548(19) Uani 1 1 d . . .
C17 C 0.36885(15) 0.38443(12) 0.17465(11) 0.0356(2) Uani 1 1 d . . .
H17A H 0.3516 0.5005 0.1200 0.053 Uiso 0.50 1 calc PR . .
H17B H 0.2937 0.3087 0.1286 0.053 Uiso 0.50 1 calc PR . .
H17C H 0.4990 0.3297 0.1570 0.053 Uiso 0.50 1 calc PR . .
H17D H 0.4113 0.2587 0.1504 0.053 Uiso 0.50 1 calc PR . .
H17E H 0.4691 0.4506 0.1418 0.053 Uiso 0.50 1 calc PR . .
H17F H 0.2639 0.4296 0.1134 0.053 Uiso 0.50 1 calc PR . .
C18 C 0.16746(14) 0.78797(13) 0.62974(12) 0.0364(2) Uani 1 1 d . . .
H18A H 0.2355 0.8618 0.5548 0.055 Uiso 0.50 1 calc PR . .
H18B H 0.2013 0.7959 0.7415 0.055 Uiso 0.50 1 calc PR . .
H18C H 0.0348 0.8294 0.6293 0.055 Uiso 0.50 1 calc PR . .
H18D H 0.0789 0.7963 0.7289 0.055 Uiso 0.50 1 calc PR . .
H18E H 0.1131 0.8622 0.5422 0.055 Uiso 0.50 1 calc PR . .
H18F H 0.2796 0.8287 0.6544 0.055 Uiso 0.50 1 calc PR . .
N1 N 0.10780(10) 0.83459(10) 0.13881(9) 0.02794(18) Uani 1 1 d . . .
H01 H 0.1147(15) 0.7632(16) 0.2223(14) 0.037(3) Uiso 1 1 d . . .
H02 H -0.0008(17) 0.8763(15) 0.1015(14) 0.037(3) Uiso 1 1 d . . .
C2 C 0.25318(11) 0.91448(10) 0.08945(9) 0.02083(17) Uani 1 1 d . . .
N3 N 0.40258(9) 0.86837(9) 0.17188(9) 0.02393(17) Uani 1 1 d . . .
H03 H 0.4010(15) 0.7815(15) 0.2478(14) 0.035(3) Uiso 1 1 d . . .
H04 H 0.5070(16) 0.9039(14) 0.1289(13) 0.029(2) Uiso 1 1 d . . .
O1 O 0.24989(7) 1.02516(7) -0.02582(7) 0.02473(15) 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
N11 C12 1.3460(11) . ?
N11 C16 1.3466(10) . ?
C12 C13 1.3917(12) . ?
C12 C17 1.5009(12) . ?
C13 C14 1.3809(13) . ?
C14 C15 1.3854(14) . ?
C15 C16 1.3929(12) . ?
C16 C18 1.5023(12) . ?
N1 C2 1.3478(10) . ?
C2 O1 1.2499(10) . ?
C2 N3 1.3505(10) . ?

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
C12 N11 C16 118.78(7) . . ?
N11 C12 C13 122.24(8) . . ?
N11 C12 C17 116.87(7) . . ?
C13 C12 C17 120.89(8) . . ?
C14 C13 C12 118.96(8) . . ?
C13 C14 C15 119.01(8) . . ?
C14 C15 C16 119.30(8) . . ?
N11 C16 C15 121.70(8) . . ?
N11 C16 C18 116.40(8) . . ?
C15 C16 C18 121.89(8) . . ?
O1 C2 N1 121.93(7) . . ?
O1 C2 N3 121.88(7) . . ?
N1 C2 N3 116.18(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
C16 N11 C12 C13 0.27(12) . . . . ?
C16 N11 C12 C17 -179.85(7) . . . . ?
N11 C12 C13 C14 -0.25(13) . . . . ?
C17 C12 C13 C14 179.87(8) . . . . ?
C12 C13 C14 C15 0.15(12) . . . . ?
C13 C14 C15 C16 -0.07(12) . . . . ?
C12 N11 C16 C15 -0.18(12) . . . . ?
C12 N11 C16 C18 179.80(7) . . . . ?
C14 C15 C16 N11 0.09(12) . . . . ?
C14 C15 C16 C18 -179.89(8) . . . . ?

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 H01 N11 0.864(12) 2.344(12) 3.1495(10) 155.2(10) .
N3 H03 N11 0.899(12) 2.339(12) 3.1759(10) 154.9(9) .
N1 H02 O1 0.897(13) 2.027(13) 2.9237(9) 177.7(10) 2_575
N3 H04 O1 0.896(12) 2.056(12) 2.9515(9) 177.5(10) 2_675
C14 H14 O1 0.95 2.55 3.4396(10) 156.0 1_546

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        75.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042


# end of cif file
_database_code_depnum_ccdc_archive 'CCDC 990308'
#######################################################################
#
#                 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_laufen

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H17 N5 O2'
_chemical_formula_weight         227.28

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'

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

_cell_length_a                   8.0772(3)
_cell_length_b                   7.2986(3)
_cell_length_c                   20.4169(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1203.64(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10235
_cell_measurement_theta_min      2.7030
_cell_measurement_theta_max      28.3070

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.092
_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  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38287
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         29.37
_reflns_number_total             1710
_reflns_number_gt                1517
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_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. 
  
 NH hydrogens were refined freely and aromatic hydrogens using a riding 
 model starting from calculated positions. Methyl hydrogens were identified 
 from difference syntheses and idealised, whereby the methyl group at C18 
 lay with one hydrogen in the lutidine ring plane and was then refined 
 using a riding model. The methyl group at C17, which contains half- 
 occupied hydrogen sites and is thus necessarily disordered, was allowed 
 to rotate but not tip. 
;

_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)+(0.0519P)²+0.5129P] 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         1710
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
N11 N 0.41604(16) 0.7500 0.46732(6) 0.0189(3) Uani 1 2 d S . .
C12 C 0.4151(2) 0.7500 0.53317(7) 0.0240(3) Uani 1 2 d S . .
C13 C 0.5632(3) 0.7500 0.56923(8) 0.0316(4) Uani 1 2 d S . .
H13 H 0.5607 0.7500 0.6157 0.038 Uiso 1 2 calc SR . .
C14 C 0.7119(2) 0.7500 0.53631(9) 0.0300(4) Uani 1 2 d S . .
H14 H 0.8132 0.7500 0.5599 0.036 Uiso 1 2 calc SR . .
C15 C 0.7127(2) 0.7500 0.46882(9) 0.0259(4) Uani 1 2 d S . .
H15 H 0.8142 0.7500 0.4453 0.031 Uiso 1 2 calc SR . .
C16 C 0.56272(19) 0.7500 0.43587(8) 0.0208(3) Uani 1 2 d S . .
C17 C 0.2491(3) 0.7500 0.56554(9) 0.0382(5) Uani 1 2 d S . .
H17A H 0.2152 0.8765 0.5745 0.057 Uiso 0.50 1 calc PR . .
H17B H 0.2554 0.6817 0.6068 0.057 Uiso 0.50 1 calc PR . .
H17C H 0.1679 0.6919 0.5366 0.057 Uiso 0.50 1 calc PR . .
C18 C 0.5565(2) 0.7500 0.36216(8) 0.0335(4) Uani 1 2 d S . .
H18A H 0.4979 0.6405 0.3469 0.050 Uiso 1 1 d R . .
H18B H 0.6695 0.7500 0.3446 0.050 Uiso 1 2 d SR . .
C1 C 0.07513(17) 0.7500 0.35383(7) 0.0165(3) Uani 1 2 d S . .
N1 N 0.12769(12) 0.59321(13) 0.38207(5) 0.0215(2) Uani 1 1 d . . .
H01 H 0.2071(19) 0.601(2) 0.4107(7) 0.029(4) Uiso 1 1 d . . .
H02 H 0.1024(18) 0.489(2) 0.3636(7) 0.028(4) Uiso 1 1 d . . .
O1 O -0.02090(14) 0.7500 0.30616(5) 0.0210(3) Uani 1 2 d S . .
C2 C -0.08185(17) 0.2500 0.27760(7) 0.0145(3) Uani 1 2 d S . .
N2 N -0.15430(12) 0.40715(13) 0.25925(5) 0.0206(2) Uani 1 1 d . . .
H03 H -0.2498(19) 0.402(2) 0.2388(7) 0.030(4) Uiso 1 1 d . . .
H04 H -0.1140(18) 0.511(2) 0.2732(6) 0.026(3) Uiso 1 1 d . . .
O2 O 0.05114(12) 0.2500 0.31004(5) 0.0163(2) Uani 1 2 d S . .


_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
N11 C12 1.344(2) . ?
N11 C16 1.348(2) . ?
C12 C13 1.404(3) . ?
C12 C17 1.495(2) . ?
C13 C14 1.376(3) . ?
C14 C15 1.378(3) . ?
C15 C16 1.386(2) . ?
C16 C18 1.506(2) . ?
C1 O1 1.2445(18) . ?
C1 N1 1.3498(11) . ?
C1 N1 1.3499(12) 7_575 ?
C2 O2 1.2621(17) . ?
C2 N2 1.3410(11) 7_565 ?
C2 N2 1.3410(11) . ?

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
C12 N11 C16 118.77(13) . . ?
N11 C12 C13 121.30(16) . . ?
N11 C12 C17 116.55(15) . . ?
C13 C12 C17 122.15(15) . . ?
C14 C13 C12 119.15(15) . . ?
C13 C14 C15 119.52(16) . . ?
C14 C15 C16 118.76(16) . . ?
N11 C16 C15 122.50(15) . . ?
N11 C16 C18 116.56(14) . . ?
C15 C16 C18 120.94(15) . . ?
O1 C1 N1 122.01(6) . . ?
O1 C1 N1 122.01(6) . 7_575 ?
N1 C1 N1 115.94(13) . 7_575 ?
O2 C2 N2 121.20(6) . 7_565 ?
O2 C2 N2 121.20(6) . . ?
N2 C2 N2 117.59(13) 7_565 . ?

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
C16 N11 C12 C13 0.0 . . . . ?
C16 N11 C12 C17 180.0 . . . . ?
N11 C12 C13 C14 0.0 . . . . ?
C17 C12 C13 C14 180.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C12 N11 C16 C15 0.000(1) . . . . ?
C12 N11 C16 C18 180.0 . . . . ?
C14 C15 C16 N11 0.000(1) . . . . ?
C14 C15 C16 C18 180.0 . . . . ?

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 H01 N11 0.869(15) 2.318(16) 3.1248(15) 154.4(13) .
N1 H02 O2 0.871(16) 2.102(16) 2.9698(11) 174.2(13) .
N2 H03 O2 0.878(15) 2.192(16) 2.9963(13) 152.1(14) 6_556
N2 H04 O1 0.870(15) 2.018(16) 2.8879(11) 179.5(13) .

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        28.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.045


# end of cif file 
_database_code_depnum_ccdc_archive 'CCDC 990309'
#######################################################################
#
#                 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_nuss

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H17 N5 O2'
_chemical_formula_weight         227.27

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           monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.5829(4)
_cell_length_b                   21.4843(8)
_cell_length_c                   7.2050(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.405(6)
_cell_angle_gamma                90
_cell_volume                     1209.87(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17176
_cell_measurement_theta_min      4.0920
_cell_measurement_theta_max      76.6800

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.758
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Nova microsource'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.3543
_diffrn_reflns_number            27700
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.115
_diffrn_reflns_theta_max         76.879
_diffrn_reflns_theta_full        75.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2403
_reflns_number_gt                2377
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.958

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL

_refine_special_details          
;
 Refined as a 2-component twin related by the matrix
 1 0 1   0 -1 0   0 0 -1. The relative twin volume refined to
 0.220(7) for the smaller component. Because of the C-centring, some
 reflections are almost exactly overlapped and some are non-overlapped
 (when one component is systematically absent); this is sometimes
 termed "reticular (pseudo)merohedry". The program SHELXL-2012
 takes correct account of this.

 Attempts to allow for additional racemic twinning gave two additional
 BASF parameters not significantly different from zero. The anomalous
 scattering is however a small effect (light-atom structure) even
 with copper radiation.

 NH hydrogens were refined freely but with a common isotropic
 U value and with restrained N-H and H...H distances. Methyls
 were refined as idealised rigid groups allowed to rotate but not
 tip. Other H were refined using a riding model starting from
 calculated positions.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0985P)²+0.4071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1098 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(14)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2403
_refine_ls_number_parameters     173
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1312
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.003
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9151(2) 0.30341(9) 0.8905(4) 0.0265(5) Uani 1 1 d . . . . .
C1 C 0.8190(3) 0.35055(12) 0.8419(5) 0.0236(6) Uani 1 1 d . . . . .
N1 N 0.7711(3) 0.37923(12) 0.9757(4) 0.0287(6) Uani 1 1 d D . . . .
H01 H 0.689(5) 0.4085(18) 0.924(6) 0.041(4) Uiso 1 1 d D U . . .
H02 H 0.799(5) 0.364(2) 1.101(5) 0.041(4) Uiso 1 1 d D U . . .
N2 N 0.7639(4) 0.37533(12) 0.6542(5) 0.0313(6) Uani 1 1 d D . . . .
H03 H 0.686(5) 0.4071(17) 0.622(7) 0.041(4) Uiso 1 1 d D U . . .
H04 H 0.795(5) 0.362(2) 0.557(6) 0.041(4) Uiso 1 1 d D U . . .
O2 O 0.8802(2) 0.31397(9) 0.3679(4) 0.0257(5) Uani 1 1 d . . . . .
C2 C 1.0308(3) 0.29346(11) 0.4434(5) 0.0235(5) Uani 1 1 d . . . . .
N3 N 1.1123(3) 0.27935(14) 0.3252(5) 0.0309(6) Uani 1 1 d D . . . .
H05 H 1.222(4) 0.264(2) 0.375(6) 0.041(4) Uiso 1 1 d D U . . .
H06 H 1.066(5) 0.286(2) 0.187(4) 0.041(4) Uiso 1 1 d D U . . .
N4 N 1.1175(3) 0.28651(12) 0.6480(4) 0.0273(6) Uani 1 1 d D . . . .
H07 H 1.212(4) 0.2622(19) 0.684(7) 0.041(4) Uiso 1 1 d D U . . .
H08 H 1.062(5) 0.285(2) 0.731(6) 0.041(4) Uiso 1 1 d D U . . .
N11 N 0.5143(3) 0.47732(13) 0.6961(5) 0.0356(7) Uani 1 1 d . . . . .
C12 C 0.5340(4) 0.53937(16) 0.7039(6) 0.0286(6) Uani 1 1 d . . . . .
H12 H 0.6473 0.5554 0.7594 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3988(4) 0.58186(13) 0.6359(5) 0.0271(6) Uani 1 1 d . . . . .
C14 C 0.2351(4) 0.55698(14) 0.5558(6) 0.0301(6) Uani 1 1 d . . . . .
H14 H 0.1392 0.5842 0.5068 0.036 Uiso 1 1 calc R U . . .
C15 C 0.2087(4) 0.49323(14) 0.5458(7) 0.0336(7) Uani 1 1 d . . . . .
C16 C 0.3533(4) 0.45557(15) 0.6182(6) 0.0351(7) Uani 1 1 d . . . . .
H16 H 0.3371 0.4117 0.6123 0.042 Uiso 1 1 calc R U . . .
C17 C 0.4305(4) 0.65074(14) 0.6469(7) 0.0394(8) Uani 1 1 d . . . . .
H17A H 0.3454 0.6707 0.5248 0.059 Uiso 1 1 calc R U . . .
H17B H 0.5455 0.6588 0.6548 0.059 Uiso 1 1 calc R U . . .
H17C H 0.4213 0.6677 0.7683 0.059 Uiso 1 1 calc R U . . .
C18 C 0.0331(5) 0.46536(18) 0.4588(8) 0.0492(10) Uani 1 1 d . . . . .
H18A H -0.0499 0.4964 0.4609 0.074 Uiso 1 1 calc R U . . .
H18B H 0.0306 0.4292 0.5404 0.074 Uiso 1 1 calc R U . . .
H18C H 0.0035 0.4523 0.3179 0.074 Uiso 1 1 calc R U . . .


_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 C1 1.261(3) . ?
C1 N1 1.343(5) . ?
C1 N2 1.344(5) . ?
O2 C2 1.257(3) . ?
C2 N3 1.341(5) . ?
C2 N4 1.357(4) . ?
N11 C12 1.342(4) . ?
N11 C16 1.342(4) . ?
C12 C13 1.396(4) . ?
C13 C14 1.387(4) . ?
C13 C17 1.501(4) . ?
C14 C15 1.385(4) . ?
C15 C16 1.390(5) . ?
C15 C18 1.498(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 N1 121.9(3) . . ?
O1 C1 N2 121.0(3) . . ?
N1 C1 N2 117.1(2) . . ?
O2 C2 N3 121.1(3) . . ?
O2 C2 N4 120.9(3) . . ?
N3 C2 N4 118.0(3) . . ?
C12 N11 C16 117.0(3) . . ?
N11 C12 C13 124.2(3) . . ?
C14 C13 C12 116.5(3) . . ?
C14 C13 C17 122.2(3) . . ?
C12 C13 C17 121.3(3) . . ?
C15 C14 C13 121.2(3) . . ?
C14 C15 C16 117.1(3) . . ?
C14 C15 C18 122.1(3) . . ?
C16 C15 C18 120.8(3) . . ?
N11 C16 C15 124.0(3) . . ?

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
C16 N11 C12 C13 -0.3(5) . . . . ?
N11 C12 C13 C14 0.0(6) . . . . ?
N11 C12 C13 C17 -179.2(4) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C17 C13 C14 C15 179.6(4) . . . . ?
C13 C14 C15 C16 -0.4(7) . . . . ?
C13 C14 C15 C18 -179.6(5) . . . . ?
C12 N11 C16 C15 0.3(6) . . . . ?
C14 C15 C16 N11 0.0(7) . . . . ?
C18 C15 C16 N11 179.3(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 H01 N11 0.90(2) 2.26(3) 3.113(4) 158(4) .
N1 H02 O2 0.89(2) 2.06(2) 2.939(4) 168(4) 1_556
N2 H03 N11 0.91(2) 2.32(3) 3.165(4) 153(4) .
N2 H04 O2 0.90(2) 2.07(3) 2.948(4) 168(4) .
N3 H05 O1 0.92(2) 2.16(3) 3.021(3) 154(4) 4_554
N3 H06 O1 0.92(2) 2.03(3) 2.926(4) 167(4) 1_554
N4 H07 O2 0.91(2) 2.22(3) 3.050(3) 152(4) 4
N4 H08 O1 0.91(2) 2.06(2) 2.951(4) 166(4) .

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4



# end of cif file

_database_code_depnum_ccdc_archive 'CCDC 990310'
#######################################################################
#
#                 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_nuss

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H17 N5 O2'
_chemical_formula_weight         227.28

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'A b m 2'

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

_cell_length_a                   21.7368(15)
_cell_length_b                   7.2102(6)
_cell_length_c                   15.5904(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2443.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2312
_cell_measurement_theta_min      2.7580
_cell_measurement_theta_max      23.2000

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3000
_exptl_crystal_size_mid          0.1300
_exptl_crystal_size_min          0.0200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93041
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21459
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         26.36
_reflns_number_total             1409
_reflns_number_gt                1176
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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. 
  
The NH hydrogen were refined freely. The methyl groups were refined as 
idealised rigid groups allowed to rotate but not tip. Other hydrogens were 
included using a riding model starting from calculated positions. 
;

_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)+(0.0390P)²+0.8610P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_number_reflns         1409
_refine_ls_number_parameters     217
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30505(12) 0.7500 0.92892(18) 0.0413(8) Uani 1 2 d S . .
C1 C 0.34859(18) 0.7500 0.8774(3) 0.0305(9) Uani 1 2 d S . .
N1 N 0.37393(11) 0.5920(4) 0.84871(17) 0.0407(7) Uani 1 1 d D . .
H01 H 0.4022(11) 0.601(4) 0.8087(16) 0.044(9) Uiso 1 1 d D . .
H02 H 0.3573(11) 0.489(3) 0.8671(16) 0.029(7) Uiso 1 1 d D . .
O2 O 0.30793(11) 0.2500 0.90587(16) 0.0288(6) Uani 1 2 d S . .
C2 C 0.28673(16) 0.2500 0.9809(2) 0.0269(8) Uani 1 2 d S . .
N2 N 0.27561(12) 0.0914(3) 1.02249(16) 0.0372(6) Uani 1 1 d D . .
H03 H 0.2563(13) 0.092(5) 1.0718(14) 0.054(10) Uiso 1 1 d D . .
H04 H 0.2864(12) -0.013(3) 0.9961(17) 0.034(8) Uiso 1 1 d D . .
O3 O 0.18072(11) 0.2500 0.65785(16) 0.0305(6) Uani 1 2 d S . .
C3 C 0.20632(15) 0.2500 0.7293(2) 0.0244(8) Uani 1 2 d S . .
N3 N 0.21990(11) 0.4091(3) 0.77039(15) 0.0323(6) Uani 1 1 d D . .
H05 H 0.2429(11) 0.405(4) 0.8157(14) 0.039(9) Uiso 1 1 d D . .
H06 H 0.2124(12) 0.512(3) 0.7415(16) 0.037(8) Uiso 1 1 d D . .
O4 O 0.19709(11) 0.7500 0.66902(18) 0.0272(6) Uani 1 2 d S . .
C4 C 0.14670(16) 0.7500 0.6297(2) 0.0235(8) Uani 1 2 d S . .
N4 N 0.11867(10) 0.5918(3) 0.60820(15) 0.0333(6) Uani 1 1 d D . .
H07 H 0.0855(10) 0.598(4) 0.5756(16) 0.037(8) Uiso 1 1 d D . .
H08 H 0.1380(11) 0.489(3) 0.6227(18) 0.040(8) Uiso 1 1 d D . .
N11 N 0.47182(19) 0.7500 0.7178(3) 0.0540(12) Uani 1 2 d S . .
C12 C 0.5331(2) 0.7500 0.7273(3) 0.0424(11) Uani 1 2 d S . .
H12 H 0.5491 0.7500 0.7840 0.051 Uiso 1 2 calc SR . .
C13 C 0.57413(17) 0.7500 0.6603(2) 0.0311(9) Uani 1 2 d S . .
C14 C 0.54932(19) 0.7500 0.5794(3) 0.0419(11) Uani 1 2 d S . .
H14 H 0.5760 0.7500 0.5311 0.050 Uiso 1 2 calc SR . .
C15 C 0.4868(2) 0.7500 0.5663(3) 0.0503(13) Uani 1 2 d S . .
C16 C 0.4500(2) 0.7500 0.6386(4) 0.0515(14) Uani 1 2 d S . .
H16 H 0.4067 0.7500 0.6310 0.062 Uiso 1 2 calc SR . .
C17 C 0.64236(19) 0.7500 0.6753(3) 0.0546(13) Uani 1 2 d S . .
H17A H 0.6572 0.6219 0.6784 0.082 Uiso 0.50 1 calc PR . .
H17B H 0.6515 0.8139 0.7293 0.082 Uiso 0.50 1 calc PR . .
H17C H 0.6629 0.8143 0.6279 0.082 Uiso 0.50 1 calc PR . .
C18 C 0.4594(3) 0.7500 0.4785(4) 0.102(3) Uani 1 2 d S . .
H18A H 0.4222 0.6730 0.4781 0.153 Uiso 0.50 1 calc PR . .
H18B H 0.4893 0.6998 0.4375 0.153 Uiso 0.50 1 calc PR . .
H18C H 0.4487 0.8772 0.4621 0.153 Uiso 0.50 1 calc PR . .
N21 N 0.01515(15) 0.7500 0.4887(2) 0.0344(9) Uani 1 2 d S . .
C22 C -0.04594(17) 0.7500 0.4943(2) 0.0249(8) Uani 1 2 d S . .
H22 H -0.0638 0.7500 0.5499 0.030 Uiso 1 2 calc SR . .
C23 C -0.08515(16) 0.7500 0.4242(2) 0.0260(8) Uani 1 2 d S . .
C24 C -0.05802(17) 0.7500 0.3438(3) 0.0305(9) Uani 1 2 d S . .
H24 H -0.0833 0.7500 0.2941 0.037 Uiso 1 2 calc SR . .
C25 C 0.00528(19) 0.7500 0.3349(3) 0.0337(10) Uani 1 2 d S . .
C26 C 0.03964(18) 0.7500 0.4102(3) 0.0398(11) Uani 1 2 d S . .
H26 H 0.0832 0.7500 0.4054 0.048 Uiso 1 2 calc SR . .
C27 C -0.15381(18) 0.7500 0.4344(3) 0.0433(11) Uani 1 2 d S . .
H27A H -0.1647 0.8069 0.4894 0.065 Uiso 0.50 1 calc PR . .
H27B H -0.1690 0.6221 0.4329 0.065 Uiso 0.50 1 calc PR . .
H27C H -0.1725 0.8210 0.3876 0.065 Uiso 0.50 1 calc PR . .
C28 C 0.0363(2) 0.7500 0.2488(3) 0.0602(14) Uani 1 2 d S . .
H28A H 0.0761 0.6868 0.2532 0.090 Uiso 0.50 1 calc PR . .
H28B H 0.0427 0.8781 0.2298 0.090 Uiso 0.50 1 calc PR . .
H28C H 0.0103 0.6850 0.2071 0.090 Uiso 0.50 1 calc PR . .


_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 C1 1.241(4) . ?
C1 N1 1.343(3) . ?
C1 N1 1.343(3) 3_565 ?
O2 C2 1.257(4) . ?
C2 N2 1.337(3) . ?
C2 N2 1.337(3) 3 ?
O3 C3 1.245(4) . ?
C3 N3 1.347(3) 3 ?
C3 N3 1.347(3) . ?
O4 C4 1.255(4) . ?
C4 N4 1.336(3) . ?
C4 N4 1.336(3) 3_565 ?
N11 C16 1.322(6) . ?
N11 C12 1.339(6) . ?
C12 C13 1.375(6) . ?
C13 C14 1.372(5) . ?
C13 C17 1.501(5) . ?
C14 C15 1.374(6) . ?
C15 C16 1.382(7) . ?
C15 C18 1.494(7) . ?
N21 C22 1.331(5) . ?
N21 C26 1.336(6) . ?
C22 C23 1.386(5) . ?
C23 C24 1.385(5) . ?
C23 C27 1.501(5) . ?
C24 C25 1.383(5) . ?
C25 C26 1.391(6) . ?
C25 C28 1.502(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
O1 C1 N1 121.91(18) . . ?
O1 C1 N1 121.92(18) . 3_565 ?
N1 C1 N1 116.2(4) . 3_565 ?
O2 C2 N2 121.16(17) . . ?
O2 C2 N2 121.17(17) . 3 ?
N2 C2 N2 117.7(3) . 3 ?
O3 C3 N3 121.59(16) . 3 ?
O3 C3 N3 121.59(16) . . ?
N3 C3 N3 116.8(3) 3 . ?
O4 C4 N4 121.38(16) . . ?
O4 C4 N4 121.38(16) . 3_565 ?
N4 C4 N4 117.2(3) . 3_565 ?
C16 N11 C12 117.3(4) . . ?
N11 C12 C13 124.2(5) . . ?
C14 C13 C12 116.3(4) . . ?
C14 C13 C17 122.1(4) . . ?
C12 C13 C17 121.6(4) . . ?
C13 C14 C15 121.7(4) . . ?
C14 C15 C16 116.8(5) . . ?
C14 C15 C18 122.0(5) . . ?
C16 C15 C18 121.1(5) . . ?
N11 C16 C15 123.7(4) . . ?
C22 N21 C26 117.2(3) . . ?
N21 C22 C23 124.2(4) . . ?
C24 C23 C22 116.8(3) . . ?
C24 C23 C27 121.3(3) . . ?
C22 C23 C27 121.8(3) . . ?
C25 C24 C23 121.0(4) . . ?
C24 C25 C26 116.7(4) . . ?
C24 C25 C28 122.5(4) . . ?
C26 C25 C28 120.9(4) . . ?
N21 C26 C25 124.0(4) . . ?

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
C16 N11 C12 C13 0.000(1) . . . . ?
N11 C12 C13 C14 0.000(1) . . . . ?
N11 C12 C13 C17 180.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C17 C13 C14 C15 180.0 . . . . ?
C13 C14 C15 C16 0.000(1) . . . . ?
C13 C14 C15 C18 180.000(1) . . . . ?
C12 N11 C16 C15 0.000(1) . . . . ?
C14 C15 C16 N11 0.000(1) . . . . ?
C18 C15 C16 N11 180.0 . . . . ?
C26 N21 C22 C23 0.0 . . . . ?
N21 C22 C23 C24 0.0 . . . . ?
N21 C22 C23 C27 180.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C27 C23 C24 C25 180.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C23 C24 C25 C28 180.0 . . . . ?
C22 N21 C26 C25 0.0 . . . . ?
C24 C25 C26 N21 0.0 . . . . ?
C28 C25 C26 N21 180.0 . . . . ?

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 H01 N11 0.878(16) 2.33(2) 3.161(4) 157(3) .
N1 H02 O2 0.873(16) 2.119(16) 2.988(3) 174(2) .
N4 H07 N21 0.884(16) 2.32(2) 3.136(4) 154(3) .
N4 H08 O3 0.880(17) 2.034(17) 2.914(3) 178(3) .
N3 H05 O2 0.867(16) 2.28(2) 3.072(3) 151(3) .
N3 H06 O4 0.885(16) 2.080(17) 2.964(3) 177(3) .
N2 H03 O4 0.876(17) 2.29(2) 3.072(3) 148(3) 5_545
N2 H04 O1 0.891(16) 2.043(17) 2.932(3) 175(3) 1_545

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035

_database_code_depnum_ccdc_archive 'CCDC 990311'
#######################################################################
#
#                 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_walking

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H13 N3 O'
_chemical_formula_weight         167.21

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   'C 2/c'

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

_cell_length_a                   11.426(2)
_cell_length_b                   11.1168(9)
_cell_length_c                   7.4318(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.235(15)
_cell_angle_gamma                90.00
_cell_volume                     925.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1131
_cell_measurement_theta_min      3.5270
_cell_measurement_theta_max      23.5660

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_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      200(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  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5818
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.02
_reflns_number_total             819
_reflns_number_gt                679
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_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.

 The NH hydrogens were refined freely. The methyl groups was refined as an
 ideally disordered hexagon of half-occupied hydrogen atoms. Other
 hydrogens were included using a riding model starting from calculated
 positions.
;

_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)+(0.0510P)²+1.0454P] 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         819
_refine_ls_number_parameters     66
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.5000 -0.02523(15) 0.7500 0.0434(6) Uani 1 2 d S . .
C1 C 0.5000 0.0865(2) 0.7500 0.0356(6) Uani 1 2 d S . .
N1 N 0.51460(18) 0.15028(16) 0.6023(3) 0.0485(5) Uani 1 1 d . . .
H01 H 0.5084(19) 0.228(2) 0.606(3) 0.056(7) Uiso 1 1 d . . .
H02 H 0.513(2) 0.111(2) 0.494(3) 0.053(6) Uiso 1 1 d . . .
N11 N 0.5000 0.41702(19) 0.7500 0.0429(6) Uani 1 2 d S . .
C12 C 0.3972(2) 0.4775(2) 0.7108(3) 0.0578(7) Uani 1 1 d . . .
C13 C 0.3952(4) 0.6010(3) 0.7094(3) 0.0961(14) Uani 1 1 d . . .
H13 H 0.3214 0.6428 0.6804 0.115 Uiso 1 1 calc R . .
C14 C 0.5000 0.6635(4) 0.7500 0.122(3) Uani 1 2 d S . .
H14 H 0.5000 0.7490 0.7500 0.146 Uiso 1 2 calc SR . .
C15 C 0.2860(2) 0.4034(4) 0.6685(5) 0.0960(11) Uani 1 1 d . . .
H15A H 0.3067 0.3201 0.6445 0.144 Uiso 0.50 1 calc PR . .
H15B H 0.2329 0.4361 0.5599 0.144 Uiso 0.50 1 calc PR . .
H15C H 0.2455 0.4053 0.7732 0.144 Uiso 0.50 1 calc PR . .
H15D H 0.2167 0.4542 0.6739 0.144 Uiso 0.50 1 calc PR . .
H15E H 0.2905 0.3383 0.7585 0.144 Uiso 0.50 1 calc PR . .
H15F H 0.2779 0.3690 0.5452 0.144 Uiso 0.50 1 calc PR . .


_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 C1 1.242(3) . ?
C1 N1 1.344(2) 2_656 ?
C1 N1 1.344(2) . ?
N11 C12 1.335(3) . ?
N11 C12 1.335(3) 2_656 ?
C12 C13 1.374(4) . ?
C12 C15 1.496(4) . ?
C13 C14 1.366(4) . ?
C14 C13 1.366(4) 2_656 ?

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 N1 121.84(12) . 2_656 ?
O1 C1 N1 121.84(12) . . ?
N1 C1 N1 116.3(2) 2_656 . ?
C12 N11 C12 119.6(3) . 2_656 ?
N11 C12 C13 121.2(3) . . ?
N11 C12 C15 116.4(2) . . ?
C13 C12 C15 122.5(3) . . ?
C14 C13 C12 119.6(3) . . ?
C13 C14 C13 118.9(4) . 2_656 ?

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
C12 N11 C12 C13 0.23(17) 2_656 . . . ?
C12 N11 C12 C15 -180.0(3) 2_656 . . . ?
N11 C12 C13 C14 -0.5(3) . . . . ?
C15 C12 C13 C14 179.8(2) . . . . ?
C12 C13 C14 C13 0.22(16) . . . 2_656 ?

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 H01 N11 0.86(3) 2.37(2) 3.178(3) 155(2) .
N1 H02 O1 0.91(2) 2.03(3) 2.940(2) 177(2) 5_656
C14 H14 O1 0.95 2.51 3.460(4) 180.0 1_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.037


# end of cif file
_database_code_depnum_ccdc_archive 'CCDC 990312'
