# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1

_audit_creation_date             2011-06-28T15:25:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H14 N6 O1'
_chemical_formula_sum            'C10 H14 N6 O'
_chemical_formula_weight         234.27

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 42/n'
_symmetry_space_group_name_Hall  '-P 4bc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   17.028(4)
_cell_length_b                   17.028(4)
_cell_length_c                   8.0005(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2319.8(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      6.2
_cell_measurement_theta_max      12.1
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.5549
_exptl_absorpt_correction_T_max  0.9906

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
The crystals were very weakly diffracting ones.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius MACH3'
_diffrn_measurement_method       'profiled omega/2theta scans'
_diffrn_reflns_number            4528
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_unetI/netI     0.3219
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_full        25.32
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  112
_diffrn_standards_decay_%        3
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-5 -1 -1
-4 3 -2
-4 1 -2


#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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 > 2σ(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.
;
_reflns_number_total             2094
_reflns_number_gt                494
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.3034
_refine_ls_R_factor_gt           0.0924
_refine_ls_wR_factor_ref         0.1809
_refine_ls_goodness_of_fit_ref   0.842
_refine_ls_restrained_S_all      0.842
_refine_ls_number_reflns         2094
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'MACH3/PC (Enraf Nonius, 1992)'
_computing_cell_refinement       'MACH3/PC (Enraf Nonius, 1992)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C3 1.0777(5) -0.0798(4) 0.6392(10) 0.059(2) Uani d . 1 . . C
C6 0.9748(5) 0.0148(4) 0.7646(10) 0.051(2) Uani d . 1 . . C
C12 0.9144(4) 0.0722(4) 0.8179(8) 0.0432(18) Uani d . 1 . . C
C14 0.8034(4) 0.1255(5) 0.9005(11) 0.075(3) Uani d . 1 . . C
H14 0.7514 0.1316 0.9333 0.09 Uiso calc . 1 . . H
C15 0.8571(5) 0.1823(4) 0.8823(10) 0.077(3) Uani d . 1 . . C
H15 0.8487 0.2355 0.9016 0.093 Uiso calc . 1 . . H
C81 0.9977(4) 0.1931(4) 0.7950(10) 0.074(3) Uani d . 1 . . C
H81A 0.9845 0.24 0.7323 0.089 Uiso calc R 1 . . H
H81B 1.032 0.1611 0.726 0.089 Uiso calc R 1 . . H
C82 1.0401(5) 0.2159(5) 0.9492(12) 0.108(3) Uani d . 1 . . C
H82A 1.0518 0.1698 1.0161 0.129 Uiso calc R 1 . . H
H82B 1.0084 0.2515 1.0155 0.129 Uiso calc R 1 . . H
C83 1.1173(5) 0.2568(8) 0.8930(17) 0.196(7) Uani d . 1 . . C
H83A 1.1516 0.2175 0.844 0.235 Uiso calc R 1 . . H
H83B 1.1047 0.2945 0.8062 0.235 Uiso calc R 1 . . H
C84 1.1570(6) 0.2941(6) 1.0143(17) 0.185(6) Uani d . 1 . . C
H84A 1.2073 0.3103 0.9726 0.277 Uiso calc R 1 . . H
H84B 1.1642 0.2592 1.1074 0.277 Uiso calc R 1 . . H
H84C 1.1278 0.3394 1.0498 0.277 Uiso calc R 1 . . H
C91 0.8039(3) -0.0207(4) 0.8795(9) 0.076(2) Uani d . 1 . . C
H91A 0.749 -0.0138 0.9031 0.113 Uiso calc R 1 . . H
H91B 0.8283 -0.0486 0.9698 0.113 Uiso calc R 1 . . H
H91C 0.8098 -0.0501 0.7779 0.113 Uiso calc R 1 . . H
N1 0.9480(3) -0.0435(4) 0.6700(8) 0.0647(19) Uani d . 1 . . N
N2 1.0004(4) -0.0932(3) 0.6086(7) 0.068(2) Uani d . 1 . . N
N4 1.1001(3) -0.0274(4) 0.7640(8) 0.0603(18) Uani d . 1 . . N
N5 1.0472(4) 0.0215(3) 0.8199(7) 0.0599(18) Uani d . 1 . . N
N11 0.9263(4) 0.1494(4) 0.8307(8) 0.0629(18) Uani d . 1 . . N
N13 0.8409(3) 0.0558(4) 0.8606(7) 0.0577(18) Uani d . 1 . . N
O1 1.1291(3) -0.1162(3) 0.5655(7) 0.0817(18) Uani d . 1 . . O



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C3 O1 . 1.223(8) ?
C3 N2 . 1.359(8) ?
C3 N4 . 1.392(8) ?
C6 N5 . 1.314(7) ?
C6 N1 . 1.329(7) ?
C6 C12 . 1.481(8) ?
C12 N13 . 1.327(7) ?
C12 N11 . 1.335(7) ?
C14 C15 . 1.339(8) ?
C14 N13 . 1.386(7) ?
C14 H14 . 0.93 ?
C15 N11 . 1.369(8) ?
C15 H15 . 0.93 ?
C81 N11 . 1.454(7) ?
C81 C82 . 1.481(10) ?
C81 H81A . 0.97 ?
C81 H81B . 0.97 ?
C82 C83 . 1.555(11) ?
C82 H82A . 0.97 ?
C82 H82B . 0.97 ?
C83 C84 . 1.342(11) ?
C83 H83A . 0.97 ?
C83 H83B . 0.97 ?
C84 H84A . 0.96 ?
C84 H84B . 0.96 ?
C84 H84C . 0.96 ?
C91 N13 . 1.454(7) ?
C91 H91A . 0.96 ?
C91 H91B . 0.96 ?
C91 H91C . 0.96 ?
N1 N2 . 1.323(7) ?
N4 N5 . 1.305(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 C3 N2 121.4(8) . . ?
O1 C3 N4 118.4(8) . . ?
N2 C3 N4 120.1(7) . . ?
N5 C6 N1 125.3(7) . . ?
N5 C6 C12 119.8(7) . . ?
N1 C6 C12 114.8(7) . . ?
N13 C12 N11 109.3(6) . . ?
N13 C12 C6 126.1(7) . . ?
N11 C12 C6 124.6(7) . . ?
C15 C14 N13 106.2(6) . . ?
C15 C14 H14 126.9 . . ?
N13 C14 H14 126.9 . . ?
C14 C15 N11 109.0(7) . . ?
C14 C15 H15 125.5 . . ?
N11 C15 H15 125.5 . . ?
N11 C81 C82 112.2(7) . . ?
N11 C81 H81A 109.2 . . ?
C82 C81 H81A 109.2 . . ?
N11 C81 H81B 109.2 . . ?
C82 C81 H81B 109.2 . . ?
H81A C81 H81B 107.9 . . ?
C81 C82 C83 106.8(8) . . ?
C81 C82 H82A 110.4 . . ?
C83 C82 H82A 110.4 . . ?
C81 C82 H82B 110.4 . . ?
C83 C82 H82B 110.4 . . ?
H82A C82 H82B 108.6 . . ?
C84 C83 C82 115.4(11) . . ?
C84 C83 H83A 108.4 . . ?
C82 C83 H83A 108.4 . . ?
C84 C83 H83B 108.4 . . ?
C82 C83 H83B 108.4 . . ?
H83A C83 H83B 107.5 . . ?
C83 C84 H84A 109.5 . . ?
C83 C84 H84B 109.5 . . ?
H84A C84 H84B 109.5 . . ?
C83 C84 H84C 109.5 . . ?
H84A C84 H84C 109.5 . . ?
H84B C84 H84C 109.5 . . ?
N13 C91 H91A 109.5 . . ?
N13 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
N13 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
N2 N1 C6 117.2(6) . . ?
N1 N2 C3 118.6(6) . . ?
N5 N4 C3 117.8(6) . . ?
N4 N5 C6 118.4(6) . . ?
C12 N11 C15 107.2(6) . . ?
C12 N11 C81 128.0(7) . . ?
C15 N11 C81 124.8(7) . . ?
C12 N13 C14 108.3(6) . . ?
C12 N13 C91 128.7(6) . . ?
C14 N13 C91 122.9(6) . . ?
_database_code_depnum_ccdc_archive 'CCDC 1003465'
#######################################################################
#
#                 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_2

_audit_creation_date             2013-05-25T12:44:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H24 N6 O1'
_chemical_formula_sum            'C23 H24 N6 O'
_chemical_formula_weight         400.48

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7079(10)
_cell_length_b                   15.3735(10)
_cell_length_c                   11.8425(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.763(10)
_cell_angle_gamma                90
_cell_volume                     2131.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      11.7
_cell_measurement_theta_max      18.5
_cell_measurement_temperature    293(2)
_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   4
        Theta correction was applied.
        Averaged transmission function was used.
        Fourier smoothing - Window value   5
;
_exptl_absorpt_correction_T_min  0.9434
_exptl_absorpt_correction_T_max  0.9764

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius MACH3'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_reflns_number            4730
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_max 0.95
_diffrn_measured_fraction_theta_full 0.95
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         3
_diffrn_standards_interval_count 88
_diffrn_standards_interval_time  1
_diffrn_standards_decay_%        100
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
4 8 -2
7 -2 -2
2 -10 -7


#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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 > 2σ(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.
;
_reflns_number_total             3971
_reflns_number_gt                2258
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.063
_refine_ls_wR_factor_ref         0.2431
_refine_ls_goodness_of_fit_ref   1.16
_refine_ls_restrained_S_all      1.16
_refine_ls_number_reflns         3971
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1360P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'MACH3/PC (Enraf Nonius, 1992)'
_computing_cell_refinement       'MACH3/PC (Enraf Nonius, 1992)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C3 0.7921(3) 0.3637(2) 0.0871(3) 0.0488(9) Uani d . 1 . . C
C6 0.8708(3) 0.2415(2) 0.2157(3) 0.0409(8) Uani d . 1 . . C
C12 0.9135(3) 0.1665(2) 0.2798(3) 0.0402(8) Uani d . 1 . . C
C15 0.9257(3) 0.0374(2) 0.3622(3) 0.0523(9) Uani d . 1 . . C
H15 0.9055 -0.0169 0.3904 0.063 Uiso calc . 1 . . H
C14 1.0294(3) 0.0737(2) 0.3679(3) 0.0526(9) Uani d . 1 . . C
H14 1.0947 0.0493 0.4002 0.063 Uiso calc . 1 . . H
C81 0.7352(3) 0.0752(2) 0.2840(3) 0.0422(8) Uani d . 1 . . C
C82 0.6550(3) 0.0993(2) 0.3632(3) 0.0524(9) Uani d . 1 . . C
C83 0.5440(3) 0.0723(3) 0.3440(4) 0.0615(10) Uani d . 1 . . C
H83 0.488 0.0888 0.3947 0.074 Uiso calc . 1 . . H
C84 0.5131(3) 0.0218(2) 0.2519(4) 0.0605(10) Uani d . 1 . . C
C85 0.5976(3) -0.0001(2) 0.1754(3) 0.0562(10) Uani d . 1 . . C
H85 0.5773 -0.0326 0.112 0.067 Uiso calc . 1 . . H
C86 0.7098(3) 0.0245(2) 0.1896(3) 0.0448(8) Uani d . 1 . . C
C87 0.6878(4) 0.1487(3) 0.4674(3) 0.0789(13) Uani d . 1 . . C
H87A 0.6207 0.1604 0.5107 0.118 Uiso calc R 1 . . H
H87B 0.723 0.2026 0.4465 0.118 Uiso calc R 1 . . H
H87C 0.7405 0.1149 0.5119 0.118 Uiso calc R 1 . . H
C88 0.3929(3) -0.0115(3) 0.2391(5) 0.0984(17) Uani d . 1 . . C
H88A 0.3419 0.0262 0.2789 0.148 Uiso calc R 1 . . H
H88B 0.3883 -0.0692 0.2697 0.148 Uiso calc R 1 . . H
H88C 0.3718 -0.0127 0.1605 0.148 Uiso calc R 1 . . H
C89 0.8002(3) -0.0070(3) 0.1113(3) 0.0669(11) Uani d . 1 . . C
H89A 0.7684 -0.0129 0.0366 0.1 Uiso calc R 1 . . H
H89B 0.8283 -0.0623 0.1369 0.1 Uiso calc R 1 . . H
H89C 0.8618 0.0342 0.1103 0.1 Uiso calc R 1 . . H
C91 1.1173(3) 0.2135(2) 0.3178(3) 0.0407(8) Uani d . 1 . . C
C92 1.1317(3) 0.2676(2) 0.4110(3) 0.0455(8) Uani d . 1 . . C
C93 1.2330(3) 0.3130(2) 0.4202(3) 0.0548(9) Uani d . 1 . . C
H93 1.2447 0.3495 0.4819 0.066 Uiso calc . 1 . . H
C94 1.3177(3) 0.3057(3) 0.3402(4) 0.0609(10) Uani d . 1 . . C
C95 1.2973(3) 0.2534(3) 0.2478(3) 0.0576(10) Uani d . 1 . . C
H95 1.3525 0.2503 0.1922 0.069 Uiso calc . 1 . . H
C96 1.1987(3) 0.2055(2) 0.2342(3) 0.0459(8) Uani d . 1 . . C
C97 1.0419(3) 0.2743(3) 0.5002(3) 0.0662(11) Uani d . 1 . . C
H97A 0.9699 0.2888 0.4654 0.099 Uiso calc R 1 . . H
H97B 1.0631 0.3187 0.5535 0.099 Uiso calc R 1 . . H
H97C 1.0354 0.2195 0.5386 0.099 Uiso calc R 1 . . H
C98 1.4306(4) 0.3535(4) 0.3540(5) 0.0950(16) Uani d . 1 . . C
H98A 1.4514 0.356 0.4326 0.142 Uiso calc R 1 . . H
H98B 1.423 0.4115 0.3247 0.142 Uiso calc R 1 . . H
H98C 1.4888 0.3231 0.3133 0.142 Uiso calc R 1 . . H
C99 1.1792(3) 0.1469(3) 0.1340(3) 0.0615(10) Uani d . 1 . . C
H99A 1.1659 0.0886 0.1596 0.092 Uiso calc R 1 . . H
H99B 1.2454 0.1479 0.087 0.092 Uiso calc R 1 . . H
H99C 1.114 0.1669 0.0915 0.092 Uiso calc R 1 . . H
N5 0.9424(2) 0.27585(19) 0.1413(2) 0.0533(8) Uani d . 1 . . N
N4 0.9055(2) 0.3392(2) 0.0777(3) 0.0608(9) Uani d . 1 . . N
N2 0.7276(2) 0.3360(2) 0.1773(3) 0.0581(8) Uani d . 1 . . N
N1 0.7677(2) 0.27218(19) 0.2400(3) 0.0545(8) Uani d . 1 . . N
N11 0.8543(2) 0.09502(17) 0.3070(2) 0.0432(7) Uani d . 1 . . N
N13 1.0213(2) 0.15404(17) 0.3170(2) 0.0437(7) Uani d . 1 . . N
O1 0.7497(2) 0.41389(16) 0.0167(2) 0.0674(8) Uani d . 1 . . O



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C3 O1 . 1.235(4) ?
C3 N2 . 1.384(5) ?
C3 N4 . 1.386(4) ?
C6 N1 . 1.332(4) ?
C6 N5 . 1.333(4) ?
C6 C12 . 1.464(4) ?
C12 N11 . 1.341(4) ?
C12 N13 . 1.345(4) ?
C15 C14 . 1.337(4) ?
C15 N11 . 1.377(4) ?
C15 H15 . 0.93 ?
C14 N13 . 1.377(4) ?
C14 H14 . 0.93 ?
C81 C82 . 1.387(5) ?
C81 C86 . 1.392(4) ?
C81 N11 . 1.450(4) ?
C82 C83 . 1.380(5) ?
C82 C87 . 1.495(5) ?
C83 C84 . 1.384(5) ?
C83 H83 . 0.93 ?
C84 C85 . 1.391(5) ?
C84 C88 . 1.502(5) ?
C85 C86 . 1.376(5) ?
C85 H85 . 0.93 ?
C86 C89 . 1.496(5) ?
C87 H87A . 0.96 ?
C87 H87B . 0.96 ?
C87 H87C . 0.96 ?
C88 H88A . 0.96 ?
C88 H88B . 0.96 ?
C88 H88C . 0.96 ?
C89 H89A . 0.96 ?
C89 H89B . 0.96 ?
C89 H89C . 0.96 ?
C91 C96 . 1.389(4) ?
C91 C92 . 1.391(4) ?
C91 N13 . 1.449(4) ?
C92 C93 . 1.379(5) ?
C92 C97 . 1.504(5) ?
C93 C94 . 1.386(5) ?
C93 H93 . 0.93 ?
C94 C95 . 1.376(5) ?
C94 C98 . 1.519(5) ?
C95 C96 . 1.378(5) ?
C95 H95 . 0.93 ?
C96 C99 . 1.505(5) ?
C97 H97A . 0.96 ?
C97 H97B . 0.96 ?
C97 H97C . 0.96 ?
C98 H98A . 0.96 ?
C98 H98B . 0.96 ?
C98 H98C . 0.96 ?
C99 H99A . 0.96 ?
C99 H99B . 0.96 ?
C99 H99C . 0.96 ?
N5 N4 . 1.301(4) ?
N2 N1 . 1.314(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 C3 N2 119.6(3) . . ?
O1 C3 N4 119.6(3) . . ?
N2 C3 N4 120.7(3) . . ?
N1 C6 N5 125.6(3) . . ?
N1 C6 C12 118.1(3) . . ?
N5 C6 C12 116.2(3) . . ?
N11 C12 N13 106.8(3) . . ?
N11 C12 C6 126.6(3) . . ?
N13 C12 C6 126.5(3) . . ?
C14 C15 N11 107.5(3) . . ?
C14 C15 H15 126.3 . . ?
N11 C15 H15 126.3 . . ?
C15 C14 N13 107.2(3) . . ?
C15 C14 H14 126.4 . . ?
N13 C14 H14 126.4 . . ?
C82 C81 C86 123.6(3) . . ?
C82 C81 N11 118.4(3) . . ?
C86 C81 N11 117.6(3) . . ?
C83 C82 C81 116.9(3) . . ?
C83 C82 C87 121.3(3) . . ?
C81 C82 C87 121.7(3) . . ?
C82 C83 C84 122.3(4) . . ?
C82 C83 H83 118.8 . . ?
C84 C83 H83 118.8 . . ?
C83 C84 C85 117.9(3) . . ?
C83 C84 C88 120.4(4) . . ?
C85 C84 C88 121.7(4) . . ?
C86 C85 C84 122.7(3) . . ?
C86 C85 H85 118.6 . . ?
C84 C85 H85 118.6 . . ?
C85 C86 C81 116.4(3) . . ?
C85 C86 C89 121.2(3) . . ?
C81 C86 C89 122.2(3) . . ?
C82 C87 H87A 109.5 . . ?
C82 C87 H87B 109.5 . . ?
H87A C87 H87B 109.5 . . ?
C82 C87 H87C 109.5 . . ?
H87A C87 H87C 109.5 . . ?
H87B C87 H87C 109.5 . . ?
C84 C88 H88A 109.5 . . ?
C84 C88 H88B 109.5 . . ?
H88A C88 H88B 109.5 . . ?
C84 C88 H88C 109.5 . . ?
H88A C88 H88C 109.5 . . ?
H88B C88 H88C 109.5 . . ?
C86 C89 H89A 109.5 . . ?
C86 C89 H89B 109.5 . . ?
H89A C89 H89B 109.5 . . ?
C86 C89 H89C 109.5 . . ?
H89A C89 H89C 109.5 . . ?
H89B C89 H89C 109.5 . . ?
C96 C91 C92 122.7(3) . . ?
C96 C91 N13 118.7(3) . . ?
C92 C91 N13 118.0(3) . . ?
C93 C92 C91 117.5(3) . . ?
C93 C92 C97 121.2(3) . . ?
C91 C92 C97 121.3(3) . . ?
C92 C93 C94 121.8(3) . . ?
C92 C93 H93 119.1 . . ?
C94 C93 H93 119.1 . . ?
C95 C94 C93 118.2(3) . . ?
C95 C94 C98 120.6(4) . . ?
C93 C94 C98 121.2(4) . . ?
C94 C95 C96 122.8(3) . . ?
C94 C95 H95 118.6 . . ?
C96 C95 H95 118.6 . . ?
C95 C96 C91 116.9(3) . . ?
C95 C96 C99 122.0(3) . . ?
C91 C96 C99 121.1(3) . . ?
C92 C97 H97A 109.5 . . ?
C92 C97 H97B 109.5 . . ?
H97A C97 H97B 109.5 . . ?
C92 C97 H97C 109.5 . . ?
H97A C97 H97C 109.5 . . ?
H97B C97 H97C 109.5 . . ?
C94 C98 H98A 109.5 . . ?
C94 C98 H98B 109.5 . . ?
H98A C98 H98B 109.5 . . ?
C94 C98 H98C 109.5 . . ?
H98A C98 H98C 109.5 . . ?
H98B C98 H98C 109.5 . . ?
C96 C99 H99A 109.5 . . ?
C96 C99 H99B 109.5 . . ?
H99A C99 H99B 109.5 . . ?
C96 C99 H99C 109.5 . . ?
H99A C99 H99C 109.5 . . ?
H99B C99 H99C 109.5 . . ?
N4 N5 C6 118.2(3) . . ?
N5 N4 C3 118.0(3) . . ?
N1 N2 C3 118.2(3) . . ?
N2 N1 C6 117.4(3) . . ?
C12 N11 C15 109.2(3) . . ?
C12 N11 C81 128.8(3) . . ?
C15 N11 C81 122.0(3) . . ?
C12 N13 C14 109.3(3) . . ?
C12 N13 C91 129.6(3) . . ?
C14 N13 C91 120.9(3) . . ?
_database_code_depnum_ccdc_archive 'CCDC 1003466'
#######################################################################
#
#                 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_3

_audit_creation_date             2014-09-10T08:35:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H20 N6 O'
_chemical_formula_sum            'C21 H20 N6 O'
_chemical_formula_weight         372.43
_chemical_absolute_configuration syn

#==============================================================================

# CRYSTAL DATA

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


_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
_cell_length_a                   6.1590(10)
_cell_length_b                   18.715(2)
_cell_length_c                   15.977(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1841.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.5
_cell_measurement_theta_max      16.3
_cell_measurement_temperature    293(2)
_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   2
        Theta correction was applied.
        Averaged transmission function was used.
        Fourier smoothing - Window value   5
;
_exptl_absorpt_correction_T_min  0.9431
_exptl_absorpt_correction_T_max  0.998

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius MACH3'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_reflns_number            1031
_diffrn_reflns_av_R_equivalents  0.0078
_diffrn_reflns_theta_min         2.522
_diffrn_reflns_theta_max         25.439
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.572
_diffrn_reflns_point_group_measured_fraction_max 0.57
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         4
_diffrn_standards_interval_count 167
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 4 4
3 5 5
-1 5 -9
-2 3 -6


#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 ?
;
_reflns_number_total             979
_reflns_number_gt                817
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1305
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_restrained_S_all      0.801
_refine_ls_number_reflns         979
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1262P)²+0.2486P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   10(5)
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'MACH3/PC (Enraf Nonius, 1992)'
_computing_cell_refinement       'MACH3/PC (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C3 0.5 0.2014(2) 0.25 0.0638(13) Uani d 1 . . C
C6 0.5 0.3396(2) 0.25 0.0411(9) Uani d 1 . . C
C12 0.5 0.4175(2) 0.25 0.0399(8) Uani d 1 . . C
C15 0.4128(6) 0.52965(15) 0.27509(17) 0.0509(8) Uani d 1 . . C
H15 0.3413 0.5697 0.2957 0.061 Uiso calc 1 . . H
C81 0.1887(5) 0.43385(15) 0.34938(16) 0.0458(7) Uani d 1 . . C
H81 0.0946 0.4004 0.3192 0.055 Uiso calc 1 . . H
C82 0.0506(5) 0.4961(2) 0.3790(2) 0.0607(9) Uani d 1 . . C
H82A 0.1381 0.528 0.4118 0.091 Uiso calc 1 . . H
H82B -0.0672 0.4785 0.4125 0.091 Uiso calc 1 . . H
H82C -0.0064 0.5212 0.3314 0.091 Uiso calc 1 . . H
C83 0.2876(5) 0.39474(14) 0.42299(16) 0.0434(7) Uani d 1 . . C
C84 0.4858(6) 0.41403(18) 0.45681(17) 0.0527(8) Uani d 1 . . C
H84 0.5692 0.449 0.4309 0.063 Uiso calc 1 . . H
C85 0.5604(6) 0.3814(2) 0.52907(19) 0.0607(9) Uani d 1 . . C
H85 0.6944 0.3945 0.5511 0.073 Uiso calc 1 . . H
C86 0.4390(7) 0.33014(18) 0.56848(19) 0.0635(10) Uani d 1 . . C
H86 0.4884 0.3091 0.6176 0.076 Uiso calc 1 . . H
C87 0.2437(8) 0.31027(18) 0.5345(2) 0.0658(10) Uani d 1 . . C
H87 0.1602 0.2753 0.5604 0.079 Uiso calc 1 . . H
C88 0.1712(6) 0.34207(17) 0.46209(19) 0.0565(9) Uani d 1 . . C
H88 0.0398 0.3274 0.4391 0.068 Uiso calc 1 . . H
N1 0.3098(4) 0.30724(13) 0.2410(2) 0.0598(8) Uani d 1 . . N
N2 0.3056(5) 0.23678(13) 0.2434(3) 0.0715(9) Uani d 1 . . N
N11 0.3590(4) 0.45964(12) 0.29045(13) 0.0442(6) Uani d 1 . . N
O1 0.5 0.1372(2) 0.25 0.137(2) Uani d 1 . . O



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C3 O1 . 1.201(6) ?
C3 N2 . 1.372(4) ?
C3 N2 4_655 1.372(4) ?
C6 N1 . 1.327(3) ?
C6 N1 4_655 1.327(3) ?
C6 C12 . 1.458(5) ?
C12 N11 4_655 1.339(3) ?
C12 N11 . 1.339(3) ?
C15 C15 4_655 1.341(6) ?
C15 N11 . 1.374(4) ?
C15 H15 . 0.93 ?
C81 N11 . 1.490(4) ?
C81 C83 . 1.513(4) ?
C81 C82 . 1.518(4) ?
C81 H81 . 0.98 ?
C82 H82A . 0.96 ?
C82 H82B . 0.96 ?
C82 H82C . 0.96 ?
C83 C88 . 1.370(4) ?
C83 C84 . 1.383(5) ?
C84 C85 . 1.384(4) ?
C84 H84 . 0.93 ?
C85 C86 . 1.370(5) ?
C85 H85 . 0.93 ?
C86 C87 . 1.371(6) ?
C86 H86 . 0.93 ?
C87 C88 . 1.375(5) ?
C87 H87 . 0.93 ?
C88 H88 . 0.93 ?
N1 N2 . 1.319(3) ?

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 C3 N2 118.85(18) . . ?
O1 C3 N2 118.85(18) . 4_655 ?
N2 C3 N2 122.3(4) . 4_655 ?
N1 C6 N1 125.6(4) . 4_655 ?
N1 C6 C12 117.18(18) . . ?
N1 C6 C12 117.18(18) 4_655 . ?
N11 C12 N11 107.9(3) 4_655 . ?
N11 C12 C6 126.04(17) 4_655 . ?
N11 C12 C6 126.04(17) . . ?
C15 C15 N11 107.46(16) 4_655 . ?
C15 C15 H15 126.3 4_655 . ?
N11 C15 H15 126.3 . . ?
N11 C81 C83 111.4(3) . . ?
N11 C81 C82 110.0(2) . . ?
C83 C81 C82 110.8(2) . . ?
N11 C81 H81 108.2 . . ?
C83 C81 H81 108.2 . . ?
C82 C81 H81 108.2 . . ?
C81 C82 H82A 109.5 . . ?
C81 C82 H82B 109.5 . . ?
H82A C82 H82B 109.5 . . ?
C81 C82 H82C 109.5 . . ?
H82A C82 H82C 109.5 . . ?
H82B C82 H82C 109.5 . . ?
C88 C83 C84 118.1(3) . . ?
C88 C83 C81 119.5(3) . . ?
C84 C83 C81 122.2(3) . . ?
C83 C84 C85 120.3(3) . . ?
C83 C84 H84 119.9 . . ?
C85 C84 H84 119.9 . . ?
C86 C85 C84 120.7(3) . . ?
C86 C85 H85 119.6 . . ?
C84 C85 H85 119.6 . . ?
C85 C86 C87 119.1(3) . . ?
C85 C86 H86 120.4 . . ?
C87 C86 H86 120.4 . . ?
C86 C87 C88 120.0(3) . . ?
C86 C87 H87 120 . . ?
C88 C87 H87 120 . . ?
C83 C88 C87 121.7(3) . . ?
C83 C88 H88 119.2 . . ?
C87 C88 H88 119.2 . . ?
N2 N1 C6 118.1(3) . . ?
N1 N2 C3 117.9(3) . . ?
C12 N11 C15 108.6(2) . . ?
C12 N11 C81 124.8(2) . . ?
C15 N11 C81 126.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C6 C12 N11 -136.4(2) . . . 4_655 ?
N1 C6 C12 N11 43.6(2) 4_655 . . 4_655 ?
N1 C6 C12 N11 43.6(2) . . . . ?
N1 C6 C12 N11 -136.4(2) 4_655 . . . ?
N11 C81 C83 C88 -151.2(3) . . . . ?
C82 C81 C83 C88 85.9(3) . . . . ?
N11 C81 C83 C84 34.0(3) . . . . ?
C82 C81 C83 C84 -88.8(4) . . . . ?
C88 C83 C84 C85 -1.1(4) . . . . ?
C81 C83 C84 C85 173.7(3) . . . . ?
C83 C84 C85 C86 -0.5(5) . . . . ?
C84 C85 C86 C87 1.3(5) . . . . ?
C85 C86 C87 C88 -0.5(5) . . . . ?
C84 C83 C88 C87 2.0(5) . . . . ?
C81 C83 C88 C87 -172.9(3) . . . . ?
C86 C87 C88 C83 -1.2(5) . . . . ?
N1 C6 N1 N2 2.0(3) 4_655 . . . ?
C12 C6 N1 N2 -178.0(3) . . . . ?
C6 N1 N2 C3 -3.8(5) . . . . ?
O1 C3 N2 N1 -178.1(3) . . . . ?
N2 C3 N2 N1 1.9(3) 4_655 . . . ?
N11 C12 N11 C15 -0.04(15) 4_655 . . . ?
C6 C12 N11 C15 179.96(15) . . . . ?
N11 C12 N11 C81 -173.9(3) 4_655 . . . ?
C6 C12 N11 C81 6.1(3) . . . . ?
C15 C15 N11 C12 0.1(4) 4_655 . . . ?
C15 C15 N11 C81 173.9(3) 4_655 . . . ?
C83 C81 N11 C12 60.3(3) . . . . ?
C82 C81 N11 C12 -176.5(2) . . . . ?
C83 C81 N11 C15 -112.5(3) . . . . ?
C82 C81 N11 C15 10.7(4) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 1003467'
#######################################################################
#
#                 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_4

_audit_creation_date             2011-06-28T15:27:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H24 N6 O1'
_chemical_formula_sum            'C22 H24 N6 O'
_chemical_formula_weight         388.47
_chemical_absolute_configuration syn

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.7674(10)
_cell_length_b                   13.8678(10)
_cell_length_c                   14.8710(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2014.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.32
_cell_measurement_theta_max      17.01
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.22
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   4
        Theta correction was applied.
        Averaged transmission function was used.
        Fourier smoothing - Window value   5
;
_exptl_absorpt_correction_T_min  0.9165
_exptl_absorpt_correction_T_max  0.9804

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius MACH3'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_reflns_number            2317
_diffrn_reflns_av_R_equivalents  0.0101
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_full        25.96
_diffrn_measured_fraction_theta_max 1
_diffrn_measured_fraction_theta_full 1
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        2
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 -2 3
-2 0 7
-3 -1 10


#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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 > 2σ(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.
;
_reflns_number_total             2242
_reflns_number_gt                1546
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.051
_refine_ls_wR_factor_ref         0.1275
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_number_reflns         2242
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0633P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.04
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -5(4)
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'MACH3/PC (Enraf Nonius, 1992)'
_computing_cell_refinement       'MACH3/PC (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C3 0.2434(4) 0.2476(3) 0.7677(3) 0.0490(10) Uani d . 1 . . C
C6 0.4650(4) 0.1650(3) 0.7129(2) 0.0354(8) Uani d . 1 . . C
C12 0.5924(4) 0.1121(3) 0.6959(2) 0.0371(8) Uani d . 1 . . C
C14 0.8048(4) 0.0447(3) 0.7160(3) 0.0580(11) Uani d . 1 . . C
H14A 0.8229 -0.0084 0.7568 0.07 Uiso calc R 1 . . H
H14B 0.8891 0.08 0.7059 0.07 Uiso calc R 1 . . H
C15 0.7450(4) 0.0087(3) 0.6282(3) 0.0532(11) Uani d . 1 . . C
H15A 0.8033 0.0256 0.5778 0.064 Uiso calc R 1 . . H
H15B 0.7326 -0.0607 0.6293 0.064 Uiso calc R 1 . . H
C81 0.5411(4) 0.0698(3) 0.5388(2) 0.0387(9) Uani d . 1 . . C
C82 0.4442(4) 0.0009(3) 0.5141(3) 0.0432(9) Uani d . 1 . . C
C83 0.3805(4) 0.0130(3) 0.4307(3) 0.0523(11) Uani d . 1 . . C
H83 0.3166 -0.0325 0.412 0.063 Uiso calc . 1 . . H
C84 0.4087(4) 0.0892(3) 0.3758(3) 0.0523(10) Uani d . 1 . . C
C85 0.5089(4) 0.1552(3) 0.4020(3) 0.0529(11) Uani d . 1 . . C
H85 0.5302 0.2063 0.364 0.064 Uiso calc . 1 . . H
C86 0.5776(4) 0.1466(3) 0.4832(3) 0.0442(9) Uani d . 1 . . C
C87 0.4112(5) -0.0837(3) 0.5738(3) 0.0584(12) Uani d . 1 . . C
H87A 0.344 -0.1237 0.5449 0.088 Uiso calc R 1 . . H
H87B 0.3758 -0.0608 0.6301 0.088 Uiso calc R 1 . . H
H87C 0.4928 -0.1206 0.5843 0.088 Uiso calc R 1 . . H
C88 0.3347(6) 0.1011(4) 0.2864(3) 0.0797(16) Uani d . 1 . . C
H88A 0.3865 0.1432 0.2481 0.12 Uiso calc R 1 . . H
H88B 0.2456 0.1283 0.2968 0.12 Uiso calc R 1 . . H
H88C 0.3251 0.0393 0.258 0.12 Uiso calc R 1 . . H
C89 0.6898(5) 0.2153(3) 0.5078(3) 0.0592(12) Uani d . 1 . . C
H89A 0.776 0.182 0.5072 0.089 Uiso calc R 1 . . H
H89B 0.6732 0.2408 0.5668 0.089 Uiso calc R 1 . . H
H89C 0.6923 0.2672 0.4651 0.089 Uiso calc R 1 . . H
C91 0.6943(4) 0.1476(3) 0.8442(2) 0.0461(10) Uani d . 1 . . C
H91 0.6596 0.2138 0.8411 0.055 Uiso calc R 1 . . H
C92 0.8393(4) 0.1514(4) 0.8820(3) 0.0682(13) Uani d . 1 . . C
H92A 0.8755 0.0872 0.8863 0.102 Uiso calc R 1 . . H
H92B 0.8376 0.1803 0.9407 0.102 Uiso calc R 1 . . H
H92C 0.8962 0.1892 0.8429 0.102 Uiso calc R 1 . . H
C93 0.5988(4) 0.0902(3) 0.9044(2) 0.0396(9) Uani d . 1 . . C
C94 0.5665(4) -0.0052(3) 0.8894(3) 0.0533(11) Uani d . 1 . . C
H94 0.6003 -0.0361 0.8385 0.064 Uiso calc . 1 . . H
C95 0.4851(5) -0.0555(3) 0.9485(3) 0.0643(13) Uani d . 1 . . C
H95 0.4644 -0.1198 0.937 0.077 Uiso calc . 1 . . H
C96 0.4346(4) -0.0120(4) 1.0236(3) 0.0587(12) Uani d . 1 . . C
H96 0.3789 -0.046 1.0632 0.07 Uiso calc . 1 . . H
C97 0.4668(5) 0.0831(4) 1.0403(3) 0.0594(12) Uani d . 1 . . C
H97 0.4337 0.1132 1.0918 0.071 Uiso calc . 1 . . H
C98 0.5471(4) 0.1332(3) 0.9814(3) 0.0515(10) Uani d . 1 . . C
H98 0.5675 0.1975 0.9931 0.062 Uiso calc . 1 . . H
N1 0.3469(3) 0.1213(2) 0.6941(2) 0.0483(9) Uani d . 1 . . N
N2 0.2332(3) 0.1635(3) 0.7168(2) 0.0570(10) Uani d . 1 . . N
N4 0.3613(3) 0.3018(2) 0.7621(2) 0.0550(9) Uani d . 1 . . N
N5 0.4743(3) 0.2574(2) 0.7391(2) 0.0495(8) Uani d . 1 . . N
N11 0.6116(3) 0.0591(2) 0.62273(19) 0.0410(8) Uani d . 1 . . N
N13 0.6968(3) 0.1086(2) 0.7519(2) 0.0436(8) Uani d . 1 . . N
O1 0.1452(3) 0.2766(3) 0.8099(3) 0.0881(12) Uani d . 1 . . O



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C3 O1 . 1.216(5) ?
C3 N4 . 1.377(5) ?
C3 N2 . 1.394(5) ?
C6 N1 . 1.333(5) ?
C6 N5 . 1.342(5) ?
C6 C12 . 1.467(5) ?
C12 N13 . 1.317(4) ?
C12 N11 . 1.327(5) ?
C14 N13 . 1.478(5) ?
C14 C15 . 1.515(6) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 N11 . 1.481(5) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C81 C82 . 1.393(5) ?
C81 C86 . 1.395(5) ?
C81 N11 . 1.434(5) ?
C82 C83 . 1.398(6) ?
C82 C87 . 1.506(5) ?
C83 C84 . 1.363(6) ?
C83 H83 . 0.93 ?
C84 C85 . 1.396(6) ?
C84 C88 . 1.522(6) ?
C85 C86 . 1.386(6) ?
C85 H85 . 0.93 ?
C86 C89 . 1.498(5) ?
C87 H87A . 0.96 ?
C87 H87B . 0.96 ?
C87 H87C . 0.96 ?
C88 H88A . 0.96 ?
C88 H88B . 0.96 ?
C88 H88C . 0.96 ?
C89 H89A . 0.96 ?
C89 H89B . 0.96 ?
C89 H89C . 0.96 ?
C91 N13 . 1.474(5) ?
C91 C93 . 1.518(5) ?
C91 C92 . 1.525(6) ?
C91 H91 . 0.98 ?
C92 H92A . 0.96 ?
C92 H92B . 0.96 ?
C92 H92C . 0.96 ?
C93 C94 . 1.378(5) ?
C93 C98 . 1.386(5) ?
C94 C95 . 1.374(6) ?
C94 H94 . 0.93 ?
C95 C96 . 1.363(6) ?
C95 H95 . 0.93 ?
C96 C97 . 1.378(7) ?
C96 H96 . 0.93 ?
C97 C98 . 1.366(6) ?
C97 H97 . 0.93 ?
C98 H98 . 0.93 ?
N1 N2 . 1.300(4) ?
N4 N5 . 1.310(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 C3 N4 120.7(4) . . ?
O1 C3 N2 120.0(4) . . ?
N4 C3 N2 119.0(4) . . ?
N1 C6 N5 123.6(3) . . ?
N1 C6 C12 118.1(3) . . ?
N5 C6 C12 118.0(3) . . ?
N13 C12 N11 112.9(3) . . ?
N13 C12 C6 124.5(3) . . ?
N11 C12 C6 122.6(3) . . ?
N13 C14 C15 103.5(3) . . ?
N13 C14 H14A 111.1 . . ?
C15 C14 H14A 111.1 . . ?
N13 C14 H14B 111.1 . . ?
C15 C14 H14B 111.1 . . ?
H14A C14 H14B 109 . . ?
N11 C15 C14 103.3(3) . . ?
N11 C15 H15A 111.1 . . ?
C14 C15 H15A 111.1 . . ?
N11 C15 H15B 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
C82 C81 C86 122.8(3) . . ?
C82 C81 N11 119.0(3) . . ?
C86 C81 N11 118.2(3) . . ?
C81 C82 C83 117.0(4) . . ?
C81 C82 C87 121.6(3) . . ?
C83 C82 C87 121.4(4) . . ?
C84 C83 C82 122.3(4) . . ?
C84 C83 H83 118.8 . . ?
C82 C83 H83 118.8 . . ?
C83 C84 C85 118.9(4) . . ?
C83 C84 C88 120.7(4) . . ?
C85 C84 C88 120.4(4) . . ?
C86 C85 C84 121.7(4) . . ?
C86 C85 H85 119.1 . . ?
C84 C85 H85 119.1 . . ?
C85 C86 C81 117.3(4) . . ?
C85 C86 C89 120.8(4) . . ?
C81 C86 C89 121.9(4) . . ?
C82 C87 H87A 109.5 . . ?
C82 C87 H87B 109.5 . . ?
H87A C87 H87B 109.5 . . ?
C82 C87 H87C 109.5 . . ?
H87A C87 H87C 109.5 . . ?
H87B C87 H87C 109.5 . . ?
C84 C88 H88A 109.5 . . ?
C84 C88 H88B 109.5 . . ?
H88A C88 H88B 109.5 . . ?
C84 C88 H88C 109.5 . . ?
H88A C88 H88C 109.5 . . ?
H88B C88 H88C 109.5 . . ?
C86 C89 H89A 109.5 . . ?
C86 C89 H89B 109.5 . . ?
H89A C89 H89B 109.5 . . ?
C86 C89 H89C 109.5 . . ?
H89A C89 H89C 109.5 . . ?
H89B C89 H89C 109.5 . . ?
N13 C91 C93 111.5(3) . . ?
N13 C91 C92 110.0(3) . . ?
C93 C91 C92 111.8(3) . . ?
N13 C91 H91 107.8 . . ?
C93 C91 H91 107.8 . . ?
C92 C91 H91 107.8 . . ?
C91 C92 H92A 109.5 . . ?
C91 C92 H92B 109.5 . . ?
H92A C92 H92B 109.5 . . ?
C91 C92 H92C 109.5 . . ?
H92A C92 H92C 109.5 . . ?
H92B C92 H92C 109.5 . . ?
C94 C93 C98 117.6(4) . . ?
C94 C93 C91 123.3(4) . . ?
C98 C93 C91 119.0(4) . . ?
C95 C94 C93 121.1(4) . . ?
C95 C94 H94 119.5 . . ?
C93 C94 H94 119.5 . . ?
C96 C95 C94 120.6(4) . . ?
C96 C95 H95 119.7 . . ?
C94 C95 H95 119.7 . . ?
C95 C96 C97 119.3(4) . . ?
C95 C96 H96 120.4 . . ?
C97 C96 H96 120.4 . . ?
C98 C97 C96 120.1(4) . . ?
C98 C97 H97 119.9 . . ?
C96 C97 H97 119.9 . . ?
C97 C98 C93 121.3(4) . . ?
C97 C98 H98 119.3 . . ?
C93 C98 H98 119.3 . . ?
N2 N1 C6 118.7(3) . . ?
N1 N2 C3 117.2(3) . . ?
N5 N4 C3 117.6(3) . . ?
N4 N5 C6 117.8(3) . . ?
C12 N11 C81 126.1(3) . . ?
C12 N11 C15 109.9(3) . . ?
C81 N11 C15 121.3(3) . . ?
C12 N13 C91 124.2(3) . . ?
C12 N13 C14 110.2(3) . . ?
C91 N13 C14 124.6(3) . . ?
_database_code_depnum_ccdc_archive 'CCDC 1003468'
#######################################################################
#
#                 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_5

_audit_creation_date             2013-05-28T12:07:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H15 N7 O1'
_chemical_formula_sum            'C22 H15 N7 O'
_chemical_formula_weight         393.41

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1099(10)
_cell_length_b                   9.7574(10)
_cell_length_c                   11.9033(10)
_cell_angle_alpha                97.231(10)
_cell_angle_beta                 112.188(10)
_cell_angle_gamma                95.337(10)
_cell_volume                     960.48(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.2
_cell_measurement_theta_max      17
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.36
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   4
        Theta correction was applied.
        Averaged transmission function was used.
        Fourier smoothing - Window value   5
;
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_T_max  0.9851

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius MACH3'
_diffrn_measurement_method       'profiled omega/2theta scans'
_diffrn_reflns_number            3876
_diffrn_reflns_av_R_equivalents  0.0085
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_max 1
_diffrn_measured_fraction_theta_full 1
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         3
_diffrn_standards_interval_count 108
_diffrn_standards_interval_time  56
_diffrn_standards_decay_%        100
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 2 -7
0 2 -6
4 0 -4


#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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 > 2σ(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.
;
_reflns_number_total             3525
_reflns_number_gt                3207
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1307
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_refine_ls_number_reflns         3525
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.2438P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'MACH3/PC(Enraf Nonius, 1992)'
_computing_cell_refinement       'MACH3/PC (Enraf Nonius, 1992)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C3 -0.2704(2) 0.12402(18) -0.10212(17) 0.0490(4) Uani d . 1 . . C
C6 -0.09048(19) 0.08887(16) 0.11647(15) 0.0401(4) Uani d . 1 . . C
C12 0.02353(19) 0.07104(16) 0.23595(15) 0.0392(4) Uani d . 1 . . C
C15 0.15002(19) -0.01475(17) 0.40252(15) 0.0408(4) Uani d . 1 . . C
C81 -0.08690(19) -0.17416(16) 0.23411(14) 0.0389(4) Uani d . 1 . . C
C82 -0.0275(2) -0.29081(17) 0.20249(17) 0.0478(4) Uani d . 1 . . C
H82 0.0794 -0.2856 0.2128 0.057 Uiso calc . 1 . . H
C83 -0.1310(3) -0.41591(19) 0.1550(2) 0.0636(6) Uani d . 1 . . C
H83 -0.0931 -0.4967 0.1346 0.076 Uiso calc . 1 . . H
C84 -0.2889(3) -0.4219(2) 0.1377(2) 0.0693(6) Uani d . 1 . . C
H84 -0.3579 -0.5064 0.1046 0.083 Uiso calc . 1 . . H
C85 -0.3463(2) -0.3037(2) 0.1691(2) 0.0679(6) Uani d . 1 . . C
H85 -0.4539 -0.3084 0.1566 0.081 Uiso calc . 1 . . H
C86 -0.2441(2) -0.1778(2) 0.21909(18) 0.0537(5) Uani d . 1 . . C
H86 -0.2812 -0.0977 0.242 0.064 Uiso calc . 1 . . H
C91 0.2084(2) 0.30156(16) 0.30690(16) 0.0426(4) Uani d . 1 . . C
C92 0.2216(2) 0.32743(18) 0.20013(18) 0.0522(4) Uani d . 1 . . C
H92 0.1878 0.2576 0.131 0.063 Uiso calc . 1 . . H
C93 0.2869(3) 0.4609(2) 0.1985(2) 0.0610(5) Uani d . 1 . . C
H93 0.2961 0.4816 0.127 0.073 Uiso calc . 1 . . H
C94 0.3379(2) 0.56289(19) 0.3014(2) 0.0604(5) Uani d . 1 . . C
H94 0.3825 0.6518 0.2995 0.072 Uiso calc . 1 . . H
C95 0.3237(2) 0.53454(19) 0.4064(2) 0.0590(5) Uani d . 1 . . C
H95 0.3579 0.6044 0.4756 0.071 Uiso calc . 1 . . H
C96 0.2589(2) 0.40306(19) 0.41072(17) 0.0519(4) Uani d . 1 . . C
H96 0.2494 0.3832 0.4823 0.062 Uiso calc . 1 . . H
C101 0.1983(2) -0.10571(17) 0.49561(15) 0.0416(4) Uani d . 1 . . C
C102 0.3575(2) -0.08041(18) 0.57929(16) 0.0481(4) Uani d . 1 . . C
H102 0.4293 -0.0112 0.5722 0.058 Uiso calc . 1 . . H
C103 0.4097(2) -0.1574(2) 0.67283(17) 0.0546(5) Uani d . 1 . . C
H103 0.5163 -0.1405 0.7282 0.066 Uiso calc . 1 . . H
C104 0.3031(3) -0.2591(2) 0.68369(18) 0.0597(5) Uani d . 1 . . C
H104 0.3378 -0.311 0.7467 0.072 Uiso calc . 1 . . H
C105 0.1458(3) -0.2843(2) 0.60199(19) 0.0596(5) Uani d . 1 . . C
H105 0.0749 -0.3535 0.61 0.072 Uiso calc . 1 . . H
C106 0.0917(2) -0.2085(2) 0.50825(17) 0.0509(4) Uani d . 1 . . C
H106 -0.0154 -0.2257 0.4538 0.061 Uiso calc . 1 . . H
N1 -0.1449(2) -0.02343(15) 0.02791(14) 0.0549(4) Uani d . 1 . . N
N2 -0.2388(2) -0.00835(16) -0.08230(14) 0.0584(4) Uani d . 1 . . N
N4 -0.2333(2) 0.23259(16) -0.00342(15) 0.0565(4) Uani d . 1 . . N
N5 -0.13836(19) 0.21387(15) 0.10562(14) 0.0511(4) Uani d . 1 . . N
N11 0.02383(16) -0.04426(13) 0.28866(12) 0.0392(3) Uani d . 1 . . N
N13 0.14683(17) 0.16297(13) 0.31584(12) 0.0423(3) Uani d . 1 . . N
N14 0.22561(17) 0.11180(14) 0.42083(13) 0.0449(3) Uani d . 1 . . N
O1 -0.3326(2) 0.14376(16) -0.20749(14) 0.0818(5) Uani d . 1 . . O



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C3 O1 . 1.215(2) ?
C3 N2 . 1.379(2) ?
C3 N4 . 1.392(2) ?
C6 N1 . 1.331(2) ?
C6 N5 . 1.338(2) ?
C6 C12 . 1.453(2) ?
C12 N13 . 1.327(2) ?
C12 N11 . 1.355(2) ?
C15 N14 . 1.307(2) ?
C15 N11 . 1.380(2) ?
C15 C101 . 1.470(2) ?
C81 C86 . 1.371(2) ?
C81 C82 . 1.375(2) ?
C81 N11 . 1.4512(19) ?
C82 C83 . 1.381(3) ?
C82 H82 . 0.93 ?
C83 C84 . 1.369(3) ?
C83 H83 . 0.93 ?
C84 C85 . 1.376(3) ?
C84 H84 . 0.93 ?
C85 C86 . 1.384(3) ?
C85 H85 . 0.93 ?
C86 H86 . 0.93 ?
C91 C92 . 1.373(3) ?
C91 C96 . 1.377(2) ?
C91 N13 . 1.447(2) ?
C92 C93 . 1.386(3) ?
C92 H92 . 0.93 ?
C93 C94 . 1.372(3) ?
C93 H93 . 0.93 ?
C94 C95 . 1.364(3) ?
C94 H94 . 0.93 ?
C95 C96 . 1.377(3) ?
C95 H95 . 0.93 ?
C96 H96 . 0.93 ?
C101 C102 . 1.392(2) ?
C101 C106 . 1.393(2) ?
C102 C103 . 1.381(3) ?
C102 H102 . 0.93 ?
C103 C104 . 1.375(3) ?
C103 H103 . 0.93 ?
C104 C105 . 1.371(3) ?
C104 H104 . 0.93 ?
C105 C106 . 1.377(3) ?
C105 H105 . 0.93 ?
C106 H106 . 0.93 ?
N1 N2 . 1.303(2) ?
N4 N5 . 1.307(2) ?
N13 N14 . 1.3685(19) ?

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 C3 N2 118.69(18) . . ?
O1 C3 N4 120.60(17) . . ?
N2 C3 N4 120.71(16) . . ?
N1 C6 N5 125.18(15) . . ?
N1 C6 C12 116.83(14) . . ?
N5 C6 C12 117.90(14) . . ?
N13 C12 N11 105.99(14) . . ?
N13 C12 C6 127.66(14) . . ?
N11 C12 C6 126.35(14) . . ?
N14 C15 N11 110.33(14) . . ?
N14 C15 C101 121.98(14) . . ?
N11 C15 C101 127.68(14) . . ?
C86 C81 C82 122.44(16) . . ?
C86 C81 N11 119.61(15) . . ?
C82 C81 N11 117.93(15) . . ?
C81 C82 C83 118.16(17) . . ?
C81 C82 H82 120.9 . . ?
C83 C82 H82 120.9 . . ?
C84 C83 C82 120.50(19) . . ?
C84 C83 H83 119.7 . . ?
C82 C83 H83 119.7 . . ?
C83 C84 C85 120.42(18) . . ?
C83 C84 H84 119.8 . . ?
C85 C84 H84 119.8 . . ?
C84 C85 C86 120.08(19) . . ?
C84 C85 H85 120 . . ?
C86 C85 H85 120 . . ?
C81 C86 C85 118.38(18) . . ?
C81 C86 H86 120.8 . . ?
C85 C86 H86 120.8 . . ?
C92 C91 C96 122.05(16) . . ?
C92 C91 N13 120.54(15) . . ?
C96 C91 N13 117.34(16) . . ?
C91 C92 C93 117.95(18) . . ?
C91 C92 H92 121 . . ?
C93 C92 H92 121 . . ?
C94 C93 C92 120.56(19) . . ?
C94 C93 H93 119.7 . . ?
C92 C93 H93 119.7 . . ?
C95 C94 C93 120.38(17) . . ?
C95 C94 H94 119.8 . . ?
C93 C94 H94 119.8 . . ?
C94 C95 C96 120.37(18) . . ?
C94 C95 H95 119.8 . . ?
C96 C95 H95 119.8 . . ?
C95 C96 C91 118.68(18) . . ?
C95 C96 H96 120.7 . . ?
C91 C96 H96 120.7 . . ?
C102 C101 C106 119.19(16) . . ?
C102 C101 C15 117.26(15) . . ?
C106 C101 C15 123.43(15) . . ?
C103 C102 C101 120.45(17) . . ?
C103 C102 H102 119.8 . . ?
C101 C102 H102 119.8 . . ?
C104 C103 C102 119.69(17) . . ?
C104 C103 H103 120.2 . . ?
C102 C103 H103 120.2 . . ?
C105 C104 C103 120.25(18) . . ?
C105 C104 H104 119.9 . . ?
C103 C104 H104 119.9 . . ?
C104 C105 C106 120.88(18) . . ?
C104 C105 H105 119.6 . . ?
C106 C105 H105 119.6 . . ?
C105 C106 C101 119.54(17) . . ?
C105 C106 H106 120.2 . . ?
C101 C106 H106 120.2 . . ?
N2 N1 C6 118.14(14) . . ?
N1 N2 C3 118.27(15) . . ?
N5 N4 C3 117.82(14) . . ?
N4 N5 C6 117.94(15) . . ?
C12 N11 C15 106.95(13) . . ?
C12 N11 C81 126.09(13) . . ?
C15 N11 C81 126.96(13) . . ?
C12 N13 N14 111.64(13) . . ?
C12 N13 C91 130.51(14) . . ?
N14 N13 C91 117.84(13) . . ?
C15 N14 N13 105.07(13) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF


_database_code_depnum_ccdc_archive 'CCDC 1003469'
