# Electronic Supplementary Material (ESI) for ChemComm.
# 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_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 N4 O2'
_chemical_formula_sum            'C13 H14 N4 O2'
_chemical_formula_weight         258.28

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   8.1976(5)
_cell_length_b                   12.7958(7)
_cell_length_c                   11.9888(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.2270(10)
_cell_angle_gamma                90.00
_cell_volume                     1218.99(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4644
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.74

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9542
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
  Bruker-Nonius X8kappa APEX II CCD area detector'
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11401
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2164
_reflns_number_gt                2022
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_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.

  ADDSYM detects (Pseudo) Centre of Symmetry. Model and data transformation
  to new cell parammeters and space group P 21/c, disprove this issue.
  The new structure was observed with the morpholine ring disordered, which
  was modeled in two positions and refined with anisotropic displacement
  parameters and geometric restrains; the occupancy factors for these two
  disordered moieties were all set to 0.5. Nevertheless, at the end of
  refinement the R1 factor was not possible to lover it of 20.

;

_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)+(0.0496P)²+0.1403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2164
_refine_ls_number_parameters     344
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0727
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.1765(2) 0.45793(13) 0.83261(16) 0.0317(4) Uani 1 1 d . . .
O2 O 1.0318(2) 0.10325(14) 0.72996(16) 0.0399(5) Uani 1 1 d . . .
N1 N 0.9331(2) 0.49191(15) 0.70094(16) 0.0221(4) Uani 1 1 d . . .
N2 N 0.7623(2) 0.47864(16) 0.66523(18) 0.0271(4) Uani 1 1 d . . .
N3 N 0.7003(2) 0.56423(16) 0.61373(17) 0.0268(4) Uani 1 1 d . . .
N4 N 1.0052(2) 0.31974(16) 0.77206(17) 0.0261(5) Uani 1 1 d . . .
C1 C 1.0476(3) 0.42048(18) 0.7740(2) 0.0235(5) Uani 1 1 d . . .
C2 C 0.8650(3) 0.26362(19) 0.6957(2) 0.0320(6) Uani 1 1 d . . .
H2A H 0.8059 0.3107 0.6332 0.038 Uiso 1 1 calc R . .
H2B H 0.7836 0.2411 0.7397 0.038 Uiso 1 1 calc R . .
C3 C 0.9310(3) 0.1690(2) 0.6447(2) 0.0379(6) Uani 1 1 d . . .
H3A H 0.8346 0.1283 0.5994 0.045 Uiso 1 1 calc R . .
H3B H 0.9986 0.1928 0.5915 0.045 Uiso 1 1 calc R . .
C4 C 1.1710(3) 0.1601(2) 0.7954(2) 0.0354(6) Uani 1 1 d . . .
H4A H 1.2392 0.1868 0.7440 0.042 Uiso 1 1 calc R . .
H4B H 1.2429 0.1131 0.8526 0.042 Uiso 1 1 calc R . .
C5 C 1.1127(3) 0.2503(2) 0.8566(2) 0.0330(6) Uani 1 1 d . . .
H5A H 1.0489 0.2236 0.9109 0.040 Uiso 1 1 calc R . .
H5B H 1.2113 0.2896 0.9012 0.040 Uiso 1 1 calc R . .
C6 C 0.9757(3) 0.58884(17) 0.67182(19) 0.0234(5) Uani 1 1 d . . .
H6 H 1.0851 0.6187 0.6874 0.028 Uiso 1 1 calc R . .
C7 C 0.8281(3) 0.63399(17) 0.61548(19) 0.0222(5) Uani 1 1 d . . .
C8 C 0.7952(3) 0.73808(18) 0.5619(2) 0.0233(5) Uani 1 1 d . . .
C9 C 0.9234(3) 0.8127(2) 0.5796(2) 0.0278(5) Uani 1 1 d . . .
H9 H 1.0304 0.7974 0.6290 0.033 Uiso 1 1 calc R . .
C10 C 0.8949(3) 0.90896(19) 0.5253(2) 0.0303(6) Uani 1 1 d . . .
H10 H 0.9823 0.9596 0.5382 0.036 Uiso 1 1 calc R . .
C11 C 0.7399(3) 0.9318(2) 0.4525(2) 0.0313(6) Uani 1 1 d . . .
H11 H 0.7212 0.9975 0.4146 0.038 Uiso 1 1 calc R . .
C12 C 0.6127(3) 0.8584(2) 0.4354(2) 0.0325(6) Uani 1 1 d . . .
H12 H 0.5062 0.8739 0.3855 0.039 Uiso 1 1 calc R . .
C13 C 0.6390(3) 0.76252(19) 0.4904(2) 0.0281(5) Uani 1 1 d . . .
H13 H 0.5498 0.7132 0.4791 0.034 Uiso 1 1 calc R . .
O3 O 0.3281(2) 0.70396(14) 0.68200(16) 0.0347(4) Uani 1 1 d . . .
O4 O 0.5658(2) 1.05816(13) 0.75904(16) 0.0382(4) Uani 1 1 d . . .
N5 N 0.5663(2) 0.66836(15) 0.81876(17) 0.0238(4) Uani 1 1 d . . .
N6 N 0.7363(2) 0.68415(15) 0.85623(18) 0.0275(5) Uani 1 1 d . . .
N7 N 0.8000(2) 0.59879(15) 0.90707(17) 0.0275(4) Uani 1 1 d . . .
N8 N 0.4886(2) 0.84269(17) 0.76193(17) 0.0283(5) Uani 1 1 d . . .
C14 C 0.4508(3) 0.74100(19) 0.7487(2) 0.0258(5) Uani 1 1 d . . .
C15 C 0.6000(3) 0.89472(19) 0.8618(2) 0.0323(6) Uani 1 1 d . . .
H15A H 0.6854 0.8446 0.9037 0.039 Uiso 1 1 calc R . .
H15B H 0.5334 0.9195 0.9152 0.039 Uiso 1 1 calc R . .
C16 C 0.6856(3) 0.9857(2) 0.8208(3) 0.0378(6) Uani 1 1 d . . .
H16A H 0.7599 1.0211 0.8877 0.045 Uiso 1 1 calc R . .
H16B H 0.7563 0.9600 0.7705 0.045 Uiso 1 1 calc R . .
C17 C 0.4637(4) 1.0090(2) 0.6601(2) 0.0397(6) Uani 1 1 d . . .
H17A H 0.5355 0.9867 0.6090 0.048 Uiso 1 1 calc R . .
H17B H 0.3812 1.0603 0.6174 0.048 Uiso 1 1 calc R . .
C18 C 0.3706(3) 0.9156(2) 0.6891(2) 0.0341(6) Uani 1 1 d . . .
H18A H 0.2857 0.9387 0.7300 0.041 Uiso 1 1 calc R . .
H18B H 0.3110 0.8799 0.6174 0.041 Uiso 1 1 calc R . .
C19 C 0.5260(3) 0.57037(18) 0.84476(19) 0.0243(5) Uani 1 1 d . . .
H19 H 0.4177 0.5390 0.8270 0.029 Uiso 1 1 calc R . .
C20 C 0.6749(3) 0.52638(18) 0.9020(2) 0.0235(5) Uani 1 1 d . . .
C21 C 0.7108(3) 0.42139(19) 0.9510(2) 0.0239(5) Uani 1 1 d . . .
C22 C 0.6038(3) 0.3383(2) 0.9106(2) 0.0289(6) Uani 1 1 d . . .
H22 H 0.5061 0.3493 0.8501 0.035 Uiso 1 1 calc R . .
C23 C 0.6382(3) 0.2396(2) 0.9577(2) 0.0332(6) Uani 1 1 d . . .
H23 H 0.5643 0.1831 0.9294 0.040 Uiso 1 1 calc R . .
C24 C 0.7802(3) 0.2229(2) 1.0461(2) 0.0326(6) Uani 1 1 d . . .
H24 H 0.8040 0.1551 1.0782 0.039 Uiso 1 1 calc R . .
C25 C 0.8866(3) 0.3048(2) 1.0872(2) 0.0338(6) Uani 1 1 d . . .
H25 H 0.9834 0.2933 1.1484 0.041 Uiso 1 1 calc R . .
C26 C 0.8541(3) 0.4036(2) 1.0404(2) 0.0296(6) Uani 1 1 d . . .
H26 H 0.9290 0.4595 1.0690 0.036 Uiso 1 1 calc R . .


_geom_special_details            
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate (isotropic)
  treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.215(3) . ?
O2 C4 1.416(3) . ?
O2 C3 1.422(3) . ?
N1 C6 1.357(3) . ?
N1 N2 1.370(3) . ?
N1 C1 1.442(3) . ?
N2 N3 1.298(3) . ?
N3 C7 1.372(3) . ?
N4 C1 1.334(3) . ?
N4 C5 1.468(3) . ?
N4 C2 1.469(3) . ?
C2 C3 1.515(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.507(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.361(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.474(3) . ?
C8 C13 1.391(3) . ?
C8 C9 1.397(3) . ?
C9 C10 1.386(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O3 C14 1.216(3) . ?
O4 C16 1.419(3) . ?
O4 C17 1.420(3) . ?
N5 C19 1.352(3) . ?
N5 N6 1.370(3) . ?
N5 C14 1.441(3) . ?
N6 N7 1.296(3) . ?
N7 C20 1.373(3) . ?
N8 C14 1.338(3) . ?
N8 C18 1.467(3) . ?
N8 C15 1.475(3) . ?
C15 C16 1.503(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.504(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.366(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.467(3) . ?
C21 C22 1.387(3) . ?
C21 C26 1.401(4) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C3 109.95(19) . . ?
C6 N1 N2 109.92(19) . . ?
C6 N1 C1 124.42(19) . . ?
N2 N1 C1 125.01(18) . . ?
N3 N2 N1 107.16(18) . . ?
N2 N3 C7 109.45(18) . . ?
C1 N4 C5 117.6(2) . . ?
C1 N4 C2 130.1(2) . . ?
C5 N4 C2 112.3(2) . . ?
O1 C1 N4 125.2(2) . . ?
O1 C1 N1 116.4(2) . . ?
N4 C1 N1 118.3(2) . . ?
N4 C2 C3 109.9(2) . . ?
N4 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
N4 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
O2 C3 C2 112.6(2) . . ?
O2 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
O2 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
O2 C4 C5 110.8(2) . . ?
O2 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
O2 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N4 C5 C4 109.6(2) . . ?
N4 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
N4 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 C7 105.16(19) . . ?
N1 C6 H6 127.4 . . ?
C7 C6 H6 127.4 . . ?
C6 C7 N3 108.3(2) . . ?
C6 C7 C8 130.1(2) . . ?
N3 C7 C8 121.6(2) . . ?
C13 C8 C9 119.0(2) . . ?
C13 C8 C7 120.9(2) . . ?
C9 C8 C7 120.1(2) . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.5(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C16 O4 C17 109.69(19) . . ?
C19 N5 N6 110.33(19) . . ?
C19 N5 C14 124.74(19) . . ?
N6 N5 C14 124.46(18) . . ?
N7 N6 N5 106.85(18) . . ?
N6 N7 C20 109.73(18) . . ?
C14 N8 C18 116.6(2) . . ?
C14 N8 C15 127.9(2) . . ?
C18 N8 C15 112.5(2) . . ?
O3 C14 N8 125.9(2) . . ?
O3 C14 N5 116.8(2) . . ?
N8 C14 N5 117.3(2) . . ?
N8 C15 C16 109.2(2) . . ?
N8 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
N8 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
O4 C16 C15 111.0(2) . . ?
O4 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
O4 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O4 C17 C18 112.8(2) . . ?
O4 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
O4 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
N8 C18 C17 110.2(2) . . ?
N8 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
N8 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
N5 C19 C20 105.0(2) . . ?
N5 C19 H19 127.5 . . ?
C20 C19 H19 127.5 . . ?
C19 C20 N7 108.0(2) . . ?
C19 C20 C21 130.2(2) . . ?
N7 C20 C21 121.8(2) . . ?
C22 C21 C26 118.8(2) . . ?
C22 C21 C20 121.0(2) . . ?
C26 C21 C20 120.2(2) . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 120.1(3) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?

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
C6 N1 N2 N3 0.9(2) . . . . ?
C1 N1 N2 N3 171.98(19) . . . . ?
N1 N2 N3 C7 -0.2(2) . . . . ?
C5 N4 C1 O1 7.3(3) . . . . ?
C2 N4 C1 O1 -171.6(2) . . . . ?
C5 N4 C1 N1 -172.85(19) . . . . ?
C2 N4 C1 N1 8.2(3) . . . . ?
C6 N1 C1 O1 17.2(3) . . . . ?
N2 N1 C1 O1 -152.6(2) . . . . ?
C6 N1 C1 N4 -162.6(2) . . . . ?
N2 N1 C1 N4 27.6(3) . . . . ?
C1 N4 C2 C3 128.0(3) . . . . ?
C5 N4 C2 C3 -51.0(3) . . . . ?
C4 O2 C3 C2 -59.0(3) . . . . ?
N4 C2 C3 O2 53.5(3) . . . . ?
C3 O2 C4 C5 61.3(3) . . . . ?
C1 N4 C5 C4 -125.1(2) . . . . ?
C2 N4 C5 C4 54.0(3) . . . . ?
O2 C4 C5 N4 -58.8(3) . . . . ?
N2 N1 C6 C7 -1.2(2) . . . . ?
C1 N1 C6 C7 -172.32(18) . . . . ?
N1 C6 C7 N3 1.0(2) . . . . ?
N1 C6 C7 C8 -178.8(2) . . . . ?
N2 N3 C7 C6 -0.5(2) . . . . ?
N2 N3 C7 C8 179.31(19) . . . . ?
C6 C7 C8 C13 168.2(2) . . . . ?
N3 C7 C8 C13 -11.6(3) . . . . ?
C6 C7 C8 C9 -9.7(4) . . . . ?
N3 C7 C8 C9 170.6(2) . . . . ?
C13 C8 C9 C10 -0.7(3) . . . . ?
C7 C8 C9 C10 177.2(2) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C8 -1.2(4) . . . . ?
C9 C8 C13 C12 1.6(3) . . . . ?
C7 C8 C13 C12 -176.3(2) . . . . ?
C19 N5 N6 N7 -1.6(2) . . . . ?
C14 N5 N6 N7 -174.07(19) . . . . ?
N5 N6 N7 C20 1.0(2) . . . . ?
C18 N8 C14 O3 0.0(3) . . . . ?
C15 N8 C14 O3 158.9(2) . . . . ?
C18 N8 C14 N5 179.4(2) . . . . ?
C15 N8 C14 N5 -21.7(3) . . . . ?
C19 N5 C14 O3 -22.9(3) . . . . ?
N6 N5 C14 O3 148.6(2) . . . . ?
C19 N5 C14 N8 157.7(2) . . . . ?
N6 N5 C14 N8 -30.9(3) . . . . ?
C14 N8 C15 C16 147.0(2) . . . . ?
C18 N8 C15 C16 -53.3(3) . . . . ?
C17 O4 C16 C15 -61.7(3) . . . . ?
N8 C15 C16 O4 58.7(3) . . . . ?
C16 O4 C17 C18 59.1(3) . . . . ?
C14 N8 C18 C17 -147.3(2) . . . . ?
C15 N8 C18 C17 50.5(3) . . . . ?
O4 C17 C18 N8 -53.3(3) . . . . ?
N6 N5 C19 C20 1.5(2) . . . . ?
C14 N5 C19 C20 173.97(19) . . . . ?
N5 C19 C20 N7 -0.9(2) . . . . ?
N5 C19 C20 C21 -179.7(2) . . . . ?
N6 N7 C20 C19 -0.1(2) . . . . ?
N6 N7 C20 C21 178.89(19) . . . . ?
C19 C20 C21 C22 23.2(4) . . . . ?
N7 C20 C21 C22 -155.5(2) . . . . ?
C19 C20 C21 C26 -156.3(2) . . . . ?
N7 C20 C21 C26 25.0(3) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?
C20 C21 C22 C23 -179.7(2) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 C25 0.2(4) . . . . ?
C23 C24 C25 C26 -0.6(4) . . . . ?
C24 C25 C26 C21 0.6(4) . . . . ?
C22 C21 C26 C25 -0.2(3) . . . . ?
C20 C21 C26 C25 179.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 1002750'
#######################################################################
#
#                 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_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?

_chemical_formula_moiety         'C13 H13 Br N4 O2'
_chemical_formula_sum            'C13 H13 Br N4 O2'
_chemical_formula_weight         337.18

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'
Br Br -0.2901 2.4595 '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'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   28.3878(14)
_cell_length_b                   5.0616(3)
_cell_length_c                   18.7871(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.781(3)
_cell_angle_gamma                90.00
_cell_volume                     2685.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5622
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      29.62

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    3.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5807
_exptl_absorpt_correction_T_max  0.7359
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
  Bruker-Nonius X8kappa APEX II CCD area detector'
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12029
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2248
_reflns_number_gt                1967
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0599P)²+4.2100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2248
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
Br1 Br 0.060168(10) 0.80393(7) 0.154967(16) 0.03319(15) Uani 1 1 d . . .
O1 O 0.31925(7) -0.2705(4) 0.01056(10) 0.0271(5) Uani 1 1 d . . .
O2 O 0.47496(7) -0.3160(5) 0.15120(12) 0.0389(6) Uani 1 1 d . . .
N1 N 0.30919(7) 0.0259(5) 0.09815(11) 0.0195(5) Uani 1 1 d . . .
N2 N 0.32822(8) 0.2393(5) 0.13544(13) 0.0242(5) Uani 1 1 d . . .
N3 N 0.29304(8) 0.3850(5) 0.15078(12) 0.0242(5) Uani 1 1 d . . .
N4 N 0.38096(8) -0.2104(5) 0.09624(12) 0.0213(5) Uani 1 1 d . . .
C1 C 0.33666(10) -0.1689(5) 0.06550(14) 0.0212(6) Uani 1 1 d . . .
C2 C 0.41095(10) -0.3823(7) 0.05751(15) 0.0287(7) Uani 1 1 d . . .
H2A H 0.4023 -0.3652 0.0053 0.034 Uiso 1 1 calc R . .
H2B H 0.4065 -0.5688 0.0712 0.034 Uiso 1 1 calc R . .
C3 C 0.46200(11) -0.3019(8) 0.07614(18) 0.0385(8) Uani 1 1 d . . .
H3A H 0.4828 -0.4196 0.0512 0.046 Uiso 1 1 calc R . .
H3B H 0.4666 -0.1190 0.0594 0.046 Uiso 1 1 calc R . .
C4 C 0.44660(10) -0.1409(7) 0.18785(16) 0.0316(7) Uani 1 1 d . . .
H4A H 0.4517 0.0425 0.1720 0.038 Uiso 1 1 calc R . .
H4B H 0.4564 -0.1506 0.2399 0.038 Uiso 1 1 calc R . .
C5 C 0.39478(10) -0.2093(6) 0.17385(14) 0.0232(6) Uani 1 1 d . . .
H5A H 0.3889 -0.3855 0.1941 0.028 Uiso 1 1 calc R . .
H5B H 0.3756 -0.0779 0.1972 0.028 Uiso 1 1 calc R . .
C6 C 0.26156(9) 0.0438(6) 0.08939(14) 0.0211(6) Uani 1 1 d . . .
H6 H 0.2399 -0.0760 0.0647 0.025 Uiso 1 1 calc R . .
C7 C 0.25112(10) 0.2712(5) 0.12361(14) 0.0204(6) Uani 1 1 d . . .
C8 C 0.20500(10) 0.3929(6) 0.13303(14) 0.0213(6) Uani 1 1 d . . .
C9 C 0.20202(10) 0.6048(6) 0.17886(14) 0.0243(6) Uani 1 1 d . . .
H9 H 0.2298 0.6673 0.2060 0.029 Uiso 1 1 calc R . .
C10 C 0.15909(11) 0.7271(6) 0.18565(15) 0.0268(7) Uani 1 1 d . . .
H10 H 0.1573 0.8749 0.2164 0.032 Uiso 1 1 calc R . .
C11 C 0.11882(10) 0.6304(6) 0.14689(15) 0.0261(6) Uani 1 1 d . . .
C12 C 0.12077(10) 0.4157(6) 0.10226(16) 0.0276(6) Uani 1 1 d . . .
H12 H 0.0927 0.3494 0.0766 0.033 Uiso 1 1 calc R . .
C13 C 0.16376(11) 0.2980(6) 0.09521(16) 0.0264(7) Uani 1 1 d . . .
H13 H 0.1653 0.1506 0.0642 0.032 Uiso 1 1 calc R . .


_geom_special_details            
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate (isotropic)
  treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.902(3) . ?
O1 C1 1.213(3) . ?
O2 C4 1.421(4) . ?
O2 C3 1.423(4) . ?
N1 C6 1.349(3) . ?
N1 N2 1.368(3) . ?
N1 C1 1.433(4) . ?
N2 N3 1.297(4) . ?
N3 C7 1.374(4) . ?
N4 C1 1.346(3) . ?
N4 C2 1.462(4) . ?
N4 C5 1.471(3) . ?
C2 C3 1.512(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.508(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.365(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.473(4) . ?
C8 C9 1.384(4) . ?
C8 C13 1.392(4) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(4) . ?
C12 C13 1.376(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C3 110.3(2) . . ?
C6 N1 N2 110.4(2) . . ?
C6 N1 C1 125.2(2) . . ?
N2 N1 C1 124.0(2) . . ?
N3 N2 N1 106.8(2) . . ?
N2 N3 C7 109.7(2) . . ?
C1 N4 C2 116.4(2) . . ?
C1 N4 C5 124.7(2) . . ?
C2 N4 C5 112.7(2) . . ?
O1 C1 N4 125.6(3) . . ?
O1 C1 N1 117.6(2) . . ?
N4 C1 N1 116.7(2) . . ?
N4 C2 C3 108.5(2) . . ?
N4 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
N4 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
O2 C3 C2 111.2(3) . . ?
O2 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
O2 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O2 C4 C5 111.3(2) . . ?
O2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
O2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N4 C5 C4 109.4(2) . . ?
N4 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
N4 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 C7 105.2(2) . . ?
N1 C6 H6 127.4 . . ?
C7 C6 H6 127.4 . . ?
C6 C7 N3 107.9(2) . . ?
C6 C7 C8 130.3(2) . . ?
N3 C7 C8 121.8(2) . . ?
C9 C8 C13 119.0(3) . . ?
C9 C8 C7 120.6(2) . . ?
C13 C8 C7 120.4(3) . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 Br1 120.1(2) . . ?
C10 C11 Br1 118.6(2) . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C8 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?

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
C6 N1 N2 N3 1.1(3) . . . . ?
C1 N1 N2 N3 173.7(2) . . . . ?
N1 N2 N3 C7 -0.4(3) . . . . ?
C2 N4 C1 O1 3.4(4) . . . . ?
C5 N4 C1 O1 -146.7(3) . . . . ?
C2 N4 C1 N1 -172.0(2) . . . . ?
C5 N4 C1 N1 37.9(4) . . . . ?
C6 N1 C1 O1 24.4(4) . . . . ?
N2 N1 C1 O1 -147.1(3) . . . . ?
C6 N1 C1 N4 -159.9(3) . . . . ?
N2 N1 C1 N4 28.6(4) . . . . ?
C1 N4 C2 C3 151.7(3) . . . . ?
C5 N4 C2 C3 -54.7(3) . . . . ?
C4 O2 C3 C2 -61.2(4) . . . . ?
N4 C2 C3 O2 57.7(4) . . . . ?
C3 O2 C4 C5 60.0(4) . . . . ?
C1 N4 C5 C4 -154.9(3) . . . . ?
C2 N4 C5 C4 54.0(3) . . . . ?
O2 C4 C5 N4 -55.7(3) . . . . ?
N2 N1 C6 C7 -1.3(3) . . . . ?
C1 N1 C6 C7 -173.8(2) . . . . ?
N1 C6 C7 N3 1.1(3) . . . . ?
N1 C6 C7 C8 -179.2(3) . . . . ?
N2 N3 C7 C6 -0.4(3) . . . . ?
N2 N3 C7 C8 179.8(2) . . . . ?
C6 C7 C8 C9 170.3(3) . . . . ?
N3 C7 C8 C9 -10.0(4) . . . . ?
C6 C7 C8 C13 -10.5(5) . . . . ?
N3 C7 C8 C13 169.3(3) . . . . ?
C13 C8 C9 C10 -2.0(4) . . . . ?
C7 C8 C9 C10 177.2(3) . . . . ?
C8 C9 C10 C11 1.3(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C9 C10 C11 Br1 -178.7(2) . . . . ?
C10 C11 C12 C13 -1.1(4) . . . . ?
Br1 C11 C12 C13 177.8(2) . . . . ?
C11 C12 C13 C8 0.4(5) . . . . ?
C9 C8 C13 C12 1.1(4) . . . . ?
C7 C8 C13 C12 -178.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 1002751'
#######################################################################
#
#                 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_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 N4 O2 S'
_chemical_formula_sum            'C11 H12 N4 O2 S'
_chemical_formula_weight         264.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_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                   5.2958(3)
_cell_length_b                   11.8997(6)
_cell_length_c                   18.8466(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.808(2)
_cell_angle_gamma                90.00
_cell_volume                     1185.06(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8097
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      30.38

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8715
_exptl_absorpt_correction_T_max  0.8966
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
  Bruker-Nonius X8kappa APEX II CCD area detector'
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19721
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0097
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2145
_reflns_number_gt                1999
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_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 thiophene ring was observed disordered in two similar positions
  alterning the sulfur atom with a carbon atom. These two disordered atoms
  were refined with anisotropic displacement parameters and geometric
  restrains; the occupancy factors for these two disordered atoms were
  fixed both to 0.5.
  All non-hydrogen atoms were refined with anisotropic displacement
  parameters. The hydrogen atoms were included from calculated positions
  and refined riding on their respective carbon atoms.
;

_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)+(0.0686P)²+0.8170P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2145
_refine_ls_number_parameters     163
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.036
_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 -0.2466(2) 0.12111(11) -0.01477(7) 0.0326(3) Uani 1 1 d . . .
O2 O 0.3236(3) 0.42415(12) 0.07003(8) 0.0462(4) Uani 1 1 d . . .
N1 N -0.1026(3) 0.06603(12) 0.09621(7) 0.0232(3) Uani 1 1 d . . .
N2 N 0.1136(3) 0.05727(12) 0.13980(8) 0.0282(3) Uani 1 1 d . . .
N3 N 0.1023(3) -0.03865(12) 0.17268(8) 0.0285(3) Uani 1 1 d . . .
N4 N -0.0355(3) 0.25036(12) 0.05528(7) 0.0269(3) Uani 1 1 d . . .
C1 C -0.1361(3) 0.14912(14) 0.04104(9) 0.0242(4) Uani 1 1 d . . .
C2 C -0.0015(4) 0.32763(15) -0.00415(10) 0.0311(4) Uani 1 1 d . . .
H2A H -0.1220 0.3911 -0.0027 0.037 Uiso 1 1 calc R . .
H2B H -0.0329 0.2879 -0.0500 0.037 Uiso 1 1 calc R . .
C3 C 0.2675(4) 0.37063(17) 0.00320(10) 0.0366(5) Uani 1 1 d . . .
H3A H 0.3855 0.3070 -0.0018 0.044 Uiso 1 1 calc R . .
H3B H 0.2936 0.4248 -0.0355 0.044 Uiso 1 1 calc R . .
C4 C 0.2942(4) 0.34702(17) 0.12692(10) 0.0407(5) Uani 1 1 d . . .
H4A H 0.3342 0.3854 0.1729 0.049 Uiso 1 1 calc R . .
H4B H 0.4146 0.2839 0.1233 0.049 Uiso 1 1 calc R . .
C5 C 0.0276(4) 0.30163(15) 0.12494(9) 0.0314(4) Uani 1 1 d . . .
H5A H 0.0139 0.2448 0.1629 0.038 Uiso 1 1 calc R . .
H5B H -0.0923 0.3633 0.1332 0.038 Uiso 1 1 calc R . .
C6 C -0.2476(3) -0.02715(14) 0.10142(9) 0.0239(4) Uani 1 1 d . . .
H6 H -0.4053 -0.0430 0.0764 0.029 Uiso 1 1 calc R . .
C7 C -0.1181(3) -0.09294(14) 0.15026(9) 0.0232(4) Uani 1 1 d . . .
C8 C -0.1790(3) -0.20543(14) 0.17553(8) 0.0238(4) Uani 1 1 d . B .
C9 C -0.0138(3) -0.27257(15) 0.21637(9) 0.0295(4) Uani 1 1 d . . .
H9 H 0.1506 -0.2502 0.2341 0.035 Uiso 1 1 calc R A 1
S1A S -0.14213(13) -0.39921(6) 0.23057(4) 0.0391(2) Uani 0.65 1 d PU B 1
C10A C -0.4061(2) -0.38503(11) 0.19043(6) 0.0501(3) Uani 0.65 1 d PU B 1
H10A H -0.5383 -0.4390 0.1860 0.060 Uiso 0.65 1 calc PR B 1
C10B C -0.14213(13) -0.39921(6) 0.23057(4) 0.0391(2) Uani 0.35 1 d PU B 2
H10B H -0.0725 -0.4620 0.2561 0.047 Uiso 0.35 1 calc PR B 2
S1B S -0.4061(2) -0.38503(11) 0.19043(6) 0.0501(3) Uani 0.35 1 d P B 2
C11 C -0.4094(4) -0.25942(15) 0.15764(10) 0.0306(4) Uani 1 1 d . . .
H11 H -0.5477 -0.2270 0.1302 0.037 Uiso 1 1 calc R B 1


_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 1.216(2) . ?
O2 C3 1.425(2) . ?
O2 C4 1.428(2) . ?
N1 C6 1.356(2) . ?
N1 N2 1.3679(19) . ?
N1 C1 1.437(2) . ?
N2 N3 1.302(2) . ?
N3 C7 1.375(2) . ?
N4 C1 1.337(2) . ?
N4 C5 1.466(2) . ?
N4 C2 1.470(2) . ?
C2 C3 1.511(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.510(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.359(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.464(2) . ?
C8 C9 1.381(2) . ?
C8 C11 1.400(2) . ?
C9 S1A 1.6819(19) . ?
C9 H9 0.9500 . ?
S1A C10A 1.5537(14) . ?
C10A C11 1.617(2) . ?
C10A H10A 0.9500 . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C4 110.47(14) . . ?
C6 N1 N2 110.46(14) . . ?
C6 N1 C1 124.85(14) . . ?
N2 N1 C1 123.05(13) . . ?
N3 N2 N1 106.83(13) . . ?
N2 N3 C7 109.29(14) . . ?
C1 N4 C5 128.22(14) . . ?
C1 N4 C2 118.57(14) . . ?
C5 N4 C2 112.95(14) . . ?
O1 C1 N4 125.67(16) . . ?
O1 C1 N1 117.81(15) . . ?
N4 C1 N1 116.49(14) . . ?
N4 C2 C3 107.74(15) . . ?
N4 C2 H2A 110.2 . . ?
C3 C2 H2A 110.2 . . ?
N4 C2 H2B 110.2 . . ?
C3 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 C2 111.86(16) . . ?
O2 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
O2 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O2 C4 C5 111.09(16) . . ?
O2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
O2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N4 C5 C4 109.16(15) . . ?
N4 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
N4 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N1 C6 C7 104.90(14) . . ?
N1 C6 H6 127.5 . . ?
C7 C6 H6 127.5 . . ?
C6 C7 N3 108.50(15) . . ?
C6 C7 C8 129.40(15) . . ?
N3 C7 C8 122.03(15) . . ?
C9 C8 C11 112.24(16) . . ?
C9 C8 C7 124.41(16) . . ?
C11 C8 C7 123.27(15) . . ?
C8 C9 S1A 111.06(14) . . ?
C8 C9 H9 124.5 . . ?
S1A C9 H9 124.5 . . ?
C10A S1A C9 100.67(8) . . ?
S1A C10A C11 105.85(9) . . ?
S1A C10A H10A 127.1 . . ?
C11 C10A H10A 127.1 . . ?
C8 C11 C10A 110.17(14) . . ?
C8 C11 H11 124.9 . . ?
C10A C11 H11 124.9 . . ?

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
C6 N1 N2 N3 -1.09(18) . . . . ?
C1 N1 N2 N3 -167.09(15) . . . . ?
N1 N2 N3 C7 0.66(18) . . . . ?
C5 N4 C1 O1 159.06(18) . . . . ?
C2 N4 C1 O1 -14.7(3) . . . . ?
C5 N4 C1 N1 -22.9(3) . . . . ?
C2 N4 C1 N1 163.33(14) . . . . ?
C6 N1 C1 O1 -22.5(2) . . . . ?
N2 N1 C1 O1 141.45(16) . . . . ?
C6 N1 C1 N4 159.33(16) . . . . ?
N2 N1 C1 N4 -36.7(2) . . . . ?
C1 N4 C2 C3 -130.05(17) . . . . ?
C5 N4 C2 C3 55.3(2) . . . . ?
C4 O2 C3 C2 60.5(2) . . . . ?
N4 C2 C3 O2 -57.2(2) . . . . ?
C3 O2 C4 C5 -59.2(2) . . . . ?
C1 N4 C5 C4 130.67(19) . . . . ?
C2 N4 C5 C4 -55.3(2) . . . . ?
O2 C4 C5 N4 56.0(2) . . . . ?
N2 N1 C6 C7 1.05(18) . . . . ?
C1 N1 C6 C7 166.75(15) . . . . ?
N1 C6 C7 N3 -0.63(18) . . . . ?
N1 C6 C7 C8 -177.64(16) . . . . ?
N2 N3 C7 C6 -0.02(19) . . . . ?
N2 N3 C7 C8 177.25(15) . . . . ?
C6 C7 C8 C9 168.52(17) . . . . ?
N3 C7 C8 C9 -8.1(3) . . . . ?
C6 C7 C8 C11 -8.1(3) . . . . ?
N3 C7 C8 C11 175.29(16) . . . . ?
C11 C8 C9 S1A 0.82(19) . . . . ?
C7 C8 C9 S1A -176.09(13) . . . . ?
C8 C9 S1A C10A -0.72(14) . . . . ?
C9 S1A C10A C11 0.36(11) . . . . ?
C9 C8 C11 C10A -0.6(2) . . . . ?
C7 C8 C11 C10A 176.39(13) . . . . ?
S1A C10A C11 C8 0.05(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.083
_database_code_depnum_ccdc_archive 'CCDC 1002752'
#######################################################################
#
#                 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_8


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H14 N4 O3'
_chemical_formula_sum            'C9 H14 N4 O3'
_chemical_formula_weight         226.24

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P n'
_symmetry_space_group_name_Hall  'P -2yac'

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

_cell_length_a                   4.7202(3)
_cell_length_b                   13.9971(8)
_cell_length_c                   8.1756(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.621(2)
_cell_angle_gamma                90.00
_cell_volume                     539.59(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3218
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      30.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9485
_exptl_absorpt_correction_T_max  0.9584
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
  Bruker-Nonius X8kappa APEX II CCD area detector'
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5133
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.24
_reflns_number_total             965
_reflns_number_gt                936
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         965
_refine_ls_number_parameters     147
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1045(4) 0.69560(10) 1.23580(18) 0.0378(4) Uani 1 1 d . . .
O2 O -0.2155(3) 0.54395(10) 0.6898(2) 0.0355(4) Uani 1 1 d . . .
O3 O 0.3459(3) 1.11199(10) 1.04591(18) 0.0299(3) Uani 1 1 d . . .
N1 N 0.1122(3) 0.80431(10) 1.07582(19) 0.0227(4) Uani 1 1 d . . .
N2 N 0.3204(3) 0.81331(12) 0.9671(2) 0.0304(4) Uani 1 1 d . . .
N3 N 0.4320(4) 0.89791(12) 0.9904(2) 0.0312(4) Uani 1 1 d . . .
N4 N -0.0987(4) 0.66467(11) 0.9616(2) 0.0244(3) Uani 1 1 d . . .
C1 C -0.0448(4) 0.71642(15) 1.0984(2) 0.0255(4) Uani 1 1 d . . .
C2 C -0.2444(5) 0.57309(14) 0.9821(2) 0.0309(5) Uani 1 1 d . . .
H2A H -0.4523 0.5829 0.9748 0.037 Uiso 1 1 calc R . .
H2B H -0.1920 0.5458 1.0911 0.037 Uiso 1 1 calc R . .
C3 C -0.1587(5) 0.50525(14) 0.8494(3) 0.0353(5) Uani 1 1 d . . .
H3A H 0.0464 0.4912 0.8642 0.042 Uiso 1 1 calc R . .
H3B H -0.2634 0.4444 0.8595 0.042 Uiso 1 1 calc R . .
C4 C -0.0587(4) 0.62975(14) 0.6722(3) 0.0289(4) Uani 1 1 d . . .
H4A H -0.0935 0.6552 0.5601 0.035 Uiso 1 1 calc R . .
H4B H 0.1465 0.6159 0.6878 0.035 Uiso 1 1 calc R . .
C5 C -0.1419(4) 0.70372(13) 0.7950(2) 0.0269(4) Uani 1 1 d . . .
H5A H -0.0253 0.7619 0.7835 0.032 Uiso 1 1 calc R . .
H5B H -0.3436 0.7214 0.7748 0.032 Uiso 1 1 calc R . .
C6 C 0.0974(4) 0.88347(12) 1.1690(2) 0.0225(4) Uani 1 1 d . . .
H6 H -0.0272 0.8950 1.2549 0.027 Uiso 1 1 calc R . .
C7 C 0.2989(4) 0.94313(14) 1.1139(2) 0.0236(4) Uani 1 1 d . . .
C8 C 0.3864(4) 1.04109(14) 1.1699(2) 0.0281(4) Uani 1 1 d . . .
H8A H 0.2757 1.0590 1.2652 0.034 Uiso 1 1 calc R . .
H8B H 0.5892 1.0398 1.2065 0.034 Uiso 1 1 calc R . .
C9 C 0.0555(5) 1.13448(16) 1.0153(3) 0.0341(5) Uani 1 1 d . . .
H9A H -0.0456 1.0778 0.9734 0.051 Uiso 1 1 calc R . .
H9B H 0.0380 1.1859 0.9341 0.051 Uiso 1 1 calc R . .
H9C H -0.0267 1.1553 1.1173 0.051 Uiso 1 1 calc R . .


_geom_special_details            
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate (isotropic)
  treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.206(3) . ?
O2 C4 1.421(2) . ?
O2 C3 1.427(3) . ?
O3 C9 1.418(3) . ?
O3 C8 1.425(2) . ?
N1 C6 1.348(2) . ?
N1 N2 1.361(2) . ?
N1 C1 1.452(2) . ?
N2 N3 1.306(2) . ?
N3 C7 1.368(3) . ?
N4 C1 1.347(3) . ?
N4 C2 1.468(2) . ?
N4 C5 1.473(3) . ?
C2 C3 1.511(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.507(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.358(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.498(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C3 109.65(15) . . ?
C9 O3 C8 112.16(16) . . ?
C6 N1 N2 110.53(14) . . ?
C6 N1 C1 125.74(16) . . ?
N2 N1 C1 123.34(14) . . ?
N3 N2 N1 106.67(14) . . ?
N2 N3 C7 109.35(15) . . ?
C1 N4 C2 116.51(16) . . ?
C1 N4 C5 125.53(16) . . ?
C2 N4 C5 112.57(15) . . ?
O1 C1 N4 126.9(2) . . ?
O1 C1 N1 117.73(18) . . ?
N4 C1 N1 115.34(17) . . ?
N4 C2 C3 108.93(16) . . ?
N4 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
N4 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
O2 C3 C2 111.91(17) . . ?
O2 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
O2 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O2 C4 C5 111.12(17) . . ?
O2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
O2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N4 C5 C4 109.37(15) . . ?
N4 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
N4 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 C7 105.21(17) . . ?
N1 C6 H6 127.4 . . ?
C7 C6 H6 127.4 . . ?
C6 C7 N3 108.22(17) . . ?
C6 C7 C8 130.46(18) . . ?
N3 C7 C8 121.31(17) . . ?
O3 C8 C7 113.19(15) . . ?
O3 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
O3 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
C6 N1 N2 N3 -0.9(2) . . . . ?
C1 N1 N2 N3 -174.16(16) . . . . ?
N1 N2 N3 C7 0.4(2) . . . . ?
C2 N4 C1 O1 -0.3(3) . . . . ?
C5 N4 C1 O1 151.8(2) . . . . ?
C2 N4 C1 N1 176.98(16) . . . . ?
C5 N4 C1 N1 -31.0(3) . . . . ?
C6 N1 C1 O1 -30.4(3) . . . . ?
N2 N1 C1 O1 141.8(2) . . . . ?
C6 N1 C1 N4 152.14(18) . . . . ?
N2 N1 C1 N4 -35.7(2) . . . . ?
C1 N4 C2 C3 -151.39(18) . . . . ?
C5 N4 C2 C3 53.0(2) . . . . ?
C4 O2 C3 C2 60.8(2) . . . . ?
N4 C2 C3 O2 -56.2(2) . . . . ?
C3 O2 C4 C5 -61.0(2) . . . . ?
C1 N4 C5 C4 153.15(19) . . . . ?
C2 N4 C5 C4 -53.9(2) . . . . ?
O2 C4 C5 N4 57.3(2) . . . . ?
N2 N1 C6 C7 1.0(2) . . . . ?
C1 N1 C6 C7 174.06(15) . . . . ?
N1 C6 C7 N3 -0.8(2) . . . . ?
N1 C6 C7 C8 -179.20(18) . . . . ?
N2 N3 C7 C6 0.2(2) . . . . ?
N2 N3 C7 C8 178.82(16) . . . . ?
C9 O3 C8 C7 72.9(2) . . . . ?
C6 C7 C8 O3 -118.7(2) . . . . ?
N3 C7 C8 O3 63.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.034


###END






_database_code_depnum_ccdc_archive 'CCDC 1002753'
