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

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

# =============================================================================
_audit_creation_method           'SHELXL-97, manual editing plus enCIFer'
_audit_creation_date             '25 February 2014'
# =============================================================================

# =============================================================================
# GENERAL AND CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 La N10 O10'
_chemical_formula_sum            'C14 H15 La N10 O10'
_chemical_formula_weight         622.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 2/c'
_symmetry_space_group_name_Hall  '-P 2yc'


#=============================================================================
# CRYSTAL DATA
#=============================================================================

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

_cell_length_a                   13.013(2)
_cell_length_b                   8.7755(16)
_cell_length_c                   8.4187(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.902(5)
_cell_angle_gamma                90.00
_cell_volume                     933.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    831
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      23.62

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    2.377
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9109
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_process_details   
;
 SADABS (Sheldrick, 1997)
;


#=============================================================================
# EXPERIMENTAL DATA
#=============================================================================

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8544
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_sigmaI/netI    0.1063
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.98
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2112
_reflns_number_gt                1619
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT+ (Bruker, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

#=============================================================================
# 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 > 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)+(0.0232P)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         2112
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.0766
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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
La1 La 0.5000 0.92172(6) 0.2500 0.01042(13) Uani 1 2 d S . .
O1 O 0.3059(3) 0.8258(4) 0.0933(4) 0.0163(8) Uani 1 1 d . . .
O2 O 0.3180(3) 1.0195(4) 0.2642(4) 0.0210(9) Uani 1 1 d . . .
O3 O 0.4507(3) 0.6639(4) 0.3805(4) 0.0159(8) Uani 1 1 d . . .
O4 O 0.4713(3) 0.8573(4) 0.5515(4) 0.0158(8) Uani 1 1 d . . .
O5 O 0.0823(3) 0.2448(5) 0.1487(4) 0.0234(9) Uani 1 1 d . . .
N1 N 0.0980(3) 0.7621(5) 0.1234(5) 0.0137(10) Uani 1 1 d . . .
H1 H 0.0448 0.7598 0.0362 0.016 Uiso 1 1 calc R . .
N2 N 0.2077(3) 0.6417(5) 0.3387(5) 0.0138(10) Uani 1 1 d . . .
N3 N 0.2021(3) 0.3733(5) 0.3428(5) 0.0160(10) Uani 1 1 d . . .
H3 H 0.2292 0.2880 0.3897 0.019 Uiso 1 1 calc R . .
N4 N 0.0847(3) 0.5031(6) 0.1344(5) 0.0159(10) Uani 1 1 d . . .
H4 H 0.0326 0.5066 0.0458 0.019 Uiso 0.50 1 calc PR . .
N5 N 0.3197(3) 0.5079(5) 0.5430(5) 0.0146(10) Uani 1 1 d . . .
H5 H 0.3407 0.4209 0.5924 0.018 Uiso 1 1 calc R . .
C1 C 0.2650(4) 0.9165(7) 0.1774(5) 0.0132(11) Uani 1 1 d . . .
C2 C 0.1481(4) 0.9077(7) 0.1789(6) 0.0166(12) Uani 1 1 d . . .
H2A H 0.1411 0.9270 0.2917 0.020 Uiso 1 1 calc R . .
H2B H 0.1095 0.9896 0.1082 0.020 Uiso 1 1 calc R . .
C3 C 0.1310(4) 0.6329(6) 0.2014(6) 0.0127(12) Uani 1 1 d . . .
C4 C 0.2421(4) 0.5088(7) 0.4070(6) 0.0136(12) Uani 1 1 d . . .
C5 C 0.1187(4) 0.3671(7) 0.2039(6) 0.0177(13) Uani 1 1 d . . .
C6 C 0.3701(4) 0.6490(6) 0.6105(5) 0.0158(12) Uani 1 1 d . . .
H6A H 0.4164 0.6277 0.7199 0.019 Uiso 1 1 calc R . .
H6B H 0.3146 0.7210 0.6255 0.019 Uiso 1 1 calc R . .
C7 C 0.4356(4) 0.7255(7) 0.5066(6) 0.0161(12) Uani 1 1 d . . .


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

#=============================================================================
# GEOMETRY
#=============================================================================

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
La1 O4 2.528(3) 3_676 ?
La1 O4 2.528(3) 4_575 ?
La1 O2 2.549(3) 2_655 ?
La1 O2 2.549(3) . ?
La1 O3 2.660(3) . ?
La1 O3 2.660(3) 2_655 ?
La1 O1 2.688(3) . ?
La1 O1 2.688(3) 2_655 ?
La1 O4 2.713(3) 2_655 ?
La1 O4 2.713(3) . ?
La1 C1 2.972(5) 2_655 ?
La1 C7 3.034(5) 2_655 ?
O1 C1 1.265(6) . ?
O2 C1 1.259(6) . ?
O3 C7 1.248(6) . ?
O4 C7 1.270(6) . ?
O4 La1 2.528(3) 3_676 ?
O5 C5 1.219(6) . ?
N1 C3 1.329(6) . ?
N1 C2 1.459(6) . ?
N1 H1 0.8800 . ?
N2 C4 1.329(6) . ?
N2 C3 1.336(6) . ?
N3 C4 1.357(6) . ?
N3 C5 1.392(6) . ?
N3 H3 0.8800 . ?
N4 C3 1.347(6) . ?
N4 C5 1.355(7) . ?
N4 H4 0.8800 . ?
N5 C4 1.333(6) . ?
N5 C6 1.452(6) . ?
N5 H5 0.8800 . ?
C1 C2 1.526(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C6 C7 1.517(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 La1 O4 79.82(15) 3_676 4_575 ?
O4 La1 O2 77.36(11) 3_676 2_655 ?
O4 La1 O2 72.67(11) 4_575 2_655 ?
O4 La1 O2 72.67(11) 3_676 . ?
O4 La1 O2 77.36(11) 4_575 . ?
O2 La1 O2 140.64(17) 2_655 . ?
O4 La1 O3 113.04(10) 3_676 . ?
O4 La1 O3 155.97(10) 4_575 . ?
O2 La1 O3 128.66(11) 2_655 . ?
O2 La1 O3 87.02(11) . . ?
O4 La1 O3 155.97(10) 3_676 2_655 ?
O4 La1 O3 113.04(10) 4_575 2_655 ?
O2 La1 O3 87.02(11) 2_655 2_655 ?
O2 La1 O3 128.66(11) . 2_655 ?
O3 La1 O3 63.47(14) . 2_655 ?
O4 La1 O1 122.46(11) 3_676 . ?
O4 La1 O1 86.76(10) 4_575 . ?
O2 La1 O1 148.93(10) 2_655 . ?
O2 La1 O1 49.78(11) . . ?
O3 La1 O1 69.22(10) . . ?
O3 La1 O1 79.77(11) 2_655 . ?
O4 La1 O1 86.76(10) 3_676 2_655 ?
O4 La1 O1 122.46(11) 4_575 2_655 ?
O2 La1 O1 49.78(11) 2_655 2_655 ?
O2 La1 O1 148.93(10) . 2_655 ?
O3 La1 O1 79.77(11) . 2_655 ?
O3 La1 O1 69.22(10) 2_655 2_655 ?
O1 La1 O1 143.52(16) . 2_655 ?
O4 La1 O4 138.29(9) 3_676 2_655 ?
O4 La1 O4 64.74(13) 4_575 2_655 ?
O2 La1 O4 71.81(11) 2_655 2_655 ?
O2 La1 O4 116.91(10) . 2_655 ?
O3 La1 O4 108.08(11) . 2_655 ?
O3 La1 O4 48.32(10) 2_655 2_655 ?
O1 La1 O4 78.46(10) . 2_655 ?
O1 La1 O4 93.99(10) 2_655 2_655 ?
O4 La1 O4 64.74(13) 3_676 . ?
O4 La1 O4 138.29(9) 4_575 . ?
O2 La1 O4 116.91(10) 2_655 . ?
O2 La1 O4 71.81(11) . . ?
O3 La1 O4 48.32(10) . . ?
O3 La1 O4 108.08(11) 2_655 . ?
O1 La1 O4 93.99(10) . . ?
O1 La1 O4 78.46(10) 2_655 . ?
O4 La1 O4 155.93(16) 2_655 . ?
O4 La1 C1 83.94(12) 3_676 2_655 ?
O4 La1 C1 97.42(14) 4_575 2_655 ?
O2 La1 C1 24.88(13) 2_655 2_655 ?
O2 La1 C1 156.56(14) . 2_655 ?
O3 La1 C1 103.91(14) . 2_655 ?
O3 La1 C1 74.55(13) 2_655 2_655 ?
O1 La1 C1 153.55(13) . 2_655 ?
O1 La1 C1 25.19(12) 2_655 2_655 ?
O4 La1 C1 79.80(11) 2_655 2_655 ?
O4 La1 C1 99.83(11) . 2_655 ?
O4 La1 C7 152.09(12) 3_676 2_655 ?
O4 La1 C7 89.27(14) 4_575 2_655 ?
O2 La1 C7 74.88(13) 2_655 2_655 ?
O2 La1 C7 130.03(11) . 2_655 ?
O3 La1 C7 86.94(14) . 2_655 ?
O3 La1 C7 24.19(12) 2_655 2_655 ?
O1 La1 C7 81.98(12) . 2_655 ?
O1 La1 C7 77.53(11) 2_655 2_655 ?
O4 La1 C7 24.73(12) 2_655 2_655 ?
O4 La1 C7 132.19(14) . 2_655 ?
C1 La1 C7 72.01(13) 2_655 2_655 ?
C1 O1 La1 90.1(3) . . ?
C1 O2 La1 96.7(3) . . ?
C7 O3 La1 94.9(3) . . ?
C7 O4 La1 151.8(3) . 3_676 ?
C7 O4 La1 91.9(3) . . ?
La1 O4 La1 115.26(13) 3_676 . ?
C3 N1 C2 121.5(4) . . ?
C3 N1 H1 119.2 . . ?
C2 N1 H1 119.2 . . ?
C4 N2 C3 115.3(4) . . ?
C4 N3 C5 121.0(4) . . ?
C4 N3 H3 119.5 . . ?
C5 N3 H3 119.5 . . ?
C3 N4 C5 119.8(4) . . ?
C3 N4 H4 120.1 . . ?
C5 N4 H4 120.1 . . ?
C4 N5 C6 120.6(4) . . ?
C4 N5 H5 119.7 . . ?
C6 N5 H5 119.7 . . ?
O2 C1 O1 122.1(4) . . ?
O2 C1 C2 116.1(5) . . ?
O1 C1 C2 121.8(5) . . ?
N1 C2 C1 114.3(5) . . ?
N1 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
N1 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
N1 C3 N2 117.6(5) . . ?
N1 C3 N4 117.1(4) . . ?
N2 C3 N4 125.2(5) . . ?
N2 C4 N5 118.9(5) . . ?
N2 C4 N3 122.6(4) . . ?
N5 C4 N3 118.4(5) . . ?
O5 C5 N4 123.6(5) . . ?
O5 C5 N3 120.5(5) . . ?
N4 C5 N3 115.9(5) . . ?
N5 C6 C7 114.5(4) . . ?
N5 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
N5 C6 H6B 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
O3 C7 O4 121.8(5) . . ?
O3 C7 C6 121.6(5) . . ?
O4 C7 C6 116.5(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
O4 La1 O1 C1 -6.9(3) 3_676 . . . ?
O4 La1 O1 C1 -82.6(3) 4_575 . . . ?
O2 La1 O1 C1 -130.4(3) 2_655 . . . ?
O2 La1 O1 C1 -6.5(3) . . . . ?
O3 La1 O1 C1 97.9(3) . . . . ?
O3 La1 O1 C1 163.3(3) 2_655 . . . ?
O1 La1 O1 C1 131.5(3) 2_655 . . . ?
O4 La1 O1 C1 -147.5(3) 2_655 . . . ?
O4 La1 O1 C1 55.6(3) . . . . ?
C1 La1 O1 C1 177.2(4) 2_655 . . . ?
C7 La1 O1 C1 -172.3(3) 2_655 . . . ?
O4 La1 O2 C1 -173.8(3) 3_676 . . . ?
O4 La1 O2 C1 103.1(3) 4_575 . . . ?
O2 La1 O2 C1 144.1(3) 2_655 . . . ?
O3 La1 O2 C1 -58.5(3) . . . . ?
O3 La1 O2 C1 -6.4(3) 2_655 . . . ?
O1 La1 O2 C1 6.5(3) . . . . ?
O1 La1 O2 C1 -123.0(3) 2_655 . . . ?
O4 La1 O2 C1 50.3(3) 2_655 . . . ?
O4 La1 O2 C1 -105.4(3) . . . . ?
C1 La1 O2 C1 -177.6(3) 2_655 . . . ?
C7 La1 O2 C1 24.9(4) 2_655 . . . ?
O4 La1 O3 C7 11.2(3) 3_676 . . . ?
O4 La1 O3 C7 -107.6(3) 4_575 . . . ?
O2 La1 O3 C7 103.3(3) 2_655 . . . ?
O2 La1 O3 C7 -58.5(3) . . . . ?
O3 La1 O3 C7 165.0(3) 2_655 . . . ?
O1 La1 O3 C7 -106.3(3) . . . . ?
O1 La1 O3 C7 93.2(3) 2_655 . . . ?
O4 La1 O3 C7 -175.9(3) 2_655 . . . ?
O4 La1 O3 C7 9.6(3) . . . . ?
C1 La1 O3 C7 100.5(3) 2_655 . . . ?
C7 La1 O3 C7 171.1(2) 2_655 . . . ?
O4 La1 O4 C7 172.2(4) 3_676 . . . ?
O4 La1 O4 C7 137.6(2) 4_575 . . . ?
O2 La1 O4 C7 -128.5(3) 2_655 . . . ?
O2 La1 O4 C7 93.3(3) . . . . ?
O3 La1 O4 C7 -9.4(3) . . . . ?
O3 La1 O4 C7 -32.5(3) 2_655 . . . ?
O1 La1 O4 C7 48.0(3) . . . . ?
O1 La1 O4 C7 -95.9(3) 2_655 . . . ?
O4 La1 O4 C7 -22.4(3) 2_655 . . . ?
C1 La1 O4 C7 -109.3(3) 2_655 . . . ?
C7 La1 O4 C7 -34.8(4) 2_655 . . . ?
O4 La1 O4 La1 0.0 3_676 . . 3_676 ?
O4 La1 O4 La1 -34.6(3) 4_575 . . 3_676 ?
O2 La1 O4 La1 59.28(17) 2_655 . . 3_676 ?
O2 La1 O4 La1 -78.95(14) . . . 3_676 ?
O3 La1 O4 La1 178.4(2) . . . 3_676 ?
O3 La1 O4 La1 155.28(12) 2_655 . . 3_676 ?
O1 La1 O4 La1 -124.19(14) . . . 3_676 ?
O1 La1 O4 La1 91.87(14) 2_655 . . 3_676 ?
O4 La1 O4 La1 165.42(13) 2_655 . . 3_676 ?
C1 La1 O4 La1 78.45(17) 2_655 . . 3_676 ?
C7 La1 O4 La1 153.02(13) 2_655 . . 3_676 ?
La1 O2 C1 O1 -12.6(5) . . . . ?
La1 O2 C1 C2 167.6(4) . . . . ?
La1 O1 C1 O2 11.9(5) . . . . ?
La1 O1 C1 C2 -168.4(4) . . . . ?
C3 N1 C2 C1 61.5(6) . . . . ?
O2 C1 C2 N1 -161.0(4) . . . . ?
O1 C1 C2 N1 19.2(7) . . . . ?
C2 N1 C3 N2 3.9(7) . . . . ?
C2 N1 C3 N4 -175.5(4) . . . . ?
C4 N2 C3 N1 -176.3(4) . . . . ?
C4 N2 C3 N4 3.1(7) . . . . ?
C5 N4 C3 N1 176.7(4) . . . . ?
C5 N4 C3 N2 -2.7(8) . . . . ?
C3 N2 C4 N5 179.0(4) . . . . ?
C3 N2 C4 N3 -0.3(7) . . . . ?
C6 N5 C4 N2 -3.5(7) . . . . ?
C6 N5 C4 N3 175.9(4) . . . . ?
C5 N3 C4 N2 -2.7(7) . . . . ?
C5 N3 C4 N5 178.0(4) . . . . ?
C3 N4 C5 O5 -178.5(5) . . . . ?
C3 N4 C5 N3 -0.5(7) . . . . ?
C4 N3 C5 O5 -178.8(5) . . . . ?
C4 N3 C5 N4 3.0(7) . . . . ?
C4 N5 C6 C7 -67.9(6) . . . . ?
La1 O3 C7 O4 -18.3(5) . . . . ?
La1 O3 C7 C6 159.4(4) . . . . ?
La1 O4 C7 O3 -177.2(4) 3_676 . . . ?
La1 O4 C7 O3 17.8(5) . . . . ?
La1 O4 C7 C6 5.0(9) 3_676 . . . ?
La1 O4 C7 C6 -159.9(4) . . . . ?
N5 C6 C7 O3 -5.4(7) . . . . ?
N5 C6 C7 O4 172.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O5 0.88 1.98 2.859(5) 175.7 3_565
N3 H3 O1 0.88 2.03 2.821(5) 149.5 4_566
N4 H4 N4 0.88 1.88 2.755(8) 174.1 3_565
N5 H5 O1 0.88 2.21 2.970(6) 144.1 4_566

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.110
_refine_diff_density_min         -1.202
_refine_diff_density_rms         0.201

#=============================================================================
#   END
#=============================================================================


_database_code_depnum_ccdc_archive 'CCDC 988889'
#######################################################################
#
#                 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_L'

# =============================================================================
_audit_creation_method           'SHELXL-97, manual editing plus enCIFer'
_audit_creation_date             '25 February 2014'
# =============================================================================

# =============================================================================
# GENERAL AND CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H10 N5 O5, Cl'
_chemical_formula_sum            'C7 H10 Cl N5 O5'
_chemical_formula_weight         279.65

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

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

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

_cell_length_a                   11.2216(3)
_cell_length_b                   15.0063(4)
_cell_length_c                   6.8432(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.245(2)
_cell_angle_gamma                90.00
_cell_volume                     1152.35(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5576
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      35.86

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9653
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_process_details   
;
 SADABS (Sheldrick, 1997)
;


#=============================================================================
# EXPERIMENTAL DATA
#=============================================================================

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20434
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         36.31
_reflns_number_total             5566
_reflns_number_gt                4009
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT+ (Bruker, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

#=============================================================================
# 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 > 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)+(0.0520P)²+0.1484P] 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         5566
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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
Cl1 Cl 0.15204(2) 0.123434(16) 0.63154(4) 0.02064(6) Uani 1 1 d . . .
O1 O -0.10225(8) 0.17377(6) 0.24832(15) 0.0349(2) Uani 1 1 d . . .
O2 O 0.29220(8) -0.07804(6) 0.49966(13) 0.03037(19) Uani 1 1 d . . .
O3 O 0.40508(8) -0.17328(7) 0.32923(13) 0.0347(2) Uani 1 1 d . . .
H3 H 0.4517 -0.1671 0.4247 0.052 Uiso 1 1 calc R . .
O4 O 0.44698(7) 0.15969(6) 0.37329(12) 0.02558(17) Uani 1 1 d . . .
O5 O 0.57063(8) 0.07846(7) 0.18708(13) 0.0329(2) Uani 1 1 d . . .
H5A H 0.6122 0.0776 0.2894 0.049 Uiso 1 1 calc R . .
N1 N 0.09075(8) 0.17714(6) 0.15063(13) 0.02082(17) Uani 1 1 d . . .
H1 H 0.0880 0.2348 0.1280 0.031 Uiso 1 1 calc R . .
N2 N 0.00198(8) 0.04369(6) 0.23280(13) 0.01999(16) Uani 1 1 d . . .
H2 H -0.0601 0.0115 0.2666 0.030 Uiso 1 1 calc R . .
N3 N 0.20538(8) 0.04504(6) 0.14125(12) 0.01818(16) Uani 1 1 d . . .
N4 N 0.11213(8) -0.08562(6) 0.22319(14) 0.02151(17) Uani 1 1 d . . .
H4 H 0.0470 -0.1140 0.2583 0.032 Uiso 1 1 calc R . .
N5 N 0.28878(8) 0.18078(6) 0.06898(13) 0.01995(16) Uani 1 1 d . . .
H5 H 0.2819 0.2389 0.0564 0.030 Uiso 1 1 calc R . .
C1 C -0.01047(10) 0.13492(7) 0.21463(16) 0.0222(2) Uani 1 1 d . . .
C2 C 0.10872(9) 0.00216(7) 0.19948(14) 0.01774(17) Uani 1 1 d . . .
C3 C 0.19496(9) 0.13302(6) 0.12101(14) 0.01745(17) Uani 1 1 d . . .
C4 C 0.22069(10) -0.13542(7) 0.19238(17) 0.0222(2) Uani 1 1 d . . .
H4A H 0.2582 -0.1151 0.0694 0.027 Uiso 1 1 calc R . .
H4B H 0.2008 -0.1993 0.1773 0.027 Uiso 1 1 calc R . .
C5 C 0.30872(10) -0.12489(7) 0.35773(16) 0.02179(19) Uani 1 1 d . . .
C6 C 0.40236(10) 0.13875(7) 0.03254(15) 0.02135(19) Uani 1 1 d . . .
H6A H 0.4482 0.1757 -0.0605 0.026 Uiso 1 1 calc R . .
H6B H 0.3887 0.0799 -0.0289 0.026 Uiso 1 1 calc R . .
C7 C 0.47461(10) 0.12642(7) 0.21670(16) 0.02163(19) Uani 1 1 d . . .


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

#=============================================================================
# GEOMETRY
#=============================================================================

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 1.2066(14) . ?
O2 C5 1.2138(14) . ?
O3 C5 1.3178(14) . ?
O3 H3 0.8400 . ?
O4 C7 1.2234(13) . ?
O5 C7 1.3122(14) . ?
O5 H5A 0.8400 . ?
N1 C3 1.3597(14) . ?
N1 C1 1.3740(14) . ?
N1 H1 0.8800 . ?
N2 C2 1.3702(13) . ?
N2 C1 1.3816(13) . ?
N2 H2 0.8800 . ?
N3 C2 1.3240(13) . ?
N3 C3 1.3327(13) . ?
N4 C2 1.3278(13) . ?
N4 C4 1.4453(14) . ?
N4 H4 0.8800 . ?
N5 C3 1.3236(13) . ?
N5 C6 1.4447(14) . ?
N5 H5 0.8800 . ?
C4 C5 1.5072(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C7 1.5070(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 H3 109.5 . . ?
C7 O5 H5A 109.5 . . ?
C3 N1 C1 122.39(9) . . ?
C3 N1 H1 118.8 . . ?
C1 N1 H1 118.8 . . ?
C2 N2 C1 121.59(9) . . ?
C2 N2 H2 119.2 . . ?
C1 N2 H2 119.2 . . ?
C2 N3 C3 116.18(9) . . ?
C2 N4 C4 121.26(9) . . ?
C2 N4 H4 119.4 . . ?
C4 N4 H4 119.4 . . ?
C3 N5 C6 120.89(9) . . ?
C3 N5 H5 119.6 . . ?
C6 N5 H5 119.6 . . ?
O1 C1 N1 123.07(10) . . ?
O1 C1 N2 123.21(11) . . ?
N1 C1 N2 113.71(9) . . ?
N3 C2 N4 119.72(9) . . ?
N3 C2 N2 123.15(9) . . ?
N4 C2 N2 117.11(9) . . ?
N5 C3 N3 119.65(9) . . ?
N5 C3 N1 117.52(9) . . ?
N3 C3 N1 122.82(9) . . ?
N4 C4 C5 112.73(9) . . ?
N4 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
N4 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
O2 C5 O3 124.46(11) . . ?
O2 C5 C4 124.03(10) . . ?
O3 C5 C4 111.51(9) . . ?
N5 C6 C7 112.41(9) . . ?
N5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
N5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O4 C7 O5 124.79(11) . . ?
O4 C7 C6 123.02(10) . . ?
O5 C7 C6 112.17(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
C3 N1 C1 O1 177.21(11) . . . . ?
C3 N1 C1 N2 -4.07(14) . . . . ?
C2 N2 C1 O1 -177.81(11) . . . . ?
C2 N2 C1 N1 3.47(14) . . . . ?
C3 N3 C2 N4 -179.94(9) . . . . ?
C3 N3 C2 N2 1.80(14) . . . . ?
C4 N4 C2 N3 1.91(15) . . . . ?
C4 N4 C2 N2 -179.73(9) . . . . ?
C1 N2 C2 N3 -2.56(15) . . . . ?
C1 N2 C2 N4 179.14(9) . . . . ?
C6 N5 C3 N3 0.40(14) . . . . ?
C6 N5 C3 N1 -179.27(9) . . . . ?
C2 N3 C3 N5 177.97(9) . . . . ?
C2 N3 C3 N1 -2.38(14) . . . . ?
C1 N1 C3 N5 -176.57(9) . . . . ?
C1 N1 C3 N3 3.78(15) . . . . ?
C2 N4 C4 C5 75.73(13) . . . . ?
N4 C4 C5 O2 -1.73(16) . . . . ?
N4 C4 C5 O3 177.85(10) . . . . ?
C3 N5 C6 C7 -85.56(12) . . . . ?
N5 C6 C7 O4 -9.68(15) . . . . ?
N5 C6 C7 O5 172.02(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O4 0.84 1.79 2.6291(12) 177.2 3_656
O5 H5A O2 0.84 1.79 2.6337(12) 176.9 3_656
N1 H1 Cl1 0.88 2.24 3.0735(9) 156.8 4_565
N2 H2 Cl1 0.88 2.38 3.1863(9) 152.8 3_556
N4 H4 Cl1 0.88 2.37 3.1817(10) 154.5 3_556
N5 H5 Cl1 0.88 2.58 3.3430(9) 145.4 4_565

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        36.31
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.065

#=============================================================================
#   END
#=============================================================================

_database_code_depnum_ccdc_archive 'CCDC 988890'
#######################################################################
#
#                 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_L'

# =============================================================================
_audit_creation_method           'SHELXL-97, manual editing plus enCIFer'
_audit_creation_date             '25 February 2014'
# =============================================================================

# =============================================================================
# GENERAL AND CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H12 Cl N5 O4'
_chemical_formula_sum            'C9 H12 Cl N5 O4'
_chemical_formula_weight         289.69

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_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                   7.2191(5)
_cell_length_b                   24.9432(19)
_cell_length_c                   7.4918(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.281(5)
_cell_angle_gamma                90.00
_cell_volume                     1239.19(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3201
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      29.80

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9195
_exptl_absorpt_correction_T_max  0.9433
_exptl_absorpt_process_details   
;
 SADABS (Sheldrick, 1997)
;


#=============================================================================
# EXPERIMENTAL DATA
#=============================================================================

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13354
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2810
_reflns_number_gt                1910
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT+ (Bruker, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

#=============================================================================
# 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 > 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)+(0.0633P)²+0.3332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2810
_refine_ls_number_parameters     180
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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
Cl1 Cl 0.56983(9) 1.08580(3) 0.58075(9) 0.02657(19) Uani 1 1 d . . .
N1 N 0.8303(3) 1.00951(8) 0.6378(3) 0.0179(4) Uani 1 1 d . . .
N2 N 0.6347(3) 1.00873(8) 0.8302(3) 0.0174(4) Uani 1 1 d . . .
N3 N 0.8844(3) 0.94075(8) 0.8765(3) 0.0171(4) Uani 1 1 d . . .
N4 N 1.0668(3) 0.94266(8) 0.6873(3) 0.0185(4) Uani 1 1 d D . .
H4 H 1.090(4) 0.9597(10) 0.585(3) 0.028 Uiso 1 1 d D . .
N5 N 0.6941(3) 0.94203(8) 1.0591(3) 0.0188(4) Uani 1 1 d D . .
H5 H 0.595(3) 0.9589(10) 1.091(3) 0.028 Uiso 1 1 d D . .
O1 O 1.0857(3) 0.81155(8) 0.8842(3) 0.0341(5) Uani 1 1 d . . .
O2 O 0.8920(3) 0.84445(7) 0.5907(2) 0.0261(4) Uani 1 1 d . . .
O3 O 0.5978(3) 0.84086(7) 0.8841(3) 0.0265(4) Uani 1 1 d . . .
O4 O 0.8264(3) 0.80199(7) 1.1503(2) 0.0266(4) Uani 1 1 d . . .
C1 C 0.6925(3) 1.02789(10) 0.6970(3) 0.0175(5) Uani 1 1 d . . .
C2 C 0.7393(3) 0.96392(10) 0.9182(3) 0.0163(5) Uani 1 1 d . . .
C3 C 0.9238(3) 0.96465(9) 0.7357(3) 0.0160(5) Uani 1 1 d . . .
C4 C 1.1744(3) 0.89567(10) 0.7870(4) 0.0207(5) Uani 1 1 d . . .
H4A H 1.2416 0.9040 0.9273 0.025 Uiso 1 1 calc R . .
H4B H 1.2811 0.8875 0.7394 0.025 Uiso 1 1 calc R . .
C5 C 1.0461(4) 0.84632(10) 0.7631(3) 0.0221(6) Uani 1 1 d . . .
C6 C 0.7638(4) 0.79789(12) 0.5551(4) 0.0334(7) Uani 1 1 d . . .
H6A H 0.8464 0.7654 0.5798 0.050 Uiso 1 1 calc R . .
H6B H 0.6663 0.7981 0.4197 0.050 Uiso 1 1 calc R . .
H6C H 0.6915 0.7986 0.6417 0.050 Uiso 1 1 calc R . .
C7 C 0.7951(4) 0.89466(10) 1.1635(3) 0.0207(5) Uani 1 1 d . . .
H7A H 0.7702 0.8914 1.2839 0.025 Uiso 1 1 calc R . .
H7B H 0.9422 0.8987 1.2016 0.025 Uiso 1 1 calc R . .
C8 C 0.7251(3) 0.84378(10) 1.0450(3) 0.0198(5) Uani 1 1 d . . .
C9 C 0.7765(4) 0.75033(11) 1.0549(4) 0.0308(6) Uani 1 1 d . . .
H9A H 0.6298 0.7455 0.9998 0.046 Uiso 1 1 calc R . .
H9B H 0.8398 0.7219 1.1496 0.046 Uiso 1 1 calc R . .
H9C H 0.8261 0.7487 0.9507 0.046 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. 
;

#=============================================================================
# GEOMETRY
#=============================================================================

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
Cl1 C1 1.737(2) . ?
N1 C1 1.321(3) . ?
N1 C3 1.362(3) . ?
N2 C1 1.315(3) . ?
N2 C2 1.364(3) . ?
N3 C2 1.336(3) . ?
N3 C3 1.337(3) . ?
N4 C3 1.339(3) . ?
N4 C4 1.441(3) . ?
N4 H4 0.944(10) . ?
N5 C2 1.339(3) . ?
N5 C7 1.445(3) . ?
N5 H5 0.941(10) . ?
O1 C5 1.205(3) . ?
O2 C5 1.331(3) . ?
O2 C6 1.443(3) . ?
O3 C8 1.195(3) . ?
O4 C8 1.337(3) . ?
O4 C9 1.448(3) . ?
C4 C5 1.508(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.517(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 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
C1 N1 C3 112.55(19) . . ?
C1 N2 C2 112.53(19) . . ?
C2 N3 C3 115.0(2) . . ?
C3 N4 C4 120.51(19) . . ?
C3 N4 H4 115.7(17) . . ?
C4 N4 H4 123.7(17) . . ?
C2 N5 C7 122.15(19) . . ?
C2 N5 H5 117.8(16) . . ?
C7 N5 H5 120.1(16) . . ?
C5 O2 C6 115.9(2) . . ?
C8 O4 C9 115.5(2) . . ?
N2 C1 N1 129.5(2) . . ?
N2 C1 Cl1 115.52(17) . . ?
N1 C1 Cl1 115.01(17) . . ?
N3 C2 N5 117.8(2) . . ?
N3 C2 N2 125.2(2) . . ?
N5 C2 N2 116.99(19) . . ?
N3 C3 N4 117.3(2) . . ?
N3 C3 N1 125.2(2) . . ?
N4 C3 N1 117.5(2) . . ?
N4 C4 C5 114.99(19) . . ?
N4 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
N4 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
O1 C5 O2 124.3(2) . . ?
O1 C5 C4 123.1(2) . . ?
O2 C5 C4 112.5(2) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N5 C7 C8 112.8(2) . . ?
N5 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N5 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O3 C8 O4 124.8(2) . . ?
O3 C8 C7 126.0(2) . . ?
O4 C8 C7 109.2(2) . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O4 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
C2 N2 C1 N1 1.3(4) . . . . ?
C2 N2 C1 Cl1 -178.84(16) . . . . ?
C3 N1 C1 N2 -1.1(4) . . . . ?
C3 N1 C1 Cl1 179.02(16) . . . . ?
C3 N3 C2 N5 -179.5(2) . . . . ?
C3 N3 C2 N2 -0.4(3) . . . . ?
C7 N5 C2 N3 -0.6(3) . . . . ?
C7 N5 C2 N2 -179.8(2) . . . . ?
C1 N2 C2 N3 -0.4(3) . . . . ?
C1 N2 C2 N5 178.7(2) . . . . ?
C2 N3 C3 N4 -179.4(2) . . . . ?
C2 N3 C3 N1 0.6(3) . . . . ?
C4 N4 C3 N3 -1.0(3) . . . . ?
C4 N4 C3 N1 178.9(2) . . . . ?
C1 N1 C3 N3 0.0(3) . . . . ?
C1 N1 C3 N4 -179.9(2) . . . . ?
C3 N4 C4 C5 63.3(3) . . . . ?
C6 O2 C5 O1 2.2(3) . . . . ?
C6 O2 C5 C4 178.95(19) . . . . ?
N4 C4 C5 O1 -151.0(2) . . . . ?
N4 C4 C5 O2 32.2(3) . . . . ?
C2 N5 C7 C8 -75.3(3) . . . . ?
C9 O4 C8 O3 1.4(3) . . . . ?
C9 O4 C8 C7 -179.52(18) . . . . ?
N5 C7 C8 O3 -1.6(3) . . . . ?
N5 C7 C8 O4 179.38(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 N1 0.944(10) 2.117(11) 3.055(3) 173(2) 3_776
N5 H5 N2 0.941(10) 2.124(10) 3.063(3) 176(2) 3_677

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.075

#=============================================================================
#   END
#=============================================================================

_database_code_depnum_ccdc_archive 'CCDC 988891'
