# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lx-0203
_audit_block_doi                 10.5517/cc1j7sg0
_database_code_depnum_ccdc_archive 'CCDC 1407662'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C10 H16 N5, Br'
_chemical_formula_sum            'C10 H16 Br N5'
_chemical_formula_weight         286.19

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'
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   'P 1 21/n 1'
_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                   12.2189(10)
_cell_length_b                   5.8949(4)
_cell_length_c                   18.2917(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.995(2)
_cell_angle_gamma                90.00
_cell_volume                     1266.53(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6973
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.4

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    3.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3463
_exptl_absorpt_correction_T_max  0.7499
_exptl_absorpt_process_details   'Higashi, T. (1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9373
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2224
_reflns_number_gt                1504
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.2000P)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         2224
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1608
_refine_ls_R_factor_gt           0.1344
_refine_ls_wR_factor_ref         0.4318
_refine_ls_wR_factor_gt          0.4046
_refine_ls_goodness_of_fit_ref   1.711
_refine_ls_restrained_S_all      1.711
_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
C1 C 0.4975(7) 0.4681(13) 0.2982(4) 0.0242(18) Uani 1 1 d . . .
C2 C 0.4788(9) 0.2761(16) 0.2501(6) 0.035(2) Uani 1 1 d . . .
H2 H 0.5172 0.2594 0.2130 0.042 Uiso 1 1 calc R . .
C3 C 0.4021(10) 0.1134(18) 0.2595(6) 0.046(3) Uani 1 1 d . . .
H3 H 0.3906 -0.0180 0.2302 0.056 Uiso 1 1 calc R . .
C4 C 0.3436(10) 0.1480(19) 0.3122(8) 0.058(3) Uani 1 1 d . . .
H4 H 0.2883 0.0433 0.3157 0.069 Uiso 1 1 calc R . .
C5 C 0.3629(10) 0.329(2) 0.3597(7) 0.047(3) Uani 1 1 d . . .
H5 H 0.3250 0.3429 0.3971 0.057 Uiso 1 1 calc R . .
C6 C 0.4408(8) 0.4952(16) 0.3517(6) 0.037(2) Uani 1 1 d . . .
H6 H 0.4535 0.6228 0.3828 0.044 Uiso 1 1 calc R . .
C7 C 0.6564(8) 0.7462(13) 0.3365(5) 0.0262(19) Uani 1 1 d . . .
C8 C 0.7536(8) 0.8199(15) 0.4611(4) 0.0266(19) Uani 1 1 d . . .
C9 C 0.8339(9) 1.0958(18) 0.5597(5) 0.041(2) Uani 1 1 d . . .
H9A H 0.8094 1.2323 0.5791 0.062 Uiso 1 1 calc R . .
H9B H 0.8979 1.1287 0.5406 0.062 Uiso 1 1 calc R . .
H9C H 0.8555 0.9855 0.5997 0.062 Uiso 1 1 calc R . .
C10 C 0.6363(10) 1.145(2) 0.4738(6) 0.050(3) Uani 1 1 d . . .
H10A H 0.6425 1.2732 0.5072 0.074 Uiso 1 1 calc R . .
H10B H 0.5715 1.0554 0.4755 0.074 Uiso 1 1 calc R . .
H10C H 0.6270 1.1978 0.4227 0.074 Uiso 1 1 calc R . .
N1 N 0.5746(6) 0.6285(12) 0.2834(4) 0.0292(17) Uani 1 1 d . . .
H1 H 0.5699 0.6553 0.2364 0.035 Uiso 1 1 calc R . .
N2 N 0.7235(7) 0.8794(14) 0.3047(4) 0.038(2) Uani 1 1 d . . .
H2A H 0.7783 0.9667 0.3281 0.046 Uiso 1 1 d R . .
N3 N 0.6650(7) 0.7327(12) 0.4072(4) 0.0319(18) Uani 1 1 d . . .
H3A H 0.6120 0.6649 0.4214 0.038 Uiso 1 1 calc R . .
N4 N 0.8505(8) 0.7072(15) 0.4801(5) 0.047(2) Uani 1 1 d . . .
H4A H 0.9060 0.7545 0.5170 0.056 Uiso 1 1 calc R . .
H4B H 0.8583 0.5863 0.4557 0.056 Uiso 1 1 calc R . .
N5 N 0.7407(6) 1.0060(12) 0.4982(4) 0.0295(17) Uani 1 1 d . . .
Br1 Br 0.59247(14) 0.7836(3) 0.11668(8) 0.0756(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.020(4) 0.021(4) 0.025(4) 0.001(3) -0.004(3) 0.000(3)
C2 0.031(5) 0.040(5) 0.031(5) -0.001(4) 0.002(4) 0.000(4)
C3 0.038(6) 0.039(5) 0.056(6) 0.005(5) 0.002(5) -0.013(5)
C4 0.035(6) 0.044(6) 0.083(8) 0.020(6) -0.003(6) -0.017(5)
C5 0.034(6) 0.060(6) 0.054(6) 0.018(5) 0.019(5) 0.003(5)
C6 0.029(5) 0.036(5) 0.048(5) 0.003(4) 0.015(4) 0.003(4)
C7 0.022(5) 0.024(4) 0.030(5) -0.002(3) 0.004(4) -0.005(3)
C8 0.028(5) 0.033(4) 0.018(4) -0.001(3) 0.007(3) -0.003(4)
C9 0.041(6) 0.043(5) 0.030(5) -0.016(4) -0.006(4) -0.004(4)
C10 0.036(6) 0.053(6) 0.050(6) -0.006(5) -0.005(5) 0.019(5)
N1 0.033(4) 0.035(4) 0.016(3) 0.005(3) -0.001(3) -0.009(3)
N2 0.033(5) 0.047(5) 0.035(4) -0.003(4) 0.009(3) -0.021(4)
N3 0.025(4) 0.044(4) 0.028(4) -0.001(3) 0.009(3) -0.010(3)
N4 0.034(5) 0.053(5) 0.047(5) -0.025(4) 0.001(4) 0.003(4)
N5 0.024(4) 0.035(4) 0.027(3) 0.001(3) 0.003(3) 0.009(3)
Br1 0.0761(14) 0.0834(14) 0.0617(12) 0.0102(6) 0.0096(9) -0.0046(7)

_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
C1 C6 1.355(13) . ?
C1 C2 1.413(13) . ?
C1 N1 1.412(11) . ?
C2 C3 1.385(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(15) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N3 1.271(12) . ?
C7 N2 1.376(12) . ?
C7 N1 1.375(11) . ?
C8 N4 1.318(13) . ?
C8 N5 1.323(11) . ?
C8 N3 1.348(12) . ?
C9 N5 1.461(11) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N5 1.480(12) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 H1 0.8600 . ?
N2 H2A 0.8595 . ?
N3 H3A 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?

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
C6 C1 C2 121.1(9) . . ?
C6 C1 N1 124.0(8) . . ?
C2 C1 N1 114.8(8) . . ?
C3 C2 C1 118.4(10) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 119.3(11) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 122.5(10) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 119.2(11) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 119.3(10) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N3 C7 N2 125.1(8) . . ?
N3 C7 N1 121.9(8) . . ?
N2 C7 N1 113.0(8) . . ?
N4 C8 N5 120.5(8) . . ?
N4 C8 N3 118.9(8) . . ?
N5 C8 N3 120.4(8) . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N5 C10 H10A 109.5 . . ?
N5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 N1 C1 126.6(7) . . ?
C7 N1 H1 116.7 . . ?
C1 N1 H1 116.7 . . ?
C7 N2 H2A 127.1 . . ?
C7 N3 C8 123.0(8) . . ?
C7 N3 H3A 118.5 . . ?
C8 N3 H3A 118.5 . . ?
C8 N4 H4A 120.0 . . ?
C8 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C8 N5 C9 121.2(8) . . ?
C8 N5 C10 121.4(8) . . ?
C9 N5 C10 117.1(8) . . ?

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 C1 C2 C3 -0.9(14) . . . . ?
N1 C1 C2 C3 -178.4(8) . . . . ?
C1 C2 C3 C4 2.9(15) . . . . ?
C2 C3 C4 C5 -4.6(18) . . . . ?
C3 C4 C5 C6 4.0(18) . . . . ?
C2 C1 C6 C5 0.4(14) . . . . ?
N1 C1 C6 C5 177.6(8) . . . . ?
C4 C5 C6 C1 -1.9(16) . . . . ?
N3 C7 N1 C1 -5.5(14) . . . . ?
N2 C7 N1 C1 175.9(8) . . . . ?
C6 C1 N1 C7 43.0(13) . . . . ?
C2 C1 N1 C7 -139.7(9) . . . . ?
N2 C7 N3 C8 -11.2(15) . . . . ?
N1 C7 N3 C8 170.4(8) . . . . ?
N4 C8 N3 C7 -78.6(12) . . . . ?
N5 C8 N3 C7 106.6(10) . . . . ?
N4 C8 N5 C9 1.8(14) . . . . ?
N3 C8 N5 C9 176.5(9) . . . . ?
N4 C8 N5 C10 174.9(10) . . . . ?
N3 C8 N5 C10 -10.4(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.544
_refine_diff_density_min         -1.379
_refine_diff_density_rms         0.277
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_baq-2
_audit_block_doi                 10.5517/cc1jf76d
_database_code_depnum_ccdc_archive 'CCDC 1412893'
_audit_update_record             
;
2015-07-15 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 N5 O, I'
_chemical_formula_sum            'C11 H18 I N5 O'
_chemical_formula_weight         363.20

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   10.7823(4)
_cell_length_b                   11.5658(3)
_cell_length_c                   11.9326(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.080(3)
_cell_angle_gamma                90.00
_cell_volume                     1488.06(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7200
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      28.8

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    2.150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3883
_exptl_absorpt_correction_T_max  0.6176
_exptl_absorpt_process_details   'Higashi, T. (1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12966
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2935
_reflns_number_gt                2544
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0292P)²+1.8629P] 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         2935
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
C1 C 0.6645(4) 0.8024(4) 0.3210(4) 0.0733(11) Uiso 1 1 d . . .
H1A H 0.6525 0.8501 0.3859 0.110 Uiso 1 1 calc R . .
H1B H 0.7121 0.8440 0.2663 0.110 Uiso 1 1 calc R . .
H1C H 0.7081 0.7333 0.3420 0.110 Uiso 1 1 calc R . .
C2 C 0.4689(3) 0.7090(3) 0.3405(3) 0.0461(7) Uiso 1 1 d . . .
C3 C 0.3606(3) 0.6736(3) 0.2891(3) 0.0513(8) Uiso 1 1 d . . .
H3 H 0.3459 0.6931 0.2147 0.062 Uiso 1 1 calc R . .
C4 C 0.2741(3) 0.6098(3) 0.3471(3) 0.0465(7) Uiso 1 1 d . . .
H4 H 0.2016 0.5865 0.3113 0.056 Uiso 1 1 calc R . .
C5 C 0.2941(3) 0.5797(3) 0.4586(2) 0.0382(6) Uiso 1 1 d . . .
C6 C 0.4022(3) 0.6161(3) 0.5100(3) 0.0466(7) Uiso 1 1 d . . .
H6 H 0.4169 0.5970 0.5846 0.056 Uiso 1 1 calc R . .
C7 C 0.4889(3) 0.6808(3) 0.4517(3) 0.0500(8) Uiso 1 1 d . . .
H7 H 0.5609 0.7054 0.4875 0.060 Uiso 1 1 calc R . .
C8 C 0.1698(3) 0.5056(3) 0.6199(2) 0.0383(6) Uiso 1 1 d . . .
C9 C 0.1932(3) 0.5782(3) 0.8007(2) 0.0389(6) Uiso 1 1 d . . .
C10 C 0.2429(3) 0.5814(3) 0.9991(3) 0.0553(8) Uiso 1 1 d . . .
H10A H 0.2170 0.6606 1.0036 0.083 Uiso 1 1 calc R . .
H10B H 0.3158 0.5704 1.0441 0.083 Uiso 1 1 calc R . .
H10C H 0.1777 0.5322 1.0261 0.083 Uiso 1 1 calc R . .
C11 C 0.3832(3) 0.4859(3) 0.8619(3) 0.0593(9) Uiso 1 1 d . . .
H11A H 0.3694 0.4064 0.8812 0.089 Uiso 1 1 calc R . .
H11B H 0.4497 0.5164 0.9066 0.089 Uiso 1 1 calc R . .
H11C H 0.4045 0.4914 0.7840 0.089 Uiso 1 1 calc R . .
N1 N 0.2029(2) 0.5097(2) 0.5107(2) 0.0441(6) Uani 1 1 d . . .
H1 H 0.1633 0.4636 0.4669 0.053 Uiso 1 1 calc R . .
N2 N 0.0719(2) 0.4363(2) 0.6430(2) 0.0472(6) Uani 1 1 d . . .
H2A H 0.0470 0.4282 0.7110 0.057 Uiso 1 1 calc R . .
H2B H 0.0346 0.4004 0.5896 0.057 Uiso 1 1 calc R . .
N3 N 0.2326(2) 0.5637(2) 0.6940(2) 0.0460(6) Uani 1 1 d . . .
N4 N 0.0840(2) 0.6262(3) 0.8223(2) 0.0508(7) Uani 1 1 d . . .
H4A H 0.0630 0.6407 0.8904 0.061 Uiso 1 1 calc R . .
H4B H 0.0343 0.6428 0.7683 0.061 Uiso 1 1 calc R . .
N5 N 0.2703(2) 0.5524(2) 0.8831(2) 0.0419(6) Uani 1 1 d . . .
O1 O 0.5480(3) 0.7725(2) 0.2749(2) 0.0639(7) Uani 1 1 d . . .
I1 I 0.07362(2) 0.226622(19) 0.413268(16) 0.04839(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0550(16) 0.0466(15) 0.0306(12) -0.0073(11) -0.0005(11) -0.0116(12)
N2 0.0566(17) 0.0504(16) 0.0347(13) -0.0054(11) 0.0014(11) -0.0115(13)
N3 0.0456(15) 0.0607(17) 0.0316(13) -0.0098(12) 0.0002(11) -0.0081(12)
N4 0.0520(16) 0.0688(19) 0.0316(13) -0.0053(12) -0.0031(11) 0.0091(14)
N5 0.0501(15) 0.0412(14) 0.0344(13) -0.0033(10) -0.0049(11) -0.0001(11)
O1 0.0675(16) 0.0662(17) 0.0581(15) 0.0041(12) 0.0159(13) -0.0114(13)
I1 0.06410(15) 0.04551(14) 0.03557(12) -0.00381(9) 0.00376(9) 0.00061(10)

_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
C1 O1 1.414(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.372(4) . ?
C2 C3 1.379(5) . ?
C2 C7 1.384(5) . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 N1 1.418(4) . ?
C6 C7 1.386(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N3 1.299(4) . ?
C8 N1 1.353(4) . ?
C8 N2 1.354(4) . ?
C9 N5 1.320(4) . ?
C9 N4 1.328(4) . ?
C9 N3 1.353(4) . ?
C10 N5 1.456(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N5 1.461(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 115.6(3) . . ?
O1 C2 C7 125.3(3) . . ?
C3 C2 C7 119.2(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 N1 124.3(3) . . ?
C4 C5 N1 117.1(3) . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 120.3(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N3 C8 N1 119.9(3) . . ?
N3 C8 N2 125.0(3) . . ?
N1 C8 N2 115.0(3) . . ?
N5 C9 N4 120.5(3) . . ?
N5 C9 N3 118.3(3) . . ?
N4 C9 N3 121.0(3) . . ?
N5 C10 H10A 109.5 . . ?
N5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 H11A 109.5 . . ?
N5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 N1 C5 128.8(3) . . ?
C8 N1 H1 115.6 . . ?
C5 N1 H1 115.6 . . ?
C8 N2 H2A 120.0 . . ?
C8 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C8 N3 C9 122.7(3) . . ?
C9 N4 H4A 120.0 . . ?
C9 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C9 N5 C10 121.8(3) . . ?
C9 N5 C11 120.9(3) . . ?
C10 N5 C11 117.1(3) . . ?
C2 O1 C1 117.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.7(3) . . . . ?
C7 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C3 C4 C5 N1 -177.4(3) . . . . ?
C4 C5 C6 C7 -0.2(5) . . . . ?
N1 C5 C6 C7 177.5(3) . . . . ?
O1 C2 C7 C6 179.9(3) . . . . ?
C3 C2 C7 C6 1.1(5) . . . . ?
C5 C6 C7 C2 -0.6(5) . . . . ?
N3 C8 N1 C5 -6.7(5) . . . . ?
N2 C8 N1 C5 174.8(3) . . . . ?
C6 C5 N1 C8 31.8(5) . . . . ?
C4 C5 N1 C8 -150.5(3) . . . . ?
N1 C8 N3 C9 169.2(3) . . . . ?
N2 C8 N3 C9 -12.5(5) . . . . ?
N5 C9 N3 C8 128.4(3) . . . . ?
N4 C9 N3 C8 -57.2(5) . . . . ?
N4 C9 N5 C10 -3.8(5) . . . . ?
N3 C9 N5 C10 170.7(3) . . . . ?
N4 C9 N5 C11 171.9(3) . . . . ?
N3 C9 N5 C11 -13.7(4) . . . . ?
C3 C2 O1 C1 -174.9(3) . . . . ?
C7 C2 O1 C1 6.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.063
