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

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_cl2
_database_code_depnum_ccdc_archive 'CCDC 672064'
_audit_update_record             
;
2007-12-28 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;
#TrackingRef '5.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Cl2 N6 O'
_chemical_formula_sum            'C10 H10 Cl2 N6 O'
_chemical_formula_weight         301.14

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'
Cl Cl 0.1484 0.1585 '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           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1 '

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

_cell_length_a                   7.3765(2)
_cell_length_b                   7.5213(3)
_cell_length_c                   12.1712(3)
_cell_angle_alpha                97.744(2)
_cell_angle_beta                 92.657(2)
_cell_angle_gamma                110.3030(10)
_cell_volume                     624.38(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2791
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.794996
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'

_exptl_special_details           
;
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12782
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2864
_reflns_number_gt                2390
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_reduction        'DENZO & COLLECT'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  '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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_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)+(0.0429P)²+0.3597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2864
_refine_ls_number_parameters     185
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.071
_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
Cl1 Cl 0.54040(7) -0.29734(6) 0.18329(4) 0.02942(14) Uani 1 1 d . . .
Cl2 Cl 0.95496(7) 0.29352(7) -0.11917(4) 0.03035(14) Uani 1 1 d . . .
O1 O 0.96241(17) 0.81772(17) 0.38894(10) 0.0192(3) Uani 1 1 d . . .
N1 N 1.3269(2) 1.0815(2) 0.47420(13) 0.0194(3) Uani 1 1 d D . .
H1N H 1.307(3) 1.132(3) 0.4153(12) 0.023 Uiso 1 1 d D . .
H2N H 1.241(2) 1.092(3) 0.5198(14) 0.023 Uiso 1 1 d D . .
N2 N 1.2815(2) 0.8821(2) 0.43932(13) 0.0191(3) Uani 1 1 d D . .
H3N H 1.379(2) 0.843(3) 0.4503(17) 0.023 Uiso 1 1 d D . .
N3 N 1.2329(2) 0.4984(2) 0.35896(12) 0.0190(3) Uani 1 1 d . . .
N4 N 1.1673(2) 0.3136(2) 0.32063(12) 0.0195(3) Uani 1 1 d . . .
N5 N 0.9697(2) 0.2584(2) 0.30807(11) 0.0164(3) Uani 1 1 d . . .
N6 N 0.8496(2) 0.0726(2) 0.26413(12) 0.0193(3) Uani 1 1 d D . .
H4N H 0.881(3) -0.013(2) 0.2950(16) 0.023 Uiso 1 1 d D . .
C1 C 1.1025(2) 0.7635(2) 0.39949(13) 0.0160(3) Uani 1 1 d . . .
C2 C 1.0791(2) 0.5603(2) 0.36689(13) 0.0162(3) Uani 1 1 d . . .
C3 C 0.9079(2) 0.4066(2) 0.33524(13) 0.0160(3) Uani 1 1 d . . .
C4 C 0.6994(2) 0.3836(3) 0.32854(16) 0.0225(4) Uani 1 1 d . . .
H4A H 0.6582 0.4010 0.2543 0.034 Uiso 1 1 calc R . .
H4B H 0.6804 0.4799 0.3849 0.034 Uiso 1 1 calc R . .
H4C H 0.6219 0.2547 0.3420 0.034 Uiso 1 1 calc R . .
C5 C 0.8056(2) 0.0371(2) 0.14679(14) 0.0176(3) Uani 1 1 d . . .
C6 C 0.6608(3) -0.1369(2) 0.09800(15) 0.0214(4) Uani 1 1 d . . .
C7 C 0.6113(3) -0.1792(3) -0.01612(16) 0.0271(4) Uani 1 1 d . . .
H7 H 0.5157 -0.2993 -0.0481 0.032 Uiso 1 1 calc R . .
C8 C 0.7008(3) -0.0470(3) -0.08394(16) 0.0270(4) Uani 1 1 d . . .
H8 H 0.6673 -0.0750 -0.1623 0.032 Uiso 1 1 calc R . .
C9 C 0.8400(3) 0.1265(3) -0.03523(15) 0.0218(4) Uani 1 1 d . . .
C10 C 0.8948(2) 0.1705(2) 0.07863(14) 0.0186(4) Uani 1 1 d . . .
H10 H 0.9920 0.2901 0.1098 0.022 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.7323(19) . ?
Cl2 C9 1.7400(19) . ?
O1 C1 1.243(2) . ?
N1 N2 1.417(2) . ?
N1 H1N 0.883(9) . ?
N1 H2N 0.877(9) . ?
N2 C1 1.335(2) . ?
N2 H3N 0.879(9) . ?
N3 N4 1.312(2) . ?
N3 C2 1.370(2) . ?
N4 N5 1.365(2) . ?
N5 C3 1.352(2) . ?
N5 N6 1.3856(19) . ?
N6 C5 1.418(2) . ?
N6 H4N 0.876(9) . ?
C1 C2 1.473(2) . ?
C2 C3 1.379(2) . ?
C3 C4 1.484(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.394(2) . ?
C5 C6 1.403(2) . ?
C6 C7 1.385(3) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(2) . ?
C10 H10 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
N2 N1 H1N 107.9(14) . . ?
N2 N1 H2N 106.1(14) . . ?
H1N N1 H2N 107.2(19) . . ?
C1 N2 N1 122.37(14) . . ?
C1 N2 H3N 123.4(14) . . ?
N1 N2 H3N 114.1(14) . . ?
N4 N3 C2 109.08(14) . . ?
N3 N4 N5 105.92(13) . . ?
C3 N5 N4 112.62(13) . . ?
C3 N5 N6 124.64(14) . . ?
N4 N5 N6 122.58(14) . . ?
N5 N6 C5 114.99(13) . . ?
N5 N6 H4N 111.8(14) . . ?
C5 N6 H4N 117.8(14) . . ?
O1 C1 N2 123.28(15) . . ?
O1 C1 C2 120.96(15) . . ?
N2 C1 C2 115.75(14) . . ?
N3 C2 C3 109.48(15) . . ?
N3 C2 C1 123.13(15) . . ?
C3 C2 C1 127.32(15) . . ?
N5 C3 C2 102.86(14) . . ?
N5 C3 C4 122.94(15) . . ?
C2 C3 C4 134.21(16) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 118.77(16) . . ?
C10 C5 N6 122.83(15) . . ?
C6 C5 N6 118.35(15) . . ?
C7 C6 C5 120.90(17) . . ?
C7 C6 Cl1 120.19(14) . . ?
C5 C6 Cl1 118.89(14) . . ?
C6 C7 C8 120.27(17) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 118.65(17) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 122.11(17) . . ?
C8 C9 Cl2 119.28(14) . . ?
C10 C9 Cl2 118.59(14) . . ?
C9 C10 C5 119.25(16) . . ?
C9 C10 H10 120.4 . . ?
C5 C10 H10 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N3 N4 N5 -2.01(17) . . . . ?
N3 N4 N5 C3 1.56(18) . . . . ?
N3 N4 N5 N6 177.03(14) . . . . ?
C3 N5 N6 C5 85.1(2) . . . . ?
N4 N5 N6 C5 -89.83(18) . . . . ?
N1 N2 C1 O1 0.6(3) . . . . ?
N1 N2 C1 C2 -179.96(14) . . . . ?
N4 N3 C2 C3 1.83(18) . . . . ?
N4 N3 C2 C1 -175.46(14) . . . . ?
O1 C1 C2 N3 168.61(15) . . . . ?
N2 C1 C2 N3 -10.9(2) . . . . ?
O1 C1 C2 C3 -8.2(3) . . . . ?
N2 C1 C2 C3 172.35(16) . . . . ?
N4 N5 C3 C2 -0.44(18) . . . . ?
N6 N5 C3 C2 -175.81(14) . . . . ?
N4 N5 C3 C4 179.96(15) . . . . ?
N6 N5 C3 C4 4.6(2) . . . . ?
N3 C2 C3 N5 -0.81(17) . . . . ?
C1 C2 C3 N5 176.33(15) . . . . ?
N3 C2 C3 C4 178.72(17) . . . . ?
C1 C2 C3 C4 -4.1(3) . . . . ?
N5 N6 C5 C10 7.7(2) . . . . ?
N5 N6 C5 C6 -169.78(15) . . . . ?
C10 C5 C6 C7 2.2(3) . . . . ?
N6 C5 C6 C7 179.82(16) . . . . ?
C10 C5 C6 Cl1 -176.50(13) . . . . ?
N6 C5 C6 Cl1 1.1(2) . . . . ?
C5 C6 C7 C8 -1.9(3) . . . . ?
Cl1 C6 C7 C8 176.83(14) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C7 C8 C9 Cl2 179.58(14) . . . . ?
C8 C9 C10 C5 -0.8(3) . . . . ?
Cl2 C9 C10 C5 -179.22(13) . . . . ?
C6 C5 C10 C9 -0.9(2) . . . . ?
N6 C5 C10 C9 -178.36(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.068


####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_h
_database_code_depnum_ccdc_archive 'CCDC 933968'
_audit_update_record             
;
2013-04-15 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;
#TrackingRef '1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N6 O'
_chemical_formula_sum            'C10 H12 N6 O'
_chemical_formula_weight         232.26

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1 '

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

_cell_length_a                   7.4637(14)
_cell_length_b                   11.481(2)
_cell_length_c                   13.395(3)
_cell_angle_alpha                95.849(3)
_cell_angle_beta                 98.205(4)
_cell_angle_gamma                93.393(5)
_cell_volume                     1126.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4284
_cell_measurement_theta_min      1.7880
_cell_measurement_theta_max      27.4874

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8457
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC12Κ/SATURN724
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        '< 1'
_diffrn_reflns_number            30705
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         27.49
_reflns_number_total             5112
_reflns_number_gt                4935
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
'CrystalClear (Rigaku Americas Corporation, 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  '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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_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)+(0.0649P)²+0.2470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5112
_refine_ls_number_parameters     333
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.119
_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 0.15317(13) 0.89596(9) 0.51649(7) 0.0379(2) Uani 1 1 d . . .
N1 N -0.02873(16) 0.92507(12) 0.32870(9) 0.0377(3) Uani 1 1 d D . .
H1N H -0.097(2) 0.8660(12) 0.3460(13) 0.045 Uiso 1 1 d D . .
H2N H -0.038(2) 0.9860(11) 0.3733(11) 0.045 Uiso 1 1 d D . .
N2 N 0.15115(15) 0.89320(10) 0.34751(8) 0.0347(3) Uani 1 1 d D . .
H3N H 0.204(2) 0.8791(14) 0.2931(9) 0.042 Uiso 1 1 d D . .
N3 N 0.50074(16) 0.81205(10) 0.36901(9) 0.0356(3) Uani 1 1 d . . .
N4 N 0.66196(16) 0.77969(11) 0.40134(9) 0.0378(3) Uani 1 1 d . . .
N5 N 0.68082(15) 0.79349(10) 0.50475(8) 0.0331(2) Uani 1 1 d . . .
N6 N 0.84046(15) 0.77107(10) 0.56359(9) 0.0357(3) Uani 1 1 d D . .
H4N H 0.9352(17) 0.8050(14) 0.5423(13) 0.043 Uiso 1 1 d D . .
C1 C 0.23127(18) 0.87943(11) 0.44098(10) 0.0307(3) Uani 1 1 d . . .
C2 C 0.41727(17) 0.84337(11) 0.45082(9) 0.0308(3) Uani 1 1 d . . .
C3 C 0.53202(18) 0.83284(11) 0.53933(10) 0.0314(3) Uani 1 1 d . . .
C4 C 0.5173(2) 0.85506(14) 0.64880(10) 0.0403(3) Uani 1 1 d . . .
H4A H 0.4595 0.7852 0.6709 0.060 Uiso 1 1 calc R . .
H4B H 0.4438 0.9218 0.6598 0.060 Uiso 1 1 calc R . .
H4C H 0.6388 0.8728 0.6880 0.060 Uiso 1 1 calc R . .
C5 C 0.85805(19) 0.65355(12) 0.58560(10) 0.0351(3) Uani 1 1 d . . .
C6 C 1.0324(2) 0.61894(13) 0.61235(11) 0.0410(3) Uani 1 1 d . . .
H6 H 1.1350 0.6707 0.6092 0.049 Uiso 1 1 calc R . .
C7 C 1.0560(3) 0.50913(15) 0.64356(12) 0.0526(4) Uani 1 1 d . . .
H7 H 1.1751 0.4858 0.6622 0.063 Uiso 1 1 calc R . .
C8 C 0.9077(3) 0.43308(15) 0.64779(13) 0.0578(5) Uani 1 1 d . . .
H8 H 0.9246 0.3578 0.6696 0.069 Uiso 1 1 calc R . .
C9 C 0.7344(3) 0.46692(15) 0.62009(14) 0.0553(4) Uani 1 1 d . . .
H9 H 0.6323 0.4143 0.6225 0.066 Uiso 1 1 calc R . .
C10 C 0.7083(2) 0.57724(14) 0.58874(12) 0.0442(3) Uani 1 1 d . . .
H10 H 0.5891 0.6001 0.5697 0.053 Uiso 1 1 calc R . .
O11 O 1.32708(12) 0.11543(9) 0.03831(7) 0.0366(2) Uani 1 1 d . . .
N11 N 1.39610(16) 0.02924(11) -0.15519(9) 0.0360(3) Uani 1 1 d D . .
H5N H 1.442(2) -0.0149(13) -0.1085(11) 0.043 Uiso 1 1 d D . .
H6N H 1.473(2) 0.0917(11) -0.1506(13) 0.043 Uiso 1 1 d D . .
N12 N 1.23015(15) 0.06706(10) -0.13010(8) 0.0319(2) Uani 1 1 d D . .
H7N H 1.1416(17) 0.0667(14) -0.1817(10) 0.038 Uiso 1 1 d D . .
N13 N 0.89500(15) 0.15565(10) -0.10973(8) 0.0315(2) Uani 1 1 d . . .
N14 N 0.75182(15) 0.19841(10) -0.07800(8) 0.0333(2) Uani 1 1 d . . .
N15 N 0.78886(15) 0.21431(9) 0.02504(8) 0.0310(2) Uani 1 1 d . . .
N16 N 0.66514(15) 0.25861(10) 0.08380(9) 0.0343(3) Uani 1 1 d D . .
H8N H 0.5572(15) 0.2203(13) 0.0660(13) 0.041 Uiso 1 1 d D . .
C11 C 1.20664(17) 0.10854(10) -0.03697(9) 0.0291(3) Uani 1 1 d . . .
C12 C 1.02388(17) 0.14711(11) -0.02755(9) 0.0290(3) Uani 1 1 d . . .
C13 C 0.95643(17) 0.18379(11) 0.06001(10) 0.0306(3) Uani 1 1 d . . .
C14 C 1.0299(2) 0.19248(14) 0.16955(10) 0.0411(3) Uani 1 1 d . . .
H14A H 0.9304 0.1792 0.2085 0.062 Uiso 1 1 calc R . .
H14B H 1.0905 0.2708 0.1916 0.062 Uiso 1 1 calc R . .
H14C H 1.1175 0.1331 0.1809 0.062 Uiso 1 1 calc R . .
C15 C 0.66529(19) 0.38270(12) 0.09951(10) 0.0342(3) Uani 1 1 d . . .
C16 C 0.5138(2) 0.42975(14) 0.13261(12) 0.0440(3) Uani 1 1 d . . .
H16 H 0.4119 0.3795 0.1399 0.053 Uiso 1 1 calc R . .
C17 C 0.5119(3) 0.54995(16) 0.15490(13) 0.0551(4) Uani 1 1 d . . .
H17 H 0.4078 0.5819 0.1770 0.066 Uiso 1 1 calc R . .
C18 C 0.6589(3) 0.62357(14) 0.14546(13) 0.0568(5) Uani 1 1 d . . .
H18 H 0.6572 0.7060 0.1617 0.068 Uiso 1 1 calc R . .
C19 C 0.8090(3) 0.57719(14) 0.11224(13) 0.0516(4) Uani 1 1 d . . .
H19 H 0.9106 0.6281 0.1054 0.062 Uiso 1 1 calc R . .
C20 C 0.8132(2) 0.45633(13) 0.08862(11) 0.0405(3) Uani 1 1 d . . .
H20 H 0.9166 0.4249 0.0653 0.049 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2413(16) . ?
N1 N2 1.4072(17) . ?
N1 H1N 0.895(9) . ?
N1 H2N 0.886(9) . ?
N2 C1 1.3372(17) . ?
N2 H3N 0.880(9) . ?
N3 N4 1.3079(17) . ?
N3 C2 1.3636(17) . ?
N4 N5 1.3640(16) . ?
N5 C3 1.3475(17) . ?
N5 N6 1.3844(15) . ?
N6 C5 1.4197(18) . ?
N6 H4N 0.883(9) . ?
C1 C2 1.4639(18) . ?
C2 C3 1.3804(17) . ?
C3 C4 1.4834(18) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.387(2) . ?
C5 C6 1.392(2) . ?
C6 C7 1.381(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
O11 C11 1.2441(15) . ?
N11 N12 1.4101(16) . ?
N11 H5N 0.887(9) . ?
N11 H6N 0.885(9) . ?
N12 C11 1.3285(17) . ?
N12 H7N 0.885(9) . ?
N13 N14 1.3087(16) . ?
N13 C12 1.3702(16) . ?
N14 N15 1.3596(15) . ?
N15 C13 1.3507(17) . ?
N15 N16 1.3828(15) . ?
N16 C15 1.4187(17) . ?
N16 H8N 0.884(9) . ?
C11 C12 1.4771(18) . ?
C12 C13 1.3782(18) . ?
C13 C14 1.4825(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.390(2) . ?
C15 C20 1.384(2) . ?
C16 C17 1.383(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.395(2) . ?
C19 H19 0.9500 . ?
C20 H20 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
N2 N1 H1N 105.5(11) . . ?
N2 N1 H2N 107.1(12) . . ?
H1N N1 H2N 105.4(16) . . ?
C1 N2 N1 121.77(11) . . ?
C1 N2 H3N 123.0(11) . . ?
N1 N2 H3N 115.1(11) . . ?
N4 N3 C2 108.71(11) . . ?
N3 N4 N5 106.31(11) . . ?
C3 N5 N4 112.47(11) . . ?
C3 N5 N6 126.18(11) . . ?
N4 N5 N6 121.33(11) . . ?
N5 N6 C5 116.74(11) . . ?
N5 N6 H4N 110.6(11) . . ?
C5 N6 H4N 115.4(11) . . ?
O1 C1 N2 122.24(12) . . ?
O1 C1 C2 120.92(12) . . ?
N2 C1 C2 116.84(12) . . ?
N3 C2 C3 109.91(12) . . ?
N3 C2 C1 122.69(12) . . ?
C3 C2 C1 127.38(12) . . ?
N5 C3 C2 102.58(11) . . ?
N5 C3 C4 123.27(12) . . ?
C2 C3 C4 134.15(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 120.07(14) . . ?
C10 C5 N6 122.01(13) . . ?
C6 C5 N6 117.73(13) . . ?
C7 C6 C5 119.86(15) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.44(16) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 119.73(15) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.55(17) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C5 119.35(15) . . ?
C9 C10 H10 120.3 . . ?
C5 C10 H10 120.3 . . ?
N12 N11 H5N 108.3(11) . . ?
N12 N11 H6N 108.2(11) . . ?
H5N N11 H6N 106.5(16) . . ?
C11 N12 N11 123.73(11) . . ?
C11 N12 H7N 120.4(11) . . ?
N11 N12 H7N 115.7(11) . . ?
N14 N13 C12 109.00(11) . . ?
N13 N14 N15 106.35(10) . . ?
C13 N15 N14 112.28(11) . . ?
C13 N15 N16 125.93(11) . . ?
N14 N15 N16 121.78(11) . . ?
N15 N16 C15 116.31(11) . . ?
N15 N16 H8N 111.1(11) . . ?
C15 N16 H8N 115.6(11) . . ?
O11 C11 N12 123.80(12) . . ?
O11 C11 C12 121.04(12) . . ?
N12 C11 C12 115.16(11) . . ?
N13 C12 C13 109.20(11) . . ?
N13 C12 C11 122.96(11) . . ?
C13 C12 C11 127.79(11) . . ?
N15 C13 C12 103.15(11) . . ?
N15 C13 C14 123.03(12) . . ?
C12 C13 C14 133.82(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 119.88(13) . . ?
C16 C15 N16 117.63(13) . . ?
C20 C15 N16 122.38(13) . . ?
C17 C16 C15 119.85(16) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.67(16) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.60(15) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 120.65(16) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 119.35(15) . . ?
C15 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?

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
C2 N3 N4 N5 -1.32(14) . . . . ?
N3 N4 N5 C3 0.92(15) . . . . ?
N3 N4 N5 N6 -177.49(11) . . . . ?
C3 N5 N6 C5 94.77(16) . . . . ?
N4 N5 N6 C5 -87.05(15) . . . . ?
N1 N2 C1 O1 -1.3(2) . . . . ?
N1 N2 C1 C2 178.56(12) . . . . ?
N4 N3 C2 C3 1.32(15) . . . . ?
N4 N3 C2 C1 -177.37(12) . . . . ?
O1 C1 C2 N3 172.69(12) . . . . ?
N2 C1 C2 N3 -7.21(19) . . . . ?
O1 C1 C2 C3 -5.8(2) . . . . ?
N2 C1 C2 C3 174.35(12) . . . . ?
N4 N5 C3 C2 -0.12(14) . . . . ?
N6 N5 C3 C2 178.20(12) . . . . ?
N4 N5 C3 C4 179.92(12) . . . . ?
N6 N5 C3 C4 -1.8(2) . . . . ?
N3 C2 C3 N5 -0.71(14) . . . . ?
C1 C2 C3 N5 177.90(12) . . . . ?
N3 C2 C3 C4 179.25(14) . . . . ?
C1 C2 C3 C4 -2.1(2) . . . . ?
N5 N6 C5 C10 -26.94(18) . . . . ?
N5 N6 C5 C6 158.15(12) . . . . ?
C10 C5 C6 C7 -1.0(2) . . . . ?
N6 C5 C6 C7 174.00(13) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C5 -0.1(2) . . . . ?
C6 C5 C10 C9 0.9(2) . . . . ?
N6 C5 C10 C9 -173.93(14) . . . . ?
C12 N13 N14 N15 -1.44(13) . . . . ?
N13 N14 N15 C13 0.99(14) . . . . ?
N13 N14 N15 N16 -179.88(10) . . . . ?
C13 N15 N16 C15 94.31(15) . . . . ?
N14 N15 N16 C15 -84.71(15) . . . . ?
N11 N12 C11 O11 -2.0(2) . . . . ?
N11 N12 C11 C12 178.04(11) . . . . ?
N14 N13 C12 C13 1.43(14) . . . . ?
N14 N13 C12 C11 -176.29(11) . . . . ?
O11 C11 C12 N13 171.17(11) . . . . ?
N12 C11 C12 N13 -8.87(17) . . . . ?
O11 C11 C12 C13 -6.1(2) . . . . ?
N12 C11 C12 C13 173.85(12) . . . . ?
N14 N15 C13 C12 -0.11(14) . . . . ?
N16 N15 C13 C12 -179.21(11) . . . . ?
N14 N15 C13 C14 -179.85(12) . . . . ?
N16 N15 C13 C14 1.1(2) . . . . ?
N13 C12 C13 N15 -0.78(13) . . . . ?
C11 C12 C13 N15 176.81(12) . . . . ?
N13 C12 C13 C14 178.92(14) . . . . ?
C11 C12 C13 C14 -3.5(2) . . . . ?
N15 N16 C15 C16 162.36(12) . . . . ?
N15 N16 C15 C20 -21.38(19) . . . . ?
C20 C15 C16 C17 -0.2(2) . . . . ?
N16 C15 C16 C17 176.11(14) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C16 C15 C20 C19 0.7(2) . . . . ?
N16 C15 C20 C19 -175.45(13) . . . . ?
C18 C19 C20 C15 -0.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_1296
_database_code_depnum_ccdc_archive 'CCDC 933969'
_audit_update_record             
;
2013-04-15 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;
#TrackingRef '3.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 Cl N6 O'
_chemical_formula_sum            'C10 H11 Cl N6 O'
_chemical_formula_weight         266.70

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   11.4176(4)
_cell_length_b                   7.2174(2)
_cell_length_c                   29.6018(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2439.35(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3030
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'

_exptl_special_details           
;
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16729
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2765
_reflns_number_gt                1972
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_reduction        'DENZO & COLLECT'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  '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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_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)+(0.0430P)²+1.0634P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2765
_refine_ls_number_parameters     176
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
Cl1 Cl 0.10701(5) 0.80652(8) 0.662092(17) 0.04196(18) Uani 1 1 d . . .
O1 O -0.17459(12) 1.0625(2) 0.97406(5) 0.0414(4) Uani 1 1 d . . .
N1 N -0.12212(15) 1.3969(3) 1.01348(6) 0.0368(5) Uani 1 1 d D . .
H1N H -0.1471(19) 1.310(2) 1.0322(7) 0.044 Uiso 1 1 d D . .
H2N H -0.1858(13) 1.438(3) 0.9997(7) 0.044 Uiso 1 1 d D . .
N2 N -0.05336(15) 1.3048(2) 0.98048(5) 0.0305(4) Uani 1 1 d D . .
H3N H 0.0126(12) 1.360(3) 0.9744(7) 0.037 Uiso 1 1 d D . .
N3 N 0.10242(13) 1.1414(2) 0.92026(5) 0.0267(4) Uani 1 1 d . . .
N4 N 0.15828(14) 1.0337(2) 0.89232(5) 0.0277(4) Uani 1 1 d . . .
N5 N 0.09154(13) 0.8794(2) 0.88706(5) 0.0243(3) Uani 1 1 d . . .
N6 N 0.12760(14) 0.7329(2) 0.86038(5) 0.0268(4) Uani 1 1 d D . .
H4N H 0.1920(12) 0.683(2) 0.8710(6) 0.032 Uiso 1 1 d D . .
C1 C -0.08385(16) 1.1419(3) 0.96387(6) 0.0266(4) Uani 1 1 d . . .
C2 C 0.00010(15) 1.0570(2) 0.93238(6) 0.0228(4) Uani 1 1 d . . .
C3 C -0.00833(15) 0.8880(3) 0.91133(6) 0.0232(4) Uani 1 1 d . . .
C4 C -0.09755(17) 0.7393(3) 0.91142(7) 0.0329(5) Uani 1 1 d . . .
H4A H -0.0593 0.6194 0.9065 0.049 Uiso 1 1 calc R . .
H4B H -0.1544 0.7620 0.8872 0.049 Uiso 1 1 calc R . .
H4C H -0.1380 0.7379 0.9406 0.049 Uiso 1 1 calc R . .
C5 C 0.12521(15) 0.7615(3) 0.81329(6) 0.0224(4) Uani 1 1 d . . .
C6 C 0.21451(16) 0.6904(2) 0.78683(6) 0.0252(4) Uani 1 1 d . . .
H6 H 0.2798 0.6320 0.8007 0.030 Uiso 1 1 calc R . .
C7 C 0.20909(17) 0.7039(2) 0.74047(6) 0.0271(4) Uani 1 1 d . . .
H7 H 0.2698 0.6533 0.7223 0.033 Uiso 1 1 calc R . .
C8 C 0.11506(16) 0.7913(3) 0.72056(6) 0.0265(4) Uani 1 1 d . . .
C9 C 0.02642(17) 0.8663(2) 0.74645(6) 0.0266(4) Uani 1 1 d . . .
H9 H -0.0375 0.9280 0.7324 0.032 Uiso 1 1 calc R . .
C10 C 0.03150(16) 0.8507(2) 0.79294(6) 0.0252(4) Uani 1 1 d . . .
H10 H -0.0294 0.9013 0.8110 0.030 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.7368(19) . ?
O1 C1 1.222(2) . ?
N1 N2 1.418(2) . ?
N1 H1N 0.883(10) . ?
N1 H2N 0.884(10) . ?
N2 C1 1.321(3) . ?
N2 H3N 0.870(10) . ?
N3 N4 1.302(2) . ?
N3 C2 1.365(2) . ?
N4 N5 1.358(2) . ?
N5 C3 1.349(2) . ?
N5 N6 1.383(2) . ?
N6 C5 1.410(2) . ?
N6 H4N 0.877(9) . ?
C1 C2 1.471(3) . ?
C2 C3 1.373(3) . ?
C3 C4 1.480(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.384(2) . ?
C5 C10 1.386(3) . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 H10 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
N2 N1 H1N 106.2(16) . . ?
N2 N1 H2N 107.2(15) . . ?
H1N N1 H2N 105(2) . . ?
C1 N2 N1 121.83(17) . . ?
C1 N2 H3N 123.8(14) . . ?
N1 N2 H3N 114.1(14) . . ?
N4 N3 C2 108.66(15) . . ?
N3 N4 N5 106.70(14) . . ?
C3 N5 N4 112.04(15) . . ?
C3 N5 N6 126.24(16) . . ?
N4 N5 N6 121.70(15) . . ?
N5 N6 C5 116.55(15) . . ?
N5 N6 H4N 111.1(13) . . ?
C5 N6 H4N 115.4(13) . . ?
O1 C1 N2 123.30(18) . . ?
O1 C1 C2 120.92(18) . . ?
N2 C1 C2 115.77(17) . . ?
N3 C2 C3 109.69(16) . . ?
N3 C2 C1 122.58(17) . . ?
C3 C2 C1 127.73(17) . . ?
N5 C3 C2 102.91(15) . . ?
N5 C3 C4 123.32(17) . . ?
C2 C3 C4 133.78(17) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 119.66(17) . . ?
C6 C5 N6 119.39(16) . . ?
C10 C5 N6 120.84(16) . . ?
C7 C6 C5 120.29(17) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.58(17) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.90(18) . . ?
C7 C8 Cl1 119.77(15) . . ?
C9 C8 Cl1 119.33(15) . . ?
C8 C9 C10 119.36(18) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C5 120.18(17) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 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
C2 N3 N4 N5 -0.63(19) . . . . ?
N3 N4 N5 C3 0.6(2) . . . . ?
N3 N4 N5 N6 -177.92(15) . . . . ?
C3 N5 N6 C5 109.36(19) . . . . ?
N4 N5 N6 C5 -72.3(2) . . . . ?
N1 N2 C1 O1 3.1(3) . . . . ?
N1 N2 C1 C2 -175.76(16) . . . . ?
N4 N3 C2 C3 0.5(2) . . . . ?
N4 N3 C2 C1 179.81(16) . . . . ?
O1 C1 C2 N3 -179.88(17) . . . . ?
N2 C1 C2 N3 -1.0(3) . . . . ?
O1 C1 C2 C3 -0.6(3) . . . . ?
N2 C1 C2 C3 178.21(17) . . . . ?
N4 N5 C3 C2 -0.32(19) . . . . ?
N6 N5 C3 C2 178.13(16) . . . . ?
N4 N5 C3 C4 179.36(16) . . . . ?
N6 N5 C3 C4 -2.2(3) . . . . ?
N3 C2 C3 N5 -0.07(19) . . . . ?
C1 C2 C3 N5 -179.39(17) . . . . ?
N3 C2 C3 C4 -179.70(19) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
N5 N6 C5 C6 141.12(17) . . . . ?
N5 N6 C5 C10 -42.5(2) . . . . ?
C10 C5 C6 C7 -1.6(3) . . . . ?
N6 C5 C6 C7 174.80(17) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C6 C7 C8 Cl1 -179.29(14) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
Cl1 C8 C9 C10 178.61(14) . . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
C6 C5 C10 C9 0.9(3) . . . . ?
N6 C5 C10 C9 -175.44(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_br
_database_code_depnum_ccdc_archive 'CCDC 933970'
_audit_update_record             
;
2013-04-15 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;
#TrackingRef '4.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 Br N6 O'
_chemical_formula_sum            'C10 H11 Br N6 O'
_chemical_formula_weight         311.16

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   11.3672(4)
_cell_length_b                   7.2817(2)
_cell_length_c                   30.1714(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2497.36(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3211
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    3.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.736348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'

_exptl_special_details           
;
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13981
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2856
_reflns_number_gt                2078
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_reduction        'DENZO & COLLECT'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  '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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_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+1.5145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2856
_refine_ls_number_parameters     176
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_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 0.89309(3) 0.81774(4) 0.837804(8) 0.03841(10) Uani 1 1 d . . .
O1 O 1.17419(15) 1.0628(2) 0.52449(6) 0.0391(4) Uani 1 1 d . . .
N1 N 1.12186(18) 1.3962(3) 0.48636(7) 0.0347(5) Uani 1 1 d D . .
H1N H 1.154(2) 1.306(3) 0.4707(8) 0.042 Uiso 1 1 d D . .
H2N H 1.1877(15) 1.437(3) 0.4982(8) 0.042 Uiso 1 1 d D . .
N2 N 1.05369(18) 1.3061(3) 0.51928(6) 0.0286(4) Uani 1 1 d D . .
H3N H 0.9875(14) 1.360(3) 0.5265(8) 0.034 Uiso 1 1 d D . .
N3 N 0.89750(16) 1.1430(3) 0.57893(6) 0.0248(4) Uani 1 1 d . . .
N4 N 0.84167(16) 1.0360(3) 0.60654(6) 0.0253(4) Uani 1 1 d . . .
N5 N 0.90903(16) 0.8823(3) 0.61141(6) 0.0222(4) Uani 1 1 d . . .
N6 N 0.87344(16) 0.7365(3) 0.63788(6) 0.0247(4) Uani 1 1 d D . .
H4N H 0.8083(13) 0.687(3) 0.6285(7) 0.030 Uiso 1 1 d D . .
C1 C 1.0836(2) 1.1423(3) 0.53513(7) 0.0251(5) Uani 1 1 d . . .
C2 C 0.99944(19) 1.0588(3) 0.56653(6) 0.0212(5) Uani 1 1 d . . .
C3 C 1.00893(19) 0.8908(3) 0.58712(7) 0.0214(5) Uani 1 1 d . . .
C4 C 1.0977(2) 0.7420(3) 0.58642(8) 0.0303(5) Uani 1 1 d . . .
H4A H 1.0578 0.6227 0.5867 0.045 Uiso 1 1 calc R . .
H4B H 1.1484 0.7522 0.6126 0.045 Uiso 1 1 calc R . .
H4C H 1.1456 0.7525 0.5596 0.045 Uiso 1 1 calc R . .
C5 C 0.87567(18) 0.7658(3) 0.68405(7) 0.0207(5) Uani 1 1 d . . .
C6 C 0.78522(19) 0.6960(3) 0.71012(7) 0.0228(5) Uani 1 1 d . . .
H6 H 0.7197 0.6378 0.6965 0.027 Uiso 1 1 calc R . .
C7 C 0.79006(19) 0.7107(3) 0.75576(8) 0.0243(5) Uani 1 1 d . . .
H7 H 0.7290 0.6612 0.7736 0.029 Uiso 1 1 calc R . .
C8 C 0.8849(2) 0.7985(3) 0.77517(7) 0.0226(5) Uani 1 1 d . . .
C9 C 0.9744(2) 0.8715(3) 0.74985(8) 0.0232(5) Uani 1 1 d . . .
H9 H 1.0382 0.9332 0.7637 0.028 Uiso 1 1 calc R . .
C10 C 0.97065(19) 0.8542(3) 0.70415(7) 0.0227(5) Uani 1 1 d . . .
H10 H 1.0327 0.9023 0.6865 0.027 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C8 1.897(2) . ?
O1 C1 1.224(3) . ?
N1 N2 1.421(3) . ?
N1 H1N 0.886(10) . ?
N1 H2N 0.882(10) . ?
N2 C1 1.329(3) . ?
N2 H3N 0.877(10) . ?
N3 N4 1.305(3) . ?
N3 C2 1.363(3) . ?
N4 N5 1.364(3) . ?
N5 C3 1.353(3) . ?
N5 N6 1.389(3) . ?
N6 C5 1.409(3) . ?
N6 H4N 0.870(10) . ?
C1 C2 1.477(3) . ?
C2 C3 1.376(3) . ?
C3 C4 1.481(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.391(3) . ?
C5 C10 1.395(3) . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(3) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 H10 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
N2 N1 H1N 105.0(18) . . ?
N2 N1 H2N 109.6(18) . . ?
H1N N1 H2N 96(2) . . ?
C1 N2 N1 121.8(2) . . ?
C1 N2 H3N 122.3(17) . . ?
N1 N2 H3N 115.6(17) . . ?
N4 N3 C2 108.65(17) . . ?
N3 N4 N5 106.60(17) . . ?
C3 N5 N4 112.04(18) . . ?
C3 N5 N6 126.23(19) . . ?
N4 N5 N6 121.71(17) . . ?
N5 N6 C5 116.57(17) . . ?
N5 N6 H4N 112.1(16) . . ?
C5 N6 H4N 113.5(16) . . ?
O1 C1 N2 123.0(2) . . ?
O1 C1 C2 121.2(2) . . ?
N2 C1 C2 115.8(2) . . ?
N3 C2 C3 110.03(19) . . ?
N3 C2 C1 122.8(2) . . ?
C3 C2 C1 127.2(2) . . ?
N5 C3 C2 102.68(19) . . ?
N5 C3 C4 123.1(2) . . ?
C2 C3 C4 134.2(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 119.7(2) . . ?
C6 C5 N6 119.36(19) . . ?
C10 C5 N6 120.9(2) . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 119.2(2) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 Br1 119.19(17) . . ?
C7 C8 Br1 119.58(16) . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C5 119.9(2) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?

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 N3 N4 N5 -0.3(2) . . . . ?
N3 N4 N5 C3 0.4(2) . . . . ?
N3 N4 N5 N6 -178.20(18) . . . . ?
C3 N5 N6 C5 110.2(2) . . . . ?
N4 N5 N6 C5 -71.4(2) . . . . ?
N1 N2 C1 O1 4.1(3) . . . . ?
N1 N2 C1 C2 -175.25(19) . . . . ?
N4 N3 C2 C3 0.0(2) . . . . ?
N4 N3 C2 C1 179.60(19) . . . . ?
O1 C1 C2 N3 -179.7(2) . . . . ?
N2 C1 C2 N3 -0.3(3) . . . . ?
O1 C1 C2 C3 -0.2(3) . . . . ?
N2 C1 C2 C3 179.2(2) . . . . ?
N4 N5 C3 C2 -0.4(2) . . . . ?
N6 N5 C3 C2 178.15(19) . . . . ?
N4 N5 C3 C4 179.98(19) . . . . ?
N6 N5 C3 C4 -1.5(3) . . . . ?
N3 C2 C3 N5 0.2(2) . . . . ?
C1 C2 C3 N5 -179.3(2) . . . . ?
N3 C2 C3 C4 179.8(2) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
N5 N6 C5 C6 140.4(2) . . . . ?
N5 N6 C5 C10 -43.4(3) . . . . ?
C10 C5 C6 C7 -1.2(3) . . . . ?
N6 C5 C6 C7 175.03(19) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C6 C7 C8 Br1 -179.49(16) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
Br1 C8 C9 C10 178.43(16) . . . . ?
C8 C9 C10 C5 1.0(3) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
N6 C5 C10 C9 -176.04(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.071
