# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_3a
_audit_creation_date             2013-11-08
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C21 H18 N6, H2 O'
_chemical_formula_sum            'C21 H20 N6 O'
_chemical_formula_weight         372.43
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.05239 0.03377 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_cell_length_a                   12.8104(4)
_cell_length_b                   9.7998(2)
_cell_length_c                   15.3326(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.436(3)
_cell_angle_gamma                90
_cell_volume                     1766.04(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4006
_exptl_crystal_description       needle
_exptl_crystal_F_000             786.4025
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.4
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6629
_diffrn_reflns_theta_full        70.711752
_diffrn_reflns_theta_max         70.71
_diffrn_reflns_theta_min         3.14
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.980224
_diffrn_measured_fraction_theta_max 0.980224
_diffrn_radiation_wavelength     1.54184
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2957
_reflns_number_total             3321
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.264012
_refine_diff_density_min         -0.265748
_refine_diff_density_rms         0.056071
_refine_ls_d_res_high            0.816766
_refine_ls_d_res_low             11.753533
_refine_ls_goodness_of_fit_ref   1.052801
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.044808
_refine_ls_R_factor_gt           0.040048
_refine_ls_restrained_S_all      1.052801
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+0.4220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.107918
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_refinement_flags_posn
C1 C 1.11583(12) 0.14952(15) 0.32054(9) 0.0292(3) Uani 1.000000 .
H1 H 1.10317(12) 0.24368(15) 0.32742(9) 0.0350(4) Uiso 1.000000 R
C2 C 1.11393(12) -0.05035(15) 0.25429(10) 0.0306(3) Uani 1.000000 .
H2 H 1.10147(12) -0.12244(15) 0.20984(10) 0.0368(4) Uiso 1.000000 R
C3 C 1.16892(13) -0.05750(15) 0.35064(10) 0.0336(3) Uani 1.000000 .
H3 H 1.20248(13) -0.13792(15) 0.38492(10) 0.0403(4) Uiso 1.000000 R
C4 C 1.02565(11) 0.14598(14) 0.14342(9) 0.0252(3) Uani 1.000000 .
C5 C 1.08121(11) 0.25241(14) 0.12028(10) 0.0275(3) Uani 1.000000 .
H5 H 1.15415(11) 0.28068(14) 0.16417(10) 0.0330(4) Uiso 1.000000 R
C6 C 1.03053(12) 0.31783(15) 0.03313(10) 0.0302(3) Uani 1.000000 .
H6 H 1.06899(12) 0.38983(15) 0.01671(10) 0.0362(4) Uiso 1.000000 R
C7 C 0.92357(12) 0.27720(14) -0.02953(10) 0.0287(3) Uani 1.000000 .
H7 H 0.88860(12) 0.32239(14) -0.08896(10) 0.0345(4) Uiso 1.000000 R
C8 C 0.86604(11) 0.17091(14) -0.00699(9) 0.0249(3) Uani 1.000000 .
C9 C 0.74466(11) 0.13785(14) -0.07377(9) 0.0268(3) Uani 1.000000 .
H9a H 0.70127(18) 0.2240(3) -0.0936(7) 0.0322(4) Uiso 1.000000 R
H9b H 0.7456(5) 0.0911(8) -0.1307(4) 0.0322(4) Uiso 1.000000 R
C10 C 0.65264(11) 0.12334(13) 0.03613(9) 0.0255(3) Uani 1.000000 .
C11 C 0.71195(11) 0.11204(14) 0.13468(9) 0.0269(3) Uani 1.000000 .
C12 C 0.81804(12) 0.02614(15) 0.17592(10) 0.0287(3) Uani 1.000000 .
H12a H 0.87695(12) 0.0766(9) 0.2285(5) 0.0344(4) Uiso 1.000000 R
H12b H 0.8011(7) -0.0581(4) 0.2035(7) 0.0344(4) Uiso 1.000000 R
C13 C 0.91783(11) 0.10188(13) 0.07967(9) 0.0240(3) Uani 1.000000 .
C14 C 0.76659(11) -0.06078(14) 0.02037(10) 0.0275(3) Uani 1.000000 .
H14a H 0.7952(4) -0.1040(10) -0.02421(13) 0.0330(4) Uiso 1.000000 R
H14b H 0.7256(2) -0.1320(8) 0.0401(5) 0.0330(4) Uiso 1.000000 R
C15 C 0.55606(12) 0.20805(14) 0.00097(10) 0.0289(3) Uani 1.000000 .
C16 C 0.52020(13) 0.27882(15) 0.06233(11) 0.0351(3) Uani 1.000000 .
H16 H 0.45515(13) 0.33616(15) 0.03768(11) 0.0422(4) Uiso 1.000000 R
C17 C 0.57978(13) 0.26568(16) 0.16029(11) 0.0370(4) Uani 1.000000 .
H17 H 0.55549(13) 0.31412(16) 0.20255(11) 0.0445(4) Uiso 1.000000 R
C18 C 0.67387(12) 0.18237(15) 0.19561(10) 0.0324(3) Uani 1.000000 .
H18 H 0.71348(12) 0.17258(15) 0.26242(10) 0.0389(4) Uiso 1.000000 R
C19 C 0.45278(12) 0.12288(15) -0.16503(10) 0.0296(3) Uani 1.000000 .
H19 H 0.47263(12) 0.02935(15) -0.15260(10) 0.0356(4) Uiso 1.000000 R
C20 C 0.44455(14) 0.34363(17) -0.14457(13) 0.0433(4) Uani 1.000000 .
H20 H 0.45550(14) 0.43233(17) -0.11738(13) 0.0519(5) Uiso 1.000000 R
C21 C 0.38005(13) 0.31008(18) -0.23500(12) 0.0438(4) Uani 1.000000 .
H21 H 0.33758(13) 0.37317(18) -0.28307(12) 0.0525(5) Uiso 1.000000 R
H1a H 0.3242(18) 0.051(2) 0.6365(16) 0.058(6) Uiso 1.000000 .
H1b H 0.2657(18) 0.035(2) 0.5340(16) 0.060(6) Uiso 1.000000 .
N1 N 1.16926(11) 0.06776(13) 0.39164(8) 0.0339(3) Uani 1.000000 .
N2 N 1.08026(9) 0.08360(12) 0.23506(8) 0.0259(3) Uani 1.000000 .
N3 N 0.86332(9) -0.01085(11) 0.10431(8) 0.0262(3) Uani 1.000000 .
N4 N 0.68764(9) 0.04917(11) -0.02844(8) 0.0255(3) Uani 1.000000 .
N5 N 0.49178(10) 0.22342(12) -0.09899(8) 0.0299(3) Uani 1.000000 .
N6 N 0.38401(10) 0.17083(14) -0.24853(9) 0.0362(3) Uani 1.000000 .
O1 O 0.30331(12) -0.01126(13) 0.58840(9) 0.0523(3) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9500 .
C1 N1 1.3059(19) .
C1 N2 1.3666(17) .
C2 H2 0.9500 .
C2 C3 1.362(2) .
C2 N2 1.3765(18) .
C3 H3 0.9500 .
C3 N1 1.3784(19) .
C4 C5 1.3860(19) .
C4 C13 1.4057(18) .
C4 N2 1.4338(17) .
C5 H5 0.9500 .
C5 C6 1.3885(19) .
C6 H6 0.9500 .
C6 C7 1.383(2) .
C7 H7 0.9500 .
C7 C8 1.3964(19) .
C8 C9 1.5181(18) .
C8 C13 1.4007(18) .
C9 H9a 0.9900 .
C9 H9b 0.9900 .
C9 N4 1.4751(17) .
C10 C11 1.3999(19) .
C10 C15 1.4071(19) .
C10 N4 1.4361(17) .
C11 C12 1.5073(19) .
C11 C18 1.3957(19) .
C12 H12a 0.9900 .
C12 H12b 0.9900 .
C12 N3 1.4764(17) .
C13 N3 1.4355(17) .
C14 H14a 0.9900 .
C14 H14b 0.9900 .
C14 N3 1.4707(17) .
C14 N4 1.4635(17) .
C15 C16 1.386(2) .
C15 N5 1.4303(18) .
C16 H16 0.9500 .
C16 C17 1.394(2) .
C17 H17 0.9500 .
C17 C18 1.376(2) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C19 N5 1.3577(18) .
C19 N6 1.3186(18) .
C20 H20 0.9500 .
C20 C21 1.342(2) .
C20 N5 1.381(2) .
C21 H21 0.9500 .
C21 N6 1.384(2) .
H1a O1 0.91(2) .
H1b O1 0.90(2) .

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
N1 C1 H1 124.00(8) . .
N2 C1 H1 124.00(8) . .
N2 C1 N1 112.01(12) . .
C3 C2 H2 127.34(9) . .
N2 C2 H2 127.34(7) . .
N2 C2 C3 105.32(12) . .
H3 C3 C2 124.60(9) . .
N1 C3 C2 110.81(13) . .
N1 C3 H3 124.60(8) . .
C13 C4 C5 121.06(12) . .
N2 C4 C5 118.14(12) . .
N2 C4 C13 120.79(12) . .
H5 C5 C4 119.91(8) . .
C6 C5 C4 120.17(13) . .
C6 C5 H5 119.91(8) . .
H6 C6 C5 120.31(8) . .
C7 C6 C5 119.37(13) . .
C7 C6 H6 120.31(8) . .
H7 C7 C6 119.42(8) . .
C8 C7 C6 121.17(13) . .
C8 C7 H7 119.42(8) . .
C9 C8 C7 119.47(12) . .
C13 C8 C7 119.84(12) . .
C13 C8 C9 120.56(12) . .
H9a C9 C8 108.9(3) . .
H9b C9 C8 108.9(3) . .
H9b C9 H9a 109.0(13) . .
N4 C9 C8 111.98(11) . .
N4 C9 H9a 108.9(3) . .
N4 C9 H9b 108.9(3) . .
C15 C10 C11 118.50(12) . .
N4 C10 C11 121.33(12) . .
N4 C10 C15 120.16(12) . .
C12 C11 C10 120.57(12) . .
C18 C11 C10 119.95(13) . .
C18 C11 C12 119.46(12) . .
H12a C12 C11 109.3(3) . .
H12b C12 C11 109.3(3) . .
H12b C12 H12a 107.1(13) . .
N3 C12 C11 112.37(11) . .
N3 C12 H12a 109.3(3) . .
N3 C12 H12b 109.3(3) . .
C8 C13 C4 118.35(12) . .
N3 C13 C4 119.99(11) . .
N3 C13 C8 121.66(11) . .
H14b C14 H14a 107.2(13) . .
N3 C14 H14a 109.4(3) . .
N3 C14 H14b 109.4(3) . .
N4 C14 H14a 109.4(3) . .
N4 C14 H14b 109.4(3) . .
N4 C14 N3 111.90(11) . .
C16 C15 C10 120.90(13) . .
N5 C15 C10 121.09(12) . .
N5 C15 C16 118.01(13) . .
H16 C16 C15 120.07(9) . .
C17 C16 C15 119.86(14) . .
C17 C16 H16 120.07(9) . .
H17 C17 C16 120.09(9) . .
C18 C17 C16 119.83(13) . .
C18 C17 H17 120.09(9) . .
C17 C18 C11 120.94(14) . .
H18 C18 C11 119.53(9) . .
H18 C18 C17 119.53(9) . .
N5 C19 H19 124.11(8) . .
N6 C19 H19 124.11(9) . .
N6 C19 N5 111.79(13) . .
C21 C20 H20 126.88(10) . .
N5 C20 H20 126.88(9) . .
N5 C20 C21 106.24(14) . .
H21 C21 C20 124.69(10) . .
N6 C21 C20 110.61(14) . .
N6 C21 H21 124.69(8) . .
C3 N1 C1 105.08(12) . .
C2 N2 C1 106.79(11) . .
C4 N2 C1 125.80(12) . .
C4 N2 C2 127.28(11) . .
C13 N3 C12 112.52(11) . .
C14 N3 C12 106.80(10) . .
C14 N3 C13 110.76(10) . .
C10 N4 C9 112.06(10) . .
C14 N4 C9 107.68(10) . .
C14 N4 C10 111.21(10) . .
C19 N5 C15 127.38(12) . .
C20 N5 C15 125.59(13) . .
C20 N5 C19 106.53(12) . .
C21 N6 C19 104.83(13) . .
H1b O1 H1a 106.9(19) . .

_database_code_depnum_ccdc_archive 'CCDC 979765'
#######################################################################
#
#                 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_3b
_audit_creation_date             2013-10-31
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'H2 O, C21 H18 N6'
_chemical_formula_sum            'C21 H20 N6 O'
_chemical_formula_weight         372.43
_chemical_oxdiff_formula         'C18 H20 N6 Zn'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.05239 0.03377 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_cell_length_a                   12.9360(5)
_cell_length_b                   9.8962(3)
_cell_length_c                   15.4643(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.922(4)
_cell_angle_gamma                90
_cell_volume                     1809.63(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3386
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.6526
_cell_measurement_theta_min      3.7350
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3669
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             786.4025
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7054
_diffrn_reflns_theta_full        70.788372
_diffrn_reflns_theta_max         70.79
_diffrn_reflns_theta_min         3.74
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.979292
_diffrn_measured_fraction_theta_max 0.979292
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   12.00   37.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -87.0000   59.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega -100.00  -34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -120.0000 86

#__ type_ start__ end____ width___ exp.time_
  5 omega    0.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   60.0000 65

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
  7 omega   74.00  100.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   51.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  9 omega   93.00  164.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -150.0000 71

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
 11 omega  103.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 71

#__ type_ start__ end____ width___ exp.time_
 12 omega   69.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00  129.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
 14 omega   48.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
 15 omega   43.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 16 omega   66.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 43
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0249734000
_diffrn_orient_matrix_UB_12      -0.0666181000
_diffrn_orient_matrix_UB_13      0.0795290000
_diffrn_orient_matrix_UB_21      0.0532390000
_diffrn_orient_matrix_UB_22      0.1219937000
_diffrn_orient_matrix_UB_23      0.0646954000
_diffrn_orient_matrix_UB_31      -0.1161757000
_diffrn_orient_matrix_UB_32      0.0702686000
_diffrn_orient_matrix_UB_33      -0.0368967000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2936
_reflns_number_total             3405
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.699076
_refine_diff_density_min         -0.646321
_refine_diff_density_rms         0.058091
_refine_ls_d_res_high            0.816385
_refine_ls_d_res_low             11.824749
_refine_ls_goodness_of_fit_ref   1.043928
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3405
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.065177
_refine_ls_R_factor_gt           0.057767
_refine_ls_restrained_S_all      1.043928
_refine_ls_shift/su_max          0.0111
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0775P)²+0.8857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.157140
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_refinement_flags_posn
O1 O 0.3005(2) 1.0081(3) 0.58844(19) 0.0943(7) Uiso 1.000000 .
N1 N 0.16805(18) 0.9311(2) 0.39043(13) 0.0578(5) Uani 1.000000 .
N2 N 0.07933(14) 0.91600(17) 0.23483(11) 0.0414(4) Uani 1.000000 .
N3 N -0.13742(14) 1.00822(17) 0.10503(12) 0.0421(4) Uani 1.000000 .
N4 N -0.31198(13) 0.94932(16) -0.02838(11) 0.0406(4) Uani 1.000000 .
N5 N -0.50663(15) 0.77718(18) -0.10037(13) 0.0488(4) Uani 1.000000 .
N6 N -0.61380(16) 0.8287(2) -0.24894(14) 0.0627(6) Uani 1.000000 .
C1 C 0.1121(2) 1.0485(2) 0.25492(16) 0.0508(5) Uani 1.000000 .
C2 C 0.1665(2) 1.0548(2) 0.35010(17) 0.0581(6) Uani 1.000000 .
C3 C 0.11524(19) 0.8509(2) 0.31907(15) 0.0496(5) Uani 1.000000 .
C4 C 0.02497(16) 0.8548(2) 0.14345(13) 0.0402(4) Uani 1.000000 .
C5 C 0.08066(17) 0.7509(2) 0.12023(15) 0.0450(5) Uani 1.000000 .
C6 C 0.02997(19) 0.6867(2) 0.03327(16) 0.0510(5) Uani 1.000000 .
C7 C -0.07657(18) 0.7266(2) -0.02891(15) 0.0475(5) Uani 1.000000 .
C8 C -0.13413(16) 0.8304(2) -0.00638(13) 0.0398(4) Uani 1.000000 .
C9 C -0.08278(16) 0.89788(19) 0.08039(13) 0.0377(4) Uani 1.000000 .
C10 C -0.25491(17) 0.8628(2) -0.07304(14) 0.0436(5) Uani 1.000000 .
C11 C -0.23363(17) 1.0580(2) 0.02121(15) 0.0450(5) Uani 1.000000 .
C12 C -0.18245(18) 0.9705(2) 0.17523(15) 0.0474(5) Uani 1.000000 .
C13 C -0.28816(17) 0.8858(2) 0.13336(14) 0.0429(5) Uani 1.000000 .
C14 C -0.34688(16) 0.87521(19) 0.03497(14) 0.0396(4) Uani 1.000000 .
C15 C -0.44308(17) 0.7919(2) -0.00085(15) 0.0450(5) Uani 1.000000 .
C16 C -0.4790(2) 0.7223(2) 0.05938(19) 0.0584(6) Uani 1.000000 .
C17 C -0.4202(2) 0.7341(3) 0.15666(19) 0.0622(7) Uani 1.000000 .
C18 C -0.3263(2) 0.8160(2) 0.19292(16) 0.0529(6) Uani 1.000000 .
C19 C -0.54724(18) 0.8760(2) -0.16588(16) 0.0500(5) Uani 1.000000 .
C20 C -0.6155(2) 0.6918(3) -0.2362(2) 0.0759(8) Uani 1.000000 .
C21 C -0.5516(2) 0.6582(3) -0.1469(2) 0.0742(8) Uani 1.000000 .
H1 H 0.0991(2) 1.1205(2) 0.21111(16) 0.0610(6) Uiso 1.000000 R
H1a H 0.326(3) 0.961(3) 0.556(3) 0.1415(10) Uiso 1.000000 G
H1b H 0.251(3) 0.985(3) 0.609(3) 0.1415(10) Uiso 1.000000 G
H2 H 0.1994(2) 1.1345(2) 0.38450(17) 0.0697(7) Uiso 1.000000 R
H3 H 0.10332(19) 0.7574(2) 0.32546(15) 0.0595(6) Uiso 1.000000 R
H5 H 0.15361(17) 0.7235(2) 0.16382(15) 0.0540(6) Uiso 1.000000 R
H6 H 0.06822(19) 0.6160(2) 0.01672(16) 0.0612(6) Uiso 1.000000 R
H7 H -0.11137(18) 0.6824(2) -0.08831(15) 0.0570(6) Uiso 1.000000 R
H10a H -0.2977(3) 0.7774(4) -0.0935(11) 0.0524(6) Uiso 1.000000 R
H10b H -0.2544(7) 0.9097(12) -0.1294(6) 0.0524(6) Uiso 1.000000 R
H11a H -0.2744(3) 1.1287(11) 0.0403(7) 0.0540(6) Uiso 1.000000 R
H11b H -0.2056(6) 1.1024(14) -0.0225(2) 0.0540(6) Uiso 1.000000 R
H12a H -0.12393(18) 0.9201(13) 0.2276(8) 0.0569(6) Uiso 1.000000 R
H12b H -0.1988(10) 1.0534(5) 0.2032(11) 0.0569(6) Uiso 1.000000 R
H16 H -0.5440(2) 0.6663(2) 0.03418(19) 0.0700(7) Uiso 1.000000 R
H17 H -0.4446(2) 0.6859(3) 0.19804(19) 0.0746(8) Uiso 1.000000 R
H18 H -0.2870(2) 0.8250(2) 0.25952(16) 0.0635(7) Uiso 1.000000 R
H19 H -0.52952(18) 0.9691(2) -0.15311(16) 0.0600(6) Uiso 1.000000 R
H20 H -0.6567(2) 0.6293(3) -0.2845(2) 0.0910(10) Uiso 1.000000 R
H21 H -0.5395(2) 0.5699(3) -0.1205(2) 0.0890(10) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1a 0.8500 .
O1 H1b 0.8500 .
N1 C2 1.370(3) .
N1 C3 1.305(3) .
N2 C1 1.374(3) .
N2 C3 1.355(3) .
N2 C4 1.432(2) .
N3 C9 1.434(2) .
N3 C11 1.471(2) .
N3 C12 1.473(3) .
N4 C10 1.472(3) .
N4 C11 1.463(3) .
N4 C14 1.435(2) .
N5 C15 1.428(3) .
N5 C19 1.352(3) .
N5 C21 1.379(3) .
N6 C19 1.309(3) .
N6 C20 1.371(4) .
C1 C2 1.351(3) .
C1 H1 0.9500 .
C2 H2 0.9500 .
C3 H3 0.9500 .
C4 C5 1.384(3) .
C4 C9 1.405(3) .
C5 C6 1.388(3) .
C5 H5 0.9500 .
C6 C7 1.380(3) .
C6 H6 0.9500 .
C7 C8 1.393(3) .
C7 H7 0.9500 .
C8 C9 1.402(3) .
C8 C10 1.517(3) .
C10 H10a 0.9900 .
C10 H10b 0.9900 .
C11 H11a 0.9900 .
C11 H11b 0.9900 .
C12 C13 1.508(3) .
C12 H12a 0.9900 .
C12 H12b 0.9900 .
C13 C14 1.402(3) .
C13 C18 1.392(3) .
C14 C15 1.406(3) .
C15 C16 1.381(3) .
C16 C17 1.388(4) .
C16 H16 0.9500 .
C17 C18 1.376(4) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 C21 1.333(4) .
C20 H20 0.9500 .
C21 H21 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
H1b O1 H1a 127.1 . .
C3 N1 C2 104.63(19) . .
C3 N2 C1 106.38(17) . .
C4 N2 C1 127.55(17) . .
C4 N2 C3 125.95(18) . .
C11 N3 C9 110.67(16) . .
C12 N3 C9 112.80(16) . .
C12 N3 C11 106.75(16) . .
C11 N4 C10 107.49(16) . .
C14 N4 C10 112.31(15) . .
C14 N4 C11 111.13(16) . .
C19 N5 C15 127.78(19) . .
C21 N5 C15 125.9(2) . .
C21 N5 C19 105.9(2) . .
C20 N6 C19 104.8(2) . .
C2 C1 N2 105.52(19) . .
H1 C1 N2 127.24(12) . .
H1 C1 C2 127.24(14) . .
C1 C2 N1 111.0(2) . .
H2 C2 N1 124.48(12) . .
H2 C2 C1 124.48(14) . .
N2 C3 N1 112.4(2) . .
H3 C3 N1 123.79(13) . .
H3 C3 N2 123.79(12) . .
C5 C4 N2 118.10(18) . .
C9 C4 N2 120.58(18) . .
C9 C4 C5 121.31(18) . .
C6 C5 C4 120.02(19) . .
H5 C5 C4 119.99(12) . .
H5 C5 C6 119.99(12) . .
C7 C6 C5 119.3(2) . .
H6 C6 C5 120.34(12) . .
H6 C6 C7 120.34(13) . .
C8 C7 C6 121.38(19) . .
H7 C7 C6 119.31(13) . .
H7 C7 C8 119.31(12) . .
C9 C8 C7 119.79(18) . .
C10 C8 C7 119.60(18) . .
C10 C8 C9 120.48(18) . .
C4 C9 N3 120.26(17) . .
C8 C9 N3 121.60(17) . .
C8 C9 C4 118.14(18) . .
C8 C10 N4 112.24(16) . .
H10a C10 N4 108.9(5) . .
H10a C10 C8 108.9(5) . .
H10b C10 N4 108.9(4) . .
H10b C10 C8 108.9(5) . .
H10b C10 H10a 108.8(19) . .
N4 C11 N3 112.00(16) . .
H11a C11 N3 109.7(5) . .
H11a C11 N4 109.7(5) . .
H11b C11 N3 109.7(5) . .
H11b C11 N4 109.7(5) . .
H11b C11 H11a 106.0(19) . .
C13 C12 N3 112.66(16) . .
H12a C12 N3 109.3(5) . .
H12a C12 C13 109.3(5) . .
H12b C12 N3 109.3(5) . .
H12b C12 C13 109.3(5) . .
H12b C12 H12a 107(2) . .
C14 C13 C12 120.35(18) . .
C18 C13 C12 119.65(19) . .
C18 C13 C14 120.0(2) . .
C13 C14 N4 121.38(18) . .
C15 C14 N4 120.25(18) . .
C15 C14 C13 118.35(19) . .
C14 C15 N5 121.02(18) . .
C16 C15 N5 118.2(2) . .
C16 C15 C14 120.8(2) . .
C17 C16 C15 120.2(2) . .
H16 C16 C15 119.92(14) . .
H16 C16 C17 119.92(14) . .
C18 C17 C16 119.8(2) . .
H17 C17 C16 120.12(14) . .
H17 C17 C18 120.12(14) . .
C17 C18 C13 120.9(2) . .
H18 C18 C13 119.55(14) . .
H18 C18 C17 119.55(14) . .
N6 C19 N5 112.2(2) . .
H19 C19 N5 123.91(13) . .
H19 C19 N6 123.91(14) . .
C21 C20 N6 110.9(2) . .
H20 C20 N6 124.56(15) . .
H20 C20 C21 124.56(17) . .
C20 C21 N5 106.3(2) . .
H21 C21 N5 126.86(15) . .
H21 C21 C20 126.86(17) . .

_database_code_depnum_ccdc_archive 'CCDC 979766'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4
_audit_creation_date             2014-04-20
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_formula_moiety         'C21 H18 N6'
_chemical_formula_sum            'C21 H18 N6'
_chemical_formula_weight         354.42
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_cell_length_a                   25.140(4)
_cell_length_b                   5.5409(5)
_cell_length_c                   13.9897(17)
_cell_angle_alpha                90
_cell_angle_beta                 122.157(19)
_cell_angle_gamma                90
_cell_volume                     1649.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_exptl_absorpt_coefficient_mu    0.712
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4268
_exptl_crystal_description       needle
_exptl_crystal_F_000             746.1955
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2878
_diffrn_reflns_theta_full        70.3768
_diffrn_reflns_theta_max         70.38
_diffrn_reflns_theta_min         4.15
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.9785
_diffrn_measured_fraction_theta_max 0.9779
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              25
_reflns_limit_h_min              -30
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1281
_reflns_number_total             1547
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.2321
_refine_diff_density_min         -0.2986
_refine_diff_density_rms         0.0582
_refine_ls_d_res_high            0.8185
_refine_ls_d_res_low             10.6416
_refine_ls_goodness_of_fit_ref   1.0401
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.0401
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.7096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1152
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H1a(0.5) H1b(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C5(H5), C9(H9), C10(H10), C11(H11)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.500000 1.1963(4) 0.250000 0.0270(5) Uani 1.000000 S T
C2 C 0.57158(7) 0.9360(3) 0.23965(13) 0.0262(4) Uani 1.000000 . .
C3 C 0.58175(7) 0.8207(3) 0.34645(13) 0.0240(4) Uani 1.000000 . .
C4 C 0.54069(7) 0.8711(3) 0.38324(13) 0.0238(4) Uani 1.000000 . .
C5 C 0.54800(7) 0.7513(3) 0.47731(13) 0.0269(4) Uani 1.000000 . .
C6 C 0.59689(7) 0.5890(3) 0.53714(13) 0.0270(4) Uani 1.000000 . .
C7 C 0.63810(7) 0.5423(3) 0.50149(13) 0.0250(4) Uani 1.000000 . .
C8 C 0.63027(7) 0.6548(3) 0.40655(13) 0.0245(4) Uani 1.000000 . .
C9 C 0.75030(7) 0.4114(3) 0.59750(13) 0.0281(4) Uani 1.000000 . .
C10 C 0.74566(8) 0.0694(3) 0.66228(14) 0.0309(4) Uani 1.000000 . .
C11 C 0.68606(8) 0.1559(3) 0.60574(14) 0.0290(4) Uani 1.000000 . .
N1 N 0.50861(6) 1.0473(2) 0.17260(11) 0.0253(3) Uani 1.000000 . .
N2 N 0.68889(6) 0.3769(2) 0.56369(11) 0.0262(3) Uani 1.000000 . .
N3 N 0.78622(7) 0.2297(3) 0.65782(12) 0.0318(4) Uani 1.000000 . .
H8 H 0.65811(7) 0.6188(3) 0.38205(13) 0.0294(4) Uiso 1.000000 R .
H6 H 0.60222(7) 0.5102(3) 0.60201(13) 0.0324(5) Uiso 1.000000 R .
H5 H 0.51929(7) 0.7810(3) 0.50050(13) 0.0323(5) Uiso 1.000000 R .
H1a H 0.462807 1.3014(4) 0.205769 0.0324(6) Uiso 0.500000 R .
H1b H 0.537193 1.3014(4) 0.294231 0.0324(6) Uiso 0.500000 R .
H2a H 0.60407(7) 1.0610(3) 0.25991(13) 0.0315(5) Uiso 1.000000 R .
H2b H 0.57611(7) 0.8119(3) 0.19354(13) 0.0315(5) Uiso 1.000000 R .
H9 H 0.76534(7) 0.5506(3) 0.57949(13) 0.0337(5) Uiso 1.000000 R .
H10 H 0.75787(8) -0.0818(3) 0.70002(14) 0.0371(5) Uiso 1.000000 R .
H11 H 0.64985(8) 0.0798(3) 0.59698(14) 0.0348(5) Uiso 1.000000 R .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.4667(18) .
C1 N1 1.4667(18) 2_655
C2 C3 1.516(2) .
C2 N1 1.4782(19) .
C3 C4 1.405(2) .
C3 C8 1.396(2) .
C4 C5 1.396(2) .
C4 N1 1.4381(19) 2_655
C5 C6 1.387(2) .
C6 C7 1.392(2) .
C7 C8 1.383(2) .
C7 N2 1.4300(19) .
C9 N2 1.366(2) .
C9 N3 1.315(2) .
C10 C11 1.356(2) .
C10 N3 1.378(2) .
C11 N2 1.377(2) .

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
N1 C1 N1 111.45(18) . 2_655
N1 C2 C3 111.27(12) . .
C4 C3 C2 120.39(14) . .
C8 C3 C2 120.39(14) . .
C8 C3 C4 119.16(14) . .
C5 C4 C3 119.80(15) . .
N1 C4 C3 121.66(14) 2_655 .
N1 C4 C5 118.53(14) 2_655 .
C6 C5 C4 120.45(15) . .
C7 C6 C5 119.57(15) . .
C8 C7 C6 120.50(14) . .
N2 C7 C6 119.65(14) . .
N2 C7 C8 119.85(14) . .
C7 C8 C3 120.48(14) . .
N3 C9 N2 112.26(15) . .
N3 C10 C11 111.12(15) . .
N2 C11 C10 105.73(15) . .
C2 N1 C1 107.18(10) . 2_655
C4 N1 C1 111.09(11) 2_655 2_655
C4 N1 C2 112.59(12) 2_655 .
C9 N2 C7 126.85(14) . .
C11 N2 C7 126.70(14) . .
C11 N2 C9 106.39(14) . .
C10 N3 C9 104.50(14) . .

_database_code_depnum_ccdc_archive 'CCDC 979767'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5
_audit_creation_date             2013-12-21
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(I), C23 H24 N6'
_chemical_formula_sum            'C23 H24 I2 N6'
_chemical_formula_weight         638.30
_chemical_oxdiff_formula         'C22 H22 N6 I2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I -0.19206 6.94430 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_cell_length_a                   10.9300(2)
_cell_length_b                   16.8443(3)
_cell_length_c                   14.0472(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.695(3)
_cell_angle_gamma                90
_cell_volume                     2463.83(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4450
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.6311
_cell_measurement_theta_min      3.2997
_exptl_absorpt_coefficient_mu    20.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.7206
_exptl_crystal_description       needle
_exptl_crystal_F_000             1242.1119
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10257
_diffrn_reflns_theta_full        70.766692
_diffrn_reflns_theta_max         70.77
_diffrn_reflns_theta_min         3.30
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.981029
_diffrn_measured_fraction_theta_max 0.981029
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -82.0000  -13.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega -101.00  -44.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega  -67.00  -35.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega   13.00  124.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000   60.0000 111

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00   61.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   26.00   56.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00  103.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
  8 omega   36.00   73.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
  9 omega   58.00  129.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000 -120.0000 71

#__ type_ start__ end____ width___ exp.time_
 10 omega   67.00   93.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  100.00  168.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 68

#__ type_ start__ end____ width___ exp.time_
 12 omega   55.00   85.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 13 omega   89.00  178.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
 14 omega   80.00  126.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
 15 omega   87.00  178.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
 16 omega   43.00   73.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 17 omega   66.00   91.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00   65.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1070038000
_diffrn_orient_matrix_UB_12      0.0544198000
_diffrn_orient_matrix_UB_13      0.0131697000
_diffrn_orient_matrix_UB_21      -0.1021944000
_diffrn_orient_matrix_UB_22      -0.0582509000
_diffrn_orient_matrix_UB_23      -0.0618083000
_diffrn_orient_matrix_UB_31      0.0027771000
_diffrn_orient_matrix_UB_32      -0.0448629000
_diffrn_orient_matrix_UB_33      0.0961552000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3914
_reflns_number_total             4654
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         1.404677
_refine_diff_density_min         -2.080394
_refine_diff_density_rms         0.186271
_refine_ls_d_res_high            0.816493
_refine_ls_d_res_low             10.478140
_refine_ls_goodness_of_fit_ref   1.045289
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.060348
_refine_ls_R_factor_gt           0.052040
_refine_ls_restrained_S_all      1.045289
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0845P)²+0.0937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.142201
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_refinement_flags_posn
I2 I 0.37114(4) 0.39337(3) 0.75670(3) 0.05461(16) Uani 1.000000 .
I1 I 0.92356(4) 0.06878(2) 0.31909(3) 0.05641(16) Uani 1.000000 .
N4 N 0.7727(4) 0.2422(2) 0.9354(3) 0.0400(9) Uani 1.000000 .
N5 N 0.3956(4) 0.0958(3) 0.7023(3) 0.0393(9) Uani 1.000000 .
N6 N 0.3277(5) 0.0355(3) 0.5610(4) 0.0488(11) Uani 1.000000 .
N1 N 1.0953(5) 0.2646(3) 1.2332(3) 0.0399(9) Uani 1.000000 .
N2 N 1.0118(4) 0.2225(2) 1.0824(3) 0.0336(8) Uani 1.000000 .
N3 N 0.6101(4) 0.1928(3) 0.7886(3) 0.0405(9) Uani 1.000000 .
C13 C 0.6967(5) 0.2223(4) 1.0031(4) 0.0457(12) Uani 1.000000 .
H13a H 0.7525(7) 0.1925(19) 1.058(2) 0.0548(15) Uiso 1.000000 R
H13b H 0.664(2) 0.2718(6) 1.021(3) 0.0548(15) Uiso 1.000000 R
C14 C 0.5442(5) 0.1574(3) 0.8507(4) 0.0383(11) Uani 1.000000 .
C15 C 0.5819(5) 0.1703(3) 0.9548(4) 0.0415(11) Uani 1.000000 .
C12 C 0.6827(6) 0.2625(3) 0.8381(5) 0.0458(12) Uani 1.000000 .
H12a H 0.6249(17) 0.3043(16) 0.845(2) 0.0549(15) Uiso 1.000000 R
H12b H 0.728(2) 0.287(2) 0.7958(5) 0.0549(15) Uiso 1.000000 R
C9 C 0.8245(5) 0.1279(3) 0.8432(4) 0.0369(10) Uani 1.000000 .
C10 C 0.8554(5) 0.1788(3) 0.9260(4) 0.0351(10) Uani 1.000000 .
C11 C 0.6971(5) 0.1371(3) 0.7610(4) 0.0429(12) Uani 1.000000 .
H11a H 0.6557(6) 0.0856(4) 0.747(3) 0.0514(14) Uiso 1.000000 R
H11b H 0.7136(19) 0.156(2) 0.7009(17) 0.0514(14) Uiso 1.000000 R
C16 C 0.5117(6) 0.1345(4) 1.0114(5) 0.0529(14) Uani 1.000000 .
H16 H 0.5350(6) 0.1442(4) 1.0797(5) 0.0634(17) Uiso 1.000000 R
C21 C 0.3779(6) 0.1533(4) 0.6281(5) 0.0582(16) Uani 1.000000 .
H21 H 0.3910(6) 0.2077(4) 0.6374(5) 0.0699(19) Uiso 1.000000 R
C22 C 0.3380(8) 0.1147(4) 0.5405(5) 0.0618(17) Uani 1.000000 .
H22 H 0.3205(8) 0.1373(4) 0.4774(5) 0.074(2) Uiso 1.000000 R
C23 C 0.2829(8) -0.0281(5) 0.4872(6) 0.076(2) Uani 1.000000 .
H23a H 0.2639(8) -0.0064(5) 0.4211(6) 0.114(3) Uiso 1.000000 R
H23b H 0.3487(8) -0.0677(5) 0.4968(6) 0.114(3) Uiso 1.000000 R
H23c H 0.2068(8) -0.0518(5) 0.4954(6) 0.114(3) Uiso 1.000000 R
C20 C 0.3620(5) 0.0259(3) 0.6590(4) 0.0411(11) Uani 1.000000 .
H20 H 0.3624(5) -0.0220(3) 0.6920(4) 0.0493(13) Uiso 1.000000 R
C17 C 0.4086(6) 0.0849(4) 0.9687(5) 0.0532(14) Uani 1.000000 .
H17 H 0.3649(6) 0.0607(4) 1.0082(5) 0.0638(17) Uiso 1.000000 R
C18 C 0.3709(6) 0.0716(4) 0.8663(5) 0.0467(13) Uani 1.000000 .
H18 H 0.3019(6) 0.0384(4) 0.8366(5) 0.0560(15) Uiso 1.000000 R
C19 C 0.4377(5) 0.1086(3) 0.8089(4) 0.0390(11) Uani 1.000000 .
C8 C 0.9102(6) 0.0689(3) 0.8370(4) 0.0420(12) Uani 1.000000 .
H8 H 0.8898(6) 0.0358(3) 0.7815(4) 0.0504(14) Uiso 1.000000 R
C2 C 1.0630(5) 0.1999(3) 1.1765(4) 0.0351(10) Uani 1.000000 .
H2 H 1.0745(5) 0.1477(3) 1.1991(4) 0.0422(12) Uiso 1.000000 R
C6 C 1.0582(5) 0.1081(3) 0.9942(4) 0.0404(11) Uani 1.000000 .
H6 H 1.1350(5) 0.1010(3) 1.0451(4) 0.0484(14) Uiso 1.000000 R
C4 C 1.0125(5) 0.3060(3) 1.0785(4) 0.0426(12) Uani 1.000000 .
H4 H 0.9829(5) 0.3376(3) 1.0219(4) 0.0511(14) Uiso 1.000000 R
C5 C 0.9740(5) 0.1686(3) 0.9993(4) 0.0355(10) Uani 1.000000 .
C1 C 1.1575(7) 0.2621(4) 1.3408(4) 0.0561(16) Uani 1.000000 .
H1a H 1.1719(7) 0.3152(4) 1.3664(4) 0.084(2) Uiso 1.000000 R
H1b H 1.1033(7) 0.2345(4) 1.3723(4) 0.084(2) Uiso 1.000000 R
H1c H 1.2382(7) 0.2349(4) 1.3546(4) 0.084(2) Uiso 1.000000 R
C3 C 1.0640(5) 0.3306(3) 1.1724(4) 0.0418(12) Uani 1.000000 .
H3 H 1.0766(5) 0.3832(3) 1.1934(4) 0.0502(14) Uiso 1.000000 R
C7 C 1.0251(6) 0.0584(3) 0.9115(4) 0.0433(12) Uani 1.000000 .
H7 H 1.0804(6) 0.0178(3) 0.9063(4) 0.0520(15) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N4 C13 1.479(7) .
N4 C12 1.461(7) .
N4 C10 1.431(6) .
N5 C21 1.392(7) .
N5 C20 1.326(7) .
N5 C19 1.442(7) .
N6 C22 1.376(8) .
N6 C23 1.468(8) .
N6 C20 1.321(7) .
N1 C2 1.333(6) .
N1 C1 1.458(7) .
N1 C3 1.380(7) .
N2 C2 1.325(6) .
N2 C4 1.408(6) .
N2 C5 1.436(6) .
N3 C14 1.421(7) .
N3 C12 1.468(7) .
N3 C11 1.470(7) .
C13 H13a 0.9700 .
C13 H13b 0.9700 .
C13 C15 1.510(8) .
C14 C15 1.411(7) .
C14 C19 1.399(8) .
C15 C16 1.398(8) .
C12 H12a 0.9700 .
C12 H12b 0.9700 .
C9 C10 1.402(7) .
C9 C11 1.522(8) .
C9 C8 1.386(8) .
C10 C5 1.399(7) .
C11 H11a 0.9700 .
C11 H11b 0.9700 .
C16 H16 0.9300 .
C16 C17 1.384(9) .
C21 H21 0.9300 .
C21 C22 1.342(10) .
C22 H22 0.9300 .
C23 H23a 0.9600 .
C23 H23b 0.9600 .
C23 H23c 0.9600 .
C20 H20 0.9300 .
C17 H17 0.9300 .
C17 C18 1.388(9) .
C18 H18 0.9300 .
C18 C19 1.390(8) .
C8 H8 0.9300 .
C8 C7 1.380(9) .
C2 H2 0.9300 .
C6 H6 0.9300 .
C6 C5 1.390(7) .
C6 C7 1.388(8) .
C4 H4 0.9300 .
C4 C3 1.333(8) .
C1 H1a 0.9600 .
C1 H1b 0.9600 .
C1 H1c 0.9600 .
C3 H3 0.9300 .
C7 H7 0.9300 .

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
C12 N4 C13 107.8(4) . .
C10 N4 C13 112.5(4) . .
C10 N4 C12 110.7(4) . .
C20 N5 C21 108.5(5) . .
C19 N5 C21 127.0(5) . .
C19 N5 C20 124.5(5) . .
C23 N6 C22 126.2(6) . .
C20 N6 C22 108.7(5) . .
C20 N6 C23 125.1(6) . .
C1 N1 C2 123.4(5) . .
C3 N1 C2 108.6(4) . .
C3 N1 C1 127.9(5) . .
C4 N2 C2 108.7(4) . .
C5 N2 C2 124.0(4) . .
C5 N2 C4 127.1(4) . .
C12 N3 C14 110.3(4) . .
C11 N3 C14 112.5(4) . .
C11 N3 C12 109.6(4) . .
H13a C13 N4 107.1(13) . .
H13b C13 N4 107.1(13) . .
H13b C13 H13a 115(5) . .
C15 C13 N4 113.3(4) . .
C15 C13 H13a 107.1(13) . .
C15 C13 H13b 107.1(13) . .
C15 C14 N3 121.9(5) . .
C19 C14 N3 120.1(5) . .
C19 C14 C15 118.0(5) . .
C14 C15 C13 119.8(5) . .
C16 C15 C13 121.3(5) . .
C16 C15 C14 118.9(5) . .
N3 C12 N4 111.7(4) . .
H12a C12 N4 110.6(13) . .
H12a C12 N3 110.6(13) . .
H12b C12 N4 110.6(13) . .
H12b C12 N3 110.6(13) . .
H12b C12 H12a 102(6) . .
C11 C9 C10 120.1(5) . .
C8 C9 C10 119.5(5) . .
C8 C9 C11 120.3(5) . .
C9 C10 N4 122.2(5) . .
C5 C10 N4 119.6(4) . .
C5 C10 C9 118.2(5) . .
C9 C11 N3 112.4(4) . .
H11a C11 N3 108.9(14) . .
H11a C11 C9 108.9(14) . .
H11b C11 N3 108.9(14) . .
H11b C11 C9 108.9(14) . .
H11b C11 H11a 109(6) . .
H16 C16 C15 119.0(3) . .
C17 C16 C15 122.0(6) . .
C17 C16 H16 119.0(4) . .
H21 C21 N5 126.8(4) . .
C22 C21 N5 106.3(6) . .
C22 C21 H21 126.8(4) . .
C21 C22 N6 107.6(6) . .
H22 C22 N6 126.2(4) . .
H22 C22 C21 126.2(4) . .
H23a C23 N6 109.5 . .
H23b C23 N6 109.5 . .
H23b C23 H23a 109.5 . .
H23c C23 N6 109.5 . .
H23c C23 H23a 109.5 . .
H23c C23 H23b 109.5 . .
N6 C20 N5 108.7(5) . .
H20 C20 N5 125.6(3) . .
H20 C20 N6 125.6(3) . .
H17 C17 C16 120.2(4) . .
C18 C17 C16 119.5(6) . .
C18 C17 H17 120.2(4) . .
H18 C18 C17 120.5(4) . .
C19 C18 C17 119.1(5) . .
C19 C18 H18 120.5(3) . .
C14 C19 N5 119.0(5) . .
C18 C19 N5 118.5(5) . .
C18 C19 C14 122.4(5) . .
H8 C8 C9 119.3(3) . .
C7 C8 C9 121.4(5) . .
C7 C8 H8 119.3(3) . .
N2 C2 N1 108.4(4) . .
H2 C2 N1 125.8(3) . .
H2 C2 N2 125.8(3) . .
C5 C6 H6 120.7(3) . .
C7 C6 H6 120.7(3) . .
C7 C6 C5 118.5(5) . .
H4 C4 N2 126.9(3) . .
C3 C4 N2 106.1(5) . .
C3 C4 H4 126.9(3) . .
C10 C5 N2 119.6(4) . .
C6 C5 N2 118.3(5) . .
C6 C5 C10 122.1(5) . .
H1a C1 N1 109.5 . .
H1b C1 N1 109.5 . .
H1b C1 H1a 109.5 . .
H1c C1 N1 109.5 . .
H1c C1 H1a 109.5 . .
H1c C1 H1b 109.5 . .
C4 C3 N1 108.2(4) . .
H3 C3 N1 125.9(3) . .
H3 C3 C4 125.9(3) . .
C6 C7 C8 120.2(5) . .
H7 C7 C8 119.9(3) . .
H7 C7 C6 119.9(3) . .

_database_code_depnum_ccdc_archive 'CCDC 979768'
#######################################################################
#
#                 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_6
_audit_creation_date             2014-04-20
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_formula_moiety         '0.5(C54 H64 N12), 0.25(I8)'
_chemical_formula_sum            'C27 H32 I2 N6'
_chemical_formula_weight         694.40
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I -0.19206 6.94430 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_cell_length_a                   10.1807(5)
_cell_length_b                   13.9648(7)
_cell_length_c                   20.5397(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.629(5)
_cell_angle_gamma                90
_cell_volume                     2860.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_exptl_absorpt_coefficient_mu    17.468
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6125
_exptl_crystal_description       needle
_exptl_crystal_F_000             1370.2893
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5536
_diffrn_reflns_theta_full        70.692082
_diffrn_reflns_theta_max         70.69
_diffrn_reflns_theta_min         4.40
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.979378
_diffrn_measured_fraction_theta_max 0.979378
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                2283
_reflns_number_total             2707
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.710422
_refine_diff_density_min         -0.763886
_refine_diff_density_rms         0.120288
_refine_ls_d_res_high            0.816864
_refine_ls_d_res_low             10.059025
_refine_ls_goodness_of_fit_ref   1.020541
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.041248
_refine_ls_R_factor_gt           0.032518
_refine_ls_restrained_S_all      1.020541
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.083808
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_refinement_flags_posn
N2 N 0.5837(3) 0.3075(2) 0.43799(15) 0.0299(7) Uani 1.000000 .
C4 C 0.5540(4) 0.3656(3) 0.48513(18) 0.0328(9) Uani 1.000000 .
H4 H 0.5642(4) 0.4332(3) 0.48635(18) 0.0394(10) Uiso 1.000000 R
C13 C 0.500000 0.1720(4) 0.250000 0.0354(13) Uani 1.000000 S
H13a H 0.581(3) 0.132(3) 0.2597(3) 0.0425(16) Uiso 0.500000 R
H13b H 0.419(3) 0.132(3) 0.2403(3) 0.0425(16) Uiso 0.500000 R
N3 N 0.4953(4) 0.2316(2) 0.30861(15) 0.0324(7) Uani 1.000000 .
C11 C 0.3291(4) 0.3274(3) 0.22903(19) 0.0325(9) Uani 1.000000 .
C5 C 0.5076(4) 0.2189(3) 0.51098(19) 0.0343(9) Uani 1.000000 .
H5 H 0.4795(4) 0.1662(3) 0.53403(19) 0.0412(11) Uiso 1.000000 R
C6 C 0.5545(4) 0.2148(3) 0.45389(19) 0.0346(9) Uani 1.000000 .
H6 H 0.5653(4) 0.1587(3) 0.42933(19) 0.0415(11) Uiso 1.000000 R
C12 C 0.6033(4) 0.2988(3) 0.32034(18) 0.0303(8) Uani 1.000000 .
C7 C 0.6448(4) 0.3397(3) 0.38417(18) 0.0290(8) Uani 1.000000 .
C2 C 0.4629(5) 0.3535(3) 0.5884(2) 0.0384(10) Uani 1.000000 .
H2 H 0.4761(5) 0.4244(3) 0.5886(2) 0.0461(12) Uiso 1.000000 R
C8 C 0.2562(4) 0.4090(3) 0.1027(2) 0.0357(9) Uani 1.000000 .
H8 H 0.2312(4) 0.4361(3) 0.0596(2) 0.0429(11) Uiso 1.000000 R
N1 N 0.5083(3) 0.3138(2) 0.52944(16) 0.0324(7) Uani 1.000000 .
C3 C 0.3160(5) 0.3344(4) 0.5818(2) 0.0508(13) Uani 1.000000 .
H3a H 0.2672(6) 0.360(2) 0.5394(8) 0.0762(19) Uiso 1.000000 G
H3b H 0.3008(6) 0.2652(4) 0.5831(17) 0.0762(19) Uiso 1.000000 G
H3c H 0.2840(9) 0.365(2) 0.6185(10) 0.0762(19) Uiso 1.000000 G
C10 C 0.2296(4) 0.3971(3) 0.2159(2) 0.0379(9) Uani 1.000000 .
H10 H 0.1856(4) 0.4168(3) 0.2503(2) 0.0455(11) Uiso 1.000000 R
C1 C 0.5484(6) 0.3135(4) 0.6514(2) 0.0591(15) Uani 1.000000 .
H1a H 0.532(3) 0.2445(7) 0.6538(10) 0.089(2) Uiso 1.000000 G
H1b H 0.6433(6) 0.325(3) 0.6511(9) 0.089(2) Uiso 1.000000 G
H1c H 0.525(3) 0.345(2) 0.6900(2) 0.089(2) Uiso 1.000000 G
C14 C 0.3651(4) 0.2805(3) 0.29745(19) 0.0343(9) Uani 1.000000 .
H14a H 0.2946(7) 0.2335(12) 0.3019(12) 0.0412(11) Uiso 1.000000 R
H14b H 0.367(2) 0.3301(11) 0.3320(5) 0.0412(11) Uiso 1.000000 R
C9 C 0.1937(4) 0.4382(3) 0.1538(2) 0.0377(9) Uani 1.000000 .
H9 H 0.1265(4) 0.4864(3) 0.1459(2) 0.0453(11) Uiso 1.000000 R
I1 I 0.28969(3) 0.024687(19) 0.594103(13) 0.03896(11) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C4 1.343(5) .
N2 C6 1.382(5) .
N2 C7 1.445(5) .
C4 H4 0.9500 .
C4 N1 1.318(5) .
C13 H13a 0.9900 .
C13 H13a 0.9900 2_655
C13 H13b 0.9900 2_655
C13 H13b 0.9900 .
C13 N3 1.473(4) 2_655
C13 N3 1.473(4) .
H13a H13b 0.0000 2_655
N3 C12 1.429(5) .
N3 C14 1.467(5) .
C11 C12 1.394(5) 2_655
C11 C10 1.391(6) .
C11 C14 1.527(5) .
C5 H5 0.9500 .
C5 C6 1.353(5) .
C5 N1 1.378(5) .
C6 H6 0.9500 .
C12 C7 1.414(5) .
C7 C8 1.384(6) 2_655
C2 H2 1.0000 .
C2 N1 1.487(5) .
C2 C3 1.498(7) .
C2 C1 1.514(6) .
C8 H8 0.9500 .
C8 C9 1.394(6) .
C3 H3a 0.9800 .
C3 H3b 0.9800 .
C3 H3c 0.9800 .
C10 H10 0.9500 .
C10 C9 1.378(6) .
C1 H1a 0.9800 .
C1 H1b 0.9800 .
C1 H1c 0.9800 .
C14 H14a 0.9900 .
C14 H14b 0.9900 .
C9 H9 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
C6 N2 C4 107.7(3) . .
C7 N2 C4 123.9(3) . .
C7 N2 C6 128.2(3) . .
H4 C4 N2 125.4(2) . .
N1 C4 N2 109.2(4) . .
N1 C4 H4 125.4(2) . .
H13a C13 H13a 110(5) . 2_655
H13b C13 H13a 0.0 2_655 .
H13b C13 H13a 110(5) 2_655 2_655
H13b C13 H13a 110(5) . .
H13b C13 H13a 0.0 . 2_655
H13b C13 H13b 110(5) 2_655 .
N3 C13 H13a 108.8(13) 2_655 2_655
N3 C13 H13a 108.8(13) 2_655 .
N3 C13 H13a 108.8(13) . .
N3 C13 H13a 108.8(13) . 2_655
N3 C13 H13b 108.8(13) 2_655 .
N3 C13 H13b 108.8(13) 2_655 2_655
N3 C13 H13b 108.8(13) . .
N3 C13 H13b 108.8(13) . 2_655
N3 C13 N3 111.1(5) 2_655 .
C12 N3 C13 111.0(3) . .
C14 N3 C13 108.2(3) . .
C14 N3 C12 111.2(3) . .
C10 C11 C12 120.4(4) . 2_655
C14 C11 C12 119.0(4) . 2_655
C14 C11 C10 120.6(4) . .
C6 C5 H5 126.4(2) . .
N1 C5 H5 126.4(2) . .
N1 C5 C6 107.2(3) . .
C5 C6 N2 107.2(3) . .
H6 C6 N2 126.4(2) . .
H6 C6 C5 126.4(2) . .
C11 C12 N3 122.8(3) 2_655 .
C7 C12 N3 119.8(3) . .
C7 C12 C11 117.4(4) . 2_655
C12 C7 N2 119.3(4) . .
C8 C7 N2 118.5(3) 2_655 .
C8 C7 C12 122.2(4) 2_655 .
N1 C2 H2 108.0(2) . .
C3 C2 H2 108.0(2) . .
C3 C2 N1 109.2(4) . .
C1 C2 H2 108.0(3) . .
C1 C2 N1 109.8(4) . .
C1 C2 C3 113.8(4) . .
H8 C8 C7 120.6(2) . 2_655
C9 C8 C7 118.9(4) . 2_655
C9 C8 H8 120.6(3) . .
C5 N1 C4 108.7(3) . .
C2 N1 C4 124.6(3) . .
C2 N1 C5 126.7(3) . .
H3a C3 C2 109.5 . .
H3b C3 C2 109.5 . .
H3b C3 H3a 109.5 . .
H3c C3 C2 109.5 . .
H3c C3 H3a 109.5 . .
H3c C3 H3b 109.5 . .
H10 C10 C11 119.4(2) . .
C9 C10 C11 121.2(4) . .
C9 C10 H10 119.4(3) . .
H1a C1 C2 109.5 . .
H1b C1 C2 109.5 . .
H1b C1 H1a 109.5 . .
H1c C1 C2 109.5 . .
H1c C1 H1a 109.5 . .
H1c C1 H1b 109.5 . .
C11 C14 N3 112.7(3) . .
H14a C14 N3 109.0(9) . .
H14a C14 C11 109.0(9) . .
H14b C14 N3 109.0(9) . .
H14b C14 C11 109.0(9) . .
H14b C14 H14a 108(4) . .
C10 C9 C8 119.9(4) . .
H9 C9 C8 120.1(3) . .
H9 C9 C10 120.1(3) . .

_database_code_depnum_ccdc_archive 'CCDC 979769'
#######################################################################
#
#                 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_7
_audit_creation_date             2014-04-21
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C33 H30 N8, 2(Cl), H2 O'
_chemical_formula_sum            'C33 H32 Cl2 N8 O'
_chemical_formula_weight         627.56
_chemical_oxdiff_formula         'C33 H32 Cl2 N8 O'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Cl 0.36843 0.69943 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.05239 0.03377 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.3442(10)
_cell_length_b                   12.5633(12)
_cell_length_c                   15.0779(16)
_cell_angle_alpha                84.154(8)
_cell_angle_beta                 79.178(10)
_cell_angle_gamma                87.113(9)
_cell_volume                     1543.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2700
_cell_measurement_temperature    150
_cell_measurement_theta_max      71.0985
_cell_measurement_theta_min      3.5353
_exptl_absorpt_coefficient_mu    2.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3458
_exptl_crystal_description       needle
_exptl_crystal_F_000             655.2367
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8560
_diffrn_reflns_theta_full        71.237702
_diffrn_reflns_theta_max         71.24
_diffrn_reflns_theta_min         3.54
_diffrn_ambient_temperature      153
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.865131
_diffrn_measured_fraction_theta_max 0.865131
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   36.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   50.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega -101.00  -29.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -180.0000 72

#__ type_ start__ end____ width___ exp.time_
  3 omega  -61.00   -6.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   82.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega  -14.00   72.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00  120.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega   76.00  122.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
  8 omega   42.00  102.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -134.0000   27.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega   56.00   86.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00   78.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 11 omega  103.00  129.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   76.00  107.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
 13 omega   89.00  132.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
 14 omega   49.00  105.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
 15 omega   53.00   93.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
 16 omega  100.00  177.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
 17 omega   83.00  171.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
 18 omega  101.00  178.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
 19 omega   39.00  102.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  150.0000 63

#__ type_ start__ end____ width___ exp.time_
 20 omega   47.00  141.00   1.0000    1.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -30.0000 94
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0314860000
_diffrn_orient_matrix_UB_12      -0.1117788000
_diffrn_orient_matrix_UB_13      0.0509762000
_diffrn_orient_matrix_UB_21      -0.0225765000
_diffrn_orient_matrix_UB_22      0.0492175000
_diffrn_orient_matrix_UB_23      0.0912090000
_diffrn_orient_matrix_UB_31      -0.1840317000
_diffrn_orient_matrix_UB_32      0.0171161000
_diffrn_orient_matrix_UB_33      -0.0002835000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3204
_reflns_number_total             5183
_reflns_odcompleteness_completeness 90.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.544832
_refine_diff_density_min         -0.505653
_refine_diff_density_rms         0.113318
_refine_ls_d_res_high            0.814185
_refine_ls_d_res_low             12.491575
_refine_ls_goodness_of_fit_ref   1.089649
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    55
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.114942
_refine_ls_R_factor_gt           0.072302
_refine_ls_restrained_S_all      1.089649
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+3.3671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.224077
_refine_special_details          ?
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_refinement_flags_posn
C1 C 0.8138(9) 1.4233(6) 0.3835(4) 0.091(2) Uani 1.000000 .
H1 H 0.8329(9) 1.3960(6) 0.3258(4) 0.109(3) Uiso 1.000000 R
C2 C 0.7659(9) 1.5276(6) 0.3876(4) 0.087(2) Uani 1.000000 .
H2 H 0.7560(9) 1.5726(6) 0.3342(4) 0.104(2) Uiso 1.000000 R
C3 C 0.7330(11) 1.5657(5) 0.4693(5) 0.108(3) Uani 1.000000 .
H3 H 0.6986(11) 1.6384(5) 0.4745(5) 0.129(3) Uiso 1.000000 R
C4 C 0.7495(10) 1.4986(5) 0.5458(4) 0.093(2) Uani 1.000000 .
H4 H 0.7239(10) 1.5237(5) 0.6043(4) 0.111(3) Uiso 1.000000 R
C5 C 0.8030(7) 1.3961(4) 0.5355(4) 0.0624(15) Uani 1.000000 .
C6 C 0.8310(9) 1.3202(5) 0.6163(4) 0.079(2) Uani 1.000000 .
H6a H 0.9432(13) 1.2886(15) 0.604(2) 0.095(2) Uiso 1.000000 R
H6b H 0.820(5) 1.3604(11) 0.6704(5) 0.095(2) Uiso 1.000000 R
C7 C 0.7424(7) 1.1341(4) 0.6135(4) 0.0617(14) Uani 1.000000 .
H7 H 0.8437(7) 1.1054(4) 0.5841(4) 0.0741(17) Uiso 1.000000 R
C8 C 0.5530(9) 1.2454(5) 0.6765(4) 0.0778(18) Uani 1.000000 .
H8 H 0.5005(9) 1.3089(5) 0.6984(4) 0.093(2) Uiso 1.000000 R
C9 C 0.4843(8) 1.1497(5) 0.6809(4) 0.0712(16) Uani 1.000000 .
H9 H 0.3745(8) 1.1330(5) 0.7064(4) 0.085(2) Uiso 1.000000 R
C10 C 0.5842(7) 0.9680(4) 0.6384(3) 0.0538(13) Uani 1.000000 .
C11 C 0.4540(7) 0.9347(4) 0.6048(3) 0.0610(14) Uani 1.000000 .
H11 H 0.3795(7) 0.9856(4) 0.5826(3) 0.0732(17) Uiso 1.000000 R
C12 C 0.4334(7) 0.8260(5) 0.6038(4) 0.0651(15) Uani 1.000000 .
H12 H 0.3447(7) 0.8021(5) 0.5805(4) 0.0781(18) Uiso 1.000000 R
C13 C 0.5421(7) 0.7523(4) 0.6367(3) 0.0619(14) Uani 1.000000 .
H13 H 0.5283(7) 0.6780(4) 0.6351(3) 0.0743(17) Uiso 1.000000 R
C14 C 0.6707(7) 0.7858(4) 0.6720(3) 0.0539(13) Uani 1.000000 .
C15 C 0.6936(6) 0.8946(4) 0.6726(3) 0.0516(12) Uani 1.000000 .
C16 C 0.7877(7) 0.7038(4) 0.7097(3) 0.0599(14) Uani 1.000000 .
H16a H 0.724(2) 0.648(2) 0.7498(15) 0.0719(17) Uiso 1.000000 R
H16b H 0.8557(19) 0.669(3) 0.6589(11) 0.0719(17) Uiso 1.000000 R
C17 C 0.9568(7) 0.8517(4) 0.7086(4) 0.0614(14) Uani 1.000000 .
H17a H 1.000(4) 0.8354(10) 0.6455(5) 0.0737(17) Uiso 1.000000 R
H17b H 1.040(3) 0.8791(5) 0.739(2) 0.0737(17) Uiso 1.000000 R
C18 C 0.8168(7) 0.7729(4) 0.8504(3) 0.0550(13) Uani 1.000000 .
C19 C 0.7596(7) 0.8755(4) 0.8719(4) 0.0579(13) Uani 1.000000 .
C20 C 0.7779(7) 0.9688(4) 0.7981(4) 0.0623(15) Uani 1.000000 .
H20a H 0.675(2) 1.013(2) 0.8024(6) 0.0748(18) Uiso 1.000000 R
H20b H 0.857(3) 1.020(2) 0.8091(4) 0.0748(18) Uiso 1.000000 R
C21 C 0.7935(7) 0.6902(4) 0.9209(4) 0.0581(14) Uani 1.000000 .
C22 C 0.7204(8) 0.7062(5) 1.0078(4) 0.0717(16) Uani 1.000000 .
H22 H 0.7063(8) 0.6479(5) 1.0536(4) 0.086(2) Uiso 1.000000 R
C23 C 0.6671(9) 0.8085(5) 1.0278(4) 0.0798(18) Uani 1.000000 .
H23 H 0.6167(9) 0.8213(5) 1.0879(4) 0.096(2) Uiso 1.000000 R
C24 C 0.6875(8) 0.8919(5) 0.9603(4) 0.0715(17) Uani 1.000000 .
H24 H 0.6515(8) 0.9621(5) 0.9746(4) 0.086(2) Uiso 1.000000 R
C25 C 0.7540(8) 0.5008(5) 0.9052(4) 0.0654(15) Uani 1.000000 .
H25 H 0.6387(8) 0.5025(5) 0.9235(4) 0.0785(18) Uiso 1.000000 R
C26 C 1.0100(8) 0.5481(5) 0.8715(4) 0.0769(18) Uani 1.000000 .
H26 H 1.1046(8) 0.5898(5) 0.8619(4) 0.092(2) Uiso 1.000000 R
C27 C 1.0058(8) 0.4434(6) 0.8597(4) 0.0774(18) Uani 1.000000 .
H27 H 1.0970(8) 0.3975(6) 0.8406(4) 0.093(2) Uiso 1.000000 R
C28 C 0.7805(9) 0.3080(5) 0.8830(4) 0.080(2) Uani 1.000000 .
H28a H 0.858(4) 0.2656(6) 0.8409(16) 0.096(2) Uiso 1.000000 R
H28b H 0.672(2) 0.316(2) 0.865(2) 0.096(2) Uiso 1.000000 R
C29 C 0.7626(8) 0.2518(4) 0.9775(4) 0.0671(16) Uani 1.000000 .
C30 C 0.8388(9) 0.1539(5) 0.9934(4) 0.0762(18) Uani 1.000000 .
H30 H 0.9093(9) 0.1211(5) 0.9460(4) 0.091(2) Uiso 1.000000 R
C31 C 0.8085(9) 0.1044(5) 1.0820(5) 0.0827(19) Uani 1.000000 .
H31 H 0.8562(9) 0.0360(5) 1.0961(5) 0.099(2) Uiso 1.000000 R
C33 C 0.6448(9) 0.2561(6) 1.1251(4) 0.0841(19) Uani 1.000000 .
H33 H 0.5797(9) 0.2926(6) 1.1721(4) 0.101(2) Uiso 1.000000 R
C32 C 0.7097(9) 0.1559(6) 1.1476(4) 0.0810(19) Uani 1.000000 .
H32 H 0.6857(9) 0.1233(6) 1.2081(4) 0.097(2) Uiso 1.000000 R
Cl Cl 0.4660(2) 0.47840(11) 0.78904(10) 0.0706(4) Uani 1.000000 .
Cl2A Cl 0.0849(2) 0.15925(17) 0.74657(14) 0.1047(7) Uani 1.000000 .
N1 N 0.8359(7) 1.3561(4) 0.4550(4) 0.0803(15) Uani 1.000000 .
N2 N 0.7127(7) 1.2342(4) 0.6344(3) 0.0673(13) Uani 1.000000 .
N3 N 0.6041(5) 1.0809(3) 0.6412(3) 0.0552(11) Uani 1.000000 .
N4 N 0.8264(5) 0.9336(3) 0.7065(3) 0.0563(11) Uani 1.000000 .
N5 N 0.8954(6) 0.7521(3) 0.7612(3) 0.0580(11) Uani 1.000000 .
N6 N 0.8499(6) 0.5838(4) 0.9002(3) 0.0607(12) Uani 1.000000 .
N7 N 0.8455(7) 0.4155(4) 0.8805(3) 0.0679(13) Uani 1.000000 .
N8 N 0.6688(7) 0.3040(4) 1.0414(3) 0.0791(15) Uani 1.000000 .
O1 O 0.1277(7) 0.0928(6) 0.5490(4) 0.154(3) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9500 .
C1 C2 1.355(9) .
C1 N1 1.335(8) .
C2 H2 0.9500 .
C2 C3 1.342(9) .
C3 H3 0.9500 .
C3 C4 1.383(8) .
C4 H4 0.9500 .
C4 C5 1.357(7) .
C5 C6 1.515(7) .
C5 N1 1.337(7) .
C6 H6a 0.9900 .
C6 H6b 0.9900 .
C6 N2 1.471(7) .
C7 H7 0.9500 .
C7 N2 1.327(7) .
C7 N3 1.339(7) .
C8 H8 0.9500 .
C8 C9 1.348(8) .
C8 N2 1.371(8) .
C9 H9 0.9500 .
C9 N3 1.378(7) .
C10 C11 1.381(7) .
C10 C15 1.395(7) .
C10 N3 1.441(6) .
C11 H11 0.9500 .
C11 C12 1.386(7) .
C12 H12 0.9500 .
C12 C13 1.385(7) .
C13 H13 0.9500 .
C13 C14 1.385(7) .
C14 C15 1.391(7) .
C14 C16 1.524(7) .
C15 N4 1.431(6) .
C16 H16a 0.9900 .
C16 H16b 0.9900 .
C16 N5 1.480(6) .
C17 H17a 0.9900 .
C17 H17b 0.9900 .
C17 N4 1.462(6) .
C17 N5 1.471(6) .
C18 C19 1.399(7) .
C18 C21 1.402(7) .
C18 N5 1.426(6) .
C19 C20 1.525(7) .
C19 C24 1.387(7) .
C20 H20a 0.9900 .
C20 H20b 0.9900 .
C20 N4 1.471(7) .
C21 C22 1.367(8) .
C21 N6 1.439(7) .
C22 H22 0.9500 .
C22 C23 1.383(8) .
C23 H23 0.9500 .
C23 C24 1.377(8) .
C24 H24 0.9500 .
C25 H25 0.9500 .
C25 N6 1.332(7) .
C25 N7 1.327(7) .
C26 H26 0.9500 .
C26 C27 1.348(9) .
C26 N6 1.391(7) .
C27 H27 0.9500 .
C27 N7 1.370(8) .
C28 H28a 0.9900 .
C28 H28b 0.9900 .
C28 C29 1.509(7) .
C28 N7 1.475(7) .
C29 C30 1.376(8) .
C29 N8 1.330(7) .
C30 H30 0.9500 .
C30 C31 1.398(8) .
C31 H31 0.9500 .
C31 C32 1.359(9) .
C33 H33 0.9500 .
C33 C32 1.381(9) .
C33 N8 1.326(7) .
C32 H32 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
C2 C1 H1 117.7(4) . .
N1 C1 H1 117.7(4) . .
N1 C1 C2 124.5(6) . .
H2 C2 C1 120.9(4) . .
C3 C2 C1 118.1(6) . .
C3 C2 H2 120.9(4) . .
H3 C3 C2 120.2(4) . .
C4 C3 C2 119.7(6) . .
C4 C3 H3 120.2(4) . .
H4 C4 C3 120.8(4) . .
C5 C4 C3 118.5(6) . .
C5 C4 H4 120.8(4) . .
C6 C5 C4 120.9(6) . .
N1 C5 C4 123.0(5) . .
N1 C5 C6 116.1(5) . .
H6a C6 C5 109.5(13) . .
H6b C6 C5 109.5(13) . .
H6b C6 H6a 108(5) . .
N2 C6 C5 110.8(5) . .
N2 C6 H6a 109.5(13) . .
N2 C6 H6b 109.5(13) . .
N2 C7 H7 126.1(4) . .
N3 C7 H7 126.1(3) . .
N3 C7 N2 107.8(5) . .
C9 C8 H8 126.3(4) . .
N2 C8 H8 126.3(3) . .
N2 C8 C9 107.3(5) . .
H9 C9 C8 126.6(4) . .
N3 C9 C8 106.8(6) . .
N3 C9 H9 126.6(3) . .
C15 C10 C11 121.3(5) . .
N3 C10 C11 119.4(5) . .
N3 C10 C15 119.3(5) . .
H11 C11 C10 120.4(3) . .
C12 C11 C10 119.2(5) . .
C12 C11 H11 120.4(3) . .
H12 C12 C11 120.0(3) . .
C13 C12 C11 120.0(5) . .
C13 C12 H12 120.0(3) . .
H13 C13 C12 119.7(3) . .
C14 C13 C12 120.7(5) . .
C14 C13 H13 119.7(3) . .
C15 C14 C13 119.8(5) . .
C16 C14 C13 120.2(5) . .
C16 C14 C15 119.9(5) . .
C14 C15 C10 118.9(5) . .
N4 C15 C10 118.9(5) . .
N4 C15 C14 122.2(5) . .
H16a C16 C14 109.1(10) . .
H16b C16 C14 109.1(10) . .
H16b C16 H16a 107(4) . .
N5 C16 C14 112.7(4) . .
N5 C16 H16a 109.1(10) . .
N5 C16 H16b 109.1(10) . .
H17b C17 H17a 114(5) . .
N4 C17 H17a 108.0(11) . .
N4 C17 H17b 108.0(11) . .
N5 C17 H17a 108.0(11) . .
N5 C17 H17b 108.0(11) . .
N5 C17 N4 111.4(5) . .
C21 C18 C19 117.0(5) . .
N5 C18 C19 122.2(4) . .
N5 C18 C21 120.8(5) . .
C20 C19 C18 119.8(5) . .
C24 C19 C18 119.8(5) . .
C24 C19 C20 120.3(5) . .
H20a C20 C19 110.2(10) . .
H20b C20 C19 110.2(10) . .
H20b C20 H20a 103(4) . .
N4 C20 C19 112.6(4) . .
N4 C20 H20a 110.2(10) . .
N4 C20 H20b 110.2(10) . .
C22 C21 C18 123.0(5) . .
N6 C21 C18 118.0(5) . .
N6 C21 C22 118.9(5) . .
H22 C22 C21 120.5(3) . .
C23 C22 C21 119.0(5) . .
C23 C22 H22 120.5(3) . .
H23 C23 C22 120.2(3) . .
C24 C23 C22 119.7(6) . .
C24 C23 H23 120.2(4) . .
C23 C24 C19 121.4(6) . .
H24 C24 C19 119.3(3) . .
H24 C24 C23 119.3(4) . .
N6 C25 H25 125.4(3) . .
N7 C25 H25 125.4(4) . .
N7 C25 N6 109.1(6) . .
C27 C26 H26 126.4(4) . .
N6 C26 H26 126.4(4) . .
N6 C26 C27 107.2(6) . .
H27 C27 C26 126.4(4) . .
N7 C27 C26 107.3(6) . .
N7 C27 H27 126.4(4) . .
H28b C28 H28a 111(6) . .
C29 C28 H28a 108.9(14) . .
C29 C28 H28b 108.9(14) . .
N7 C28 H28a 108.9(14) . .
N7 C28 H28b 108.9(14) . .
N7 C28 C29 110.3(5) . .
C30 C29 C28 121.0(6) . .
N8 C29 C28 114.7(5) . .
N8 C29 C30 124.2(5) . .
H30 C30 C29 121.3(4) . .
C31 C30 C29 117.4(6) . .
C31 C30 H30 121.3(4) . .
H31 C31 C30 120.5(4) . .
C32 C31 C30 118.9(6) . .
C32 C31 H31 120.5(4) . .
C32 C33 H33 118.3(4) . .
N8 C33 H33 118.3(4) . .
N8 C33 C32 123.3(6) . .
C33 C32 C31 119.1(6) . .
H32 C32 C31 120.5(4) . .
H32 C32 C33 120.5(4) . .
C5 N1 C1 116.2(5) . .
C7 N2 C6 126.0(6) . .
C8 N2 C6 124.7(5) . .
C8 N2 C7 109.2(5) . .
C9 N3 C7 108.9(5) . .
C10 N3 C7 126.5(5) . .
C10 N3 C9 124.4(5) . .
C17 N4 C15 110.9(4) . .
C20 N4 C15 113.2(4) . .
C20 N4 C17 108.1(4) . .
C17 N5 C16 107.8(4) . .
C18 N5 C16 113.5(4) . .
C18 N5 C17 110.4(4) . .
C25 N6 C21 125.0(5) . .
C26 N6 C21 127.4(5) . .
C26 N6 C25 107.6(5) . .
C27 N7 C25 108.8(5) . .
C28 N7 C25 123.7(6) . .
C28 N7 C27 127.3(6) . .
C33 N8 C29 117.0(6) . .

_database_code_depnum_ccdc_archive 'CCDC 979770'
