# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1044390'
_audit_update_record             
;
2015-01-20 deposited with the CCDC.
2015-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'2-(2-azidophenyl)-N-tert-butyl-N-phenyl-2-(phenylamino)acetimidamide '
_chemical_name_common            'alpha amino amidine'
_chemical_melting_point          402.15
_chemical_formula_moiety         'C24 H26 N6'
_chemical_formula_sum            'C24 H26 N6'
_chemical_formula_weight         398.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.920(2)
_cell_length_b                   9.0785(9)
_cell_length_c                   15.7191(19)
_cell_angle_alpha                90
_cell_angle_beta                 110.502(13)
_cell_angle_gamma                90
_cell_volume                     2261.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       cubic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.568
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85178
_exptl_absorpt_correction_T_max  1.00000
_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.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8360
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.583
_diffrn_reflns_theta_max         72.865
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4306
_reflns_number_gt                2272
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1662P)²+0.6144P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4306
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.0927
_refine_ls_wR_factor_ref         0.3260
_refine_ls_wR_factor_gt          0.2269
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.017

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.2173(2) 0.7727(3) 0.2744(2) 0.0564(8) Uani 1 1 d . . . . .
H1 H 0.2364 0.7284 0.3259 0.068 Uiso 1 1 calc R U . . .
N2 N 0.2344(2) 0.6299(4) 0.0636(2) 0.0610(8) Uani 1 1 d . . . . .
N1 N 0.2044(2) 0.5156(3) 0.1803(2) 0.0590(8) Uani 1 1 d . . . . .
H11 H 0.2026 0.5287 0.2338 0.071 Uiso 1 1 calc R U . . .
C2 C 0.2317(2) 0.6321(4) 0.1445(3) 0.0524(9) Uani 1 1 d . . . . .
C16 C 0.0862(2) 0.8609(4) 0.1627(3) 0.0615(10) Uani 1 1 d . . . . .
H4 H 0.0974 0.8078 0.1176 0.074 Uiso 1 1 calc R U . . .
C15 C 0.1426(2) 0.8562(4) 0.2513(2) 0.0504(8) Uani 1 1 d . . . . .
C9 C 0.3565(2) 0.7485(4) 0.2624(3) 0.0555(9) Uani 1 1 d . . . . .
C3 C 0.2644(3) 0.7541(4) 0.0301(3) 0.0597(10) Uani 1 1 d . . . . .
C14 C 0.4013(3) 0.6180(5) 0.2714(3) 0.0673(11) Uani 1 1 d . . . . .
H12 H 0.3733 0.5342 0.2418 0.081 Uiso 1 1 calc R U . . .
C20 C 0.1234(3) 0.9330(5) 0.3181(3) 0.0644(10) Uani 1 1 d . . . . .
H5 H 0.1597 0.9289 0.3782 0.077 Uiso 1 1 calc R U . . .
C8 C 0.2104(3) 0.8683(5) -0.0127(3) 0.0679(11) Uani 1 1 d . . . . .
H20 H 0.1544 0.8662 -0.0161 0.082 Uiso 1 1 calc R U . . .
C1 C 0.2623(2) 0.7616(4) 0.2104(3) 0.0524(9) Uani 1 1 d . . . . .
H3 H 0.2525 0.8527 0.1747 0.063 Uiso 1 1 calc R U . . .
C21 C 0.1776(3) 0.3703(4) 0.1404(3) 0.0633(10) Uani 1 1 d . . . . .
C10 C 0.4010(3) 0.8723(4) 0.3065(3) 0.0648(11) Uani 1 1 d . . . . .
C17 C 0.0131(3) 0.9446(5) 0.1409(3) 0.0715(12) Uani 1 1 d . . . . .
H8 H -0.0240 0.9484 0.0811 0.086 Uiso 1 1 calc R U . . .
N5 N 0.3932(3) 1.1159(5) 0.3331(4) 0.1040(16) Uani 1 1 d . . . . .
N4 N 0.3538(3) 1.0055(4) 0.2956(3) 0.0904(14) Uani 1 1 d . . . . .
C11 C 0.4878(3) 0.8628(5) 0.3584(4) 0.0801(14) Uani 1 1 d . . . . .
H1A H 0.5171 0.9460 0.3874 0.096 Uiso 1 1 calc R U . . .
C19 C 0.0504(3) 1.0155(5) 0.2950(3) 0.0720(12) Uani 1 1 d . . . . .
H9 H 0.0383 1.0677 0.3399 0.086 Uiso 1 1 calc R U . . .
C18 C -0.0048(3) 1.0218(5) 0.2070(3) 0.0747(12) Uani 1 1 d . . . . .
H14 H -0.0538 1.0778 0.1923 0.090 Uiso 1 1 calc R U . . .
C6 C 0.3219(4) 0.9877(6) -0.0473(3) 0.0845(15) Uani 1 1 d . . . . .
H30 H 0.3414 1.0669 -0.0719 0.101 Uiso 1 1 calc R U . . .
C4 C 0.3468(3) 0.7568(5) 0.0305(3) 0.0769(13) Uani 1 1 d . . . . .
H21 H 0.3833 0.6796 0.0569 0.092 Uiso 1 1 calc R U . . .
C5 C 0.3748(3) 0.8741(6) -0.0080(4) 0.0891(15) Uani 1 1 d . . . . .
H29 H 0.4300 0.8751 -0.0071 0.107 Uiso 1 1 calc R U . . .
C13 C 0.4861(3) 0.6083(5) 0.3226(3) 0.0744(12) Uani 1 1 d . . . . .
H17 H 0.5143 0.5189 0.3278 0.089 Uiso 1 1 calc R U . . .
C12 C 0.5286(3) 0.7314(6) 0.3659(4) 0.0793(14) Uani 1 1 d . . . . .
H25 H 0.5857 0.7251 0.4006 0.095 Uiso 1 1 calc R U . . .
C7 C 0.2392(4) 0.9850(5) -0.0503(3) 0.0777(13) Uani 1 1 d . . . . .
H27 H 0.2030 1.0620 -0.0776 0.093 Uiso 1 1 calc R U . . .
C24 C 0.1632(4) 0.2776(5) 0.2140(4) 0.0853(15) Uani 1 1 d . . . . .
H22A H 0.2146 0.2720 0.2656 0.128 Uiso 1 1 calc R U . . .
H22B H 0.1459 0.1803 0.1912 0.128 Uiso 1 1 calc R U . . .
H22C H 0.1199 0.3220 0.2319 0.128 Uiso 1 1 calc R U . . .
C23 C 0.2466(4) 0.3000(5) 0.1125(4) 0.0909(16) Uani 1 1 d . . . . .
H23A H 0.2512 0.3517 0.0611 0.136 Uiso 1 1 calc R U . . .
H23B H 0.2327 0.1988 0.0965 0.136 Uiso 1 1 calc R U . . .
H23C H 0.2994 0.3053 0.1622 0.136 Uiso 1 1 calc R U . . .
C22 C 0.0959(3) 0.3848(7) 0.0596(4) 0.0988(17) Uani 1 1 d . . . . .
H3CA H 0.0526 0.4233 0.0796 0.148 Uiso 1 1 calc R U . . .
H3CB H 0.0793 0.2898 0.0325 0.148 Uiso 1 1 calc R U . . .
H3CC H 0.1044 0.4505 0.0157 0.148 Uiso 1 1 calc R U . . .
N6 N 0.4207(4) 1.2250(6) 0.3624(5) 0.150(3) Uani 1 1 d . . . . .


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

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
N3 C15 1.408(4) . ?
N3 C1 1.461(5) . ?
N3 H1 0.8600 . ?
N2 C2 1.289(4) . ?
N2 C3 1.412(5) . ?
N1 C2 1.353(5) . ?
N1 C21 1.462(5) . ?
N1 H11 0.8600 . ?
C2 C1 1.532(5) . ?
C16 C15 1.387(5) . ?
C16 C17 1.388(6) . ?
C16 H4 0.9300 . ?
C15 C20 1.391(5) . ?
C9 C14 1.387(5) . ?
C9 C10 1.394(5) . ?
C9 C1 1.520(5) . ?
C3 C8 1.390(6) . ?
C3 C4 1.392(6) . ?
C14 C13 1.380(6) . ?
C14 H12 0.9300 . ?
C20 C19 1.381(6) . ?
C20 H5 0.9300 . ?
C8 C7 1.383(6) . ?
C8 H20 0.9300 . ?
C1 H3 0.9800 . ?
C21 C24 1.519(6) . ?
C21 C22 1.520(6) . ?
C21 C23 1.524(6) . ?
C10 C11 1.411(6) . ?
C10 N4 1.427(5) . ?
C17 C18 1.372(6) . ?
C17 H8 0.9300 . ?
N5 N6 1.121(6) . ?
N5 N4 1.233(6) . ?
C11 C12 1.363(6) . ?
C11 H1A 0.9300 . ?
C19 C18 1.372(6) . ?
C19 H9 0.9300 . ?
C18 H14 0.9300 . ?
C6 C5 1.363(7) . ?
C6 C7 1.384(7) . ?
C6 H30 0.9300 . ?
C4 C5 1.388(7) . ?
C4 H21 0.9300 . ?
C5 H29 0.9300 . ?
C13 C12 1.374(7) . ?
C13 H17 0.9300 . ?
C12 H25 0.9300 . ?
C7 H27 0.9300 . ?
C24 H22A 0.9600 . ?
C24 H22B 0.9600 . ?
C24 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C22 H3CA 0.9600 . ?
C22 H3CB 0.9600 . ?
C22 H3CC 0.9600 . ?

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
C15 N3 C1 119.8(3) . . ?
C15 N3 H1 120.1 . . ?
C1 N3 H1 120.1 . . ?
C2 N2 C3 119.8(3) . . ?
C2 N1 C21 128.8(3) . . ?
C2 N1 H11 115.6 . . ?
C21 N1 H11 115.6 . . ?
N2 C2 N1 122.2(4) . . ?
N2 C2 C1 124.0(3) . . ?
N1 C2 C1 113.8(3) . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H4 119.8 . . ?
C17 C16 H4 119.8 . . ?
C16 C15 C20 118.9(4) . . ?
C16 C15 N3 121.0(3) . . ?
C20 C15 N3 120.1(3) . . ?
C14 C9 C10 117.2(4) . . ?
C14 C9 C1 123.7(3) . . ?
C10 C9 C1 119.1(3) . . ?
C8 C3 C4 118.5(4) . . ?
C8 C3 N2 121.0(4) . . ?
C4 C3 N2 120.1(4) . . ?
C13 C14 C9 122.2(4) . . ?
C13 C14 H12 118.9 . . ?
C9 C14 H12 118.9 . . ?
C19 C20 C15 119.8(4) . . ?
C19 C20 H5 120.1 . . ?
C15 C20 H5 120.1 . . ?
C7 C8 C3 120.5(4) . . ?
C7 C8 H20 119.8 . . ?
C3 C8 H20 119.8 . . ?
N3 C1 C9 109.7(3) . . ?
N3 C1 C2 112.5(3) . . ?
C9 C1 C2 110.2(3) . . ?
N3 C1 H3 108.1 . . ?
C9 C1 H3 108.1 . . ?
C2 C1 H3 108.1 . . ?
N1 C21 C24 106.3(4) . . ?
N1 C21 C22 109.6(4) . . ?
C24 C21 C22 110.1(4) . . ?
N1 C21 C23 110.3(4) . . ?
C24 C21 C23 109.3(4) . . ?
C22 C21 C23 111.1(4) . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 N4 116.2(4) . . ?
C11 C10 N4 123.1(4) . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H8 119.8 . . ?
C16 C17 H8 119.8 . . ?
N6 N5 N4 172.0(6) . . ?
N5 N4 C10 116.5(4) . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H1A 120.1 . . ?
C10 C11 H1A 120.1 . . ?
C18 C19 C20 121.2(4) . . ?
C18 C19 H9 119.4 . . ?
C20 C19 H9 119.4 . . ?
C19 C18 C17 119.3(4) . . ?
C19 C18 H14 120.3 . . ?
C17 C18 H14 120.3 . . ?
C5 C6 C7 119.8(5) . . ?
C5 C6 H30 120.1 . . ?
C7 C6 H30 120.1 . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H21 119.8 . . ?
C3 C4 H21 119.8 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H29 119.7 . . ?
C4 C5 H29 119.7 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H17 120.2 . . ?
C14 C13 H17 120.2 . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 H25 119.7 . . ?
C13 C12 H25 119.7 . . ?
C8 C7 C6 120.2(5) . . ?
C8 C7 H27 119.9 . . ?
C6 C7 H27 119.9 . . ?
C21 C24 H22A 109.5 . . ?
C21 C24 H22B 109.5 . . ?
H22A C24 H22B 109.5 . . ?
C21 C24 H22C 109.5 . . ?
H22A C24 H22C 109.5 . . ?
H22B C24 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C22 H3CA 109.5 . . ?
C21 C22 H3CB 109.5 . . ?
H3CA C22 H3CB 109.5 . . ?
C21 C22 H3CC 109.5 . . ?
H3CA C22 H3CC 109.5 . . ?
H3CB C22 H3CC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C2 N1 -179.2(4) . . . . ?
C3 N2 C2 C1 -2.2(6) . . . . ?
C21 N1 C2 N2 2.8(6) . . . . ?
C21 N1 C2 C1 -174.5(4) . . . . ?
C17 C16 C15 C20 1.9(6) . . . . ?
C17 C16 C15 N3 -179.6(4) . . . . ?
C1 N3 C15 C16 35.7(5) . . . . ?
C1 N3 C15 C20 -145.7(4) . . . . ?
C2 N2 C3 C8 -87.3(5) . . . . ?
C2 N2 C3 C4 99.7(5) . . . . ?
C10 C9 C14 C13 1.0(7) . . . . ?
C1 C9 C14 C13 -176.9(4) . . . . ?
C16 C15 C20 C19 -1.8(6) . . . . ?
N3 C15 C20 C19 179.6(4) . . . . ?
C4 C3 C8 C7 -2.9(6) . . . . ?
N2 C3 C8 C7 -176.0(4) . . . . ?
C15 N3 C1 C9 147.8(3) . . . . ?
C15 N3 C1 C2 -89.1(4) . . . . ?
C14 C9 C1 N3 104.8(4) . . . . ?
C10 C9 C1 N3 -73.1(4) . . . . ?
C14 C9 C1 C2 -19.6(5) . . . . ?
C10 C9 C1 C2 162.5(4) . . . . ?
N2 C2 C1 N3 151.4(4) . . . . ?
N1 C2 C1 N3 -31.3(4) . . . . ?
N2 C2 C1 C9 -85.8(4) . . . . ?
N1 C2 C1 C9 91.4(4) . . . . ?
C2 N1 C21 C24 173.7(4) . . . . ?
C2 N1 C21 C22 -67.4(5) . . . . ?
C2 N1 C21 C23 55.2(6) . . . . ?
C14 C9 C10 C11 -0.6(7) . . . . ?
C1 C9 C10 C11 177.5(4) . . . . ?
C14 C9 C10 N4 179.4(4) . . . . ?
C1 C9 C10 N4 -2.6(6) . . . . ?
C15 C16 C17 C18 -1.0(7) . . . . ?
C9 C10 N4 N5 -178.8(5) . . . . ?
C11 C10 N4 N5 1.2(8) . . . . ?
C9 C10 C11 C12 -0.2(8) . . . . ?
N4 C10 C11 C12 179.8(5) . . . . ?
C15 C20 C19 C18 0.9(7) . . . . ?
C20 C19 C18 C17 0.0(7) . . . . ?
C16 C17 C18 C19 0.0(7) . . . . ?
C8 C3 C4 C5 2.4(7) . . . . ?
N2 C3 C4 C5 175.5(4) . . . . ?
C7 C6 C5 C4 -1.3(8) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
C9 C14 C13 C12 -0.6(7) . . . . ?
C10 C11 C12 C13 0.6(8) . . . . ?
C14 C13 C12 C11 -0.2(8) . . . . ?
C3 C8 C7 C6 1.4(7) . . . . ?
C5 C6 C7 C8 0.7(7) . . . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-4



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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1044391'
_audit_update_record             
;
2015-01-20 deposited with the CCDC.
2015-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'N-tert-butyl-N2-diphenyl-2H-indazole-3-carboximidamide '
_chemical_name_common            '3-amidino substituted 2H-indazole'
_chemical_melting_point          404.15
_chemical_formula_moiety         'C24 H24 N4 '
_chemical_formula_sum            'C24 H24 N4 '
_chemical_formula_weight         368.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5010(11)
_cell_length_b                   11.7613(15)
_cell_length_c                   18.1827(15)
_cell_angle_alpha                81.571(9)
_cell_angle_beta                 78.506(7)
_cell_angle_gamma                61.154(12)
_cell_volume                     2107.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       cubic
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.544
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69448
_exptl_absorpt_correction_T_max  1.00000
_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.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15456
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.299
_diffrn_reflns_theta_max         71.078
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             7849
_reflns_number_gt                4125
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+2.1832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7849
_refine_ls_number_parameters     513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.2400
_refine_ls_wR_factor_gt          0.2160
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2696(3) 0.1027(3) 0.4061(2) 0.0706(14) Uani 1 1 d . . . . .
H1 H 0.3261 0.0269 0.4218 0.085 Uiso 1 1 d R U . . .
N4 N 0.6183(4) 0.1357(4) 0.4629(2) 0.0784(15) Uani 1 1 d . . . . .
N3 N 0.4833(3) 0.1895(3) 0.4677(2) 0.0691(14) Uani 1 1 d . . . . .
N2 N 0.2195(4) 0.3188(3) 0.3869(2) 0.0697(14) Uani 1 1 d . . . . .
C1 C 0.3023(4) 0.2002(4) 0.4029(2) 0.0649(15) Uani 1 1 d . . . . .
C8 C 0.6654(5) 0.0586(4) 0.4039(3) 0.0749(16) Uani 1 1 d . . . . .
C3 C 0.5614(4) 0.0636(4) 0.3732(3) 0.0705(15) Uani 1 1 d . . . . .
C15 C 0.2609(4) 0.4161(4) 0.3709(2) 0.0649(15) Uani 1 1 d . . . . .
C9 C 0.4018(5) 0.2823(4) 0.5240(3) 0.0728(16) Uani 1 1 d . . . . .
C2 C 0.4433(4) 0.1502(4) 0.4154(2) 0.0657(15) Uani 1 1 d . . . . .
C20 C 0.1819(5) 0.5323(4) 0.4054(3) 0.0841(17) Uani 1 1 d . . . . .
H42 H 0.1081 0.5421 0.4413 0.101 Uiso 1 1 calc R U . . .
C19 C 0.2130(6) 0.6334(5) 0.3865(3) 0.103(2) Uani 1 1 d . . . . .
H43 H 0.1602 0.7109 0.4104 0.123 Uiso 1 1 calc R U . . .
C16 C 0.3678(5) 0.4056(4) 0.3172(3) 0.0770(16) Uani 1 1 d . . . . .
H51 H 0.4215 0.3281 0.2935 0.092 Uiso 1 1 calc R U . . .
C17 C 0.3969(6) 0.5077(5) 0.2981(3) 0.0931(19) Uani 1 1 d . . . . .
H55 H 0.4689 0.4994 0.2612 0.112 Uiso 1 1 calc R U . . .
C4 C 0.5900(6) -0.0061(5) 0.3097(3) 0.0879(17) Uani 1 1 d . . . . .
H62 H 0.5212 -0.0021 0.2882 0.106 Uiso 1 1 calc R U . . .
C21 C 0.1484(5) 0.1132(4) 0.3850(3) 0.0752(16) Uani 1 1 d . . . . .
C23 C 0.1689(6) -0.0257(5) 0.3899(4) 0.107(2) Uani 1 1 d . . . . .
H70A H 0.1756 -0.0610 0.4408 0.161 Uiso 1 1 calc R U . . .
H70B H 0.2500 -0.0780 0.3578 0.161 Uiso 1 1 calc R U . . .
H70C H 0.0941 -0.0257 0.3740 0.161 Uiso 1 1 calc R U . . .
C7 C 0.8007(5) -0.0181(5) 0.3735(3) 0.0929(18) Uani 1 1 d . . . . .
H75 H 0.8703 -0.0219 0.3941 0.111 Uiso 1 1 calc R U . . .
C11 C 0.2042(6) 0.3821(6) 0.6120(3) 0.102(2) Uani 1 1 d . . . . .
H79 H 0.1221 0.3883 0.6359 0.123 Uiso 1 1 calc R U . . .
C22 C 0.1337(6) 0.1710(6) 0.3051(3) 0.108(2) Uani 1 1 d . . . . .
H85A H 0.2144 0.1212 0.2721 0.163 Uiso 1 1 calc R U . . .
H85B H 0.1181 0.2593 0.3027 0.163 Uiso 1 1 calc R U . . .
H85C H 0.0593 0.1693 0.2900 0.163 Uiso 1 1 calc R U . . .
C10 C 0.2819(5) 0.2906(5) 0.5593(3) 0.0843(17) Uani 1 1 d . . . . .
H88 H 0.2526 0.2350 0.5480 0.101 Uiso 1 1 calc R U . . .
C12 C 0.2470(7) 0.4629(6) 0.6290(4) 0.112(2) Uani 1 1 d . . . . .
H90 H 0.1938 0.5250 0.6641 0.135 Uiso 1 1 calc R U . . .
C14 C 0.4467(6) 0.3626(6) 0.5411(3) 0.101(2) Uani 1 1 d . . . . .
H93 H 0.5287 0.3566 0.5173 0.121 Uiso 1 1 calc R U . . .
C6 C 0.8254(6) -0.0859(5) 0.3133(4) 0.102(2) Uani 1 1 d . . . . .
H99 H 0.9139 -0.1384 0.2929 0.122 Uiso 1 1 calc R U . . .
C24 C 0.0252(5) 0.1949(6) 0.4392(4) 0.112(2) Uani 1 1 d . . . . .
H10D H 0.0153 0.2811 0.4373 0.168 Uiso 1 1 calc R U . . .
H10E H 0.0355 0.1561 0.4893 0.168 Uiso 1 1 calc R U . . .
H10F H -0.0530 0.1992 0.4251 0.168 Uiso 1 1 calc R U . . .
C5 C 0.7205(6) -0.0793(5) 0.2806(3) 0.101(2) Uani 1 1 d . . . . .
H104 H 0.7411 -0.1257 0.2385 0.121 Uiso 1 1 calc R U . . .
C18 C 0.3191(6) 0.6220(5) 0.3336(4) 0.105(2) Uani 1 1 d . . . . .
H109 H 0.3390 0.6909 0.3216 0.126 Uiso 1 1 calc R U . . .
C13 C 0.3677(7) 0.4529(6) 0.5947(4) 0.122(2) Uani 1 1 d . . . . .
H110 H 0.3976 0.5073 0.6073 0.146 Uiso 1 1 calc R U . . .
N7 N 0.8042(3) 0.6574(3) 0.0315(2) 0.0672(14) Uani 1 1 d . . . . .
N5 N 0.8779(3) 0.3363(3) 0.0989(2) 0.0751(14) Uani 1 1 d . . . . .
H4 H 0.9591 0.3223 0.0833 0.090 Uiso 1 1 d R U . . .
N6 N 0.6559(3) 0.4944(3) 0.1161(2) 0.0716(14) Uani 1 1 d . . . . .
N8 N 0.8609(4) 0.7342(4) 0.0349(2) 0.0784(15) Uani 1 1 d . . . . .
C44 C 0.4468(4) 0.6790(5) 0.0932(3) 0.0813(17) Uani 1 1 d . . . . .
H14 H 0.4398 0.6316 0.0591 0.098 Uiso 1 1 calc R U . . .
C33 C 0.7171(4) 0.6941(4) -0.0240(2) 0.0682(15) Uani 1 1 d . . . . .
C39 C 0.5583(4) 0.6242(4) 0.1289(3) 0.0671(15) Uani 1 1 d . . . . .
C32 C 0.9328(4) 0.6772(5) 0.0926(3) 0.0746(16) Uani 1 1 d . . . . .
C27 C 0.9230(4) 0.5649(5) 0.1237(3) 0.0708(15) Uani 1 1 d . . . . .
C26 C 0.8382(4) 0.5551(4) 0.0831(2) 0.0649(15) Uani 1 1 d . . . . .
C25 C 0.7803(4) 0.4629(4) 0.0992(2) 0.0652(15) Uani 1 1 d . . . . .
C43 C 0.3453(5) 0.8030(5) 0.1070(3) 0.0940(19) Uani 1 1 d . . . . .
H41 H 0.2713 0.8391 0.0817 0.113 Uiso 1 1 calc R U . . .
C47 C 0.7838(6) 0.2051(6) 0.0673(4) 0.111(2) Uani 1 1 d . . . . .
H44A H 0.6968 0.2795 0.0672 0.166 Uiso 1 1 calc R U . . .
H44B H 0.7737 0.1281 0.0819 0.166 Uiso 1 1 calc R U . . .
H44C H 0.8344 0.1975 0.0177 0.166 Uiso 1 1 calc R U . . .
C31 C 1.0084(5) 0.7205(6) 0.1224(4) 0.0948(19) Uani 1 1 d . . . . .
H45 H 1.0155 0.7946 0.1022 0.114 Uiso 1 1 calc R U . . .
C45 C 0.8574(5) 0.2213(4) 0.1227(3) 0.0794(17) Uani 1 1 d . . . . .
C40 C 0.5646(5) 0.6949(5) 0.1809(3) 0.0796(16) Uani 1 1 d . . . . .
H48 H 0.6382 0.6594 0.2065 0.096 Uiso 1 1 calc R U . . .
C36 C 0.5480(6) 0.7687(7) -0.1287(3) 0.100(2) Uani 1 1 d . . . . .
H53 H 0.4904 0.7941 -0.1641 0.120 Uiso 1 1 calc R U . . .
C38 C 0.7113(5) 0.6012(5) -0.0583(3) 0.0780(16) Uani 1 1 d . . . . .
H57 H 0.7645 0.5134 -0.0465 0.094 Uiso 1 1 calc R U . . .
C37 C 0.6251(5) 0.6398(6) -0.1107(3) 0.0902(18) Uani 1 1 d . . . . .
H58 H 0.6197 0.5775 -0.1340 0.108 Uiso 1 1 calc R U . . .
C28 C 0.9887(5) 0.4940(6) 0.1856(3) 0.0895(18) Uani 1 1 d . . . . .
H64 H 0.9828 0.4196 0.2066 0.107 Uiso 1 1 calc R U . . .
C34 C 0.6395(5) 0.8246(5) -0.0416(3) 0.0926(18) Uani 1 1 d . . . . .
H66 H 0.6438 0.8874 -0.0182 0.111 Uiso 1 1 calc R U . . .
C46 C 0.9982(5) 0.1066(5) 0.1212(4) 0.110(2) Uani 1 1 d . . . . .
H80A H 1.0447 0.0972 0.0707 0.165 Uiso 1 1 calc R U . . .
H80B H 0.9919 0.0286 0.1394 0.165 Uiso 1 1 calc R U . . .
H80C H 1.0464 0.1219 0.1528 0.165 Uiso 1 1 calc R U . . .
C35 C 0.5556(6) 0.8603(6) -0.0945(4) 0.107(2) Uani 1 1 d . . . . .
H83 H 0.5034 0.9480 -0.1071 0.129 Uiso 1 1 calc R U . . .
C30 C 1.0702(6) 0.6484(7) 0.1821(4) 0.107(2) Uani 1 1 d . . . . .
H95 H 1.1208 0.6743 0.2028 0.129 Uiso 1 1 calc R U . . .
C29 C 1.0602(5) 0.5358(7) 0.2136(3) 0.104(2) Uani 1 1 d . . . . .
H101 H 1.1039 0.4897 0.2544 0.125 Uiso 1 1 calc R U . . .
C42 C 0.3531(5) 0.8728(5) 0.1577(4) 0.102(2) Uani 1 1 d . . . . .
H86 H 0.2862 0.9576 0.1673 0.122 Uiso 1 1 d R U . . .
C41 C 0.4611(6) 0.8190(6) 0.1950(3) 0.098(2) Uani 1 1 d . . . . .
H106 H 0.4656 0.8661 0.2302 0.117 Uiso 1 1 calc R U . . .
C48 C 0.7810(6) 0.2333(5) 0.2020(3) 0.105(2) Uani 1 1 d . . . . .
H10G H 0.8262 0.2496 0.2350 0.158 Uiso 1 1 calc R U . . .
H10H H 0.7768 0.1539 0.2188 0.158 Uiso 1 1 calc R U . . .
H10I H 0.6916 0.3040 0.2023 0.158 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.359(5) . ?
N1 C21 1.463(5) . ?
N1 H1 0.8600 . ?
N4 N3 1.354(5) . ?
N4 C8 1.359(6) . ?
N3 C2 1.356(5) . ?
N3 C9 1.440(6) . ?
N2 C1 1.283(5) . ?
N2 C15 1.413(5) . ?
C1 C2 1.487(6) . ?
C8 C3 1.392(6) . ?
C8 C7 1.410(7) . ?
C3 C2 1.396(6) . ?
C3 C4 1.406(6) . ?
C15 C16 1.374(6) . ?
C15 C20 1.383(6) . ?
C9 C10 1.362(6) . ?
C9 C14 1.370(6) . ?
C20 C19 1.379(6) . ?
C20 H42 0.9300 . ?
C19 C18 1.358(7) . ?
C19 H43 0.9300 . ?
C16 C17 1.376(6) . ?
C16 H51 0.9300 . ?
C17 C18 1.374(7) . ?
C17 H55 0.9300 . ?
C4 C5 1.358(7) . ?
C4 H62 0.9300 . ?
C21 C22 1.516(7) . ?
C21 C24 1.520(7) . ?
C21 C23 1.525(6) . ?
C23 H70A 0.9600 . ?
C23 H70B 0.9600 . ?
C23 H70C 0.9600 . ?
C7 C6 1.352(7) . ?
C7 H75 0.9300 . ?
C11 C12 1.356(8) . ?
C11 C10 1.381(7) . ?
C11 H79 0.9300 . ?
C22 H85A 0.9600 . ?
C22 H85B 0.9600 . ?
C22 H85C 0.9600 . ?
C10 H88 0.9300 . ?
C12 C13 1.360(8) . ?
C12 H90 0.9300 . ?
C14 C13 1.386(8) . ?
C14 H93 0.9300 . ?
C6 C5 1.412(8) . ?
C6 H99 0.9300 . ?
C24 H10D 0.9600 . ?
C24 H10E 0.9600 . ?
C24 H10F 0.9600 . ?
C5 H104 0.9300 . ?
C18 H109 0.9300 . ?
C13 H110 0.9300 . ?
N7 C26 1.357(5) . ?
N7 N8 1.359(5) . ?
N7 C33 1.437(5) . ?
N5 C25 1.364(5) . ?
N5 C45 1.472(5) . ?
N5 H4 0.8600 . ?
N6 C25 1.275(5) . ?
N6 C39 1.411(5) . ?
N8 C32 1.356(6) . ?
C44 C39 1.376(6) . ?
C44 C43 1.379(6) . ?
C44 H14 0.9300 . ?
C33 C38 1.369(6) . ?
C33 C34 1.380(6) . ?
C39 C40 1.382(6) . ?
C32 C27 1.406(6) . ?
C32 C31 1.416(7) . ?
C27 C26 1.390(6) . ?
C27 C28 1.410(6) . ?
C26 C25 1.493(6) . ?
C43 C42 1.363(7) . ?
C43 H41 0.9300 . ?
C47 C45 1.524(7) . ?
C47 H44A 0.9600 . ?
C47 H44B 0.9600 . ?
C47 H44C 0.9600 . ?
C31 C30 1.364(8) . ?
C31 H45 0.9300 . ?
C45 C48 1.519(7) . ?
C45 C46 1.525(6) . ?
C40 C41 1.387(7) . ?
C40 H48 0.9300 . ?
C36 C35 1.366(8) . ?
C36 C37 1.365(7) . ?
C36 H53 0.9300 . ?
C38 C37 1.382(7) . ?
C38 H57 0.9300 . ?
C37 H58 0.9300 . ?
C28 C29 1.345(7) . ?
C28 H64 0.9300 . ?
C34 C35 1.374(7) . ?
C34 H66 0.9300 . ?
C46 H80A 0.9600 . ?
C46 H80B 0.9600 . ?
C46 H80C 0.9600 . ?
C35 H83 0.9300 . ?
C30 C29 1.411(8) . ?
C30 H95 0.9300 . ?
C29 H101 0.9300 . ?
C42 C41 1.361(7) . ?
C42 H86 0.9354 . ?
C41 H106 0.9300 . ?
C48 H10G 0.9600 . ?
C48 H10H 0.9600 . ?
C48 H10I 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C21 126.7(4) . . ?
C1 N1 H1 116.8 . . ?
C21 N1 H1 116.5 . . ?
N3 N4 C8 103.7(4) . . ?
C2 N3 N4 113.7(4) . . ?
C2 N3 C9 128.5(4) . . ?
N4 N3 C9 117.7(4) . . ?
C1 N2 C15 121.3(4) . . ?
N2 C1 N1 121.5(4) . . ?
N2 C1 C2 126.5(4) . . ?
N1 C1 C2 111.9(4) . . ?
N4 C8 C3 111.6(4) . . ?
N4 C8 C7 127.3(5) . . ?
C3 C8 C7 121.1(5) . . ?
C8 C3 C2 105.6(4) . . ?
C8 C3 C4 120.0(5) . . ?
C2 C3 C4 134.3(5) . . ?
C16 C15 C20 118.6(4) . . ?
C16 C15 N2 123.0(4) . . ?
C20 C15 N2 118.1(4) . . ?
C10 C9 C14 120.5(5) . . ?
C10 C9 N3 120.7(4) . . ?
C14 C9 N3 118.8(4) . . ?
N3 C2 C3 105.5(4) . . ?
N3 C2 C1 125.9(4) . . ?
C3 C2 C1 128.4(4) . . ?
C19 C20 C15 119.7(5) . . ?
C19 C20 H42 120.1 . . ?
C15 C20 H42 120.1 . . ?
C18 C19 C20 121.2(5) . . ?
C18 C19 H43 119.4 . . ?
C20 C19 H43 119.4 . . ?
C15 C16 C17 121.2(4) . . ?
C15 C16 H51 119.4 . . ?
C17 C16 H51 119.4 . . ?
C18 C17 C16 119.8(5) . . ?
C18 C17 H55 120.1 . . ?
C16 C17 H55 120.1 . . ?
C5 C4 C3 118.5(5) . . ?
C5 C4 H62 120.8 . . ?
C3 C4 H62 120.8 . . ?
N1 C21 C22 110.1(4) . . ?
N1 C21 C24 110.6(4) . . ?
C22 C21 C24 110.6(5) . . ?
N1 C21 C23 105.6(4) . . ?
C22 C21 C23 109.9(4) . . ?
C24 C21 C23 110.0(4) . . ?
C21 C23 H70A 109.5 . . ?
C21 C23 H70B 109.5 . . ?
H70A C23 H70B 109.5 . . ?
C21 C23 H70C 109.5 . . ?
H70A C23 H70C 109.5 . . ?
H70B C23 H70C 109.5 . . ?
C6 C7 C8 117.6(5) . . ?
C6 C7 H75 121.2 . . ?
C8 C7 H75 121.2 . . ?
C12 C11 C10 120.3(6) . . ?
C12 C11 H79 119.8 . . ?
C10 C11 H79 119.8 . . ?
C21 C22 H85A 109.5 . . ?
C21 C22 H85B 109.5 . . ?
H85A C22 H85B 109.5 . . ?
C21 C22 H85C 109.5 . . ?
H85A C22 H85C 109.5 . . ?
H85B C22 H85C 109.5 . . ?
C9 C10 C11 119.7(5) . . ?
C9 C10 H88 120.1 . . ?
C11 C10 H88 120.1 . . ?
C11 C12 C13 119.9(6) . . ?
C11 C12 H90 120.1 . . ?
C13 C12 H90 120.1 . . ?
C9 C14 C13 118.8(6) . . ?
C9 C14 H93 120.6 . . ?
C13 C14 H93 120.6 . . ?
C7 C6 C5 121.8(5) . . ?
C7 C6 H99 119.1 . . ?
C5 C6 H99 119.1 . . ?
C21 C24 H10D 109.5 . . ?
C21 C24 H10E 109.5 . . ?
H10D C24 H10E 109.5 . . ?
C21 C24 H10F 109.5 . . ?
H10D C24 H10F 109.5 . . ?
H10E C24 H10F 109.5 . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 H104 119.5 . . ?
C6 C5 H104 119.5 . . ?
C19 C18 C17 119.4(5) . . ?
C19 C18 H109 120.3 . . ?
C17 C18 H109 120.3 . . ?
C12 C13 C14 120.7(6) . . ?
C12 C13 H110 119.7 . . ?
C14 C13 H110 119.7 . . ?
C26 N7 N8 113.8(4) . . ?
C26 N7 C33 128.8(4) . . ?
N8 N7 C33 117.4(4) . . ?
C25 N5 C45 126.2(4) . . ?
C25 N5 H4 117.0 . . ?
C45 N5 H4 116.8 . . ?
C25 N6 C39 121.3(4) . . ?
C32 N8 N7 103.4(4) . . ?
C39 C44 C43 121.1(5) . . ?
C39 C44 H14 119.5 . . ?
C43 C44 H14 119.5 . . ?
C38 C33 C34 120.9(5) . . ?
C38 C33 N7 120.5(4) . . ?
C34 C33 N7 118.6(4) . . ?
C44 C39 C40 118.5(4) . . ?
C44 C39 N6 119.0(4) . . ?
C40 C39 N6 122.3(4) . . ?
N8 C32 C27 111.8(4) . . ?
N8 C32 C31 127.3(5) . . ?
C27 C32 C31 120.9(5) . . ?
C26 C27 C32 105.2(4) . . ?
C26 C27 C28 134.8(5) . . ?
C32 C27 C28 120.0(5) . . ?
N7 C26 C27 105.9(4) . . ?
N7 C26 C25 126.3(4) . . ?
C27 C26 C25 127.3(4) . . ?
N6 C25 N5 122.2(4) . . ?
N6 C25 C26 125.7(4) . . ?
N5 C25 C26 111.9(4) . . ?
C42 C43 C44 120.1(5) . . ?
C42 C43 H41 119.9 . . ?
C44 C43 H41 119.9 . . ?
C45 C47 H44A 109.5 . . ?
C45 C47 H44B 109.5 . . ?
H44A C47 H44B 109.5 . . ?
C45 C47 H44C 109.5 . . ?
H44A C47 H44C 109.5 . . ?
H44B C47 H44C 109.5 . . ?
C30 C31 C32 116.9(6) . . ?
C30 C31 H45 121.6 . . ?
C32 C31 H45 121.6 . . ?
N5 C45 C48 110.3(4) . . ?
N5 C45 C47 109.7(4) . . ?
C48 C45 C47 111.3(4) . . ?
N5 C45 C46 105.2(4) . . ?
C48 C45 C46 109.8(4) . . ?
C47 C45 C46 110.3(5) . . ?
C39 C40 C41 119.9(5) . . ?
C39 C40 H48 120.1 . . ?
C41 C40 H48 120.1 . . ?
C35 C36 C37 119.7(5) . . ?
C35 C36 H53 120.1 . . ?
C37 C36 H53 120.1 . . ?
C33 C38 C37 119.1(5) . . ?
C33 C38 H57 120.5 . . ?
C37 C38 H57 120.5 . . ?
C36 C37 C38 120.6(5) . . ?
C36 C37 H58 119.7 . . ?
C38 C37 H58 119.7 . . ?
C29 C28 C27 118.7(6) . . ?
C29 C28 H64 120.6 . . ?
C27 C28 H64 120.6 . . ?
C35 C34 C33 118.8(5) . . ?
C35 C34 H66 120.6 . . ?
C33 C34 H66 120.6 . . ?
C45 C46 H80A 109.5 . . ?
C45 C46 H80B 109.5 . . ?
H80A C46 H80B 109.5 . . ?
C45 C46 H80C 109.5 . . ?
H80A C46 H80C 109.5 . . ?
H80B C46 H80C 109.5 . . ?
C36 C35 C34 120.9(5) . . ?
C36 C35 H83 119.5 . . ?
C34 C35 H83 119.5 . . ?
C31 C30 C29 122.3(6) . . ?
C31 C30 H95 118.8 . . ?
C29 C30 H95 118.8 . . ?
C28 C29 C30 121.2(6) . . ?
C28 C29 H101 119.4 . . ?
C30 C29 H101 119.4 . . ?
C43 C42 C41 119.7(5) . . ?
C43 C42 H86 121.5 . . ?
C41 C42 H86 118.8 . . ?
C42 C41 C40 120.8(5) . . ?
C42 C41 H106 119.6 . . ?
C40 C41 H106 119.6 . . ?
C45 C48 H10G 109.5 . . ?
C45 C48 H10H 109.5 . . ?
H10G C48 H10H 109.5 . . ?
C45 C48 H10I 109.5 . . ?
H10G C48 H10I 109.5 . . ?
H10H C48 H10I 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N4 N3 C2 0.3(5) . . . . ?
C8 N4 N3 C9 -177.4(4) . . . . ?
C15 N2 C1 N1 -168.8(4) . . . . ?
C15 N2 C1 C2 7.2(7) . . . . ?
C21 N1 C1 N2 6.9(7) . . . . ?
C21 N1 C1 C2 -169.7(4) . . . . ?
N3 N4 C8 C3 -0.7(5) . . . . ?
N3 N4 C8 C7 178.5(5) . . . . ?
N4 C8 C3 C2 0.8(5) . . . . ?
C7 C8 C3 C2 -178.4(4) . . . . ?
N4 C8 C3 C4 177.7(4) . . . . ?
C7 C8 C3 C4 -1.6(7) . . . . ?
C1 N2 C15 C16 53.4(6) . . . . ?
C1 N2 C15 C20 -133.3(5) . . . . ?
C2 N3 C9 C10 36.7(7) . . . . ?
N4 N3 C9 C10 -146.0(4) . . . . ?
C2 N3 C9 C14 -143.0(5) . . . . ?
N4 N3 C9 C14 34.3(6) . . . . ?
N4 N3 C2 C3 0.2(5) . . . . ?
C9 N3 C2 C3 177.6(4) . . . . ?
N4 N3 C2 C1 -174.9(4) . . . . ?
C9 N3 C2 C1 2.5(7) . . . . ?
C8 C3 C2 N3 -0.6(5) . . . . ?
C4 C3 C2 N3 -176.8(5) . . . . ?
C8 C3 C2 C1 174.4(4) . . . . ?
C4 C3 C2 C1 -1.9(8) . . . . ?
N2 C1 C2 N3 58.1(7) . . . . ?
N1 C1 C2 N3 -125.6(4) . . . . ?
N2 C1 C2 C3 -115.9(5) . . . . ?
N1 C1 C2 C3 60.4(6) . . . . ?
C16 C15 C20 C19 -1.1(7) . . . . ?
N2 C15 C20 C19 -174.7(5) . . . . ?
C15 C20 C19 C18 0.8(9) . . . . ?
C20 C15 C16 C17 0.2(7) . . . . ?
N2 C15 C16 C17 173.5(4) . . . . ?
C15 C16 C17 C18 0.8(8) . . . . ?
C8 C3 C4 C5 1.3(7) . . . . ?
C2 C3 C4 C5 177.0(5) . . . . ?
C1 N1 C21 C22 54.8(6) . . . . ?
C1 N1 C21 C24 -67.7(6) . . . . ?
C1 N1 C21 C23 173.3(5) . . . . ?
N4 C8 C7 C6 -178.8(5) . . . . ?
C3 C8 C7 C6 0.4(8) . . . . ?
C14 C9 C10 C11 1.0(8) . . . . ?
N3 C9 C10 C11 -178.7(5) . . . . ?
C12 C11 C10 C9 -0.4(9) . . . . ?
C10 C11 C12 C13 -0.7(10) . . . . ?
C10 C9 C14 C13 -0.4(9) . . . . ?
N3 C9 C14 C13 179.3(5) . . . . ?
C8 C7 C6 C5 1.2(8) . . . . ?
C3 C4 C5 C6 0.2(8) . . . . ?
C7 C6 C5 C4 -1.5(9) . . . . ?
C20 C19 C18 C17 0.2(10) . . . . ?
C16 C17 C18 C19 -1.0(9) . . . . ?
C11 C12 C13 C14 1.4(11) . . . . ?
C9 C14 C13 C12 -0.8(10) . . . . ?
C26 N7 N8 C32 -0.8(5) . . . . ?
C33 N7 N8 C32 178.5(4) . . . . ?
C26 N7 C33 C38 -34.6(6) . . . . ?
N8 N7 C33 C38 146.2(4) . . . . ?
C26 N7 C33 C34 145.2(5) . . . . ?
N8 N7 C33 C34 -34.0(6) . . . . ?
C43 C44 C39 C40 1.9(7) . . . . ?
C43 C44 C39 N6 176.5(4) . . . . ?
C25 N6 C39 C44 130.9(5) . . . . ?
C25 N6 C39 C40 -54.7(6) . . . . ?
N7 N8 C32 C27 1.1(5) . . . . ?
N7 N8 C32 C31 -177.5(4) . . . . ?
N8 C32 C27 C26 -1.0(5) . . . . ?
C31 C32 C27 C26 177.7(4) . . . . ?
N8 C32 C27 C28 -178.6(4) . . . . ?
C31 C32 C27 C28 0.1(7) . . . . ?
N8 N7 C26 C27 0.2(5) . . . . ?
C33 N7 C26 C27 -179.0(4) . . . . ?
N8 N7 C26 C25 172.5(4) . . . . ?
C33 N7 C26 C25 -6.7(7) . . . . ?
C32 C27 C26 N7 0.5(5) . . . . ?
C28 C27 C26 N7 177.5(5) . . . . ?
C32 C27 C26 C25 -171.7(4) . . . . ?
C28 C27 C26 C25 5.3(8) . . . . ?
C39 N6 C25 N5 168.8(4) . . . . ?
C39 N6 C25 C26 -6.7(7) . . . . ?
C45 N5 C25 N6 -5.1(7) . . . . ?
C45 N5 C25 C26 171.0(4) . . . . ?
N7 C26 C25 N6 -54.2(7) . . . . ?
C27 C26 C25 N6 116.5(5) . . . . ?
N7 C26 C25 N5 129.9(4) . . . . ?
C27 C26 C25 N5 -59.5(6) . . . . ?
C39 C44 C43 C42 -1.1(8) . . . . ?
N8 C32 C31 C30 178.4(5) . . . . ?
C27 C32 C31 C30 0.0(7) . . . . ?
C25 N5 C45 C48 -54.3(6) . . . . ?
C25 N5 C45 C47 68.7(6) . . . . ?
C25 N5 C45 C46 -172.7(5) . . . . ?
C44 C39 C40 C41 -1.2(7) . . . . ?
N6 C39 C40 C41 -175.5(4) . . . . ?
C34 C33 C38 C37 -0.6(7) . . . . ?
N7 C33 C38 C37 179.2(4) . . . . ?
C35 C36 C37 C38 -0.2(9) . . . . ?
C33 C38 C37 C36 0.7(8) . . . . ?
C26 C27 C28 C29 -176.7(5) . . . . ?
C32 C27 C28 C29 -0.1(7) . . . . ?
C38 C33 C34 C35 0.0(8) . . . . ?
N7 C33 C34 C35 -179.8(5) . . . . ?
C37 C36 C35 C34 -0.4(9) . . . . ?
C33 C34 C35 C36 0.5(9) . . . . ?
C32 C31 C30 C29 -0.1(8) . . . . ?
C27 C28 C29 C30 -0.1(8) . . . . ?
C31 C30 C29 C28 0.2(9) . . . . ?
C44 C43 C42 C41 -0.5(9) . . . . ?
C43 C42 C41 C40 1.2(9) . . . . ?
C39 C40 C41 C42 -0.4(8) . . . . ?

_refine_diff_density_max         0.122
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.024

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
