# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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/. 
# 
# 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_nr3003
_database_code_depnum_ccdc_archive 'CCDC 936124'
_audit_update_record             
;
2013-04-29 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;N1,N1'-(buta-1,3-diyne-1,4-diylbis(4,1-phenylene))bis
(N1-(4-(dimethylamino)phenyl)-N4,N4-dimethylbenzene-1,4-diamine)
;
_chemical_name_common            ?
_chemical_formula_moiety         'C48 H48 N6'
_chemical_formula_sum            'C48 H48 N6'
_chemical_compound_source        Synthetic
_exptl_crystal_recrystallization_method 'Slow evaporation in DMSO/EtOAc'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark yellow'

_diffrn_ambient_temperature      120(2)
_chemical_formula_weight         708.92

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.85327(19)
_cell_length_b                   11.5888(3)
_cell_length_c                   34.7326(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.691(2)
_cell_angle_gamma                90
_cell_volume                     3946.48(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7928
_cell_measurement_theta_min      3.9980
_cell_measurement_theta_max      72.1200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             1512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    0.546
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Numerical absorption correction based on gaussian integration over
   a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   microsource
_diffrn_source_type              'Agilent Technologies SuperNova'
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3147
_diffrn_reflns_number            46934
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         4.023
_diffrn_reflns_theta_max         76.254
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8129
_reflns_number_gt                5482
_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       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2011)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008) and local programs'


_vrf_PLAT220_nr3003              
;
PROBLEM: Large Non-Solvent    C     Ueq(max)/Ueq(min) ...        4.2 Ratio
RESPONSE: Discussed in _refine_special_details.
;

_vrf_DIFMN02_nr3003              
;
PROBLEM  The minimum difference density is < -0.1*ZMAX*0.75
RESPONSE: See _refine_special_details
;


_refine_special_details          
;
Atom C48 shows a larger than usual displacement ellipsoid, but a disorder 
model brought no improvement in refinement.  The largest peak is 0.54 
electrons located 1.13 A from C47.  The deepest hole is 0.56 electrons 
located 0.5 A from H48c.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0763P)²+1.5275P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8129
_refine_ls_number_parameters     495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1717
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_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 0.08294(17) 0.18003(18) 0.20431(5) 0.0379(5) Uani 1 1 d . . . . .
N2 N -0.39324(18) 0.44885(19) 0.20938(6) 0.0449(5) Uani 1 1 d . . . . .
N3 N 0.1299(2) -0.0724(2) 0.06679(6) 0.0519(6) Uani 1 1 d . . . . .
N4 N 1.1746(2) 0.25341(19) 0.53754(5) 0.0453(5) Uani 1 1 d . . . . .
N5 N 1.0760(3) 0.5398(2) 0.66281(7) 0.0696(8) Uani 1 1 d . . . . .
C1 C 0.18483(19) 0.1823(2) 0.23527(6) 0.0344(5) Uani 1 1 d . . . . .
C2 C 0.1909(2) 0.2714(2) 0.26248(6) 0.0370(5) Uani 1 1 d . . . . .
H2 H 0.1244 0.3310 0.2599 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2922(2) 0.2745(2) 0.29318(6) 0.0388(5) Uani 1 1 d . . . . .
H3 H 0.2943 0.3359 0.3113 0.047 Uiso 1 1 calc R U . . .
C4 C 0.3911(2) 0.1881(2) 0.29762(6) 0.0375(5) Uani 1 1 d . . . . .
C5 C 0.3827(2) 0.0979(2) 0.27098(7) 0.0418(6) Uani 1 1 d . . . . .
H5 H 0.4475 0.0371 0.2740 0.050 Uiso 1 1 calc R U . . .
C6 C 0.2820(2) 0.0949(2) 0.24032(6) 0.0391(5) Uani 1 1 d . . . . .
H6 H 0.2790 0.0326 0.2225 0.047 Uiso 1 1 calc R U . . .
C7 C 0.4985(2) 0.1912(2) 0.32824(6) 0.0410(5) Uani 1 1 d . . . . .
C8 C 0.5885(2) 0.1911(2) 0.35430(6) 0.0425(6) Uani 1 1 d . . . . .
C9 C -0.03807(19) 0.2482(2) 0.20538(6) 0.0347(5) Uani 1 1 d . . . . .
C10 C -0.0680(2) 0.3364(2) 0.17905(6) 0.0370(5) Uani 1 1 d . . . . .
H10 H -0.0072 0.3523 0.1601 0.044 Uiso 1 1 calc R U . . .
C11 C -0.1854(2) 0.4017(2) 0.17988(6) 0.0359(5) Uani 1 1 d . . . . .
H11 H -0.2042 0.4616 0.1614 0.043 Uiso 1 1 calc R U . . .
C12 C -0.2771(2) 0.3809(2) 0.20757(6) 0.0364(5) Uani 1 1 d . . . . .
C13 C -0.2470(2) 0.2900(2) 0.23362(6) 0.0403(5) Uani 1 1 d . . . . .
H13 H -0.3079 0.2727 0.2524 0.048 Uiso 1 1 calc R U . . .
C14 C -0.1294(2) 0.2250(2) 0.23238(6) 0.0390(5) Uani 1 1 d . . . . .
H14 H -0.1110 0.1637 0.2503 0.047 Uiso 1 1 calc R U . . .
C15 C -0.4367(3) 0.5217(3) 0.17667(8) 0.0580(7) Uani 1 1 d . . . . .
H15A H -0.4522 0.4743 0.1533 0.087 Uiso 1 1 calc R U . . .
H15B H -0.3659 0.5791 0.1732 0.087 Uiso 1 1 calc R U . . .
H15C H -0.5215 0.5612 0.1813 0.087 Uiso 1 1 calc R U . . .
C16 C -0.4993(3) 0.4060(3) 0.23182(10) 0.0639(8) Uani 1 1 d . . . . .
H16A H -0.5752 0.4610 0.2302 0.096 Uiso 1 1 calc R U . . .
H16B H -0.4624 0.3969 0.2589 0.096 Uiso 1 1 calc R U . . .
H16C H -0.5320 0.3313 0.2215 0.096 Uiso 1 1 calc R U . . .
C17 C 0.0973(2) 0.1150(2) 0.17001(6) 0.0350(5) Uani 1 1 d . . . . .
C18 C 0.2156(2) 0.1198(2) 0.15132(6) 0.0401(5) Uani 1 1 d . . . . .
H18 H 0.2900 0.1659 0.1618 0.048 Uiso 1 1 calc R U . . .
C19 C 0.2264(2) 0.0584(2) 0.11756(7) 0.0431(6) Uani 1 1 d . . . . .
H19 H 0.3089 0.0622 0.1056 0.052 Uiso 1 1 calc R U . . .
C20 C 0.1183(2) -0.0092(2) 0.10063(6) 0.0395(5) Uani 1 1 d . . . . .
C21 C -0.0010(2) -0.0130(2) 0.11975(6) 0.0382(5) Uani 1 1 d . . . . .
H21 H -0.0766 -0.0576 0.1092 0.046 Uiso 1 1 calc R U . . .
C22 C -0.0097(2) 0.0476(2) 0.15385(6) 0.0380(5) Uani 1 1 d . . . . .
H22 H -0.0908 0.0428 0.1664 0.046 Uiso 1 1 calc R U . . .
C23 C 0.2314(3) -0.0394(3) 0.04247(8) 0.0599(8) Uani 1 1 d . . . . .
H23A H 0.2270 -0.0907 0.0199 0.090 Uiso 1 1 calc R U . . .
H23B H 0.3217 -0.0452 0.0569 0.090 Uiso 1 1 calc R U . . .
H23C H 0.2153 0.0403 0.0338 0.090 Uiso 1 1 calc R U . . .
C24 C 0.0082(3) -0.1231(3) 0.04749(7) 0.0593(8) Uani 1 1 d . . . . .
H24A H -0.0579 -0.0621 0.0398 0.089 Uiso 1 1 calc R U . . .
H24B H -0.0314 -0.1768 0.0651 0.089 Uiso 1 1 calc R U . . .
H24C H 0.0310 -0.1648 0.0244 0.089 Uiso 1 1 calc R U . . .
C25 C 1.0740(2) 0.2308(2) 0.50754(6) 0.0413(6) Uani 1 1 d . . . . .
C26 C 1.1041(3) 0.1794(3) 0.47301(8) 0.0655(9) Uani 1 1 d . . . . .
H26 H 1.1943 0.1540 0.4703 0.079 Uiso 1 1 calc R U . . .
C27 C 1.0028(3) 0.1654(3) 0.44280(8) 0.0667(9) Uani 1 1 d . . . . .
H27 H 1.0254 0.1314 0.4194 0.080 Uiso 1 1 calc R U . . .
C28 C 0.8702(2) 0.1992(2) 0.44567(6) 0.0411(5) Uani 1 1 d . . . . .
C29 C 0.8402(2) 0.2486(3) 0.47996(7) 0.0471(6) Uani 1 1 d . . . . .
H29 H 0.7493 0.2717 0.4828 0.056 Uiso 1 1 calc R U . . .
C30 C 0.9401(2) 0.2651(3) 0.51019(7) 0.0486(6) Uani 1 1 d . . . . .
H30 H 0.9168 0.3006 0.5333 0.058 Uiso 1 1 calc R U . . .
C31 C 0.7693(2) 0.1911(2) 0.41311(6) 0.0436(6) Uani 1 1 d . . . . .
C32 C 0.6861(2) 0.1902(2) 0.38534(6) 0.0424(6) Uani 1 1 d . . . . .
C33 C 1.1462(2) 0.3270(2) 0.56888(6) 0.0415(6) Uani 1 1 d . . . . .
C34 C 1.1201(2) 0.4426(2) 0.56319(7) 0.0441(6) Uani 1 1 d . . . . .
H34 H 1.1188 0.4742 0.5379 0.053 Uiso 1 1 calc R U . . .
C35 C 1.0956(3) 0.5135(2) 0.59393(7) 0.0470(6) Uani 1 1 d . . . . .
H35 H 1.0763 0.5929 0.5894 0.056 Uiso 1 1 calc R U . . .
C36 C 1.0991(3) 0.4692(2) 0.63166(7) 0.0462(6) Uani 1 1 d . . . . .
C37 C 1.1272(3) 0.3526(2) 0.63688(7) 0.0480(6) Uani 1 1 d . . . . .
H37 H 1.1312 0.3204 0.6621 0.058 Uiso 1 1 calc R U . . .
C38 C 1.1493(3) 0.2828(2) 0.60601(7) 0.0476(6) Uani 1 1 d . . . . .
H38 H 1.1671 0.2030 0.6103 0.057 Uiso 1 1 calc R U . . .
C39 C 1.0300(4) 0.6549(3) 0.65592(9) 0.0728(9) Uani 1 1 d . . . . .
H39A H 1.0961 0.6969 0.6419 0.109 Uiso 1 1 calc R U . . .
H39B H 1.0209 0.6932 0.6807 0.109 Uiso 1 1 calc R U . . .
H39C H 0.9413 0.6539 0.6404 0.109 Uiso 1 1 calc R U . . .
C40 C 1.0972(3) 0.4959(3) 0.70049(8) 0.0663(9) Uani 1 1 d . . . . .
H40A H 1.0307 0.4347 0.7038 0.099 Uiso 1 1 calc R U . . .
H40B H 1.0860 0.5579 0.7191 0.099 Uiso 1 1 calc R U . . .
H40C H 1.1897 0.4642 0.7049 0.099 Uiso 1 1 calc R U . . .
C41 C 1.3025(2) 0.1933(2) 0.54234(6) 0.0408(5) Uani 1 1 d . . . . .
C42 C 1.4192(2) 0.2544(2) 0.55480(7) 0.0479(6) Uani 1 1 d . . . . .
H42 H 1.4150 0.3361 0.5568 0.058 Uiso 1 1 calc R U . . .
C43 C 1.5414(2) 0.1985(3) 0.56433(7) 0.0497(6) Uani 1 1 d . . . . .
H43 H 1.6197 0.2426 0.5731 0.060 Uiso 1 1 calc R U . . .
C44 C 1.5530(2) 0.0816(3) 0.56149(7) 0.0494(7) Uani 1 1 d . . . . .
C45 C 1.4365(3) 0.0205(3) 0.54680(9) 0.0626(8) Uani 1 1 d . . . . .
H45 H 1.4424 -0.0605 0.5431 0.075 Uiso 1 1 calc R U . . .
C46 C 1.3131(3) 0.0757(3) 0.53757(9) 0.0584(8) Uani 1 1 d . . . . .
H46 H 1.2352 0.0323 0.5279 0.070 Uiso 1 1 calc R U . . .
N6 N 1.6770(2) 0.0220(2) 0.57191(7) 0.0580(6) Uani 1 1 d . . . . .
C47 C 1.7903(3) 0.0958(4) 0.58771(14) 0.1032(15) Uani 1 1 d . . . . .
H47A H 1.8735 0.0494 0.5923 0.155 Uiso 1 1 calc R U . . .
H47B H 1.7684 0.1298 0.6122 0.155 Uiso 1 1 calc R U . . .
H47C H 1.8046 0.1575 0.5692 0.155 Uiso 1 1 calc R U . . .
C48 C 1.6664(4) -0.0750(5) 0.59526(17) 0.144(3) Uani 1 1 d . . . . .
H48A H 1.5995 -0.0602 0.6138 0.216 Uiso 1 1 calc R U . . .
H48B H 1.7554 -0.0917 0.6093 0.216 Uiso 1 1 calc R U . . .
H48C H 1.6367 -0.1414 0.5790 0.216 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 1.397(2) . ?
N1 C9 1.434(3) . ?
N1 C17 1.429(3) . ?
N2 C12 1.395(3) . ?
N2 C15 1.446(3) . ?
N2 C16 1.452(3) . ?
N3 C20 1.399(3) . ?
N3 C23 1.424(3) . ?
N3 C24 1.439(3) . ?
N4 C25 1.390(3) . ?
N4 C33 1.432(3) . ?
N4 C41 1.435(3) . ?
N5 C36 1.393(3) . ?
N5 C39 1.421(4) . ?
N5 C40 1.401(4) . ?
C1 C2 1.397(3) . ?
C1 C6 1.393(3) . ?
C2 H2 0.950 . ?
C2 C3 1.387(3) . ?
C3 H3 0.950 . ?
C3 C4 1.395(3) . ?
C4 C5 1.392(3) . ?
C4 C7 1.424(3) . ?
C5 H5 0.950 . ?
C5 C6 1.382(3) . ?
C6 H6 0.950 . ?
C7 C8 1.203(3) . ?
C8 C32 1.371(3) . ?
C9 C10 1.383(3) . ?
C9 C14 1.389(3) . ?
C10 H10 0.950 . ?
C10 C11 1.386(3) . ?
C11 H11 0.950 . ?
C11 C12 1.405(3) . ?
C12 C13 1.401(3) . ?
C13 H13 0.950 . ?
C13 C14 1.386(3) . ?
C14 H14 0.950 . ?
C15 H15A 0.980 . ?
C15 H15B 0.980 . ?
C15 H15C 0.980 . ?
C16 H16A 0.980 . ?
C16 H16B 0.980 . ?
C16 H16C 0.980 . ?
C17 C18 1.391(3) . ?
C17 C22 1.385(3) . ?
C18 H18 0.950 . ?
C18 C19 1.384(3) . ?
C19 H19 0.950 . ?
C19 C20 1.404(3) . ?
C20 C21 1.407(3) . ?
C21 H21 0.950 . ?
C21 C22 1.387(3) . ?
C22 H22 0.950 . ?
C23 H23A 0.980 . ?
C23 H23B 0.980 . ?
C23 H23C 0.980 . ?
C24 H24A 0.980 . ?
C24 H24B 0.980 . ?
C24 H24C 0.980 . ?
C25 C26 1.397(4) . ?
C25 C30 1.390(3) . ?
C26 H26 0.950 . ?
C26 C27 1.384(3) . ?
C27 H27 0.950 . ?
C27 C28 1.377(3) . ?
C28 C29 1.380(3) . ?
C28 C31 1.433(3) . ?
C29 H29 0.950 . ?
C29 C30 1.379(3) . ?
C30 H30 0.950 . ?
C31 C32 1.202(3) . ?
C33 C34 1.374(4) . ?
C33 C38 1.385(3) . ?
C34 H34 0.950 . ?
C34 C35 1.387(3) . ?
C35 H35 0.950 . ?
C35 C36 1.405(3) . ?
C36 C37 1.388(4) . ?
C37 H37 0.950 . ?
C37 C38 1.377(4) . ?
C38 H38 0.950 . ?
C39 H39A 0.980 . ?
C39 H39B 0.980 . ?
C39 H39C 0.980 . ?
C40 H40A 0.980 . ?
C40 H40B 0.980 . ?
C40 H40C 0.980 . ?
C41 C42 1.383(3) . ?
C41 C46 1.378(4) . ?
C42 H42 0.950 . ?
C42 C43 1.379(4) . ?
C43 H43 0.950 . ?
C43 C44 1.364(4) . ?
C44 C45 1.401(4) . ?
C44 N6 1.418(3) . ?
C45 H45 0.950 . ?
C45 C46 1.383(4) . ?
C46 H46 0.950 . ?
N6 C47 1.469(4) . ?
N6 C48 1.397(5) . ?
C47 H47A 0.980 . ?
C47 H47B 0.980 . ?
C47 H47C 0.980 . ?
C48 H48A 0.980 . ?
C48 H48B 0.980 . ?
C48 H48C 0.980 . ?

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 C9 120.38(18) . . ?
C1 N1 C17 121.93(17) . . ?
C9 N1 C17 117.63(16) . . ?
C12 N2 C15 118.3(2) . . ?
C12 N2 C16 117.9(2) . . ?
C15 N2 C16 116.6(2) . . ?
C20 N3 C23 118.6(2) . . ?
C20 N3 C24 118.1(2) . . ?
C23 N3 C24 115.8(2) . . ?
C25 N4 C33 120.24(19) . . ?
C25 N4 C41 123.2(2) . . ?
C33 N4 C41 115.87(17) . . ?
C36 N5 C39 119.6(2) . . ?
C36 N5 C40 119.4(3) . . ?
C39 N5 C40 120.9(3) . . ?
N1 C1 C2 120.9(2) . . ?
N1 C1 C6 121.0(2) . . ?
C2 C1 C6 118.00(18) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.2(2) . . ?
H2 C2 C3 119.4 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(2) . . ?
H3 C3 C4 119.7 . . ?
C3 C4 C5 118.04(19) . . ?
C3 C4 C7 121.5(2) . . ?
C5 C4 C7 120.4(2) . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.5(2) . . ?
H5 C5 C6 119.3 . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C4 C7 C8 178.5(3) . . ?
C7 C8 C32 177.0(3) . . ?
N1 C9 C10 120.9(2) . . ?
N1 C9 C14 120.5(2) . . ?
C10 C9 C14 118.6(2) . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 120.9(2) . . ?
H10 C10 C11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.0(2) . . ?
H11 C11 C12 119.5 . . ?
N2 C12 C11 121.3(2) . . ?
N2 C12 C13 121.2(2) . . ?
C11 C12 C13 117.5(2) . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(2) . . ?
H13 C13 C14 119.6 . . ?
C9 C14 C13 121.0(2) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 121.67(19) . . ?
N1 C17 C22 120.08(19) . . ?
C18 C17 C22 118.2(2) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.9(2) . . ?
H18 C18 C19 119.6 . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.5(2) . . ?
H19 C19 C20 119.2 . . ?
N3 C20 C19 121.5(2) . . ?
N3 C20 C21 121.5(2) . . ?
C19 C20 C21 117.0(2) . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.8(2) . . ?
H21 C21 C22 119.6 . . ?
C17 C22 C21 121.5(2) . . ?
C17 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N4 C25 C26 121.9(2) . . ?
N4 C25 C30 120.5(2) . . ?
C26 C25 C30 117.5(2) . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.2(2) . . ?
H26 C26 C27 119.9 . . ?
C26 C27 H27 119.0 . . ?
C26 C27 C28 122.0(2) . . ?
H27 C27 C28 119.0 . . ?
C27 C28 C29 117.8(2) . . ?
C27 C28 C31 120.9(2) . . ?
C29 C28 C31 121.2(2) . . ?
C28 C29 H29 119.4 . . ?
C28 C29 C30 121.2(2) . . ?
H29 C29 C30 119.4 . . ?
C25 C30 C29 121.3(2) . . ?
C25 C30 H30 119.3 . . ?
C29 C30 H30 119.3 . . ?
C28 C31 C32 176.6(3) . . ?
C8 C32 C31 178.2(3) . . ?
N4 C33 C34 121.3(2) . . ?
N4 C33 C38 120.0(2) . . ?
C34 C33 C38 118.8(2) . . ?
C33 C34 H34 119.6 . . ?
C33 C34 C35 120.7(2) . . ?
H34 C34 C35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C34 C35 C36 120.8(3) . . ?
H35 C35 C36 119.6 . . ?
N5 C36 C35 121.3(3) . . ?
N5 C36 C37 121.1(2) . . ?
C35 C36 C37 117.6(2) . . ?
C36 C37 H37 119.5 . . ?
C36 C37 C38 121.0(2) . . ?
H37 C37 C38 119.5 . . ?
C33 C38 C37 121.1(2) . . ?
C33 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
N5 C39 H39A 109.5 . . ?
N5 C39 H39B 109.5 . . ?
N5 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N5 C40 H40A 109.5 . . ?
N5 C40 H40B 109.5 . . ?
N5 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N4 C41 C42 118.7(2) . . ?
N4 C41 C46 122.8(2) . . ?
C42 C41 C46 118.3(2) . . ?
C41 C42 H42 119.6 . . ?
C41 C42 C43 120.9(3) . . ?
H42 C42 C43 119.6 . . ?
C42 C43 H43 119.1 . . ?
C42 C43 C44 121.8(2) . . ?
H43 C43 C44 119.1 . . ?
C43 C44 C45 117.2(2) . . ?
C43 C44 N6 122.7(2) . . ?
C45 C44 N6 120.0(3) . . ?
C44 C45 H45 119.3 . . ?
C44 C45 C46 121.3(3) . . ?
H45 C45 C46 119.3 . . ?
C41 C46 C45 120.3(3) . . ?
C41 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
C44 N6 C47 114.6(3) . . ?
C44 N6 C48 115.3(2) . . ?
C47 N6 C48 110.5(3) . . ?
N6 C47 H47A 109.5 . . ?
N6 C47 H47B 109.5 . . ?
N6 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
N6 C48 H48A 109.5 . . ?
N6 C48 H48B 109.5 . . ?
N6 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 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
C9 N1 C1 C2 -17.7(3) . . . . ?
C9 N1 C1 C6 161.2(2) . . . . ?
C17 N1 C1 C2 159.3(2) . . . . ?
C17 N1 C1 C6 -21.8(3) . . . . ?
N1 C1 C2 C3 -179.7(2) . . . . ?
C6 C1 C2 C3 1.4(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C2 C3 C4 C7 178.1(2) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
C7 C4 C5 C6 -177.9(2) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
N1 C1 C6 C5 179.9(2) . . . . ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C1 N1 C9 C10 116.1(2) . . . . ?
C1 N1 C9 C14 -65.5(3) . . . . ?
C17 N1 C9 C10 -61.1(3) . . . . ?
C17 N1 C9 C14 117.3(2) . . . . ?
N1 C9 C10 C11 179.51(19) . . . . ?
C14 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C15 N2 C12 C11 15.5(3) . . . . ?
C15 N2 C12 C13 -165.2(2) . . . . ?
C16 N2 C12 C11 165.1(2) . . . . ?
C16 N2 C12 C13 -15.6(3) . . . . ?
C10 C11 C12 N2 177.8(2) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
N2 C12 C13 C14 -178.1(2) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C12 C13 C14 C9 0.1(3) . . . . ?
N1 C9 C14 C13 -179.8(2) . . . . ?
C10 C9 C14 C13 -1.3(3) . . . . ?
C1 N1 C17 C18 -47.2(3) . . . . ?
C1 N1 C17 C22 134.8(2) . . . . ?
C9 N1 C17 C18 129.9(2) . . . . ?
C9 N1 C17 C22 -48.1(3) . . . . ?
N1 C17 C18 C19 -178.4(2) . . . . ?
C22 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C20 1.0(4) . . . . ?
C23 N3 C20 C19 -20.8(4) . . . . ?
C23 N3 C20 C21 160.8(3) . . . . ?
C24 N3 C20 C19 -169.3(3) . . . . ?
C24 N3 C20 C21 12.4(4) . . . . ?
C18 C19 C20 N3 -179.2(2) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
N3 C20 C21 C22 178.2(2) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
N1 C17 C22 C21 177.4(2) . . . . ?
C18 C17 C22 C21 -0.7(4) . . . . ?
C20 C21 C22 C17 0.9(4) . . . . ?
C33 N4 C25 C26 166.9(3) . . . . ?
C33 N4 C25 C30 -9.4(4) . . . . ?
C41 N4 C25 C26 -22.7(4) . . . . ?
C41 N4 C25 C30 161.0(3) . . . . ?
N4 C25 C26 C27 -175.6(3) . . . . ?
C30 C25 C26 C27 0.8(5) . . . . ?
C25 C26 C27 C28 -1.0(6) . . . . ?
C26 C27 C28 C29 0.2(5) . . . . ?
C26 C27 C28 C31 175.6(3) . . . . ?
C27 C28 C29 C30 0.9(4) . . . . ?
C31 C28 C29 C30 -174.6(3) . . . . ?
C28 C29 C30 C25 -1.1(4) . . . . ?
N4 C25 C30 C29 176.7(3) . . . . ?
C26 C25 C30 C29 0.3(4) . . . . ?
C25 N4 C33 C34 -66.5(3) . . . . ?
C25 N4 C33 C38 115.8(3) . . . . ?
C41 N4 C33 C34 122.5(3) . . . . ?
C41 N4 C33 C38 -55.3(3) . . . . ?
N4 C33 C34 C35 -178.6(2) . . . . ?
C38 C33 C34 C35 -0.8(4) . . . . ?
C33 C34 C35 C36 1.0(4) . . . . ?
C39 N5 C36 C35 8.7(4) . . . . ?
C39 N5 C36 C37 -171.7(3) . . . . ?
C40 N5 C36 C35 -172.0(3) . . . . ?
C40 N5 C36 C37 7.6(4) . . . . ?
C34 C35 C36 N5 179.3(3) . . . . ?
C34 C35 C36 C37 -0.2(4) . . . . ?
N5 C36 C37 C38 179.7(3) . . . . ?
C35 C36 C37 C38 -0.7(4) . . . . ?
C36 C37 C38 C33 0.9(4) . . . . ?
N4 C33 C38 C37 177.7(2) . . . . ?
C34 C33 C38 C37 -0.1(4) . . . . ?
C25 N4 C41 C42 141.8(3) . . . . ?
C25 N4 C41 C46 -42.7(4) . . . . ?
C33 N4 C41 C42 -47.4(3) . . . . ?
C33 N4 C41 C46 128.1(3) . . . . ?
N4 C41 C42 C43 172.1(2) . . . . ?
C46 C41 C42 C43 -3.6(4) . . . . ?
C41 C42 C43 C44 0.8(4) . . . . ?
C42 C43 C44 C45 2.8(4) . . . . ?
C42 C43 C44 N6 -178.6(2) . . . . ?
C43 C44 C45 C46 -3.5(4) . . . . ?
N6 C44 C45 C46 177.9(3) . . . . ?
N4 C41 C46 C45 -172.7(3) . . . . ?
C42 C41 C46 C45 2.9(4) . . . . ?
C44 C45 C46 C41 0.7(5) . . . . ?
C43 C44 N6 C47 2.7(4) . . . . ?
C43 C44 N6 C48 132.7(4) . . . . ?
C45 C44 N6 C47 -178.7(3) . . . . ?
C45 C44 N6 C48 -48.8(5) . . . . ?

_refine_diff_density_max         0.536
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-2

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?


