# 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 2016

####################################################################### 
# 
# 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_g150924a
_database_code_depnum_ccdc_archive 'CCDC 1495311'
_audit_update_record             
;
2016-07-22 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;
_audit_creation_date             2015-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C36 H35 N5'
_chemical_formula_sum            'C36 H35 N5'
_chemical_formula_weight         537.69
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.6424(10)
_cell_length_b                   9.5888(8)
_cell_length_c                   20.3871(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.266(6)
_cell_angle_gamma                90.00
_cell_volume                     2903.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2135
_cell_measurement_temperature    297.56(19)
_cell_measurement_theta_max      24.9580
_cell_measurement_theta_min      3.9050
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8433
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.56(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -104.00  -58.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327 -178.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega  -85.00  -59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327 -178.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00    9.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  -99.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega  -91.00  -11.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  -37.0000   60.0000 80

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00    0.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  -99.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  -92.00  -42.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  -19.0000    0.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0359054000
_diffrn_orient_matrix_UB_12      -0.0363009000
_diffrn_orient_matrix_UB_13      0.0239890000
_diffrn_orient_matrix_UB_21      0.0296823000
_diffrn_orient_matrix_UB_22      0.0554629000
_diffrn_orient_matrix_UB_23      -0.0007263000
_diffrn_orient_matrix_UB_31      -0.0105298000
_diffrn_orient_matrix_UB_32      0.0328224000
_diffrn_orient_matrix_UB_33      0.0276747000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1893
_reflns_number_total             2964
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0016(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1711
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 1.0000 1.7437(3) 0.7500 0.0851(10) Uani 1 d . . 2 S T P
H1 H 1.0000 1.8407 0.7500 0.102 Uiso 1 calc . . 2 RS T P
C2 C 1.06567(16) 1.6714(3) 0.79826(11) 0.0778(6) Uani 1 d . . 1 . . .
H2 H 1.1110 1.7197 0.8309 0.093 Uiso 1 calc . . 1 R . .
C3 C 1.06541(14) 1.5268(2) 0.79906(9) 0.0628(5) Uani 1 d . . 1 . . .
H3 H 1.1097 1.4794 0.8330 0.075 Uiso 1 calc . . 1 R . .
C4 C 1.0000 1.4522(3) 0.7500 0.0508(6) Uani 1 d . . 2 S T P
C5 C 0.91898(11) 1.22868(18) 0.72143(8) 0.0487(4) Uani 1 d . . 1 . . .
C6 C 0.91801(11) 1.1196(2) 0.67648(9) 0.0538(5) Uani 1 d . . 1 . . .
H6 H 0.9705 1.0968 0.6666 0.065 Uiso 1 calc . . 1 R . .
C7 C 0.84090(12) 1.04492(19) 0.64634(8) 0.0528(5) Uani 1 d . . 1 . . .
H7 H 0.8420 0.9717 0.6167 0.063 Uiso 1 calc . . 1 R . .
C8 C 0.76132(11) 1.07693(18) 0.65941(8) 0.0479(4) Uani 1 d . . 1 . . .
C9 C 0.76294(12) 1.1835(2) 0.70568(9) 0.0569(5) Uani 1 d . . 1 . . .
H9 H 0.7107 1.2050 0.7161 0.068 Uiso 1 calc . . 1 R . .
C10 C 0.84076(12) 1.2585(2) 0.73680(9) 0.0575(5) Uani 1 d . . 1 . . .
H10 H 0.8405 1.3290 0.7680 0.069 Uiso 1 calc . . 1 R . .
C11 C 0.67752(12) 1.0038(2) 0.62297(8) 0.0531(5) Uani 1 d . . 1 . . .
H11 H 0.6247 1.0282 0.6319 0.064 Uiso 1 calc . . 1 R . .
C12 C 0.59479(11) 0.8393(2) 0.54314(9) 0.0538(5) Uani 1 d . . 1 . . .
C13 C 0.59777(12) 0.7503(2) 0.49080(10) 0.0654(6) Uani 1 d . . 1 . . .
H13 H 0.6517 0.7404 0.4810 0.078 Uiso 1 calc . . 1 R . .
C14 C 0.52408(12) 0.6758(2) 0.45264(9) 0.0662(6) Uani 1 d . . 1 . . .
H14 H 0.5290 0.6186 0.4172 0.079 Uiso 1 calc . . 1 R . .
C15 C 0.44166(11) 0.6840(2) 0.46578(8) 0.0526(5) Uani 1 d . . 1 . . .
C16 C 0.43930(12) 0.7746(2) 0.51883(9) 0.0609(5) Uani 1 d . . 1 . . .
H16 H 0.3857 0.7846 0.5291 0.073 Uiso 1 calc . . 1 R . .
C17 C 0.51307(12) 0.8492(2) 0.55624(9) 0.0612(5) Uani 1 d . . 1 . . .
H17 H 0.5083 0.9080 0.5912 0.073 Uiso 1 calc . . 1 R . .
C18 C 0.37192(14) 0.5172(3) 0.37356(10) 0.0757(6) Uani 1 d . . 1 . . .
H18A H 0.4102 0.4395 0.3929 0.114 Uiso 1 calc . . 1 GR . .
H18B H 0.3957 0.5665 0.3421 0.114 Uiso 1 calc . . 1 GR . .
H18C H 0.3125 0.4840 0.3492 0.114 Uiso 1 calc . . 1 GR . .
C19 C 0.28881(12) 0.6010(3) 0.44989(10) 0.0724(6) Uani 1 d . . 1 . . .
H19A H 0.2540 0.6848 0.4368 0.109 Uiso 1 calc . . 1 GR . .
H19B H 0.3064 0.5901 0.4991 0.109 Uiso 1 calc . . 1 GR . .
H19C H 0.2532 0.5223 0.4281 0.109 Uiso 1 calc . . 1 GR . .
N1 N 1.0000 1.3052(2) 0.7500 0.0554(5) Uani 1 d . . 2 S T P
N2 N 0.67543(10) 0.90831(17) 0.57964(7) 0.0575(4) Uani 1 d . . 1 . . .
N3 N 0.36788(10) 0.60983(19) 0.42831(8) 0.0675(5) Uani 1 d . . 1 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.368(3) 2_756 ?
C1 C2 1.368(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(2) . ?
C4 C3 1.385(2) 2_756 ?
C4 N1 1.410(3) . ?
C5 C6 1.387(2) . ?
C5 C10 1.385(2) . ?
C5 N1 1.422(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(2) . ?
C8 C9 1.385(2) . ?
C8 C11 1.467(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 N2 1.266(2) . ?
C12 C13 1.379(2) . ?
C12 C17 1.389(2) . ?
C12 N2 1.412(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.399(2) . ?
C15 C16 1.397(2) . ?
C15 N3 1.367(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(2) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 N3 1.443(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 N3 1.439(2) . ?
N1 C5 1.422(2) 2_756 ?

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
C2 C1 H1 120.5 2_756 . ?
C2 C1 H1 120.5 . . ?
C2 C1 C2 119.1(3) 2_756 . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C3 117.8(3) . 2_756 ?
C3 C4 N1 121.12(13) . . ?
C3 C4 N1 121.12(13) 2_756 . ?
C6 C5 N1 118.91(14) . . ?
C10 C5 C6 118.54(16) . . ?
C10 C5 N1 122.55(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.03(16) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 120.99(16) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C11 120.70(16) . . ?
C9 C8 C7 117.91(16) . . ?
C9 C8 C11 121.34(16) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.40(16) . . ?
C10 C9 H9 119.3 . . ?
C5 C10 C9 120.07(16) . . ?
C5 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C8 C11 H11 119.2 . . ?
N2 C11 C8 121.52(16) . . ?
N2 C11 H11 119.2 . . ?
C13 C12 C17 116.61(17) . . ?
C13 C12 N2 117.17(16) . . ?
C17 C12 N2 126.19(16) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 C12 122.34(16) . . ?
C14 C13 H13 118.8 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.57(17) . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 115.63(16) . . ?
N3 C15 C14 122.10(16) . . ?
N3 C15 C16 122.26(15) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 C15 122.31(16) . . ?
C17 C16 H16 118.8 . . ?
C12 C17 H17 119.2 . . ?
C16 C17 C12 121.53(16) . . ?
C16 C17 H17 119.2 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
C4 N1 C5 121.07(10) . . ?
C4 N1 C5 121.07(10) . 2_756 ?
C5 N1 C5 117.9(2) . 2_756 ?
C11 N2 C12 122.02(16) . . ?
C15 N3 C18 121.22(15) . . ?
C15 N3 C19 121.04(15) . . ?
C19 N3 C18 116.77(17) . . ?

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
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C1 C2 C3 -0.80(13) 2_756 . . . ?
C2 C3 C4 C3 -0.80(13) . . . 2_756 ?
C2 C3 C4 N1 179.20(13) . . . . ?
C3 C4 N1 C5 153.79(12) . . . . ?
C3 C4 N1 C5 153.79(12) 2_756 . . 2_756 ?
C3 C4 N1 C5 -26.21(12) . . . 2_756 ?
C3 C4 N1 C5 -26.21(12) 2_756 . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C5 C10 C9 -2.3(3) . . . . ?
C6 C5 N1 C4 132.27(13) . . . . ?
C6 C5 N1 C5 -47.73(13) . . . 2_756 ?
C6 C7 C8 C9 -2.2(3) . . . . ?
C6 C7 C8 C11 175.29(15) . . . . ?
C7 C8 C9 C10 1.6(3) . . . . ?
C7 C8 C11 N2 1.2(3) . . . . ?
C8 C9 C10 C5 0.6(3) . . . . ?
C8 C11 N2 C12 -178.58(14) . . . . ?
C9 C8 C11 N2 178.57(16) . . . . ?
C10 C5 C6 C7 1.7(3) . . . . ?
C10 C5 N1 C4 -47.86(18) . . . . ?
C10 C5 N1 C5 132.14(18) . . . 2_756 ?
C11 C8 C9 C10 -175.84(15) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C13 C12 C17 C16 -0.2(3) . . . . ?
C13 C12 N2 C11 171.67(17) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C13 C14 C15 N3 -179.70(18) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C14 C15 N3 C18 0.9(3) . . . . ?
C14 C15 N3 C19 169.30(19) . . . . ?
C15 C16 C17 C12 0.3(3) . . . . ?
C16 C15 N3 C18 179.77(18) . . . . ?
C16 C15 N3 C19 -11.8(3) . . . . ?
C17 C12 C13 C14 0.7(3) . . . . ?
C17 C12 N2 C11 -10.4(3) . . . . ?
N1 C5 C6 C7 -178.43(15) . . . . ?
N1 C5 C10 C9 177.87(15) . . . . ?
N2 C12 C13 C14 178.86(17) . . . . ?
N2 C12 C17 C16 -178.15(18) . . . . ?
N3 C15 C16 C17 -179.80(18) . . . . ?

_olex2_date_sample_data_collection 2015-09-24
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1495312'
_audit_update_record             
;
2016-07-22 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 N3'
_chemical_formula_weight         391.50

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

_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                   7.6197(18)
_cell_length_b                   18.829(5)
_cell_length_c                   15.360(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.93(2)
_cell_angle_gamma                90
_cell_volume                     2203.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7271
_diffrn_reflns_av_unetI/netI     0.0950
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.440
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.926
_reflns_number_total             3697
_reflns_number_gt                1620
_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)+(0.0340P)²]
 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     SHELXL
_refine_ls_extinction_coef       0.0035(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3697
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1489
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_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_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
C1 C 0.3206(5) 0.6006(2) 0.32637(19) 0.0626(9) Uani 1 1 d . . . . .
C2 C 0.4189(5) 0.6608(2) 0.3437(2) 0.0822(11) Uani 1 1 d . . . . .
H2 H 0.5381 0.6570 0.3569 0.099 Uiso 1 1 calc R U . . .
C3 C 0.3383(7) 0.7272(2) 0.3414(2) 0.0989(14) Uani 1 1 d . . . . .
H3 H 0.4043 0.7679 0.3520 0.119 Uiso 1 1 calc R U . . .
C4 C 0.1628(8) 0.7328(3) 0.3237(3) 0.1021(16) Uani 1 1 d . . . . .
H4 H 0.1091 0.7771 0.3229 0.123 Uiso 1 1 calc R U . . .
C5 C 0.0659(6) 0.6728(3) 0.3071(2) 0.0933(14) Uani 1 1 d . . . . .
H5 H -0.0538 0.6768 0.2952 0.112 Uiso 1 1 calc R U . . .
C6 C 0.1438(5) 0.6070(2) 0.3077(2) 0.0736(11) Uani 1 1 d . . . . .
H6 H 0.0771 0.5667 0.2955 0.088 Uiso 1 1 calc R U . . .
C7 C 0.3075(4) 0.4778(2) 0.3762(2) 0.0622(9) Uani 1 1 d . . . . .
C8 C 0.2705(4) 0.4901(2) 0.4627(2) 0.0783(11) Uani 1 1 d . . . . .
H8 H 0.3103 0.5313 0.4900 0.094 Uiso 1 1 calc R U . . .
C9 C 0.1743(5) 0.4411(3) 0.5081(3) 0.0960(15) Uani 1 1 d . . . . .
H9 H 0.1494 0.4495 0.5663 0.115 Uiso 1 1 calc R U . . .
C10 C 0.1153(5) 0.3808(3) 0.4694(3) 0.0962(15) Uani 1 1 d . . . . .
H10 H 0.0495 0.3484 0.5007 0.115 Uiso 1 1 calc R U . . .
C11 C 0.1531(5) 0.3676(2) 0.3832(3) 0.0892(12) Uani 1 1 d . . . . .
H11 H 0.1142 0.3261 0.3565 0.107 Uiso 1 1 calc R U . . .
C12 C 0.2498(4) 0.4170(2) 0.3367(2) 0.0727(10) Uani 1 1 d . . . . .
H12 H 0.2753 0.4085 0.2786 0.087 Uiso 1 1 calc R U . . .
C13 C 0.5485(4) 0.51452(17) 0.28047(18) 0.0556(8) Uani 1 1 d . . . . .
C14 C 0.6427(4) 0.45276(17) 0.29853(19) 0.0627(9) Uani 1 1 d . . . . .
H14 H 0.6083 0.4236 0.3441 0.075 Uiso 1 1 calc R U . . .
C15 C 0.7854(4) 0.43419(17) 0.25009(19) 0.0602(9) Uani 1 1 d . . . . .
H15 H 0.8450 0.3922 0.2626 0.072 Uiso 1 1 calc R U . . .
C16 C 0.8423(4) 0.47714(18) 0.18262(18) 0.0535(8) Uani 1 1 d . . . . .
C17 C 0.7508(4) 0.53968(18) 0.16568(19) 0.0607(9) Uani 1 1 d . . . . .
H17 H 0.7881 0.5696 0.1215 0.073 Uiso 1 1 calc R U . . .
C18 C 0.6054(4) 0.55822(17) 0.21335(19) 0.0597(9) Uani 1 1 d . . . . .
H18 H 0.5453 0.6000 0.2006 0.072 Uiso 1 1 calc R U . . .
C19 C 0.9902(4) 0.45615(18) 0.12998(18) 0.0566(9) Uani 1 1 d . . . . .
H19 H 1.0376 0.4893 0.0921 0.068 Uiso 1 1 calc R U . . .
C20 C 1.2060(4) 0.37680(17) 0.08231(18) 0.0546(8) Uani 1 1 d . . . . .
C21 C 1.2102(4) 0.31141(18) 0.0422(2) 0.0694(10) Uani 1 1 d . . . . .
H21 H 1.1161 0.2806 0.0491 0.083 Uiso 1 1 calc R U . . .
C22 C 1.3487(4) 0.29032(17) -0.0076(2) 0.0705(10) Uani 1 1 d . . . . .
H22 H 1.3450 0.2465 -0.0354 0.085 Uiso 1 1 calc R U . . .
C23 C 1.4942(4) 0.33379(18) -0.01688(19) 0.0590(9) Uani 1 1 d . . . . .
C24 C 1.4947(4) 0.39923(18) 0.02573(19) 0.0605(9) Uani 1 1 d . . . . .
H24 H 1.5919 0.4288 0.0218 0.073 Uiso 1 1 calc R U . . .
C25 C 1.3513(4) 0.42059(17) 0.07390(18) 0.0616(9) Uani 1 1 d . . . . .
H25 H 1.3527 0.4648 0.1009 0.074 Uiso 1 1 calc R U . . .
C26 C 1.6434(5) 0.2407(2) -0.0985(3) 0.1042(15) Uani 1 1 d . . . . .
H26A H 1.6457 0.2084 -0.0501 0.156 Uiso 1 1 calc R U . . .
H26B H 1.7479 0.2347 -0.1318 0.156 Uiso 1 1 calc R U . . .
H26C H 1.5424 0.2310 -0.1347 0.156 Uiso 1 1 calc R U . . .
C27 C 1.7893(4) 0.3555(2) -0.0709(2) 0.0983(14) Uani 1 1 d . . . . .
H27A H 1.7583 0.4016 -0.0929 0.147 Uiso 1 1 calc R U . . .
H27B H 1.8729 0.3338 -0.1087 0.147 Uiso 1 1 calc R U . . .
H27C H 1.8400 0.3602 -0.0135 0.147 Uiso 1 1 calc R U . . .
N1 N 0.3992(3) 0.53159(15) 0.32908(16) 0.0656(8) Uani 1 1 d . . . . .
N2 N 1.0578(3) 0.39439(15) 0.13353(16) 0.0610(8) Uani 1 1 d . . . . .
N3 N 1.6348(3) 0.31197(16) -0.06707(18) 0.0776(9) 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
C1 C6 1.378(4) . ?
C1 C2 1.382(5) . ?
C1 N1 1.431(4) . ?
C2 C3 1.393(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.367(4) . ?
C7 C8 1.382(4) . ?
C7 N1 1.433(4) . ?
C8 C9 1.375(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.355(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.392(4) . ?
C13 C18 1.394(4) . ?
C13 N1 1.408(3) . ?
C14 C15 1.373(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.391(4) . ?
C16 C19 1.453(3) . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N2 1.272(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(4) . ?
C20 C25 1.388(4) . ?
C20 N2 1.426(3) . ?
C21 C22 1.373(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(4) . ?
C22 H22 0.9300 . ?
C23 N3 1.392(3) . ?
C23 C24 1.395(4) . ?
C24 C25 1.389(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 N3 1.428(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 N3 1.436(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C6 C1 C2 119.6(4) . . ?
C6 C1 N1 119.5(3) . . ?
C2 C1 N1 120.9(3) . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C12 C7 C8 119.9(3) . . ?
C12 C7 N1 121.6(3) . . ?
C8 C7 N1 118.4(3) . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.9(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 119.5(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 120.1(3) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C18 118.4(3) . . ?
C14 C13 N1 120.2(3) . . ?
C18 C13 N1 121.4(3) . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C17 118.1(2) . . ?
C15 C16 C19 120.7(3) . . ?
C17 C16 C19 121.2(3) . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 120.3(3) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
N2 C19 C16 122.8(3) . . ?
N2 C19 H19 118.6 . . ?
C16 C19 H19 118.6 . . ?
C21 C20 C25 117.7(3) . . ?
C21 C20 N2 118.6(3) . . ?
C25 C20 N2 123.6(3) . . ?
C22 C21 C20 122.1(3) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 N3 120.4(3) . . ?
C22 C23 C24 117.9(3) . . ?
N3 C23 C24 121.6(3) . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C20 C25 C24 120.9(3) . . ?
C20 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
N3 C26 H26A 109.5 . . ?
N3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N3 C27 H27A 109.5 . . ?
N3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C13 N1 C1 122.2(2) . . ?
C13 N1 C7 120.8(3) . . ?
C1 N1 C7 116.7(2) . . ?
C19 N2 C20 120.8(3) . . ?
C23 N3 C26 120.3(3) . . ?
C23 N3 C27 119.5(3) . . ?
C26 N3 C27 118.7(3) . . ?

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-2

