# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1503459'
_audit_update_record             
;
2016-09-08 deposited with the CCDC.
2016-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 N3'
_chemical_formula_sum            'C25 H25 N3'
_chemical_formula_weight         367.48

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                   8.4926(2)
_cell_length_b                   7.9538(2)
_cell_length_c                   28.9887(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.1000(10)
_cell_angle_gamma                90
_cell_volume                     1957.78(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4787
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.247
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            15774
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.655
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3844
_reflns_number_gt                2753
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0545P)²+0.5059P] 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         3844
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_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 0.12654(17) 0.9695(2) 0.42247(5) 0.0395(4) Uani 1 1 d . . . . .
C2 C 0.0400(2) 1.1192(2) 0.43006(6) 0.0487(4) Uani 1 1 d . . . . .
H2 H -0.0093 1.1361 0.4580 0.058 Uiso 1 1 calc R U . . .
C3 C 0.0293(2) 1.2374(2) 0.39652(6) 0.0554(5) Uani 1 1 d . . . . .
H3 H -0.0282 1.3350 0.4015 0.066 Uiso 1 1 calc R U . . .
C4 C 0.1048(2) 1.2136(2) 0.35404(6) 0.0563(5) Uani 1 1 d . . . . .
H4 H 0.0974 1.2967 0.3315 0.068 Uiso 1 1 calc R U . . .
C5 C 0.1877(2) 1.0724(2) 0.34546(6) 0.0506(4) Uani 1 1 d . . . . .
H5 H 0.2363 1.0594 0.3172 0.061 Uiso 1 1 calc R U . . .
C6 C 0.20114(17) 0.9439(2) 0.37930(5) 0.0400(4) Uani 1 1 d . . . . .
C7 C 0.28922(16) 0.68609(19) 0.40381(5) 0.0363(3) Uani 1 1 d . . . . .
C8 C 0.36966(16) 0.53073(19) 0.39807(5) 0.0363(3) Uani 1 1 d . . . . .
C9 C 0.45060(17) 0.4628(2) 0.35927(5) 0.0404(4) Uani 1 1 d . . . . .
C10 C 0.4729(2) 0.5154(2) 0.31387(5) 0.0507(4) Uani 1 1 d . . . . .
H10 H 0.4315 0.6170 0.3034 0.061 Uiso 1 1 calc R U . . .
C11 C 0.5577(2) 0.4135(3) 0.28493(6) 0.0622(5) Uani 1 1 d . . . . .
H11 H 0.5728 0.4465 0.2546 0.075 Uiso 1 1 calc R U . . .
C12 C 0.6210(2) 0.2621(3) 0.30048(6) 0.0646(5) Uani 1 1 d . . . . .
H12 H 0.6789 0.1968 0.2803 0.078 Uiso 1 1 calc R U . . .
C13 C 0.6003(2) 0.2064(2) 0.34471(6) 0.0556(5) Uani 1 1 d . . . . .
H13 H 0.6433 0.1051 0.3549 0.067 Uiso 1 1 calc R U . . .
C14 C 0.51235(18) 0.3074(2) 0.37391(5) 0.0427(4) Uani 1 1 d . . . . .
C15 C 0.5209(2) 0.1292(2) 0.44447(6) 0.0534(5) Uani 1 1 d . . . . .
H15A H 0.5993 0.1597 0.4673 0.080 Uiso 1 1 calc R U . . .
H15B H 0.5647 0.0495 0.4234 0.080 Uiso 1 1 calc R U . . .
H15C H 0.4322 0.0799 0.4594 0.080 Uiso 1 1 calc R U . . .
C16 C 0.38262(17) 0.41434(19) 0.43407(5) 0.0369(4) Uani 1 1 d . . . . .
C17 C 0.30911(17) 0.44079(19) 0.47821(5) 0.0368(3) Uani 1 1 d . . . . .
C18 C 0.22949(18) 0.5887(2) 0.48256(5) 0.0405(4) Uani 1 1 d . . . . .
H18 H 0.1800 0.6095 0.5103 0.049 Uiso 1 1 calc R U . . .
C19 C 0.21705(17) 0.71353(19) 0.44747(5) 0.0374(4) Uani 1 1 d . . . . .
C20 C 0.31536(18) 0.3158(2) 0.51762(5) 0.0400(4) Uani 1 1 d . . . . .
H20A H 0.4249 0.2930 0.5254 0.048 Uiso 1 1 calc R U . . .
H20B H 0.2682 0.2111 0.5071 0.048 Uiso 1 1 calc R U . . .
C21 C 0.23248(18) 0.3724(2) 0.56104(5) 0.0399(4) Uani 1 1 d . . . . .
H21A H 0.2772 0.4789 0.5710 0.048 Uiso 1 1 calc R U . . .
H21B H 0.1221 0.3914 0.5535 0.048 Uiso 1 1 calc R U . . .
C22 C 0.24398(18) 0.2487(2) 0.60092(5) 0.0412(4) Uani 1 1 d . . . . .
H22A H 0.2020 0.1409 0.5910 0.049 Uiso 1 1 calc R U . . .
H22B H 0.3538 0.2328 0.6096 0.049 Uiso 1 1 calc R U . . .
C23 C 0.1544(2) 0.3094(2) 0.64246(5) 0.0466(4) Uani 1 1 d . . . . .
H23A H 0.0448 0.3249 0.6334 0.056 Uiso 1 1 calc R U . . .
H23B H 0.1959 0.4181 0.6518 0.056 Uiso 1 1 calc R U . . .
C24 C 0.1627(3) 0.1919(3) 0.68360(6) 0.0632(5) Uani 1 1 d . . . . .
H24A H 0.2712 0.1827 0.6943 0.076 Uiso 1 1 calc R U . . .
H24B H 0.1277 0.0809 0.6741 0.076 Uiso 1 1 calc R U . . .
C25 C 0.0617(4) 0.2522(4) 0.72318(8) 0.1109(10) Uani 1 1 d . . . . .
H25A H 0.0989 0.3598 0.7337 0.166 Uiso 1 1 calc R U . . .
H25B H 0.0684 0.1728 0.7481 0.166 Uiso 1 1 calc R U . . .
H25C H -0.0458 0.2619 0.7127 0.166 Uiso 1 1 calc R U . . .
N1 N 0.13697(15) 0.85411(17) 0.45658(4) 0.0420(3) Uani 1 1 d . . . . .
N2 N 0.28232(15) 0.80204(17) 0.37015(4) 0.0411(3) Uani 1 1 d . . . . .
N3 N 0.47038(15) 0.27862(16) 0.41921(4) 0.0418(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
C1 N1 1.3506(19) . ?
C1 C2 1.418(2) . ?
C1 C6 1.428(2) . ?
C2 C3 1.355(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.412(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.351(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.420(2) . ?
C5 H5 0.9300 . ?
C6 N2 1.351(2) . ?
C7 N2 1.3431(19) . ?
C7 C8 1.423(2) . ?
C7 C19 1.434(2) . ?
C8 C16 1.398(2) . ?
C8 C9 1.435(2) . ?
C9 C10 1.398(2) . ?
C9 C14 1.405(2) . ?
C10 C11 1.380(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(2) . ?
C13 H13 0.9300 . ?
C14 N3 1.3865(19) . ?
C15 N3 1.456(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N3 1.3852(19) . ?
C16 C17 1.450(2) . ?
C17 C18 1.364(2) . ?
C17 C20 1.515(2) . ?
C18 C19 1.423(2) . ?
C18 H18 0.9300 . ?
C19 N1 1.3377(19) . ?
C20 C21 1.522(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.520(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.515(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.515(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.523(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
N1 C1 C2 118.94(14) . . ?
N1 C1 C6 121.38(14) . . ?
C2 C1 C6 119.68(14) . . ?
C3 C2 C1 119.97(16) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.47(17) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 121.29(16) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.41(16) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N2 C6 C5 120.00(14) . . ?
N2 C6 C1 121.84(14) . . ?
C5 C6 C1 118.16(15) . . ?
N2 C7 C8 121.71(13) . . ?
N2 C7 C19 121.57(14) . . ?
C8 C7 C19 116.72(13) . . ?
C16 C8 C7 121.25(13) . . ?
C16 C8 C9 107.69(13) . . ?
C7 C8 C9 131.05(14) . . ?
C10 C9 C14 119.43(15) . . ?
C10 C9 C8 134.52(16) . . ?
C14 C9 C8 106.03(13) . . ?
C11 C10 C9 118.57(17) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C12 121.01(17) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 121.84(17) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 117.47(18) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 H13 121.3 . . ?
N3 C14 C13 129.07(16) . . ?
N3 C14 C9 109.28(13) . . ?
C13 C14 C9 121.65(15) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C8 108.61(13) . . ?
N3 C16 C17 129.11(14) . . ?
C8 C16 C17 122.26(13) . . ?
C18 C17 C16 115.42(13) . . ?
C18 C17 C20 120.46(13) . . ?
C16 C17 C20 124.12(13) . . ?
C17 C18 C19 124.44(14) . . ?
C17 C18 H18 117.8 . . ?
C19 C18 H18 117.8 . . ?
N1 C19 C18 118.22(13) . . ?
N1 C19 C7 121.94(14) . . ?
C18 C19 C7 119.84(13) . . ?
C17 C20 C21 114.79(13) . . ?
C17 C20 H20A 108.6 . . ?
C21 C20 H20A 108.6 . . ?
C17 C20 H20B 108.6 . . ?
C21 C20 H20B 108.6 . . ?
H20A C20 H20B 107.5 . . ?
C22 C21 C20 114.41(13) . . ?
C22 C21 H21A 108.7 . . ?
C20 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C20 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C23 C22 C21 111.86(13) . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 C24 114.37(15) . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 C25 112.38(18) . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C19 N1 C1 116.75(13) . . ?
C7 N2 C6 116.49(13) . . ?
C14 N3 C16 108.39(13) . . ?
C14 N3 C15 122.17(13) . . ?
C16 N3 C15 129.41(13) . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.035

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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 1503460'
_audit_update_record             
;
2016-09-08 deposited with the CCDC.
2016-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H27 N3'
_chemical_formula_sum            'C26 H27 N3'
_chemical_formula_weight         381.50

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/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                   15.8218(7)
_cell_length_b                   8.1579(3)
_cell_length_c                   16.5439(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.532(2)
_cell_angle_gamma                90
_cell_volume                     2099.39(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4365
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.54

_exptl_crystal_description       rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.206
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            17282
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.619
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4117
_reflns_number_gt                2730
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0613P)²+0.6555P] 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       0.0052(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4117
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.72411(12) 0.4186(2) -0.12918(12) 0.0512(5) Uani 1 1 d . . . . .
C2 C 0.79780(14) 0.4641(3) -0.16141(15) 0.0656(6) Uani 1 1 d . . . . .
H2 H 0.8524 0.4470 -0.1306 0.079 Uiso 1 1 calc R U . . .
C3 C 0.78853(17) 0.5325(3) -0.23715(16) 0.0751(7) Uani 1 1 d . . . . .
H3 H 0.8373 0.5620 -0.2577 0.090 Uiso 1 1 calc R U . . .
C4 C 0.70732(16) 0.5596(3) -0.28506(15) 0.0714(6) Uani 1 1 d . . . . .
H4 H 0.7027 0.6056 -0.3371 0.086 Uiso 1 1 calc R U . . .
C5 C 0.63539(15) 0.5193(3) -0.25606(13) 0.0634(6) Uani 1 1 d . . . . .
H5 H 0.5816 0.5383 -0.2882 0.076 Uiso 1 1 calc R U . . .
C6 C 0.64157(13) 0.4485(2) -0.17717(12) 0.0512(5) Uani 1 1 d . . . . .
C7 C 0.57846(11) 0.3398(2) -0.07551(11) 0.0458(4) Uani 1 1 d . . . . .
C8 C 0.66214(11) 0.3071(2) -0.02761(11) 0.0435(4) Uani 1 1 d . . . . .
C9 C 0.66510(11) 0.2286(2) 0.04950(11) 0.0443(4) Uani 1 1 d . . . . .
C10 C 0.73647(12) 0.1764(2) 0.11000(11) 0.0498(5) Uani 1 1 d . . . . .
C11 C 0.82556(12) 0.1893(3) 0.11840(13) 0.0610(6) Uani 1 1 d . . . . .
H11 H 0.8502 0.2423 0.0787 0.073 Uiso 1 1 calc R U . . .
C12 C 0.87622(14) 0.1215(3) 0.18701(15) 0.0724(7) Uani 1 1 d . . . . .
H12 H 0.9357 0.1298 0.1936 0.087 Uiso 1 1 calc R U . . .
C13 C 0.84017(16) 0.0413(3) 0.24632(15) 0.0762(7) Uani 1 1 d . . . . .
H13 H 0.8761 -0.0036 0.2917 0.091 Uiso 1 1 calc R U . . .
C14 C 0.75326(16) 0.0267(3) 0.23966(14) 0.0707(6) Uani 1 1 d . . . . .
H14 H 0.7294 -0.0276 0.2795 0.085 Uiso 1 1 calc R U . . .
C15 C 0.70144(12) 0.0962(2) 0.17084(12) 0.0542(5) Uani 1 1 d . . . . .
C16 C 0.55942(15) 0.0101(3) 0.19983(13) 0.0697(6) Uani 1 1 d . . . . .
H16A H 0.5888 -0.0893 0.2216 0.084 Uiso 1 1 calc R U . . .
H16B H 0.5054 -0.0212 0.1655 0.084 Uiso 1 1 calc R U . . .
C17 C 0.54171(19) 0.1129(4) 0.26915(16) 0.1075(10) Uani 1 1 d . . . . .
H17A H 0.5950 0.1423 0.3039 0.161 Uiso 1 1 calc R U . . .
H17B H 0.5069 0.0522 0.3005 0.161 Uiso 1 1 calc R U . . .
H17C H 0.5118 0.2104 0.2478 0.161 Uiso 1 1 calc R U . . .
C18 C 0.58973(11) 0.1800(2) 0.07564(11) 0.0454(4) Uani 1 1 d . . . . .
C19 C 0.50538(11) 0.2167(2) 0.02885(11) 0.0443(4) Uani 1 1 d . . . . .
C20 C 0.50357(11) 0.2950(2) -0.04414(11) 0.0476(4) Uani 1 1 d . . . . .
H20 H 0.4502 0.3208 -0.0754 0.057 Uiso 1 1 calc R U . . .
C21 C 0.42296(11) 0.1721(2) 0.05728(11) 0.0486(4) Uani 1 1 d . . . . .
H21A H 0.4248 0.2189 0.1115 0.058 Uiso 1 1 calc R U . . .
H21B H 0.4212 0.0539 0.0630 0.058 Uiso 1 1 calc R U . . .
C22 C 0.34004(11) 0.2263(2) 0.00278(11) 0.0491(5) Uani 1 1 d . . . . .
H22A H 0.3369 0.1793 -0.0515 0.059 Uiso 1 1 calc R U . . .
H22B H 0.3403 0.3447 -0.0027 0.059 Uiso 1 1 calc R U . . .
C23 C 0.26132(12) 0.1750(2) 0.03680(12) 0.0535(5) Uani 1 1 d . . . . .
H23A H 0.2603 0.0564 0.0405 0.064 Uiso 1 1 calc R U . . .
H23B H 0.2659 0.2184 0.0920 0.064 Uiso 1 1 calc R U . . .
C24 C 0.17772(12) 0.2326(3) -0.01453(13) 0.0603(5) Uani 1 1 d . . . . .
H24A H 0.1724 0.1873 -0.0694 0.072 Uiso 1 1 calc R U . . .
H24B H 0.1791 0.3511 -0.0192 0.072 Uiso 1 1 calc R U . . .
C25 C 0.09924(14) 0.1834(3) 0.02118(17) 0.0833(7) Uani 1 1 d . . . . .
H25A H 0.0963 0.0647 0.0230 0.100 Uiso 1 1 calc R U . . .
H25B H 0.1062 0.2235 0.0772 0.100 Uiso 1 1 calc R U . . .
C26 C 0.01701(16) 0.2471(5) -0.0263(2) 0.1148(11) Uani 1 1 d . . . . .
H26A H 0.0200 0.3644 -0.0300 0.172 Uiso 1 1 calc R U . . .
H26B H -0.0293 0.2173 0.0009 0.172 Uiso 1 1 calc R U . . .
H26C H 0.0072 0.2009 -0.0806 0.172 Uiso 1 1 calc R U . . .
N1 N 0.73405(9) 0.34690(18) -0.05426(10) 0.0503(4) Uani 1 1 d . . . . .
N2 N 0.56874(10) 0.40958(19) -0.14975(10) 0.0522(4) Uani 1 1 d . . . . .
N3 N 0.61249(10) 0.0972(2) 0.14964(9) 0.0536(4) 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 N1 1.354(2) . ?
C1 C2 1.417(3) . ?
C1 C6 1.420(3) . ?
C2 C3 1.355(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.414(3) . ?
C5 H5 0.9300 . ?
C6 N2 1.351(2) . ?
C7 N2 1.337(2) . ?
C7 C20 1.425(2) . ?
C7 C8 1.438(2) . ?
C8 N1 1.333(2) . ?
C8 C9 1.421(3) . ?
C9 C18 1.398(2) . ?
C9 C10 1.430(2) . ?
C10 C11 1.395(3) . ?
C10 C15 1.397(3) . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(3) . ?
C14 H14 0.9300 . ?
C15 N3 1.387(2) . ?
C16 N3 1.468(3) . ?
C16 C17 1.488(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N3 1.387(2) . ?
C18 C19 1.447(2) . ?
C19 C20 1.362(2) . ?
C19 C21 1.509(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.516(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.517(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.510(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.523(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.485(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
N1 C1 C2 119.45(19) . . ?
N1 C1 C6 121.83(17) . . ?
C2 C1 C6 118.72(19) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N2 C6 C5 119.12(19) . . ?
N2 C6 C1 121.70(17) . . ?
C5 C6 C1 119.18(18) . . ?
N2 C7 C20 118.69(16) . . ?
N2 C7 C8 121.67(16) . . ?
C20 C7 C8 119.64(16) . . ?
N1 C8 C9 121.11(16) . . ?
N1 C8 C7 121.86(17) . . ?
C9 C8 C7 117.03(16) . . ?
C18 C9 C8 121.04(16) . . ?
C18 C9 C10 107.96(16) . . ?
C8 C9 C10 130.91(16) . . ?
C11 C10 C15 119.34(18) . . ?
C11 C10 C9 134.58(19) . . ?
C15 C10 C9 106.08(16) . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 117.6(2) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
N3 C15 C14 128.8(2) . . ?
N3 C15 C10 109.45(16) . . ?
C14 C15 C10 121.8(2) . . ?
N3 C16 C17 111.8(2) . . ?
N3 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 C9 108.21(15) . . ?
N3 C18 C19 129.69(17) . . ?
C9 C18 C19 122.10(16) . . ?
C20 C19 C18 116.07(16) . . ?
C20 C19 C21 120.67(16) . . ?
C18 C19 C21 123.25(16) . . ?
C19 C20 C7 123.99(17) . . ?
C19 C20 H20 118.0 . . ?
C7 C20 H20 118.0 . . ?
C19 C21 C22 116.58(16) . . ?
C19 C21 H21A 108.1 . . ?
C22 C21 H21A 108.1 . . ?
C19 C21 H21B 108.1 . . ?
C22 C21 H21B 108.1 . . ?
H21A C21 H21B 107.3 . . ?
C21 C22 C23 112.27(16) . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C22 113.55(17) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C25 113.08(19) . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C26 C25 C24 113.6(2) . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C24 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C8 N1 C1 116.41(16) . . ?
C7 N2 C6 116.53(16) . . ?
C15 N3 C18 108.29(15) . . ?
C15 N3 C16 120.88(16) . . ?
C18 N3 C16 130.69(16) . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.032

_shelxl_version_number           2014-3



