# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_yxq-zw-1206a
_database_code_depnum_ccdc_archive 'CCDC 1526799'
_audit_update_record             
;
2017-01-11 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;
_audit_creation_date             2016-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 N3'
_chemical_formula_sum            'C14 H17 N3'
_chemical_formula_weight         227.30
_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 0.0181 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'

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

_cell_length_a                   5.8794(4)
_cell_length_b                   7.4664(7)
_cell_length_c                   15.5877(15)
_cell_angle_alpha                92.948(8)
_cell_angle_beta                 93.410(7)
_cell_angle_gamma                110.440(8)
_cell_volume                     638.14(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.6690
_cell_measurement_theta_min      6.3420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73447
_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.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5423
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.516
_diffrn_reflns_theta_min         6.345
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9735
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000   90.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   38.0000 -180.0000 88

#__ type_ start__ end____ width___ exp.time_
  5 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   38.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
  7 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000 -180.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000  -30.0000 67

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   87.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 15 omega   90.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 85

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

#__ type_ start__ end____ width___ exp.time_
 17 omega   57.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 19 omega   38.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -102.0000  -76.0000 74

#__ type_ start__ end____ width___ exp.time_
 20 omega   41.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
 21 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
 22 omega   70.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 108

#__ type_ start__ end____ width___ exp.time_
 23 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
 24 omega  -33.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -38.0000  -30.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0212811000
_diffrn_orient_matrix_UB_12      0.0856388000
_diffrn_orient_matrix_UB_13      -0.0866537000
_diffrn_orient_matrix_UB_21      -0.1526581000
_diffrn_orient_matrix_UB_22      0.1088404000
_diffrn_orient_matrix_UB_23      0.0397305000
_diffrn_orient_matrix_UB_31      0.2344477000
_diffrn_orient_matrix_UB_32      0.1720181000
_diffrn_orient_matrix_UB_33      0.0278392000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2044
_reflns_number_total             2466
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2466
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0663
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1100P)²+0.0140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1641
_refine_ls_wR_factor_ref         0.1779
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H00A,H00B), C9(H00C,H00D), C10(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H005), C3(H00E), C13(H00F), C14(H00K), C2(H00L), C1(H00M)
2.c Idealised Me refined as rotating group:
 C11(H00N,H00O,H00P)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N001 N 0.7070(2) 0.25784(18) 0.45509(9) 0.0442(4) Uani 1 1 d . . . . .
N002 N 0.9211(2) 0.2483(2) 0.43242(9) 0.0525(4) Uani 1 1 d . . . . .
N003 N 0.9195(3) 0.2496(2) 0.34873(10) 0.0533(4) Uani 1 1 d . . . . .
C004 C 0.7045(3) 0.2616(2) 0.31650(11) 0.0457(4) Uani 1 1 d . . . . .
C005 C 0.5690(3) 0.2669(2) 0.38404(11) 0.0466(4) Uani 1 1 d . . . . .
H005 H 0.4145 0.2751 0.3817 0.056 Uiso 1 1 calc R . . . .
C006 C 0.6532(3) 0.2533(2) 0.54355(11) 0.0473(4) Uani 1 1 d . . . . .
C007 C 0.8466(3) 0.2354(2) 0.60539(11) 0.0466(4) Uani 1 1 d . . . . .
H00A H 0.9980 0.3389 0.5985 0.056 Uiso 1 1 calc R . . . .
H00B H 0.8701 0.1159 0.5901 0.056 Uiso 1 1 calc R . . . .
C008 C 0.6461(3) 0.2650(2) 0.22385(11) 0.0483(4) Uani 1 1 d . . . . .
C009 C 0.7962(3) 0.2399(2) 0.69962(12) 0.0514(4) Uani 1 1 d . . . . .
H00C H 0.7888 0.3642 0.7172 0.062 Uiso 1 1 calc R . . . .
H00D H 0.6387 0.1436 0.7065 0.062 Uiso 1 1 calc R . . . .
C00A C 0.7733(4) 0.2045(3) 0.16330(12) 0.0587(5) Uani 1 1 d . . . . .
H00E H 0.8967 0.1607 0.1817 0.070 Uiso 1 1 calc R . . . .
C00B C 0.4612(3) 0.3276(3) 0.19416(13) 0.0615(5) Uani 1 1 d . . . . .
H00F H 0.3720 0.3671 0.2334 0.074 Uiso 1 1 calc R . . . .
C00C C 0.4426(4) 0.2619(4) 0.56333(15) 0.0733(7) Uani 1 1 d . . . . .
C00D C 0.9880(4) 0.2035(3) 0.75750(13) 0.0617(5) Uani 1 1 d . . . . .
H00I H 1.1460 0.2969 0.7487 0.074 Uiso 1 1 calc R . . . .
H00J H 0.9910 0.0774 0.7410 0.074 Uiso 1 1 calc R . . . .
C00E C 0.4089(4) 0.3316(3) 0.10734(15) 0.0727(6) Uani 1 1 d . . . . .
H00K H 0.2851 0.3744 0.0885 0.087 Uiso 1 1 calc R . . . .
C00F C 0.7193(4) 0.2084(3) 0.07670(13) 0.0709(6) Uani 1 1 d . . . . .
H00L H 0.8062 0.1669 0.0371 0.085 Uiso 1 1 calc R . . . .
C00G C 0.5382(4) 0.2728(3) 0.04780(14) 0.0743(6) Uani 1 1 d . . . . .
H00M H 0.5034 0.2768 -0.0109 0.089 Uiso 1 1 calc R . . . .
C00H C 0.9465(5) 0.2145(4) 0.85212(14) 0.0784(7) Uani 1 1 d . . . . .
H00N H 0.7902 0.1227 0.8614 0.118 Uiso 1 1 calc GR . . . .
H00O H 0.9515 0.3411 0.8697 0.118 Uiso 1 1 calc GR . . . .
H00P H 1.0714 0.1868 0.8853 0.118 Uiso 1 1 calc GR . . . .
H00G H 0.331(4) 0.280(3) 0.5236(16) 0.078(7) Uiso 1 1 d . . . . .
H00H H 0.410(4) 0.259(3) 0.6252(16) 0.077(7) Uiso 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
N001 N002 1.3520(18) . ?
N001 C005 1.352(2) . ?
N001 C006 1.432(2) . ?
N002 N003 1.305(2) . ?
N003 C004 1.366(2) . ?
C004 C005 1.365(2) . ?
C004 C008 1.468(2) . ?
C005 H005 0.9300 . ?
C006 C007 1.493(2) . ?
C006 C00C 1.316(2) . ?
C007 H00A 0.9700 . ?
C007 H00B 0.9700 . ?
C007 C009 1.517(2) . ?
C008 C00A 1.390(3) . ?
C008 C00B 1.389(3) . ?
C009 H00C 0.9700 . ?
C009 H00D 0.9700 . ?
C009 C00D 1.509(3) . ?
C00A H00E 0.9300 . ?
C00A C00F 1.372(3) . ?
C00B H00F 0.9300 . ?
C00B C00E 1.374(3) . ?
C00C H00G 0.92(2) . ?
C00C H00H 0.99(2) . ?
C00D H00I 0.9700 . ?
C00D H00J 0.9700 . ?
C00D C00H 1.512(3) . ?
C00E H00K 0.9300 . ?
C00E C00G 1.381(3) . ?
C00F H00L 0.9300 . ?
C00F C00G 1.375(3) . ?
C00G H00M 0.9300 . ?
C00H H00N 0.9600 . ?
C00H H00O 0.9600 . ?
C00H H00P 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
N002 N001 C005 109.90(13) . . ?
N002 N001 C006 120.43(13) . . ?
C005 N001 C006 129.65(13) . . ?
N003 N002 N001 107.72(13) . . ?
N002 N003 C004 109.01(14) . . ?
N003 C004 C008 122.32(15) . . ?
C005 C004 N003 108.00(15) . . ?
C005 C004 C008 129.67(16) . . ?
N001 C005 C004 105.37(14) . . ?
N001 C005 H005 127.3 . . ?
C004 C005 H005 127.3 . . ?
N001 C006 C007 115.17(13) . . ?
C00C C006 N001 118.86(16) . . ?
C00C C006 C007 125.96(17) . . ?
C006 C007 H00A 108.4 . . ?
C006 C007 H00B 108.4 . . ?
C006 C007 C009 115.48(14) . . ?
H00A C007 H00B 107.5 . . ?
C009 C007 H00A 108.4 . . ?
C009 C007 H00B 108.4 . . ?
C00A C008 C004 120.85(17) . . ?
C00B C008 C004 121.04(17) . . ?
C00B C008 C00A 118.11(18) . . ?
C007 C009 H00C 109.1 . . ?
C007 C009 H00D 109.1 . . ?
H00C C009 H00D 107.8 . . ?
C00D C009 C007 112.54(14) . . ?
C00D C009 H00C 109.1 . . ?
C00D C009 H00D 109.1 . . ?
C008 C00A H00E 119.6 . . ?
C00F C00A C008 120.85(19) . . ?
C00F C00A H00E 119.6 . . ?
C008 C00B H00F 119.7 . . ?
C00E C00B C008 120.7(2) . . ?
C00E C00B H00F 119.7 . . ?
C006 C00C H00G 123.3(15) . . ?
C006 C00C H00H 117.3(14) . . ?
H00G C00C H00H 119(2) . . ?
C009 C00D H00I 108.9 . . ?
C009 C00D H00J 108.9 . . ?
C009 C00D C00H 113.47(18) . . ?
H00I C00D H00J 107.7 . . ?
C00H C00D H00I 108.9 . . ?
C00H C00D H00J 108.9 . . ?
C00B C00E H00K 119.7 . . ?
C00B C00E C00G 120.7(2) . . ?
C00G C00E H00K 119.7 . . ?
C00A C00F H00L 119.6 . . ?
C00A C00F C00G 120.7(2) . . ?
C00G C00F H00L 119.6 . . ?
C00E C00G H00M 120.5 . . ?
C00F C00G C00E 118.9(2) . . ?
C00F C00G H00M 120.5 . . ?
C00D C00H H00N 109.5 . . ?
C00D C00H H00O 109.5 . . ?
C00D C00H H00P 109.5 . . ?
H00N C00H H00O 109.5 . . ?
H00N C00H H00P 109.5 . . ?
H00O C00H H00P 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-12-07
_olex2_submission_special_instructions 'No special instructions were received'
