# Electronic Supplementary Material (ESI) for ChemComm.
# 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_bwn16068a
_database_code_depnum_ccdc_archive 'CCDC 1499749'
_audit_update_record             
;
2016-08-18 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;
_audit_creation_date             2016-03-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        2-MTPNE
_chemical_formula_moiety         'C6 H9 N17'
_chemical_formula_sum            'C6 H9 N17'
_chemical_formula_weight         319.30
_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 0.0033 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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   15.804(3)
_cell_length_b                   10.785(2)
_cell_length_c                   8.1924(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.10(3)
_cell_angle_gamma                90.00
_cell_volume                     1378.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3977
_cell_measurement_temperature    153.1500
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      1.8883
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5975
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8237
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.30
_diffrn_ambient_temperature      153.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0422
	          2theta: -20.1827
scan:
	Number of images: 294
	           Slice: -86.0000 - 61.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0422
	          2theta: -20.1827
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             3312
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0068
_diffrn_orient_matrix_UB_12      -0.0615
_diffrn_orient_matrix_UB_13      -0.1070
_diffrn_orient_matrix_UB_21      -0.0195
_diffrn_orient_matrix_UB_22      0.0791
_diffrn_orient_matrix_UB_23      -0.0442
_diffrn_orient_matrix_UB_31      0.0612
_diffrn_orient_matrix_UB_32      0.0049
_diffrn_orient_matrix_UB_33      -0.0184
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1947
_reflns_number_total             2410
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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    
;
????
;
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1853
_refine_ls_R_factor_gt           0.1663
_refine_ls_restrained_S_all      1.205
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1471P)²+24.3673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4342
_refine_ls_wR_factor_ref         0.4465
_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 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C)
;
_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_refinement_flags_posn
N1 N 0.0940(5) 0.8692(7) -0.0850(10) 0.0255(19) Uani 1 d . . .
N2 N 0.0489(5) 0.9252(7) -0.2176(11) 0.0272(19) Uani 1 d . . .
N3 N 0.0441(6) 1.0464(8) -0.2029(10) 0.030(2) Uani 1 d . . .
N4 N 0.0868(5) 1.0752(7) -0.0559(10) 0.0273(19) Uani 1 d . . .
N5 N 0.1651(6) 0.9633(8) 0.1715(10) 0.028(2) Uani 1 d . . .
N6 N 0.1896(5) 0.8557(8) 0.2110(10) 0.027(2) Uani 1 d . . .
N7 N 0.2394(5) 0.8522(8) 0.3633(10) 0.027(2) Uani 1 d . . .
N8 N 0.2754(5) 0.7364(7) 0.3907(10) 0.027(2) Uani 1 d . . .
N9 N 0.3304(5) 0.7329(7) 0.5223(11) 0.027(2) Uani 1 d . . .
N10 N 0.3294(7) 0.5075(8) 0.4718(14) 0.046(3) Uani 1 d . . .
N11 N 0.3770(6) 0.4161(8) 0.5375(13) 0.040(2) Uani 1 d . . .
N12 N 0.4359(5) 0.4661(8) 0.6540(10) 0.0265(19) Uani 1 d . . .
N13 N 0.4289(6) 0.5887(8) 0.6658(11) 0.032(2) Uani 1 d . . .
N14 N 0.3399(6) 1.0154(8) 0.4674(13) 0.035(2) Uani 1 d . . .
N15 N 0.3371(6) 1.1121(8) 0.5630(12) 0.032(2) Uani 1 d . . .
N16 N 0.2606(6) 1.1108(7) 0.6110(10) 0.0269(19) Uani 1 d . . .
N17 N 0.2109(6) 1.0152(8) 0.5475(11) 0.033(2) Uani 1 d . . .
C1 C 0.0101(8) 0.8575(10) -0.3626(15) 0.041(3) Uani 1 d . . .
H1A H 0.0534 0.8405 -0.4330 0.061 Uiso 1 calc . . GR
H1B H -0.0362 0.9072 -0.4242 0.061 Uiso 1 calc . . GR
H1C H -0.0132 0.7791 -0.3288 0.061 Uiso 1 calc . . GR
C2 C 0.1154(6) 0.9650(9) 0.0111(12) 0.024(2) Uani 1 d . . .
C3 C 0.3619(6) 0.6105(10) 0.5481(13) 0.028(2) Uani 1 d . . .
C4 C 0.4964(8) 0.3886(11) 0.7590(17) 0.044(3) Uani 1 d . . .
H4A H 0.4937 0.4074 0.8752 0.066 Uiso 1 calc . . GR
H4B H 0.5544 0.4048 0.7362 0.066 Uiso 1 calc . . GR
H4C H 0.4819 0.3012 0.7369 0.066 Uiso 1 calc . . GR
C5 C 0.2643(6) 0.9586(9) 0.4621(13) 0.028(2) Uani 1 d . . .
C6 C 0.2325(7) 1.2080(10) 0.7139(12) 0.030(2) Uani 1 d . . .
H6A H 0.2265 1.1736 0.8223 0.044 Uiso 1 calc . . GR
H6B H 0.1771 1.2407 0.6605 0.044 Uiso 1 calc . . GR
H6C H 0.2748 1.2751 0.7281 0.044 Uiso 1 calc . . GR

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.033(5) 0.018(4) 0.025(4) -0.002(3) 0.005(4) 0.000(3)
N2 0.032(5) 0.016(4) 0.032(5) 0.004(4) 0.001(4) 0.000(4)
N3 0.036(5) 0.024(5) 0.028(4) 0.002(4) 0.001(4) 0.001(4)
N4 0.032(5) 0.019(4) 0.031(5) -0.001(4) 0.005(4) -0.001(4)
N5 0.035(5) 0.022(4) 0.026(4) -0.005(4) 0.004(4) -0.001(4)
N6 0.030(5) 0.023(4) 0.027(4) 0.000(4) 0.003(4) 0.003(4)
N7 0.030(5) 0.023(4) 0.024(4) -0.005(3) -0.001(4) 0.003(4)
N8 0.032(5) 0.014(4) 0.034(5) 0.009(4) 0.003(4) 0.007(3)
N9 0.028(4) 0.017(4) 0.036(5) 0.001(4) 0.008(4) -0.002(3)
N10 0.051(6) 0.013(4) 0.068(7) -0.006(4) -0.010(6) 0.002(4)
N11 0.045(6) 0.021(5) 0.055(6) 0.009(4) 0.006(5) 0.007(4)
N12 0.020(4) 0.029(5) 0.031(5) 0.003(4) 0.007(3) -0.002(4)
N13 0.034(5) 0.028(5) 0.035(5) -0.003(4) 0.005(4) 0.005(4)
N14 0.034(5) 0.023(5) 0.051(6) 0.002(4) 0.010(4) 0.001(4)
N15 0.033(5) 0.020(4) 0.045(5) -0.003(4) 0.011(4) -0.008(4)
N16 0.042(5) 0.014(4) 0.024(4) -0.001(3) 0.004(4) -0.001(4)
N17 0.039(5) 0.021(4) 0.037(5) -0.001(4) -0.001(4) -0.001(4)
C1 0.056(7) 0.019(5) 0.043(7) -0.009(5) -0.005(6) 0.000(5)
C2 0.022(5) 0.025(5) 0.027(5) -0.001(4) 0.010(4) 0.003(4)
C3 0.024(5) 0.025(5) 0.035(6) 0.002(4) 0.006(4) 0.003(4)
C4 0.040(6) 0.034(6) 0.055(7) -0.004(6) 0.000(6) 0.020(5)
C5 0.031(5) 0.012(5) 0.041(6) 0.000(4) 0.003(5) 0.005(4)
C6 0.036(6) 0.026(5) 0.026(5) -0.008(4) 0.005(5) 0.010(4)

_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 N2 1.345(11) . ?
N1 C2 1.311(13) . ?
N2 N3 1.317(11) . ?
N2 C1 1.445(14) . ?
N3 N4 1.321(12) . ?
N4 C2 1.356(13) . ?
N5 N6 1.250(12) . ?
N5 C2 1.420(13) . ?
N6 N7 1.366(11) . ?
N7 N8 1.376(11) . ?
N7 C5 1.424(13) . ?
N8 N9 1.273(12) . ?
N9 C3 1.415(13) . ?
N10 N11 1.303(13) . ?
N10 C3 1.337(14) . ?
N11 N12 1.337(13) . ?
N12 N13 1.332(12) . ?
N12 C4 1.446(14) . ?
N13 C3 1.336(13) . ?
N14 N15 1.309(13) . ?
N14 C5 1.337(14) . ?
N15 N16 1.329(12) . ?
N16 N17 1.350(12) . ?
N16 C6 1.458(12) . ?
N17 C5 1.327(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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 N1 N2 100.7(8) . . ?
N1 N2 C1 122.6(8) . . ?
N3 N2 N1 113.8(8) . . ?
N3 N2 C1 123.6(9) . . ?
N2 N3 N4 106.7(8) . . ?
N3 N4 C2 104.7(8) . . ?
N6 N5 C2 110.8(8) . . ?
N5 N6 N7 111.9(8) . . ?
N6 N7 N8 109.7(8) . . ?
N6 N7 C5 124.3(8) . . ?
N8 N7 C5 124.7(8) . . ?
N9 N8 N7 112.0(8) . . ?
N8 N9 C3 109.3(8) . . ?
N11 N10 C3 106.4(9) . . ?
N10 N11 N12 106.3(9) . . ?
N11 N12 C4 120.8(9) . . ?
N13 N12 N11 113.3(8) . . ?
N13 N12 C4 125.8(9) . . ?
N12 N13 C3 100.8(8) . . ?
N15 N14 C5 105.7(9) . . ?
N14 N15 N16 106.7(8) . . ?
N15 N16 N17 113.3(8) . . ?
N15 N16 C6 122.6(8) . . ?
N17 N16 C6 124.0(9) . . ?
C5 N17 N16 100.1(8) . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 N4 114.2(9) . . ?
N1 C2 N5 126.7(9) . . ?
N4 C2 N5 119.1(9) . . ?
N10 C3 N9 127.3(9) . . ?
N13 C3 N9 119.5(9) . . ?
N13 C3 N10 113.1(9) . . ?
N12 C4 H4A 109.5 . . ?
N12 C4 H4B 109.5 . . ?
N12 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N14 C5 N7 123.6(9) . . ?
N17 C5 N7 121.9(9) . . ?
N17 C5 N14 114.3(9) . . ?
N16 C6 H6A 109.5 . . ?
N16 C6 H6B 109.5 . . ?
N16 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
N1 N2 N3 N4 -0.3(12) . . . . ?
N2 N1 C2 N4 -0.7(11) . . . . ?
N2 N1 C2 N5 -179.5(9) . . . . ?
N2 N3 N4 C2 -0.2(10) . . . . ?
N3 N4 C2 N1 0.6(11) . . . . ?
N3 N4 C2 N5 179.5(8) . . . . ?
N5 N6 N7 N8 -170.8(8) . . . . ?
N5 N6 N7 C5 -3.1(13) . . . . ?
N6 N5 C2 N1 2.0(14) . . . . ?
N6 N5 C2 N4 -176.8(9) . . . . ?
N6 N7 N8 N9 172.1(8) . . . . ?
N6 N7 C5 N14 -97.3(12) . . . . ?
N6 N7 C5 N17 77.6(13) . . . . ?
N7 N8 N9 C3 177.1(8) . . . . ?
N8 N7 C5 N14 68.7(14) . . . . ?
N8 N7 C5 N17 -116.5(11) . . . . ?
N8 N9 C3 N10 -13.0(15) . . . . ?
N8 N9 C3 N13 170.6(9) . . . . ?
N10 N11 N12 N13 -0.6(12) . . . . ?
N10 N11 N12 C4 176.1(10) . . . . ?
N11 N10 C3 N9 -178.0(10) . . . . ?
N11 N10 C3 N13 -1.5(14) . . . . ?
N11 N12 N13 C3 -0.3(11) . . . . ?
N12 N13 C3 N9 177.9(9) . . . . ?
N12 N13 C3 N10 1.1(12) . . . . ?
N14 N15 N16 N17 -0.8(12) . . . . ?
N14 N15 N16 C6 -177.3(9) . . . . ?
N15 N14 C5 N7 176.5(9) . . . . ?
N15 N14 C5 N17 1.3(13) . . . . ?
N15 N16 N17 C5 1.5(11) . . . . ?
N16 N17 C5 N7 -176.9(9) . . . . ?
N16 N17 C5 N14 -1.7(12) . . . . ?
C1 N2 N3 N4 -179.8(10) . . . . ?
C2 N1 N2 N3 0.6(11) . . . . ?
C2 N1 N2 C1 -179.9(10) . . . . ?
C2 N5 N6 N7 178.5(8) . . . . ?
C3 N10 N11 N12 1.2(13) . . . . ?
C4 N12 N13 C3 -176.7(10) . . . . ?
C5 N7 N8 N9 4.4(13) . . . . ?
C5 N14 N15 N16 -0.3(11) . . . . ?
C6 N16 N17 C5 177.9(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
