# Electronic Supplementary Material (ESI) for Green 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_1
_database_code_depnum_ccdc_archive 'CCDC 873748'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11.43 H12.57 N1.14'
_chemical_formula_weight         165.94

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.815(2)
_cell_length_b                   19.201(4)
_cell_length_c                   7.8580(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.80(3)
_cell_angle_gamma                90.00
_cell_volume                     1577.8(6)
_cell_formula_units_Z            7
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12755
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3570
_reflns_number_gt                1926
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1481P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.056(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3570
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2812
_refine_ls_wR_factor_gt          0.2097
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2691(2) 1.03410(12) 0.7892(3) 0.0562(6) Uani 1 1 d . . .
C8 C 0.3330(2) 0.91131(14) 0.7523(4) 0.0502(7) Uani 1 1 d . . .
N2 N 0.3185(2) 0.83854(13) 0.9991(4) 0.0638(7) Uani 1 1 d . . .
H2N H 0.3565 0.8093 1.0781 0.077 Uiso 1 1 calc R . .
C14 C 0.2035(2) 0.87371(15) 1.0177(4) 0.0559(7) Uani 1 1 d . . .
H14 H 0.1301 0.8527 0.9339 0.067 Uiso 1 1 calc R . .
C6 C 0.1645(3) 1.05493(16) 0.4817(4) 0.0591(8) Uani 1 1 d . . .
H6 H 0.1488 1.0076 0.4625 0.071 Uiso 1 1 calc R . .
C7 C 0.2310(2) 0.96062(13) 0.7862(4) 0.0506(7) Uani 1 1 d . . .
H7 H 0.1504 0.9536 0.6966 0.061 Uiso 1 1 calc R . .
C5 C 0.2292(2) 1.07842(15) 0.6498(4) 0.0528(7) Uani 1 1 d . . .
C13 C 0.3671(2) 0.85154(14) 0.8565(4) 0.0520(7) Uani 1 1 d . . .
C18 C 0.2099(2) 0.94977(14) 0.9695(4) 0.0532(7) Uani 1 1 d . . .
H18 H 0.1282 0.9715 0.9713 0.064 Uiso 1 1 calc R . .
C20 C 0.3175(3) 1.05819(15) 0.9702(4) 0.0583(8) Uani 1 1 d . . .
H20A H 0.2626 1.0941 0.9978 0.070 Uiso 1 1 calc R . .
H20B H 0.4034 1.0767 0.9889 0.070 Uiso 1 1 calc R . .
C9 C 0.3969(3) 0.92610(16) 0.6248(4) 0.0586(7) Uani 1 1 d . . .
H9 H 0.3769 0.9667 0.5589 0.070 Uiso 1 1 calc R . .
C4 C 0.2541(3) 1.15029(15) 0.6692(5) 0.0634(8) Uani 1 1 d . . .
H4 H 0.2996 1.1676 0.7776 0.076 Uiso 1 1 calc R . .
C12 C 0.4590(3) 0.80595(16) 0.8187(4) 0.0629(8) Uani 1 1 d . . .
H12 H 0.4788 0.7647 0.8815 0.075 Uiso 1 1 calc R . .
C10 C 0.4901(3) 0.88187(17) 0.5927(4) 0.0647(8) Uani 1 1 d . . .
H10 H 0.5320 0.8927 0.5064 0.078 Uiso 1 1 calc R . .
C19 C 0.3171(3) 0.99415(15) 1.0825(4) 0.0589(8) Uani 1 1 d . . .
H19A H 0.2991 1.0063 1.1936 0.071 Uiso 1 1 calc R . .
H19B H 0.3985 0.9700 1.1057 0.071 Uiso 1 1 calc R . .
C11 C 0.5193(3) 0.82208(17) 0.6900(5) 0.0650(8) Uani 1 1 d . . .
H11 H 0.5810 0.7920 0.6685 0.078 Uiso 1 1 calc R . .
C1 C 0.1235(3) 1.10155(18) 0.3433(5) 0.0690(9) Uani 1 1 d . . .
H1 H 0.0802 1.0849 0.2330 0.083 Uiso 1 1 calc R . .
C15 C 0.1874(3) 0.86218(18) 1.1998(5) 0.0668(9) Uani 1 1 d . . .
H15 H 0.2549 0.8816 1.2957 0.080 Uiso 1 1 calc R . .
C3 C 0.2121(3) 1.19523(17) 0.5302(6) 0.0762(10) Uani 1 1 d . . .
H3 H 0.2287 1.2426 0.5472 0.091 Uiso 1 1 calc R . .
C2 C 0.1460(3) 1.17193(19) 0.3665(6) 0.0761(10) Uani 1 1 d . . .
H2 H 0.1173 1.2030 0.2740 0.091 Uiso 1 1 calc R . .
C16 C 0.1275(4) 0.7972(2) 1.2421(6) 0.0895(12) Uani 1 1 d . . .
H16A H 0.0995 0.7633 1.1486 0.107 Uiso 1 1 calc R . .
H16B H 0.1603 0.7775 1.3585 0.107 Uiso 1 1 calc R . .
C17 C 0.0566(3) 0.8632(2) 1.2281(6) 0.0847(11) Uani 1 1 d . . .
H17A H 0.0459 0.8840 1.3360 0.102 Uiso 1 1 calc R . .
H17B H -0.0149 0.8698 1.1261 0.102 Uiso 1 1 calc R . .


_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 C5 1.367(4) . ?
N1 C20 1.460(4) . ?
N1 C7 1.468(3) . ?
C8 C9 1.384(4) . ?
C8 C13 1.404(4) . ?
C8 C7 1.528(3) . ?
N2 C13 1.377(4) . ?
N2 C14 1.455(3) . ?
C14 C15 1.502(4) . ?
C14 C18 1.515(4) . ?
C6 C1 1.391(4) . ?
C6 C5 1.402(4) . ?
C7 C18 1.529(4) . ?
C5 C4 1.407(4) . ?
C13 C12 1.412(4) . ?
C18 C19 1.528(4) . ?
C20 C19 1.514(4) . ?
C9 C10 1.390(4) . ?
C4 C3 1.375(5) . ?
C12 C11 1.371(4) . ?
C10 C11 1.371(5) . ?
C1 C2 1.377(5) . ?
C15 C16 1.482(5) . ?
C15 C17 1.487(4) . ?
C3 C2 1.377(5) . ?
C16 C17 1.470(5) . ?

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
C5 N1 C20 123.0(2) . . ?
C5 N1 C7 123.8(2) . . ?
C20 N1 C7 110.4(2) . . ?
C9 C8 C13 119.0(2) . . ?
C9 C8 C7 121.0(3) . . ?
C13 C8 C7 119.9(2) . . ?
C13 N2 C14 120.8(2) . . ?
N2 C14 C15 109.8(3) . . ?
N2 C14 C18 109.1(2) . . ?
C15 C14 C18 113.9(2) . . ?
C1 C6 C5 120.8(3) . . ?
N1 C7 C8 112.7(2) . . ?
N1 C7 C18 103.0(2) . . ?
C8 C7 C18 111.6(2) . . ?
N1 C5 C6 122.3(3) . . ?
N1 C5 C4 120.8(3) . . ?
C6 C5 C4 117.0(3) . . ?
N2 C13 C8 121.7(2) . . ?
N2 C13 C12 119.7(3) . . ?
C8 C13 C12 118.6(3) . . ?
C14 C18 C19 117.9(3) . . ?
C14 C18 C7 113.2(2) . . ?
C19 C18 C7 101.4(2) . . ?
N1 C20 C19 104.9(2) . . ?
C8 C9 C10 121.7(3) . . ?
C3 C4 C5 121.0(3) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C10 C9 119.0(3) . . ?
C20 C19 C18 103.3(3) . . ?
C12 C11 C10 121.0(3) . . ?
C2 C1 C6 121.2(3) . . ?
C16 C15 C17 59.4(2) . . ?
C16 C15 C14 120.1(3) . . ?
C17 C15 C14 119.2(3) . . ?
C4 C3 C2 121.7(3) . . ?
C1 C2 C3 118.3(3) . . ?
C17 C16 C15 60.5(2) . . ?
C16 C17 C15 60.1(2) . . ?

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
C13 N2 C14 C15 -168.0(3) . . . . ?
C13 N2 C14 C18 -42.6(4) . . . . ?
C5 N1 C7 C8 99.4(3) . . . . ?
C20 N1 C7 C8 -99.1(3) . . . . ?
C5 N1 C7 C18 -140.2(2) . . . . ?
C20 N1 C7 C18 21.3(3) . . . . ?
C9 C8 C7 N1 -43.4(4) . . . . ?
C13 C8 C7 N1 133.8(3) . . . . ?
C9 C8 C7 C18 -158.7(3) . . . . ?
C13 C8 C7 C18 18.4(3) . . . . ?
C20 N1 C5 C6 -169.7(2) . . . . ?
C7 N1 C5 C6 -10.4(4) . . . . ?
C20 N1 C5 C4 11.5(4) . . . . ?
C7 N1 C5 C4 170.8(2) . . . . ?
C1 C6 C5 N1 179.0(2) . . . . ?
C1 C6 C5 C4 -2.2(4) . . . . ?
C14 N2 C13 C8 18.5(4) . . . . ?
C14 N2 C13 C12 -165.1(3) . . . . ?
C9 C8 C13 N2 171.9(3) . . . . ?
C7 C8 C13 N2 -5.3(4) . . . . ?
C9 C8 C13 C12 -4.6(4) . . . . ?
C7 C8 C13 C12 178.2(2) . . . . ?
N2 C14 C18 C19 -63.1(3) . . . . ?
C15 C14 C18 C19 59.9(3) . . . . ?
N2 C14 C18 C7 55.0(3) . . . . ?
C15 C14 C18 C7 178.0(2) . . . . ?
N1 C7 C18 C14 -164.8(2) . . . . ?
C8 C7 C18 C14 -43.7(3) . . . . ?
N1 C7 C18 C19 -37.5(3) . . . . ?
C8 C7 C18 C19 83.7(3) . . . . ?
C5 N1 C20 C19 165.7(2) . . . . ?
C7 N1 C20 C19 4.0(3) . . . . ?
C13 C8 C9 C10 2.7(4) . . . . ?
C7 C8 C9 C10 179.8(2) . . . . ?
N1 C5 C4 C3 -178.7(2) . . . . ?
C6 C5 C4 C3 2.4(4) . . . . ?
N2 C13 C12 C11 -172.5(3) . . . . ?
C8 C13 C12 C11 4.0(4) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
N1 C20 C19 C18 -27.8(3) . . . . ?
C14 C18 C19 C20 164.5(2) . . . . ?
C7 C18 C19 C20 40.3(3) . . . . ?
C13 C12 C11 C10 -1.4(5) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C5 C6 C1 C2 0.5(4) . . . . ?
N2 C14 C15 C16 -82.6(4) . . . . ?
C18 C14 C15 C16 154.7(3) . . . . ?
N2 C14 C15 C17 -152.1(3) . . . . ?
C18 C14 C15 C17 85.2(4) . . . . ?
C5 C4 C3 C2 -1.0(4) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C4 C3 C2 C1 -0.7(5) . . . . ?
C14 C15 C16 C17 -108.2(4) . . . . ?
C14 C15 C17 C16 109.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.080
