# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1437555'
_audit_update_record             
;
2016-03-15 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;
_audit_creation_date             2015-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         '0.25(C18 H20 N4 O2)'
_chemical_formula_sum            'C4.5 H5 N O0.5'
_chemical_formula_weight         81.10
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   5.016(1)
_cell_length_b                   5.4660(11)
_cell_length_c                   16.124(3)
_cell_angle_alpha                93.12(3)
_cell_angle_beta                 96.16(3)
_cell_angle_gamma                93.03(3)
_cell_volume                     438.11(15)
_cell_formula_units_Z            4
_exptl_absorpt_coefficient_mu    0.083
_exptl_crystal_density_diffrn    1.2294
_exptl_crystal_F_000             172.0736
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1515
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1394
_diffrn_reflns_theta_full        25.3755
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.27
_diffrn_measured_fraction_theta_full 0.8653
_diffrn_measured_fraction_theta_max 0.8653
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              6
_reflns_limit_k_min              -6
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                583
_reflns_number_total             1394
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.4921
_refine_diff_density_min         -0.5576
_refine_diff_density_rms         0.1224
_refine_ls_d_res_high            0.8292
_refine_ls_d_res_low             16.0015
_refine_ls_goodness_of_fit_ref   0.9548
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1394
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1943
_refine_ls_R_factor_gt           0.0795
_refine_ls_restrained_S_all      0.9537
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0884P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.2173
_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. Rigid bond restraints
 C1, C2
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C2, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3, N4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b)
3.b Me refined with riding coordinates:
 C1(H1a,H1b,H1c)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
O O -0.2023(6) 0.7330(7) 0.7461(2) 0.0839(14) Uani 1.000000 . .
N N 0.2282(8) 0.2689(7) 0.9752(2) 0.0519(11) Uani 1.000000 . .
C1 C 0.3218(16) 1.2810(13) 0.5706(4) 0.137(3) Uani 1.000000 . U
H1a H 0.4746(16) 1.3899(13) 0.5650(4) 0.205(5) Uiso 1.000000 R .
H1b H 0.2886(16) 1.1689(13) 0.5222(4) 0.205(5) Uiso 1.000000 R .
H1c H 0.1672(16) 1.3748(13) 0.5756(4) 0.205(5) Uiso 1.000000 R .
C2 C 0.3773(14) 1.1383(13) 0.6479(4) 0.110(2) Uani 1.000000 . U
H2a H 0.5375(14) 1.0494(13) 0.6426(4) 0.132(3) Uiso 1.000000 R .
H2b H 0.4164(14) 1.2547(13) 0.6959(4) 0.132(3) Uiso 1.000000 R .
C3 C 0.1756(12) 0.9742(14) 0.6641(4) 0.115(3) Uani 1.000000 . U
H3a H 0.0198(12) 1.0638(14) 0.6749(4) 0.138(3) Uiso 1.000000 R .
H3b H 0.1251(12) 0.8653(14) 0.6148(4) 0.138(3) Uiso 1.000000 R .
N4 N 0.2485(8) 0.8264(8) 0.7352(3) 0.0773(15) Uani 1.000000 . U
C5 C 0.0303(9) 0.7202(9) 0.7718(3) 0.0582(14) Uani 1.000000 . .
C6 C 0.1102(8) 0.5569(8) 0.8426(3) 0.0411(11) Uani 1.000000 . .
C7 C 0.3313(8) 0.6176(8) 0.8998(3) 0.0489(13) Uani 1.000000 . .
H7 H 0.4435(8) 0.7547(8) 0.8934(3) 0.0587(15) Uiso 1.000000 R .
C8 C 0.3860(8) 0.4703(8) 0.9678(3) 0.0433(12) Uani 1.000000 . .
C9 C 0.0219(9) 0.2157(8) 0.9192(3) 0.0472(12) Uani 1.000000 . .
H9 H -0.0832(9) 0.0735(8) 0.9248(3) 0.0567(15) Uiso 1.000000 R .
C10 C -0.0516(8) 0.3540(8) 0.8525(3) 0.0466(12) Uani 1.000000 . .
H10 H -0.2049(8) 0.3111(8) 0.8157(3) 0.0559(14) Uiso 1.000000 R .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O 0.0424(19) 0.118(3) 0.097(3) 0.018(2) -0.0003(19) 0.059(3)
N 0.052(2) 0.035(2) 0.072(3) 0.006(2) 0.013(2) 0.008(2)
C1 0.193(8) 0.138(6) 0.104(5) 0.079(6) 0.061(5) 0.081(5)
C2 0.123(6) 0.115(6) 0.097(5) 0.006(4) 0.007(4) 0.048(4)
C3 0.073(4) 0.163(7) 0.122(6) 0.014(4) 0.022(4) 0.108(6)
N4 0.067(3) 0.097(3) 0.076(3) 0.020(3) 0.016(2) 0.055(3)
C5 0.051(3) 0.067(3) 0.062(3) 0.024(3) 0.012(2) 0.024(3)
C6 0.032(2) 0.046(3) 0.049(3) 0.018(2) 0.013(2) 0.004(2)
C7 0.041(3) 0.044(3) 0.068(3) 0.017(2) 0.019(2) 0.018(3)
C8 0.037(2) 0.038(2) 0.056(3) 0.013(2) 0.006(2) 0.002(2)
C9 0.046(3) 0.040(3) 0.056(3) 0.005(2) 0.004(2) 0.002(2)
C10 0.042(2) 0.046(3) 0.054(3) 0.002(2) 0.012(2) 0.011(2)

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
O C5 1.202(5) . ?
N C8 1.340(5) . ?
N C9 1.307(5) . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C1 C2 1.515(7) . ?
C2 H2a 0.9700 . ?
C2 H2b 0.9700 . ?
C2 C3 1.372(7) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C3 N4 1.464(6) . ?
N4 C5 1.412(6) . ?
C5 C6 1.520(6) . ?
C6 C7 1.378(6) . ?
C6 C10 1.366(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.408(6) . ?
C8 C8 1.469(8) 2_667 ?
C9 H9 0.9300 . ?
C9 C10 1.378(6) . ?
C10 H10 0.9300 . ?

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
C9 N C8 118.8(4) . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
C2 C1 H1a 109.5 . . ?
C2 C1 H1b 109.5 . . ?
C2 C1 H1c 109.5 . . ?
H2a C2 C1 108.3(4) . . ?
H2b C2 C1 108.3(4) . . ?
H2b C2 H2a 107.4 . . ?
C3 C2 C1 116.1(6) . . ?
C3 C2 H2a 108.3(4) . . ?
C3 C2 H2b 108.3(4) . . ?
H3a C3 C2 108.8(4) . . ?
H3b C3 C2 108.8(4) . . ?
H3b C3 H3a 107.7 . . ?
N4 C3 C2 113.8(6) . . ?
N4 C3 H3a 108.8(3) . . ?
N4 C3 H3b 108.8(4) . . ?
C5 N4 C3 115.3(4) . . ?
N4 C5 O 124.8(4) . . ?
C6 C5 O 120.4(5) . . ?
C6 C5 N4 114.4(4) . . ?
C7 C6 C5 121.5(4) . . ?
C10 C6 C5 118.8(4) . . ?
C10 C6 C7 119.6(4) . . ?
H7 C7 C6 120.3(3) . . ?
C8 C7 C6 119.4(4) . . ?
C8 C7 H7 120.3(3) . . ?
C7 C8 N 120.0(4) . . ?
C8 C8 N 118.1(5) 2_667 . ?
C8 C8 C7 122.0(5) 2_667 . ?
H9 C9 N 117.5(3) . . ?
C10 C9 N 125.0(5) . . ?
C10 C9 H9 117.5(3) . . ?
C9 C10 C6 117.1(4) . . ?
H10 C10 C6 121.4(3) . . ?
H10 C10 C9 121.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_rigid_atom_site_label_1
_restr_U_rigid_atom_site_label_2
_restr_U_rigid_target_weight_param
_restr_U_rigid_U_parallel
_restr_U_rigid_diff
C1 C2 0.0050 0.0534 -0.0168
C2 C3 0.0100 0.0899 0.0271
C3 N4 0.0100 0.0363 0.0060

