# Electronic Supplementary Material (ESI) for Nanoscale.
# This journal is © The Royal Society of Chemistry 2016

 
data_shelx
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C21 H12 N3 O3' 
_chemical_formula_weight          354.34

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'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 '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'
 
_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                    7.5752(18)
_cell_length_b                    25.656(5)
_cell_length_c                    11.692(2)
_cell_angle_alpha                 90
_cell_angle_beta                  100.740(13)
_cell_angle_gamma                 90
_cell_volume                      2232.6(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     3045 
_cell_measurement_theta_min       2.38 
_cell_measurement_theta_max       19.62
 
_exptl_crystal_description        block 
_exptl_crystal_colour             blue 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.054          
_exptl_crystal_F_000              732
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.073
_shelx_estimated_absorpt_T_min    0.986
_shelx_estimated_absorpt_T_max    0.986
_exptl_absorpt_correction_T_max   0.7461
_exptl_absorpt_correction_T_min   0.6402
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.0920 before and 0.0683 after correction. 
The Ratio of minimum to maximum transmission is 0.8581. 
The λ/2 correction factor is 0.0015.
; 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?                       
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             25125
_diffrn_reflns_av_unetI/netI      0.0850
_diffrn_reflns_av_R_equivalents   0.0807
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -30
_diffrn_reflns_limit_k_max        30
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          1.587
_diffrn_reflns_theta_max          25.000
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.991
_diffrn_measured_fraction_theta_full  0.962
_diffrn_reflns_Laue_measured_fraction_max    0.991
_diffrn_reflns_Laue_measured_fraction_full   0.962
_diffrn_reflns_point_group_measured_fraction_max   0.991
_diffrn_reflns_point_group_measured_fraction_full  0.962
_reflns_number_total              3881
_reflns_number_gt                 1908
_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        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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)+(0.2000P)²]
 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        0.002(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3881
_refine_ls_number_parameters      245
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2061
_refine_ls_R_factor_gt            0.1417
_refine_ls_wR_factor_ref          0.4303
_refine_ls_wR_factor_gt           0.4057
_refine_ls_goodness_of_fit_ref    1.359
_refine_ls_restrained_S_all       1.359
_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
C0AA C 0.4663(13) 0.5980(4) 0.0058(11) 0.100(4) Uani 1 1 d . . . . .
H0AA H 0.4706 0.6340 0.0254 0.121 Uiso 1 1 calc R U . . .
C1AA C 0.6794(16) 0.5732(4) 0.1964(15) 0.127(5) Uani 1 1 d . . . . .
H1AA H 0.6948 0.6082 0.2225 0.153 Uiso 1 1 calc R U . . .
C2 C 0.2341(18) 0.5178(4) -0.2410(11) 0.123(4) Uani 1 1 d . . . . .
H2 H 0.1654 0.5420 -0.2925 0.148 Uiso 1 1 calc R U . . .
C2AA C 0.7599(14) 0.5340(4) 0.2590(10) 0.105(3) Uani 1 1 d . . . . .
H2AA H 0.8277 0.5446 0.3320 0.126 Uiso 1 1 calc R U . . .
C3AA C 0.3498(12) 0.5309(2) -0.1301(12) 0.106(4) Uani 1 1 d . . . . .
C4AA C 0.3681(17) 0.5855(3) -0.0941(12) 0.111(4) Uani 1 1 d . . . . .
H4AA H 0.3083 0.6120 -0.1437 0.133 Uiso 1 1 calc R U . . .
C6 C 0.5766(16) 0.5610(3) 0.0960(15) 0.120(4) Uani 1 1 d . . . . .
C8 C 0.5530(14) 0.5070(3) 0.0483(9) 0.095(3) Uani 1 1 d . . . . .
C10 C 0.9601(10) 0.1380(3) 0.0568(7) 0.068(2) Uani 1 1 d . . . . .
H10 H 0.9459 0.1149 0.1179 0.082 Uiso 1 1 calc R U . . .
C11 C 0.9352(8) 0.1885(2) 0.0712(5) 0.0495(16) Uani 1 1 d . . . . .
H11 H 0.9029 0.2009 0.1410 0.059 Uiso 1 1 calc R U . . .
C12 C 0.9295(9) 0.2798(2) 0.0057(5) 0.0506(17) Uani 1 1 d . . . . .
C14 C 1.1143(11) 0.3845(2) 0.0632(7) 0.066(2) Uani 1 1 d . . . . .
C15 C 1.1111(9) 0.4426(2) 0.0795(5) 0.0503(17) Uani 1 1 d . . . . .
C16 C 1.2058(11) 0.4666(2) 0.1750(6) 0.062(2) Uani 1 1 d . . . . .
H16 H 1.2755 0.4464 0.2350 0.074 Uiso 1 1 calc R U . . .
C17 C 1.2017(11) 0.5198(2) 0.1856(5) 0.061(2) Uani 1 1 d . . . . .
H17 H 1.2734 0.5357 0.2517 0.074 Uiso 1 1 calc R U . . .
C18 C 1.1004(9) 0.5499(2) 0.1064(5) 0.0513(17) Uani 1 1 d . . . . .
C19 C 1.0962(11) 0.6068(3) 0.1192(7) 0.065(2) Uani 1 1 d . . . . .
C20 C 1.0088(14) 0.2051(2) -0.1149(7) 0.090(3) Uani 1 1 d . . . . .
H20 H 1.0372 0.2274 -0.1738 0.108 Uiso 1 1 calc R U . . .
C21 C 1.0184(10) 0.1490(2) -0.1240(6) 0.0617(19) Uani 1 1 d . . . . .
H21 H 1.0356 0.1349 -0.1962 0.074 Uiso 1 1 calc R U . . .
C22 C 0.9998(8) 0.4720(2) -0.0066(5) 0.0437(15) Uani 1 1 d . . . . .
C27 C 0.9572(9) 0.2243(2) -0.0183(5) 0.0523(17) Uani 1 1 d . . . . .
N2 N 1.0269(9) 0.36485(18) -0.0333(5) 0.0651(18) Uani 1 1 d . . . . .
N7 N 1.0057(9) 0.11741(19) -0.0433(6) 0.0720(18) Uani 1 1 d . . . . .
N8 N 1.0244(11) 0.31088(19) -0.0591(5) 0.090(2) Uani 1 1 d . . . . .
H8 H 1.0794 0.2979 -0.1126 0.108 Uiso 1 1 calc R U . . .
O0AA O 1.1854(9) 0.62976(18) 0.2061(5) 0.0890(19) Uani 1 1 d . . . . .
O1AA O 1.2044(8) 0.35708(17) 0.1401(4) 0.0783(16) Uani 1 1 d . . . . .
O3 O 0.8415(8) 0.29666(15) 0.0712(4) 0.0729(17) 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
C0AA C4AA 1.303(14) . ?
C0AA C6 1.543(16) . ?
C0AA H0AA 0.9500 . ?
C1AA C6 1.319(17) . ?
C1AA C2AA 1.323(16) . ?
C1AA H1AA 0.9500 . ?
C2 C2AA 1.346(14) 3_665 ?
C2 C3AA 1.463(15) . ?
C2 H2 0.9500 . ?
C2AA C2 1.346(14) 3_665 ?
C2AA H2AA 0.9500 . ?
C3AA C4AA 1.462(12) . ?
C3AA C8 1.463(15) 3_665 ?
C4AA H4AA 0.9500 . ?
C6 C8 1.493(14) . ?
C8 C8 1.31(2) 3_665 ?
C8 C3AA 1.463(15) 3_665 ?
C10 C11 1.324(8) . ?
C10 N7 1.385(9) . ?
C10 H10 0.9500 . ?
C11 C27 1.425(8) . ?
C11 H11 0.9500 . ?
C12 O3 1.187(7) . ?
C12 N8 1.389(8) . ?
C12 C27 1.474(9) . ?
C14 O1AA 1.242(8) . ?
C14 N2 1.300(10) . ?
C14 C15 1.502(9) . ?
C15 C16 1.357(9) . ?
C15 C22 1.407(8) . ?
C16 C17 1.370(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.334(9) . ?
C17 H17 0.9500 . ?
C18 C22 1.387(8) 3_765 ?
C18 C19 1.468(9) . ?
C19 O0AA 1.257(9) . ?
C19 N2 1.434(10) 3_765 ?
C20 C27 1.355(9) . ?
C20 C21 1.444(9) . ?
C20 H20 0.9500 . ?
C21 N7 1.262(8) . ?
C21 H21 0.9500 . ?
C22 C18 1.387(8) 3_765 ?
C22 C22 1.443(11) 3_765 ?
N2 N8 1.416(7) . ?
N2 C19 1.434(10) 3_765 ?
N8 H8 0.8800 . ?
 
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
C4AA C0AA C6 127.4(11) . . ?
C4AA C0AA H0AA 116.3 . . ?
C6 C0AA H0AA 116.3 . . ?
C6 C1AA C2AA 116.6(9) . . ?
C6 C1AA H1AA 121.7 . . ?
C2AA C1AA H1AA 121.7 . . ?
C2AA C2 C3AA 109.5(10) 3_665 . ?
C2AA C2 H2 125.2 3_665 . ?
C3AA C2 H2 125.2 . . ?
C1AA C2AA C2 133.5(12) . 3_665 ?
C1AA C2AA H2AA 113.3 . . ?
C2 C2AA H2AA 113.3 3_665 . ?
C4AA C3AA C8 116.1(11) . 3_665 ?
C4AA C3AA C2 119.0(10) . . ?
C8 C3AA C2 124.9(7) 3_665 . ?
C0AA C4AA C3AA 120.1(12) . . ?
C0AA C4AA H4AA 120.0 . . ?
C3AA C4AA H4AA 120.0 . . ?
C1AA C6 C8 124.1(10) . . ?
C1AA C6 C0AA 128.2(11) . . ?
C8 C6 C0AA 107.7(12) . . ?
C8 C8 C3AA 122.4(10) 3_665 3_665 ?
C8 C8 C6 126.1(13) 3_665 . ?
C3AA C8 C6 111.3(10) 3_665 . ?
C11 C10 N7 123.0(7) . . ?
C11 C10 H10 118.5 . . ?
N7 C10 H10 118.5 . . ?
C10 C11 C27 119.9(6) . . ?
C10 C11 H11 120.1 . . ?
C27 C11 H11 120.1 . . ?
O3 C12 N8 123.5(6) . . ?
O3 C12 C27 126.3(6) . . ?
N8 C12 C27 110.2(6) . . ?
O1AA C14 N2 122.0(6) . . ?
O1AA C14 C15 119.4(8) . . ?
N2 C14 C15 118.5(6) . . ?
C16 C15 C22 119.9(6) . . ?
C16 C15 C14 122.4(6) . . ?
C22 C15 C14 117.6(6) . . ?
C15 C16 C17 120.6(6) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 122.2(7) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C22 120.2(6) . 3_765 ?
C17 C18 C19 121.7(7) . . ?
C22 C18 C19 118.1(6) 3_765 . ?
O0AA C19 N2 120.6(6) . 3_765 ?
O0AA C19 C18 122.0(7) . . ?
N2 C19 C18 117.1(7) 3_765 . ?
C27 C20 C21 116.7(6) . . ?
C27 C20 H20 121.6 . . ?
C21 C20 H20 121.6 . . ?
N7 C21 C20 125.0(6) . . ?
N7 C21 H21 117.5 . . ?
C20 C21 H21 117.5 . . ?
C18 C22 C15 123.0(6) 3_765 . ?
C18 C22 C22 118.9(7) 3_765 3_765 ?
C15 C22 C22 117.9(7) . 3_765 ?
C20 C27 C11 118.0(6) . . ?
C20 C27 C12 125.7(6) . . ?
C11 C27 C12 116.2(5) . . ?
C14 N2 N8 123.3(6) . . ?
C14 N2 C19 124.8(6) . 3_765 ?
N8 N2 C19 111.5(6) . 3_765 ?
C21 N7 C10 116.9(5) . . ?
C12 N8 N2 115.7(6) . . ?
C12 N8 H8 122.1 . . ?
N2 N8 H8 122.1 . . ?
 
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
C6 C1AA C2AA C2 2.7(19) . . . 3_665 ?
C2AA C2 C3AA C4AA 178.2(8) 3_665 . . . ?
C2AA C2 C3AA C8 -3.7(13) 3_665 . . 3_665 ?
C6 C0AA C4AA C3AA 1.7(14) . . . . ?
C8 C3AA C4AA C0AA -0.1(12) 3_665 . . . ?
C2 C3AA C4AA C0AA 178.1(9) . . . . ?
C2AA C1AA C6 C8 -2.5(16) . . . . ?
C2AA C1AA C6 C0AA 179.6(8) . . . . ?
C4AA C0AA C6 C1AA 178.6(11) . . . . ?
C4AA C0AA C6 C8 0.5(12) . . . . ?
C1AA C6 C8 C8 176.9(12) . . . 3_665 ?
C0AA C6 C8 C8 -4.9(15) . . . 3_665 ?
C1AA C6 C8 C3AA 3.2(13) . . . 3_665 ?
C0AA C6 C8 C3AA -178.6(7) . . . 3_665 ?
N7 C10 C11 C27 -0.6(11) . . . . ?
O1AA C14 C15 C16 1.0(9) . . . . ?
N2 C14 C15 C16 -176.6(6) . . . . ?
O1AA C14 C15 C22 -176.6(6) . . . . ?
N2 C14 C15 C22 5.8(9) . . . . ?
C22 C15 C16 C17 -3.6(9) . . . . ?
C14 C15 C16 C17 178.9(6) . . . . ?
C15 C16 C17 C18 2.8(10) . . . . ?
C16 C17 C18 C22 -2.8(10) . . . 3_765 ?
C16 C17 C18 C19 179.5(6) . . . . ?
C17 C18 C19 O0AA -1.1(10) . . . . ?
C22 C18 C19 O0AA -178.8(6) 3_765 . . . ?
C17 C18 C19 N2 -175.7(6) . . . 3_765 ?
C22 C18 C19 N2 6.6(8) 3_765 . . 3_765 ?
C27 C20 C21 N7 -9.8(13) . . . . ?
C16 C15 C22 C18 179.9(6) . . . 3_765 ?
C14 C15 C22 C18 -2.5(8) . . . 3_765 ?
C16 C15 C22 C22 4.2(9) . . . 3_765 ?
C14 C15 C22 C22 -178.1(6) . . . 3_765 ?
C21 C20 C27 C11 6.5(12) . . . . ?
C21 C20 C27 C12 -176.7(7) . . . . ?
C10 C11 C27 C20 -2.0(10) . . . . ?
C10 C11 C27 C12 -179.2(6) . . . . ?
O3 C12 C27 C20 158.6(8) . . . . ?
N8 C12 C27 C20 -22.3(10) . . . . ?
O3 C12 C27 C11 -24.5(10) . . . . ?
N8 C12 C27 C11 154.7(6) . . . . ?
O1AA C14 N2 N8 0.8(11) . . . . ?
C15 C14 N2 N8 178.4(6) . . . . ?
O1AA C14 N2 C19 172.2(6) . . . 3_765 ?
C15 C14 N2 C19 -10.2(10) . . . 3_765 ?
C20 C21 N7 C10 7.3(12) . . . . ?
C11 C10 N7 C21 -2.0(11) . . . . ?
O3 C12 N8 N2 6.7(11) . . . . ?
C27 C12 N8 N2 -172.5(6) . . . . ?
C14 N2 N8 C12 70.0(10) . . . . ?
C19 N2 N8 C12 -102.3(7) 3_765 . . . ?
 
_refine_diff_density_max    0.417
_refine_diff_density_min   -0.346
_refine_diff_density_rms    0.101

_shelxl_version_number 2013-2



# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1 -0.247  0.011 -0.022       802       300 ' '
_platon_squeeze_details
;
;

