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

 
data_3
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C27 H24 N2 O3'
_chemical_formula_sum
 'C27 H24 N2 O3' 
_chemical_formula_weight          424.48

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'
 'O'  'O'   0.0106   0.0060
 '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                    10.2888(5)
_cell_length_b                    16.2882(10)
_cell_length_c                    13.2480(6)
_cell_angle_alpha                 90
_cell_angle_beta                  91.491(5)
_cell_angle_gamma                 90
_cell_volume                      2219.4(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     5017
_cell_measurement_theta_min       3.191
_cell_measurement_theta_max       28.712
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.270          
_exptl_crystal_F_000              736
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_absorpt_coefficient_mu     0.083
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'CCD area detector'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             9684
_diffrn_reflns_av_unetI/netI      0.0526
_diffrn_reflns_av_R_equivalents   0.0248
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.191
_diffrn_reflns_theta_max          28.712
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.876
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.876
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.876
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              5017
_reflns_number_gt                 2549
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1800P)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      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          5017
_refine_ls_number_parameters      290
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1447
_refine_ls_R_factor_gt            0.0799
_refine_ls_wR_factor_ref          0.3323
_refine_ls_wR_factor_gt           0.2671
_refine_ls_goodness_of_fit_ref    1.062
_refine_ls_restrained_S_all       1.062
_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
O O 0.5761(2) 0.33738(14) 0.25861(15) 0.0595(7) Uani 1 1 d . . . . .
O1 O 0.5905(2) 0.47469(16) 0.77192(15) 0.0709(8) Uani 1 1 d . . . . .
O1AA O 0.8858(3) 0.57910(19) 0.55805(19) 0.0866(9) Uani 1 1 d . . . . .
N2 N 0.7358(3) 0.52798(18) 0.66336(18) 0.0585(7) Uani 1 1 d . . . . .
C1AA C 0.6358(3) 0.38473(18) 0.3320(2) 0.0455(7) Uani 1 1 d . . . . .
C2AA C 0.5802(3) 0.42475(18) 0.60404(19) 0.0450(7) Uani 1 1 d . . . . .
C3AA C 0.6329(3) 0.42899(17) 0.5067(2) 0.0411(7) Uani 1 1 d . . . . .
N1 N 0.7841(3) 0.23790(19) 0.2135(2) 0.0655(8) Uani 1 1 d . . . . .
C4AA C 0.6347(3) 0.4758(2) 0.6862(2) 0.0519(8) Uani 1 1 d . . . . .
C5AA C 0.7263(3) 0.28360(19) 0.1381(2) 0.0492(8) Uani 1 1 d . . . . .
C6AA C 0.5781(3) 0.38006(18) 0.42797(19) 0.0436(7) Uani 1 1 d . . . . .
C1 C 0.7396(3) 0.48128(19) 0.4880(2) 0.0479(8) Uani 1 1 d . . . . .
C2 C 0.7640(3) 0.2788(2) 0.0358(2) 0.0569(9) Uani 1 1 d . . . . .
C8AA C 0.6244(3) 0.3381(2) 0.1607(2) 0.0520(8) Uani 1 1 d . . . . .
C9AA C 0.7403(3) 0.4341(2) 0.3154(2) 0.0566(8) Uani 1 1 d . . . . .
H9AA H 0.7767 0.4361 0.2520 0.068 Uiso 1 1 calc R U . . .
C0BA C 0.4776(3) 0.3724(2) 0.6216(2) 0.0566(9) Uani 1 1 d . . . . .
H0BA H 0.4438 0.3691 0.6859 0.068 Uiso 1 1 calc R U . . .
C1BA C 0.7921(3) 0.4818(2) 0.3947(2) 0.0563(8) Uani 1 1 d . . . . .
H1BA H 0.8642 0.5147 0.3833 0.068 Uiso 1 1 calc R U . . .
C2BA C 0.7942(3) 0.5326(2) 0.5689(2) 0.0597(9) Uani 1 1 d . . . . .
C3BA C 0.4733(3) 0.3282(2) 0.4486(2) 0.0541(8) Uani 1 1 d . . . . .
H3BA H 0.4367 0.2960 0.3973 0.065 Uiso 1 1 calc R U . . .
C4BA C 0.4243(3) 0.3247(2) 0.5440(2) 0.0608(9) Uani 1 1 d . . . . .
H4BA H 0.3549 0.2900 0.5568 0.073 Uiso 1 1 calc R U . . .
C3 C 0.5668(4) 0.3868(2) 0.0899(3) 0.0640(9) Uani 1 1 d . . . . .
H3 H 0.5015 0.4231 0.1076 0.077 Uiso 1 1 calc R U . . .
C5BA C 0.6064(4) 0.3820(3) -0.0100(3) 0.0733(11) Uani 1 1 d . . . . .
H5BA H 0.5681 0.4161 -0.0587 0.088 Uiso 1 1 calc R U . . .
C6BA C 0.7852(4) 0.5838(3) 0.7451(3) 0.0777(12) Uani 1 1 d . . . . .
H6BA H 0.8205 0.6330 0.7150 0.093 Uiso 1 1 calc R U . . .
H6BB H 0.7135 0.6000 0.7868 0.093 Uiso 1 1 calc R U . . .
C4 C 0.7005(4) 0.3280(3) -0.0371(2) 0.0684(11) Uani 1 1 d . . . . .
H4 H 0.7228 0.3237 -0.1045 0.082 Uiso 1 1 calc R U . . .
C5 C 0.8625(4) 0.2222(3) 0.0139(3) 0.0747(12) Uani 1 1 d . . . . .
H5 H 0.8886 0.2155 -0.0523 0.090 Uiso 1 1 calc R U . . .
C6 C 0.8773(4) 0.1886(3) 0.1869(3) 0.0803(12) Uani 1 1 d . . . . .
H6 H 0.9189 0.1583 0.2377 0.096 Uiso 1 1 calc R U . . .
C7 C 0.9194(4) 0.1776(3) 0.0888(4) 0.0815(12) Uani 1 1 d . . . . .
H7 H 0.9852 0.1404 0.0752 0.098 Uiso 1 1 calc R U . . .
C8 C 0.8873(4) 0.5439(3) 0.8093(3) 0.0939(14) Uani 1 1 d . . . . .
H8A H 0.9627 0.5326 0.7690 0.113 Uiso 1 1 calc R U . . .
H8B H 0.8548 0.4920 0.8342 0.113 Uiso 1 1 calc R U . . .
C9 C 0.8272(5) 0.6020(4) 0.9816(4) 0.1092(18) Uani 1 1 d . . . . .
H9A H 0.7495 0.6280 0.9536 0.131 Uiso 1 1 calc R U . . .
H9B H 0.8043 0.5460 0.9987 0.131 Uiso 1 1 calc R U . . .
C10 C 0.9277(5) 0.5988(4) 0.8991(3) 0.1175(19) Uani 1 1 d . . . . .
H10A H 1.0092 0.5787 0.9281 0.141 Uiso 1 1 calc R U . . .
H10B H 0.9425 0.6541 0.8746 0.141 Uiso 1 1 calc R U . . .
C11 C 0.8644(6) 0.6453(5) 1.0763(4) 0.132(2) Uani 1 1 d . . . . .
H11A H 0.9456 0.6221 1.1020 0.158 Uiso 1 1 calc R U . . .
H11B H 0.8806 0.7024 1.0603 0.158 Uiso 1 1 calc R U . . .
C12 C 0.7703(6) 0.6421(4) 1.1563(4) 0.127(2) Uani 1 1 d . . . . .
H12A H 0.6887 0.6639 1.1318 0.190 Uiso 1 1 calc R U . . .
H12B H 0.8014 0.6741 1.2127 0.190 Uiso 1 1 calc R U . . .
H12C H 0.7586 0.5862 1.1770 0.190 Uiso 1 1 calc R U . . .
 
 
_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
O C1AA 1.374(3) . ?
O C8AA 1.401(3) . ?
O1 C4AA 1.234(3) . ?
O1AA C2BA 1.221(4) . ?
N2 C4AA 1.383(4) . ?
N2 C2BA 1.404(4) . ?
N2 C6BA 1.493(4) . ?
C1AA C9AA 1.365(4) . ?
C1AA C6AA 1.419(4) . ?
C2AA C0BA 1.381(4) . ?
C2AA C3AA 1.413(4) . ?
C2AA C4AA 1.469(4) . ?
C3AA C1 1.417(4) . ?
C3AA C6AA 1.418(4) . ?
N1 C6 1.307(5) . ?
N1 C5AA 1.368(4) . ?
C5AA C8AA 1.412(4) . ?
C5AA C2 1.422(4) . ?
C6AA C3BA 1.402(4) . ?
C1 C1BA 1.362(4) . ?
C1 C2BA 1.460(5) . ?
C2 C4 1.403(5) . ?
C2 C5 1.406(5) . ?
C8AA C3 1.354(4) . ?
C9AA C1BA 1.400(4) . ?
C0BA C4BA 1.390(5) . ?
C3BA C4BA 1.374(4) . ?
C3 C5BA 1.397(5) . ?
C5BA C4 1.363(5) . ?
C6BA C8 1.485(6) . ?
C5 C7 1.352(6) . ?
C6 C7 1.391(6) . ?
C8 C10 1.538(6) . ?
C9 C11 1.480(7) . ?
C9 C10 1.524(6) . ?
C11 C12 1.455(7) . ?
 
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
C1AA O C8AA 119.2(2) . . ?
C4AA N2 C2BA 124.7(3) . . ?
C4AA N2 C6BA 117.4(3) . . ?
C2BA N2 C6BA 117.9(3) . . ?
C9AA C1AA O 123.8(3) . . ?
C9AA C1AA C6AA 121.7(3) . . ?
O C1AA C6AA 114.5(3) . . ?
C0BA C2AA C3AA 119.8(3) . . ?
C0BA C2AA C4AA 120.2(3) . . ?
C3AA C2AA C4AA 120.0(3) . . ?
C2AA C3AA C1 120.5(3) . . ?
C2AA C3AA C6AA 119.3(3) . . ?
C1 C3AA C6AA 120.3(2) . . ?
C6 N1 C5AA 116.5(3) . . ?
O1 C4AA N2 120.5(3) . . ?
O1 C4AA C2AA 122.1(3) . . ?
N2 C4AA C2AA 117.4(2) . . ?
N1 C5AA C8AA 119.9(3) . . ?
N1 C5AA C2 122.8(3) . . ?
C8AA C5AA C2 117.3(3) . . ?
C3BA C6AA C3AA 119.2(3) . . ?
C3BA C6AA C1AA 123.3(3) . . ?
C3AA C6AA C1AA 117.5(3) . . ?
C1BA C1 C3AA 119.3(3) . . ?
C1BA C1 C2BA 120.6(3) . . ?
C3AA C1 C2BA 120.0(3) . . ?
C4 C2 C5 123.9(3) . . ?
C4 C2 C5AA 119.5(3) . . ?
C5 C2 C5AA 116.7(3) . . ?
C3 C8AA O 119.2(3) . . ?
C3 C8AA C5AA 122.4(3) . . ?
O C8AA C5AA 118.3(3) . . ?
C1AA C9AA C1BA 119.5(3) . . ?
C2AA C0BA C4BA 120.6(3) . . ?
C1 C1BA C9AA 121.7(3) . . ?
O1AA C2BA N2 119.2(3) . . ?
O1AA C2BA C1 123.5(3) . . ?
N2 C2BA C1 117.3(3) . . ?
C4BA C3BA C6AA 120.5(3) . . ?
C3BA C4BA C0BA 120.6(3) . . ?
C8AA C3 C5BA 119.4(3) . . ?
C4 C5BA C3 120.8(3) . . ?
C8 C6BA N2 111.7(4) . . ?
C5BA C4 C2 120.6(3) . . ?
C7 C5 C2 120.1(4) . . ?
N1 C6 C7 125.4(4) . . ?
C5 C7 C6 118.5(4) . . ?
C6BA C8 C10 111.2(4) . . ?
C11 C9 C10 117.3(4) . . ?
C9 C10 C8 113.6(4) . . ?
C12 C11 C9 116.0(5) . . ?
 
_refine_diff_density_max    0.277
_refine_diff_density_min   -0.242
_refine_diff_density_rms    0.044



