# Electronic Supplementary Material (ESI) for Analytical Methods.
# 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_kh695h
_database_code_depnum_ccdc_archive 'CCDC 1420169'
_audit_update_record             
;
2015-08-24 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N3 O3'
_chemical_formula_sum            'C16 H15 N3 O3'
_chemical_formula_weight         297.31

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.0689(16)
_cell_length_b                   13.762(3)
_cell_length_c                   14.911(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.54(2)
_cell_angle_gamma                90.00
_cell_volume                     1494.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3997
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      29.16

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10101
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_sigmaI/netI    0.1324
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         29.16
_reflns_number_total             3997
_reflns_number_gt                1333
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0310P)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       0.0048(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3997
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1986
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_restrained_S_all      0.823
_refine_ls_shift/su_max          0.001
_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
O1 O 0.4039(2) 0.39674(12) 0.58423(13) 0.0719(6) Uani 1 1 d . . .
O2 O 0.4202(2) 0.30258(12) 0.46720(13) 0.0669(5) Uani 1 1 d . . .
O3 O 1.0487(3) -0.35567(15) 0.41574(16) 0.0983(7) Uani 1 1 d . . .
N1 N 0.6206(3) 0.14175(15) 0.52527(16) 0.0513(6) Uani 1 1 d . . .
N2 N 0.6954(3) 0.06049(13) 0.51042(15) 0.0480(5) Uani 1 1 d . . .
N3 N 0.6620(2) 0.04774(13) 0.42053(15) 0.0498(5) Uani 1 1 d . . .
C1 C 0.2838(4) 0.4621(2) 0.5078(2) 0.0922(10) Uani 1 1 d . . .
H1A H 0.3118 0.4593 0.4515 0.138 Uiso 1 1 calc R . .
H1B H 0.3014 0.5272 0.5333 0.138 Uiso 1 1 calc R . .
H1C H 0.1583 0.4431 0.4879 0.138 Uiso 1 1 calc R . .
C2 C 0.4602(3) 0.31745(18) 0.5543(2) 0.0506(6) Uani 1 1 d . . .
C3 C 0.5696(3) 0.25288(17) 0.63719(17) 0.0435(5) Uani 1 1 d . . .
C4 C 0.5959(3) 0.27431(18) 0.73389(18) 0.0528(7) Uani 1 1 d . . .
H4 H 0.5457 0.3310 0.7456 0.063 Uiso 1 1 calc R . .
C5 C 0.6938(3) 0.2138(2) 0.81206(19) 0.0626(7) Uani 1 1 d . . .
H5 H 0.7080 0.2286 0.8758 0.075 Uiso 1 1 calc R . .
C6 C 0.7709(3) 0.1307(2) 0.7947(2) 0.0659(7) Uani 1 1 d . . .
H6 H 0.8393 0.0899 0.8475 0.079 Uiso 1 1 calc R . .
C7 C 0.7484(3) 0.10709(18) 0.70066(19) 0.0568(7) Uani 1 1 d . . .
H7 H 0.8016 0.0508 0.6903 0.068 Uiso 1 1 calc R . .
C8 C 0.6463(3) 0.16710(17) 0.62099(18) 0.0441(6) Uani 1 1 d . . .
C9 C 0.7434(3) -0.03961(16) 0.40635(17) 0.0422(6) Uani 1 1 d . . .
C10 C 0.8413(3) -0.10425(18) 0.48196(19) 0.0529(6) Uani 1 1 d . . .
H10 H 0.8603 -0.0910 0.5469 0.063 Uiso 1 1 calc R . .
C11 C 0.9099(3) -0.18776(18) 0.46085(18) 0.0530(6) Uani 1 1 d . . .
H11 H 0.9747 -0.2309 0.5121 0.064 Uiso 1 1 calc R . .
C12 C 0.8851(3) -0.20976(17) 0.36472(18) 0.0452(6) Uani 1 1 d . . .
C13 C 0.9585(3) -0.30257(19) 0.3469(2) 0.0571(7) Uani 1 1 d . . .
C14 C 0.9202(4) -0.33144(19) 0.24311(19) 0.0754(8) Uani 1 1 d . . .
H14A H 0.9838 -0.3908 0.2445 0.113 Uiso 1 1 calc R . .
H14B H 0.9616 -0.2811 0.2130 0.113 Uiso 1 1 calc R . .
H14C H 0.7905 -0.3409 0.2051 0.113 Uiso 1 1 calc R . .
C15 C 0.7888(3) -0.14442(17) 0.29022(18) 0.0520(6) Uani 1 1 d . . .
H15 H 0.7700 -0.1573 0.2253 0.062 Uiso 1 1 calc R . .
C16 C 0.7196(3) -0.05969(17) 0.31128(17) 0.0530(7) Uani 1 1 d . . .
H16 H 0.6564 -0.0159 0.2604 0.064 Uiso 1 1 calc R . .
H1 H 0.555(3) 0.1806(18) 0.4760(18) 0.072(9) Uiso 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
O1 C2 1.331(3) . ?
O1 C1 1.447(3) . ?
O2 C2 1.213(3) . ?
O3 C13 1.214(3) . ?
N1 N2 1.334(2) . ?
N1 C8 1.395(3) . ?
N1 H1 0.88(2) . ?
N2 N3 1.260(2) . ?
N3 C9 1.429(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.468(3) . ?
C3 C4 1.396(3) . ?
C3 C8 1.401(3) . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9300 . ?
C9 C16 1.374(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.370(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9300 . ?
C12 C15 1.379(3) . ?
C12 C13 1.480(3) . ?
C13 C14 1.495(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C16 H16 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
C2 O1 C1 117.1(2) . . ?
N2 N1 C8 120.1(2) . . ?
N2 N1 H1 121.7(16) . . ?
C8 N1 H1 118.2(16) . . ?
N3 N2 N1 112.9(2) . . ?
N2 N3 C9 111.93(19) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 121.7(2) . . ?
O2 C2 C3 125.8(2) . . ?
O1 C2 C3 112.5(2) . . ?
C4 C3 C8 118.3(2) . . ?
C4 C3 C2 120.7(2) . . ?
C8 C3 C2 121.0(2) . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 N1 119.9(2) . . ?
C7 C8 C3 119.8(2) . . ?
N1 C8 C3 120.3(2) . . ?
C16 C9 C10 119.2(2) . . ?
C16 C9 N3 117.0(2) . . ?
C10 C9 N3 123.9(2) . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.7(2) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C15 C12 C11 117.9(2) . . ?
C15 C12 C13 123.3(2) . . ?
C11 C12 C13 118.8(2) . . ?
O3 C13 C12 120.6(2) . . ?
O3 C13 C14 119.8(2) . . ?
C12 C13 C14 119.7(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 C16 120.5(2) . . ?
C12 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C9 C16 C15 120.8(2) . . ?
C9 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?

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
C8 N1 N2 N3 -179.3(2) . . . . ?
N1 N2 N3 C9 179.99(17) . . . . ?
C1 O1 C2 O2 3.5(3) . . . . ?
C1 O1 C2 C3 -175.7(2) . . . . ?
O2 C2 C3 C4 -175.4(2) . . . . ?
O1 C2 C3 C4 3.7(3) . . . . ?
O2 C2 C3 C8 3.0(3) . . . . ?
O1 C2 C3 C8 -177.9(2) . . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C5 178.4(2) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 N1 -178.7(2) . . . . ?
C6 C7 C8 C3 1.4(3) . . . . ?
N2 N1 C8 C7 -0.6(3) . . . . ?
N2 N1 C8 C3 179.3(2) . . . . ?
C4 C3 C8 C7 -1.3(3) . . . . ?
C2 C3 C8 C7 -179.7(2) . . . . ?
C4 C3 C8 N1 178.8(2) . . . . ?
C2 C3 C8 N1 0.4(3) . . . . ?
N2 N3 C9 C16 -178.4(2) . . . . ?
N2 N3 C9 C10 2.3(3) . . . . ?
C16 C9 C10 C11 -1.2(3) . . . . ?
N3 C9 C10 C11 178.0(2) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C15 0.1(3) . . . . ?
C10 C11 C12 C13 -178.3(2) . . . . ?
C15 C12 C13 O3 177.0(2) . . . . ?
C11 C12 C13 O3 -4.6(3) . . . . ?
C15 C12 C13 C14 -3.4(3) . . . . ?
C11 C12 C13 C14 175.0(2) . . . . ?
C11 C12 C15 C16 0.1(3) . . . . ?
C13 C12 C15 C16 178.5(2) . . . . ?
C10 C9 C16 C15 1.4(3) . . . . ?
N3 C9 C16 C15 -177.9(2) . . . . ?
C12 C15 C16 C9 -0.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.88(2) 1.97(3) 2.656(3) 134(2) .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.16
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.029
