# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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_5118
_database_code_depnum_ccdc_archive 'CCDC 1026285'
_audit_update_record             
;
2014-09-26 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

#==============================================================================


# 6. CRYSTALLOGRAPHY 
_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 N3 O3'
_chemical_formula_sum            'C14 H11 N3 O3'
_chemical_formula_weight         269.26

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9782(11)
_cell_length_b                   9.8343(8)
_cell_length_c                   11.7533(11)
_cell_angle_alpha                90
_cell_angle_beta                 109.846(10)
_cell_angle_gamma                90
_cell_volume                     1193.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2264
_cell_measurement_theta_min      4.2420
_cell_measurement_theta_max      30.1010

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (80) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.4041
_diffrn_reflns_number            7235
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         30.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3141
_reflns_number_gt                2479
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0750P)²+0.6120P] 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         3141
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
O1 O 0.38315(11) 0.37596(12) 0.01739(10) 0.0236(3) Uani 1 1 d . . . . .
C4 C 0.46291(14) 0.23320(16) 0.19168(14) 0.0183(3) Uani 1 1 d . . . . .
N2 N 0.69071(12) 0.25369(14) 0.30243(12) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.7639 0.2111 0.3399 0.022 Uiso 1 1 calc R U . . .
N1 N 0.59071(12) 0.40364(14) 0.13937(11) 0.0193(3) Uani 1 1 d . . . . .
H1N H 0.6068 0.4537 0.0840 0.023 Uiso 1 1 calc R U . . .
O3 O 1.00198(12) 0.66586(15) 0.59871(12) 0.0326(3) Uani 1 1 d . . . . .
N3 N 0.89773(15) 0.71973(17) 0.58672(14) 0.0293(4) Uani 1 1 d . . . . .
C14 C 0.79156(15) 0.55926(17) 0.42410(14) 0.0195(3) Uani 1 1 d . . . . .
H14 H 0.8743 0.5345 0.4218 0.023 Uiso 1 1 calc R U . . .
C3 C 0.34522(15) 0.16641(17) 0.17148(15) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.2701 0.1967 0.1084 0.025 Uiso 1 1 calc R U . . .
C8 C 0.47411(15) 0.34329(17) 0.11019(14) 0.0189(3) Uani 1 1 d . . . . .
C5 C 0.56533(16) 0.07816(17) 0.35672(14) 0.0206(3) Uani 1 1 d . . . . .
H5 H 0.6397 0.0471 0.4201 0.025 Uiso 1 1 calc R U . . .
C9 C 0.67990(14) 0.49842(16) 0.34680(14) 0.0177(3) Uani 1 1 d . . . . .
C13 C 0.77953(15) 0.65663(17) 0.50445(14) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.44760(16) 0.01307(17) 0.33376(15) 0.0226(3) Uani 1 1 d . . . . .
H1 H 0.4424 -0.0631 0.3816 0.027 Uiso 1 1 calc R U . . .
C6 C 0.57454(14) 0.19033(16) 0.28597(14) 0.0170(3) Uani 1 1 d . . . . .
C10 C 0.56033(15) 0.53607(17) 0.35419(15) 0.0224(3) Uani 1 1 d . . . . .
H10 H 0.4837 0.4940 0.3024 0.027 Uiso 1 1 calc R U . . .
C7 C 0.69249(14) 0.39101(17) 0.25789(13) 0.0176(3) Uani 1 1 d . . . . .
H7 H 0.7777 0.4050 0.2462 0.021 Uiso 1 1 calc R U . . .
C2 C 0.33634(16) 0.05685(18) 0.24188(15) 0.0237(4) Uani 1 1 d . . . . .
H2N H 0.2559 0.0121 0.2280 0.028 Uiso 1 1 calc R U . . .
C12 C 0.66152(17) 0.69712(18) 0.51190(15) 0.0243(4) Uani 1 1 d . . . . .
H12 H 0.6565 0.7656 0.5671 0.029 Uiso 1 1 calc R U . . .
O2 O 0.88596(15) 0.82381(18) 0.63905(16) 0.0532(5) Uani 1 1 d . . . . .
C11 C 0.55164(16) 0.63414(19) 0.43604(17) 0.0265(4) Uani 1 1 d . . . . .
H11 H 0.4693 0.6581 0.4398 0.032 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
O1 C8 1.2452(18) . ?
C4 C3 1.396(2) . ?
C4 C6 1.409(2) . ?
C4 C8 1.478(2) . ?
N2 C6 1.373(2) . ?
N2 C7 1.451(2) . ?
N2 H2 0.8800 . ?
N1 C8 1.346(2) . ?
N1 C7 1.4654(18) . ?
N1 H1N 0.8800 . ?
O3 N3 1.225(2) . ?
N3 O2 1.223(2) . ?
N3 C13 1.467(2) . ?
C14 C13 1.382(2) . ?
C14 C9 1.389(2) . ?
C14 H14 0.9500 . ?
C3 C2 1.382(2) . ?
C3 H3 0.9500 . ?
C5 C1 1.384(2) . ?
C5 C6 1.406(2) . ?
C5 H5 0.9500 . ?
C9 C10 1.395(2) . ?
C9 C7 1.525(2) . ?
C13 C12 1.386(2) . ?
C1 C2 1.396(2) . ?
C1 H1 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C7 H7 1.0000 . ?
C2 H2N 0.9500 . ?
C12 C11 1.380(3) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?

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
C3 C4 C6 120.03(15) . . ?
C3 C4 C8 120.68(14) . . ?
C6 C4 C8 119.17(14) . . ?
C6 N2 C7 119.82(12) . . ?
C6 N2 H2 120.1 . . ?
C7 N2 H2 120.1 . . ?
C8 N1 C7 123.87(13) . . ?
C8 N1 H1N 118.1 . . ?
C7 N1 H1N 118.1 . . ?
O3 N3 O2 123.91(16) . . ?
O3 N3 C13 118.40(15) . . ?
O2 N3 C13 117.68(16) . . ?
C13 C14 C9 118.52(15) . . ?
C13 C14 H14 120.7 . . ?
C9 C14 H14 120.7 . . ?
C2 C3 C4 120.95(15) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
O1 C8 N1 121.34(15) . . ?
O1 C8 C4 122.56(14) . . ?
N1 C8 C4 116.05(13) . . ?
C1 C5 C6 119.83(15) . . ?
C1 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C14 C9 C10 119.02(15) . . ?
C14 C9 C7 118.78(14) . . ?
C10 C9 C7 122.19(14) . . ?
C14 C13 C12 123.38(15) . . ?
C14 C13 N3 118.36(14) . . ?
C12 C13 N3 118.25(15) . . ?
C5 C1 C2 121.47(16) . . ?
C5 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
N2 C6 C5 121.52(14) . . ?
N2 C6 C4 119.56(14) . . ?
C5 C6 C4 118.82(14) . . ?
C11 C10 C9 121.01(15) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
N2 C7 N1 108.82(12) . . ?
N2 C7 C9 112.46(12) . . ?
N1 C7 C9 112.06(13) . . ?
N2 C7 H7 107.8 . . ?
N1 C7 H7 107.8 . . ?
C9 C7 H7 107.8 . . ?
C3 C2 C1 118.87(15) . . ?
C3 C2 H2N 120.6 . . ?
C1 C2 H2N 120.6 . . ?
C11 C12 C13 117.45(16) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C12 C11 C10 120.60(15) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?

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 C4 C3 C2 -0.9(2) . . . . ?
C8 C4 C3 C2 175.18(15) . . . . ?
C7 N1 C8 O1 166.85(15) . . . . ?
C7 N1 C8 C4 -15.6(2) . . . . ?
C3 C4 C8 O1 -4.2(2) . . . . ?
C6 C4 C8 O1 171.84(15) . . . . ?
C3 C4 C8 N1 178.25(15) . . . . ?
C6 C4 C8 N1 -5.7(2) . . . . ?
C13 C14 C9 C10 -0.9(2) . . . . ?
C13 C14 C9 C7 179.96(14) . . . . ?
C9 C14 C13 C12 -0.1(3) . . . . ?
C9 C14 C13 N3 179.44(14) . . . . ?
O3 N3 C13 C14 -14.6(2) . . . . ?
O2 N3 C13 C14 165.16(17) . . . . ?
O3 N3 C13 C12 164.99(16) . . . . ?
O2 N3 C13 C12 -15.3(3) . . . . ?
C6 C5 C1 C2 -0.5(2) . . . . ?
C7 N2 C6 C5 -160.34(14) . . . . ?
C7 N2 C6 C4 23.3(2) . . . . ?
C1 C5 C6 N2 -177.04(15) . . . . ?
C1 C5 C6 C4 -0.7(2) . . . . ?
C3 C4 C6 N2 177.78(14) . . . . ?
C8 C4 C6 N2 1.7(2) . . . . ?
C3 C4 C6 C5 1.4(2) . . . . ?
C8 C4 C6 C5 -174.74(14) . . . . ?
C14 C9 C10 C11 0.9(2) . . . . ?
C7 C9 C10 C11 179.96(15) . . . . ?
C6 N2 C7 N1 -40.12(19) . . . . ?
C6 N2 C7 C9 84.64(16) . . . . ?
C8 N1 C7 N2 37.1(2) . . . . ?
C8 N1 C7 C9 -87.86(18) . . . . ?
C14 C9 C7 N2 96.95(16) . . . . ?
C10 C9 C7 N2 -82.13(18) . . . . ?
C14 C9 C7 N1 -140.09(14) . . . . ?
C10 C9 C7 N1 40.8(2) . . . . ?
C4 C3 C2 C1 -0.3(2) . . . . ?
C5 C1 C2 C3 1.0(2) . . . . ?
C14 C13 C12 C11 1.2(3) . . . . ?
N3 C13 C12 C11 -178.34(16) . . . . ?
C13 C12 C11 C10 -1.2(3) . . . . ?
C9 C10 C11 C12 0.2(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
N2 H2 O1 0.88 2.22 2.9745(17) 143.1 4_666
N1 H1N O1 0.88 2.08 2.9212(18) 159.5 3_665
C14 H14 O3 0.95 2.45 3.244(2) 140.9 3_766
C7 H7 O3 1.00 2.58 3.250(2) 124.2 3_766
N2 H2 O1 0.88 2.22 2.9745(17) 143.1 4_666
N1 H1N O1 0.88 2.08 2.9212(18) 159.5 3_665
C14 H14 O3 0.95 2.45 3.244(2) 140.9 3_766
C7 H7 O3 1.00 2.58 3.250(2) 124.2 3_766

_refine_diff_density_max         0.583
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.059

_shelxl_version_number           2014/6

