# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1965927'
loop_
_audit_author_name
_audit_author_address
'Debarshi saha'
;IIT Ropar
India
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_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'

_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                   10.3000(14)
_cell_length_b                   13.3590(18)
_cell_length_c                   10.7467(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.880(5)
_cell_angle_gamma                90
_cell_volume                     1435.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.097
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19165
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.477
_diffrn_reflns_theta_max         27.327
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3226
_reflns_number_gt                1859
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0715P)²+0.1815P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3226
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1330
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.39807(17) 0.32984(10) 0.29245(17) 0.0770(5) Uani 1 1 d . . . . .
O2 O 0.45159(17) 0.62670(11) 0.36327(15) 0.0722(5) Uani 1 1 d . . . . .
O3 O 0.26427(17) 0.54459(11) 0.46252(14) 0.0710(5) Uani 1 1 d . . . . .
N2 N 0.49350(17) 0.48249(11) 0.26790(15) 0.0526(5) Uani 1 1 d . . . . .
N1 N 0.54625(18) 0.33734(12) 0.17086(17) 0.0630(5) Uani 1 1 d . . . . .
H3 H 0.540649 0.273336 0.162742 0.076 Uiso 1 1 calc R U . . .
C14 C -0.1020(3) 0.69870(17) 0.6264(2) 0.0691(7) Uani 1 1 d . . . . .
H1 H -0.156197 0.723517 0.677112 0.083 Uiso 1 1 calc R U . . .
C15 C 0.0263(3) 0.66961(17) 0.6811(2) 0.0671(6) Uani 1 1 d . . . . .
H5 H 0.058972 0.674016 0.769459 0.080 Uiso 1 1 calc R U . . .
C16 C 0.1080(2) 0.63362(16) 0.60586(19) 0.0618(6) Uani 1 1 d . . . . .
H4 H 0.195598 0.615019 0.643811 0.074 Uiso 1 1 calc R U . . .
C11 C 0.0601(2) 0.62523(14) 0.47485(18) 0.0518(5) Uani 1 1 d . . . . .
C10 C 0.1423(2) 0.58527(17) 0.3885(2) 0.0659(6) Uani 1 1 d . . . . .
H15 H 0.092477 0.533715 0.333497 0.079 Uiso 1 1 calc R U . . .
H14 H 0.161471 0.638680 0.334396 0.079 Uiso 1 1 calc R U . . .
N3 N 0.3277(2) 0.49215(14) 0.38147(19) 0.0793(7) Uani 1 1 d . . . . .
H13 H 0.305039 0.431819 0.358000 0.095 Uiso 1 1 calc R U . . .
C9 C 0.4245(2) 0.53888(15) 0.34192(19) 0.0559(5) Uani 1 1 d . . . . .
C7 C 0.5962(2) 0.54078(15) 0.2248(2) 0.0617(6) Uani 1 1 d . . . . .
H9 H 0.668272 0.556459 0.298576 0.074 Uiso 1 1 calc R U . . .
H10 H 0.557177 0.603510 0.188482 0.074 Uiso 1 1 calc R U . . .
C6 C 0.6528(2) 0.48742(15) 0.12761(18) 0.0528(5) Uani 1 1 d . . . . .
C5 C 0.6284(2) 0.38659(15) 0.10432(18) 0.0525(5) Uani 1 1 d . . . . .
C4 C 0.6851(2) 0.33538(17) 0.0183(2) 0.0650(6) Uani 1 1 d . . . . .
H12 H 0.666901 0.267763 0.002319 0.078 Uiso 1 1 calc R U . . .
C3 C 0.7685(3) 0.3855(2) -0.0435(2) 0.0779(7) Uani 1 1 d . . . . .
H2 H 0.808574 0.351145 -0.099657 0.093 Uiso 1 1 calc R U . . .
C13 C -0.1501(2) 0.69110(17) 0.4967(2) 0.0738(7) Uani 1 1 d . . . . .
H3 H -0.237463 0.710433 0.459079 0.089 Uiso 1 1 calc R U . . .
C12 C -0.0691(2) 0.65468(16) 0.4215(2) 0.0644(6) Uani 1 1 d . . . . .
H16 H -0.102655 0.650022 0.333268 0.077 Uiso 1 1 calc R U . . .
C8 C 0.4748(2) 0.38027(15) 0.2467(2) 0.0569(5) Uani 1 1 d . . . . .
C2 C 0.7927(3) 0.4864(2) -0.0221(2) 0.0806(8) Uani 1 1 d . . . . .
H11 H 0.847965 0.520299 -0.064780 0.097 Uiso 1 1 calc R U . . .
C1 C 0.7345(2) 0.53675(17) 0.0627(2) 0.0661(6) Uani 1 1 d . . . . .
H8 H 0.750627 0.604835 0.076480 0.079 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 1.227(2) . ?
O2 C9 1.215(2) . ?
O3 N3 1.396(2) . ?
O3 C10 1.424(3) . ?
N2 C8 1.390(3) . ?
N2 C9 1.406(2) . ?
N2 C7 1.474(3) . ?
N1 C8 1.350(2) . ?
N1 C5 1.397(2) . ?
N1 H3 0.8600 . ?
C14 C13 1.366(3) . ?
C14 C15 1.368(3) . ?
C14 H1 0.9300 . ?
C15 C16 1.386(3) . ?
C15 H5 0.9300 . ?
C16 C11 1.380(3) . ?
C16 H4 0.9300 . ?
C11 C12 1.375(3) . ?
C11 C10 1.497(3) . ?
C10 H15 0.9700 . ?
C10 H14 0.9700 . ?
N3 C9 1.329(3) . ?
N3 H13 0.8600 . ?
C7 C6 1.494(3) . ?
C7 H9 0.9700 . ?
C7 H10 0.9700 . ?
C6 C5 1.382(3) . ?
C6 C1 1.383(3) . ?
C5 C4 1.387(3) . ?
C4 C3 1.378(3) . ?
C4 H12 0.9300 . ?
C3 C2 1.380(4) . ?
C3 H2 0.9300 . ?
C13 C12 1.382(3) . ?
C13 H3 0.9300 . ?
C12 H16 0.9300 . ?
C2 C1 1.380(3) . ?
C2 H11 0.9300 . ?
C1 H8 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
N3 O3 C10 108.98(16) . . ?
C8 N2 C9 123.36(17) . . ?
C8 N2 C7 123.30(16) . . ?
C9 N2 C7 113.13(16) . . ?
C8 N1 C5 126.44(17) . . ?
C8 N1 H3 116.8 . . ?
C5 N1 H3 116.8 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H1 120.2 . . ?
C15 C14 H1 120.2 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H5 119.8 . . ?
C16 C15 H5 119.8 . . ?
C11 C16 C15 120.3(2) . . ?
C11 C16 H4 119.8 . . ?
C15 C16 H4 119.8 . . ?
C12 C11 C16 118.42(19) . . ?
C12 C11 C10 118.58(19) . . ?
C16 C11 C10 123.0(2) . . ?
O3 C10 C11 110.11(17) . . ?
O3 C10 H15 109.6 . . ?
C11 C10 H15 109.6 . . ?
O3 C10 H14 109.6 . . ?
C11 C10 H14 109.6 . . ?
H15 C10 H14 108.2 . . ?
C9 N3 O3 117.58(18) . . ?
C9 N3 H13 121.2 . . ?
O3 N3 H13 121.2 . . ?
O2 C9 N3 123.31(19) . . ?
O2 C9 N2 119.97(19) . . ?
N3 C9 N2 116.68(18) . . ?
N2 C7 C6 113.39(16) . . ?
N2 C7 H9 108.9 . . ?
C6 C7 H9 108.9 . . ?
N2 C7 H10 108.9 . . ?
C6 C7 H10 108.9 . . ?
H9 C7 H10 107.7 . . ?
C5 C6 C1 118.63(19) . . ?
C5 C6 C7 120.50(18) . . ?
C1 C6 C7 120.82(19) . . ?
C6 C5 C4 120.97(19) . . ?
C6 C5 N1 118.19(17) . . ?
C4 C5 N1 120.84(19) . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H12 120.3 . . ?
C5 C4 H12 120.3 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H2 119.9 . . ?
C2 C3 H2 119.9 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H3 120.0 . . ?
C12 C13 H3 120.0 . . ?
C11 C12 C13 121.1(2) . . ?
C11 C12 H16 119.4 . . ?
C13 C12 H16 119.4 . . ?
O1 C8 N1 120.36(18) . . ?
O1 C8 N2 123.41(18) . . ?
N1 C8 N2 116.23(18) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H11 120.1 . . ?
C1 C2 H11 120.1 . . ?
C2 C1 C6 120.9(2) . . ?
C2 C1 H8 119.5 . . ?
C6 C1 H8 119.5 . . ?

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
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C11 -1.0(3) . . . . ?
C15 C16 C11 C12 0.9(3) . . . . ?
C15 C16 C11 C10 -178.9(2) . . . . ?
N3 O3 C10 C11 169.47(16) . . . . ?
C12 C11 C10 O3 -170.92(18) . . . . ?
C16 C11 C10 O3 8.9(3) . . . . ?
C10 O3 N3 C9 98.2(2) . . . . ?
O3 N3 C9 O2 -6.8(3) . . . . ?
O3 N3 C9 N2 175.61(16) . . . . ?
C8 N2 C9 O2 175.4(2) . . . . ?
C7 N2 C9 O2 0.6(3) . . . . ?
C8 N2 C9 N3 -6.9(3) . . . . ?
C7 N2 C9 N3 178.25(19) . . . . ?
C8 N2 C7 C6 15.5(3) . . . . ?
C9 N2 C7 C6 -169.70(16) . . . . ?
N2 C7 C6 C5 -12.5(3) . . . . ?
N2 C7 C6 C1 170.01(19) . . . . ?
C1 C6 C5 C4 0.3(3) . . . . ?
C7 C6 C5 C4 -177.24(19) . . . . ?
C1 C6 C5 N1 179.65(19) . . . . ?
C7 C6 C5 N1 2.1(3) . . . . ?
C8 N1 C5 C6 7.9(3) . . . . ?
C8 N1 C5 C4 -172.8(2) . . . . ?
C6 C5 C4 C3 1.0(3) . . . . ?
N1 C5 C4 C3 -178.3(2) . . . . ?
C5 C4 C3 C2 -1.6(4) . . . . ?
C15 C14 C13 C12 -0.3(4) . . . . ?
C16 C11 C12 C13 -0.5(3) . . . . ?
C10 C11 C12 C13 179.3(2) . . . . ?
C14 C13 C12 C11 0.3(3) . . . . ?
C5 N1 C8 O1 174.4(2) . . . . ?
C5 N1 C8 N2 -5.3(3) . . . . ?
C9 N2 C8 O1 -1.3(3) . . . . ?
C7 N2 C8 O1 173.0(2) . . . . ?
C9 N2 C8 N1 178.45(19) . . . . ?
C7 N2 C8 N1 -7.2(3) . . . . ?
C4 C3 C2 C1 0.9(4) . . . . ?
C3 C2 C1 C6 0.4(4) . . . . ?
C5 C6 C1 C2 -1.0(3) . . . . ?
C7 C6 C1 C2 176.5(2) . . . . ?

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
_geom_hbond_publ_flag
N3 H13 O1 0.86 1.90 2.545(2) 131.0 . yes
N3 H13 O1 0.86 1.90 2.545(2) 131.0 . yes

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.036



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1983427'
loop_
_audit_author_name
_audit_author_address
'Debarshi saha'
;IIT Ropar
India
;
_audit_update_record             
;
2020-02-11 deposited with the CCDC.	2020-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N3 O3'
_chemical_formula_sum            'C15 H13 N3 O3'
_chemical_formula_weight         283.28

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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   5.0971(6)
_cell_length_b                   5.3649(7)
_cell_length_c                   12.3429(16)
_cell_angle_alpha                99.966(5)
_cell_angle_beta                 96.111(4)
_cell_angle_gamma                90.897(4)
_cell_volume                     330.34(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4129
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      29.6

_exptl_crystal_description       flakes
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             148
_exptl_transmission_factor_min   0.3660
_exptl_transmission_factor_max   0.7459
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.120
_shelx_estimated_absorpt_T_max   0.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean 10.233
_diffrn_reflns_number            4129
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.372
_diffrn_reflns_theta_max         29.621
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.756
_diffrn_reflns_point_group_measured_fraction_full 0.852
_reflns_number_total             2817
_reflns_number_gt                2328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_max     0.589
_reflns_Friedel_fraction_full    0.723

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP, Platon, Mercury'
_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)+(0.1302P)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_abs_structure_details 
;
 Flack x determined using 742 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2817
_refine_ls_number_parameters     190
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.2058
_refine_ls_wR_factor_gt          0.1853
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.065
_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 0.4145(6) 1.1022(6) 0.3069(3) 0.0469(8) Uani 1 1 d . . . . .
O2 O 0.6428(6) 0.9213(7) 0.1278(3) 0.0543(9) Uani 1 1 d . . . . .
N2 N 0.1346(6) 0.7542(6) 0.2820(3) 0.0372(7) Uani 1 1 d . . . . .
O3 O 0.0932(7) 0.4075(6) 0.1348(3) 0.0521(8) Uani 1 1 d . . . . .
N1 N 0.4140(7) 0.8052(8) 0.1525(3) 0.0526(10) Uani 1 1 d . . . . .
H1 H 0.3323 0.6795 0.1085 0.063 Uiso 1 1 calc R U . . .
N3 N -0.1543(7) 0.4458(7) 0.2849(3) 0.0466(9) Uani 1 1 d . . . . .
H3 H -0.2487 0.3075 0.2671 0.056 Uiso 1 1 calc R U . . .
C1 C -0.3285(8) 0.6262(9) 0.4649(4) 0.0483(10) Uani 1 1 d . . . . .
H1A H -0.4493 0.4946 0.4650 0.058 Uiso 1 1 calc R U . . .
C2 C 0.3319(7) 0.9040(7) 0.2497(3) 0.0373(8) Uani 1 1 d . . . . .
C3 C 0.5254(8) 0.8103(9) -0.0733(4) 0.0480(10) Uani 1 1 d . . . . .
C4 C -0.1691(7) 0.6212(7) 0.3796(4) 0.0400(9) Uani 1 1 d . . . . .
C5 C 0.5843(11) 1.0174(10) 0.0255(4) 0.0585(12) Uani 1 1 d . . . . .
H5A H 0.7338 1.1204 0.0143 0.070 Uiso 1 1 calc R U . . .
H5B H 0.4335 1.1250 0.0316 0.070 Uiso 1 1 calc R U . . .
C6 C 0.0108(6) 0.8207(7) 0.3799(3) 0.0372(8) Uani 1 1 d . . . . .
C7 C -0.3004(8) 0.8336(10) 0.5491(4) 0.0510(10) Uani 1 1 d . . . . .
H7 H -0.4031 0.8409 0.6075 0.061 Uiso 1 1 calc R U . . .
C8 C -0.1202(9) 1.0340(10) 0.5488(4) 0.0502(10) Uani 1 1 d . . . . .
H8 H -0.1065 1.1724 0.6063 0.060 Uiso 1 1 calc R U . . .
C9 C 0.0386(8) 1.0274(9) 0.4630(4) 0.0445(9) Uani 1 1 d . . . . .
H9 H 0.1592 1.1589 0.4624 0.053 Uiso 1 1 calc R U . . .
C10 C 0.3120(10) 0.8226(12) -0.1525(5) 0.0627(13) Uani 1 1 d . . . . .
H10 H 0.2006 0.9585 -0.1436 0.075 Uiso 1 1 calc R U . . .
C11 C 0.2653(11) 0.6318(14) -0.2450(6) 0.0731(17) Uani 1 1 d . . . . .
H11 H 0.1226 0.6409 -0.2977 0.088 Uiso 1 1 calc R U . . .
C12 C 0.6336(12) 0.4115(13) -0.1812(5) 0.0654(14) Uani 1 1 d . . . . .
H12 H 0.7397 0.2714 -0.1894 0.079 Uiso 1 1 calc R U . . .
C13 C 0.4286(12) 0.4299(12) -0.2590(5) 0.0671(15) Uani 1 1 d . . . . .
H13 H 0.3986 0.3055 -0.3220 0.081 Uiso 1 1 calc R U . . .
C14 C 0.0280(7) 0.5186(8) 0.2231(4) 0.0426(9) Uani 1 1 d . . . . .
C15 C 0.6844(10) 0.6028(12) -0.0893(4) 0.0575(12) Uani 1 1 d . . . . .
H15 H 0.8281 0.5912 -0.0375 0.069 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 C2 1.212(5) . ?
O2 N1 1.400(4) . ?
O2 C5 1.449(6) . ?
N2 C2 1.410(5) . ?
N2 C14 1.413(4) . ?
N2 C6 1.416(5) . ?
O3 C14 1.230(6) . ?
N1 C2 1.338(6) . ?
N1 H1 0.8600 . ?
N3 C14 1.356(6) . ?
N3 C4 1.378(6) . ?
N3 H3 0.8600 . ?
C1 C7 1.379(8) . ?
C1 C4 1.394(6) . ?
C1 H1A 0.9300 . ?
C3 C15 1.387(8) . ?
C3 C10 1.394(7) . ?
C3 C5 1.501(7) . ?
C4 C6 1.398(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C9 1.368(6) . ?
C7 C8 1.404(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(7) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.392(10) . ?
C10 H10 0.9300 . ?
C11 C13 1.375(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.359(9) . ?
C12 C15 1.391(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 H15 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
N1 O2 C5 109.1(3) . . ?
C2 N2 C14 126.2(4) . . ?
C2 N2 C6 124.3(3) . . ?
C14 N2 C6 109.4(3) . . ?
C2 N1 O2 115.1(3) . . ?
C2 N1 H1 122.5 . . ?
O2 N1 H1 122.5 . . ?
C14 N3 C4 111.4(3) . . ?
C14 N3 H3 124.3 . . ?
C4 N3 H3 124.3 . . ?
C7 C1 C4 117.5(4) . . ?
C7 C1 H1A 121.2 . . ?
C4 C1 H1A 121.2 . . ?
O1 C2 N1 125.0(4) . . ?
O1 C2 N2 121.5(4) . . ?
N1 C2 N2 113.5(3) . . ?
C15 C3 C10 118.0(5) . . ?
C15 C3 C5 120.9(4) . . ?
C10 C3 C5 121.1(5) . . ?
N3 C4 C1 131.1(4) . . ?
N3 C4 C6 108.1(4) . . ?
C1 C4 C6 120.8(4) . . ?
O2 C5 C3 112.7(4) . . ?
O2 C5 H5A 109.0 . . ?
C3 C5 H5A 109.0 . . ?
O2 C5 H5B 109.0 . . ?
C3 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C9 C6 C4 121.9(4) . . ?
C9 C6 N2 132.6(3) . . ?
C4 C6 N2 105.5(3) . . ?
C1 C7 C8 121.5(5) . . ?
C1 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C6 C9 C8 117.7(4) . . ?
C6 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C11 C10 C3 120.1(6) . . ?
C11 C10 H10 119.9 . . ?
C3 C10 H10 119.9 . . ?
C13 C11 C10 120.4(5) . . ?
C13 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C15 119.8(6) . . ?
C13 C12 H12 120.1 . . ?
C15 C12 H12 120.1 . . ?
C12 C13 C11 120.3(6) . . ?
C12 C13 H13 119.9 . . ?
C11 C13 H13 119.9 . . ?
O3 C14 N3 128.7(4) . . ?
O3 C14 N2 125.8(4) . . ?
N3 C14 N2 105.5(4) . . ?
C3 C15 C12 121.4(5) . . ?
C3 C15 H15 119.3 . . ?
C12 C15 H15 119.3 . . ?

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
C5 O2 N1 C2 -120.9(4) . . . . ?
O2 N1 C2 O1 11.7(6) . . . . ?
O2 N1 C2 N2 -168.2(3) . . . . ?
C14 N2 C2 O1 -178.7(4) . . . . ?
C6 N2 C2 O1 1.8(6) . . . . ?
C14 N2 C2 N1 1.3(5) . . . . ?
C6 N2 C2 N1 -178.3(4) . . . . ?
C14 N3 C4 C1 179.1(4) . . . . ?
C14 N3 C4 C6 0.5(4) . . . . ?
C7 C1 C4 N3 -178.8(4) . . . . ?
C7 C1 C4 C6 -0.4(6) . . . . ?
N1 O2 C5 C3 -67.6(5) . . . . ?
C15 C3 C5 O2 -46.2(6) . . . . ?
C10 C3 C5 O2 134.8(5) . . . . ?
N3 C4 C6 C9 178.8(4) . . . . ?
C1 C4 C6 C9 0.1(5) . . . . ?
N3 C4 C6 N2 -0.7(4) . . . . ?
C1 C4 C6 N2 -179.4(3) . . . . ?
C2 N2 C6 C9 0.8(6) . . . . ?
C14 N2 C6 C9 -178.9(4) . . . . ?
C2 N2 C6 C4 -179.8(3) . . . . ?
C14 N2 C6 C4 0.6(4) . . . . ?
C4 C1 C7 C8 0.6(7) . . . . ?
C1 C7 C8 C9 -0.7(7) . . . . ?
C4 C6 C9 C8 -0.1(6) . . . . ?
N2 C6 C9 C8 179.3(4) . . . . ?
C7 C8 C9 C6 0.4(7) . . . . ?
C15 C3 C10 C11 -0.7(7) . . . . ?
C5 C3 C10 C11 178.2(5) . . . . ?
C3 C10 C11 C13 0.0(9) . . . . ?
C15 C12 C13 C11 -2.5(9) . . . . ?
C10 C11 C13 C12 1.6(10) . . . . ?
C4 N3 C14 O3 179.4(4) . . . . ?
C4 N3 C14 N2 -0.2(4) . . . . ?
C2 N2 C14 O3 0.5(6) . . . . ?
C6 N2 C14 O3 -179.9(4) . . . . ?
C2 N2 C14 N3 -179.9(3) . . . . ?
C6 N2 C14 N3 -0.3(4) . . . . ?
C10 C3 C15 C12 -0.2(7) . . . . ?
C5 C3 C15 C12 -179.1(5) . . . . ?
C13 C12 C15 C3 1.8(8) . . . . ?

_refine_diff_density_max         0.571
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.193



