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

####################################################################### 
# 
# 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_yaojia2
_database_code_depnum_ccdc_archive 'CCDC 1522408'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         297.30

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.3645(5)
_cell_length_b                   14.4689(12)
_cell_length_c                   15.7267(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.228(3)
_cell_angle_gamma                90
_cell_volume                     1429.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2271
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.34
_cell_measurement_temperature    173(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'

_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            9259
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_full        25.41
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_reflns_number_total             2602
_reflns_number_gt                1666
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1426
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      0.955
_refine_ls_number_reflns         2602
_refine_ls_number_parameters     277
_refine_ls_number_restraints     531
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²+1.1173P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2016)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6684(4) 1.09700(17) 0.63338(16) 0.0263(6) Uani d . . . 1.0 . .
C C2 0.7529(4) 1.01094(19) 0.65659(18) 0.0311(7) Uani d . . . 1.0 . .
H H2 0.8978 1.0042 0.682 0.037 Uiso calc U . R 1.0 . .
C C3 0.6204(4) 0.93500(18) 0.64171(18) 0.0304(7) Uani d . . . 1.0 . .
H H3 0.6744 0.8751 0.6572 0.037 Uiso calc U . R 1.0 . .
C C4 0.4090(4) 0.94559(17) 0.60431(17) 0.0252(6) Uani d . . . 1.0 . .
C C5 0.3292(4) 1.03328(17) 0.58168(17) 0.0266(6) Uani d . . . 1.0 . .
H H5 0.1845 1.0405 0.5561 0.032 Uiso calc U . R 1.0 . .
C C6 0.4599(4) 1.11014(18) 0.59632(17) 0.0278(6) Uani d . . . 1.0 . .
H H6 0.4068 1.1703 0.5812 0.033 Uiso calc U . R 1.0 . .
C C7 0.2593(4) 0.86591(18) 0.58522(19) 0.0308(6) Uani d U . D 1.0 . .
C C8 0.3288(7) 0.7686(2) 0.6102(4) 0.0274(12) Uani d U P D 0.888(5) A 1
H H8A 0.4285 0.7702 0.6654 0.033 Uiso calc U P R 0.888(5) A 1
H H8B 0.4062 0.7428 0.5658 0.033 Uiso calc U P R 0.888(5) A 1
C C9 0.1414(6) 0.7049(3) 0.6199(3) 0.0230(8) Uani d U P D 0.888(5) A 1
C C10 0.2103(5) 0.60174(16) 0.6271(2) 0.0253(7) Uani d U P DG 0.888(5) A 1
C C11 0.4063(4) 0.57164(18) 0.6096(2) 0.0340(9) Uani d U P DG 0.888(5) A 1
H H11 0.5055 0.6149 0.5939 0.041 Uiso calc U P R 0.888(5) A 1
C C12 0.4572(4) 0.4782(2) 0.6151(2) 0.0410(10) Uani d U P DG 0.888(5) A 1
H H12 0.5911 0.4576 0.6031 0.049 Uiso calc U P R 0.888(5) A 1
C C13 0.3120(5) 0.41480(15) 0.6381(2) 0.0408(10) Uani d U P DG 0.888(5) A 1
H H13 0.3468 0.3509 0.6418 0.049 Uiso calc U P R 0.888(5) A 1
C C14 0.1160(5) 0.44490(18) 0.6556(2) 0.0465(10) Uani d U P DG 0.888(5) A 1
H H14 0.0168 0.4016 0.6713 0.056 Uiso calc U P R 0.888(5) A 1
C C15 0.0651(4) 0.5384(2) 0.6501(2) 0.0388(10) Uani d U P DG 0.888(5) A 1
H H15 -0.0688 0.5589 0.6621 0.047 Uiso calc U P R 0.888(5) A 1
C C16 -0.0276(8) 0.7092(3) 0.5395(3) 0.0270(10) Uani d U P D 0.888(5) A 1
H H16 0.0199 0.7085 0.4852 0.032 Uiso calc U P R 0.888(5) A 1
C C17 0.0458(7) 0.7351(4) 0.6988(3) 0.0325(10) Uani d U P D 0.888(5) A 1
H H17A 0.0152 0.8015 0.6952 0.049 Uiso calc U P R 0.888(5) A 1
H H17B 0.1472 0.7222 0.7512 0.049 Uiso calc U P R 0.888(5) A 1
H H17C -0.0864 0.7009 0.7006 0.049 Uiso calc U P R 0.888(5) A 1
O O4 -0.2167(3) 0.71358(15) 0.53950(14) 0.0352(7) Uani d U P D 0.888(5) A 1
C C8' 0.322(6) 0.7653(13) 0.594(4) 0.027(3) Uani d U P D 0.112(5) A 2
H H8'1 0.4381 0.759 0.6443 0.033 Uiso calc U P R 0.112(5) A 2
H H8'2 0.3808 0.7464 0.5424 0.033 Uiso calc U P R 0.112(5) A 2
C C9' 0.142(5) 0.6981(18) 0.607(2) 0.028(2) Uani d U P D 0.112(5) A 2
C C10' 0.226(4) 0.5984(14) 0.6250(17) 0.031(2) Uani d U P DG 0.112(5) A 2
C C11' 0.390(4) 0.5719(17) 0.5817(17) 0.034(2) Uani d U P DG 0.112(5) A 2
H H11' 0.4555 0.6162 0.5497 0.041 Uiso calc U P R 0.112(5) A 2
C C12' 0.459(4) 0.4806(19) 0.5852(18) 0.039(3) Uani d U P DG 0.112(5) A 2
H H12' 0.5714 0.4625 0.5556 0.047 Uiso calc U P R 0.112(5) A 2
C C13' 0.364(5) 0.4158(15) 0.6319(19) 0.040(3) Uani d U P DG 0.112(5) A 2
H H13' 0.4108 0.3534 0.6343 0.048 Uiso calc U P R 0.112(5) A 2
C C14' 0.199(4) 0.4423(16) 0.6752(18) 0.037(3) Uani d U P DG 0.112(5) A 2
H H14' 0.1342 0.398 0.7072 0.044 Uiso calc U P R 0.112(5) A 2
C C15' 0.131(4) 0.5335(17) 0.6717(17) 0.033(2) Uani d U P DG 0.112(5) A 2
H H15' 0.0182 0.5516 0.7013 0.04 Uiso calc U P R 0.112(5) A 2
C C16' 0.033(4) 0.724(3) 0.682(2) 0.029(3) Uani d U P D 0.112(5) A 2
H H16' 0.1161 0.7475 0.7324 0.035 Uiso calc U P R 0.112(5) A 2
C C17' -0.012(7) 0.695(3) 0.521(2) 0.036(5) Uani d U P D 0.112(5) A 2
H H17D -0.132 0.6542 0.527 0.053 Uiso calc U P R 0.112(5) A 2
H H17E 0.0623 0.6714 0.4757 0.053 Uiso calc U P R 0.112(5) A 2
H H17F -0.0655 0.7574 0.506 0.053 Uiso calc U P R 0.112(5) A 2
O O4' -0.156(3) 0.7145(14) 0.6789(12) 0.047(5) Uani d U P D 0.112(5) A 2
N N1 0.8072(4) 1.17858(16) 0.64875(15) 0.0340(6) Uani d . . . 1.0 . .
O O1 0.9955(4) 1.16665(15) 0.67762(16) 0.0585(7) Uani d . . . 1.0 . .
O O2 0.7297(4) 1.25505(14) 0.63103(16) 0.0509(6) Uani d . . . 1.0 . .
O O3 0.0812(3) 0.87959(14) 0.54506(16) 0.0532(7) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.375(4) ?
C1 C2 . 1.382(4) ?
C1 N1 . 1.471(3) ?
C2 C3 . 1.382(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.387(4) ?
C3 H3 . 0.95 ?
C4 C5 . 1.392(3) ?
C4 C7 . 1.495(4) ?
C5 C6 . 1.386(4) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 O3 . 1.222(3) ?
C7 C8 . 1.509(4) ?
C7 C8' . 1.511(18) ?
C8 C9 . 1.534(4) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C16 . 1.524(5) ?
C9 C17 . 1.530(4) ?
C9 C10 . 1.555(3) ?
C10 C11 . 1.39 ?
C10 C15 . 1.39 ?
C11 C12 . 1.39 ?
C11 H11 . 0.95 ?
C12 C13 . 1.39 ?
C12 H12 . 0.95 ?
C13 C14 . 1.39 ?
C13 H13 . 0.95 ?
C14 C15 . 1.39 ?
C14 H14 . 0.95 ?
C15 H15 . 0.95 ?
C16 O4 . 1.205(5) ?
C16 H16 . 0.95 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C8' C9' . 1.540(18) ?
C8' H8'1 . 0.99 ?
C8' H8'2 . 0.99 ?
C9' C16' . 1.503(19) ?
C9' C17' . 1.54(2) ?
C9' C10' . 1.550(16) ?
C10' C11' . 1.39 ?
C10' C15' . 1.39 ?
C11' C12' . 1.39 ?
C11' H11' . 0.95 ?
C12' C13' . 1.39 ?
C12' H12' . 0.95 ?
C13' C14' . 1.39 ?
C13' H13' . 0.95 ?
C14' C15' . 1.39 ?
C14' H14' . 0.95 ?
C15' H15' . 0.95 ?
C16' O4' . 1.21(2) ?
C16' H16' . 0.95 ?
C17' H17D . 0.98 ?
C17' H17E . 0.98 ?
C17' H17F . 0.98 ?
N1 O1 . 1.224(3) ?
N1 O2 . 1.225(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 123.0(2) ?
C6 C1 N1 . . 118.2(2) ?
C2 C1 N1 . . 118.8(2) ?
C3 C2 C1 . . 118.1(3) ?
C3 C2 H2 . . 121.0 ?
C1 C2 H2 . . 121.0 ?
C2 C3 C4 . . 120.5(2) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C3 C4 C5 . . 119.9(2) ?
C3 C4 C7 . . 122.9(2) ?
C5 C4 C7 . . 117.2(2) ?
C6 C5 C4 . . 120.3(3) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C1 C6 C5 . . 118.2(2) ?
C1 C6 H6 . . 120.9 ?
C5 C6 H6 . . 120.9 ?
O3 C7 C4 . . 119.2(2) ?
O3 C7 C8 . . 119.7(3) ?
C4 C7 C8 . . 121.1(3) ?
O3 C7 C8' . . 114.6(18) ?
C4 C7 C8' . . 124.9(15) ?
C7 C8 C9 . . 112.7(3) ?
C7 C8 H8A . . 109.1 ?
C9 C8 H8A . . 109.1 ?
C7 C8 H8B . . 109.1 ?
C9 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.8 ?
C16 C9 C17 . . 110.0(3) ?
C16 C9 C8 . . 110.4(3) ?
C17 C9 C8 . . 109.0(3) ?
C16 C9 C10 . . 104.6(3) ?
C17 C9 C10 . . 111.0(3) ?
C8 C9 C10 . . 111.6(3) ?
C11 C10 C15 . . 120.0 ?
C11 C10 C9 . . 122.6(2) ?
C15 C10 C9 . . 117.4(2) ?
C10 C11 C12 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C13 C12 C11 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C15 C14 C13 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C10 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C10 C15 H15 . . 120.0 ?
O4 C16 C9 . . 125.0(4) ?
O4 C16 H16 . . 117.5 ?
C9 C16 H16 . . 117.5 ?
C9 C17 H17A . . 109.5 ?
C9 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C9 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C7 C8' C9' . . 115.(2) ?
C7 C8' H8'1 . . 108.4 ?
C9' C8' H8'1 . . 108.4 ?
C7 C8' H8'2 . . 108.4 ?
C9' C8' H8'2 . . 108.4 ?
H8'1 C8' H8'2 . . 107.5 ?
C16' C9' C17' . . 113.(2) ?
C16' C9' C8' . . 113.(2) ?
C17' C9' C8' . . 107.(2) ?
C16' C9' C10' . . 106.(2) ?
C17' C9' C10' . . 107.(2) ?
C8' C9' C10' . . 111.7(16) ?
C11' C10' C15' . . 120.0 ?
C11' C10' C9' . . 115.5(14) ?
C15' C10' C9' . . 124.0(14) ?
C10' C11' C12' . . 120.0 ?
C10' C11' H11' . . 120.0 ?
C12' C11' H11' . . 120.0 ?
C13' C12' C11' . . 120.0 ?
C13' C12' H12' . . 120.0 ?
C11' C12' H12' . . 120.0 ?
C14' C13' C12' . . 120.0 ?
C14' C13' H13' . . 120.0 ?
C12' C13' H13' . . 120.0 ?
C13' C14' C15' . . 120.0 ?
C13' C14' H14' . . 120.0 ?
C15' C14' H14' . . 120.0 ?
C14' C15' C10' . . 120.0 ?
C14' C15' H15' . . 120.0 ?
C10' C15' H15' . . 120.0 ?
O4' C16' C9' . . 122.(3) ?
O4' C16' H16' . . 119.0 ?
C9' C16' H16' . . 119.0 ?
C9' C17' H17D . . 109.5 ?
C9' C17' H17E . . 109.5 ?
H17D C17' H17E . . 109.5 ?
C9' C17' H17F . . 109.5 ?
H17D C17' H17F . . 109.5 ?
H17E C17' H17F . . 109.5 ?
O1 N1 O2 . . 123.1(2) ?
O1 N1 C1 . . 118.3(2) ?
O2 N1 C1 . . 118.6(2) ?

