# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_20161208_Nanligong_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1523402'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-11-23 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         ?
_chemical_formula_sum            'C16 H15 N3 O5'
_chemical_formula_weight         329.31

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      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   7.4889(7)
_cell_length_b                   8.9633(8)
_cell_length_c                   12.2743(11)
_cell_angle_alpha                98.953(3)
_cell_angle_beta                 106.482(3)
_cell_angle_gamma                98.679(3)
_cell_volume                     763.71(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1852
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.79
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.977
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5614
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.351
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2678
_reflns_number_gt                1897
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0384P)²+0.1747P] 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         2678
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C 0.6503(3) 0.6379(3) 0.77691(19) 0.0240(6) Uani 1 1 d . . . . .
H1 H 0.6107 0.5743 0.7034 0.029 Uiso 1 1 calc R U . . .
C2 C 0.6355(3) 0.5767(3) 0.8713(2) 0.0276(6) Uani 1 1 d . . . . .
H2 H 0.5864 0.4720 0.8611 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6937(3) 0.6707(3) 0.9813(2) 0.0290(6) Uani 1 1 d . . . . .
H3 H 0.6837 0.6292 1.0447 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7668(3) 0.8267(3) 0.9965(2) 0.0283(6) Uani 1 1 d . . . . .
H4 H 0.8051 0.8902 1.0700 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7827(3) 0.8879(3) 0.90226(18) 0.0245(6) Uani 1 1 d . . . . .
H5 H 0.8330 0.9925 0.9130 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7243(3) 0.7946(2) 0.79143(18) 0.0190(5) Uani 1 1 d . . . . .
C7 C 0.7478(3) 0.8683(3) 0.69390(19) 0.0193(5) Uani 1 1 d . . . . .
C8 C 0.6004(3) 0.8380(2) 0.47875(17) 0.0179(5) Uani 1 1 d . . . . .
C9 C 0.7450(3) 0.9339(2) 0.45749(18) 0.0212(5) Uani 1 1 d . . . . .
H9 H 0.8582 0.9771 0.5172 0.025 Uiso 1 1 calc R U . . .
C10 C 0.7220(3) 0.9658(3) 0.34815(19) 0.0235(5) Uani 1 1 d . . . . .
H10 H 0.8194 1.0311 0.3352 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5555(3) 0.9015(3) 0.25779(19) 0.0234(6) Uani 1 1 d . . . . .
H11 H 0.5423 0.9203 0.1838 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4090(3) 0.8089(2) 0.27896(18) 0.0221(5) Uani 1 1 d . . . . .
H12 H 0.2965 0.7664 0.2186 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4266(3) 0.7780(2) 0.38914(18) 0.0184(5) Uani 1 1 d . . . . .
C14 C 0.2622(3) 0.6836(2) 0.41069(18) 0.0200(5) Uani 1 1 d . . . . .
C15 C -0.0831(3) 0.6066(2) 0.35658(19) 0.0231(5) Uani 1 1 d . . . . .
H15A H -0.1910 0.6500 0.3212 0.028 Uiso 1 1 calc R U . . .
H15B H -0.0720 0.6146 0.4381 0.028 Uiso 1 1 calc R U . . .
C16 C -0.1214(3) 0.4378(2) 0.29910(17) 0.0218(5) Uani 1 1 d . . . . .
H16A H -0.0125 0.3928 0.3296 0.026 Uiso 1 1 calc R U . . .
H16B H -0.2316 0.3806 0.3119 0.026 Uiso 1 1 calc R U . . .
N1 N -0.2077(3) 0.2862(2) 0.10722(17) 0.0302(5) Uani 1 1 d . . . . .
N2 N 0.0879(3) 0.6968(2) 0.34762(15) 0.0215(5) Uani 1 1 d . . . . .
H2A H 0.0780 0.7599 0.3012 0.026 Uiso 1 1 calc R U . . .
N3 N 0.6196(2) 0.7980(2) 0.58762(14) 0.0203(4) Uani 1 1 d . . . . .
H3A H 0.5395 0.7181 0.5871 0.024 Uiso 1 1 calc R U . . .
O1 O 0.8717(2) 0.98344(17) 0.70985(12) 0.0232(4) Uani 1 1 d . . . . .
O2 O 0.2821(2) 0.59718(17) 0.48116(13) 0.0255(4) Uani 1 1 d . . . . .
O3 O -0.2204(3) 0.17968(19) 0.15464(14) 0.0403(5) Uani 1 1 d . . . . .
O4 O -0.2333(3) 0.2862(2) 0.00596(14) 0.0459(5) Uani 1 1 d . . . . .
O5 O -0.1560(2) 0.43578(16) 0.17637(12) 0.0258(4) Uani 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
C1 C2 1.382(3) . ?
C1 C6 1.394(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.494(3) . ?
C7 O1 1.228(3) . ?
C7 N3 1.368(3) . ?
C8 C9 1.389(3) . ?
C8 C13 1.409(3) . ?
C8 N3 1.411(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.396(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.497(3) . ?
C14 O2 1.241(2) . ?
C14 N2 1.349(3) . ?
C15 N2 1.449(3) . ?
C15 C16 1.513(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O5 1.451(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
N1 O3 1.199(2) . ?
N1 O4 1.202(2) . ?
N1 O5 1.403(2) . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?

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 C1 C6 120.3(2) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 117.8(2) . . ?
C1 C6 C7 123.27(19) . . ?
O1 C7 N3 123.8(2) . . ?
O1 C7 C6 121.8(2) . . ?
N3 C7 C6 114.4(2) . . ?
C9 C8 C13 119.4(2) . . ?
C9 C8 N3 122.5(2) . . ?
C13 C8 N3 118.0(2) . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.2(2) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 118.8(2) . . ?
C12 C13 C14 120.0(2) . . ?
C8 C13 C14 121.1(2) . . ?
O2 C14 N2 121.2(2) . . ?
O2 C14 C13 123.0(2) . . ?
N2 C14 C13 115.8(2) . . ?
N2 C15 C16 113.50(18) . . ?
N2 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N2 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
O5 C16 C15 105.16(17) . . ?
O5 C16 H16A 110.7 . . ?
C15 C16 H16A 110.7 . . ?
O5 C16 H16B 110.7 . . ?
C15 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
O3 N1 O4 129.6(2) . . ?
O3 N1 O5 117.79(19) . . ?
O4 N1 O5 112.61(19) . . ?
C14 N2 C15 121.28(19) . . ?
C14 N2 H2A 119.4 . . ?
C15 N2 H2A 119.4 . . ?
C7 N3 C8 129.1(2) . . ?
C7 N3 H3A 115.4 . . ?
C8 N3 H3A 115.4 . . ?
N1 O5 C16 113.30(16) . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.054

