# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1879290'
loop_
_audit_author_name
_audit_author_address
'Lianghua zou'
;Jiangnan University
China
;
_audit_update_record             
;
2018-11-16 deposited with the CCDC.	2019-05-21 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            'C15 H11 N O3'
_chemical_formula_weight         253.25

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   12.8593(8)
_cell_length_b                   14.1412(10)
_cell_length_c                   6.7109(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1220.35(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3767
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_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      173(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            5786
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.168
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2105
_reflns_number_gt                1984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.973

_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)+(0.0428P)²+0.1561P] 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 817 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2105
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.096
_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 0.38822(18) 0.80957(17) 0.5475(4) 0.0313(6) Uani 1 1 d . . . . .
H1 H 0.366484 0.750382 0.599955 0.038 Uiso 1 1 calc R U . . .
C2 C 0.31690(19) 0.88178(19) 0.5211(5) 0.0416(7) Uani 1 1 d . . . . .
H2 H 0.246335 0.872411 0.558062 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3477(2) 0.96764(18) 0.4410(5) 0.0427(7) Uani 1 1 d . . . . .
H3 H 0.298320 1.016823 0.422556 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4503(2) 0.98160(17) 0.3881(4) 0.0367(7) Uani 1 1 d . . . . .
H4 H 0.471090 1.040084 0.331062 0.044 Uiso 1 1 calc R U . . .
C5 C 0.52313(18) 0.91056(15) 0.4180(4) 0.0287(6) Uani 1 1 d . . . . .
H5 H 0.593989 0.920993 0.384525 0.034 Uiso 1 1 calc R U . . .
C6 C 0.49223(17) 0.82416(15) 0.4969(4) 0.0243(5) Uani 1 1 d . . . . .
C7 C 0.56532(17) 0.74310(14) 0.5181(4) 0.0227(5) Uani 1 1 d . . . . .
C8 C 0.68212(17) 0.76399(15) 0.5453(3) 0.0216(5) Uani 1 1 d . . . . .
C9 C 0.85013(16) 0.68069(14) 0.5017(4) 0.0217(5) Uani 1 1 d . . . . .
C10 C 0.89521(16) 0.58990(14) 0.4804(4) 0.0250(5) Uani 1 1 d . . . . .
C11 C 1.00359(17) 0.58108(15) 0.4858(4) 0.0303(6) Uani 1 1 d . . . . .
H11 H 1.034282 0.520302 0.472507 0.036 Uiso 1 1 calc R U . . .
C12 C 1.06676(18) 0.65947(16) 0.5101(5) 0.0307(5) Uani 1 1 d . . . . .
H12 H 1.140222 0.652762 0.514844 0.037 Uiso 1 1 calc R U . . .
C13 C 1.02122(17) 0.74782(16) 0.5273(4) 0.0283(5) Uani 1 1 d . . . . .
H13 H 1.064306 0.801971 0.541553 0.034 Uiso 1 1 calc R U . . .
C14 C 0.91445(16) 0.75895(15) 0.5243(4) 0.0244(5) Uani 1 1 d . . . . .
H14 H 0.884967 0.820218 0.537699 0.029 Uiso 1 1 calc R U . . .
C15 C 0.83501(18) 0.50371(15) 0.4455(4) 0.0314(6) Uani 1 1 d . . . . .
H15 H 0.872339 0.445756 0.442863 0.038 Uiso 1 1 calc R U . . .
N1 N 0.74130(13) 0.68841(11) 0.4948(3) 0.0220(4) Uani 1 1 d . . . . .
H1A H 0.707484 0.638137 0.452725 0.026 Uiso 1 1 calc R U . . .
O1 O 0.53610(11) 0.66134(10) 0.5167(3) 0.0293(4) Uani 1 1 d . . . . .
O2 O 0.71274(11) 0.83907(10) 0.6112(3) 0.0290(4) Uani 1 1 d . . . . .
O3 O 0.74145(12) 0.49949(10) 0.4195(3) 0.0359(5) 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 1.384(3) . ?
C1 C6 1.395(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.489(3) . ?
C7 O1 1.216(3) . ?
C7 C8 1.542(3) . ?
C8 O2 1.216(3) . ?
C8 N1 1.355(3) . ?
C9 C14 1.390(3) . ?
C9 N1 1.405(3) . ?
C9 C10 1.416(3) . ?
C10 C11 1.400(3) . ?
C10 C15 1.463(3) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O3 1.217(3) . ?
C15 H15 0.9500 . ?
N1 H1A 0.8800 . ?

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 119.7(2) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 122.2(2) . . ?
C1 C6 C7 117.9(2) . . ?
O1 C7 C6 122.4(2) . . ?
O1 C7 C8 118.97(18) . . ?
C6 C7 C8 118.61(18) . . ?
O2 C8 N1 126.7(2) . . ?
O2 C8 C7 121.74(18) . . ?
N1 C8 C7 111.49(18) . . ?
C14 C9 N1 122.31(18) . . ?
C14 C9 C10 119.30(19) . . ?
N1 C9 C10 118.37(18) . . ?
C11 C10 C9 119.07(19) . . ?
C11 C10 C15 117.18(19) . . ?
C9 C10 C15 123.71(19) . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C9 120.14(19) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
O3 C15 C10 125.9(2) . . ?
O3 C15 H15 117.0 . . ?
C10 C15 H15 117.0 . . ?
C8 N1 C9 127.79(18) . . ?
C8 N1 H1A 116.1 . . ?
C9 N1 H1A 116.1 . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.033



