# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_160616_ywl8_032_1
_database_code_depnum_ccdc_archive 'CCDC 1486236'
_audit_update_record             
;
2016-06-17 deposited with the CCDC.
2016-10-08 downloaded from the CCDC.
;
_audit_creation_date             2016-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H16 N2 O3'
_chemical_formula_sum            'C15 H16 N2 O3'
_chemical_formula_weight         272.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3103(8)
_cell_length_b                   4.8793(5)
_cell_length_c                   30.741(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.596(8)
_cell_angle_gamma                90.00
_cell_volume                     1387.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1106
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4493
_cell_measurement_theta_min      3.1352
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5605
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.14
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0758445000
_diffrn_orient_matrix_UB_12      -0.0135183000
_diffrn_orient_matrix_UB_13      0.0053476000
_diffrn_orient_matrix_UB_21      0.0035740000
_diffrn_orient_matrix_UB_22      0.1359123000
_diffrn_orient_matrix_UB_23      0.0082624000
_diffrn_orient_matrix_UB_31      -0.0109178000
_diffrn_orient_matrix_UB_32      -0.0497593000
_diffrn_orient_matrix_UB_33      0.0210354000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1739
_reflns_number_total             2530
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.4633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1436
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.32029(18) 0.8897(3) 0.39367(6) 0.0541(5) Uani 1 d . . .
O2 O 0.3429(2) 0.6065(5) 0.28683(7) 0.0856(7) Uani 1 d . . .
O3 O 0.6260(2) 0.0981(5) 0.20831(6) 0.0802(7) Uani 1 d . . .
N1 N 0.41006(19) 0.4613(4) 0.39377(6) 0.0417(5) Uani 1 d . . .
H1 H 0.3927 0.2906 0.3978 0.050 Uiso 1 calc . . R
N2 N 0.4752(2) 0.3868(5) 0.23968(6) 0.0509(6) Uani 1 d . . .
C1 C 0.7553(3) 0.8606(6) 0.40515(9) 0.0580(7) Uani 1 d . . .
H1A H 0.7787 0.8512 0.3766 0.070 Uiso 1 calc . . R
C2 C 0.8381(3) 1.0211(7) 0.43554(11) 0.0785(10) Uani 1 d . . .
H2 H 0.9170 1.1171 0.4274 0.094 Uiso 1 calc . . R
C3 C 0.8043(4) 1.0390(8) 0.47752(12) 0.0861(11) Uani 1 d . . .
H3 H 0.8601 1.1471 0.4979 0.103 Uiso 1 calc . . R
C4 C 0.6891(4) 0.8989(8) 0.48959(10) 0.0830(11) Uani 1 d . . .
H4 H 0.6660 0.9125 0.5181 0.100 Uiso 1 calc . . R
C5 C 0.6056(3) 0.7352(6) 0.45946(8) 0.0611(8) Uani 1 d . . .
H5 H 0.5273 0.6393 0.4681 0.073 Uiso 1 calc . . R
C6 C 0.6381(2) 0.7139(5) 0.41665(7) 0.0432(6) Uani 1 d . . .
C7 C 0.5513(2) 0.5362(5) 0.38440(7) 0.0388(5) Uani 1 d . . .
C8 C 0.3029(3) 0.6410(5) 0.39666(7) 0.0415(6) Uani 1 d . . .
C9 C 0.1597(3) 0.5204(6) 0.40401(9) 0.0614(8) Uani 1 d . . .
H9A H 0.1264 0.6032 0.4293 0.092 Uiso 1 calc . . GR
H9B H 0.1701 0.3264 0.4085 0.092 Uiso 1 calc . . GR
H9C H 0.0910 0.5543 0.3789 0.092 Uiso 1 calc . . GR
C10 C 0.6017(3) 0.4338(5) 0.34910(7) 0.0449(6) Uani 1 d . . .
H10 H 0.6976 0.4727 0.3457 0.054 Uiso 1 calc . . R
C11 C 0.5200(3) 0.2617(5) 0.31409(8) 0.0491(6) Uani 1 d . . .
H11 H 0.4550 0.1369 0.3274 0.059 Uiso 1 calc . . R
C12 C 0.4332(3) 0.4400(6) 0.28041(8) 0.0555(7) Uani 1 d . . .
C13 C 0.5774(3) 0.1840(6) 0.24079(9) 0.0541(7) Uani 1 d . . .
C14 C 0.6179(3) 0.0966(6) 0.28682(8) 0.0578(7) Uani 1 d . . .
H14A H 0.7189 0.1363 0.2960 0.069 Uiso 1 calc . . R
H14B H 0.6019 -0.0984 0.2900 0.069 Uiso 1 calc . . R
C15 C 0.4132(3) 0.5226(7) 0.19984(9) 0.0738(9) Uani 1 d . . .
H15A H 0.3406 0.4071 0.1846 0.111 Uiso 1 calc . . GR
H15B H 0.4878 0.5575 0.1814 0.111 Uiso 1 calc . . GR
H15C H 0.3702 0.6928 0.2071 0.111 Uiso 1 calc . . GR

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0561(11) 0.0295(10) 0.0765(12) 0.0003(8) 0.0063(8) 0.0002(8)
O2 0.0713(14) 0.1001(19) 0.0836(14) -0.0275(13) 0.0006(11) 0.0346(14)
O3 0.0885(15) 0.0831(16) 0.0772(13) -0.0244(12) 0.0443(12) -0.0083(12)
N1 0.0445(11) 0.0277(10) 0.0560(12) 0.0021(9) 0.0183(9) -0.0033(9)
N2 0.0482(12) 0.0524(14) 0.0529(12) -0.0101(10) 0.0092(9) -0.0055(11)
C1 0.0493(16) 0.0615(19) 0.0630(16) -0.0016(14) 0.0050(12) -0.0112(14)
C2 0.0544(19) 0.079(2) 0.099(3) -0.0163(19) -0.0020(16) -0.0203(17)
C3 0.061(2) 0.099(3) 0.092(2) -0.038(2) -0.0197(17) 0.004(2)
C4 0.079(2) 0.111(3) 0.0548(17) -0.0221(19) -0.0076(15) 0.017(2)
C5 0.0634(18) 0.070(2) 0.0507(16) -0.0031(14) 0.0084(13) 0.0014(16)
C6 0.0406(13) 0.0413(14) 0.0474(13) 0.0031(11) 0.0039(10) 0.0041(12)
C7 0.0414(13) 0.0323(13) 0.0441(13) 0.0048(10) 0.0110(10) -0.0016(11)
C8 0.0438(14) 0.0354(14) 0.0459(13) -0.0019(11) 0.0074(10) -0.0001(11)
C9 0.0474(15) 0.0499(17) 0.090(2) -0.0042(14) 0.0215(13) -0.0060(14)
C10 0.0405(13) 0.0430(15) 0.0529(14) 0.0013(12) 0.0128(10) -0.0051(12)
C11 0.0519(15) 0.0443(15) 0.0540(14) -0.0079(12) 0.0187(12) -0.0082(13)
C12 0.0443(15) 0.0586(18) 0.0642(17) -0.0204(14) 0.0088(12) -0.0025(14)
C13 0.0559(16) 0.0468(16) 0.0639(17) -0.0131(13) 0.0256(13) -0.0178(14)
C14 0.0609(17) 0.0414(15) 0.0743(18) -0.0088(13) 0.0216(13) -0.0003(13)
C15 0.072(2) 0.080(2) 0.0664(18) 0.0016(17) -0.0043(14) -0.0125(18)

_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 1.229(3) . ?
O2 C12 1.202(3) . ?
O3 C13 1.217(3) . ?
N1 H1 0.8600 . ?
N1 C7 1.426(3) . ?
N1 C8 1.339(3) . ?
N2 C12 1.378(3) . ?
N2 C13 1.371(3) . ?
N2 C15 1.452(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.384(4) . ?
C1 C6 1.384(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.358(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(3) . ?
C6 C7 1.485(3) . ?
C7 C10 1.328(3) . ?
C8 C9 1.498(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C11 1.501(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.513(4) . ?
C11 C14 1.536(3) . ?
C13 C14 1.484(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C7 N1 H1 118.1 . . ?
C8 N1 H1 118.1 . . ?
C8 N1 C7 123.9(2) . . ?
C12 N2 C15 123.6(2) . . ?
C13 N2 C12 112.5(2) . . ?
C13 N2 C15 123.9(2) . . ?
C2 C1 H1A 119.5 . . ?
C2 C1 C6 121.0(3) . . ?
C6 C1 H1A 119.5 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.9(2) . . ?
C1 C6 C7 121.1(2) . . ?
C5 C6 C7 121.1(2) . . ?
N1 C7 C6 117.30(18) . . ?
C10 C7 N1 119.3(2) . . ?
C10 C7 C6 123.3(2) . . ?
O1 C8 N1 122.4(2) . . ?
O1 C8 C9 121.8(2) . . ?
N1 C8 C9 115.8(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10 116.6 . . ?
C7 C10 C11 126.8(2) . . ?
C11 C10 H10 116.6 . . ?
C10 C11 H11 109.6 . . ?
C10 C11 C12 110.8(2) . . ?
C10 C11 C14 113.7(2) . . ?
C12 C11 H11 109.6 . . ?
C12 C11 C14 103.4(2) . . ?
C14 C11 H11 109.6 . . ?
O2 C12 N2 123.6(3) . . ?
O2 C12 C11 127.2(2) . . ?
N2 C12 C11 109.2(2) . . ?
O3 C13 N2 123.4(3) . . ?
O3 C13 C14 127.2(3) . . ?
N2 C13 C14 109.3(2) . . ?
C11 C14 H14A 110.6 . . ?
C11 C14 H14B 110.6 . . ?
C13 C14 C11 105.5(2) . . ?
C13 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
H14A C14 H14B 108.8 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O3 C13 C14 C11 -177.8(3) . . . . ?
N1 C7 C10 C11 6.3(4) . . . . ?
N2 C13 C14 C11 3.2(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C6 C7 N1 -161.0(2) . . . . ?
C1 C6 C7 C10 22.8(4) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C2 C1 C6 C7 -178.5(3) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C4 C5 C6 C7 178.9(2) . . . . ?
C5 C6 C7 N1 19.9(3) . . . . ?
C5 C6 C7 C10 -156.3(2) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
C6 C7 C10 C11 -177.6(2) . . . . ?
C7 N1 C8 O1 -3.9(3) . . . . ?
C7 N1 C8 C9 176.3(2) . . . . ?
C7 C10 C11 C12 83.8(3) . . . . ?
C7 C10 C11 C14 -160.3(2) . . . . ?
C8 N1 C7 C6 63.4(3) . . . . ?
C8 N1 C7 C10 -120.2(3) . . . . ?
C10 C11 C12 O2 -57.0(4) . . . . ?
C10 C11 C12 N2 121.9(2) . . . . ?
C10 C11 C14 C13 -122.0(2) . . . . ?
C12 N2 C13 O3 177.4(2) . . . . ?
C12 N2 C13 C14 -3.6(3) . . . . ?
C12 C11 C14 C13 -1.7(3) . . . . ?
C13 N2 C12 O2 -178.6(3) . . . . ?
C13 N2 C12 C11 2.4(3) . . . . ?
C14 C11 C12 O2 -179.2(3) . . . . ?
C14 C11 C12 N2 -0.2(3) . . . . ?
C15 N2 C12 O2 -1.1(4) . . . . ?
C15 N2 C12 C11 179.9(2) . . . . ?
C15 N2 C13 O3 -0.1(4) . . . . ?
C15 N2 C13 C14 178.9(2) . . . . ?

