# 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_140328_lg_1_100p
_audit_block_doi                 10.5517/ccdc.csd.cc1md1z1
_database_code_depnum_ccdc_archive 'CCDC 1501143'
_audit_update_record             
;
2016-08-26 deposited with the CCDC.
2017-06-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N O3'
_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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2462(9)
_cell_length_b                   8.2150(10)
_cell_length_c                   20.228(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.583(10)
_cell_angle_gamma                90.00
_cell_volume                     1201.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1156
_cell_measurement_theta_min      2.8109
_cell_measurement_theta_max      29.2369

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4684
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2190
_reflns_number_gt                1421
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0537P)²+0.0969P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0079(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2190
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31917(17) 0.89478(14) 0.11936(6) 0.0498(4) Uani 1 1 d . . .
O2 O 0.1550(2) 1.44455(19) 0.13804(9) 0.0844(6) Uani 1 1 d . . .
O3 O 0.2313(2) 1.25128(17) 0.21283(8) 0.0685(5) Uani 1 1 d . . .
N1 N 0.2863(2) 0.8264(3) -0.08564(9) 0.0674(5) Uani 1 1 d . . .
C1 C 0.3059(2) 0.8752(2) 0.05096(10) 0.0448(5) Uani 1 1 d . . .
C2 C 0.3460(3) 0.7271(2) 0.02593(11) 0.0565(5) Uani 1 1 d . . .
H2 H 0.3800 0.6400 0.0534 0.068 Uiso 1 1 calc R . .
C3 C 0.3340(3) 0.7113(3) -0.04281(12) 0.0674(6) Uani 1 1 d . . .
H3 H 0.3624 0.6099 -0.0599 0.081 Uiso 1 1 calc R . .
C4 C 0.2440(2) 0.9737(3) -0.05992(10) 0.0537(5) Uani 1 1 d . . .
C5 C 0.2516(2) 1.0046(2) 0.00870(9) 0.0434(5) Uani 1 1 d . . .
C6 C 0.2044(2) 1.1601(2) 0.03295(10) 0.0457(5) Uani 1 1 d . . .
C7 C 0.1475(3) 1.2806(3) -0.01024(12) 0.0608(6) Uani 1 1 d . . .
H7 H 0.1146 1.3823 0.0054 0.073 Uiso 1 1 calc R . .
C8 C 0.1394(3) 1.2492(3) -0.07822(12) 0.0719(7) Uani 1 1 d . . .
H8 H 0.0997 1.3311 -0.1075 0.086 Uiso 1 1 calc R . .
C9 C 0.1876(3) 1.1030(3) -0.10281(11) 0.0679(6) Uani 1 1 d . . .
H9 H 0.1836 1.0874 -0.1484 0.081 Uiso 1 1 calc R . .
C10 C 0.2217(2) 1.1701(2) 0.10430(10) 0.0459(5) Uani 1 1 d . . .
C11 C 0.2759(2) 1.0447(2) 0.14133(9) 0.0459(5) Uani 1 1 d . . .
C12 C 0.2907(3) 1.0811(2) 0.21327(10) 0.0583(6) Uani 1 1 d . . .
C13 C 0.1962(3) 1.3052(3) 0.14957(12) 0.0616(6) Uani 1 1 d . . .
C14 C 0.4883(3) 1.0750(3) 0.24211(12) 0.0771(7) Uani 1 1 d . . .
H14A H 0.5311 0.9644 0.2427 0.116 Uiso 1 1 calc R . .
H14B H 0.4940 1.1168 0.2865 0.116 Uiso 1 1 calc R . .
H14C H 0.5651 1.1399 0.2155 0.116 Uiso 1 1 calc R . .
C15 C 0.1584(4) 0.9820(3) 0.25212(12) 0.0870(8) Uani 1 1 d . . .
H15A H 0.0334 1.0099 0.2380 0.130 Uiso 1 1 calc R . .
H15B H 0.1796 1.0050 0.2985 0.130 Uiso 1 1 calc R . .
H15C H 0.1783 0.8682 0.2444 0.130 Uiso 1 1 calc R . .

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 0.0569(8) 0.0452(8) 0.0475(9) 0.0045(6) 0.0057(6) 0.0039(6)
O2 0.0934(13) 0.0526(9) 0.1084(14) -0.0049(9) 0.0151(10) 0.0184(9)
O3 0.0750(10) 0.0658(10) 0.0653(11) -0.0135(8) 0.0089(8) 0.0097(8)
N1 0.0578(11) 0.0867(14) 0.0584(12) -0.0103(11) 0.0101(9) -0.0072(10)
C1 0.0360(10) 0.0493(11) 0.0498(12) 0.0008(9) 0.0073(8) -0.0034(8)
C2 0.0553(12) 0.0482(12) 0.0669(15) -0.0036(10) 0.0112(10) 0.0016(9)
C3 0.0627(14) 0.0662(15) 0.0750(17) -0.0193(13) 0.0175(12) -0.0022(11)
C4 0.0358(10) 0.0717(14) 0.0542(13) -0.0002(11) 0.0074(9) -0.0076(10)
C5 0.0285(9) 0.0537(11) 0.0485(12) 0.0044(9) 0.0058(8) -0.0045(8)
C6 0.0289(9) 0.0494(11) 0.0594(13) 0.0100(9) 0.0070(8) -0.0013(8)
C7 0.0469(11) 0.0616(13) 0.0741(16) 0.0213(12) 0.0046(10) 0.0050(10)
C8 0.0530(13) 0.0900(18) 0.0722(18) 0.0360(14) -0.0014(11) 0.0046(13)
C9 0.0498(12) 0.1035(19) 0.0502(14) 0.0162(13) 0.0024(10) -0.0054(13)
C10 0.0388(10) 0.0437(11) 0.0560(13) 0.0013(9) 0.0086(8) 0.0029(9)
C11 0.0423(10) 0.0438(11) 0.0524(12) 0.0003(9) 0.0095(8) -0.0003(9)
C12 0.0661(14) 0.0561(13) 0.0535(13) -0.0043(10) 0.0098(10) 0.0015(10)
C13 0.0525(12) 0.0523(13) 0.0808(17) -0.0041(12) 0.0109(11) 0.0047(10)
C14 0.0832(16) 0.0802(16) 0.0658(16) -0.0077(12) -0.0115(12) 0.0058(13)
C15 0.102(2) 0.1038(19) 0.0582(16) -0.0007(14) 0.0272(14) -0.0164(16)

_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 C11 1.353(2) . ?
O1 C1 1.390(2) . ?
O2 C13 1.202(2) . ?
O3 C13 1.363(3) . ?
O3 C12 1.463(2) . ?
N1 C3 1.314(3) . ?
N1 C4 1.360(3) . ?
C1 C2 1.356(3) . ?
C1 C5 1.405(2) . ?
C2 C3 1.394(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.409(3) . ?
C4 C9 1.416(3) . ?
C5 C6 1.418(3) . ?
C6 C7 1.366(3) . ?
C6 C10 1.443(3) . ?
C7 C8 1.397(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.354(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.319(2) . ?
C10 C13 1.458(3) . ?
C11 C12 1.483(3) . ?
C12 C14 1.512(3) . ?
C12 C15 1.515(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
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
C11 O1 C1 115.41(14) . . ?
C13 O3 C12 110.74(15) . . ?
C3 N1 C4 116.4(2) . . ?
C2 C1 O1 118.18(17) . . ?
C2 C1 C5 120.65(19) . . ?
O1 C1 C5 121.17(16) . . ?
C1 C2 C3 117.1(2) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
N1 C3 C2 126.0(2) . . ?
N1 C3 H3 117.0 . . ?
C2 C3 H3 117.0 . . ?
N1 C4 C5 122.81(19) . . ?
N1 C4 C9 119.8(2) . . ?
C5 C4 C9 117.4(2) . . ?
C1 C5 C4 117.08(18) . . ?
C1 C5 C6 122.39(17) . . ?
C4 C5 C6 120.53(17) . . ?
C7 C6 C5 120.05(19) . . ?
C7 C6 C10 127.03(19) . . ?
C5 C6 C10 112.91(16) . . ?
C6 C7 C8 119.2(2) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 122.0(2) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C4 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C11 C10 C6 121.85(17) . . ?
C11 C10 C13 106.43(19) . . ?
C6 C10 C13 131.68(18) . . ?
C10 C11 O1 126.26(18) . . ?
C10 C11 C12 113.62(17) . . ?
O1 C11 C12 120.11(16) . . ?
O3 C12 C11 100.56(15) . . ?
O3 C12 C14 107.78(16) . . ?
C11 C12 C14 112.37(18) . . ?
O3 C12 C15 108.73(18) . . ?
C11 C12 C15 113.05(18) . . ?
C14 C12 C15 113.4(2) . . ?
O2 C13 O3 121.4(2) . . ?
O2 C13 C10 130.0(2) . . ?
O3 C13 C10 108.58(17) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.039
