# 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_160711gyq_0m
_database_code_depnum_ccdc_archive 'CCDC 1551041'
_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N O5'
_chemical_formula_weight         291.30

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           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   9.8219(11)
_cell_length_b                   16.4158(18)
_cell_length_c                   18.583(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2996.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    55
_cell_measurement_theta_min      7.5
_cell_measurement_theta_max      20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9723
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17691
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2938
_reflns_number_gt                2319
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0409P)²+0.9714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0062(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2938
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C1 C 0.75398(16) 0.29469(9) 0.62127(9) 0.0421(4) Uani 1 1 d . . .
H1 H 0.7988 0.2672 0.5845 0.051 Uiso 1 1 calc R . .
C2 C 0.81577(17) 0.36074(10) 0.65404(10) 0.0510(4) Uani 1 1 d . . .
H2 H 0.9020 0.3773 0.6394 0.061 Uiso 1 1 calc R . .
C3 C 0.7503(2) 0.40184(10) 0.70810(10) 0.0547(5) Uani 1 1 d . . .
H3 H 0.7927 0.4455 0.7308 0.066 Uiso 1 1 calc R . .
C4 C 0.6217(2) 0.37835(10) 0.72874(10) 0.0574(5) Uani 1 1 d . . .
H4 H 0.5766 0.4070 0.7647 0.069 Uiso 1 1 calc R . .
C5 C 0.55909(18) 0.31245(10) 0.69644(9) 0.0480(4) Uani 1 1 d . . .
H5 H 0.4720 0.2970 0.7107 0.058 Uiso 1 1 calc R . .
C6 C 0.62576(15) 0.26923(9) 0.64284(8) 0.0350(3) Uani 1 1 d . . .
C7 C 0.56265(14) 0.19770(8) 0.60858(8) 0.0330(3) Uani 1 1 d . . .
C8 C 0.49091(14) 0.13926(8) 0.64154(8) 0.0319(3) Uani 1 1 d . . .
C9 C 0.37204(15) 0.11843(8) 0.75361(8) 0.0347(3) Uani 1 1 d . . .
C10 C 0.38950(19) 0.09972(11) 0.83185(9) 0.0484(4) Uani 1 1 d . . .
H10A H 0.3028 0.1029 0.8556 0.073 Uiso 1 1 calc R . .
H10B H 0.4509 0.1384 0.8530 0.073 Uiso 1 1 calc R . .
H10C H 0.4260 0.0458 0.8372 0.073 Uiso 1 1 calc R . .
C11 C 0.43042(14) 0.06693(8) 0.60448(8) 0.0333(3) Uani 1 1 d . . .
C12 C 0.2964(2) 0.01675(11) 0.50960(10) 0.0579(5) Uani 1 1 d . . .
H12A H 0.3565 -0.0301 0.5104 0.070 Uiso 1 1 calc R . .
H12B H 0.2785 0.0306 0.4597 0.070 Uiso 1 1 calc R . .
C13 C 0.1659(2) -0.00413(15) 0.54616(15) 0.0871(8) Uani 1 1 d . . .
H13A H 0.1841 -0.0205 0.5948 0.131 Uiso 1 1 calc R . .
H13B H 0.1223 -0.0480 0.5209 0.131 Uiso 1 1 calc R . .
H13C H 0.1072 0.0426 0.5463 0.131 Uiso 1 1 calc R . .
C14 C 0.57370(16) 0.24097(10) 0.48637(9) 0.0413(4) Uani 1 1 d . . .
C15 C 0.6544(2) 0.22545(13) 0.42021(9) 0.0595(5) Uani 1 1 d . . .
H15A H 0.6264 0.2625 0.3831 0.089 Uiso 1 1 calc R . .
H15B H 0.6397 0.1705 0.4044 0.089 Uiso 1 1 calc R . .
H15C H 0.7494 0.2333 0.4303 0.089 Uiso 1 1 calc R . .
N1 N 0.48788(12) 0.13416(7) 0.71736(6) 0.0357(3) Uani 1 1 d . . .
H1A H 0.5621 0.1413 0.7411 0.043 Uiso 1 1 calc R . .
O1 O 0.26159(11) 0.11874(8) 0.72313(6) 0.0494(3) Uani 1 1 d . . .
O2 O 0.44249(12) -0.00086(6) 0.62800(6) 0.0490(3) Uani 1 1 d . . .
O3 O 0.36286(12) 0.08541(6) 0.54522(6) 0.0470(3) Uani 1 1 d . . .
O4 O 0.60219(11) 0.18301(6) 0.53743(5) 0.0387(3) Uani 1 1 d . . .
O5 O 0.49440(14) 0.29426(8) 0.49696(7) 0.0600(4) Uani 1 1 d . . .

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
C1 0.0368(8) 0.0411(8) 0.0483(9) 0.0001(7) 0.0041(7) -0.0031(7)
C2 0.0419(9) 0.0456(9) 0.0656(12) 0.0036(8) -0.0035(8) -0.0112(8)
C3 0.0651(12) 0.0385(9) 0.0604(11) -0.0042(8) -0.0137(9) -0.0091(8)
C4 0.0746(13) 0.0443(9) 0.0533(11) -0.0113(8) 0.0101(10) -0.0027(9)
C5 0.0506(10) 0.0410(9) 0.0524(10) -0.0061(7) 0.0138(8) -0.0057(8)
C6 0.0350(8) 0.0334(7) 0.0367(8) 0.0018(6) 0.0024(6) -0.0017(6)
C7 0.0299(7) 0.0341(7) 0.0352(8) -0.0006(6) 0.0033(6) 0.0021(6)
C8 0.0256(7) 0.0356(7) 0.0346(8) 0.0014(6) 0.0004(6) 0.0020(6)
C9 0.0332(8) 0.0349(7) 0.0361(8) -0.0021(6) 0.0027(6) -0.0014(6)
C10 0.0548(10) 0.0526(10) 0.0376(9) -0.0002(8) 0.0031(8) -0.0035(8)
C11 0.0293(7) 0.0350(8) 0.0356(8) 0.0028(6) 0.0028(6) 0.0024(6)
C12 0.0803(14) 0.0460(9) 0.0475(10) -0.0063(8) -0.0169(9) -0.0125(9)
C13 0.0491(12) 0.0797(15) 0.133(2) -0.0342(15) -0.0168(13) -0.0096(11)
C14 0.0414(9) 0.0427(9) 0.0398(9) 0.0012(7) -0.0053(7) -0.0058(7)
C15 0.0665(12) 0.0728(12) 0.0394(9) 0.0058(9) 0.0064(9) -0.0057(10)
N1 0.0272(6) 0.0456(7) 0.0343(7) 0.0021(5) -0.0030(5) -0.0053(5)
O1 0.0280(6) 0.0746(8) 0.0456(6) -0.0007(6) 0.0022(5) -0.0030(5)
O2 0.0578(7) 0.0326(6) 0.0565(7) 0.0069(5) -0.0069(6) 0.0034(5)
O3 0.0624(7) 0.0368(6) 0.0419(6) 0.0036(5) -0.0164(5) -0.0072(5)
O4 0.0458(6) 0.0341(5) 0.0363(6) -0.0007(4) 0.0093(5) -0.0016(5)
O5 0.0644(8) 0.0610(8) 0.0547(8) 0.0037(6) -0.0075(6) 0.0175(7)

_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(2) . ?
C1 C6 1.386(2) . ?
C2 C3 1.370(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.382(2) . ?
C5 C6 1.387(2) . ?
C6 C7 1.473(2) . ?
C7 C8 1.3386(19) . ?
C7 O4 1.3988(17) . ?
C8 N1 1.4119(18) . ?
C8 C11 1.496(2) . ?
C9 O1 1.2238(18) . ?
C9 N1 1.3472(18) . ?
C9 C10 1.496(2) . ?
C11 O2 1.2014(17) . ?
C11 O3 1.3211(18) . ?
C12 O3 1.4611(19) . ?
C12 C13 1.491(3) . ?
C14 O5 1.188(2) . ?
C14 O4 1.3725(19) . ?
C14 C15 1.485(2) . ?

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 120.49(15) . . ?
C3 C2 C1 120.16(16) . . ?
C2 C3 C4 119.85(16) . . ?
C3 C4 C5 120.49(17) . . ?
C4 C5 C6 120.14(16) . . ?
C1 C6 C5 118.84(14) . . ?
C1 C6 C7 119.86(13) . . ?
C5 C6 C7 121.30(13) . . ?
C8 C7 O4 117.07(12) . . ?
C8 C7 C6 126.52(14) . . ?
O4 C7 C6 115.42(12) . . ?
C7 C8 N1 120.68(13) . . ?
C7 C8 C11 124.56(13) . . ?
N1 C8 C11 113.83(12) . . ?
O1 C9 N1 121.10(14) . . ?
O1 C9 C10 123.52(14) . . ?
N1 C9 C10 115.38(13) . . ?
O2 C11 O3 124.44(14) . . ?
O2 C11 C8 121.92(13) . . ?
O3 C11 C8 113.64(12) . . ?
O3 C12 C13 110.80(16) . . ?
O5 C14 O4 121.99(15) . . ?
O5 C14 C15 127.85(16) . . ?
O4 C14 C15 110.17(14) . . ?
C9 N1 C8 121.88(12) . . ?
C11 O3 C12 115.15(12) . . ?
C14 O4 C7 118.52(12) . . ?

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
C6 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C2 C1 C6 C7 -178.61(14) . . . . ?
C4 C5 C6 C1 -1.7(2) . . . . ?
C4 C5 C6 C7 178.67(16) . . . . ?
C1 C6 C7 C8 139.55(16) . . . . ?
C5 C6 C7 C8 -40.8(2) . . . . ?
C1 C6 C7 O4 -28.7(2) . . . . ?
C5 C6 C7 O4 150.97(14) . . . . ?
O4 C7 C8 N1 157.33(12) . . . . ?
C6 C7 C8 N1 -10.7(2) . . . . ?
O4 C7 C8 C11 -11.0(2) . . . . ?
C6 C7 C8 C11 -179.03(13) . . . . ?
C7 C8 C11 O2 133.18(16) . . . . ?
N1 C8 C11 O2 -35.84(19) . . . . ?
C7 C8 C11 O3 -47.55(19) . . . . ?
N1 C8 C11 O3 143.43(13) . . . . ?
O1 C9 N1 C8 -9.9(2) . . . . ?
C10 C9 N1 C8 169.13(13) . . . . ?
C7 C8 N1 C9 137.82(15) . . . . ?
C11 C8 N1 C9 -52.69(18) . . . . ?
O2 C11 O3 C12 2.3(2) . . . . ?
C8 C11 O3 C12 -176.96(13) . . . . ?
C13 C12 O3 C11 79.7(2) . . . . ?
O5 C14 O4 C7 -15.4(2) . . . . ?
C15 C14 O4 C7 164.74(13) . . . . ?
C8 C7 O4 C14 128.64(14) . . . . ?
C6 C7 O4 C14 -61.97(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.86 2.10 2.9179(16) 158.2 6_657

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.033
