# 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_xb7771_0m
_database_code_depnum_ccdc_archive 'CCDC 1540163'
_audit_update_record             
;
2017-03-25 deposited with the CCDC.
2017-05-10 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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   8.385(2)
_cell_length_b                   7.230(2)
_cell_length_c                   23.546(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.540(6)
_cell_angle_gamma                90.00
_cell_volume                     1426.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1239
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      23.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      1.356
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_process_details   ?

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6923
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2534
_reflns_number_gt                1830
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_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)+(0.0670P)²+0.1411P] 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       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2534
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
N1 N 0.41646(19) 0.1943(2) 0.23999(7) 0.0468(5) Uani 1 1 d . . .
H1 H 0.4728 0.1670 0.2112 0.056 Uiso 1 1 calc R . .
O1 O 0.7089(2) 0.1014(3) 0.49116(7) 0.0716(5) Uani 1 1 d . . .
O2 O 0.45012(16) 0.1289(2) 0.13197(6) 0.0525(4) Uani 1 1 d . . .
O3 O 0.24215(16) 0.1904(2) 0.07474(6) 0.0524(4) Uani 1 1 d . . .
O4 O -0.03186(15) 0.1242(2) 0.12940(6) 0.0508(4) Uani 1 1 d . . .
O5 O -0.0373(2) 0.3962(3) 0.17234(8) 0.0786(6) Uani 1 1 d . . .
C1 C 0.9440(3) 0.2114(4) 0.45034(11) 0.0726(8) Uani 1 1 d . . .
H1A H 0.9864 0.1991 0.4884 0.109 Uiso 1 1 calc R . .
H1B H 0.9523 0.3380 0.4384 0.109 Uiso 1 1 calc R . .
H1C H 1.0034 0.1341 0.4254 0.109 Uiso 1 1 calc R . .
C2 C 0.7728(3) 0.1539(3) 0.44846(10) 0.0511(6) Uani 1 1 d . . .
C3 C 0.6807(2) 0.1643(3) 0.39356(8) 0.0424(5) Uani 1 1 d . . .
C4 C 0.7471(2) 0.2292(3) 0.34413(9) 0.0456(5) Uani 1 1 d . . .
H4 H 0.8534 0.2660 0.3446 0.055 Uiso 1 1 calc R . .
C5 C 0.6580(2) 0.2399(3) 0.29446(9) 0.0445(5) Uani 1 1 d . . .
H5 H 0.7043 0.2842 0.2617 0.053 Uiso 1 1 calc R . .
C6 C 0.4996(2) 0.1852(3) 0.29291(8) 0.0418(5) Uani 1 1 d . . .
C7 C 0.4334(3) 0.1147(3) 0.34147(9) 0.0492(6) Uani 1 1 d . . .
H7 H 0.3284 0.0730 0.3405 0.059 Uiso 1 1 calc R . .
C8 C 0.5230(2) 0.1062(3) 0.39131(9) 0.0479(5) Uani 1 1 d . . .
H8 H 0.4770 0.0607 0.4240 0.057 Uiso 1 1 calc R . .
C9 C 0.2643(2) 0.2385(3) 0.22722(8) 0.0404(5) Uani 1 1 d . . .
C10 C 0.1618(3) 0.3082(3) 0.27397(9) 0.0567(6) Uani 1 1 d . . .
H10A H 0.0999 0.2080 0.2885 0.085 Uiso 1 1 calc R . .
H10B H 0.0915 0.4027 0.2593 0.085 Uiso 1 1 calc R . .
H10C H 0.2283 0.3586 0.3040 0.085 Uiso 1 1 calc R . .
C11 C 0.2061(2) 0.2235(3) 0.17205(8) 0.0385(5) Uani 1 1 d . . .
C12 C 0.3109(2) 0.1734(3) 0.12631(8) 0.0401(5) Uani 1 1 d . . .
C13 C 0.3426(3) 0.1520(4) 0.02739(9) 0.0644(7) Uani 1 1 d . . .
H13A H 0.4351 0.2302 0.0296 0.097 Uiso 1 1 calc R . .
H13B H 0.2843 0.1755 -0.0075 0.097 Uiso 1 1 calc R . .
H13C H 0.3752 0.0248 0.0286 0.097 Uiso 1 1 calc R . .
C14 C 0.0371(2) 0.2621(3) 0.15859(8) 0.0440(5) Uani 1 1 d . . .
C15 C -0.1952(2) 0.1530(4) 0.11140(11) 0.0665(7) Uani 1 1 d . . .
H15A H -0.2566 0.1878 0.1435 0.100 Uiso 1 1 calc R . .
H15B H -0.2374 0.0408 0.0952 0.100 Uiso 1 1 calc R . .
H15C H -0.2004 0.2496 0.0834 0.100 Uiso 1 1 calc R . .


_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
N1 C9 1.342(2) . ?
N1 C6 1.413(2) . ?
N1 H1 0.8600 . ?
O1 C2 1.213(3) . ?
O2 C12 1.215(2) . ?
O3 C12 1.336(2) . ?
O3 C13 1.442(2) . ?
O4 C14 1.334(2) . ?
O4 C15 1.438(2) . ?
O5 C14 1.202(2) . ?
C1 C2 1.494(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.490(3) . ?
C3 C4 1.386(3) . ?
C3 C8 1.387(3) . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(3) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C11 1.380(3) . ?
C9 C10 1.502(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.454(3) . ?
C11 C14 1.470(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C9 N1 C6 130.73(17) . . ?
C9 N1 H1 114.6 . . ?
C6 N1 H1 114.6 . . ?
C12 O3 C13 116.01(16) . . ?
C14 O4 C15 116.11(18) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 120.3(2) . . ?
O1 C2 C1 120.6(2) . . ?
C3 C2 C1 119.1(2) . . ?
C4 C3 C8 118.35(18) . . ?
C4 C3 C2 122.36(19) . . ?
C8 C3 C2 119.28(19) . . ?
C5 C4 C3 120.86(19) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.38(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 119.31(19) . . ?
C7 C6 N1 123.19(18) . . ?
C5 C6 N1 117.38(18) . . ?
C8 C7 C6 119.97(19) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C3 121.08(19) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
N1 C9 C11 120.17(18) . . ?
N1 C9 C10 118.39(18) . . ?
C11 C9 C10 121.43(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 120.76(17) . . ?
C9 C11 C14 120.17(17) . . ?
C12 C11 C14 119.06(17) . . ?
O2 C12 O3 120.93(17) . . ?
O2 C12 C11 125.65(18) . . ?
O3 C12 C11 113.32(16) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O4 121.38(19) . . ?
O5 C14 C11 126.8(2) . . ?
O4 C14 C11 111.79(18) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 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
O1 C2 C3 C4 177.8(2) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
O1 C2 C3 C8 -2.7(3) . . . . ?
C1 C2 C3 C8 178.2(2) . . . . ?
C8 C3 C4 C5 1.5(3) . . . . ?
C2 C3 C4 C5 -178.91(19) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C7 -1.8(3) . . . . ?
C4 C5 C6 N1 -178.02(18) . . . . ?
C9 N1 C6 C7 40.2(3) . . . . ?
C9 N1 C6 C5 -143.8(2) . . . . ?
C5 C6 C7 C8 2.5(3) . . . . ?
N1 C6 C7 C8 178.47(19) . . . . ?
C6 C7 C8 C3 -1.2(3) . . . . ?
C4 C3 C8 C7 -0.8(3) . . . . ?
C2 C3 C8 C7 179.60(19) . . . . ?
C6 N1 C9 C11 -174.82(19) . . . . ?
C6 N1 C9 C10 6.6(3) . . . . ?
N1 C9 C11 C12 -4.7(3) . . . . ?
C10 C9 C11 C12 173.83(19) . . . . ?
N1 C9 C11 C14 176.63(19) . . . . ?
C10 C9 C11 C14 -4.8(3) . . . . ?
C13 O3 C12 O2 0.3(3) . . . . ?
C13 O3 C12 C11 176.89(17) . . . . ?
C9 C11 C12 O2 5.4(3) . . . . ?
C14 C11 C12 O2 -175.9(2) . . . . ?
C9 C11 C12 O3 -170.98(17) . . . . ?
C14 C11 C12 O3 7.7(3) . . . . ?
C15 O4 C14 O5 5.1(3) . . . . ?
C15 O4 C14 C11 -176.68(17) . . . . ?
C9 C11 C14 O5 50.0(3) . . . . ?
C12 C11 C14 O5 -128.7(2) . . . . ?
C9 C11 C14 O4 -128.08(19) . . . . ?
C12 C11 C14 O4 53.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.045
