# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 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_FO5561
_database_code_depnum_ccdc_archive 'CCDC 1434099'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O5'
_chemical_formula_sum            'C15 H15 N O5'
_chemical_formula_weight         289.28

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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   28.1106(7)
_cell_length_b                   5.8720(2)
_cell_length_c                   21.0927(6)
_cell_angle_alpha                90
_cell_angle_beta                 130.543(1)
_cell_angle_gamma                90
_cell_volume                     2645.79(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.046
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.040
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9256
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3026
_reflns_number_gt                2663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0389P)²+3.0651P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3026
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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 0.78823(4) 0.61616(17) 0.69038(6) 0.0211(2) Uani 1 1 d . . .
O2 O 0.83039(5) 0.8090(2) 0.64527(7) 0.0308(3) Uani 1 1 d . . .
O3 O 0.60244(5) 1.18204(17) 0.56437(6) 0.0232(2) Uani 1 1 d . . .
O4 O 0.59288(5) 1.15729(18) 0.34084(6) 0.0228(2) Uani 1 1 d . . .
O5 O 0.58212(4) 0.66552(16) 0.44983(6) 0.0189(2) Uani 1 1 d . . .
N1 N 0.61388(5) 1.17184(19) 0.46575(6) 0.0154(2) Uani 1 1 d . . .
C1 C 0.82775(7) 0.1296(3) 0.80317(9) 0.0270(3) Uani 1 1 d . . .
H1 H 0.8234(10) -0.002(4) 0.8250(13) 0.049(6) Uiso 1 1 d . . .
C2 C 0.83489(6) 0.2909(2) 0.77644(8) 0.0209(3) Uani 1 1 d . . .
C3 C 0.84606(6) 0.4862(3) 0.74471(9) 0.0221(3) Uani 1 1 d . . .
H3B H 0.8781(8) 0.587(3) 0.7898(11) 0.024(4) Uiso 1 1 d . . .
H3A H 0.8585(8) 0.439(3) 0.7133(10) 0.024(4) Uiso 1 1 d . . .
C4 C 0.78805(6) 0.7804(2) 0.64527(8) 0.0191(3) Uani 1 1 d . . .
C5 C 0.72879(6) 0.9184(2) 0.59757(8) 0.0193(3) Uani 1 1 d . . .
H5B H 0.7248(8) 0.978(3) 0.6382(11) 0.025(4) Uiso 1 1 d . . .
H5A H 0.6930(8) 0.815(3) 0.5608(11) 0.026(4) Uiso 1 1 d . . .
C6 C 0.72677(6) 1.1068(2) 0.54614(8) 0.0193(3) Uani 1 1 d . . .
H6B H 0.7671(8) 1.187(3) 0.5804(11) 0.025(4) Uiso 1 1 d . . .
H6A H 0.7205(7) 1.040(3) 0.4981(10) 0.021(4) Uiso 1 1 d . . .
C7 C 0.67525(6) 1.2813(2) 0.51419(8) 0.0180(3) Uani 1 1 d . . .
H7B H 0.6724(7) 1.396(3) 0.4779(10) 0.018(4) Uiso 1 1 d . . .
H7A H 0.6812(7) 1.360(3) 0.5590(10) 0.019(4) Uiso 1 1 d . . .
C8 C 0.58393(6) 1.1243(2) 0.49633(8) 0.0164(3) Uani 1 1 d . . .
C9 C 0.52616(6) 0.9829(2) 0.43206(8) 0.0155(3) Uani 1 1 d . . .
H9 H 0.4894(8) 1.045(3) 0.4205(10) 0.023(4) Uiso 1 1 d . . .
C10 C 0.53947(6) 0.7294(2) 0.46259(8) 0.0184(3) Uani 1 1 d . . .
H10 H 0.5584(7) 0.708(3) 0.5212(10) 0.018(4) Uiso 1 1 d . . .
C11 C 0.48142(7) 0.5947(2) 0.39548(9) 0.0204(3) Uani 1 1 d . . .
H11 H 0.4483(8) 0.552(3) 0.3961(11) 0.029(4) Uiso 1 1 d . . .
C12 C 0.48147(7) 0.5775(2) 0.33263(9) 0.0207(3) Uani 1 1 d . . .
H12 H 0.4484(9) 0.517(3) 0.2769(12) 0.034(5) Uiso 1 1 d . . .
C13 C 0.53944(6) 0.7049(2) 0.36111(8) 0.0181(3) Uani 1 1 d . . .
H13 H 0.5588(7) 0.663(3) 0.3372(10) 0.018(4) Uiso 1 1 d . . .
C14 C 0.52450(6) 0.9651(2) 0.35769(8) 0.0157(3) Uani 1 1 d . . .
H14 H 0.4863(8) 1.011(3) 0.3048(10) 0.018(4) Uiso 1 1 d . . .
C15 C 0.57932(6) 1.1074(2) 0.38323(8) 0.0160(3) 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
O1 C4 1.3523(16) . ?
O1 C3 1.4546(16) . ?
O2 C4 1.2021(17) . ?
O3 C8 1.2144(15) . ?
O4 C15 1.2142(15) . ?
O5 C10 1.4389(16) . ?
O5 C13 1.4409(15) . ?
N1 C8 1.3816(16) . ?
N1 C15 1.3849(16) . ?
N1 C7 1.4634(16) . ?
C1 C2 1.184(2) . ?
C1 H1 0.95(2) . ?
C2 C3 1.461(2) . ?
C3 H3B 0.976(18) . ?
C3 H3A 0.968(17) . ?
C4 C5 1.5048(18) . ?
C5 C6 1.5242(19) . ?
C5 H5B 0.997(17) . ?
C5 H5A 0.985(18) . ?
C6 C7 1.5273(19) . ?
C6 H6B 0.981(18) . ?
C6 H6A 0.990(16) . ?
C7 H7B 0.982(17) . ?
C7 H7A 0.966(16) . ?
C8 C9 1.5175(18) . ?
C9 C14 1.5420(17) . ?
C9 C10 1.5673(18) . ?
C9 H9 0.965(17) . ?
C10 C11 1.5130(19) . ?
C10 H10 0.986(16) . ?
C11 C12 1.330(2) . ?
C11 H11 0.972(18) . ?
C12 C13 1.5180(19) . ?
C12 H12 0.976(19) . ?
C13 C14 1.5738(19) . ?
C13 H13 0.984(16) . ?
C14 C15 1.5110(18) . ?
C14 H14 0.956(16) . ?

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
C4 O1 C3 114.81(10) . . ?
C10 O5 C13 96.28(9) . . ?
C8 N1 C15 112.89(11) . . ?
C8 N1 C7 124.21(11) . . ?
C15 N1 C7 122.90(11) . . ?
C2 C1 H1 177.9(13) . . ?
C1 C2 C3 177.75(15) . . ?
O1 C3 C2 108.04(11) . . ?
O1 C3 H3B 107.4(10) . . ?
C2 C3 H3B 111.4(10) . . ?
O1 C3 H3A 109.0(10) . . ?
C2 C3 H3A 111.8(11) . . ?
H3B C3 H3A 109.0(14) . . ?
O2 C4 O1 123.28(13) . . ?
O2 C4 C5 126.18(13) . . ?
O1 C4 C5 110.54(11) . . ?
C4 C5 C6 112.31(11) . . ?
C4 C5 H5B 108.0(10) . . ?
C6 C5 H5B 112.5(10) . . ?
C4 C5 H5A 108.4(10) . . ?
C6 C5 H5A 109.9(10) . . ?
H5B C5 H5A 105.4(14) . . ?
C5 C6 C7 112.78(11) . . ?
C5 C6 H6B 109.4(10) . . ?
C7 C6 H6B 108.2(10) . . ?
C5 C6 H6A 109.8(10) . . ?
C7 C6 H6A 109.2(9) . . ?
H6B C6 H6A 107.3(13) . . ?
N1 C7 C6 111.26(11) . . ?
N1 C7 H7B 107.1(9) . . ?
C6 C7 H7B 112.1(9) . . ?
N1 C7 H7A 105.7(10) . . ?
C6 C7 H7A 112.3(10) . . ?
H7B C7 H7A 108.0(13) . . ?
O3 C8 N1 124.93(12) . . ?
O3 C8 C9 126.60(12) . . ?
N1 C8 C9 108.45(10) . . ?
C8 C9 C14 104.66(10) . . ?
C8 C9 C10 108.77(10) . . ?
C14 C9 C10 101.25(10) . . ?
C8 C9 H9 111.5(10) . . ?
C14 C9 H9 116.6(10) . . ?
C10 C9 H9 113.2(10) . . ?
O5 C10 C11 102.22(10) . . ?
O5 C10 C9 100.14(10) . . ?
C11 C10 C9 106.74(10) . . ?
O5 C10 H10 111.4(9) . . ?
C11 C10 H10 118.8(9) . . ?
C9 C10 H10 115.2(10) . . ?
C12 C11 C10 105.84(12) . . ?
C12 C11 H11 128.0(10) . . ?
C10 C11 H11 125.5(10) . . ?
C11 C12 C13 105.33(12) . . ?
C11 C12 H12 127.6(11) . . ?
C13 C12 H12 126.5(11) . . ?
O5 C13 C12 102.02(10) . . ?
O5 C13 C14 100.80(10) . . ?
C12 C13 C14 105.93(11) . . ?
O5 C13 H13 110.8(9) . . ?
C12 C13 H13 119.0(9) . . ?
C14 C13 H13 116.0(10) . . ?
C15 C14 C9 104.50(10) . . ?
C15 C14 C13 109.90(10) . . ?
C9 C14 C13 100.85(10) . . ?
C15 C14 H14 111.9(10) . . ?
C9 C14 H14 115.8(9) . . ?
C13 C14 H14 113.1(10) . . ?
O4 C15 N1 124.05(12) . . ?
O4 C15 C14 127.34(12) . . ?
N1 C15 C14 108.60(10) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043
