# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_121121jxx_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 N2 O6'
_chemical_formula_weight         286.28

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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'

_cell_length_a                   7.8669(13)
_cell_length_b                   10.4681(18)
_cell_length_c                   17.696(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1457.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3724
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      23.54

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_T_max  0.9711
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8635
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3028
_reflns_number_gt                2638
_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, 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)+(0.0753P)²+0.4400P] 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       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(17)
_refine_ls_number_reflns         3028
_refine_ls_number_parameters     185
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1435
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.076
_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 0.1105(3) 0.4198(2) 0.08069(12) 0.0393(5) Uani 1 1 d . . .
C2 C 0.2765(3) 0.4783(2) 0.10625(12) 0.0371(5) Uani 1 1 d . . .
H2 H 0.2787 0.4872 0.1614 0.045 Uiso 1 1 calc R . .
C3 C 0.4023(3) 0.3736(2) 0.08019(12) 0.0392(5) Uani 1 1 d . . .
H3 H 0.4757 0.4070 0.0401 0.047 Uiso 1 1 calc R . .
C4 C -0.0581(3) 0.4762(2) 0.09013(15) 0.0452(5) Uani 1 1 d . . .
C5 C -0.2061(4) 0.6479(3) 0.1486(2) 0.0779(10) Uani 1 1 d . . .
H5A H -0.2301 0.7046 0.1066 0.093 Uiso 1 1 calc R . .
H5B H -0.3001 0.5885 0.1537 0.093 Uiso 1 1 calc R . .
C6 C -0.1866(7) 0.7206(5) 0.2171(3) 0.1245(19) Uani 1 1 d . . .
H6A H -0.1812 0.6635 0.2595 0.187 Uiso 1 1 calc R . .
H6B H -0.2818 0.7771 0.2229 0.187 Uiso 1 1 calc R . .
H6C H -0.0837 0.7697 0.2145 0.187 Uiso 1 1 calc R . .
C7 C 0.3072(3) 0.6057(2) 0.06875(15) 0.0477(6) Uani 1 1 d . . .
C8 C 0.3690(7) 0.8236(3) 0.0879(3) 0.1173(18) Uani 1 1 d D . .
H8A H 0.4793 0.8543 0.1042 0.141 Uiso 1 1 calc R . .
H8B H 0.3683 0.8215 0.0331 0.141 Uiso 1 1 calc R . .
C9 C 0.2411(9) 0.9075(4) 0.1137(4) 0.135(2) Uani 1 1 d D . .
H9A H 0.1348 0.8856 0.0905 0.202 Uiso 1 1 calc R . .
H9B H 0.2708 0.9937 0.1007 0.202 Uiso 1 1 calc R . .
H9C H 0.2307 0.9003 0.1676 0.202 Uiso 1 1 calc R . .
C10 C 0.5095(3) 0.3243(2) 0.14473(14) 0.0466(5) Uani 1 1 d . . .
C11 C 0.6823(8) 0.1560(5) 0.1866(2) 0.130(2) Uani 1 1 d D . .
H11A H 0.7348 0.2241 0.2156 0.156 Uiso 1 1 calc R . .
H11B H 0.6148 0.1049 0.2211 0.156 Uiso 1 1 calc R . .
C12 C 0.8094(6) 0.0795(5) 0.1550(3) 0.1204(18) Uani 1 1 d D . .
H12A H 0.7614 0.0276 0.1157 0.181 Uiso 1 1 calc R . .
H12B H 0.8570 0.0255 0.1934 0.181 Uiso 1 1 calc R . .
H12C H 0.8970 0.1328 0.1342 0.181 Uiso 1 1 calc R . .
N1 N 0.1271(3) 0.31112(19) 0.04811(11) 0.0449(5) Uani 1 1 d . . .
N2 N 0.2896(3) 0.2755(2) 0.04957(14) 0.0589(6) Uani 1 1 d . . .
H2A H 0.3246 0.2022 0.0341 0.071 Uiso 1 1 calc R . .
O1 O -0.1872(2) 0.4364(2) 0.06187(12) 0.0607(5) Uani 1 1 d . . .
O2 O -0.0493(2) 0.57842(18) 0.13469(13) 0.0635(6) Uani 1 1 d . . .
O3 O 0.3033(5) 0.6223(2) 0.00278(13) 0.1096(11) Uani 1 1 d . . .
O4 O 0.3413(4) 0.69579(19) 0.11706(14) 0.0845(8) Uani 1 1 d . . .
O5 O 0.5380(3) 0.3842(2) 0.20103(11) 0.0674(6) Uani 1 1 d . . .
O6 O 0.5720(3) 0.2112(2) 0.13019(12) 0.0767(7) 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 0.0357(10) 0.0388(11) 0.0435(11) -0.0057(9) 0.0025(9) -0.0027(9)
C2 0.0346(11) 0.0383(11) 0.0384(11) -0.0047(8) -0.0002(9) -0.0008(8)
C3 0.0369(11) 0.0423(11) 0.0384(10) -0.0027(9) -0.0007(9) 0.0011(9)
C4 0.0390(12) 0.0435(12) 0.0532(13) -0.0082(10) 0.0045(10) -0.0018(9)
C5 0.0527(16) 0.071(2) 0.110(3) -0.0313(19) 0.0063(18) 0.0208(15)
C6 0.110(3) 0.147(5) 0.116(3) -0.046(3) 0.017(3) 0.057(3)
C7 0.0457(13) 0.0402(12) 0.0571(14) -0.0018(10) 0.0004(11) -0.0030(10)
C8 0.163(5) 0.0413(16) 0.147(4) -0.003(2) 0.042(4) -0.025(2)
C9 0.171(5) 0.077(3) 0.157(5) 0.041(3) 0.043(4) 0.030(3)
C10 0.0428(12) 0.0538(12) 0.0431(12) 0.0032(10) 0.0025(10) 0.0050(11)
C11 0.183(5) 0.148(4) 0.0596(19) 0.006(2) -0.019(3) 0.112(4)
C12 0.109(3) 0.139(4) 0.113(3) 0.005(3) -0.028(3) 0.052(3)
N1 0.0414(10) 0.0429(10) 0.0504(11) -0.0111(8) 0.0001(9) 0.0002(8)
N2 0.0422(11) 0.0517(12) 0.0828(16) -0.0291(11) -0.0086(11) 0.0076(9)
O1 0.0351(9) 0.0654(12) 0.0816(13) -0.0217(10) -0.0028(9) -0.0019(8)
O2 0.0399(9) 0.0574(10) 0.0934(14) -0.0333(11) 0.0008(9) 0.0074(8)
O3 0.206(4) 0.0652(14) 0.0582(13) 0.0112(11) -0.0041(17) -0.0305(18)
O4 0.129(2) 0.0419(11) 0.0823(15) -0.0106(10) 0.0106(14) -0.0237(12)
O5 0.0692(13) 0.0809(13) 0.0523(11) -0.0071(10) -0.0166(9) 0.0138(11)
O6 0.1053(18) 0.0699(13) 0.0549(11) 0.0000(10) -0.0101(11) 0.0429(13)

_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 N1 1.282(3) . ?
C1 C4 1.462(3) . ?
C1 C2 1.512(3) . ?
C2 C7 1.508(3) . ?
C2 C3 1.547(3) . ?
C2 H2 0.9800 . ?
C3 N2 1.461(3) . ?
C3 C10 1.511(3) . ?
C3 H3 0.9800 . ?
C4 O1 1.206(3) . ?
C4 O2 1.331(3) . ?
C5 C6 1.440(5) . ?
C5 O2 1.453(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 O3 1.181(3) . ?
C7 O4 1.301(3) . ?
C8 C9 1.412(6) . ?
C8 O4 1.450(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O5 1.198(3) . ?
C10 O6 1.308(3) . ?
C11 C12 1.398(5) . ?
C11 O6 1.443(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 N2 1.332(3) . ?
N2 H2A 0.8600 . ?

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
N1 C1 C4 120.1(2) . . ?
N1 C1 C2 114.0(2) . . ?
C4 C1 C2 125.85(18) . . ?
C7 C2 C1 111.41(19) . . ?
C7 C2 C3 113.13(19) . . ?
C1 C2 C3 100.11(17) . . ?
C7 C2 H2 110.6 . . ?
C1 C2 H2 110.6 . . ?
C3 C2 H2 110.6 . . ?
N2 C3 C10 112.3(2) . . ?
N2 C3 C2 102.73(18) . . ?
C10 C3 C2 111.95(19) . . ?
N2 C3 H3 109.9 . . ?
C10 C3 H3 109.9 . . ?
C2 C3 H3 109.9 . . ?
O1 C4 O2 124.5(2) . . ?
O1 C4 C1 125.3(2) . . ?
O2 C4 C1 110.21(19) . . ?
C6 C5 O2 108.4(3) . . ?
C6 C5 H5A 110.0 . . ?
O2 C5 H5A 110.0 . . ?
C6 C5 H5B 110.0 . . ?
O2 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 O4 123.3(3) . . ?
O3 C7 C2 124.1(2) . . ?
O4 C7 C2 112.6(2) . . ?
C9 C8 O4 110.6(4) . . ?
C9 C8 H8A 109.5 . . ?
O4 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
O4 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 C10 O6 124.5(2) . . ?
O5 C10 C3 123.7(2) . . ?
O6 C10 C3 111.7(2) . . ?
C12 C11 O6 112.5(3) . . ?
C12 C11 H11A 109.1 . . ?
O6 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
O6 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 N2 109.69(19) . . ?
N1 N2 C3 113.15(19) . . ?
N1 N2 H2A 123.4 . . ?
C3 N2 H2A 123.4 . . ?
C4 O2 C5 117.3(2) . . ?
C7 O4 C8 117.8(3) . . ?
C10 O6 C11 116.9(3) . . ?

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
N1 C1 C2 C7 119.7(2) . . . . ?
C4 C1 C2 C7 -60.2(3) . . . . ?
N1 C1 C2 C3 -0.2(2) . . . . ?
C4 C1 C2 C3 179.9(2) . . . . ?
C7 C2 C3 N2 -121.5(2) . . . . ?
C1 C2 C3 N2 -2.8(2) . . . . ?
C7 C2 C3 C10 117.8(2) . . . . ?
C1 C2 C3 C10 -123.5(2) . . . . ?
N1 C1 C4 O1 -9.1(4) . . . . ?
C2 C1 C4 O1 170.7(3) . . . . ?
N1 C1 C4 O2 170.8(2) . . . . ?
C2 C1 C4 O2 -9.3(3) . . . . ?
C1 C2 C7 O3 -53.1(4) . . . . ?
C3 C2 C7 O3 58.8(4) . . . . ?
C1 C2 C7 O4 128.0(2) . . . . ?
C3 C2 C7 O4 -120.2(2) . . . . ?
N2 C3 C10 O5 -138.8(3) . . . . ?
C2 C3 C10 O5 -23.8(3) . . . . ?
N2 C3 C10 O6 43.7(3) . . . . ?
C2 C3 C10 O6 158.6(2) . . . . ?
C4 C1 N1 N2 -176.6(2) . . . . ?
C2 C1 N1 N2 3.6(3) . . . . ?
C1 N1 N2 C3 -5.7(3) . . . . ?
C10 C3 N2 N1 125.8(2) . . . . ?
C2 C3 N2 N1 5.3(3) . . . . ?
O1 C4 O2 C5 -1.4(4) . . . . ?
C1 C4 O2 C5 178.6(3) . . . . ?
C6 C5 O2 C4 158.5(4) . . . . ?
O3 C7 O4 C8 2.5(6) . . . . ?
C2 C7 O4 C8 -178.5(3) . . . . ?
C9 C8 O4 C7 115.3(5) . . . . ?
O5 C10 O6 C11 0.2(5) . . . . ?
C3 C10 O6 C11 177.7(3) . . . . ?
C12 C11 O6 C10 -147.3(5) . . . . ?

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
N2 H2A O1 0.86 2.24 2.974(3) 143.9 4

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 987002'
