# 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_FO5849
_database_code_depnum_ccdc_archive 'CCDC 1477579'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 N2 O3'
_chemical_formula_sum            'C8 H14 N2 O3'
_chemical_formula_weight         186.21

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/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.7713(7)
_cell_length_b                   9.5154(7)
_cell_length_c                   11.5372(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.738(4)
_cell_angle_gamma                90
_cell_volume                     981.95(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    6408
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.37

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.068
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6395
_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            6408
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2004
_reflns_number_gt                1736
_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)+(0.0137P)²+1.0619P] 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         2004
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.307
_refine_ls_restrained_S_all      1.307
_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 0.3252(2) 0.5625(2) 0.29094(18) 0.0388(5) Uani 1 1 d . . .
O2 O 0.2474(2) 0.4180(2) 0.59671(17) 0.0366(5) Uani 1 1 d . . .
O3 O 0.3475(2) 0.21947(18) 0.55269(16) 0.0296(4) Uani 1 1 d . . .
N1 N 0.3229(2) 0.4069(2) 0.43354(18) 0.0257(5) Uani 1 1 d . . .
N2 N 0.2261(3) 0.6430(2) 0.4254(2) 0.0355(6) Uani 1 1 d . . .
H1N2 H 0.208(3) 0.613(3) 0.490(3) 0.045(9) Uiso 1 1 d . . .
C1 C 0.3899(3) 0.3289(3) 0.3593(2) 0.0289(6) Uani 1 1 d . . .
H1B H 0.340(3) 0.237(3) 0.330(2) 0.025(7) Uiso 1 1 d . . .
H1A H 0.493(3) 0.309(3) 0.414(3) 0.038(8) Uiso 1 1 d . . .
C2 C 0.3658(5) 0.4309(4) 0.2537(4) 0.0540(10) Uani 1 1 d . . .
H2B H 0.442(5) 0.441(4) 0.229(4) 0.085(14) Uiso 1 1 d . . .
H2A H 0.271(5) 0.391(5) 0.175(4) 0.106(17) Uiso 1 1 d . . .
C3 C 0.2847(3) 0.5446(3) 0.3895(2) 0.0274(6) Uani 1 1 d . . .
C4 C 0.3012(3) 0.3523(3) 0.5355(2) 0.0276(6) Uani 1 1 d . . .
C5 C 0.3339(3) 0.1336(3) 0.6555(2) 0.0307(6) Uani 1 1 d . . .
C6 C 0.4003(4) -0.0057(3) 0.6403(3) 0.0422(8) Uani 1 1 d . . .
H6C H 0.505(4) 0.016(3) 0.650(3) 0.051(9) Uiso 1 1 d . . .
H6B H 0.402(3) -0.073(3) 0.706(3) 0.046(9) Uiso 1 1 d . . .
H6A H 0.337(4) -0.045(4) 0.562(3) 0.056(10) Uiso 1 1 d . . .
C7 C 0.1706(4) 0.1185(4) 0.6313(3) 0.0451(8) Uani 1 1 d . . .
H7C H 0.130(4) 0.207(4) 0.641(3) 0.052(10) Uiso 1 1 d . . .
H7B H 0.164(4) 0.055(4) 0.689(3) 0.059(10) Uiso 1 1 d . . .
H7A H 0.114(4) 0.080(4) 0.548(4) 0.071(12) Uiso 1 1 d . . .
C8 C 0.4264(4) 0.1993(3) 0.7830(3) 0.0372(7) Uani 1 1 d . . .
H8C H 0.528(4) 0.225(3) 0.791(3) 0.042(8) Uiso 1 1 d . . .
H8B H 0.382(4) 0.287(4) 0.800(3) 0.052(9) Uiso 1 1 d . . .
H8A H 0.440(4) 0.132(4) 0.847(3) 0.054(10) Uiso 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
O1 0.0538(13) 0.0326(11) 0.0419(11) 0.0095(9) 0.0317(10) 0.0052(9)
O2 0.0547(13) 0.0318(10) 0.0299(9) 0.0039(8) 0.0239(9) 0.0089(9)
O3 0.0386(11) 0.0243(9) 0.0271(9) 0.0044(7) 0.0144(8) 0.0041(8)
N1 0.0302(11) 0.0246(11) 0.0240(10) -0.0010(8) 0.0127(9) -0.0004(9)
N2 0.0496(15) 0.0273(12) 0.0336(12) 0.0017(10) 0.0210(12) 0.0043(11)
C1 0.0304(14) 0.0310(15) 0.0280(13) -0.0042(11) 0.0144(12) 0.0000(12)
C2 0.094(3) 0.0350(17) 0.060(2) 0.0079(16) 0.058(2) 0.0107(19)
C3 0.0320(14) 0.0282(14) 0.0212(12) 0.0016(10) 0.0099(11) -0.0031(11)
C4 0.0326(14) 0.0263(13) 0.0216(12) 0.0008(10) 0.0084(11) -0.0004(11)
C5 0.0352(15) 0.0291(14) 0.0262(13) 0.0075(11) 0.0107(12) 0.0013(12)
C6 0.057(2) 0.0298(16) 0.0370(17) 0.0076(13) 0.0158(16) 0.0076(15)
C7 0.0396(18) 0.045(2) 0.0465(19) 0.0153(16) 0.0129(15) -0.0063(15)
C8 0.0422(18) 0.0403(17) 0.0255(13) 0.0052(13) 0.0100(12) 0.0031(14)

_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 C3 1.357(3) . ?
O1 C2 1.431(4) . ?
O2 C4 1.210(3) . ?
O3 C4 1.330(3) . ?
O3 C5 1.490(3) . ?
N1 C4 1.378(3) . ?
N1 C3 1.401(3) . ?
N1 C1 1.471(3) . ?
N2 C3 1.252(3) . ?
N2 H1N2 0.88(3) . ?
C1 C2 1.499(4) . ?
C1 H1B 0.99(3) . ?
C1 H1A 0.97(3) . ?
C2 H2B 0.91(4) . ?
C2 H2A 1.07(5) . ?
C5 C7 1.511(4) . ?
C5 C8 1.517(4) . ?
C5 C6 1.517(4) . ?
C6 H6C 1.01(3) . ?
C6 H6B 0.98(3) . ?
C6 H6A 0.94(3) . ?
C7 H7C 0.96(3) . ?
C7 H7B 0.92(4) . ?
C7 H7A 0.97(4) . ?
C8 H8C 0.99(3) . ?
C8 H8B 1.00(3) . ?
C8 H8A 0.95(3) . ?

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
C3 O1 C2 110.6(2) . . ?
C4 O3 C5 120.40(19) . . ?
C4 N1 C3 123.5(2) . . ?
C4 N1 C1 124.4(2) . . ?
C3 N1 C1 112.1(2) . . ?
C3 N2 H1N2 108(2) . . ?
N1 C1 C2 100.7(2) . . ?
N1 C1 H1B 111.9(15) . . ?
C2 C1 H1B 113.6(15) . . ?
N1 C1 H1A 108.0(17) . . ?
C2 C1 H1A 115.7(17) . . ?
H1B C1 H1A 107(2) . . ?
O1 C2 C1 107.1(2) . . ?
O1 C2 H2B 112(3) . . ?
C1 C2 H2B 117(3) . . ?
O1 C2 H2A 108(3) . . ?
C1 C2 H2A 105(2) . . ?
H2B C2 H2A 108(3) . . ?
N2 C3 O1 120.7(2) . . ?
N2 C3 N1 132.1(2) . . ?
O1 C3 N1 107.2(2) . . ?
O2 C4 O3 127.2(2) . . ?
O2 C4 N1 123.8(2) . . ?
O3 C4 N1 109.0(2) . . ?
O3 C5 C7 109.3(2) . . ?
O3 C5 C8 109.7(2) . . ?
C7 C5 C8 113.0(3) . . ?
O3 C5 C6 102.0(2) . . ?
C7 C5 C6 111.4(3) . . ?
C8 C5 C6 110.9(2) . . ?
C5 C6 H6C 105.6(19) . . ?
C5 C6 H6B 111.0(18) . . ?
H6C C6 H6B 110(3) . . ?
C5 C6 H6A 108(2) . . ?
H6C C6 H6A 116(3) . . ?
H6B C6 H6A 106(3) . . ?
C5 C7 H7C 111(2) . . ?
C5 C7 H7B 108(2) . . ?
H7C C7 H7B 110(3) . . ?
C5 C7 H7A 111(2) . . ?
H7C C7 H7A 110(3) . . ?
H7B C7 H7A 107(3) . . ?
C5 C8 H8C 111.9(17) . . ?
C5 C8 H8B 113.6(19) . . ?
H8C C8 H8B 106(3) . . ?
C5 C8 H8A 109(2) . . ?
H8C C8 H8A 106(3) . . ?
H8B C8 H8A 110(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046
