# Electronic Supplementary Material (ESI) for Polymer Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Polym.Chem.
_journal_coden_cambridge         1478
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       f.wiesbrock@tugraz.at
_publ_contact_author_name        'Frank Wiesbrock'
loop_
_publ_author_name
'Elisabeth Rossegger'
'Laszlo Olah'
'Roland Fischer'
'Petra Kaschnitz'
'Olivia Varga'
'Mihaly Kallay'
'Gregor Scheipl'
'Franz Stelzer'
'Frank Wiesbrock'

data_rf257_fin
_database_code_depnum_ccdc_archive 'CCDC 876454'
#TrackingRef '- rf257_fin_.cif.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_weight         257.32

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)

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

_cell_length_a                   11.3513(19)
_cell_length_b                   5.7944(10)
_cell_length_c                   11.730(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.303(6)
_cell_angle_gamma                90.00
_cell_volume                     685.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1542
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      23.89

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6920
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_sigmaI/netI    0.1014
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         27.26
_reflns_number_total             2876
_reflns_number_gt                1890
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0358P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(16)
_refine_ls_number_reflns         2876
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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 0.82372(18) 0.1968(3) 0.18471(18) 0.0204(5) Uani 1 1 d . . .
O2 O 1.06008(16) -0.0511(3) 0.26966(16) 0.0304(5) Uani 1 1 d . . .
O1 O 1.16625(17) 0.2735(3) 0.26846(19) 0.0362(5) Uani 1 1 d . . .
C3 C 0.7619(3) 0.3595(5) -0.0650(2) 0.0288(6) Uani 1 1 d . . .
H3 H 0.7611 0.4774 -0.1217 0.035 Uiso 1 1 calc R . .
C1 C 0.9295(2) 0.2709(4) 0.1513(2) 0.0216(6) Uani 1 1 d . . .
H1 H 0.9364 0.4430 0.1558 0.026 Uiso 1 1 calc R . .
C2 C 0.8743(2) 0.1931(4) 0.0085(2) 0.0260(6) Uani 1 1 d . . .
H2 H 0.9408 0.1724 -0.0243 0.031 Uiso 1 1 calc R . .
C6 C 0.7956(2) -0.0229(4) 0.0089(2) 0.0252(6) Uani 1 1 d . . .
H6A H 0.7416 -0.0882 -0.0777 0.030 Uiso 1 1 calc R . .
H6B H 0.8515 -0.1440 0.0689 0.030 Uiso 1 1 calc R . .
C7 C 1.0638(3) 0.1683(4) 0.2369(2) 0.0227(6) Uani 1 1 d . . .
C4 C 0.6652(3) 0.3107(4) -0.0359(2) 0.0271(6) Uani 1 1 d . . .
H4 H 0.5815 0.3850 -0.0681 0.032 Uiso 1 1 calc R . .
C8 C 1.1871(2) -0.1579(4) 0.3494(2) 0.0287(6) Uani 1 1 d . . .
H8A H 1.2305 -0.0767 0.4318 0.043 Uiso 1 1 calc R . .
H8B H 1.2431 -0.1493 0.3061 0.043 Uiso 1 1 calc R . .
H8C H 1.1735 -0.3199 0.3643 0.043 Uiso 1 1 calc R . .
C5 C 0.7145(2) 0.1123(4) 0.0591(2) 0.0236(6) Uani 1 1 d . . .
H5 H 0.6433 0.0218 0.0665 0.028 Uiso 1 1 calc R . .
C11 C 0.5724(2) 0.3993(5) 0.2723(2) 0.0286(7) Uani 1 1 d . . .
H11 H 0.5538 0.5428 0.2283 0.034 Uiso 1 1 calc R . .
C9 C 0.7830(2) 0.3733(4) 0.2493(2) 0.0212(6) Uani 1 1 d . . .
H9 H 0.7417 0.5059 0.1896 0.025 Uiso 1 1 calc R . .
C10 C 0.6829(2) 0.2719(4) 0.2879(2) 0.0197(6) Uani 1 1 d . . .
C14 C 0.6224(3) -0.0223(5) 0.3975(2) 0.0337(7) Uani 1 1 d . . .
H14 H 0.6395 -0.1675 0.4398 0.040 Uiso 1 1 calc R . .
C15 C 0.7052(3) 0.0591(5) 0.3489(2) 0.0261(6) Uani 1 1 d . . .
H15 H 0.7784 -0.0321 0.3575 0.031 Uiso 1 1 calc R . .
C16 C 0.9027(2) 0.4597(5) 0.3706(2) 0.0286(6) Uani 1 1 d . . .
H16A H 0.9639 0.5404 0.3467 0.043 Uiso 1 1 calc R . .
H16B H 0.9481 0.3281 0.4258 0.043 Uiso 1 1 calc R . .
H16C H 0.8726 0.5658 0.4169 0.043 Uiso 1 1 calc R . .
C12 C 0.4890(3) 0.3175(5) 0.3210(2) 0.0365(8) Uani 1 1 d . . .
H12 H 0.4143 0.4059 0.3106 0.044 Uiso 1 1 calc R . .
C13 C 0.5147(3) 0.1083(5) 0.3844(3) 0.0395(8) Uani 1 1 d . . .
H13 H 0.4586 0.0542 0.4188 0.047 Uiso 1 1 calc R . .

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
N1 0.0189(11) 0.0219(11) 0.0210(11) -0.0026(9) 0.0096(10) -0.0027(9)
O2 0.0194(9) 0.0266(11) 0.0381(11) 0.0105(9) 0.0071(9) -0.0021(8)
O1 0.0230(10) 0.0308(11) 0.0536(12) 0.0002(9) 0.0165(9) -0.0058(9)
C3 0.0367(17) 0.0296(15) 0.0175(14) 0.0016(12) 0.0103(13) 0.0042(13)
C1 0.0213(13) 0.0224(14) 0.0226(14) -0.0012(12) 0.0115(12) -0.0017(12)
C2 0.0287(15) 0.0297(15) 0.0245(15) -0.0011(13) 0.0165(13) 0.0020(13)
C6 0.0289(15) 0.0245(15) 0.0197(14) -0.0064(12) 0.0090(12) 0.0006(12)
C7 0.0281(15) 0.0231(15) 0.0238(15) -0.0043(12) 0.0179(13) -0.0016(13)
C4 0.0261(14) 0.0288(16) 0.0200(14) -0.0025(12) 0.0053(12) 0.0033(12)
C8 0.0199(13) 0.0307(17) 0.0309(15) 0.0048(13) 0.0076(12) 0.0021(12)
C5 0.0220(14) 0.0235(16) 0.0246(15) -0.0032(12) 0.0101(13) -0.0032(11)
C11 0.0260(15) 0.0375(18) 0.0201(14) -0.0042(13) 0.0087(12) 0.0021(13)
C9 0.0264(13) 0.0200(14) 0.0194(13) -0.0042(11) 0.0123(12) -0.0010(11)
C10 0.0201(13) 0.0231(14) 0.0148(13) -0.0021(11) 0.0071(11) -0.0013(11)
C14 0.0445(18) 0.0297(16) 0.0283(16) -0.0064(14) 0.0178(15) -0.0128(14)
C15 0.0271(15) 0.0247(14) 0.0269(15) -0.0007(13) 0.0127(13) -0.0009(12)
C16 0.0281(15) 0.0329(16) 0.0287(15) -0.0054(13) 0.0163(13) -0.0077(13)
C12 0.0188(14) 0.065(2) 0.0257(15) -0.0097(16) 0.0099(12) 0.0009(15)
C13 0.0300(17) 0.062(2) 0.0330(18) -0.0097(17) 0.0198(15) -0.0203(16)

_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 1.468(3) . ?
N1 C1 1.487(3) . ?
N1 C5 1.507(3) . ?
O2 C7 1.334(3) . ?
O2 C8 1.449(3) . ?
O1 C7 1.211(3) . ?
C3 C4 1.321(3) . ?
C3 C2 1.514(3) . ?
C3 H3 0.9500 . ?
C1 C7 1.510(3) . ?
C1 C2 1.562(3) . ?
C1 H1 1.0000 . ?
C2 C6 1.539(3) . ?
C2 H2 1.0000 . ?
C6 C5 1.519(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C4 C5 1.518(3) . ?
C4 H4 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C5 H5 1.0000 . ?
C11 C12 1.393(4) . ?
C11 C10 1.394(3) . ?
C11 H11 0.9500 . ?
C9 C10 1.520(3) . ?
C9 C16 1.532(3) . ?
C9 H9 1.0000 . ?
C10 C15 1.389(4) . ?
C14 C13 1.385(4) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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 C1 114.73(17) . . ?
C9 N1 C5 114.73(18) . . ?
C1 N1 C5 103.75(17) . . ?
C7 O2 C8 116.08(19) . . ?
C4 C3 C2 107.4(2) . . ?
C4 C3 H3 126.3 . . ?
C2 C3 H3 126.3 . . ?
N1 C1 C7 113.71(19) . . ?
N1 C1 C2 102.94(18) . . ?
C7 C1 C2 112.69(19) . . ?
N1 C1 H1 109.1 . . ?
C7 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C3 C2 C6 100.5(2) . . ?
C3 C2 C1 104.24(19) . . ?
C6 C2 C1 100.34(19) . . ?
C3 C2 H2 116.4 . . ?
C6 C2 H2 116.4 . . ?
C1 C2 H2 116.4 . . ?
C5 C6 C2 92.13(18) . . ?
C5 C6 H6A 113.3 . . ?
C2 C6 H6A 113.3 . . ?
C5 C6 H6B 113.3 . . ?
C2 C6 H6B 113.3 . . ?
H6A C6 H6B 110.6 . . ?
O1 C7 O2 123.0(2) . . ?
O1 C7 C1 122.7(2) . . ?
O2 C7 C1 114.3(2) . . ?
C3 C4 C5 106.4(2) . . ?
C3 C4 H4 126.8 . . ?
C5 C4 H4 126.8 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C5 C4 109.45(19) . . ?
N1 C5 C6 100.00(18) . . ?
C4 C5 C6 101.0(2) . . ?
N1 C5 H5 114.9 . . ?
C4 C5 H5 114.9 . . ?
C6 C5 H5 114.9 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N1 C9 C10 109.84(19) . . ?
N1 C9 C16 110.60(19) . . ?
C10 C9 C16 108.39(19) . . ?
N1 C9 H9 109.3 . . ?
C10 C9 H9 109.3 . . ?
C16 C9 H9 109.3 . . ?
C15 C10 C11 118.5(2) . . ?
C15 C10 C9 120.8(2) . . ?
C11 C10 C9 120.5(2) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 121.1(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?

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
C9 N1 C1 C7 105.6(2) . . . . ?
C5 N1 C1 C7 -128.5(2) . . . . ?
C9 N1 C1 C2 -132.2(2) . . . . ?
C5 N1 C1 C2 -6.3(2) . . . . ?
C4 C3 C2 C6 33.6(3) . . . . ?
C4 C3 C2 C1 -70.0(3) . . . . ?
N1 C1 C2 C3 72.0(2) . . . . ?
C7 C1 C2 C3 -165.1(2) . . . . ?
N1 C1 C2 C6 -31.7(2) . . . . ?
C7 C1 C2 C6 91.2(2) . . . . ?
C3 C2 C6 C5 -51.1(2) . . . . ?
C1 C2 C6 C5 55.6(2) . . . . ?
C8 O2 C7 O1 1.7(3) . . . . ?
C8 O2 C7 C1 178.65(19) . . . . ?
N1 C1 C7 O1 -144.4(2) . . . . ?
C2 C1 C7 O1 99.0(3) . . . . ?
N1 C1 C7 O2 38.7(3) . . . . ?
C2 C1 C7 O2 -78.0(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C9 N1 C5 C4 63.3(2) . . . . ?
C1 N1 C5 C4 -62.6(2) . . . . ?
C9 N1 C5 C6 168.82(18) . . . . ?
C1 N1 C5 C6 42.9(2) . . . . ?
C3 C4 C5 N1 69.4(2) . . . . ?
C3 C4 C5 C6 -35.5(2) . . . . ?
C2 C6 C5 N1 -60.4(2) . . . . ?
C2 C6 C5 C4 51.8(2) . . . . ?
C1 N1 C9 C10 -175.52(19) . . . . ?
C5 N1 C9 C10 64.5(3) . . . . ?
C1 N1 C9 C16 -55.9(2) . . . . ?
C5 N1 C9 C16 -175.94(19) . . . . ?
C12 C11 C10 C15 2.1(3) . . . . ?
C12 C11 C10 C9 -172.6(2) . . . . ?
N1 C9 C10 C15 46.9(3) . . . . ?
C16 C9 C10 C15 -74.0(3) . . . . ?
N1 C9 C10 C11 -138.5(2) . . . . ?
C16 C9 C10 C11 100.6(3) . . . . ?
C13 C14 C15 C10 0.6(4) . . . . ?
C11 C10 C15 C14 -2.2(4) . . . . ?
C9 C10 C15 C14 172.5(2) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
C15 C14 C13 C12 1.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.044