# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_(R,R)-10
_database_code_depnum_ccdc_archive 'CCDC 1024381'
_audit_update_record             
;
2014-09-14 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 N O3'
_chemical_formula_sum            'C15 H19 N O3'
_chemical_formula_weight         261.31
_chemical_absolute_configuration syn

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'

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

_cell_length_a                   9.7435(8)
_cell_length_b                   6.5523(4)
_cell_length_c                   11.9590(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.802(10)
_cell_angle_gamma                90.00
_cell_volume                     734.63(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2659
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2297
_reflns_number_gt                1647
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0630P)²+0.0000P] 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       0.019(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2297
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.8590(3) 1.0663(4) 0.8753(2) 0.0680(9) Uani 1 1 d . . .
O2 O 0.8745(3) 1.1673(4) 0.6201(2) 0.0622(8) Uani 1 1 d . . .
O3 O 0.6575(3) 1.0269(4) 0.5677(3) 0.0725(9) Uani 1 1 d . . .
N1 N 0.9682(3) 0.8533(4) 0.7819(2) 0.0433(7) Uani 1 1 d . . .
C1 C 1.1086(4) 1.0154(6) 0.9617(3) 0.0560(10) Uani 1 1 d . . .
H1A H 1.1070 1.1461 0.9975 0.084 Uiso 1 1 calc R . .
H1B H 1.1862 1.0108 0.9266 0.084 Uiso 1 1 calc R . .
H1C H 1.1209 0.9102 1.0195 0.084 Uiso 1 1 calc R . .
C2 C 0.9698(4) 0.9823(5) 0.8698(3) 0.0446(8) Uani 1 1 d . . .
C3 C 0.8374(4) 0.8315(5) 0.6888(3) 0.0502(10) Uani 1 1 d . . .
H3A H 0.7599 0.7795 0.7186 0.060 Uiso 1 1 calc R . .
C4 C 0.7961(4) 1.0318(5) 0.6256(3) 0.0456(9) Uani 1 1 d . . .
C5 C 0.6049(5) 1.1972(8) 0.4910(5) 0.0985(18) Uani 1 1 d . . .
H5A H 0.6268 1.3225 0.5338 0.148 Uiso 1 1 calc R . .
H5B H 0.5035 1.1852 0.4597 0.148 Uiso 1 1 calc R . .
H5C H 0.6496 1.1969 0.4287 0.148 Uiso 1 1 calc R . .
C6 C 0.8772(6) 0.6780(6) 0.6081(4) 0.0787(15) Uani 1 1 d . . .
H6A H 0.8576 0.5398 0.6284 0.094 Uiso 1 1 calc R . .
H6B H 0.8252 0.7038 0.5279 0.094 Uiso 1 1 calc R . .
C7 C 1.0355(5) 0.7102(6) 0.6265(3) 0.0731(14) Uani 1 1 d . . .
H7A H 1.0535 0.8261 0.5820 0.088 Uiso 1 1 calc R . .
H7B H 1.0799 0.5899 0.6044 0.088 Uiso 1 1 calc R . .
C8 C 1.0903(4) 0.7502(5) 0.7565(3) 0.0464(9) Uani 1 1 d . . .
H8A H 1.1720 0.8433 0.7717 0.056 Uiso 1 1 calc R . .
C9 C 1.1328(4) 0.5533(5) 0.8260(3) 0.0533(10) Uani 1 1 d . . .
H9A H 1.1426 0.5810 0.9075 0.064 Uiso 1 1 calc R . .
H9B H 1.0574 0.4534 0.8001 0.064 Uiso 1 1 calc R . .
C10 C 1.2691(4) 0.4658(6) 0.8133(3) 0.0596(11) Uani 1 1 d . . .
C11 C 1.2717(6) 0.2924(6) 0.7484(4) 0.0753(14) Uani 1 1 d . . .
H11A H 1.1865 0.2286 0.7105 0.090 Uiso 1 1 calc R . .
C12 C 1.3996(8) 0.2124(9) 0.7392(5) 0.114(2) Uani 1 1 d . . .
H12A H 1.4000 0.0936 0.6967 0.137 Uiso 1 1 calc R . .
C13 C 1.5250(8) 0.3069(16) 0.7921(6) 0.135(3) Uani 1 1 d . . .
H13A H 1.6107 0.2519 0.7861 0.162 Uiso 1 1 calc R . .
C14 C 1.5252(6) 0.4819(15) 0.8537(6) 0.144(3) Uani 1 1 d . . .
H14A H 1.6104 0.5488 0.8881 0.173 Uiso 1 1 calc R . .
C15 C 1.3969(5) 0.5589(10) 0.8644(5) 0.1002(19) Uani 1 1 d . . .
H15A H 1.3975 0.6771 0.9076 0.120 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
O1 C2 1.230(4) . ?
O2 C4 1.185(4) . ?
O3 C4 1.340(4) . ?
O3 C5 1.447(5) . ?
N1 C2 1.345(4) . ?
N1 C3 1.453(5) . ?
N1 C8 1.470(4) . ?
C1 C2 1.508(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C4 1.513(5) . ?
C3 C6 1.516(6) . ?
C3 H3A 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.512(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.523(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.529(5) . ?
C8 H8A 0.9800 . ?
C9 C10 1.492(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.372(6) . ?
C10 C11 1.380(6) . ?
C11 C12 1.384(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.362(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.362(10) . ?
C13 H13A 0.9300 . ?
C14 C15 1.386(8) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?

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 O3 C5 116.3(3) . . ?
C2 N1 C3 118.8(3) . . ?
C2 N1 C8 127.7(3) . . ?
C3 N1 C8 112.7(3) . . ?
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 N1 120.0(3) . . ?
O1 C2 C1 121.5(3) . . ?
N1 C2 C1 118.5(3) . . ?
N1 C3 C4 110.8(3) . . ?
N1 C3 C6 103.3(3) . . ?
C4 C3 C6 109.7(3) . . ?
N1 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C6 C3 H3A 110.9 . . ?
O2 C4 O3 124.3(3) . . ?
O2 C4 C3 126.2(3) . . ?
O3 C4 C3 109.3(3) . . ?
O3 C5 H5A 109.5 . . ?
O3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C3 104.0(3) . . ?
C7 C6 H6A 110.9 . . ?
C3 C6 H6A 110.9 . . ?
C7 C6 H6B 110.9 . . ?
C3 C6 H6B 110.9 . . ?
H6A C6 H6B 109.0 . . ?
C6 C7 C8 103.4(3) . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.0 . . ?
N1 C8 C7 102.2(3) . . ?
N1 C8 C9 113.0(3) . . ?
C7 C8 C9 112.2(3) . . ?
N1 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C10 C9 C8 112.7(3) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C15 C10 C11 117.6(4) . . ?
C15 C10 C9 120.6(4) . . ?
C11 C10 C9 121.8(4) . . ?
C10 C11 C12 120.8(5) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C13 C12 C11 120.2(6) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C14 C13 C12 120.2(6) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C15 119.2(7) . . ?
C13 C14 H14A 120.4 . . ?
C15 C14 H14A 120.4 . . ?
C10 C15 C14 121.9(6) . . ?
C10 C15 H15A 119.0 . . ?
C14 C15 H15A 119.0 . . ?

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
C3 N1 C2 O1 6.0(5) . . . . ?
C8 N1 C2 O1 175.6(3) . . . . ?
C3 N1 C2 C1 -175.7(3) . . . . ?
C8 N1 C2 C1 -6.2(5) . . . . ?
C2 N1 C3 C4 62.2(4) . . . . ?
C8 N1 C3 C4 -108.8(3) . . . . ?
C2 N1 C3 C6 179.7(3) . . . . ?
C8 N1 C3 C6 8.6(4) . . . . ?
C5 O3 C4 O2 2.3(6) . . . . ?
C5 O3 C4 C3 -172.6(4) . . . . ?
N1 C3 C4 O2 24.8(6) . . . . ?
C6 C3 C4 O2 -88.7(4) . . . . ?
N1 C3 C4 O3 -160.4(3) . . . . ?
C6 C3 C4 O3 86.1(4) . . . . ?
N1 C3 C6 C7 -28.8(4) . . . . ?
C4 C3 C6 C7 89.4(4) . . . . ?
C3 C6 C7 C8 38.3(4) . . . . ?
C2 N1 C8 C7 -155.3(3) . . . . ?
C3 N1 C8 C7 14.8(4) . . . . ?
C2 N1 C8 C9 83.9(4) . . . . ?
C3 N1 C8 C9 -106.0(3) . . . . ?
C6 C7 C8 N1 -32.1(4) . . . . ?
C6 C7 C8 C9 89.2(4) . . . . ?
N1 C8 C9 C10 -171.5(3) . . . . ?
C7 C8 C9 C10 73.6(4) . . . . ?
C8 C9 C10 C15 71.6(5) . . . . ?
C8 C9 C10 C11 -107.0(4) . . . . ?
C15 C10 C11 C12 2.2(7) . . . . ?
C9 C10 C11 C12 -179.1(4) . . . . ?
C10 C11 C12 C13 -1.5(8) . . . . ?
C11 C12 C13 C14 -0.5(10) . . . . ?
C12 C13 C14 C15 1.8(11) . . . . ?
C11 C10 C15 C14 -1.0(8) . . . . ?
C9 C10 C15 C14 -179.6(5) . . . . ?
C13 C14 C15 C10 -1.0(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033
