# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
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#######################################################################

data_dm14319
_database_code_depnum_ccdc_archive 'CCDC 1011578'
_audit_update_record             
;
2014-07-01 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 N O3'
_chemical_formula_weight         260.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.9370(3)
_cell_length_b                   5.9425(3)
_cell_length_c                   10.0505(7)
_cell_angle_alpha                105.428(4)
_cell_angle_beta                 101.284(4)
_cell_angle_gamma                99.757(3)
_cell_volume                     325.87(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    2302
_cell_measurement_theta_min      4.72
_cell_measurement_theta_max      68.76

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             139
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.750
_shelx_estimated_absorpt_T_min   0.795
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2435
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.718
_diffrn_reflns_theta_max         65.989
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.898
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.898
_diffrn_reflns_point_group_measured_fraction_max 0.655
_diffrn_reflns_point_group_measured_fraction_full 0.624
_reflns_number_total             1466
_reflns_number_gt                1464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.390
_reflns_Friedel_fraction_max     0.367
_reflns_Friedel_fraction_full    0.350

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_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-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1145P)²+0.0544P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 407 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.29(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1466
_refine_ls_number_parameters     175
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1544
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.008

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6834(5) -0.2678(6) 0.2548(4) 0.0236(8) Uani 1 1 d . . . . .
O1 O 0.4627(5) -0.3507(6) 0.6969(4) 0.0357(8) Uani 1 1 d . . . . .
O2 O 1.0248(5) 0.0313(6) 0.7151(3) 0.0291(7) Uani 1 1 d . . . . .
H2 H 0.9792 -0.0906 0.6425 0.044 Uiso 1 1 calc R U . . .
O3 O 0.8327(5) -0.3320(5) 0.4661(3) 0.0256(7) Uani 1 1 d . . . . .
C1 C 0.7538(6) 0.1926(7) 0.5663(4) 0.0210(8) Uani 1 1 d . . . . .
H1A H 0.8889 0.2388 0.5271 0.025 Uiso 1 1 calc R U . . .
H1B H 0.6695 0.3240 0.5768 0.025 Uiso 1 1 calc R U . . .
C2 C 0.8513(6) 0.1745(7) 0.7145(4) 0.0219(9) Uani 1 1 d . . . . .
C3 C 0.6517(7) 0.0689(8) 0.7730(4) 0.0285(9) Uani 1 1 d . . . . .
H3A H 0.7207 0.0405 0.8633 0.034 Uiso 1 1 calc R U . . .
H3B H 0.5525 0.1856 0.7938 0.034 Uiso 1 1 calc R U . . .
C4 C 0.4995(7) -0.1647(7) 0.6671(4) 0.0250(9) Uani 1 1 d . . . . .
C5 C 0.3973(6) -0.1474(7) 0.5226(4) 0.0248(9) Uani 1 1 d . . . . .
H5A H 0.2794 -0.0483 0.5304 0.030 Uiso 1 1 calc R U . . .
H5B H 0.3138 -0.3101 0.4580 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5838(6) -0.0374(7) 0.4559(4) 0.0192(8) Uani 1 1 d . . . . .
C7 C 0.7171(6) -0.2293(7) 0.3977(4) 0.0195(8) Uani 1 1 d . . . . .
C8 C 0.4692(6) 0.0079(7) 0.3211(4) 0.0213(9) Uani 1 1 d . . . . .
C9 C 0.3172(7) 0.1553(8) 0.2981(5) 0.0297(10) Uani 1 1 d . . . . .
H9 H 0.2713 0.2514 0.3753 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2331(9) 0.1593(9) 0.1588(5) 0.0373(11) Uani 1 1 d . . . . .
H10 H 0.1300 0.2601 0.1413 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2990(8) 0.0175(8) 0.0459(5) 0.0329(10) Uani 1 1 d . . . . .
H11 H 0.2385 0.0211 -0.0481 0.039 Uiso 1 1 calc R U . . .
C12 C 0.4511(7) -0.1289(8) 0.0677(4) 0.0275(9) Uani 1 1 d . . . . .
H12 H 0.4969 -0.2247 -0.0097 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5346(6) -0.1314(7) 0.2061(4) 0.0229(9) Uani 1 1 d . . . . .
C14 C 0.7881(8) -0.4326(9) 0.1660(5) 0.0352(11) Uani 1 1 d . . . . .
H14A H 0.9184 -0.3413 0.1411 0.053 Uiso 1 1 calc R U . . .
H14B H 0.6684 -0.5311 0.0787 0.053 Uiso 1 1 calc R U . . .
H14C H 0.8485 -0.5367 0.2182 0.053 Uiso 1 1 calc R U . . .
C15 C 0.9846(7) 0.4234(8) 0.8148(4) 0.0320(10) Uani 1 1 d . . . . .
H15A H 1.0277 0.4169 0.9127 0.048 Uiso 1 1 calc R U . . .
H15B H 0.8836 0.5370 0.8100 0.048 Uiso 1 1 calc R U . . .
H15C H 1.1281 0.4763 0.7862 0.048 Uiso 1 1 calc R U . . .


_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 C7 1.361(5) . ?
N1 C13 1.400(5) . ?
N1 C14 1.449(5) . ?
O1 C4 1.216(6) . ?
O2 C2 1.443(4) . ?
O2 H2 0.8400 . ?
O3 C7 1.223(5) . ?
C1 C2 1.528(5) . ?
C1 C6 1.551(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C15 1.526(5) . ?
C2 C3 1.536(6) . ?
C3 C4 1.513(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.498(6) . ?
C5 C6 1.543(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C8 1.506(6) . ?
C6 C7 1.550(5) . ?
C8 C9 1.389(6) . ?
C8 C13 1.396(6) . ?
C9 C10 1.399(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(5) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C7 N1 C13 111.5(3) . . ?
C7 N1 C14 123.3(3) . . ?
C13 N1 C14 125.1(4) . . ?
C2 O2 H2 109.5 . . ?
C2 C1 C6 116.2(3) . . ?
C2 C1 H1A 108.2 . . ?
C6 C1 H1A 108.2 . . ?
C2 C1 H1B 108.2 . . ?
C6 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
O2 C2 C15 104.7(3) . . ?
O2 C2 C1 112.3(3) . . ?
C15 C2 C1 109.2(3) . . ?
O2 C2 C3 109.2(3) . . ?
C15 C2 C3 110.3(3) . . ?
C1 C2 C3 111.0(3) . . ?
C4 C3 C2 111.2(3) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O1 C4 C5 122.8(4) . . ?
O1 C4 C3 122.9(4) . . ?
C5 C4 C3 114.3(3) . . ?
C4 C5 C6 113.5(3) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C8 C6 C5 111.3(3) . . ?
C8 C6 C7 101.3(3) . . ?
C5 C6 C7 109.0(3) . . ?
C8 C6 C1 112.2(3) . . ?
C5 C6 C1 110.6(3) . . ?
C7 C6 C1 112.1(3) . . ?
O3 C7 N1 124.8(3) . . ?
O3 C7 C6 126.9(3) . . ?
N1 C7 C6 108.3(3) . . ?
C9 C8 C13 119.7(4) . . ?
C9 C8 C6 130.9(4) . . ?
C13 C8 C6 109.4(3) . . ?
C8 C9 C10 118.6(4) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 117.9(4) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C12 C13 C8 121.9(4) . . ?
C12 C13 N1 128.7(3) . . ?
C8 C13 N1 109.4(3) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C6 C1 C2 O2 72.5(4) . . . . ?
C6 C1 C2 C15 -171.8(3) . . . . ?
C6 C1 C2 C3 -50.0(4) . . . . ?
O2 C2 C3 C4 -72.1(4) . . . . ?
C15 C2 C3 C4 173.4(3) . . . . ?
C1 C2 C3 C4 52.2(4) . . . . ?
C2 C3 C4 O1 124.7(4) . . . . ?
C2 C3 C4 C5 -55.4(4) . . . . ?
O1 C4 C5 C6 -127.0(4) . . . . ?
C3 C4 C5 C6 53.2(4) . . . . ?
C4 C5 C6 C8 -172.0(3) . . . . ?
C4 C5 C6 C7 77.1(4) . . . . ?
C4 C5 C6 C1 -46.6(4) . . . . ?
C2 C1 C6 C8 171.4(3) . . . . ?
C2 C1 C6 C5 46.5(4) . . . . ?
C2 C1 C6 C7 -75.3(4) . . . . ?
C13 N1 C7 O3 177.4(4) . . . . ?
C14 N1 C7 O3 -1.9(6) . . . . ?
C13 N1 C7 C6 -2.3(4) . . . . ?
C14 N1 C7 C6 178.4(4) . . . . ?
C8 C6 C7 O3 -177.3(4) . . . . ?
C5 C6 C7 O3 -59.9(5) . . . . ?
C1 C6 C7 O3 62.9(5) . . . . ?
C8 C6 C7 N1 2.4(4) . . . . ?
C5 C6 C7 N1 119.8(3) . . . . ?
C1 C6 C7 N1 -117.5(3) . . . . ?
C5 C6 C8 C9 61.7(5) . . . . ?
C7 C6 C8 C9 177.4(4) . . . . ?
C1 C6 C8 C9 -62.8(6) . . . . ?
C5 C6 C8 C13 -117.4(4) . . . . ?
C7 C6 C8 C13 -1.7(4) . . . . ?
C1 C6 C8 C13 118.1(3) . . . . ?
C13 C8 C9 C10 0.1(6) . . . . ?
C6 C8 C9 C10 -178.9(4) . . . . ?
C8 C9 C10 C11 0.5(7) . . . . ?
C9 C10 C11 C12 -0.8(8) . . . . ?
C10 C11 C12 C13 0.5(7) . . . . ?
C11 C12 C13 C8 0.0(6) . . . . ?
C11 C12 C13 N1 178.1(4) . . . . ?
C9 C8 C13 C12 -0.4(6) . . . . ?
C6 C8 C13 C12 178.8(3) . . . . ?
C9 C8 C13 N1 -178.7(4) . . . . ?
C6 C8 C13 N1 0.4(4) . . . . ?
C7 N1 C13 C12 -177.0(4) . . . . ?
C14 N1 C13 C12 2.3(6) . . . . ?
C7 N1 C13 C8 1.2(4) . . . . ?
C14 N1 C13 C8 -179.5(4) . . . . ?

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
O2 H2 O3 0.84 1.89 2.720(4) 168.6 .
C1 H1B O1 0.99 2.62 3.558(5) 158.9 1_565
C5 H5A O2 0.99 2.61 3.337(5) 130.1 1_455
C15 H15C O1 0.98 2.51 3.484(5) 171.6 1_665

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.089

_shelxl_version_number           2014-3

