# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_maa
_database_code_depnum_ccdc_archive 'CCDC 1033099'
_audit_update_record             
;
2014-11-07 deposited with the CCDC.
2015-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32

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)/c  '

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

_cell_length_a                   13.9327(12)
_cell_length_b                   5.8545(5)
_cell_length_c                   18.9127(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.456(5)
_cell_angle_gamma                90.00
_cell_volume                     1454.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1761
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      22.25

_exptl_crystal_description       block
_exptl_crystal_colour            colour-less
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   multi-scan

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13334
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2549
_reflns_number_gt                1946
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.0100P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2549
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1735
_refine_ls_R_factor_gt           0.0901
_refine_ls_wR_factor_ref         0.1667
_refine_ls_wR_factor_gt          0.1455
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_restrained_S_all      1.235
_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
C8 C 0.2735(4) 0.3940(9) 0.0365(3) 0.0654(14) Uani 1 1 d . . .
H8 H 0.3085 0.2462 0.0460 0.078 Uiso 1 1 calc R . .
C7 C 0.2240(4) 0.4251(9) 0.0941(3) 0.0690(14) Uani 1 1 d . . .
H7 H 0.1888 0.5725 0.0839 0.083 Uiso 1 1 calc R . .
C6 C 0.1412(3) 0.2395(9) 0.0829(3) 0.0725(15) Uani 1 1 d . . .
H6A H 0.1733 0.0913 0.0958 0.087 Uiso 1 1 calc R . .
H6B H 0.1025 0.2699 0.1161 0.087 Uiso 1 1 calc R . .
C9 C 0.2023(3) 0.3928(9) -0.0448(3) 0.0689(14) Uani 1 1 d . . .
H9 H 0.1679 0.5413 -0.0529 0.083 Uiso 1 1 calc R . .
C10 C 0.1179(3) 0.2134(9) -0.0549(3) 0.0629(13) Uani 1 1 d . . .
H10 H 0.1515 0.0640 -0.0474 0.075 Uiso 1 1 calc R . .
C4 C 0.0437(4) 0.2156(12) -0.1353(3) 0.109(2) Uani 1 1 d . . .
H4A H -0.0028 0.0878 -0.1418 0.131 Uiso 1 1 calc R . .
H4B H 0.0037 0.3548 -0.1431 0.131 Uiso 1 1 calc R . .
C5 C 0.0708(4) 0.2354(10) 0.0036(3) 0.0833(17) Uani 1 1 d . . .
C2 C 0.1752(4) 0.3797(11) -0.1820(3) 0.0893(18) Uani 1 1 d . . .
H2A H 0.1446 0.5300 -0.1932 0.107 Uiso 1 1 calc R . .
H2B H 0.2116 0.3490 -0.2167 0.107 Uiso 1 1 calc R . .
C1 C 0.2501(4) 0.3752(12) -0.1010(3) 0.109(2) Uani 1 1 d . . .
H1A H 0.2886 0.2339 -0.0933 0.131 Uiso 1 1 calc R . .
H1B H 0.2978 0.5004 -0.0946 0.131 Uiso 1 1 calc R . .
C3 C 0.0926(4) 0.2019(12) -0.1920(3) 0.100(2) Uani 1 1 d . . .
H3A H 0.0414 0.2210 -0.2410 0.120 Uiso 1 1 calc R . .
H3B H 0.1221 0.0511 -0.1903 0.120 Uiso 1 1 calc R . .
C11 C 0.2955(3) 0.4328(9) 0.1743(2) 0.0565(12) Uani 1 1 d . . .
C12 C 0.3634(4) 0.2609(9) 0.2055(3) 0.0660(14) Uani 1 1 d . . .
H12 H 0.3671 0.1356 0.1763 0.079 Uiso 1 1 calc R . .
C16 C 0.2925(4) 0.6180(9) 0.2196(3) 0.0778(16) Uani 1 1 d . . .
H16 H 0.2469 0.7368 0.2004 0.093 Uiso 1 1 calc R . .
C13 C 0.4258(4) 0.2704(11) 0.2788(3) 0.0796(16) Uani 1 1 d . . .
H13 H 0.4708 0.1513 0.2987 0.096 Uiso 1 1 calc R . .
C15 C 0.3581(5) 0.6262(11) 0.2943(3) 0.0843(17) Uani 1 1 d . . .
H15 H 0.3573 0.7515 0.3243 0.101 Uiso 1 1 calc R . .
C14 C 0.4225(4) 0.4500(12) 0.3222(3) 0.0839(18) Uani 1 1 d . . .
H14 H 0.4650 0.4533 0.3719 0.101 Uiso 1 1 calc R . .
O1 O -0.0249(3) 0.2496(7) -0.0109(2) 0.1013(13) Uani 1 1 d . . .
O2 O 0.4396(3) 0.5124(9) 0.0574(2) 0.1215(19) Uani 1 1 d . . .
O3 O 0.3274(4) 0.7760(9) 0.0410(2) 0.1172(18) Uani 1 1 d . . .
N1 N 0.3541(4) 0.5767(11) 0.0453(2) 0.0845(16) 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
C8 0.068(3) 0.065(3) 0.061(3) -0.005(3) 0.018(3) -0.025(3)
C7 0.066(3) 0.071(4) 0.066(3) 0.005(3) 0.017(3) -0.002(3)
C6 0.058(3) 0.087(4) 0.069(3) 0.005(3) 0.016(3) -0.016(3)
C9 0.061(3) 0.085(4) 0.057(3) 0.006(3) 0.015(3) -0.022(3)
C10 0.057(3) 0.064(3) 0.062(3) -0.004(3) 0.012(3) -0.012(3)
C4 0.090(4) 0.143(6) 0.077(4) 0.001(4) 0.004(4) -0.053(4)
C5 0.062(4) 0.069(4) 0.104(5) 0.015(3) 0.008(4) -0.007(3)
C2 0.082(4) 0.126(5) 0.056(3) -0.002(3) 0.018(3) -0.019(4)
C1 0.097(4) 0.162(7) 0.070(4) -0.022(4) 0.029(4) -0.051(5)
C3 0.092(4) 0.134(6) 0.069(4) -0.032(4) 0.020(3) -0.029(4)
C11 0.052(3) 0.063(3) 0.052(3) 0.006(3) 0.014(2) -0.001(3)
C12 0.069(3) 0.062(4) 0.070(3) 0.003(3) 0.027(3) 0.009(3)
C16 0.074(4) 0.066(4) 0.096(4) 0.014(3) 0.032(3) 0.019(3)
C13 0.068(4) 0.091(5) 0.073(4) 0.013(4) 0.014(3) 0.012(3)
C15 0.105(5) 0.078(4) 0.072(4) -0.019(3) 0.033(4) -0.006(4)
C14 0.076(4) 0.109(6) 0.060(4) 0.004(4) 0.014(3) -0.011(4)
O1 0.079(3) 0.086(3) 0.118(3) 0.005(2) 0.006(2) 0.012(3)
O2 0.077(3) 0.187(5) 0.102(3) -0.023(3) 0.031(3) -0.043(3)
O3 0.128(4) 0.096(3) 0.117(4) 0.005(3) 0.025(3) -0.045(3)
N1 0.082(4) 0.112(5) 0.054(3) -0.004(3) 0.017(3) -0.037(4)

_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
C8 C7 1.481(6) . ?
C8 N1 1.519(6) . ?
C8 C9 1.527(6) . ?
C7 C11 1.513(6) . ?
C7 C6 1.548(6) . ?
C6 C5 1.494(6) . ?
C9 C1 1.434(6) . ?
C9 C10 1.540(6) . ?
C10 C5 1.467(7) . ?
C10 C4 1.529(6) . ?
C4 C3 1.451(7) . ?
C5 O1 1.271(6) . ?
C2 C3 1.517(7) . ?
C2 C1 1.541(6) . ?
C11 C12 1.373(6) . ?
C11 C16 1.391(6) . ?
C12 C13 1.370(6) . ?
C16 C15 1.404(7) . ?
C13 C14 1.344(7) . ?
C15 C14 1.354(7) . ?
O2 N1 1.196(6) . ?
O3 N1 1.219(6) . ?

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 C8 N1 109.9(4) . . ?
C7 C8 C9 115.8(4) . . ?
N1 C8 C9 108.8(4) . . ?
C8 C7 C11 115.4(4) . . ?
C8 C7 C6 108.8(4) . . ?
C11 C7 C6 111.7(4) . . ?
C5 C6 C7 111.0(4) . . ?
C1 C9 C8 116.1(4) . . ?
C1 C9 C10 112.5(5) . . ?
C8 C9 C10 109.9(4) . . ?
C5 C10 C4 115.1(4) . . ?
C5 C10 C9 111.2(4) . . ?
C4 C10 C9 110.7(4) . . ?
C3 C4 C10 114.0(5) . . ?
O1 C5 C10 123.0(5) . . ?
O1 C5 C6 120.3(6) . . ?
C10 C5 C6 116.7(5) . . ?
C3 C2 C1 110.2(5) . . ?
C9 C1 C2 114.1(5) . . ?
C4 C3 C2 113.2(5) . . ?
C12 C11 C16 117.6(4) . . ?
C12 C11 C7 122.6(5) . . ?
C16 C11 C7 119.8(5) . . ?
C13 C12 C11 121.3(5) . . ?
C11 C16 C15 120.2(5) . . ?
C14 C13 C12 120.7(6) . . ?
C14 C15 C16 119.4(5) . . ?
C13 C14 C15 120.7(5) . . ?
O2 N1 O3 125.2(6) . . ?
O2 N1 C8 116.9(6) . . ?
O3 N1 C8 117.9(6) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.054
