# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_phs

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35

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           Hexagonal
_symmetry_space_group_name_H-M   P6(5)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   11.2648(8)
_cell_length_b                   11.2648(8)
_cell_length_c                   21.2304(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2333.1(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2533
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      20.92

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14031
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.58
_reflns_number_total             3606
_reflns_number_gt                2275
_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 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)+(0.0533P)²+0.3280P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.6(17)
_refine_ls_number_reflns         3606
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.90400(17) 0.77668(18) 0.14885(10) 0.0476(5) Uani 1 1 d . . .
O2 O 0.8741(3) 0.5159(2) 0.21710(10) 0.0663(6) Uani 1 1 d . . .
O3 O 0.6414(2) 0.4074(2) 0.13173(15) 0.0827(8) Uani 1 1 d . . .
N1 N 0.8133(2) 0.5151(2) 0.05859(11) 0.0463(6) Uani 1 1 d . . .
C1 C 1.2487(3) 1.0650(3) 0.15563(13) 0.0434(6) Uani 1 1 d . . .
H1A H 1.3002 1.0196 0.1510 0.052 Uiso 1 1 calc R . .
C2 C 1.3153(3) 1.2061(3) 0.15979(14) 0.0565(8) Uani 1 1 d . . .
H2A H 1.4125 1.2574 0.1577 0.068 Uiso 1 1 calc R . .
C3 C 1.2434(4) 1.2722(3) 0.16682(14) 0.0578(8) Uani 1 1 d . . .
H3A H 1.2904 1.3694 0.1694 0.069 Uiso 1 1 calc R . .
C4 C 1.1017(3) 1.1986(3) 0.17031(15) 0.0534(8) Uani 1 1 d . . .
H4A H 1.0514 1.2450 0.1757 0.064 Uiso 1 1 calc R . .
C5 C 1.0347(3) 1.0586(2) 0.16601(13) 0.0425(7) Uani 1 1 d . . .
H5A H 0.9375 1.0081 0.1684 0.051 Uiso 1 1 calc R . .
C6 C 1.1066(2) 0.9893(2) 0.15818(11) 0.0325(5) Uani 1 1 d . . .
C7 C 1.0290(3) 0.8376(2) 0.15173(11) 0.0340(5) Uani 1 1 d . . .
C8 C 1.1029(3) 0.7581(3) 0.14764(12) 0.0397(6) Uani 1 1 d . . .
H8A H 1.1380 0.7545 0.1899 0.048 Uiso 1 1 calc R . .
H8B H 1.1826 0.8069 0.1192 0.048 Uiso 1 1 calc R . .
C9 C 1.0130(3) 0.6126(3) 0.12363(12) 0.0367(6) Uani 1 1 d . . .
C10 C 0.8828(3) 0.5358(3) 0.16091(14) 0.0460(7) Uani 1 1 d . . .
C11 C 0.7621(3) 0.4774(3) 0.11608(17) 0.0549(8) Uani 1 1 d . . .
C12 C 0.9609(2) 0.6082(3) 0.05617(12) 0.0395(6) Uani 1 1 d . . .
H12A H 0.9817 0.7007 0.0425 0.047 Uiso 1 1 calc R . .
H12B H 1.0046 0.5739 0.0264 0.047 Uiso 1 1 calc R . .
C13 C 1.0918(3) 0.5339(3) 0.12769(15) 0.0528(8) Uani 1 1 d . . .
H13A H 1.0335 0.4402 0.1123 0.079 Uiso 1 1 calc R . .
H13B H 1.1172 0.5312 0.1716 0.079 Uiso 1 1 calc R . .
H13C H 1.1748 0.5802 0.1018 0.079 Uiso 1 1 calc R . .
C14 C 0.7317(3) 0.4811(3) 0.00130(16) 0.0662(9) Uani 1 1 d . . .
H14A H 0.6394 0.4022 0.0099 0.079 Uiso 1 1 calc R . .
H14B H 0.7749 0.4527 -0.0315 0.079 Uiso 1 1 calc R . .
C15 C 0.7165(4) 0.5993(4) -0.02399(18) 0.0713(10) Uani 1 1 d . B .
H15A H 0.8089 0.6800 -0.0301 0.086 Uiso 1 1 calc R . .
H15B H 0.6714 0.5733 -0.0657 0.086 Uiso 1 1 calc R . .
C16 C 0.6353(5) 0.6391(5) 0.0181(2) 0.0940(14) Uani 1 1 d . . .
H16A H 0.5554 0.5547 0.0345 0.113 Uiso 0.50 1 calc PR A 1
H16B H 0.6930 0.6905 0.0545 0.113 Uiso 0.50 1 calc PR A 1
H16C H 0.6519 0.6194 0.0616 0.113 Uiso 0.50 1 d PR A 2
H16D H 0.6787 0.7400 0.0148 0.113 Uiso 0.50 1 d PR A 2
C17 C 0.5866(7) 0.7223(7) -0.0125(3) 0.0498(15) Uani 0.50 1 d P B 1
H17A H 0.5355 0.7450 0.0179 0.060 Uiso 0.50 1 calc PR B 1
H17B H 0.5264 0.6711 -0.0477 0.060 Uiso 0.50 1 calc PR B 1
H17C H 0.6650 0.8070 -0.0283 0.060 Uiso 0.50 1 calc PR B 1
C17' C 0.5131(13) 0.594(2) 0.0139(7) 0.199(9) Uani 0.50 1 d P B 2
H17D H 0.4843 0.6376 0.0459 0.238 Uiso 0.50 1 calc PR B 2
H17E H 0.4645 0.4951 0.0205 0.238 Uiso 0.50 1 calc PR B 2
H17F H 0.4914 0.6146 -0.0280 0.238 Uiso 0.50 1 calc PR B 2

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 0.0284(10) 0.0318(9) 0.0782(14) -0.0030(9) 0.0088(9) 0.0117(8)
O2 0.1039(18) 0.0538(13) 0.0527(13) 0.0191(10) 0.0354(12) 0.0482(13)
O3 0.0471(14) 0.0461(13) 0.131(2) 0.0088(14) 0.0403(13) 0.0057(11)
N1 0.0370(12) 0.0288(12) 0.0628(15) -0.0045(10) 0.0084(12) 0.0088(10)
C1 0.0354(15) 0.0409(16) 0.0444(15) -0.0057(12) -0.0003(12) 0.0119(13)
C2 0.0403(17) 0.0452(18) 0.0532(17) -0.0037(14) 0.0028(14) -0.0016(14)
C3 0.073(2) 0.0306(16) 0.0561(19) -0.0009(13) -0.0038(16) 0.0159(16)
C4 0.060(2) 0.0344(15) 0.067(2) -0.0005(14) -0.0110(16) 0.0244(16)
C5 0.0407(16) 0.0328(14) 0.0511(17) -0.0004(12) -0.0047(12) 0.0162(13)
C6 0.0329(13) 0.0316(13) 0.0278(11) 0.0024(10) 0.0002(10) 0.0123(11)
C7 0.0303(14) 0.0336(13) 0.0363(14) 0.0029(11) 0.0051(11) 0.0146(12)
C8 0.0390(15) 0.0400(15) 0.0434(16) 0.0004(12) 0.0039(12) 0.0220(13)
C9 0.0465(15) 0.0336(14) 0.0366(13) 0.0062(11) 0.0092(12) 0.0250(13)
C10 0.066(2) 0.0300(14) 0.0492(17) 0.0122(13) 0.0274(15) 0.0292(14)
C11 0.0440(19) 0.0249(14) 0.087(2) 0.0049(15) 0.0202(17) 0.0104(14)
C12 0.0328(14) 0.0326(14) 0.0475(15) 0.0021(12) 0.0079(12) 0.0121(12)
C13 0.067(2) 0.0515(18) 0.0570(18) -0.0002(14) 0.0066(15) 0.0428(17)
C14 0.0519(19) 0.055(2) 0.075(2) -0.0288(17) -0.0136(17) 0.0139(16)
C15 0.067(2) 0.084(3) 0.068(2) -0.0364(19) -0.0283(18) 0.042(2)
C16 0.089(3) 0.143(4) 0.083(3) -0.045(3) -0.030(2) 0.083(3)
C17 0.044(4) 0.062(4) 0.048(3) -0.005(3) -0.002(3) 0.031(3)
C17' 0.112(10) 0.35(2) 0.159(13) -0.157(15) -0.079(10) 0.132(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 C7 1.221(3) . ?
O2 C10 1.209(3) . ?
O3 C11 1.228(3) . ?
N1 C11 1.326(4) . ?
N1 C14 1.456(4) . ?
N1 C12 1.457(3) . ?
C1 C2 1.380(4) . ?
C1 C6 1.388(3) . ?
C2 C3 1.355(5) . ?
C3 C4 1.384(5) . ?
C4 C5 1.370(4) . ?
C5 C6 1.388(4) . ?
C6 C7 1.486(3) . ?
C7 C8 1.499(3) . ?
C8 C9 1.520(4) . ?
C9 C10 1.502(4) . ?
C9 C12 1.539(4) . ?
C9 C13 1.539(4) . ?
C10 C11 1.514(5) . ?
C14 C15 1.522(5) . ?
C15 C16 1.498(5) . ?
C16 C17' 1.210(12) . ?
C16 C17 1.455(7) . ?

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
C11 N1 C14 124.6(3) . . ?
C11 N1 C12 114.8(2) . . ?
C14 N1 C12 120.2(2) . . ?
C2 C1 C6 120.0(3) . . ?
C3 C2 C1 120.7(3) . . ?
C2 C3 C4 120.3(3) . . ?
C5 C4 C3 119.5(3) . . ?
C4 C5 C6 121.0(3) . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 119.0(2) . . ?
C1 C6 C7 122.5(2) . . ?
O1 C7 C6 120.1(2) . . ?
O1 C7 C8 119.3(2) . . ?
C6 C7 C8 120.6(2) . . ?
C7 C8 C9 113.2(2) . . ?
C10 C9 C8 112.1(2) . . ?
C10 C9 C12 103.0(2) . . ?
C8 C9 C12 112.6(2) . . ?
C10 C9 C13 108.5(2) . . ?
C8 C9 C13 109.7(2) . . ?
C12 C9 C13 110.7(2) . . ?
O2 C10 C9 126.3(3) . . ?
O2 C10 C11 124.6(3) . . ?
C9 C10 C11 109.0(2) . . ?
O3 C11 N1 128.3(3) . . ?
O3 C11 C10 125.0(3) . . ?
N1 C11 C10 106.7(2) . . ?
N1 C12 C9 105.6(2) . . ?
N1 C14 C15 113.4(3) . . ?
C16 C15 C14 113.8(4) . . ?
C17' C16 C17 61.2(10) . . ?
C17' C16 C15 124.8(7) . . ?
C17 C16 C15 114.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 933766'
