# 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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:
#                         www.ccdc.cam.ac.uk
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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.
#
data_gao1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N O'
_chemical_formula_weight         255.35

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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5188(13)
_cell_length_b                   6.6901(13)
_cell_length_c                   16.077(3)
_cell_angle_alpha                93.17(3)
_cell_angle_beta                 91.18(3)
_cell_angle_gamma                98.90(3)
_cell_volume                     691.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_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            6626
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3128
_reflns_number_gt                2011
_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)+(0.1233P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3128
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1946
_refine_ls_wR_factor_gt          0.1584
_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
N1 N 0.5945(2) -0.0462(2) 0.24222(9) 0.0367(4) Uani 1 1 d . . .
C1 C 0.7835(3) -0.0221(3) 0.29096(10) 0.0360(4) Uani 1 1 d . . .
C13 C 0.5866(3) 0.1194(3) 0.10441(11) 0.0426(5) Uani 1 1 d . . .
H13A H 0.4932 0.0023 0.0788 0.051 Uiso 1 1 calc R . .
O1 O 0.4645(2) -0.3636(2) 0.27519(11) 0.0635(5) Uani 1 1 d . . .
C3 C 1.0871(3) 0.2243(3) 0.32289(12) 0.0433(4) Uani 1 1 d . . .
H3A H 1.1642 0.3508 0.3155 0.052 Uiso 1 1 calc R . .
C6 C 0.8557(3) -0.1552(3) 0.34369(11) 0.0428(5) Uani 1 1 d . . .
H6A H 0.7779 -0.2815 0.3508 0.051 Uiso 1 1 calc R . .
C2 C 0.8969(3) 0.1665(3) 0.28096(11) 0.0374(4) Uani 1 1 d . . .
C8 C 0.7874(3) 0.2863(3) 0.22312(11) 0.0381(4) Uani 1 1 d . . .
H8A H 0.7618 0.4143 0.2505 0.046 Uiso 1 1 calc R . .
C9 C 0.4436(3) -0.2106(3) 0.23960(13) 0.0431(5) Uani 1 1 d . . .
C7 C 0.5801(3) 0.1425(3) 0.19942(11) 0.0369(4) Uani 1 1 d . . .
H7A H 0.4594 0.2029 0.2174 0.044 Uiso 1 1 calc R . .
C5 C 1.0474(3) -0.0961(3) 0.38591(12) 0.0452(5) Uani 1 1 d . . .
C10 C 0.8887(3) 0.3196(3) 0.13829(13) 0.0459(5) Uani 1 1 d . . .
H10A H 1.0395 0.3624 0.1412 0.055 Uiso 1 1 calc R . .
C4 C 1.1626(3) 0.0929(3) 0.37604(12) 0.0461(5) Uani 1 1 d . . .
C14 C 0.8166(3) 0.1168(3) 0.09009(12) 0.0480(5) Uani 1 1 d . . .
H14A H 0.8504 0.1191 0.0316 0.058 Uiso 1 1 calc R . .
H14B H 0.8674 0.0044 0.1151 0.058 Uiso 1 1 calc R . .
C15 C 0.2462(3) -0.2002(3) 0.19041(14) 0.0537(5) Uani 1 1 d . . .
H15A H 0.1526 -0.3252 0.1935 0.080 Uiso 1 1 calc R . .
H15B H 0.2782 -0.1787 0.1333 0.080 Uiso 1 1 calc R . .
H15C H 0.1822 -0.0902 0.2132 0.080 Uiso 1 1 calc R . .
C12 C 0.5557(3) 0.3244(3) 0.07149(14) 0.0538(6) Uani 1 1 d . . .
H12A H 0.4434 0.3777 0.0994 0.065 Uiso 1 1 calc R . .
H12B H 0.5259 0.3120 0.0119 0.065 Uiso 1 1 calc R . .
C11 C 0.7662(3) 0.4609(3) 0.09226(14) 0.0546(6) Uani 1 1 d . . .
H11A H 0.8347 0.5051 0.0420 0.066 Uiso 1 1 calc R . .
H11B H 0.7485 0.5788 0.1277 0.066 Uiso 1 1 calc R . .
C16 C 1.3688(3) 0.1627(4) 0.42200(14) 0.0654(7) Uani 1 1 d . . .
H16A H 1.4246 0.2966 0.4068 0.098 Uiso 1 1 calc R . .
H16B H 1.4641 0.0714 0.4073 0.098 Uiso 1 1 calc R . .
H16C H 1.3484 0.1643 0.4810 0.098 Uiso 1 1 calc R . .
C17 C 1.1242(4) -0.2430(4) 0.44272(14) 0.0637(7) Uani 1 1 d . . .
H17A H 1.0246 -0.3649 0.4420 0.095 Uiso 1 1 calc R . .
H17B H 1.1420 -0.1826 0.4985 0.095 Uiso 1 1 calc R . .
H17C H 1.2547 -0.2748 0.4238 0.095 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 0.0333(7) 0.0342(8) 0.0421(8) 0.0052(6) 0.0002(6) 0.0029(6)
C1 0.0360(8) 0.0374(10) 0.0351(9) 0.0015(7) 0.0009(7) 0.0078(7)
C13 0.0455(9) 0.0381(10) 0.0431(10) 0.0031(8) -0.0075(8) 0.0040(7)
O1 0.0555(9) 0.0413(9) 0.0921(12) 0.0171(8) 0.0049(8) -0.0024(7)
C3 0.0412(9) 0.0446(11) 0.0424(10) -0.0016(8) -0.0027(8) 0.0031(7)
C6 0.0503(10) 0.0402(11) 0.0389(10) 0.0041(8) 0.0041(8) 0.0095(8)
C2 0.0376(9) 0.0359(10) 0.0381(9) 0.0011(7) -0.0002(7) 0.0044(7)
C8 0.0387(9) 0.0285(9) 0.0464(10) 0.0016(7) -0.0044(7) 0.0037(7)
C9 0.0383(9) 0.0372(10) 0.0523(11) -0.0009(8) 0.0065(8) 0.0016(7)
C7 0.0341(8) 0.0320(9) 0.0450(10) 0.0026(7) -0.0033(7) 0.0070(6)
C5 0.0490(10) 0.0552(13) 0.0349(9) 0.0045(8) 0.0007(8) 0.0185(9)
C10 0.0392(9) 0.0440(11) 0.0551(12) 0.0132(9) 0.0017(8) 0.0046(8)
C4 0.0424(10) 0.0595(13) 0.0366(10) -0.0022(9) -0.0045(8) 0.0113(9)
C14 0.0567(11) 0.0488(12) 0.0420(11) 0.0069(8) 0.0069(8) 0.0166(9)
C15 0.0377(10) 0.0517(13) 0.0669(14) -0.0046(10) 0.0009(9) -0.0047(8)
C12 0.0579(12) 0.0504(13) 0.0549(12) 0.0136(10) -0.0079(10) 0.0117(9)
C11 0.0592(12) 0.0452(12) 0.0604(13) 0.0199(10) -0.0019(10) 0.0059(9)
C16 0.0508(12) 0.0904(19) 0.0542(13) -0.0033(12) -0.0156(10) 0.0131(12)
C17 0.0787(15) 0.0702(16) 0.0490(12) 0.0118(11) -0.0059(11) 0.0315(13)

_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 1.356(2) . ?
N1 C1 1.429(2) . ?
N1 C7 1.485(2) . ?
C1 C2 1.380(3) . ?
C1 C6 1.389(2) . ?
C13 C14 1.524(3) . ?
C13 C7 1.529(3) . ?
C13 C12 1.537(3) . ?
O1 C9 1.224(2) . ?
C3 C2 1.389(2) . ?
C3 C4 1.395(3) . ?
C6 C5 1.400(3) . ?
C2 C8 1.500(2) . ?
C8 C10 1.540(3) . ?
C8 C7 1.560(2) . ?
C9 C15 1.510(3) . ?
C5 C4 1.386(3) . ?
C5 C17 1.511(2) . ?
C10 C14 1.528(3) . ?
C10 C11 1.538(2) . ?
C4 C16 1.516(3) . ?
C12 C11 1.545(3) . ?

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 125.39(15) . . ?
C9 N1 C7 124.64(14) . . ?
C1 N1 C7 109.83(14) . . ?
C2 C1 C6 120.77(16) . . ?
C2 C1 N1 109.78(14) . . ?
C6 C1 N1 129.44(17) . . ?
C14 C13 C7 102.33(14) . . ?
C14 C13 C12 102.09(16) . . ?
C7 C13 C12 106.83(16) . . ?
C2 C3 C4 120.09(19) . . ?
C1 C6 C5 118.97(19) . . ?
C1 C2 C3 120.06(16) . . ?
C1 C2 C8 111.69(15) . . ?
C3 C2 C8 128.25(17) . . ?
C2 C8 C10 115.18(15) . . ?
C2 C8 C7 103.47(13) . . ?
C10 C8 C7 103.07(15) . . ?
O1 C9 N1 122.04(17) . . ?
O1 C9 C15 120.33(18) . . ?
N1 C9 C15 117.63(17) . . ?
N1 C7 C13 114.48(15) . . ?
N1 C7 C8 105.16(12) . . ?
C13 C7 C8 102.60(14) . . ?
C4 C5 C6 120.65(17) . . ?
C4 C5 C17 121.05(19) . . ?
C6 C5 C17 118.3(2) . . ?
C14 C10 C11 101.48(16) . . ?
C14 C10 C8 102.35(15) . . ?
C11 C10 C8 106.97(16) . . ?
C5 C4 C3 119.46(17) . . ?
C5 C4 C16 121.93(19) . . ?
C3 C4 C16 118.6(2) . . ?
C13 C14 C10 94.56(16) . . ?
C13 C12 C11 103.50(15) . . ?
C10 C11 C12 102.67(16) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 988826'
