# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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:
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#  from this site to visualise CIF-encoded structures and 
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data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2 O'
_chemical_formula_weight         266.33
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   5.19550(10)
_cell_length_b                   8.58560(10)
_cell_length_c                   32.9171(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1468.32(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    11298
_cell_measurement_theta_min      4.0256
_cell_measurement_theta_max      71.6438

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8139
_exptl_absorpt_correction_T_max  0.8555
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16033
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         5.32
_diffrn_reflns_theta_max         71.79
_reflns_number_total             2840
_reflns_number_gt                2723
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0825P)²+0.0165P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_number_reflns         2840
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_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 0.20942(16) 0.45691(11) 0.55410(3) 0.0575(2) Uani 1 1 d . . .
N1 N 0.62964(19) 0.36516(11) 0.50745(3) 0.0467(2) Uani 1 1 d . . .
N2 N 0.63619(18) 0.41432(11) 0.54850(3) 0.0493(2) Uani 1 1 d . . .
H2 H 0.7820 0.4153 0.5609 0.059 Uiso 1 1 calc R . .
C11 C 0.4256(2) 0.45954(12) 0.56905(3) 0.0451(2) Uani 1 1 d . . .
C16 C 0.3195(3) 0.66601(18) 0.66841(4) 0.0689(4) Uani 1 1 d . . .
H16 H 0.2056 0.7391 0.6790 0.083 Uiso 1 1 calc R . .
C12 C 0.4674(2) 0.51108(13) 0.61211(3) 0.0470(3) Uani 1 1 d . . .
C10 C 0.8270(3) 0.61130(16) 0.48537(4) 0.0646(3) Uani 1 1 d . . .
H10A H 0.9860 0.5567 0.4811 0.097 Uiso 1 1 calc R . .
H10B H 0.8229 0.6522 0.5125 0.097 Uiso 1 1 calc R . .
H10C H 0.8136 0.6953 0.4662 0.097 Uiso 1 1 calc R . .
C17 C 0.2961(3) 0.61806(15) 0.62839(4) 0.0583(3) Uani 1 1 d . . .
H17 H 0.1644 0.6579 0.6123 0.070 Uiso 1 1 calc R . .
C14 C 0.6815(3) 0.4985(2) 0.67669(4) 0.0698(4) Uani 1 1 d . . .
H14 H 0.8104 0.4575 0.6931 0.084 Uiso 1 1 calc R . .
C7 C 0.4532(3) 0.49150(16) 0.40766(4) 0.0557(3) Uani 1 1 d . . .
H7 H 0.3232 0.5597 0.4155 0.067 Uiso 1 1 calc R . .
C3 C 0.6512(3) 0.35426(19) 0.34763(4) 0.0677(4) Uani 1 1 d . . .
H3 H 0.7729 0.3087 0.3646 0.081 Uiso 1 1 calc R . .
C15 C 0.5111(3) 0.60556(18) 0.69246(4) 0.0699(4) Uani 1 1 d . . .
H15 H 0.5257 0.6369 0.7194 0.084 Uiso 1 1 calc R . .
C8 C 0.6047(3) 0.44028(13) 0.43664(3) 0.0523(3) Uani 1 1 d . . .
H8 H 0.7208 0.3616 0.4302 0.063 Uiso 1 1 calc R . .
C9 C 0.6034(2) 0.50011(12) 0.47944(3) 0.0474(3) Uani 1 1 d . . .
H9 H 0.4410 0.5544 0.4848 0.057 Uiso 1 1 calc R . .
C13 C 0.6621(3) 0.45148(16) 0.63642(4) 0.0595(3) Uani 1 1 d . . .
H13 H 0.7791 0.3803 0.6258 0.071 Uiso 1 1 calc R . .
C2 C 0.6569(3) 0.3228(2) 0.30643(4) 0.0807(5) Uani 1 1 d . . .
H2A H 0.7807 0.2555 0.2960 0.097 Uiso 1 1 calc R . .
C4 C 0.4662(2) 0.45296(14) 0.36413(4) 0.0549(3) Uani 1 1 d . . .
C5 C 0.2887(3) 0.5194(2) 0.33774(4) 0.0731(4) Uani 1 1 d . . .
H5 H 0.1623 0.5855 0.3479 0.088 Uiso 1 1 calc R . .
C1 C 0.4798(4) 0.3908(2) 0.28069(4) 0.0834(5) Uani 1 1 d . . .
H1A H 0.4846 0.3704 0.2530 0.100 Uiso 1 1 calc R . .
C6 C 0.2976(4) 0.4883(3) 0.29637(5) 0.0864(5) Uani 1 1 d . . .
H6 H 0.1780 0.5344 0.2791 0.104 Uiso 1 1 calc R . .
H1 H 0.492(4) 0.3012(16) 0.5050(4) 0.061(4) Uiso 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
O1 0.0367(4) 0.0742(5) 0.0616(5) -0.0049(4) -0.0051(3) 0.0009(4)
N1 0.0438(5) 0.0479(4) 0.0485(4) -0.0033(4) -0.0027(4) 0.0003(4)
N2 0.0364(5) 0.0627(5) 0.0489(4) -0.0061(4) -0.0043(4) 0.0022(4)
C11 0.0371(5) 0.0448(5) 0.0534(5) 0.0016(4) -0.0030(4) -0.0017(4)
C16 0.0666(9) 0.0769(8) 0.0632(7) -0.0101(6) 0.0131(6) 0.0012(8)
C12 0.0395(6) 0.0496(5) 0.0518(5) 0.0016(4) 0.0022(4) -0.0031(5)
C10 0.0601(8) 0.0596(6) 0.0742(7) 0.0053(6) -0.0088(6) -0.0122(6)
C17 0.0504(6) 0.0657(6) 0.0586(6) -0.0018(5) 0.0038(5) 0.0038(6)
C14 0.0642(8) 0.0879(9) 0.0574(6) 0.0049(7) -0.0118(6) -0.0017(8)
C7 0.0475(7) 0.0613(6) 0.0584(6) 0.0037(5) -0.0010(5) 0.0025(6)
C3 0.0629(8) 0.0808(8) 0.0594(6) 0.0049(6) -0.0013(6) 0.0070(8)
C15 0.0716(9) 0.0883(9) 0.0498(6) -0.0063(6) 0.0045(6) -0.0139(8)
C8 0.0519(7) 0.0512(5) 0.0537(6) -0.0001(4) -0.0021(5) 0.0049(5)
C9 0.0407(6) 0.0460(5) 0.0554(5) -0.0021(4) -0.0028(4) 0.0044(5)
C13 0.0514(7) 0.0680(6) 0.0589(6) 0.0010(5) -0.0060(5) 0.0047(6)
C2 0.0756(10) 0.1018(11) 0.0646(8) -0.0039(8) 0.0097(8) 0.0012(10)
C4 0.0497(6) 0.0588(6) 0.0562(6) 0.0079(5) -0.0032(5) -0.0061(6)
C5 0.0689(8) 0.0838(8) 0.0666(7) 0.0060(7) -0.0140(7) 0.0090(8)
C1 0.0853(11) 0.1113(12) 0.0537(7) 0.0033(8) -0.0028(7) -0.0185(11)
C6 0.0847(11) 0.1073(12) 0.0671(8) 0.0130(8) -0.0216(8) -0.0013(11)

_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 C11 1.2264(14) . ?
N1 N2 1.4161(12) . ?
N1 C9 1.4870(14) . ?
N1 H1 0.905(18) . ?
N2 C11 1.3436(15) . ?
N2 H2 0.8600 . ?
C11 C12 1.5006(15) . ?
C16 C15 1.373(2) . ?
C16 C17 1.3854(17) . ?
C16 H16 0.9300 . ?
C12 C17 1.3871(17) . ?
C12 C13 1.3874(17) . ?
C10 C9 1.5162(17) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C17 H17 0.9300 . ?
C14 C15 1.378(2) . ?
C14 C13 1.3896(18) . ?
C14 H14 0.9300 . ?
C7 C8 1.3128(18) . ?
C7 C4 1.4721(17) . ?
C7 H7 0.9300 . ?
C3 C2 1.3833(19) . ?
C3 C4 1.391(2) . ?
C3 H3 0.9300 . ?
C15 H15 0.9300 . ?
C8 C9 1.4997(15) . ?
C8 H8 0.9300 . ?
C9 H9 0.9800 . ?
C13 H13 0.9300 . ?
C2 C1 1.380(2) . ?
C2 H2A 0.9300 . ?
C4 C5 1.3898(18) . ?
C5 C6 1.389(2) . ?
C5 H5 0.9300 . ?
C1 C6 1.365(3) . ?
C1 H1A 0.9300 . ?
C6 H6 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
N2 N1 C9 111.20(8) . . ?
N2 N1 H1 106.6(9) . . ?
C9 N1 H1 110.1(9) . . ?
C11 N2 N1 123.15(9) . . ?
C11 N2 H2 118.4 . . ?
N1 N2 H2 118.4 . . ?
O1 C11 N2 122.58(10) . . ?
O1 C11 C12 121.14(10) . . ?
N2 C11 C12 116.27(9) . . ?
C15 C16 C17 119.96(13) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C17 C12 C13 119.29(11) . . ?
C17 C12 C11 117.86(10) . . ?
C13 C12 C11 122.80(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C17 C12 120.52(12) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C15 C14 C13 120.45(14) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C8 C7 C4 127.18(12) . . ?
C8 C7 H7 116.4 . . ?
C4 C7 H7 116.4 . . ?
C2 C3 C4 121.10(13) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C16 C15 C14 120.04(12) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C7 C8 C9 124.41(11) . . ?
C7 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
N1 C9 C8 108.37(9) . . ?
N1 C9 C10 109.91(9) . . ?
C8 C9 C10 109.44(10) . . ?
N1 C9 H9 109.7 . . ?
C8 C9 H9 109.7 . . ?
C10 C9 H9 109.7 . . ?
C12 C13 C14 119.73(13) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C1 C2 C3 120.31(16) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C5 C4 C3 117.68(12) . . ?
C5 C4 C7 119.04(12) . . ?
C3 C4 C7 123.27(11) . . ?
C6 C5 C4 120.78(15) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C6 C1 C2 119.32(13) . . ?
C6 C1 H1A 120.3 . . ?
C2 C1 H1A 120.3 . . ?
C1 C6 C5 120.79(15) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?

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
C9 N1 N2 C11 76.24(13) . . . . ?
N1 N2 C11 O1 2.40(17) . . . . ?
N1 N2 C11 C12 -178.84(9) . . . . ?
O1 C11 C12 C17 -28.94(17) . . . . ?
N2 C11 C12 C17 152.29(11) . . . . ?
O1 C11 C12 C13 148.29(13) . . . . ?
N2 C11 C12 C13 -30.48(16) . . . . ?
C15 C16 C17 C12 -1.1(2) . . . . ?
C13 C12 C17 C16 0.5(2) . . . . ?
C11 C12 C17 C16 177.79(12) . . . . ?
C17 C16 C15 C14 0.7(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C4 C7 C8 C9 171.51(12) . . . . ?
N2 N1 C9 C8 178.53(9) . . . . ?
N2 N1 C9 C10 58.97(12) . . . . ?
C7 C8 C9 N1 138.73(13) . . . . ?
C7 C8 C9 C10 -101.41(15) . . . . ?
C17 C12 C13 C14 0.5(2) . . . . ?
C11 C12 C13 C14 -176.66(12) . . . . ?
C15 C14 C13 C12 -0.9(2) . . . . ?
C4 C3 C2 C1 0.8(3) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C2 C3 C4 C7 -179.38(15) . . . . ?
C8 C7 C4 C5 -179.74(14) . . . . ?
C8 C7 C4 C3 -0.7(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C7 C4 C5 C6 178.78(16) . . . . ?
C3 C2 C1 C6 -0.6(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?

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
N2 H2 O1 0.86 2.26 3.0062(13) 145.1 1_655

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        71.79
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.026
_database_code_depnum_ccdc_archive 'CCDC 997538'
