# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_20131014bb_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 N3 O2'
_chemical_formula_weight         311.38

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)/n  '
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   12.3807(10)
_cell_length_b                   10.2922(8)
_cell_length_c                   13.3591(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.8390(10)
_cell_angle_gamma                90.00
_cell_volume                     1659.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3159
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.59

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9820
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_process_details   sadabs

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9437
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3094
_reflns_number_gt                2409
_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)+(0.0624P)²+0.3241P] 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_number_reflns         3094
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.68073(18) 0.2253(2) 0.16711(19) 0.0792(6) Uani 1 1 d . . .
H1A H 0.7478 0.2523 0.1484 0.119 Uiso 1 1 calc R . .
H1B H 0.6420 0.1648 0.1171 0.119 Uiso 1 1 calc R . .
H1C H 0.6984 0.1843 0.2333 0.119 Uiso 1 1 calc R . .
C2 C 0.60963(14) 0.34012(18) 0.17107(13) 0.0538(4) Uani 1 1 d . . .
C3 C 0.61771(17) 0.4659(2) 0.15209(18) 0.0766(6) Uani 1 1 d . . .
H3 H 0.6757 0.5065 0.1305 0.092 Uiso 1 1 calc R . .
C4 C 0.52114(17) 0.52678(19) 0.17098(18) 0.0726(6) Uani 1 1 d . . .
H4 H 0.5044 0.6149 0.1645 0.087 Uiso 1 1 calc R . .
C5 C 0.45926(13) 0.43474(14) 0.19948(11) 0.0428(4) Uani 1 1 d . . .
C6 C 0.34814(12) 0.43564(14) 0.22413(11) 0.0409(4) Uani 1 1 d . . .
H6A H 0.3365 0.3540 0.2564 0.049 Uiso 1 1 calc R . .
H6B H 0.3449 0.5050 0.2726 0.049 Uiso 1 1 calc R . .
C7 C 0.23357(12) 0.35824(13) 0.05487(11) 0.0374(3) Uani 1 1 d . . .
C8 C 0.12353(12) 0.49849(14) -0.05623(11) 0.0388(3) Uani 1 1 d . . .
C9 C 0.13968(12) 0.59951(14) 0.01535(11) 0.0413(4) Uani 1 1 d . . .
C10 C 0.21269(13) 0.57822(14) 0.11534(12) 0.0446(4) Uani 1 1 d . . .
C11 C 0.08784(15) 0.71963(16) -0.00956(14) 0.0533(4) Uani 1 1 d . . .
H11 H 0.0986 0.7860 0.0389 0.064 Uiso 1 1 calc R . .
C12 C 0.02150(15) 0.74010(17) -0.10444(14) 0.0575(5) Uani 1 1 d . . .
H12 H -0.0118 0.8206 -0.1211 0.069 Uiso 1 1 calc R . .
C13 C 0.00399(15) 0.63972(17) -0.17608(14) 0.0555(4) Uani 1 1 d . . .
H13 H -0.0421 0.6533 -0.2404 0.067 Uiso 1 1 calc R . .
C14 C 0.05383(14) 0.52097(16) -0.15309(12) 0.0495(4) Uani 1 1 d . . .
H14 H 0.0414 0.4550 -0.2019 0.059 Uiso 1 1 calc R . .
C15 C 0.28450(14) 0.13001(14) 0.01242(11) 0.0446(4) Uani 1 1 d . . .
C16 C 0.34829(18) 0.17151(18) -0.06801(15) 0.0679(5) Uani 1 1 d . . .
H16A H 0.3081 0.2389 -0.1102 0.102 Uiso 1 1 calc R . .
H16B H 0.3568 0.0983 -0.1101 0.102 Uiso 1 1 calc R . .
H16C H 0.4200 0.2034 -0.0342 0.102 Uiso 1 1 calc R . .
C17 C 0.34923(17) 0.02470(16) 0.08073(14) 0.0599(5) Uani 1 1 d . . .
H17A H 0.4224 0.0558 0.1105 0.090 Uiso 1 1 calc R . .
H17B H 0.3541 -0.0513 0.0403 0.090 Uiso 1 1 calc R . .
H17C H 0.3120 0.0034 0.1344 0.090 Uiso 1 1 calc R . .
C18 C 0.16965(16) 0.07995(16) -0.03776(15) 0.0615(5) Uani 1 1 d . . .
H18A H 0.1317 0.0542 0.0144 0.092 Uiso 1 1 calc R . .
H18B H 0.1763 0.0066 -0.0804 0.092 Uiso 1 1 calc R . .
H18C H 0.1285 0.1474 -0.0790 0.092 Uiso 1 1 calc R . .
N1 N 0.27875(11) 0.24031(11) 0.08221(9) 0.0448(3) Uani 1 1 d . . .
H1 H 0.3048 0.2282 0.1485 0.054 Uiso 1 1 d R . .
N2 N 0.17118(10) 0.37758(11) -0.03575(9) 0.0409(3) Uani 1 1 d . . .
N3 N 0.25886(10) 0.45455(11) 0.13091(9) 0.0381(3) Uani 1 1 d . . .
O1 O 0.51246(9) 0.31782(10) 0.20181(8) 0.0475(3) Uani 1 1 d . . .
O2 O 0.23566(12) 0.66123(11) 0.18287(9) 0.0681(4) Uani 1 1 d . . .


_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
C1 C2 1.481(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.327(3) . ?
C2 O1 1.374(2) . ?
C3 C4 1.421(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.326(2) . ?
C4 H4 0.9300 . ?
C5 O1 1.3689(18) . ?
C5 C6 1.484(2) . ?
C6 N3 1.4828(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.2986(19) . ?
C7 N1 1.3523(18) . ?
C7 N3 1.4040(17) . ?
C8 N2 1.3783(18) . ?
C8 C9 1.397(2) . ?
C8 C14 1.406(2) . ?
C9 C11 1.399(2) . ?
C9 C10 1.454(2) . ?
C10 O2 1.2290(18) . ?
C10 N3 1.3919(18) . ?
C11 C12 1.365(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N1 1.4807(18) . ?
C15 C18 1.521(2) . ?
C15 C17 1.525(2) . ?
C15 C16 1.529(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 H1 0.8817 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O1 109.16(15) . . ?
C3 C2 C1 134.47(18) . . ?
O1 C2 C1 116.36(16) . . ?
C2 C3 C4 107.11(16) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
C5 C4 C3 107.36(17) . . ?
C5 C4 H4 126.3 . . ?
C3 C4 H4 126.3 . . ?
C4 C5 O1 109.19(15) . . ?
C4 C5 C6 133.03(16) . . ?
O1 C5 C6 117.74(13) . . ?
N3 C6 C5 111.67(12) . . ?
N3 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N3 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 N1 120.93(12) . . ?
N2 C7 N3 123.85(12) . . ?
N1 C7 N3 115.21(12) . . ?
N2 C8 C9 123.12(13) . . ?
N2 C8 C14 118.65(13) . . ?
C9 C8 C14 118.23(14) . . ?
C8 C9 C11 120.45(14) . . ?
C8 C9 C10 118.83(13) . . ?
C11 C9 C10 120.70(14) . . ?
O2 C10 N3 120.37(14) . . ?
O2 C10 C9 124.40(14) . . ?
N3 C10 C9 115.21(12) . . ?
C12 C11 C9 120.46(16) . . ?
C12 C11 H11 119.8 . . ?
C9 C11 H11 119.8 . . ?
C11 C12 C13 119.57(15) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.88(16) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C8 120.39(15) . . ?
C13 C14 H14 119.8 . . ?
C8 C14 H14 119.8 . . ?
N1 C15 C18 111.48(13) . . ?
N1 C15 C17 105.10(12) . . ?
C18 C15 C17 109.79(14) . . ?
N1 C15 C16 109.45(13) . . ?
C18 C15 C16 111.29(15) . . ?
C17 C15 C16 109.53(14) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 N1 C15 126.37(12) . . ?
C7 N1 H1 115.8 . . ?
C15 N1 H1 117.8 . . ?
C7 N2 C8 117.60(12) . . ?
C10 N3 C7 121.29(12) . . ?
C10 N3 C6 116.76(11) . . ?
C7 N3 C6 121.31(11) . . ?
C5 O1 C2 107.17(12) . . ?

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
O1 C2 C3 C4 -0.3(2) . . . . ?
C1 C2 C3 C4 -179.6(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 O1 1.2(2) . . . . ?
C3 C4 C5 C6 -176.46(18) . . . . ?
C4 C5 C6 N3 71.4(2) . . . . ?
O1 C5 C6 N3 -106.07(15) . . . . ?
N2 C8 C9 C11 -179.14(14) . . . . ?
C14 C8 C9 C11 -0.2(2) . . . . ?
N2 C8 C9 C10 1.9(2) . . . . ?
C14 C8 C9 C10 -179.20(14) . . . . ?
C8 C9 C10 O2 177.59(16) . . . . ?
C11 C9 C10 O2 -1.4(3) . . . . ?
C8 C9 C10 N3 -1.3(2) . . . . ?
C11 C9 C10 N3 179.76(14) . . . . ?
C8 C9 C11 C12 -0.5(2) . . . . ?
C10 C9 C11 C12 178.40(15) . . . . ?
C9 C11 C12 C13 1.1(3) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C12 C13 C14 C8 0.2(3) . . . . ?
N2 C8 C14 C13 179.38(14) . . . . ?
C9 C8 C14 C13 0.4(2) . . . . ?
N2 C7 N1 C15 13.2(2) . . . . ?
N3 C7 N1 C15 -167.08(13) . . . . ?
C18 C15 N1 C7 -64.5(2) . . . . ?
C17 C15 N1 C7 176.59(15) . . . . ?
C16 C15 N1 C7 59.0(2) . . . . ?
N1 C7 N2 C8 176.78(13) . . . . ?
N3 C7 N2 C8 -2.9(2) . . . . ?
C9 C8 N2 C7 0.2(2) . . . . ?
C14 C8 N2 C7 -178.72(13) . . . . ?
O2 C10 N3 C7 179.88(15) . . . . ?
C9 C10 N3 C7 -1.2(2) . . . . ?
O2 C10 N3 C6 -9.1(2) . . . . ?
C9 C10 N3 C6 169.80(12) . . . . ?
N2 C7 N3 C10 3.5(2) . . . . ?
N1 C7 N3 C10 -176.18(13) . . . . ?
N2 C7 N3 C6 -167.08(13) . . . . ?
N1 C7 N3 C6 13.23(19) . . . . ?
C5 C6 N3 C10 -102.28(15) . . . . ?
C5 C6 N3 C7 68.72(16) . . . . ?
C4 C5 O1 C2 -1.4(2) . . . . ?
C6 C5 O1 C2 176.67(13) . . . . ?
C3 C2 O1 C5 1.0(2) . . . . ?
C1 C2 O1 C5 -179.53(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 966928'
