# 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N O3'
_chemical_formula_sum            'C21 H21 N O3'
_chemical_formula_weight         335.39

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   P21/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                   10.7869(4)
_cell_length_b                   21.5015(8)
_cell_length_c                   8.1152(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.0980(10)
_cell_angle_gamma                90.00
_cell_volume                     1767.58(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7661
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      24.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9527
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27065
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3467
_reflns_number_gt                2547
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0490P)²+0.8265P] 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     SHELXL
_refine_ls_extinction_coef       0.0045(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3467
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
C1 C 0.9943(2) 0.87198(11) 0.6927(3) 0.0558(6) Uani 1 1 d . . .
H1 H 0.9949 0.8917 0.7949 0.067 Uiso 1 1 calc R . .
C2 C 1.0934(2) 0.83130(12) 0.6972(3) 0.0634(7) Uani 1 1 d . . .
H2 H 1.1611 0.8234 0.8027 0.076 Uiso 1 1 calc R . .
C3 C 1.0928(2) 0.80225(12) 0.5464(3) 0.0631(7) Uani 1 1 d . . .
H3 H 1.1606 0.7751 0.5493 0.076 Uiso 1 1 calc R . .
C4 C 0.9911(2) 0.81344(10) 0.3902(3) 0.0510(5) Uani 1 1 d . . .
H4 H 0.9916 0.7937 0.2885 0.061 Uiso 1 1 calc R . .
C5 C 0.88822(18) 0.85356(9) 0.3820(2) 0.0401(5) Uani 1 1 d . . .
C6 C 0.8931(2) 0.88377(9) 0.5350(3) 0.0445(5) Uani 1 1 d . . .
C7 C 0.7183(2) 0.95449(9) 0.3824(3) 0.0441(5) Uani 1 1 d . . .
H7 H 0.6412 0.9729 0.4014 0.053 Uiso 1 1 calc R . .
C8 C 0.67055(19) 0.90430(8) 0.2476(2) 0.0367(4) Uani 1 1 d . . .
C9 C 0.77277(19) 0.86445(9) 0.2135(2) 0.0402(5) Uani 1 1 d . . .
H9 H 0.8038 0.8844 0.1262 0.048 Uiso 1 1 calc R . .
C10 C 0.7942(2) 1.00609(10) 0.3341(3) 0.0639(7) Uani 1 1 d . . .
H10A H 0.8205 1.0362 0.4269 0.096 Uiso 1 1 calc R . .
H10B H 0.7392 1.0257 0.2278 0.096 Uiso 1 1 calc R . .
H10C H 0.8711 0.9892 0.3167 0.096 Uiso 1 1 calc R . .
C11 C 0.54918(18) 0.88182(8) 0.1695(2) 0.0351(4) Uani 1 1 d . . .
C12 C 0.55762(19) 0.82159(8) 0.0780(2) 0.0389(4) Uani 1 1 d . . .
H12 H 0.5133 0.7891 0.1220 0.047 Uiso 1 1 calc R . .
C13 C 0.49253(19) 0.82480(8) -0.1208(2) 0.0386(4) Uani 1 1 d . . .
C14 C 0.4835(3) 0.87533(13) -0.3810(3) 0.0866(10) Uani 1 1 d . . .
H14A H 0.5195 0.9110 -0.4195 0.130 Uiso 1 1 calc R . .
H14B H 0.3890 0.8787 -0.4204 0.130 Uiso 1 1 calc R . .
H14C H 0.5077 0.8384 -0.4290 0.130 Uiso 1 1 calc R . .
C15 C 0.7443(3) 0.77035(14) 0.0237(4) 0.0872(10) Uani 1 1 d . . .
H15A H 0.8379 0.7642 0.0756 0.131 Uiso 1 1 calc R . .
H15B H 0.7248 0.7912 -0.0870 0.131 Uiso 1 1 calc R . .
H15C H 0.7005 0.7308 0.0057 0.131 Uiso 1 1 calc R . .
C16 C 0.42196(18) 0.90704(8) 0.1675(2) 0.0364(4) Uani 1 1 d . . .
C17 C 0.3984(2) 0.97104(9) 0.1587(3) 0.0456(5) Uani 1 1 d . . .
H17 H 0.4634 0.9981 0.1509 0.055 Uiso 1 1 calc R . .
C18 C 0.2799(2) 0.99463(11) 0.1616(3) 0.0583(6) Uani 1 1 d . . .
H18 H 0.2662 1.0374 0.1571 0.070 Uiso 1 1 calc R . .
C19 C 0.1832(2) 0.95541(13) 0.1708(3) 0.0650(7) Uani 1 1 d . . .
H19 H 0.1040 0.9714 0.1741 0.078 Uiso 1 1 calc R . .
C20 C 0.2028(2) 0.89215(13) 0.1754(3) 0.0636(7) Uani 1 1 d . . .
H20 H 0.1361 0.8655 0.1795 0.076 Uiso 1 1 calc R . .
C21 C 0.3214(2) 0.86800(10) 0.1738(3) 0.0494(5) Uani 1 1 d . . .
H21 H 0.3338 0.8251 0.1769 0.059 Uiso 1 1 calc R . .
N1 N 0.69856(17) 0.80786(7) 0.1395(2) 0.0478(5) Uani 1 1 d . . .
O1 O 0.79891(15) 0.92512(7) 0.54486(17) 0.0547(4) Uani 1 1 d . . .
O2 O 0.53524(18) 0.87213(7) -0.19075(18) 0.0627(5) Uani 1 1 d . . .
O3 O 0.41396(16) 0.78778(8) -0.2047(2) 0.0651(5) 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 1.372(3) . ?
C1 C6 1.391(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 C9 1.518(3) . ?
C6 O1 1.373(2) . ?
C7 O1 1.451(2) . ?
C7 C8 1.496(3) . ?
C7 C10 1.509(3) . ?
C7 H7 0.9800 . ?
C8 C11 1.334(3) . ?
C8 C9 1.496(3) . ?
C9 N1 1.467(2) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.471(3) . ?
C11 C12 1.511(2) . ?
C12 N1 1.458(3) . ?
C12 C13 1.524(2) . ?
C12 H12 0.9800 . ?
C13 O3 1.191(2) . ?
C13 O2 1.323(2) . ?
C14 O2 1.452(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N1 1.447(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.386(3) . ?
C16 C17 1.396(3) . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
C2 C1 C6 120.0(2) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 120.1(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 117.68(18) . . ?
C6 C5 C9 120.07(17) . . ?
C4 C5 C9 122.25(18) . . ?
O1 C6 C5 123.71(18) . . ?
O1 C6 C1 115.29(18) . . ?
C5 C6 C1 121.0(2) . . ?
O1 C7 C8 107.36(15) . . ?
O1 C7 C10 110.28(17) . . ?
C8 C7 C10 114.93(17) . . ?
O1 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C10 C7 H7 108.0 . . ?
C11 C8 C9 111.71(16) . . ?
C11 C8 C7 130.08(18) . . ?
C9 C8 C7 117.28(16) . . ?
N1 C9 C8 102.58(15) . . ?
N1 C9 C5 113.84(15) . . ?
C8 C9 C5 110.51(15) . . ?
N1 C9 H9 109.9 . . ?
C8 C9 H9 109.9 . . ?
C5 C9 H9 109.9 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 C16 129.13(16) . . ?
C8 C11 C12 109.23(16) . . ?
C16 C11 C12 121.63(16) . . ?
N1 C12 C11 103.72(15) . . ?
N1 C12 C13 114.73(16) . . ?
C11 C12 C13 113.43(14) . . ?
N1 C12 H12 108.2 . . ?
C11 C12 H12 108.2 . . ?
C13 C12 H12 108.2 . . ?
O3 C13 O2 123.56(18) . . ?
O3 C13 C12 123.61(18) . . ?
O2 C13 C12 112.80(15) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 117.91(19) . . ?
C21 C16 C11 121.00(17) . . ?
C17 C16 C11 121.09(17) . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.3(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.7(2) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C15 N1 C12 116.01(16) . . ?
C15 N1 C9 117.9(2) . . ?
C12 N1 C9 109.29(14) . . ?
C6 O1 C7 116.97(15) . . ?
C13 O2 C14 115.45(18) . . ?

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
C6 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 2.1(3) . . . . ?
C3 C4 C5 C9 -177.4(2) . . . . ?
C4 C5 C6 O1 179.20(18) . . . . ?
C9 C5 C6 O1 -1.2(3) . . . . ?
C4 C5 C6 C1 -3.0(3) . . . . ?
C9 C5 C6 C1 176.61(19) . . . . ?
C2 C1 C6 O1 179.94(19) . . . . ?
C2 C1 C6 C5 1.9(3) . . . . ?
O1 C7 C8 C11 111.4(2) . . . . ?
C10 C7 C8 C11 -125.5(2) . . . . ?
O1 C7 C8 C9 -56.5(2) . . . . ?
C10 C7 C8 C9 66.6(2) . . . . ?
C11 C8 C9 N1 -12.8(2) . . . . ?
C7 C8 C9 N1 157.27(16) . . . . ?
C11 C8 C9 C5 -134.52(17) . . . . ?
C7 C8 C9 C5 35.6(2) . . . . ?
C6 C5 C9 N1 -120.4(2) . . . . ?
C4 C5 C9 N1 59.2(2) . . . . ?
C6 C5 C9 C8 -5.6(2) . . . . ?
C4 C5 C9 C8 173.97(17) . . . . ?
C9 C8 C11 C16 -178.99(17) . . . . ?
C7 C8 C11 C16 12.5(3) . . . . ?
C9 C8 C11 C12 2.3(2) . . . . ?
C7 C8 C11 C12 -166.20(18) . . . . ?
C8 C11 C12 N1 9.4(2) . . . . ?
C16 C11 C12 N1 -169.50(16) . . . . ?
C8 C11 C12 C13 -115.73(18) . . . . ?
C16 C11 C12 C13 65.4(2) . . . . ?
N1 C12 C13 O3 111.9(2) . . . . ?
C11 C12 C13 O3 -129.1(2) . . . . ?
N1 C12 C13 O2 -66.4(2) . . . . ?
C11 C12 C13 O2 52.6(2) . . . . ?
C8 C11 C16 C21 -142.8(2) . . . . ?
C12 C11 C16 C21 35.9(2) . . . . ?
C8 C11 C16 C17 37.5(3) . . . . ?
C12 C11 C16 C17 -143.90(18) . . . . ?
C21 C16 C17 C18 1.9(3) . . . . ?
C11 C16 C17 C18 -178.31(18) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C17 C18 C19 C20 -0.8(4) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?
C17 C16 C21 C20 -1.5(3) . . . . ?
C11 C16 C21 C20 178.74(19) . . . . ?
C11 C12 N1 C15 -153.9(2) . . . . ?
C13 C12 N1 C15 -29.6(3) . . . . ?
C11 C12 N1 C9 -17.59(19) . . . . ?
C13 C12 N1 C9 106.67(17) . . . . ?
C8 C9 N1 C15 153.98(19) . . . . ?
C5 C9 N1 C15 -86.6(2) . . . . ?
C8 C9 N1 C12 18.63(19) . . . . ?
C5 C9 N1 C12 138.03(16) . . . . ?
C5 C6 O1 C7 -22.0(3) . . . . ?
C1 C6 O1 C7 160.10(18) . . . . ?
C8 C7 O1 C6 48.0(2) . . . . ?
C10 C7 O1 C6 -77.9(2) . . . . ?
O3 C13 O2 C14 -2.3(3) . . . . ?
C12 C13 O2 C14 176.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 982489'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37

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           Triclinic
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   8.0279(7)
_cell_length_b                   10.0480(8)
_cell_length_c                   11.5774(9)
_cell_angle_alpha                111.220(3)
_cell_angle_beta                 99.322(3)
_cell_angle_gamma                101.074(3)
_cell_volume                     826.55(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6943
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      25.46

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9582
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23656
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2915
_reflns_number_gt                2180
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0450P)²+0.2660P] 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     SHELXL
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2915
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
C1 C 0.0557(3) 0.3469(2) 0.0382(2) 0.0549(5) Uani 1 1 d . . .
H1 H 0.0744 0.2863 -0.0382 0.066 Uiso 1 1 calc R . .
C2 C 0.1959(3) 0.4477(2) 0.13586(19) 0.0490(5) Uani 1 1 d . . .
H2 H 0.3092 0.4555 0.1253 0.059 Uiso 1 1 calc R . .
C3 C 0.1683(2) 0.53701(19) 0.24935(17) 0.0388(4) Uani 1 1 d . . .
C4 C -0.0013(2) 0.52363(18) 0.26941(16) 0.0356(4) Uani 1 1 d . . .
C5 C -0.1396(2) 0.42232(19) 0.16695(17) 0.0428(4) Uani 1 1 d . . .
H5 H -0.2539 0.4132 0.1757 0.051 Uiso 1 1 calc R . .
C6 C -0.1112(3) 0.3357(2) 0.05347(19) 0.0512(5) Uani 1 1 d . . .
H6 H -0.2059 0.2690 -0.0135 0.061 Uiso 1 1 calc R . .
C7 C -0.0091(2) 0.62381(18) 0.39375(16) 0.0342(4) Uani 1 1 d . . .
C8 C 0.1299(2) 0.74507(18) 0.47091(16) 0.0338(4) Uani 1 1 d . . .
C9 C 0.2926(2) 0.77471(19) 0.42641(17) 0.0410(4) Uani 1 1 d . . .
H9 H 0.3932 0.8205 0.5015 0.049 Uiso 1 1 calc R . .
C10 C 0.2924(3) 0.8774(2) 0.3587(2) 0.0567(6) Uani 1 1 d . . .
H10A H 0.3969 0.8882 0.3288 0.085 Uiso 1 1 calc R . .
H10B H 0.2888 0.9727 0.4169 0.085 Uiso 1 1 calc R . .
H10C H 0.1913 0.8368 0.2871 0.085 Uiso 1 1 calc R . .
C11 C 0.0858(2) 0.82222(18) 0.58376(16) 0.0331(4) Uani 1 1 d . . .
C12 C -0.0833(2) 0.74328(18) 0.57271(16) 0.0344(4) Uani 1 1 d . . .
C13 C -0.3004(2) 0.50072(19) 0.41490(18) 0.0445(5) Uani 1 1 d . . .
H13A H -0.3320 0.4919 0.4888 0.067 Uiso 1 1 calc R . .
H13B H -0.2807 0.4094 0.3621 0.067 Uiso 1 1 calc R . .
H13C H -0.3937 0.5215 0.3670 0.067 Uiso 1 1 calc R . .
C14 C -0.1988(2) 0.77834(19) 0.65712(17) 0.0393(4) Uani 1 1 d . . .
C15 C -0.2151(3) 0.9249(2) 0.8616(2) 0.0618(6) Uani 1 1 d . . .
H15A H -0.1420 1.0018 0.9409 0.093 Uiso 1 1 calc R . .
H15B H -0.2696 0.8411 0.8767 0.093 Uiso 1 1 calc R . .
H15C H -0.3040 0.9614 0.8266 0.093 Uiso 1 1 calc R . .
C16 C 0.1963(2) 0.96373(18) 0.68786(15) 0.0330(4) Uani 1 1 d . . .
C17 C 0.2039(3) 1.0965(2) 0.67541(18) 0.0465(5) Uani 1 1 d . . .
H17 H 0.1363 1.0966 0.6022 0.056 Uiso 1 1 calc R . .
C18 C 0.3104(3) 1.2287(2) 0.7700(2) 0.0543(5) Uani 1 1 d . . .
H18 H 0.3137 1.3170 0.7602 0.065 Uiso 1 1 calc R . .
C19 C 0.4111(2) 1.2307(2) 0.87818(18) 0.0465(5) Uani 1 1 d . . .
H19 H 0.4827 1.3198 0.9421 0.056 Uiso 1 1 calc R . .
C20 C 0.4055(3) 1.1004(2) 0.89135(18) 0.0481(5) Uani 1 1 d . . .
H20 H 0.4743 1.1009 0.9644 0.058 Uiso 1 1 calc R . .
C21 C 0.2991(2) 0.9683(2) 0.79751(17) 0.0445(5) Uani 1 1 d . . .
H21 H 0.2965 0.8806 0.8082 0.053 Uiso 1 1 calc R . .
N1 N -0.13980(17) 0.62180(15) 0.45582(13) 0.0350(3) Uani 1 1 d . . .
O1 O 0.31345(15) 0.63459(13) 0.34300(12) 0.0450(3) Uani 1 1 d . . .
O2 O -0.35470(18) 0.72690(16) 0.62872(15) 0.0662(5) Uani 1 1 d . . .
O3 O -0.11066(17) 0.88111(15) 0.77328(12) 0.0519(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 C6 1.369(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 O1 1.370(2) . ?
C3 C4 1.407(2) . ?
C4 C5 1.393(2) . ?
C4 C7 1.447(2) . ?
C5 C6 1.371(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.365(2) . ?
C7 C8 1.377(2) . ?
C8 C11 1.398(2) . ?
C8 C9 1.497(2) . ?
C9 O1 1.450(2) . ?
C9 C10 1.505(3) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.395(2) . ?
C11 C16 1.480(2) . ?
C12 N1 1.386(2) . ?
C12 C14 1.453(2) . ?
C13 N1 1.466(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O2 1.198(2) . ?
C14 O3 1.335(2) . ?
C15 O3 1.427(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.378(2) . ?
C16 C17 1.384(2) . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
C6 C1 C2 120.08(19) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 119.98(18) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
O1 C3 C2 117.12(16) . . ?
O1 C3 C4 121.74(15) . . ?
C2 C3 C4 121.09(17) . . ?
C5 C4 C3 116.88(16) . . ?
C5 C4 C7 128.32(16) . . ?
C3 C4 C7 114.73(15) . . ?
C6 C5 C4 121.56(18) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 120.32(19) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C8 108.38(15) . . ?
N1 C7 C4 130.52(15) . . ?
C8 C7 C4 121.11(15) . . ?
C7 C8 C11 108.82(14) . . ?
C7 C8 C9 119.88(15) . . ?
C11 C8 C9 131.30(15) . . ?
O1 C9 C8 108.82(13) . . ?
O1 C9 C10 110.04(15) . . ?
C8 C9 C10 113.35(15) . . ?
O1 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
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 . . ?
C12 C11 C8 106.01(14) . . ?
C12 C11 C16 128.52(15) . . ?
C8 C11 C16 125.38(14) . . ?
N1 C12 C11 108.66(14) . . ?
N1 C12 C14 121.29(15) . . ?
C11 C12 C14 129.85(16) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 O3 122.45(17) . . ?
O2 C14 C12 126.01(18) . . ?
O3 C14 C12 111.51(15) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 117.73(16) . . ?
C21 C16 C11 121.89(15) . . ?
C17 C16 C11 120.34(15) . . ?
C18 C17 C16 120.93(17) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 120.36(18) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.30(18) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 120.59(18) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 121.09(17) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C7 N1 C12 108.14(13) . . ?
C7 N1 C13 125.74(15) . . ?
C12 N1 C13 125.53(14) . . ?
C3 O1 C9 116.99(13) . . ?
C14 O3 C15 115.22(15) . . ?

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
C6 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 O1 179.72(17) . . . . ?
C1 C2 C3 C4 2.3(3) . . . . ?
O1 C3 C4 C5 179.14(15) . . . . ?
C2 C3 C4 C5 -3.5(2) . . . . ?
O1 C3 C4 C7 2.0(2) . . . . ?
C2 C3 C4 C7 179.33(16) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C7 C4 C5 C6 179.06(17) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C5 C4 C7 N1 18.8(3) . . . . ?
C3 C4 C7 N1 -164.45(17) . . . . ?
C5 C4 C7 C8 -161.16(17) . . . . ?
C3 C4 C7 C8 15.6(2) . . . . ?
N1 C7 C8 C11 -0.52(19) . . . . ?
C4 C7 C8 C11 179.47(14) . . . . ?
N1 C7 C8 C9 179.95(14) . . . . ?
C4 C7 C8 C9 -0.1(2) . . . . ?
C7 C8 C9 O1 -30.0(2) . . . . ?
C11 C8 C9 O1 150.56(17) . . . . ?
C7 C8 C9 C10 92.7(2) . . . . ?
C11 C8 C9 C10 -86.7(2) . . . . ?
C7 C8 C11 C12 0.44(18) . . . . ?
C9 C8 C11 C12 179.89(17) . . . . ?
C7 C8 C11 C16 -176.24(15) . . . . ?
C9 C8 C11 C16 3.2(3) . . . . ?
C8 C11 C12 N1 -0.19(18) . . . . ?
C16 C11 C12 N1 176.34(15) . . . . ?
C8 C11 C12 C14 -174.96(17) . . . . ?
C16 C11 C12 C14 1.6(3) . . . . ?
N1 C12 C14 O2 -13.6(3) . . . . ?
C11 C12 C14 O2 160.60(19) . . . . ?
N1 C12 C14 O3 168.27(14) . . . . ?
C11 C12 C14 O3 -17.5(3) . . . . ?
C12 C11 C16 C21 84.9(2) . . . . ?
C8 C11 C16 C21 -99.2(2) . . . . ?
C12 C11 C16 C17 -97.4(2) . . . . ?
C8 C11 C16 C17 78.5(2) . . . . ?
C21 C16 C17 C18 -0.3(3) . . . . ?
C11 C16 C17 C18 -178.05(17) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C16 0.3(3) . . . . ?
C17 C16 C21 C20 0.0(3) . . . . ?
C11 C16 C21 C20 177.77(17) . . . . ?
C8 C7 N1 C12 0.39(18) . . . . ?
C4 C7 N1 C12 -179.60(16) . . . . ?
C8 C7 N1 C13 -171.15(15) . . . . ?
C4 C7 N1 C13 8.9(3) . . . . ?
C11 C12 N1 C7 -0.12(18) . . . . ?
C14 C12 N1 C7 175.18(15) . . . . ?
C11 C12 N1 C13 171.44(15) . . . . ?
C14 C12 N1 C13 -13.3(2) . . . . ?
C2 C3 O1 C9 147.24(16) . . . . ?
C4 C3 O1 C9 -35.3(2) . . . . ?
C8 C9 O1 C3 47.13(19) . . . . ?
C10 C9 O1 C3 -77.62(18) . . . . ?
O2 C14 O3 C15 0.3(3) . . . . ?
C12 C14 O3 C15 178.51(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.033
_database_code_depnum_ccdc_archive 'CCDC 982490'
