# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_784

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   12.0655(14)
_cell_length_b                   7.4251(8)
_cell_length_c                   18.788(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.551(8)
_cell_angle_gamma                90.00
_cell_volume                     1565.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   multi-scan

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9563
_diffrn_reflns_av_R_equivalents  0.1759
_diffrn_reflns_av_sigmaI/netI    0.1079
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         31.51
_reflns_number_total             5207
_reflns_number_gt                4514
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1000P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5207
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.2505
_refine_ls_wR_factor_gt          0.1770
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_restrained_S_all      1.221
_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 0.83858(11) 0.5783(2) 0.52221(7) 0.0735(4) Uani 1 1 d . . .
N1 N 0.74803(11) 0.53019(18) 0.39530(8) 0.0472(3) Uani 1 1 d . . .
C1 C 0.84799(13) 0.3652(2) 0.32380(9) 0.0473(4) Uani 1 1 d . . .
C6 C 0.74246(13) 0.3631(2) 0.25953(9) 0.0457(4) Uani 1 1 d . . .
C2 C 0.93982(14) 0.2475(2) 0.32806(10) 0.0553(4) Uani 1 1 d . . .
H2 H 1.0100 0.2489 0.3709 0.066 Uiso 1 1 calc R . .
C16 C 0.86400(12) 0.4991(2) 0.38711(9) 0.0511(4) Uani 1 1 d . . .
H16 H 0.9195 0.4482 0.4351 0.061 Uiso 1 1 calc R . .
C3 C 0.92768(16) 0.1282(3) 0.26895(11) 0.0642(5) Uani 1 1 d . . .
H3 H 0.9894 0.0495 0.2724 0.077 Uiso 1 1 calc R . .
C5 C 0.73202(15) 0.2424(2) 0.20066(10) 0.0552(4) Uani 1 1 d . . .
H5 H 0.6620 0.2394 0.1577 0.066 Uiso 1 1 calc R . .
C15 C 0.64784(12) 0.5439(2) 0.32804(9) 0.0450(4) Uani 1 1 d . . .
H15 H 0.5810 0.6030 0.3299 0.054 Uiso 1 1 calc R . .
C18 C 0.74713(15) 0.5697(2) 0.46631(10) 0.0526(4) Uani 1 1 d . . .
C8 C 0.53422(13) 0.5078(2) 0.19241(9) 0.0456(4) Uani 1 1 d . . .
C10 C 0.43617(16) 0.6006(3) 0.06108(10) 0.0601(5) Uani 1 1 d . . .
H10 H 0.4422 0.6417 0.0159 0.072 Uiso 1 1 calc R . .
C11 C 0.32399(16) 0.5745(2) 0.06409(10) 0.0579(5) Uani 1 1 d . . .
C12 C 0.31913(14) 0.5185(2) 0.13313(11) 0.0567(5) Uani 1 1 d . . .
H12 H 0.2452 0.5032 0.1373 0.068 Uiso 1 1 calc R . .
C13 C 0.42175(14) 0.4846(2) 0.19629(10) 0.0516(4) Uani 1 1 d . . .
H13 H 0.4155 0.4460 0.2418 0.062 Uiso 1 1 calc R . .
C14 C 0.2120(2) 0.5988(3) -0.00531(13) 0.0833(7) Uani 1 1 d . . .
H14A H 0.2268 0.6819 -0.0400 0.125 Uiso 1 1 calc R . .
H14B H 0.1500 0.6452 0.0101 0.125 Uiso 1 1 calc R . .
H14C H 0.1878 0.4848 -0.0303 0.125 Uiso 1 1 calc R . .
C4 C 0.82468(17) 0.1262(3) 0.20526(11) 0.0641(5) Uani 1 1 d . . .
H4 H 0.8169 0.0473 0.1653 0.077 Uiso 1 1 calc R . .
C19 C 0.62759(16) 0.5983(3) 0.47270(11) 0.0627(5) Uani 1 1 d . . .
H19A H 0.6372 0.6027 0.5257 0.094 Uiso 1 1 calc R . .
H19B H 0.5754 0.5007 0.4481 0.094 Uiso 1 1 calc R . .
H19C H 0.5940 0.7097 0.4484 0.094 Uiso 1 1 calc R . .
C9 C 0.53915(14) 0.5671(2) 0.12369(10) 0.0555(4) Uani 1 1 d . . .
H9 H 0.6129 0.5846 0.1196 0.067 Uiso 1 1 calc R . .
C7 C 0.64307(12) 0.4762(2) 0.26108(9) 0.0455(4) Uani 1 1 d . . .
C17 C 0.91437(15) 0.6767(3) 0.37258(12) 0.0665(5) Uani 1 1 d . . .
H17A H 0.8625 0.7260 0.3247 0.100 Uiso 1 1 calc R . .
H17B H 0.9919 0.6570 0.3708 0.100 Uiso 1 1 calc R . .
H17C H 0.9205 0.7596 0.4131 0.100 Uiso 1 1 calc R . .


_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 C18 1.2138(19) . ?
N1 C18 1.370(2) . ?
N1 C15 1.395(2) . ?
N1 C16 1.4809(18) . ?
C1 C2 1.390(2) . ?
C1 C6 1.396(2) . ?
C1 C16 1.507(2) . ?
C6 C5 1.393(2) . ?
C6 C7 1.473(2) . ?
C2 C3 1.386(2) . ?
C2 H2 0.9300 . ?
C16 C17 1.518(3) . ?
C16 H16 0.9800 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C5 C4 1.389(2) . ?
C5 H5 0.9300 . ?
C15 C7 1.336(2) . ?
C15 H15 0.9300 . ?
C18 C19 1.506(2) . ?
C8 C9 1.386(2) . ?
C8 C13 1.396(2) . ?
C8 C7 1.483(2) . ?
C10 C9 1.384(2) . ?
C10 C11 1.389(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 C14 1.505(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C4 H4 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C9 H9 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C18 N1 C15 123.53(12) . . ?
C18 N1 C16 118.71(13) . . ?
C15 N1 C16 117.04(12) . . ?
C2 C1 C6 119.81(15) . . ?
C2 C1 C16 120.05(14) . . ?
C6 C1 C16 120.10(13) . . ?
C5 C6 C1 118.79(14) . . ?
C5 C6 C7 123.08(14) . . ?
C1 C6 C7 117.83(13) . . ?
C3 C2 C1 120.55(16) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
N1 C16 C1 109.43(12) . . ?
N1 C16 C17 109.83(14) . . ?
C1 C16 C17 112.03(14) . . ?
N1 C16 H16 108.5 . . ?
C1 C16 H16 108.5 . . ?
C17 C16 H16 108.5 . . ?
C4 C3 C2 120.06(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C5 C6 120.94(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C15 N1 123.29(13) . . ?
C7 C15 H15 118.4 . . ?
N1 C15 H15 118.4 . . ?
O1 C18 N1 121.60(15) . . ?
O1 C18 C19 121.11(16) . . ?
N1 C18 C19 117.28(15) . . ?
C9 C8 C13 117.58(14) . . ?
C9 C8 C7 122.23(14) . . ?
C13 C8 C7 120.14(14) . . ?
C9 C10 C11 121.61(17) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 117.24(15) . . ?
C12 C11 C14 120.96(18) . . ?
C10 C11 C14 121.76(19) . . ?
C11 C12 C13 121.62(15) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C8 120.81(16) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C4 C5 119.85(17) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C9 C8 121.11(16) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C15 C7 C6 118.63(13) . . ?
C15 C7 C8 118.54(13) . . ?
C6 C7 C8 122.70(14) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C2 C1 C6 C5 -0.2(2) . . . . ?
C16 C1 C6 C5 177.60(15) . . . . ?
C2 C1 C6 C7 173.65(15) . . . . ?
C16 C1 C6 C7 -8.5(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C16 C1 C2 C3 -177.69(16) . . . . ?
C18 N1 C16 C1 148.51(15) . . . . ?
C15 N1 C16 C1 -40.86(19) . . . . ?
C18 N1 C16 C17 -88.12(18) . . . . ?
C15 N1 C16 C17 82.50(17) . . . . ?
C2 C1 C16 N1 -147.58(15) . . . . ?
C6 C1 C16 N1 34.6(2) . . . . ?
C2 C1 C16 C17 90.37(18) . . . . ?
C6 C1 C16 C17 -87.43(17) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C7 C6 C5 C4 -173.76(16) . . . . ?
C18 N1 C15 C7 -167.89(16) . . . . ?
C16 N1 C15 C7 22.0(2) . . . . ?
C15 N1 C18 O1 -170.56(16) . . . . ?
C16 N1 C18 O1 -0.6(2) . . . . ?
C15 N1 C18 C19 10.7(2) . . . . ?
C16 N1 C18 C19 -179.29(16) . . . . ?
C9 C10 C11 C12 1.9(3) . . . . ?
C9 C10 C11 C14 -175.81(18) . . . . ?
C10 C11 C12 C13 -1.8(3) . . . . ?
C14 C11 C12 C13 175.90(17) . . . . ?
C11 C12 C13 C8 0.6(3) . . . . ?
C9 C8 C13 C12 0.6(2) . . . . ?
C7 C8 C13 C12 178.20(15) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C6 C5 C4 C3 0.8(3) . . . . ?
C11 C10 C9 C8 -0.8(3) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 C10 -178.09(16) . . . . ?
N1 C15 C7 C6 7.5(2) . . . . ?
N1 C15 C7 C8 -176.60(13) . . . . ?
C5 C6 C7 C15 159.32(16) . . . . ?
C1 C6 C7 C15 -14.2(2) . . . . ?
C5 C6 C7 C8 -16.4(2) . . . . ?
C1 C6 C7 C8 170.07(15) . . . . ?
C9 C8 C7 C15 132.42(18) . . . . ?
C13 C8 C7 C15 -45.1(2) . . . . ?
C9 C8 C7 C6 -51.9(2) . . . . ?
C13 C8 C7 C6 130.57(17) . . . . ?

_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        31.51
_diffrn_measured_fraction_theta_full 1.00
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.139
_database_code_depnum_ccdc_archive 'CCDC 994242'
#######################################################################
#
#                 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_790

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N O'
_chemical_formula_sum            'C21 H23 N O'
_chemical_formula_weight         305.40

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   'P 21/n'

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                   10.0609(9)
_cell_length_b                   7.6268(6)
_cell_length_c                   22.661(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.027(4)
_cell_angle_gamma                90.00
_cell_volume                     1700.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656.0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      99(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_reflns_number            2721
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         24.90
_reflns_number_total             2649
_reflns_number_gt                2351
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1000P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2649
_refine_ls_number_parameters     210
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.046
_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 0.73802(16) 0.5954(2) 0.97347(10) 0.0284(6) Uani 1 1 d U . .
N1 N 0.63005(19) 0.6087(2) 0.87482(11) 0.0189(7) Uani 1 1 d U . .
C6 C 0.5006(2) 0.4024(3) 0.77713(13) 0.0209(8) Uani 1 1 d U . .
C7 C 0.5547(2) 0.5776(3) 0.76726(14) 0.0164(7) Uani 1 1 d U . .
C8 C 0.5447(2) 0.6485(3) 0.70605(14) 0.0199(8) Uani 1 1 d U . .
C1 C 0.4943(2) 0.3526(3) 0.83582(13) 0.0193(8) Uani 1 1 d U . .
C5 C 0.4666(2) 0.2803(3) 0.73059(14) 0.0236(8) Uani 1 1 d U . .
H5 H 0.4689 0.3138 0.6904 0.028 Uiso 1 1 calc R . .
C14 C 0.6222(2) 0.6662(3) 0.81567(14) 0.0180(7) Uani 1 1 d U . .
H14 H 0.6665 0.7725 0.8093 0.022 Uiso 1 1 calc R . .
C9 C 0.4184(2) 0.6714(3) 0.66752(15) 0.0229(8) Uani 1 1 d U . .
H9 H 0.3385 0.6377 0.6807 0.027 Uiso 1 1 calc R . .
C17 C 0.5210(2) 0.4885(3) 0.88535(13) 0.0229(8) Uani 1 1 d U . .
H17 H 0.5529 0.4276 0.9248 0.028 Uiso 1 1 calc R . .
C13 C 0.6612(2) 0.6986(3) 0.68524(14) 0.0256(8) Uani 1 1 d U . .
H13 H 0.7485 0.6848 0.7106 0.031 Uiso 1 1 calc R . .
C15 C 0.7352(2) 0.6483(3) 0.92217(15) 0.0214(8) Uani 1 1 d U . .
C10 C 0.4071(2) 0.7423(3) 0.61041(15) 0.0251(8) Uani 1 1 d U . .
H10 H 0.3201 0.7572 0.5849 0.030 Uiso 1 1 calc R . .
C2 C 0.4570(2) 0.1824(3) 0.84700(14) 0.0256(8) Uani 1 1 d U . .
H2 H 0.4532 0.1482 0.8869 0.031 Uiso 1 1 calc R . .
C11 C 0.5236(3) 0.7919(3) 0.59032(15) 0.0293(9) Uani 1 1 d U . .
H11 H 0.5166 0.8414 0.5513 0.035 Uiso 1 1 calc R . .
C4 C 0.4294(2) 0.1104(3) 0.74221(15) 0.0270(8) Uani 1 1 d U . .
H4 H 0.4071 0.0281 0.7102 0.032 Uiso 1 1 calc R . .
C3 C 0.4251(2) 0.0618(3) 0.80021(15) 0.0276(8) Uani 1 1 d U . .
H3 H 0.4003 -0.0545 0.8083 0.033 Uiso 1 1 calc R . .
C18 C 0.3897(2) 0.5894(3) 0.88759(14) 0.0249(8) Uani 1 1 d U . .
H18A H 0.3580 0.6490 0.8484 0.030 Uiso 1 1 calc R . .
H18B H 0.3188 0.5039 0.8926 0.030 Uiso 1 1 calc R . .
C19 C 0.4032(2) 0.7250(3) 0.93743(14) 0.0239(8) Uani 1 1 d U . .
H19A H 0.4632 0.8208 0.9293 0.029 Uiso 1 1 calc R . .
H19B H 0.4464 0.6700 0.9763 0.029 Uiso 1 1 calc R . .
C16 C 0.8497(2) 0.7574(3) 0.90763(15) 0.0280(8) Uani 1 1 d U . .
H16A H 0.9193 0.7753 0.9444 0.042 Uiso 1 1 calc R . .
H16B H 0.8142 0.8713 0.8916 0.042 Uiso 1 1 calc R . .
H16C H 0.8898 0.6964 0.8775 0.042 Uiso 1 1 calc R . .
C20 C 0.2663(3) 0.8016(3) 0.94277(15) 0.0302(9) Uani 1 1 d U . .
H20A H 0.2249 0.8599 0.9043 0.036 Uiso 1 1 calc R . .
H20B H 0.2053 0.7049 0.9492 0.036 Uiso 1 1 calc R . .
C12 C 0.6492(3) 0.7680(3) 0.62793(16) 0.0308(9) Uani 1 1 d U . .
H12 H 0.7289 0.7999 0.6142 0.037 Uiso 1 1 calc R . .
C21 C 0.2763(3) 0.9325(3) 0.99359(14) 0.0371(9) Uani 1 1 d U . .
H21A H 0.3155 0.8753 1.0320 0.056 Uiso 1 1 calc R . .
H21B H 0.1854 0.9765 0.9948 0.056 Uiso 1 1 calc R . .
H21C H 0.3344 1.0305 0.9869 0.056 Uiso 1 1 calc R . .


_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 C15 1.225(3) . ?
N1 C15 1.374(4) . ?
N1 C14 1.397(3) . ?
N1 C17 1.486(2) . ?
C6 C5 1.395(4) . ?
C6 C1 1.398(3) . ?
C6 C7 1.477(3) . ?
C7 C14 1.346(4) . ?
C7 C8 1.472(4) . ?
C8 C9 1.395(4) . ?
C8 C13 1.404(3) . ?
C1 C2 1.389(3) . ?
C1 C17 1.510(4) . ?
C5 C4 1.389(3) . ?
C9 C10 1.385(4) . ?
C17 C18 1.539(3) . ?
C13 C12 1.384(4) . ?
C15 C16 1.512(3) . ?
C10 C11 1.394(3) . ?
C2 C3 1.390(4) . ?
C11 C12 1.382(4) . ?
C4 C3 1.375(4) . ?
C18 C19 1.516(4) . ?
C19 C20 1.524(3) . ?
C20 C21 1.511(4) . ?

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
C15 N1 C14 124.08(19) . . ?
C15 N1 C17 118.9(2) . . ?
C14 N1 C17 116.9(2) . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 122.0(2) . . ?
C1 C6 C7 118.8(3) . . ?
C14 C7 C8 120.5(2) . . ?
C14 C7 C6 118.0(3) . . ?
C8 C7 C6 121.3(3) . . ?
C9 C8 C13 118.1(3) . . ?
C9 C8 C7 120.68(19) . . ?
C13 C8 C7 121.2(2) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 C17 121.3(2) . . ?
C6 C1 C17 118.95(19) . . ?
C4 C5 C6 120.8(2) . . ?
C7 C14 N1 122.8(2) . . ?
C10 C9 C8 121.4(2) . . ?
N1 C17 C1 109.10(16) . . ?
N1 C17 C18 111.39(17) . . ?
C1 C17 C18 110.3(2) . . ?
C12 C13 C8 120.3(3) . . ?
O1 C15 N1 122.0(2) . . ?
O1 C15 C16 121.3(3) . . ?
N1 C15 C16 116.6(3) . . ?
C9 C10 C11 120.0(3) . . ?
C1 C2 C3 120.5(2) . . ?
C12 C11 C10 119.1(3) . . ?
C3 C4 C5 119.7(3) . . ?
C4 C3 C2 120.2(2) . . ?
C19 C18 C17 114.9(2) . . ?
C18 C19 C20 112.2(2) . . ?
C21 C20 C19 113.3(2) . . ?
C11 C12 C13 121.2(2) . . ?

_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        24.90
_diffrn_measured_fraction_theta_full 1.00
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 994243'
