# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 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. 
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data_uv07cja1n
_database_code_depnum_ccdc_archive 'CCDC 860535'
#TrackingRef 'ccdc_deposit.cif'


_audit_creation_date             2011-12-02T11:47:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_name_common            RAUL004
_chemical_formula_moiety         'C18 H19 N O'
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.34
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   9.7754(7)
_cell_length_b                   17.6008(15)
_cell_length_c                   9.5625(7)
_cell_angle_alpha                90
_cell_angle_beta                 113.841(4)
_cell_angle_gamma                90
_cell_volume                     1504.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2553
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      22.01
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9145
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_process_details   'BRUKER AXS - SADABS'

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker X8 kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_number            23367
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             3070
_reflns_number_gt                2067
_reflns_threshold_expression     >2\s(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX2 v2011.4-1 (Bruker AXS, 2011)'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS, 2011)'
_computing_data_reduction        'APEX2 v2011.4-1 (Bruker AXS, 2011)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0469P)^2^+0.4554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3070
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.17103(13) 0.21540(7) 0.38943(12) 0.0253(3) Uani 1 1 d . . .
N2 N 0.22935(16) 0.21178(8) 0.18130(17) 0.0213(3) Uani 1 1 d . . .
H2 H 0.200(2) 0.2306(11) 0.089(2) 0.030(5) Uiso 1 1 d . . .
C3 C 0.14614(19) 0.23480(10) 0.25684(18) 0.0205(4) Uani 1 1 d . . .
C4 C 0.01930(19) 0.28890(10) 0.16877(19) 0.0241(4) Uani 1 1 d . . .
H4 H 0.0129 0.2939 0.0621 0.029 Uiso 1 1 calc R . .
C5 C -0.13060(19) 0.25802(10) 0.16175(19) 0.0252(4) Uani 1 1 d . . .
H5A H -0.1184 0.2435 0.2661 0.03 Uiso 1 1 calc R . .
H5B H -0.2062 0.2991 0.1263 0.03 Uiso 1 1 calc R . .
C6 C 0.35605(19) 0.16364(10) 0.23240(18) 0.0204(4) Uani 1 1 d . . .
C7 C 0.4194(2) 0.13192(10) 0.37786(19) 0.0252(4) Uani 1 1 d . . .
H7 H 0.3761 0.1408 0.4492 0.03 Uiso 1 1 calc R . .
C8 C 0.5464(2) 0.08720(11) 0.4178(2) 0.0298(5) Uani 1 1 d . . .
H8 H 0.5907 0.0662 0.5177 0.036 Uiso 1 1 calc R . .
C9 C 0.6096(2) 0.07271(11) 0.3148(2) 0.0295(5) Uani 1 1 d . . .
H9 H 0.6965 0.042 0.3435 0.035 Uiso 1 1 calc R . .
C10 C 0.5449(2) 0.10342(11) 0.1694(2) 0.0289(5) Uani 1 1 d . . .
H10 H 0.5869 0.0931 0.0975 0.035 Uiso 1 1 calc R . .
C11 C 0.41982(19) 0.14904(10) 0.12824(19) 0.0249(4) Uani 1 1 d . . .
H11 H 0.377 0.1705 0.0287 0.03 Uiso 1 1 calc R . .
C12 C 0.0550(2) 0.36575(11) 0.2450(2) 0.0295(5) Uani 1 1 d . . .
H12 H 0.0523 0.369 0.3483 0.035 Uiso 1 1 calc R . .
C13 C 0.1693(2) 0.41470(12) 0.2213(2) 0.0388(5) Uani 1 1 d . . .
H13A H 0.2163 0.395 0.1542 0.047 Uiso 1 1 calc R . .
H13B H 0.2356 0.4459 0.3084 0.047 Uiso 1 1 calc R . .
C14 C 0.0063(2) 0.43553(11) 0.1482(2) 0.0396(5) Uani 1 1 d . . .
H14A H -0.0274 0.4796 0.1904 0.047 Uiso 1 1 calc R . .
H14B H -0.0467 0.4287 0.0363 0.047 Uiso 1 1 calc R . .
C15 C -0.18806(19) 0.19036(10) 0.05755(19) 0.0227(4) Uani 1 1 d . . .
C16 C -0.1186(2) 0.11975(11) 0.0940(2) 0.0264(4) Uani 1 1 d . . .
H16 H -0.0333 0.1136 0.1873 0.032 Uiso 1 1 calc R . .
C17 C -0.1718(2) 0.05834(11) -0.0036(2) 0.0301(5) Uani 1 1 d . . .
H17 H -0.1216 0.0109 0.0226 0.036 Uiso 1 1 calc R . .
C18 C -0.2971(2) 0.06544(12) -0.1384(2) 0.0332(5) Uani 1 1 d . . .
H18 H -0.3342 0.0231 -0.2045 0.04 Uiso 1 1 calc R . .
C19 C -0.3679(2) 0.13505(12) -0.1759(2) 0.0343(5) Uani 1 1 d . . .
H19 H -0.4547 0.1404 -0.2682 0.041 Uiso 1 1 calc R . .
C20 C -0.3134(2) 0.19735(11) -0.0801(2) 0.0286(4) Uani 1 1 d . . .
H20 H -0.362 0.2451 -0.1086 0.034 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
O1 0.0283(7) 0.0301(7) 0.0194(6) -0.0024(5) 0.0115(5) 0.0013(6)
N2 0.0209(8) 0.0248(9) 0.0180(8) 0.0037(7) 0.0078(6) 0.0023(7)
C3 0.0212(9) 0.0200(10) 0.0206(9) -0.0041(7) 0.0086(7) -0.0046(8)
C4 0.0246(10) 0.0236(10) 0.0240(9) -0.0009(8) 0.0097(8) -0.0007(8)
C5 0.0240(10) 0.0248(10) 0.0281(9) -0.0003(8) 0.0119(8) 0.0023(8)
C6 0.0196(9) 0.0189(10) 0.0212(9) -0.0018(7) 0.0068(7) -0.0030(8)
C7 0.0276(10) 0.0266(11) 0.0212(9) -0.0001(8) 0.0096(8) 0.0018(9)
C8 0.0315(11) 0.0300(11) 0.0234(9) 0.0007(8) 0.0064(8) 0.0033(9)
C9 0.0234(10) 0.0267(11) 0.0366(11) -0.0037(9) 0.0103(9) 0.0031(9)
C10 0.0283(11) 0.0309(11) 0.0327(10) -0.0048(9) 0.0178(9) -0.0018(9)
C11 0.0246(10) 0.0296(11) 0.0214(9) 0.0016(8) 0.0104(8) -0.0009(8)
C12 0.0331(11) 0.0273(11) 0.0267(10) -0.0006(8) 0.0107(9) -0.0005(9)
C13 0.0438(13) 0.0290(12) 0.0432(12) 0.0001(10) 0.0170(10) -0.0103(10)
C14 0.0452(14) 0.0245(11) 0.0389(12) 0.0061(9) 0.0066(10) 0.0031(10)
C15 0.0204(9) 0.0256(11) 0.0251(9) -0.0005(8) 0.0124(8) -0.0032(8)
C16 0.0201(10) 0.0287(11) 0.0297(10) -0.0007(9) 0.0095(8) -0.0013(9)
C17 0.0319(11) 0.0254(11) 0.0383(11) -0.0015(9) 0.0197(10) -0.0019(9)
C18 0.0406(12) 0.0333(12) 0.0296(10) -0.0090(9) 0.0183(10) -0.0095(10)
C19 0.0328(11) 0.0458(14) 0.0200(9) -0.0027(9) 0.0061(8) -0.0059(10)
C20 0.0274(11) 0.0315(11) 0.0276(10) 0.0050(9) 0.0118(9) 0.0014(9)


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.2385(19) . ?
N2 C3 1.350(2) . ?
N2 C6 1.415(2) . ?
N2 H2 0.875(19) . ?
C3 C4 1.520(2) . ?
C4 C12 1.509(3) . ?
C4 C5 1.539(2) . ?
C4 H4 1 . ?
C5 C15 1.508(2) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.391(2) . ?
C6 C11 1.396(2) . ?
C7 C8 1.387(3) . ?
C7 H7 0.95 . ?
C8 C9 1.381(2) . ?
C8 H8 0.95 . ?
C9 C10 1.383(3) . ?
C9 H9 0.95 . ?
C10 C11 1.381(3) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C14 1.495(3) . ?
C12 C13 1.499(3) . ?
C12 H12 1 . ?
C13 C14 1.504(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C16 1.391(3) . ?
C15 C20 1.395(2) . ?
C16 C17 1.384(3) . ?
C16 H16 0.95 . ?
C17 C18 1.379(3) . ?
C17 H17 0.95 . ?
C18 C19 1.381(3) . ?
C18 H18 0.95 . ?
C19 C20 1.390(3) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?

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
C3 N2 C6 128.87(15) . . ?
C3 N2 H2 114.0(12) . . ?
C6 N2 H2 117.1(12) . . ?
O1 C3 N2 123.61(16) . . ?
O1 C3 C4 121.25(14) . . ?
N2 C3 C4 115.13(14) . . ?
C12 C4 C3 108.44(14) . . ?
C12 C4 C5 111.57(14) . . ?
C3 C4 C5 110.63(14) . . ?
C12 C4 H4 108.7 . . ?
C3 C4 H4 108.7 . . ?
C5 C4 H4 108.7 . . ?
C15 C5 C4 113.67(13) . . ?
C15 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C15 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C11 119.53(16) . . ?
C7 C6 N2 124.04(15) . . ?
C11 C6 N2 116.42(15) . . ?
C8 C7 C6 119.38(16) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 121.11(17) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.35(17) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.41(16) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 120.20(16) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C14 C12 C13 60.28(13) . . ?
C14 C12 C4 118.91(16) . . ?
C13 C12 C4 118.85(16) . . ?
C14 C12 H12 115.8 . . ?
C13 C12 H12 115.8 . . ?
C4 C12 H12 115.8 . . ?
C12 C13 C14 59.73(13) . . ?
C12 C13 H13A 117.8 . . ?
C14 C13 H13A 117.8 . . ?
C12 C13 H13B 117.8 . . ?
C14 C13 H13B 117.8 . . ?
H13A C13 H13B 114.9 . . ?
C12 C14 C13 59.99(13) . . ?
C12 C14 H14A 117.8 . . ?
C13 C14 H14A 117.8 . . ?
C12 C14 H14B 117.8 . . ?
C13 C14 H14B 117.8 . . ?
H14A C14 H14B 114.9 . . ?
C16 C15 C20 117.95(16) . . ?
C16 C15 C5 121.76(16) . . ?
C20 C15 C5 120.29(16) . . ?
C17 C16 C15 121.10(17) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.59(19) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.08(18) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C20 120.67(18) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.60(18) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?

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 N2 C3 O1 -0.2(3) . . . . ?
C6 N2 C3 C4 178.26(16) . . . . ?
O1 C3 C4 C12 66.5(2) . . . . ?
N2 C3 C4 C12 -112.00(16) . . . . ?
O1 C3 C4 C5 -56.1(2) . . . . ?
N2 C3 C4 C5 125.35(16) . . . . ?
C12 C4 C5 C15 167.37(15) . . . . ?
C3 C4 C5 C15 -71.82(18) . . . . ?
C3 N2 C6 C7 -1.3(3) . . . . ?
C3 N2 C6 C11 179.61(17) . . . . ?
C11 C6 C7 C8 1.0(3) . . . . ?
N2 C6 C7 C8 -178.12(16) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C9 C10 C11 C6 -1.0(3) . . . . ?
C7 C6 C11 C10 0.0(3) . . . . ?
N2 C6 C11 C10 179.17(16) . . . . ?
C3 C4 C12 C14 146.07(16) . . . . ?
C5 C4 C12 C14 -91.85(19) . . . . ?
C3 C4 C12 C13 76.09(19) . . . . ?
C5 C4 C12 C13 -161.84(16) . . . . ?
C4 C12 C13 C14 108.73(19) . . . . ?
C4 C12 C14 C13 -108.63(19) . . . . ?
C4 C5 C15 C16 70.0(2) . . . . ?
C4 C5 C15 C20 -109.61(18) . . . . ?
C20 C15 C16 C17 0.3(2) . . . . ?
C5 C15 C16 C17 -179.36(15) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C15 -1.4(3) . . . . ?
C16 C15 C20 C19 1.0(2) . . . . ?
C5 C15 C20 C19 -179.33(15) . . . . ?

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 0.875(19) 2.05(2) 2.9105(19) 169.3(17) 4_565


data_uv07cja1n2
_database_code_depnum_ccdc_archive 'CCDC 860536'
#TrackingRef 'uv07cja1n.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.34

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

_cell_length_a                   9.7754(7)
_cell_length_b                   17.6008(15)
_cell_length_c                   9.5625(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.841(4)
_cell_angle_gamma                90.00
_cell_volume                     1504.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9676
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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            3070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3070
_reflns_number_gt                2067
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0469P)^2^+0.4554P] where P=(Fo^2^+2Fc^2^)/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         3070
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.17103(13) 0.21540(7) 0.38943(12) 0.0253(3) Uani 1 1 d . . .
N2 N 0.22935(16) 0.21178(8) 0.18130(17) 0.0213(3) Uani 1 1 d . . .
H2 H 0.200(2) 0.2306(11) 0.089(2) 0.030(5) Uiso 1 1 d . . .
C3 C 0.14614(19) 0.23480(10) 0.25684(18) 0.0205(4) Uani 1 1 d . . .
C4 C 0.01930(19) 0.28890(10) 0.16877(19) 0.0241(4) Uani 1 1 d . . .
H4 H 0.0129 0.2939 0.0621 0.029 Uiso 1 1 calc R . .
C5 C -0.13060(19) 0.25802(10) 0.16175(19) 0.0252(4) Uani 1 1 d . . .
H5A H -0.1184 0.2435 0.2661 0.030 Uiso 1 1 calc R . .
H5B H -0.2062 0.2991 0.1263 0.030 Uiso 1 1 calc R . .
C6 C 0.35605(19) 0.16364(10) 0.23240(18) 0.0204(4) Uani 1 1 d . . .
C7 C 0.4194(2) 0.13192(10) 0.37786(19) 0.0252(4) Uani 1 1 d . . .
H7 H 0.3761 0.1408 0.4492 0.030 Uiso 1 1 calc R . .
C8 C 0.5464(2) 0.08720(11) 0.4178(2) 0.0298(5) Uani 1 1 d . . .
H8 H 0.5907 0.0662 0.5177 0.036 Uiso 1 1 calc R . .
C9 C 0.6096(2) 0.07271(11) 0.3148(2) 0.0295(5) Uani 1 1 d . . .
H9 H 0.6965 0.0420 0.3435 0.035 Uiso 1 1 calc R . .
C10 C 0.5449(2) 0.10342(11) 0.1694(2) 0.0289(5) Uani 1 1 d . . .
H10 H 0.5869 0.0931 0.0975 0.035 Uiso 1 1 calc R . .
C11 C 0.41982(19) 0.14904(10) 0.12824(19) 0.0249(4) Uani 1 1 d . . .
H11 H 0.3770 0.1705 0.0287 0.030 Uiso 1 1 calc R . .
C12 C 0.0550(2) 0.36575(11) 0.2450(2) 0.0295(5) Uani 1 1 d . . .
H12 H 0.0523 0.3690 0.3483 0.035 Uiso 1 1 calc R . .
C13 C 0.1693(2) 0.41470(12) 0.2213(2) 0.0388(5) Uani 1 1 d . . .
H13A H 0.2163 0.3950 0.1542 0.047 Uiso 1 1 calc R . .
H13B H 0.2356 0.4459 0.3084 0.047 Uiso 1 1 calc R . .
C14 C 0.0063(2) 0.43553(11) 0.1482(2) 0.0396(5) Uani 1 1 d . . .
H14A H -0.0274 0.4796 0.1904 0.047 Uiso 1 1 calc R . .
H14B H -0.0467 0.4287 0.0363 0.047 Uiso 1 1 calc R . .
C15 C -0.18806(19) 0.19036(10) 0.05755(19) 0.0227(4) Uani 1 1 d . . .
C16 C -0.1186(2) 0.11975(11) 0.0940(2) 0.0264(4) Uani 1 1 d . . .
H16 H -0.0333 0.1136 0.1873 0.032 Uiso 1 1 calc R . .
C17 C -0.1718(2) 0.05834(11) -0.0036(2) 0.0301(5) Uani 1 1 d . . .
H17 H -0.1216 0.0109 0.0226 0.036 Uiso 1 1 calc R . .
C18 C -0.2971(2) 0.06544(12) -0.1384(2) 0.0332(5) Uani 1 1 d . . .
H18 H -0.3342 0.0231 -0.2045 0.040 Uiso 1 1 calc R . .
C19 C -0.3679(2) 0.13505(12) -0.1759(2) 0.0343(5) Uani 1 1 d . . .
H19 H -0.4547 0.1404 -0.2682 0.041 Uiso 1 1 calc R . .
C20 C -0.3134(2) 0.19735(11) -0.0801(2) 0.0286(4) Uani 1 1 d . . .
H20 H -0.3620 0.2451 -0.1086 0.034 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
O1 0.0283(7) 0.0301(7) 0.0194(6) -0.0024(5) 0.0115(5) 0.0013(6)
N2 0.0209(8) 0.0248(9) 0.0180(8) 0.0037(7) 0.0078(6) 0.0023(7)
C3 0.0212(9) 0.0200(10) 0.0206(9) -0.0041(7) 0.0086(7) -0.0046(8)
C4 0.0246(10) 0.0236(10) 0.0240(9) -0.0009(8) 0.0097(8) -0.0007(8)
C5 0.0240(10) 0.0248(10) 0.0281(9) -0.0003(8) 0.0119(8) 0.0023(8)
C6 0.0196(9) 0.0189(10) 0.0212(9) -0.0018(7) 0.0068(7) -0.0030(8)
C7 0.0276(10) 0.0266(11) 0.0212(9) -0.0001(8) 0.0096(8) 0.0018(9)
C8 0.0315(11) 0.0300(11) 0.0234(9) 0.0007(8) 0.0064(8) 0.0033(9)
C9 0.0234(10) 0.0267(11) 0.0366(11) -0.0037(9) 0.0103(9) 0.0031(9)
C10 0.0283(11) 0.0309(11) 0.0327(10) -0.0048(9) 0.0178(9) -0.0018(9)
C11 0.0246(10) 0.0296(11) 0.0214(9) 0.0016(8) 0.0104(8) -0.0009(8)
C12 0.0331(11) 0.0273(11) 0.0267(10) -0.0006(8) 0.0107(9) -0.0005(9)
C13 0.0438(13) 0.0290(12) 0.0432(12) 0.0001(10) 0.0170(10) -0.0103(10)
C14 0.0452(14) 0.0245(11) 0.0389(12) 0.0061(9) 0.0066(10) 0.0031(10)
C15 0.0204(9) 0.0256(11) 0.0251(9) -0.0005(8) 0.0124(8) -0.0032(8)
C16 0.0201(10) 0.0287(11) 0.0297(10) -0.0007(9) 0.0095(8) -0.0013(9)
C17 0.0319(11) 0.0254(11) 0.0383(11) -0.0015(9) 0.0197(10) -0.0019(9)
C18 0.0406(12) 0.0333(12) 0.0296(10) -0.0090(9) 0.0183(10) -0.0095(10)
C19 0.0328(11) 0.0458(14) 0.0200(9) -0.0027(9) 0.0061(8) -0.0059(10)
C20 0.0274(11) 0.0315(11) 0.0276(10) 0.0050(9) 0.0118(9) 0.0014(9)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.2385(19) . ?
N2 C3 1.350(2) . ?
N2 C6 1.415(2) . ?
N2 H2 0.875(19) . ?
C3 C4 1.520(2) . ?
C4 C12 1.509(3) . ?
C4 C5 1.539(2) . ?
C4 H4 1.0000 . ?
C5 C15 1.508(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.391(2) . ?
C6 C11 1.396(2) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C14 1.495(3) . ?
C12 C13 1.499(3) . ?
C12 H12 1.0000 . ?
C13 C14 1.504(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.391(3) . ?
C15 C20 1.395(2) . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
C3 N2 C6 128.87(15) . . ?
C3 N2 H2 114.0(12) . . ?
C6 N2 H2 117.1(12) . . ?
O1 C3 N2 123.61(16) . . ?
O1 C3 C4 121.25(14) . . ?
N2 C3 C4 115.13(14) . . ?
C12 C4 C3 108.44(14) . . ?
C12 C4 C5 111.57(14) . . ?
C3 C4 C5 110.63(14) . . ?
C12 C4 H4 108.7 . . ?
C3 C4 H4 108.7 . . ?
C5 C4 H4 108.7 . . ?
C15 C5 C4 113.67(13) . . ?
C15 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C15 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C11 119.53(16) . . ?
C7 C6 N2 124.04(15) . . ?
C11 C6 N2 116.42(15) . . ?
C8 C7 C6 119.38(16) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 121.11(17) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.35(17) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.41(16) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 120.20(16) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C14 C12 C13 60.28(13) . . ?
C14 C12 C4 118.91(16) . . ?
C13 C12 C4 118.85(16) . . ?
C14 C12 H12 115.8 . . ?
C13 C12 H12 115.8 . . ?
C4 C12 H12 115.8 . . ?
C12 C13 C14 59.73(13) . . ?
C12 C13 H13A 117.8 . . ?
C14 C13 H13A 117.8 . . ?
C12 C13 H13B 117.8 . . ?
C14 C13 H13B 117.8 . . ?
H13A C13 H13B 114.9 . . ?
C12 C14 C13 59.99(13) . . ?
C12 C14 H14A 117.8 . . ?
C13 C14 H14A 117.8 . . ?
C12 C14 H14B 117.8 . . ?
C13 C14 H14B 117.8 . . ?
H14A C14 H14B 114.9 . . ?
C16 C15 C20 117.95(16) . . ?
C16 C15 C5 121.76(16) . . ?
C20 C15 C5 120.29(16) . . ?
C17 C16 C15 121.10(17) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.59(19) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.08(18) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C20 120.67(18) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.60(18) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?

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 N2 C3 O1 -0.2(3) . . . . ?
C6 N2 C3 C4 178.26(16) . . . . ?
O1 C3 C4 C12 66.5(2) . . . . ?
N2 C3 C4 C12 -112.00(16) . . . . ?
O1 C3 C4 C5 -56.1(2) . . . . ?
N2 C3 C4 C5 125.35(16) . . . . ?
C12 C4 C5 C15 167.37(15) . . . . ?
C3 C4 C5 C15 -71.82(18) . . . . ?
C3 N2 C6 C7 -1.3(3) . . . . ?
C3 N2 C6 C11 179.61(17) . . . . ?
C11 C6 C7 C8 1.0(3) . . . . ?
N2 C6 C7 C8 -178.12(16) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C9 C10 C11 C6 -1.0(3) . . . . ?
C7 C6 C11 C10 0.0(3) . . . . ?
N2 C6 C11 C10 179.17(16) . . . . ?
C3 C4 C12 C14 146.07(16) . . . . ?
C5 C4 C12 C14 -91.85(19) . . . . ?
C3 C4 C12 C13 76.09(19) . . . . ?
C5 C4 C12 C13 -161.84(16) . . . . ?
C4 C12 C13 C14 108.73(19) . . . . ?
C4 C12 C14 C13 -108.63(19) . . . . ?
C4 C5 C15 C16 70.0(2) . . . . ?
C4 C5 C15 C20 -109.61(18) . . . . ?
C20 C15 C16 C17 0.3(2) . . . . ?
C5 C15 C16 C17 -179.36(15) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C15 -1.4(3) . . . . ?
C16 C15 C20 C19 1.0(2) . . . . ?
C5 C15 C20 C19 -179.33(15) . . . . ?

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 0.875(19) 2.05(2) 2.9105(19) 169.3(17) 4_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.046