# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'L Barbour'
'Martin W Bredenkamp'
'Tia Jacobs'
'Gareth O Lloyd'

_publ_contact_author_name        'L Barbour'
_publ_contact_author_email       LJB@SUN.AC.ZA

_publ_section_title              
;
Breaking the trigonal host packing motif of
Dianin's compound
;

# Attachment 'dianinpiperazine.CIF'

data_dianinpiperazine
_database_code_depnum_ccdc_archive 'CCDC 716677'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 O2, 0.5(C4 H10 N2)'
_chemical_formula_sum            'C20 H25 N O2'
_chemical_formula_weight         311.41

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'
_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                   8.1953(14)
_cell_length_b                   16.005(3)
_cell_length_c                   12.769(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.830(3)
_cell_angle_gamma                90.00
_cell_volume                     1650.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4011
_cell_measurement_theta_min      2.566
_cell_measurement_theta_max      28.122

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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 CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7642
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         28.22
_reflns_number_total             3719
_reflns_number_gt                2752
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
X-Seed (Barbour, 2001; Atwood & Barbour, 2003)
;
_computing_publication_material  
;
X-Seed (Atwood & Barbour, 2003; Barbour, 2001)
;

_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)+(0.0418P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3719
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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 -0.10826(12) 0.10475(7) -0.01342(8) 0.0177(3) Uani 1 1 d . . .
N1 N 0.86227(16) -0.01707(9) 0.55008(11) 0.0197(3) Uani 1 1 d . . .
C1 C -0.16205(18) 0.13987(10) 0.08006(12) 0.0157(3) Uani 1 1 d . . .
H1 H 0.818(2) -0.0244(11) 0.6071(14) 0.030(5) Uiso 1 1 d . . .
H2 H 0.699(3) -0.0353(13) 0.4386(17) 0.054(7) Uiso 1 1 d . . .
O2 O 0.62454(14) -0.05791(7) 0.37943(9) 0.0206(3) Uani 1 1 d . . .
C2 C -0.02083(17) 0.13225(10) 0.17375(12) 0.0164(4) Uani 1 1 d . . .
H2A H -0.0041 0.0722 0.1911 0.020 Uiso 1 1 calc R . .
H2B H -0.0555 0.1596 0.2359 0.020 Uiso 1 1 calc R . .
C3 C 0.14876(18) 0.17000(9) 0.15873(12) 0.0142(3) Uani 1 1 d . . .
C4 C 0.16225(18) 0.16861(9) 0.04067(12) 0.0138(3) Uani 1 1 d . . .
C5 C 0.30530(19) 0.19751(10) 0.00632(13) 0.0168(4) Uani 1 1 d . . .
H5 H 0.3910 0.2215 0.0568 0.020 Uiso 1 1 calc R . .
C6 C 0.32604(19) 0.19227(10) -0.09859(12) 0.0197(4) Uani 1 1 d . . .
H6 H 0.4241 0.2131 -0.1196 0.024 Uiso 1 1 calc R . .
C7 C 0.20285(19) 0.15644(10) -0.17306(13) 0.0196(4) Uani 1 1 d . . .
H7 H 0.2175 0.1509 -0.2449 0.024 Uiso 1 1 calc R . .
C8 C 0.05886(19) 0.12891(10) -0.14202(12) 0.0173(4) Uani 1 1 d . . .
H8 H -0.0268 0.1054 -0.1930 0.021 Uiso 1 1 calc R . .
C9 C 0.03848(18) 0.13542(9) -0.03633(12) 0.0139(3) Uani 1 1 d . . .
C10 C 0.28590(18) 0.11392(10) 0.21939(12) 0.0136(3) Uani 1 1 d . . .
C11 C 0.29975(18) 0.03183(9) 0.18406(12) 0.0148(3) Uani 1 1 d . . .
H11 H 0.2290 0.0139 0.1213 0.018 Uiso 1 1 calc R . .
C12 C 0.41244(18) -0.02362(10) 0.23730(12) 0.0160(4) Uani 1 1 d . . .
H12 H 0.4183 -0.0789 0.2109 0.019 Uiso 1 1 calc R . .
C13 C 0.51807(17) 0.00051(10) 0.32958(12) 0.0153(3) Uani 1 1 d . . .
C14 C 0.50857(18) 0.08200(10) 0.36541(12) 0.0170(4) Uani 1 1 d . . .
H14 H 0.5803 0.0998 0.4279 0.020 Uiso 1 1 calc R . .
C15 C 0.39434(18) 0.13782(10) 0.31026(12) 0.0163(4) Uani 1 1 d . . .
H15 H 0.3906 0.1935 0.3354 0.020 Uiso 1 1 calc R . .
C16 C -0.22030(19) 0.22891(10) 0.05405(12) 0.0189(4) Uani 1 1 d . . .
H16A H -0.1264 0.2631 0.0413 0.028 Uiso 1 1 calc R . .
H16B H -0.2661 0.2522 0.1138 0.028 Uiso 1 1 calc R . .
H16C H -0.3059 0.2288 -0.0098 0.028 Uiso 1 1 calc R . .
C17 C -0.30599(18) 0.08481(10) 0.09737(13) 0.0206(4) Uani 1 1 d . . .
H17A H -0.2659 0.0279 0.1147 0.031 Uiso 1 1 calc R . .
H17B H -0.3894 0.0838 0.0325 0.031 Uiso 1 1 calc R . .
H17C H -0.3555 0.1072 0.1561 0.031 Uiso 1 1 calc R . .
C18 C 0.16448(19) 0.26031(10) 0.19994(12) 0.0182(4) Uani 1 1 d . . .
H18A H 0.0762 0.2945 0.1595 0.027 Uiso 1 1 calc R . .
H18B H 0.2724 0.2829 0.1912 0.027 Uiso 1 1 calc R . .
H18C H 0.1548 0.2611 0.2754 0.027 Uiso 1 1 calc R . .
C19 C 0.9367(2) 0.06651(10) 0.55517(13) 0.0221(4) Uani 1 1 d . . .
H19A H 1.0239 0.0711 0.6189 0.027 Uiso 1 1 calc R . .
H19B H 0.8512 0.1093 0.5603 0.027 Uiso 1 1 calc R . .
C20 C 0.9893(2) -0.08083(10) 0.54383(13) 0.0219(4) Uani 1 1 d . . .
H20A H 0.9390 -0.1372 0.5416 0.026 Uiso 1 1 calc R . .
H20B H 1.0770 -0.0774 0.6074 0.026 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 C9 1.3759(17) . ?
O1 C1 1.4542(18) . ?
N1 C19 1.467(2) . ?
N1 C20 1.470(2) . ?
N1 H1 0.875(18) . ?
C1 C17 1.519(2) . ?
C1 C2 1.521(2) . ?
C1 C16 1.522(2) . ?
O2 C13 1.3606(18) . ?
O2 H2 0.96(2) . ?
C2 C3 1.557(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.530(2) . ?
C3 C18 1.536(2) . ?
C3 C10 1.540(2) . ?
C4 C9 1.392(2) . ?
C4 C5 1.399(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C10 C15 1.389(2) . ?
C10 C11 1.400(2) . ?
C11 C12 1.374(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C14 C15 1.395(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.510(2) 3_756 ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C19 1.510(2) 3_756 ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
C9 O1 C1 115.78(11) . . ?
C19 N1 C20 110.05(13) . . ?
C19 N1 H1 108.3(12) . . ?
C20 N1 H1 110.5(11) . . ?
O1 C1 C17 104.30(12) . . ?
O1 C1 C2 108.55(12) . . ?
C17 C1 C2 110.16(13) . . ?
O1 C1 C16 108.10(12) . . ?
C17 C1 C16 110.66(13) . . ?
C2 C1 C16 114.53(13) . . ?
C13 O2 H2 112.5(12) . . ?
C1 C2 C3 116.57(13) . . ?
C1 C2 H2A 108.1 . . ?
C3 C2 H2A 108.1 . . ?
C1 C2 H2B 108.1 . . ?
C3 C2 H2B 108.1 . . ?
H2A C2 H2B 107.3 . . ?
C4 C3 C18 109.58(12) . . ?
C4 C3 C10 108.52(12) . . ?
C18 C3 C10 111.40(12) . . ?
C4 C3 C2 109.38(12) . . ?
C18 C3 C2 110.32(13) . . ?
C10 C3 C2 107.58(12) . . ?
C9 C4 C5 116.97(14) . . ?
C9 C4 C3 122.33(14) . . ?
C5 C4 C3 120.62(13) . . ?
C6 C5 C4 122.17(14) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 119.62(15) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 119.55(15) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.31(14) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
O1 C9 C4 122.96(14) . . ?
O1 C9 C8 115.68(13) . . ?
C4 C9 C8 121.33(14) . . ?
C15 C10 C11 116.87(14) . . ?
C15 C10 C3 124.57(14) . . ?
C11 C10 C3 118.51(13) . . ?
C12 C11 C10 122.09(14) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.51(15) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
O2 C13 C14 123.97(13) . . ?
O2 C13 C12 117.49(14) . . ?
C14 C13 C12 118.54(14) . . ?
C13 C14 C15 120.38(14) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 121.59(15) . . ?
C10 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 108.94(13) . 3_756 ?
N1 C19 H19A 109.9 . . ?
C20 C19 H19A 109.9 3_756 . ?
N1 C19 H19B 109.9 . . ?
C20 C19 H19B 109.9 3_756 . ?
H19A C19 H19B 108.3 . . ?
N1 C20 C19 109.25(13) . 3_756 ?
N1 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 3_756 . ?
N1 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 3_756 . ?
H20A C20 H20B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C17 -170.08(12) . . . . ?
C9 O1 C1 C2 -52.65(16) . . . . ?
C9 O1 C1 C16 72.13(15) . . . . ?
O1 C1 C2 C3 54.24(17) . . . . ?
C17 C1 C2 C3 167.87(13) . . . . ?
C16 C1 C2 C3 -66.64(18) . . . . ?
C1 C2 C3 C4 -27.41(18) . . . . ?
C1 C2 C3 C18 93.19(16) . . . . ?
C1 C2 C3 C10 -145.11(13) . . . . ?
C18 C3 C4 C9 -122.71(15) . . . . ?
C10 C3 C4 C9 115.45(15) . . . . ?
C2 C3 C4 C9 -1.65(19) . . . . ?
C18 C3 C4 C5 60.42(18) . . . . ?
C10 C3 C4 C5 -61.43(18) . . . . ?
C2 C3 C4 C5 -178.53(13) . . . . ?
C9 C4 C5 C6 -1.3(2) . . . . ?
C3 C4 C5 C6 175.78(14) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C8 2.1(2) . . . . ?
C6 C7 C8 C9 -1.3(2) . . . . ?
C1 O1 C9 C4 26.3(2) . . . . ?
C1 O1 C9 C8 -155.73(13) . . . . ?
C5 C4 C9 O1 179.94(14) . . . . ?
C3 C4 C9 O1 3.0(2) . . . . ?
C5 C4 C9 C8 2.0(2) . . . . ?
C3 C4 C9 C8 -174.95(14) . . . . ?
C7 C8 C9 O1 -178.85(14) . . . . ?
C7 C8 C9 C4 -0.8(2) . . . . ?
C4 C3 C10 C15 130.10(16) . . . . ?
C18 C3 C10 C15 9.4(2) . . . . ?
C2 C3 C10 C15 -111.66(16) . . . . ?
C4 C3 C10 C11 -52.60(17) . . . . ?
C18 C3 C10 C11 -173.32(14) . . . . ?
C2 C3 C10 C11 65.65(17) . . . . ?
C15 C10 C11 C12 1.3(2) . . . . ?
C3 C10 C11 C12 -176.19(14) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 O2 178.82(14) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
O2 C13 C14 C15 -179.21(14) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C11 C10 C15 C14 -1.7(2) . . . . ?
C3 C10 C15 C14 175.61(14) . . . . ?
C13 C14 C15 C10 0.8(2) . . . . ?
C20 N1 C19 C20 60.25(17) . . . 3_756 ?
C19 N1 C20 C19 -60.43(17) . . . 3_756 ?

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
O2 H2 N1 0.96(2) 1.80(2) 2.7426(17) 166.4(18) .
C11 H11 O1 0.95 2.45 3.2895(18) 146.9 3

_diffrn_measured_fraction_theta_max 0.915
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049

# Attachment 'dianinpiperidine.CIF'

data_c:\tia\work\paperw~1\dianin~2\dianin~2\xx
_database_code_depnum_ccdc_archive 'CCDC 716678'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 O2, C5 H11 N1'
_chemical_formula_sum            'C23 H31 N O2'
_chemical_formula_weight         353.49

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                   15.4360(18)
_cell_length_b                   12.9411(15)
_cell_length_c                   10.3343(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.800(2)
_cell_angle_gamma                90.00
_cell_volume                     2027.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5064
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12574
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         28.23
_reflns_number_total             4690
_reflns_number_gt                3517
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
X-Seed (Barbour, 2001; Atwood & Barbour, 2003)
;
_computing_publication_material  
;
X-Seed (Atwood & Barbour, 2003; Barbour, 2001)
;

_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)+(0.0708P)²+0.0399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4690
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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 0.82948(6) -0.09467(6) 0.40875(9) 0.0228(2) Uani 1 1 d . . .
N1 N 0.57006(8) 0.55249(9) 0.35848(12) 0.0256(3) Uani 1 1 d . . .
C1 C 0.81063(9) -0.00549(10) 0.32117(13) 0.0223(3) Uani 1 1 d . . .
H1 H 0.5253(10) 0.5842(12) 0.3851(16) 0.035(4) Uiso 1 1 d . . .
H2 H 0.5785(12) 0.4488(15) 0.4526(18) 0.059(6) Uiso 1 1 d . . .
O2 O 0.57755(6) 0.38866(7) 0.51188(10) 0.0263(2) Uani 1 1 d . . .
C2 C 0.87378(8) 0.08135(10) 0.37354(13) 0.0204(3) Uani 1 1 d . . .
H2A H 0.8609 0.1413 0.3136 0.024 Uiso 1 1 calc R . .
H2B H 0.9346 0.0583 0.3711 0.024 Uiso 1 1 calc R . .
C3 C 0.87029(8) 0.11730(9) 0.51466(13) 0.0181(3) Uani 1 1 d . . .
C4 C 0.86851(8) 0.02037(10) 0.59851(13) 0.0183(3) Uani 1 1 d . . .
C5 C 0.89045(9) 0.02371(11) 0.73607(14) 0.0258(3) Uani 1 1 d . . .
H5 H 0.9062 0.0882 0.7777 0.031 Uiso 1 1 calc R . .
C6 C 0.89015(9) -0.06337(12) 0.81385(14) 0.0315(4) Uani 1 1 d . . .
H6 H 0.9043 -0.0580 0.9071 0.038 Uiso 1 1 calc R . .
C7 C 0.86912(9) -0.15819(12) 0.75449(15) 0.0314(4) Uani 1 1 d . . .
H7 H 0.8690 -0.2186 0.8067 0.038 Uiso 1 1 calc R . .
C8 C 0.84836(9) -0.16452(10) 0.61947(15) 0.0264(3) Uani 1 1 d . . .
H8 H 0.8342 -0.2297 0.5787 0.032 Uiso 1 1 calc R . .
C9 C 0.84788(8) -0.07641(10) 0.54158(13) 0.0201(3) Uani 1 1 d . . .
C10 C 0.79066(8) 0.18851(9) 0.51711(12) 0.0166(3) Uani 1 1 d . . .
C11 C 0.72756(8) 0.17148(10) 0.59466(13) 0.0181(3) Uani 1 1 d . . .
H11 H 0.7328 0.1124 0.6501 0.022 Uiso 1 1 calc R . .
C12 C 0.65723(8) 0.23841(10) 0.59329(13) 0.0200(3) Uani 1 1 d . . .
H12 H 0.6154 0.2248 0.6479 0.024 Uiso 1 1 calc R . .
C13 C 0.64749(8) 0.32497(9) 0.51280(13) 0.0188(3) Uani 1 1 d . . .
C14 C 0.71073(9) 0.34416(10) 0.43596(13) 0.0208(3) Uani 1 1 d . . .
H14 H 0.7059 0.4037 0.3813 0.025 Uiso 1 1 calc R . .
C15 C 0.78058(8) 0.27686(10) 0.43883(13) 0.0206(3) Uani 1 1 d . . .
H15 H 0.8231 0.2913 0.3857 0.025 Uiso 1 1 calc R . .
C16 C 0.82889(10) -0.04340(11) 0.18977(14) 0.0326(4) Uani 1 1 d . . .
H16A H 0.7878 -0.0993 0.1568 0.049 Uiso 1 1 calc R . .
H16B H 0.8896 -0.0691 0.2014 0.049 Uiso 1 1 calc R . .
H16C H 0.8210 0.0137 0.1264 0.049 Uiso 1 1 calc R . .
C17 C 0.71314(9) 0.02014(11) 0.31035(14) 0.0272(3) Uani 1 1 d . . .
H17A H 0.6775 -0.0402 0.2768 0.041 Uiso 1 1 calc R . .
H17B H 0.6977 0.0784 0.2498 0.041 Uiso 1 1 calc R . .
H17C H 0.7016 0.0387 0.3975 0.041 Uiso 1 1 calc R . .
C18 C 0.95442(8) 0.18061(10) 0.56577(15) 0.0256(3) Uani 1 1 d . . .
H18A H 0.9550 0.2423 0.5109 0.038 Uiso 1 1 calc R . .
H18B H 1.0065 0.1383 0.5617 0.038 Uiso 1 1 calc R . .
H18C H 0.9552 0.2015 0.6571 0.038 Uiso 1 1 calc R . .
C19 C 0.64433(9) 0.62466(11) 0.37613(16) 0.0326(4) Uani 1 1 d . . .
H19A H 0.6955 0.5904 0.3493 0.039 Uiso 1 1 calc R . .
H19B H 0.6611 0.6425 0.4707 0.039 Uiso 1 1 calc R . .
C20 C 0.62336(11) 0.72309(12) 0.2969(2) 0.0468(5) Uani 1 1 d . . .
H20A H 0.5773 0.7623 0.3310 0.056 Uiso 1 1 calc R . .
H20B H 0.6769 0.7668 0.3070 0.056 Uiso 1 1 calc R . .
C21 C 0.59150(12) 0.69886(15) 0.15324(19) 0.0540(5) Uani 1 1 d . . .
H21A H 0.6407 0.6697 0.1158 0.065 Uiso 1 1 calc R . .
H21B H 0.5719 0.7634 0.1051 0.065 Uiso 1 1 calc R . .
C22 C 0.51576(12) 0.62243(14) 0.13482(16) 0.0461(5) Uani 1 1 d . . .
H22A H 0.4633 0.6556 0.1593 0.055 Uiso 1 1 calc R . .
H22B H 0.5005 0.6020 0.0410 0.055 Uiso 1 1 calc R . .
C23 C 0.54008(10) 0.52720(12) 0.21888(16) 0.0350(4) Uani 1 1 d . . .
H23A H 0.4881 0.4811 0.2099 0.042 Uiso 1 1 calc R . .
H23B H 0.5875 0.4893 0.1863 0.042 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 C9 1.3692(16) . ?
O1 C1 1.4619(15) . ?
N1 C19 1.4635(19) . ?
N1 C23 1.4671(19) . ?
N1 H1 0.891(16) . ?
C1 C16 1.5191(19) . ?
C1 C2 1.5193(18) . ?
C1 C17 1.5245(18) . ?
O2 C13 1.3568(15) . ?
O2 H2 0.992(19) . ?
C2 C3 1.5413(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5277(17) . ?
C3 C10 1.5402(16) . ?
C3 C18 1.5426(17) . ?
C4 C9 1.3949(18) . ?
C4 C5 1.3989(18) . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3949(18) . ?
C8 H8 0.9500 . ?
C10 C11 1.3899(17) . ?
C10 C15 1.3923(17) . ?
C11 C12 1.3869(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3865(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3913(18) . ?
C14 C15 1.3820(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.516(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.507(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.516(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.514(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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
C9 O1 C1 117.66(9) . . ?
C19 N1 C23 111.12(12) . . ?
C19 N1 H1 107.6(10) . . ?
C23 N1 H1 106.6(10) . . ?
O1 C1 C16 104.46(10) . . ?
O1 C1 C2 108.87(10) . . ?
C16 C1 C2 110.07(12) . . ?
O1 C1 C17 107.24(11) . . ?
C16 C1 C17 110.52(11) . . ?
C2 C1 C17 115.08(11) . . ?
C13 O2 H2 112.2(10) . . ?
C1 C2 C3 115.24(11) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C10 112.51(10) . . ?
C4 C3 C2 107.24(10) . . ?
C10 C3 C2 111.45(10) . . ?
C4 C3 C18 110.20(10) . . ?
C10 C3 C18 107.44(10) . . ?
C2 C3 C18 107.92(10) . . ?
C9 C4 C5 116.68(12) . . ?
C9 C4 C3 121.66(11) . . ?
C5 C4 C3 121.62(12) . . ?
C6 C5 C4 122.56(14) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C7 C6 C5 119.38(14) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C6 119.59(13) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.81(13) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
O1 C9 C4 124.46(11) . . ?
O1 C9 C8 114.53(12) . . ?
C4 C9 C8 120.96(12) . . ?
C11 C10 C15 116.82(11) . . ?
C11 C10 C3 124.20(11) . . ?
C15 C10 C3 118.97(11) . . ?
C12 C11 C10 121.80(12) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C13 C12 C11 120.49(12) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O2 C13 C12 119.45(12) . . ?
O2 C13 C14 122.01(11) . . ?
C12 C13 C14 118.54(11) . . ?
C15 C14 C13 120.22(12) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 122.12(12) . . ?
C14 C15 H15 118.9 . . ?
C10 C15 H15 118.9 . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 112.70(12) . . ?
N1 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N1 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 110.75(14) . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 C22 111.17(14) . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C23 C22 C21 110.89(13) . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.0 . . ?
N1 C23 C22 112.41(12) . . ?
N1 C23 H23A 109.1 . . ?
C22 C23 H23A 109.1 . . ?
N1 C23 H23B 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C16 158.44(11) . . . . ?
C9 O1 C1 C2 40.88(14) . . . . ?
C9 O1 C1 C17 -84.23(12) . . . . ?
O1 C1 C2 C3 -58.50(14) . . . . ?
C16 C1 C2 C3 -172.44(11) . . . . ?
C17 C1 C2 C3 61.88(15) . . . . ?
C1 C2 C3 C4 45.07(13) . . . . ?
C1 C2 C3 C10 -78.47(13) . . . . ?
C1 C2 C3 C18 163.78(10) . . . . ?
C10 C3 C4 C9 106.51(13) . . . . ?
C2 C3 C4 C9 -16.39(15) . . . . ?
C18 C3 C4 C9 -133.61(12) . . . . ?
C10 C3 C4 C5 -75.72(15) . . . . ?
C2 C3 C4 C5 161.39(11) . . . . ?
C18 C3 C4 C5 44.16(15) . . . . ?
C9 C4 C5 C6 -1.45(19) . . . . ?
C3 C4 C5 C6 -179.32(12) . . . . ?
C4 C5 C6 C7 1.3(2) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C1 O1 C9 C4 -14.43(17) . . . . ?
C1 O1 C9 C8 168.20(11) . . . . ?
C5 C4 C9 O1 -176.44(11) . . . . ?
C3 C4 C9 O1 1.44(18) . . . . ?
C5 C4 C9 C8 0.77(18) . . . . ?
C3 C4 C9 C8 178.64(11) . . . . ?
C7 C8 C9 O1 177.52(11) . . . . ?
C7 C8 C9 C4 0.05(19) . . . . ?
C4 C3 C10 C11 4.79(17) . . . . ?
C2 C3 C10 C11 125.29(13) . . . . ?
C18 C3 C10 C11 -116.68(13) . . . . ?
C4 C3 C10 C15 -176.17(11) . . . . ?
C2 C3 C10 C15 -55.67(15) . . . . ?
C18 C3 C10 C15 62.36(15) . . . . ?
C15 C10 C11 C12 0.75(18) . . . . ?
C3 C10 C11 C12 179.80(11) . . . . ?
C10 C11 C12 C13 0.41(19) . . . . ?
C11 C12 C13 O2 179.19(11) . . . . ?
C11 C12 C13 C14 -1.37(19) . . . . ?
O2 C13 C14 C15 -179.42(12) . . . . ?
C12 C13 C14 C15 1.15(19) . . . . ?
C13 C14 C15 C10 0.0(2) . . . . ?
C11 C10 C15 C14 -0.97(19) . . . . ?
C3 C10 C15 C14 179.92(12) . . . . ?
C23 N1 C19 C20 56.21(17) . . . . ?
N1 C19 C20 C21 -54.93(18) . . . . ?
C19 C20 C21 C22 52.84(18) . . . . ?
C20 C21 C22 C23 -52.96(19) . . . . ?
C19 N1 C23 C22 -56.09(16) . . . . ?
C21 C22 C23 N1 54.73(19) . . . . ?

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
O2 H2 N1 0.992(19) 1.65(2) 2.6368(15) 173.9(16) .
N1 H1 O2 0.891(16) 2.100(16) 2.9513(15) 159.7(14) 3_666
C18 H18B O1 0.98 2.56 3.4792(16) 157.0 3_756

_diffrn_measured_fraction_theta_max 0.936
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043


