# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Muthusubramanian, Shanmugam'
_publ_contact_author_email       muthumanian2001@yahoo.com

_publ_section_title              
;
Synthesis of novel N-hydroxy heterocycles via intramolecular
reductive cyclization of diketoximes by NaBH3CN
;
loop_
_publ_author_name
M.Nagaraj
M.Boominathan
S.Muthusubramanian
N.Bhuvanesh

# Attachment '13a.cif'

#==========================================================================
data_emku37
_database_code_depnum_ccdc_archive 'CCDC 801741'
#TrackingRef '13a.cif'

#==========================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
2,4-diphenyloctahydroquinolin-1(2H)-ol

;

_chemical_name_common            2,4-diphenyloctahydroquinolin-1(2H)-ol
_chemical_melting_point          196
_chemical_formula_moiety         'C21 H25 N O, 0.5(C6 H6)'
_chemical_formula_sum            'C24 H28 N O'
_chemical_formula_weight         346.47

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'

#==========================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   21.472(3)
_cell_length_b                   7.807(6)
_cell_length_c                   25.852(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.95(2)
_cell_angle_gamma                90.00
_cell_volume                     3897(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2234
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      20.0
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1496
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

#==========================================================================

# Experimental data

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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       '\w and \f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8626
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         28.99
_reflns_number_total             4438
_reflns_number_gt                2597
_reflns_threshold_expression     >2sigma(I)
_diffrn_measured_fraction_theta_max 0.854
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLUTON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#==========================================================================

# Refinement data

_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^ > 2sigma(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^)+(0.0341P)^2^+1.0659P] 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     SHELXL
_refine_ls_extinction_coef       0.0056(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4438
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.035

#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.47355(6) 0.34568(17) 0.02924(6) 0.0463(4) Uani 1 1 d . . .
N1 N 0.54397(7) 0.40969(16) 0.06274(6) 0.0340(4) Uani 1 1 d . . .
C2 C 0.59194(8) 0.27799(19) 0.05936(8) 0.0342(4) Uani 1 1 d . . .
H2 H 0.5839 0.2741 0.0190 0.041 Uiso 1 1 calc R . .
C3 C 0.58111(9) 0.0954(2) 0.07528(9) 0.0439(5) Uani 1 1 d . . .
H3A H 0.5882 0.0924 0.1150 0.053 Uiso 1 1 calc R . .
H3B H 0.5340 0.0593 0.0511 0.053 Uiso 1 1 calc R . .
C4 C 0.63168(10) -0.0265(2) 0.06741(10) 0.0531(6) Uani 1 1 d . . .
H4A H 0.6255 -0.1409 0.0791 0.064 Uiso 1 1 calc R . .
H4B H 0.6218 -0.0307 0.0270 0.064 Uiso 1 1 calc R . .
C5 C 0.70623(10) 0.0296(2) 0.10256(9) 0.0506(5) Uani 1 1 d . . .
H5A H 0.7371 -0.0472 0.0953 0.061 Uiso 1 1 calc R . .
H5B H 0.7176 0.0241 0.1432 0.061 Uiso 1 1 calc R . .
C6 C 0.71638(9) 0.2119(2) 0.08669(8) 0.0430(5) Uani 1 1 d . . .
H6A H 0.7095 0.2139 0.0470 0.052 Uiso 1 1 calc R . .
H6B H 0.7636 0.2473 0.1108 0.052 Uiso 1 1 calc R . .
C7 C 0.66662(8) 0.3398(2) 0.09388(7) 0.0327(4) Uani 1 1 d . . .
H7 H 0.6713 0.4486 0.0770 0.039 Uiso 1 1 calc R . .
C8 C 0.68248(8) 0.3748(2) 0.15706(7) 0.0344(4) Uani 1 1 d . . .
H8 H 0.6807 0.2654 0.1749 0.041 Uiso 1 1 calc R . .
C9 C 0.62628(8) 0.4917(2) 0.15917(7) 0.0372(4) Uani 1 1 d . . .
H9A H 0.6333 0.5007 0.1988 0.045 Uiso 1 1 calc R . .
H9B H 0.6318 0.6054 0.1466 0.045 Uiso 1 1 calc R . .
C10 C 0.55202(8) 0.4311(2) 0.12219(7) 0.0363(4) Uani 1 1 d . . .
H10 H 0.5452 0.3199 0.1366 0.044 Uiso 1 1 calc R . .
C81 C 0.75436(8) 0.4499(2) 0.19054(8) 0.0358(4) Uani 1 1 d . . .
C82 C 0.80420(9) 0.3641(2) 0.23679(8) 0.0497(5) Uani 1 1 d . . .
H82 H 0.7928 0.2608 0.2485 0.060 Uiso 1 1 calc R . .
C83 C 0.87064(10) 0.4280(3) 0.26622(9) 0.0633(6) Uani 1 1 d . . .
H83 H 0.9035 0.3670 0.2969 0.076 Uiso 1 1 calc R . .
C84 C 0.88793(10) 0.5809(3) 0.25017(10) 0.0624(6) Uani 1 1 d . . .
H84 H 0.9325 0.6243 0.2699 0.075 Uiso 1 1 calc R . .
C85 C 0.83925(11) 0.6698(3) 0.20490(10) 0.0594(6) Uani 1 1 d . . .
H85 H 0.8507 0.7744 0.1941 0.071 Uiso 1 1 calc R . .
C86 C 0.77305(9) 0.6049(2) 0.17509(9) 0.0492(5) Uani 1 1 d . . .
H86 H 0.7406 0.6660 0.1442 0.059 Uiso 1 1 calc R . .
C101 C 0.50148(8) 0.5582(2) 0.12619(8) 0.0379(4) Uani 1 1 d . . .
C102 C 0.49118(9) 0.7172(2) 0.10030(8) 0.0442(5) Uani 1 1 d . . .
H102 H 0.5127 0.7436 0.0769 0.053 Uiso 1 1 calc R . .
C103 C 0.44922(10) 0.8376(3) 0.10873(9) 0.0544(6) Uani 1 1 d . . .
H103 H 0.4424 0.9438 0.0908 0.065 Uiso 1 1 calc R . .
C104 C 0.41738(11) 0.8008(3) 0.14365(10) 0.0672(7) Uani 1 1 d . . .
H104 H 0.3895 0.8822 0.1495 0.081 Uiso 1 1 calc R . .
C105 C 0.42716(12) 0.6444(3) 0.16944(12) 0.0779(8) Uani 1 1 d . . .
H105 H 0.4059 0.6189 0.1931 0.094 Uiso 1 1 calc R . .
C106 C 0.46853(11) 0.5234(3) 0.16054(10) 0.0619(6) Uani 1 1 d . . .
H106 H 0.4743 0.4166 0.1780 0.074 Uiso 1 1 calc R . .
C1A C 0.70429(13) 0.6158(3) -0.01283(11) 0.0708(7) Uani 1 1 d . . .
H1A H 0.6734 0.5249 -0.0214 0.085 Uiso 1 1 calc R . .
C2A C 0.77102(14) 0.5983(3) 0.02843(11) 0.0728(7) Uani 1 1 d . . .
H2A H 0.7855 0.4947 0.0478 0.087 Uiso 1 1 calc R . .
C3A C 0.81666(12) 0.7316(3) 0.04147(11) 0.0714(7) Uani 1 1 d . . .
H3A1 H 0.8619 0.7188 0.0697 0.086 Uiso 1 1 calc R . .
H1 H 0.4582(12) 0.416(3) -0.0035(11) 0.107(10) Uiso 1 1 d . . .

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 0.0296(7) 0.0547(8) 0.0449(8) -0.0045(7) 0.0073(6) -0.0055(6)
N1 0.0248(7) 0.0403(8) 0.0319(8) -0.0017(7) 0.0077(6) -0.0007(6)
C2 0.0343(10) 0.0347(9) 0.0324(10) -0.0014(8) 0.0133(8) 0.0021(7)
C3 0.0429(11) 0.0373(9) 0.0493(12) -0.0030(9) 0.0182(10) -0.0035(8)
C4 0.0594(13) 0.0352(10) 0.0660(15) -0.0019(10) 0.0286(12) 0.0025(9)
C5 0.0520(12) 0.0398(10) 0.0624(14) 0.0042(10) 0.0271(11) 0.0118(9)
C6 0.0393(10) 0.0451(10) 0.0473(12) -0.0018(9) 0.0214(9) 0.0051(8)
C7 0.0334(9) 0.0314(8) 0.0338(10) 0.0033(8) 0.0153(8) 0.0009(7)
C8 0.0309(9) 0.0331(9) 0.0360(10) 0.0040(8) 0.0115(8) 0.0024(7)
C9 0.0339(10) 0.0435(10) 0.0310(10) -0.0020(8) 0.0112(8) 0.0031(8)
C10 0.0339(10) 0.0400(9) 0.0351(10) 0.0018(8) 0.0153(8) 0.0029(7)
C81 0.0322(9) 0.0386(9) 0.0350(10) -0.0013(8) 0.0132(8) 0.0035(7)
C82 0.0409(11) 0.0580(12) 0.0407(11) 0.0073(10) 0.0091(9) 0.0041(9)
C83 0.0418(12) 0.0837(16) 0.0457(13) -0.0008(12) 0.0020(10) 0.0050(11)
C84 0.0353(11) 0.0859(16) 0.0564(14) -0.0257(13) 0.0112(11) -0.0110(11)
C85 0.0501(13) 0.0549(12) 0.0717(16) -0.0129(12) 0.0253(12) -0.0131(10)
C86 0.0396(11) 0.0448(10) 0.0557(13) 0.0028(10) 0.0140(10) 0.0010(9)
C101 0.0289(9) 0.0469(10) 0.0340(10) -0.0033(9) 0.0102(8) 0.0004(8)
C102 0.0367(10) 0.0526(11) 0.0420(11) -0.0022(9) 0.0160(9) 0.0049(8)
C103 0.0442(12) 0.0557(12) 0.0549(14) -0.0034(11) 0.0140(11) 0.0137(10)
C104 0.0486(13) 0.0847(17) 0.0694(17) -0.0132(14) 0.0267(13) 0.0203(12)
C105 0.0747(17) 0.0937(18) 0.090(2) 0.0084(16) 0.0585(16) 0.0217(14)
C106 0.0612(14) 0.0682(13) 0.0716(16) 0.0121(12) 0.0433(13) 0.0138(11)
C1A 0.0751(18) 0.0711(16) 0.0793(18) 0.0046(14) 0.0460(16) -0.0027(13)
C2A 0.0826(19) 0.0669(15) 0.0774(18) 0.0223(14) 0.0430(16) 0.0186(14)
C3A 0.0639(16) 0.0863(17) 0.0676(17) 0.0110(15) 0.0320(14) 0.0162(14)

#==========================================================================

# MOLECULAR GEOMETRY

_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 N1 1.4628(17) . ?
O1 H1 0.94(3) . ?
N1 C10 1.479(2) . ?
N1 C2 1.4849(19) . ?
C2 C3 1.529(2) . ?
C2 C7 1.532(2) . ?
C2 H2 0.9800 . ?
C3 C4 1.523(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.519(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.523(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.532(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.540(2) . ?
C7 H7 0.9800 . ?
C8 C81 1.518(2) . ?
C8 C9 1.533(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.532(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C101 1.507(2) . ?
C10 H10 0.9800 . ?
C81 C82 1.380(2) . ?
C81 C86 1.387(2) . ?
C82 C83 1.383(3) . ?
C82 H82 0.9300 . ?
C83 C84 1.368(3) . ?
C83 H83 0.9300 . ?
C84 C85 1.369(3) . ?
C84 H84 0.9300 . ?
C85 C86 1.383(2) . ?
C85 H85 0.9300 . ?
C86 H86 0.9300 . ?
C101 C102 1.381(2) . ?
C101 C106 1.383(3) . ?
C102 C103 1.384(2) . ?
C102 H102 0.9300 . ?
C103 C104 1.380(3) . ?
C103 H103 0.9300 . ?
C104 C105 1.363(3) . ?
C104 H104 0.9300 . ?
C105 C106 1.383(3) . ?
C105 H105 0.9300 . ?
C106 H106 0.9300 . ?
C1A C2A 1.368(3) . ?
C1A C3A 1.370(3) 7_665 ?
C1A H1A 0.9300 . ?
C2A C3A 1.367(3) . ?
C2A H2A 0.9300 . ?
C3A C1A 1.370(3) 7_665 ?
C3A H3A1 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

N1 O1 H1 101.3(14) . . ?
O1 N1 C10 105.93(12) . . ?
O1 N1 C2 107.01(11) . . ?
C10 N1 C2 111.77(13) . . ?
N1 C2 C3 116.00(14) . . ?
N1 C2 C7 108.90(12) . . ?
C3 C2 C7 112.35(14) . . ?
N1 C2 H2 106.3 . . ?
C3 C2 H2 106.3 . . ?
C7 C2 H2 106.3 . . ?
C4 C3 C2 110.20(15) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 111.46(15) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 110.24(15) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C7 112.74(15) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 C2 109.40(13) . . ?
C6 C7 C8 113.72(14) . . ?
C2 C7 C8 111.28(14) . . ?
C6 C7 H7 107.4 . . ?
C2 C7 H7 107.4 . . ?
C8 C7 H7 107.4 . . ?
C81 C8 C9 111.69(13) . . ?
C81 C8 C7 111.78(14) . . ?
C9 C8 C7 109.36(13) . . ?
C81 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C7 C8 H8 107.9 . . ?
C10 C9 C8 114.49(13) . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
N1 C10 C101 112.67(14) . . ?
N1 C10 C9 107.45(14) . . ?
C101 C10 C9 109.75(13) . . ?
N1 C10 H10 109.0 . . ?
C101 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C82 C81 C86 117.42(17) . . ?
C82 C81 C8 121.08(16) . . ?
C86 C81 C8 121.49(15) . . ?
C81 C82 C83 121.60(19) . . ?
C81 C82 H82 119.2 . . ?
C83 C82 H82 119.2 . . ?
C84 C83 C82 120.0(2) . . ?
C84 C83 H83 120.0 . . ?
C82 C83 H83 120.0 . . ?
C83 C84 C85 119.67(19) . . ?
C83 C84 H84 120.2 . . ?
C85 C84 H84 120.2 . . ?
C84 C85 C86 120.3(2) . . ?
C84 C85 H85 119.8 . . ?
C86 C85 H85 119.8 . . ?
C85 C86 C81 121.03(18) . . ?
C85 C86 H86 119.5 . . ?
C81 C86 H86 119.5 . . ?
C102 C101 C106 118.00(17) . . ?
C102 C101 C10 121.73(16) . . ?
C106 C101 C10 120.03(17) . . ?
C101 C102 C103 120.76(19) . . ?
C101 C102 H102 119.6 . . ?
C103 C102 H102 119.6 . . ?
C104 C103 C102 120.3(2) . . ?
C104 C103 H103 119.8 . . ?
C102 C103 H103 119.8 . . ?
C105 C104 C103 119.5(2) . . ?
C105 C104 H104 120.3 . . ?
C103 C104 H104 120.3 . . ?
C104 C105 C106 120.2(2) . . ?
C104 C105 H105 119.9 . . ?
C106 C105 H105 119.9 . . ?
C105 C106 C101 121.2(2) . . ?
C105 C106 H106 119.4 . . ?
C101 C106 H106 119.4 . . ?
C2A C1A C3A 119.5(2) . 7_665 ?
C2A C1A H1A 120.3 . . ?
C3A C1A H1A 120.3 7_665 . ?
C3A C2A C1A 120.6(2) . . ?
C3A C2A H2A 119.7 . . ?
C1A C2A H2A 119.7 . . ?
C2A C3A C1A 119.9(2) . 7_665 ?
C2A C3A H3A1 120.1 . . ?
C1A C3A H3A1 120.1 7_665 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

O1 N1 C2 C3 -52.20(19) . . . . ?
C10 N1 C2 C3 63.34(18) . . . . ?
O1 N1 C2 C7 179.91(13) . . . . ?
C10 N1 C2 C7 -64.55(17) . . . . ?
N1 C2 C3 C4 177.58(15) . . . . ?
C7 C2 C3 C4 -56.2(2) . . . . ?
C2 C3 C4 C5 56.8(2) . . . . ?
C3 C4 C5 C6 -56.6(2) . . . . ?
C4 C5 C6 C7 56.2(2) . . . . ?
C5 C6 C7 C2 -54.7(2) . . . . ?
C5 C6 C7 C8 70.37(19) . . . . ?
N1 C2 C7 C6 -175.41(13) . . . . ?
C3 C2 C7 C6 54.66(19) . . . . ?
N1 C2 C7 C8 58.08(17) . . . . ?
C3 C2 C7 C8 -71.84(17) . . . . ?
C6 C7 C8 C81 60.57(18) . . . . ?
C2 C7 C8 C81 -175.34(12) . . . . ?
C6 C7 C8 C9 -175.22(13) . . . . ?
C2 C7 C8 C9 -51.12(17) . . . . ?
C81 C8 C9 C10 175.22(14) . . . . ?
C7 C8 C9 C10 50.95(19) . . . . ?
O1 N1 C10 C101 -61.09(16) . . . . ?
C2 N1 C10 C101 -177.29(13) . . . . ?
O1 N1 C10 C9 177.91(12) . . . . ?
C2 N1 C10 C9 61.70(16) . . . . ?
C8 C9 C10 N1 -55.42(18) . . . . ?
C8 C9 C10 C101 -178.24(14) . . . . ?
C9 C8 C81 C82 119.46(18) . . . . ?
C7 C8 C81 C82 -117.63(18) . . . . ?
C9 C8 C81 C86 -62.1(2) . . . . ?
C7 C8 C81 C86 60.8(2) . . . . ?
C86 C81 C82 C83 -1.0(3) . . . . ?
C8 C81 C82 C83 177.46(18) . . . . ?
C81 C82 C83 C84 0.9(3) . . . . ?
C82 C83 C84 C85 -0.1(3) . . . . ?
C83 C84 C85 C86 -0.6(3) . . . . ?
C84 C85 C86 C81 0.6(3) . . . . ?
C82 C81 C86 C85 0.3(3) . . . . ?
C8 C81 C86 C85 -178.20(18) . . . . ?
N1 C10 C101 C102 -47.9(2) . . . . ?
C9 C10 C101 C102 71.7(2) . . . . ?
N1 C10 C101 C106 137.83(18) . . . . ?
C9 C10 C101 C106 -102.5(2) . . . . ?
C106 C101 C102 C103 0.1(3) . . . . ?
C10 C101 C102 C103 -174.21(17) . . . . ?
C101 C102 C103 C104 0.5(3) . . . . ?
C102 C103 C104 C105 -0.5(3) . . . . ?
C103 C104 C105 C106 -0.2(4) . . . . ?
C104 C105 C106 C101 0.8(4) . . . . ?
C102 C101 C106 C105 -0.8(3) . . . . ?
C10 C101 C106 C105 173.6(2) . . . . ?
C3A C1A C2A C3A 0.4(4) 7_665 . . . ?
C1A C2A C3A C1A -0.4(4) . . . 7_665 ?

# End of CIF ============================================================

# Attachment '14b.cif'

#==========================================================================
data_14b
_database_code_depnum_ccdc_archive 'CCDC 811676'
#TrackingRef '14b.cif'

#==========================================================================
# CHEMICAL DATA

_chemical_name_systematic        
;
4-(4-chlorophenyl)-2-phenyl-N-hydroxy decahydroquinoline

;
_chemical_name_common            
'4-(4-chlorophenyl)-2-phenyl-N-hydroxy decahydroquinoline'
_chemical_melting_point          201-203
_chemical_formula_moiety         'C21 H24 Cl N O'
_chemical_formula_sum            'C21 H24 Cl N O'
_chemical_formula_weight         341.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==========================================================================

# CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   19.532(3)
_cell_length_b                   5.3933(7)
_cell_length_c                   16.414(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.279(12)
_cell_angle_gamma                90.00
_cell_volume                     1729.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    1234
_cell_measurement_theta_min      4.53
_cell_measurement_theta_max      59.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    1.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7815
_exptl_absorpt_correction_T_max  0.8897
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
#==========================================================================

# Experimental data

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6910
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0687
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         59.99

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        59.99
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.051
_chemical_absolute_configuration ad
_reflns_number_total             2353
_reflns_number_gt                1907
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'FRAMBO (BRUKER-NONIUS, 2003)'
_computing_cell_refinement       
;
CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003)
;
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'Bruker SHELXTL'
#==========================================================================

# Refinement data

_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^ > 2sigma(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
[0.00000+1.00000exp(1.00(sin\q/\l)^2^)]/
[\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0471P)^2^+0.0000sin\q/\l]
where P = 0.33333Fo^2^ + 0.66667Fc^2^

;
_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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_number_reflns         2353
_refine_ls_number_parameters     217
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
Cl1 Cl 0.09750(4) -0.01817(18) 0.50694(5) 0.0347(3) Uani 1 1 d . . .
O1 O 0.49176(12) 0.2251(5) 0.90721(14) 0.0281(6) Uani 1 1 d D . .
H1O H 0.5273 0.1374 0.8998 0.042 Uiso 1 1 d RD . .
C1 C 0.45266(18) 0.2473(7) 0.7735(2) 0.0225(8) Uani 1 1 d . . .
H1A H 0.4473 0.4282 0.7852 0.027 Uiso 1 1 calc R . .
N1 N 0.44353(14) 0.1075(5) 0.85030(17) 0.0211(7) Uani 1 1 d . . .
C4 C 0.32072(17) 0.0653(7) 0.8280(2) 0.0213(8) Uani 1 1 d . . .
H4A H 0.2750 0.0906 0.8524 0.026 Uiso 1 1 calc R . .
H4B H 0.3267 -0.1144 0.8180 0.026 Uiso 1 1 calc R . .
C3 C 0.32505(17) 0.2067(7) 0.7471(2) 0.0203(8) Uani 1 1 d . . .
H3A H 0.3206 0.3869 0.7603 0.024 Uiso 1 1 calc R . .
C7 C 0.53354(18) -0.0621(7) 0.7100(2) 0.0257(9) Uani 1 1 d . . .
H7A H 0.5803 -0.0827 0.6881 0.031 Uiso 1 1 calc R . .
H7B H 0.5281 -0.1775 0.7565 0.031 Uiso 1 1 calc R . .
C19 C 0.16427(16) 0.0448(7) 0.5744(2) 0.0214(9) Uani 1 1 d . . .
C21 C 0.22821(17) -0.0662(7) 0.6936(2) 0.0243(9) Uani 1 1 d . . .
H21A H 0.2363 -0.1780 0.7373 0.029 Uiso 1 1 calc R . .
C18 C 0.20306(18) 0.2546(7) 0.5653(2) 0.0272(9) Uani 1 1 d . . .
H18A H 0.1944 0.3655 0.5215 0.033 Uiso 1 1 calc R . .
C16 C 0.26836(18) 0.1452(7) 0.6867(2) 0.0209(8) Uani 1 1 d . . .
C13 C 0.35451(19) -0.1978(7) 1.1207(2) 0.0291(9) Uani 1 1 d . . .
H13A H 0.3496 -0.2739 1.1725 0.035 Uiso 1 1 calc R . .
C20 C 0.17615(18) -0.1178(7) 0.6376(2) 0.0252(9) Uani 1 1 d . . .
H20A H 0.1492 -0.2635 0.6430 0.030 Uiso 1 1 calc R . .
C12 C 0.31743(18) 0.0120(8) 1.1015(2) 0.0283(9) Uani 1 1 d . . .
H12A H 0.2868 0.0799 1.1404 0.034 Uiso 1 1 calc R . .
C17 C 0.25557(19) 0.3034(7) 0.6213(2) 0.0270(9) Uani 1 1 d . . .
H17A H 0.2830 0.4472 0.6146 0.032 Uiso 1 1 calc R . .
C9 C 0.40868(18) -0.0891(7) 0.6771(2) 0.0253(9) Uani 1 1 d . . .
H9A H 0.3752 -0.1205 0.6328 0.030 Uiso 1 1 calc R . .
H9B H 0.4004 -0.2121 0.7207 0.030 Uiso 1 1 calc R . .
C5 C 0.37589(17) 0.1558(7) 0.8870(2) 0.0208(8) Uani 1 1 d . . .
H5A H 0.3705 0.3386 0.8949 0.025 Uiso 1 1 calc R . .
C6 C 0.52400(18) 0.2035(7) 0.7394(2) 0.0264(9) Uani 1 1 d . . .
H6A H 0.5585 0.2404 0.7821 0.032 Uiso 1 1 calc R . .
H6B H 0.5319 0.3186 0.6933 0.032 Uiso 1 1 calc R . .
C15 C 0.40606(19) -0.1857(7) 0.9876(2) 0.0259(9) Uani 1 1 d . . .
H15A H 0.4359 -0.2563 0.9484 0.031 Uiso 1 1 calc R . .
C2 C 0.39740(17) 0.1693(7) 0.7107(2) 0.0215(8) Uani 1 1 d . . .
H2A H 0.4013 0.2863 0.6637 0.026 Uiso 1 1 calc R . .
C14 C 0.3989(2) -0.2968(7) 1.0639(2) 0.0282(9) Uani 1 1 d . . .
H14A H 0.4247 -0.4411 1.0768 0.034 Uiso 1 1 calc R . .
C10 C 0.36939(17) 0.0290(7) 0.9689(2) 0.0220(8) Uani 1 1 d . . .
C8 C 0.48120(17) -0.1243(7) 0.6441(2) 0.0271(9) Uani 1 1 d . . .
H8A H 0.4874 -0.2982 0.6262 0.032 Uiso 1 1 calc R . .
H8B H 0.4882 -0.0151 0.5964 0.032 Uiso 1 1 calc R . .
C11 C 0.32429(18) 0.1246(7) 1.0262(2) 0.0237(9) Uani 1 1 d . . .
H11A H 0.2980 0.2680 1.0136 0.028 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
Cl1 0.0252(5) 0.0560(7) 0.0229(4) -0.0020(5) -0.0064(4) -0.0026(5)
O1 0.0196(14) 0.0390(16) 0.0255(13) -0.0023(12) -0.0096(11) -0.0058(12)
C1 0.026(2) 0.022(2) 0.0191(18) 0.0019(15) -0.0031(16) -0.0029(16)
N1 0.0145(15) 0.0311(18) 0.0178(15) 0.0039(13) -0.0063(13) -0.0053(13)
C4 0.0147(17) 0.029(2) 0.0200(17) 0.0010(15) -0.0029(15) 0.0004(14)
C3 0.0196(19) 0.021(2) 0.0202(18) -0.0014(15) -0.0066(16) 0.0011(16)
C7 0.0200(18) 0.030(2) 0.0271(19) -0.0030(17) -0.0004(16) 0.0011(17)
C19 0.0144(18) 0.033(2) 0.0170(18) -0.0062(17) 0.0002(15) 0.0004(16)
C21 0.0211(18) 0.028(2) 0.0236(18) 0.0053(17) -0.0026(16) -0.0015(17)
C18 0.024(2) 0.037(2) 0.022(2) 0.0000(18) -0.0056(17) 0.0014(18)
C16 0.020(2) 0.027(2) 0.0160(18) 0.0014(16) -0.0001(16) 0.0006(16)
C13 0.026(2) 0.038(3) 0.0227(19) 0.0038(18) -0.0065(18) -0.0113(18)
C20 0.024(2) 0.031(2) 0.021(2) -0.0011(17) 0.0010(17) -0.0022(17)
C12 0.031(2) 0.034(2) 0.0192(18) -0.0073(19) 0.0024(16) -0.003(2)
C17 0.026(2) 0.033(2) 0.0221(19) 0.0021(18) -0.0038(17) -0.0011(16)
C9 0.026(2) 0.029(2) 0.0199(18) -0.0021(16) -0.0022(16) -0.0026(16)
C5 0.020(2) 0.022(2) 0.0197(18) -0.0008(16) -0.0022(16) 0.0006(15)
C6 0.018(2) 0.034(2) 0.028(2) 0.0037(17) 0.0001(17) -0.0040(17)
C15 0.021(2) 0.026(2) 0.030(2) -0.0002(17) -0.0047(18) 0.0026(16)
C2 0.0170(18) 0.027(2) 0.0200(18) 0.0058(16) 0.0012(16) 0.0010(15)
C14 0.031(2) 0.025(2) 0.028(2) 0.0075(17) -0.0087(19) -0.0079(17)
C10 0.0214(18) 0.026(2) 0.0189(17) -0.0007(16) -0.0034(16) -0.0051(16)
C8 0.023(2) 0.031(2) 0.027(2) -0.0036(17) -0.0028(17) 0.0037(16)
C11 0.024(2) 0.022(2) 0.025(2) -0.0036(17) -0.0047(17) -0.0001(16)
#==========================================================================

# MOLECULAR GEOMETRY

_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
Cl1 C19 1.740(3) . ?
O1 H1O 0.8499 . ?
O1 N1 1.468(3) . ?
O1 H1O 0.8499 . ?
C1 N1 1.481(4) . ?
C1 C6 1.523(5) . ?
C1 C2 1.546(5) . ?
C1 H1A 1.0000 . ?
N1 C5 1.478(4) . ?
C4 C5 1.526(5) . ?
C4 C3 1.535(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 C16 1.518(5) . ?
C3 C2 1.550(5) . ?
C3 H3A 1.0000 . ?
C7 C8 1.523(5) . ?
C7 C6 1.523(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C19 C18 1.370(5) . ?
C19 C20 1.376(5) . ?
C21 C16 1.389(5) . ?
C21 C20 1.396(5) . ?
C21 H21A 0.9500 . ?
C18 C17 1.399(5) . ?
C18 H18A 0.9500 . ?
C16 C17 1.393(5) . ?
C13 C12 1.379(6) . ?
C13 C14 1.384(5) . ?
C13 H13A 0.9500 . ?
C20 H20A 0.9500 . ?
C12 C11 1.384(5) . ?
C12 H12A 0.9500 . ?
C17 H17A 0.9500 . ?
C9 C2 1.516(5) . ?
C9 C8 1.531(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C5 C10 1.514(5) . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C15 C10 1.395(5) . ?
C15 C14 1.396(5) . ?
C15 H15A 0.9500 . ?
C2 H2A 1.0000 . ?
C14 H14A 0.9500 . ?
C10 C11 1.390(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C11 H11A 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
H1O O1 N1 101.0 . . ?
H1O O1 H1O 0.0 . . ?
N1 O1 H1O 101.0 . . ?
N1 C1 C6 110.4(3) . . ?
N1 C1 C2 110.0(3) . . ?
C6 C1 C2 110.5(3) . . ?
N1 C1 H1A 108.6 . . ?
C6 C1 H1A 108.6 . . ?
C2 C1 H1A 108.6 . . ?
O1 N1 C5 103.7(2) . . ?
O1 N1 C1 104.0(2) . . ?
C5 N1 C1 111.7(3) . . ?
C5 C4 C3 110.4(3) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C16 C3 C4 114.4(3) . . ?
C16 C3 C2 112.6(3) . . ?
C4 C3 C2 108.8(3) . . ?
C16 C3 H3A 106.9 . . ?
C4 C3 H3A 106.9 . . ?
C2 C3 H3A 106.9 . . ?
C8 C7 C6 110.4(3) . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C18 C19 C20 121.1(3) . . ?
C18 C19 Cl1 120.3(3) . . ?
C20 C19 Cl1 118.6(3) . . ?
C16 C21 C20 121.3(3) . . ?
C16 C21 H21A 119.3 . . ?
C20 C21 H21A 119.3 . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
C21 C16 C17 117.8(3) . . ?
C21 C16 C3 122.5(3) . . ?
C17 C16 C3 119.8(3) . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C19 C20 C21 119.3(3) . . ?
C19 C20 H20A 120.4 . . ?
C21 C20 H20A 120.4 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C16 C17 C18 121.3(4) . . ?
C16 C17 H17A 119.4 . . ?
C18 C17 H17A 119.4 . . ?
C2 C9 C8 112.3(3) . . ?
C2 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C2 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
N1 C5 C10 111.2(3) . . ?
N1 C5 C4 108.3(3) . . ?
C10 C5 C4 110.9(3) . . ?
N1 C5 H5A 108.8 . . ?
C10 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C1 C6 C7 112.1(3) . . ?
C1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C10 C15 C14 120.0(4) . . ?
C10 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C9 C2 C1 113.0(3) . . ?
C9 C2 C3 113.2(3) . . ?
C1 C2 C3 110.1(3) . . ?
C9 C2 H2A 106.7 . . ?
C1 C2 H2A 106.7 . . ?
C3 C2 H2A 106.7 . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C11 C10 C15 119.1(3) . . ?
C11 C10 C5 119.3(3) . . ?
C15 C10 C5 121.6(3) . . ?
C7 C8 C9 109.9(3) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?

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
H1O O1 N1 C5 152.3 . . . . ?
H1O O1 N1 C1 -90.8 . . . . ?
C6 C1 N1 O1 66.1(3) . . . . ?
C2 C1 N1 O1 -171.8(3) . . . . ?
C6 C1 N1 C5 177.2(3) . . . . ?
C2 C1 N1 C5 -60.6(4) . . . . ?
C5 C4 C3 C16 -175.1(3) . . . . ?
C5 C4 C3 C2 58.1(4) . . . . ?
C20 C19 C18 C17 0.0(5) . . . . ?
Cl1 C19 C18 C17 178.7(3) . . . . ?
C20 C21 C16 C17 -0.8(5) . . . . ?
C20 C21 C16 C3 179.6(3) . . . . ?
C4 C3 C16 C21 -17.4(5) . . . . ?
C2 C3 C16 C21 107.5(4) . . . . ?
C4 C3 C16 C17 163.0(3) . . . . ?
C2 C3 C16 C17 -72.0(4) . . . . ?
C18 C19 C20 C21 0.6(5) . . . . ?
Cl1 C19 C20 C21 -178.1(3) . . . . ?
C16 C21 C20 C19 -0.2(5) . . . . ?
C14 C13 C12 C11 -0.1(5) . . . . ?
C21 C16 C17 C18 1.4(5) . . . . ?
C3 C16 C17 C18 -179.0(4) . . . . ?
C19 C18 C17 C16 -1.0(6) . . . . ?
O1 N1 C5 C10 -63.9(3) . . . . ?
C1 N1 C5 C10 -175.3(3) . . . . ?
O1 N1 C5 C4 174.0(3) . . . . ?
C1 N1 C5 C4 62.6(4) . . . . ?
C3 C4 C5 N1 -61.2(4) . . . . ?
C3 C4 C5 C10 176.5(3) . . . . ?
N1 C1 C6 C7 68.0(4) . . . . ?
C2 C1 C6 C7 -53.9(4) . . . . ?
C8 C7 C6 C1 59.0(4) . . . . ?
C8 C9 C2 C1 -52.1(4) . . . . ?
C8 C9 C2 C3 -178.1(3) . . . . ?
N1 C1 C2 C9 -71.6(4) . . . . ?
C6 C1 C2 C9 50.5(4) . . . . ?
N1 C1 C2 C3 56.1(4) . . . . ?
C6 C1 C2 C3 178.2(3) . . . . ?
C16 C3 C2 C9 -55.3(4) . . . . ?
C4 C3 C2 C9 72.6(4) . . . . ?
C16 C3 C2 C1 177.2(3) . . . . ?
C4 C3 C2 C1 -54.9(4) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C10 C15 C14 C13 1.3(5) . . . . ?
C14 C15 C10 C11 -2.1(5) . . . . ?
C14 C15 C10 C5 179.8(3) . . . . ?
N1 C5 C10 C11 154.6(3) . . . . ?
C4 C5 C10 C11 -84.7(4) . . . . ?
N1 C5 C10 C15 -27.3(4) . . . . ?
C4 C5 C10 C15 93.4(4) . . . . ?
C6 C7 C8 C9 -58.4(4) . . . . ?
C2 C9 C8 C7 55.5(4) . . . . ?
C13 C12 C11 C10 -0.7(5) . . . . ?
C15 C10 C11 C12 1.8(5) . . . . ?
C5 C10 C11 C12 180.0(3) . . . . ?

# End of CIF ============================================================

# Attachment '3a.cif'

#==========================================================================
data_3a
_database_code_depnum_ccdc_archive 'CCDC 811677'
#TrackingRef '3a.cif'

#==========================================================================
# CHEMICAL DATA

_chemical_name_systematic        
;
1-hydroxy2,4, 6-triiphenylpiperazine

;
_chemical_name_common            '1-hydroxy2,4, 6-triiphenylpiperazine'
_chemical_melting_point          140-142
_chemical_formula_moiety         'C22 H22 N2 O'
_chemical_formula_sum            'C22 H22 N2 O'
_chemical_formula_weight         330.42

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'
#==========================================================================

# CRYSTAL DATA

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   26.535(3)
_cell_length_b                   26.535(3)
_cell_length_c                   13.671(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     8336(2)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3168
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_T_max  0.9784
_exptl_absorpt_process_details   ?

#==========================================================================

# Experimental data

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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            29871
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         27.49
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.033
_reflns_number_total             4236
_reflns_number_gt                2591
_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  ?
#==========================================================================

# Refinement data

_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^ > 2sigma(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^)+(0.1057P)^2^+0.0000P] 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         4236
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1962
_refine_ls_wR_factor_gt          0.1764
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.75656(7) 0.03325(8) 0.58992(12) 0.0534(4) Uani 1 1 d . . .
H1 H 0.7520 -0.0038 0.6127 0.064 Uiso 1 1 calc R . .
C2 C 0.78819(8) 0.07908(11) 0.66769(15) 0.0783(7) Uani 1 1 d . . .
H2A H 0.7913 0.1155 0.6471 0.094 Uiso 1 1 calc R . .
H2B H 0.7662 0.0671 0.7282 0.094 Uiso 1 1 calc R . .
C3 C 0.87950(8) 0.10294(11) 0.59396(14) 0.0773(7) Uani 1 1 d . . .
H3A H 0.9176 0.1076 0.6066 0.093 Uiso 1 1 calc R . .
H3B H 0.8850 0.1398 0.5700 0.093 Uiso 1 1 calc R . .
C4 C 0.84854(7) 0.05652(8) 0.51718(12) 0.0542(4) Uani 1 1 d . . .
H4 H 0.8434 0.0195 0.5417 0.065 Uiso 1 1 calc R . .
C5 C 0.69724(7) 0.02571(7) 0.57241(13) 0.0530(4) Uani 1 1 d . . .
C6 C 0.68991(9) 0.06806(9) 0.52740(16) 0.0698(6) Uani 1 1 d . . .
H6 H 0.7222 0.1014 0.5038 0.084 Uiso 1 1 calc R . .
C7 C 0.63532(11) 0.06168(12) 0.51685(18) 0.0847(7) Uani 1 1 d . . .
H7 H 0.6312 0.0910 0.4872 0.102 Uiso 1 1 calc R . .
C8 C 0.58762(10) 0.01292(14) 0.5495(2) 0.0895(8) Uani 1 1 d . . .
H8 H 0.5508 0.0084 0.5410 0.107 Uiso 1 1 calc R . .
C9 C 0.59378(10) -0.02948(12) 0.5949(2) 0.0927(8) Uani 1 1 d . . .
H9 H 0.5612 -0.0627 0.6182 0.111 Uiso 1 1 calc R . .
C10 C 0.64848(8) -0.02309(9) 0.60628(16) 0.0728(6) Uani 1 1 d . . .
H10 H 0.6523 -0.0522 0.6372 0.087 Uiso 1 1 calc R . .
C11 C 0.87123(8) 0.09846(8) 0.77502(14) 0.0609(5) Uani 1 1 d . . .
C12 C 0.84182(11) 0.09853(12) 0.85789(16) 0.0919(8) Uani 1 1 d . . .
H12 H 0.8048 0.0939 0.8519 0.110 Uiso 1 1 calc R . .
C13 C 0.86592(14) 0.10530(15) 0.94953(19) 0.1202(12) Uani 1 1 d . . .
H13 H 0.8451 0.1056 1.0041 0.144 Uiso 1 1 calc R . .
C14 C 0.91962(16) 0.11157(14) 0.9617(2) 0.1163(10) Uani 1 1 d . . .
H14 H 0.9351 0.1147 1.0239 0.140 Uiso 1 1 calc R . .
C15 C 0.95020(13) 0.11324(12) 0.8806(2) 0.1008(9) Uani 1 1 d . . .
H15 H 0.9873 0.1182 0.8876 0.121 Uiso 1 1 calc R . .
C16 C 0.92716(10) 0.10765(11) 0.78883(17) 0.0841(7) Uani 1 1 d . . .
H16 H 0.9494 0.1101 0.7346 0.101 Uiso 1 1 calc R . .
C17 C 0.88383(7) 0.07253(8) 0.42438(12) 0.0543(5) Uani 1 1 d . . .
C18 C 0.91727(9) 0.04743(10) 0.40252(15) 0.0712(6) Uani 1 1 d . . .
H18 H 0.9165 0.0192 0.4438 0.085 Uiso 1 1 calc R . .
C19 C 0.95204(10) 0.06407(12) 0.31954(19) 0.0931(8) Uani 1 1 d . . .
H19 H 0.9744 0.0470 0.3058 0.112 Uiso 1 1 calc R . .
C20 C 0.95367(10) 0.10485(13) 0.25857(18) 0.0935(8) Uani 1 1 d . . .
H20 H 0.9769 0.1156 0.2029 0.112 Uiso 1 1 calc R . .
C21 C 0.92119(11) 0.13026(13) 0.27894(16) 0.0906(8) Uani 1 1 d . . .
H21 H 0.9224 0.1585 0.2370 0.109 Uiso 1 1 calc R . .
C22 C 0.88629(9) 0.11438(10) 0.36182(15) 0.0729(6) Uani 1 1 d . . .
H22 H 0.8644 0.1321 0.3752 0.087 Uiso 1 1 calc R . .
N1 N 0.79096(6) 0.05031(6) 0.49970(10) 0.0481(4) Uani 1 1 d . . .
N2 N 0.84612(7) 0.08752(10) 0.68432(12) 0.0907(7) Uani 1 1 d . . .
O1 O 0.76134(5) 0.00046(5) 0.43536(9) 0.0615(4) Uani 1 1 d . . .
H1O H 0.7534 0.0141 0.3853 0.092 Uiso 1 1 d 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
C1 0.0501(10) 0.0568(10) 0.0498(10) 0.0030(8) 0.0027(8) 0.0241(8)
C2 0.0541(12) 0.1099(18) 0.0578(12) -0.0250(11) -0.0046(9) 0.0311(11)
C3 0.0503(11) 0.1123(17) 0.0539(12) -0.0186(11) -0.0033(8) 0.0291(11)
C4 0.0512(10) 0.0648(11) 0.0477(9) 0.0019(8) 0.0008(8) 0.0298(9)
C5 0.0492(10) 0.0528(10) 0.0512(10) -0.0086(8) 0.0008(7) 0.0212(8)
C6 0.0607(12) 0.0688(13) 0.0782(14) 0.0027(10) -0.0008(10) 0.0312(10)
C7 0.0755(15) 0.0999(18) 0.0925(17) -0.0095(14) -0.0133(13) 0.0542(15)
C8 0.0607(14) 0.115(2) 0.0968(18) -0.0348(15) -0.0144(12) 0.0473(15)
C9 0.0506(13) 0.0882(17) 0.112(2) -0.0153(15) 0.0115(12) 0.0141(12)
C10 0.0583(12) 0.0636(12) 0.0858(15) 0.0011(10) 0.0091(10) 0.0223(10)
C11 0.0634(12) 0.0526(10) 0.0507(11) -0.0118(8) -0.0065(9) 0.0171(9)
C12 0.0783(15) 0.116(2) 0.0557(13) -0.0021(12) 0.0042(11) 0.0291(14)
C13 0.106(2) 0.153(3) 0.0552(15) 0.0082(15) 0.0034(14) 0.031(2)
C14 0.130(3) 0.124(2) 0.0661(17) 0.0094(15) -0.0279(17) 0.042(2)
C15 0.105(2) 0.112(2) 0.0854(18) -0.0133(15) -0.0310(16) 0.0537(17)
C16 0.0768(15) 0.1043(18) 0.0691(14) -0.0239(12) -0.0162(11) 0.0436(13)
C17 0.0469(9) 0.0627(11) 0.0471(10) -0.0052(8) -0.0034(7) 0.0228(8)
C18 0.0629(12) 0.0777(13) 0.0714(13) -0.0093(10) 0.0046(10) 0.0341(11)
C19 0.0724(15) 0.116(2) 0.0866(18) -0.0253(16) 0.0103(13) 0.0437(15)
C20 0.0634(14) 0.126(2) 0.0598(14) -0.0082(15) 0.0085(11) 0.0237(15)
C21 0.0737(15) 0.1108(19) 0.0591(13) 0.0220(13) 0.0019(11) 0.0249(14)
C22 0.0678(13) 0.0867(14) 0.0606(12) 0.0118(11) 0.0023(10) 0.0360(11)
N1 0.0480(8) 0.0452(7) 0.0462(8) -0.0055(6) -0.0033(6) 0.0195(6)
N2 0.0528(10) 0.1547(19) 0.0488(10) -0.0242(11) -0.0060(8) 0.0401(11)
O1 0.0619(8) 0.0546(7) 0.0605(8) -0.0141(6) -0.0069(6) 0.0235(6)
#==========================================================================

# MOLECULAR GEOMETRY

_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 N1 1.465(2) . ?
C1 C5 1.503(2) . ?
C1 C2 1.514(2) . ?
C2 N2 1.456(3) . ?
C3 N2 1.454(3) . ?
C3 C4 1.511(3) . ?
C4 N1 1.472(2) . ?
C4 C17 1.506(2) . ?
C5 C10 1.375(3) . ?
C5 C6 1.378(3) . ?
C6 C7 1.379(3) . ?
C7 C8 1.356(4) . ?
C8 C9 1.364(4) . ?
C9 C10 1.383(3) . ?
C11 N2 1.368(2) . ?
C11 C12 1.376(3) . ?
C11 C16 1.391(3) . ?
C12 C13 1.377(3) . ?
C13 C14 1.359(4) . ?
C14 C15 1.361(4) . ?
C15 C16 1.371(3) . ?
C17 C18 1.383(3) . ?
C17 C22 1.377(3) . ?
C18 C19 1.388(3) . ?
C19 C20 1.349(4) . ?
C20 C21 1.362(4) . ?
C21 C22 1.389(3) . ?
N1 O1 1.4496(16) . ?

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
N1 C1 C5 110.87(14) . . ?
N1 C1 C2 109.47(15) . . ?
C5 C1 C2 109.98(15) . . ?
N2 C2 C1 110.60(17) . . ?
N2 C3 C4 110.75(17) . . ?
N1 C4 C17 111.03(14) . . ?
N1 C4 C3 108.35(15) . . ?
C17 C4 C3 110.32(15) . . ?
C10 C5 C6 117.95(18) . . ?
C10 C5 C1 120.09(17) . . ?
C6 C5 C1 121.87(16) . . ?
C7 C6 C5 121.0(2) . . ?
C8 C7 C6 120.3(2) . . ?
C7 C8 C9 119.8(2) . . ?
C8 C9 C10 120.1(2) . . ?
C5 C10 C9 120.9(2) . . ?
N2 C11 C12 122.0(2) . . ?
N2 C11 C16 121.59(19) . . ?
C12 C11 C16 116.4(2) . . ?
C11 C12 C13 121.5(3) . . ?
C14 C13 C12 121.1(3) . . ?
C15 C14 C13 118.4(2) . . ?
C14 C15 C16 121.0(3) . . ?
C15 C16 C11 121.5(2) . . ?
C18 C17 C22 118.10(18) . . ?
C18 C17 C4 120.29(17) . . ?
C22 C17 C4 121.52(17) . . ?
C17 C18 C19 120.5(2) . . ?
C20 C19 C18 120.6(2) . . ?
C19 C20 C21 119.7(2) . . ?
C20 C21 C22 120.5(2) . . ?
C17 C22 C21 120.5(2) . . ?
O1 N1 C1 105.02(12) . . ?
O1 N1 C4 105.04(12) . . ?
C1 N1 C4 110.45(13) . . ?
C11 N2 C3 123.12(16) . . ?
C11 N2 C2 122.61(16) . . ?
C3 N2 C2 110.99(17) . . ?

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
N1 C1 C2 N2 -57.0(2) . . . . ?
C5 C1 C2 N2 -179.10(18) . . . . ?
N2 C3 C4 N1 59.0(2) . . . . ?
N2 C3 C4 C17 -179.26(17) . . . . ?
N1 C1 C5 C10 132.24(18) . . . . ?
C2 C1 C5 C10 -106.5(2) . . . . ?
N1 C1 C5 C6 -51.3(2) . . . . ?
C2 C1 C5 C6 69.9(2) . . . . ?
C10 C5 C6 C7 0.1(3) . . . . ?
C1 C5 C6 C7 -176.39(19) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
C6 C7 C8 C9 1.4(4) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C6 C5 C10 C9 0.3(3) . . . . ?
C1 C5 C10 C9 176.93(19) . . . . ?
C8 C9 C10 C5 0.0(4) . . . . ?
N2 C11 C12 C13 175.1(3) . . . . ?
C16 C11 C12 C13 -2.2(4) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C12 C13 C14 C15 2.4(5) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C14 C15 C16 C11 -1.8(4) . . . . ?
N2 C11 C16 C15 -173.9(2) . . . . ?
C12 C11 C16 C15 3.5(3) . . . . ?
N1 C4 C17 C18 -139.22(17) . . . . ?
C3 C4 C17 C18 100.6(2) . . . . ?
N1 C4 C17 C22 44.2(2) . . . . ?
C3 C4 C17 C22 -75.9(2) . . . . ?
C22 C17 C18 C19 -0.2(3) . . . . ?
C4 C17 C18 C19 -176.88(18) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C18 C17 C22 C21 0.5(3) . . . . ?
C4 C17 C22 C21 177.10(19) . . . . ?
C20 C21 C22 C17 -0.3(3) . . . . ?
C5 C1 N1 O1 -66.20(16) . . . . ?
C2 C1 N1 O1 172.29(15) . . . . ?
C5 C1 N1 C4 -178.95(13) . . . . ?
C2 C1 N1 C4 59.53(19) . . . . ?
C17 C4 N1 O1 65.78(16) . . . . ?
C3 C4 N1 O1 -172.92(14) . . . . ?
C17 C4 N1 C1 178.52(14) . . . . ?
C3 C4 N1 C1 -60.18(19) . . . . ?
C12 C11 N2 C3 161.9(2) . . . . ?
C16 C11 N2 C3 -20.9(4) . . . . ?
C12 C11 N2 C2 4.3(4) . . . . ?
C16 C11 N2 C2 -178.6(2) . . . . ?
C4 C3 N2 C11 142.1(2) . . . . ?
C4 C3 N2 C2 -58.0(3) . . . . ?
C1 C2 N2 C11 -143.3(2) . . . . ?
C1 C2 N2 C3 56.6(3) . . . . ?

# End of CIF ============================================================

# Attachment '8b.cif'

#==========================================================================
data_8b
_database_code_depnum_ccdc_archive 'CCDC 811678'
#TrackingRef '8b.cif'

#==========================================================================

# CHEMICAL DATA

_chemical_name_common            '14 December 2010'
_chemical_melting_point          171-173
_chemical_formula_moiety         'C22 H22 N2 O'
_chemical_formula_sum            'C22 H22 N2 O'
_chemical_formula_weight         330.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==========================================================================

# CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.2211(3)
_cell_length_b                   14.2500(7)
_cell_length_c                   19.7004(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1746.45(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    5447
_cell_measurement_theta_min      3.83
_cell_measurement_theta_max      60.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8537
_exptl_absorpt_correction_T_max  0.8885
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24442
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         60.00
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        60.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.039
_chemical_absolute_configuration unk
_reflns_number_total             2557
_reflns_number_gt                2365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'FRAMBO (BRUKER-NONIUS, 2003)'
_computing_cell_refinement       
;
CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003)
;
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'Bruker SHELXTL'
#==========================================================================

# Refinement data

_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^ > 2sigma(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^)+(0.0460P)^2^+0.0000P] 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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0125(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_number_reflns         2557
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.3974(2) 0.51109(9) 0.83060(6) 0.0195(3) Uani 1 1 d . . .
H1A H 0.5404 0.5093 0.8538 0.023 Uiso 1 1 calc R . .
C2 C 0.2933(2) 0.60660(10) 0.84318(7) 0.0231(3) Uani 1 1 d . . .
H2A H 0.2819 0.6168 0.8928 0.028 Uiso 1 1 calc R . .
H2B H 0.1456 0.6056 0.8245 0.028 Uiso 1 1 calc R . .
C3 C 0.4156(2) 0.68931(9) 0.81180(7) 0.0220(3) Uani 1 1 d . . .
H3A H 0.3149 0.7440 0.8120 0.026 Uiso 1 1 calc R . .
C4 C 0.4615(2) 0.66608(9) 0.73695(7) 0.0211(3) Uani 1 1 d . . .
H4A H 0.3246 0.6663 0.7113 0.025 Uiso 1 1 calc R . .
H4B H 0.5552 0.7154 0.7175 0.025 Uiso 1 1 calc R . .
C5 C 0.5704(2) 0.57047(9) 0.72838(6) 0.0206(3) Uani 1 1 d . . .
H5A H 0.7098 0.5705 0.7536 0.025 Uiso 1 1 calc R . .
C6 C 0.2600(2) 0.43121(9) 0.85708(6) 0.0202(3) Uani 1 1 d . . .
C7 C 0.0537(2) 0.41699(10) 0.83180(7) 0.0233(3) Uani 1 1 d . . .
H7A H -0.0022 0.4589 0.7987 0.028 Uiso 1 1 calc R . .
C8 C -0.0713(2) 0.34286(10) 0.85401(7) 0.0249(4) Uani 1 1 d . . .
H8A H -0.2116 0.3340 0.8361 0.030 Uiso 1 1 calc R . .
C9 C 0.0081(2) 0.28166(10) 0.90224(7) 0.0271(4) Uani 1 1 d . . .
H9A H -0.0782 0.2312 0.9180 0.033 Uiso 1 1 calc R . .
C10 C 0.2129(2) 0.29407(10) 0.92743(7) 0.0284(4) Uani 1 1 d . . .
H10A H 0.2684 0.2515 0.9601 0.034 Uiso 1 1 calc R . .
C11 C 0.3380(2) 0.36843(9) 0.90526(7) 0.0240(4) Uani 1 1 d . . .
H11A H 0.4786 0.3767 0.9231 0.029 Uiso 1 1 calc R . .
C12 C 0.6175(2) 0.72043(9) 0.84916(7) 0.0209(3) Uani 1 1 d . . .
C13 C 0.6883(2) 0.68388(10) 0.91065(7) 0.0250(3) Uani 1 1 d . . .
H13A H 0.6127 0.6336 0.9315 0.030 Uiso 1 1 calc R . .
C14 C 0.8698(3) 0.72107(10) 0.94146(7) 0.0272(4) Uani 1 1 d . . .
H14A H 0.9194 0.6967 0.9835 0.033 Uiso 1 1 calc R . .
C15 C 0.9772(2) 0.79373(10) 0.91040(7) 0.0268(4) Uani 1 1 d . . .
H15A H 1.1020 0.8204 0.9303 0.032 Uiso 1 1 calc R . .
C16 C 0.8979(2) 0.82686(10) 0.84909(7) 0.0281(4) Uani 1 1 d . . .
H16A H 0.9719 0.8768 0.8273 0.034 Uiso 1 1 calc R . .
C17 C 0.6129(2) 0.54988(9) 0.65410(7) 0.0207(3) Uani 1 1 d . . .
C18 C 0.8173(2) 0.55689(10) 0.62754(7) 0.0250(4) Uani 1 1 d . . .
H18A H 0.9343 0.5715 0.6567 0.030 Uiso 1 1 calc R . .
C19 C 0.8549(3) 0.54294(10) 0.55875(7) 0.0286(4) Uani 1 1 d . . .
H19A H 0.9966 0.5484 0.5412 0.034 Uiso 1 1 calc R . .
C20 C 0.6875(2) 0.52135(10) 0.51612(7) 0.0276(4) Uani 1 1 d . . .
H20A H 0.7124 0.5131 0.4689 0.033 Uiso 1 1 calc R . .
C21 C 0.4828(3) 0.51166(12) 0.54223(7) 0.0321(4) Uani 1 1 d . . .
H21A H 0.3673 0.4949 0.5131 0.038 Uiso 1 1 calc R . .
C22 C 0.4455(2) 0.52627(10) 0.61054(7) 0.0292(4) Uani 1 1 d . . .
H22A H 0.3038 0.5201 0.6280 0.035 Uiso 1 1 calc R . .
N1 N 0.42946(17) 0.49819(7) 0.75699(5) 0.0197(3) Uani 1 1 d . . .
N2 N 0.72264(19) 0.79186(8) 0.81938(6) 0.0259(3) Uani 1 1 d . . .
O1 O 0.55066(14) 0.41169(6) 0.75084(4) 0.0231(2) Uani 1 1 d . . .
H1O H 0.4537 0.3738 0.7376 0.035 Uiso 1 1 d 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
C1 0.0196(7) 0.0211(8) 0.0178(7) 0.0000(6) -0.0007(6) 0.0001(6)
C2 0.0239(8) 0.0222(8) 0.0232(7) -0.0010(6) 0.0019(7) 0.0003(6)
C3 0.0237(8) 0.0170(7) 0.0253(7) 0.0012(6) 0.0001(7) 0.0030(6)
C4 0.0222(8) 0.0180(7) 0.0230(7) 0.0006(6) -0.0009(7) -0.0003(6)
C5 0.0201(7) 0.0206(8) 0.0210(7) 0.0006(6) -0.0018(6) -0.0004(6)
C6 0.0228(8) 0.0198(8) 0.0179(7) -0.0036(6) 0.0024(6) 0.0013(6)
C7 0.0254(8) 0.0219(8) 0.0225(7) 0.0016(6) -0.0001(7) 0.0027(7)
C8 0.0224(8) 0.0253(8) 0.0271(8) -0.0032(6) 0.0001(7) -0.0017(6)
C9 0.0304(9) 0.0242(8) 0.0267(7) 0.0010(7) 0.0042(7) -0.0040(7)
C10 0.0376(9) 0.0232(8) 0.0243(8) 0.0052(7) -0.0016(7) 0.0003(7)
C11 0.0268(8) 0.0241(8) 0.0210(8) -0.0008(6) -0.0038(7) 0.0000(6)
C12 0.0251(7) 0.0147(7) 0.0229(7) -0.0028(6) 0.0028(6) 0.0037(6)
C13 0.0304(8) 0.0217(8) 0.0229(8) -0.0014(6) 0.0032(7) 0.0002(7)
C14 0.0336(9) 0.0270(8) 0.0211(7) -0.0011(7) -0.0017(7) 0.0035(7)
C15 0.0275(8) 0.0263(8) 0.0267(8) -0.0052(7) -0.0023(7) 0.0014(7)
C16 0.0291(9) 0.0223(8) 0.0327(9) -0.0006(7) -0.0018(8) -0.0038(7)
C17 0.0250(8) 0.0153(7) 0.0218(7) 0.0020(6) 0.0010(7) 0.0018(6)
C18 0.0251(9) 0.0235(8) 0.0265(8) -0.0008(6) -0.0013(7) 0.0019(6)
C19 0.0288(9) 0.0284(9) 0.0286(8) -0.0003(7) 0.0074(7) 0.0015(7)
C20 0.0393(10) 0.0235(8) 0.0202(7) -0.0011(6) 0.0035(8) 0.0061(7)
C21 0.0318(9) 0.0414(10) 0.0229(8) -0.0042(7) -0.0048(7) 0.0029(8)
C22 0.0222(9) 0.0399(9) 0.0254(8) -0.0006(7) 0.0006(7) 0.0000(7)
N1 0.0234(6) 0.0143(6) 0.0214(6) -0.0006(5) 0.0018(5) 0.0044(5)
N2 0.0289(7) 0.0206(7) 0.0282(6) 0.0010(5) 0.0000(6) -0.0020(6)
O1 0.0255(5) 0.0154(5) 0.0284(5) -0.0026(4) -0.0004(5) 0.0039(4)

_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 N1 1.4754(16) . ?
C1 C6 1.5163(19) . ?
C1 C2 1.527(2) . ?
C1 H1A 1.0000 . ?
C2 C3 1.5329(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C12 1.522(2) . ?
C3 C4 1.5381(18) . ?
C3 H3A 1.0000 . ?
C4 C5 1.5308(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.4651(17) . ?
C5 C17 1.5159(18) . ?
C5 H5A 1.0000 . ?
C6 C7 1.3915(19) . ?
C6 C11 1.3917(18) . ?
C7 C8 1.383(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.381(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.379(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 N2 1.3447(18) . ?
C12 C13 1.3902(18) . ?
C13 C14 1.387(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.376(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15A 0.9500 . ?
C16 N2 1.3344(19) . ?
C16 H16A 0.9500 . ?
C17 C18 1.379(2) . ?
C17 C22 1.391(2) . ?
C18 C19 1.3894(19) . ?
C18 H18A 0.9500 . ?
C19 C20 1.373(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.380(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.382(2) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
N1 O1 1.4500(13) . ?
O1 H1O 0.8500 . ?

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
N1 C1 C6 108.71(10) . . ?
N1 C1 C2 109.13(10) . . ?
C6 C1 C2 111.96(11) . . ?
N1 C1 H1A 109.0 . . ?
C6 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
C1 C2 C3 114.16(11) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C12 C3 C2 116.01(12) . . ?
C12 C3 C4 111.90(11) . . ?
C2 C3 C4 108.26(11) . . ?
C12 C3 H3A 106.7 . . ?
C2 C3 H3A 106.7 . . ?
C4 C3 H3A 106.7 . . ?
C5 C4 C3 112.30(11) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 C17 109.87(11) . . ?
N1 C5 C4 108.57(10) . . ?
C17 C5 C4 110.85(11) . . ?
N1 C5 H5A 109.2 . . ?
C17 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C7 C6 C11 118.18(13) . . ?
C7 C6 C1 120.42(12) . . ?
C11 C6 C1 121.37(12) . . ?
C8 C7 C6 121.10(13) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C9 C8 C7 119.94(13) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C10 C9 C8 119.81(14) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 120.25(14) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C10 C11 C6 120.71(14) . . ?
C10 C11 H11A 119.6 . . ?
C6 C11 H11A 119.6 . . ?
N2 C12 C13 120.63(13) . . ?
N2 C12 C3 114.28(12) . . ?
C13 C12 C3 125.01(13) . . ?
C14 C13 C12 119.74(14) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C15 C14 C13 119.22(13) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C14 C15 C16 118.08(14) . . ?
C14 C15 H15A 121.0 . . ?
C16 C15 H15A 121.0 . . ?
N2 C16 C15 123.03(14) . . ?
N2 C16 H16A 118.5 . . ?
C15 C16 H16A 118.5 . . ?
C18 C17 C22 118.30(13) . . ?
C18 C17 C5 120.90(12) . . ?
C22 C17 C5 120.77(12) . . ?
C17 C18 C19 121.00(14) . . ?
C17 C18 H18A 119.5 . . ?
C19 C18 H18A 119.5 . . ?
C20 C19 C18 120.07(14) . . ?
C20 C19 H19A 120.0 . . ?
C18 C19 H19A 120.0 . . ?
C19 C20 C21 119.63(13) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C20 C21 C22 120.20(14) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C21 C22 C17 120.76(14) . . ?
C21 C22 H22A 119.6 . . ?
C17 C22 H22A 119.6 . . ?
O1 N1 C5 104.74(9) . . ?
O1 N1 C1 104.96(9) . . ?
C5 N1 C1 111.80(10) . . ?
C16 N2 C12 119.29(12) . . ?
N1 O1 H1O 101.3 . . ?

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
N1 C1 C2 C3 -54.40(14) . . . . ?
C6 C1 C2 C3 -174.80(11) . . . . ?
C1 C2 C3 C12 -76.50(15) . . . . ?
C1 C2 C3 C4 50.23(15) . . . . ?
C12 C3 C4 C5 76.93(14) . . . . ?
C2 C3 C4 C5 -52.14(15) . . . . ?
C3 C4 C5 N1 59.18(14) . . . . ?
C3 C4 C5 C17 179.94(11) . . . . ?
N1 C1 C6 C7 -60.05(15) . . . . ?
C2 C1 C6 C7 60.60(15) . . . . ?
N1 C1 C6 C11 117.72(13) . . . . ?
C2 C1 C6 C11 -121.63(14) . . . . ?
C11 C6 C7 C8 0.3(2) . . . . ?
C1 C6 C7 C8 178.12(12) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C9 C10 C11 C6 -0.4(2) . . . . ?
C7 C6 C11 C10 -0.18(19) . . . . ?
C1 C6 C11 C10 -178.00(12) . . . . ?
C2 C3 C12 N2 178.72(11) . . . . ?
C4 C3 C12 N2 53.84(15) . . . . ?
C2 C3 C12 C13 -4.48(19) . . . . ?
C4 C3 C12 C13 -129.36(13) . . . . ?
N2 C12 C13 C14 -0.3(2) . . . . ?
C3 C12 C13 C14 -176.96(12) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 N2 0.4(2) . . . . ?
N1 C5 C17 C18 -135.36(13) . . . . ?
C4 C5 C17 C18 104.64(14) . . . . ?
N1 C5 C17 C22 46.66(16) . . . . ?
C4 C5 C17 C22 -73.34(16) . . . . ?
C22 C17 C18 C19 1.5(2) . . . . ?
C5 C17 C18 C19 -176.54(12) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C18 C19 C20 C21 -1.4(2) . . . . ?
C19 C20 C21 C22 1.9(2) . . . . ?
C20 C21 C22 C17 -0.7(2) . . . . ?
C18 C17 C22 C21 -1.0(2) . . . . ?
C5 C17 C22 C21 177.06(13) . . . . ?
C17 C5 N1 O1 62.33(12) . . . . ?
C4 C5 N1 O1 -176.29(9) . . . . ?
C17 C5 N1 C1 175.46(11) . . . . ?
C4 C5 N1 C1 -63.17(13) . . . . ?
C6 C1 N1 O1 -64.14(12) . . . . ?
C2 C1 N1 O1 173.48(10) . . . . ?
C6 C1 N1 C5 -177.12(10) . . . . ?
C2 C1 N1 C5 60.50(13) . . . . ?
C15 C16 N2 C12 -0.8(2) . . . . ?
C13 C12 N2 C16 0.78(19) . . . . ?
C3 C12 N2 C16 177.73(11) . . . . ?

# End of CIF ============================================================