# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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data_ao80m
#TrackingRef 'web_deposit_cif_file_0_B.Sridhar_1365510979.ao80mf.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1-(2-(dimethylamino)-5-iso-propylphenyl) dibenzo[b,d]furan-2-ol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 N O2'
_chemical_formula_weight         345.42

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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                   7.8847(5)
_cell_length_b                   11.3771(7)
_cell_length_c                   20.8098(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1866.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8434
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      26.90

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.078
_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      294(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  'CCD Area Detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18068
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0121
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1908
_reflns_number_gt                1805
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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^)+(0.0462P)^2^+0.2348P] 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         1908
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
C1 C 0.4980(3) 0.32112(17) 0.04249(10) 0.0525(5) Uani 1 1 d . . .
C2 C 0.5217(3) 0.2849(2) -0.01983(11) 0.0670(6) Uani 1 1 d . . .
H2 H 0.5902 0.2209 -0.0298 0.080 Uiso 1 1 calc R . .
C3 C 0.4396(3) 0.3478(2) -0.06676(11) 0.0669(6) Uani 1 1 d . . .
H3 H 0.4526 0.3259 -0.1095 0.080 Uiso 1 1 calc R . .
C4 C 0.3375(3) 0.44353(19) -0.05170(9) 0.0556(5) Uani 1 1 d . . .
H4 H 0.2829 0.4839 -0.0846 0.067 Uiso 1 1 calc R . .
C5 C 0.3155(3) 0.47971(17) 0.01076(9) 0.0471(5) Uani 1 1 d . . .
H5 H 0.2477 0.5443 0.0203 0.057 Uiso 1 1 calc R . .
C6 C 0.3973(2) 0.41727(15) 0.05954(9) 0.0422(4) Uani 1 1 d . . .
C7 C 0.3992(2) 0.41974(15) 0.12961(9) 0.0420(4) Uani 1 1 d . . .
C8 C 0.3197(2) 0.48930(16) 0.17672(8) 0.0425(4) Uani 1 1 d . . .
C9 C 0.3374(3) 0.45149(17) 0.24046(9) 0.0501(5) Uani 1 1 d . . .
C10 C 0.4396(3) 0.35613(19) 0.25652(10) 0.0588(6) Uani 1 1 d . . .
H10 H 0.4516 0.3358 0.2996 0.071 Uiso 1 1 calc R . .
C11 C 0.5232(3) 0.29102(19) 0.21081(11) 0.0606(6) Uani 1 1 d . . .
H11 H 0.5929 0.2282 0.2218 0.073 Uiso 1 1 calc R . .
C12 C 0.4979(3) 0.32398(17) 0.14786(10) 0.0504(5) Uani 1 1 d . . .
C13 C 0.2342(2) 0.60077(15) 0.15890(8) 0.0403(4) Uani 1 1 d . . .
C14 C 0.3244(3) 0.68077(15) 0.12147(8) 0.0423(4) Uani 1 1 d . . .
H14 H 0.4323 0.6596 0.1076 0.051 Uiso 1 1 calc R . .
C15 C 0.2627(3) 0.78972(16) 0.10376(9) 0.0469(4) Uani 1 1 d . . .
C16 C 0.1035(3) 0.81916(18) 0.12587(10) 0.0573(5) Uani 1 1 d . . .
H16 H 0.0586 0.8924 0.1156 0.069 Uiso 1 1 calc R . .
C17 C 0.0088(3) 0.74261(19) 0.16290(10) 0.0560(5) Uani 1 1 d . . .
H17 H -0.0978 0.7656 0.1773 0.067 Uiso 1 1 calc R . .
C18 C 0.0700(3) 0.63193(17) 0.17897(9) 0.0458(4) Uani 1 1 d . . .
C19 C -0.0705(3) 0.4424(2) 0.18175(13) 0.0718(7) Uani 1 1 d . . .
H19A H -0.1597 0.4596 0.1518 0.108 Uiso 1 1 calc R . .
H19B H -0.1086 0.3836 0.2116 0.108 Uiso 1 1 calc R . .
H19C H 0.0268 0.4137 0.1589 0.108 Uiso 1 1 calc R . .
C20 C -0.1747(4) 0.5969(3) 0.24941(14) 0.0879(9) Uani 1 1 d . . .
H20A H -0.1430 0.6641 0.2745 0.132 Uiso 1 1 calc R . .
H20B H -0.2219 0.5378 0.2770 0.132 Uiso 1 1 calc R . .
H20C H -0.2575 0.6196 0.2180 0.132 Uiso 1 1 calc R . .
C21 C 0.3656(3) 0.86920(18) 0.05996(10) 0.0588(6) Uani 1 1 d . . .
H21 H 0.4822 0.8395 0.0596 0.071 Uiso 1 1 calc R . .
C22 C 0.2978(6) 0.8608(3) -0.00839(12) 0.1108(12) Uani 1 1 d . . .
H22A H 0.3054 0.7810 -0.0230 0.166 Uiso 1 1 calc R . .
H22B H 0.3638 0.9105 -0.0361 0.166 Uiso 1 1 calc R . .
H22C H 0.1815 0.8857 -0.0092 0.166 Uiso 1 1 calc R . .
C23 C 0.3715(4) 0.9957(2) 0.08210(14) 0.0806(8) Uani 1 1 d . . .
H23A H 0.2602 1.0296 0.0791 0.121 Uiso 1 1 calc R . .
H23B H 0.4484 1.0392 0.0554 0.121 Uiso 1 1 calc R . .
H23C H 0.4095 0.9988 0.1259 0.121 Uiso 1 1 calc R . .
N1 N -0.0248(2) 0.54975(16) 0.21694(8) 0.0566(5) Uani 1 1 d . . .
O1 O 0.56246(19) 0.26473(12) 0.09547(8) 0.0609(4) Uani 1 1 d . . .
O2 O 0.2552(2) 0.50809(15) 0.28949(6) 0.0647(4) Uani 1 1 d . . .
H1O H 0.148(4) 0.529(3) 0.2701(12) 0.091(9) 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
C1 0.0490(11) 0.0410(9) 0.0676(12) -0.0002(9) 0.0110(11) -0.0011(10)
C2 0.0681(15) 0.0541(12) 0.0789(15) -0.0104(11) 0.0229(13) 0.0027(12)
C3 0.0758(15) 0.0643(13) 0.0604(12) -0.0187(12) 0.0208(13) -0.0150(13)
C4 0.0591(12) 0.0581(12) 0.0497(11) -0.0008(9) 0.0013(10) -0.0124(11)
C5 0.0487(11) 0.0434(10) 0.0491(10) -0.0019(8) 0.0011(9) -0.0020(9)
C6 0.0396(10) 0.0359(9) 0.0513(10) -0.0010(8) 0.0035(8) -0.0043(8)
C7 0.0402(10) 0.0354(9) 0.0504(10) 0.0053(8) -0.0026(8) -0.0043(8)
C8 0.0425(10) 0.0403(9) 0.0448(9) 0.0033(8) -0.0031(8) -0.0051(9)
C9 0.0554(11) 0.0491(10) 0.0458(10) 0.0076(9) -0.0074(9) -0.0096(10)
C10 0.0598(13) 0.0603(12) 0.0563(11) 0.0220(10) -0.0134(11) -0.0095(11)
C11 0.0512(12) 0.0499(11) 0.0807(14) 0.0245(11) -0.0107(12) 0.0002(10)
C12 0.0435(10) 0.0396(9) 0.0683(12) 0.0080(9) 0.0000(10) -0.0010(9)
C13 0.0472(10) 0.0381(9) 0.0356(8) -0.0022(7) -0.0051(8) -0.0012(8)
C14 0.0467(10) 0.0388(9) 0.0415(9) -0.0031(8) 0.0008(8) -0.0010(8)
C15 0.0553(11) 0.0386(9) 0.0468(10) -0.0017(8) -0.0001(9) -0.0006(9)
C16 0.0650(13) 0.0411(10) 0.0657(12) 0.0050(10) 0.0022(11) 0.0084(10)
C17 0.0498(12) 0.0552(11) 0.0629(12) -0.0022(10) 0.0071(10) 0.0088(10)
C18 0.0493(11) 0.0463(10) 0.0417(9) -0.0022(8) 0.0013(9) -0.0022(10)
C19 0.0627(14) 0.0648(14) 0.0880(17) 0.0071(13) 0.0011(13) -0.0199(13)
C20 0.0726(17) 0.0965(19) 0.0946(19) 0.0212(16) 0.0349(16) 0.0089(16)
C21 0.0656(14) 0.0467(11) 0.0641(13) 0.0110(10) 0.0096(11) 0.0034(11)
C22 0.151(3) 0.123(2) 0.0587(15) 0.0148(16) 0.0125(19) -0.043(3)
C23 0.0824(17) 0.0510(12) 0.1084(19) 0.0135(14) 0.0168(16) -0.0081(13)
N1 0.0531(10) 0.0604(10) 0.0564(9) 0.0058(8) 0.0110(8) -0.0027(9)
O1 0.0570(8) 0.0453(7) 0.0805(9) 0.0065(7) 0.0071(9) 0.0118(7)
O2 0.0805(11) 0.0737(10) 0.0400(7) 0.0018(7) -0.0043(8) -0.0027(10)

_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 O1 1.373(3) . ?
C1 C2 1.373(3) . ?
C1 C6 1.397(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.458(3) . ?
C7 C12 1.391(3) . ?
C7 C8 1.407(3) . ?
C8 C9 1.401(2) . ?
C8 C13 1.484(3) . ?
C9 O2 1.370(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 O1 1.379(2) . ?
C13 C14 1.393(2) . ?
C13 C18 1.405(3) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(3) . ?
C15 C21 1.519(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9300 . ?
C18 N1 1.435(2) . ?
C19 N1 1.469(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N1 1.463(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C23 1.512(3) . ?
C21 C22 1.522(3) . ?
C21 H21 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O2 H1O 0.97(3) . ?

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
O1 C1 C2 124.58(19) . . ?
O1 C1 C6 111.84(17) . . ?
C2 C1 C6 123.5(2) . . ?
C3 C2 C1 116.8(2) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.47(19) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 118.41(17) . . ?
C5 C6 C7 136.18(18) . . ?
C1 C6 C7 105.26(17) . . ?
C12 C7 C8 119.95(17) . . ?
C12 C7 C6 105.28(17) . . ?
C8 C7 C6 134.64(17) . . ?
C9 C8 C7 116.25(17) . . ?
C9 C8 C13 122.98(17) . . ?
C7 C8 C13 120.61(15) . . ?
O2 C9 C10 117.47(17) . . ?
O2 C9 C8 120.90(19) . . ?
C10 C9 C8 121.6(2) . . ?
C11 C10 C9 122.10(19) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 116.25(19) . . ?
C10 C11 H11 121.9 . . ?
C12 C11 H11 121.9 . . ?
C11 C12 O1 124.44(19) . . ?
C11 C12 C7 123.6(2) . . ?
O1 C12 C7 111.92(17) . . ?
C14 C13 C18 118.13(17) . . ?
C14 C13 C8 117.78(17) . . ?
C18 C13 C8 124.07(17) . . ?
C15 C14 C13 123.75(19) . . ?
C15 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
C16 C15 C14 116.72(19) . . ?
C16 C15 C21 122.84(18) . . ?
C14 C15 C21 120.41(18) . . ?
C15 C16 C17 121.7(2) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C18 121.2(2) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C13 118.50(19) . . ?
C17 C18 N1 122.82(19) . . ?
C13 C18 N1 118.65(17) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C21 C15 113.60(18) . . ?
C23 C21 C22 110.8(2) . . ?
C15 C21 C22 109.6(2) . . ?
C23 C21 H21 107.5 . . ?
C15 C21 H21 107.5 . . ?
C22 C21 H21 107.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 N1 C20 115.90(19) . . ?
C18 N1 C19 113.29(16) . . ?
C20 N1 C19 109.7(2) . . ?
C1 O1 C12 105.64(14) . . ?
C9 O2 H1O 102.5(16) . . ?

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 C1 C2 C3 176.2(2) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -174.7(2) . . . . ?
O1 C1 C6 C5 -176.66(17) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
O1 C1 C6 C7 -0.4(2) . . . . ?
C2 C1 C6 C7 176.7(2) . . . . ?
C5 C6 C7 C12 174.2(2) . . . . ?
C1 C6 C7 C12 -1.1(2) . . . . ?
C5 C6 C7 C8 -1.5(4) . . . . ?
C1 C6 C7 C8 -176.7(2) . . . . ?
C12 C7 C8 C9 -4.0(3) . . . . ?
C6 C7 C8 C9 171.2(2) . . . . ?
C12 C7 C8 C13 171.50(17) . . . . ?
C6 C7 C8 C13 -13.3(3) . . . . ?
C7 C8 C9 O2 -175.37(17) . . . . ?
C13 C8 C9 O2 9.2(3) . . . . ?
C7 C8 C9 C10 5.1(3) . . . . ?
C13 C8 C9 C10 -170.27(18) . . . . ?
O2 C9 C10 C11 177.9(2) . . . . ?
C8 C9 C10 C11 -2.6(3) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
C10 C11 C12 O1 -175.77(19) . . . . ?
C10 C11 C12 C7 2.3(3) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C6 C7 C12 C11 -176.1(2) . . . . ?
C8 C7 C12 O1 178.65(17) . . . . ?
C6 C7 C12 O1 2.2(2) . . . . ?
C9 C8 C13 C14 124.9(2) . . . . ?
C7 C8 C13 C14 -50.3(2) . . . . ?
C9 C8 C13 C18 -53.1(3) . . . . ?
C7 C8 C13 C18 131.67(19) . . . . ?
C18 C13 C14 C15 1.0(3) . . . . ?
C8 C13 C14 C15 -177.18(16) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C13 C14 C15 C21 -176.81(18) . . . . ?
C14 C15 C16 C17 -1.2(3) . . . . ?
C21 C15 C16 C17 176.5(2) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C13 2.6(3) . . . . ?
C16 C17 C18 N1 -179.58(19) . . . . ?
C14 C13 C18 C17 -2.7(3) . . . . ?
C8 C13 C18 C17 175.34(18) . . . . ?
C14 C13 C18 N1 179.32(16) . . . . ?
C8 C13 C18 N1 -2.6(3) . . . . ?
C16 C15 C21 C23 47.3(3) . . . . ?
C14 C15 C21 C23 -135.0(2) . . . . ?
C16 C15 C21 C22 -77.3(3) . . . . ?
C14 C15 C21 C22 100.4(3) . . . . ?
C17 C18 N1 C20 -12.4(3) . . . . ?
C13 C18 N1 C20 165.4(2) . . . . ?
C17 C18 N1 C19 115.7(2) . . . . ?
C13 C18 N1 C19 -66.5(2) . . . . ?
C2 C1 O1 C12 -175.3(2) . . . . ?
C6 C1 O1 C12 1.7(2) . . . . ?
C11 C12 O1 C1 175.8(2) . . . . ?
C7 C12 O1 C1 -2.4(2) . . . . ?

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 H1O N1 0.97(3) 1.77(3) 2.717(3) 165(2) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.023



_database_code_depnum_ccdc_archive 'CCDC 933432'