# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       leeyib268@126.com
_publ_contact_author_name        'Li Yibiao'
loop_
_publ_author_name
'Huanfeng Jiang'
'Yibiao Li'
'Jian Zhao'
'Huoji Chen'
'Bifu Liu'

data_1
_database_code_depnum_ccdc_archive 'CCDC 847837'
#TrackingRef '1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H32 N2 O'
_chemical_formula_sum            'C22 H32 N2 O'
_chemical_formula_weight         340.50

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/c'
_symmetry_space_group_name_Hall  '-P 2ybc '

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                   13.143(5)
_cell_length_b                   14.656(5)
_cell_length_c                   11.278(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.40(3)
_cell_angle_gamma                90.00
_cell_volume                     2121.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2895
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.89

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   '(Jacobson, 1998)'

_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  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26191
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.20
_reflns_number_total             3822
_reflns_number_gt                2499
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_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^)+(0.0715P)^2^+0.8297P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3822
_refine_ls_number_parameters     235
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.021
_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 0.65463(16) 0.25379(14) 0.48272(19) 0.0552(5) Uani 1 1 d . . .
C2 C 0.57115(16) 0.22577(14) 0.54258(19) 0.0548(5) Uani 1 1 d . . .
C3 C 0.51647(17) 0.14444(14) 0.5130(2) 0.0587(5) Uani 1 1 d . . .
H3 H 0.5334 0.1063 0.4542 0.070 Uiso 1 1 calc R . .
C4 C 0.43758(17) 0.11990(14) 0.5698(2) 0.0585(5) Uani 1 1 d . . .
H4 H 0.4019 0.0657 0.5476 0.070 Uiso 1 1 calc R . .
C5 C 0.40966(16) 0.17375(14) 0.65955(19) 0.0544(5) Uani 1 1 d . . .
C6 C 0.46453(18) 0.25436(16) 0.6884(2) 0.0652(6) Uani 1 1 d . . .
H6 H 0.4480 0.2922 0.7478 0.078 Uiso 1 1 calc R . .
C7 C 0.54330(18) 0.28008(15) 0.6311(2) 0.0648(6) Uani 1 1 d . . .
H7 H 0.5782 0.3349 0.6524 0.078 Uiso 1 1 calc R . .
C8 C 0.32406(18) 0.14217(16) 0.7222(2) 0.0648(6) Uani 1 1 d U . .
C9 C 0.2235(2) 0.1292(2) 0.6266(3) 0.1003(10) Uani 1 1 d . . .
H9A H 0.2347 0.0848 0.5681 0.150 Uiso 1 1 calc R . .
H9B H 0.2034 0.1862 0.5864 0.150 Uiso 1 1 calc R . .
H9C H 0.1693 0.1084 0.6651 0.150 Uiso 1 1 calc R . .
C10 C 0.3041(2) 0.2091(2) 0.8181(3) 0.0976(10) Uani 1 1 d . . .
H10A H 0.2503 0.1855 0.8551 0.146 Uiso 1 1 calc R . .
H10B H 0.2826 0.2667 0.7806 0.146 Uiso 1 1 calc R . .
H10C H 0.3669 0.2170 0.8789 0.146 Uiso 1 1 calc R . .
C11 C 0.3552(3) 0.0502(2) 0.7833(3) 0.0990(10) Uani 1 1 d . . .
H11A H 0.3702 0.0078 0.7244 0.149 Uiso 1 1 calc R . .
H11B H 0.2991 0.0271 0.8167 0.149 Uiso 1 1 calc R . .
H11C H 0.4160 0.0578 0.8471 0.149 Uiso 1 1 calc R . .
C12 C 0.67895(17) 0.33647(15) 0.4494(2) 0.0599(6) Uani 1 1 d . . .
H12 H 0.6426 0.3896 0.4584 0.072 Uiso 1 1 calc R . .
C13 C 0.77181(17) 0.33185(15) 0.39616(19) 0.0574(5) Uani 1 1 d . . .
C14 C 0.73285(17) 0.18883(16) 0.4522(2) 0.0606(6) Uani 1 1 d . . .
C15 C 0.78858(19) 0.48666(15) 0.3273(2) 0.0678(6) Uani 1 1 d U . .
C16 C 0.6789(2) 0.4976(2) 0.2520(3) 0.1009(10) Uani 1 1 d . . .
H16A H 0.6704 0.4600 0.1809 0.151 Uiso 1 1 calc R . .
H16B H 0.6671 0.5602 0.2283 0.151 Uiso 1 1 calc R . .
H16C H 0.6296 0.4794 0.2993 0.151 Uiso 1 1 calc R . .
C17 C 0.8032(3) 0.5349(2) 0.4473(3) 0.1132(12) Uani 1 1 d . . .
H17A H 0.7531 0.5127 0.4910 0.170 Uiso 1 1 calc R . .
H17B H 0.7936 0.5993 0.4339 0.170 Uiso 1 1 calc R . .
H17C H 0.8722 0.5236 0.4938 0.170 Uiso 1 1 calc R . .
C18 C 0.8634(3) 0.5262(2) 0.2547(3) 0.1105(11) Uani 1 1 d . . .
H18A H 0.9337 0.5198 0.3003 0.166 Uiso 1 1 calc R . .
H18B H 0.8481 0.5896 0.2390 0.166 Uiso 1 1 calc R . .
H18C H 0.8557 0.4941 0.1791 0.166 Uiso 1 1 calc R . .
C19 C 0.90020(17) 0.20250(17) 0.3708(2) 0.0657(6) Uani 1 1 d U . .
C20 C 0.9922(2) 0.2655(2) 0.4166(4) 0.1220(13) Uani 1 1 d . . .
H20A H 1.0539 0.2396 0.3977 0.183 Uiso 1 1 calc R . .
H20B H 1.0019 0.2725 0.5029 0.183 Uiso 1 1 calc R . .
H20C H 0.9788 0.3240 0.3782 0.183 Uiso 1 1 calc R . .
C21 C 0.8762(3) 0.1947(3) 0.2357(3) 0.1481(18) Uani 1 1 d . . .
H21A H 0.8219 0.1506 0.2106 0.222 Uiso 1 1 calc R . .
H21B H 0.9376 0.1757 0.2092 0.222 Uiso 1 1 calc R . .
H21C H 0.8537 0.2529 0.2005 0.222 Uiso 1 1 calc R . .
C22 C 0.9323(3) 0.1119(2) 0.4312(4) 0.1123(12) Uani 1 1 d . . .
H22A H 0.8819 0.0662 0.3978 0.168 Uiso 1 1 calc R . .
H22B H 0.9362 0.1171 0.5169 0.168 Uiso 1 1 calc R . .
H22C H 0.9993 0.0947 0.4173 0.168 Uiso 1 1 calc R . .
N1 N 0.80537(14) 0.23910(12) 0.40851(17) 0.0608(5) Uani 1 1 d . . .
N2 N 0.81840(15) 0.38964(13) 0.34428(17) 0.0649(5) Uani 1 1 d . . .
O1 O 0.73023(14) 0.10608(11) 0.46365(18) 0.0851(6) Uani 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 0.0538(12) 0.0555(12) 0.0575(12) -0.0007(10) 0.0151(9) -0.0021(10)
C2 0.0518(12) 0.0535(12) 0.0604(12) 0.0020(10) 0.0152(10) 0.0006(9)
C3 0.0634(14) 0.0530(12) 0.0620(12) -0.0028(10) 0.0185(11) -0.0005(10)
C4 0.0577(13) 0.0503(12) 0.0683(13) -0.0011(10) 0.0153(11) -0.0054(9)
C5 0.0479(12) 0.0540(12) 0.0619(12) 0.0022(10) 0.0132(9) -0.0014(9)
C6 0.0629(14) 0.0662(14) 0.0713(14) -0.0140(11) 0.0251(11) -0.0087(11)
C7 0.0626(14) 0.0585(13) 0.0776(15) -0.0103(11) 0.0247(12) -0.0122(10)
C8 0.0565(13) 0.0657(14) 0.0755(15) 0.0004(11) 0.0214(11) -0.0050(11)
C9 0.0593(17) 0.123(3) 0.118(2) 0.0012(19) 0.0169(16) -0.0172(16)
C10 0.092(2) 0.099(2) 0.119(2) -0.0253(18) 0.0616(19) -0.0210(16)
C11 0.110(2) 0.092(2) 0.107(2) 0.0310(17) 0.0511(19) 0.0042(17)
C12 0.0571(13) 0.0569(13) 0.0684(13) -0.0004(10) 0.0196(11) -0.0004(10)
C13 0.0526(12) 0.0603(13) 0.0604(12) 0.0006(10) 0.0145(10) -0.0024(10)
C14 0.0577(13) 0.0600(14) 0.0657(13) 0.0031(11) 0.0171(11) 0.0016(10)
C15 0.0732(16) 0.0584(13) 0.0770(15) 0.0008(11) 0.0278(12) -0.0073(11)
C16 0.091(2) 0.0744(18) 0.130(3) 0.0209(17) 0.0066(19) 0.0036(15)
C17 0.169(3) 0.084(2) 0.092(2) -0.0188(17) 0.039(2) -0.024(2)
C18 0.122(3) 0.083(2) 0.148(3) 0.0272(19) 0.076(2) -0.0021(18)
C19 0.0529(13) 0.0781(15) 0.0694(14) 0.0038(11) 0.0205(11) 0.0100(11)
C20 0.0608(18) 0.109(2) 0.198(4) 0.005(2) 0.031(2) 0.0039(17)
C21 0.124(3) 0.250(5) 0.0722(19) -0.017(3) 0.0259(19) 0.083(3)
C22 0.088(2) 0.097(2) 0.165(3) 0.033(2) 0.058(2) 0.0362(17)
N1 0.0536(10) 0.0608(11) 0.0725(12) 0.0054(9) 0.0235(9) 0.0041(8)
N2 0.0647(12) 0.0630(11) 0.0711(12) 0.0061(9) 0.0238(10) -0.0028(9)
O1 0.0848(13) 0.0578(11) 0.1240(16) 0.0093(10) 0.0476(11) 0.0074(8)

_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 C12 1.328(3) . ?
C1 C2 1.465(3) . ?
C1 C14 1.495(3) . ?
C2 C7 1.386(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 C8 1.523(3) . ?
C6 C7 1.386(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C10 1.523(3) . ?
C8 C9 1.527(4) . ?
C8 C11 1.530(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.473(3) . ?
C12 H12 0.9300 . ?
C13 N2 1.260(3) . ?
C13 N1 1.427(3) . ?
C14 O1 1.221(3) . ?
C14 N1 1.377(3) . ?
C15 N2 1.476(3) . ?
C15 C17 1.502(4) . ?
C15 C16 1.516(4) . ?
C15 C18 1.523(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C21 1.492(4) . ?
C19 N1 1.500(3) . ?
C19 C22 1.511(4) . ?
C19 C20 1.521(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C1 C2 129.48(19) . . ?
C12 C1 C14 107.27(19) . . ?
C2 C1 C14 123.22(19) . . ?
C7 C2 C3 117.45(19) . . ?
C7 C2 C1 120.70(19) . . ?
C3 C2 C1 121.84(19) . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 122.1(2) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 116.65(19) . . ?
C6 C5 C8 123.29(19) . . ?
C4 C5 C8 120.05(19) . . ?
C5 C6 C7 121.7(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C2 121.3(2) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C5 C8 C10 112.98(19) . . ?
C5 C8 C9 108.9(2) . . ?
C10 C8 C9 109.1(2) . . ?
C5 C8 C11 108.9(2) . . ?
C10 C8 C11 108.5(2) . . ?
C9 C8 C11 108.4(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C12 C13 110.14(19) . . ?
C1 C12 H12 124.9 . . ?
C13 C12 H12 124.9 . . ?
N2 C13 N1 121.0(2) . . ?
N2 C13 C12 133.3(2) . . ?
N1 C13 C12 105.66(17) . . ?
O1 C14 N1 127.4(2) . . ?
O1 C14 C1 124.9(2) . . ?
N1 C14 C1 107.75(19) . . ?
N2 C15 C17 110.9(2) . . ?
N2 C15 C16 111.6(2) . . ?
C17 C15 C16 112.2(3) . . ?
N2 C15 C18 104.6(2) . . ?
C17 C15 C18 109.4(2) . . ?
C16 C15 C18 107.8(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 N1 108.1(2) . . ?
C21 C19 C22 111.8(3) . . ?
N1 C19 C22 110.8(2) . . ?
C21 C19 C20 111.8(3) . . ?
N1 C19 C20 109.6(2) . . ?
C22 C19 C20 104.8(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 N1 C13 108.75(17) . . ?
C14 N1 C19 126.26(19) . . ?
C13 N1 C19 124.84(18) . . ?
C13 N2 C15 124.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.045