# 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       wangmx@mail.tsinghua.edu.cn
_publ_contact_author_name        'Mei-Xiang Wang'
loop_
_publ_author_name
'Mei-Xiang Wang'
'P. Chen'
'Ming Gao'
'De-Xian Wang'
'Liang Zhao'

data_mx1267
_database_code_depnum_ccdc_archive 'CCDC 853593'
#TrackingRef '8130_web_deposit_cif_file_0_Mei-XiangWang_1321005784.mx1267.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 Cl N2 O3.23'
_chemical_formula_weight         378.53
_chemical_absolute_configuration ad

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.614(2)
_cell_length_b                   8.720(3)
_cell_length_c                   10.053(4)
_cell_angle_alpha                78.575(11)
_cell_angle_beta                 82.289(12)
_cell_angle_gamma                87.570(15)
_cell_volume                     478.0(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1877
_cell_measurement_theta_min      2.08
_cell_measurement_theta_max      27.47

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             200
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9567
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8503
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         27.46
_reflns_number_total             4323
_reflns_number_gt                4148
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'

_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^)+(0.0611P)^2^+0.0801P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_number_reflns         4323
_refine_ls_number_parameters     240
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
Cl1 Cl 1.51415(9) 0.03580(6) -0.01906(6) 0.03839(15) Uani 1 1 d . . .
O1 O 1.4720(3) 0.28976(19) -0.32013(17) 0.0339(4) Uani 1 1 d . . .
O2 O 1.1265(3) 0.3342(3) -0.1913(2) 0.0525(6) Uani 1 1 d . . .
O3 O 0.9030(3) 0.6128(2) -0.0068(2) 0.0389(4) Uani 1 1 d . . .
N1 N 1.3422(3) 0.4870(2) -0.03426(18) 0.0263(4) Uani 1 1 d . . .
H1 H 1.1888 0.4494 -0.0317 0.032 Uiso 1 1 calc R . .
N2 N 1.0284(4) 0.8535(3) 0.0029(3) 0.0444(5) Uani 1 1 d . . .
H2A H 0.8816 0.8898 0.0216 0.053 Uiso 1 1 calc R . .
H2B H 1.1523 0.9144 -0.0042 0.053 Uiso 1 1 calc R . .
C1 C 1.4959(4) 0.4409(3) -0.1560(2) 0.0288(4) Uani 1 1 d . . .
H1A H 1.6369 0.3756 -0.1260 0.035 Uiso 1 1 calc R . .
C2 C 1.5801(4) 0.5951(3) -0.2485(3) 0.0344(5) Uani 1 1 d . . .
H2D H 1.7384 0.6244 -0.2289 0.041 Uiso 1 1 calc R . .
H2C H 1.5920 0.5880 -0.3462 0.041 Uiso 1 1 calc R . .
C3 C 1.3857(4) 0.7125(3) -0.2128(2) 0.0349(5) Uani 1 1 d . . .
H3A H 1.2442 0.7065 -0.2605 0.042 Uiso 1 1 calc R . .
H3B H 1.4470 0.8205 -0.2374 0.042 Uiso 1 1 calc R . .
C4 C 1.3222(4) 0.6627(3) -0.0583(2) 0.0281(4) Uani 1 1 d . . .
H4 H 1.4360 0.7073 -0.0081 0.034 Uiso 1 1 calc R . .
C5 C 1.3391(4) 0.3493(3) -0.2230(3) 0.0335(5) Uani 1 1 d . . .
C6 C 1.3537(5) 0.1776(3) -0.3784(3) 0.0373(5) Uani 1 1 d . . .
H6B H 1.2341 0.2319 -0.4361 0.045 Uiso 1 1 calc R . .
H6A H 1.2697 0.0985 -0.3046 0.045 Uiso 1 1 calc R . .
C7 C 1.5447(4) 0.1005(3) -0.4631(3) 0.0328(5) Uani 1 1 d . . .
C8 C 1.5163(5) 0.0895(3) -0.5953(3) 0.0401(6) Uani 1 1 d . . .
H8 H 1.3765 0.1333 -0.6330 0.048 Uiso 1 1 calc R . .
C9 C 1.6886(6) 0.0154(4) -0.6734(3) 0.0482(7) Uani 1 1 d . . .
H9 H 1.6675 0.0084 -0.7642 0.058 Uiso 1 1 calc R . .
C10 C 1.8913(6) -0.0481(4) -0.6184(3) 0.0478(7) Uani 1 1 d . . .
H10 H 2.0112 -0.0980 -0.6719 0.057 Uiso 1 1 calc R . .
C11 C 1.9208(5) -0.0396(3) -0.4866(3) 0.0428(6) Uani 1 1 d . . .
H11 H 2.0601 -0.0850 -0.4493 0.051 Uiso 1 1 calc R . .
C12 C 1.7488(5) 0.0346(3) -0.4073(3) 0.0363(5) Uani 1 1 d . . .
H12 H 1.7700 0.0404 -0.3162 0.044 Uiso 1 1 calc R . .
C13 C 1.0626(4) 0.7079(3) -0.0143(2) 0.0316(5) Uani 1 1 d . . .
C14 C 1.4352(4) 0.4100(3) 0.0986(2) 0.0296(4) Uani 1 1 d . . .
H14A H 1.4152 0.2954 0.1125 0.036 Uiso 1 1 calc R . .
H14B H 1.6092 0.4301 0.0907 0.036 Uiso 1 1 calc R . .
C15 C 1.3088(4) 0.4674(3) 0.2222(2) 0.0292(5) Uani 1 1 d . . .
C16 C 1.4192(4) 0.5752(3) 0.2765(3) 0.0359(5) Uani 1 1 d . . .
H16 H 1.5696 0.6168 0.2324 0.043 Uiso 1 1 calc R . .
C17 C 1.3134(5) 0.6235(3) 0.3943(3) 0.0438(6) Uani 1 1 d . . .
H17 H 1.3910 0.6975 0.4309 0.053 Uiso 1 1 calc R . .
C18 C 1.0940(5) 0.5633(4) 0.4582(3) 0.0468(7) Uani 1 1 d . . .
H18 H 1.0216 0.5951 0.5396 0.056 Uiso 1 1 calc R . .
C19 C 0.9802(5) 0.4575(4) 0.4043(3) 0.0454(7) Uani 1 1 d . . .
H19 H 0.8288 0.4174 0.4481 0.054 Uiso 1 1 calc R . .
C20 C 1.0851(4) 0.4091(3) 0.2865(3) 0.0362(5) Uani 1 1 d . . .
H20 H 1.0054 0.3365 0.2494 0.043 Uiso 1 1 calc R . .
O1W O 0.9956(14) 0.2086(10) 0.0651(8) 0.046(3) Uiso 0.245(9) 1 d P . .

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 0.0396(3) 0.0319(3) 0.0458(3) -0.0102(2) -0.0106(2) 0.0038(2)
O1 0.0361(9) 0.0339(9) 0.0339(9) -0.0129(7) -0.0027(7) -0.0012(7)
O2 0.0269(9) 0.0671(14) 0.0741(15) -0.0408(12) -0.0031(9) -0.0032(9)
O3 0.0250(8) 0.0419(10) 0.0494(11) -0.0091(8) -0.0032(7) -0.0014(7)
N1 0.0220(8) 0.0299(9) 0.0270(9) -0.0063(7) -0.0017(7) 0.0004(7)
N2 0.0250(10) 0.0428(12) 0.0686(16) -0.0223(11) -0.0017(10) 0.0037(9)
C1 0.0233(10) 0.0335(11) 0.0309(11) -0.0102(9) -0.0037(8) 0.0039(8)
C2 0.0286(11) 0.0411(13) 0.0317(12) -0.0076(10) 0.0046(9) -0.0048(10)
C3 0.0345(12) 0.0340(12) 0.0338(12) -0.0019(9) -0.0024(9) -0.0002(9)
C4 0.0237(10) 0.0288(11) 0.0324(11) -0.0063(9) -0.0049(8) 0.0011(8)
C5 0.0318(12) 0.0352(12) 0.0346(12) -0.0089(9) -0.0060(9) 0.0028(9)
C6 0.0366(12) 0.0361(13) 0.0440(14) -0.0154(10) -0.0122(10) 0.0030(10)
C7 0.0357(12) 0.0264(11) 0.0372(12) -0.0072(9) -0.0069(10) -0.0002(9)
C8 0.0454(15) 0.0379(14) 0.0400(14) -0.0103(11) -0.0145(11) 0.0066(11)
C9 0.0588(18) 0.0497(16) 0.0407(15) -0.0169(12) -0.0132(12) 0.0091(13)
C10 0.0497(16) 0.0480(16) 0.0482(16) -0.0200(13) -0.0024(12) 0.0105(13)
C11 0.0384(13) 0.0406(14) 0.0501(16) -0.0106(12) -0.0085(11) 0.0091(11)
C12 0.0368(13) 0.0361(13) 0.0379(13) -0.0082(10) -0.0105(10) -0.0004(10)
C13 0.0242(11) 0.0382(12) 0.0321(11) -0.0065(9) -0.0045(8) 0.0027(9)
C14 0.0251(10) 0.0335(11) 0.0293(11) -0.0043(9) -0.0035(8) 0.0022(8)
C15 0.0261(11) 0.0310(11) 0.0270(11) -0.0007(8) -0.0002(8) 0.0050(8)
C16 0.0296(12) 0.0433(14) 0.0345(12) -0.0073(10) -0.0040(9) 0.0016(10)
C17 0.0461(15) 0.0492(16) 0.0382(14) -0.0133(12) -0.0082(11) 0.0061(12)
C18 0.0455(15) 0.0542(17) 0.0368(14) -0.0098(12) 0.0041(11) 0.0167(13)
C19 0.0324(12) 0.0534(16) 0.0396(14) 0.0067(12) 0.0075(10) 0.0096(12)
C20 0.0282(11) 0.0379(13) 0.0378(13) 0.0016(10) -0.0018(9) 0.0019(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
O1 C5 1.323(3) . ?
O1 C6 1.458(3) . ?
O2 C5 1.199(3) . ?
O3 C13 1.231(3) . ?
N1 C4 1.505(3) . ?
N1 C1 1.512(3) . ?
N1 C14 1.520(3) . ?
N1 H1 0.9300 . ?
N2 C13 1.318(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C5 1.516(3) . ?
C1 C2 1.529(3) . ?
C1 H1A 1.0000 . ?
C2 C3 1.521(3) . ?
C2 H2D 0.9900 . ?
C2 H2C 0.9900 . ?
C3 C4 1.524(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C13 1.524(3) . ?
C4 H4 1.0000 . ?
C6 C7 1.499(3) . ?
C6 H6B 0.9900 . ?
C6 H6A 0.9900 . ?
C7 C8 1.382(4) . ?
C7 C12 1.396(3) . ?
C8 C9 1.383(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.509(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.382(3) . ?
C15 C20 1.400(3) . ?
C16 C17 1.386(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C6 115.98(19) . . ?
C4 N1 C1 108.47(17) . . ?
C4 N1 C14 115.22(17) . . ?
C1 N1 C14 110.97(17) . . ?
C4 N1 H1 107.3 . . ?
C1 N1 H1 107.3 . . ?
C14 N1 H1 107.3 . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C5 107.40(17) . . ?
N1 C1 C2 105.25(17) . . ?
C5 C1 C2 112.7(2) . . ?
N1 C1 H1A 110.4 . . ?
C5 C1 H1A 110.4 . . ?
C2 C1 H1A 110.4 . . ?
C3 C2 C1 103.72(18) . . ?
C3 C2 H2D 111.0 . . ?
C1 C2 H2D 111.0 . . ?
C3 C2 H2C 111.0 . . ?
C1 C2 H2C 111.0 . . ?
H2D C2 H2C 109.0 . . ?
C2 C3 C4 103.63(19) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
N1 C4 C13 108.31(17) . . ?
N1 C4 C3 103.66(17) . . ?
C13 C4 C3 110.54(19) . . ?
N1 C4 H4 111.3 . . ?
C13 C4 H4 111.3 . . ?
C3 C4 H4 111.3 . . ?
O2 C5 O1 125.9(2) . . ?
O2 C5 C1 124.3(2) . . ?
O1 C5 C1 109.84(19) . . ?
O1 C6 C7 107.4(2) . . ?
O1 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
O1 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
H6B C6 H6A 108.5 . . ?
C8 C7 C12 119.5(2) . . ?
C8 C7 C6 120.3(2) . . ?
C12 C7 C6 120.2(2) . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 119.1(2) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
O3 C13 N2 125.4(2) . . ?
O3 C13 C4 119.2(2) . . ?
N2 C13 C4 115.2(2) . . ?
C15 C14 N1 113.41(18) . . ?
C15 C14 H14A 108.9 . . ?
N1 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
N1 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C20 119.1(2) . . ?
C16 C15 C14 119.6(2) . . ?
C20 C15 C14 121.3(2) . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 119.9(3) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?

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
C4 N1 C1 C5 -116.65(19) . . . . ?
C14 N1 C1 C5 115.8(2) . . . . ?
C4 N1 C1 C2 3.7(2) . . . . ?
C14 N1 C1 C2 -123.82(19) . . . . ?
N1 C1 C2 C3 -26.1(2) . . . . ?
C5 C1 C2 C3 90.7(2) . . . . ?
C1 C2 C3 C4 38.7(2) . . . . ?
C1 N1 C4 C13 137.48(18) . . . . ?
C14 N1 C4 C13 -97.5(2) . . . . ?
C1 N1 C4 C3 20.0(2) . . . . ?
C14 N1 C4 C3 145.10(18) . . . . ?
C2 C3 C4 N1 -36.1(2) . . . . ?
C2 C3 C4 C13 -152.0(2) . . . . ?
C6 O1 C5 O2 -9.7(4) . . . . ?
C6 O1 C5 C1 170.31(19) . . . . ?
N1 C1 C5 O2 7.5(3) . . . . ?
C2 C1 C5 O2 -107.9(3) . . . . ?
N1 C1 C5 O1 -172.43(18) . . . . ?
C2 C1 C5 O1 72.1(2) . . . . ?
C5 O1 C6 C7 -168.4(2) . . . . ?
O1 C6 C7 C8 -130.8(2) . . . . ?
O1 C6 C7 C12 51.5(3) . . . . ?
C12 C7 C8 C9 -0.7(4) . . . . ?
C6 C7 C8 C9 -178.5(3) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C10 C11 C12 C7 0.1(4) . . . . ?
C8 C7 C12 C11 0.6(4) . . . . ?
C6 C7 C12 C11 178.4(2) . . . . ?
N1 C4 C13 O3 -20.9(3) . . . . ?
C3 C4 C13 O3 92.0(3) . . . . ?
N1 C4 C13 N2 163.9(2) . . . . ?
C3 C4 C13 N2 -83.2(3) . . . . ?
C4 N1 C14 C15 48.9(2) . . . . ?
C1 N1 C14 C15 172.65(18) . . . . ?
N1 C14 C15 C16 -101.6(2) . . . . ?
N1 C14 C15 C20 80.9(3) . . . . ?
C20 C15 C16 C17 1.2(4) . . . . ?
C14 C15 C16 C17 -176.4(2) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 C20 0.7(4) . . . . ?
C18 C19 C20 C15 0.4(4) . . . . ?
C16 C15 C20 C19 -1.3(4) . . . . ?
C14 C15 C20 C19 176.3(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
N1 H1 O3 0.93 2.12 2.659(3) 115.4 .
N1 H1 O2 0.93 2.13 2.687(3) 117.6 .
N1 H1 O1W 0.93 2.37 3.098(8) 134.6 .
N2 H2A Cl1 0.88 2.42 3.249(2) 157.8 1_465
N2 H2B Cl1 0.88 2.30 3.175(3) 170.5 1_565

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.054