# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2011

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Chun-Jiang Wang'
_publ_contact_author_address     
;
Hubei Wuchang
430072
;

_publ_contact_author_email       cjwang@whu.edu.cn
loop_
_publ_author_name
'Tang-Lin Liu'
'Zhi-Yong Xue'
'Hai-Yan Tao'
'Chun-Jiang Wang'
# Attachment '- 100118ltl_0m.cif'

data_100118ltl_0m
_database_code_depnum_ccdc_archive 'CCDC 775772'
#TrackingRef '- 100118ltl_0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration 7R,8S,9R,10R
_chemical_formula_sum            'C25 H21 Cl N2 O3'

_chemical_formula_weight         432.89

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           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                   10.270(3)
_cell_length_b                   11.202(3)
_cell_length_c                   18.897(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2174.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_T_max  0.9467
_exptl_absorpt_process_details   SADABS

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12338
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         25.99
_reflns_number_total             4250
_reflns_number_gt                3860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_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^)+(0.0390P)^2^+0.3464P] 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       0.0141(11)
_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   0.03(6)
_refine_ls_number_reflns         4250
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.4901(2) -0.16392(17) -0.11718(11) 0.0600(5) Uani 1 1 d . . .
C2 C 0.4248(2) -0.20394(19) -0.05875(11) 0.0649(5) Uani 1 1 d . . .
H2 H 0.3501 -0.2501 -0.0637 0.078 Uiso 1 1 calc R . .
C3 C 0.4709(2) -0.17505(17) 0.00762(11) 0.0587(5) Uani 1 1 d . . .
H3 H 0.4275 -0.2036 0.0474 0.070 Uiso 1 1 calc R . .
C4 C 0.58066(17) -0.10432(14) 0.01635(9) 0.0438(4) Uani 1 1 d . . .
C5 C 0.64574(19) -0.06751(18) -0.04394(10) 0.0556(4) Uani 1 1 d . . .
H5 H 0.7207 -0.0215 -0.0397 0.067 Uiso 1 1 calc R . .
C6 C 0.6007(2) -0.09834(19) -0.11062(11) 0.0629(5) Uani 1 1 d . . .
H6 H 0.6461 -0.0742 -0.1507 0.075 Uiso 1 1 calc R . .
C7 C 0.61738(15) -0.06455(14) 0.09028(9) 0.0413(4) Uani 1 1 d . . .
H7 H 0.6018 -0.1319 0.1223 0.050 Uiso 1 1 calc R . .
C8 C 0.53501(15) 0.04360(13) 0.11789(8) 0.0377(3) Uani 1 1 d . . .
C9 C 0.62140(16) 0.09212(14) 0.17905(8) 0.0408(4) Uani 1 1 d . . .
H9 H 0.6099 0.1788 0.1823 0.049 Uiso 1 1 calc R . .
C10 C 0.76101(17) 0.06525(15) 0.15210(9) 0.0461(4) Uani 1 1 d . . .
H10 H 0.8118 0.0344 0.1920 0.055 Uiso 1 1 calc R . .
C11 C 0.83174(18) 0.17323(17) 0.12268(9) 0.0520(4) Uani 1 1 d . . .
C12 C 0.8945(4) 0.3723(3) 0.14396(15) 0.1318(16) Uani 1 1 d . . .
H12A H 0.9829 0.3516 0.1329 0.198 Uiso 1 1 calc R . .
H12B H 0.8936 0.4296 0.1817 0.198 Uiso 1 1 calc R . .
H12C H 0.8536 0.4061 0.1029 0.198 Uiso 1 1 calc R . .
C13 C 0.59120(17) 0.03703(15) 0.25051(8) 0.0431(4) Uani 1 1 d . . .
C14 C 0.5056(2) 0.09377(19) 0.29542(10) 0.0579(5) Uani 1 1 d . . .
H14 H 0.4678 0.1656 0.2817 0.069 Uiso 1 1 calc R . .
C15 C 0.4750(3) 0.0450(2) 0.36104(11) 0.0750(7) Uani 1 1 d . . .
H15 H 0.4170 0.0840 0.3909 0.090 Uiso 1 1 calc R . .
C16 C 0.5310(3) -0.0617(2) 0.38174(11) 0.0756(7) Uani 1 1 d . . .
H16 H 0.5110 -0.0948 0.4255 0.091 Uiso 1 1 calc R . .
C17 C 0.6152(2) -0.11765(19) 0.33773(11) 0.0655(6) Uani 1 1 d . . .
H17 H 0.6531 -0.1893 0.3517 0.079 Uiso 1 1 calc R . .
C18 C 0.64605(19) -0.07002(16) 0.27216(9) 0.0500(4) Uani 1 1 d . . .
H18 H 0.7038 -0.1100 0.2426 0.060 Uiso 1 1 calc R . .
C19 C 0.52520(16) 0.14013(13) 0.06028(8) 0.0389(3) Uani 1 1 d . . .
C20 C 0.31833(16) 0.07575(15) 0.08287(8) 0.0411(4) Uani 1 1 d . . .
C21 C 0.18549(18) 0.06072(19) 0.07819(10) 0.0567(5) Uani 1 1 d . . .
H21 H 0.1355 0.1056 0.0469 0.068 Uiso 1 1 calc R . .
C22 C 0.12947(19) -0.0242(2) 0.12211(12) 0.0619(5) Uani 1 1 d . . .
H22 H 0.0401 -0.0372 0.1200 0.074 Uiso 1 1 calc R . .
C23 C 0.20389(18) -0.09000(19) 0.16898(10) 0.0563(5) Uani 1 1 d . . .
H23 H 0.1642 -0.1472 0.1973 0.068 Uiso 1 1 calc R . .
C24 C 0.33656(17) -0.07167(16) 0.17414(9) 0.0471(4) Uani 1 1 d . . .
H24 H 0.3860 -0.1151 0.2063 0.056 Uiso 1 1 calc R . .
C25 C 0.39485(16) 0.01249(14) 0.13061(8) 0.0387(3) Uani 1 1 d . . .
Cl1 Cl 0.42927(8) -0.19584(6) -0.20143(3) 0.0899(2) Uani 1 1 d . . .
N1 N 0.75302(14) -0.02807(13) 0.09888(9) 0.0508(4) Uani 1 1 d . . .
H1 H 0.8180 -0.0573 0.0760 0.061 Uiso 1 1 calc R . .
N2 N 0.39810(13) 0.15124(12) 0.04260(7) 0.0428(3) Uani 1 1 d . . .
H2A H 0.3696 0.1989 0.0105 0.051 Uiso 1 1 calc R . .
O1 O 0.89268(12) 0.17171(12) 0.06821(7) 0.0576(3) Uani 1 1 d . . .
O2 O 0.82385(19) 0.26555(14) 0.16576(7) 0.0863(6) Uani 1 1 d . . .
O3 O 0.61534(12) 0.19754(11) 0.03597(6) 0.0503(3) 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 0.0750(13) 0.0498(10) 0.0552(11) -0.0132(9) -0.0078(10) 0.0132(9)
C2 0.0731(13) 0.0524(11) 0.0692(13) -0.0138(10) -0.0027(11) -0.0127(10)
C3 0.0692(12) 0.0482(11) 0.0586(11) -0.0049(9) 0.0075(9) -0.0130(9)
C4 0.0492(9) 0.0324(8) 0.0499(9) 0.0004(7) 0.0047(7) 0.0037(7)
C5 0.0544(10) 0.0580(11) 0.0545(10) -0.0018(9) 0.0082(8) -0.0029(9)
C6 0.0749(13) 0.0657(12) 0.0480(10) -0.0021(9) 0.0113(10) 0.0057(11)
C7 0.0444(9) 0.0315(7) 0.0479(9) 0.0057(7) 0.0011(7) 0.0012(7)
C8 0.0443(8) 0.0341(8) 0.0348(7) 0.0057(6) -0.0004(7) 0.0015(7)
C9 0.0504(9) 0.0347(8) 0.0374(8) 0.0066(6) -0.0035(7) -0.0018(7)
C10 0.0492(9) 0.0465(9) 0.0425(8) 0.0146(7) -0.0059(7) -0.0075(8)
C11 0.0571(10) 0.0573(11) 0.0417(9) 0.0104(8) -0.0036(8) -0.0158(9)
C12 0.233(4) 0.0863(19) 0.0757(17) -0.0107(14) 0.032(2) -0.106(2)
C13 0.0501(9) 0.0438(9) 0.0354(8) 0.0045(7) -0.0052(7) -0.0090(7)
C14 0.0742(13) 0.0519(11) 0.0475(10) -0.0011(9) 0.0041(9) -0.0031(10)
C15 0.0971(17) 0.0785(16) 0.0494(12) -0.0072(11) 0.0199(11) -0.0131(13)
C16 0.1064(18) 0.0770(15) 0.0434(10) 0.0143(11) 0.0041(12) -0.0293(14)
C17 0.0842(15) 0.0584(12) 0.0538(12) 0.0227(9) -0.0062(11) -0.0116(11)
C18 0.0569(10) 0.0473(10) 0.0459(9) 0.0122(8) -0.0030(8) -0.0081(8)
C19 0.0526(9) 0.0336(8) 0.0306(7) 0.0013(6) 0.0001(7) 0.0031(7)
C20 0.0466(9) 0.0398(9) 0.0368(8) -0.0029(7) -0.0013(7) 0.0045(7)
C21 0.0509(10) 0.0630(12) 0.0562(11) 0.0021(9) -0.0085(8) 0.0078(9)
C22 0.0420(10) 0.0749(13) 0.0689(12) -0.0013(11) -0.0001(9) -0.0044(9)
C23 0.0515(10) 0.0616(12) 0.0558(11) 0.0040(9) 0.0061(9) -0.0107(9)
C24 0.0504(9) 0.0479(9) 0.0429(9) 0.0075(7) 0.0008(7) -0.0034(8)
C25 0.0420(8) 0.0385(8) 0.0355(8) -0.0003(6) 0.0005(7) 0.0022(7)
Cl1 0.1168(5) 0.0894(4) 0.0637(3) -0.0221(3) -0.0221(3) 0.0155(4)
N1 0.0389(7) 0.0440(8) 0.0696(10) -0.0031(7) -0.0014(7) 0.0049(6)
N2 0.0539(8) 0.0407(7) 0.0339(6) 0.0061(6) -0.0054(6) 0.0066(6)
O1 0.0536(7) 0.0631(8) 0.0561(8) 0.0178(6) 0.0072(6) -0.0075(6)
O2 0.1394(15) 0.0689(9) 0.0505(8) -0.0060(7) 0.0176(9) -0.0587(10)
O3 0.0571(7) 0.0454(6) 0.0486(7) 0.0143(5) 0.0020(5) -0.0021(6)

_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 C6 1.359(3) . ?
C1 C2 1.367(3) . ?
C1 Cl1 1.747(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C4 C7 1.514(2) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.461(2) . ?
C7 C8 1.567(2) . ?
C7 H7 0.9800 . ?
C8 C25 1.500(2) . ?
C8 C19 1.538(2) . ?
C8 C9 1.555(2) . ?
C9 C13 1.517(2) . ?
C9 C10 1.551(2) . ?
C9 H9 0.9800 . ?
C10 N1 1.453(2) . ?
C10 C11 1.517(2) . ?
C10 H10 0.9800 . ?
C11 O1 1.205(2) . ?
C11 O2 1.319(2) . ?
C12 O2 1.459(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.377(3) . ?
C13 C18 1.387(2) . ?
C14 C15 1.391(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.354(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O3 1.2172(19) . ?
C19 N2 1.353(2) . ?
C20 C21 1.377(3) . ?
C20 C25 1.391(2) . ?
C20 N2 1.402(2) . ?
C21 C22 1.388(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.381(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.387(2) . ?
C24 H24 0.9300 . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?

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
C6 C1 C2 120.91(19) . . ?
C6 C1 Cl1 119.52(17) . . ?
C2 C1 Cl1 119.57(17) . . ?
C1 C2 C3 119.30(18) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 121.39(18) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 117.68(17) . . ?
C5 C4 C7 123.48(16) . . ?
C3 C4 C7 118.69(15) . . ?
C4 C5 C6 120.89(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.77(19) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
N1 C7 C4 115.00(14) . . ?
N1 C7 C8 105.16(13) . . ?
C4 C7 C8 113.60(13) . . ?
N1 C7 H7 107.6 . . ?
C4 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C25 C8 C19 102.35(12) . . ?
C25 C8 C9 120.63(13) . . ?
C19 C8 C9 108.53(12) . . ?
C25 C8 C7 113.06(13) . . ?
C19 C8 C7 110.07(12) . . ?
C9 C8 C7 102.11(12) . . ?
C13 C9 C10 113.74(13) . . ?
C13 C9 C8 113.75(13) . . ?
C10 C9 C8 102.44(13) . . ?
C13 C9 H9 108.9 . . ?
C10 C9 H9 108.9 . . ?
C8 C9 H9 108.9 . . ?
N1 C10 C11 110.32(14) . . ?
N1 C10 C9 108.35(13) . . ?
C11 C10 C9 114.10(15) . . ?
N1 C10 H10 108.0 . . ?
C11 C10 H10 108.0 . . ?
C9 C10 H10 108.0 . . ?
O1 C11 O2 124.78(17) . . ?
O1 C11 C10 123.42(18) . . ?
O2 C11 C10 111.70(15) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 118.46(16) . . ?
C14 C13 C9 119.43(16) . . ?
C18 C13 C9 122.10(16) . . ?
C13 C14 C15 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 119.48(19) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.1(2) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C13 120.27(19) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
O3 C19 N2 126.29(14) . . ?
O3 C19 C8 126.08(14) . . ?
N2 C19 C8 107.62(13) . . ?
C21 C20 C25 122.62(16) . . ?
C21 C20 N2 128.15(16) . . ?
C25 C20 N2 109.23(14) . . ?
C20 C21 C22 117.13(17) . . ?
C20 C21 H21 121.4 . . ?
C22 C21 H21 121.4 . . ?
C23 C22 C21 121.29(18) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 120.75(18) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 119.00(17) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C24 C25 C20 119.16(16) . . ?
C24 C25 C8 131.83(15) . . ?
C20 C25 C8 108.66(13) . . ?
C10 N1 C7 109.40(13) . . ?
C10 N1 H1 125.3 . . ?
C7 N1 H1 125.3 . . ?
C19 N2 C20 111.97(13) . . ?
C19 N2 H2A 124.0 . . ?
C20 N2 H2A 124.0 . . ?
C11 O2 C12 115.99(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
C6 C1 C2 C3 1.3(3) . . . . ?
Cl1 C1 C2 C3 -177.83(17) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C2 C3 C4 C5 -2.6(3) . . . . ?
C2 C3 C4 C7 173.26(18) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C7 C4 C5 C6 -174.22(18) . . . . ?
C2 C1 C6 C5 -2.5(3) . . . . ?
Cl1 C1 C6 C5 176.67(16) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C5 C4 C7 N1 -24.9(2) . . . . ?
C3 C4 C7 N1 159.50(15) . . . . ?
C5 C4 C7 C8 96.29(19) . . . . ?
C3 C4 C7 C8 -79.27(19) . . . . ?
N1 C7 C8 C25 -165.45(13) . . . . ?
C4 C7 C8 C25 67.96(17) . . . . ?
N1 C7 C8 C19 80.79(16) . . . . ?
C4 C7 C8 C19 -45.80(18) . . . . ?
N1 C7 C8 C9 -34.33(15) . . . . ?
C4 C7 C8 C9 -160.92(13) . . . . ?
C25 C8 C9 C13 35.8(2) . . . . ?
C19 C8 C9 C13 153.26(14) . . . . ?
C7 C8 C9 C13 -90.50(16) . . . . ?
C25 C8 C9 C10 159.02(13) . . . . ?
C19 C8 C9 C10 -83.55(14) . . . . ?
C7 C8 C9 C10 32.68(14) . . . . ?
C13 C9 C10 N1 102.31(15) . . . . ?
C8 C9 C10 N1 -20.89(15) . . . . ?
C13 C9 C10 C11 -134.39(15) . . . . ?
C8 C9 C10 C11 102.41(15) . . . . ?
N1 C10 C11 O1 -12.8(2) . . . . ?
C9 C10 C11 O1 -134.99(18) . . . . ?
N1 C10 C11 O2 170.66(16) . . . . ?
C9 C10 C11 O2 48.4(2) . . . . ?
C10 C9 C13 C14 149.11(16) . . . . ?
C8 C9 C13 C14 -94.11(19) . . . . ?
C10 C9 C13 C18 -31.6(2) . . . . ?
C8 C9 C13 C18 85.2(2) . . . . ?
C18 C13 C14 C15 0.1(3) . . . . ?
C9 C13 C14 C15 179.42(19) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C13 0.4(3) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C9 C13 C18 C17 -179.61(17) . . . . ?
C25 C8 C19 O3 175.31(15) . . . . ?
C9 C8 C19 O3 46.7(2) . . . . ?
C7 C8 C19 O3 -64.2(2) . . . . ?
C25 C8 C19 N2 -3.51(16) . . . . ?
C9 C8 C19 N2 -132.07(14) . . . . ?
C7 C8 C19 N2 116.95(14) . . . . ?
C25 C20 C21 C22 -2.0(3) . . . . ?
N2 C20 C21 C22 177.03(17) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C21 C22 C23 C24 0.9(3) . . . . ?
C22 C23 C24 C25 -1.1(3) . . . . ?
C23 C24 C25 C20 -0.2(2) . . . . ?
C23 C24 C25 C8 -172.53(18) . . . . ?
C21 C20 C25 C24 1.8(2) . . . . ?
N2 C20 C25 C24 -177.37(14) . . . . ?
C21 C20 C25 C8 175.79(16) . . . . ?
N2 C20 C25 C8 -3.39(17) . . . . ?
C19 C8 C25 C24 177.07(17) . . . . ?
C9 C8 C25 C24 -62.4(2) . . . . ?
C7 C8 C25 C24 58.7(2) . . . . ?
C19 C8 C25 C20 4.13(16) . . . . ?
C9 C8 C25 C20 124.64(15) . . . . ?
C7 C8 C25 C20 -114.23(14) . . . . ?
C11 C10 N1 C7 -126.31(15) . . . . ?
C9 C10 N1 C7 -0.74(17) . . . . ?
C4 C7 N1 C10 147.89(14) . . . . ?
C8 C7 N1 C10 22.16(17) . . . . ?
O3 C19 N2 C20 -177.11(15) . . . . ?
C8 C19 N2 C20 1.70(17) . . . . ?
C21 C20 N2 C19 -178.08(18) . . . . ?
C25 C20 N2 C19 1.04(18) . . . . ?
O1 C11 O2 C12 0.4(4) . . . . ?
C10 C11 O2 C12 177.0(3) . . . . ?

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
N2 H2A O1 0.86 2.09 2.8845(18) 153.5 4_455

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.026