# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
#TrackingRef '- CIF.cif'

_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       liangfs112@nenu.edu.cn
_publ_contact_author_name        'F. Liang'
loop_
_publ_author_name
'Y. Wei'
'S. Lin'
'J. Zhang'
'Z. Niu'
'Q. Fu'
'F. Liang'

data_1
#TrackingRef '- CIF.cif'

#TrackingRef '- CIF.cif'

_database_code_depnum_ccdc_archive 'CCDC 826841'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37

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           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   11.2914(17)
_cell_length_b                   8.1975(13)
_cell_length_c                   18.139(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1679.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8567
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
Higashi, T. (1995) A program for absorption correction.
RIGAKU corporation, Tokyo, Japan.
;

_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 APEX area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7918
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2341
_reflns_number_gt                1654
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  '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^)+(0.0835P)^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       0.0057(17)
_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   -4(2)
_refine_ls_number_reflns         2341
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_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
O1 O 0.1739(2) 0.1264(3) 0.47596(17) 0.0525(8) Uani 1 1 d . . .
O2 O 0.3325(2) -0.0409(4) 0.25187(18) 0.0632(9) Uani 1 1 d . . .
N1 N 0.3729(3) 0.1663(3) 0.45347(17) 0.0443(8) Uani 1 1 d . . .
C1 C 0.2617(3) 0.1133(4) 0.4327(2) 0.0446(10) Uani 1 1 d . . .
C2 C 0.2562(3) 0.0456(4) 0.3615(2) 0.0455(10) Uani 1 1 d . . .
C3 C 0.1500(4) -0.0245(6) 0.3211(3) 0.0621(12) Uani 1 1 d . . .
H3A H 0.0860 0.0541 0.3177 0.075 Uiso 1 1 calc R . .
H3B H 0.1212 -0.1231 0.3445 0.075 Uiso 1 1 calc R . .
C4 C 0.2035(4) -0.0600(7) 0.2458(3) 0.0695(14) Uani 1 1 d . . .
H4A H 0.1841 -0.1703 0.2306 0.083 Uiso 1 1 calc R . .
H4B H 0.1722 0.0151 0.2094 0.083 Uiso 1 1 calc R . .
C5 C 0.3532(4) 0.0299(5) 0.3184(2) 0.0464(10) Uani 1 1 d . . .
C6 C 0.4677(3) 0.0778(5) 0.3417(2) 0.0476(10) Uani 1 1 d . . .
C7 C 0.4699(3) 0.1475(5) 0.4099(2) 0.0447(9) Uani 1 1 d . . .
H7A H 0.5423 0.1845 0.4277 0.054 Uiso 1 1 calc R . .
C8 C 0.3843(3) 0.2511(5) 0.5251(2) 0.0501(10) Uani 1 1 d . . .
H8A H 0.4674 0.2587 0.5381 0.060 Uiso 1 1 calc R . .
H8B H 0.3448 0.1875 0.5629 0.060 Uiso 1 1 calc R . .
C9 C 0.3315(3) 0.4206(5) 0.5232(2) 0.0452(10) Uani 1 1 d . . .
C10 C 0.3951(4) 0.5463(5) 0.4890(3) 0.0538(11) Uani 1 1 d . . .
H10A H 0.4709 0.5274 0.4710 0.065 Uiso 1 1 calc R . .
C11 C 0.3440(5) 0.6988(6) 0.4823(3) 0.0676(12) Uani 1 1 d . . .
H11A H 0.3847 0.7813 0.4579 0.081 Uiso 1 1 calc R . .
C12 C 0.2358(5) 0.7296(6) 0.5107(3) 0.0712(14) Uani 1 1 d . . .
H12A H 0.2039 0.8338 0.5068 0.085 Uiso 1 1 calc R . .
C13 C 0.1715(4) 0.6079(6) 0.5455(3) 0.0638(13) Uani 1 1 d . . .
H13A H 0.0962 0.6285 0.5640 0.077 Uiso 1 1 calc R . .
C14 C 0.2226(4) 0.4541(5) 0.5521(3) 0.0571(11) Uani 1 1 d . . .
H14A H 0.1816 0.3723 0.5768 0.068 Uiso 1 1 calc R . .
C15 C 0.5771(4) 0.0562(5) 0.2981(2) 0.0472(10) Uani 1 1 d . . .
C16 C 0.5792(4) 0.0792(5) 0.2222(3) 0.0571(12) Uani 1 1 d . . .
H16A H 0.5097 0.1079 0.1978 0.069 Uiso 1 1 calc R . .
C17 C 0.6828(4) 0.0603(5) 0.1820(3) 0.0562(11) Uani 1 1 d . . .
H17A H 0.6817 0.0788 0.1314 0.067 Uiso 1 1 calc R . .
C18 C 0.7869(4) 0.0147(6) 0.2152(3) 0.0576(12) Uani 1 1 d . . .
C19 C 0.7854(4) -0.0059(7) 0.2899(3) 0.0651(13) Uani 1 1 d . . .
H19A H 0.8554 -0.0332 0.3139 0.078 Uiso 1 1 calc R . .
C20 C 0.6814(4) 0.0131(6) 0.3317(3) 0.0589(12) Uani 1 1 d . . .
H20A H 0.6832 -0.0037 0.3824 0.071 Uiso 1 1 calc R . .
C21 C 0.8965(4) -0.0125(7) 0.1705(3) 0.0776(15) Uani 1 1 d . . .
H21A H 0.9603 -0.0435 0.2025 0.116 Uiso 1 1 calc R . .
H21B H 0.9169 0.0862 0.1451 0.116 Uiso 1 1 calc R . .
H21C H 0.8825 -0.0978 0.1353 0.116 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
O1 0.0447(16) 0.0528(15) 0.0599(19) -0.0037(14) 0.0066(15) 0.0007(12)
O2 0.0493(17) 0.083(2) 0.058(2) -0.0200(17) -0.0046(16) -0.0025(14)
N1 0.048(2) 0.0427(17) 0.0421(19) -0.0024(14) -0.0022(16) 0.0018(14)
C1 0.032(2) 0.041(2) 0.061(3) 0.0037(19) -0.003(2) 0.0007(17)
C2 0.036(2) 0.047(2) 0.054(3) -0.0057(19) -0.001(2) 0.0008(16)
C3 0.034(2) 0.076(3) 0.076(3) -0.016(3) -0.011(2) -0.006(2)
C4 0.045(3) 0.091(4) 0.073(4) -0.017(3) -0.010(2) -0.001(2)
C5 0.046(2) 0.050(2) 0.043(2) -0.0040(19) -0.004(2) 0.0042(18)
C6 0.046(2) 0.048(2) 0.049(3) -0.0014(18) -0.006(2) 0.0023(17)
C7 0.037(2) 0.049(2) 0.049(2) -0.0013(18) 0.001(2) -0.0001(16)
C8 0.053(2) 0.053(2) 0.044(2) 0.000(2) -0.005(2) 0.0021(19)
C9 0.050(2) 0.050(2) 0.035(2) -0.0016(18) -0.0051(19) 0.0022(18)
C10 0.052(3) 0.056(3) 0.054(3) -0.003(2) 0.000(2) -0.003(2)
C11 0.091(4) 0.052(3) 0.059(3) 0.002(2) 0.001(3) -0.006(3)
C12 0.104(4) 0.052(3) 0.057(3) -0.005(2) -0.004(3) 0.006(3)
C13 0.058(3) 0.070(3) 0.063(3) -0.012(2) 0.008(2) 0.013(2)
C14 0.072(3) 0.050(3) 0.049(3) -0.002(2) 0.012(2) 0.001(2)
C15 0.047(3) 0.054(2) 0.041(3) -0.0008(18) 0.0007(19) -0.0025(18)
C16 0.048(3) 0.066(3) 0.058(3) 0.005(2) -0.003(2) 0.003(2)
C17 0.053(3) 0.073(3) 0.042(2) 0.003(2) -0.002(2) -0.004(2)
C18 0.053(3) 0.068(3) 0.052(3) -0.005(2) 0.009(2) -0.004(2)
C19 0.035(2) 0.097(4) 0.063(3) -0.003(3) -0.002(2) 0.011(2)
C20 0.049(3) 0.084(3) 0.044(3) 0.000(2) -0.003(2) 0.004(2)
C21 0.047(3) 0.117(4) 0.069(4) -0.012(3) 0.012(3) -0.005(3)

_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 C1 1.269(5) . ?
O2 C5 1.359(5) . ?
O2 C4 1.469(5) . ?
N1 C7 1.359(5) . ?
N1 C1 1.382(5) . ?
N1 C8 1.479(5) . ?
C1 C2 1.405(6) . ?
C2 C5 1.352(6) . ?
C2 C3 1.519(5) . ?
C3 C4 1.521(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.416(5) . ?
C6 C7 1.362(6) . ?
C6 C15 1.477(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.512(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.364(6) . ?
C9 C10 1.401(6) . ?
C10 C11 1.382(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.349(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.386(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.392(6) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C20 1.372(6) . ?
C15 C16 1.391(6) . ?
C16 C17 1.387(6) . ?
C16 H16A 0.9300 . ?
C17 C18 1.373(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.366(6) . ?
C18 C21 1.496(6) . ?
C19 C20 1.407(6) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C5 O2 C4 106.4(3) . . ?
C7 N1 C1 122.5(3) . . ?
C7 N1 C8 119.6(3) . . ?
C1 N1 C8 117.8(3) . . ?
O1 C1 N1 120.9(4) . . ?
O1 C1 C2 124.6(3) . . ?
N1 C1 C2 114.5(3) . . ?
C5 C2 C1 122.2(4) . . ?
C5 C2 C3 108.9(4) . . ?
C1 C2 C3 128.9(4) . . ?
C2 C3 C4 101.1(3) . . ?
C2 C3 H3A 111.6 . . ?
C4 C3 H3A 111.6 . . ?
C2 C3 H3B 111.6 . . ?
C4 C3 H3B 111.6 . . ?
H3A C3 H3B 109.4 . . ?
O2 C4 C3 107.9(4) . . ?
O2 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
O2 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C2 C5 O2 114.6(4) . . ?
C2 C5 C6 122.7(4) . . ?
O2 C5 C6 122.7(4) . . ?
C7 C6 C5 113.8(4) . . ?
C7 C6 C15 121.4(3) . . ?
C5 C6 C15 124.8(4) . . ?
N1 C7 C6 124.1(3) . . ?
N1 C7 H7A 117.9 . . ?
C6 C7 H7A 117.9 . . ?
N1 C8 C9 112.3(3) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 118.9(4) . . ?
C14 C9 C8 122.2(4) . . ?
C10 C9 C8 118.9(4) . . ?
C11 C10 C9 119.4(4) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
C12 C11 C10 120.9(5) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C11 C12 C13 120.9(5) . . ?
C11 C12 H12A 119.5 . . ?
C13 C12 H12A 119.5 . . ?
C12 C13 C14 118.2(4) . . ?
C12 C13 H13A 120.9 . . ?
C14 C13 H13A 120.9 . . ?
C9 C14 C13 121.6(4) . . ?
C9 C14 H14A 119.2 . . ?
C13 C14 H14A 119.2 . . ?
C20 C15 C16 117.4(4) . . ?
C20 C15 C6 120.7(4) . . ?
C16 C15 C6 121.9(4) . . ?
C17 C16 C15 121.3(4) . . ?
C17 C16 H16A 119.3 . . ?
C15 C16 H16A 119.3 . . ?
C18 C17 C16 121.5(5) . . ?
C18 C17 H17A 119.3 . . ?
C16 C17 H17A 119.3 . . ?
C19 C18 C17 117.3(4) . . ?
C19 C18 C21 121.9(5) . . ?
C17 C18 C21 120.7(4) . . ?
C18 C19 C20 122.1(5) . . ?
C18 C19 H19A 119.0 . . ?
C20 C19 H19A 119.0 . . ?
C15 C20 C19 120.4(4) . . ?
C15 C20 H20A 119.8 . . ?
C19 C20 H20A 119.8 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033

#######################################################################

data_t1
#TrackingRef '- CIF.cif'

_database_code_depnum_ccdc_archive 'CCDC 829460'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N O4'
_chemical_formula_weight         347.36

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'
O O 0.0106 0.0060 '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'

_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                   19.023(5)
_cell_length_b                   8.279(5)
_cell_length_c                   11.214(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.913(5)
_cell_angle_gamma                90.00
_cell_volume                     1714.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3980
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      29.13

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
CrysAlis (Oxford Diffraction, 2006)
;

_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  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7634
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0811
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         29.13
_reflns_number_total             3980
_reflns_number_gt                1741
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2006)'
_computing_cell_refinement       CrysAlis
_computing_data_reduction        CrysAlis
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0624P)^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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3980
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1644
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_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 0.69984(14) 0.3440(3) 1.1844(2) 0.0457(7) Uani 1 1 d . . .
H1 H 0.6816 0.3026 1.2479 0.055 Uiso 1 1 calc R . .
C2 C 0.76765(14) 0.4095(3) 1.2134(2) 0.0453(6) Uani 1 1 d . . .
C3 C 0.79120(15) 0.4663(3) 1.1110(2) 0.0489(7) Uani 1 1 d . . .
C4 C 0.86311(18) 0.5758(4) 0.9971(3) 0.0760(10) Uani 1 1 d . . .
H4A H 0.9014 0.5138 0.9750 0.091 Uiso 1 1 calc R . .
H4B H 0.8742 0.6897 0.9928 0.091 Uiso 1 1 calc R . .
C5 C 0.78976(17) 0.5371(4) 0.9087(3) 0.0676(9) Uani 1 1 d . . .
H5A H 0.7658 0.6342 0.8708 0.081 Uiso 1 1 calc R . .
H5B H 0.7952 0.4620 0.8451 0.081 Uiso 1 1 calc R . .
C6 C 0.74959(15) 0.4620(3) 0.9943(2) 0.0479(7) Uani 1 1 d . . .
C7 C 0.67953(15) 0.3953(3) 0.9663(2) 0.0449(7) Uani 1 1 d . . .
C8 C 0.58658(14) 0.2534(3) 1.0454(2) 0.0493(7) Uani 1 1 d . . .
H8A H 0.5509 0.3168 0.9879 0.059 Uiso 1 1 calc R . .
H8B H 0.5713 0.2467 1.1218 0.059 Uiso 1 1 calc R . .
C9 C 0.58928(13) 0.0855(3) 0.9942(2) 0.0434(6) Uani 1 1 d . . .
C10 C 0.56117(14) 0.0549(3) 0.8706(2) 0.0502(7) Uani 1 1 d . . .
H10 H 0.5398 0.1382 0.8188 0.060 Uiso 1 1 calc R . .
C11 C 0.56456(16) -0.0979(4) 0.8234(3) 0.0622(8) Uani 1 1 d . . .
H11 H 0.5454 -0.1171 0.7402 0.075 Uiso 1 1 calc R . .
C12 C 0.59597(17) -0.2212(4) 0.8987(3) 0.0677(9) Uani 1 1 d . . .
H12 H 0.5993 -0.3237 0.8665 0.081 Uiso 1 1 calc R . .
C13 C 0.62258(16) -0.1931(4) 1.0219(3) 0.0667(9) Uani 1 1 d . . .
H13 H 0.6429 -0.2775 1.0735 0.080 Uiso 1 1 calc R . .
C14 C 0.61940(15) -0.0406(3) 1.0696(2) 0.0552(7) Uani 1 1 d . . .
H14 H 0.6377 -0.0226 1.1531 0.066 Uiso 1 1 calc R . .
C15 C 0.81080(15) 0.4167(3) 1.3424(2) 0.0481(7) Uani 1 1 d . . .
C16 C 0.78226(16) 0.4783(4) 1.4344(2) 0.0587(8) Uani 1 1 d . . .
H16 H 0.7352 0.5185 1.4150 0.070 Uiso 1 1 calc R . .
C17 C 0.82262(18) 0.4817(4) 1.5571(2) 0.0652(8) Uani 1 1 d . . .
H17 H 0.8033 0.5234 1.6194 0.078 Uiso 1 1 calc R . .
C18 C 0.89093(17) 0.4216(3) 1.5807(2) 0.0580(8) Uani 1 1 d . . .
C19 C 1.0001(2) 0.3223(5) 1.6675(3) 0.0926(12) Uani 1 1 d . . .
H19A H 1.0459 0.3762 1.7011 0.111 Uiso 1 1 calc R . .
H19B H 1.0017 0.2167 1.7056 0.111 Uiso 1 1 calc R . .
C20 C 0.91926(16) 0.3581(4) 1.4906(3) 0.0596(8) Uani 1 1 d . . .
C21 C 0.88129(15) 0.3539(4) 1.3714(2) 0.0588(8) Uani 1 1 d . . .
H21 H 0.9015 0.3106 1.3108 0.071 Uiso 1 1 calc R . .
O1 O 0.94223(14) 0.4147(3) 1.69264(17) 0.0819(7) Uani 1 1 d . . .
O2 O 0.98895(12) 0.3055(3) 1.5389(2) 0.0907(8) Uani 1 1 d . . .
O3 O 0.85775(11) 0.5336(2) 1.12167(16) 0.0704(6) Uani 1 1 d . . .
O4 O 0.63725(10) 0.3876(2) 0.86228(15) 0.0553(5) Uani 1 1 d . . .
N1 N 0.65734(11) 0.3358(2) 1.06817(17) 0.0430(5) 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 0.0500(18) 0.0511(15) 0.0387(14) -0.0021(12) 0.0161(13) -0.0007(14)
C2 0.0441(17) 0.0527(16) 0.0413(14) -0.0048(12) 0.0145(12) -0.0056(13)
C3 0.0468(17) 0.0490(16) 0.0551(17) -0.0057(13) 0.0203(14) -0.0096(13)
C4 0.084(3) 0.084(2) 0.070(2) 0.0052(17) 0.0372(18) -0.0191(19)
C5 0.077(2) 0.071(2) 0.0598(18) 0.0089(16) 0.0251(17) -0.0086(17)
C6 0.0574(19) 0.0456(16) 0.0430(15) 0.0000(12) 0.0169(13) -0.0041(14)
C7 0.0589(19) 0.0390(14) 0.0390(14) -0.0037(12) 0.0159(14) 0.0036(13)
C8 0.0386(16) 0.0604(17) 0.0503(15) -0.0058(14) 0.0137(12) -0.0003(13)
C9 0.0326(15) 0.0500(16) 0.0492(15) -0.0019(13) 0.0128(12) -0.0035(12)
C10 0.0422(17) 0.0531(17) 0.0517(16) 0.0009(14) 0.0041(13) -0.0059(13)
C11 0.065(2) 0.062(2) 0.0569(17) -0.0100(17) 0.0081(15) -0.0109(16)
C12 0.071(2) 0.0513(18) 0.083(2) -0.0159(18) 0.0229(18) -0.0075(16)
C13 0.067(2) 0.0531(19) 0.081(2) 0.0108(17) 0.0197(17) 0.0066(16)
C14 0.0512(18) 0.0626(19) 0.0506(16) 0.0036(15) 0.0098(13) -0.0001(15)
C15 0.0450(17) 0.0547(16) 0.0453(15) 0.0001(13) 0.0125(13) -0.0045(13)
C16 0.0541(19) 0.075(2) 0.0471(16) -0.0012(14) 0.0131(14) 0.0004(15)
C17 0.070(2) 0.083(2) 0.0450(17) -0.0043(15) 0.0203(15) 0.0011(18)
C18 0.061(2) 0.0625(18) 0.0446(16) 0.0057(14) 0.0022(15) -0.0153(16)
C19 0.066(3) 0.117(3) 0.085(3) 0.027(2) 0.000(2) -0.016(2)
C20 0.0437(19) 0.066(2) 0.067(2) 0.0068(16) 0.0096(16) -0.0057(15)
C21 0.053(2) 0.075(2) 0.0507(17) -0.0080(14) 0.0156(14) -0.0042(16)
O1 0.0834(18) 0.0958(17) 0.0564(13) 0.0081(12) -0.0030(12) -0.0100(14)
O2 0.0553(16) 0.125(2) 0.0826(16) 0.0044(14) -0.0004(12) 0.0081(13)
O3 0.0594(14) 0.0924(16) 0.0622(13) -0.0018(11) 0.0199(10) -0.0275(12)
O4 0.0691(13) 0.0541(12) 0.0400(10) -0.0028(8) 0.0077(9) -0.0004(10)
N1 0.0448(14) 0.0463(12) 0.0392(12) -0.0045(10) 0.0127(10) -0.0032(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 N1 1.360(3) . ?
C1 C2 1.364(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.410(3) . ?
C2 C15 1.483(3) . ?
C3 C6 1.358(3) . ?
C3 O3 1.362(3) . ?
C4 O3 1.467(3) . ?
C4 C5 1.539(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.498(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.407(4) . ?
C7 O4 1.249(3) . ?
C7 N1 1.400(3) . ?
C8 N1 1.475(3) . ?
C8 C9 1.509(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.378(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.378(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.374(3) . ?
C15 C21 1.402(4) . ?
C16 C17 1.406(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.357(4) . ?
C17 H17 0.9300 . ?
C18 C20 1.360(4) . ?
C18 O1 1.393(3) . ?
C19 O2 1.414(4) . ?
C19 O1 1.423(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.358(4) . ?
C20 O2 1.377(3) . ?
C21 H21 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 C1 C2 124.0(2) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 113.9(2) . . ?
C1 C2 C15 121.2(2) . . ?
C3 C2 C15 124.8(2) . . ?
C6 C3 O3 114.2(2) . . ?
C6 C3 C2 123.4(3) . . ?
O3 C3 C2 122.4(2) . . ?
O3 C4 C5 107.7(2) . . ?
O3 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 . . ?
O3 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C6 C5 C4 101.4(2) . . ?
C6 C5 H5A 111.5 . . ?
C4 C5 H5A 111.5 . . ?
C6 C5 H5B 111.5 . . ?
C4 C5 H5B 111.5 . . ?
H5A C5 H5B 109.3 . . ?
C3 C6 C7 121.8(2) . . ?
C3 C6 C5 109.8(2) . . ?
C7 C6 C5 128.4(2) . . ?
O4 C7 N1 119.4(2) . . ?
O4 C7 C6 126.3(2) . . ?
N1 C7 C6 114.3(2) . . ?
N1 C8 C9 112.2(2) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 118.6(2) . . ?
C14 C9 C8 120.8(2) . . ?
C10 C9 C8 120.6(2) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.5(3) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C21 119.5(2) . . ?
C16 C15 C2 121.4(3) . . ?
C21 C15 C2 119.1(2) . . ?
C15 C16 C17 121.4(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 117.1(3) . . ?
C18 C17 H17 121.5 . . ?
C16 C17 H17 121.5 . . ?
C17 C18 C20 121.9(3) . . ?
C17 C18 O1 128.4(3) . . ?
C20 C18 O1 109.7(3) . . ?
O2 C19 O1 108.8(3) . . ?
O2 C19 H19A 109.9 . . ?
O1 C19 H19A 109.9 . . ?
O2 C19 H19B 109.9 . . ?
O1 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
C21 C20 C18 121.9(3) . . ?
C21 C20 O2 127.8(3) . . ?
C18 C20 O2 110.3(3) . . ?
C20 C21 C15 118.2(3) . . ?
C20 C21 H21 120.9 . . ?
C15 C21 H21 120.9 . . ?
C18 O1 C19 104.6(2) . . ?
C20 O2 C19 105.3(3) . . ?
C3 O3 C4 106.9(2) . . ?
C1 N1 C7 122.6(2) . . ?
C1 N1 C8 119.8(2) . . ?
C7 N1 C8 117.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.861
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038

#######################################################################

data_2
#TrackingRef '- CIF.cif'

#TrackingRef '- CIF.cif'

_database_code_depnum_ccdc_archive 'CCDC 839385'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl N O4'
_chemical_formula_weight         295.71

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           Monoclinic
_symmetry_space_group_name_H-M   Cc

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'

_cell_length_a                   4.670(3)
_cell_length_b                   24.712(3)
_cell_length_c                   12.388(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.024(3)
_cell_angle_gamma                90.00
_cell_volume                     1429.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3634
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9043
_exptl_absorpt_correction_T_max  0.9365
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
Higashi, T. (1995) A program for absorption correction.
RIGAKU corporation, Tokyo, Japan.
;

_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 APEX area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3555
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.04
_reflns_number_total             1957
_reflns_number_gt                1467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  '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^)+(0.0677P)^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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(11)
_refine_ls_number_reflns         1957
_refine_ls_number_parameters     185
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.002
_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 0.0580(8) 0.14848(15) 0.5017(4) 0.0585(10) Uani 1 1 d . . .
C2 C 0.2510(9) 0.18595(17) 0.5418(5) 0.0792(15) Uani 1 1 d . . .
C3 C 0.3787(15) 0.2233(2) 0.4742(9) 0.134(3) Uani 1 1 d . . .
H3 H 0.5101 0.2482 0.5020 0.160 Uiso 1 1 calc R . .
C4 C 0.309(2) 0.2232(3) 0.3663(11) 0.164(6) Uani 1 1 d . . .
H4 H 0.3964 0.2479 0.3207 0.197 Uiso 1 1 calc R . .
C5 C 0.119(2) 0.1882(3) 0.3260(6) 0.138(4) Uani 1 1 d . . .
H5 H 0.0704 0.1895 0.2528 0.166 Uiso 1 1 calc R . .
C6 C -0.0096(12) 0.14981(19) 0.3915(4) 0.0861(15) Uani 1 1 d . . .
H6 H -0.1397 0.1252 0.3621 0.103 Uiso 1 1 calc R . .
C7 C -0.0818(8) 0.10682(17) 0.5717(3) 0.0640(11) Uani 1 1 d . . .
H7A H -0.1595 0.1244 0.6347 0.077 Uiso 1 1 calc R . .
H7B H -0.2394 0.0902 0.5319 0.077 Uiso 1 1 calc R . .
C8 C 0.1533(7) 0.04760(14) 0.7064(3) 0.0456(9) Uani 1 1 d . . .
C9 C 0.3367(7) 0.00871(14) 0.7481(3) 0.0444(8) Uani 1 1 d . . .
C10 C 0.2870(7) 0.00547(17) 0.8580(3) 0.0526(9) Uani 1 1 d . . .
C11 C 0.0540(8) 0.04549(18) 0.8817(3) 0.0623(11) Uani 1 1 d . . .
H11A H -0.1110 0.0273 0.9114 0.075 Uiso 1 1 calc R . .
H11B H 0.1216 0.0725 0.9330 0.075 Uiso 1 1 calc R . .
C13 C 0.5445(7) -0.02504(14) 0.6877(3) 0.0481(9) Uani 1 1 d . . .
H13A H 0.6012 -0.0058 0.6232 0.058 Uiso 1 1 calc R . .
H13B H 0.7146 -0.0308 0.7323 0.058 Uiso 1 1 calc R . .
C14 C 0.4211(8) -0.07837(15) 0.6563(4) 0.0596(10) Uani 1 1 d . . .
H14A H 0.3680 -0.0985 0.7201 0.071 Uiso 1 1 calc R . .
H14B H 0.2513 -0.0733 0.6112 0.071 Uiso 1 1 calc R . .
C16 C 0.5522(14) -0.1492(2) 0.5409(6) 0.103(2) Uani 1 1 d . . .
H16 H 0.6906 -0.1677 0.5023 0.123 Uiso 1 1 calc R . .
Cl1 Cl 0.3276(3) 0.18703(6) 0.67995(16) 0.1254(7) Uani 1 1 d . . .
N1 N 0.1215(6) 0.06477(12) 0.6065(3) 0.0490(8) Uani 1 1 d . . .
O1 O 0.4068(6) -0.02262(12) 0.9292(2) 0.0688(8) Uani 1 1 d . . .
O2 O -0.0189(5) 0.07016(10) 0.7802(2) 0.0558(7) Uani 1 1 d . . .
O3 O 0.6377(7) -0.10748(13) 0.5976(4) 0.0980(12) Uani 1 1 d . . .
O4 O 0.3150(11) -0.16561(17) 0.5342(5) 0.1256(16) Uani 1 1 d . . .
H1 H 0.222(8) 0.0511(14) 0.552(3) 0.046(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
C1 0.059(2) 0.052(2) 0.064(3) -0.0015(18) 0.008(2) 0.0124(18)
C2 0.061(3) 0.048(2) 0.129(5) -0.022(3) 0.020(3) 0.010(2)
C3 0.096(4) 0.046(3) 0.261(11) 0.007(5) 0.064(7) 0.011(3)
C4 0.158(8) 0.081(5) 0.258(13) 0.068(8) 0.120(10) 0.050(5)
C5 0.204(9) 0.114(5) 0.098(5) 0.053(5) 0.070(6) 0.091(6)
C6 0.107(4) 0.076(3) 0.076(4) 0.006(3) 0.003(3) 0.036(3)
C7 0.053(2) 0.072(3) 0.066(3) 0.004(2) -0.006(2) 0.006(2)
C8 0.0414(18) 0.055(2) 0.041(2) -0.0119(17) 0.0089(16) -0.0051(16)
C9 0.0424(18) 0.053(2) 0.038(2) -0.0017(16) 0.0066(15) -0.0017(16)
C10 0.0426(18) 0.079(3) 0.036(2) 0.0016(19) -0.0008(16) -0.0128(18)
C11 0.059(2) 0.091(3) 0.037(2) -0.014(2) 0.0093(18) -0.004(2)
C13 0.0445(18) 0.050(2) 0.050(2) 0.0004(16) 0.0065(16) 0.0005(16)
C14 0.051(2) 0.061(2) 0.067(3) -0.008(2) 0.008(2) 0.0009(18)
C16 0.092(4) 0.070(3) 0.148(6) -0.031(3) 0.024(4) 0.008(3)
Cl1 0.0997(10) 0.1154(11) 0.1600(17) -0.0828(11) -0.0305(10) 0.0184(9)
N1 0.0482(17) 0.0558(18) 0.043(2) -0.0021(15) 0.0067(15) 0.0088(15)
O1 0.0638(17) 0.101(2) 0.0411(16) 0.0137(15) 0.0011(14) -0.0092(16)
O2 0.0536(15) 0.0702(16) 0.0441(16) -0.0094(12) 0.0121(13) 0.0065(12)
O3 0.0663(17) 0.072(2) 0.157(4) -0.047(2) 0.0205(19) 0.0021(16)
O4 0.109(3) 0.091(3) 0.176(5) -0.061(3) 0.007(3) -0.005(2)

_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 C2 1.379(6) . ?
C1 C6 1.396(7) . ?
C1 C7 1.503(5) . ?
C2 C3 1.388(9) . ?
C2 Cl1 1.742(6) . ?
C3 C4 1.370(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.333(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.467(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.314(4) . ?
C8 O2 1.349(4) . ?
C8 C9 1.381(5) . ?
C9 C10 1.386(5) . ?
C9 C13 1.492(5) . ?
C10 O1 1.247(5) . ?
C10 C11 1.504(6) . ?
C11 O2 1.434(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C14 1.487(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O3 1.448(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 O4 1.181(7) . ?
C16 O3 1.307(7) . ?
C16 H16 0.9300 . ?
N1 H1 0.89(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
C2 C1 C6 118.1(4) . . ?
C2 C1 C7 122.7(4) . . ?
C6 C1 C7 119.2(4) . . ?
C1 C2 C3 121.0(6) . . ?
C1 C2 Cl1 119.1(4) . . ?
C3 C2 Cl1 120.0(6) . . ?
C4 C3 C2 119.4(8) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120.8(8) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.0(9) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.6(6) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N1 C7 C1 111.7(3) . . ?
N1 C7 H7A 109.3 . . ?
C1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C1 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 O2 116.5(3) . . ?
N1 C8 C9 129.5(3) . . ?
O2 C8 C9 114.1(3) . . ?
C8 C9 C10 107.1(3) . . ?
C8 C9 C13 127.3(3) . . ?
C10 C9 C13 125.6(3) . . ?
O1 C10 C9 130.2(4) . . ?
O1 C10 C11 123.0(4) . . ?
C9 C10 C11 106.8(3) . . ?
O2 C11 C10 105.6(3) . . ?
O2 C11 H11A 110.6 . . ?
C10 C11 H11A 110.6 . . ?
O2 C11 H11B 110.6 . . ?
C10 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C14 C13 C9 112.0(3) . . ?
C14 C13 H13A 109.2 . . ?
C9 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C9 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O3 C14 C13 107.5(3) . . ?
O3 C14 H14A 110.2 . . ?
C13 C14 H14A 110.2 . . ?
O3 C14 H14B 110.2 . . ?
C13 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
O4 C16 O3 125.8(5) . . ?
O4 C16 H16 117.1 . . ?
O3 C16 H16 117.1 . . ?
C8 N1 C7 124.6(3) . . ?
C8 N1 H1 122(2) . . ?
C7 N1 H1 113(2) . . ?
C8 O2 C11 106.5(3) . . ?
C16 O3 C14 116.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.035

#END