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


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#
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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_o11_15mo
_database_code_depnum_ccdc_archive 'CCDC 875574'
#TrackingRef 'o11_15mo.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H58 Cl3 N3 O3'
_chemical_formula_weight         723.23

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   P2(1)/n

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

_cell_length_a                   13.590(3)
_cell_length_b                   19.104(4)
_cell_length_c                   17.224(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.86(3)
_cell_angle_gamma                90.00
_cell_volume                     4178.6(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    21052
_cell_measurement_theta_min      6.37
_cell_measurement_theta_max      54.95

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9294
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_process_details   'Rigaku Rapid Auto'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40579
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_sigmaI/netI    0.0724
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         27.48
_reflns_number_total             9561
_reflns_number_gt                4808
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rigaku Rapid Auto'
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Diamond 3.2g,ORTEP3'
_computing_publication_material  WinGX

_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^)+(0.0635P)^2^+0.2858P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         9561
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Cl1 Cl 0.23651(5) 0.24431(4) 0.49443(4) 0.04014(18) Uani 1 1 d . . .
Cl2 Cl 0.39164(6) -0.10348(5) 0.81331(5) 0.0592(2) Uani 1 1 d . . .
Cl3 Cl 0.28625(7) 0.10371(5) 0.04115(5) 0.0628(3) Uani 1 1 d . . .
O1 O 0.35537(16) 0.00351(11) 0.43220(12) 0.0529(5) Uani 1 1 d . . .
O2 O 0.00908(15) 0.18691(12) 0.45622(12) 0.0514(6) Uani 1 1 d . . .
H2O H 0.077(3) 0.207(2) 0.474(2) 0.097(13) Uiso 1 1 d . . .
O3 O 0.30789(16) 0.37922(12) 0.41540(15) 0.0543(6) Uani 1 1 d . . .
H3O H 0.285(3) 0.343(2) 0.443(3) 0.113(16) Uiso 1 1 d . . .
N1 N 0.30377(17) 0.07632(13) 0.51607(13) 0.0361(5) Uani 1 1 d . . .
H1N H 0.271(2) 0.1158(17) 0.5177(17) 0.050(9) Uiso 1 1 d . . .
N2 N 0.29931(18) 0.11473(13) 0.38879(14) 0.0402(5) Uani 1 1 d . . .
H2N H 0.291(2) 0.1571(18) 0.4074(19) 0.060(10) Uiso 1 1 d . . .
C1 C 0.3219(2) 0.05993(15) 0.44430(16) 0.0388(6) Uani 1 1 d . . .
C2 C 0.32485(18) 0.03137(14) 0.58448(15) 0.0335(6) Uani 1 1 d . . .
C3 C 0.25742(18) 0.03322(13) 0.63031(15) 0.0333(6) Uani 1 1 d . . .
C4 C 0.2789(2) -0.00783(14) 0.70128(16) 0.0387(6) Uani 1 1 d . . .
H4 H 0.2347 -0.0055 0.7332 0.046 Uiso 1 1 calc R . .
C5 C 0.3653(2) -0.05205(15) 0.72489(16) 0.0422(7) Uani 1 1 d . . .
C6 C 0.43121(19) -0.05446(15) 0.68024(17) 0.0417(7) Uani 1 1 d . . .
H6 H 0.4904 -0.0848 0.6973 0.050 Uiso 1 1 calc R . .
C7 C 0.4119(2) -0.01290(14) 0.61052(17) 0.0405(6) Uani 1 1 d . . .
H7 H 0.4583 -0.0146 0.5803 0.049 Uiso 1 1 calc R . .
C8 C 0.16425(19) 0.07662(14) 0.60160(15) 0.0352(6) Uani 1 1 d . . .
C9 C 0.08778(19) 0.11188(14) 0.57057(15) 0.0354(6) Uani 1 1 d . . .
C10 C -0.00725(19) 0.15360(15) 0.52491(16) 0.0378(6) Uani 1 1 d . . .
C11 C -0.0292(3) 0.20861(19) 0.58015(19) 0.0611(9) Uani 1 1 d . . .
H11A H 0.0302 0.2413 0.5995 0.092 Uiso 1 1 calc R . .
H11B H -0.0383 0.1858 0.6281 0.092 Uiso 1 1 calc R . .
H11C H -0.0935 0.2342 0.5486 0.092 Uiso 1 1 calc R . .
C12 C -0.1006(2) 0.10501(17) 0.4881(2) 0.0553(8) Uani 1 1 d . . .
H12A H -0.1618 0.1321 0.4537 0.083 Uiso 1 1 calc R . .
H12B H -0.1168 0.0820 0.5330 0.083 Uiso 1 1 calc R . .
H12C H -0.0835 0.0695 0.4538 0.083 Uiso 1 1 calc R . .
C13 C 0.29901(19) 0.10964(15) 0.30712(16) 0.0386(6) Uani 1 1 d . . .
C14 C 0.32138(19) 0.17010(15) 0.27018(16) 0.0383(6) Uani 1 1 d . . .
C15 C 0.3167(2) 0.16725(16) 0.18766(17) 0.0440(7) Uani 1 1 d . . .
H15 H 0.3305 0.2081 0.1618 0.053 Uiso 1 1 calc R . .
C16 C 0.2921(2) 0.10565(17) 0.14405(17) 0.0448(7) Uani 1 1 d . . .
C17 C 0.2718(2) 0.04539(17) 0.17989(17) 0.0460(7) Uani 1 1 d . . .
H17 H 0.2558 0.0029 0.1492 0.055 Uiso 1 1 calc R . .
C18 C 0.2751(2) 0.04761(16) 0.26164(17) 0.0453(7) Uani 1 1 d . . .
H18 H 0.2608 0.0064 0.2866 0.054 Uiso 1 1 calc R . .
C19 C 0.3496(2) 0.23434(16) 0.31580(17) 0.0402(7) Uani 1 1 d . . .
C20 C 0.3737(2) 0.28726(16) 0.35438(17) 0.0421(7) Uani 1 1 d . . .
C21 C 0.3998(2) 0.35374(15) 0.40174(19) 0.0458(7) Uani 1 1 d . . .
C22 C 0.4886(2) 0.34208(18) 0.4845(2) 0.0604(9) Uani 1 1 d . . .
H22A H 0.5060 0.3865 0.5148 0.091 Uiso 1 1 calc R . .
H22B H 0.5507 0.3243 0.4746 0.091 Uiso 1 1 calc R . .
H22C H 0.4662 0.3080 0.5174 0.091 Uiso 1 1 calc R . .
C23 C 0.4282(3) 0.40901(18) 0.3498(3) 0.0723(11) Uani 1 1 d . . .
H23A H 0.3690 0.4156 0.2974 0.108 Uiso 1 1 calc R . .
H23B H 0.4903 0.3937 0.3380 0.108 Uiso 1 1 calc R . .
H23C H 0.4438 0.4533 0.3805 0.108 Uiso 1 1 calc R . .
N1A N 0.95848(15) 0.27821(11) 0.24396(12) 0.0326(5) Uani 1 1 d . . .
C1A C 1.03070(19) 0.31650(14) 0.32077(15) 0.0382(6) Uani 1 1 d . . .
H1A1 H 1.0152 0.2996 0.3695 0.046 Uiso 1 1 calc R . .
H1A2 H 1.1044 0.3034 0.3295 0.046 Uiso 1 1 calc R . .
C2A C 1.0228(3) 0.39522(16) 0.31834(17) 0.0519(8) Uani 1 1 d . . .
H2A1 H 0.9487 0.4089 0.2882 0.062 Uiso 1 1 calc R . .
H2A2 H 1.0658 0.4141 0.2873 0.062 Uiso 1 1 calc R . .
C3A C 1.0598(2) 0.42726(17) 0.40438(18) 0.0513(8) Uani 1 1 d . . .
H3A1 H 1.1307 0.4089 0.4368 0.062 Uiso 1 1 calc R . .
H3A2 H 1.0658 0.4786 0.3995 0.062 Uiso 1 1 calc R . .
C4A C 0.9867(4) 0.4119(2) 0.4503(3) 0.0936(14) Uani 1 1 d . . .
H4A1 H 0.9162 0.4294 0.4182 0.140 Uiso 1 1 calc R . .
H4A2 H 1.0128 0.4350 0.5047 0.140 Uiso 1 1 calc R . .
H4A3 H 0.9836 0.3613 0.4581 0.140 Uiso 1 1 calc R . .
C5A C 0.84386(18) 0.28911(15) 0.23358(15) 0.0352(6) Uani 1 1 d . . .
H5A1 H 0.8290 0.3400 0.2282 0.042 Uiso 1 1 calc R . .
H5A2 H 0.7996 0.2669 0.1807 0.042 Uiso 1 1 calc R . .
C6A C 0.80976(19) 0.26099(16) 0.30241(16) 0.0407(7) Uani 1 1 d . . .
H6A1 H 0.8128 0.2092 0.3026 0.049 Uiso 1 1 calc R . .
H6A2 H 0.8589 0.2779 0.3567 0.049 Uiso 1 1 calc R . .
C7A C 0.7000(2) 0.2840(2) 0.29108(19) 0.0577(9) Uani 1 1 d . . .
H7A1 H 0.6521 0.2694 0.2353 0.069 Uiso 1 1 calc R . .
H7A2 H 0.6984 0.3358 0.2934 0.069 Uiso 1 1 calc R . .
C8A C 0.6596(2) 0.25443(19) 0.3556(2) 0.0595(9) Uani 1 1 d . . .
H8A1 H 0.6598 0.2032 0.3531 0.089 Uiso 1 1 calc R . .
H8A2 H 0.5877 0.2711 0.3445 0.089 Uiso 1 1 calc R . .
H8A3 H 0.7052 0.2699 0.4110 0.089 Uiso 1 1 calc R . .
C9A C 0.97127(19) 0.30714(15) 0.16607(14) 0.0353(6) Uani 1 1 d . . .
H9A1 H 0.9193 0.2836 0.1175 0.042 Uiso 1 1 calc R . .
H9A2 H 0.9531 0.3575 0.1621 0.042 Uiso 1 1 calc R . .
C10A C 1.07895(19) 0.29970(16) 0.15928(16) 0.0405(7) Uani 1 1 d . . .
H10A H 1.0945 0.2497 0.1540 0.049 Uiso 1 1 calc R . .
H10B H 1.1337 0.3186 0.2098 0.049 Uiso 1 1 calc R . .
C11A C 1.0794(2) 0.34001(16) 0.08290(18) 0.0469(7) Uani 1 1 d . . .
H11D H 1.0211 0.3228 0.0335 0.056 Uiso 1 1 calc R . .
H11E H 1.0665 0.3902 0.0901 0.056 Uiso 1 1 calc R . .
C12A C 1.1822(2) 0.33273(19) 0.0677(2) 0.0606(9) Uani 1 1 d . . .
H12D H 1.2408 0.3473 0.1175 0.091 Uiso 1 1 calc R . .
H12E H 1.1803 0.3624 0.0207 0.091 Uiso 1 1 calc R . .
H12F H 1.1920 0.2838 0.0549 0.091 Uiso 1 1 calc R . .
C13A C 0.9872(2) 0.20125(14) 0.25595(16) 0.0406(6) Uani 1 1 d . B .
H13A H 1.0605 0.1957 0.2581 0.049 Uiso 1 1 calc R . .
H13B H 0.9852 0.1864 0.3104 0.049 Uiso 1 1 calc R . .
C14A C 0.9173(2) 0.15273(16) 0.1899(2) 0.0537(8) Uani 1 1 d . . .
H14A H 0.9132 0.1696 0.1345 0.064 Uiso 1 1 calc R A 1
H14B H 0.8453 0.1534 0.1917 0.064 Uiso 1 1 calc R A 1
C151 C 0.9587(5) 0.0785(2) 0.2022(3) 0.1032(16) Uani 0.459(6) 1 d P B 1
H15A H 1.0100 0.0745 0.1736 0.124 Uiso 0.459(6) 1 calc PR B 1
H15B H 0.8989 0.0474 0.1724 0.124 Uiso 0.459(6) 1 calc PR B 1
C161 C 1.0142(6) 0.0467(4) 0.2940(5) 0.062(2) Uani 0.459(6) 1 d P B 1
H16A H 1.0703 0.0783 0.3270 0.093 Uiso 0.459(6) 1 calc PR B 1
H16B H 1.0442 0.0008 0.2903 0.093 Uiso 0.459(6) 1 calc PR B 1
H16C H 0.9618 0.0418 0.3207 0.093 Uiso 0.459(6) 1 calc PR B 1
C152 C 0.9587(5) 0.0785(2) 0.2022(3) 0.1032(16) Uani 0.541(6) 1 d P B 2
H15C H 0.9705 0.0617 0.2592 0.124 Uiso 0.541(6) 1 calc PR B 2
H15D H 1.0252 0.0745 0.1912 0.124 Uiso 0.541(6) 1 calc PR B 2
C162 C 0.8567(5) 0.0323(3) 0.1283(4) 0.065(2) Uani 0.541(6) 1 d P B 2
H16D H 0.7891 0.0462 0.1321 0.098 Uiso 0.541(6) 1 calc PR B 2
H16E H 0.8672 -0.0181 0.1390 0.098 Uiso 0.541(6) 1 calc PR B 2
H16F H 0.8565 0.0428 0.0726 0.098 Uiso 0.541(6) 1 calc PR B 2

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 0.0352(3) 0.0397(4) 0.0426(3) 0.0059(3) 0.0103(3) 0.0022(3)
Cl2 0.0619(5) 0.0570(5) 0.0517(4) 0.0216(4) 0.0117(4) 0.0073(4)
Cl3 0.0762(5) 0.0733(6) 0.0436(4) 0.0072(4) 0.0269(4) 0.0193(5)
O1 0.0741(14) 0.0391(13) 0.0529(12) 0.0042(9) 0.0318(11) 0.0174(10)
O2 0.0346(10) 0.0710(16) 0.0425(11) 0.0195(10) 0.0061(9) 0.0007(10)
O3 0.0533(12) 0.0366(13) 0.0857(16) 0.0062(11) 0.0404(12) 0.0083(10)
N1 0.0409(12) 0.0304(13) 0.0393(12) 0.0039(10) 0.0168(10) 0.0056(10)
N2 0.0507(14) 0.0334(14) 0.0400(12) 0.0009(11) 0.0205(11) 0.0012(11)
C1 0.0388(14) 0.0352(17) 0.0431(15) 0.0036(13) 0.0156(12) 0.0001(12)
C2 0.0307(12) 0.0304(15) 0.0382(13) 0.0023(11) 0.0110(11) -0.0021(11)
C3 0.0295(12) 0.0298(15) 0.0374(13) -0.0010(11) 0.0080(11) -0.0033(11)
C4 0.0366(14) 0.0379(16) 0.0401(14) 0.0017(12) 0.0118(12) -0.0028(12)
C5 0.0409(15) 0.0326(16) 0.0459(15) 0.0048(13) 0.0068(12) -0.0034(12)
C6 0.0299(13) 0.0379(17) 0.0512(16) 0.0055(13) 0.0069(12) 0.0041(12)
C7 0.0362(14) 0.0351(16) 0.0492(15) 0.0031(13) 0.0141(12) 0.0012(12)
C8 0.0302(13) 0.0366(15) 0.0384(13) 0.0017(12) 0.0118(11) -0.0017(12)
C9 0.0320(13) 0.0365(16) 0.0370(13) -0.0002(12) 0.0115(11) -0.0005(12)
C10 0.0327(13) 0.0413(17) 0.0383(14) 0.0025(12) 0.0113(11) 0.0025(12)
C11 0.0592(19) 0.061(2) 0.0576(18) -0.0051(17) 0.0135(16) 0.0217(17)
C12 0.0333(14) 0.060(2) 0.068(2) -0.0013(17) 0.0112(14) -0.0033(14)
C13 0.0333(13) 0.0439(17) 0.0392(14) 0.0012(13) 0.0138(11) 0.0006(12)
C14 0.0341(13) 0.0394(17) 0.0433(14) 0.0053(13) 0.0161(12) 0.0057(12)
C15 0.0455(16) 0.0441(18) 0.0460(15) 0.0100(14) 0.0208(13) 0.0096(13)
C16 0.0408(15) 0.052(2) 0.0435(15) 0.0057(14) 0.0178(12) 0.0089(14)
C17 0.0422(15) 0.0503(19) 0.0452(15) -0.0059(14) 0.0154(13) -0.0003(14)
C18 0.0489(16) 0.0433(18) 0.0461(15) -0.0010(14) 0.0197(13) -0.0049(14)
C19 0.0371(14) 0.0407(18) 0.0454(15) 0.0106(14) 0.0180(12) 0.0051(13)
C20 0.0421(15) 0.0362(17) 0.0514(16) 0.0109(14) 0.0209(13) 0.0036(13)
C21 0.0458(16) 0.0351(17) 0.0654(19) 0.0034(14) 0.0306(15) 0.0032(13)
C22 0.0502(18) 0.058(2) 0.072(2) -0.0098(18) 0.0206(16) -0.0032(16)
C23 0.081(2) 0.045(2) 0.115(3) 0.017(2) 0.065(2) 0.0015(17)
N1A 0.0297(10) 0.0365(13) 0.0297(10) 0.0015(9) 0.0082(9) 0.0033(9)
C1A 0.0337(13) 0.0457(18) 0.0295(12) -0.0004(12) 0.0040(11) -0.0010(12)
C2A 0.0659(19) 0.0426(18) 0.0409(15) -0.0028(13) 0.0113(14) -0.0109(15)
C3A 0.0528(17) 0.051(2) 0.0491(16) -0.0117(14) 0.0169(14) -0.0023(15)
C4A 0.156(4) 0.065(3) 0.095(3) -0.021(2) 0.089(3) -0.012(3)
C5A 0.0269(12) 0.0411(16) 0.0343(12) 0.0025(12) 0.0069(10) 0.0033(11)
C6A 0.0359(14) 0.0473(18) 0.0397(14) 0.0056(13) 0.0143(12) 0.0021(12)
C7A 0.0415(16) 0.074(2) 0.0615(19) 0.0129(17) 0.0229(14) 0.0101(15)
C8A 0.0483(17) 0.076(2) 0.067(2) 0.0032(18) 0.0351(15) 0.0015(16)
C9A 0.0365(13) 0.0398(16) 0.0295(12) 0.0029(11) 0.0117(11) 0.0011(12)
C10A 0.0349(13) 0.0440(17) 0.0419(14) 0.0013(13) 0.0131(12) -0.0002(12)
C11A 0.0484(16) 0.0412(18) 0.0588(17) 0.0091(14) 0.0286(14) 0.0025(13)
C12A 0.0600(19) 0.063(2) 0.075(2) 0.0097(18) 0.0431(17) 0.0051(17)
C13A 0.0453(15) 0.0342(16) 0.0472(15) 0.0061(13) 0.0225(13) 0.0068(12)
C14A 0.0645(19) 0.0409(19) 0.066(2) -0.0102(16) 0.0352(17) -0.0073(15)
C151 0.203(5) 0.040(2) 0.075(3) -0.0020(19) 0.059(3) 0.006(3)
C161 0.076(5) 0.036(4) 0.082(5) 0.005(4) 0.039(4) 0.005(4)
C152 0.203(5) 0.040(2) 0.075(3) -0.0020(19) 0.059(3) 0.006(3)
C162 0.077(4) 0.040(4) 0.077(4) -0.013(3) 0.025(3) -0.003(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
Cl2 C5 1.739(3) . ?
Cl3 C16 1.746(3) . ?
O1 C1 1.216(3) . ?
O2 C10 1.429(3) . ?
O3 C21 1.436(3) . ?
N1 C1 1.380(3) . ?
N1 C2 1.403(3) . ?
N2 C1 1.377(3) . ?
N2 C13 1.408(3) . ?
C2 C7 1.393(4) . ?
C2 C3 1.407(4) . ?
C3 C4 1.393(4) . ?
C3 C8 1.445(3) . ?
C4 C5 1.384(4) . ?
C5 C6 1.374(4) . ?
C6 C7 1.385(4) . ?
C8 C9 1.193(3) . ?
C9 C10 1.483(4) . ?
C10 C11 1.517(4) . ?
C10 C12 1.517(4) . ?
C13 C18 1.394(4) . ?
C13 C14 1.403(4) . ?
C14 C15 1.401(4) . ?
C14 C19 1.434(4) . ?
C15 C16 1.372(4) . ?
C16 C17 1.380(4) . ?
C17 C18 1.393(4) . ?
C19 C20 1.190(4) . ?
C20 C21 1.483(4) . ?
C21 C23 1.520(4) . ?
C21 C22 1.521(4) . ?
N1A C13A 1.516(3) . ?
N1A C9A 1.517(3) . ?
N1A C5A 1.518(3) . ?
N1A C1A 1.524(3) . ?
C1A C2A 1.507(4) . ?
C2A C3A 1.514(4) . ?
C3A C4A 1.502(5) . ?
C5A C6A 1.517(4) . ?
C6A C7A 1.500(4) . ?
C7A C8A 1.513(4) . ?
C9A C10A 1.516(3) . ?
C10A C11A 1.527(4) . ?
C11A C12A 1.517(4) . ?
C13A C14A 1.511(4) . ?
C14A C151 1.513(5) . ?
C151 C161 1.609(8) . ?

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
C1 N1 C2 124.4(2) . . ?
C1 N2 C13 124.2(3) . . ?
O1 C1 N2 124.0(3) . . ?
O1 C1 N1 123.5(3) . . ?
N2 C1 N1 112.5(3) . . ?
C7 C2 N1 122.6(2) . . ?
C7 C2 C3 118.9(2) . . ?
N1 C2 C3 118.5(2) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 C8 120.5(2) . . ?
C2 C3 C8 119.3(2) . . ?
C5 C4 C3 119.5(3) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 Cl2 119.9(2) . . ?
C4 C5 Cl2 119.4(2) . . ?
C5 C6 C7 120.4(2) . . ?
C6 C7 C2 120.3(3) . . ?
C9 C8 C3 173.8(3) . . ?
C8 C9 C10 175.0(3) . . ?
O2 C10 C9 108.4(2) . . ?
O2 C10 C11 109.5(2) . . ?
C9 C10 C11 111.6(2) . . ?
O2 C10 C12 106.2(2) . . ?
C9 C10 C12 109.5(2) . . ?
C11 C10 C12 111.4(2) . . ?
C18 C13 C14 119.3(2) . . ?
C18 C13 N2 122.5(3) . . ?
C14 C13 N2 118.2(3) . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 C19 119.7(3) . . ?
C13 C14 C19 121.0(2) . . ?
C16 C15 C14 120.2(3) . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 Cl3 119.2(2) . . ?
C17 C16 Cl3 119.5(2) . . ?
C16 C17 C18 119.2(3) . . ?
C17 C18 C13 120.7(3) . . ?
C20 C19 C14 179.3(3) . . ?
C19 C20 C21 178.0(3) . . ?
O3 C21 C20 109.2(2) . . ?
O3 C21 C23 106.2(2) . . ?
C20 C21 C23 109.4(3) . . ?
O3 C21 C22 110.0(3) . . ?
C20 C21 C22 110.1(2) . . ?
C23 C21 C22 111.7(3) . . ?
C13A N1A C9A 111.7(2) . . ?
C13A N1A C5A 110.6(2) . . ?
C9A N1A C5A 106.37(17) . . ?
C13A N1A C1A 106.99(18) . . ?
C9A N1A C1A 110.6(2) . . ?
C5A N1A C1A 110.7(2) . . ?
C2A C1A N1A 115.9(2) . . ?
C1A C2A C3A 112.4(2) . . ?
C4A C3A C2A 112.7(3) . . ?
C6A C5A N1A 116.48(19) . . ?
C7A C6A C5A 111.2(2) . . ?
C6A C7A C8A 113.5(3) . . ?
C10A C9A N1A 116.9(2) . . ?
C9A C10A C11A 108.6(2) . . ?
C12A C11A C10A 112.9(2) . . ?
C14A C13A N1A 115.5(2) . . ?
C13A C14A C151 111.6(3) . . ?
C14A C151 C161 120.8(4) . . ?

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 H2N Cl1 0.89(3) 2.52(3) 3.358(3) 156(3) .
N1 H1N Cl1 0.88(3) 2.51(3) 3.321(3) 154(3) .
O3 H3O Cl1 0.95(4) 2.27(5) 3.221(2) 171(4) .
O2 H2O Cl1 0.95(4) 2.18(4) 3.121(2) 170(3) .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.064