# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008

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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,   
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#  anisotropic displacement parameters and molecular geometry data,
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data_kv4(5q)
_database_code_depnum_ccdc_archive 'CCDC 676867'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
11-Hydroxy-4-isopropyl-8,13-diaza-tricyclo[7.3.1.0^2,7^]trideca-
2(7),3,5,10-tetraene-8,10,13-tricarboxylic acid trimethyl ester
;
_chemical_name_common            
;
11-Hydroxy-4-isopropyl-8,13-diaza-
tricyclo(7.3.1.0$2,7!)trideca-2(7),3,5,10-tetraene-8,10,13-
tricarboxylic acid trimethyl ester
;
_chemical_melting_point          424
_chemical_formula_moiety         'C20 H24 N2 O7'
_chemical_formula_sum            'C20 H24 N2 O7'
_chemical_formula_weight         404.41

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           Triclinic
_symmetry_space_group_name_H-M   'P-1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4794(5)
_cell_length_b                   12.6941(6)
_cell_length_c                   16.9496(9)
_cell_angle_alpha                102.5480(10)
_cell_angle_beta                 102.9830(10)
_cell_angle_gamma                90.4220(10)
_cell_volume                     1936.59(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5165
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      31.69

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23764
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         30.00
_reflns_number_total             11025
_reflns_number_gt                7531
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0634P)^2^+0.2808P] 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         11025
_refine_ls_number_parameters     536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.67670(12) 0.75018(10) 0.44512(7) 0.0312(3) Uani 1 1 d . . .
H1A H 0.6620 0.8137 0.4397 0.047 Uiso 1 1 calc R . .
O2 O 0.21706(13) 0.57477(11) 0.06694(7) 0.0352(3) Uani 1 1 d . . .
O3 O 0.12133(12) 0.67514(10) 0.16662(7) 0.0297(3) Uani 1 1 d . . .
O4 O 0.54070(13) 0.90027(10) 0.38447(8) 0.0356(3) Uani 1 1 d . . .
O5 O 0.33398(12) 0.85084(9) 0.28654(7) 0.0297(3) Uani 1 1 d . . .
O6 O 0.26850(13) 0.43258(10) 0.40028(7) 0.0315(3) Uani 1 1 d . . .
O7 O 0.13750(12) 0.57273(10) 0.36942(7) 0.0301(3) Uani 1 1 d . . .
N1 N 0.33575(13) 0.53645(10) 0.31984(8) 0.0219(3) Uani 1 1 d . . .
N2 N 0.33976(13) 0.60894(10) 0.20349(7) 0.0197(2) Uani 1 1 d . . .
C1 C 0.32953(16) 0.63714(12) 0.29108(8) 0.0195(3) Uani 1 1 d . . .
H1 H 0.2350 0.6699 0.2949 0.023 Uiso 1 1 calc R . .
C2 C 0.45362(16) 0.71579(12) 0.34383(8) 0.0206(3) Uani 1 1 d . . .
C3 C 0.56744(16) 0.68311(13) 0.39521(9) 0.0231(3) Uani 1 1 d . . .
C4 C 0.58279(17) 0.56813(13) 0.40177(9) 0.0248(3) Uani 1 1 d . . .
H4A H 0.5597 0.5587 0.4540 0.030 Uiso 1 1 calc R . .
H4B H 0.6841 0.5488 0.4029 0.030 Uiso 1 1 calc R . .
C5 C 0.48001(16) 0.49393(12) 0.32752(9) 0.0215(3) Uani 1 1 d . . .
H5 H 0.4763 0.4191 0.3372 0.026 Uiso 1 1 calc R . .
C6 C 0.52876(15) 0.49135(12) 0.24790(8) 0.0196(3) Uani 1 1 d . . .
C7 C 0.46117(15) 0.54754(12) 0.18883(8) 0.0191(3) Uani 1 1 d . . .
C8 C 0.22446(16) 0.61542(13) 0.13925(9) 0.0228(3) Uani 1 1 d . . .
C9 C 0.00381(19) 0.69555(18) 0.10202(12) 0.0404(5) Uani 1 1 d . . .
H9A H 0.0426 0.7330 0.0659 0.061 Uiso 1 1 calc R . .
H9B H -0.0649 0.7407 0.1272 0.061 Uiso 1 1 calc R . .
H9C H -0.0459 0.6268 0.0691 0.061 Uiso 1 1 calc R . .
C10 C 0.44945(17) 0.82974(13) 0.34121(9) 0.0240(3) Uani 1 1 d . . .
C11 C 0.3216(2) 0.96341(15) 0.28240(13) 0.0391(4) Uani 1 1 d . . .
H11A H 0.3061 1.0056 0.3352 0.059 Uiso 1 1 calc R . .
H11B H 0.2394 0.9697 0.2372 0.059 Uiso 1 1 calc R . .
H11C H 0.4110 0.9910 0.2720 0.059 Uiso 1 1 calc R . .
C12 C 0.51852(16) 0.54666(12) 0.11965(9) 0.0212(3) Uani 1 1 d . . .
H12 H 0.4759 0.5871 0.0803 0.025 Uiso 1 1 calc R . .
C13 C 0.63741(16) 0.48703(13) 0.10813(9) 0.0232(3) Uani 1 1 d . . .
H13 H 0.6744 0.4865 0.0604 0.028 Uiso 1 1 calc R . .
C14 C 0.70381(16) 0.42763(12) 0.16545(9) 0.0229(3) Uani 1 1 d . . .
C15 C 0.64882(16) 0.43279(12) 0.23522(9) 0.0222(3) Uani 1 1 d . . .
H15 H 0.6944 0.3951 0.2759 0.027 Uiso 1 1 calc R . .
C16 C 0.83165(17) 0.35987(14) 0.15341(10) 0.0275(3) Uani 1 1 d . . .
H16 H 0.8608 0.3271 0.2028 0.033 Uiso 1 1 calc R . .
C17 C 0.96167(19) 0.42960(16) 0.15112(13) 0.0400(4) Uani 1 1 d . . .
H17A H 0.9395 0.4585 0.1009 0.060 Uiso 1 1 calc R . .
H17B H 1.0461 0.3856 0.1507 0.060 Uiso 1 1 calc R . .
H17C H 0.9829 0.4895 0.2003 0.060 Uiso 1 1 calc R . .
C18 C 0.7931(2) 0.26730(14) 0.07677(11) 0.0349(4) Uani 1 1 d . . .
H18A H 0.7129 0.2214 0.0811 0.052 Uiso 1 1 calc R . .
H18B H 0.8777 0.2243 0.0729 0.052 Uiso 1 1 calc R . .
H18C H 0.7639 0.2967 0.0270 0.052 Uiso 1 1 calc R . .
C19 C 0.24850(17) 0.50829(13) 0.36678(9) 0.0231(3) Uani 1 1 d . . .
C20 C 0.0428(2) 0.54983(17) 0.42044(12) 0.0386(4) Uani 1 1 d . . .
H20A H -0.0140 0.4816 0.3931 0.058 Uiso 1 1 calc R . .
H20B H -0.0229 0.6085 0.4280 0.058 Uiso 1 1 calc R . .
H20C H 0.1012 0.5438 0.4747 0.058 Uiso 1 1 calc R . .
O8 O 1.16269(14) 0.03351(11) 0.45878(7) 0.0359(3) Uani 1 1 d . . .
H8 H 1.1533 -0.0337 0.4535 0.054 Uiso 1 1 calc R . .
O9 O 0.71361(13) -0.03914(11) 0.07048(7) 0.0369(3) Uani 1 1 d . . .
O10 O 0.61576(12) -0.07818(10) 0.17087(7) 0.0312(3) Uani 1 1 d . . .
O11 O 1.03930(14) -0.15894(10) 0.39806(8) 0.0383(3) Uani 1 1 d . . .
O12 O 0.84528(13) -0.17774(9) 0.29071(7) 0.0309(3) Uani 1 1 d . . .
O13 O 0.75279(14) 0.30474(9) 0.39910(7) 0.0331(3) Uani 1 1 d . . .
O14 O 0.63379(14) 0.14191(10) 0.37620(8) 0.0364(3) Uani 1 1 d . . .
N3 N 0.82273(14) 0.15512(10) 0.31922(8) 0.0217(3) Uani 1 1 d . . .
N4 N 0.83481(13) 0.01114(10) 0.20735(7) 0.0205(3) Uani 1 1 d . . .
C21 C 0.82252(16) 0.03734(12) 0.29464(9) 0.0208(3) Uani 1 1 d . . .
H21 H 0.7288 0.0046 0.2985 0.025 Uiso 1 1 calc R . .
C22 C 0.94762(17) -0.00363(13) 0.35125(9) 0.0237(3) Uani 1 1 d . . .
C23 C 1.05520(17) 0.06488(13) 0.40394(9) 0.0252(3) Uani 1 1 d . . .
C24 C 1.06695(17) 0.18250(13) 0.40510(9) 0.0255(3) Uani 1 1 d . . .
H24A H 1.1683 0.2046 0.4072 0.031 Uiso 1 1 calc R . .
H24B H 1.0398 0.2250 0.4552 0.031 Uiso 1 1 calc R . .
C25 C 0.96636(16) 0.20502(12) 0.32708(9) 0.0215(3) Uani 1 1 d . . .
H25 H 0.9596 0.2849 0.3333 0.026 Uiso 1 1 calc R . .
C26 C 1.02036(16) 0.15849(12) 0.24977(9) 0.0200(3) Uani 1 1 d . . .
C27 C 0.95503(15) 0.06542(12) 0.19180(9) 0.0199(3) Uani 1 1 d . . .
C28 C 0.71993(16) -0.03524(13) 0.14312(10) 0.0245(3) Uani 1 1 d . . .
C29 C 0.4979(2) -0.13747(17) 0.10593(12) 0.0431(5) Uani 1 1 d . . .
H29A H 0.4501 -0.0887 0.0720 0.065 Uiso 1 1 calc R . .
H29B H 0.4276 -0.1670 0.1311 0.065 Uiso 1 1 calc R . .
H29C H 0.5364 -0.1967 0.0708 0.065 Uiso 1 1 calc R . .
C30 C 0.95002(17) -0.11872(13) 0.35031(10) 0.0263(3) Uani 1 1 d . . .
C31 C 0.8427(2) -0.29326(14) 0.28328(13) 0.0379(4) Uani 1 1 d . . .
H31A H 0.9366 -0.3198 0.2754 0.057 Uiso 1 1 calc R . .
H31B H 0.7659 -0.3285 0.2354 0.057 Uiso 1 1 calc R . .
H31C H 0.8240 -0.3099 0.3339 0.057 Uiso 1 1 calc R . .
C32 C 1.01310(16) 0.02579(12) 0.12297(9) 0.0220(3) Uani 1 1 d . . .
H32 H 0.9708 -0.0384 0.0840 0.026 Uiso 1 1 calc R . .
C33 C 1.13197(16) 0.07947(13) 0.11110(9) 0.0237(3) Uani 1 1 d . . .
H33 H 1.1691 0.0521 0.0635 0.028 Uiso 1 1 calc R . .
C34 C 1.19817(16) 0.17333(13) 0.16811(9) 0.0234(3) Uani 1 1 d . . .
C35 C 1.14143(16) 0.20992(12) 0.23722(9) 0.0229(3) Uani 1 1 d . . .
H35 H 1.1866 0.2722 0.2774 0.027 Uiso 1 1 calc R . .
C36 C 1.32824(17) 0.23350(13) 0.15676(10) 0.0281(3) Uani 1 1 d . . .
H36 H 1.3559 0.2972 0.2048 0.034 Uiso 1 1 calc R . .
C37 C 1.4580(2) 0.16271(18) 0.15807(15) 0.0463(5) Uani 1 1 d . . .
H37A H 1.4765 0.1340 0.2084 0.069 Uiso 1 1 calc R . .
H37B H 1.5437 0.2061 0.1577 0.069 Uiso 1 1 calc R . .
H37C H 1.4370 0.1027 0.1090 0.069 Uiso 1 1 calc R . .
C38 C 1.2958(2) 0.27598(15) 0.07733(11) 0.0353(4) Uani 1 1 d . . .
H38A H 1.2684 0.2151 0.0291 0.053 Uiso 1 1 calc R . .
H38B H 1.3823 0.3157 0.0737 0.053 Uiso 1 1 calc R . .
H38C H 1.2159 0.3244 0.0782 0.053 Uiso 1 1 calc R . .
C39 C 0.73778(17) 0.20864(13) 0.36827(9) 0.0248(3) Uani 1 1 d . . .
C40 C 0.5414(3) 0.19077(19) 0.42959(15) 0.0564(6) Uani 1 1 d . . .
H40A H 0.6014 0.2334 0.4818 0.085 Uiso 1 1 calc R . .
H40B H 0.4841 0.1340 0.4414 0.085 Uiso 1 1 calc R . .
H40C H 0.4762 0.2380 0.4018 0.085 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 0.0307(6) 0.0315(6) 0.0243(6) 0.0018(5) -0.0040(5) -0.0020(5)
O2 0.0290(6) 0.0562(8) 0.0190(5) 0.0096(5) 0.0012(5) 0.0082(6)
O3 0.0227(5) 0.0401(7) 0.0275(6) 0.0125(5) 0.0035(5) 0.0083(5)
O4 0.0380(7) 0.0267(6) 0.0360(7) 0.0048(5) -0.0015(5) -0.0032(5)
O5 0.0298(6) 0.0265(6) 0.0325(6) 0.0120(5) 0.0014(5) 0.0024(5)
O6 0.0403(7) 0.0318(6) 0.0269(6) 0.0137(5) 0.0104(5) -0.0013(5)
O7 0.0287(6) 0.0387(7) 0.0299(6) 0.0137(5) 0.0153(5) 0.0038(5)
N1 0.0237(6) 0.0242(6) 0.0212(6) 0.0100(5) 0.0075(5) 0.0028(5)
N2 0.0187(6) 0.0252(6) 0.0156(5) 0.0062(5) 0.0032(5) 0.0028(5)
C1 0.0213(7) 0.0222(7) 0.0160(6) 0.0066(5) 0.0044(5) 0.0018(5)
C2 0.0231(7) 0.0237(7) 0.0148(6) 0.0035(5) 0.0046(5) 0.0003(6)
C3 0.0243(7) 0.0276(8) 0.0163(6) 0.0030(6) 0.0040(6) 0.0012(6)
C4 0.0277(8) 0.0302(8) 0.0165(6) 0.0085(6) 0.0018(6) 0.0048(6)
C5 0.0250(7) 0.0234(7) 0.0178(6) 0.0080(5) 0.0051(6) 0.0039(6)
C6 0.0215(7) 0.0205(7) 0.0159(6) 0.0031(5) 0.0033(5) -0.0009(5)
C7 0.0183(6) 0.0210(7) 0.0172(6) 0.0041(5) 0.0025(5) 0.0005(5)
C8 0.0206(7) 0.0279(8) 0.0218(7) 0.0105(6) 0.0037(6) 0.0009(6)
C9 0.0266(9) 0.0600(13) 0.0398(10) 0.0258(9) 0.0036(8) 0.0161(8)
C10 0.0262(7) 0.0261(8) 0.0208(7) 0.0053(6) 0.0076(6) 0.0016(6)
C11 0.0418(10) 0.0269(9) 0.0513(11) 0.0183(8) 0.0070(9) 0.0069(8)
C12 0.0224(7) 0.0247(7) 0.0160(6) 0.0065(5) 0.0016(5) -0.0004(6)
C13 0.0232(7) 0.0282(8) 0.0177(6) 0.0034(6) 0.0052(6) 0.0002(6)
C14 0.0210(7) 0.0243(7) 0.0220(7) 0.0029(6) 0.0041(6) 0.0018(6)
C15 0.0233(7) 0.0223(7) 0.0200(7) 0.0062(6) 0.0020(6) 0.0027(6)
C16 0.0274(8) 0.0310(8) 0.0269(8) 0.0099(6) 0.0086(6) 0.0096(7)
C17 0.0244(8) 0.0389(10) 0.0547(12) 0.0062(9) 0.0092(8) 0.0045(7)
C18 0.0417(10) 0.0262(8) 0.0413(10) 0.0072(7) 0.0194(8) 0.0064(7)
C19 0.0268(7) 0.0261(8) 0.0152(6) 0.0026(6) 0.0045(6) -0.0040(6)
C20 0.0338(9) 0.0533(12) 0.0370(10) 0.0150(9) 0.0208(8) -0.0001(8)
O8 0.0378(7) 0.0373(7) 0.0282(6) 0.0121(5) -0.0055(5) 0.0020(6)
O9 0.0309(6) 0.0518(8) 0.0209(6) -0.0019(5) 0.0010(5) -0.0098(6)
O10 0.0245(6) 0.0354(7) 0.0290(6) -0.0010(5) 0.0045(5) -0.0099(5)
O11 0.0443(7) 0.0315(7) 0.0390(7) 0.0149(6) 0.0023(6) 0.0067(6)
O12 0.0344(6) 0.0209(6) 0.0359(6) 0.0045(5) 0.0066(5) -0.0006(5)
O13 0.0429(7) 0.0254(6) 0.0313(6) 0.0008(5) 0.0147(5) 0.0039(5)
O14 0.0415(7) 0.0328(7) 0.0384(7) -0.0008(5) 0.0248(6) -0.0037(5)
N3 0.0239(6) 0.0197(6) 0.0205(6) 0.0024(5) 0.0050(5) -0.0003(5)
N4 0.0201(6) 0.0220(6) 0.0173(6) 0.0012(5) 0.0032(5) -0.0032(5)
C21 0.0237(7) 0.0187(7) 0.0191(7) 0.0017(5) 0.0057(6) -0.0006(5)
C22 0.0269(8) 0.0249(8) 0.0196(7) 0.0065(6) 0.0043(6) 0.0026(6)
C23 0.0279(8) 0.0298(8) 0.0180(7) 0.0075(6) 0.0039(6) 0.0020(6)
C24 0.0284(8) 0.0271(8) 0.0173(7) 0.0017(6) 0.0009(6) -0.0037(6)
C25 0.0240(7) 0.0206(7) 0.0182(6) 0.0015(5) 0.0041(6) -0.0017(6)
C26 0.0213(7) 0.0201(7) 0.0177(6) 0.0048(5) 0.0021(5) 0.0016(5)
C27 0.0197(7) 0.0198(7) 0.0188(6) 0.0047(5) 0.0013(5) -0.0004(5)
C28 0.0204(7) 0.0248(7) 0.0245(7) -0.0012(6) 0.0039(6) -0.0008(6)
C29 0.0276(9) 0.0478(12) 0.0429(10) -0.0077(9) 0.0033(8) -0.0160(8)
C30 0.0290(8) 0.0259(8) 0.0257(7) 0.0066(6) 0.0089(6) 0.0020(6)
C31 0.0439(10) 0.0206(8) 0.0513(11) 0.0066(8) 0.0168(9) 0.0007(7)
C32 0.0228(7) 0.0218(7) 0.0183(6) 0.0014(5) 0.0012(6) -0.0005(6)
C33 0.0244(7) 0.0258(8) 0.0196(7) 0.0035(6) 0.0041(6) 0.0015(6)
C34 0.0213(7) 0.0254(8) 0.0233(7) 0.0071(6) 0.0034(6) -0.0004(6)
C35 0.0232(7) 0.0207(7) 0.0216(7) 0.0032(6) 0.0003(6) -0.0016(6)
C36 0.0283(8) 0.0271(8) 0.0285(8) 0.0036(6) 0.0085(7) -0.0065(6)
C37 0.0269(9) 0.0475(12) 0.0705(14) 0.0268(11) 0.0103(9) -0.0012(8)
C38 0.0408(10) 0.0308(9) 0.0391(10) 0.0101(7) 0.0171(8) 0.0000(7)
C39 0.0290(8) 0.0269(8) 0.0183(7) 0.0043(6) 0.0058(6) 0.0033(6)
C40 0.0625(14) 0.0539(13) 0.0596(14) -0.0059(11) 0.0467(12) -0.0045(11)

_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 C3 1.3393(18) . ?
O1 H1A 0.8400 . ?
O2 C8 1.2081(18) . ?
O3 C8 1.3445(18) . ?
O3 C9 1.4444(19) . ?
O4 C10 1.2271(19) . ?
O5 C10 1.3360(19) . ?
O5 C11 1.450(2) . ?
O6 C19 1.2138(19) . ?
O7 C19 1.3403(19) . ?
O7 C20 1.4464(19) . ?
N1 C19 1.3637(19) . ?
N1 C1 1.4607(19) . ?
N1 C5 1.4629(19) . ?
N2 C8 1.3756(18) . ?
N2 C7 1.4322(18) . ?
N2 C1 1.4751(17) . ?
C1 C2 1.517(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.355(2) . ?
C2 C10 1.457(2) . ?
C3 C4 1.493(2) . ?
C4 C5 1.530(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.516(2) . ?
C5 H5 1.0000 . ?
C6 C15 1.395(2) . ?
C6 C7 1.397(2) . ?
C7 C12 1.397(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(2) . ?
C14 C16 1.517(2) . ?
C15 H15 0.9500 . ?
C16 C18 1.523(2) . ?
C16 C17 1.525(3) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O8 C23 1.3424(19) . ?
O8 H8 0.8400 . ?
O9 C28 1.2092(19) . ?
O10 C28 1.3436(19) . ?
O10 C29 1.450(2) . ?
O11 C30 1.229(2) . ?
O12 C30 1.333(2) . ?
O12 C31 1.444(2) . ?
O13 C39 1.2119(19) . ?
O14 C39 1.343(2) . ?
O14 C40 1.446(2) . ?
N3 C39 1.3656(19) . ?
N3 C21 1.4621(19) . ?
N3 C25 1.4635(19) . ?
N4 C28 1.3774(19) . ?
N4 C27 1.4302(19) . ?
N4 C21 1.4755(18) . ?
C21 C22 1.521(2) . ?
C21 H21 1.0000 . ?
C22 C23 1.354(2) . ?
C22 C30 1.458(2) . ?
C23 C24 1.492(2) . ?
C24 C25 1.530(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5157(19) . ?
C25 H25 1.0000 . ?
C26 C35 1.396(2) . ?
C26 C27 1.399(2) . ?
C27 C32 1.398(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.387(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.401(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(2) . ?
C34 C36 1.516(2) . ?
C35 H35 0.9500 . ?
C36 C38 1.526(2) . ?
C36 C37 1.528(2) . ?
C36 H36 1.0000 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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
C3 O1 H1A 109.5 . . ?
C8 O3 C9 114.84(13) . . ?
C10 O5 C11 115.63(13) . . ?
C19 O7 C20 114.73(13) . . ?
C19 N1 C1 124.46(12) . . ?
C19 N1 C5 118.47(12) . . ?
C1 N1 C5 111.67(12) . . ?
C8 N2 C7 121.11(12) . . ?
C8 N2 C1 122.12(12) . . ?
C7 N2 C1 114.67(11) . . ?
N1 C1 N2 106.85(11) . . ?
N1 C1 C2 110.01(12) . . ?
N2 C1 C2 111.05(12) . . ?
N1 C1 H1 109.6 . . ?
N2 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
C3 C2 C10 118.83(14) . . ?
C3 C2 C1 121.50(13) . . ?
C10 C2 C1 119.65(13) . . ?
O1 C3 C2 123.63(14) . . ?
O1 C3 C4 113.37(13) . . ?
C2 C3 C4 123.00(14) . . ?
C3 C4 C5 109.77(12) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C6 108.95(12) . . ?
N1 C5 C4 107.90(12) . . ?
C6 C5 C4 111.03(12) . . ?
N1 C5 H5 109.6 . . ?
C6 C5 H5 109.6 . . ?
C4 C5 H5 109.6 . . ?
C15 C6 C7 119.41(13) . . ?
C15 C6 C5 117.94(13) . . ?
C7 C6 C5 122.61(13) . . ?
C6 C7 C12 119.06(13) . . ?
C6 C7 N2 118.75(12) . . ?
C12 C7 N2 122.10(13) . . ?
O2 C8 O3 123.75(14) . . ?
O2 C8 N2 124.71(14) . . ?
O3 C8 N2 111.52(12) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 O5 122.58(15) . . ?
O4 C10 C2 124.49(14) . . ?
O5 C10 C2 112.92(13) . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C7 120.36(13) . . ?
C13 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C12 C13 C14 121.30(14) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 117.48(13) . . ?
C15 C14 C16 120.16(14) . . ?
C13 C14 C16 122.36(13) . . ?
C14 C15 C6 122.31(14) . . ?
C14 C15 H15 118.8 . . ?
C6 C15 H15 118.8 . . ?
C14 C16 C18 112.49(14) . . ?
C14 C16 C17 111.28(14) . . ?
C18 C16 C17 110.96(14) . . ?
C14 C16 H16 107.3 . . ?
C18 C16 H16 107.3 . . ?
C17 C16 H16 107.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 C19 O7 124.78(14) . . ?
O6 C19 N1 123.56(14) . . ?
O7 C19 N1 111.65(13) . . ?
O7 C20 H20A 109.5 . . ?
O7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 O8 H8 109.5 . . ?
C28 O10 C29 114.45(13) . . ?
C30 O12 C31 116.64(14) . . ?
C39 O14 C40 115.42(14) . . ?
C39 N3 C21 123.88(13) . . ?
C39 N3 C25 117.49(12) . . ?
C21 N3 C25 110.87(11) . . ?
C28 N4 C27 120.70(12) . . ?
C28 N4 C21 121.97(12) . . ?
C27 N4 C21 114.76(11) . . ?
N3 C21 N4 106.55(12) . . ?
N3 C21 C22 110.11(12) . . ?
N4 C21 C22 111.82(12) . . ?
N3 C21 H21 109.4 . . ?
N4 C21 H21 109.4 . . ?
C22 C21 H21 109.4 . . ?
C23 C22 C30 119.26(14) . . ?
C23 C22 C21 121.38(14) . . ?
C30 C22 C21 119.35(13) . . ?
O8 C23 C22 123.51(15) . . ?
O8 C23 C24 113.58(13) . . ?
C22 C23 C24 122.89(14) . . ?
C23 C24 C25 109.71(12) . . ?
C23 C24 H24A 109.7 . . ?
C25 C24 H24A 109.7 . . ?
C23 C24 H24B 109.7 . . ?
C25 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
N3 C25 C26 109.34(11) . . ?
N3 C25 C24 107.81(12) . . ?
C26 C25 C24 111.60(12) . . ?
N3 C25 H25 109.4 . . ?
C26 C25 H25 109.4 . . ?
C24 C25 H25 109.4 . . ?
C35 C26 C27 119.18(13) . . ?
C35 C26 C25 118.33(13) . . ?
C27 C26 C25 122.48(13) . . ?
C32 C27 C26 119.22(13) . . ?
C32 C27 N4 122.24(13) . . ?
C26 C27 N4 118.47(12) . . ?
O9 C28 O10 123.69(14) . . ?
O9 C28 N4 124.73(15) . . ?
O10 C28 N4 111.57(13) . . ?
O10 C29 H29A 109.5 . . ?
O10 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O10 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O11 C30 O12 122.58(15) . . ?
O11 C30 C22 124.53(15) . . ?
O12 C30 C22 112.89(13) . . ?
O12 C31 H31A 109.5 . . ?
O12 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O12 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C27 120.51(13) . . ?
C33 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C32 C33 C34 121.10(14) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C35 C34 C33 117.60(14) . . ?
C35 C34 C36 120.17(14) . . ?
C33 C34 C36 122.22(14) . . ?
C34 C35 C26 122.36(14) . . ?
C34 C35 H35 118.8 . . ?
C26 C35 H35 118.8 . . ?
C34 C36 C38 112.73(14) . . ?
C34 C36 C37 111.09(14) . . ?
C38 C36 C37 109.85(15) . . ?
C34 C36 H36 107.7 . . ?
C38 C36 H36 107.7 . . ?
C37 C36 H36 107.7 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O13 C39 O14 124.49(14) . . ?
O13 C39 N3 124.02(15) . . ?
O14 C39 N3 111.48(13) . . ?
O14 C40 H40A 109.5 . . ?
O14 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O14 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

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
C19 N1 C1 N2 -136.53(14) . . . . ?
C5 N1 C1 N2 69.98(14) . . . . ?
C19 N1 C1 C2 102.83(16) . . . . ?
C5 N1 C1 C2 -50.66(15) . . . . ?
C8 N2 C1 N1 110.79(15) . . . . ?
C7 N2 C1 N1 -52.88(15) . . . . ?
C8 N2 C1 C2 -129.24(14) . . . . ?
C7 N2 C1 C2 67.09(15) . . . . ?
N1 C1 C2 C3 14.01(18) . . . . ?
N2 C1 C2 C3 -104.07(15) . . . . ?
N1 C1 C2 C10 -164.38(12) . . . . ?
N2 C1 C2 C10 77.54(16) . . . . ?
C10 C2 C3 O1 0.9(2) . . . . ?
C1 C2 C3 O1 -177.49(13) . . . . ?
C10 C2 C3 C4 -179.28(13) . . . . ?
C1 C2 C3 C4 2.3(2) . . . . ?
O1 C3 C4 C5 -164.25(12) . . . . ?
C2 C3 C4 C5 15.9(2) . . . . ?
C19 N1 C5 C6 154.87(13) . . . . ?
C1 N1 C5 C6 -49.88(15) . . . . ?
C19 N1 C5 C4 -84.50(16) . . . . ?
C1 N1 C5 C4 70.76(14) . . . . ?
C3 C4 C5 N1 -49.92(16) . . . . ?
C3 C4 C5 C6 69.40(16) . . . . ?
N1 C5 C6 C15 -166.69(13) . . . . ?
C4 C5 C6 C15 74.61(17) . . . . ?
N1 C5 C6 C7 15.29(19) . . . . ?
C4 C5 C6 C7 -103.41(16) . . . . ?
C15 C6 C7 C12 -2.1(2) . . . . ?
C5 C6 C7 C12 175.89(13) . . . . ?
C15 C6 C7 N2 -178.83(13) . . . . ?
C5 C6 C7 N2 -0.8(2) . . . . ?
C8 N2 C7 C6 -143.67(14) . . . . ?
C1 N2 C7 C6 20.18(18) . . . . ?
C8 N2 C7 C12 39.7(2) . . . . ?
C1 N2 C7 C12 -156.44(13) . . . . ?
C9 O3 C8 O2 -5.0(2) . . . . ?
C9 O3 C8 N2 173.62(14) . . . . ?
C7 N2 C8 O2 -2.6(2) . . . . ?
C1 N2 C8 O2 -165.23(15) . . . . ?
C7 N2 C8 O3 178.84(12) . . . . ?
C1 N2 C8 O3 16.2(2) . . . . ?
C11 O5 C10 O4 -1.0(2) . . . . ?
C11 O5 C10 C2 178.55(13) . . . . ?
C3 C2 C10 O4 -2.2(2) . . . . ?
C1 C2 C10 O4 176.23(14) . . . . ?
C3 C2 C10 O5 178.25(13) . . . . ?
C1 C2 C10 O5 -3.32(19) . . . . ?
C6 C7 C12 C13 2.6(2) . . . . ?
N2 C7 C12 C13 179.27(13) . . . . ?
C7 C12 C13 C14 -0.8(2) . . . . ?
C12 C13 C14 C15 -1.6(2) . . . . ?
C12 C13 C14 C16 178.62(14) . . . . ?
C13 C14 C15 C6 2.2(2) . . . . ?
C16 C14 C15 C6 -178.05(14) . . . . ?
C7 C6 C15 C14 -0.3(2) . . . . ?
C5 C6 C15 C14 -178.43(14) . . . . ?
C15 C14 C16 C18 116.67(17) . . . . ?
C13 C14 C16 C18 -63.6(2) . . . . ?
C15 C14 C16 C17 -118.10(17) . . . . ?
C13 C14 C16 C17 61.6(2) . . . . ?
C20 O7 C19 O6 3.4(2) . . . . ?
C20 O7 C19 N1 -178.06(13) . . . . ?
C1 N1 C19 O6 -168.82(14) . . . . ?
C5 N1 C19 O6 -17.0(2) . . . . ?
C1 N1 C19 O7 12.6(2) . . . . ?
C5 N1 C19 O7 164.45(13) . . . . ?
C39 N3 C21 N4 140.84(14) . . . . ?
C25 N3 C21 N4 -70.84(14) . . . . ?
C39 N3 C21 C22 -97.71(16) . . . . ?
C25 N3 C21 C22 50.61(15) . . . . ?
C28 N4 C21 N3 -108.18(15) . . . . ?
C27 N4 C21 N3 53.75(15) . . . . ?
C28 N4 C21 C22 131.46(15) . . . . ?
C27 N4 C21 C22 -66.61(16) . . . . ?
N3 C21 C22 C23 -12.0(2) . . . . ?
N4 C21 C22 C23 106.27(16) . . . . ?
N3 C21 C22 C30 166.48(13) . . . . ?
N4 C21 C22 C30 -75.27(17) . . . . ?
C30 C22 C23 O8 -2.9(2) . . . . ?
C21 C22 C23 O8 175.57(14) . . . . ?
C30 C22 C23 C24 175.75(14) . . . . ?
C21 C22 C23 C24 -5.8(2) . . . . ?
O8 C23 C24 C25 165.10(13) . . . . ?
C22 C23 C24 C25 -13.7(2) . . . . ?
C39 N3 C25 C26 -159.73(13) . . . . ?
C21 N3 C25 C26 49.72(15) . . . . ?
C39 N3 C25 C24 78.77(16) . . . . ?
C21 N3 C25 C24 -71.78(14) . . . . ?
C23 C24 C25 N3 50.13(16) . . . . ?
C23 C24 C25 C26 -69.95(16) . . . . ?
N3 C25 C26 C35 167.48(13) . . . . ?
C24 C25 C26 C35 -73.34(17) . . . . ?
N3 C25 C26 C27 -13.65(19) . . . . ?
C24 C25 C26 C27 105.53(16) . . . . ?
C35 C26 C27 C32 0.4(2) . . . . ?
C25 C26 C27 C32 -178.46(13) . . . . ?
C35 C26 C27 N4 177.43(13) . . . . ?
C25 C26 C27 N4 -1.4(2) . . . . ?
C28 N4 C27 C32 -40.1(2) . . . . ?
C21 N4 C27 C32 157.68(13) . . . . ?
C28 N4 C27 C26 142.93(14) . . . . ?
C21 N4 C27 C26 -19.25(18) . . . . ?
C29 O10 C28 O9 4.3(2) . . . . ?
C29 O10 C28 N4 -174.35(14) . . . . ?
C27 N4 C28 O9 3.9(2) . . . . ?
C21 N4 C28 O9 164.74(15) . . . . ?
C27 N4 C28 O10 -177.46(12) . . . . ?
C21 N4 C28 O10 -16.6(2) . . . . ?
C31 O12 C30 O11 -1.3(2) . . . . ?
C31 O12 C30 C22 177.82(13) . . . . ?
C23 C22 C30 O11 4.6(2) . . . . ?
C21 C22 C30 O11 -173.88(15) . . . . ?
C23 C22 C30 O12 -174.43(14) . . . . ?
C21 C22 C30 O12 7.1(2) . . . . ?
C26 C27 C32 C33 -1.6(2) . . . . ?
N4 C27 C32 C33 -178.48(14) . . . . ?
C27 C32 C33 C34 1.0(2) . . . . ?
C32 C33 C34 C35 0.6(2) . . . . ?
C32 C33 C34 C36 179.91(14) . . . . ?
C33 C34 C35 C26 -1.9(2) . . . . ?
C36 C34 C35 C26 178.87(14) . . . . ?
C27 C26 C35 C34 1.3(2) . . . . ?
C25 C26 C35 C34 -179.75(14) . . . . ?
C35 C34 C36 C38 -119.40(16) . . . . ?
C33 C34 C36 C38 61.4(2) . . . . ?
C35 C34 C36 C37 116.81(17) . . . . ?
C33 C34 C36 C37 -62.4(2) . . . . ?
C40 O14 C39 O13 -3.6(3) . . . . ?
C40 O14 C39 N3 177.91(16) . . . . ?
C21 N3 C39 O13 168.31(14) . . . . ?
C25 N3 C39 O13 21.9(2) . . . . ?
C21 N3 C39 O14 -13.2(2) . . . . ?
C25 N3 C39 O14 -159.62(13) . . . . ?

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
O1 H1A O4 0.84 1.84 2.5769(17) 145.5 .
O8 H8 O11 0.84 1.86 2.5923(18) 145.3 .
O1 H1A O8 0.84 2.59 3.0645(17) 117.1 2_766

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.051


data_kv6(5t)
_database_code_depnum_ccdc_archive 'CCDC 676868'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4-tert-Butyl-11-hydroxy-8,13-diaza-tricyclo[7.3.1.0^2,7^]trideca-2(7),3,5,10-
tetraene-8,10,13-tricarboxylic acid trimetyl ester
;
_chemical_name_common            
;
4-tert-Butyl-11-hydroxy-8,13-diaza-
tricyclo(7.3.1.0$2,7!)trideca-2(7),3,5,10-tetraene-8,10,13-
tricarboxylic acid trimetyl ester
;
_chemical_melting_point          423
_chemical_formula_moiety         'C21 H26 N2 O7'
_chemical_formula_sum            'C21 H26 N2 O7'
_chemical_formula_weight         418.44

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           Triclinic
_symmetry_space_group_name_H-M   'P-1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.44490(10)
_cell_length_b                   9.4430(2)
_cell_length_c                   13.2714(2)
_cell_angle_alpha                95.0010(10)
_cell_angle_beta                 100.0610(10)
_cell_angle_gamma                99.2380(10)
_cell_volume                     1021.29(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7682
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      37.83

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9591
_exptl_absorpt_correction_T_max  0.9738
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16045
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5871
_reflns_number_gt                4608
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0710P)^2^+0.3986P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5871
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.007
_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 -0.02050(14) 0.19172(12) 0.45139(8) 0.0362(2) Uani 1 1 d . . .
H1O H -0.133(4) 0.171(3) 0.410(2) 0.092(9) Uiso 1 1 d . . .
O2A O 0.0246(16) -0.2743(14) 0.0954(11) 0.048(3) Uani 0.483(3) 1 d P A -1
O2B O 0.203(2) -0.1355(18) 0.0242(12) 0.045(3) Uani 0.517(3) 1 d P A 2
O3A O 0.183(2) -0.1174(19) 0.0195(12) 0.041(2) Uani 0.483(3) 1 d P A -1
O3B O 0.0178(11) -0.2810(10) 0.0880(9) 0.0271(13) Uani 0.517(3) 1 d P A 2
O4 O -0.27206(14) 0.08552(15) 0.31426(9) 0.0461(3) Uani 1 1 d . . .
O5 O -0.24581(12) -0.07053(12) 0.18330(8) 0.0361(2) Uani 1 1 d . . .
O6 O 0.36096(15) -0.21651(12) 0.45788(9) 0.0420(3) Uani 1 1 d . . .
O7 O 0.14063(14) -0.33838(10) 0.34257(9) 0.0377(3) Uani 1 1 d . . .
N1 N 0.22276(13) -0.10347(11) 0.33604(8) 0.0241(2) Uani 1 1 d . . .
N2 N 0.11691(12) -0.05031(11) 0.17027(8) 0.0234(2) Uani 1 1 d . A .
C1 C 0.07163(14) -0.09527(13) 0.26638(9) 0.0227(2) Uani 1 1 d . . .
H1A H 0.0004 -0.1929 0.2515 0.027 Uiso 1 1 calc R . .
C2 C -0.01736(15) 0.01073(13) 0.31571(10) 0.0243(2) Uani 1 1 d . . .
C3 C 0.05653(16) 0.10242(14) 0.40192(10) 0.0266(3) Uani 1 1 d . . .
C4 C 0.23305(16) 0.11362(14) 0.44966(10) 0.0275(3) Uani 1 1 d . . .
H4A H 0.2425 0.0663 0.5136 0.033 Uiso 1 1 calc R . .
H4B H 0.2850 0.2165 0.4678 0.033 Uiso 1 1 calc R . .
C5 C 0.31997(15) 0.04036(13) 0.37345(9) 0.0234(2) Uani 1 1 d . . .
H5A H 0.4319 0.0313 0.4089 0.028 Uiso 1 1 calc R . .
C6 C 0.33173(14) 0.12631(13) 0.28253(9) 0.0220(2) Uani 1 1 d . . .
C7 C 0.23418(14) 0.08107(13) 0.18516(9) 0.0232(2) Uani 1 1 d . . .
C8 C 0.11202(18) -0.15685(15) 0.09157(11) 0.0329(3) Uani 1 1 d . . .
C9A C 0.0239(5) -0.3941(4) 0.0128(3) 0.0475(9) Uani 0.483(3) 1 d P A -1
H9AA H -0.0517 -0.4803 0.0216 0.071 Uiso 0.483(3) 1 calc PR A -1
H9AB H 0.1342 -0.4163 0.0180 0.071 Uiso 0.483(3) 1 calc PR A -1
H9AC H -0.0114 -0.3637 -0.0550 0.071 Uiso 0.483(3) 1 calc PR A -1
C9B C 0.1679(5) -0.2268(4) -0.0636(3) 0.0511(9) Uani 0.517(3) 1 d P A 2
H9BA H 0.2370 -0.1906 -0.1113 0.077 Uiso 0.517(3) 1 calc PR A 2
H9BB H 0.0526 -0.2337 -0.0953 0.077 Uiso 0.517(3) 1 calc PR A 2
H9BC H 0.1885 -0.3226 -0.0481 0.077 Uiso 0.517(3) 1 calc PR A 2
C10 C -0.18780(16) 0.01265(16) 0.27256(11) 0.0303(3) Uani 1 1 d . . .
C11 C -0.4128(2) -0.0638(3) 0.13627(15) 0.0561(5) Uani 1 1 d . . .
H11A H -0.4448 -0.1284 0.0714 0.084 Uiso 1 1 calc R . .
H11B H -0.4201 0.0355 0.1224 0.084 Uiso 1 1 calc R . .
H11C H -0.4860 -0.0937 0.1832 0.084 Uiso 1 1 calc R . .
C12 C 0.24787(16) 0.16634(15) 0.10553(10) 0.0297(3) Uani 1 1 d . . .
H12A H 0.1798 0.1369 0.0396 0.036 Uiso 1 1 calc R . .
C13 C 0.36053(18) 0.29390(16) 0.12227(11) 0.0334(3) Uani 1 1 d . . .
H13A H 0.3697 0.3502 0.0670 0.040 Uiso 1 1 calc R . .
C14 C 0.46102(16) 0.34191(15) 0.21847(12) 0.0311(3) Uani 1 1 d . A .
C15 C 0.44302(15) 0.25666(14) 0.29772(10) 0.0265(3) Uani 1 1 d . . .
H15A H 0.5084 0.2880 0.3642 0.032 Uiso 1 1 calc R . .
C16 C 0.5892(2) 0.48090(19) 0.23541(14) 0.0465(4) Uani 1 1 d . . .
C17A C 0.6044(4) 0.5440(4) 0.1290(3) 0.0407(8) Uani 0.483(3) 1 d P A 31
H17A H 0.6299 0.4701 0.0809 0.061 Uiso 0.483(3) 1 calc PR A 31
H17B H 0.6918 0.6290 0.1414 0.061 Uiso 0.483(3) 1 calc PR A 31
H17C H 0.5007 0.5716 0.0994 0.061 Uiso 0.483(3) 1 calc PR A 31
C17B C 0.7164(7) 0.4574(9) 0.1759(4) 0.112(3) Uani 0.517(3) 1 d P A 4
H17D H 0.6665 0.4320 0.1028 0.168 Uiso 0.517(3) 1 calc PR A 4
H17E H 0.7693 0.3787 0.2009 0.168 Uiso 0.517(3) 1 calc PR A 4
H17F H 0.7982 0.5461 0.1844 0.168 Uiso 0.517(3) 1 calc PR A 4
C18A C 0.7559(5) 0.4529(6) 0.2809(4) 0.0699(16) Uani 0.483(3) 1 d P A 31
H18A H 0.8017 0.4052 0.2270 0.105 Uiso 0.483(3) 1 calc PR A 31
H18B H 0.7467 0.3904 0.3356 0.105 Uiso 0.483(3) 1 calc PR A 31
H18C H 0.8279 0.5448 0.3098 0.105 Uiso 0.483(3) 1 calc PR A 31
C18B C 0.6751(6) 0.5222(5) 0.3537(3) 0.0654(13) Uani 0.517(3) 1 d P A 4
H18D H 0.7367 0.4471 0.3759 0.098 Uiso 0.517(3) 1 calc PR A 4
H18E H 0.5916 0.5297 0.3957 0.098 Uiso 0.517(3) 1 calc PR A 4
H18F H 0.7498 0.6150 0.3620 0.098 Uiso 0.517(3) 1 calc PR A 4
C19A C 0.5388(7) 0.5929(4) 0.3034(3) 0.0628(13) Uani 0.483(3) 1 d P A 3
H19A H 0.4497 0.6318 0.2639 0.094 Uiso 0.483(3) 1 calc PR A 3
H19B H 0.6322 0.6712 0.3295 0.094 Uiso 0.483(3) 1 calc PR A 3
H19C H 0.5016 0.5494 0.3614 0.094 Uiso 0.483(3) 1 calc PR A 3
C19B C 0.5062(9) 0.6079(5) 0.2080(5) 0.099(2) Uani 0.517(3) 1 d P A 4
H19D H 0.4496 0.5898 0.1358 0.149 Uiso 0.517(3) 1 calc PR A 4
H19E H 0.5886 0.6963 0.2181 0.149 Uiso 0.517(3) 1 calc PR A 4
H19F H 0.4269 0.6194 0.2526 0.149 Uiso 0.517(3) 1 calc PR A 4
C20 C 0.25044(17) -0.21928(14) 0.38556(10) 0.0281(3) Uani 1 1 d . . .
C21 C 0.1568(3) -0.46802(19) 0.39052(19) 0.0632(6) Uani 1 1 d . . .
H21A H 0.0722 -0.5479 0.3536 0.095 Uiso 1 1 calc R . .
H21B H 0.1444 -0.4524 0.4625 0.095 Uiso 1 1 calc R . .
H21C H 0.2650 -0.4918 0.3880 0.095 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 0.0418(6) 0.0348(5) 0.0352(5) 0.0000(4) 0.0150(5) 0.0098(4)
O2A 0.059(5) 0.040(4) 0.037(4) -0.015(2) 0.012(3) -0.007(3)
O2B 0.044(3) 0.048(5) 0.039(3) -0.006(3) 0.019(2) -0.010(4)
O3A 0.063(6) 0.036(2) 0.024(2) 0.0006(15) 0.014(2) 0.002(2)
O3B 0.031(2) 0.020(2) 0.028(2) -0.0020(19) 0.0048(17) -0.0018(17)
O4 0.0355(6) 0.0648(8) 0.0433(6) 0.0021(6) 0.0097(5) 0.0244(5)
O5 0.0225(4) 0.0479(6) 0.0363(5) 0.0008(4) 0.0014(4) 0.0085(4)
O6 0.0459(6) 0.0335(5) 0.0409(6) 0.0118(5) -0.0097(5) 0.0064(5)
O7 0.0422(6) 0.0203(4) 0.0459(6) 0.0071(4) -0.0016(5) 0.0007(4)
N1 0.0217(5) 0.0207(5) 0.0274(5) 0.0048(4) -0.0008(4) 0.0013(4)
N2 0.0211(5) 0.0242(5) 0.0231(5) 0.0027(4) 0.0017(4) 0.0007(4)
C1 0.0197(5) 0.0229(5) 0.0242(5) 0.0037(4) 0.0019(4) 0.0018(4)
C2 0.0227(5) 0.0249(6) 0.0266(6) 0.0058(4) 0.0066(4) 0.0046(4)
C3 0.0310(6) 0.0241(6) 0.0267(6) 0.0055(5) 0.0107(5) 0.0039(5)
C4 0.0308(6) 0.0264(6) 0.0225(5) 0.0018(4) 0.0039(5) -0.0013(5)
C5 0.0215(5) 0.0214(5) 0.0244(5) 0.0036(4) -0.0001(4) -0.0003(4)
C6 0.0182(5) 0.0226(5) 0.0252(5) 0.0043(4) 0.0038(4) 0.0028(4)
C7 0.0194(5) 0.0242(5) 0.0255(6) 0.0037(4) 0.0039(4) 0.0028(4)
C8 0.0364(7) 0.0306(7) 0.0277(6) -0.0005(5) -0.0037(5) 0.0070(6)
C9A 0.052(2) 0.0354(17) 0.050(2) -0.0162(14) 0.0157(16) -0.0015(14)
C9B 0.071(2) 0.0450(18) 0.0409(17) -0.0046(14) 0.0253(17) 0.0108(16)
C10 0.0258(6) 0.0363(7) 0.0318(6) 0.0088(5) 0.0080(5) 0.0088(5)
C11 0.0271(7) 0.0882(15) 0.0498(10) -0.0033(10) -0.0048(7) 0.0200(8)
C12 0.0270(6) 0.0343(7) 0.0270(6) 0.0099(5) 0.0026(5) 0.0033(5)
C13 0.0317(7) 0.0347(7) 0.0352(7) 0.0153(6) 0.0080(5) 0.0026(5)
C14 0.0253(6) 0.0279(6) 0.0401(7) 0.0095(5) 0.0077(5) 0.0004(5)
C15 0.0212(5) 0.0259(6) 0.0304(6) 0.0040(5) 0.0031(5) 0.0003(4)
C16 0.0418(8) 0.0423(9) 0.0485(9) 0.0162(7) 0.0053(7) -0.0152(7)
C17A 0.0405(17) 0.0369(16) 0.0465(18) 0.0189(14) 0.0147(14) -0.0029(13)
C17B 0.065(3) 0.177(7) 0.067(3) -0.007(4) 0.032(3) -0.068(4)
C18A 0.0351(19) 0.074(3) 0.092(4) 0.046(3) -0.004(2) -0.0179(19)
C18B 0.065(3) 0.057(2) 0.055(2) -0.0009(18) 0.0088(19) -0.037(2)
C19A 0.094(3) 0.0358(18) 0.050(2) -0.0019(16) 0.022(2) -0.021(2)
C19B 0.144(6) 0.037(2) 0.094(4) 0.027(2) -0.014(4) -0.024(3)
C20 0.0310(6) 0.0228(6) 0.0303(6) 0.0049(5) 0.0041(5) 0.0050(5)
C21 0.0708(13) 0.0274(8) 0.0845(15) 0.0231(9) -0.0045(11) 0.0007(8)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3394(16) . ?
O1 H1O 0.99(3) . ?
O2A C8 1.240(13) . ?
O2A C9A 1.504(15) . ?
O2B C8 1.285(15) . ?
O2B C9B 1.346(17) . ?
O3A C8 1.266(15) . ?
O3B C8 1.299(10) . ?
O4 C10 1.2307(18) . ?
O5 C10 1.3311(18) . ?
O5 C11 1.4526(18) . ?
O6 C20 1.2116(17) . ?
O7 C20 1.3486(16) . ?
O7 C21 1.4427(19) . ?
N1 C20 1.3550(16) . ?
N1 C1 1.4566(15) . ?
N1 C5 1.4653(15) . ?
N2 C8 1.3759(18) . ?
N2 C7 1.4330(15) . ?
N2 C1 1.4717(15) . ?
C1 C2 1.5148(18) . ?
C1 H1A 1.0000 . ?
C2 C3 1.3611(18) . ?
C2 C10 1.4567(18) . ?
C3 C4 1.4975(19) . ?
C4 C5 1.5299(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5203(16) . ?
C5 H5A 1.0000 . ?
C6 C7 1.3963(17) . ?
C6 C15 1.3993(16) . ?
C7 C12 1.3928(17) . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3846(19) . ?
C12 H12A 0.9500 . ?
C13 C14 1.397(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3933(18) . ?
C14 C16 1.5336(19) . ?
C15 H15A 0.9500 . ?
C16 C17B 1.473(6) . ?
C16 C19A 1.492(5) . ?
C16 C18A 1.506(5) . ?
C16 C19B 1.523(6) . ?
C16 C18B 1.595(4) . ?
C16 C17A 1.597(4) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C3 O1 H1O 103.2(18) . . ?
C8 O2A C9A 116.3(10) . . ?
C8 O2B C9B 118.3(10) . . ?
C10 O5 C11 115.29(13) . . ?
C20 O7 C21 115.83(13) . . ?
C20 N1 C1 124.78(10) . . ?
C20 N1 C5 120.88(10) . . ?
C1 N1 C5 111.56(9) . . ?
C8 N2 C7 120.98(11) . . ?
C8 N2 C1 117.70(11) . . ?
C7 N2 C1 113.70(10) . . ?
N1 C1 N2 106.99(9) . . ?
N1 C1 C2 109.78(10) . . ?
N2 C1 C2 111.90(10) . . ?
N1 C1 H1A 109.4 . . ?
N2 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C3 C2 C10 118.56(12) . . ?
C3 C2 C1 121.61(11) . . ?
C10 C2 C1 119.80(11) . . ?
O1 C3 C2 123.49(13) . . ?
O1 C3 C4 113.73(12) . . ?
C2 C3 C4 122.78(12) . . ?
C3 C4 C5 109.45(10) . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C6 109.08(10) . . ?
N1 C5 C4 107.58(10) . . ?
C6 C5 C4 110.60(10) . . ?
N1 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
C7 C6 C15 118.95(11) . . ?
C7 C6 C5 122.49(10) . . ?
C15 C6 C5 118.55(11) . . ?
C12 C7 C6 119.79(11) . . ?
C12 C7 N2 121.16(11) . . ?
C6 C7 N2 119.00(10) . . ?
O2A C8 O3A 128.5(10) . . ?
O2A C8 O2B 123.8(10) . . ?
O3A C8 O2B 11.8(17) . . ?
O2A C8 O3B 4.4(12) . . ?
O3A C8 O3B 124.5(9) . . ?
O2B C8 O3B 120.4(9) . . ?
O2A C8 N2 115.5(7) . . ?
O3A C8 N2 115.6(8) . . ?
O2B C8 N2 120.5(7) . . ?
O3B C8 N2 119.1(5) . . ?
O2A C9A H9AA 109.5 . . ?
O2A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
O2A C9A H9AC 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
O2B C9B H9BA 109.5 . . ?
O2B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
O2B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
O4 C10 O5 122.24(13) . . ?
O4 C10 C2 123.23(13) . . ?
O5 C10 C2 114.53(12) . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C7 120.07(12) . . ?
C13 C12 H12A 120.0 . . ?
C7 C12 H12A 120.0 . . ?
C12 C13 C14 121.67(12) . . ?
C12 C13 H13A 119.2 . . ?
C14 C13 H13A 119.2 . . ?
C15 C14 C13 117.38(12) . . ?
C15 C14 C16 121.30(13) . . ?
C13 C14 C16 121.30(13) . . ?
C14 C15 C6 122.11(12) . . ?
C14 C15 H15A 118.9 . . ?
C6 C15 H15A 118.9 . . ?
C17B C16 C19A 142.3(3) . . ?
C17B C16 C18A 55.2(3) . . ?
C19A C16 C18A 110.9(3) . . ?
C17B C16 C19B 114.1(4) . . ?
C19A C16 C19B 49.9(3) . . ?
C18A C16 C19B 139.1(3) . . ?
C17B C16 C14 108.3(3) . . ?
C19A C16 C14 109.4(2) . . ?
C18A C16 C14 111.0(2) . . ?
C19B C16 C14 109.7(2) . . ?
C17B C16 C18B 108.0(3) . . ?
C19A C16 C18B 58.3(3) . . ?
C18A C16 C18B 55.5(3) . . ?
C19B C16 C18B 104.8(3) . . ?
C14 C16 C18B 112.00(17) . . ?
C17B C16 C17A 55.9(3) . . ?
C19A C16 C17A 107.6(2) . . ?
C18A C16 C17A 106.7(2) . . ?
C19B C16 C17A 60.9(3) . . ?
C14 C16 C17A 111.17(18) . . ?
C18B C16 C17A 136.8(2) . . ?
C16 C17A H17A 109.5 . . ?
C16 C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C16 C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C16 C17B H17D 109.5 . . ?
C16 C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C16 C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C16 C18A H18A 109.5 . . ?
C16 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C16 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C16 C18B H18D 109.5 . . ?
C16 C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C16 C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C16 C19A H19A 109.5 . . ?
C16 C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C16 C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C16 C19B H19D 109.5 . . ?
C16 C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C16 C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
O6 C20 O7 124.53(12) . . ?
O6 C20 N1 124.38(12) . . ?
O7 C20 N1 111.09(11) . . ?
O7 C21 H21A 109.5 . . ?
O7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C20 N1 C1 N2 -128.13(13) . . . . ?
C5 N1 C1 N2 70.77(12) . . . . ?
C20 N1 C1 C2 110.24(13) . . . . ?
C5 N1 C1 C2 -50.86(13) . . . . ?
C8 N2 C1 N1 95.04(13) . . . . ?
C7 N2 C1 N1 -54.89(13) . . . . ?
C8 N2 C1 C2 -144.68(11) . . . . ?
C7 N2 C1 C2 65.39(13) . . . . ?
N1 C1 C2 C3 12.48(15) . . . . ?
N2 C1 C2 C3 -106.16(13) . . . . ?
N1 C1 C2 C10 -165.54(11) . . . . ?
N2 C1 C2 C10 75.82(14) . . . . ?
C10 C2 C3 O1 2.11(19) . . . . ?
C1 C2 C3 O1 -175.94(11) . . . . ?
C10 C2 C3 C4 -177.24(11) . . . . ?
C1 C2 C3 C4 4.72(18) . . . . ?
O1 C3 C4 C5 -164.79(10) . . . . ?
C2 C3 C4 C5 14.61(16) . . . . ?
C20 N1 C5 C6 150.08(12) . . . . ?
C1 N1 C5 C6 -47.97(13) . . . . ?
C20 N1 C5 C4 -89.91(14) . . . . ?
C1 N1 C5 C4 72.04(12) . . . . ?
C3 C4 C5 N1 -50.15(13) . . . . ?
C3 C4 C5 C6 68.89(12) . . . . ?
N1 C5 C6 C7 12.39(16) . . . . ?
C4 C5 C6 C7 -105.73(13) . . . . ?
N1 C5 C6 C15 -168.56(11) . . . . ?
C4 C5 C6 C15 73.31(14) . . . . ?
C15 C6 C7 C12 -0.60(18) . . . . ?
C5 C6 C7 C12 178.44(12) . . . . ?
C15 C6 C7 N2 -178.24(11) . . . . ?
C5 C6 C7 N2 0.80(18) . . . . ?
C8 N2 C7 C12 54.44(17) . . . . ?
C1 N2 C7 C12 -156.73(12) . . . . ?
C8 N2 C7 C6 -127.96(13) . . . . ?
C1 N2 C7 C6 20.87(16) . . . . ?
C9A O2A C8 O3A 11.1(17) . . . . ?
C9A O2A C8 O2B -2.4(16) . . . . ?
C9A O2A C8 O3B 37(12) . . . . ?
C9A O2A C8 N2 -177.3(6) . . . . ?
C9B O2B C8 O2A 21(2) . . . . ?
C9B O2B C8 O3A -96(7) . . . . ?
C9B O2B C8 O3B 17.5(19) . . . . ?
C9B O2B C8 N2 -164.6(9) . . . . ?
C7 N2 C8 O2A 168.9(6) . . . . ?
C1 N2 C8 O2A 21.3(7) . . . . ?
C7 N2 C8 O3A -18.3(10) . . . . ?
C1 N2 C8 O3A -166.0(10) . . . . ?
C7 N2 C8 O2B -6.1(10) . . . . ?
C1 N2 C8 O2B -153.8(10) . . . . ?
C7 N2 C8 O3B 171.7(4) . . . . ?
C1 N2 C8 O3B 24.1(5) . . . . ?
C11 O5 C10 O4 2.9(2) . . . . ?
C11 O5 C10 C2 -176.71(14) . . . . ?
C3 C2 C10 O4 -5.4(2) . . . . ?
C1 C2 C10 O4 172.64(13) . . . . ?
C3 C2 C10 O5 174.12(12) . . . . ?
C1 C2 C10 O5 -7.80(17) . . . . ?
C6 C7 C12 C13 1.5(2) . . . . ?
N2 C7 C12 C13 179.06(12) . . . . ?
C7 C12 C13 C14 -1.0(2) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C12 C13 C14 C16 178.05(15) . . . . ?
C13 C14 C15 C6 1.3(2) . . . . ?
C16 C14 C15 C6 -177.15(14) . . . . ?
C7 C6 C15 C14 -0.80(19) . . . . ?
C5 C6 C15 C14 -179.88(12) . . . . ?
C15 C14 C16 C17B 111.2(3) . . . . ?
C13 C14 C16 C17B -67.2(4) . . . . ?
C15 C14 C16 C19A -70.5(3) . . . . ?
C13 C14 C16 C19A 111.1(3) . . . . ?
C15 C14 C16 C18A 52.2(3) . . . . ?
C13 C14 C16 C18A -126.1(3) . . . . ?
C15 C14 C16 C19B -123.7(3) . . . . ?
C13 C14 C16 C19B 57.9(3) . . . . ?
C15 C14 C16 C18B -7.8(3) . . . . ?
C13 C14 C16 C18B 173.9(3) . . . . ?
C15 C14 C16 C17A 170.81(19) . . . . ?
C13 C14 C16 C17A -7.6(3) . . . . ?
C21 O7 C20 O6 2.2(2) . . . . ?
C21 O7 C20 N1 -178.92(16) . . . . ?
C1 N1 C20 O6 -164.73(14) . . . . ?
C5 N1 C20 O6 -5.3(2) . . . . ?
C1 N1 C20 O7 16.37(18) . . . . ?
C5 N1 C20 O7 175.82(11) . . . . ?

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
O1 H1O O4 0.99(3) 1.63(3) 2.5452(17) 152(3) .

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.050


data_kv9(5z)
_database_code_depnum_ccdc_archive 'CCDC 676869'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
11-Hydroxy-4,5(1',3')-propylene-8,13-diaza-
tricyclo[7.3.1.0^2,7^]trideca-2(7),3,5,10-tetraene-8,10,13-
tricarboxylic acid trimethyl ester
;
_chemical_name_common            
;
11-Hydroxy-4,5(1',3')-propylene-8,13-diaza-
tricyclo(7.3.1.0$2,7!)trideca-2(7),3,5,10-tetraene-8,10,13-
tricarboxylic acid trimethyl ester
;
_chemical_melting_point          371
_chemical_formula_moiety         'C20 H22 N2 O7'
_chemical_formula_sum            'C20 H22 N2 O7'
_chemical_formula_weight         402.40

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           Triclinic
_symmetry_space_group_name_H-M   'P-1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2926(2)
_cell_length_b                   8.4322(2)
_cell_length_c                   13.9059(3)
_cell_angle_alpha                91.2360(10)
_cell_angle_beta                 98.8450(10)
_cell_angle_gamma                95.8850(10)
_cell_volume                     955.05(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8603
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      39.73

_exptl_crystal_description       'fragment of plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.18
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_max          0.6
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29775
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5469
_reflns_number_gt                4810
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0867P)^2^+0.4115P] 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         5469
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001

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 0.56124(14) 0.33656(13) 0.10016(9) 0.0363(2) Uani 1 1 d . . .
H1B H 0.6612 0.3660 0.1190 0.055 Uiso 1 1 calc R . .
O2 O 0.34565(17) 0.90874(14) 0.40336(9) 0.0445(3) Uani 1 1 d . . .
O3 O 0.49977(14) 0.99653(12) 0.29135(8) 0.0348(2) Uani 1 1 d . . .
O4 O 0.80972(13) 0.52682(14) 0.17455(9) 0.0376(3) Uani 1 1 d . A .
O5A O 0.76998(14) 0.77472(19) 0.22138(15) 0.0277(3) Uani 0.907(7) 1 d P A 3
O5B O 0.7594(18) 0.7490(18) 0.2526(15) 0.030(3) Uiso 0.093(7) 1 d P A 4
O6 O 0.09015(13) 0.73497(13) -0.00931(8) 0.0360(2) Uani 1 1 d . . .
O7 O 0.31127(12) 0.91214(11) 0.04465(7) 0.0287(2) Uani 1 1 d . . .
N1 N 0.27046(12) 0.69016(12) 0.12584(8) 0.0234(2) Uani 1 1 d . . .
N2 N 0.40673(13) 0.73605(13) 0.28725(8) 0.0231(2) Uani 1 1 d . . .
C1 C 0.43177(14) 0.72444(14) 0.18486(9) 0.0214(2) Uani 1 1 d . . .
H1A H 0.4848 0.8289 0.1664 0.026 Uiso 1 1 calc R . .
C2 C 0.53770(14) 0.59372(15) 0.16723(9) 0.0232(2) Uani 1 1 d . A .
C3 C 0.47164(16) 0.45147(15) 0.12231(10) 0.0267(3) Uani 1 1 d . . .
C4 C 0.29097(17) 0.41084(16) 0.09084(10) 0.0294(3) Uani 1 1 d . . .
H4A H 0.2578 0.3010 0.1094 0.035 Uiso 1 1 calc R . .
H4B H 0.2646 0.4152 0.0191 0.035 Uiso 1 1 calc R . .
C5 C 0.19601(15) 0.52904(15) 0.13909(10) 0.0250(2) Uani 1 1 d . . .
H5A H 0.0783 0.5166 0.1077 0.030 Uiso 1 1 calc R . .
C6 C 0.20771(15) 0.50115(15) 0.24712(10) 0.0253(2) Uani 1 1 d . B .
C7 C 0.30907(15) 0.60197(15) 0.31784(9) 0.0248(2) Uani 1 1 d . . .
C8 C 0.41066(16) 0.88386(16) 0.33346(10) 0.0277(3) Uani 1 1 d . . .
C9 C 0.5199(3) 1.1530(2) 0.33873(15) 0.0492(4) Uani 1 1 d . . .
H9A H 0.5857 1.2274 0.3033 0.074 Uiso 1 1 calc R . .
H9B H 0.5756 1.1474 0.4058 0.074 Uiso 1 1 calc R . .
H9C H 0.4119 1.1903 0.3392 0.074 Uiso 1 1 calc R . .
C10 C 0.71545(16) 0.62532(17) 0.18912(9) 0.0269(3) Uani 1 1 d . . .
C11A C 0.94627(18) 0.8134(2) 0.23329(15) 0.0375(5) Uani 0.907(7) 1 d P A 3
H11A H 0.9750 0.9240 0.2580 0.056 Uiso 0.907(7) 1 calc PR A 3
H11B H 0.9835 0.8006 0.1703 0.056 Uiso 0.907(7) 1 calc PR A 3
H11C H 0.9996 0.7417 0.2796 0.056 Uiso 0.907(7) 1 calc PR A 3
C11B C 0.942(2) 0.779(2) 0.2876(18) 0.044(5) Uiso 0.093(7) 1 d P A 4
H11D H 0.9633 0.8542 0.3440 0.066 Uiso 0.093(7) 1 calc PR A 4
H11E H 0.9971 0.8243 0.2352 0.066 Uiso 0.093(7) 1 calc PR A 4
H11F H 0.9854 0.6783 0.3063 0.066 Uiso 0.093(7) 1 calc PR A 4
C12 C 0.31945(18) 0.56924(18) 0.41674(10) 0.0316(3) Uani 1 1 d . B .
H12A H 0.3898 0.6367 0.4646 0.038 Uiso 1 1 calc R . .
C13 C 0.2257(2) 0.43711(19) 0.44375(12) 0.0366(3) Uani 1 1 d . . .
C14A C 0.213(3) 0.385(2) 0.5442(19) 0.0466(16) Uani 0.590(13) 1 d P B 1
H14A H 0.1314 0.4417 0.5731 0.056 Uiso 0.590(13) 1 calc PR B 1
H14B H 0.3200 0.4022 0.5874 0.056 Uiso 0.590(13) 1 calc PR B 1
C15A C 0.1533(11) 0.2039(5) 0.5246(3) 0.0578(16) Uani 0.590(13) 1 d P B 1
H15A H 0.2460 0.1409 0.5189 0.069 Uiso 0.590(13) 1 calc PR B 1
H15B H 0.0932 0.1602 0.5761 0.069 Uiso 0.590(13) 1 calc PR B 1
C16A C 0.0395(19) 0.2081(17) 0.4271(10) 0.0452(15) Uani 0.590(13) 1 d P B 1
H16A H 0.0266 0.1039 0.3910 0.054 Uiso 0.590(13) 1 calc PR B 1
H16B H -0.0702 0.2358 0.4369 0.054 Uiso 0.590(13) 1 calc PR B 1
C14B C 0.215(4) 0.365(4) 0.542(3) 0.0466(16) Uani 0.410(13) 1 d P B 2
H14C H 0.1956 0.4457 0.5902 0.056 Uiso 0.410(13) 1 calc PR B 2
H14D H 0.3159 0.3162 0.5669 0.056 Uiso 0.410(13) 1 calc PR B 2
C15B C 0.0610(15) 0.2319(11) 0.5184(5) 0.067(2) Uani 0.410(13) 1 d P B 2
H15C H 0.0805 0.1375 0.5579 0.080 Uiso 0.410(13) 1 calc PR B 2
H15D H -0.0391 0.2746 0.5341 0.080 Uiso 0.410(13) 1 calc PR B 2
C16B C 0.039(3) 0.186(3) 0.4112(15) 0.0452(15) Uani 0.410(13) 1 d P B 2
H16C H -0.0780 0.1674 0.3820 0.054 Uiso 0.410(13) 1 calc PR B 2
H16D H 0.0941 0.0897 0.3993 0.054 Uiso 0.410(13) 1 calc PR B 2
C17 C 0.1253(2) 0.33564(19) 0.37379(13) 0.0385(3) Uani 1 1 d . B .
C18 C 0.11608(18) 0.36619(17) 0.27644(12) 0.0334(3) Uani 1 1 d . . .
H18A H 0.0479 0.2962 0.2291 0.040 Uiso 1 1 calc R B .
C19 C 0.21440(15) 0.77503(15) 0.04821(9) 0.0240(2) Uani 1 1 d . . .
C20 C 0.2661(2) 1.00802(18) -0.03760(12) 0.0374(3) Uani 1 1 d . . .
H20A H 0.3433 1.1049 -0.0336 0.056 Uiso 1 1 calc R . .
H20B H 0.1548 1.0373 -0.0373 0.056 Uiso 1 1 calc R . .
H20C H 0.2695 0.9471 -0.0979 0.056 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 0.0387(5) 0.0307(5) 0.0425(6) -0.0053(4) 0.0122(5) 0.0101(4)
O2 0.0596(8) 0.0387(6) 0.0407(6) -0.0060(5) 0.0240(6) 0.0089(5)
O3 0.0450(6) 0.0245(5) 0.0350(5) -0.0039(4) 0.0099(4) 0.0004(4)
O4 0.0276(5) 0.0444(6) 0.0428(6) -0.0040(5) 0.0059(4) 0.0148(4)
O5A 0.0188(5) 0.0367(6) 0.0276(8) -0.0012(6) 0.0027(4) 0.0039(4)
O6 0.0319(5) 0.0359(5) 0.0348(6) 0.0049(4) -0.0088(4) -0.0009(4)
O7 0.0304(5) 0.0246(4) 0.0294(5) 0.0063(3) 0.0000(4) 0.0008(3)
N1 0.0192(4) 0.0236(5) 0.0261(5) 0.0040(4) 0.0006(4) -0.0002(3)
N2 0.0238(5) 0.0248(5) 0.0215(5) 0.0007(4) 0.0062(4) 0.0028(4)
C1 0.0188(5) 0.0245(5) 0.0209(5) 0.0013(4) 0.0030(4) 0.0027(4)
C2 0.0216(5) 0.0273(6) 0.0219(5) 0.0008(4) 0.0052(4) 0.0057(4)
C3 0.0301(6) 0.0262(6) 0.0258(6) 0.0005(4) 0.0090(5) 0.0056(5)
C4 0.0312(6) 0.0262(6) 0.0300(6) -0.0036(5) 0.0055(5) -0.0009(5)
C5 0.0221(5) 0.0235(5) 0.0286(6) 0.0023(4) 0.0031(4) -0.0005(4)
C6 0.0223(5) 0.0249(5) 0.0304(6) 0.0047(4) 0.0076(4) 0.0043(4)
C7 0.0236(5) 0.0266(6) 0.0263(6) 0.0047(4) 0.0082(4) 0.0052(4)
C8 0.0282(6) 0.0288(6) 0.0266(6) -0.0008(5) 0.0035(5) 0.0069(5)
C9 0.0730(13) 0.0263(7) 0.0480(10) -0.0074(6) 0.0124(9) 0.0022(7)
C10 0.0244(5) 0.0355(6) 0.0219(6) 0.0009(5) 0.0040(4) 0.0081(5)
C11A 0.0196(7) 0.0516(10) 0.0396(11) -0.0042(8) 0.0024(6) 0.0016(6)
C12 0.0338(7) 0.0375(7) 0.0259(6) 0.0052(5) 0.0095(5) 0.0076(5)
C13 0.0410(7) 0.0403(8) 0.0344(7) 0.0144(6) 0.0177(6) 0.0123(6)
C14A 0.0629(12) 0.048(5) 0.0330(13) 0.011(3) 0.0176(9) 0.007(2)
C15A 0.099(5) 0.0438(18) 0.0338(16) 0.0128(12) 0.023(2) 0.001(2)
C16A 0.0677(12) 0.035(4) 0.032(4) 0.002(2) 0.019(2) -0.014(2)
C14B 0.0629(12) 0.048(5) 0.0330(13) 0.011(3) 0.0176(9) 0.007(2)
C15B 0.083(6) 0.067(4) 0.055(3) 0.020(3) 0.031(4) -0.003(4)
C16B 0.0677(12) 0.035(4) 0.032(4) 0.002(2) 0.019(2) -0.014(2)
C17 0.0378(7) 0.0335(7) 0.0483(9) 0.0142(6) 0.0175(6) 0.0045(6)
C18 0.0307(6) 0.0268(6) 0.0440(8) 0.0071(5) 0.0100(6) 0.0014(5)
C19 0.0234(5) 0.0243(5) 0.0245(6) 0.0007(4) 0.0033(4) 0.0041(4)
C20 0.0449(8) 0.0306(7) 0.0358(8) 0.0125(5) 0.0014(6) 0.0049(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
O1 C3 1.3382(16) . ?
O1 H1B 0.8400 . ?
O2 C8 1.2062(17) . ?
O3 C8 1.3434(17) . ?
O3 C9 1.4443(18) . ?
O4 C10 1.2315(16) . ?
O5A C10 1.3376(19) . ?
O5A C11A 1.4479(18) . ?
O5B C10 1.336(15) . ?
O5B C11B 1.51(2) . ?
O6 C19 1.2162(16) . ?
O7 C19 1.3449(15) . ?
O7 C20 1.4395(16) . ?
N1 C19 1.3567(16) . ?
N1 C1 1.4558(15) . ?
N1 C5 1.4611(15) . ?
N2 C8 1.3849(17) . ?
N2 C7 1.4331(15) . ?
N2 C1 1.4728(15) . ?
C1 C2 1.5165(16) . ?
C1 H1A 1.0000 . ?
C2 C3 1.3626(18) . ?
C2 C10 1.4541(17) . ?
C3 C4 1.4967(19) . ?
C4 C5 1.5357(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5154(18) . ?
C5 H5A 1.0000 . ?
C6 C7 1.3999(19) . ?
C6 C18 1.4059(17) . ?
C7 C12 1.4000(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12 C13 1.385(2) . ?
C12 H12A 0.9500 . ?
C13 C17 1.393(3) . ?
C13 C14A 1.49(3) . ?
C13 C14B 1.52(4) . ?
C14A C15A 1.56(2) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A C16A 1.532(15) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A C17 1.501(16) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C14B C15B 1.60(3) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B C16B 1.51(2) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B C17 1.53(2) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C17 C18 1.376(2) . ?
C18 H18A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C3 O1 H1B 109.5 . . ?
C8 O3 C9 114.92(13) . . ?
C10 O5A C11A 115.12(12) . . ?
C10 O5B C11B 114.1(13) . . ?
C19 O7 C20 115.59(11) . . ?
C19 N1 C1 124.22(10) . . ?
C19 N1 C5 121.22(10) . . ?
C1 N1 C5 112.08(9) . . ?
C8 N2 C7 119.35(10) . . ?
C8 N2 C1 120.33(10) . . ?
C7 N2 C1 114.40(10) . . ?
N1 C1 N2 107.22(9) . . ?
N1 C1 C2 109.61(10) . . ?
N2 C1 C2 112.02(10) . . ?
N1 C1 H1A 109.3 . . ?
N2 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
C3 C2 C10 118.40(11) . . ?
C3 C2 C1 121.60(11) . . ?
C10 C2 C1 119.69(11) . . ?
O1 C3 C2 123.59(12) . . ?
O1 C3 C4 113.59(12) . . ?
C2 C3 C4 122.80(11) . . ?
C3 C4 C5 110.00(11) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C6 108.97(10) . . ?
N1 C5 C4 107.88(10) . . ?
C6 C5 C4 110.40(11) . . ?
N1 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
C7 C6 C18 119.26(13) . . ?
C7 C6 C5 122.49(11) . . ?
C18 C6 C5 118.23(12) . . ?
C6 C7 C12 120.56(12) . . ?
C6 C7 N2 118.98(11) . . ?
C12 C7 N2 120.42(12) . . ?
O2 C8 O3 124.08(13) . . ?
O2 C8 N2 124.91(13) . . ?
O3 C8 N2 111.00(11) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 O5B 122.7(6) . . ?
O4 C10 O5A 121.99(13) . . ?
O5B C10 O5A 21.8(8) . . ?
O4 C10 C2 123.54(13) . . ?
O5B C10 C2 110.7(7) . . ?
O5A C10 C2 114.36(11) . . ?
O5A C11A H11A 109.5 . . ?
O5A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
O5A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
O5B C11B H11D 109.5 . . ?
O5B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
O5B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C13 C12 C7 118.99(14) . . ?
C13 C12 H12A 120.5 . . ?
C7 C12 H12A 120.5 . . ?
C12 C13 C17 120.79(14) . . ?
C12 C13 C14A 127.6(8) . . ?
C17 C13 C14A 111.6(8) . . ?
C12 C13 C14B 132.2(12) . . ?
C17 C13 C14B 106.9(12) . . ?
C14A C13 C14B 6.8(19) . . ?
C13 C14A C15A 101.0(14) . . ?
C13 C14A H14A 111.6 . . ?
C15A C14A H14A 111.6 . . ?
C13 C14A H14B 111.6 . . ?
C15A C14A H14B 111.6 . . ?
H14A C14A H14B 109.4 . . ?
C16A C15A C14A 100.7(11) . . ?
C16A C15A H15A 111.6 . . ?
C14A C15A H15A 111.6 . . ?
C16A C15A H15B 111.6 . . ?
C14A C15A H15B 111.6 . . ?
H15A C15A H15B 109.4 . . ?
C17 C16A C15A 103.7(9) . . ?
C17 C16A H16A 111.0 . . ?
C15A C16A H16A 111.0 . . ?
C17 C16A H16B 111.0 . . ?
C15A C16A H16B 111.0 . . ?
H16A C16A H16B 109.0 . . ?
C13 C14B C15B 103(2) . . ?
C13 C14B H14C 111.1 . . ?
C15B C14B H14C 111.1 . . ?
C13 C14B H14D 111.1 . . ?
C15B C14B H14D 111.1 . . ?
H14C C14B H14D 109.1 . . ?
C16B C15B C14B 107.9(17) . . ?
C16B C15B H15C 110.1 . . ?
C14B C15B H15C 110.1 . . ?
C16B C15B H15D 110.1 . . ?
C14B C15B H15D 110.1 . . ?
H15C C15B H15D 108.4 . . ?
C15B C16B C17 99.8(11) . . ?
C15B C16B H16C 111.8 . . ?
C17 C16B H16C 111.8 . . ?
C15B C16B H16D 111.8 . . ?
C17 C16B H16D 111.8 . . ?
H16C C16B H16D 109.5 . . ?
C18 C17 C13 120.45(13) . . ?
C18 C17 C16A 132.4(5) . . ?
C13 C17 C16A 107.2(5) . . ?
C18 C17 C16B 123.1(7) . . ?
C13 C17 C16B 116.2(7) . . ?
C16A C17 C16B 10.8(9) . . ?
C17 C18 C6 119.93(14) . . ?
C17 C18 H18A 120.0 . . ?
C6 C18 H18A 120.0 . . ?
O6 C19 O7 124.15(12) . . ?
O6 C19 N1 124.58(12) . . ?
O7 C19 N1 111.24(11) . . ?
O7 C20 H20A 109.5 . . ?
O7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C19 N1 C1 N2 127.93(12) . . . . ?
C5 N1 C1 N2 -69.83(12) . . . . ?
C19 N1 C1 C2 -110.26(13) . . . . ?
C5 N1 C1 C2 51.98(13) . . . . ?
C8 N2 C1 N1 -100.24(12) . . . . ?
C7 N2 C1 N1 52.50(13) . . . . ?
C8 N2 C1 C2 139.47(11) . . . . ?
C7 N2 C1 C2 -67.79(13) . . . . ?
N1 C1 C2 C3 -14.99(16) . . . . ?
N2 C1 C2 C3 103.90(13) . . . . ?
N1 C1 C2 C10 158.45(11) . . . . ?
N2 C1 C2 C10 -82.67(13) . . . . ?
C10 C2 C3 O1 2.4(2) . . . . ?
C1 C2 C3 O1 175.93(12) . . . . ?
C10 C2 C3 C4 -176.04(12) . . . . ?
C1 C2 C3 C4 -2.53(19) . . . . ?
O1 C3 C4 C5 166.89(11) . . . . ?
C2 C3 C4 C5 -14.51(18) . . . . ?
C19 N1 C5 C6 -148.12(11) . . . . ?
C1 N1 C5 C6 49.03(13) . . . . ?
C19 N1 C5 C4 91.99(14) . . . . ?
C1 N1 C5 C4 -70.86(13) . . . . ?
C3 C4 C5 N1 48.40(14) . . . . ?
C3 C4 C5 C6 -70.58(13) . . . . ?
N1 C5 C6 C7 -13.86(16) . . . . ?
C4 C5 C6 C7 104.46(13) . . . . ?
N1 C5 C6 C18 167.87(11) . . . . ?
C4 C5 C6 C18 -73.81(14) . . . . ?
C18 C6 C7 C12 -0.01(19) . . . . ?
C5 C6 C7 C12 -178.26(12) . . . . ?
C18 C6 C7 N2 177.73(11) . . . . ?
C5 C6 C7 N2 -0.53(18) . . . . ?
C8 N2 C7 C6 133.74(13) . . . . ?
C1 N2 C7 C6 -19.29(15) . . . . ?
C8 N2 C7 C12 -48.52(17) . . . . ?
C1 N2 C7 C12 158.45(11) . . . . ?
C9 O3 C8 O2 2.7(2) . . . . ?
C9 O3 C8 N2 -176.09(13) . . . . ?
C7 N2 C8 O2 5.1(2) . . . . ?
C1 N2 C8 O2 156.54(14) . . . . ?
C7 N2 C8 O3 -176.14(11) . . . . ?
C1 N2 C8 O3 -24.73(16) . . . . ?
C11B O5B C10 O4 13.1(18) . . . . ?
C11B O5B C10 O5A -82(2) . . . . ?
C11B O5B C10 C2 173.8(12) . . . . ?
C11A O5A C10 O4 2.8(3) . . . . ?
C11A O5A C10 O5B 101.5(18) . . . . ?
C11A O5A C10 C2 -173.47(14) . . . . ?
C3 C2 C10 O4 -4.5(2) . . . . ?
C1 C2 C10 O4 -178.12(12) . . . . ?
C3 C2 C10 O5B -165.0(9) . . . . ?
C1 C2 C10 O5B 21.3(9) . . . . ?
C3 C2 C10 O5A 171.70(15) . . . . ?
C1 C2 C10 O5A -1.9(2) . . . . ?
C6 C7 C12 C13 -1.1(2) . . . . ?
N2 C7 C12 C13 -178.84(12) . . . . ?
C7 C12 C13 C17 1.6(2) . . . . ?
C7 C12 C13 C14A -177.0(10) . . . . ?
C7 C12 C13 C14B 176.5(16) . . . . ?
C12 C13 C14A C15A -157.5(6) . . . . ?
C17 C13 C14A C15A 23.8(13) . . . . ?
C14B C13 C14A C15A -23(16) . . . . ?
C13 C14A C15A C16A -36.7(13) . . . . ?
C14A C15A C16A C17 37.5(12) . . . . ?
C12 C13 C14B C15B 171.3(7) . . . . ?
C17 C13 C14B C15B -13.2(19) . . . . ?
C14A C13 C14B C15B 122(17) . . . . ?
C13 C14B C15B C16B 24(2) . . . . ?
C14B C15B C16B C17 -23(2) . . . . ?
C12 C13 C17 C18 -0.8(2) . . . . ?
C14A C13 C17 C18 177.9(8) . . . . ?
C14B C13 C17 C18 -176.9(12) . . . . ?
C12 C13 C17 C16A -178.9(6) . . . . ?
C14A C13 C17 C16A -0.2(10) . . . . ?
C14B C13 C17 C16A 5.0(13) . . . . ?
C12 C13 C17 C16B 174.7(9) . . . . ?
C14A C13 C17 C16B -6.6(13) . . . . ?
C14B C13 C17 C16B -1.4(15) . . . . ?
C15A C16A C17 C18 157.9(4) . . . . ?
C15A C16A C17 C13 -24.3(9) . . . . ?
C15A C16A C17 C16B 124(9) . . . . ?
C15B C16B C17 C18 -168.6(8) . . . . ?
C15B C16B C17 C13 16.0(16) . . . . ?
C15B C16B C17 C16A -18(7) . . . . ?
C13 C17 C18 C6 -0.4(2) . . . . ?
C16A C17 C18 C6 177.2(8) . . . . ?
C16B C17 C18 C6 -175.5(10) . . . . ?
C7 C6 C18 C17 0.8(2) . . . . ?
C5 C6 C18 C17 179.09(13) . . . . ?
C20 O7 C19 O6 -4.4(2) . . . . ?
C20 O7 C19 N1 177.48(12) . . . . ?
C1 N1 C19 O6 169.43(13) . . . . ?
C5 N1 C19 O6 8.7(2) . . . . ?
C1 N1 C19 O7 -12.51(17) . . . . ?
C5 N1 C19 O7 -173.21(11) . . . . ?

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
O1 H1B O4 0.84 1.81 2.5465(16) 145.6 .

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         1.061
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.058

#======================================================================

#_eof # End of Crystallographic Information File



data_avkv11
_database_code_depnum_ccdc_archive 'CCDC 677226'

_audit_author_name               'Villinger, A.'
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
11-Hydroxy-4,5-dimethyl-8,13-diaza-tricyclo[7.3.1.02,7]trideca-2(7),3,5,10-
tetraene-8,13-tricarboxylic acid trimethyl ester
;
_chemical_name_common            
;
11-Hydroxy-4,5-dimethyl-8,13-diaza-
tricyclo(7.3.1.02,7)trideca-2(7),3,5,10-tetraene-8,13-tricarboxylic
acid trimethyl ester
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 N2 O7'
_chemical_formula_sum            'C19 H22 N2 O7'
_chemical_formula_weight         390.39

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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1758(16)
_cell_length_b                   8.9304(18)
_cell_length_c                   13.714(3)
_cell_angle_alpha                103.88(3)
_cell_angle_beta                 96.73(3)
_cell_angle_gamma                105.83(3)
_cell_volume                     917.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5006
_cell_measurement_theta_min      4.950
_cell_measurement_theta_max      62.672

#==============================================================================

# EXPERIMENTAL DATA

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20522
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         27.50
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.986
_reflns_number_total             4169
_reflns_number_gt                3601
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex v2.0-2'
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), DIAMOND v3.0a (Brandenburg, 2005)
;
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
The H atom bonded to O2 was located in a difference map and refined freely.
Other H atoms were positioned geometrically and refined using a riding
model , with C---H = 0.95 (aryl CH), 1.00 (methine group), 0.99 (methylene
groups) or 0.98 \%A (methyl groups) and with <i>U</i>~iso~(H) = 1.5 times
<i>U</i>~eq~(C) (methyl groups) or with <i>U</i>~iso~(H) = 1.2 times
<i>U</i>~eq~(C) (aryl-CH, methylene groups, methine group). Torsion angles of
all methyl groups were allowed to refine. The aryl part of the molecule (C6,C7,
C12,C13,C14,C15,C16) was disordered, with two possible positions. The occupancy
factors of each part A/B were refined freely (A = 0.655(4)/B = 0.345(4)).
The displacement parameters of the atoms in the pairs A/B were constrained.
For the six-membered phenyl ring, a rigid group refinement was performed for
both parts.

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^)+(0.0368P)^2^+0.6087P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4169
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.042

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.50648(16) 0.29579(14) 0.03072(10) 0.0342(3) Uani 1 1 d . . .
H2 H 0.615(3) 0.319(3) 0.0641(17) 0.048(6) Uiso 1 1 d . . .
N1 N 0.28238(15) 0.61622(15) 0.17994(10) 0.0255(3) Uani 1 1 d . . .
C1 C 0.43940(17) 0.61643(17) 0.24340(11) 0.0218(3) Uani 1 1 d . B .
H1 H 0.5239 0.7286 0.2665 0.026 Uiso 1 1 calc R . .
C2 C 0.52117(18) 0.50071(17) 0.18250(12) 0.0237(3) Uani 1 1 d . . .
C3 C 0.43599(19) 0.39384(18) 0.09016(13) 0.0269(3) Uani 1 1 d . B .
C4 C 0.2509(2) 0.3720(2) 0.04626(13) 0.0321(4) Uani 1 1 d . . .
H4A H 0.1853 0.2547 0.0217 0.039 Uiso 1 1 calc R A 1
H4B H 0.2473 0.4166 -0.0132 0.039 Uiso 1 1 calc R A 1
N2 N 0.38674(15) 0.56820(14) 0.33284(10) 0.0228(3) Uani 1 1 d . . .
C8 C 0.42160(19) 0.69417(18) 0.42129(12) 0.0262(3) Uani 1 1 d . B .
C9 C 0.3578(3) 0.7834(3) 0.58389(15) 0.0485(5) Uani 1 1 d . B .
H9A H 0.4731 0.8012 0.6231 0.073 Uiso 1 1 calc R . .
H9B H 0.2701 0.7525 0.6245 0.073 Uiso 1 1 calc R . .
H9C H 0.3532 0.8835 0.5678 0.073 Uiso 1 1 calc R . .
O2 O 0.32400(16) 0.65426(14) 0.48936(9) 0.0352(3) Uani 1 1 d . . .
O3 O 0.52883(17) 0.82484(14) 0.43576(9) 0.0386(3) Uani 1 1 d . . .
C10 C 0.69566(19) 0.50356(18) 0.22286(12) 0.0255(3) Uani 1 1 d . B .
C11 C 0.9335(2) 0.6035(2) 0.36165(15) 0.0383(4) Uani 1 1 d . B .
H11A H 0.9323 0.4932 0.3607 0.057 Uiso 1 1 calc R . .
H11B H 0.9679 0.6734 0.4324 0.057 Uiso 1 1 calc R . .
H11C H 1.0163 0.6460 0.3211 0.057 Uiso 1 1 calc R . .
O4 O 0.77563(15) 0.42261(15) 0.17481(10) 0.0373(3) Uani 1 1 d . . .
O5 O 0.76135(13) 0.60048(14) 0.31812(9) 0.0306(3) Uani 1 1 d . . .
C18 C 0.2670(2) 0.73973(19) 0.14179(12) 0.0281(3) Uani 1 1 d . B .
C19 C 0.3964(3) 1.0133(2) 0.14770(15) 0.0419(4) Uani 1 1 d . B .
H19A H 0.3849 0.9795 0.0731 0.063 Uiso 1 1 calc R . .
H19B H 0.5046 1.1024 0.1781 0.063 Uiso 1 1 calc R . .
H19C H 0.2980 1.0500 0.1650 0.063 Uiso 1 1 calc R . .
O6 O 0.14806(17) 0.72840(17) 0.07578(11) 0.0461(3) Uani 1 1 d . . .
O7 O 0.39861(15) 0.87782(13) 0.18741(9) 0.0308(3) Uani 1 1 d . . .
C5A C 0.1657(12) 0.4569(11) 0.1254(6) 0.0213(10) Uani 0.655(4) 1 d P B 1
H5A H 0.0524 0.4627 0.0929 0.026 Uiso 0.655(4) 1 calc PR B 1
C6A C 0.1413(5) 0.3588(4) 0.2049(3) 0.0228(5) Uani 0.655(4) 1 d PG B 1
C7A C 0.2467(6) 0.4107(4) 0.3015(3) 0.0224(5) Uani 0.655(4) 1 d PG B 1
C12A C 0.2239(5) 0.3126(3) 0.3668(2) 0.0263(6) Uani 0.655(4) 1 d PG B 1
H12A H 0.2959 0.3481 0.4328 0.032 Uiso 0.655(4) 1 calc PR B 1
C13A C 0.0957(3) 0.1624(3) 0.3355(2) 0.0259(6) Uani 0.655(4) 1 d PG B 1
C14A C -0.0097(3) 0.1105(2) 0.2389(2) 0.0282(7) Uani 0.655(4) 1 d PG B 1
C15A C 0.0131(3) 0.2087(3) 0.17361(19) 0.0252(6) Uani 0.655(4) 1 d PG B 1
H15A H -0.0590 0.1732 0.1076 0.030 Uiso 0.655(4) 1 calc PR B 1
C16A C 0.0836(4) 0.0561(3) 0.4069(2) 0.0451(8) Uani 0.655(4) 1 d P B 1
H16A H 0.1629 0.1171 0.4724 0.068 Uiso 0.655(4) 1 calc PR B 1
H16B H 0.1154 -0.0403 0.3762 0.068 Uiso 0.655(4) 1 calc PR B 1
H16C H -0.0354 0.0227 0.4185 0.068 Uiso 0.655(4) 1 calc PR B 1
C17A C -0.1515(4) -0.0530(4) 0.2041(3) 0.0377(7) Uani 0.655(4) 1 d P B 1
H17A H -0.2256 -0.0614 0.1401 0.057 Uiso 0.655(4) 1 calc PR B 1
H17B H -0.2216 -0.0625 0.2569 0.057 Uiso 0.655(4) 1 calc PR B 1
H17C H -0.0987 -0.1403 0.1927 0.057 Uiso 0.655(4) 1 calc PR B 1
C5B C 0.169(3) 0.436(2) 0.1419(14) 0.0213(10) Uani 0.345(4) 1 d P B 2
H5B H 0.0496 0.4343 0.1136 0.026 Uiso 0.345(4) 1 calc PR B 2
C6B C 0.1513(11) 0.3503(8) 0.2244(5) 0.0228(5) Uani 0.345(4) 1 d PG B 2
C7B C 0.2612(13) 0.4219(8) 0.3196(6) 0.0224(5) Uani 0.345(4) 1 d PG B 2
C12B C 0.2509(10) 0.3403(7) 0.3943(5) 0.0263(6) Uani 0.345(4) 1 d PG B 2
H12B H 0.3260 0.3892 0.4594 0.032 Uiso 0.345(4) 1 calc PR B 2
C13B C 0.1307(6) 0.1872(6) 0.3738(3) 0.0252(6) Uani 0.345(4) 1 d PG B 2
H13B H 0.1236 0.1315 0.4249 0.030 Uiso 0.345(4) 1 calc PR B 2
C14B C 0.0208(7) 0.1157(5) 0.2786(4) 0.0282(7) Uani 0.345(4) 1 d PG B 2
C15B C 0.0311(7) 0.1972(7) 0.2039(4) 0.0259(6) Uani 0.345(4) 1 d PG B 2
C16B C -0.0891(6) 0.1115(6) 0.1021(4) 0.0339(12) Uani 0.345(4) 1 d P B 2
H16D H -0.0900 0.1890 0.0623 0.051 Uiso 0.345(4) 1 calc PR B 2
H16E H -0.2065 0.0652 0.1129 0.051 Uiso 0.345(4) 1 calc PR B 2
H16F H -0.0493 0.0243 0.0647 0.051 Uiso 0.345(4) 1 calc PR B 2
C17B C -0.1139(9) -0.0563(7) 0.2585(6) 0.0446(16) Uani 0.345(4) 1 d P B 2
H17G H -0.2314 -0.0505 0.2415 0.067 Uiso 0.345(4) 1 calc PR B 2
H17H H -0.1027 -0.0931 0.3200 0.067 Uiso 0.345(4) 1 calc PR B 2
H17I H -0.0919 -0.1331 0.2012 0.067 Uiso 0.345(4) 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
O1 0.0323(6) 0.0327(6) 0.0357(7) 0.0006(5) 0.0118(5) 0.0126(5)
N1 0.0170(5) 0.0237(6) 0.0298(7) 0.0017(5) -0.0026(5) 0.0049(5)
C1 0.0161(6) 0.0194(6) 0.0267(8) 0.0038(6) 0.0012(5) 0.0039(5)
C2 0.0189(6) 0.0212(7) 0.0311(8) 0.0067(6) 0.0064(6) 0.0062(5)
C3 0.0246(7) 0.0226(7) 0.0327(8) 0.0052(6) 0.0101(6) 0.0065(6)
C4 0.0233(7) 0.0308(8) 0.0314(9) -0.0040(7) 0.0031(6) 0.0032(6)
N2 0.0193(6) 0.0192(6) 0.0277(7) 0.0045(5) 0.0044(5) 0.0046(5)
C8 0.0235(7) 0.0269(7) 0.0269(8) 0.0058(6) 0.0014(6) 0.0089(6)
C9 0.0551(12) 0.0515(12) 0.0307(10) -0.0014(8) 0.0133(9) 0.0130(10)
O2 0.0382(6) 0.0356(6) 0.0280(6) 0.0046(5) 0.0096(5) 0.0081(5)
O3 0.0414(7) 0.0281(6) 0.0328(7) -0.0006(5) 0.0035(5) -0.0010(5)
C10 0.0222(7) 0.0245(7) 0.0328(8) 0.0107(6) 0.0080(6) 0.0086(6)
C11 0.0238(8) 0.0444(10) 0.0452(11) 0.0100(8) -0.0008(7) 0.0140(7)
O4 0.0294(6) 0.0449(7) 0.0422(7) 0.0080(6) 0.0100(5) 0.0214(5)
O5 0.0207(5) 0.0329(6) 0.0361(6) 0.0056(5) 0.0014(5) 0.0108(4)
C18 0.0249(7) 0.0308(8) 0.0280(8) 0.0028(6) 0.0022(6) 0.0138(6)
C19 0.0552(11) 0.0319(9) 0.0423(11) 0.0147(8) 0.0035(9) 0.0184(8)
O6 0.0387(7) 0.0479(8) 0.0464(8) 0.0082(6) -0.0141(6) 0.0188(6)
O7 0.0346(6) 0.0252(5) 0.0312(6) 0.0074(5) -0.0008(5) 0.0105(5)
C5A 0.0167(7) 0.021(2) 0.023(3) 0.0042(13) -0.0013(17) 0.0042(13)
C6A 0.0171(8) 0.0211(8) 0.0273(15) 0.0011(8) 0.0042(10) 0.0065(6)
C7A 0.0172(10) 0.0169(8) 0.0289(17) 0.0003(9) 0.0052(10) 0.0038(6)
C12A 0.0240(14) 0.0182(13) 0.0296(19) 0.0001(12) 0.0017(12) 0.0028(9)
C13A 0.0250(12) 0.0175(10) 0.0273(17) 0.0020(9) 0.0014(12) -0.0005(9)
C14A 0.0212(13) 0.0218(8) 0.032(2) -0.0030(14) 0.0017(13) 0.0021(8)
C15A 0.0186(10) 0.0273(11) 0.0246(16) -0.0004(10) 0.0014(11) 0.0069(8)
C16A 0.0494(17) 0.0320(14) 0.0454(17) 0.0175(13) 0.0001(13) -0.0027(12)
C17A 0.0353(15) 0.0274(14) 0.0406(19) 0.0065(14) 0.0050(14) -0.0022(11)
C5B 0.0167(7) 0.021(2) 0.023(3) 0.0042(13) -0.0013(17) 0.0042(13)
C6B 0.0171(8) 0.0211(8) 0.0273(15) 0.0011(8) 0.0042(10) 0.0065(6)
C7B 0.0172(10) 0.0169(8) 0.0289(17) 0.0003(9) 0.0052(10) 0.0038(6)
C12B 0.0240(14) 0.0182(13) 0.0296(19) 0.0001(12) 0.0017(12) 0.0028(9)
C13B 0.0186(10) 0.0273(11) 0.0246(16) -0.0004(10) 0.0014(11) 0.0069(8)
C14B 0.0212(13) 0.0218(8) 0.032(2) -0.0030(14) 0.0017(13) 0.0021(8)
C15B 0.0250(12) 0.0175(10) 0.0273(17) 0.0020(9) 0.0014(12) -0.0005(9)
C16B 0.029(2) 0.026(2) 0.036(3) 0.006(2) -0.001(2) -0.0011(18)
C17B 0.049(4) 0.032(3) 0.049(4) 0.015(3) 0.013(3) 0.001(3)

#==============================================================================

# MOLECULAR GEOMETRY

_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 C3 1.3440(19) . ?
O1 H2 0.89(2) . ?
N1 C18 1.358(2) . ?
N1 C5A 1.441(10) . ?
N1 C1 1.4634(18) . ?
N1 C5B 1.547(19) . ?
C1 N2 1.4668(19) . ?
C1 C2 1.519(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.360(2) . ?
C2 C10 1.460(2) . ?
C3 C4 1.503(2) . ?
C4 C5A 1.519(10) . ?
C4 C5B 1.60(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N2 C7B 1.380(4) . ?
N2 C8 1.381(2) . ?
N2 C7A 1.480(2) . ?
C8 O3 1.208(2) . ?
C8 O2 1.347(2) . ?
C9 O2 1.453(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 O4 1.2307(19) . ?
C10 O5 1.336(2) . ?
C11 O5 1.4534(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C18 O6 1.213(2) . ?
C18 O7 1.348(2) . ?
C19 O7 1.445(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C5A C6A 1.552(5) . ?
C5A H5A 1.0000 . ?
C6A C7A 1.3900 . ?
C6A C15A 1.3900 . ?
C7A C12A 1.3900 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3900 . ?
C13A C16A 1.512(4) . ?
C14A C15A 1.3900 . ?
C14A C17A 1.522(3) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C5B C6B 1.509(14) . ?
C5B H5B 1.0000 . ?
C6B C7B 1.3900 . ?
C6B C15B 1.3900 . ?
C7B C12B 1.3900 . ?
C12B C13B 1.3900 . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3900 . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3900 . ?
C14B C17B 1.565(7) . ?
C15B C16B 1.502(7) . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17G 0.9800 . ?
C17B H17H 0.9800 . ?
C17B H17I 0.9800 . ?

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
C3 O1 H2 105.6(14) . . ?
C18 N1 C5A 116.4(2) . . ?
C18 N1 C1 124.99(12) . . ?
C5A N1 C1 114.4(3) . . ?
C18 N1 C5B 127.9(5) . . ?
C5A N1 C5B 12.0(7) . . ?
C1 N1 C5B 104.8(6) . . ?
N1 C1 N2 106.61(11) . . ?
N1 C1 C2 110.13(12) . . ?
N2 C1 C2 111.88(12) . . ?
N1 C1 H1 109.4 . . ?
N2 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
C3 C2 C10 118.63(14) . . ?
C3 C2 C1 121.58(13) . . ?
C10 C2 C1 119.79(13) . . ?
O1 C3 C2 123.79(14) . . ?
O1 C3 C4 113.63(14) . . ?
C2 C3 C4 122.57(14) . . ?
C3 C4 C5A 111.4(3) . . ?
C3 C4 C5B 105.6(6) . . ?
C5A C4 C5B 11.7(6) . . ?
C3 C4 H4A 109.4 . . ?
C5A C4 H4A 109.4 . . ?
C5B C4 H4A 103.0 . . ?
C3 C4 H4B 109.4 . . ?
C5A C4 H4B 109.4 . . ?
C5B C4 H4B 121.1 . . ?
H4A C4 H4B 108.0 . . ?
C7B N2 C8 121.1(5) . . ?
C7B N2 C1 120.0(4) . . ?
C8 N2 C1 115.14(12) . . ?
C7B N2 C7A 9.0(4) . . ?
C8 N2 C7A 128.3(2) . . ?
C1 N2 C7A 111.17(18) . . ?
O3 C8 O2 124.11(15) . . ?
O3 C8 N2 123.43(15) . . ?
O2 C8 N2 112.45(13) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 O2 C9 114.12(14) . . ?
O4 C10 O5 122.33(14) . . ?
O4 C10 C2 123.60(15) . . ?
O5 C10 C2 114.06(13) . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 O5 C11 115.56(13) . . ?
O6 C18 O7 123.91(16) . . ?
O6 C18 N1 124.27(16) . . ?
O7 C18 N1 111.81(13) . . ?
O7 C19 H19A 109.5 . . ?
O7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 O7 C19 115.29(13) . . ?
N1 C5A C4 109.5(6) . . ?
N1 C5A C6A 106.5(5) . . ?
C4 C5A C6A 106.7(5) . . ?
N1 C5A H5A 111.3 . . ?
C4 C5A H5A 111.3 . . ?
C6A C5A H5A 111.3 . . ?
C7A C6A C15A 120.0 . . ?
C7A C6A C5A 123.0(4) . . ?
C15A C6A C5A 116.9(4) . . ?
C6A C7A C12A 120.0 . . ?
C6A C7A N2 119.6(2) . . ?
C12A C7A N2 120.3(2) . . ?
C13A C12A C7A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C7A C12A H12A 120.0 . . ?
C12A C13A C14A 120.0 . . ?
C12A C13A C16A 117.81(19) . . ?
C14A C13A C16A 122.08(19) . . ?
C15A C14A C13A 120.0 . . ?
C15A C14A C17A 119.47(19) . . ?
C13A C14A C17A 120.53(19) . . ?
C14A C15A C6A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C6A C15A H15A 120.0 . . ?
C6B C5B N1 114.6(12) . . ?
C6B C5B C4 120.4(12) . . ?
N1 C5B C4 100.5(10) . . ?
C6B C5B H5B 106.8 . . ?
N1 C5B H5B 106.8 . . ?
C4 C5B H5B 106.8 . . ?
C7B C6B C15B 120.0 . . ?
C7B C6B C5B 119.7(9) . . ?
C15B C6B C5B 120.2(9) . . ?
N2 C7B C6B 117.4(4) . . ?
N2 C7B C12B 122.4(4) . . ?
C6B C7B C12B 120.0 . . ?
C13B C12B C7B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C7B C12B H12B 120.0 . . ?
C12B C13B C14B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C15B C14B C13B 120.0 . . ?
C15B C14B C17B 121.4(4) . . ?
C13B C14B C17B 118.6(4) . . ?
C14B C15B C6B 120.0 . . ?
C14B C15B C16B 117.2(4) . . ?
C6B C15B C16B 122.8(4) . . ?
C15B C16B H16D 109.5 . . ?
C15B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C14B C17B H17G 109.5 . . ?
C14B C17B H17H 109.5 . . ?
H17G C17B H17H 109.5 . . ?
C14B C17B H17I 109.5 . . ?
H17G C17B H17I 109.5 . . ?
H17H C17B H17I 109.5 . . ?

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
C18 N1 C1 N2 130.16(15) . . . . ?
C5A N1 C1 N2 -73.7(4) . . . . ?
C5B N1 C1 N2 -66.2(8) . . . . ?
C18 N1 C1 C2 -108.26(16) . . . . ?
C5A N1 C1 C2 47.9(4) . . . . ?
C5B N1 C1 C2 55.4(8) . . . . ?
N1 C1 C2 C3 -11.40(19) . . . . ?
N2 C1 C2 C3 106.98(16) . . . . ?
N1 C1 C2 C10 168.25(13) . . . . ?
N2 C1 C2 C10 -73.37(16) . . . . ?
C10 C2 C3 O1 -3.7(2) . . . . ?
C1 C2 C3 O1 175.96(14) . . . . ?
C10 C2 C3 C4 174.80(14) . . . . ?
C1 C2 C3 C4 -5.5(2) . . . . ?
O1 C3 C4 C5A 167.5(3) . . . . ?
C2 C3 C4 C5A -11.1(3) . . . . ?
O1 C3 C4 C5B 156.7(6) . . . . ?
C2 C3 C4 C5B -21.9(6) . . . . ?
N1 C1 N2 C7B 57.4(6) . . . . ?
C2 C1 N2 C7B -63.1(6) . . . . ?
N1 C1 N2 C8 -101.08(14) . . . . ?
C2 C1 N2 C8 138.46(13) . . . . ?
N1 C1 N2 C7A 55.3(3) . . . . ?
C2 C1 N2 C7A -65.2(3) . . . . ?
C7B N2 C8 O3 -179.1(5) . . . . ?
C1 N2 C8 O3 -21.0(2) . . . . ?
C7A N2 C8 O3 -172.5(3) . . . . ?
C7B N2 C8 O2 1.4(6) . . . . ?
C1 N2 C8 O2 159.57(12) . . . . ?
C7A N2 C8 O2 8.0(3) . . . . ?
O3 C8 O2 C9 0.1(2) . . . . ?
N2 C8 O2 C9 179.55(15) . . . . ?
C3 C2 C10 O4 5.4(2) . . . . ?
C1 C2 C10 O4 -174.29(14) . . . . ?
C3 C2 C10 O5 -173.59(14) . . . . ?
C1 C2 C10 O5 6.7(2) . . . . ?
O4 C10 O5 C11 -0.3(2) . . . . ?
C2 C10 O5 C11 178.67(13) . . . . ?
C5A N1 C18 O6 11.1(5) . . . . ?
C1 N1 C18 O6 166.86(16) . . . . ?
C5B N1 C18 O6 7.1(10) . . . . ?
C5A N1 C18 O7 -169.9(4) . . . . ?
C1 N1 C18 O7 -14.2(2) . . . . ?
C5B N1 C18 O7 -174.0(10) . . . . ?
O6 C18 O7 C19 -3.9(2) . . . . ?
N1 C18 O7 C19 177.16(14) . . . . ?
C18 N1 C5A C4 92.2(4) . . . . ?
C1 N1 C5A C4 -66.1(4) . . . . ?
C5B N1 C5A C4 -103(6) . . . . ?
C18 N1 C5A C6A -152.8(4) . . . . ?
C1 N1 C5A C6A 48.9(6) . . . . ?
C5B N1 C5A C6A 12(5) . . . . ?
C3 C4 C5A N1 44.5(4) . . . . ?
C5B C4 C5A N1 107(5) . . . . ?
C3 C4 C5A C6A -70.5(6) . . . . ?
C5B C4 C5A C6A -8(5) . . . . ?
N1 C5A C6A C7A -13.1(7) . . . . ?
C4 C5A C6A C7A 103.8(5) . . . . ?
N1 C5A C6A C15A 170.4(4) . . . . ?
C4 C5A C6A C15A -72.6(6) . . . . ?
C15A C6A C7A C12A 0.0 . . . . ?
C5A C6A C7A C12A -176.3(5) . . . . ?
C15A C6A C7A N2 177.9(5) . . . . ?
C5A C6A C7A N2 1.6(5) . . . . ?
C7B N2 C7A C6A 168(5) . . . . ?
C8 N2 C7A C6A 129.12(19) . . . . ?
C1 N2 C7A C6A -23.3(3) . . . . ?
C7B N2 C7A C12A -14(5) . . . . ?
C8 N2 C7A C12A -53.0(4) . . . . ?
C1 N2 C7A C12A 154.6(2) . . . . ?
C6A C7A C12A C13A 0.0 . . . . ?
N2 C7A C12A C13A -177.9(5) . . . . ?
C7A C12A C13A C14A 0.0 . . . . ?
C7A C12A C13A C16A 176.3(2) . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
C16A C13A C14A C15A -176.2(2) . . . . ?
C12A C13A C14A C17A -179.5(3) . . . . ?
C16A C13A C14A C17A 4.3(3) . . . . ?
C13A C14A C15A C6A 0.0 . . . . ?
C17A C14A C15A C6A 179.5(3) . . . . ?
C7A C6A C15A C14A 0.0 . . . . ?
C5A C6A C15A C14A 176.6(5) . . . . ?
C18 N1 C5B C6B -149.3(8) . . . . ?
C5A N1 C5B C6B -167(7) . . . . ?
C1 N1 C5B C6B 47.7(14) . . . . ?
C18 N1 C5B C4 80.1(10) . . . . ?
C5A N1 C5B C4 62(5) . . . . ?
C1 N1 C5B C4 -82.8(7) . . . . ?
C3 C4 C5B C6B -64.4(14) . . . . ?
C5A C4 C5B C6B 174(6) . . . . ?
C3 C4 C5B N1 62.4(7) . . . . ?
C5A C4 C5B N1 -59(5) . . . . ?
N1 C5B C6B C7B -13.3(16) . . . . ?
C4 C5B C6B C7B 106.7(13) . . . . ?
N1 C5B C6B C15B 169.5(9) . . . . ?
C4 C5B C6B C15B -70.5(16) . . . . ?
C8 N2 C7B C6B 137.0(3) . . . . ?
C1 N2 C7B C6B -20.1(8) . . . . ?
C7A N2 C7B C6B -8(5) . . . . ?
C8 N2 C7B C12B -48.0(9) . . . . ?
C1 N2 C7B C12B 154.8(4) . . . . ?
C7A N2 C7B C12B 167(6) . . . . ?
C15B C6B C7B N2 175.1(10) . . . . ?
C5B C6B C7B N2 -2.1(10) . . . . ?
C15B C6B C7B C12B 0.0 . . . . ?
C5B C6B C7B C12B -177.2(11) . . . . ?
N2 C7B C12B C13B -174.8(11) . . . . ?
C6B C7B C12B C13B 0.0 . . . . ?
C7B C12B C13B C14B 0.0 . . . . ?
C12B C13B C14B C15B 0.0 . . . . ?
C12B C13B C14B C17B -179.6(7) . . . . ?
C13B C14B C15B C6B 0.0 . . . . ?
C17B C14B C15B C6B 179.6(7) . . . . ?
C13B C14B C15B C16B 178.8(5) . . . . ?
C17B C14B C15B C16B -1.6(6) . . . . ?
C7B C6B C15B C14B 0.0 . . . . ?
C5B C6B C15B C14B 177.2(11) . . . . ?
C7B C6B C15B C16B -178.8(5) . . . . ?
C5B C6B C15B C16B -1.6(12) . . . . ?

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
O1 H2 O4 0.89(2) 1.76(2) 2.565(2) 150(2) .
#===================== End of CIF submission =================================