# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2006


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Jonathan L. Sessler'
_publ_contact_author_address     
;
Department of Chemistry and Biochemistry
University of Texas at Austin
24th & Speedway
Austin
TX
USA
UNITED STATES OF AMERICA
;

_publ_contact_author_email       SESSLER@MAIL.UTEXAS.EDU

_publ_section_title              
;
2-Amino-3,4-diethylpyrrole: a new building block for
coiled structures
;
loop_
_publ_author_name
'Jonathan L. Sessler'
'Vince Lynch'
'G. Dan Pantos'
'M. Salome Rodriguez-Morgade'
'Tomas Torres'

# Attachment 'Helix_CC_1.cif'

data_s231
_database_code_depnum_ccdc_archive 'CCDC 299137'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C49 H43 N11 O6'
_chemical_formula_weight         881.94

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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.7239(4)
_cell_length_b                   13.6559(5)
_cell_length_c                   15.0447(7)
_cell_angle_alpha                65.588(2)
_cell_angle_beta                 69.964(2)
_cell_angle_gamma                67.954(2)
_cell_volume                     2151.24(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7563
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needles
_exptl_crystal_colour            'dark blue'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_absorpt_coefficient_mu    0.093
_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      153(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  'Nonius Kappa CCD'
_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            7477
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0938
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7477
_reflns_number_gt                4672
_reflns_threshold_expression     >2sigma(I)

_publ_section_references         
;
Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C.,
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97.
(1999) J. Appl. Cryst. 32, 115-119.

Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology,
276, Macromolecular Crystallography, part A, 307-326, C. W. Carter,
Jr. and R. M. Sweets, Eds., Academic Press.

Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens
Analytical X-ray Instruments, Inc., Madison, WI, USA.

;
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_reduction        
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C.,
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+1.8006P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0074(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         7477
_refine_ls_number_parameters     612
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.064
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1042(3) 0.5851(3) 0.3158(3) 0.0510(10) Uani 1 1 d . . .
H1A H -0.1170 0.6342 0.3515 0.076 Uiso 1 1 d R . .
H1B H -0.0963 0.6263 0.2455 0.076 Uiso 1 1 d R . .
H1C H -0.1689 0.5541 0.3394 0.076 Uiso 1 1 d R . .
O2 O 0.00034(19) 0.49375(19) 0.33313(18) 0.0459(6) Uani 1 1 d . . .
C3 C 0.0296(3) 0.4188(3) 0.2860(3) 0.0390(8) Uani 1 1 d . . .
O4 O -0.0274(2) 0.4206(2) 0.23539(18) 0.0504(7) Uani 1 1 d . . .
C5 C 0.1406(3) 0.3343(3) 0.3041(2) 0.0338(8) Uani 1 1 d . . .
C6 C 0.1957(3) 0.3391(3) 0.3702(3) 0.0358(8) Uani 1 1 d . . .
N7 N 0.2410(3) 0.3406(2) 0.4245(2) 0.0446(8) Uani 1 1 d . . .
C8 C 0.1896(3) 0.2575(3) 0.2552(2) 0.0369(8) Uani 1 1 d . . .
H8 H 0.1451 0.2637 0.2120 0.044 Uiso 1 1 d R . .
C9 C 0.2944(3) 0.1719(3) 0.2567(2) 0.0346(8) Uani 1 1 d . . .
C10 C 0.3410(3) 0.0922(3) 0.2057(2) 0.0383(8) Uani 1 1 d . . .
C11 C 0.4489(3) 0.0267(3) 0.2282(2) 0.0358(8) Uani 1 1 d . . .
C12 C 0.4677(3) 0.0658(3) 0.2929(2) 0.0337(8) Uani 1 1 d . . .
N13 N 0.3740(2) 0.1528(2) 0.30931(19) 0.0325(6) Uani 1 1 d . . .
N14 N 0.5636(2) 0.0221(2) 0.33357(19) 0.0339(6) Uani 1 1 d . . .
C15 C 0.5756(3) 0.0679(2) 0.3890(2) 0.0323(8) Uani 1 1 d . . .
C16 C 0.6753(3) 0.0294(2) 0.4343(2) 0.0318(8) Uani 1 1 d . . .
C17 C 0.7749(3) -0.0584(3) 0.4320(2) 0.0383(8) Uani 1 1 d . . .
H17 H 0.7863 -0.1083 0.3975 0.046 Uiso 1 1 d R . .
C18 C 0.8576(3) -0.0711(3) 0.4802(2) 0.0410(9) Uani 1 1 d . . .
H18 H 0.9286 -0.1302 0.4787 0.049 Uiso 1 1 d R . .
C19 C 0.8380(3) 0.0014(3) 0.5304(2) 0.0389(8) Uani 1 1 d . . .
H19 H 0.8959 -0.0095 0.5636 0.047 Uiso 1 1 d R . .
C20 C 0.7366(3) 0.0888(3) 0.5359(2) 0.0359(8) Uani 1 1 d . . .
H20 H 0.7229 0.1390 0.5707 0.043 Uiso 1 1 d R . .
C21 C 0.6548(3) 0.1021(2) 0.4865(2) 0.0304(7) Uani 1 1 d . . .
C22 C 0.5403(3) 0.1830(2) 0.4689(2) 0.0289(7) Uani 1 1 d . . .
N23 N 0.4974(2) 0.1623(2) 0.41278(18) 0.0305(6) Uani 1 1 d . . .
N24 N 0.4769(2) 0.2763(2) 0.4965(2) 0.0322(7) Uani 1 1 d . . .
C25 C 0.4887(3) 0.3151(2) 0.5620(2) 0.0301(7) Uani 1 1 d . . .
O26 O 0.55970(19) 0.26626(17) 0.61452(16) 0.0365(6) Uani 1 1 d . . .
C27 C 0.4046(3) 0.4260(2) 0.5652(2) 0.0279(7) Uani 1 1 d . . .
C28 C 0.3948(3) 0.4660(3) 0.6399(2) 0.0312(7) Uani 1 1 d . . .
H28 H 0.4403 0.4231 0.6898 0.037 Uiso 1 1 d R . .
C29 C 0.3170(3) 0.5687(3) 0.6412(2) 0.0336(8) Uani 1 1 d . . .
H29 H 0.3081 0.5987 0.6918 0.040 Uiso 1 1 d R . .
C30 C 0.2526(3) 0.6281(3) 0.5685(2) 0.0329(8) Uani 1 1 d . . .
H30 H 0.1976 0.6993 0.5676 0.039 Uiso 1 1 d R . .
C31 C 0.2700(3) 0.5831(2) 0.4956(2) 0.0297(7) Uani 1 1 d . . .
N32 N 0.3441(2) 0.4836(2) 0.49267(18) 0.0270(6) Uani 1 1 d . . .
C33 C 0.2043(3) 0.6506(3) 0.4129(2) 0.0335(8) Uani 1 1 d . . .
O34 O 0.1339(2) 0.7394(2) 0.41373(18) 0.0554(7) Uani 1 1 d . . .
N35 N 0.2329(2) 0.6029(2) 0.34078(19) 0.0304(6) Uani 1 1 d . . .
C36 C 0.1902(3) 0.6375(2) 0.2570(2) 0.0289(7) Uani 1 1 d . . .
C37 C 0.0978(3) 0.7382(2) 0.2178(2) 0.0293(7) Uani 1 1 d . . .
C38 C 0.0240(3) 0.8303(3) 0.2457(2) 0.0362(8) Uani 1 1 d . . .
H38 H 0.0264 0.8387 0.3052 0.043 Uiso 1 1 d R . .
C39 C -0.0526(3) 0.9090(3) 0.1852(3) 0.0401(8) Uani 1 1 d . . .
H39 H -0.1050 0.9731 0.2035 0.048 Uiso 1 1 d R . .
C40 C -0.0556(3) 0.8959(3) 0.0996(2) 0.0377(8) Uani 1 1 d . . .
H40 H -0.1088 0.9516 0.0590 0.045 Uiso 1 1 d R . .
C41 C 0.0169(3) 0.8043(3) 0.0711(2) 0.0344(8) Uani 1 1 d . . .
H41 H 0.0158 0.7954 0.0114 0.041 Uiso 1 1 d R . .
C42 C 0.0923(3) 0.7260(2) 0.1314(2) 0.0289(7) Uani 1 1 d . . .
C43 C 0.1781(3) 0.6209(2) 0.1225(2) 0.0291(7) Uani 1 1 d . . .
N44 N 0.2366(2) 0.5723(2) 0.20118(18) 0.0291(6) Uani 1 1 d . . .
N45 N 0.1942(2) 0.5797(2) 0.05379(19) 0.0307(6) Uani 1 1 d . . .
C46 C 0.2813(3) 0.4845(2) 0.0466(2) 0.0280(7) Uani 1 1 d . . .
C47 C 0.2984(3) 0.4249(2) -0.0163(2) 0.0300(7) Uani 1 1 d . . .
C48 C 0.4014(3) 0.3390(2) -0.0056(2) 0.0286(7) Uani 1 1 d . . .
C49 C 0.4465(3) 0.3475(2) 0.0643(2) 0.0280(7) Uani 1 1 d . . .
N50 N 0.3707(2) 0.4366(2) 0.09472(19) 0.0289(6) Uani 1 1 d . . .
C51 C 0.5527(3) 0.2849(2) 0.0947(2) 0.0284(7) Uani 1 1 d . . .
H51 H 0.5981 0.2248 0.0683 0.034 Uiso 1 1 d R . .
C52 C 0.5995(3) 0.2968(2) 0.1573(2) 0.0287(7) Uani 1 1 d . . .
C53 C 0.5403(3) 0.3735(3) 0.2119(2) 0.0320(8) Uani 1 1 d . . .
N54 N 0.4892(2) 0.4351(2) 0.2567(2) 0.0389(7) Uani 1 1 d . . .
C55 C 0.7183(3) 0.2290(3) 0.1685(2) 0.0309(7) Uani 1 1 d . . .
O56 O 0.77691(18) 0.15711(18) 0.13112(17) 0.0381(6) Uani 1 1 d . . .
O57 O 0.75559(18) 0.25898(17) 0.22539(16) 0.0361(6) Uani 1 1 d . . .
C58 C 0.8745(3) 0.2035(3) 0.2355(3) 0.0433(9) Uani 1 1 d . . .
H58A H 0.8917 0.2304 0.2772 0.065 Uiso 1 1 d R . .
H58B H 0.8853 0.1242 0.2652 0.065 Uiso 1 1 d R . .
H58C H 0.9256 0.2197 0.1705 0.065 Uiso 1 1 d R . .
C59 C 0.2813(3) 0.0806(3) 0.1418(3) 0.0457(9) Uani 1 1 d . . .
H59A H 0.3394 0.0455 0.0954 0.055 Uiso 1 1 d R . .
H59B H 0.2415 0.1535 0.1042 0.055 Uiso 1 1 d R . .
C60 C 0.1957(3) 0.0109(3) 0.2004(3) 0.0548(10) Uani 1 1 d . . .
H60A H 0.1599 0.0049 0.1569 0.082 Uiso 1 1 d R . .
H60B H 0.2357 -0.0625 0.2373 0.082 Uiso 1 1 d R . .
H60C H 0.1370 0.0466 0.2462 0.082 Uiso 1 1 d R . .
C61 C 0.5334(3) -0.0667(3) 0.1919(3) 0.0476(9) Uani 1 1 d . . .
H61A H 0.4938 -0.0901 0.1635 0.057 Uiso 1 1 d R . .
H61B H 0.5579 -0.1286 0.2483 0.057 Uiso 1 1 d R . .
C62 C 0.6384(3) -0.0373(3) 0.1150(3) 0.0539(10) Uani 1 1 d . . .
H62A H 0.6884 -0.1009 0.0949 0.081 Uiso 1 1 d R . .
H62B H 0.6146 0.0235 0.0577 0.081 Uiso 1 1 d R . .
H62C H 0.6794 -0.0153 0.1434 0.081 Uiso 1 1 d R . .
C63 C 0.2158(3) 0.4514(3) -0.0797(2) 0.0349(8) Uani 1 1 d . . .
H63A H 0.2592 0.4359 -0.1409 0.042 Uiso 1 1 d R . .
H63B H 0.1759 0.5297 -0.0965 0.042 Uiso 1 1 d R . .
C64 C 0.1260(3) 0.3842(3) -0.0284(3) 0.0510(10) Uani 1 1 d . . .
H64A H 0.0750 0.4037 -0.0711 0.076 Uiso 1 1 d R . .
H64B H 0.1656 0.3059 -0.0125 0.076 Uiso 1 1 d R . .
H64C H 0.0815 0.4005 0.0323 0.076 Uiso 1 1 d R . .
C65 C 0.4569(3) 0.2551(3) -0.0597(2) 0.0339(8) Uani 1 1 d . . .
H65A H 0.4023 0.2619 -0.0944 0.041 Uiso 1 1 d R . .
H65B H 0.4704 0.1814 -0.0115 0.041 Uiso 1 1 d R . .
C66 C 0.5710(3) 0.2697(3) -0.1353(2) 0.0394(8) Uani 1 1 d . . .
H66A H 0.6005 0.2140 -0.1676 0.059 Uiso 1 1 d R . .
H66B H 0.5577 0.3427 -0.1847 0.059 Uiso 1 1 d R . .
H66C H 0.6265 0.2613 -0.1009 0.059 Uiso 1 1 d R . .
H24 H 0.417(3) 0.321(3) 0.466(2) 0.046(10) Uiso 1 1 d . . .
H35 H 0.286(3) 0.540(3) 0.349(2) 0.038(10) Uiso 1 1 d . . .
H13 H 0.373(3) 0.196(3) 0.348(3) 0.057(11) Uiso 1 1 d . . .
H50 H 0.370(3) 0.460(3) 0.145(3) 0.047(10) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.034(2) 0.043(2) 0.070(3) -0.0159(19) -0.0110(19) -0.0072(18)
O2 0.0390(14) 0.0441(14) 0.0582(16) -0.0209(13) -0.0143(12) -0.0073(12)
C3 0.037(2) 0.042(2) 0.038(2) -0.0098(17) -0.0044(17) -0.0187(17)
O4 0.0465(15) 0.0630(17) 0.0496(16) -0.0181(13) -0.0213(13) -0.0140(13)
C5 0.038(2) 0.0369(19) 0.0323(19) -0.0105(16) -0.0102(16) -0.0150(16)
C6 0.041(2) 0.0301(19) 0.040(2) -0.0152(16) -0.0108(17) -0.0085(16)
N7 0.0520(19) 0.0331(17) 0.055(2) -0.0179(14) -0.0223(17) -0.0047(14)
C8 0.046(2) 0.042(2) 0.0289(18) -0.0053(16) -0.0115(16) -0.0216(18)
C9 0.043(2) 0.0380(19) 0.0311(19) -0.0099(15) -0.0112(16) -0.0192(17)
C10 0.056(2) 0.042(2) 0.0283(18) -0.0127(16) -0.0040(17) -0.0295(18)
C11 0.045(2) 0.0335(19) 0.037(2) -0.0167(16) -0.0007(17) -0.0210(17)
C12 0.042(2) 0.0298(18) 0.0307(18) -0.0122(15) -0.0018(16) -0.0149(16)
N13 0.0402(17) 0.0323(16) 0.0314(16) -0.0130(13) -0.0071(13) -0.0145(13)
N14 0.0417(17) 0.0283(15) 0.0343(16) -0.0115(12) -0.0059(13) -0.0132(13)
C15 0.0363(19) 0.0273(18) 0.0291(18) -0.0085(14) -0.0026(15) -0.0093(15)
C16 0.039(2) 0.0256(17) 0.0275(18) -0.0055(14) -0.0072(15) -0.0083(15)
C17 0.045(2) 0.0302(19) 0.035(2) -0.0112(15) -0.0069(17) -0.0068(17)
C18 0.036(2) 0.036(2) 0.037(2) -0.0073(16) -0.0046(17) -0.0030(16)
C19 0.035(2) 0.039(2) 0.0347(19) -0.0057(16) -0.0120(16) -0.0045(16)
C20 0.040(2) 0.0334(19) 0.0331(19) -0.0061(15) -0.0122(16) -0.0101(16)
C21 0.0359(19) 0.0252(17) 0.0289(18) -0.0080(14) -0.0061(15) -0.0091(15)
C22 0.0339(18) 0.0264(17) 0.0268(17) -0.0072(14) -0.0077(15) -0.0095(15)
N23 0.0362(16) 0.0282(15) 0.0294(15) -0.0124(12) -0.0075(13) -0.0075(12)
N24 0.0369(16) 0.0279(15) 0.0360(16) -0.0144(13) -0.0154(14) -0.0022(13)
C25 0.0321(18) 0.0324(18) 0.0280(18) -0.0085(15) -0.0078(16) -0.0116(15)
O26 0.0400(13) 0.0368(13) 0.0350(13) -0.0128(10) -0.0149(11) -0.0058(11)
C27 0.0286(17) 0.0297(17) 0.0296(18) -0.0106(14) -0.0055(15) -0.0122(14)
C28 0.0338(19) 0.0374(19) 0.0276(18) -0.0120(15) -0.0085(15) -0.0122(16)
C29 0.0399(19) 0.040(2) 0.0297(18) -0.0164(15) -0.0067(16) -0.0157(16)
C30 0.0385(19) 0.0313(18) 0.0350(19) -0.0155(15) -0.0063(16) -0.0127(15)
C31 0.0322(18) 0.0293(18) 0.0301(18) -0.0113(14) -0.0050(15) -0.0108(15)
N32 0.0290(14) 0.0294(15) 0.0264(14) -0.0110(11) -0.0063(12) -0.0098(12)
C33 0.040(2) 0.0313(19) 0.0346(19) -0.0151(15) -0.0101(16) -0.0086(16)
O34 0.0659(18) 0.0446(15) 0.0573(17) -0.0320(13) -0.0331(14) 0.0179(14)
N35 0.0345(16) 0.0271(15) 0.0322(16) -0.0123(13) -0.0150(13) -0.0015(13)
C36 0.0312(18) 0.0278(17) 0.0308(18) -0.0102(15) -0.0087(15) -0.0088(14)
C37 0.0289(17) 0.0249(17) 0.0326(18) -0.0087(14) -0.0062(15) -0.0074(14)
C38 0.038(2) 0.0327(19) 0.039(2) -0.0139(16) -0.0099(17) -0.0075(16)
C39 0.039(2) 0.0289(19) 0.047(2) -0.0136(16) -0.0116(18) -0.0007(16)
C40 0.0332(19) 0.0337(19) 0.040(2) -0.0087(16) -0.0114(16) -0.0038(16)
C41 0.0352(19) 0.0346(19) 0.0313(19) -0.0090(15) -0.0100(16) -0.0068(16)
C42 0.0298(17) 0.0283(17) 0.0284(17) -0.0096(14) -0.0049(15) -0.0089(14)
C43 0.0312(18) 0.0306(18) 0.0288(18) -0.0086(14) -0.0080(15) -0.0120(15)
N44 0.0323(15) 0.0289(14) 0.0288(15) -0.0107(12) -0.0103(12) -0.0067(12)
N45 0.0309(15) 0.0311(15) 0.0305(15) -0.0110(12) -0.0086(12) -0.0064(12)
C46 0.0276(17) 0.0311(18) 0.0273(17) -0.0101(14) -0.0088(15) -0.0070(15)
C47 0.0345(19) 0.0329(18) 0.0244(17) -0.0066(14) -0.0079(15) -0.0133(15)
C48 0.0357(19) 0.0267(17) 0.0268(17) -0.0085(14) -0.0072(15) -0.0123(15)
C49 0.0327(18) 0.0235(17) 0.0298(18) -0.0110(14) -0.0072(15) -0.0071(14)
N50 0.0332(15) 0.0288(15) 0.0290(15) -0.0126(12) -0.0102(13) -0.0066(12)
C51 0.0330(18) 0.0230(16) 0.0318(18) -0.0124(14) -0.0053(15) -0.0082(14)
C52 0.0317(18) 0.0238(17) 0.0321(18) -0.0114(14) -0.0081(15) -0.0057(14)
C53 0.0339(19) 0.0289(18) 0.0350(19) -0.0090(16) -0.0149(16) -0.0057(15)
N54 0.0423(17) 0.0377(17) 0.0435(17) -0.0189(15) -0.0195(15) -0.0027(14)
C55 0.0344(19) 0.0260(18) 0.0334(19) -0.0100(15) -0.0102(16) -0.0067(15)
O56 0.0355(13) 0.0348(13) 0.0468(14) -0.0201(12) -0.0141(11) -0.0005(11)
O57 0.0336(13) 0.0356(13) 0.0455(14) -0.0201(11) -0.0173(11) -0.0011(10)
C58 0.036(2) 0.048(2) 0.052(2) -0.0210(18) -0.0193(18) -0.0033(17)
C59 0.060(2) 0.052(2) 0.039(2) -0.0192(18) -0.0087(19) -0.028(2)
C60 0.055(2) 0.071(3) 0.057(3) -0.026(2) -0.010(2) -0.033(2)
C61 0.058(2) 0.044(2) 0.050(2) -0.0262(18) -0.0005(19) -0.0217(19)
C62 0.050(2) 0.049(2) 0.063(3) -0.026(2) -0.007(2) -0.0095(19)
C63 0.041(2) 0.0366(19) 0.0314(19) -0.0128(15) -0.0131(16) -0.0091(16)
C64 0.053(2) 0.048(2) 0.059(3) -0.0076(19) -0.029(2) -0.0179(19)
C65 0.039(2) 0.0326(18) 0.0354(19) -0.0157(15) -0.0080(16) -0.0106(15)
C66 0.043(2) 0.038(2) 0.042(2) -0.0193(16) -0.0070(17) -0.0121(17)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.454(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9599 . ?
C1 H1C 0.9600 . ?
O2 C3 1.350(4) . ?
C3 O4 1.207(4) . ?
C3 C5 1.476(4) . ?
C5 C8 1.365(4) . ?
C5 C6 1.432(4) . ?
C6 N7 1.160(4) . ?
C8 C9 1.405(4) . ?
C8 H8 0.9600 . ?
C9 N13 1.379(4) . ?
C9 C10 1.420(4) . ?
C10 C11 1.395(5) . ?
C10 C59 1.498(4) . ?
C11 C12 1.405(4) . ?
C11 C61 1.492(4) . ?
C12 N13 1.368(4) . ?
C12 N14 1.372(4) . ?
N13 H13 0.99(3) . ?
N14 C15 1.303(4) . ?
C15 N23 1.398(4) . ?
C15 C16 1.466(4) . ?
C16 C17 1.380(4) . ?
C16 C21 1.407(4) . ?
C17 C18 1.395(4) . ?
C17 H17 0.9600 . ?
C18 C19 1.386(5) . ?
C18 H18 0.9601 . ?
C19 C20 1.395(4) . ?
C19 H19 0.9601 . ?
C20 C21 1.394(4) . ?
C20 H20 0.9599 . ?
C21 C22 1.493(4) . ?
C22 N23 1.311(4) . ?
C22 N24 1.372(4) . ?
N24 C25 1.367(4) . ?
N24 H24 0.90(3) . ?
C25 O26 1.219(3) . ?
C25 C27 1.499(4) . ?
C27 N32 1.347(3) . ?
C27 C28 1.390(4) . ?
C28 C29 1.384(4) . ?
C28 H28 0.9600 . ?
C29 C30 1.381(4) . ?
C29 H29 0.9600 . ?
C30 C31 1.386(4) . ?
C30 H30 0.9601 . ?
C31 N32 1.341(4) . ?
C31 C33 1.510(4) . ?
C33 O34 1.210(4) . ?
C33 N35 1.368(4) . ?
N35 C36 1.375(4) . ?
N35 H35 0.87(3) . ?
C36 N44 1.317(4) . ?
C36 C37 1.487(4) . ?
C37 C38 1.386(4) . ?
C37 C42 1.403(4) . ?
C38 C39 1.394(4) . ?
C38 H38 0.9600 . ?
C39 C40 1.387(4) . ?
C39 H39 0.9601 . ?
C40 C41 1.380(4) . ?
C40 H40 0.9601 . ?
C41 C42 1.383(4) . ?
C41 H41 0.9600 . ?
C42 C43 1.467(4) . ?
C43 N45 1.294(4) . ?
C43 N44 1.407(4) . ?
N45 C46 1.372(4) . ?
C46 N50 1.364(4) . ?
C46 C47 1.403(4) . ?
C47 C48 1.398(4) . ?
C47 C63 1.504(4) . ?
C48 C49 1.419(4) . ?
C48 C65 1.498(4) . ?
C49 N50 1.377(4) . ?
C49 C51 1.414(4) . ?
N50 H50 0.93(3) . ?
C51 C52 1.361(4) . ?
C51 H51 0.9600 . ?
C52 C53 1.426(4) . ?
C52 C55 1.471(4) . ?
C53 N54 1.158(4) . ?
C55 O56 1.206(3) . ?
C55 O57 1.357(3) . ?
O57 C58 1.445(3) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 C60 1.515(5) . ?
C59 H59A 0.9601 . ?
C59 H59B 0.9600 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C61 C62 1.497(5) . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9601 . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
C63 C64 1.529(4) . ?
C63 H63A 0.9602 . ?
C63 H63B 0.9599 . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 0.9599 . ?
C65 C66 1.530(4) . ?
C65 H65A 0.9599 . ?
C65 H65B 0.9600 . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9599 . ?
C66 H66C 0.9601 . ?

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
O2 C1 H1A 109.9 . . ?
O2 C1 H1B 110.0 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 108.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 O2 C1 116.2(3) . . ?
O4 C3 O2 124.4(3) . . ?
O4 C3 C5 124.3(3) . . ?
O2 C3 C5 111.3(3) . . ?
C8 C5 C6 122.1(3) . . ?
C8 C5 C3 119.8(3) . . ?
C6 C5 C3 118.1(3) . . ?
N7 C6 C5 178.6(3) . . ?
C5 C8 C9 131.0(3) . . ?
C5 C8 H8 114.3 . . ?
C9 C8 H8 114.7 . . ?
N13 C9 C8 123.9(3) . . ?
N13 C9 C10 107.0(3) . . ?
C8 C9 C10 129.1(3) . . ?
C11 C10 C9 107.9(3) . . ?
C11 C10 C59 127.1(3) . . ?
C9 C10 C59 125.0(3) . . ?
C10 C11 C12 107.0(3) . . ?
C10 C11 C61 128.8(3) . . ?
C12 C11 C61 124.1(3) . . ?
N13 C12 N14 126.1(3) . . ?
N13 C12 C11 108.6(3) . . ?
N14 C12 C11 125.2(3) . . ?
C12 N13 C9 109.4(3) . . ?
C12 N13 H13 121(2) . . ?
C9 N13 H13 129(2) . . ?
C15 N14 C12 120.6(3) . . ?
N14 C15 N23 125.7(3) . . ?
N14 C15 C16 125.0(3) . . ?
N23 C15 C16 109.3(3) . . ?
C17 C16 C21 121.6(3) . . ?
C17 C16 C15 131.6(3) . . ?
C21 C16 C15 106.8(3) . . ?
C16 C17 C18 118.1(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 121.6 . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 122.5(3) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 H19 118.7 . . ?
C21 C20 C19 117.0(3) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 122.6 . . ?
C20 C21 C16 120.5(3) . . ?
C20 C21 C22 135.7(3) . . ?
C16 C21 C22 103.8(2) . . ?
N23 C22 N24 115.8(3) . . ?
N23 C22 C21 112.5(3) . . ?
N24 C22 C21 131.5(3) . . ?
C22 N23 C15 107.6(2) . . ?
C25 N24 C22 131.1(3) . . ?
C25 N24 H24 114(2) . . ?
C22 N24 H24 115(2) . . ?
O26 C25 N24 124.7(3) . . ?
O26 C25 C27 121.3(3) . . ?
N24 C25 C27 113.9(3) . . ?
N32 C27 C28 123.2(3) . . ?
N32 C27 C25 117.3(2) . . ?
C28 C27 C25 119.4(3) . . ?
C29 C28 C27 118.5(3) . . ?
C29 C28 H28 120.6 . . ?
C27 C28 H28 120.9 . . ?
C28 C29 C30 119.1(3) . . ?
C28 C29 H29 120.6 . . ?
C30 C29 H29 120.3 . . ?
C29 C30 C31 118.5(3) . . ?
C29 C30 H30 121.2 . . ?
C31 C30 H30 120.3 . . ?
N32 C31 C30 123.7(3) . . ?
N32 C31 C33 117.7(3) . . ?
C30 C31 C33 118.6(3) . . ?
C31 N32 C27 116.9(2) . . ?
O34 C33 N35 125.4(3) . . ?
O34 C33 C31 120.3(3) . . ?
N35 C33 C31 114.4(3) . . ?
C33 N35 C36 130.9(3) . . ?
C33 N35 H35 116(2) . . ?
C36 N35 H35 113(2) . . ?
N44 C36 N35 116.4(3) . . ?
N44 C36 C37 113.0(3) . . ?
N35 C36 C37 130.6(3) . . ?
C38 C37 C42 119.6(3) . . ?
C38 C37 C36 136.6(3) . . ?
C42 C37 C36 103.8(2) . . ?
C37 C38 C39 118.1(3) . . ?
C37 C38 H38 120.1 . . ?
C39 C38 H38 121.8 . . ?
C40 C39 C38 121.3(3) . . ?
C40 C39 H39 119.2 . . ?
C38 C39 H39 119.5 . . ?
C41 C40 C39 121.2(3) . . ?
C41 C40 H40 119.1 . . ?
C39 C40 H40 119.7 . . ?
C40 C41 C42 117.5(3) . . ?
C40 C41 H41 121.5 . . ?
C42 C41 H41 121.0 . . ?
C41 C42 C37 122.3(3) . . ?
C41 C42 C43 130.7(3) . . ?
C37 C42 C43 107.1(2) . . ?
N45 C43 N44 126.3(3) . . ?
N45 C43 C42 124.5(3) . . ?
N44 C43 C42 109.1(2) . . ?
C36 N44 C43 106.9(2) . . ?
C43 N45 C46 121.0(2) . . ?
N50 C46 N45 125.2(3) . . ?
N50 C46 C47 108.5(3) . . ?
N45 C46 C47 126.1(3) . . ?
C48 C47 C46 107.3(2) . . ?
C48 C47 C63 128.7(3) . . ?
C46 C47 C63 124.0(3) . . ?
C47 C48 C49 107.3(3) . . ?
C47 C48 C65 126.8(3) . . ?
C49 C48 C65 125.8(3) . . ?
N50 C49 C51 123.7(2) . . ?
N50 C49 C48 107.3(3) . . ?
C51 C49 C48 128.8(3) . . ?
C46 N50 C49 109.5(2) . . ?
C46 N50 H50 121(2) . . ?
C49 N50 H50 130(2) . . ?
C52 C51 C49 129.1(3) . . ?
C52 C51 H51 115.1 . . ?
C49 C51 H51 115.8 . . ?
C51 C52 C53 123.5(3) . . ?
C51 C52 C55 118.8(3) . . ?
C53 C52 C55 117.7(3) . . ?
N54 C53 C52 178.0(3) . . ?
O56 C55 O57 123.6(3) . . ?
O56 C55 C52 125.3(3) . . ?
O57 C55 C52 111.1(3) . . ?
C55 O57 C58 116.1(2) . . ?
O57 C58 H58A 109.3 . . ?
O57 C58 H58B 109.9 . . ?
H58A C58 H58B 109.5 . . ?
O57 C58 H58C 109.2 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C10 C59 C60 113.9(3) . . ?
C10 C59 H59A 108.4 . . ?
C60 C59 H59A 108.0 . . ?
C10 C59 H59B 109.2 . . ?
C60 C59 H59B 109.2 . . ?
H59A C59 H59B 108.1 . . ?
C59 C60 H60A 111.3 . . ?
C59 C60 H60B 109.2 . . ?
H60A C60 H60B 109.5 . . ?
C59 C60 H60C 107.9 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C11 C61 C62 114.4(3) . . ?
C11 C61 H61A 108.2 . . ?
C62 C61 H61A 108.6 . . ?
C11 C61 H61B 108.6 . . ?
C62 C61 H61B 109.2 . . ?
H61A C61 H61B 107.8 . . ?
C61 C62 H62A 109.8 . . ?
C61 C62 H62B 109.6 . . ?
H62A C62 H62B 109.5 . . ?
C61 C62 H62C 109.0 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C47 C63 C64 113.3(3) . . ?
C47 C63 H63A 109.2 . . ?
C64 C63 H63A 108.3 . . ?
C47 C63 H63B 108.9 . . ?
C64 C63 H63B 109.0 . . ?
H63A C63 H63B 107.9 . . ?
C63 C64 H64A 110.7 . . ?
C63 C64 H64B 109.3 . . ?
H64A C64 H64B 109.5 . . ?
C63 C64 H64C 108.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C48 C65 C66 114.3(3) . . ?
C48 C65 H65A 107.6 . . ?
C66 C65 H65A 108.8 . . ?
C48 C65 H65B 108.9 . . ?
C66 C65 H65B 109.3 . . ?
H65A C65 H65B 107.8 . . ?
C65 C66 H66A 109.5 . . ?
C65 C66 H66B 109.7 . . ?
H66A C66 H66B 109.5 . . ?
C65 C66 H66C 109.2 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 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
C1 O2 C3 O4 -3.4(5) . . . . ?
C1 O2 C3 C5 176.4(3) . . . . ?
O4 C3 C5 C8 5.7(5) . . . . ?
O2 C3 C5 C8 -174.1(3) . . . . ?
O4 C3 C5 C6 -176.7(3) . . . . ?
O2 C3 C5 C6 3.5(4) . . . . ?
C8 C5 C6 N7 -41(16) . . . . ?
C3 C5 C6 N7 142(15) . . . . ?
C6 C5 C8 C9 0.4(6) . . . . ?
C3 C5 C8 C9 177.9(3) . . . . ?
C5 C8 C9 N13 -3.0(6) . . . . ?
C5 C8 C9 C10 178.7(3) . . . . ?
N13 C9 C10 C11 -0.4(4) . . . . ?
C8 C9 C10 C11 178.2(3) . . . . ?
N13 C9 C10 C59 178.0(3) . . . . ?
C8 C9 C10 C59 -3.4(6) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C59 C10 C11 C12 -178.1(3) . . . . ?
C9 C10 C11 C61 -178.6(3) . . . . ?
C59 C10 C11 C61 3.0(6) . . . . ?
C10 C11 C12 N13 -0.1(4) . . . . ?
C61 C11 C12 N13 178.9(3) . . . . ?
C10 C11 C12 N14 179.0(3) . . . . ?
C61 C11 C12 N14 -2.0(5) . . . . ?
N14 C12 N13 C9 -179.3(3) . . . . ?
C11 C12 N13 C9 -0.2(4) . . . . ?
C8 C9 N13 C12 -178.3(3) . . . . ?
C10 C9 N13 C12 0.3(3) . . . . ?
N13 C12 N14 C15 -4.4(5) . . . . ?
C11 C12 N14 C15 176.6(3) . . . . ?
C12 N14 C15 N23 -0.3(5) . . . . ?
C12 N14 C15 C16 -178.8(3) . . . . ?
N14 C15 C16 C17 -0.5(6) . . . . ?
N23 C15 C16 C17 -179.2(3) . . . . ?
N14 C15 C16 C21 179.2(3) . . . . ?
N23 C15 C16 C21 0.5(3) . . . . ?
C21 C16 C17 C18 -2.2(5) . . . . ?
C15 C16 C17 C18 177.4(3) . . . . ?
C16 C17 C18 C19 1.4(5) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C21 -1.1(5) . . . . ?
C19 C20 C21 C16 0.3(5) . . . . ?
C19 C20 C21 C22 -177.3(3) . . . . ?
C17 C16 C21 C20 1.4(5) . . . . ?
C15 C16 C21 C20 -178.3(3) . . . . ?
C17 C16 C21 C22 179.6(3) . . . . ?
C15 C16 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 N23 177.4(3) . . . . ?
C16 C21 C22 N23 -0.4(3) . . . . ?
C20 C21 C22 N24 1.3(6) . . . . ?
C16 C21 C22 N24 -176.5(3) . . . . ?
N24 C22 N23 C15 177.5(3) . . . . ?
C21 C22 N23 C15 0.7(3) . . . . ?
N14 C15 N23 C22 -179.4(3) . . . . ?
C16 C15 N23 C22 -0.8(3) . . . . ?
N23 C22 N24 C25 171.9(3) . . . . ?
C21 C22 N24 C25 -12.1(6) . . . . ?
C22 N24 C25 O26 -4.1(5) . . . . ?
C22 N24 C25 C27 176.2(3) . . . . ?
O26 C25 C27 N32 168.1(3) . . . . ?
N24 C25 C27 N32 -12.1(4) . . . . ?
O26 C25 C27 C28 -10.1(4) . . . . ?
N24 C25 C27 C28 169.7(3) . . . . ?
N32 C27 C28 C29 1.6(5) . . . . ?
C25 C27 C28 C29 179.7(3) . . . . ?
C27 C28 C29 C30 -0.3(4) . . . . ?
C28 C29 C30 C31 -1.2(5) . . . . ?
C29 C30 C31 N32 1.6(5) . . . . ?
C29 C30 C31 C33 -176.8(3) . . . . ?
C30 C31 N32 C27 -0.4(4) . . . . ?
C33 C31 N32 C27 178.0(3) . . . . ?
C28 C27 N32 C31 -1.2(4) . . . . ?
C25 C27 N32 C31 -179.4(3) . . . . ?
N32 C31 C33 O34 177.8(3) . . . . ?
C30 C31 C33 O34 -3.7(5) . . . . ?
N32 C31 C33 N35 -2.7(4) . . . . ?
C30 C31 C33 N35 175.8(3) . . . . ?
O34 C33 N35 C36 -2.4(6) . . . . ?
C31 C33 N35 C36 178.1(3) . . . . ?
C33 N35 C36 N44 179.8(3) . . . . ?
C33 N35 C36 C37 -0.6(5) . . . . ?
N44 C36 C37 C38 -179.9(3) . . . . ?
N35 C36 C37 C38 0.5(6) . . . . ?
N44 C36 C37 C42 0.6(3) . . . . ?
N35 C36 C37 C42 -179.0(3) . . . . ?
C42 C37 C38 C39 -0.9(5) . . . . ?
C36 C37 C38 C39 179.7(3) . . . . ?
C37 C38 C39 C40 0.2(5) . . . . ?
C38 C39 C40 C41 0.2(5) . . . . ?
C39 C40 C41 C42 0.2(5) . . . . ?
C40 C41 C42 C37 -0.9(5) . . . . ?
C40 C41 C42 C43 179.4(3) . . . . ?
C38 C37 C42 C41 1.3(5) . . . . ?
C36 C37 C42 C41 -179.1(3) . . . . ?
C38 C37 C42 C43 -179.0(3) . . . . ?
C36 C37 C42 C43 0.6(3) . . . . ?
C41 C42 C43 N45 -3.4(5) . . . . ?
C37 C42 C43 N45 176.9(3) . . . . ?
C41 C42 C43 N44 178.1(3) . . . . ?
C37 C42 C43 N44 -1.6(3) . . . . ?
N35 C36 N44 C43 178.0(3) . . . . ?
C37 C36 N44 C43 -1.6(3) . . . . ?
N45 C43 N44 C36 -176.5(3) . . . . ?
C42 C43 N44 C36 2.0(3) . . . . ?
N44 C43 N45 C46 -5.9(5) . . . . ?
C42 C43 N45 C46 175.8(3) . . . . ?
C43 N45 C46 N50 -13.0(5) . . . . ?
C43 N45 C46 C47 171.9(3) . . . . ?
N50 C46 C47 C48 -0.2(3) . . . . ?
N45 C46 C47 C48 175.6(3) . . . . ?
N50 C46 C47 C63 178.4(3) . . . . ?
N45 C46 C47 C63 -5.8(5) . . . . ?
C46 C47 C48 C49 -0.1(3) . . . . ?
C63 C47 C48 C49 -178.6(3) . . . . ?
C46 C47 C48 C65 -178.4(3) . . . . ?
C63 C47 C48 C65 3.2(5) . . . . ?
C47 C48 C49 N50 0.4(3) . . . . ?
C65 C48 C49 N50 178.7(3) . . . . ?
C47 C48 C49 C51 -175.1(3) . . . . ?
C65 C48 C49 C51 3.2(5) . . . . ?
N45 C46 N50 C49 -175.4(3) . . . . ?
C47 C46 N50 C49 0.5(3) . . . . ?
C51 C49 N50 C46 175.2(3) . . . . ?
C48 C49 N50 C46 -0.5(3) . . . . ?
N50 C49 C51 C52 1.0(5) . . . . ?
C48 C49 C51 C52 175.8(3) . . . . ?
C49 C51 C52 C53 5.6(5) . . . . ?
C49 C51 C52 C55 -173.1(3) . . . . ?
C51 C52 C53 N54 39(10) . . . . ?
C55 C52 C53 N54 -142(10) . . . . ?
C51 C52 C55 O56 -5.0(5) . . . . ?
C53 C52 C55 O56 176.2(3) . . . . ?
C51 C52 C55 O57 173.9(3) . . . . ?
C53 C52 C55 O57 -4.9(4) . . . . ?
O56 C55 O57 C58 3.2(4) . . . . ?
C52 C55 O57 C58 -175.7(3) . . . . ?
C11 C10 C59 C60 94.6(4) . . . . ?
C9 C10 C59 C60 -83.5(4) . . . . ?
C10 C11 C61 C62 105.5(4) . . . . ?
C12 C11 C61 C62 -73.3(4) . . . . ?
C48 C47 C63 C64 85.0(4) . . . . ?
C46 C47 C63 C64 -93.3(4) . . . . ?
C47 C48 C65 C66 110.7(3) . . . . ?
C49 C48 C65 C66 -67.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N24 H24 N32 0.90(3) 2.21(3) 2.685(4) 112(2) .
N24 H24 N7 0.90(3) 2.42(3) 3.228(4) 149(3) .
N35 H35 N32 0.87(3) 2.26(3) 2.699(3) 111(3) .
N13 H13 N23 0.99(3) 1.95(3) 2.627(3) 124(3) .
N13 H13 N7 0.99(3) 2.47(4) 3.294(4) 141(3) .
N50 H50 N44 0.93(3) 2.01(3) 2.668(4) 125(3) .
N50 H50 N54 0.93(3) 2.48(3) 3.266(4) 142(3) .

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.056

# Attachment 'Helix_CC_4.cif'

data_gdp22
_database_code_depnum_ccdc_archive 'CCDC 299138'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H17 N3 O2'
_chemical_formula_weight         247.30

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           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   10.5504(10)
_cell_length_b                   9.0899(8)
_cell_length_c                   13.5949(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.867(4)
_cell_angle_gamma                90.00
_cell_volume                     1294.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2850
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.088
_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      153(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  'Nonius Kappa CCD'
_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            3999
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_av_sigmaI/netI    0.1147
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2273
_reflns_number_gt                1365
_reflns_threshold_expression     >2sigma(I)

_publ_section_references         
;
Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C.,
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97.
(1999) J. Appl. Cryst. 32, 115-119.

Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology,
276, Macromolecular Crystallography, part A, 307-326, C. W. Carter,
Jr. and R. M. Sweets, Eds., Academic Press.

Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens
Analytical X-ray Instruments, Inc., Madison, WI, USA.

;
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_reduction        
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C.,
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.02P)^2^+2.5P] 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         2273
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1945
_refine_ls_R_factor_gt           0.1189
_refine_ls_wR_factor_ref         0.1888
_refine_ls_wR_factor_gt          0.1647
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_restrained_S_all      1.252
_refine_ls_shift/su_max          0.007
_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 0.6519(3) 0.0694(4) 0.3329(3) 0.0426(11) Uani 1 1 d . . .
O2 O 0.8304(3) 0.0608(4) 0.4409(2) 0.0332(9) Uani 1 1 d . . .
N1 N 0.4953(4) 0.3646(5) 0.6292(3) 0.0323(12) Uani 1 1 d . . .
N2 N 0.4074(4) 0.5118(5) 0.7465(3) 0.0410(13) Uani 1 1 d . . .
H2NA H 0.4768 0.5025 0.7889 0.049 Uiso 1 1 d R . .
H2NB H 0.3428 0.5644 0.7624 0.049 Uiso 1 1 d R . .
N3 N 0.7893(4) 0.2185(5) 0.6617(3) 0.0381(12) Uani 1 1 d . . .
C1 C 0.4001(5) 0.4465(6) 0.6582(4) 0.0305(13) Uani 1 1 d . . .
C2 C 0.2972(4) 0.4545(6) 0.5808(4) 0.0319(13) Uani 1 1 d . . .
C3 C 0.3349(5) 0.3776(6) 0.5021(4) 0.0345(14) Uani 1 1 d . . .
C4 C 0.4593(5) 0.3172(6) 0.5299(4) 0.0357(14) Uani 1 1 d . . .
C5 C 0.5305(5) 0.2346(6) 0.4731(4) 0.0359(15) Uani 1 1 d . . .
H5 H 0.484(5) 0.212(6) 0.400(4) 0.07(2) Uiso 1 1 d . . .
C6 C 0.6538(4) 0.1761(6) 0.4926(3) 0.0278(13) Uani 1 1 d . . .
C7 C 0.7071(5) 0.0978(6) 0.4150(4) 0.0327(13) Uani 1 1 d . . .
C8 C 0.8908(5) -0.0146(6) 0.3647(4) 0.0444(16) Uani 1 1 d . . .
H8A H 0.8426 -0.1040 0.3446 0.067 Uiso 1 1 calc R . .
H8B H 0.9784 -0.0409 0.3908 0.067 Uiso 1 1 calc R . .
H8C H 0.8920 0.0503 0.3073 0.067 Uiso 1 1 calc R . .
C9 C 0.7318(5) 0.1986(6) 0.5847(4) 0.0283(13) Uani 1 1 d . . .
C10 C 0.1745(4) 0.5355(6) 0.5894(4) 0.0336(14) Uani 1 1 d . . .
H10A H 0.1317 0.5556 0.5245 0.040 Uiso 1 1 d R . .
H10B H 0.1949 0.6279 0.6217 0.040 Uiso 1 1 d R . .
C11 C 0.0852(5) 0.4516(7) 0.6494(4) 0.0432(16) Uani 1 1 d . . .
H11A H 0.0583 0.3600 0.6151 0.065 Uiso 1 1 calc R . .
H11B H 0.0100 0.5121 0.6567 0.065 Uiso 1 1 calc R . .
H11C H 0.1298 0.4287 0.7150 0.065 Uiso 1 1 calc R . .
C12 C 0.2591(5) 0.3605(6) 0.4000(4) 0.0407(15) Uani 1 1 d . . .
H12A H 0.3150 0.3364 0.3516 0.049 Uiso 1 1 d R . .
H12B H 0.2172 0.4518 0.3812 0.049 Uiso 1 1 d R . .
C13 C 0.1598(6) 0.2441(7) 0.4015(4) 0.0548(18) Uani 1 1 d . . .
H13A H 0.2012 0.1484 0.4143 0.082 Uiso 1 1 calc R . .
H13B H 0.1067 0.2416 0.3372 0.082 Uiso 1 1 calc R . .
H13C H 0.1063 0.2659 0.4538 0.082 Uiso 1 1 calc R . .
H1N H 0.563(5) 0.357(7) 0.663(4) 0.06(2) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.031(2) 0.065(3) 0.032(2) -0.011(2) 0.0056(18) 0.005(2)
O2 0.0246(19) 0.042(2) 0.034(2) -0.0018(19) 0.0085(16) 0.0084(18)
N1 0.020(3) 0.045(3) 0.032(3) 0.000(2) 0.005(2) 0.007(2)
N2 0.026(2) 0.060(3) 0.035(3) -0.019(3) -0.004(2) 0.009(2)
N3 0.035(3) 0.047(3) 0.033(3) 0.005(2) 0.007(2) 0.007(2)
C1 0.023(3) 0.036(3) 0.034(3) -0.003(3) 0.009(2) 0.002(3)
C2 0.020(3) 0.048(4) 0.028(3) 0.001(3) 0.002(2) 0.006(3)
C3 0.023(3) 0.054(4) 0.027(3) -0.003(3) 0.005(2) 0.009(3)
C4 0.030(3) 0.047(4) 0.029(3) -0.006(3) -0.001(2) 0.002(3)
C5 0.021(3) 0.049(4) 0.038(4) -0.008(3) 0.007(3) 0.006(3)
C6 0.022(3) 0.036(3) 0.025(3) 0.000(3) 0.004(2) 0.003(2)
C7 0.020(3) 0.040(4) 0.039(3) 0.002(3) 0.009(2) 0.004(3)
C8 0.036(3) 0.056(4) 0.044(3) -0.007(3) 0.016(3) 0.017(3)
C9 0.024(3) 0.032(3) 0.033(3) 0.010(3) 0.020(3) 0.009(2)
C10 0.021(3) 0.050(4) 0.030(3) 0.005(3) 0.001(2) 0.009(3)
C11 0.029(3) 0.056(4) 0.046(3) 0.012(3) 0.013(3) 0.009(3)
C12 0.022(3) 0.051(4) 0.048(4) 0.007(3) 0.004(3) 0.005(3)
C13 0.078(5) 0.037(4) 0.049(4) -0.002(3) 0.006(3) -0.002(4)

_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 C7 1.223(6) . ?
O2 C7 1.349(5) . ?
O2 C8 1.450(6) . ?
N1 C1 1.346(6) . ?
N1 C4 1.425(6) . ?
N1 H1N 0.81(6) . ?
N2 C1 1.334(6) . ?
N2 H2NA 0.8800 . ?
N2 H2NB 0.8800 . ?
N3 C9 1.159(6) . ?
C1 C2 1.421(6) . ?
C2 C3 1.376(7) . ?
C2 C10 1.507(6) . ?
C3 C4 1.431(7) . ?
C3 C12 1.524(7) . ?
C4 C5 1.365(7) . ?
C5 C6 1.401(7) . ?
C5 H5 1.07(6) . ?
C6 C9 1.429(7) . ?
C6 C7 1.441(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 C11 1.522(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.491(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C7 O2 C8 115.1(4) . . ?
C1 N1 C4 108.7(4) . . ?
C1 N1 H1N 122(4) . . ?
C4 N1 H1N 129(4) . . ?
C1 N2 H2NA 120.0 . . ?
C1 N2 H2NB 120.0 . . ?
H2NA N2 H2NB 120.0 . . ?
N2 C1 N1 123.0(5) . . ?
N2 C1 C2 126.9(5) . . ?
N1 C1 C2 110.0(5) . . ?
C3 C2 C1 106.5(4) . . ?
C3 C2 C10 129.8(4) . . ?
C1 C2 C10 123.7(4) . . ?
C2 C3 C4 109.3(4) . . ?
C2 C3 C12 126.2(5) . . ?
C4 C3 C12 124.5(5) . . ?
C5 C4 N1 126.9(5) . . ?
C5 C4 C3 127.7(5) . . ?
N1 C4 C3 105.4(4) . . ?
C4 C5 C6 131.6(5) . . ?
C4 C5 H5 114(3) . . ?
C6 C5 H5 114(3) . . ?
C5 C6 C9 122.4(5) . . ?
C5 C6 C7 119.0(4) . . ?
C9 C6 C7 118.5(4) . . ?
O1 C7 O2 121.6(5) . . ?
O1 C7 C6 125.9(5) . . ?
O2 C7 C6 112.4(4) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C6 176.4(5) . . ?
C2 C10 C11 112.9(4) . . ?
C2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C2 C10 H10B 108.4 . . ?
C11 C10 H10B 108.2 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C3 110.7(5) . . ?
C13 C12 H12A 109.7 . . ?
C3 C12 H12A 110.4 . . ?
C13 C12 H12B 108.3 . . ?
C3 C12 H12B 109.2 . . ?
H12A C12 H12B 108.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C4 N1 C1 N2 -177.2(5) . . . . ?
C4 N1 C1 C2 1.1(6) . . . . ?
N2 C1 C2 C3 176.5(5) . . . . ?
N1 C1 C2 C3 -1.7(7) . . . . ?
N2 C1 C2 C10 -2.9(9) . . . . ?
N1 C1 C2 C10 178.8(5) . . . . ?
C1 C2 C3 C4 1.7(7) . . . . ?
C10 C2 C3 C4 -178.9(5) . . . . ?
C1 C2 C3 C12 -177.1(5) . . . . ?
C10 C2 C3 C12 2.3(10) . . . . ?
C1 N1 C4 C5 178.5(6) . . . . ?
C1 N1 C4 C3 0.0(6) . . . . ?
C2 C3 C4 C5 -179.6(6) . . . . ?
C12 C3 C4 C5 -0.8(10) . . . . ?
C2 C3 C4 N1 -1.0(6) . . . . ?
C12 C3 C4 N1 177.7(5) . . . . ?
N1 C4 C5 C6 -1.0(11) . . . . ?
C3 C4 C5 C6 177.3(6) . . . . ?
C4 C5 C6 C9 -0.8(10) . . . . ?
C4 C5 C6 C7 -177.0(6) . . . . ?
C8 O2 C7 O1 -0.2(7) . . . . ?
C8 O2 C7 C6 -178.3(4) . . . . ?
C5 C6 C7 O1 -4.3(8) . . . . ?
C9 C6 C7 O1 179.4(5) . . . . ?
C5 C6 C7 O2 173.7(5) . . . . ?
C9 C6 C7 O2 -2.6(7) . . . . ?
C5 C6 C9 N3 20(10) . . . . ?
C7 C6 C9 N3 -163(9) . . . . ?
C3 C2 C10 C11 103.6(7) . . . . ?
C1 C2 C10 C11 -77.1(7) . . . . ?
C2 C3 C12 C13 -80.3(7) . . . . ?
C4 C3 C12 C13 101.1(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2NA O1 0.88 1.98 2.803(5) 154.3 4_566
N1 H1N O1 0.81(6) 2.48(6) 3.108(6) 136(5) 4_566
N1 H1N N3 0.81(6) 2.70(6) 3.355(6) 140(5) .
N2 H2NB N3 0.88 2.31 3.165(6) 165.2 2_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.061