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


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       deba_h76@yahoo.com
_publ_contact_author_name        'DEBASISH HALDAR '
loop_
_publ_author_name
'Suman Maity'
'Sibaprasad Maity'
'Poulami Jana'
'Debashis Haldar'

data_sm
_database_code_depnum_ccdc_archive 'CCDC 832142'
#TrackingRef '- gaba-aib-ecp.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H37 N3 O6'
_chemical_formula_sum            'C20 H37 N3 O6'
_chemical_formula_weight         415.53

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                   9.350(2)
_cell_length_b                   9.826(2)
_cell_length_c                   26.846(7)
_cell_angle_alpha                80.603(5)
_cell_angle_beta                 86.257(5)
_cell_angle_gamma                75.615(5)
_cell_volume                     2356.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5662
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      23.29

_exptl_crystal_description       blocked
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.372
_exptl_crystal_size_min          0.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'SADABS v.2.03 (Bruker, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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            29853
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_sigmaI/netI    0.0724
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.10
_reflns_number_total             8389
_reflns_number_gt                5470
_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^)+(0.1057P)^2^+10.2332P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0095(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         8192
_refine_ls_number_parameters     527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1415
_refine_ls_R_factor_gt           0.0998
_refine_ls_wR_factor_ref         0.2779
_refine_ls_wR_factor_gt          0.2467
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.9184(3) 0.9981(3) 0.12522(12) 0.0231(7) Uani 1 1 d . . .
N1 N 0.9194(4) 0.8062(4) 0.18134(15) 0.0264(9) Uani 1 1 d . . .
H1A H 1.0095 0.8085 0.1849 0.032 Uiso 1 1 calc R . .
C1 C 0.7328(6) 1.2217(6) 0.10019(19) 0.0324(12) Uani 1 1 d . . .
H1B H 0.7645 1.2604 0.1270 0.049 Uiso 1 1 calc R . .
H1C H 0.6524 1.1794 0.1122 0.049 Uiso 1 1 calc R . .
H1D H 0.7008 1.2962 0.0725 0.049 Uiso 1 1 calc R . .
O2 O 0.7069(3) 0.9187(3) 0.13950(12) 0.0247(7) Uani 1 1 d . . .
N2 N 0.4637(4) 0.9249(4) 0.22945(14) 0.0192(8) Uani 1 1 d . . .
H2A H 0.4907 1.0035 0.2229 0.023 Uiso 1 1 calc R . .
C2 C 0.8166(6) 1.0431(6) 0.03976(18) 0.0304(11) Uani 1 1 d . . .
H2B H 0.8996 0.9728 0.0296 0.046 Uiso 1 1 calc R . .
H2C H 0.7853 1.1161 0.0115 0.046 Uiso 1 1 calc R . .
H2D H 0.7370 0.9993 0.0513 0.046 Uiso 1 1 calc R . .
O3 O 0.5264(3) 0.6931(3) 0.26506(13) 0.0252(8) Uani 1 1 d . . .
N3 N 0.4573(4) 0.7855(4) 0.14702(14) 0.0237(9) Uani 1 1 d . . .
H3A H 0.5235 0.8302 0.1503 0.028 Uiso 1 1 calc R . .
C3 C 0.8611(5) 1.1088(5) 0.08250(17) 0.0238(10) Uani 1 1 d . . .
O4 O 0.2372(3) 0.7429(4) 0.17567(13) 0.0269(8) Uani 1 1 d . . .
C4 C 0.9936(6) 1.1703(6) 0.06643(19) 0.0316(12) Uani 1 1 d . . .
H4A H 1.0729 1.0979 0.0554 0.047 Uiso 1 1 calc R . .
H4B H 1.0246 1.2042 0.0945 0.047 Uiso 1 1 calc R . .
H4C H 0.9670 1.2476 0.0392 0.047 Uiso 1 1 calc R . .
O5 O 0.8025(4) 0.4105(4) -0.02862(15) 0.0484(11) Uani 1 1 d . . .
C5 C 0.8362(5) 0.9080(5) 0.14799(17) 0.0195(10) Uani 1 1 d . . .
O6 O 0.9117(4) 0.5267(4) -0.09189(13) 0.0353(9) Uani 1 1 d . . .
C6 C 0.8636(5) 0.6925(5) 0.21163(19) 0.0257(11) Uani 1 1 d . . .
H6A H 0.9363 0.6033 0.2107 0.031 Uiso 1 1 calc R . .
H6B H 0.7745 0.6858 0.1966 0.031 Uiso 1 1 calc R . .
C7 C 0.8291(5) 0.7127(5) 0.26624(19) 0.0276(11) Uani 1 1 d . . .
H7A H 0.9150 0.7290 0.2805 0.033 Uiso 1 1 calc R . .
H7B H 0.8092 0.6261 0.2851 0.033 Uiso 1 1 calc R . .
C8 C 0.6967(5) 0.8368(5) 0.27236(18) 0.0238(10) Uani 1 1 d . . .
H8A H 0.6856 0.8504 0.3075 0.029 Uiso 1 1 calc R . .
H8B H 0.7148 0.9229 0.2525 0.029 Uiso 1 1 calc R . .
C9 C 0.5553(5) 0.8112(5) 0.25563(17) 0.0205(10) Uani 1 1 d . . .
C10 C 0.3197(5) 0.9205(5) 0.21159(17) 0.0218(10) Uani 1 1 d . . .
C11 C 0.2569(6) 1.0620(5) 0.1779(2) 0.0344(12) Uani 1 1 d . . .
H11A H 0.2431 1.1384 0.1973 0.052 Uiso 1 1 calc R . .
H11B H 0.1638 1.0605 0.1652 0.052 Uiso 1 1 calc R . .
H11C H 0.3245 1.0757 0.1502 0.052 Uiso 1 1 calc R . .
C12 C 0.2150(5) 0.8972(6) 0.2565(2) 0.0335(12) Uani 1 1 d . . .
H12A H 0.2058 0.9706 0.2770 0.050 Uiso 1 1 calc R . .
H12B H 0.2536 0.8063 0.2764 0.050 Uiso 1 1 calc R . .
H12C H 0.1197 0.8999 0.2445 0.050 Uiso 1 1 calc R . .
C13 C 0.3381(5) 0.8048(5) 0.17748(17) 0.0205(10) Uani 1 1 d . . .
C14 C 0.4819(5) 0.6925(5) 0.10840(18) 0.0266(11) Uani 1 1 d . . .
H14A H 0.3899 0.6695 0.1027 0.032 Uiso 1 1 calc R . .
H14B H 0.5525 0.6044 0.1204 0.032 Uiso 1 1 calc R . .
C15 C 0.5394(5) 0.7608(5) 0.05914(18) 0.0250(10) Uani 1 1 d . . .
H15A H 0.6302 0.7858 0.0651 0.030 Uiso 1 1 calc R . .
H15B H 0.4678 0.8478 0.0468 0.030 Uiso 1 1 calc R . .
C16 C 0.5690(5) 0.6633(5) 0.01866(17) 0.0236(10) Uani 1 1 d . . .
H16A H 0.6380 0.5750 0.0315 0.028 Uiso 1 1 calc R . .
H16B H 0.4774 0.6408 0.0120 0.028 Uiso 1 1 calc R . .
C17 C 0.6318(6) 0.7293(5) -0.03087(18) 0.0275(11) Uani 1 1 d . . .
H17A H 0.7227 0.7527 -0.0240 0.033 Uiso 1 1 calc R . .
H17B H 0.5623 0.8172 -0.0437 0.033 Uiso 1 1 calc R . .
C18 C 0.6639(6) 0.6326(5) -0.07200(18) 0.0292(11) Uani 1 1 d . . .
H18A H 0.5782 0.5958 -0.0749 0.035 Uiso 1 1 calc R . .
H18B H 0.6800 0.6888 -0.1042 0.035 Uiso 1 1 calc R . .
C19 C 0.7964(5) 0.5103(5) -0.06108(17) 0.0258(11) Uani 1 1 d . . .
C20 C 1.0464(7) 0.4169(8) -0.0826(3) 0.0556(18) Uani 1 1 d . . .
H20A H 1.1219 0.4378 -0.1065 0.083 Uiso 1 1 calc R . .
H20B H 1.0290 0.3268 -0.0862 0.083 Uiso 1 1 calc R . .
H20C H 1.0778 0.4132 -0.0489 0.083 Uiso 1 1 calc R . .
O7 O 0.8456(4) 0.3678(4) 0.39027(13) 0.0323(8) Uani 1 1 d . A 1
O8 O 0.6555(4) 0.2871(4) 0.36688(14) 0.0329(9) Uani 1 1 d . A 1
O9 O 0.5453(4) 0.2076(4) 0.22520(14) 0.0344(9) Uani 1 1 d . A 1
O10 O 0.1945(4) 0.2000(5) 0.30357(18) 0.0501(12) Uani 1 1 d . A 1
O11 O 0.1517(6) 0.1203(7) 0.6143(2) 0.097(2) Uani 1 1 d . A 1
O12 O -0.0591(4) 0.1605(5) 0.57276(16) 0.0477(11) Uani 1 1 d . A 1
N4 N 0.8839(4) 0.2351(5) 0.32912(15) 0.0286(10) Uani 1 1 d . A 1
H4D H 0.9720 0.2471 0.3289 0.034 Uiso 1 1 calc R A 1
N5 N 0.4624(5) 0.4059(4) 0.2609(2) 0.0399(12) Uani 1 1 d . A 1
H5A H 0.4855 0.4760 0.2711 0.048 Uiso 1 1 calc R A 1
N6 N 0.4180(5) 0.1873(5) 0.33462(17) 0.0368(11) Uani 1 1 d . A 1
H6C H 0.4950 0.2212 0.3316 0.044 Uiso 1 1 calc R A 1
C21 C 0.6933(8) 0.3565(7) 0.4687(2) 0.0514(16) Uani 1 1 d . A 1
H21A H 0.6225 0.3175 0.4551 0.077 Uiso 1 1 calc R A 1
H21B H 0.6465 0.4106 0.4945 0.077 Uiso 1 1 calc R A 1
H21C H 0.7729 0.2806 0.4828 0.077 Uiso 1 1 calc R A 1
C22 C 0.7536(6) 0.4525(6) 0.42684(19) 0.0332(12) Uani 1 1 d . A 1
C23 C 0.6315(7) 0.5683(6) 0.4004(2) 0.0477(16) Uani 1 1 d . A 1
H23A H 0.5622 0.5259 0.3876 0.072 Uiso 1 1 calc R A 1
H23B H 0.6732 0.6229 0.3729 0.072 Uiso 1 1 calc R A 1
H23C H 0.5817 0.6293 0.4239 0.072 Uiso 1 1 calc R A 1
C24 C 0.8669(8) 0.5155(8) 0.4478(3) 0.065(2) Uani 1 1 d . A 1
H24A H 0.9044 0.5759 0.4211 0.098 Uiso 1 1 calc R A 1
H24B H 0.9468 0.4401 0.4619 0.098 Uiso 1 1 calc R A 1
H24C H 0.8206 0.5701 0.4736 0.098 Uiso 1 1 calc R A 1
C25 C 0.7832(5) 0.2961(5) 0.36186(18) 0.0252(11) Uani 1 1 d . A 1
C26 C 0.8504(5) 0.1494(5) 0.29403(18) 0.0267(11) Uani 1 1 d . A 1
H26A H 0.7563 0.1269 0.3040 0.032 Uiso 1 1 calc R A 1
H26B H 0.9254 0.0606 0.2964 0.032 Uiso 1 1 calc R A 1
C27 C 0.8432(5) 0.2218(5) 0.23961(19) 0.0289(11) Uani 1 1 d . A 1
H27A H 0.8341 0.1544 0.2181 0.035 Uiso 1 1 calc R A 1
H27B H 0.9350 0.2498 0.2303 0.035 Uiso 1 1 calc R A 1
C28 C 0.7150(6) 0.3525(5) 0.23017(19) 0.0293(11) Uani 1 1 d . A 1
H28A H 0.7217 0.4185 0.2526 0.035 Uiso 1 1 calc R A 1
H28B H 0.7228 0.3994 0.1957 0.035 Uiso 1 1 calc R A 1
C29 C 0.5669(6) 0.3162(5) 0.23837(19) 0.0278(11) Uani 1 1 d . A 1
C30 C 0.3104(6) 0.3919(6) 0.2692(3) 0.057(2) Uani 1 1 d . A 1
C31 C 0.2375(8) 0.4066(7) 0.2169(3) 0.067(2) Uani 1 1 d . A 1
H31A H 0.2431 0.4957 0.1969 0.101 Uiso 1 1 calc R A 1
H31B H 0.1359 0.4031 0.2222 0.101 Uiso 1 1 calc R A 1
H31C H 0.2891 0.3301 0.1994 0.101 Uiso 1 1 calc R A 1
C32 C 0.2307(7) 0.5091(8) 0.2988(4) 0.095(4) Uani 1 1 d . A 1
H32A H 0.2780 0.4971 0.3304 0.143 Uiso 1 1 calc R A 1
H32B H 0.1297 0.5043 0.3049 0.143 Uiso 1 1 calc R A 1
H32C H 0.2343 0.5998 0.2797 0.143 Uiso 1 1 calc R A 1
C33 C 0.3054(5) 0.2488(6) 0.3035(3) 0.0427(16) Uani 1 1 d . A 1
C34 C 0.4145(9) 0.0679(9) 0.3724(2) 0.067(2) Uani 1 1 d . A 1
H34A H 0.5134 0.0158 0.3823 0.080 Uiso 1 1 calc R A 1
H34B H 0.3643 0.0041 0.3607 0.080 Uiso 1 1 calc R A 1
C35 C 0.3230(11) 0.1410(11) 0.4183(3) 0.051(3) Uani 0.70 1 d P A 1
H35A H 0.3769 0.2025 0.4295 0.061 Uiso 1 1 calc R A 1
H35B H 0.2283 0.1993 0.4063 0.061 Uiso 1 1 calc R A 1
C36 C 0.299(2) 0.0324(17) 0.4617(4) 0.125(7) Uani 0.70 1 d P A 1
H36A H 0.3924 -0.0212 0.4760 0.150 Uiso 1 1 calc R A 1
H36B H 0.2499 -0.0332 0.4506 0.150 Uiso 1 1 calc R A 1
C37 C 0.1901(10) 0.1219(10) 0.5058(3) 0.041(2) Uani 0.70 1 d P A 1
H37A H 0.2438 0.1804 0.5190 0.049 Uiso 1 1 calc R A 1
H37B H 0.1020 0.1838 0.4901 0.049 Uiso 1 1 calc R A 1
C38 C 0.1559(10) 0.0400(14) 0.5396(7) 0.144(7) Uani 1 1 d . A 1
H38A H 0.2430 -0.0318 0.5518 0.173 Uiso 1 1 calc R A 1
H38B H 0.0883 -0.0074 0.5276 0.173 Uiso 1 1 calc R A 1
C39 C 0.0886(8) 0.1117(7) 0.5787(3) 0.064(2) Uani 1 1 d . A 1
C40 C -0.1385(7) 0.2154(10) 0.6136(2) 0.138(6) Uani 1 1 d . A 1
H40A H -0.2414 0.2470 0.6058 0.207 Uiso 1 1 calc R A 1
H40B H -0.1033 0.2942 0.6204 0.207 Uiso 1 1 calc R A 1
H40C H -0.1257 0.1430 0.6428 0.207 Uiso 1 1 calc R A 1
C35' C 0.3568(7) 0.0243(10) 0.4228(2) 0.039(4) Uiso 0.30 1 d PR A 2
C36' C 0.3911(7) 0.1186(10) 0.4556(2) 0.044(5) Uiso 0.30 1 d PR A 2
C37' C 0.3260(7) 0.0474(10) 0.5164(2) 0.037(4) Uiso 0.30 1 d PR A 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 0.0161(16) 0.0222(17) 0.0309(18) 0.0042(14) -0.0045(13) -0.0083(13)
N1 0.0113(19) 0.023(2) 0.042(2) 0.0080(18) -0.0051(16) -0.0070(16)
C1 0.029(3) 0.029(3) 0.035(3) -0.004(2) -0.003(2) 0.002(2)
O2 0.0153(17) 0.0267(18) 0.0323(18) -0.0014(14) -0.0039(13) -0.0067(13)
N2 0.0169(19) 0.0147(19) 0.027(2) -0.0044(15) -0.0030(15) -0.0045(15)
C2 0.028(3) 0.038(3) 0.026(3) -0.005(2) -0.001(2) -0.010(2)
O3 0.0196(17) 0.0151(17) 0.044(2) -0.0073(14) -0.0023(14) -0.0073(13)
N3 0.0157(19) 0.030(2) 0.033(2) -0.0148(18) 0.0028(16) -0.0140(17)
C3 0.025(3) 0.017(2) 0.026(2) 0.0006(19) -0.0030(19) -0.003(2)
O4 0.0164(17) 0.0300(19) 0.0393(19) -0.0104(15) -0.0008(14) -0.0114(14)
C4 0.030(3) 0.032(3) 0.034(3) 0.005(2) -0.008(2) -0.016(2)
O5 0.039(2) 0.040(2) 0.051(2) 0.013(2) 0.0086(18) 0.0045(18)
C5 0.016(2) 0.018(2) 0.027(2) -0.0059(19) 0.0027(18) -0.0068(18)
O6 0.028(2) 0.036(2) 0.042(2) -0.0075(17) 0.0077(16) -0.0075(16)
C6 0.011(2) 0.016(2) 0.047(3) 0.003(2) -0.0033(19) -0.0030(18)
C7 0.015(2) 0.024(3) 0.042(3) 0.007(2) -0.011(2) -0.008(2)
C8 0.022(2) 0.023(3) 0.028(2) -0.0006(19) -0.0082(19) -0.011(2)
C9 0.020(2) 0.015(2) 0.028(2) -0.0104(19) 0.0001(18) -0.0030(19)
C10 0.013(2) 0.023(2) 0.031(2) -0.011(2) -0.0020(18) -0.0014(18)
C11 0.026(3) 0.025(3) 0.051(3) -0.008(2) -0.016(2) 0.003(2)
C12 0.020(3) 0.038(3) 0.046(3) -0.019(3) 0.008(2) -0.008(2)
C13 0.012(2) 0.019(2) 0.030(2) -0.0042(19) -0.0031(18) -0.0014(18)
C14 0.024(3) 0.026(3) 0.033(3) -0.013(2) 0.004(2) -0.009(2)
C15 0.020(2) 0.023(3) 0.036(3) -0.010(2) 0.0005(19) -0.008(2)
C16 0.023(2) 0.021(2) 0.028(2) -0.0043(19) 0.0001(19) -0.008(2)
C17 0.028(3) 0.020(3) 0.033(3) -0.004(2) 0.005(2) -0.005(2)
C18 0.031(3) 0.026(3) 0.026(3) 0.000(2) 0.004(2) -0.001(2)
C19 0.028(3) 0.026(3) 0.024(2) -0.004(2) 0.0037(19) -0.007(2)
C20 0.028(3) 0.072(5) 0.057(4) -0.012(3) 0.007(3) 0.005(3)
O7 0.0233(18) 0.040(2) 0.041(2) -0.0178(17) -0.0015(15) -0.0129(16)
O8 0.0156(18) 0.039(2) 0.050(2) -0.0204(17) 0.0030(15) -0.0109(15)
O9 0.044(2) 0.0195(19) 0.045(2) -0.0040(15) -0.0124(17) -0.0158(16)
O10 0.023(2) 0.053(3) 0.093(3) -0.046(2) 0.016(2) -0.0241(19)
O11 0.070(4) 0.127(5) 0.095(4) 0.056(4) -0.054(3) -0.059(4)
O12 0.034(2) 0.060(3) 0.052(2) -0.010(2) -0.0083(18) -0.013(2)
N4 0.0127(19) 0.039(3) 0.039(2) -0.0162(19) 0.0004(17) -0.0087(18)
N5 0.020(2) 0.015(2) 0.090(4) -0.017(2) -0.013(2) -0.0052(18)
N6 0.024(2) 0.045(3) 0.054(3) -0.029(2) 0.015(2) -0.023(2)
C21 0.062(4) 0.048(4) 0.040(3) -0.006(3) 0.005(3) -0.009(3)
C22 0.034(3) 0.033(3) 0.035(3) -0.014(2) 0.000(2) -0.008(2)
C23 0.060(4) 0.037(3) 0.041(3) -0.011(3) 0.001(3) 0.002(3)
C24 0.058(4) 0.075(5) 0.081(5) -0.050(4) -0.006(4) -0.023(4)
C25 0.018(2) 0.029(3) 0.031(3) -0.007(2) -0.0044(19) -0.007(2)
C26 0.017(2) 0.027(3) 0.037(3) -0.010(2) 0.0011(19) -0.004(2)
C27 0.024(3) 0.030(3) 0.036(3) -0.012(2) 0.004(2) -0.011(2)
C28 0.039(3) 0.023(3) 0.031(3) -0.004(2) -0.002(2) -0.016(2)
C29 0.031(3) 0.012(2) 0.041(3) -0.002(2) -0.014(2) -0.006(2)
C30 0.018(3) 0.022(3) 0.137(7) -0.029(3) -0.013(3) -0.005(2)
C31 0.043(4) 0.032(4) 0.132(7) -0.003(4) -0.041(4) -0.015(3)
C32 0.021(3) 0.045(4) 0.232(11) -0.069(6) 0.025(5) -0.007(3)
C33 0.009(2) 0.036(3) 0.094(5) -0.041(3) 0.010(3) -0.008(2)
C34 0.087(5) 0.119(7) 0.024(3) -0.009(3) 0.007(3) -0.084(5)
C35 0.066(6) 0.075(7) 0.036(4) -0.025(4) 0.018(4) -0.055(5)
C36 0.246(19) 0.166(14) 0.037(6) -0.042(7) 0.054(8) -0.184(15)
C37 0.044(5) 0.035(5) 0.041(5) -0.011(4) -0.022(4) 0.002(4)
C38 0.033(5) 0.125(10) 0.31(2) -0.143(13) 0.007(8) -0.015(6)
C39 0.044(4) 0.028(3) 0.123(7) -0.002(4) -0.031(4) -0.011(3)
C40 0.066(6) 0.339(19) 0.050(5) -0.073(8) 0.031(4) -0.106(9)

_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 C5 1.359(5) . ?
O1 C3 1.473(5) . ?
N1 C5 1.349(6) . ?
N1 C6 1.455(6) . ?
N1 H1A 0.8600 . ?
C1 C3 1.527(7) . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
O2 C5 1.221(5) . ?
N2 C9 1.350(6) . ?
N2 C10 1.470(6) . ?
N2 H2A 0.8600 . ?
C2 C3 1.531(7) . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 H2D 0.9600 . ?
O3 C9 1.239(5) . ?
N3 C13 1.332(6) . ?
N3 C14 1.462(6) . ?
N3 H3A 0.8600 . ?
C3 C4 1.517(7) . ?
O4 C13 1.250(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
O5 C19 1.193(6) . ?
O6 C19 1.342(6) . ?
O6 C20 1.446(7) . ?
C6 C7 1.515(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.528(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.514(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C12 1.528(7) . ?
C10 C11 1.532(7) . ?
C10 C13 1.544(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.512(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.532(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.530(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.539(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.503(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O7 C25 1.362(6) . ?
O7 C22 1.482(6) . ?
O8 C25 1.216(6) . ?
O9 C29 1.242(6) . ?
O10 C33 1.246(6) . ?
O11 C39 1.181(9) . ?
O12 C39 1.355(8) . ?
O12 C40 1.390(8) . ?
N4 C25 1.343(6) . ?
N4 C26 1.457(6) . ?
N4 H4D 0.8600 . ?
N5 C29 1.329(7) . ?
N5 C30 1.461(7) . ?
N5 H5A 0.8600 . ?
N6 C33 1.343(8) . ?
N6 C34 1.425(8) . ?
N6 H6C 0.8600 . ?
C21 C22 1.518(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.516(8) . ?
C22 C24 1.530(8) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C26 C27 1.515(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.522(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.508(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C30 C32 1.519(9) . ?
C30 C33 1.560(9) . ?
C30 C31 1.570(10) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C34 C35 1.616(11) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.493(14) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.718(16) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.194(16) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.389(14) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C35' C36' 1.4769 . ?
C36' C37' 1.7995 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C3 121.0(3) . . ?
C5 N1 C6 123.0(4) . . ?
C5 N1 H1A 118.5 . . ?
C6 N1 H1A 118.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C9 N2 C10 123.1(4) . . ?
C9 N2 H2A 118.4 . . ?
C10 N2 H2A 118.4 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2D 109.5 . . ?
H2B C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
C13 N3 C14 123.7(4) . . ?
C13 N3 H3A 118.1 . . ?
C14 N3 H3A 118.1 . . ?
O1 C3 C4 102.3(4) . . ?
O1 C3 C1 110.4(4) . . ?
C4 C3 C1 110.7(4) . . ?
O1 C3 C2 110.8(4) . . ?
C4 C3 C2 110.7(4) . . ?
C1 C3 C2 111.7(4) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 N1 125.6(4) . . ?
O2 C5 O1 124.9(4) . . ?
N1 C5 O1 109.5(4) . . ?
C19 O6 C20 115.7(4) . . ?
N1 C6 C7 114.0(4) . . ?
N1 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 112.8(4) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 111.8(4) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
O3 C9 N2 122.2(4) . . ?
O3 C9 C8 122.0(4) . . ?
N2 C9 C8 115.7(4) . . ?
N2 C10 C12 110.0(4) . . ?
N2 C10 C11 108.1(4) . . ?
C12 C10 C11 110.5(4) . . ?
N2 C10 C13 110.8(3) . . ?
C12 C10 C13 111.4(4) . . ?
C11 C10 C13 105.8(4) . . ?
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 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 N3 122.3(4) . . ?
O4 C13 C10 120.2(4) . . ?
N3 C13 C10 117.1(4) . . ?
N3 C14 C15 111.9(4) . . ?
N3 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 112.5(4) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 113.1(4) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 C18 114.0(4) . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 112.8(4) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
O5 C19 O6 122.7(5) . . ?
O5 C19 C18 125.5(4) . . ?
O6 C19 C18 111.9(4) . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C25 O7 C22 120.2(4) . . ?
C39 O12 C40 115.7(6) . . ?
C25 N4 C26 122.8(4) . . ?
C25 N4 H4D 118.6 . . ?
C26 N4 H4D 118.6 . . ?
C29 N5 C30 123.5(4) . . ?
C29 N5 H5A 118.2 . . ?
C30 N5 H5A 118.2 . . ?
C33 N6 C34 122.5(5) . . ?
C33 N6 H6C 118.8 . . ?
C34 N6 H6C 118.8 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O7 C22 C23 111.0(4) . . ?
O7 C22 C21 110.5(4) . . ?
C23 C22 C21 111.9(5) . . ?
O7 C22 C24 101.6(4) . . ?
C23 C22 C24 111.2(5) . . ?
C21 C22 C24 110.2(5) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O8 C25 N4 125.9(4) . . ?
O8 C25 O7 124.0(4) . . ?
N4 C25 O7 110.0(4) . . ?
N4 C26 C27 113.6(4) . . ?
N4 C26 H26A 108.9 . . ?
C27 C26 H26A 108.9 . . ?
N4 C26 H26B 108.9 . . ?
C27 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C26 C27 C28 113.3(4) . . ?
C26 C27 H27A 108.9 . . ?
C28 C27 H27A 108.9 . . ?
C26 C27 H27B 108.9 . . ?
C28 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
C29 C28 C27 112.5(4) . . ?
C29 C28 H28A 109.1 . . ?
C27 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
C27 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
O9 C29 N5 122.4(5) . . ?
O9 C29 C28 121.5(5) . . ?
N5 C29 C28 116.1(4) . . ?
N5 C30 C32 106.6(5) . . ?
N5 C30 C33 110.7(5) . . ?
C32 C30 C33 106.2(7) . . ?
N5 C30 C31 109.5(6) . . ?
C32 C30 C31 111.6(6) . . ?
C33 C30 C31 112.2(5) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O10 C33 N6 122.2(6) . . ?
O10 C33 C30 119.4(6) . . ?
N6 C33 C30 118.2(4) . . ?
N6 C34 C35 102.6(7) . . ?
N6 C34 H34A 111.3 . . ?
C35 C34 H34A 111.3 . . ?
N6 C34 H34B 111.3 . . ?
C35 C34 H34B 111.3 . . ?
H34A C34 H34B 109.2 . . ?
C36 C35 C34 111.6(9) . . ?
C36 C35 H35A 109.3 . . ?
C34 C35 H35A 109.3 . . ?
C36 C35 H35B 109.3 . . ?
C34 C35 H35B 109.3 . . ?
H35A C35 H35B 108.0 . . ?
C35 C36 C37 107.2(11) . . ?
C35 C36 H36A 110.3 . . ?
C37 C36 H36A 110.3 . . ?
C35 C36 H36B 110.3 . . ?
C37 C36 H36B 110.3 . . ?
H36A C36 H36B 108.5 . . ?
C38 C37 C36 110.4(9) . . ?
C38 C37 H37A 109.6 . . ?
C36 C37 H37A 109.6 . . ?
C38 C37 H37B 109.6 . . ?
C36 C37 H37B 109.6 . . ?
H37A C37 H37B 108.1 . . ?
C37 C38 C39 109.8(10) . . ?
C37 C38 H38A 109.7 . . ?
C39 C38 H38A 109.7 . . ?
C37 C38 H38B 109.7 . . ?
C39 C38 H38B 109.7 . . ?
H38A C38 H38B 108.2 . . ?
O11 C39 O12 124.4(8) . . ?
O11 C39 C38 123.6(8) . . ?
O12 C39 C38 111.8(7) . . ?
O12 C40 H40A 109.5 . . ?
O12 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O12 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C35' C36' C37' 101.8 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.089

# Attachment '- gaba-aib-gaba.cif'

data_ab
_database_code_depnum_ccdc_archive 'CCDC 832143'
#TrackingRef '- gaba-aib-gaba.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H33 N3 O6'
_chemical_formula_sum            'C18 H33 N3 O6'
_chemical_formula_weight         387.47

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   'P2(1)/c '
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.3487(8)
_cell_length_b                   24.295(3)
_cell_length_c                   9.7998(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.135(3)
_cell_angle_gamma                90.00
_cell_volume                     2176.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6401
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.55

_exptl_crystal_description       niddle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.484
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.133
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840.0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS v.2.03 (Bruker, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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            16738
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.97
_reflns_number_total             4244
_reflns_number_gt                2909
_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^)+(0.1350P)^2^+1.5685P] 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         4244
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.2076
_refine_ls_wR_factor_gt          0.1761
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_restrained_S_all      0.867
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.29920(17) 0.11099(8) 0.3253(2) 0.0497(5) Uani 1 1 d . . .
N4 N 0.13875(19) 0.22897(8) 0.30932(19) 0.0365(5) Uani 1 1 d . . .
H4 H 0.1087 0.2216 0.3844 0.044 Uiso 1 1 calc R . .
O3 O 0.4582(3) -0.04428(10) 0.1621(3) 0.0866(8) Uani 1 1 d . . .
O4 O -0.09250(17) 0.12965(9) 0.2482(2) 0.0587(6) Uani 1 1 d . . .
O5 O 0.38042(16) 0.17486(8) 0.10584(17) 0.0486(5) Uani 1 1 d . . .
O6 O 0.08207(18) 0.26805(8) 0.09630(16) 0.0453(5) Uani 1 1 d . . .
N1 N -0.3042(2) 0.17516(9) 0.1667(2) 0.0459(6) Uani 1 1 d . . .
H1 H -0.3932 0.1793 0.1754 0.055 Uiso 1 1 calc R . .
N2 N 0.1600(2) 0.14347(9) 0.1275(2) 0.0442(5) Uani 1 1 d . . .
H2 H 0.0950 0.1437 0.1779 0.053 Uiso 1 1 calc R . .
O7 O 0.2256(4) -0.06270(14) 0.1204(5) 0.1383(14) Uani 1 1 d . . .
C1 C -0.3618(4) 0.04453(17) 0.4719(4) 0.0857(12) Uani 1 1 d . . .
H1A H -0.3926 0.0734 0.5261 0.129 Uiso 1 1 calc R . .
H1B H -0.3317 0.0132 0.5306 0.129 Uiso 1 1 calc R . .
H1C H -0.4417 0.0343 0.3975 0.129 Uiso 1 1 calc R . .
C2 C -0.2350(3) 0.06444(11) 0.4114(3) 0.0541(7) Uani 1 1 d . . .
C3 C -0.2212(2) 0.13800(11) 0.2456(3) 0.0422(6) Uani 1 1 d . . .
C4 C -0.2507(2) 0.20900(11) 0.0667(3) 0.0434(6) Uani 1 1 d . . .
H4A H -0.3224 0.2089 -0.0207 0.052 Uiso 1 1 calc R . .
H4B H -0.1613 0.1929 0.0492 0.052 Uiso 1 1 calc R . .
C5 C -0.2206(3) 0.26769(11) 0.1141(3) 0.0449(6) Uani 1 1 d . . .
H5A H -0.3086 0.2830 0.1367 0.054 Uiso 1 1 calc R . .
H5B H -0.1985 0.2889 0.0373 0.054 Uiso 1 1 calc R . .
C6 C -0.0955(2) 0.27413(11) 0.2397(2) 0.0410(6) Uani 1 1 d . . .
H6A H -0.0900 0.3123 0.2697 0.049 Uiso 1 1 calc R . .
H6B H -0.1153 0.2519 0.3158 0.049 Uiso 1 1 calc R . .
C7 C 0.0500(2) 0.25722(10) 0.2089(2) 0.0350(5) Uani 1 1 d . . .
C8 C 0.2846(2) 0.20996(11) 0.2981(2) 0.0429(6) Uani 1 1 d . . .
C9 C 0.2770(2) 0.17529(10) 0.1661(2) 0.0379(6) Uani 1 1 d . . .
C10 C 0.1357(3) 0.10835(12) 0.0051(3) 0.0558(7) Uani 1 1 d . . .
H10A H 0.2041 0.1186 -0.0525 0.067 Uiso 1 1 calc R . .
H10B H 0.0377 0.1148 -0.0489 0.067 Uiso 1 1 calc R . .
C11 C 0.1528(3) 0.04853(15) 0.0375(4) 0.0749(10) Uani 1 1 d . . .
H11A H 0.0908 0.0389 0.1018 0.090 Uiso 1 1 calc R . .
H11B H 0.1189 0.0278 -0.0478 0.090 Uiso 1 1 calc R . .
C12 C 0.3042(4) 0.03188(15) 0.0990(4) 0.0768(10) Uani 1 1 d . . .
H12A H 0.3367 0.0514 0.1864 0.092 Uiso 1 1 calc R . .
H12B H 0.3669 0.0429 0.0366 0.092 Uiso 1 1 calc R . .
C13 C 0.3224(4) -0.02970(15) 0.1266(4) 0.0730(9) Uani 1 1 d . . .
C14 C 0.4933(5) -0.10109(15) 0.1848(5) 0.0954(13) Uani 1 1 d . . .
H14A H 0.4257 -0.1178 0.2336 0.143 Uiso 1 1 calc R . .
H14B H 0.5910 -0.1046 0.2394 0.143 Uiso 1 1 calc R . .
H14C H 0.4870 -0.1191 0.0965 0.143 Uiso 1 1 calc R . .
C15 C -0.1922(5) 0.02000(15) 0.3208(5) 0.0925(12) Uani 1 1 d . . .
H15A H -0.2730 0.0122 0.2451 0.139 Uiso 1 1 calc R . .
H15B H -0.1662 -0.0127 0.3754 0.139 Uiso 1 1 calc R . .
H15C H -0.1100 0.0321 0.2842 0.139 Uiso 1 1 calc R . .
C16 C 0.3407(3) 0.17163(17) 0.4216(3) 0.0753(11) Uani 1 1 d . . .
H16A H 0.3536 0.1921 0.5070 0.113 Uiso 1 1 calc R . .
H16B H 0.4326 0.1560 0.4127 0.113 Uiso 1 1 calc R . .
H16C H 0.2710 0.1427 0.4225 0.113 Uiso 1 1 calc R . .
C17 C 0.3876(3) 0.25842(15) 0.3003(3) 0.0680(10) Uani 1 1 d . . .
H17A H 0.3484 0.2831 0.2252 0.102 Uiso 1 1 calc R . .
H17B H 0.4815 0.2453 0.2896 0.102 Uiso 1 1 calc R . .
H17C H 0.3982 0.2775 0.3877 0.102 Uiso 1 1 calc R . .
C18 C -0.1109(4) 0.08345(17) 0.5239(4) 0.0876(12) Uani 1 1 d . . .
H18A H -0.0315 0.0954 0.4830 0.131 Uiso 1 1 calc R . .
H18B H -0.0787 0.0537 0.5873 0.131 Uiso 1 1 calc R . .
H18C H -0.1429 0.1135 0.5737 0.131 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 0.0322(8) 0.0612(12) 0.0615(11) 0.0199(9) 0.0226(8) 0.0049(7)
N4 0.0299(9) 0.0585(13) 0.0240(9) -0.0011(9) 0.0122(7) 0.0002(8)
O3 0.0840(17) 0.0519(14) 0.127(2) -0.0011(14) 0.0302(16) -0.0010(12)
O4 0.0268(8) 0.0758(13) 0.0780(14) 0.0227(11) 0.0213(9) 0.0051(8)
O5 0.0230(8) 0.0849(14) 0.0412(9) -0.0087(9) 0.0145(7) -0.0035(8)
O6 0.0430(9) 0.0680(12) 0.0286(9) 0.0024(8) 0.0159(7) -0.0036(8)
N1 0.0208(9) 0.0678(15) 0.0512(12) 0.0151(11) 0.0123(8) 0.0002(9)
N2 0.0278(9) 0.0601(14) 0.0495(12) -0.0137(10) 0.0192(9) -0.0049(9)
O7 0.090(2) 0.105(2) 0.206(4) 0.020(3) -0.002(2) -0.0199(19)
C1 0.080(2) 0.091(3) 0.096(3) 0.044(2) 0.042(2) 0.004(2)
C2 0.0497(15) 0.0461(16) 0.0691(19) 0.0123(13) 0.0187(14) 0.0035(12)
C3 0.0252(11) 0.0561(16) 0.0469(14) 0.0047(12) 0.0116(10) -0.0024(10)
C4 0.0264(11) 0.0665(18) 0.0368(13) 0.0092(12) 0.0055(9) -0.0025(10)
C5 0.0335(12) 0.0572(17) 0.0456(14) 0.0145(12) 0.0122(10) 0.0111(11)
C6 0.0408(13) 0.0501(15) 0.0356(12) 0.0013(11) 0.0161(10) 0.0046(10)
C7 0.0321(11) 0.0472(14) 0.0275(11) -0.0071(10) 0.0099(9) -0.0051(10)
C8 0.0255(11) 0.0709(18) 0.0325(12) -0.0068(12) 0.0064(9) 0.0001(10)
C9 0.0222(10) 0.0598(16) 0.0329(12) 0.0002(11) 0.0082(9) 0.0031(9)
C10 0.0397(13) 0.069(2) 0.0585(17) -0.0211(14) 0.0094(12) -0.0037(12)
C11 0.0573(18) 0.083(2) 0.087(2) -0.033(2) 0.0201(17) -0.0183(16)
C12 0.0638(19) 0.070(2) 0.097(3) -0.0185(19) 0.0181(18) -0.0187(16)
C13 0.074(2) 0.067(2) 0.077(2) -0.0131(17) 0.0127(18) -0.0168(18)
C14 0.122(3) 0.051(2) 0.123(3) -0.005(2) 0.049(3) 0.008(2)
C15 0.105(3) 0.059(2) 0.125(3) -0.004(2) 0.050(3) 0.005(2)
C16 0.0584(18) 0.127(3) 0.0376(15) 0.0057(17) 0.0042(13) 0.0392(19)
C17 0.0385(14) 0.105(3) 0.0626(19) -0.0371(18) 0.0156(13) -0.0253(15)
C18 0.088(3) 0.079(3) 0.085(3) 0.027(2) -0.007(2) 0.002(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.346(3) . ?
O1 C2 1.462(3) . ?
N4 C7 1.336(3) . ?
N4 C8 1.466(3) . ?
N4 H4 0.8600 . ?
O3 C13 1.294(4) . ?
O3 C14 1.425(4) . ?
O4 C3 1.216(3) . ?
O5 C9 1.234(3) . ?
O6 C7 1.231(3) . ?
N1 C3 1.327(3) . ?
N1 C4 1.447(3) . ?
N1 H1 0.8600 . ?
N2 C9 1.328(3) . ?
N2 C10 1.451(3) . ?
N2 H2 0.8600 . ?
O7 C13 1.201(4) . ?
C1 C2 1.513(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C18 1.496(5) . ?
C2 C15 1.505(5) . ?
C4 C5 1.508(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.518(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.511(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C17 1.518(4) . ?
C8 C16 1.529(4) . ?
C8 C9 1.533(3) . ?
C10 C11 1.489(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.474(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.524(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 120.36(18) . . ?
C7 N4 C8 123.38(18) . . ?
C7 N4 H4 118.3 . . ?
C8 N4 H4 118.3 . . ?
C13 O3 C14 119.2(3) . . ?
C3 N1 C4 122.59(19) . . ?
C3 N1 H1 118.7 . . ?
C4 N1 H1 118.7 . . ?
C9 N2 C10 123.7(2) . . ?
C9 N2 H2 118.2 . . ?
C10 N2 H2 118.2 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C18 110.3(2) . . ?
O1 C2 C15 110.0(3) . . ?
C18 C2 C15 113.3(3) . . ?
O1 C2 C1 102.3(2) . . ?
C18 C2 C1 111.1(3) . . ?
C15 C2 C1 109.3(3) . . ?
O4 C3 N1 125.4(2) . . ?
O4 C3 O1 124.2(2) . . ?
N1 C3 O1 110.40(18) . . ?
N1 C4 C5 113.4(2) . . ?
N1 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N1 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 114.2(2) . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C7 C6 C5 112.48(19) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
O6 C7 N4 122.7(2) . . ?
O6 C7 C6 121.3(2) . . ?
N4 C7 C6 115.98(19) . . ?
N4 C8 C17 110.6(2) . . ?
N4 C8 C16 107.6(2) . . ?
C17 C8 C16 110.5(2) . . ?
N4 C8 C9 110.93(17) . . ?
C17 C8 C9 110.8(2) . . ?
C16 C8 C9 106.3(2) . . ?
O5 C9 N2 122.7(2) . . ?
O5 C9 C8 120.4(2) . . ?
N2 C9 C8 116.72(18) . . ?
N2 C10 C11 114.0(3) . . ?
N2 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 113.9(3) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 113.8(3) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
O7 C13 O3 121.2(4) . . ?
O7 C13 C12 126.3(4) . . ?
O3 C13 C12 112.5(3) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C8 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.047