# 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        'Gangadhar Sanjayan'
_publ_contact_author_address     
;
Division of Organic Synthesis
National Chemical Laboratory
Dr. Homi Bhabha Road
Pune
Maharashtra
411008
INDIA
;

_publ_contact_author_email       GJ.SANJAYAN@NCL.RES.IN

_publ_section_title              
;
Isotactic N-Acrylamide Oligomers Assume self-assembled
Sheet Structure: First Unequivocal Evidence From Crystal Structures
;
loop_
_publ_author_name
'Sanjayan Gangadhar'
'R. G. Gonnade'
'Amol Kendhale'
'P. R. Rajamohanan'

# Attachment '1a.cif'

data_akbt1
_database_code_depnum_ccdc_archive 'CCDC 273802'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
'4,6-Bis-methylcarbamonyl-nonanedioic acid bis-methylamide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H28 N4 O4'
_chemical_formula_sum            'C15 H28 N4 O4'
_chemical_formula_weight         328.41

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

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

_cell_length_a                   4.8971(8)
_cell_length_b                   7.7453(13)
_cell_length_c                   23.813(4)
_cell_angle_alpha                85.109(3)
_cell_angle_beta                 88.701(3)
_cell_angle_gamma                76.425(3)
_cell_volume                     874.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4141
_cell_measurement_theta_min      2.564
_cell_measurement_theta_max      27.889

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9305
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_process_details   'Bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7633
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3046
_reflns_number_gt                2636
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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^)+(0.0702P)^2^+0.2075P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3046
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1302
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 1.1621(2) -0.19360(18) 0.47293(5) 0.0332(3) Uani 1 1 d . . .
O2 O 1.0479(2) 0.22398(17) 0.31493(5) 0.0321(3) Uani 1 1 d . . .
O3 O 1.0333(2) 0.22738(17) 0.17735(5) 0.0322(3) Uani 1 1 d . . .
O4 O 1.1626(2) -0.19170(18) 0.04005(5) 0.0329(3) Uani 1 1 d . . .
N4 N 0.7409(3) -0.22507(19) 0.01213(6) 0.0243(3) Uani 1 1 d . . .
H4 H 0.5664 -0.2135 0.0207 0.029 Uiso 1 1 calc R . .
N3 N 0.5634(3) 0.30879(19) 0.17009(6) 0.0267(4) Uani 1 1 d . . .
H3 H 0.4075 0.2758 0.1732 0.032 Uiso 1 1 calc R . .
N2 N 0.5769(3) 0.31646(19) 0.31304(6) 0.0261(3) Uani 1 1 d . . .
H2 H 0.4191 0.2871 0.3105 0.031 Uiso 1 1 calc R . .
N1 N 0.7376(3) -0.23859(19) 0.49945(6) 0.0254(3) Uani 1 1 d . . .
H1 H 0.5626 -0.2190 0.4910 0.030 Uiso 1 1 calc R . .
C10 C 0.8024(3) 0.1889(2) 0.18149(6) 0.0220(4) Uani 1 1 d . . .
C11 C 0.8145(3) 0.1911(2) 0.31148(6) 0.0217(4) Uani 1 1 d . . .
C6 C 0.7816(3) -0.0016(2) 0.19758(7) 0.0220(4) Uani 1 1 d . . .
H6 H 0.5829 -0.0044 0.2012 0.026 Uiso 1 1 calc R . .
C1 C 0.9056(3) -0.1672(2) 0.46502(7) 0.0236(4) Uani 1 1 d . . .
C9 C 0.9050(3) -0.1674(2) 0.04670(7) 0.0235(4) Uani 1 1 d . . .
C5 C 0.9305(3) -0.0759(2) 0.25356(7) 0.0237(4) Uani 1 1 d . . .
H5A H 0.9499 -0.2039 0.2574 0.028 Uiso 1 1 calc R . .
H5B H 1.1182 -0.0549 0.2516 0.028 Uiso 1 1 calc R . .
C7 C 0.9141(3) -0.1166(2) 0.15021(7) 0.0243(4) Uani 1 1 d . . .
H7A H 1.1064 -0.1059 0.1446 0.029 Uiso 1 1 calc R . .
H7B H 0.9192 -0.2404 0.1619 0.029 Uiso 1 1 calc R . .
C8 C 0.7579(3) -0.0660(2) 0.09435(7) 0.0253(4) Uani 1 1 d . . .
H8A H 0.5715 -0.0880 0.0990 0.030 Uiso 1 1 calc R . .
H8B H 0.7366 0.0606 0.0845 0.030 Uiso 1 1 calc R . .
C3 C 0.9148(3) -0.1135(2) 0.35964(7) 0.0251(4) Uani 1 1 d . . .
H3A H 0.9052 -0.2358 0.3562 0.030 Uiso 1 1 calc R . .
H3B H 1.1115 -0.1112 0.3617 0.030 Uiso 1 1 calc R . .
C4 C 0.7859(3) 0.0013(2) 0.30676(7) 0.0225(4) Uani 1 1 d . . .
H4A H 0.5859 0.0017 0.3053 0.027 Uiso 1 1 calc R . .
C2 C 0.7692(3) -0.0521(2) 0.41425(7) 0.0255(4) Uani 1 1 d . . .
H2A H 0.7768 0.0705 0.4178 0.031 Uiso 1 1 calc R . .
H2B H 0.5732 -0.0565 0.4128 0.031 Uiso 1 1 calc R . .
C12 C 0.8359(4) -0.3482(3) 0.55076(7) 0.0332(4) Uani 1 1 d . . .
H12A H 1.0324 -0.4022 0.5472 0.050 Uiso 1 1 calc R . .
H12B H 0.7332 -0.4395 0.5570 0.050 Uiso 1 1 calc R . .
H12C H 0.8073 -0.2754 0.5820 0.050 Uiso 1 1 calc R . .
C15 C 0.8441(4) -0.3062(3) -0.03917(7) 0.0321(4) Uani 1 1 d . . .
H15A H 0.8132 -0.2168 -0.0703 0.048 Uiso 1 1 calc R . .
H15B H 0.7461 -0.3964 -0.0456 0.048 Uiso 1 1 calc R . .
H15C H 1.0415 -0.3591 -0.0356 0.048 Uiso 1 1 calc R . .
C14 C 0.5577(4) 0.4932(2) 0.15269(9) 0.0363(5) Uani 1 1 d . . .
H14A H 0.5590 0.5574 0.1854 0.054 Uiso 1 1 calc R . .
H14B H 0.3906 0.5450 0.1313 0.054 Uiso 1 1 calc R . .
H14C H 0.7198 0.4994 0.1299 0.054 Uiso 1 1 calc R . .
C13 C 0.5771(4) 0.5001(3) 0.31889(9) 0.0376(5) Uani 1 1 d . . .
H13A H 0.6237 0.5134 0.3570 0.056 Uiso 1 1 calc R . .
H13B H 0.3941 0.5738 0.3099 0.056 Uiso 1 1 calc R . .
H13C H 0.7134 0.5354 0.2936 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 0.0140(6) 0.0476(8) 0.0383(7) -0.0036(6) -0.0078(5) -0.0071(6)
O2 0.0166(6) 0.0396(8) 0.0439(8) -0.0083(6) -0.0032(5) -0.0124(5)
O3 0.0153(6) 0.0401(8) 0.0435(8) 0.0006(6) -0.0051(5) -0.0121(5)
O4 0.0135(6) 0.0523(9) 0.0340(7) -0.0086(6) -0.0001(5) -0.0083(6)
N4 0.0141(7) 0.0335(8) 0.0260(7) -0.0057(6) -0.0022(5) -0.0058(6)
N3 0.0154(7) 0.0282(8) 0.0369(8) -0.0040(6) -0.0045(6) -0.0053(6)
N2 0.0151(7) 0.0279(8) 0.0366(8) -0.0066(6) -0.0033(6) -0.0057(6)
N1 0.0150(7) 0.0344(8) 0.0264(7) -0.0027(6) -0.0047(5) -0.0049(6)
C10 0.0152(8) 0.0314(9) 0.0209(8) -0.0047(7) -0.0030(6) -0.0070(7)
C11 0.0163(8) 0.0310(9) 0.0192(8) -0.0038(7) -0.0020(6) -0.0077(7)
C6 0.0115(7) 0.0294(9) 0.0257(8) -0.0036(7) -0.0023(6) -0.0055(7)
C1 0.0168(8) 0.0282(9) 0.0269(9) -0.0093(7) -0.0033(6) -0.0048(7)
C9 0.0162(8) 0.0282(9) 0.0257(9) 0.0006(7) -0.0047(6) -0.0053(7)
C5 0.0160(8) 0.0268(9) 0.0279(9) -0.0033(7) -0.0029(6) -0.0037(7)
C7 0.0169(8) 0.0290(9) 0.0276(9) -0.0042(7) -0.0029(6) -0.0054(7)
C8 0.0147(8) 0.0323(10) 0.0287(9) -0.0052(7) -0.0040(6) -0.0037(7)
C3 0.0179(8) 0.0269(9) 0.0305(9) -0.0050(7) -0.0045(7) -0.0040(7)
C4 0.0122(7) 0.0292(9) 0.0267(9) -0.0039(7) -0.0032(6) -0.0052(7)
C2 0.0160(8) 0.0309(9) 0.0292(9) -0.0032(7) -0.0023(7) -0.0041(7)
C12 0.0285(10) 0.0412(11) 0.0277(9) 0.0003(8) -0.0044(7) -0.0045(8)
C15 0.0254(9) 0.0421(11) 0.0277(9) -0.0090(8) -0.0030(7) -0.0033(8)
C14 0.0306(10) 0.0278(10) 0.0496(12) -0.0056(8) -0.0065(8) -0.0037(8)
C13 0.0317(10) 0.0289(10) 0.0526(12) -0.0085(9) -0.0017(9) -0.0058(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 C1 1.2404(19) . ?
O2 C11 1.2342(19) . ?
O3 C10 1.2352(19) . ?
O4 C9 1.240(2) . ?
N4 C9 1.336(2) . ?
N4 C15 1.448(2) . ?
N4 H4 0.8600 . ?
N3 C10 1.329(2) . ?
N3 C14 1.447(2) . ?
N3 H3 0.8600 . ?
N2 C11 1.331(2) . ?
N2 C13 1.441(2) . ?
N2 H2 0.8600 . ?
N1 C1 1.327(2) . ?
N1 C12 1.450(2) . ?
N1 H1 0.8600 . ?
C10 C6 1.518(2) . ?
C11 C4 1.522(2) . ?
C6 C7 1.534(2) . ?
C6 C5 1.535(2) . ?
C6 H6 0.9800 . ?
C1 C2 1.509(2) . ?
C9 C8 1.508(2) . ?
C5 C4 1.534(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C8 1.525(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C3 C2 1.527(2) . ?
C3 C4 1.535(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9800 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C9 N4 C15 122.85(14) . . ?
C9 N4 H4 118.6 . . ?
C15 N4 H4 118.6 . . ?
C10 N3 C14 121.97(15) . . ?
C10 N3 H3 119.0 . . ?
C14 N3 H3 119.0 . . ?
C11 N2 C13 121.77(14) . . ?
C11 N2 H2 119.1 . . ?
C13 N2 H2 119.1 . . ?
C1 N1 C12 122.90(14) . . ?
C1 N1 H1 118.6 . . ?
C12 N1 H1 118.6 . . ?
O3 C10 N3 122.17(16) . . ?
O3 C10 C6 120.78(15) . . ?
N3 C10 C6 117.00(14) . . ?
O2 C11 N2 122.47(16) . . ?
O2 C11 C4 120.81(15) . . ?
N2 C11 C4 116.70(14) . . ?
C10 C6 C7 108.35(13) . . ?
C10 C6 C5 111.75(13) . . ?
C7 C6 C5 109.92(13) . . ?
C10 C6 H6 108.9 . . ?
C7 C6 H6 108.9 . . ?
C5 C6 H6 108.9 . . ?
O1 C1 N1 122.85(16) . . ?
O1 C1 C2 120.74(15) . . ?
N1 C1 C2 116.40(14) . . ?
O4 C9 N4 122.83(15) . . ?
O4 C9 C8 121.09(14) . . ?
N4 C9 C8 116.07(14) . . ?
C4 C5 C6 115.97(13) . . ?
C4 C5 H5A 108.3 . . ?
C6 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
C6 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C8 C7 C6 113.62(13) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 113.23(13) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C2 C3 C4 113.50(13) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C11 C4 C5 111.72(14) . . ?
C11 C4 C3 108.31(13) . . ?
C5 C4 C3 110.34(13) . . ?
C11 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C1 C2 C3 111.55(13) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 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
C14 N3 C10 O3 -0.8(2) . . . . ?
C14 N3 C10 C6 -178.15(15) . . . . ?
C13 N2 C11 O2 0.0(3) . . . . ?
C13 N2 C11 C4 178.41(16) . . . . ?
O3 C10 C6 C7 -65.44(18) . . . . ?
N3 C10 C6 C7 111.99(15) . . . . ?
O3 C10 C6 C5 55.81(19) . . . . ?
N3 C10 C6 C5 -126.76(15) . . . . ?
C12 N1 C1 O1 2.6(3) . . . . ?
C12 N1 C1 C2 -178.27(15) . . . . ?
C15 N4 C9 O4 -6.0(3) . . . . ?
C15 N4 C9 C8 172.66(15) . . . . ?
C10 C6 C5 C4 71.39(17) . . . . ?
C7 C6 C5 C4 -168.28(13) . . . . ?
C10 C6 C7 C8 -64.39(17) . . . . ?
C5 C6 C7 C8 173.24(14) . . . . ?
O4 C9 C8 C7 -43.3(2) . . . . ?
N4 C9 C8 C7 138.01(16) . . . . ?
C6 C7 C8 C9 174.39(14) . . . . ?
O2 C11 C4 C5 -61.07(19) . . . . ?
N2 C11 C4 C5 120.50(15) . . . . ?
O2 C11 C4 C3 60.66(19) . . . . ?
N2 C11 C4 C3 -117.77(15) . . . . ?
C6 C5 C4 C11 -72.93(17) . . . . ?
C6 C5 C4 C3 166.52(13) . . . . ?
C2 C3 C4 C11 61.15(17) . . . . ?
C2 C3 C4 C5 -176.28(13) . . . . ?
O1 C1 C2 C3 53.0(2) . . . . ?
N1 C1 C2 C3 -126.07(15) . . . . ?
C4 C3 C2 C1 -179.17(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
N1 H1 O1 0.86 1.98 2.8360(18) 175.6 1_455
N2 H2 O2 0.86 1.99 2.8437(18) 172.7 1_455
N3 H3 O3 0.86 1.95 2.8098(18) 173.8 1_455
N4 H4 O4 0.86 1.99 2.8513(18) 178.8 1_455

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.062

# Attachment '1e.cif'

data_amol5
_database_code_depnum_ccdc_archive 'CCDC 273803'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
;
4,6-Bis-methylcabamoyl-2,2,8,8-Tetramethyl carbamoyl-
nonanedioic acid bis-methylamide
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H36 N4 O4'
_chemical_formula_sum            'C19 H36 N4 O4'
_chemical_formula_weight         384.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.676(3)
_cell_length_b                   12.826(4)
_cell_length_c                   17.434(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2163.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1003
_cell_measurement_theta_min      2.335
_cell_measurement_theta_max      17.153

_exptl_crystal_description       'Thin needle'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.95
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9252
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10757
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_sigmaI/netI    0.1235
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3801
_reflns_number_gt                2231
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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^)+(0.0352P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(19)
_chemical_absolute_configuration SYN
_refine_ls_number_reflns         3801
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_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 -0.0159(3) 0.5639(2) 1.14848(15) 0.0755(9) Uani 1 1 d . . .
O2 O -0.0281(3) 0.3289(2) 1.07351(12) 0.0612(7) Uani 1 1 d . . .
O3 O -0.0279(3) 0.14216(17) 0.95316(13) 0.0590(7) Uani 1 1 d . . .
O4 O -0.0150(3) 0.00694(19) 0.79280(14) 0.0688(8) Uani 1 1 d . . .
N1 N 0.2016(3) 0.5439(2) 1.18429(15) 0.0538(8) Uani 1 1 d . . .
H1 H 0.2875 0.5451 1.1717 0.065 Uiso 1 1 calc R . .
N2 N 0.1950(3) 0.3065(2) 1.09890(14) 0.0505(8) Uani 1 1 d . . .
H2 H 0.2788 0.3168 1.0844 0.061 Uiso 1 1 calc R . .
N3 N 0.1952(3) 0.1122(2) 0.97417(15) 0.0493(7) Uani 1 1 d . . .
H3 H 0.2791 0.1297 0.9643 0.059 Uiso 1 1 calc R . .
N4 N 0.2047(3) -0.0330(2) 0.81510(15) 0.0503(7) Uani 1 1 d . . .
H4 H 0.2900 -0.0148 0.8116 0.060 Uiso 1 1 calc R . .
C9 C 0.1081(4) 0.0325(3) 0.79176(17) 0.0459(9) Uani 1 1 d . . .
C11 C 0.0939(4) 0.3431(3) 1.05641(18) 0.0402(8) Uani 1 1 d . . .
C7 C 0.0831(3) 0.2270(2) 0.80550(16) 0.0406(8) Uani 1 1 d . . .
H7A H 0.0943 0.2903 0.7757 0.049 Uiso 1 1 calc R . .
H7B H -0.0152 0.2128 0.8082 0.049 Uiso 1 1 calc R . .
C5 C 0.0702(3) 0.3540(2) 0.91340(16) 0.0389(8) Uani 1 1 d . . .
H5A H -0.0276 0.3433 0.9227 0.047 Uiso 1 1 calc R . .
H5B H 0.0785 0.4036 0.8717 0.047 Uiso 1 1 calc R . .
C4 C 0.1339(3) 0.4029(2) 0.98552(15) 0.0352(8) Uani 1 1 d . . .
H4A H 0.2347 0.4023 0.9806 0.042 Uiso 1 1 calc R . .
C1 C 0.1069(4) 0.5628(3) 1.1314(2) 0.0494(9) Uani 1 1 d . . .
C3 C 0.0844(4) 0.5164(2) 0.99210(17) 0.0433(8) Uani 1 1 d . . .
H3A H 0.0945 0.5482 0.9419 0.052 Uiso 1 1 calc R . .
H3B H -0.0137 0.5148 1.0034 0.052 Uiso 1 1 calc R . .
C10 C 0.0941(4) 0.1632(3) 0.94057(17) 0.0389(8) Uani 1 1 d . . .
C12 C 0.3094(4) 0.5916(3) 1.0393(2) 0.0585(10) Uani 1 1 d . . .
H12A H 0.3492 0.6443 1.0715 0.088 Uiso 1 1 calc R . .
H12B H 0.3301 0.6069 0.9866 0.088 Uiso 1 1 calc R . .
H12C H 0.3473 0.5248 1.0526 0.088 Uiso 1 1 calc R . .
C8 C 0.1497(3) 0.1382(3) 0.76005(16) 0.0410(8) Uani 1 1 d . . .
C6 C 0.1327(3) 0.2502(2) 0.88699(15) 0.0356(8) Uani 1 1 d . . .
H6A H 0.2336 0.2569 0.8864 0.043 Uiso 1 1 calc R . .
C15 C 0.3064(3) 0.1535(3) 0.75380(18) 0.0519(9) Uani 1 1 d . . .
H15A H 0.3255 0.2220 0.7343 0.078 Uiso 1 1 calc R . .
H15B H 0.3442 0.1022 0.7196 0.078 Uiso 1 1 calc R . .
H15C H 0.3476 0.1458 0.8036 0.078 Uiso 1 1 calc R . .
C19 C 0.1715(4) -0.1338(3) 0.8462(2) 0.0683(12) Uani 1 1 d . . .
H19A H 0.1156 -0.1254 0.8913 0.102 Uiso 1 1 calc R . .
H19B H 0.2553 -0.1697 0.8595 0.102 Uiso 1 1 calc R . .
H19C H 0.1216 -0.1736 0.8087 0.102 Uiso 1 1 calc R . .
C2 C 0.1526(3) 0.5897(3) 1.05054(18) 0.0462(9) Uani 1 1 d . . .
C14 C 0.0891(4) 0.1421(3) 0.67827(17) 0.0585(10) Uani 1 1 d . . .
H14A H 0.1172 0.2056 0.6536 0.088 Uiso 1 1 calc R . .
H14B H -0.0100 0.1396 0.6810 0.088 Uiso 1 1 calc R . .
H14C H 0.1222 0.0836 0.6493 0.088 Uiso 1 1 calc R . .
C13 C 0.0953(4) 0.6994(3) 1.0349(2) 0.0721(12) Uani 1 1 d . . .
H13A H 0.1308 0.7470 1.0726 0.108 Uiso 1 1 calc R . .
H13B H -0.0037 0.6979 1.0378 0.108 Uiso 1 1 calc R . .
H13C H 0.1231 0.7217 0.9847 0.108 Uiso 1 1 calc R . .
C17 C 0.1705(4) 0.2496(4) 1.1690(2) 0.0802(14) Uani 1 1 d . . .
H17A H 0.1502 0.2978 1.2096 0.120 Uiso 1 1 calc R . .
H17B H 0.2514 0.2100 1.1820 0.120 Uiso 1 1 calc R . .
H17C H 0.0936 0.2033 1.1621 0.120 Uiso 1 1 calc R . .
C18 C 0.1696(5) 0.0282(3) 1.0269(2) 0.0809(13) Uani 1 1 d . . .
H18A H 0.2067 0.0457 1.0763 0.121 Uiso 1 1 calc R . .
H18B H 0.2132 -0.0342 1.0084 0.121 Uiso 1 1 calc R . .
H18C H 0.0718 0.0168 1.0312 0.121 Uiso 1 1 calc R . .
C16 C 0.1639(4) 0.5213(4) 1.2627(2) 0.0757(13) Uani 1 1 d . . .
H16A H 0.1268 0.5829 1.2862 0.114 Uiso 1 1 calc R . .
H16B H 0.2443 0.4989 1.2904 0.114 Uiso 1 1 calc R . .
H16C H 0.0956 0.4670 1.2635 0.114 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 0.0275(18) 0.121(3) 0.0774(17) 0.0010(15) 0.0050(13) 0.0071(15)
O2 0.0284(16) 0.0983(19) 0.0570(14) 0.0171(13) 0.0033(12) 0.0015(14)
O3 0.0322(16) 0.0699(17) 0.0749(16) 0.0188(13) 0.0034(13) -0.0071(14)
O4 0.0250(16) 0.0751(19) 0.106(2) 0.0050(15) 0.0021(14) -0.0113(13)
N1 0.0279(18) 0.079(2) 0.0543(18) 0.0030(15) -0.0050(16) 0.0007(16)
N2 0.0308(19) 0.072(2) 0.0491(16) 0.0136(14) -0.0005(14) 0.0034(15)
N3 0.0296(18) 0.0588(18) 0.0594(17) 0.0162(15) -0.0088(15) -0.0008(15)
N4 0.0289(18) 0.0509(18) 0.0712(19) 0.0099(16) 0.0008(15) -0.0038(16)
C9 0.035(3) 0.054(2) 0.048(2) -0.0132(18) 0.0027(17) -0.002(2)
C11 0.030(2) 0.043(2) 0.047(2) -0.0023(16) -0.0026(17) 0.0029(17)
C7 0.029(2) 0.050(2) 0.0433(19) 0.0038(16) -0.0031(15) -0.0006(16)
C5 0.028(2) 0.047(2) 0.0414(16) 0.0038(15) -0.0007(15) -0.0005(16)
C4 0.0211(18) 0.047(2) 0.0379(17) 0.0036(15) -0.0021(15) -0.0012(15)
C1 0.038(3) 0.050(2) 0.061(2) -0.0132(17) -0.005(2) 0.0014(19)
C3 0.033(2) 0.046(2) 0.0511(19) 0.0004(16) -0.0080(15) 0.0052(17)
C10 0.028(2) 0.047(2) 0.0409(18) -0.0059(16) -0.0029(17) -0.0041(19)
C12 0.046(3) 0.061(2) 0.069(2) -0.0012(18) -0.001(2) -0.0152(19)
C8 0.029(2) 0.056(2) 0.0384(17) -0.0017(16) -0.0012(15) -0.0008(17)
C6 0.0227(19) 0.0441(19) 0.0398(18) 0.0016(16) -0.0003(14) -0.0026(16)
C15 0.035(2) 0.069(2) 0.052(2) 0.0038(18) 0.0078(17) -0.0078(19)
C19 0.058(3) 0.058(3) 0.088(3) 0.007(2) 0.005(2) -0.005(2)
C2 0.030(2) 0.050(2) 0.059(2) -0.0049(17) -0.0035(18) 0.0020(17)
C14 0.053(3) 0.078(3) 0.0438(19) -0.0078(19) -0.0071(17) 0.009(2)
C13 0.076(3) 0.049(2) 0.090(3) -0.004(2) -0.018(3) 0.009(2)
C17 0.055(3) 0.118(4) 0.067(3) 0.038(3) 0.003(2) 0.017(3)
C18 0.071(3) 0.079(3) 0.093(3) 0.037(3) -0.016(3) -0.006(2)
C16 0.062(3) 0.107(4) 0.059(2) 0.001(2) -0.007(2) -0.008(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.225(4) . ?
O2 C11 1.231(4) . ?
O3 C10 1.231(4) . ?
O4 C9 1.235(4) . ?
N1 C1 1.323(4) . ?
N1 C16 1.443(4) . ?
N1 H1 0.8600 . ?
N2 C11 1.314(4) . ?
N2 C17 1.443(4) . ?
N2 H2 0.8600 . ?
N3 C10 1.314(4) . ?
N3 C18 1.439(4) . ?
N3 H3 0.8600 . ?
N4 C9 1.321(4) . ?
N4 C19 1.438(4) . ?
N4 H4 0.8600 . ?
C9 C8 1.518(5) . ?
C11 C4 1.505(4) . ?
C7 C6 1.529(4) . ?
C7 C8 1.530(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 C6 1.532(4) . ?
C5 C4 1.534(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 C3 1.537(4) . ?
C4 H4A 0.9800 . ?
C1 C2 1.517(5) . ?
C3 C2 1.535(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C10 C6 1.502(4) . ?
C12 C2 1.530(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C8 C15 1.532(4) . ?
C8 C14 1.543(4) . ?
C6 H6A 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C2 C13 1.536(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 N1 C16 121.5(3) . . ?
C1 N1 H1 119.3 . . ?
C16 N1 H1 119.3 . . ?
C11 N2 C17 122.4(3) . . ?
C11 N2 H2 118.8 . . ?
C17 N2 H2 118.8 . . ?
C10 N3 C18 122.0(3) . . ?
C10 N3 H3 119.0 . . ?
C18 N3 H3 119.0 . . ?
C9 N4 C19 122.0(3) . . ?
C9 N4 H4 119.0 . . ?
C19 N4 H4 119.0 . . ?
O4 C9 N4 120.5(3) . . ?
O4 C9 C8 119.9(3) . . ?
N4 C9 C8 119.5(3) . . ?
O2 C11 N2 121.6(3) . . ?
O2 C11 C4 121.4(3) . . ?
N2 C11 C4 117.0(3) . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7A 107.4 . . ?
C8 C7 H7A 107.4 . . ?
C6 C7 H7B 107.4 . . ?
C8 C7 H7B 107.4 . . ?
H7A C7 H7B 106.9 . . ?
C6 C5 C4 116.3(2) . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
C4 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
C11 C4 C5 111.2(2) . . ?
C11 C4 C3 110.0(2) . . ?
C5 C4 C3 108.9(2) . . ?
C11 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
O1 C1 N1 120.2(4) . . ?
O1 C1 C2 120.5(3) . . ?
N1 C1 C2 119.2(3) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3A 107.4 . . ?
C4 C3 H3A 107.4 . . ?
C2 C3 H3B 107.4 . . ?
C4 C3 H3B 107.4 . . ?
H3A C3 H3B 106.9 . . ?
O3 C10 N3 121.7(3) . . ?
O3 C10 C6 120.8(3) . . ?
N3 C10 C6 117.5(3) . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C8 C7 111.4(2) . . ?
C9 C8 C15 113.8(3) . . ?
C7 C8 C15 111.0(3) . . ?
C9 C8 C14 105.4(3) . . ?
C7 C8 C14 107.1(3) . . ?
C15 C8 C14 107.8(3) . . ?
C10 C6 C7 110.8(3) . . ?
C10 C6 C5 111.1(2) . . ?
C7 C6 C5 109.0(2) . . ?
C10 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 C2 C12 114.3(3) . . ?
C1 C2 C3 110.6(3) . . ?
C12 C2 C3 110.5(3) . . ?
C1 C2 C13 105.5(3) . . ?
C12 C2 C13 108.7(3) . . ?
C3 C2 C13 106.7(3) . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 N4 C9 O4 -3.3(5) . . . . ?
C19 N4 C9 C8 179.5(3) . . . . ?
C17 N2 C11 O2 -1.5(5) . . . . ?
C17 N2 C11 C4 178.8(3) . . . . ?
O2 C11 C4 C5 -56.8(4) . . . . ?
N2 C11 C4 C5 122.8(3) . . . . ?
O2 C11 C4 C3 63.9(4) . . . . ?
N2 C11 C4 C3 -116.5(3) . . . . ?
C6 C5 C4 C11 -72.3(3) . . . . ?
C6 C5 C4 C3 166.4(3) . . . . ?
C16 N1 C1 O1 1.7(5) . . . . ?
C16 N1 C1 C2 177.9(3) . . . . ?
C11 C4 C3 C2 69.0(4) . . . . ?
C5 C4 C3 C2 -168.9(3) . . . . ?
C18 N3 C10 O3 0.7(5) . . . . ?
C18 N3 C10 C6 179.5(3) . . . . ?
O4 C9 C8 C7 60.5(4) . . . . ?
N4 C9 C8 C7 -122.3(3) . . . . ?
O4 C9 C8 C15 -173.2(3) . . . . ?
N4 C9 C8 C15 4.0(4) . . . . ?
O4 C9 C8 C14 -55.3(4) . . . . ?
N4 C9 C8 C14 121.9(3) . . . . ?
C6 C7 C8 C9 71.2(4) . . . . ?
C6 C7 C8 C15 -56.7(4) . . . . ?
C6 C7 C8 C14 -174.1(3) . . . . ?
O3 C10 C6 C7 -63.4(4) . . . . ?
N3 C10 C6 C7 117.8(3) . . . . ?
O3 C10 C6 C5 57.9(4) . . . . ?
N3 C10 C6 C5 -120.9(3) . . . . ?
C8 C7 C6 C10 -68.2(4) . . . . ?
C8 C7 C6 C5 169.3(3) . . . . ?
C4 C5 C6 C10 71.5(3) . . . . ?
C4 C5 C6 C7 -166.2(3) . . . . ?
O1 C1 C2 C12 176.4(3) . . . . ?
N1 C1 C2 C12 0.1(4) . . . . ?
O1 C1 C2 C3 -58.1(4) . . . . ?
N1 C1 C2 C3 125.7(3) . . . . ?
O1 C1 C2 C13 57.0(4) . . . . ?
N1 C1 C2 C13 -119.2(3) . . . . ?
C4 C3 C2 C1 -73.6(4) . . . . ?
C4 C3 C2 C12 54.1(4) . . . . ?
C4 C3 C2 C13 172.1(3) . . . . ?

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
N1 H1 O4 0.86 2.12 2.847(4) 142.5 4_557
N2 H2 O3 0.86 2.05 2.906(4) 173.7 4_557
N3 H3 O2 0.86 2.05 2.903(4) 172.7 4_557
N4 H4 O1 0.86 2.10 2.805(4) 138.9 4_557
C4 H4A O3 0.98 2.63 3.491(4) 146.3 4_557
C6 H6A O2 0.98 2.65 3.503(4) 145.9 4_557
C15 H15C O2 0.96 2.48 3.417(4) 165.8 4_557
C12 H12C O3 0.96 2.46 3.389(4) 162.5 4_557
C19 H19B O1 0.96 2.60 3.156(5) 117.1 4_557

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.040