# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

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

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
  Glycyl-glycyl-glycyl-glycine
;
_chemical_name_common            Tetraglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 N4 O5'
_chemical_formula_sum            'C8 H14 N4 O5'
_chemical_formula_weight         246.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8042(2)
_cell_length_b                   14.8701(5)
_cell_length_c                   15.6243(5)
_cell_angle_alpha                67.284(3)
_cell_angle_beta                 85.298(3)
_cell_angle_gamma                88.190(3)
_cell_volume                     1026.14(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    11175
_cell_measurement_theta_min      3.0725
_cell_measurement_theta_max      75.1159

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.146
_shelx_estimated_absorpt_T_min   0.657
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6571
_exptl_absorpt_correction_T_max  0.9664

_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET)
(compiled Mar  7 2011,18:06:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3693
_diffrn_reflns_number            19837
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         75.296
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4181
_reflns_number_gt                3963
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET)
(compiled Mar  7 2011,18:06:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET)
(compiled Mar  7 2011,18:06:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET)
(compiled Mar  7 2011,18:06:32)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0719P)²+0.2181P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4181
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.5428(2) 0.13649(8) 0.87273(7) 0.0280(2) Uani 1 1 d . . . . .
H1AA H 0.6484 0.0763 0.8878 0.034 Uiso 1 1 calc R U . . .
H1AB H 0.6702 0.1882 0.8670 0.034 Uiso 1 1 calc R U . . .
C2A C 0.4121(2) 0.16026(8) 0.78161(7) 0.0267(2) Uani 1 1 d . . . . .
C3A C 0.4502(3) 0.15121(9) 0.63123(8) 0.0301(3) Uani 1 1 d . . . . .
H3AA H 0.4397 0.2214 0.5990 0.036 Uiso 1 1 calc R U . . .
H3AB H 0.2643 0.1246 0.6377 0.036 Uiso 1 1 calc R U . . .
C4A C 0.6464(2) 0.10909(8) 0.57551(7) 0.0253(2) Uani 1 1 d . . . . .
C5A C 0.7657(3) 0.10264(8) 0.42481(8) 0.0286(2) Uani 1 1 d . . . . .
H5AA H 0.7717 0.0320 0.4518 0.034 Uiso 1 1 calc R U . . .
H5AB H 0.9549 0.1268 0.4174 0.034 Uiso 1 1 calc R U . . .
C6A C 0.6450(2) 0.13696(8) 0.33063(7) 0.0250(2) Uani 1 1 d . . . . .
C7A C 0.6833(2) 0.12364(9) 0.17936(8) 0.0299(2) Uani 1 1 d . . . . .
H7AA H 0.6960 0.1929 0.1415 0.036 Uiso 1 1 calc R U . . .
H7AB H 0.4889 0.1045 0.1866 0.036 Uiso 1 1 calc R U . . .
C8A C 0.8566(2) 0.06713(8) 0.13051(7) 0.0265(2) Uani 1 1 d . . . . .
N1A N 0.3227(2) 0.12593(7) 0.94748(6) 0.0304(2) Uani 1 1 d . . . . .
H1AC H 0.4007 0.1136 1.0006 0.037 Uiso 1 1 calc R U . . .
H1AD H 0.2102 0.0769 0.9541 0.037 Uiso 1 1 calc R U . . .
H1AE H 0.2244 0.1809 0.9329 0.037 Uiso 1 1 calc R U . . .
N2A N 0.5503(2) 0.12758(7) 0.72240(6) 0.0299(2) Uani 1 1 d . . . . .
H2A H 0.6980 0.0927 0.7380 0.036 Uiso 1 1 calc R U . . .
N3A N 0.5949(2) 0.13793(7) 0.48597(7) 0.0290(2) Uani 1 1 d . . . . .
H3A H 0.4597 0.1776 0.4647 0.035 Uiso 1 1 calc R U . . .
N4A N 0.7815(2) 0.10491(8) 0.27023(7) 0.0316(2) Uani 1 1 d . . . . .
H4A H 0.9328 0.0720 0.2855 0.038 Uiso 1 1 calc R U . . .
O1A O 0.1959(2) 0.20747(8) 0.76481(6) 0.0490(3) Uani 1 1 d . . . . .
O2A O 0.8348(2) 0.05289(7) 0.61024(6) 0.0397(2) Uani 1 1 d . . . . .
O3A O 0.4389(2) 0.19001(7) 0.31275(6) 0.0371(2) Uani 1 1 d . . . . .
O4A O 0.76258(18) 0.06565(7) 0.05822(6) 0.0345(2) Uani 1 1 d . . . . .
O5A O 1.0763(2) 0.02877(8) 0.16294(7) 0.0486(3) Uani 1 1 d . . . . .
C1B C 0.2034(2) 0.33889(8) 0.13940(7) 0.0297(2) Uani 1 1 d . . . . .
H1BA H 0.3829 0.3354 0.1648 0.036 Uiso 1 1 calc R U . . .
H1BB H 0.1538 0.2739 0.1453 0.036 Uiso 1 1 calc R U . . .
C2B C -0.0175(2) 0.37708(8) 0.19250(7) 0.0252(2) Uani 1 1 d . . . . .
C3B C -0.1752(2) 0.37916(9) 0.34339(7) 0.0284(2) Uani 1 1 d . . . . .
H3BA H -0.3601 0.3511 0.3523 0.034 Uiso 1 1 calc R U . . .
H3BB H -0.1918 0.4496 0.3150 0.034 Uiso 1 1 calc R U . . .
C4B C -0.0482(2) 0.34917(8) 0.43669(7) 0.0245(2) Uani 1 1 d . . . . .
C5B C -0.0637(2) 0.36112(9) 0.58606(7) 0.0287(2) Uani 1 1 d . . . . .
H5BA H 0.1254 0.3857 0.5779 0.034 Uiso 1 1 calc R U . . .
H5BB H -0.0577 0.2907 0.6176 0.034 Uiso 1 1 calc R U . . .
C6B C -0.2444(2) 0.40381(8) 0.64569(7) 0.0251(2) Uani 1 1 d . . . . .
C7B C -0.3137(2) 0.40635(8) 0.80179(7) 0.0282(2) Uani 1 1 d . . . . .
H7BA H -0.5059 0.3840 0.8139 0.034 Uiso 1 1 calc R U . . .
H7BB H -0.3151 0.4770 0.7774 0.034 Uiso 1 1 calc R U . . .
C8B C -0.1694(2) 0.36752(8) 0.89240(7) 0.0257(2) Uani 1 1 d . . . . .
N1B N 0.2210(2) 0.40530(7) 0.04084(6) 0.0291(2) Uani 1 1 d . . . . .
H1BC H 0.2348 0.4665 0.0365 0.035 Uiso 1 1 calc R U . . .
H1BD H 0.0681 0.3991 0.0150 0.035 Uiso 1 1 calc R U . . .
H1BE H 0.3707 0.3905 0.0113 0.035 Uiso 1 1 calc R U . . .
N2B N 0.0057(2) 0.34436(7) 0.28384(6) 0.0290(2) Uani 1 1 d . . . . .
H2B H 0.1312 0.3015 0.3081 0.035 Uiso 1 1 calc R U . . .
N3B N -0.1721(2) 0.38633(7) 0.49556(6) 0.0281(2) Uani 1 1 d . . . . .
H3B H -0.3136 0.4245 0.4801 0.034 Uiso 1 1 calc R U . . .
N4B N -0.1724(2) 0.37370(7) 0.73318(6) 0.0290(2) Uani 1 1 d . . . . .
H4B H -0.0363 0.3332 0.7496 0.035 Uiso 1 1 calc R U . . .
O1B O -0.19653(19) 0.43454(7) 0.15185(6) 0.0370(2) Uani 1 1 d . . . . .
O2B O 0.15135(19) 0.29362(7) 0.45555(6) 0.0367(2) Uani 1 1 d . . . . .
O3B O -0.4349(2) 0.46100(7) 0.61519(6) 0.0403(2) Uani 1 1 d . . . . .
O4B O -0.26453(17) 0.39873(6) 0.95458(5) 0.0325(2) Uani 1 1 d . . . . .
O5B O 0.0286(2) 0.31030(7) 0.90166(6) 0.0408(2) Uani 1 1 d . . . . .


_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
C1A N1A 1.4740(14) . ?
C1A C2A 1.5132(14) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C2A O1A 1.2232(14) . ?
C2A N2A 1.3264(14) . ?
C3A N2A 1.4488(13) . ?
C3A C4A 1.5128(14) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C4A O2A 1.2225(14) . ?
C4A N3A 1.3375(14) . ?
C5A N3A 1.4470(13) . ?
C5A C6A 1.5176(14) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C6A O3A 1.2275(14) . ?
C6A N4A 1.3319(14) . ?
C7A N4A 1.4533(13) . ?
C7A C8A 1.5257(14) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8A O5A 1.2342(14) . ?
C8A O4A 1.2584(13) . ?
N1A H1AC 0.8900 . ?
N1A H1AD 0.8900 . ?
N1A H1AE 0.8900 . ?
N2A H2A 0.8600 . ?
N3A H3A 0.8600 . ?
N4A H4A 0.8600 . ?
C1B N1B 1.4708(14) . ?
C1B C2B 1.5226(14) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C2B O1B 1.2237(14) . ?
C2B N2B 1.3313(14) . ?
C3B N2B 1.4490(13) . ?
C3B C4B 1.5239(14) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C4B O2B 1.2235(14) . ?
C4B N3B 1.3371(14) . ?
C5B N3B 1.4526(13) . ?
C5B C6B 1.5211(14) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C6B O3B 1.2234(14) . ?
C6B N4B 1.3357(14) . ?
C7B N4B 1.4516(13) . ?
C7B C8B 1.5241(15) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C8B O5B 1.2353(14) . ?
C8B O4B 1.2767(13) . ?
N1B H1BC 0.8900 . ?
N1B H1BD 0.8900 . ?
N1B H1BE 0.8900 . ?
N2B H2B 0.8600 . ?
N3B H3B 0.8600 . ?
N4B H4B 0.8600 . ?

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
N1A C1A C2A 109.76(9) . . ?
N1A C1A H1AA 109.7 . . ?
C2A C1A H1AA 109.7 . . ?
N1A C1A H1AB 109.7 . . ?
C2A C1A H1AB 109.7 . . ?
H1AA C1A H1AB 108.2 . . ?
O1A C2A N2A 123.46(10) . . ?
O1A C2A C1A 121.29(10) . . ?
N2A C2A C1A 115.25(9) . . ?
N2A C3A C4A 109.65(9) . . ?
N2A C3A H3AA 109.7 . . ?
C4A C3A H3AA 109.7 . . ?
N2A C3A H3AB 109.7 . . ?
C4A C3A H3AB 109.7 . . ?
H3AA C3A H3AB 108.2 . . ?
O2A C4A N3A 123.24(10) . . ?
O2A C4A C3A 122.31(9) . . ?
N3A C4A C3A 114.44(9) . . ?
N3A C5A C6A 109.74(9) . . ?
N3A C5A H5AA 109.7 . . ?
C6A C5A H5AA 109.7 . . ?
N3A C5A H5AB 109.7 . . ?
C6A C5A H5AB 109.7 . . ?
H5AA C5A H5AB 108.2 . . ?
O3A C6A N4A 123.62(10) . . ?
O3A C6A C5A 121.98(9) . . ?
N4A C6A C5A 114.40(9) . . ?
N4A C7A C8A 110.82(9) . . ?
N4A C7A H7AA 109.5 . . ?
C8A C7A H7AA 109.5 . . ?
N4A C7A H7AB 109.5 . . ?
C8A C7A H7AB 109.5 . . ?
H7AA C7A H7AB 108.1 . . ?
O5A C8A O4A 125.46(10) . . ?
O5A C8A C7A 118.57(9) . . ?
O4A C8A C7A 115.96(10) . . ?
C1A N1A H1AC 109.5 . . ?
C1A N1A H1AD 109.5 . . ?
H1AC N1A H1AD 109.5 . . ?
C1A N1A H1AE 109.5 . . ?
H1AC N1A H1AE 109.5 . . ?
H1AD N1A H1AE 109.5 . . ?
C2A N2A C3A 119.39(9) . . ?
C2A N2A H2A 120.3 . . ?
C3A N2A H2A 120.3 . . ?
C4A N3A C5A 120.22(9) . . ?
C4A N3A H3A 119.9 . . ?
C5A N3A H3A 119.9 . . ?
C6A N4A C7A 122.17(9) . . ?
C6A N4A H4A 118.9 . . ?
C7A N4A H4A 118.9 . . ?
N1B C1B C2B 108.75(9) . . ?
N1B C1B H1BA 109.9 . . ?
C2B C1B H1BA 109.9 . . ?
N1B C1B H1BB 109.9 . . ?
C2B C1B H1BB 109.9 . . ?
H1BA C1B H1BB 108.3 . . ?
O1B C2B N2B 124.29(10) . . ?
O1B C2B C1B 120.96(9) . . ?
N2B C2B C1B 114.74(9) . . ?
N2B C3B C4B 108.24(9) . . ?
N2B C3B H3BA 110.0 . . ?
C4B C3B H3BA 110.0 . . ?
N2B C3B H3BB 110.0 . . ?
C4B C3B H3BB 110.0 . . ?
H3BA C3B H3BB 108.4 . . ?
O2B C4B N3B 123.22(10) . . ?
O2B C4B C3B 121.25(9) . . ?
N3B C4B C3B 115.53(9) . . ?
N3B C5B C6B 111.19(9) . . ?
N3B C5B H5BA 109.4 . . ?
C6B C5B H5BA 109.4 . . ?
N3B C5B H5BB 109.4 . . ?
C6B C5B H5BB 109.4 . . ?
H5BA C5B H5BB 108.0 . . ?
O3B C6B N4B 123.89(10) . . ?
O3B C6B C5B 122.57(9) . . ?
N4B C6B C5B 113.54(9) . . ?
N4B C7B C8B 111.15(9) . . ?
N4B C7B H7BA 109.4 . . ?
C8B C7B H7BA 109.4 . . ?
N4B C7B H7BB 109.4 . . ?
C8B C7B H7BB 109.4 . . ?
H7BA C7B H7BB 108.0 . . ?
O5B C8B O4B 124.18(10) . . ?
O5B C8B C7B 119.97(9) . . ?
O4B C8B C7B 115.85(9) . . ?
C1B N1B H1BC 109.5 . . ?
C1B N1B H1BD 109.5 . . ?
H1BC N1B H1BD 109.5 . . ?
C1B N1B H1BE 109.5 . . ?
H1BC N1B H1BE 109.5 . . ?
H1BD N1B H1BE 109.5 . . ?
C2B N2B C3B 121.63(9) . . ?
C2B N2B H2B 119.2 . . ?
C3B N2B H2B 119.2 . . ?
C4B N3B C5B 118.90(9) . . ?
C4B N3B H3B 120.5 . . ?
C5B N3B H3B 120.5 . . ?
C6B N4B C7B 122.91(9) . . ?
C6B N4B H4B 118.5 . . ?
C7B N4B H4B 118.5 . . ?

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
N1A C1A C2A O1A 31.60(16) . . . . ?
N1A C1A C2A N2A -149.29(10) . . . . ?
N2A C3A C4A O2A 9.23(17) . . . . ?
N2A C3A C4A N3A -171.22(10) . . . . ?
N3A C5A C6A O3A 2.68(16) . . . . ?
N3A C5A C6A N4A -177.45(10) . . . . ?
N4A C7A C8A O5A -12.32(16) . . . . ?
N4A C7A C8A O4A 169.09(10) . . . . ?
O1A C2A N2A C3A 2.45(19) . . . . ?
C1A C2A N2A C3A -176.64(10) . . . . ?
C4A C3A N2A C2A 178.05(10) . . . . ?
O2A C4A N3A C5A -0.04(19) . . . . ?
C3A C4A N3A C5A -179.58(10) . . . . ?
C6A C5A N3A C4A 173.75(10) . . . . ?
O3A C6A N4A C7A -5.25(19) . . . . ?
C5A C6A N4A C7A 174.88(10) . . . . ?
C8A C7A N4A C6A -172.26(10) . . . . ?
N1B C1B C2B O1B 19.70(15) . . . . ?
N1B C1B C2B N2B -159.17(10) . . . . ?
N2B C3B C4B O2B -8.98(15) . . . . ?
N2B C3B C4B N3B 171.98(10) . . . . ?
N3B C5B C6B O3B -7.92(17) . . . . ?
N3B C5B C6B N4B 172.83(10) . . . . ?
N4B C7B C8B O5B -4.77(16) . . . . ?
N4B C7B C8B O4B 174.50(10) . . . . ?
O1B C2B N2B C3B -3.44(18) . . . . ?
C1B C2B N2B C3B 175.40(10) . . . . ?
C4B C3B N2B C2B -165.23(10) . . . . ?
O2B C4B N3B C5B 0.90(18) . . . . ?
C3B C4B N3B C5B 179.91(10) . . . . ?
C6B C5B N3B C4B -175.62(10) . . . . ?
O3B C6B N4B C7B -0.22(19) . . . . ?
C5B C6B N4B C7B 179.02(10) . . . . ?
C8B C7B N4B C6B -174.63(10) . . . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 993137'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 Glycyl-glycyl-glycyl-glycyl-glycine
;
_chemical_name_common            Pentaglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H17 N5 O6'
_chemical_formula_sum            'C10 H17 N5 O6'
_chemical_formula_weight         303.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7995(3)
_cell_length_b                   14.9108(15)
_cell_length_c                   17.6905(19)
_cell_angle_alpha                90.203(8)
_cell_angle_beta                 94.866(7)
_cell_angle_gamma                91.976(7)
_cell_volume                     1260.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3113
_cell_measurement_theta_min      3.8687
_cell_measurement_theta_max      71.9283

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.142
_shelx_estimated_absorpt_T_min   0.726
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7257
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET)
(compiled Mar  7 2011,18:06:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3693
_diffrn_reflns_number            17005
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.872
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             4425
_reflns_number_gt                3162
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET)
(compiled Mar  7 2011,18:06:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET)
(compiled Mar  7 2011,18:06:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET)
(compiled Mar  7 2011,18:06:32)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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     
'w=1/[σ²(Fo²)+(0.1572P)²+0.3578P] where P=(Fo²+2Fc²)/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         4425
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_ref         0.2538
_refine_ls_wR_factor_gt          0.2350
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.7279(7) 0.3937(2) 0.88576(19) 0.0429(8) Uani 1 1 d . . . . .
H1AA H 0.5349 0.3989 0.8655 0.051 Uiso 1 1 calc R U . . .
H1AB H 0.7762 0.3313 0.8818 0.051 Uiso 1 1 calc R U . . .
C2A C 0.9187(6) 0.4520(2) 0.83972(19) 0.0361(7) Uani 1 1 d . . . . .
C3A C 1.0035(7) 0.5130(2) 0.71669(18) 0.0380(8) Uani 1 1 d . . . . .
H3AA H 1.1828 0.4882 0.7086 0.046 Uiso 1 1 calc R U . . .
H3AB H 1.0373 0.5720 0.7397 0.046 Uiso 1 1 calc R U . . .
C4A C 0.8309(6) 0.5208(2) 0.64188(18) 0.0331(7) Uani 1 1 d . . . . .
C5A C 0.7768(6) 0.5935(2) 0.52025(18) 0.0366(7) Uani 1 1 d . . . . .
H5AA H 0.5925 0.6158 0.5264 0.044 Uiso 1 1 calc R U . . .
H5AB H 0.7535 0.5364 0.4938 0.044 Uiso 1 1 calc R U . . .
C6A C 0.9380(6) 0.6597(2) 0.47390(18) 0.0320(7) Uani 1 1 d . . . . .
C7A C 0.9722(6) 0.7295(2) 0.35165(18) 0.0374(7) Uani 1 1 d . . . . .
H7AA H 1.1591 0.7096 0.3451 0.045 Uiso 1 1 calc R U . . .
H7AB H 0.9890 0.7892 0.3738 0.045 Uiso 1 1 calc R U . . .
C8A C 0.8067(6) 0.7325(2) 0.27568(18) 0.0331(7) Uani 1 1 d . . . . .
C9A C 0.7677(7) 0.8054(2) 0.1519(2) 0.0435(8) Uani 1 1 d . . . . .
H9AA H 0.5761 0.8211 0.1577 0.052 Uiso 1 1 calc R U . . .
H9AB H 0.7627 0.7506 0.1221 0.052 Uiso 1 1 calc R U . . .
C10A C 0.9136(7) 0.8808(2) 0.10964(19) 0.0394(8) Uani 1 1 d . . . . .
N1A N 0.7574(6) 0.4213(2) 0.96414(16) 0.0448(7) Uani 1 1 d . . . . .
H1AC H 0.6202 0.3958 0.9883 0.054 Uiso 1 1 calc R U . . .
H1AD H 0.7485 0.4807 0.9671 0.054 Uiso 1 1 calc R U . . .
H1AE H 0.9217 0.4045 0.9855 0.054 Uiso 1 1 calc R U . . .
N2A N 0.8533(5) 0.45484(19) 0.76694(16) 0.0388(7) Uani 1 1 d . . . . .
H2A H 0.7163 0.4211 0.7476 0.047 Uiso 1 1 calc R U . . .
N3A N 0.9254(5) 0.58131(19) 0.59407(15) 0.0377(7) Uani 1 1 d . . . . .
H3A H 1.0747 0.6131 0.6071 0.045 Uiso 1 1 calc R U . . .
N4A N 0.8379(5) 0.66895(19) 0.40237(16) 0.0381(7) Uani 1 1 d . . . . .
H4A H 0.6900 0.6384 0.3857 0.046 Uiso 1 1 calc R U . . .
N5A N 0.9080(5) 0.7897(2) 0.22566(16) 0.0406(7) Uani 1 1 d . . . . .
H5A H 1.0638 0.8184 0.2382 0.049 Uiso 1 1 calc R U . . .
O1A O 1.1206(5) 0.49444(19) 0.87313(14) 0.0508(7) Uani 1 1 d . . . . .
O2A O 0.6198(5) 0.47215(17) 0.62591(14) 0.0474(6) Uani 1 1 d . . . . .
O3A O 1.1489(5) 0.70176(17) 0.50228(14) 0.0466(6) Uani 1 1 d . . . . .
O4A O 0.5927(5) 0.68555(17) 0.26071(14) 0.0478(7) Uani 1 1 d . . . . .
O5A O 1.1506(5) 0.9071(2) 0.13593(16) 0.0631(9) Uani 1 1 d . . . . .
O6A O 0.7890(5) 0.90829(18) 0.05070(14) 0.0486(7) Uani 1 1 d . . . . .
C1B C 0.4851(7) -0.0865(2) 0.8981(2) 0.0417(8) Uani 1 1 d . . . . .
H1BA H 0.6106 -0.1356 0.8942 0.050 Uiso 1 1 calc R U . . .
H1BB H 0.5975 -0.0323 0.9103 0.050 Uiso 1 1 calc R U . . .
C2B C 0.3157(7) -0.0752(2) 0.82380(19) 0.0389(8) Uani 1 1 d . . . . .
C3B C 0.2785(7) -0.0080(2) 0.70069(19) 0.0395(8) Uani 1 1 d . . . . .
H3BA H 0.0940 0.0147 0.7059 0.047 Uiso 1 1 calc R U . . .
H3BB H 0.2554 -0.0655 0.6747 0.047 Uiso 1 1 calc R U . . .
C4B C 0.4427(6) 0.0570(2) 0.65427(18) 0.0339(7) Uani 1 1 d . . . . .
C5B C 0.4825(7) 0.1255(2) 0.53187(18) 0.0367(7) Uani 1 1 d . . . . .
H5BA H 0.6679 0.1052 0.5241 0.044 Uiso 1 1 calc R U . . .
H5BB H 0.5024 0.1849 0.5545 0.044 Uiso 1 1 calc R U . . .
C6B C 0.3122(6) 0.1295(2) 0.45723(18) 0.0340(7) Uani 1 1 d . . . . .
C7B C 0.2537(6) 0.2003(2) 0.33436(18) 0.0368(8) Uani 1 1 d . . . . .
H7BA H 0.0687 0.2218 0.3408 0.044 Uiso 1 1 calc R U . . .
H7BB H 0.2313 0.1425 0.3088 0.044 Uiso 1 1 calc R U . . .
C8B C 0.4060(6) 0.2656(2) 0.28576(18) 0.0340(7) Uani 1 1 d . . . . .
C9B C 0.4072(7) 0.3297(2) 0.15913(19) 0.0402(8) Uani 1 1 d . . . . .
H9BA H 0.5939 0.3123 0.1494 0.048 Uiso 1 1 calc R U . . .
H9BB H 0.4205 0.3905 0.1790 0.048 Uiso 1 1 calc R U . . .
C10B C 0.2210(7) 0.3269(2) 0.08535(19) 0.0398(8) Uani 1 1 d . . . . .
N1B N 0.2995(6) -0.1052(2) 0.95884(16) 0.0449(7) Uani 1 1 d . . . . .
H1BC H 0.1974 -0.1552 0.9477 0.054 Uiso 1 1 calc R U . . .
H1BD H 0.1867 -0.0596 0.9629 0.054 Uiso 1 1 calc R U . . .
H1BE H 0.4022 -0.1121 1.0026 0.054 Uiso 1 1 calc R U . . .
N2B N 0.4214(6) -0.0196(2) 0.77467(16) 0.0412(7) Uani 1 1 d . . . . .
H2B H 0.5761 0.0098 0.7870 0.049 Uiso 1 1 calc R U . . .
N3B N 0.3481(6) 0.06425(19) 0.58278(16) 0.0384(7) Uani 1 1 d . . . . .
H3B H 0.2039 0.0322 0.5656 0.046 Uiso 1 1 calc R U . . .
N4B N 0.4035(5) 0.18937(19) 0.40839(15) 0.0368(6) Uani 1 1 d . . . . .
H4B H 0.5523 0.2217 0.4208 0.044 Uiso 1 1 calc R U . . .
N5B N 0.2991(6) 0.27010(19) 0.21504(16) 0.0408(7) Uani 1 1 d . . . . .
H5B H 0.1564 0.2356 0.2011 0.049 Uiso 1 1 calc R U . . .
O1B O 0.0878(6) -0.1161(2) 0.81014(15) 0.0635(9) Uani 1 1 d . . . . .
O2B O 0.6498(5) 0.10035(18) 0.68301(14) 0.0497(7) Uani 1 1 d . . . . .
O3B O 0.1028(5) 0.08005(17) 0.44229(13) 0.0466(6) Uani 1 1 d . . . . .
O4B O 0.6138(5) 0.31080(18) 0.31238(14) 0.0504(7) Uani 1 1 d . . . . .
O5B O 0.0196(6) 0.27225(19) 0.07691(16) 0.0558(7) Uani 1 1 d . . . . .
O6B O 0.2858(5) 0.38257(17) 0.03505(14) 0.0465(6) Uani 1 1 d . . . . .


_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
C1A N1A 1.439(5) . ?
C1A C2A 1.529(4) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C2A O1A 1.243(4) . ?
C2A N2A 1.300(4) . ?
C3A N2A 1.461(4) . ?
C3A C4A 1.507(4) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C4A O2A 1.237(4) . ?
C4A N3A 1.334(4) . ?
C5A N3A 1.449(4) . ?
C5A C6A 1.518(4) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C6A O3A 1.241(4) . ?
C6A N4A 1.324(4) . ?
C7A N4A 1.449(4) . ?
C7A C8A 1.504(4) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8A O4A 1.232(4) . ?
C8A N5A 1.340(4) . ?
C9A N5A 1.440(4) . ?
C9A C10A 1.534(4) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C10A O6A 1.236(4) . ?
C10A O5A 1.242(4) . ?
N1A H1AC 0.8900 . ?
N1A H1AD 0.8900 . ?
N1A H1AE 0.8900 . ?
N2A H2A 0.8600 . ?
N3A H3A 0.8600 . ?
N4A H4A 0.8600 . ?
N5A H5A 0.8600 . ?
C1B N1B 1.475(4) . ?
C1B C2B 1.499(5) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C2B O1B 1.238(4) . ?
C2B N2B 1.324(4) . ?
C3B N2B 1.439(4) . ?
C3B C4B 1.516(4) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C4B O2B 1.238(4) . ?
C4B N3B 1.313(4) . ?
C5B N3B 1.458(4) . ?
C5B C6B 1.495(5) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C6B O3B 1.236(4) . ?
C6B N4B 1.333(4) . ?
C7B N4B 1.452(4) . ?
C7B C8B 1.512(4) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C8B O4B 1.242(4) . ?
C8B N5B 1.314(4) . ?
C9B N5B 1.448(4) . ?
C9B C10B 1.518(5) . ?
C9B H9BA 0.9700 . ?
C9B H9BB 0.9700 . ?
C10B O5B 1.241(4) . ?
C10B O6B 1.270(4) . ?
N1B H1BC 0.8900 . ?
N1B H1BD 0.8900 . ?
N1B H1BE 0.8900 . ?
N2B H2B 0.8600 . ?
N3B H3B 0.8600 . ?
N4B H4B 0.8600 . ?
N5B H5B 0.8600 . ?

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
N1A C1A C2A 110.2(3) . . ?
N1A C1A H1AA 109.6 . . ?
C2A C1A H1AA 109.6 . . ?
N1A C1A H1AB 109.6 . . ?
C2A C1A H1AB 109.6 . . ?
H1AA C1A H1AB 108.1 . . ?
O1A C2A N2A 124.2(3) . . ?
O1A C2A C1A 119.2(3) . . ?
N2A C2A C1A 116.5(3) . . ?
N2A C3A C4A 109.2(2) . . ?
N2A C3A H3AA 109.8 . . ?
C4A C3A H3AA 109.8 . . ?
N2A C3A H3AB 109.8 . . ?
C4A C3A H3AB 109.8 . . ?
H3AA C3A H3AB 108.3 . . ?
O2A C4A N3A 122.8(3) . . ?
O2A C4A C3A 121.6(3) . . ?
N3A C4A C3A 115.6(3) . . ?
N3A C5A C6A 110.2(2) . . ?
N3A C5A H5AA 109.6 . . ?
C6A C5A H5AA 109.6 . . ?
N3A C5A H5AB 109.6 . . ?
C6A C5A H5AB 109.6 . . ?
H5AA C5A H5AB 108.1 . . ?
O3A C6A N4A 123.1(3) . . ?
O3A C6A C5A 121.2(3) . . ?
N4A C6A C5A 115.6(3) . . ?
N4A C7A C8A 110.9(2) . . ?
N4A C7A H7AA 109.5 . . ?
C8A C7A H7AA 109.5 . . ?
N4A C7A H7AB 109.5 . . ?
C8A C7A H7AB 109.5 . . ?
H7AA C7A H7AB 108.1 . . ?
O4A C8A N5A 122.5(3) . . ?
O4A C8A C7A 122.1(3) . . ?
N5A C8A C7A 115.4(2) . . ?
N5A C9A C10A 112.0(2) . . ?
N5A C9A H9AA 109.2 . . ?
C10A C9A H9AA 109.2 . . ?
N5A C9A H9AB 109.2 . . ?
C10A C9A H9AB 109.2 . . ?
H9AA C9A H9AB 107.9 . . ?
O6A C10A O5A 125.3(3) . . ?
O6A C10A C9A 117.1(3) . . ?
O5A C10A C9A 117.5(3) . . ?
C1A N1A H1AC 109.5 . . ?
C1A N1A H1AD 109.5 . . ?
H1AC N1A H1AD 109.5 . . ?
C1A N1A H1AE 109.5 . . ?
H1AC N1A H1AE 109.5 . . ?
H1AD N1A H1AE 109.5 . . ?
C2A N2A C3A 122.6(3) . . ?
C2A N2A H2A 118.7 . . ?
C3A N2A H2A 118.7 . . ?
C4A N3A C5A 120.1(3) . . ?
C4A N3A H3A 120.0 . . ?
C5A N3A H3A 120.0 . . ?
C6A N4A C7A 121.4(2) . . ?
C6A N4A H4A 119.3 . . ?
C7A N4A H4A 119.3 . . ?
C8A N5A C9A 122.9(2) . . ?
C8A N5A H5A 118.5 . . ?
C9A N5A H5A 118.5 . . ?
N1B C1B C2B 110.2(3) . . ?
N1B C1B H1BA 109.6 . . ?
C2B C1B H1BA 109.6 . . ?
N1B C1B H1BB 109.6 . . ?
C2B C1B H1BB 109.6 . . ?
H1BA C1B H1BB 108.1 . . ?
O1B C2B N2B 122.5(3) . . ?
O1B C2B C1B 120.9(3) . . ?
N2B C2B C1B 116.6(3) . . ?
N2B C3B C4B 110.5(2) . . ?
N2B C3B H3BA 109.6 . . ?
C4B C3B H3BA 109.6 . . ?
N2B C3B H3BB 109.6 . . ?
C4B C3B H3BB 109.6 . . ?
H3BA C3B H3BB 108.1 . . ?
O2B C4B N3B 123.1(3) . . ?
O2B C4B C3B 121.4(3) . . ?
N3B C4B C3B 115.5(3) . . ?
N3B C5B C6B 110.3(2) . . ?
N3B C5B H5BA 109.6 . . ?
C6B C5B H5BA 109.6 . . ?
N3B C5B H5BB 109.6 . . ?
C6B C5B H5BB 109.6 . . ?
H5BA C5B H5BB 108.1 . . ?
O3B C6B N4B 122.9(3) . . ?
O3B C6B C5B 121.8(3) . . ?
N4B C6B C5B 115.4(2) . . ?
N4B C7B C8B 111.7(2) . . ?
N4B C7B H7BA 109.3 . . ?
C8B C7B H7BA 109.3 . . ?
N4B C7B H7BB 109.3 . . ?
C8B C7B H7BB 109.3 . . ?
H7BA C7B H7BB 107.9 . . ?
O4B C8B N5B 124.2(3) . . ?
O4B C8B C7B 121.2(3) . . ?
N5B C8B C7B 114.6(3) . . ?
N5B C9B C10B 111.5(2) . . ?
N5B C9B H9BA 109.3 . . ?
C10B C9B H9BA 109.3 . . ?
N5B C9B H9BB 109.3 . . ?
C10B C9B H9BB 109.3 . . ?
H9BA C9B H9BB 108.0 . . ?
O5B C10B O6B 123.9(3) . . ?
O5B C10B C9B 120.1(3) . . ?
O6B C10B C9B 116.0(3) . . ?
C1B N1B H1BC 109.5 . . ?
C1B N1B H1BD 109.5 . . ?
H1BC N1B H1BD 109.5 . . ?
C1B N1B H1BE 109.5 . . ?
H1BC N1B H1BE 109.5 . . ?
H1BD N1B H1BE 109.5 . . ?
C2B N2B C3B 120.2(3) . . ?
C2B N2B H2B 119.9 . . ?
C3B N2B H2B 119.9 . . ?
C4B N3B C5B 121.4(2) . . ?
C4B N3B H3B 119.3 . . ?
C5B N3B H3B 119.3 . . ?
C6B N4B C7B 120.5(2) . . ?
C6B N4B H4B 119.8 . . ?
C7B N4B H4B 119.8 . . ?
C8B N5B C9B 123.9(3) . . ?
C8B N5B H5B 118.1 . . ?
C9B N5B H5B 118.1 . . ?

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
N1A C1A C2A O1A 20.0(5) . . . . ?
N1A C1A C2A N2A -158.9(3) . . . . ?
N2A C3A C4A O2A -10.2(5) . . . . ?
N2A C3A C4A N3A 171.5(3) . . . . ?
N3A C5A C6A O3A -7.1(5) . . . . ?
N3A C5A C6A N4A 173.0(3) . . . . ?
N4A C7A C8A O4A -2.7(5) . . . . ?
N4A C7A C8A N5A 177.3(3) . . . . ?
N5A C9A C10A O6A -170.0(3) . . . . ?
N5A C9A C10A O5A 12.3(5) . . . . ?
O1A C2A N2A C3A -3.6(6) . . . . ?
C1A C2A N2A C3A 175.2(3) . . . . ?
C4A C3A N2A C2A -163.9(3) . . . . ?
O2A C4A N3A C5A 1.1(5) . . . . ?
C3A C4A N3A C5A 179.4(3) . . . . ?
C6A C5A N3A C4A -175.0(3) . . . . ?
O3A C6A N4A C7A 0.5(5) . . . . ?
C5A C6A N4A C7A -179.7(3) . . . . ?
C8A C7A N4A C6A -176.0(3) . . . . ?
O4A C8A N5A C9A 3.8(6) . . . . ?
C7A C8A N5A C9A -176.2(3) . . . . ?
C10A C9A N5A C8A 174.2(3) . . . . ?
N1B C1B C2B O1B -30.8(5) . . . . ?
N1B C1B C2B N2B 148.8(3) . . . . ?
N2B C3B C4B O2B -8.5(5) . . . . ?
N2B C3B C4B N3B 172.3(3) . . . . ?
N3B C5B C6B O3B -5.9(5) . . . . ?
N3B C5B C6B N4B 174.6(3) . . . . ?
N4B C7B C8B O4B -8.4(5) . . . . ?
N4B C7B C8B N5B 172.1(3) . . . . ?
N5B C9B C10B O5B -5.9(5) . . . . ?
N5B C9B C10B O6B 174.2(3) . . . . ?
O1B C2B N2B C3B -3.3(6) . . . . ?
C1B C2B N2B C3B 177.1(3) . . . . ?
C4B C3B N2B C2B -178.6(3) . . . . ?
O2B C4B N3B C5B -0.4(5) . . . . ?
C3B C4B N3B C5B 178.9(3) . . . . ?
C6B C5B N3B C4B -172.6(3) . . . . ?
O3B C6B N4B C7B 1.2(5) . . . . ?
C5B C6B N4B C7B -179.3(3) . . . . ?
C8B C7B N4B C6B -175.1(3) . . . . ?
O4B C8B N5B C9B -1.1(6) . . . . ?
C7B C8B N5B C9B 178.4(3) . . . . ?
C10B C9B N5B C8B -173.7(3) . . . . ?

_refine_diff_density_max         0.665
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.113

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 993138'
