#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/58/2205871.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2205871
loop_
_publ_author_name
'K. Anitha'
'S. Athimoolam'
'R. K. Rajaram'
_publ_section_title
;
 <small>L</small>-Leucine <small>L</small>-leucinium picrate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1604
_journal_page_last               o1606
_journal_paper_doi               10.1107/S1600536805014030
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C6 H13 N O2, C6 H14 N O2 +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C6 H13 N O2, C6 H14 N O2 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C18 H29 N5 O11'
_chemical_formula_weight         491.46
_chemical_name_common
;
L-Leucine L-leucinium picrate
;
_chemical_name_systematic
;
L-Leucine L-leucinium picrate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.45(2)
_cell_angle_beta                 95.170(10)
_cell_angle_gamma                91.02(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1470(5)
_cell_length_b                   11.8540(8)
_cell_length_c                   15.4560(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.91
_cell_measurement_theta_min      10.40
_cell_volume                     1249.4(2)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'PLATON (Spek, 2003) and SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius MACH3 sealed tube'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5538
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      1.297
_exptl_crystal_density_method
'flotation in a mixture of carbon tetracholride and xylene'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.501
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     609
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0871P)²+0.3632P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1495
_reflns_number_gt                3495
_reflns_number_total             4392
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6660.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (8
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (12
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (34 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (8
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (12
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (34 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1249.5(2)
_cod_database_code               2205871
_cod_database_fobs_code          2205871
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.6176(7) 0.7671(4) 0.8035(3) 0.0417(11) Uani d . 1 C
C2 0.4548(7) 0.7822(4) 0.8537(3) 0.0433(11) Uani d . 1 C
C3 0.4338(7) 0.7357(5) 0.9250(3) 0.0462(12) Uani d . 1 C
H3 0.3256 0.7477 0.9551 0.055 Uiso calc R 1 H
C4 0.5764(8) 0.6711(5) 0.9507(3) 0.0474(13) Uani d . 1 C
C5 0.7364(8) 0.6505(4) 0.9058(3) 0.0457(12) Uani d . 1 C
H5 0.8306 0.6065 0.9240 0.055 Uiso calc R 1 H
C6 0.7554(7) 0.6956(4) 0.8337(3) 0.0412(11) Uani d . 1 C
N3 0.3022(7) 0.8483(5) 0.8289(3) 0.0579(12) Uani d . 1 N
N1 0.9216(7) 0.6659(5) 0.7873(3) 0.0581(12) Uani d . 1 N
N2 0.5577(9) 0.6264(5) 1.0273(3) 0.0649(14) Uani d . 1 N
O1 0.6372(5) 0.8156(4) 0.7423(2) 0.0559(10) Uani d . 1 O
O7 0.2739(7) 0.8528(6) 0.7507(3) 0.0908(17) Uani d . 1 O
O6 0.2046(7) 0.8986(5) 0.8866(3) 0.0858(15) Uani d . 1 O
O5 0.4181(8) 0.6490(5) 1.0677(3) 0.0853(15) Uani d . 1 O
O4 0.6892(9) 0.5737(6) 1.0520(4) 0.1029(19) Uani d . 1 O
O3 1.0540(7) 0.6235(5) 0.8222(4) 0.0882(15) Uani d . 1 O
O2 0.9304(8) 0.6832(7) 0.7137(4) 0.116(2) Uani d . 1 O
C11 0.6452(7) 0.8929(4) 0.1905(3) 0.0421(11) Uani d . 1 C
C12 0.5065(7) 0.9652(5) 0.1574(3) 0.0451(12) Uani d . 1 C
C13 0.5272(8) 1.0089(5) 0.0865(3) 0.0480(12) Uani d . 1 C
H13 0.4326 1.0523 0.0679 0.058 Uiso calc R 1 H
C14 0.6860(7) 0.9897(5) 0.0421(3) 0.0438(11) Uani d . 1 C
C15 0.8262(8) 0.9214(5) 0.0663(3) 0.0486(12) Uani d . 1 C
H15 0.9312 0.9057 0.0341 0.058 Uiso calc R 1 H
C16 0.8075(7) 0.8781(5) 0.1374(3) 0.0456(12) Uani d . 1 C
N11 0.3374(7) 0.9942(5) 0.2041(4) 0.0627(13) Uani d . 1 N
N12 0.7062(8) 1.0359(5) -0.0342(3) 0.0594(13) Uani d . 1 N
N13 0.9586(7) 0.8070(4) 0.1595(3) 0.0580(12) Uani d . 1 N
O11 0.6263(6) 0.8484(4) 0.2529(2) 0.0551(10) Uani d . 1 O
O12 0.3182(8) 0.9669(7) 0.2719(4) 0.117(2) Uani d . 1 O
O13 0.2168(8) 1.0415(7) 0.1701(5) 0.119(2) Uani d . 1 O
O14 0.5792(8) 1.0890(5) -0.0587(4) 0.0920(17) Uani d . 1 O
O15 0.8502(8) 1.0184(5) -0.0720(3) 0.0886(16) Uani d . 1 O
O16 1.0580(7) 0.7590(5) 0.1010(3) 0.0888(16) Uani d . 1 O
O17 0.9861(7) 0.8032(5) 0.2383(3) 0.0820(15) Uani d . 1 O
C21 0.6535(6) 0.0380(4) 0.6472(3) 0.0403(10) Uani d . 1 C
C22 0.7999(6) 0.0708(4) 0.7294(3) 0.0401(10) Uani d . 1 C
H22 0.7342 0.0876 0.7844 0.048 Uiso calc R 1 H
C23 0.9235(9) 0.1801(5) 0.7332(4) 0.0566(14) Uani d . 1 C
H23A 1.0174 0.1566 0.6907 0.068 Uiso calc R 1 H
H23B 0.8453 0.2358 0.7133 0.068 Uiso calc R 1 H
C24 1.0223(12) 0.2413(6) 0.8256(4) 0.080(2) Uani d . 1 C
H24 1.0679 0.1828 0.8554 0.096 Uiso calc R 1 H
C25 0.8706(18) 0.3188(11) 0.8823(8) 0.154(3) Uani d . 1 C
H25A 0.7651 0.3270 0.8419 0.231 Uiso calc R 1 H
H25B 0.9262 0.3952 0.9145 0.231 Uiso calc R 1 H
H25C 0.8291 0.2807 0.9249 0.231 Uiso calc R 1 H
C26 1.181(2) 0.3242(10) 0.8235(8) 0.154(3) Uani d . 1 C
H26A 1.2548 0.2877 0.7751 0.231 Uiso calc R 1 H
H26B 1.2586 0.3432 0.8802 0.231 Uiso calc R 1 H
H26C 1.1314 0.3949 0.8140 0.231 Uiso calc R 1 H
N21 0.9190(6) -0.0321(4) 0.7267(3) 0.0456(10) Uani d . 1 N
H21A 0.8456 -0.0957 0.7213 0.068 Uiso calc R 1 H
H21B 0.9958 -0.0172 0.7776 0.068 Uiso calc R 1 H
H21C 0.9865 -0.0449 0.6795 0.068 Uiso calc R 1 H
O21B 0.5289(6) 0.1114(3) 0.6490(3) 0.0684(11) Uani d . 1 O
O21A 0.6664(5) -0.0557(3) 0.5861(2) 0.0454(8) Uani d . 1 O
C31 0.0903(7) 0.6128(4) 0.3338(3) 0.0439(11) Uani d . 1 C
C32 0.2107(6) 0.5778(4) 0.2540(3) 0.0405(10) Uani d . 1 C
H32 0.1276 0.5614 0.1975 0.049 Uiso calc R 1 H
C33 0.3199(8) 0.4691(5) 0.2533(4) 0.0519(13) Uani d . 1 C
H33A 0.4177 0.4900 0.3036 0.062 Uiso calc R 1 H
H33B 0.2353 0.4106 0.2639 0.062 Uiso calc R 1 H
C34 0.4100(17) 0.4133(9) 0.1681(6) 0.127(2) Uani d . 1 C
H34 0.4761 0.4773 0.1530 0.153 Uiso calc R 1 H
C35 0.2847(17) 0.3577(9) 0.0917(6) 0.127(2) Uani d . 1 C
H35A 0.2075 0.2992 0.1054 0.191 Uiso calc R 1 H
H35B 0.3547 0.3209 0.0419 0.191 Uiso calc R 1 H
H35C 0.2064 0.4151 0.0757 0.191 Uiso calc R 1 H
C36 0.5588(17) 0.3284(9) 0.1826(6) 0.127(2) Uani d . 1 C
H36A 0.4990 0.2601 0.1918 0.191 Uiso calc R 1 H
H36B 0.6437 0.3665 0.2350 0.191 Uiso calc R 1 H
H36C 0.6274 0.3051 0.1303 0.191 Uiso calc R 1 H
N31 0.3424(6) 0.6795(4) 0.2591(3) 0.0462(10) Uani d . 1 N
H31A 0.4260 0.6909 0.3074 0.069 Uiso calc R 1 H
H31B 0.2776 0.7440 0.2638 0.069 Uiso calc R 1 H
H31C 0.4020 0.6641 0.2092 0.069 Uiso calc R 1 H
O31B -0.0397(6) 0.5388(3) 0.3302(3) 0.0732(12) Uani d . 1 O
O31A 0.1296(5) 0.7062(3) 0.3954(2) 0.0461(8) Uani d . 1 O
C41 1.1462(6) 0.0021(4) 0.5153(3) 0.0409(10) Uani d . 1 C
C42 0.9944(6) 0.0011(4) 0.4392(3) 0.0372(10) Uani d . 1 C
H42 1.0547 -0.0028 0.3840 0.045 Uiso calc R 1 H
C43 0.8846(8) 0.1146(4) 0.4642(3) 0.0446(12) Uani d . 1 C
H43A 0.8015 0.1089 0.5092 0.053 Uiso calc R 1 H
H43B 0.9736 0.1803 0.4923 0.053 Uiso calc R 1 H
C45 0.8862(12) 0.1732(7) 0.3202(5) 0.086(2) Uani d . 1 C
H45A 0.8071 0.1836 0.2697 0.129 Uiso calc R 1 H
H45B 0.9694 0.1108 0.2990 0.129 Uiso calc R 1 H
H45C 0.9586 0.2449 0.3500 0.129 Uiso calc R 1 H
C44 0.7669(8) 0.1424(5) 0.3856(4) 0.0567(13) Uani d . 1 C
H44 0.6904 0.0713 0.3525 0.068 Uiso calc R 1 H
C46 0.6333(10) 0.2383(6) 0.4227(5) 0.082(2) Uani d . 1 C
H46A 0.7042 0.3085 0.4575 0.123 Uiso calc R 1 H
H46B 0.5531 0.2127 0.4607 0.123 Uiso calc R 1 H
H46C 0.5579 0.2545 0.3733 0.123 Uiso calc R 1 H
N41 0.8670(6) -0.1047(4) 0.4223(3) 0.0399(9) Uani d . 1 N
H41A 0.9346 -0.1667 0.4233 0.060 Uiso calc R 1 H
H41B 0.8016 -0.1180 0.3683 0.060 Uiso calc R 1 H
H41C 0.7883 -0.0929 0.4652 0.060 Uiso calc R 1 H
O41A 1.1312(5) -0.0613(3) 0.5647(2) 0.0483(9) Uani d . 1 O
O41B 1.2785(6) 0.0786(4) 0.5222(3) 0.0718(12) Uani d . 1 O
H41D 1.3615 0.0730 0.5608 0.108 Uiso calc R 1 H
C51 0.6333(7) 0.6409(4) 0.4631(3) 0.0418(10) Uani d . 1 C
C52 0.5207(6) 0.6460(4) 0.5426(3) 0.0368(9) Uani d . 1 C
H52 0.6083 0.6518 0.5964 0.044 Uiso calc R 1 H
C53 0.3900(7) 0.5363(4) 0.5256(3) 0.0438(11) Uani d . 1 C
H53A 0.2832 0.5420 0.4839 0.053 Uiso calc R 1 H
H53B 0.4571 0.4677 0.4962 0.053 Uiso calc R 1 H
C54 0.3170(9) 0.5167(5) 0.6097(4) 0.0586(14) Uani d . 1 C
H54 0.2761 0.5919 0.6471 0.070 Uiso calc R 1 H
C55 0.4686(13) 0.4722(7) 0.6655(5) 0.093(3) Uani d . 1 C
H55A 0.4835 0.3899 0.6377 0.139 Uiso calc R 1 H
H55B 0.4328 0.4833 0.7257 0.139 Uiso calc R 1 H
H55C 0.5853 0.5152 0.6685 0.139 Uiso calc R 1 H
C56 0.1461(11) 0.4290(7) 0.5805(6) 0.095(2) Uani d . 1 C
H56A 0.0498 0.4603 0.5478 0.142 Uiso calc R 1 H
H56B 0.0984 0.4162 0.6333 0.142 Uiso calc R 1 H
H56C 0.1834 0.3556 0.5424 0.142 Uiso calc R 1 H
N51 0.4088(6) 0.7542(3) 0.5598(3) 0.0417(9) Uani d . 1 N
H51A 0.4820 0.8154 0.5591 0.063 Uiso calc R 1 H
H51B 0.3647 0.7679 0.6137 0.063 Uiso calc R 1 H
H51C 0.3131 0.7438 0.5169 0.063 Uiso calc R 1 H
O51B 0.7605(6) 0.5641(4) 0.4548(3) 0.0674(11) Uani d . 1 O
H51D 0.8161 0.5631 0.4104 0.101 Uiso calc R 1 H
O51A 0.6049(5) 0.7054(3) 0.4153(2) 0.0490(9) Uani d . 1 O
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C6 124.5(5) ?
O1 C1 C2 122.5(5) ?
C6 C1 C2 113.0(4) ?
C3 C2 N3 116.9(5) ?
C3 C2 C1 123.9(5) ?
N3 C2 C1 119.2(4) ?
C2 C3 C4 118.7(5) ?
C2 C3 H3 120.6 ?
C4 C3 H3 120.6 ?
C5 C4 C3 121.5(4) ?
C5 C4 N2 119.7(5) ?
C3 C4 N2 118.8(5) ?
C4 C5 C6 119.5(5) ?
C4 C5 H5 120.3 ?
C6 C5 H5 120.3 ?
C5 C6 N1 116.5(5) ?
C5 C6 C1 123.3(4) ?
N1 C6 C1 120.2(4) ?
O6 N3 O7 121.4(5) ?
O6 N3 C2 118.7(5) ?
O7 N3 C2 119.9(5) ?
O2 N1 O3 120.4(5) ?
O2 N1 C6 119.7(5) ?
O3 N1 C6 119.9(5) ?
O5 N2 O4 123.2(5) ?
O5 N2 C4 118.6(5) ?
O4 N2 C4 118.1(5) ?
O11 C11 C16 124.6(5) ?
O11 C11 C12 125.1(5) ?
C16 C11 C12 110.3(4) ?
C13 C12 N11 117.4(5) ?
C13 C12 C11 123.9(5) ?
N11 C12 C11 118.6(5) ?
C12 C13 C14 120.6(5) ?
C12 C13 H13 119.7 ?
C14 C13 H13 119.7 ?
C13 C14 C15 120.8(5) ?
C13 C14 N12 120.2(5) ?
C15 C14 N12 118.9(5) ?
C16 C15 C14 119.0(5) ?
C16 C15 H15 120.5 ?
C14 C15 H15 120.5 ?
C15 C16 N13 116.5(5) ?
C15 C16 C11 125.3(5) ?
N13 C16 C11 118.2(4) ?
O13 N11 O12 121.8(6) ?
O13 N11 C12 117.4(5) ?
O12 N11 C12 120.7(5) ?
O14 N12 O15 122.4(5) ?
O14 N12 C14 118.8(5) ?
O15 N12 C14 118.8(5) ?
O16 N13 O17 122.8(5) ?
O16 N13 C16 119.2(5) ?
O17 N13 C16 118.0(5) ?
O21A C21 O21B 126.4(4) y
O21A C21 C22 119.3(4) y
O21B C21 C22 114.2(4) y
N21 C22 C21 108.7(4) ?
N21 C22 C23 110.3(4) ?
C21 C22 C23 112.3(4) ?
N21 C22 H22 108.5 ?
C21 C22 H22 108.5 ?
C23 C22 H22 108.5 ?
C24 C23 C22 114.6(5) ?
C24 C23 H23A 108.6 ?
C22 C23 H23A 108.6 ?
C24 C23 H23B 108.6 ?
C22 C23 H23B 108.6 ?
H23A C23 H23B 107.6 ?
C26 C24 C23 113.7(7) ?
C26 C24 C25 106.7(8) ?
C23 C24 C25 106.6(7) ?
C26 C24 H24 109.9 ?
C23 C24 H24 109.9 ?
C25 C24 H24 109.9 ?
C24 C25 H25A 109.5 ?
C24 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
C24 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
C24 C26 H26A 109.5 ?
C24 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
C24 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
C22 N21 H21A 109.5 ?
C22 N21 H21B 109.5 ?
H21A N21 H21B 109.5 ?
C22 N21 H21C 109.5 ?
H21A N21 H21C 109.5 ?
H21B N21 H21C 109.5 ?
O31A C31 O31B 126.4(4) y
O31A C31 C32 119.8(4) y
O31B C31 C32 113.7(4) y
N31 C32 C33 110.3(4) ?
N31 C32 C31 108.6(4) ?
C33 C32 C31 112.3(4) ?
N31 C32 H32 108.5 ?
C33 C32 H32 108.5 ?
C31 C32 H32 108.5 ?
C34 C33 C32 116.2(5) ?
C34 C33 H33A 108.2 ?
C32 C33 H33A 108.2 ?
C34 C33 H33B 108.2 ?
C32 C33 H33B 108.2 ?
H33A C33 H33B 107.4 ?
C35 C34 C33 115.4(9) ?
C35 C34 C36 109.7(8) ?
C33 C34 C36 112.0(7) ?
C35 C34 H34 106.4 ?
C33 C34 H34 106.4 ?
C36 C34 H34 106.4 ?
C34 C35 H35A 109.5 ?
C34 C35 H35B 109.5 ?
H35A C35 H35B 109.5 ?
C34 C35 H35C 109.5 ?
H35A C35 H35C 109.5 ?
H35B C35 H35C 109.5 ?
C34 C36 H36A 109.5 ?
C34 C36 H36B 109.5 ?
H36A C36 H36B 109.5 ?
C34 C36 H36C 109.5 ?
H36A C36 H36C 109.5 ?
H36B C36 H36C 109.5 ?
C32 N31 H31A 109.5 ?
C32 N31 H31B 109.5 ?
H31A N31 H31B 109.5 ?
C32 N31 H31C 109.5 ?
H31A N31 H31C 109.5 ?
H31B N31 H31C 109.5 ?
O41A C41 O41B 126.4(5) y
O41A C41 C42 121.5(4) y
O41B C41 C42 112.1(4) y
N41 C42 C41 109.2(3) ?
N41 C42 C43 111.0(4) ?
C41 C42 C43 110.2(4) ?
N41 C42 H42 108.8 ?
C41 C42 H42 108.8 ?
C43 C42 H42 108.8 ?
C44 C43 C42 115.8(4) ?
C44 C43 H43A 108.3 ?
C42 C43 H43A 108.3 ?
C44 C43 H43B 108.3 ?
C42 C43 H43B 108.3 ?
H43A C43 H43B 107.4 ?
C44 C45 H45A 109.5 ?
C44 C45 H45B 109.5 ?
H45A C45 H45B 109.5 ?
C44 C45 H45C 109.5 ?
H45A C45 H45C 109.5 ?
H45B C45 H45C 109.5 ?
C45 C44 C46 112.2(5) ?
C45 C44 C43 112.3(5) ?
C46 C44 C43 109.6(5) ?
C45 C44 H44 107.5 ?
C46 C44 H44 107.5 ?
C43 C44 H44 107.5 ?
C44 C46 H46A 109.5 ?
C44 C46 H46B 109.5 ?
H46A C46 H46B 109.5 ?
C44 C46 H46C 109.5 ?
H46A C46 H46C 109.5 ?
H46B C46 H46C 109.5 ?
C42 N41 H41A 109.5 ?
C42 N41 H41B 109.5 ?
H41A N41 H41B 109.5 ?
C42 N41 H41C 109.5 ?
H41A N41 H41C 109.5 ?
H41B N41 H41C 109.5 ?
C41 O41B H41D 109.5 ?
O51A C51 O51B 125.5(4) y
O51A C51 C52 121.8(4) y
O51B C51 C52 112.7(4) y
N51 C52 C51 108.7(3) ?
N51 C52 C53 110.2(4) ?
C51 C52 C53 112.1(4) ?
N51 C52 H52 108.6 ?
C51 C52 H52 108.6 ?
C53 C52 H52 108.6 ?
C54 C53 C52 115.2(4) ?
C54 C53 H53A 108.5 ?
C52 C53 H53A 108.5 ?
C54 C53 H53B 108.5 ?
C52 C53 H53B 108.5 ?
H53A C53 H53B 107.5 ?
C53 C54 C55 111.4(5) ?
C53 C54 C56 108.8(5) ?
C55 C54 C56 110.8(5) ?
C53 C54 H54 108.6 ?
C55 C54 H54 108.6 ?
C56 C54 H54 108.6 ?
C54 C55 H55A 109.5 ?
C54 C55 H55B 109.5 ?
H55A C55 H55B 109.5 ?
C54 C55 H55C 109.5 ?
H55A C55 H55C 109.5 ?
H55B C55 H55C 109.5 ?
C54 C56 H56A 109.5 ?
C54 C56 H56B 109.5 ?
H56A C56 H56B 109.5 ?
C54 C56 H56C 109.5 ?
H56A C56 H56C 109.5 ?
H56B C56 H56C 109.5 ?
C52 N51 H51A 109.5 ?
C52 N51 H51B 109.5 ?
H51A N51 H51B 109.5 ?
C52 N51 H51C 109.5 ?
H51A N51 H51C 109.5 ?
H51B N51 H51C 109.5 ?
C51 O51B H51D 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.253(6) ?
C1 C6 1.442(7) ?
C1 C2 1.442(7) ?
C2 C3 1.382(7) ?
C2 N3 1.441(7) ?
C3 C4 1.382(8) ?
C3 H3 0.9300 ?
C4 C5 1.380(7) ?
C4 N2 1.443(7) ?
C5 C6 1.382(7) ?
C5 H5 0.9300 ?
C6 N1 1.441(7) ?
N3 O6 1.210(6) ?
N3 O7 1.224(6) ?
N1 O2 1.218(7) ?
N1 O3 1.231(7) ?
N2 O5 1.219(7) ?
N2 O4 1.228(7) ?
C11 O11 1.239(6) ?
C11 C16 1.464(7) ?
C11 C12 1.472(7) ?
C12 C13 1.355(7) ?
C12 N11 1.461(7) ?
C13 C14 1.369(7) ?
C13 H13 0.9300 ?
C14 C15 1.390(8) ?
C14 N12 1.450(6) ?
C15 C16 1.355(7) ?
C15 H15 0.9300 ?
C16 N13 1.456(7) ?
N11 O13 1.198(7) ?
N11 O12 1.199(7) ?
N12 O14 1.207(7) ?
N12 O15 1.222(7) ?
N13 O16 1.218(6) ?
N13 O17 1.229(6) ?
C21 O21A 1.249(6) y
C21 O21B 1.253(6) y
C21 C22 1.525(6) ?
C22 N21 1.493(6) ?
C22 C23 1.540(7) ?
C22 H22 0.9800 ?
C23 C24 1.510(8) ?
C23 H23A 0.9700 ?
C23 H23B 0.9700 ?
C24 C26 1.495(13) ?
C24 C25 1.594(15) ?
C24 H24 0.9800 ?
C25 H25A 0.9600 ?
C25 H25B 0.9600 ?
C25 H25C 0.9600 ?
C26 H26A 0.9600 ?
C26 H26B 0.9600 ?
C26 H26C 0.9600 ?
N21 H21A 0.8900 ?
N21 H21B 0.8900 ?
N21 H21C 0.8900 ?
C31 O31A 1.247(6) y
C31 O31B 1.253(6) y
C31 C32 1.532(6) ?
C32 N31 1.496(6) ?
C32 C33 1.517(7) ?
C32 H32 0.9800 ?
C33 C34 1.503(10) ?
C33 H33A 0.9700 ?
C33 H33B 0.9700 ?
C34 C35 1.406(15) ?
C34 C36 1.522(12) ?
C34 H34 0.9800 ?
C35 H35A 0.9600 ?
C35 H35B 0.9600 ?
C35 H35C 0.9600 ?
C36 H36A 0.9600 ?
C36 H36B 0.9600 ?
C36 H36C 0.9600 ?
N31 H31A 0.8900 ?
N31 H31B 0.8900 ?
N31 H31C 0.8900 ?
C41 O41A 1.223(6) y
C41 O41B 1.275(6) y
C41 C42 1.524(6) ?
C42 N41 1.484(6) ?
C42 C43 1.541(7) ?
C42 H42 0.9800 ?
C43 C44 1.532(7) ?
C43 H43A 0.9700 ?
C43 H43B 0.9700 ?
C45 C44 1.493(9) ?
C45 H45A 0.9600 ?
C45 H45B 0.9600 ?
C45 H45C 0.9600 ?
C44 C46 1.517(8) ?
C44 H44 0.9800 ?
C46 H46A 0.9600 ?
C46 H46B 0.9600 ?
C46 H46C 0.9600 ?
N41 H41A 0.8900 ?
N41 H41B 0.8900 ?
N41 H41C 0.8900 ?
O41B H41D 0.8200 ?
C51 O51A 1.212(6) y
C51 O51B 1.286(6) y
C51 C52 1.516(6) ?
C52 N51 1.496(6) ?
C52 C53 1.534(6) ?
C52 H52 0.9800 ?
C53 C54 1.518(7) ?
C53 H53A 0.9700 ?
C53 H53B 0.9700 ?
C54 C55 1.518(10) ?
C54 C56 1.539(9) ?
C54 H54 0.9800 ?
C55 H55A 0.9600 ?
C55 H55B 0.9600 ?
C55 H55C 0.9600 ?
C56 H56A 0.9600 ?
C56 H56B 0.9600 ?
C56 H56C 0.9600 ?
N51 H51A 0.8900 ?
N51 H51B 0.8900 ?
N51 H51C 0.8900 ?
O51B H51D 0.8200 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O51B H51D O31B 1_655 0.82 1.65 2.454(5) 166
N51 H51C O31A . 0.89 2.12 2.999(5) 168
N51 H51B O7 . 0.89 2.23 3.098(6) 164
N51 H51A O21A 1_565 0.89 1.93 2.798(5) 166
O41B H41D O21B 1_655 0.82 1.68 2.471(5) 161
N41 H41C O21A . 0.89 2.07 2.942(5) 166
N41 H41B O11 1_545 0.89 2.02 2.907(5) 173
N41 H41A O31A 1_645 0.89 2.05 2.913(5) 162
N31 H31C O5 1_554 0.89 2.16 2.977(6) 153
N31 H31B O17 1_455 0.89 2.25 2.998(6) 142
N31 H31B O12 . 0.89 2.62 3.364(9) 142
N31 H31A O51A . 0.89 1.97 2.861(5) 176
N21 H21C O41A . 0.89 2.10 2.983(5) 174
N21 H21B O6 1_645 0.89 2.57 3.355(6) 147
N21 H21B O15 1_546 0.89 2.56 3.084(6) 118
N21 H21A O1 1_545 0.89 1.91 2.753(6) 157
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . -176.1(5) ?
C6 C1 C2 C3 . . . 1.5(7) ?
O1 C1 C2 N3 . . . 4.6(7) ?
C6 C1 C2 N3 . . . -177.8(5) ?
N3 C2 C3 C4 . . . 179.6(5) ?
C1 C2 C3 C4 . . . 0.3(8) ?
C2 C3 C4 C5 . . . -1.3(8) ?
C2 C3 C4 N2 . . . 177.7(5) ?
C3 C4 C5 C6 . . . 0.3(8) ?
N2 C4 C5 C6 . . . -178.6(5) ?
C4 C5 C6 N1 . . . -177.1(5) ?
C4 C5 C6 C1 . . . 1.7(7) ?
O1 C1 C6 C5 . . . 175.0(5) ?
C2 C1 C6 C5 . . . -2.5(7) ?
O1 C1 C6 N1 . . . -6.2(7) ?
C2 C1 C6 N1 . . . 176.3(4) ?
C3 C2 N3 O6 . . . 28.3(8) y
C1 C2 N3 O6 . . . -152.3(5) y
C3 C2 N3 O7 . . . -151.8(6) ?
C1 C2 N3 O7 . . . 27.5(8) ?
C5 C6 N1 O2 . . . 166.1(6) y
C1 C6 N1 O2 . . . -12.8(8) y
C5 C6 N1 O3 . . . -14.2(8) ?
C1 C6 N1 O3 . . . 166.9(5) ?
C5 C4 N2 O5 . . . 177.6(5) ?
C3 C4 N2 O5 . . . -1.3(8) ?
C5 C4 N2 O4 . . . 2.2(9) y
C3 C4 N2 O4 . . . -176.8(6) y
O11 C11 C12 C13 . . . -177.3(5) ?
C16 C11 C12 C13 . . . 1.3(7) ?
O11 C11 C12 N11 . . . 4.0(8) ?
C16 C11 C12 N11 . . . -177.5(5) ?
N11 C12 C13 C14 . . . 177.1(5) ?
C11 C12 C13 C14 . . . -1.7(8) ?
C12 C13 C14 C15 . . . 2.5(8) ?
C12 C13 C14 N12 . . . 179.5(5) ?
C13 C14 C15 C16 . . . -2.9(8) ?
N12 C14 C15 C16 . . . -179.9(5) ?
C14 C15 C16 N13 . . . 179.9(5) ?
C14 C15 C16 C11 . . . 2.7(8) ?
O11 C11 C16 C15 . . . 176.7(5) ?
C12 C11 C16 C15 . . . -1.8(7) ?
O11 C11 C16 N13 . . . -0.4(7) ?
C12 C11 C16 N13 . . . -179.0(4) ?
C13 C12 N11 O13 . . . 9.4(9) ?
C11 C12 N11 O13 . . . -171.7(6) ?
C13 C12 N11 O12 . . . -173.6(6) y
C11 C12 N11 O12 . . . 5.3(9) y
C13 C14 N12 O14 . . . -1.6(9) y
C15 C14 N12 O14 . . . 175.4(6) y
C13 C14 N12 O15 . . . 179.3(6) ?
C15 C14 N12 O15 . . . -3.6(8) ?
C15 C16 N13 O16 . . . -23.1(8) y
C11 C16 N13 O16 . . . 154.3(6) y
C15 C16 N13 O17 . . . 153.3(6) ?
C11 C16 N13 O17 . . . -29.3(8) ?
O21A C21 C22 N21 . . . -9.5(6) y
O21B C21 C22 N21 . . . 170.4(4) y
O21A C21 C22 C23 . . . 112.8(5) ?
O21B C21 C22 C23 . . . -67.3(6) ?
N21 C22 C23 C24 . . . -78.6(6) y
C21 C22 C23 C24 . . . 160.0(5) ?
C22 C23 C24 C26 . . . 163.5(8) y
C22 C23 C24 C25 . . . -79.2(7) y
O31A C31 C32 N31 . . . -9.5(6) y
O31B C31 C32 N31 . . . 172.3(4) y
O31A C31 C32 C33 . . . 112.7(5) ?
O31B C31 C32 C33 . . . -65.5(6) ?
N31 C32 C33 C34 . . . -71.0(8) y
C31 C32 C33 C34 . . . 167.8(7) ?
C32 C33 C34 C35 . . . -69.7(11) y
C32 C33 C34 C36 . . . 163.9(8) y
O41A C41 C42 N41 . . . -14.8(6) y
O41B C41 C42 N41 . . . 168.3(4) y
O41A C41 C42 C43 . . . 107.4(5) ?
O41B C41 C42 C43 . . . -69.5(5) ?
N41 C42 C43 C44 . . . -75.3(5) y
C41 C42 C43 C44 . . . 163.6(4) ?
C42 C43 C44 C45 . . . -67.9(6) y
C42 C43 C44 C46 . . . 166.7(5) y
O51A C51 C52 N51 . . . -11.3(6) y
O51B C51 C52 N51 . . . 167.2(4) y
O51A C51 C52 C53 . . . 110.7(5) ?
O51B C51 C52 C53 . . . -70.8(5) ?
N51 C52 C53 C54 . . . -76.2(5) y
C51 C52 C53 C54 . . . 162.6(5) ?
C52 C53 C54 C55 . . . -74.6(6) y
C52 C53 C54 C56 . . . 162.9(5) y
H41D O21B C21 O21A 1_655 1_655 1_655 2.5 y
H51D O31B C31 O31A 1_655 1_655 1_655 2.4 y
