##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section B. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section B, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_leu_300
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2016-07-13
_journal_date_accepted     2016-10-05
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2016
_journal_volume     72
_journal_issue      6
_journal_page_first     885
_journal_page_last     892
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2052520616015699
_journal_coeditor_code     FX5005
_database_code_depnum_ccdc_archive     'CCDC 1508363'
_chemical_name_systematic     '2-amino-4-methylpentanoic acid'
_chemical_name_common     'l-leucine at 300 K'
_chemical_formula_moiety     'C6 H13 N O2'
_chemical_formula_sum     'C6 H13 N O2'
_chemical_formula_weight     131.17
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     9.606(3)
_cell_length_b     5.324(7)
_cell_length_c     14.666(2)
_cell_angle_alpha     90
_cell_angle_beta     94.06(3)
_cell_angle_gamma     90
_cell_volume     748.2(10)
_cell_formula_units_Z     4
_cell_measurement_temperature     300
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     2
_exptl_crystal_size_mid     0.5
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.165
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     288
_exptl_absorpt_coefficient_mu     0.132
_exptl_absorpt_correction_type     ?
_exptl_absorpt_process_details     ?
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     300
_diffrn_radiation_type     'neutron'
_diffrn_radiation_wavelength     0.80
_diffrn_measurement_device_type     'KOALA'
_diffrn_measurement_device     'Laue image-plate diffractometer'
_diffrn_measurement_method     'Laue'
_diffrn_reflns_number     24819
_diffrn_reflns_av_R_equivalents     0.1116
_diffrn_reflns_theta_max     71.41
_diffrn_reflns_theta_full     71.31
_diffrn_measured_fraction_theta_max     0.887
_diffrn_measured_fraction_theta_full     0.887
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_reflns_reduction_process     'LaueG (Piltz, 2011)'
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     1648
_reflns_number_gt     1367
_reflns_threshold_expression     '>2sigma(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0818
_refine_ls_R_factor_gt     0.0582
_refine_ls_wR_factor_gt     0.1203
_refine_ls_wR_factor_ref     0.1341
_refine_ls_goodness_of_fit_ref     1.102
_refine_ls_restrained_S_all     1.140
_refine_ls_number_reflns     1647
_refine_ls_number_parameters     397
_refine_ls_number_restraints     361
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0353P)²+6.3211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.553
_refine_diff_density_min     -0.631
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Absolute structure known from synthesis
;
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0060 0.0020
          'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
    'H' 'H' 0.0000 0.0000
          'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
    'N' 'N' 0.0100 0.0050
          'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
    'O' 'O' 0.0170 0.0090
          'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
_computing_data_collection     'MAATEL/ANSTO control program'
_computing_cell_refinement     'LaueG (Piltz, 2011)'
_computing_data_reduction
;
argonne_boxes (Wilkinson et al., 1988) & LaueG (Piltz, 2011)'
;
_computing_structure_solution     ?
_computing_structure_refinement     'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.2384(3) 0.4884(7) 0.6180(2) 0.0288(7) Uani d 1 . .
    O O1 0.1387(4) 0.6232(9) 0.5871(3) 0.0355(10) Uani d 1 . .
    O O2 0.2300(5) 0.2611(10) 0.6362(4) 0.0464(12) Uani d 1 . .
    C C2 0.3798(3) 0.6203(7) 0.6367(2) 0.0278(7) Uani d 1 . .
    N N1 0.3885(3) 0.8406(5) 0.57485(18) 0.0311(6) Uani d 1 . .
    C C3 0.3997(4) 0.7190(9) 0.7349(3) 0.0385(9) Uani d 1 . .
    C C4 0.4057(5) 0.5193(12) 0.8098(3) 0.0517(11) Uani d 1 . .
    C C5 0.5333(7) 0.3522(14) 0.8057(5) 0.0721(16) Uani d 1 . .
    C C6 0.4078(11) 0.658(2) 0.9035(4) 0.0843(19) Uani d 1 . .
    C C7 0.2532(3) 0.4009(7) 0.3867(2) 0.0279(7) Uani d 1 . .
    O O3 0.3469(4) 0.5525(9) 0.4141(3) 0.0352(9) Uani d 1 . .
    O O4 0.2665(6) 0.1690(11) 0.3817(5) 0.0525(14) Uani d 1 . .
    C C8 0.1136(3) 0.5157(8) 0.3521(3) 0.0324(8) Uani d 1 . .
    N N2 0.0874(3) 0.7497(6) 0.4056(2) 0.0391(7) Uani d 1 . .
    C C9 0.1115(5) 0.5906(11) 0.2518(3) 0.0508(11) Uani d 1 . .
    C C10 0.1137(6) 0.3740(16) 0.1839(3) 0.0677(15) Uani d 1 . .
    C C11 -0.0254(10) 0.231(2) 0.1775(6) 0.091(2) Uani d 1 . .
    C C12 0.1427(15) 0.475(3) 0.0900(5) 0.122(3) Uani d 1 . .
    H H1 0.4627(8) 0.4897(18) 0.6210(6) 0.0464(18) Uani d 1 . .
    H H2 0.3220(8) 0.9803(18) 0.5910(6) 0.0451(16) Uani d 1 . .
    H H3 0.4915(8) 0.9138(17) 0.5793(6) 0.0432(17) Uani d 1 . .
    H H4 0.3639(8) 0.7819(18) 0.5076(5) 0.0465(17) Uani d 1 . .
    H H5 0.3177(12) 0.853(2) 0.7448(7) 0.065(2) Uani d 1 . .
    H H6 0.4982(10) 0.818(2) 0.7416(6) 0.057(2) Uani d 1 . .
    H H7 0.3127(13) 0.412(3) 0.8019(8) 0.080(3) Uani d 1 . .
    H H8 0.6254(16) 0.454(3) 0.8161(13) 0.097(4) Uani d 1 . .
    H H9 0.530(2) 0.256(4) 0.7459(12) 0.097(4) Uani d 1 . .
    H H10 0.535(2) 0.213(4) 0.8567(13) 0.106(4) Uani d 1 . .
    H H11 0.410(2) 0.528(5) 0.9577(11) 0.118(5) Uani d 1 . .
    H H12 0.496(2) 0.765(4) 0.9151(11) 0.108(4) Uani d 1 . .
    H H13 0.323(2) 0.771(5) 0.9099(11) 0.118(5) Uani d 1 . .
    H H14 0.0298(8) 0.387(2) 0.3641(6) 0.051(2) Uani d 1 . .
    H H15 0.1537(9) 0.8928(19) 0.3895(7) 0.0495(18) Uani d 1 . .
    H H16 0.1035(9) 0.7114(19) 0.4754(6) 0.0507(18) Uani d 1 . .
    H H17 -0.0139(9) 0.813(3) 0.3940(8) 0.065(3) Uani d 1 . .
    H H18 0.1967(14) 0.718(3) 0.2437(8) 0.081(3) Uani d 1 . .
    H H19 0.0163(13) 0.705(3) 0.2369(8) 0.076(3) Uani d 1 . .
    H H20 0.1892(18) 0.241(4) 0.2079(10) 0.100(4) Uani d 1 . .
    H H21 0.147(3) 0.323(6) 0.0424(13) 0.155(6) Uani d 1 . .
    H H22 0.230(3) 0.584(7) 0.0922(14) 0.156(7) Uani d 1 . .
    H H23 0.059(3) 0.599(7) 0.0626(15) 0.151(6) Uani d 1 . .
    H H24 -0.051(3) 0.162(5) 0.2422(14) 0.125(5) Uani d 1 . .
    H H25 -0.026(3) 0.079(5) 0.1344(14) 0.123(5) Uani d 1 . .
    H H26 -0.102(2) 0.341(5) 0.1548(15) 0.116(4) Uani d 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O2 . 1.243(7) ?
    C1 O1 . 1.256(6) ?
    C1 C2 . 1.536(4) ?
    C2 H1 . 1.094(9) ?
    C2 N1 . 1.489(5) ?
    C2 C3 . 1.532(5) ?
    N1 H2 . 1.019(10) ?
    N1 H4 . 1.045(8) ?
    N1 H3 . 1.061(7) ?
    C3 H5 . 1.079(12) ?
    C3 H6 . 1.081(10) ?
    C3 C4 . 1.527(7) ?
    C4 H7 . 1.059(14) ?
    C4 C5 . 1.520(9) ?
    C4 C6 . 1.558(9) ?
    C5 H9 . 1.01(2) ?
    C5 H8 . 1.04(2) ?
    C5 H10 . 1.05(2) ?
    C6 H13 . 1.02(3) ?
    C6 H12 . 1.03(3) ?
    C6 H11 . 1.05(2) ?
    C7 O4 . 1.244(7) ?
    C7 O3 . 1.254(6) ?
    C7 C8 . 1.527(5) ?
    C8 H14 . 1.082(9) ?
    C8 N2 . 1.503(6) ?
    C8 C9 . 1.524(6) ?
    N2 H15 . 1.032(11) ?
    N2 H17 . 1.033(8) ?
    N2 H16 . 1.044(10) ?
    C9 H18 . 1.077(13) ?
    C9 H19 . 1.108(15) ?
    C9 C10 . 1.524(9) ?
    C10 H20 . 1.05(2) ?
    C10 C12 . 1.522(10) ?
    C10 C11 . 1.537(10) ?
    C11 H26 . 0.98(4) ?
    C11 H25 . 1.02(3) ?
    C11 H24 . 1.06(3) ?
    C12 H22 . 1.02(4) ?
    C12 H21 . 1.07(3) ?
    C12 H23 . 1.09(5) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 C1 O1 . . 125.0(4) ?
    O2 C1 C2 . . 118.5(4) ?
    O1 C1 C2 . . 116.4(4) ?
    H1 C2 N1 . . 107.4(6) ?
    H1 C2 C3 . . 111.8(6) ?
    N1 C2 C3 . . 107.1(3) ?
    H1 C2 C1 . . 108.6(6) ?
    N1 C2 C1 . . 109.8(3) ?
    C3 C2 C1 . . 112.0(3) ?
    H2 N1 H4 . . 109.5(8) ?
    H2 N1 H3 . . 108.4(8) ?
    H4 N1 H3 . . 108.4(7) ?
    H2 N1 C2 . . 111.7(5) ?
    H4 N1 C2 . . 108.7(6) ?
    H3 N1 C2 . . 110.2(5) ?
    H5 C3 H6 . . 107.9(10) ?
    H5 C3 C4 . . 110.6(7) ?
    H6 C3 C4 . . 106.7(7) ?
    H5 C3 C2 . . 108.0(7) ?
    H6 C3 C2 . . 107.6(6) ?
    C4 C3 C2 . . 115.7(4) ?
    H7 C4 C5 . . 110.9(11) ?
    H7 C4 C3 . . 107.9(7) ?
    C5 C4 C3 . . 111.6(5) ?
    H7 C4 C6 . . 108.0(9) ?
    C5 C4 C6 . . 110.6(5) ?
    C3 C4 C6 . . 107.6(6) ?
    H9 C5 H8 . . 111.1(17) ?
    H9 C5 H10 . . 104.9(17) ?
    H8 C5 H10 . . 107.1(15) ?
    H9 C5 C4 . . 110.9(11) ?
    H8 C5 C4 . . 111.7(11) ?
    H10 C5 C4 . . 110.9(13) ?
    H13 C6 H12 . . 108(2) ?
    H13 C6 H11 . . 106.9(19) ?
    H12 C6 H11 . . 105.7(17) ?
    H13 C6 C4 . . 113.6(11) ?
    H12 C6 C4 . . 111.6(11) ?
    H11 C6 C4 . . 110.7(14) ?
    O4 C7 O3 . . 125.7(5) ?
    O4 C7 C8 . . 118.0(4) ?
    O3 C7 C8 . . 116.2(4) ?
    H14 C8 N2 . . 106.7(6) ?
    H14 C8 C9 . . 111.3(6) ?
    N2 C8 C9 . . 107.2(4) ?
    H14 C8 C7 . . 109.8(6) ?
    N2 C8 C7 . . 109.5(3) ?
    C9 C8 C7 . . 112.1(3) ?
    H15 N2 H17 . . 108.1(9) ?
    H15 N2 H16 . . 108.5(8) ?
    H17 N2 H16 . . 107.4(8) ?
    H15 N2 C8 . . 111.3(6) ?
    H17 N2 C8 . . 112.0(8) ?
    H16 N2 C8 . . 109.3(6) ?
    H18 C9 H19 . . 104.7(13) ?
    H18 C9 C8 . . 108.3(7) ?
    H19 C9 C8 . . 106.8(8) ?
    H18 C9 C10 . . 111.1(10) ?
    H19 C9 C10 . . 109.7(9) ?
    C8 C9 C10 . . 115.6(5) ?
    H20 C10 C12 . . 111.9(12) ?
    H20 C10 C9 . . 109.3(10) ?
    C12 C10 C9 . . 109.7(8) ?
    H20 C10 C11 . . 105.2(13) ?
    C12 C10 C11 . . 109.4(7) ?
    C9 C10 C11 . . 111.3(6) ?
    H26 C11 H25 . . 106.7(19) ?
    H26 C11 H24 . . 107(2) ?
    H25 C11 H24 . . 107(2) ?
    H26 C11 C10 . . 110.7(14) ?
    H25 C11 C10 . . 113.6(15) ?
    H24 C11 C10 . . 111.6(14) ?
    H22 C12 H21 . . 113(2) ?
    H22 C12 H23 . . 104(3) ?
    H21 C12 H23 . . 106(2) ?
    H22 C12 C10 . . 112.0(14) ?
    H21 C12 C10 . . 110.0(17) ?
    H23 C12 C10 . . 111.6(14) ?
data_leu_120
_audit_creation_method     'SHELXL-2014/7'
_database_code_depnum_ccdc_archive     'CCDC 1508364'
_chemical_name_systematic     '2-amino-4-methylpentanoic acid'
_chemical_name_common     'l-leucine at 120 K'
_chemical_formula_moiety     'C6 H13 N O2'
_chemical_formula_sum     'C6 H13 N O2'
_chemical_formula_weight     131.17
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     9.562(2)
_cell_length_b     5.3010(10)
_cell_length_c     14.519(3)
_cell_angle_alpha     90
_cell_angle_beta     94.20(2)
_cell_angle_gamma     90
_cell_volume     734.0(3)
_cell_formula_units_Z     4
_cell_measurement_temperature     120
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     2
_exptl_crystal_size_mid     0.5
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.187
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     288
_exptl_absorpt_coefficient_mu     0.0
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details     ?
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     120
_diffrn_radiation_type     'neutron'
_diffrn_radiation_wavelength     0.80
_diffrn_measurement_device_type     'KOALA'
_diffrn_measurement_device     'Laue image-plate diffractometer'
_diffrn_measurement_method     'Laue'
_diffrn_reflns_number     21729
_diffrn_reflns_av_R_equivalents     0.1555
_diffrn_reflns_theta_max     71.36
_diffrn_reflns_theta_full     71.26
_diffrn_measured_fraction_theta_max     0.868
_diffrn_measured_fraction_theta_full     0.868
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_reflns_reduction_process     'LaueG (Piltz, 2011)'
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     2430
_reflns_number_gt     1955
_reflns_threshold_expression     '>2sigma(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1183
_refine_ls_R_factor_gt     0.0790
_refine_ls_wR_factor_gt     0.1525
_refine_ls_wR_factor_ref     0.1713
_refine_ls_goodness_of_fit_ref     1.141
_refine_ls_restrained_S_all     1.128
_refine_ls_number_reflns     2429
_refine_ls_number_parameters     397
_refine_ls_number_restraints     361
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'w=1/[σ²(Fo²)+(0.0484P)²+12.6665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.291
_refine_diff_density_min     -1.396
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Not applicable, absolute structure determined from synthesis
;
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0060 0.0020
          'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
    'H' 'H' 0.0000 0.0000
          'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
    'N' 'N' 0.0100 0.0050
          'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
    'O' 'O' 0.0170 0.0090
          'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
_computing_data_collection     'MAATEL/ANSTO control program'
_computing_cell_refinement     'LaueG (Piltz, 2011)'
_computing_data_reduction
;
argonne_boxes (Wilkinson et al., 1988) & LaueG (Piltz, 2011)
;
_computing_structure_solution     ?
_computing_structure_refinement     'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.2364(3) 0.5018(7) 0.6168(2) 0.0132(6) Uani d 1 . .
    O O1 0.1364(4) 0.6377(9) 0.5851(3) 0.0168(7) Uani d 1 . .
    O O2 0.2267(4) 0.2744(8) 0.6365(3) 0.0196(8) Uani d 1 . .
    C C2 0.3793(3) 0.6312(7) 0.6347(2) 0.0130(6) Uani d 1 . .
    N N1 0.3863(2) 0.8535(5) 0.57206(16) 0.0143(4) Uani d 1 . .
    C C3 0.4010(4) 0.7295(7) 0.7346(2) 0.0160(6) Uani d 1 . .
    C C4 0.4055(4) 0.5299(8) 0.8106(3) 0.0209(7) Uani d 1 . .
    C C5 0.5306(5) 0.3530(9) 0.8055(3) 0.0276(8) Uani d 1 . .
    C C6 0.4135(5) 0.6616(11) 0.9045(3) 0.0321(9) Uani d 1 . .
    C C7 0.2524(3) 0.3905(7) 0.3862(2) 0.0147(6) Uani d 1 . .
    O O3 0.3463(4) 0.5453(8) 0.4147(3) 0.0166(7) Uani d 1 . .
    O O4 0.2674(5) 0.1553(9) 0.3824(3) 0.0222(8) Uani d 1 . .
    C C8 0.1113(3) 0.5015(7) 0.3487(2) 0.0150(6) Uani d 1 . .
    N N2 0.0823(3) 0.7371(5) 0.39997(18) 0.0177(5) Uani d 1 . .
    C C9 0.1130(4) 0.5668(8) 0.2461(3) 0.0209(7) Uani d 1 . .
    C C10 0.1156(4) 0.3402(11) 0.1804(3) 0.0281(8) Uani d 1 . .
    C C11 -0.0243(6) 0.2017(11) 0.1749(4) 0.0367(11) Uani d 1 . .
    C C12 0.1500(7) 0.4288(16) 0.0852(3) 0.0513(16) Uani d 1 . .
    H H1 0.4639(8) 0.5013(16) 0.6190(6) 0.0262(13) Uani d 1 . .
    H H2 0.3205(8) 0.9932(16) 0.5906(6) 0.0270(14) Uani d 1 . .
    H H3 0.4914(7) 0.9255(15) 0.5764(6) 0.0242(13) Uani d 1 . .
    H H4 0.3598(9) 0.7944(17) 0.5043(5) 0.0278(14) Uani d 1 . .
    H H5 0.3183(9) 0.8679(18) 0.7462(6) 0.0329(16) Uani d 1 . .
    H H6 0.5021(9) 0.8321(18) 0.7409(6) 0.0312(16) Uani d 1 . .
    H H7 0.3086(10) 0.415(2) 0.8029(7) 0.039(2) Uani d 1 . .
    H H8 0.6263(11) 0.462(2) 0.8153(10) 0.051(3) Uani d 1 . .
    H H9 0.5298(15) 0.257(2) 0.7400(8) 0.050(2) Uani d 1 . .
    H H10 0.5331(15) 0.205(2) 0.8584(9) 0.053(3) Uani d 1 . .
    H H11 0.4135(16) 0.522(3) 0.9619(7) 0.057(3) Uani d 1 . .
    H H12 0.5110(13) 0.764(3) 0.9155(8) 0.052(2) Uani d 1 . .
    H H13 0.3277(15) 0.789(3) 0.9125(8) 0.061(3) Uani d 1 . .
    H H14 0.0276(8) 0.3666(17) 0.3607(5) 0.0270(14) Uani d 1 . .
    H H15 0.1478(8) 0.8845(16) 0.3832(6) 0.0288(14) Uani d 1 . .
    H H16 0.0976(9) 0.7084(18) 0.4726(5) 0.0299(15) Uani d 1 . .
    H H17 -0.0212(8) 0.789(2) 0.3860(6) 0.0327(17) Uani d 1 . .
    H H18 0.2009(12) 0.691(2) 0.2373(7) 0.046(2) Uani d 1 . .
    H H19 0.0159(11) 0.676(2) 0.2272(7) 0.0399(19) Uani d 1 . .
    H H20 0.1939(13) 0.210(3) 0.2082(8) 0.053(3) Uani d 1 . .
    H H21 0.1560(18) 0.264(4) 0.0377(9) 0.074(3) Uani d 1 . .
    H H22 0.2486(19) 0.529(5) 0.0869(10) 0.080(4) Uani d 1 . .
    H H23 0.0681(19) 0.559(4) 0.0553(9) 0.071(3) Uani d 1 . .
    H H24 -0.0556(17) 0.133(3) 0.2401(9) 0.059(3) Uani d 1 . .
    H H25 -0.0255(18) 0.044(3) 0.1283(10) 0.061(3) Uani d 1 . .
    H H26 -0.1059(14) 0.326(3) 0.1469(11) 0.059(3) Uani d 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O2 . 1.244(5) ?
    C1 O1 . 1.257(5) ?
    C1 C2 . 1.534(4) ?
    C2 H1 . 1.099(8) ?
    C2 N1 . 1.493(4) ?
    C2 C3 . 1.540(5) ?
    N1 H2 . 1.020(8) ?
    N1 H4 . 1.046(7) ?
    N1 H3 . 1.073(7) ?
    C3 H5 . 1.101(9) ?
    C3 H6 . 1.108(8) ?
    C3 C4 . 1.527(5) ?
    C4 H7 . 1.107(9) ?
    C4 C5 . 1.526(6) ?
    C4 C6 . 1.529(6) ?
    C5 H9 . 1.078(12) ?
    C5 H8 . 1.081(12) ?
    C5 H10 . 1.098(13) ?
    C6 H13 . 1.075(15) ?
    C6 H12 . 1.079(14) ?
    C6 H11 . 1.115(13) ?
    C7 O4 . 1.257(6) ?
    C7 O3 . 1.263(6) ?
    C7 C8 . 1.535(5) ?
    C8 H14 . 1.096(8) ?
    C8 N2 . 1.491(5) ?
    C8 C9 . 1.530(5) ?
    N2 H17 . 1.033(8) ?
    N2 H15 . 1.041(9) ?
    N2 H16 . 1.064(8) ?
    C9 H18 . 1.082(11) ?
    C9 H19 . 1.113(11) ?
    C9 C10 . 1.536(7) ?
    C10 H20 . 1.075(13) ?
    C10 C12 . 1.519(7) ?
    C10 C11 . 1.523(7) ?
    C11 H25 . 1.073(15) ?
    C11 H24 . 1.077(14) ?
    C11 H26 . 1.079(17) ?
    C12 H22 . 1.081(18) ?
    C12 H23 . 1.11(2) ?
    C12 H21 . 1.115(19) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 C1 O1 . . 124.9(4) ?
    O2 C1 C2 . . 118.3(3) ?
    O1 C1 C2 . . 116.8(3) ?
    H1 C2 N1 . . 107.5(5) ?
    H1 C2 C1 . . 110.2(5) ?
    N1 C2 C1 . . 109.2(3) ?
    H1 C2 C3 . . 110.9(5) ?
    N1 C2 C3 . . 107.3(3) ?
    C1 C2 C3 . . 111.6(3) ?
    H2 N1 H4 . . 110.8(7) ?
    H2 N1 H3 . . 108.6(7) ?
    H4 N1 H3 . . 108.9(7) ?
    H2 N1 C2 . . 110.9(5) ?
    H4 N1 C2 . . 108.6(5) ?
    H3 N1 C2 . . 109.2(5) ?
    H5 C3 H6 . . 107.0(8) ?
    H5 C3 C4 . . 109.5(6) ?
    H6 C3 C4 . . 107.6(5) ?
    H5 C3 C2 . . 108.7(6) ?
    H6 C3 C2 . . 107.5(5) ?
    C4 C3 C2 . . 116.1(3) ?
    H7 C4 C5 . . 108.0(7) ?
    H7 C4 C3 . . 109.3(6) ?
    C5 C4 C3 . . 111.8(3) ?
    H7 C4 C6 . . 109.1(7) ?
    C5 C4 C6 . . 109.6(3) ?
    C3 C4 C6 . . 109.0(4) ?
    H9 C5 H8 . . 108.6(12) ?
    H9 C5 H10 . . 106.2(11) ?
    H8 C5 H10 . . 108.2(11) ?
    H9 C5 C4 . . 112.2(8) ?
    H8 C5 C4 . . 109.0(7) ?
    H10 C5 C4 . . 112.5(9) ?
    H13 C6 H12 . . 109.2(13) ?
    H13 C6 H11 . . 107.1(12) ?
    H12 C6 H11 . . 105.7(11) ?
    H13 C6 C4 . . 113.2(8) ?
    H12 C6 C4 . . 110.3(7) ?
    H11 C6 C4 . . 111.1(9) ?
    O4 C7 O3 . . 125.3(4) ?
    O4 C7 C8 . . 117.7(4) ?
    O3 C7 C8 . . 116.9(3) ?
    H14 C8 N2 . . 107.6(5) ?
    H14 C8 C9 . . 111.2(5) ?
    N2 C8 C9 . . 108.2(3) ?
    H14 C8 C7 . . 109.1(5) ?
    N2 C8 C7 . . 109.5(3) ?
    C9 C8 C7 . . 111.1(3) ?
    H17 N2 H15 . . 109.7(8) ?
    H17 N2 H16 . . 107.0(7) ?
    H15 N2 H16 . . 107.3(7) ?
    H17 N2 C8 . . 109.7(6) ?
    H15 N2 C8 . . 112.0(5) ?
    H16 N2 C8 . . 111.0(6) ?
    H18 C9 H19 . . 107.1(10) ?
    H18 C9 C8 . . 108.5(6) ?
    H19 C9 C8 . . 106.9(6) ?
    H18 C9 C10 . . 110.7(8) ?
    H19 C9 C10 . . 107.8(7) ?
    C8 C9 C10 . . 115.5(4) ?
    H20 C10 C12 . . 110.5(8) ?
    H20 C10 C11 . . 107.2(9) ?
    C12 C10 C11 . . 110.5(4) ?
    H20 C10 C9 . . 108.1(8) ?
    C12 C10 C9 . . 109.8(5) ?
    C11 C10 C9 . . 110.9(4) ?
    H25 C11 H24 . . 107.6(13) ?
    H25 C11 H26 . . 105.4(13) ?
    H24 C11 H26 . . 107.3(14) ?
    H25 C11 C10 . . 112.1(10) ?
    H24 C11 C10 . . 114.5(9) ?
    H26 C11 C10 . . 109.4(9) ?
    H22 C12 H23 . . 107.0(18) ?
    H22 C12 H21 . . 108.3(15) ?
    H23 C12 H21 . . 108.3(14) ?
    H22 C12 C10 . . 112.2(9) ?
    H23 C12 C10 . . 110.8(8) ?
    H21 C12 C10 . . 110.2(11) ?
