#------------------------------------------------------------------------------
#$Date: 2019-11-11 17:23:07 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226705 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/52/4035239.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4035239
loop_
_publ_author_name
'Halli, Juliette'
'Kramer, Philipp'
'Grimmer, Jennifer'
'Bolte, Michael'
'Manolikakes, Georg'
_publ_section_title
;
 Bi(OTf)₃-Catalyzed Diastereoselective One-Pot Synthesis of
 1,3-Diamines with Three Continuous Stereogenic Centers.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12007
_journal_page_last               12022
_journal_paper_doi               10.1021/acs.joc.8b01925
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         '(C25 H23 N3 O2), 0.25(C3 H6 O)'
_chemical_formula_sum            'C25.75 H24.5 N3 O2.25'
_chemical_formula_weight         411.98
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   22.7789(15)
_cell_length_b                   22.7789(15)
_cell_length_c                   34.781(3)
_cell_measurement_reflns_used    13200
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      3.2
_cell_volume                     18047(2)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2160
_diffrn_reflns_av_unetI/netI     0.2373
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            30078
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.712
_diffrn_reflns_theta_min         3.207
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       needle
_exptl_crystal_F_000             6976
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.802
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     573
_refine_ls_number_reflns         8484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.802
_refine_ls_R_factor_all          0.1994
_refine_ls_R_factor_gt           0.0688
_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)+(0.0160P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3141
_reflns_number_total             8484
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01925_si_001.cif
_cod_data_source_block           ma3
_cod_original_cell_volume        18047(3)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_original_formula_sum        'C25.75 H24.50 N3 O2.25'
_cod_database_code               4035239
_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.
;
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.995
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
O1 O 0.72739(15) 0.59864(14) 0.74780(9) 0.0383(8) Uani 1 1 d . . .
O2 O 0.79222(13) 0.36630(13) 0.76348(8) 0.0306(7) Uani 1 1 d . . .
N1 N 0.67140(17) 0.55267(15) 0.70450(11) 0.0283(9) Uani 1 1 d . . .
H1 H 0.6483(19) 0.5546(19) 0.6818(13) 0.034 Uiso 1 1 d . U .
N2 N 0.77248(15) 0.40000(16) 0.70351(10) 0.0263(8) Uani 1 1 d . . .
H2 H 0.7942(18) 0.4172(19) 0.6800(13) 0.032 Uiso 1 1 d . U .
N3 N 0.6483(2) 0.4832(2) 0.78835(12) 0.0531(12) Uani 1 1 d . . .
C1 C 0.6924(2) 0.6023(2) 0.72102(13) 0.0323(11) Uani 1 1 d . . .
C2 C 0.6914(2) 0.49640(18) 0.71895(12) 0.0256(10) Uani 1 1 d . . .
H2AA H 0.7352 0.4978 0.7208 0.031 Uiso 1 1 calc R U .
C3 C 0.67482(19) 0.44463(19) 0.69291(12) 0.0275(10) Uani 1 1 d . . .
H3 H 0.6873 0.4550 0.6662 0.033 Uiso 1 1 calc R U .
C4 C 0.70849(18) 0.38893(19) 0.70455(12) 0.0255(10) Uani 1 1 d . . .
H4 H 0.6975 0.3791 0.7316 0.031 Uiso 1 1 calc R U .
C5 C 0.80903(19) 0.38754(18) 0.73252(11) 0.0245(10) Uani 1 1 d . . .
C6 C 0.60920(19) 0.4342(2) 0.69198(13) 0.0325(11) Uani 1 1 d . . .
H6A H 0.6006 0.4008 0.6751 0.049 Uiso 1 1 calc R U .
H6B H 0.5952 0.4255 0.7180 0.049 Uiso 1 1 calc R U .
H6C H 0.5894 0.4693 0.6822 0.049 Uiso 1 1 calc R U .
C7 C 0.6675(2) 0.48837(19) 0.75842(14) 0.0335(11) Uani 1 1 d . . .
C11 C 0.6699(2) 0.65965(19) 0.70710(13) 0.0324(11) Uani 1 1 d . . .
C12 C 0.6335(2) 0.6666(2) 0.67544(14) 0.0380(12) Uani 1 1 d . . .
H12 H 0.6233 0.6335 0.6602 0.046 Uiso 1 1 calc R U .
C13 C 0.6119(2) 0.7216(2) 0.66585(17) 0.0495(14) Uani 1 1 d . . .
H13 H 0.5880 0.7261 0.6436 0.059 Uiso 1 1 calc R U .
C14 C 0.6248(3) 0.7696(2) 0.68828(18) 0.0530(15) Uani 1 1 d . . .
H14 H 0.6087 0.8069 0.6822 0.064 Uiso 1 1 calc R U .
C15 C 0.6617(3) 0.7633(2) 0.72002(17) 0.0577(16) Uani 1 1 d . . .
H15 H 0.6712 0.7964 0.7354 0.069 Uiso 1 1 calc R U .
C16 C 0.6841(2) 0.7091(2) 0.72906(14) 0.0439(13) Uani 1 1 d . . .
H16 H 0.7097 0.7052 0.7505 0.053 Uiso 1 1 calc R U .
C41 C 0.69344(19) 0.33661(19) 0.67954(12) 0.0274(10) Uani 1 1 d . . .
C42 C 0.7057(2) 0.3365(2) 0.64061(13) 0.0347(12) Uani 1 1 d . . .
H42 H 0.7237 0.3700 0.6293 0.042 Uiso 1 1 calc R U .
C43 C 0.6921(2) 0.2881(2) 0.61745(15) 0.0427(13) Uani 1 1 d . . .
H43 H 0.7004 0.2890 0.5907 0.051 Uiso 1 1 calc R U .
C44 C 0.6669(2) 0.2399(2) 0.63353(16) 0.0466(14) Uani 1 1 d . . .
H44 H 0.6574 0.2069 0.6180 0.056 Uiso 1 1 calc R U .
C45 C 0.6554(2) 0.2391(2) 0.67223(16) 0.0478(14) Uani 1 1 d . . .
H45 H 0.6380 0.2052 0.6833 0.057 Uiso 1 1 calc R U .
C46 C 0.6684(2) 0.2867(2) 0.69555(15) 0.0401(12) Uani 1 1 d . . .
H46 H 0.6603 0.2852 0.7223 0.048 Uiso 1 1 calc R U .
C51 C 0.87216(19) 0.40088(19) 0.72509(12) 0.0269(10) Uani 1 1 d . . .
C52 C 0.8891(2) 0.4503(2) 0.70453(14) 0.0399(12) Uani 1 1 d . . .
H52 H 0.8602 0.4759 0.6943 0.048 Uiso 1 1 calc R U .
C53 C 0.9479(2) 0.4623(3) 0.69889(18) 0.0578(16) Uani 1 1 d . . .
H53 H 0.9595 0.4963 0.6850 0.069 Uiso 1 1 calc R U .
C54 C 0.9897(2) 0.4248(3) 0.71352(17) 0.0499(15) Uani 1 1 d . . .
H54 H 1.0300 0.4334 0.7097 0.060 Uiso 1 1 calc R U .
C55 C 0.9745(2) 0.3755(2) 0.73335(15) 0.0446(13) Uani 1 1 d . . .
H55 H 1.0038 0.3492 0.7425 0.053 Uiso 1 1 calc R U .
C56 C 0.91473(19) 0.3643(2) 0.74004(13) 0.0297(10) Uani 1 1 d . . .
H56 H 0.9035 0.3312 0.7550 0.036 Uiso 1 1 calc R U .
O1A O 0.81288(13) 0.43154(13) 0.62930(8) 0.0339(8) Uani 1 1 d . . .
O2A O 0.61343(14) 0.54871(13) 0.62804(8) 0.0336(8) Uani 1 1 d . . .
N1A N 0.83349(16) 0.50019(16) 0.58576(11) 0.0266(9) Uani 1 1 d . . .
H1A H 0.847(2) 0.511(2) 0.5670(14) 0.032 Uiso 1 1 d . U .
N2A N 0.65914(17) 0.53820(17) 0.57059(10) 0.0293(9) Uani 1 1 d . . .
H2A H 0.658(2) 0.523(2) 0.5501(14) 0.035 Uiso 1 1 d . U .
N3A N 0.7982(2) 0.5784(2) 0.66435(13) 0.0602(14) Uani 1 1 d . . .
C1A C 0.84491(19) 0.44849(19) 0.60316(12) 0.0267(10) Uani 1 1 d . . .
C2A C 0.78115(19) 0.5309(2) 0.59693(12) 0.0285(10) Uani 1 1 d . . .
H2A1 H 0.7490 0.5013 0.5996 0.034 Uiso 1 1 calc R U .
C3A C 0.76106(18) 0.57683(18) 0.56716(12) 0.0248(10) Uani 1 1 d . . .
H3A H 0.7650 0.5591 0.5410 0.030 Uiso 1 1 calc R U .
C4A C 0.69562(19) 0.59095(19) 0.57401(13) 0.0291(11) Uani 1 1 d . . .
H4A H 0.6915 0.6061 0.6009 0.035 Uiso 1 1 calc R U .
C5A C 0.61984(18) 0.52173(19) 0.59732(12) 0.0252(10) Uani 1 1 d . . .
C6A C 0.7987(2) 0.6321(2) 0.56846(14) 0.0353(11) Uani 1 1 d . . .
H6A1 H 0.7845 0.6601 0.5492 0.053 Uiso 1 1 calc R U .
H6A2 H 0.7960 0.6499 0.5941 0.053 Uiso 1 1 calc R U .
H6A3 H 0.8396 0.6219 0.5630 0.053 Uiso 1 1 calc R U .
C7A C 0.7904(2) 0.5581(2) 0.63504(15) 0.0390(12) Uani 1 1 d . . .
C11A C 0.89685(18) 0.41380(19) 0.59036(11) 0.0241(10) Uani 1 1 d . . .
C12A C 0.94281(19) 0.4371(2) 0.56952(14) 0.0346(12) Uani 1 1 d . . .
H12A H 0.9423 0.4774 0.5625 0.042 Uiso 1 1 calc R U .
C13A C 0.9898(2) 0.4018(2) 0.55882(16) 0.0485(14) Uani 1 1 d . . .
H13A H 1.0219 0.4180 0.5450 0.058 Uiso 1 1 calc R U .
C14A C 0.9896(2) 0.3428(2) 0.56846(16) 0.0483(14) Uani 1 1 d . . .
H14A H 1.0213 0.3183 0.5608 0.058 Uiso 1 1 calc R U .
C15A C 0.9435(2) 0.3196(2) 0.58907(16) 0.0487(14) Uani 1 1 d . . .
H15A H 0.9434 0.2791 0.5957 0.058 Uiso 1 1 calc R U .
C16A C 0.8977(2) 0.3548(2) 0.60011(14) 0.0377(12) Uani 1 1 d . . .
H16A H 0.8662 0.3386 0.6146 0.045 Uiso 1 1 calc R U .
C41A C 0.6739(2) 0.6386(2) 0.54665(16) 0.0399(12) Uani 1 1 d . . .
C42A C 0.6622(2) 0.6269(3) 0.50843(17) 0.0515(15) Uani 1 1 d . . .
H42A H 0.6673 0.5880 0.4991 0.062 Uiso 1 1 calc R U .
C43A C 0.6434(3) 0.6698(4) 0.4833(2) 0.087(3) Uani 1 1 d . . .
H43A H 0.6350 0.6611 0.4572 0.105 Uiso 1 1 calc R U .
C44A C 0.6372(4) 0.7271(5) 0.4980(4) 0.120(4) Uani 1 1 d . . .
H44A H 0.6236 0.7573 0.4815 0.144 Uiso 1 1 calc R U .
C45A C 0.6499(4) 0.7401(3) 0.5347(4) 0.114(4) Uani 1 1 d . . .
H45A H 0.6463 0.7794 0.5434 0.137 Uiso 1 1 calc R U .
C46A C 0.6685(3) 0.6960(2) 0.5604(2) 0.0659(18) Uani 1 1 d . . .
H46A H 0.6771 0.7050 0.5865 0.079 Uiso 1 1 calc R U .
C51A C 0.58416(19) 0.4682(2) 0.58878(12) 0.0291(10) Uani 1 1 d . . .
C52A C 0.6095(2) 0.4177(2) 0.57479(15) 0.0411(12) Uani 1 1 d . . .
H52A H 0.6508 0.4160 0.5708 0.049 Uiso 1 1 calc R U .
C53A C 0.5746(3) 0.3693(2) 0.56652(16) 0.0521(15) Uani 1 1 d . . .
H53A H 0.5921 0.3339 0.5577 0.063 Uiso 1 1 calc R U .
C54A C 0.5142(3) 0.3724(3) 0.57117(18) 0.0587(17) Uani 1 1 d . . .
H54A H 0.4901 0.3398 0.5647 0.070 Uiso 1 1 calc R U .
C55A C 0.4894(2) 0.4233(3) 0.58535(16) 0.0511(15) Uani 1 1 d . . .
H55A H 0.4481 0.4257 0.5889 0.061 Uiso 1 1 calc R U .
C56A C 0.5237(2) 0.4701(2) 0.59430(14) 0.0383(12) Uani 1 1 d . . .
H56A H 0.5062 0.5046 0.6045 0.046 Uiso 1 1 calc R U .
O61 O 1.0000 0.7500 0.5297(2) 0.099(3) Uani 1 2 d S T P
C61 C 1.0000 0.7500 0.5640(3) 0.062(2) Uani 1 2 d S T P
C62 C 0.9432(3) 0.7512(3) 0.5868(2) 0.087(2) Uani 1 1 d . . .
H62A H 0.9391 0.7893 0.5996 0.130 Uiso 1 1 calc R U .
H62B H 0.9437 0.7199 0.6061 0.130 Uiso 1 1 calc R U .
H62C H 0.9099 0.7452 0.5693 0.130 Uiso 1 1 calc R U .
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_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C2 118.6(4) . .
C1 N1 H1 121(3) . .
C2 N1 H1 120(3) . .
C5 N2 C4 123.9(4) . .
C5 N2 H2 112(2) . .
C4 N2 H2 124(2) . .
O1 C1 N1 119.6(4) . .
O1 C1 C11 122.0(4) . .
N1 C1 C11 118.3(4) . .
N1 C2 C7 108.3(4) . .
N1 C2 C3 113.4(3) . .
C7 C2 C3 111.1(4) . .
N1 C2 H2AA 107.9 . .
C7 C2 H2AA 107.9 . .
C3 C2 H2AA 107.9 . .
C6 C3 C2 112.1(4) . .
C6 C3 C4 111.6(4) . .
C2 C3 C4 110.9(3) . .
C6 C3 H3 107.3 . .
C2 C3 H3 107.3 . .
C4 C3 H3 107.3 . .
N2 C4 C41 110.1(3) . .
N2 C4 C3 110.1(3) . .
C41 C4 C3 112.7(4) . .
N2 C4 H4 107.9 . .
C41 C4 H4 107.9 . .
C3 C4 H4 107.9 . .
O2 C5 N2 123.0(4) . .
O2 C5 C51 121.8(4) . .
N2 C5 C51 115.2(4) . .
C3 C6 H6A 109.5 . .
C3 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C3 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N3 C7 C2 178.4(6) . .
C12 C11 C16 118.7(5) . .
C12 C11 C1 124.4(4) . .
C16 C11 C1 116.8(4) . .
C11 C12 C13 120.4(5) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
C14 C13 C12 120.4(5) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C13 C14 C15 119.7(5) . .
C13 C14 H14 120.1 . .
C15 C14 H14 120.1 . .
C16 C15 C14 119.9(5) . .
C16 C15 H15 120.1 . .
C14 C15 H15 120.1 . .
C15 C16 C11 120.8(5) . .
C15 C16 H16 119.6 . .
C11 C16 H16 119.6 . .
C42 C41 C46 118.3(4) . .
C42 C41 C4 121.2(4) . .
C46 C41 C4 120.5(4) . .
C41 C42 C43 121.3(5) . .
C41 C42 H42 119.3 . .
C43 C42 H42 119.3 . .
C44 C43 C42 119.5(5) . .
C44 C43 H43 120.2 . .
C42 C43 H43 120.2 . .
C43 C44 C45 119.6(5) . .
C43 C44 H44 120.2 . .
C45 C44 H44 120.2 . .
C44 C45 C46 121.5(5) . .
C44 C45 H45 119.2 . .
C46 C45 H45 119.2 . .
C45 C46 C41 119.6(5) . .
C45 C46 H46 120.2 . .
C41 C46 H46 120.2 . .
C56 C51 C52 119.2(4) . .
C56 C51 C5 119.2(4) . .
C52 C51 C5 121.5(4) . .
C53 C52 C51 120.2(5) . .
C53 C52 H52 119.9 . .
C51 C52 H52 119.9 . .
C54 C53 C52 119.6(5) . .
C54 C53 H53 120.2 . .
C52 C53 H53 120.2 . .
C55 C54 C53 121.7(5) . .
C55 C54 H54 119.2 . .
C53 C54 H54 119.2 . .
C54 C55 C56 118.6(5) . .
C54 C55 H55 120.7 . .
C56 C55 H55 120.7 . .
C51 C56 C55 120.6(4) . .
C51 C56 H56 119.7 . .
C55 C56 H56 119.7 . .
C1A N1A C2A 117.6(4) . .
C1A N1A H1A 127(4) . .
C2A N1A H1A 113(4) . .
C5A N2A C4A 123.4(4) . .
C5A N2A H2A 119(4) . .
C4A N2A H2A 117(4) . .
O1A C1A N1A 119.5(4) . .
O1A C1A C11A 121.7(4) . .
N1A C1A C11A 118.8(4) . .
N1A C2A C7A 109.2(4) . .
N1A C2A C3A 113.3(3) . .
C7A C2A C3A 111.1(4) . .
N1A C2A H2A1 107.7 . .
C7A C2A H2A1 107.7 . .
C3A C2A H2A1 107.7 . .
C6A C3A C2A 112.0(4) . .
C6A C3A C4A 111.5(3) . .
C2A C3A C4A 108.9(3) . .
C6A C3A H3A 108.1 . .
C2A C3A H3A 108.1 . .
C4A C3A H3A 108.1 . .
N2A C4A C41A 110.4(4) . .
N2A C4A C3A 111.4(3) . .
C41A C4A C3A 111.4(4) . .
N2A C4A H4A 107.8 . .
C41A C4A H4A 107.8 . .
C3A C4A H4A 107.8 . .
O2A C5A N2A 122.4(4) . .
O2A C5A C51A 120.7(4) . .
N2A C5A C51A 116.9(4) . .
C3A C6A H6A1 109.5 . .
C3A C6A H6A2 109.5 . .
H6A1 C6A H6A2 109.5 . .
C3A C6A H6A3 109.5 . .
H6A1 C6A H6A3 109.5 . .
H6A2 C6A H6A3 109.5 . .
N3A C7A C2A 178.9(6) . .
C12A C11A C16A 119.4(4) . .
C12A C11A C1A 123.7(4) . .
C16A C11A C1A 116.9(4) . .
C11A C12A C13A 120.2(4) . .
C11A C12A H12A 119.9 . .
C13A C12A H12A 119.9 . .
C14A C13A C12A 119.5(5) . .
C14A C13A H13A 120.2 . .
C12A C13A H13A 120.2 . .
C15A C14A C13A 120.1(5) . .
C15A C14A H14A 119.9 . .
C13A C14A H14A 119.9 . .
C16A C15A C14A 120.1(5) . .
C16A C15A H15A 119.9 . .
C14A C15A H15A 119.9 . .
C15A C16A C11A 120.6(5) . .
C15A C16A H16A 119.7 . .
C11A C16A H16A 119.7 . .
C42A C41A C46A 119.6(5) . .
C42A C41A C4A 121.6(5) . .
C46A C41A C4A 118.7(5) . .
C43A C42A C41A 122.1(7) . .
C43A C42A H42A 119.0 . .
C41A C42A H42A 119.0 . .
C42A C43A C44A 117.3(8) . .
C42A C43A H43A 121.3 . .
C44A C43A H43A 121.3 . .
C45A C44A C43A 121.9(8) . .
C45A C44A H44A 119.1 . .
C43A C44A H44A 119.1 . .
C44A C45A C46A 120.7(9) . .
C44A C45A H45A 119.6 . .
C46A C45A H45A 119.6 . .
C41A C46A C45A 118.4(8) . .
C41A C46A H46A 120.8 . .
C45A C46A H46A 120.8 . .
C52A C51A C56A 119.3(5) . .
C52A C51A C5A 121.6(4) . .
C56A C51A C5A 119.1(4) . .
C51A C52A C53A 119.7(5) . .
C51A C52A H52A 120.1 . .
C53A C52A H52A 120.1 . .
C54A C53A C52A 120.2(5) . .
C54A C53A H53A 119.9 . .
C52A C53A H53A 119.9 . .
C55A C54A C53A 119.4(5) . .
C55A C54A H54A 120.3 . .
C53A C54A H54A 120.3 . .
C56A C55A C54A 120.3(5) . .
C56A C55A H55A 119.9 . .
C54A C55A H55A 119.9 . .
C55A C56A C51A 121.0(5) . .
C55A C56A H56A 119.5 . .
C51A C56A H56A 119.5 . .
O61 C61 C62 121.4(5) . 6_664
O61 C61 C62 121.4(5) . .
C62 C61 C62 117.1(9) 6_664 .
C61 C62 H62A 109.5 . .
C61 C62 H62B 109.5 . .
H62A C62 H62B 109.5 . .
C61 C62 H62C 109.5 . .
H62A C62 H62C 109.5 . .
H62B C62 H62C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.229(5) .
O2 C5 1.241(5) .
N1 C1 1.355(6) .
N1 C2 1.450(5) .
N1 H1 0.95(5) .
N2 C5 1.339(5) .
N2 C4 1.480(5) .
N2 H2 1.03(4) .
N3 C7 1.135(6) .
C1 C11 1.485(6) .
C2 C7 1.488(6) .
C2 C3 1.534(6) .
C2 H2AA 1.0000 .
C3 C6 1.514(6) .
C3 C4 1.537(6) .
C3 H3 1.0000 .
C4 C41 1.515(6) .
C4 H4 1.0000 .
C5 C51 1.492(6) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C11 C12 1.387(6) .
C11 C16 1.400(6) .
C12 C13 1.386(7) .
C12 H12 0.9500 .
C13 C14 1.376(8) .
C13 H13 0.9500 .
C14 C15 1.395(8) .
C14 H14 0.9500 .
C15 C16 1.372(7) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C41 C42 1.383(6) .
C41 C46 1.388(6) .
C42 C43 1.400(7) .
C42 H42 0.9500 .
C43 C44 1.360(7) .
C43 H43 0.9500 .
C44 C45 1.372(7) .
C44 H44 0.9500 .
C45 C46 1.386(7) .
C45 H45 0.9500 .
C46 H46 0.9500 .
C51 C56 1.381(6) .
C51 C52 1.389(6) .
C52 C53 1.381(7) .
C52 H52 0.9500 .
C53 C54 1.376(8) .
C53 H53 0.9500 .
C54 C55 1.363(8) .
C54 H54 0.9500 .
C55 C56 1.405(6) .
C55 H55 0.9500 .
C56 H56 0.9500 .
O1A C1A 1.228(5) .
O2A C5A 1.241(5) .
N1A C1A 1.349(5) .
N1A C2A 1.436(5) .
N1A H1A 0.76(5) .
N2A C5A 1.344(5) .
N2A C4A 1.466(6) .
N2A H2A 0.79(5) .
N3A C7A 1.134(6) .
C1A C11A 1.491(6) .
C2A C7A 1.478(7) .
C2A C3A 1.541(6) .
C2A H2A1 1.0000 .
C3A C6A 1.524(6) .
C3A C4A 1.543(6) .
C3A H3A 1.0000 .
C4A C41A 1.527(7) .
C4A H4A 1.0000 .
C5A C51A 1.495(6) .
C6A H6A1 0.9800 .
C6A H6A2 0.9800 .
C6A H6A3 0.9800 .
C11A C12A 1.379(6) .
C11A C16A 1.387(6) .
C12A C13A 1.390(7) .
C12A H12A 0.9500 .
C13A C14A 1.386(7) .
C13A H13A 0.9500 .
C14A C15A 1.377(7) .
C14A H14A 0.9500 .
C15A C16A 1.371(7) .
C15A H15A 0.9500 .
C16A H16A 0.9500 .
C41A C42A 1.382(8) .
C41A C46A 1.396(8) .
C42A C43A 1.378(8) .
C42A H42A 0.9500 .
C43A C44A 1.408(13) .
C43A H43A 0.9500 .
C44A C45A 1.341(14) .
C44A H44A 0.9500 .
C45A C46A 1.410(11) .
C45A H45A 0.9500 .
C46A H46A 0.9500 .
C51A C52A 1.376(6) .
C51A C56A 1.391(6) .
C52A C53A 1.392(7) .
C52A H52A 0.9500 .
C53A C54A 1.387(8) .
C53A H53A 0.9500 .
C54A C55A 1.383(8) .
C54A H54A 0.9500 .
C55A C56A 1.357(7) .
C55A H55A 0.9500 .
C56A H56A 0.9500 .
O61 C61 1.194(11) .
C61 C62 1.518(8) 6_664
C61 C62 1.518(8) .
C62 H62A 0.9800 .
C62 H62B 0.9800 .
C62 H62C 0.9800 .
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 O2A 0.95(5) 2.04(5) 2.971(5) 167(4) .
N2 H2 O1A 1.03(4) 1.84(5) 2.833(5) 159(4) .
N1A H1A O2 0.76(5) 2.16(5) 2.923(5) 179(5) 7_544
N2A H2A O1 0.79(5) 2.10(5) 2.891(5) 176(5) 7_544
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
C2 N1 C1 O1 -0.4(6)
C2 N1 C1 C11 -177.6(4)
C1 N1 C2 C7 68.2(5)
C1 N1 C2 C3 -168.0(4)
N1 C2 C3 C6 -67.3(5)
C7 C2 C3 C6 54.9(5)
N1 C2 C3 C4 167.2(3)
C7 C2 C3 C4 -70.5(5)
C5 N2 C4 C41 -106.0(4)
C5 N2 C4 C3 129.1(4)
C6 C3 C4 N2 177.5(3)
C2 C3 C4 N2 -56.7(4)
C6 C3 C4 C41 54.2(5)
C2 C3 C4 C41 180.0(4)
C4 N2 C5 O2 -1.3(6)
C4 N2 C5 C51 178.5(4)
O1 C1 C11 C12 175.5(5)
N1 C1 C11 C12 -7.4(7)
O1 C1 C11 C16 -8.3(7)
N1 C1 C11 C16 168.9(4)
C16 C11 C12 C13 0.1(7)
C1 C11 C12 C13 176.3(5)
C11 C12 C13 C14 -2.0(8)
C12 C13 C14 C15 2.5(9)
C13 C14 C15 C16 -1.0(9)
C14 C15 C16 C11 -0.9(9)
C12 C11 C16 C15 1.3(8)
C1 C11 C16 C15 -175.1(5)
N2 C4 C41 C42 -60.1(5)
C3 C4 C41 C42 63.2(5)
N2 C4 C41 C46 118.0(5)
C3 C4 C41 C46 -118.7(5)
C46 C41 C42 C43 1.6(7)
C4 C41 C42 C43 179.7(4)
C41 C42 C43 C44 -0.8(8)
C42 C43 C44 C45 -0.2(8)
C43 C44 C45 C46 0.4(9)
C44 C45 C46 C41 0.5(8)
C42 C41 C46 C45 -1.4(7)
C4 C41 C46 C45 -179.5(4)
O2 C5 C51 C56 35.6(6)
N2 C5 C51 C56 -144.3(4)
O2 C5 C51 C52 -142.3(4)
N2 C5 C51 C52 37.8(6)
C56 C51 C52 C53 0.5(7)
C5 C51 C52 C53 178.4(5)
C51 C52 C53 C54 0.5(9)
C52 C53 C54 C55 0.4(9)
C53 C54 C55 C56 -2.3(8)
C52 C51 C56 C55 -2.4(7)
C5 C51 C56 C55 179.6(4)
C54 C55 C56 C51 3.3(7)
C2A N1A C1A O1A -4.7(6)
C2A N1A C1A C11A 176.1(4)
C1A N1A C2A C7A 75.0(5)
C1A N1A C2A C3A -160.6(4)
N1A C2A C3A C6A -76.2(5)
C7A C2A C3A C6A 47.2(5)
N1A C2A C3A C4A 160.1(4)
C7A C2A C3A C4A -76.5(4)
C5A N2A C4A C41A -106.5(5)
C5A N2A C4A C3A 129.2(4)
C6A C3A C4A N2A 176.8(4)
C2A C3A C4A N2A -59.2(4)
C6A C3A C4A C41A 53.0(5)
C2A C3A C4A C41A 177.1(4)
C4A N2A C5A O2A -3.5(7)
C4A N2A C5A C51A 177.4(4)
O1A C1A C11A C12A -161.0(4)
N1A C1A C11A C12A 18.1(6)
O1A C1A C11A C16A 19.5(6)
N1A C1A C11A C16A -161.4(4)
C16A C11A C12A C13A -0.8(7)
C1A C11A C12A C13A 179.7(4)
C11A C12A C13A C14A 1.5(8)
C12A C13A C14A C15A -1.1(9)
C13A C14A C15A C16A 0.0(9)
C14A C15A C16A C11A 0.7(8)
C12A C11A C16A C15A -0.3(7)
C1A C11A C16A C15A 179.2(4)
N2A C4A C41A C42A -48.5(6)
C3A C4A C41A C42A 75.8(6)
N2A C4A C41A C46A 134.6(5)
C3A C4A C41A C46A -101.2(5)
C46A C41A C42A C43A -2.1(8)
C4A C41A C42A C43A -179.0(5)
C41A C42A C43A C44A 0.9(10)
C42A C43A C44A C45A 1.1(14)
C43A C44A C45A C46A -1.9(16)
C42A C41A C46A C45A 1.3(8)
C4A C41A C46A C45A 178.3(6)
C44A C45A C46A C41A 0.7(13)
O2A C5A C51A C52A -133.1(5)
N2A C5A C51A C52A 46.0(6)
O2A C5A C51A C56A 48.4(6)
N2A C5A C51A C56A -132.5(5)
C56A C51A C52A C53A -0.3(7)
C5A C51A C52A C53A -178.8(4)
C51A C52A C53A C54A 2.1(8)
C52A C53A C54A C55A -2.2(9)
C53A C54A C55A C56A 0.6(9)
C54A C55A C56A C51A 1.2(8)
C52A C51A C56A C55A -1.4(7)
C5A C51A C56A C55A 177.2(5)
