#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:57:26 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178413 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/34/4023459.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_4023459
loop_
_publ_author_name
'Jonathan Clayden'
'Hazel Turner'
'Madeleine Helliwell'
'Elizabeth Moir'
_publ_contact_author_address
; 
Department of Chemistry 
University of Manchester 
Manchester M13 9PL 
England  UK 
;
_publ_contact_author_email       jrtest@spec.ch.man.ac.uk
_publ_contact_author_fax         44(161)275-4734
_publ_contact_author_name        'Raftery, James'
_publ_contact_author_phone       44(161)275-4700
_publ_section_title
;
 N,N'-Diarylureas: A New Family of Atropisomers Exhibiting
 Highly Diastereoselective Reactivity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4415
_journal_page_last               4423
_journal_paper_doi               10.1021/jo702706c
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C22 H30 N2 O2'
_chemical_formula_weight         354.48
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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                106.016(2)
_cell_angle_beta                 94.723(2)
_cell_angle_gamma                97.553(2)
_cell_formula_units_Z            4
_cell_length_a                   10.5380(11)
_cell_length_b                   11.4950(11)
_cell_length_c                   17.3280(17)
_cell_measurement_reflns_used    3850
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.232
_cell_measurement_theta_min      2.181
_cell_volume                     1984.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al, 2005)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0901
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17204
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9776
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     522
_refine_ls_number_reflns         9013
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1027P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.1797
_reflns_number_gt                5591
_reflns_number_total             9013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702706c-File005.cif
_cod_data_source_block           s2407m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023459
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0841(2) 0.75583(19) 0.10036(12) 0.0193(5) Uani 1 1 d . . .
C2 C -0.0172(2) 0.6753(2) 0.13042(12) 0.0204(5) Uani 1 1 d D A .
C3 C -0.0900(2) 0.5630(2) 0.12738(13) 0.0246(5) Uani 1 1 d . . .
H3 H -0.0479 0.5048 0.1447 0.029 Uiso 1 1 calc R . .
C4 C -0.2198(2) 0.5329(2) 0.10044(14) 0.0251(5) Uani 1 1 d . . .
H4 H -0.2657 0.4558 0.1000 0.030 Uiso 1 1 calc R . .
C5 C -0.2829(2) 0.6149(2) 0.07403(13) 0.0245(5) Uani 1 1 d . . .
H5 H -0.3730 0.5945 0.0567 0.029 Uiso 1 1 calc R . .
C6 C -0.2172(2) 0.7271(2) 0.07221(13) 0.0213(5) Uani 1 1 d . . .
C7 C 0.1269(2) 0.6970(2) 0.16568(13) 0.0241(5) Uani 1 1 d D . .
C8 C 0.1565(7) 0.6088(8) 0.2150(5) 0.046(2) Uani 0.546(12) 1 d PD A 1
H8A H 0.1433 0.5248 0.1790 0.070 Uiso 0.546(12) 1 calc PR A 1
H8B H 0.0989 0.6139 0.2570 0.070 Uiso 0.546(12) 1 calc PR A 1
H8C H 0.2463 0.6317 0.2404 0.070 Uiso 0.546(12) 1 calc PR A 1
C9 C 0.1699(7) 0.8265(5) 0.2253(6) 0.057(3) Uani 0.546(12) 1 d PD A 1
H9A H 0.1798 0.8868 0.1949 0.086 Uiso 0.546(12) 1 calc PR A 1
H9B H 0.2525 0.8292 0.2567 0.086 Uiso 0.546(12) 1 calc PR A 1
H9C H 0.1047 0.8455 0.2620 0.086 Uiso 0.546(12) 1 calc PR A 1
C10 C 0.2164(7) 0.6782(11) 0.0999(4) 0.059(3) Uani 0.546(12) 1 d PD A 1
H10A H 0.1876 0.5978 0.0602 0.089 Uiso 0.546(12) 1 calc PR A 1
H10B H 0.3046 0.6821 0.1244 0.089 Uiso 0.546(12) 1 calc PR A 1
H10C H 0.2143 0.7426 0.0730 0.089 Uiso 0.546(12) 1 calc PR A 1
C8S C 0.2087(7) 0.8196(7) 0.1746(7) 0.049(3) Uani 0.454(12) 1 d PD A 2
H8D H 0.2231 0.8272 0.1210 0.073 Uiso 0.454(12) 1 calc PR A 2
H8E H 0.2918 0.8251 0.2063 0.073 Uiso 0.454(12) 1 calc PR A 2
H8F H 0.1641 0.8857 0.2024 0.073 Uiso 0.454(12) 1 calc PR A 2
C9S C 0.1328(8) 0.6731(12) 0.2474(5) 0.048(3) Uani 0.454(12) 1 d PD A 2
H9D H 0.0837 0.5920 0.2418 0.071 Uiso 0.454(12) 1 calc PR A 2
H9E H 0.0957 0.7359 0.2852 0.071 Uiso 0.454(12) 1 calc PR A 2
H9F H 0.2229 0.6757 0.2680 0.071 Uiso 0.454(12) 1 calc PR A 2
C10S C 0.1875(8) 0.5986(11) 0.1064(6) 0.061(3) Uani 0.454(12) 1 d PD A 2
H10D H 0.1863 0.6155 0.0539 0.092 Uiso 0.454(12) 1 calc PR A 2
H10E H 0.1378 0.5174 0.0994 0.092 Uiso 0.454(12) 1 calc PR A 2
H10F H 0.2768 0.6007 0.1283 0.092 Uiso 0.454(12) 1 calc PR A 2
C11 C -0.2895(2) 0.8144(2) 0.04132(13) 0.0232(5) Uani 1 1 d . . .
H11 H -0.2289 0.8936 0.0537 0.028 Uiso 1 1 calc R . .
C12 C -0.4060(2) 0.8424(2) 0.08684(16) 0.0329(6) Uani 1 1 d . . .
H12A H -0.4634 0.7656 0.0817 0.049 Uiso 1 1 calc R . .
H12B H -0.4530 0.8956 0.0637 0.049 Uiso 1 1 calc R . .
H12C H -0.3761 0.8839 0.1441 0.049 Uiso 1 1 calc R . .
C13 C -0.3296(2) 0.7722(2) -0.05110(14) 0.0259(5) Uani 1 1 d . . .
H13 H -0.3741 0.8367 -0.0650 0.031 Uiso 1 1 calc R . .
C14 C -0.4185(2) 0.6512(2) -0.08606(16) 0.0342(6) Uani 1 1 d . . .
H14A H -0.4481 0.6409 -0.1430 0.051 Uiso 1 1 calc R . .
H14B H -0.4931 0.6500 -0.0559 0.051 Uiso 1 1 calc R . .
H14C H -0.3722 0.5842 -0.0820 0.051 Uiso 1 1 calc R . .
C15 C -0.0337(2) 0.9795(2) 0.16906(13) 0.0248(5) Uani 1 1 d . . .
H15A H 0.0322 1.0496 0.1716 0.037 Uiso 1 1 calc R . .
H15B H -0.0236 0.9579 0.2199 0.037 Uiso 1 1 calc R . .
H15C H -0.1196 1.0012 0.1608 0.037 Uiso 1 1 calc R . .
C16 C 0.0579(2) 0.8927(2) 0.04574(13) 0.0199(5) Uani 1 1 d . . .
C17 C 0.1232(2) 0.7848(2) -0.08567(14) 0.0231(5) Uani 1 1 d . . .
C18 C 0.0643(2) 0.7187(2) -0.16350(14) 0.0260(5) Uani 1 1 d . . .
H18 H -0.0251 0.6864 -0.1719 0.031 Uiso 1 1 calc R . .
C19 C 0.1350(3) 0.7002(2) -0.22840(16) 0.0335(6) Uani 1 1 d . . .
H19 H 0.0945 0.6544 -0.2810 0.040 Uiso 1 1 calc R . .
C20 C 0.2658(3) 0.7487(3) -0.21654(17) 0.0380(7) Uani 1 1 d . . .
H20 H 0.3150 0.7355 -0.2608 0.046 Uiso 1 1 calc R . .
C21 C 0.3232(2) 0.8160(2) -0.14014(17) 0.0338(6) Uani 1 1 d . . .
H21 H 0.4119 0.8507 -0.1323 0.041 Uiso 1 1 calc R . .
C22 C 0.2531(2) 0.8337(2) -0.07419(16) 0.0293(5) Uani 1 1 d . . .
H22 H 0.2942 0.8792 -0.0216 0.035 Uiso 1 1 calc R . .
C23 C 0.69225(19) 0.74618(19) 0.50528(13) 0.0183(4) Uani 1 1 d . . .
C24 C 0.7065(2) 0.6662(2) 0.55410(13) 0.0194(5) Uani 1 1 d . . .
C25 C 0.7397(2) 0.5529(2) 0.51548(14) 0.0242(5) Uani 1 1 d . . .
H25 H 0.7468 0.4956 0.5454 0.029 Uiso 1 1 calc R . .
C26 C 0.7628(2) 0.5205(2) 0.43555(14) 0.0251(5) Uani 1 1 d . . .
H26 H 0.7872 0.4430 0.4120 0.030 Uiso 1 1 calc R . .
C27 C 0.7506(2) 0.6000(2) 0.39017(14) 0.0224(5) Uani 1 1 d . . .
H27 H 0.7683 0.5778 0.3356 0.027 Uiso 1 1 calc R . .
C28 C 0.7126(2) 0.71310(19) 0.42328(13) 0.0191(4) Uani 1 1 d . . .
C29 C 0.6892(2) 0.6930(2) 0.64509(13) 0.0231(5) Uani 1 1 d . . .
C30 C 0.5472(3) 0.6767(4) 0.6564(2) 0.0735(12) Uani 1 1 d . . .
H30A H 0.5387 0.6858 0.7136 0.110 Uiso 1 1 calc R . .
H30B H 0.5048 0.5948 0.6237 0.110 Uiso 1 1 calc R . .
H30C H 0.5064 0.7389 0.6393 0.110 Uiso 1 1 calc R . .
C31 C 0.7542(5) 0.8187(3) 0.69634(19) 0.0862(15) Uani 1 1 d . . .
H31A H 0.7025 0.8802 0.6881 0.129 Uiso 1 1 calc R . .
H31B H 0.8403 0.8366 0.6807 0.129 Uiso 1 1 calc R . .
H31C H 0.7620 0.8210 0.7535 0.129 Uiso 1 1 calc R . .
C32 C 0.7468(4) 0.6024(4) 0.68306(18) 0.0645(11) Uani 1 1 d . . .
H32A H 0.8375 0.6035 0.6740 0.097 Uiso 1 1 calc R . .
H32B H 0.6987 0.5196 0.6580 0.097 Uiso 1 1 calc R . .
H32C H 0.7410 0.6264 0.7413 0.097 Uiso 1 1 calc R . .
C33 C 0.6958(2) 0.7968(2) 0.37008(13) 0.0218(5) Uani 1 1 d . . .
H33 H 0.6867 0.8785 0.4068 0.026 Uiso 1 1 calc R . .
C34 C 0.8147(2) 0.8175(2) 0.32729(16) 0.0324(6) Uani 1 1 d . . .
H34A H 0.8912 0.8496 0.3676 0.049 Uiso 1 1 calc R . .
H34B H 0.8026 0.8766 0.2971 0.049 Uiso 1 1 calc R . .
H34C H 0.8265 0.7396 0.2898 0.049 Uiso 1 1 calc R . .
C35 C 0.5730(2) 0.7539(2) 0.30799(14) 0.0251(5) Uani 1 1 d . . .
H35 H 0.5732 0.8118 0.2742 0.030 Uiso 1 1 calc R . .
C36 C 0.5564(3) 0.6251(2) 0.25116(15) 0.0347(6) Uani 1 1 d . . .
H36A H 0.5430 0.5657 0.2820 0.052 Uiso 1 1 calc R . .
H36B H 0.6339 0.6141 0.2241 0.052 Uiso 1 1 calc R . .
H36C H 0.4814 0.6120 0.2105 0.052 Uiso 1 1 calc R . .
C37 C 0.7756(2) 0.9688(2) 0.56266(14) 0.0241(5) Uani 1 1 d . . .
H37A H 0.8010 0.9870 0.5135 0.036 Uiso 1 1 calc R . .
H37B H 0.8484 0.9450 0.5903 0.036 Uiso 1 1 calc R . .
H37C H 0.7505 1.0418 0.5987 0.036 Uiso 1 1 calc R . .
C38 C 0.5467(2) 0.8942(2) 0.55505(12) 0.0182(4) Uani 1 1 d . . .
C39 C 0.3169(2) 0.7992(2) 0.52682(14) 0.0220(5) Uani 1 1 d . . .
C40 C 0.2270(2) 0.7334(2) 0.46035(15) 0.0256(5) Uani 1 1 d . . .
H40 H 0.2554 0.6976 0.4098 0.031 Uiso 1 1 calc R . .
C41 C 0.0967(2) 0.7204(2) 0.46788(17) 0.0337(6) Uani 1 1 d . . .
H41 H 0.0358 0.6746 0.4227 0.040 Uiso 1 1 calc R . .
C42 C 0.0548(2) 0.7738(2) 0.54103(19) 0.0370(6) Uani 1 1 d . . .
H42 H -0.0347 0.7639 0.5463 0.044 Uiso 1 1 calc R . .
C43 C 0.1422(2) 0.8406(2) 0.60555(17) 0.0340(6) Uani 1 1 d . . .
H43 H 0.1126 0.8787 0.6552 0.041 Uiso 1 1 calc R . .
C44 C 0.2747(2) 0.8540(2) 0.59986(15) 0.0273(5) Uani 1 1 d . . .
H44 H 0.3349 0.9000 0.6453 0.033 Uiso 1 1 calc R . .
N1 N -0.01871(17) 0.87511(16) 0.10194(11) 0.0211(4) Uani 1 1 d . . .
N2 N 0.04820(19) 0.79366(18) -0.02144(11) 0.0226(4) Uani 1 1 d . . .
N3 N 0.66630(17) 0.86813(16) 0.54086(11) 0.0198(4) Uani 1 1 d . . .
N4 N 0.44849(17) 0.80086(17) 0.51689(12) 0.0205(4) Uani 1 1 d . . .
O1 O -0.21860(16) 0.76393(15) -0.09314(10) 0.0273(4) Uani 1 1 d . . .
H1 H -0.1785 0.8347 -0.0869 0.041 Uiso 1 1 calc R . .
O2 O 0.13234(16) 0.98882(14) 0.05447(10) 0.0283(4) Uani 1 1 d . . .
O3 O 0.46003(15) 0.75978(14) 0.34811(9) 0.0244(4) Uani 1 1 d . . .
H3A H 0.4512 0.8334 0.3671 0.037 Uiso 1 1 calc R . .
O4 O 0.52831(16) 0.99280(14) 0.59939(10) 0.0279(4) Uani 1 1 d . . .
H2N H -0.025(3) 0.752(3) -0.0345(17) 0.042(9) Uiso 1 1 d . . .
H4N H 0.461(2) 0.749(2) 0.4682(16) 0.025(7) Uiso 1 1 d . . .
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
_geom_angle_publ_flag
C6 C1 C2 122.3(2) . . ?
C6 C1 N1 117.25(19) . . ?
C2 C1 N1 120.38(19) . . ?
C3 C2 C1 115.8(2) . . ?
C3 C2 C7 116.58(19) . . ?
C1 C2 C7 127.62(19) . . ?
C4 C3 C2 123.0(2) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 117.9(2) . . ?
C5 C6 C11 119.8(2) . . ?
C1 C6 C11 122.31(19) . . ?
C9S C7 C8S 108.7(4) . . ?
C9S C7 C10 132.7(5) . . ?
C8S C7 C10 72.3(5) . . ?
C9S C7 C8 33.3(3) . . ?
C8S C7 C8 124.6(4) . . ?
C10 C7 C8 105.6(4) . . ?
C9S C7 C9 77.1(5) . . ?
C8S C7 C9 37.6(4) . . ?
C10 C7 C9 108.6(4) . . ?
C8 C7 C9 104.8(4) . . ?
C9S C7 C10S 109.3(5) . . ?
C8S C7 C10S 106.9(5) . . ?
C10 C7 C10S 36.6(4) . . ?
C8 C7 C10S 76.4(5) . . ?
C9 C7 C10S 138.2(4) . . ?
C9S C7 C2 107.7(3) . . ?
C8S C7 C2 118.9(3) . . ?
C10 C7 C2 112.4(3) . . ?
C8 C7 C2 112.8(3) . . ?
C9 C7 C2 112.2(3) . . ?
C10S C7 C2 105.0(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
C7 C8S H8D 109.5 . . ?
C7 C8S H8E 109.5 . . ?
H8D C8S H8E 109.5 . . ?
C7 C8S H8F 109.5 . . ?
H8D C8S H8F 109.5 . . ?
H8E C8S H8F 109.5 . . ?
C7 C9S H9D 109.5 . . ?
C7 C9S H9E 109.5 . . ?
H9D C9S H9E 109.5 . . ?
C7 C9S H9F 109.5 . . ?
H9D C9S H9F 109.5 . . ?
H9E C9S H9F 109.5 . . ?
C7 C10S H10D 109.5 . . ?
C7 C10S H10E 109.5 . . ?
H10D C10S H10E 109.5 . . ?
C7 C10S H10F 109.5 . . ?
H10D C10S H10F 109.5 . . ?
H10E C10S H10F 109.5 . . ?
C6 C11 C12 111.56(19) . . ?
C6 C11 C13 113.94(19) . . ?
C12 C11 C13 110.98(19) . . ?
C6 C11 H11 106.6 . . ?
C12 C11 H11 106.6 . . ?
C13 C11 H11 106.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C14 106.6(2) . . ?
O1 C13 C11 110.66(18) . . ?
C14 C13 C11 117.2(2) . . ?
O1 C13 H13 107.3 . . ?
C14 C13 H13 107.3 . . ?
C11 C13 H13 107.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 N1 123.1(2) . . ?
O2 C16 N2 122.3(2) . . ?
N1 C16 N2 114.59(19) . . ?
C22 C17 C18 119.4(2) . . ?
C22 C17 N2 122.7(2) . . ?
C18 C17 N2 117.8(2) . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 121.0(2) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C17 C22 C21 119.7(2) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C28 C23 C24 121.78(19) . . ?
C28 C23 N3 117.93(18) . . ?
C24 C23 N3 120.11(18) . . ?
C25 C24 C23 116.0(2) . . ?
C25 C24 C29 117.46(19) . . ?
C23 C24 C29 126.57(19) . . ?
C26 C25 C24 122.8(2) . . ?
C26 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
C27 C26 C25 120.1(2) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.7(2) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C27 C28 C23 118.6(2) . . ?
C27 C28 C33 119.06(19) . . ?
C23 C28 C33 122.35(19) . . ?
C31 C29 C30 109.2(3) . . ?
C31 C29 C32 105.4(3) . . ?
C30 C29 C32 105.2(2) . . ?
C31 C29 C24 113.9(2) . . ?
C30 C29 C24 110.9(2) . . ?
C32 C29 C24 111.8(2) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C28 C33 C34 112.16(18) . . ?
C28 C33 C35 113.69(18) . . ?
C34 C33 C35 110.21(19) . . ?
C28 C33 H33 106.8 . . ?
C34 C33 H33 106.8 . . ?
C35 C33 H33 106.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O3 C35 C36 105.84(19) . . ?
O3 C35 C33 110.64(17) . . ?
C36 C35 C33 116.96(19) . . ?
O3 C35 H35 107.7 . . ?
C36 C35 H35 107.7 . . ?
C33 C35 H35 107.7 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N3 C37 H37A 109.5 . . ?
N3 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N3 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O4 C38 N3 123.0(2) . . ?
O4 C38 N4 122.7(2) . . ?
N3 C38 N4 114.25(18) . . ?
C44 C39 C40 119.7(2) . . ?
C44 C39 N4 122.9(2) . . ?
C40 C39 N4 117.3(2) . . ?
C41 C40 C39 120.1(2) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C40 C41 C42 120.1(3) . . ?
C40 C41 H41 119.9 . . ?
C42 C41 H41 119.9 . . ?
C43 C42 C41 119.9(2) . . ?
C43 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
C42 C43 C44 121.2(2) . . ?
C42 C43 H43 119.4 . . ?
C44 C43 H43 119.4 . . ?
C39 C44 C43 119.0(2) . . ?
C39 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
C16 N1 C1 122.93(18) . . ?
C16 N1 C15 119.49(18) . . ?
C1 N1 C15 117.55(17) . . ?
C16 N2 C17 126.0(2) . . ?
C16 N2 H2N 114(2) . . ?
C17 N2 H2N 114(2) . . ?
C38 N3 C23 123.61(17) . . ?
C38 N3 C37 118.79(18) . . ?
C23 N3 C37 117.60(17) . . ?
C38 N4 C39 125.97(19) . . ?
C38 N4 H4N 117.3(16) . . ?
C39 N4 H4N 112.8(16) . . ?
C13 O1 H1 109.5 . . ?
C35 O3 H3A 109.5 . . ?
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
C1 C6 1.410(3) . ?
C1 C2 1.415(3) . ?
C1 N1 1.444(3) . ?
C2 C3 1.398(3) . ?
C2 C7 1.551(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C11 1.518(3) . ?
C7 C9S 1.513(6) . ?
C7 C8S 1.513(6) . ?
C7 C10 1.526(5) . ?
C7 C8 1.540(5) . ?
C7 C9 1.544(5) . ?
C7 C10S 1.549(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8S H8D 0.9800 . ?
C8S H8E 0.9800 . ?
C8S H8F 0.9800 . ?
C9S H9D 0.9800 . ?
C9S H9E 0.9800 . ?
C9S H9F 0.9800 . ?
C10S H10D 0.9800 . ?
C10S H10E 0.9800 . ?
C10S H10F 0.9800 . ?
C11 C12 1.535(3) . ?
C11 C13 1.544(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O1 1.428(3) . ?
C13 C14 1.509(3) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N1 1.459(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O2 1.233(3) . ?
C16 N1 1.355(3) . ?
C16 N2 1.371(3) . ?
C17 C22 1.386(3) . ?
C17 C18 1.398(3) . ?
C17 N2 1.406(3) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.377(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.408(3) . ?
C23 C24 1.424(3) . ?
C23 N3 1.439(3) . ?
C24 C25 1.394(3) . ?
C24 C29 1.552(3) . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.372(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.394(3) . ?
C27 H27 0.9500 . ?
C28 C33 1.522(3) . ?
C29 C31 1.509(4) . ?
C29 C30 1.520(4) . ?
C29 C32 1.537(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.533(3) . ?
C33 C35 1.544(3) . ?
C33 H33 1.0000 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 O3 1.428(3) . ?
C35 C36 1.514(3) . ?
C35 H35 1.0000 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 N3 1.465(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 O4 1.230(3) . ?
C38 N3 1.360(3) . ?
C38 N4 1.365(3) . ?
C39 C44 1.386(3) . ?
C39 C40 1.395(3) . ?
C39 N4 1.410(3) . ?
C40 C41 1.382(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.383(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.363(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.400(3) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
N2 H2N 0.83(3) . ?
N4 H4N 0.92(3) . ?
O1 H1 0.8400 . ?
O3 H3A 0.8400 . ?
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
N4 H4N O3 0.92(3) 2.12(3) 2.847(2) 135(2) .
N2 H2N O1 0.83(3) 2.24(3) 2.916(3) 139(3) .
O3 H3A O4 0.84 1.90 2.719(2) 165.6 2_676
O1 H1 O2 0.84 1.93 2.743(2) 161.7 2_575
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
C6 C1 C2 C3 2.6(3) . . . . ?
N1 C1 C2 C3 178.92(19) . . . . ?
C6 C1 C2 C7 -177.8(2) . . . . ?
N1 C1 C2 C7 -1.5(3) . . . . ?
C1 C2 C3 C4 -2.7(3) . . . . ?
C7 C2 C3 C4 177.6(2) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C4 C5 C6 C1 -1.7(3) . . . . ?
C4 C5 C6 C11 179.0(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
N1 C1 C6 C5 -176.92(19) . . . . ?
C2 C1 C6 C11 178.9(2) . . . . ?
N1 C1 C6 C11 2.4(3) . . . . ?
C3 C2 C7 C9S -52.6(6) . . . . ?
C1 C2 C7 C9S 127.7(6) . . . . ?
C3 C2 C7 C8S -176.8(6) . . . . ?
C1 C2 C7 C8S 3.6(7) . . . . ?
C3 C2 C7 C10 101.7(5) . . . . ?
C1 C2 C7 C10 -77.9(5) . . . . ?
C3 C2 C7 C8 -17.5(5) . . . . ?
C1 C2 C7 C8 162.9(5) . . . . ?
C3 C2 C7 C9 -135.5(6) . . . . ?
C1 C2 C7 C9 44.9(6) . . . . ?
C3 C2 C7 C10S 63.8(6) . . . . ?
C1 C2 C7 C10S -115.8(6) . . . . ?
C5 C6 C11 C12 54.7(3) . . . . ?
C1 C6 C11 C12 -124.7(2) . . . . ?
C5 C6 C11 C13 -71.9(3) . . . . ?
C1 C6 C11 C13 108.7(2) . . . . ?
C6 C11 C13 O1 -61.7(2) . . . . ?
C12 C11 C13 O1 171.33(18) . . . . ?
C6 C11 C13 C14 60.7(3) . . . . ?
C12 C11 C13 C14 -66.2(3) . . . . ?
C22 C17 C18 C19 1.3(3) . . . . ?
N2 C17 C18 C19 -175.9(2) . . . . ?
C17 C18 C19 C20 -0.8(4) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
C19 C20 C21 C22 1.5(4) . . . . ?
C18 C17 C22 C21 -0.4(3) . . . . ?
N2 C17 C22 C21 176.7(2) . . . . ?
C20 C21 C22 C17 -1.0(4) . . . . ?
C28 C23 C24 C25 -0.9(3) . . . . ?
N3 C23 C24 C25 -175.97(19) . . . . ?
C28 C23 C24 C29 178.8(2) . . . . ?
N3 C23 C24 C29 3.8(3) . . . . ?
C23 C24 C25 C26 2.5(3) . . . . ?
C29 C24 C25 C26 -177.3(2) . . . . ?
C24 C25 C26 C27 -1.5(3) . . . . ?
C25 C26 C27 C28 -1.2(3) . . . . ?
C26 C27 C28 C23 2.6(3) . . . . ?
C26 C27 C28 C33 -178.0(2) . . . . ?
C24 C23 C28 C27 -1.6(3) . . . . ?
N3 C23 C28 C27 173.60(18) . . . . ?
C24 C23 C28 C33 179.07(19) . . . . ?
N3 C23 C28 C33 -5.8(3) . . . . ?
C25 C24 C29 C31 134.4(3) . . . . ?
C23 C24 C29 C31 -45.3(4) . . . . ?
C25 C24 C29 C30 -101.9(3) . . . . ?
C23 C24 C29 C30 78.3(3) . . . . ?
C25 C24 C29 C32 15.1(3) . . . . ?
C23 C24 C29 C32 -164.6(2) . . . . ?
C27 C28 C33 C34 -51.9(3) . . . . ?
C23 C28 C33 C34 127.5(2) . . . . ?
C27 C28 C33 C35 74.0(2) . . . . ?
C23 C28 C33 C35 -106.7(2) . . . . ?
C28 C33 C35 O3 65.6(2) . . . . ?
C34 C33 C35 O3 -167.48(18) . . . . ?
C28 C33 C35 C36 -55.6(3) . . . . ?
C34 C33 C35 C36 71.3(3) . . . . ?
C44 C39 C40 C41 -1.7(3) . . . . ?
N4 C39 C40 C41 175.1(2) . . . . ?
C39 C40 C41 C42 0.9(3) . . . . ?
C40 C41 C42 C43 0.7(4) . . . . ?
C41 C42 C43 C44 -1.5(4) . . . . ?
C40 C39 C44 C43 0.9(3) . . . . ?
N4 C39 C44 C43 -175.7(2) . . . . ?
C42 C43 C44 C39 0.7(3) . . . . ?
O2 C16 N1 C1 -166.1(2) . . . . ?
N2 C16 N1 C1 12.6(3) . . . . ?
O2 C16 N1 C15 11.8(3) . . . . ?
N2 C16 N1 C15 -169.48(18) . . . . ?
C6 C1 N1 C16 -102.8(2) . . . . ?
C2 C1 N1 C16 80.6(3) . . . . ?
C6 C1 N1 C15 79.2(2) . . . . ?
C2 C1 N1 C15 -97.3(2) . . . . ?
O2 C16 N2 C17 3.5(3) . . . . ?
N1 C16 N2 C17 -175.23(19) . . . . ?
C22 C17 N2 C16 37.4(3) . . . . ?
C18 C17 N2 C16 -145.5(2) . . . . ?
O4 C38 N3 C23 165.03(19) . . . . ?
N4 C38 N3 C23 -14.0(3) . . . . ?
O4 C38 N3 C37 -15.0(3) . . . . ?
N4 C38 N3 C37 166.02(18) . . . . ?
C28 C23 N3 C38 103.0(2) . . . . ?
C24 C23 N3 C38 -81.8(3) . . . . ?
C28 C23 N3 C37 -77.0(2) . . . . ?
C24 C23 N3 C37 98.3(2) . . . . ?
O4 C38 N4 C39 -5.1(3) . . . . ?
N3 C38 N4 C39 173.92(19) . . . . ?
C44 C39 N4 C38 -34.3(3) . . . . ?
C40 C39 N4 C38 149.0(2) . . . . ?
