#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024823.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_4024823
loop_
_publ_author_name
'Christopher W. Bond'
'Alexander J. Cresswell'
'Stephen G. Davies'
'Ai M. Fletcher'
'Wataru Kurosawa'
'James A. Lee'
'Paul M. Roberts'
'Angela J. Russell'
'Andrew D. Smith'
'James E. Thomson'
_publ_contact_author_address
;Department of Chemistry
Chemistry Research laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
_publ_contact_author_email       steve.davies@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 275633'
_publ_contact_author_name        'Stephen G. davies'
_publ_contact_author_phone       '+44 1865 275695'
_publ_section_title
;
Ammonium-Directed Oxidation of Cyclic Allylic and Homoallylic Amines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6735
_journal_page_last               6748
_journal_paper_doi               10.1021/jo9012783
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C21 H27 N1 O2'
_chemical_formula_sum            'C21 H27 N O2'
_chemical_formula_weight         325.45
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_creation_date             05-04-29
_audit_creation_method           CRYSTALS_ver_12.50
_cell_angle_alpha                100.7822(6)
_cell_angle_beta                 93.3074(7)
_cell_angle_gamma                109.7640(10)
_cell_formula_units_Z            4
_cell_length_a                   9.80800(10)
_cell_length_b                   12.7341(2)
_cell_length_c                   15.9205(3)
_cell_measurement_reflns_used    7701
_cell_measurement_temperature    123
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1822.44(5)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15239
_diffrn_reflns_theta_full        26.598
_diffrn_reflns_theta_max         27.421
_diffrn_reflns_theta_min         5.106
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         8195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0787
_refine_ls_shift/su_max          0.000255
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 p=(max(Fo²,0) + 2Fc²)/3 
 Method = SHELXL 97 (Sheldrick, 1997) 
 w=1/[sigma²(F²) + 0.04 + 0.49p] 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1140
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1140
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                8195
_reflns_number_total             8196
_reflns_threshold_expression     I>-10.00u(I)
_oxford_diffrn_Wilson_B_factor   3.03
_oxford_diffrn_Wilson_scale      1.53
_oxford_refine_ls_scale          0.7652(16)
_oxford_structure_analysis_title '4260951 pr73'
_cod_data_source_file            jo9012783_si_018.cif
_cod_data_source_block           CRYSTALS_cif
_cod_original_formula_sum        'C21 H27 N1 O2'
_cod_database_code               4024823
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.20063(11) 0.30416(9) 0.37737(7) 0.0319 1.0000 Uani . . . . . .
C2 C 0.11139(15) 0.35776(11) 0.42923(9) 0.0338 1.0000 Uani . . . . . .
C3 C 0.04091(14) 0.29394(10) 0.49722(8) 0.0304 1.0000 Uani . . . . . .
C4 C -0.06323(14) 0.17256(11) 0.45689(8) 0.0323 1.0000 Uani . . . . . .
C5 C -0.13998(15) 0.11206(12) 0.52409(9) 0.0381 1.0000 Uani . . . . . .
O6 O -0.03732(12) 0.10246(8) 0.58659(6) 0.0481 1.0000 Uani . . . . . .
O7 O 0.01178(10) 0.10513(8) 0.41146(6) 0.0408 1.0000 Uani . . . . . .
C8 C -0.04169(16) 0.36204(12) 0.54810(9) 0.0406 1.0000 Uani . . . . . .
C9 C -0.12274(17) 0.30121(13) 0.61424(10) 0.0472 1.0000 Uani . . . . . .
C10 C 0.22432(15) 0.34890(12) 0.29790(9) 0.0381 1.0000 Uani . . . . . .
C11 C 0.08600(14) 0.31392(12) 0.23666(8) 0.0352 1.0000 Uani . . . . . .
C12 C 0.00609(16) 0.19933(13) 0.20215(9) 0.0428 1.0000 Uani . . . . . .
C13 C -0.12048(17) 0.16638(14) 0.14488(10) 0.0497 1.0000 Uani . . . . . .
C14 C -0.16795(18) 0.24775(15) 0.12079(10) 0.0528 1.0000 Uani . . . . . .
C15 C -0.09051(19) 0.36154(16) 0.15427(11) 0.0586 1.0000 Uani . . . . . .
C16 C 0.03594(18) 0.39467(14) 0.21214(10) 0.0490 1.0000 Uani . . . . . .
C17 C 0.34363(14) 0.33028(12) 0.42861(9) 0.0376 1.0000 Uani . . . . . .
C18 C 0.43321(14) 0.26511(12) 0.38543(9) 0.0347 1.0000 Uani . . . . . .
C19 C 0.56794(15) 0.32300(13) 0.36161(9) 0.0415 1.0000 Uani . . . . . .
C20 C 0.65002(16) 0.26306(14) 0.32147(10) 0.0470 1.0000 Uani . . . . . .
C21 C 0.59918(16) 0.14562(14) 0.30453(10) 0.0458 1.0000 Uani . . . . . .
C22 C 0.46652(17) 0.08712(13) 0.32863(10) 0.0468 1.0000 Uani . . . . . .
C23 C 0.38408(15) 0.14625(12) 0.36889(10) 0.0424 1.0000 Uani . . . . . .
N24 N 0.08332(11) 0.18650(9) -0.13759(7) 0.0327 1.0000 Uani . . . . . .
C25 C 0.18004(14) 0.13697(11) -0.18547(8) 0.0331 1.0000 Uani . . . . . .
C26 C 0.24371(13) 0.19708(10) -0.25651(8) 0.0291 1.0000 Uani . . . . . .
C27 C 0.34107(14) 0.32158(11) -0.21926(8) 0.0329 1.0000 Uani . . . . . .
C28 C 0.41646(15) 0.38177(12) -0.28706(9) 0.0400 1.0000 Uani . . . . . .
O29 O 0.31077(12) 0.39797(8) -0.34401(6) 0.0484 1.0000 Uani . . . . . .
O30 O 0.25811(11) 0.38692(8) -0.18066(6) 0.0425 1.0000 Uani . . . . . .
C31 C 0.33127(15) 0.13289(12) -0.30615(9) 0.0366 1.0000 Uani . . . . . .
C32 C 0.39630(16) 0.19078(12) -0.37751(9) 0.0425 1.0000 Uani . . . . . .
C33 C 0.07253(15) 0.15648(13) -0.05225(9) 0.0392 1.0000 Uani . . . . . .
C34 C 0.21393(14) 0.21459(12) 0.00825(8) 0.0364 1.0000 Uani . . . . . .
C35 C 0.28474(17) 0.33272(13) 0.02444(9) 0.0448 1.0000 Uani . . . . . .
C36 C 0.41293(18) 0.38655(14) 0.08066(10) 0.0507 1.0000 Uani . . . . . .
C37 C 0.47202(17) 0.32387(15) 0.12338(10) 0.0496 1.0000 Uani . . . . . .
C38 C 0.40282(17) 0.20704(15) 0.10906(10) 0.0510 1.0000 Uani . . . . . .
C39 C 0.27482(16) 0.15271(14) 0.05144(9) 0.0446 1.0000 Uani . . . . . .
C40 C -0.06385(14) 0.14355(13) -0.18777(9) 0.0399 1.0000 Uani . . . . . .
C41 C -0.16156(15) 0.20312(15) -0.14786(9) 0.0456 1.0000 Uani . . . . . .
C42 C -0.1198(2) 0.32086(17) -0.13193(12) 0.0632 1.0000 Uani . . . . . .
C43 C -0.2063(3) 0.3773(2) -0.09383(14) 0.0863 1.0000 Uani . . . . . .
C44 C -0.3364(3) 0.3174(3) -0.07158(13) 0.0933 1.0000 Uani . . . . . .
C45 C -0.29589(16) 0.14137(19) -0.12636(11) 0.0649 1.0000 Uani . . . . . .
C46 C 0.49525(16) 0.31459(13) -0.33967(10) 0.0475 1.0000 Uani . . . . . .
C49 C -0.22412(17) 0.18035(14) 0.57095(11) 0.0510 1.0000 Uani . . . . . .
C50 C -0.3838(2) 0.1997(3) -0.08797(13) 0.0893 1.0000 Uani . . . . . .
H21 H 0.1736 0.4393 0.4575 0.0513 1.0000 Uiso R . . . . .
H22 H 0.0292 0.3603 0.3873 0.0509 1.0000 Uiso R . . . . .
H31 H 0.1207 0.2890 0.5391 0.0453 1.0000 Uiso R . . . . .
H41 H -0.1438 0.1758 0.4140 0.0460 1.0000 Uiso R . . . . .
H51 H -0.2093 0.0332 0.4926 0.0516 1.0000 Uiso R . . . . .
H81 H 0.0277 0.4402 0.5783 0.0642 1.0000 Uiso R . . . . .
H82 H -0.1156 0.3712 0.5067 0.0632 1.0000 Uiso R . . . . .
H91 H -0.1825 0.3458 0.6417 0.0702 1.0000 Uiso R . . . . .
H92 H -0.0473 0.2960 0.6577 0.0695 1.0000 Uiso R . . . . .
H101 H 0.2681 0.4351 0.3149 0.0558 1.0000 Uiso R . . . . .
H102 H 0.2973 0.3190 0.2687 0.0560 1.0000 Uiso R . . . . .
H121 H 0.0384 0.1388 0.2172 0.0602 1.0000 Uiso R . . . . .
H131 H -0.1765 0.0837 0.1225 0.0727 1.0000 Uiso R . . . . .
H141 H -0.2586 0.2257 0.0801 0.0804 1.0000 Uiso R . . . . .
H151 H -0.1253 0.4204 0.1377 0.0888 1.0000 Uiso R . . . . .
H161 H 0.0924 0.4767 0.2366 0.0747 1.0000 Uiso R . . . . .
H171 H 0.3238 0.3092 0.4863 0.0527 1.0000 Uiso R . . . . .
H172 H 0.3987 0.4155 0.4379 0.0527 1.0000 Uiso R . . . . .
H191 H 0.6019 0.4068 0.3721 0.0613 1.0000 Uiso R . . . . .
H201 H 0.7428 0.3063 0.3054 0.0722 1.0000 Uiso R . . . . .
H211 H 0.6587 0.1039 0.2760 0.0702 1.0000 Uiso R . . . . .
H221 H 0.4331 0.0028 0.3168 0.0733 1.0000 Uiso R . . . . .
H231 H 0.2863 0.1050 0.3860 0.0630 1.0000 Uiso R . . . . .
H251 H 0.2637 0.1453 -0.1426 0.0488 1.0000 Uiso R . . . . .
H252 H 0.1255 0.0521 -0.2108 0.0479 1.0000 Uiso R . . . . .
H261 H 0.1603 0.1981 -0.2976 0.0403 1.0000 Uiso R . . . . .
H271 H 0.4204 0.3233 -0.1725 0.0450 1.0000 Uiso R . . . . .
H281 H 0.4895 0.4601 -0.2557 0.0528 1.0000 Uiso R . . . . .
H311 H 0.4147 0.1346 -0.2645 0.0540 1.0000 Uiso R . . . . .
H312 H 0.2659 0.0495 -0.3302 0.0536 1.0000 Uiso R . . . . .
H321 H 0.4550 0.1481 -0.4077 0.0585 1.0000 Uiso R . . . . .
H322 H 0.3123 0.1899 -0.4195 0.0575 1.0000 Uiso R . . . . .
H331 H -0.0038 0.1834 -0.0252 0.0599 1.0000 Uiso R . . . . .
H332 H 0.0435 0.0693 -0.0596 0.0587 1.0000 Uiso R . . . . .
H351 H 0.2438 0.3777 -0.0051 0.0634 1.0000 Uiso R . . . . .
H361 H 0.4617 0.4696 0.0904 0.0731 1.0000 Uiso R . . . . .
H371 H 0.5649 0.3628 0.1629 0.0704 1.0000 Uiso R . . . . .
H381 H 0.4442 0.1604 0.1380 0.0770 1.0000 Uiso R . . . . .
H391 H 0.2270 0.0695 0.0399 0.0672 1.0000 Uiso R . . . . .
H401 H -0.0518 0.1592 -0.2478 0.0558 1.0000 Uiso R . . . . .
H402 H -0.1086 0.0582 -0.1913 0.0553 1.0000 Uiso R . . . . .
H421 H -0.0269 0.3638 -0.1481 0.1053 1.0000 Uiso R . . . . .
H431 H -0.1765 0.4587 -0.0834 0.1568 1.0000 Uiso R . . . . .
H441 H -0.3971 0.3554 -0.0436 0.1565 1.0000 Uiso R . . . . .
H451 H -0.3267 0.0602 -0.1374 0.1047 1.0000 Uiso R . . . . .
H461 H 0.5305 0.3532 -0.3882 0.0639 1.0000 Uiso R . . . . .
H462 H 0.5784 0.3143 -0.2984 0.0629 1.0000 Uiso R . . . . .
H491 H -0.2696 0.1410 0.6149 0.0742 1.0000 Uiso R . . . . .
H492 H -0.3021 0.1841 0.5266 0.0739 1.0000 Uiso R . . . . .
H501 H -0.4723 0.1574 -0.0733 0.1324 1.0000 Uiso R . . . . .
H39 H -0.0341 0.0336 0.5738 0.0836 1.0000 Uiso R . . . . .
H46 H 0.0778 0.1515 0.3864 0.0748 1.0000 Uiso R . . . . .
H53 H 0.2452 0.4116 -0.3133 0.0892 1.0000 Uiso R . . . . .
H55 H 0.1882 0.3355 -0.1608 0.0763 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C10 . 109.88(10) yes
C2 . N1 . C17 . 109.55(10) yes
C10 . N1 . C17 . 109.43(10) yes
N1 . C2 . C3 . 114.44(10) yes
N1 . C2 . H21 . 109.109 no
C3 . C2 . H21 . 110.054 no
N1 . C2 . H22 . 107.449 no
C3 . C2 . H22 . 108.114 no
H21 . C2 . H22 . 107.409 no
C2 . C3 . C4 . 112.08(11) yes
C2 . C3 . C8 . 108.42(10) yes
C4 . C3 . C8 . 110.00(10) yes
C2 . C3 . H31 . 109.494 no
C4 . C3 . H31 . 108.250 no
C8 . C3 . H31 . 108.527 no
C3 . C4 . C5 . 111.88(11) yes
C3 . C4 . O7 . 111.44(10) yes
C5 . C4 . O7 . 108.77(10) yes
C3 . C4 . H41 . 109.340 no
C5 . C4 . H41 . 106.705 no
O7 . C4 . H41 . 108.540 no
C4 . C5 . O6 . 111.11(11) yes
C4 . C5 . C49 . 109.53(11) yes
O6 . C5 . C49 . 107.90(12) yes
C4 . C5 . H51 . 107.537 no
O6 . C5 . H51 . 110.301 no
C49 . C5 . H51 . 110.468 no
C5 . O6 . H39 . 108.926 no
C4 . O7 . H46 . 106.345 no
C3 . C8 . C9 . 112.07(11) yes
C3 . C8 . H81 . 110.332 no
C9 . C8 . H81 . 109.261 no
C3 . C8 . H82 . 108.600 no
C9 . C8 . H82 . 107.979 no
H81 . C8 . H82 . 108.503 no
C8 . C9 . C49 . 110.53(12) yes
C8 . C9 . H91 . 108.661 no
C49 . C9 . H91 . 109.183 no
C8 . C9 . H92 . 107.660 no
C49 . C9 . H92 . 108.454 no
H91 . C9 . H92 . 112.353 no
N1 . C10 . C11 . 113.07(11) yes
N1 . C10 . H101 . 108.377 no
C11 . C10 . H101 . 109.180 no
N1 . C10 . H102 . 107.304 no
C11 . C10 . H102 . 109.909 no
H101 . C10 . H102 . 108.911 no
C10 . C11 . C12 . 120.60(12) yes
C10 . C11 . C16 . 121.29(13) yes
C12 . C11 . C16 . 118.10(14) yes
C11 . C12 . C13 . 120.99(14) yes
C11 . C12 . H121 . 120.890 no
C13 . C12 . H121 . 118.120 no
C12 . C13 . C14 . 120.11(15) yes
C12 . C13 . H131 . 118.988 no
C14 . C13 . H131 . 120.898 no
C13 . C14 . C15 . 119.79(15) yes
C13 . C14 . H141 . 121.160 no
C15 . C14 . H141 . 119.044 no
C14 . C15 . C16 . 120.15(15) yes
C14 . C15 . H151 . 119.993 no
C16 . C15 . H151 . 119.848 no
C15 . C16 . C11 . 120.86(15) yes
C15 . C16 . H161 . 120.632 no
C11 . C16 . H161 . 118.509 no
N1 . C17 . C18 . 112.99(11) yes
N1 . C17 . H171 . 107.620 no
C18 . C17 . H171 . 109.007 no
N1 . C17 . H172 . 107.538 no
C18 . C17 . H172 . 109.907 no
H171 . C17 . H172 . 109.721 no
C17 . C18 . C19 . 120.57(12) yes
C17 . C18 . C23 . 121.14(12) yes
C19 . C18 . C23 . 118.29(12) yes
C18 . C19 . C20 . 120.59(14) yes
C18 . C19 . H191 . 118.419 no
C20 . C19 . H191 . 120.963 no
C19 . C20 . C21 . 120.45(13) yes
C19 . C20 . H201 . 118.183 no
C21 . C20 . H201 . 121.365 no
C20 . C21 . C22 . 119.60(13) yes
C20 . C21 . H211 . 119.727 no
C22 . C21 . H211 . 120.663 no
C21 . C22 . C23 . 120.32(14) yes
C21 . C22 . H221 . 118.168 no
C23 . C22 . H221 . 121.508 no
C18 . C23 . C22 . 120.73(13) yes
C18 . C23 . H231 . 117.807 no
C22 . C23 . H231 . 121.446 no
C25 . N24 . C33 . 110.56(10) yes
C25 . N24 . C40 . 109.76(10) yes
C33 . N24 . C40 . 109.75(10) yes
N24 . C25 . C26 . 114.13(10) yes
N24 . C25 . H251 . 106.791 no
C26 . C25 . H251 . 107.459 no
N24 . C25 . H252 . 109.805 no
C26 . C25 . H252 . 109.889 no
H251 . C25 . H252 . 108.561 no
C25 . C26 . C27 . 111.29(10) yes
C25 . C26 . C31 . 109.46(10) yes
C27 . C26 . C31 . 110.05(10) yes
C25 . C26 . H261 . 109.225 no
C27 . C26 . H261 . 107.042 no
C31 . C26 . H261 . 109.731 no
C26 . C27 . C28 . 112.93(11) yes
C26 . C27 . O30 . 111.23(10) yes
C28 . C27 . O30 . 106.54(11) yes
C26 . C27 . H271 . 108.523 no
C28 . C27 . H271 . 108.627 no
O30 . C27 . H271 . 108.899 no
C27 . C28 . O29 . 109.68(11) yes
C27 . C28 . C46 . 112.08(12) yes
O29 . C28 . C46 . 108.73(12) yes
C27 . C28 . H281 . 107.649 no
O29 . C28 . H281 . 108.853 no
C46 . C28 . H281 . 109.802 no
C28 . O29 . H53 . 107.291 no
C27 . O30 . H55 . 102.851 no
C26 . C31 . C32 . 110.75(11) yes
C26 . C31 . H311 . 108.421 no
C32 . C31 . H311 . 108.107 no
C26 . C31 . H312 . 109.639 no
C32 . C31 . H312 . 111.424 no
H311 . C31 . H312 . 108.407 no
C31 . C32 . C46 . 110.33(12) yes
C31 . C32 . H321 . 108.865 no
C46 . C32 . H321 . 109.317 no
C31 . C32 . H322 . 108.403 no
C46 . C32 . H322 . 109.095 no
H321 . C32 . H322 . 110.822 no
N24 . C33 . C34 . 112.71(11) yes
N24 . C33 . H331 . 107.692 no
C34 . C33 . H331 . 107.481 no
N24 . C33 . H332 . 109.696 no
C34 . C33 . H332 . 108.583 no
H331 . C33 . H332 . 110.670 no
C33 . C34 . C35 . 120.86(13) yes
C33 . C34 . C39 . 121.21(13) yes
C35 . C34 . C39 . 117.90(13) yes
C34 . C35 . C36 . 121.14(14) yes
C34 . C35 . H351 . 119.203 no
C36 . C35 . H351 . 119.653 no
C35 . C36 . C37 . 120.30(15) yes
C35 . C36 . H361 . 119.812 no
C37 . C36 . H361 . 119.887 no
C36 . C37 . C38 . 119.50(14) yes
C36 . C37 . H371 . 119.887 no
C38 . C37 . H371 . 120.592 no
C37 . C38 . C39 . 120.14(15) yes
C37 . C38 . H381 . 120.833 no
C39 . C38 . H381 . 119.008 no
C38 . C39 . C34 . 121.00(15) yes
C38 . C39 . H391 . 120.289 no
C34 . C39 . H391 . 118.698 no
N24 . C40 . C41 . 112.11(12) yes
N24 . C40 . H401 . 107.840 no
C41 . C40 . H401 . 108.230 no
N24 . C40 . H402 . 108.181 no
C41 . C40 . H402 . 110.161 no
H401 . C40 . H402 . 110.296 no
C40 . C41 . C42 . 120.91(13) yes
C40 . C41 . C45 . 121.02(16) yes
C42 . C41 . C45 . 118.07(16) yes
C41 . C42 . C43 . 121.85(19) yes
C41 . C42 . H421 . 118.049 no
C43 . C42 . H421 . 120.101 no
C42 . C43 . C44 . 120.2(2) yes
C42 . C43 . H431 . 121.014 no
C44 . C43 . H431 . 118.809 no
C43 . C44 . C50 . 120.0(2) yes
C43 . C44 . H441 . 121.370 no
C50 . C44 . H441 . 118.675 no
C41 . C45 . C50 . 119.7(2) yes
C41 . C45 . H451 . 119.120 no
C50 . C45 . H451 . 121.217 no
C32 . C46 . C28 . 112.17(11) yes
C32 . C46 . H461 . 109.073 no
C28 . C46 . H461 . 108.005 no
C32 . C46 . H462 . 108.344 no
C28 . C46 . H462 . 106.393 no
H461 . C46 . H462 . 112.892 no
C9 . C49 . C5 . 111.07(12) yes
C9 . C49 . H491 . 109.244 no
C5 . C49 . H491 . 107.826 no
C9 . C49 . H492 . 109.467 no
C5 . C49 . H492 . 108.333 no
H491 . C49 . H492 . 110.890 no
C45 . C50 . C44 . 120.3(2) yes
C45 . C50 . H501 . 118.558 no
C44 . C50 . H501 . 121.163 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.4800(15) yes
N1 . C10 . 1.4810(16) yes
N1 . C17 . 1.4812(17) yes
C2 . C3 . 1.5316(17) yes
C2 . H21 . 1.009 no
C2 . H22 . 1.030 no
C3 . C4 . 1.5263(18) yes
C3 . C8 . 1.5337(17) yes
C3 . H31 . 1.025 no
C4 . C5 . 1.5211(18) yes
C4 . O7 . 1.4346(15) yes
C4 . H41 . 1.031 no
C5 . O6 . 1.4255(16) yes
C5 . C49 . 1.519(2) yes
C5 . H51 . 1.016 no
O6 . H39 . 0.874 no
O7 . H46 . 0.887 no
C8 . C9 . 1.5252(19) yes
C8 . H81 . 1.005 no
C8 . H82 . 1.002 no
C9 . C49 . 1.524(2) yes
C9 . H91 . 1.009 no
C9 . H92 . 1.011 no
C10 . C11 . 1.5052(19) yes
C10 . H101 . 1.009 no
C10 . H102 . 1.015 no
C11 . C12 . 1.387(2) yes
C11 . C16 . 1.386(2) yes
C12 . C13 . 1.387(2) yes
C12 . H121 . 0.989 no
C13 . C14 . 1.375(2) yes
C13 . H131 . 0.992 no
C14 . C15 . 1.371(2) yes
C14 . H141 . 0.993 no
C15 . C16 . 1.391(2) yes
C15 . H151 . 0.992 no
C16 . H161 . 0.990 no
C17 . C18 . 1.5109(18) yes
C17 . H171 . 1.015 no
C17 . H172 . 1.012 no
C18 . C19 . 1.3917(19) yes
C18 . C23 . 1.3912(19) yes
C19 . C20 . 1.390(2) yes
C19 . H191 . 0.981 no
C20 . C21 . 1.374(2) yes
C20 . H201 . 0.968 no
C21 . C22 . 1.380(2) yes
C21 . H211 . 0.989 no
C22 . C23 . 1.387(2) yes
C22 . H221 . 0.988 no
C23 . H231 . 1.006 no
N24 . C25 . 1.4788(16) yes
N24 . C33 . 1.4788(16) yes
N24 . C40 . 1.4801(17) yes
C25 . C26 . 1.5288(17) yes
C25 . H251 . 1.000 no
C25 . H252 . 1.019 no
C26 . C27 . 1.5285(17) yes
C26 . C31 . 1.5302(17) yes
C26 . H261 . 1.023 no
C27 . C28 . 1.5224(18) yes
C27 . O30 . 1.4339(15) yes
C27 . H271 . 1.037 no
C28 . O29 . 1.4302(17) yes
C28 . C46 . 1.511(2) yes
C28 . H281 . 1.023 no
O29 . H53 . 0.873 no
O30 . H55 . 0.893 no
C31 . C32 . 1.5232(19) yes
C31 . H311 . 1.015 no
C31 . H312 . 1.022 no
C32 . C46 . 1.527(2) yes
C32 . H321 . 1.002 no
C32 . H322 . 1.026 no
C33 . C34 . 1.5112(19) yes
C33 . H331 . 1.009 no
C33 . H332 . 1.030 no
C34 . C35 . 1.393(2) yes
C34 . C39 . 1.387(2) yes
C35 . C36 . 1.382(2) yes
C35 . H351 . 0.972 no
C36 . C37 . 1.381(2) yes
C36 . H361 . 0.979 no
C37 . C38 . 1.378(2) yes
C37 . H371 . 0.991 no
C38 . C39 . 1.392(2) yes
C38 . H381 . 0.987 no
C39 . H391 . 0.979 no
C40 . C41 . 1.510(2) yes
C40 . H401 . 1.018 no
C40 . H402 . 1.014 no
C41 . C42 . 1.382(2) yes
C41 . C45 . 1.387(2) yes
C42 . C43 . 1.384(2) yes
C42 . H421 . 0.969 no
C43 . C44 . 1.353(3) yes
C43 . H431 . 0.955 no
C44 . C50 . 1.378(3) yes
C44 . H441 . 0.965 no
C45 . C50 . 1.412(3) yes
C45 . H451 . 0.952 no
C46 . H461 . 1.008 no
C46 . H462 . 1.018 no
C49 . H491 . 0.979 no
C49 . H492 . 1.029 no
C50 . H501 . 0.923 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_publ_flag
O6 . H39 . O7 2_556 159.87(4) 0.874 1.9072(13) yes
O7 . H46 . N1 . 151.26(4) 0.887 1.9471(14) yes
O30 . H55 . N24 . 156.13(4) 0.893 1.9442(14) yes
