#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150993.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_7150993
loop_
_publ_author_name
'Aciro, Caroline'
'Davies, Stephen G.'
'Roberts, Paul M.'
'Russell, Angela J.'
'Smith, Andrew D.'
'Thomson, James E.'
_publ_section_title
;
 Ammonium-directed dihydroxylation: metal-free synthesis of the
 diastereoisomers of 3-aminocyclohexane-1,2-diol
;
_journal_issue                   20
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3762
_journal_page_last               3770
_journal_paper_doi               10.1039/b808812h
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C20 H25 N1 O2'
_chemical_formula_sum            'C20 H25 N O2'
_chemical_formula_weight         311.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 110.5571(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.83920(10)
_cell_length_b                   28.0222(3)
_cell_length_c                   12.21180(10)
_cell_measurement_reflns_used    8039
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     3473.00(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_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      150
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15636
_diffrn_reflns_theta_full        26.990
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         5.145
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4662
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.000525
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
0.262 0.921E-01 0.701E-01
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0861
_refine_ls_wR_factor_gt          0.0459
_refine_ls_wR_factor_ref         0.0426
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              36
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                5130
_reflns_number_total             7908
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.78
_oxford_diffrn_Wilson_scale      13.10
_oxford_refine_ls_r_factor_ref   0.0403
_oxford_refine_ls_scale          0.2869(4)
_oxford_reflns_number_all        7908
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            b808812h.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 1 21/a 1 '
_cod_original_formula_sum        'C20 H25 N1 O2'
_cod_database_code               7150993
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z
x+1/2,-y+1/2,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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.72217(12) 0.68750(4) 0.30551(9) 0.0366 1.0000 Uani . . . . . . .
C2 C 0.64708(17) 0.72025(6) 0.21636(14) 0.0304 1.0000 Uani . . . . . . .
C3 C 0.63476(16) 0.70108(6) 0.09597(13) 0.0289 1.0000 Uani . . . . . . .
N4 N 0.58889(13) 0.65089(5) 0.08452(11) 0.0297 1.0000 Uani . . . . . . .
C5 C 0.44643(16) 0.64576(6) 0.06172(15) 0.0336 1.0000 Uani . . . . . . .
C6 C 0.41300(16) 0.59538(6) 0.08571(15) 0.0326 1.0000 Uani . . . . . . .
C7 C 0.47490(19) 0.57455(7) 0.19392(16) 0.0401 1.0000 Uani . . . . . . .
C8 C 0.4455(2) 0.52836(7) 0.21721(17) 0.0455 1.0000 Uani . . . . . . .
C9 C 0.3528(2) 0.50232(7) 0.13189(17) 0.0444 1.0000 Uani . . . . . . .
C10 C 0.2890(2) 0.52236(7) 0.02377(17) 0.0470 1.0000 Uani . . . . . . .
C11 C 0.31908(18) 0.56869(7) 0.00100(16) 0.0425 1.0000 Uani . . . . . . .
C12 C 0.62846(16) 0.62414(6) -0.00103(14) 0.0334 1.0000 Uani . . . . . . .
C13 C 0.77132(16) 0.60893(6) 0.04495(14) 0.0310 1.0000 Uani . . . . . . .
C14 C 0.84721(17) 0.60990(6) -0.02593(15) 0.0352 1.0000 Uani . . . . . . .
C15 C 0.97425(18) 0.59188(6) 0.01361(16) 0.0398 1.0000 Uani . . . . . . .
C16 C 1.02844(18) 0.57313(7) 0.12446(17) 0.0427 1.0000 Uani . . . . . . .
C17 C 0.95445(19) 0.57249(7) 0.19680(16) 0.0441 1.0000 Uani . . . . . . .
C18 C 0.82735(18) 0.59004(6) 0.15700(15) 0.0384 1.0000 Uani . . . . . . .
C19 C 0.55134(17) 0.73576(6) 0.00202(14) 0.0341 1.0000 Uani . . . . . . .
C20 C 0.61493(18) 0.78547(6) 0.02289(15) 0.0361 1.0000 Uani . . . . . . .
C21 C 0.63344(18) 0.80374(6) 0.14563(15) 0.0370 1.0000 Uani . . . . . . .
C22 C 0.71292(16) 0.76884(6) 0.23965(14) 0.0324 1.0000 Uani . . . . . . .
O23 O 0.84293(11) 0.76739(4) 0.23583(10) 0.0366 1.0000 Uani . . . . . . .
O24 O 0.52210(11) 0.78159(4) 0.42376(10) 0.0360 1.0000 Uani . . . . . . .
C25 C 0.55358(16) 0.76523(6) 0.54159(13) 0.0297 1.0000 Uani . . . . . . .
C26 C 0.64586(16) 0.80029(5) 0.62791(13) 0.0288 1.0000 Uani . . . . . . .
N27 N 0.59155(13) 0.84922(5) 0.60570(11) 0.0300 1.0000 Uani . . . . . . .
C28 C 0.48086(17) 0.85782(6) 0.64713(15) 0.0330 1.0000 Uani . . . . . . .
C29 C 0.40964(16) 0.90384(6) 0.59963(14) 0.0312 1.0000 Uani . . . . . . .
C30 C 0.37918(17) 0.93604(6) 0.67304(16) 0.0369 1.0000 Uani . . . . . . .
C31 C 0.31191(18) 0.97794(6) 0.62985(17) 0.0414 1.0000 Uani . . . . . . .
C32 C 0.27448(19) 0.98866(7) 0.51293(17) 0.0432 1.0000 Uani . . . . . . .
C33 C 0.3054(2) 0.95733(7) 0.43934(17) 0.0495 1.0000 Uani . . . . . . .
C34 C 0.3715(2) 0.91522(7) 0.48178(16) 0.0433 1.0000 Uani . . . . . . .
C35 C 0.69379(17) 0.88542(6) 0.65560(15) 0.0345 1.0000 Uani . . . . . . .
C36 C 0.79501(16) 0.88951(6) 0.59689(14) 0.0312 1.0000 Uani . . . . . . .
C37 C 0.76585(18) 0.87979(6) 0.47912(15) 0.0383 1.0000 Uani . . . . . . .
C38 C 0.8592(2) 0.88799(7) 0.42714(17) 0.0439 1.0000 Uani . . . . . . .
C39 C 0.98152(19) 0.90624(6) 0.49230(18) 0.0426 1.0000 Uani . . . . . . .
C40 C 1.01087(18) 0.91575(6) 0.60915(17) 0.0404 1.0000 Uani . . . . . . .
C41 C 0.91835(17) 0.90720(6) 0.66135(16) 0.0351 1.0000 Uani . . . . . . .
C42 C 0.67763(18) 0.78129(6) 0.75246(14) 0.0355 1.0000 Uani . . . . . . .
C43 C 0.73971(18) 0.73169(6) 0.76520(15) 0.0380 1.0000 Uani . . . . . . .
C44 C 0.64997(18) 0.69730(6) 0.67588(15) 0.0387 1.0000 Uani . . . . . . .
C45 C 0.61656(16) 0.71608(6) 0.55202(15) 0.0334 1.0000 Uani . . . . . . .
O46 O 0.73573(11) 0.71856(4) 0.52705(10) 0.0374 1.0000 Uani . . . . . . .
H21 H 0.5550 0.7233 0.2197 0.0384 1.0000 Uiso R . . . . . .
H31 H 0.7276 0.7008 0.0935 0.0366 1.0000 Uiso R . . . . . .
H51 H 0.4267 0.6674 0.1189 0.0421 1.0000 Uiso R . . . . . .
H52 H 0.3930 0.6549 -0.0229 0.0419 1.0000 Uiso R . . . . . .
H71 H 0.5390 0.5935 0.2537 0.0506 1.0000 Uiso R . . . . . .
H81 H 0.4910 0.5143 0.2949 0.0589 1.0000 Uiso R . . . . . .
H91 H 0.3328 0.4696 0.1466 0.0570 1.0000 Uiso R . . . . . .
H101 H 0.2249 0.5041 -0.0371 0.0579 1.0000 Uiso R . . . . . .
H111 H 0.2732 0.5831 -0.0753 0.0514 1.0000 Uiso R . . . . . .
H122 H 0.6097 0.6437 -0.0746 0.0442 1.0000 Uiso R . . . . . .
H121 H 0.5734 0.5940 -0.0207 0.0445 1.0000 Uiso R . . . . . .
H141 H 0.8111 0.6234 -0.1041 0.0445 1.0000 Uiso R . . . . . .
H151 H 1.0250 0.5930 -0.0375 0.0505 1.0000 Uiso R . . . . . .
H161 H 1.1182 0.5602 0.1515 0.0541 1.0000 Uiso R . . . . . .
H171 H 0.9934 0.5593 0.2760 0.0549 1.0000 Uiso R . . . . . .
H181 H 0.7743 0.5896 0.2075 0.0492 1.0000 Uiso R . . . . . .
H192 H 0.4615 0.7373 0.0072 0.0424 1.0000 Uiso R . . . . . .
H191 H 0.5410 0.7233 -0.0786 0.0418 1.0000 Uiso R . . . . . .
H202 H 0.5585 0.8086 -0.0363 0.0447 1.0000 Uiso R . . . . . .
H201 H 0.7052 0.7836 0.0153 0.0436 1.0000 Uiso R . . . . . .
H211 H 0.6782 0.8358 0.1570 0.0464 1.0000 Uiso R . . . . . .
H212 H 0.5437 0.8074 0.1516 0.0466 1.0000 Uiso R . . . . . .
H221 H 0.7167 0.7800 0.3204 0.0417 1.0000 Uiso R . . . . . .
H251 H 0.4685 0.7625 0.5585 0.0352 1.0000 Uiso R . . . . . .
H261 H 0.7309 0.8005 0.6092 0.0347 1.0000 Uiso R . . . . . .
H282 H 0.5140 0.8594 0.7352 0.0438 1.0000 Uiso R . . . . . .
H281 H 0.4190 0.8305 0.6211 0.0440 1.0000 Uiso R . . . . . .
H301 H 0.4080 0.9284 0.7572 0.0485 1.0000 Uiso R . . . . . .
H311 H 0.2919 0.9994 0.6831 0.0542 1.0000 Uiso R . . . . . .
H321 H 0.2265 1.0180 0.4822 0.0545 1.0000 Uiso R . . . . . .
H331 H 0.2792 0.9648 0.3569 0.0627 1.0000 Uiso R . . . . . .
H341 H 0.3910 0.8932 0.4286 0.0535 1.0000 Uiso R . . . . . .
H351 H 0.6463 0.9165 0.6458 0.0461 1.0000 Uiso R . . . . . .
H352 H 0.7405 0.8796 0.7417 0.0454 1.0000 Uiso R . . . . . .
H371 H 0.6799 0.8672 0.4337 0.0498 1.0000 Uiso R . . . . . .
H381 H 0.8375 0.8812 0.3441 0.0576 1.0000 Uiso R . . . . . .
H391 H 1.0452 0.9123 0.4548 0.0560 1.0000 Uiso R . . . . . .
H401 H 1.0968 0.9288 0.6551 0.0520 1.0000 Uiso R . . . . . .
H411 H 0.9409 0.9138 0.7450 0.0457 1.0000 Uiso R . . . . . .
H421 H 0.7380 0.8043 0.8085 0.0443 1.0000 Uiso R . . . . . .
H422 H 0.5937 0.7793 0.7702 0.0453 1.0000 Uiso R . . . . . .
H431 H 0.8257 0.7338 0.7516 0.0458 1.0000 Uiso R . . . . . .
H432 H 0.7552 0.7193 0.8452 0.0461 1.0000 Uiso R . . . . . .
H442 H 0.5656 0.6937 0.6911 0.0467 1.0000 Uiso R . . . . . .
H441 H 0.6949 0.6654 0.6831 0.0461 1.0000 Uiso R . . . . . .
H451 H 0.5531 0.6934 0.4954 0.0409 1.0000 Uiso R . . . . . .
H231 H 0.8918 0.7493 0.2956 0.0592 1.0000 Uiso R . . . . . .
H461 H 0.7197 0.7090 0.4545 0.0591 1.0000 Uiso R . . . . . .
H241 H 0.4957 0.8113 0.4223 0.0553 1.0000 Uiso R . . . . . .
H11 H 0.7048 0.6595 0.2717 0.0581 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 . O1 . H11 . 104.2 no
O1 . C2 . C3 . 109.84(13) yes
O1 . C2 . C22 . 109.09(13) yes
C3 . C2 . C22 . 111.89(13) yes
O1 . C2 . H21 . 109.0 no
C3 . C2 . H21 . 108.3 no
C22 . C2 . H21 . 108.7 no
C2 . C3 . N4 . 109.75(12) yes
C2 . C3 . C19 . 109.08(13) yes
N4 . C3 . C19 . 116.16(13) yes
C2 . C3 . H31 . 106.2 no
N4 . C3 . H31 . 107.0 no
C19 . C3 . H31 . 108.3 no
C3 . N4 . C5 . 113.84(12) yes
C3 . N4 . C12 . 112.32(12) yes
C5 . N4 . C12 . 111.33(13) yes
N4 . C5 . C6 . 111.13(13) yes
N4 . C5 . H51 . 105.9 no
C6 . C5 . H51 . 107.8 no
N4 . C5 . H52 . 110.4 no
C6 . C5 . H52 . 109.9 no
H51 . C5 . H52 . 111.6 no
C5 . C6 . C7 . 120.69(15) yes
C5 . C6 . C11 . 121.46(16) yes
C7 . C6 . C11 . 117.85(16) yes
C6 . C7 . C8 . 121.38(17) yes
C6 . C7 . H71 . 117.8 no
C8 . C7 . H71 . 120.8 no
C7 . C8 . C9 . 119.96(18) yes
C7 . C8 . H81 . 119.8 no
C9 . C8 . H81 . 120.3 no
C8 . C9 . C10 . 119.82(18) yes
C8 . C9 . H91 . 120.7 no
C10 . C9 . H91 . 119.4 no
C9 . C10 . C11 . 119.90(18) yes
C9 . C10 . H101 . 120.4 no
C11 . C10 . H101 . 119.7 no
C10 . C11 . C6 . 121.09(17) yes
C10 . C11 . H111 . 120.0 no
C6 . C11 . H111 . 118.9 no
N4 . C12 . C13 . 113.40(13) yes
N4 . C12 . H122 . 109.8 no
C13 . C12 . H122 . 110.1 no
N4 . C12 . H121 . 107.5 no
C13 . C12 . H121 . 107.1 no
H122 . C12 . H121 . 108.9 no
C12 . C13 . C14 . 121.13(15) yes
C12 . C13 . C18 . 120.59(15) yes
C14 . C13 . C18 . 118.09(16) yes
C13 . C14 . C15 . 120.65(16) yes
C13 . C14 . H141 . 119.9 no
C15 . C14 . H141 . 119.5 no
C14 . C15 . C16 . 120.72(16) yes
C14 . C15 . H151 . 118.9 no
C16 . C15 . H151 . 120.3 no
C15 . C16 . C17 . 119.27(17) yes
C15 . C16 . H161 . 120.2 no
C17 . C16 . H161 . 120.5 no
C16 . C17 . C18 . 120.01(17) yes
C16 . C17 . H171 . 119.2 no
C18 . C17 . H171 . 120.8 no
C13 . C18 . C17 . 121.23(16) yes
C13 . C18 . H181 . 118.3 no
C17 . C18 . H181 . 120.5 no
C3 . C19 . C20 . 109.79(14) yes
C3 . C19 . H192 . 108.2 no
C20 . C19 . H192 . 110.0 no
C3 . C19 . H191 . 110.1 no
C20 . C19 . H191 . 111.3 no
H192 . C19 . H191 . 107.3 no
C19 . C20 . C21 . 111.31(14) yes
C19 . C20 . H202 . 110.0 no
C21 . C20 . H202 . 109.1 no
C19 . C20 . H201 . 109.2 no
C21 . C20 . H201 . 107.9 no
H202 . C20 . H201 . 109.3 no
C20 . C21 . C22 . 111.62(14) yes
C20 . C21 . H211 . 108.9 no
C22 . C21 . H211 . 110.5 no
C20 . C21 . H212 . 107.9 no
C22 . C21 . H212 . 108.4 no
H211 . C21 . H212 . 109.4 no
C21 . C22 . C2 . 109.30(14) yes
C21 . C22 . O23 . 107.29(13) yes
C2 . C22 . O23 . 111.91(13) yes
C21 . C22 . H221 . 110.6 no
C2 . C22 . H221 . 108.2 no
O23 . C22 . H221 . 109.5 no
C22 . O23 . H231 . 107.3 no
C25 . O24 . H241 . 106.5 no
O24 . C25 . C26 . 110.75(13) yes
O24 . C25 . C45 . 108.38(13) yes
C26 . C25 . C45 . 110.98(13) yes
O24 . C25 . H251 . 108.4 no
C26 . C25 . H251 . 109.1 no
C45 . C25 . H251 . 109.2 no
C25 . C26 . N27 . 110.33(13) yes
C25 . C26 . C42 . 109.01(13) yes
N27 . C26 . C42 . 116.12(13) yes
C25 . C26 . H261 . 105.8 no
N27 . C26 . H261 . 106.6 no
C42 . C26 . H261 . 108.5 no
C26 . N27 . C28 . 114.04(12) yes
C26 . N27 . C35 . 111.75(13) yes
C28 . N27 . C35 . 109.33(12) yes
N27 . C28 . C29 . 112.03(13) yes
N27 . C28 . H282 . 110.1 no
C29 . C28 . H282 . 108.4 no
N27 . C28 . H281 . 107.7 no
C29 . C28 . H281 . 109.8 no
H282 . C28 . H281 . 108.8 no
C28 . C29 . C30 . 120.75(15) yes
C28 . C29 . C34 . 121.34(15) yes
C30 . C29 . C34 . 117.90(16) yes
C29 . C30 . C31 . 121.12(17) yes
C29 . C30 . H301 . 118.0 no
C31 . C30 . H301 . 120.9 no
C30 . C31 . C32 . 120.34(17) yes
C30 . C31 . H311 . 118.9 no
C32 . C31 . H311 . 120.7 no
C31 . C32 . C33 . 119.17(18) yes
C31 . C32 . H321 . 120.5 no
C33 . C32 . H321 . 120.3 no
C32 . C33 . C34 . 120.75(18) yes
C32 . C33 . H331 . 119.4 no
C34 . C33 . H331 . 119.9 no
C29 . C34 . C33 . 120.71(17) yes
C29 . C34 . H341 . 119.5 no
C33 . C34 . H341 . 119.8 no
N27 . C35 . C36 . 115.07(13) yes
N27 . C35 . H351 . 105.8 no
C36 . C35 . H351 . 107.8 no
N27 . C35 . H352 . 110.6 no
C36 . C35 . H352 . 109.0 no
H351 . C35 . H352 . 108.4 no
C35 . C36 . C37 . 122.55(15) yes
C35 . C36 . C41 . 118.35(15) yes
C37 . C36 . C41 . 118.90(15) yes
C36 . C37 . C38 . 120.27(17) yes
C36 . C37 . H371 . 119.2 no
C38 . C37 . H371 . 120.5 no
C37 . C38 . C39 . 120.21(17) yes
C37 . C38 . H381 . 119.6 no
C39 . C38 . H381 . 120.1 no
C38 . C39 . C40 . 119.65(17) yes
C38 . C39 . H391 . 119.5 no
C40 . C39 . H391 . 120.9 no
C39 . C40 . C41 . 120.21(17) yes
C39 . C40 . H401 . 119.8 no
C41 . C40 . H401 . 120.0 no
C40 . C41 . C36 . 120.75(17) yes
C40 . C41 . H411 . 119.4 no
C36 . C41 . H411 . 119.8 no
C26 . C42 . C43 . 110.76(14) yes
C26 . C42 . H421 . 108.7 no
C43 . C42 . H421 . 111.0 no
C26 . C42 . H422 . 109.1 no
C43 . C42 . H422 . 109.0 no
H421 . C42 . H422 . 108.2 no
C42 . C43 . C44 . 110.79(14) yes
C42 . C43 . H431 . 109.4 no
C44 . C43 . H431 . 108.4 no
C42 . C43 . H432 . 109.5 no
C44 . C43 . H432 . 109.2 no
H431 . C43 . H432 . 109.6 no
C43 . C44 . C45 . 111.26(14) yes
C43 . C44 . H442 . 109.1 no
C45 . C44 . H442 . 107.8 no
C43 . C44 . H441 . 109.4 no
C45 . C44 . H441 . 109.5 no
H442 . C44 . H441 . 109.8 no
C25 . C45 . C44 . 109.85(14) yes
C25 . C45 . O46 . 110.52(13) yes
C44 . C45 . O46 . 108.16(14) yes
C25 . C45 . H451 . 109.5 no
C44 . C45 . H451 . 109.3 no
O46 . C45 . H451 . 109.5 no
C45 . O46 . H461 . 109.0 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
O1 . C2 . 1.4379(19) yes
O1 . H11 . 0.876 no
C2 . C3 . 1.526(2) yes
C2 . C22 . 1.517(2) yes
C2 . H21 . 1.017 no
C3 . N4 . 1.482(2) yes
C3 . C19 . 1.533(2) yes
C3 . H31 . 1.017 no
N4 . C5 . 1.477(2) yes
N4 . C12 . 1.467(2) yes
C5 . C6 . 1.511(2) yes
C5 . H51 . 1.004 no
C5 . H52 . 1.024 no
C6 . C7 . 1.384(2) yes
C6 . C11 . 1.388(2) yes
C7 . C8 . 1.386(3) yes
C7 . H71 . 0.970 no
C8 . C9 . 1.376(3) yes
C8 . H81 . 0.985 no
C9 . C10 . 1.377(3) yes
C9 . H91 . 0.972 no
C10 . C11 . 1.390(3) yes
C10 . H101 . 0.966 no
C11 . H111 . 0.976 no
C12 . C13 . 1.511(2) yes
C12 . H122 . 1.010 no
C12 . H121 . 1.013 no
C13 . C14 . 1.388(2) yes
C13 . C18 . 1.392(2) yes
C14 . C15 . 1.385(2) yes
C14 . H141 . 0.972 no
C15 . C16 . 1.377(3) yes
C15 . H151 . 0.967 no
C16 . C17 . 1.386(3) yes
C16 . H161 . 0.980 no
C17 . C18 . 1.380(3) yes
C17 . H171 . 0.981 no
C18 . H181 . 0.980 no
C19 . C20 . 1.535(2) yes
C19 . H192 . 0.999 no
C19 . H191 . 1.013 no
C20 . C21 . 1.529(2) yes
C20 . H202 . 1.003 no
C20 . H201 . 1.016 no
C21 . C22 . 1.524(2) yes
C21 . H211 . 1.007 no
C21 . H212 . 1.005 no
C22 . O23 . 1.427(2) yes
C22 . H221 . 1.021 no
O23 . H231 . 0.893 no
O24 . C25 . 1.4326(18) yes
O24 . H241 . 0.877 no
C25 . C26 . 1.529(2) yes
C25 . C45 . 1.522(2) yes
C25 . H251 . 1.016 no
C26 . N27 . 1.479(2) yes
C26 . C42 . 1.532(2) yes
C26 . H261 . 1.025 no
N27 . C28 . 1.476(2) yes
N27 . C35 . 1.468(2) yes
C28 . C29 . 1.510(2) yes
C28 . H282 . 1.008 no
C28 . H281 . 0.993 no
C29 . C30 . 1.391(2) yes
C29 . C34 . 1.388(2) yes
C30 . C31 . 1.385(3) yes
C30 . H301 . 0.987 no
C31 . C32 . 1.374(3) yes
C31 . H311 . 0.965 no
C32 . C33 . 1.379(3) yes
C32 . H321 . 0.975 no
C33 . C34 . 1.383(3) yes
C33 . H331 . 0.968 no
C34 . H341 . 0.971 no
C35 . C36 . 1.511(2) yes
C35 . H351 . 0.998 no
C35 . H352 . 1.008 no
C36 . C37 . 1.387(2) yes
C36 . C41 . 1.383(2) yes
C37 . C38 . 1.389(2) yes
C37 . H371 . 0.969 no
C38 . C39 . 1.383(3) yes
C38 . H381 . 0.975 no
C39 . C40 . 1.375(3) yes
C39 . H391 . 0.969 no
C40 . C41 . 1.385(2) yes
C40 . H401 . 0.974 no
C41 . H411 . 0.980 no
C42 . C43 . 1.528(2) yes
C42 . H421 . 0.999 no
C42 . H422 . 1.008 no
C43 . C44 . 1.523(2) yes
C43 . H431 . 1.004 no
C43 . H432 . 0.993 no
C44 . C45 . 1.520(2) yes
C44 . H442 . 1.000 no
C44 . H441 . 1.008 no
C45 . O46 . 1.429(2) yes
C45 . H451 . 1.010 no
O46 . H461 . 0.882 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_distance_DA
_geom_hbond_publ_flag
C2 . H21 . O23 4_465 177 1.02 2.39 3.405(3) yes
C25 . H251 . O46 4_465 154 1.02 2.47 3.417(3) yes
C28 . H281 . O46 4_465 165 0.99 2.36 3.325(3) yes
O23 . H231 . O24 4_565 169 0.89 1.91 2.791(3) yes
O46 . H461 . O1 . 169 0.88 1.93 2.796(3) yes
O1 . H11 . N4 . 122 0.88 2.20 2.772(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190332
