#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/58/4025823.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_4025823
loop_
_publ_author_name
'Stephen G. Davies'
'Ai M. Fletcher'
'Wataru Kurosawa'
'James A. Lee'
'Giovanna Poce'
'Paul M. Roberts'
'James E. Thomson'
'David M. Williamson'
_publ_contact_author_address
;Department of Chemistry
Chemistry Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA, U.K.
;
_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
;
 One-Pot Conversions of Olefins to Cyclic Carbonates and Secondary Allylic
 and Homoallylic Amines to Cyclic Carbamates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7745
_journal_page_last               7756
_journal_paper_doi               10.1021/jo101614f
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C14 H19 N1 O3'
_chemical_formula_sum            'C14 H19 N O3'
_chemical_formula_weight         249.31
_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
_audit_creation_date             09-09-14
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                101.4022(16)
_cell_angle_beta                 104.9826(16)
_cell_angle_gamma                90.623(2)
_cell_formula_units_Z            4
_cell_length_a                   9.6645(4)
_cell_length_b                   11.3513(4)
_cell_length_c                   12.7583(5)
_cell_measurement_reflns_used    5386
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1322.54(9)
_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 0.990
_diffrn_measured_fraction_theta_max 0.980
_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  0.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9400
_diffrn_reflns_theta_full        25.061
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         5.162
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_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    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.50
_refine_diff_density_min         -1.33
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.1331
_refine_ls_shift/su_max          0.000066
_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: 
 2.42 2.52 1.48 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1712
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1344
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3111
_reflns_number_total             5982
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   1.04
_oxford_diffrn_Wilson_scale      5.06
_oxford_refine_ls_r_factor_ref   0.1269
_oxford_refine_ls_scale          0.645(10)
_oxford_reflns_number_all        4285
_oxford_reflns_threshold_expression_ref I>2.5\s(I)
_oxford_structure_analysis_title '9011415 SGD260a'
_cod_data_source_file            jo101614f_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C14 H19 N1 O3'
_cod_database_code               4025823
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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.6038(4) 0.1692(3) 0.3230(3) 0.0246 1.0000 Uani . . . . . . .
C2 C 0.5500(5) 0.2862(4) 0.3115(4) 0.0257 1.0000 Uani . . . . . . .
C3 C 0.6697(5) 0.3664(4) 0.2979(4) 0.0257 1.0000 Uani . . . . . . .
O4 O 0.7905(4) 0.3723(3) 0.3909(3) 0.0316 1.0000 Uani . . . . . . .
C5 C 0.7151(6) 0.3200(5) 0.1930(4) 0.0299 1.0000 Uani . . . . . . .
C6 C 0.8211(6) 0.4068(5) 0.1716(5) 0.0338 1.0000 Uani . . . . . . .
C7 C 0.8846(6) 0.3534(6) 0.0770(5) 0.0437 1.0000 Uani . . . . . . .
C8 C 0.5007(6) 0.3305(5) 0.4164(4) 0.0291 1.0000 Uani . . . . . . .
N9 N 0.5653(4) 0.2479(4) 0.4860(4) 0.0278 1.0000 Uani . . . . . . .
C10 C 0.6136(5) 0.1536(4) 0.4273(4) 0.0254 1.0000 Uani . . . . . . .
O11 O 0.6602(4) 0.0631(3) 0.4568(3) 0.0336 1.0000 Uani . . . . . . .
C12 C 0.5207(6) 0.2386(4) 0.5852(4) 0.0266 1.0000 Uani . . . . . . .
C13 C 0.5778(5) 0.3407(5) 0.6835(4) 0.0257 1.0000 Uani . . . . . . .
C14 C 0.5271(6) 0.3453(5) 0.7764(5) 0.0324 1.0000 Uani . . . . . . .
C15 C 0.5778(7) 0.4361(6) 0.8702(5) 0.0405 1.0000 Uani . . . . . . .
C16 C 0.6801(7) 0.5245(5) 0.8710(5) 0.0447 1.0000 Uani . . . . . . .
C17 C 0.7290(6) 0.5206(5) 0.7794(5) 0.0373 1.0000 Uani . . . . . . .
C18 C 0.6787(5) 0.4290(5) 0.6865(4) 0.0298 1.0000 Uani . . . . . . .
O19 O 0.1050(4) 0.2515(3) 0.3209(3) 0.0267 1.0000 Uani . . . . . . .
C20 C 0.1143(5) 0.3139(5) 0.4258(4) 0.0260 1.0000 Uani . . . . . . .
O21 O 0.1645(4) 0.4173(3) 0.4547(3) 0.0359 1.0000 Uani . . . . . . .
N22 N 0.0620(4) 0.2467(4) 0.4828(3) 0.0264 1.0000 Uani . . . . . . .
C23 C -0.0053(6) 0.1337(5) 0.4131(5) 0.0305 1.0000 Uani . . . . . . .
C24 C 0.0497(6) 0.1300(5) 0.3091(4) 0.0291 1.0000 Uani . . . . . . .
C25 C 0.1666(5) 0.0433(4) 0.2985(4) 0.0253 1.0000 Uani . . . . . . .
O26 O 0.2867(4) 0.0813(3) 0.3914(3) 0.0300 1.0000 Uani . . . . . . .
C27 C 0.2134(6) 0.0380(5) 0.1930(4) 0.0299 1.0000 Uani . . . . . . .
C28 C 0.3196(6) -0.0564(5) 0.1766(5) 0.0365 1.0000 Uani . . . . . . .
C29 C 0.3747(7) -0.0576(6) 0.0756(5) 0.0476 1.0000 Uani . . . . . . .
C30 C 0.0203(6) 0.2992(4) 0.5832(4) 0.0284 1.0000 Uani . . . . . . .
C31 C 0.0798(6) 0.2414(5) 0.6804(4) 0.0284 1.0000 Uani . . . . . . .
C32 C 0.0323(6) 0.2770(5) 0.7756(4) 0.0318 1.0000 Uani . . . . . . .
C33 C 0.0859(6) 0.2292(5) 0.8686(5) 0.0397 1.0000 Uani . . . . . . .
C34 C 0.1871(6) 0.1424(5) 0.8659(5) 0.0387 1.0000 Uani . . . . . . .
C35 C 0.2336(6) 0.1056(5) 0.7736(5) 0.0348 1.0000 Uani . . . . . . .
C36 C 0.1808(5) 0.1556(5) 0.6817(5) 0.0305 1.0000 Uani . . . . . . .
H21 H 0.4690 0.2764 0.2471 0.0303 1.0000 Uiso R . . . . . .
H31 H 0.6361 0.4468 0.2965 0.0300 1.0000 Uiso R . . . . . .
H51 H 0.7543 0.2430 0.1973 0.0379 1.0000 Uiso R . . . . . .
H52 H 0.6287 0.3095 0.1311 0.0381 1.0000 Uiso R . . . . . .
H61 H 0.8989 0.4297 0.2390 0.0411 1.0000 Uiso R . . . . . .
H62 H 0.7727 0.4772 0.1532 0.0408 1.0000 Uiso R . . . . . .
H71 H 0.9494 0.4120 0.0663 0.0697 1.0000 Uiso R . . . . . .
H72 H 0.9359 0.2843 0.0947 0.0700 1.0000 Uiso R . . . . . .
H73 H 0.8091 0.3272 0.0101 0.0701 1.0000 Uiso R . . . . . .
H81 H 0.5385 0.4125 0.4502 0.0381 1.0000 Uiso R . . . . . .
H82 H 0.3965 0.3262 0.3993 0.0379 1.0000 Uiso R . . . . . .
H121 H 0.5514 0.1621 0.6042 0.0321 1.0000 Uiso R . . . . . .
H122 H 0.4155 0.2366 0.5644 0.0322 1.0000 Uiso R . . . . . .
H141 H 0.4582 0.2864 0.7759 0.0419 1.0000 Uiso R . . . . . .
H151 H 0.5436 0.4375 0.9321 0.0489 1.0000 Uiso R . . . . . .
H161 H 0.7125 0.5866 0.9329 0.0509 1.0000 Uiso R . . . . . .
H171 H 0.7961 0.5799 0.7789 0.0451 1.0000 Uiso R . . . . . .
H181 H 0.7128 0.4272 0.6239 0.0392 1.0000 Uiso R . . . . . .
H231 H 0.0259 0.0664 0.4477 0.0383 1.0000 Uiso R . . . . . .
H232 H -0.1094 0.1348 0.3945 0.0377 1.0000 Uiso R . . . . . .
H241 H -0.0305 0.1106 0.2426 0.0376 1.0000 Uiso R . . . . . .
H251 H 0.1307 -0.0382 0.2994 0.0294 1.0000 Uiso R . . . . . .
H271 H 0.2545 0.1159 0.1927 0.0370 1.0000 Uiso R . . . . . .
H272 H 0.1279 0.0178 0.1304 0.0368 1.0000 Uiso R . . . . . .
H281 H 0.4007 -0.0387 0.2419 0.0438 1.0000 Uiso R . . . . . .
H282 H 0.2759 -0.1351 0.1711 0.0440 1.0000 Uiso R . . . . . .
H291 H 0.4354 -0.1236 0.0680 0.0788 1.0000 Uiso R . . . . . .
H292 H 0.4295 0.0173 0.0871 0.0788 1.0000 Uiso R . . . . . .
H293 H 0.2964 -0.0663 0.0105 0.0789 1.0000 Uiso R . . . . . .
H301 H 0.0522 0.3843 0.6023 0.0356 1.0000 Uiso R . . . . . .
H302 H -0.0845 0.2901 0.5652 0.0365 1.0000 Uiso R . . . . . .
H321 H -0.0372 0.3343 0.7762 0.0390 1.0000 Uiso R . . . . . .
H331 H 0.0548 0.2549 0.9322 0.0471 1.0000 Uiso R . . . . . .
H341 H 0.2229 0.1087 0.9273 0.0461 1.0000 Uiso R . . . . . .
H351 H 0.3007 0.0468 0.7715 0.0409 1.0000 Uiso R . . . . . .
H361 H 0.2107 0.1295 0.6180 0.0372 1.0000 Uiso R . . . . . .
H261 H 0.3011 0.0276 0.4269 0.0461 1.0000 Uiso R . . . . . .
H41 H 0.8095 0.4451 0.4004 0.0483 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 . C10 . 109.4(4) yes
O1 . C2 . C3 . 108.8(4) yes
O1 . C2 . C8 . 104.5(4) yes
C3 . C2 . C8 . 114.6(4) yes
O1 . C2 . H21 . 109.4 no
C3 . C2 . H21 . 109.8 no
C8 . C2 . H21 . 109.7 no
C2 . C3 . O4 . 108.2(4) yes
C2 . C3 . C5 . 113.0(4) yes
O4 . C3 . C5 . 108.8(4) yes
C2 . C3 . H31 . 108.6 no
O4 . C3 . H31 . 109.3 no
C5 . C3 . H31 . 108.8 no
C3 . O4 . H41 . 95.6 no
C3 . C5 . C6 . 113.4(4) yes
C3 . C5 . H51 . 108.3 no
C6 . C5 . H51 . 111.1 no
C3 . C5 . H52 . 107.2 no
C6 . C5 . H52 . 107.6 no
H51 . C5 . H52 . 109.2 no
C5 . C6 . C7 . 113.6(5) yes
C5 . C6 . H61 . 107.9 no
C7 . C6 . H61 . 108.5 no
C5 . C6 . H62 . 109.2 no
C7 . C6 . H62 . 107.5 no
H61 . C6 . H62 . 110.2 no
C6 . C7 . H71 . 110.3 no
C6 . C7 . H72 . 108.9 no
H71 . C7 . H72 . 109.5 no
C6 . C7 . H73 . 109.9 no
H71 . C7 . H73 . 109.8 no
H72 . C7 . H73 . 108.4 no
C2 . C8 . N9 . 102.0(4) yes
C2 . C8 . H81 . 110.2 no
N9 . C8 . H81 . 110.9 no
C2 . C8 . H82 . 110.7 no
N9 . C8 . H82 . 113.0 no
H81 . C8 . H82 . 109.8 no
C8 . N9 . C10 . 111.2(4) yes
C8 . N9 . C12 . 121.2(4) yes
C10 . N9 . C12 . 121.5(4) yes
O1 . C10 . N9 . 110.9(4) yes
O1 . C10 . O11 . 120.9(5) yes
N9 . C10 . O11 . 128.2(5) yes
N9 . C12 . C13 . 115.0(4) yes
N9 . C12 . H121 . 107.1 no
C13 . C12 . H121 . 110.1 no
N9 . C12 . H122 . 106.5 no
C13 . C12 . H122 . 108.6 no
H121 . C12 . H122 . 109.3 no
C12 . C13 . C14 . 118.2(5) yes
C12 . C13 . C18 . 123.5(4) yes
C14 . C13 . C18 . 118.2(5) yes
C13 . C14 . C15 . 120.7(5) yes
C13 . C14 . H141 . 119.6 no
C15 . C14 . H141 . 119.7 no
C14 . C15 . C16 . 119.9(5) yes
C14 . C15 . H151 . 119.7 no
C16 . C15 . H151 . 120.4 no
C15 . C16 . C17 . 119.4(5) yes
C15 . C16 . H161 . 120.2 no
C17 . C16 . H161 . 120.4 no
C16 . C17 . C18 . 120.3(5) yes
C16 . C17 . H171 . 119.8 no
C18 . C17 . H171 . 119.8 no
C17 . C18 . C13 . 121.4(5) yes
C17 . C18 . H181 . 119.7 no
C13 . C18 . H181 . 118.9 no
C20 . O19 . C24 . 109.3(4) yes
O19 . C20 . O21 . 119.9(4) yes
O19 . C20 . N22 . 111.0(4) yes
O21 . C20 . N22 . 129.1(5) yes
C20 . N22 . C23 . 111.5(4) yes
C20 . N22 . C30 . 122.1(4) yes
C23 . N22 . C30 . 121.1(4) yes
N22 . C23 . C24 . 101.6(4) yes
N22 . C23 . H231 . 111.4 no
C24 . C23 . H231 . 111.3 no
N22 . C23 . H232 . 111.0 no
C24 . C23 . H232 . 110.8 no
H231 . C23 . H232 . 110.5 no
C23 . C24 . O19 . 104.2(4) yes
C23 . C24 . C25 . 114.5(4) yes
O19 . C24 . C25 . 109.9(4) yes
C23 . C24 . H241 . 109.7 no
O19 . C24 . H241 . 108.6 no
C25 . C24 . H241 . 109.7 no
C24 . C25 . O26 . 108.1(4) yes
C24 . C25 . C27 . 113.0(4) yes
O26 . C25 . C27 . 109.1(4) yes
C24 . C25 . H251 . 109.0 no
O26 . C25 . H251 . 108.9 no
C27 . C25 . H251 . 108.7 no
C25 . O26 . H261 . 108.4 no
C25 . C27 . C28 . 113.3(4) yes
C25 . C27 . H271 . 110.0 no
C28 . C27 . H271 . 109.4 no
C25 . C27 . H272 . 107.7 no
C28 . C27 . H272 . 107.8 no
H271 . C27 . H272 . 108.5 no
C27 . C28 . C29 . 114.1(5) yes
C27 . C28 . H281 . 107.0 no
C29 . C28 . H281 . 108.2 no
C27 . C28 . H282 . 109.5 no
C29 . C28 . H282 . 108.9 no
H281 . C28 . H282 . 109.0 no
C28 . C29 . H291 . 108.9 no
C28 . C29 . H292 . 107.9 no
H291 . C29 . H292 . 109.7 no
C28 . C29 . H293 . 110.4 no
H291 . C29 . H293 . 109.9 no
H292 . C29 . H293 . 110.0 no
N22 . C30 . C31 . 114.8(4) yes
N22 . C30 . H301 . 107.0 no
C31 . C30 . H301 . 109.9 no
N22 . C30 . H302 . 107.2 no
C31 . C30 . H302 . 107.9 no
H301 . C30 . H302 . 110.0 no
C30 . C31 . C32 . 118.4(5) yes
C30 . C31 . C36 . 123.8(5) yes
C32 . C31 . C36 . 117.8(5) yes
C31 . C32 . C33 . 120.9(5) yes
C31 . C32 . H321 . 119.2 no
C33 . C32 . H321 . 119.8 no
C32 . C33 . C34 . 119.2(5) yes
C32 . C33 . H331 . 120.2 no
C34 . C33 . H331 . 120.6 no
C33 . C34 . C35 . 120.7(5) yes
C33 . C34 . H341 . 120.2 no
C35 . C34 . H341 . 119.0 no
C34 . C35 . C36 . 119.5(5) yes
C34 . C35 . H351 . 120.8 no
C36 . C35 . H351 . 119.7 no
C31 . C36 . C35 . 121.8(5) yes
C31 . C36 . H361 . 118.4 no
C35 . C36 . H361 . 119.8 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 . 1.452(6) yes
O1 . C10 . 1.356(6) yes
C2 . C3 . 1.530(7) yes
C2 . C8 . 1.529(7) yes
C2 . H21 . 0.964 no
C3 . O4 . 1.424(6) yes
C3 . C5 . 1.514(7) yes
C3 . H31 . 0.973 no
O4 . H41 . 0.822 no
C5 . C6 . 1.524(8) yes
C5 . H51 . 0.963 no
C5 . H52 . 0.977 no
C6 . C7 . 1.517(8) yes
C6 . H61 . 0.972 no
C6 . H62 . 0.969 no
C7 . H71 . 0.961 no
C7 . H72 . 0.966 no
C7 . H73 . 0.960 no
C8 . N9 . 1.454(6) yes
C8 . H81 . 0.969 no
C8 . H82 . 0.972 no
N9 . C10 . 1.341(7) yes
N9 . C12 . 1.460(6) yes
C10 . O11 . 1.215(6) yes
C12 . C13 . 1.508(7) yes
C12 . H121 . 0.976 no
C12 . H122 . 0.980 no
C13 . C14 . 1.386(7) yes
C13 . C18 . 1.380(7) yes
C14 . C15 . 1.391(8) yes
C14 . H141 . 0.936 no
C15 . C16 . 1.398(9) yes
C15 . H151 . 0.929 no
C16 . C17 . 1.363(9) yes
C16 . H161 . 0.930 no
C17 . C18 . 1.388(8) yes
C17 . H171 . 0.931 no
C18 . H181 . 0.936 no
O19 . C20 . 1.365(6) yes
O19 . C24 . 1.439(6) yes
C20 . O21 . 1.213(6) yes
C20 . N22 . 1.329(6) yes
N22 . C23 . 1.446(7) yes
N22 . C30 . 1.459(6) yes
C23 . C24 . 1.545(7) yes
C23 . H231 . 0.969 no
C23 . H232 . 0.973 no
C24 . C25 . 1.521(7) yes
C24 . H241 . 0.976 no
C25 . O26 . 1.419(6) yes
C25 . C27 . 1.518(7) yes
C25 . H251 . 0.988 no
O26 . H261 . 0.821 no
C27 . C28 . 1.514(7) yes
C27 . H271 . 0.966 no
C27 . H272 . 0.977 no
C28 . C29 . 1.515(8) yes
C28 . H281 . 0.970 no
C28 . H282 . 0.966 no
C29 . H291 . 0.961 no
C29 . H292 . 0.962 no
C29 . H293 . 0.956 no
C30 . C31 . 1.503(7) yes
C30 . H301 . 0.975 no
C30 . H302 . 0.979 no
C31 . C32 . 1.396(7) yes
C31 . C36 . 1.386(7) yes
C32 . C33 . 1.383(8) yes
C32 . H321 . 0.940 no
C33 . C34 . 1.397(9) yes
C33 . H331 . 0.932 no
C34 . C35 . 1.359(8) yes
C34 . H341 . 0.928 no
C35 . C36 . 1.385(8) yes
C35 . H351 . 0.937 no
C36 . H361 . 0.927 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
O26 . H261 . O11 2_656 165 0.82 1.93 2.732(8) yes
O4 . H41 . O21 2_666 130 0.82 2.13 2.729(8) yes
loop_
_oxford_twin_element_scale_factors
0.499(15)
0.501(15)
