#------------------------------------------------------------------------------
#$Date: 2021-06-03 22:49:31 +0300 (Thu, 03 Jun 2021) $
#$Revision: 265733 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/87/4518773.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_4518773
loop_
_publ_author_name
'Zeng, Ziyu'
'Kociok-Köhn, Gabriele'
'Woodman, Timothy J.'
'Rowan, Michael G.'
'Blagbrough, Ian S.'
_publ_section_title
;
 The ¹H NMR Spectroscopic Effect of Steric Compression Is Found
 in [3.3.1]Oxa- and Azabicycles and Their Analogues.
;
_journal_issue                   19
_journal_name_full               'ACS omega'
_journal_page_first              12769
_journal_page_last               12786
_journal_paper_doi               10.1021/acsomega.1c01093
_journal_volume                  6
_journal_year                    2021
_chemical_formula_moiety         'C18.60 H23.80 N5 O6'
_chemical_formula_sum            'C18.6 H23.8 N5 O6'
_chemical_formula_weight         413.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                110.066(11)
_cell_angle_beta                 90.729(7)
_cell_angle_gamma                90.190(7)
_cell_formula_units_Z            4
_cell_length_a                   7.7392(4)
_cell_length_b                   15.8949(16)
_cell_length_c                   17.396(2)
_cell_measurement_reflns_used    1749
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.8800
_cell_measurement_theta_min      3.2520
_cell_volume                     2009.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'
_computing_publication_material
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_computing_structure_refinement
;
 SHELXL-2016/6 (Sheldrick, 2016)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_structure_solution
; 
 SHELXT
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.1742
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11165
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.746
_diffrn_reflns_theta_min         2.705
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       needle
_exptl_crystal_F_000             874
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.786
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         11165
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.786
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0621
_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)+(0.0580P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1536
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4628
_reflns_number_total             11165
_reflns_threshold_expression     'I > 2σ(I)'
_twin_special_details
;
Component 2 rotated by 179.9583° 
 around [-0.00 0.94 -0.35] (reciprocal) or [0.01 1.00 -0.00] (direct)
;
_cod_data_source_file            ao1c01093_si_002.cif
_cod_data_source_block           s18phar4
_cod_original_formula_sum        'C18.60 H23.80 N5 O6'
_cod_database_code               4518773
_shelx_shelxl_version_number     2018/1
_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   0.708
_shelx_estimated_absorpt_t_max   0.979
_oxdiff_exptl_absorpt_empirical_full_min 0.639
_oxdiff_exptl_absorpt_empirical_full_max 1.288
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_twin_integration_method  simultaneous
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8716(7) -0.2209(4) 0.2152(3) 0.0370(13) Uani 1 1 d . . . . .
N2 N 0.7692(6) 0.0436(3) 0.2834(3) 0.0225(12) Uani 1 1 d . . . . .
N3 N 0.6893(7) 0.0875(4) 0.3579(3) 0.0242(13) Uani 1 1 d D . . . .
H3 H 0.650(7) 0.063(4) 0.389(3) 0.034(19) Uiso 1 1 d D . . . .
N4 N 0.5601(6) 0.1934(4) 0.5204(3) 0.0302(13) Uani 1 1 d . . . . .
N5 N 0.6818(6) 0.4625(4) 0.4545(3) 0.0292(14) Uani 1 1 d . . . . .
O1 O 1.1027(5) -0.0124(3) 0.1544(3) 0.0324(10) Uani 1 1 d . . . . .
O2 O 0.8520(5) 0.0319(3) 0.1164(3) 0.0295(10) Uani 1 1 d . . . . .
O3 O 0.5372(5) 0.1116(3) 0.4986(2) 0.0299(10) Uani 1 1 d . . . . .
O4 O 0.5265(8) 0.2441(3) 0.5894(3) 0.0634(18) Uani 1 1 d . . . . .
O5 O 0.6752(5) 0.5046(3) 0.5284(2) 0.0296(10) Uani 1 1 d . . . . .
O6 O 0.6930(6) 0.4943(3) 0.4005(3) 0.0373(12) Uani 1 1 d . . . . .
C1 C 0.8380(6) -0.0871(4) 0.1713(3) 0.0174(11) Uani 1 1 d . . . . .
C2 C 0.9475(6) -0.0197(4) 0.1475(3) 0.0187(12) Uani 1 1 d . . . . .
C3 C 0.9449(8) 0.1036(4) 0.0995(4) 0.0381(16) Uani 1 1 d . . . . .
H3A H 1.022626 0.077662 0.053512 0.057 Uiso 1 1 calc R U . . .
H3B H 1.012514 0.138520 0.148105 0.057 Uiso 1 1 calc R U . . .
H3C H 0.861911 0.142805 0.085690 0.057 Uiso 1 1 calc R U . . .
C4 C 0.9607(7) -0.1582(4) 0.1835(4) 0.0319(15) Uani 1 1 d . . . . .
H4A H 1.013584 -0.192250 0.130420 0.038 Uiso 1 1 calc R U . . .
H4B H 1.054963 -0.127567 0.222051 0.038 Uiso 1 1 calc R U . . .
C5 C 1.0037(12) -0.2838(5) 0.2319(5) 0.061(3) Uani 1 1 d . . . . .
H5A H 1.104773 -0.249074 0.262152 0.073 Uiso 1 1 calc R U . . .
H5B H 0.951595 -0.315918 0.265771 0.073 Uiso 1 1 calc R U . . .
C6 C 1.0556(15) -0.3449(7) 0.1573(6) 0.037(3) Uani 0.6 1 d . . P . .
H6A H 0.953936 -0.367719 0.122037 0.056 Uiso 0.6 1 calc R U P . .
H6B H 1.115406 -0.394862 0.166725 0.056 Uiso 0.6 1 calc R U P . .
H6C H 1.133959 -0.315204 0.130726 0.056 Uiso 0.6 1 calc R U P . .
C7 C 0.7767(9) -0.1740(5) 0.2902(4) 0.0341(17) Uani 1 1 d . . . . .
H7A H 0.860215 -0.142650 0.334435 0.041 Uiso 1 1 calc R U . . .
H7B H 0.713014 -0.218504 0.307444 0.041 Uiso 1 1 calc R U . . .
C8 C 0.6491(7) -0.1061(4) 0.2788(3) 0.0267(13) Uani 1 1 d . . . . .
H8 H 0.593657 -0.073496 0.332309 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7493(7) -0.0404(4) 0.2515(3) 0.0240(13) Uani 1 1 d . . . . .
C10 C 0.5068(8) -0.1480(5) 0.2135(3) 0.0315(16) Uani 1 1 d . . . . .
H10A H 0.447239 -0.195919 0.227434 0.038 Uiso 1 1 calc R U . . .
H10B H 0.420356 -0.101431 0.215663 0.038 Uiso 1 1 calc R U . . .
C11 C 0.5710(9) -0.1863(5) 0.1284(4) 0.0405(19) Uani 1 1 d . . . . .
H11 H 0.633345 -0.242662 0.124077 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4191(10) -0.2125(6) 0.0661(4) 0.083(4) Uani 1 1 d . . . . .
H12A H 0.463175 -0.225567 0.010700 0.124 Uiso 1 1 calc R U . . .
H12B H 0.337214 -0.162910 0.078439 0.124 Uiso 1 1 calc R U . . .
H12C H 0.360512 -0.265773 0.069712 0.124 Uiso 1 1 calc R U . . .
C13 C 0.6949(7) -0.1276(4) 0.1066(3) 0.0250(13) Uani 1 1 d . . . . .
H13A H 0.630362 -0.078111 0.097382 0.030 Uiso 1 1 calc R U . . .
H13B H 0.749854 -0.162508 0.054310 0.030 Uiso 1 1 calc R U . . .
C14 C 0.6796(6) 0.1777(4) 0.3830(3) 0.0196(13) Uani 1 1 d . . . . .
C15 C 0.6249(7) 0.2327(4) 0.4606(3) 0.0215(14) Uani 1 1 d . . . . .
C16 C 0.6240(7) 0.3250(4) 0.4849(3) 0.0245(14) Uani 1 1 d . . . . .
H16 H 0.588675 0.360503 0.538217 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6755(7) 0.3641(4) 0.4296(3) 0.0233(13) Uani 1 1 d . . . . .
C18 C 0.7229(8) 0.3137(4) 0.3503(3) 0.0264(15) Uani 1 1 d . . . . .
H18 H 0.752464 0.342081 0.312270 0.032 Uiso 1 1 calc R U . . .
C19 C 0.7260(7) 0.2213(4) 0.3280(3) 0.0258(14) Uani 1 1 d . . . . .
H19 H 0.760260 0.186417 0.274262 0.031 Uiso 1 1 calc R U . . .
N21 N 0.3832(7) 0.5092(4) 0.2137(3) 0.0368(14) Uani 1 1 d . . . . .
N22 N 0.2714(6) 0.2967(4) 0.2868(3) 0.0219(12) Uani 1 1 d . . . . .
N23 N 0.1904(6) 0.3097(4) 0.3606(3) 0.0213(12) Uani 1 1 d D . . . .
H23 H 0.162(7) 0.360(2) 0.394(3) 0.035(19) Uiso 1 1 d D . . . .
N24 N 0.0574(6) 0.3213(4) 0.5214(3) 0.0276(12) Uani 1 1 d . . . . .
N25 N 0.1805(6) 0.0058(4) 0.4551(3) 0.0249(12) Uani 1 1 d . . . . .
O21 O 0.6052(4) 0.2547(3) 0.1596(2) 0.0245(9) Uani 1 1 d . . . . .
O22 O 0.3523(4) 0.1828(3) 0.1211(2) 0.0264(9) Uani 1 1 d . . . . .
O23 O 0.0371(5) 0.3879(3) 0.5002(2) 0.0282(10) Uani 1 1 d . . . . .
O24 O 0.0198(8) 0.3222(4) 0.5905(3) 0.0626(18) Uani 1 1 d . . . . .
O25 O 0.1746(5) 0.0160(3) 0.5286(2) 0.0306(10) Uani 1 1 d . . . . .
O26 O 0.1940(6) -0.0688(3) 0.4008(3) 0.0363(11) Uani 1 1 d . . . . .
C21 C 0.3456(7) 0.3426(4) 0.1742(3) 0.0204(12) Uani 1 1 d . . . . .
C22 C 0.4510(6) 0.2567(4) 0.1511(3) 0.0201(12) Uani 1 1 d . . . . .
C23 C 0.4445(7) 0.0998(4) 0.1063(4) 0.0368(16) Uani 1 1 d . . . . .
H23A H 0.361895 0.049664 0.091349 0.055 Uiso 1 1 calc R U . . .
H23B H 0.508275 0.102059 0.156024 0.055 Uiso 1 1 calc R U . . .
H23C H 0.525679 0.091357 0.061565 0.055 Uiso 1 1 calc R U . . .
C24 C 0.4696(7) 0.4209(4) 0.1834(3) 0.0241(13) Uani 1 1 d . . . . .
H24A H 0.564312 0.420031 0.221925 0.029 Uiso 1 1 calc R U . . .
H24B H 0.521613 0.412976 0.129676 0.029 Uiso 1 1 calc R U . . .
C25 C 0.5127(12) 0.5828(5) 0.2240(6) 0.071(3) Uani 1 1 d . . . . .
H25A H 0.620830 0.570859 0.249329 0.085 Uiso 1 1 calc R U . . .
H25B H 0.466192 0.640986 0.259293 0.085 Uiso 1 1 calc R U . . .
C26 C 0.5484(15) 0.5848(9) 0.1353(8) 0.048(4) Uani 0.6 1 d . . P . .
H26A H 0.588827 0.525912 0.100339 0.072 Uiso 0.6 1 calc R U P . .
H26B H 0.636987 0.630170 0.138657 0.072 Uiso 0.6 1 calc R U P . .
H26C H 0.441564 0.599541 0.112077 0.072 Uiso 0.6 1 calc R U P . .
C27 C 0.2921(9) 0.5221(4) 0.2912(4) 0.0320(16) Uani 1 1 d . . . . .
H27A H 0.229539 0.579657 0.307476 0.038 Uiso 1 1 calc R U . . .
H27B H 0.378067 0.525485 0.334821 0.038 Uiso 1 1 calc R U . . .
C28 C 0.1622(7) 0.4452(4) 0.2833(3) 0.0256(13) Uani 1 1 d . . . . .
H28 H 0.109684 0.454124 0.337692 0.031 Uiso 1 1 calc R U . . .
C29 C 0.2593(7) 0.3588(4) 0.2555(3) 0.0203(12) Uani 1 1 d . . . . .
C30 C 0.0177(7) 0.4362(5) 0.2189(4) 0.0285(16) Uani 1 1 d . . . . .
H30A H -0.067249 0.391059 0.222597 0.034 Uiso 1 1 calc R U . . .
H30B H -0.042820 0.494193 0.233074 0.034 Uiso 1 1 calc R U . . .
C31 C 0.0755(8) 0.4100(5) 0.1326(4) 0.0319(16) Uani 1 1 d . . . . .
H31 H 0.136678 0.462838 0.126509 0.038 Uiso 1 1 calc R U . . .
C32 C -0.0766(9) 0.3871(6) 0.0729(4) 0.072(3) Uani 1 1 d . . . . .
H32A H -0.037901 0.385235 0.018925 0.108 Uiso 1 1 calc R U . . .
H32B H -0.165891 0.432811 0.092412 0.108 Uiso 1 1 calc R U . . .
H32C H -0.124234 0.328507 0.068831 0.108 Uiso 1 1 calc R U . . .
C33 C 0.1990(7) 0.3337(4) 0.1097(3) 0.0234(13) Uani 1 1 d . . . . .
H33A H 0.252041 0.328849 0.056885 0.028 Uiso 1 1 calc R U . . .
H33B H 0.133760 0.277597 0.101585 0.028 Uiso 1 1 calc R U . . .
C34 C 0.1797(6) 0.2359(4) 0.3842(3) 0.0199(13) Uani 1 1 d . . . . .
C35 C 0.1214(6) 0.2392(4) 0.4619(3) 0.0194(14) Uani 1 1 d . . . . .
C36 C 0.1212(7) 0.1641(4) 0.4856(3) 0.0246(14) Uani 1 1 d . . . . .
H36 H 0.085617 0.168303 0.538795 0.030 Uiso 1 1 calc R U . . .
C37 C 0.1733(6) 0.0839(4) 0.4307(3) 0.0215(13) Uani 1 1 d . . . . .
C38 C 0.2201(7) 0.0767(4) 0.3513(3) 0.0222(14) Uani 1 1 d . . . . .
H38 H 0.247685 0.019703 0.312875 0.027 Uiso 1 1 calc R U . . .
C39 C 0.2264(7) 0.1508(4) 0.3287(3) 0.0246(14) Uani 1 1 d . . . . .
H39 H 0.262574 0.145200 0.275183 0.029 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 8 0.0124
-5 1 -1 0.1837
0 -1 11 0.0107
0 -9 -1 0.0213
0 9 1 0.0213
5 -1 1 0.2332
0 -4 -8 0.0124
0 9 -8 0.0197
0 -9 8 0.0197
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
C4 N1 C7 111.9(5) . . ?
C4 N1 C5 109.2(6) . . ?
C7 N1 C5 109.9(5) . . ?
C9 N2 N3 118.1(5) . . ?
C14 N3 N2 117.7(5) . . ?
C14 N3 H3 117(5) . . ?
N2 N3 H3 126(5) . . ?
O4 N4 O3 122.5(6) . . ?
O4 N4 C15 118.3(6) . . ?
O3 N4 C15 119.2(5) . . ?
O6 N5 O5 126.2(6) . . ?
O6 N5 C17 117.3(5) . . ?
O5 N5 C17 116.6(6) . . ?
C2 O2 C3 116.0(4) . . ?
C9 C1 C2 110.0(5) . . ?
C9 C1 C13 107.1(4) . . ?
C2 C1 C13 110.5(4) . . ?
C9 C1 C4 108.2(5) . . ?
C2 C1 C4 107.9(4) . . ?
C13 C1 C4 113.2(5) . . ?
O1 C2 O2 122.1(5) . . ?
O1 C2 C1 125.2(5) . . ?
O2 C2 C1 112.7(4) . . ?
O2 C3 H3A 109.5 . . ?
O2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C1 112.5(5) . . ?
N1 C4 H4A 109.1 . . ?
C1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 N1 108.5(7) . . ?
C6 C5 H5A 110.0 . . ?
N1 C5 H5A 110.0 . . ?
C6 C5 H5B 110.0 . . ?
N1 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 112.5(5) . . ?
N1 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 107.7(5) . . ?
C9 C8 C10 107.6(5) . . ?
C7 C8 C10 113.9(5) . . ?
C9 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
C10 C8 H8 109.2 . . ?
N2 C9 C8 131.5(5) . . ?
N2 C9 C1 117.5(5) . . ?
C8 C9 C1 111.0(5) . . ?
C11 C10 C8 114.4(5) . . ?
C11 C10 H10A 108.7 . . ?
C8 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C8 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C13 C11 C10 113.8(6) . . ?
C13 C11 C12 110.6(6) . . ?
C10 C11 C12 110.9(6) . . ?
C13 C11 H11 107.1 . . ?
C10 C11 H11 107.1 . . ?
C12 C11 H11 107.1 . . ?
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 . . ?
C11 C13 C1 114.5(5) . . ?
C11 C13 H13A 108.6 . . ?
C1 C13 H13A 108.6 . . ?
C11 C13 H13B 108.6 . . ?
C1 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
N3 C14 C15 124.9(6) . . ?
N3 C14 C19 118.6(5) . . ?
C15 C14 C19 116.5(6) . . ?
C16 C15 C14 122.9(6) . . ?
C16 C15 N4 116.3(5) . . ?
C14 C15 N4 120.8(6) . . ?
C17 C16 C15 118.1(5) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C16 C17 C18 122.1(6) . . ?
C16 C17 N5 119.5(5) . . ?
C18 C17 N5 118.4(6) . . ?
C19 C18 C17 118.6(6) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C18 C19 C14 121.6(5) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C27 N21 C24 111.5(5) . . ?
C27 N21 C25 110.9(6) . . ?
C24 N21 C25 110.0(5) . . ?
C29 N22 N23 117.9(5) . . ?
C34 N23 N22 115.8(5) . . ?
C34 N23 H23 119(4) . . ?
N22 N23 H23 124(5) . . ?
O24 N24 O23 122.0(5) . . ?
O24 N24 C35 119.2(6) . . ?
O23 N24 C35 118.7(5) . . ?
O25 N25 O26 123.0(6) . . ?
O25 N25 C37 118.8(5) . . ?
O26 N25 C37 118.3(5) . . ?
C22 O22 C23 114.4(4) . . ?
C29 C21 C22 110.0(5) . . ?
C29 C21 C24 108.3(5) . . ?
C22 C21 C24 108.2(4) . . ?
C29 C21 C33 106.9(4) . . ?
C22 C21 C33 110.3(4) . . ?
C24 C21 C33 113.1(5) . . ?
O21 C22 O22 123.2(5) . . ?
O21 C22 C21 124.2(5) . . ?
O22 C22 C21 112.6(4) . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N21 C24 C21 112.7(5) . . ?
N21 C24 H24A 109.0 . . ?
C21 C24 H24A 109.0 . . ?
N21 C24 H24B 109.0 . . ?
C21 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
N21 C25 C26 106.5(8) . . ?
N21 C25 H25A 110.4 . . ?
C26 C25 H25A 110.4 . . ?
N21 C25 H25B 110.4 . . ?
C26 C25 H25B 110.4 . . ?
H25A C25 H25B 108.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N21 C27 C28 112.0(5) . . ?
N21 C27 H27A 109.2 . . ?
C28 C27 H27A 109.2 . . ?
N21 C27 H27B 109.2 . . ?
C28 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C29 C28 C30 106.5(5) . . ?
C29 C28 C27 108.0(5) . . ?
C30 C28 C27 113.6(5) . . ?
C29 C28 H28 109.6 . . ?
C30 C28 H28 109.6 . . ?
C27 C28 H28 109.6 . . ?
N22 C29 C28 130.7(5) . . ?
N22 C29 C21 117.1(5) . . ?
C28 C29 C21 112.0(5) . . ?
C31 C30 C28 115.5(5) . . ?
C31 C30 H30A 108.4 . . ?
C28 C30 H30A 108.4 . . ?
C31 C30 H30B 108.4 . . ?
C28 C30 H30B 108.4 . . ?
H30A C30 H30B 107.5 . . ?
C30 C31 C33 113.1(5) . . ?
C30 C31 C32 111.5(6) . . ?
C33 C31 C32 109.3(6) . . ?
C30 C31 H31 107.5 . . ?
C33 C31 H31 107.5 . . ?
C32 C31 H31 107.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 C21 114.1(5) . . ?
C31 C33 H33A 108.7 . . ?
C21 C33 H33A 108.7 . . ?
C31 C33 H33B 108.7 . . ?
C21 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
N23 C34 C35 123.4(5) . . ?
N23 C34 C39 119.6(5) . . ?
C35 C34 C39 116.9(6) . . ?
C36 C35 C34 122.0(5) . . ?
C36 C35 N24 116.2(5) . . ?
C34 C35 N24 121.8(6) . . ?
C37 C36 C35 118.8(5) . . ?
C37 C36 H36 120.6 . . ?
C35 C36 H36 120.6 . . ?
C36 C37 C38 120.8(6) . . ?
C36 C37 N25 119.7(5) . . ?
C38 C37 N25 119.4(6) . . ?
C39 C38 C37 120.5(6) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C34 120.7(5) . . ?
C38 C39 H39 119.7 . . ?
C34 C39 H39 119.7 . . ?
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
N1 C4 1.469(7) . ?
N1 C7 1.469(8) . ?
N1 C5 1.526(9) . ?
N2 C9 1.265(8) . ?
N2 N3 1.396(6) . ?
N3 C14 1.351(8) . ?
N3 H3 0.83(2) . ?
N4 O4 1.227(6) . ?
N4 O3 1.234(7) . ?
N4 C15 1.476(8) . ?
N5 O6 1.213(7) . ?
N5 O5 1.231(6) . ?
N5 C17 1.473(8) . ?
O1 C2 1.207(6) . ?
O2 C2 1.344(6) . ?
O2 C3 1.461(7) . ?
C1 C9 1.512(7) . ?
C1 C2 1.531(7) . ?
C1 C13 1.541(7) . ?
C1 C4 1.546(7) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.393(12) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.526(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.503(8) . ?
C8 C10 1.546(8) . ?
C8 H8 1.0000 . ?
C10 C11 1.487(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C13 1.476(8) . ?
C11 C12 1.543(9) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.405(7) . ?
C14 C19 1.410(8) . ?
C15 C16 1.381(8) . ?
C16 C17 1.373(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(7) . ?
C18 C19 1.385(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N21 C27 1.480(7) . ?
N21 C24 1.483(7) . ?
N21 C25 1.501(9) . ?
N22 C29 1.283(8) . ?
N22 N23 1.387(6) . ?
N23 C34 1.371(8) . ?
N23 H23 0.84(2) . ?
N24 O24 1.236(6) . ?
N24 O23 1.244(6) . ?
N24 C35 1.452(7) . ?
N25 O25 1.233(6) . ?
N25 O26 1.242(7) . ?
N25 C37 1.445(8) . ?
O21 C22 1.202(6) . ?
O22 C22 1.342(6) . ?
O22 C23 1.447(7) . ?
C21 C29 1.513(7) . ?
C21 C22 1.527(7) . ?
C21 C24 1.532(7) . ?
C21 C33 1.557(7) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.580(14) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.549(8) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.498(8) . ?
C28 C30 1.543(8) . ?
C28 H28 1.0000 . ?
C30 C31 1.489(8) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C33 1.493(8) . ?
C31 C32 1.518(9) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.416(7) . ?
C34 C39 1.418(8) . ?
C35 C36 1.389(8) . ?
C36 C37 1.369(8) . ?
C36 H36 0.9500 . ?
C37 C38 1.398(7) . ?
C38 C39 1.365(8) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
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
C9 N2 N3 C14 -166.2(5) . . . . ?
C3 O2 C2 O1 -6.3(8) . . . . ?
C3 O2 C2 C1 174.3(5) . . . . ?
C9 C1 C2 O1 103.3(6) . . . . ?
C13 C1 C2 O1 -138.8(5) . . . . ?
C4 C1 C2 O1 -14.5(7) . . . . ?
C9 C1 C2 O2 -77.4(6) . . . . ?
C13 C1 C2 O2 40.6(6) . . . . ?
C4 C1 C2 O2 164.9(5) . . . . ?
C7 N1 C4 C1 -53.5(7) . . . . ?
C5 N1 C4 C1 -175.4(5) . . . . ?
C9 C1 C4 N1 54.8(6) . . . . ?
C2 C1 C4 N1 173.8(5) . . . . ?
C13 C1 C4 N1 -63.6(6) . . . . ?
C4 N1 C5 C6 -73.7(9) . . . . ?
C7 N1 C5 C6 163.2(8) . . . . ?
C4 N1 C7 C8 55.3(7) . . . . ?
C5 N1 C7 C8 176.9(6) . . . . ?
N1 C7 C8 C9 -58.0(7) . . . . ?
N1 C7 C8 C10 61.2(7) . . . . ?
N3 N2 C9 C8 1.0(10) . . . . ?
N3 N2 C9 C1 -179.4(5) . . . . ?
C7 C8 C9 N2 -119.8(7) . . . . ?
C10 C8 C9 N2 117.0(7) . . . . ?
C7 C8 C9 C1 60.6(6) . . . . ?
C10 C8 C9 C1 -62.6(6) . . . . ?
C2 C1 C9 N2 3.6(7) . . . . ?
C13 C1 C9 N2 -116.5(6) . . . . ?
C4 C1 C9 N2 121.3(6) . . . . ?
C2 C1 C9 C8 -176.7(5) . . . . ?
C13 C1 C9 C8 63.2(6) . . . . ?
C4 C1 C9 C8 -59.1(6) . . . . ?
C9 C8 C10 C11 52.6(8) . . . . ?
C7 C8 C10 C11 -66.7(8) . . . . ?
C8 C10 C11 C13 -45.4(9) . . . . ?
C8 C10 C11 C12 -170.8(6) . . . . ?
C10 C11 C13 C1 46.4(9) . . . . ?
C12 C11 C13 C1 171.9(6) . . . . ?
C9 C1 C13 C11 -54.1(7) . . . . ?
C2 C1 C13 C11 -173.9(5) . . . . ?
C4 C1 C13 C11 65.0(7) . . . . ?
N2 N3 C14 C15 -171.1(5) . . . . ?
N2 N3 C14 C19 9.4(7) . . . . ?
N3 C14 C15 C16 177.2(5) . . . . ?
C19 C14 C15 C16 -3.3(8) . . . . ?
N3 C14 C15 N4 -4.5(8) . . . . ?
C19 C14 C15 N4 175.0(5) . . . . ?
O4 N4 C15 C16 -7.1(8) . . . . ?
O3 N4 C15 C16 170.9(5) . . . . ?
O4 N4 C15 C14 174.5(6) . . . . ?
O3 N4 C15 C14 -7.6(8) . . . . ?
C14 C15 C16 C17 1.4(8) . . . . ?
N4 C15 C16 C17 -177.0(5) . . . . ?
C15 C16 C17 C18 2.0(8) . . . . ?
C15 C16 C17 N5 -177.9(5) . . . . ?
O6 N5 C17 C16 -165.3(5) . . . . ?
O5 N5 C17 C16 14.8(8) . . . . ?
O6 N5 C17 C18 14.9(8) . . . . ?
O5 N5 C17 C18 -165.1(5) . . . . ?
C16 C17 C18 C19 -3.2(9) . . . . ?
N5 C17 C18 C19 176.6(5) . . . . ?
C17 C18 C19 C14 1.2(9) . . . . ?
N3 C14 C19 C18 -178.5(6) . . . . ?
C15 C14 C19 C18 2.0(8) . . . . ?
C29 N22 N23 C34 168.6(5) . . . . ?
C23 O22 C22 O21 5.2(8) . . . . ?
C23 O22 C22 C21 -173.9(5) . . . . ?
C29 C21 C22 O21 -100.8(6) . . . . ?
C24 C21 C22 O21 17.2(7) . . . . ?
C33 C21 C22 O21 141.4(5) . . . . ?
C29 C21 C22 O22 78.2(6) . . . . ?
C24 C21 C22 O22 -163.7(4) . . . . ?
C33 C21 C22 O22 -39.5(6) . . . . ?
C27 N21 C24 C21 54.6(7) . . . . ?
C25 N21 C24 C21 178.1(6) . . . . ?
C29 C21 C24 N21 -55.3(6) . . . . ?
C22 C21 C24 N21 -174.5(5) . . . . ?
C33 C21 C24 N21 63.0(6) . . . . ?
C27 N21 C25 C26 -158.8(7) . . . . ?
C24 N21 C25 C26 77.4(8) . . . . ?
C24 N21 C27 C28 -55.0(7) . . . . ?
C25 N21 C27 C28 -178.0(6) . . . . ?
N21 C27 C28 C29 56.8(7) . . . . ?
N21 C27 C28 C30 -61.1(7) . . . . ?
N23 N22 C29 C28 -3.5(9) . . . . ?
N23 N22 C29 C21 -178.8(5) . . . . ?
C30 C28 C29 N22 -112.6(7) . . . . ?
C27 C28 C29 N22 125.1(7) . . . . ?
C30 C28 C29 C21 63.0(6) . . . . ?
C27 C28 C29 C21 -59.4(6) . . . . ?
C22 C21 C29 N22 -7.0(7) . . . . ?
C24 C21 C29 N22 -125.0(6) . . . . ?
C33 C21 C29 N22 112.8(6) . . . . ?
C22 C21 C29 C28 176.8(5) . . . . ?
C24 C21 C29 C28 58.8(6) . . . . ?
C33 C21 C29 C28 -63.4(6) . . . . ?
C29 C28 C30 C31 -53.5(8) . . . . ?
C27 C28 C30 C31 65.2(7) . . . . ?
C28 C30 C31 C33 46.3(9) . . . . ?
C28 C30 C31 C32 170.0(6) . . . . ?
C30 C31 C33 C21 -45.8(8) . . . . ?
C32 C31 C33 C21 -170.7(6) . . . . ?
C29 C21 C33 C31 53.1(7) . . . . ?
C22 C21 C33 C31 172.7(5) . . . . ?
C24 C21 C33 C31 -66.0(6) . . . . ?
N22 N23 C34 C35 171.8(5) . . . . ?
N22 N23 C34 C39 -9.0(7) . . . . ?
N23 C34 C35 C36 -176.3(5) . . . . ?
C39 C34 C35 C36 4.5(8) . . . . ?
N23 C34 C35 N24 4.0(8) . . . . ?
C39 C34 C35 N24 -175.2(5) . . . . ?
O24 N24 C35 C36 5.5(8) . . . . ?
O23 N24 C35 C36 -172.3(5) . . . . ?
O24 N24 C35 C34 -174.8(6) . . . . ?
O23 N24 C35 C34 7.4(8) . . . . ?
C34 C35 C36 C37 -2.4(8) . . . . ?
N24 C35 C36 C37 177.3(5) . . . . ?
C35 C36 C37 C38 -2.2(8) . . . . ?
C35 C36 C37 N25 177.6(5) . . . . ?
O25 N25 C37 C36 -14.9(8) . . . . ?
O26 N25 C37 C36 165.8(5) . . . . ?
O25 N25 C37 C38 165.0(5) . . . . ?
O26 N25 C37 C38 -14.3(8) . . . . ?
C36 C37 C38 C39 4.6(8) . . . . ?
N25 C37 C38 C39 -175.2(5) . . . . ?
C37 C38 C39 C34 -2.3(8) . . . . ?
N23 C34 C39 C38 178.7(5) . . . . ?
C35 C34 C39 C38 -2.1(8) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5334 5161 7952 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.4666 5111 7952 nmt -0.9999 -0.0001 -0.0000 0.0158 0.9999 -0.0012 -0.0075
-0.7517 -0.9995
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0033 4.0058 8.0002 0.2243 0.9500 -0.0331
-4.9954 1.0058 -1.0128 0.0252 -0.0018 1.0020
-0.0019 -0.9986 11.0041 0.6714 0.7442 -0.0987
0.0040 -9.0094 -0.9950 0.4467 -0.8538 -0.0654
-0.0040 9.0094 0.9950 -0.4467 0.8538 0.0654
4.9954 -1.0058 1.0128 -0.0252 0.0018 -1.0020
0.0033 -4.0058 -8.0002 -0.2243 -0.9500 0.0331
-0.0022 9.0075 -7.5077 -0.9223 0.2119 0.1353
0.0022 -9.0075 7.5077 0.9223 -0.2119 -0.1353
