#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:23:11 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286192 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/94/7159412.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_7159412
loop_
_publ_author_name
'Šlachtová, Veronika'
'Casaretto, Nicolas'
'Brulíková, Lucie'
'Six, Yvan'
_publ_section_title
;
 Bicyclic N-dihalocyclopropylamide derivatives as precursors of
 nitrogen-containing fused polycyclic systems.
;
_journal_issue                   31
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6325
_journal_page_last               6341
_journal_paper_doi               10.1039/d3ob00643c
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H19 N O4'
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-06 deposited with the CCDC.	2023-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.052(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6585(10)
_cell_length_b                   6.8558(8)
_cell_length_c                   12.0392(14)
_cell_measurement_reflns_used    2670
_cell_measurement_temperature    149.77
_cell_measurement_theta_max      27.448
_cell_measurement_theta_min      2.414
_cell_volume                     696.20(14)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      149.77
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.736
_diffrn_source_current           31.0
_diffrn_source_power             1.705
_diffrn_source_voltage           55.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0773 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.9132.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         2852
_refine_ls_number_restraints     649
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0491
_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)+(0.0655P)²+0.2425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2377
_reflns_number_total             2852
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00643c3.cif
_cod_data_source_block           vs589a_sp1_1_0m
_cod_depositor_comments          'Adding full bibliography for 7159412.cif.'
_cod_database_code               7159412
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: -1(3)
 2(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.004 and sigma
for terminal atoms of 0.008 within 2A
4. Others
 Sof(O1B)=Sof(O2B)=Sof(O3B)=Sof(O4B)=Sof(H4B)=Sof(N1B)=Sof(C1B)=Sof(H1BA)=
 Sof(H1BB)=Sof(H1BC)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(H2BC)=Sof(C3B)=Sof(C4B)=
 Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(C7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9BA)=
 Sof(H9BB)=Sof(C10B)=Sof(H10C)=Sof(H10D)=Sof(C11B)=Sof(C12B)=Sof(H12B)=
 Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=
 Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=Sof(H4A)=Sof(N1A)=Sof(C1A)=Sof(H1AA)=
 Sof(H1AB)=Sof(H1AC)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C3A)=Sof(C4A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9AA)=
 Sof(H9AB)=Sof(C10A)=Sof(H10A)=Sof(H10B)=Sof(C11A)=Sof(C12A)=Sof(H12A)=
 Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(H16A)=Sof(H16B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12A(H12A), C15A(H15A), C12B(H12B), C15B(H15B)
5.b Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C10A(H10A,H10B), C16A(H16A,H16B), C9B(H9BA,H9BB), C10B(H10C,
 H10D), C16B(H16C,H16D)
5.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C8A(H8A), C13A(H13A), C14A(H14A), C5B(H5B), C8B(H8B), C13B(H13B),
 C14B(H14B)
5.d Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C2A(H2AA,H2AB,H2AC), C1B(H1BA,H1BB,H1BC), C2B(H2BA,H2BB,
 H2BC)
5.e Idealised tetrahedral OH refined as rotating group:
 O4A(H4A), O4B(H4B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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_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
O1A O -0.1595(12) -0.2590(7) -0.8516(8) 0.0226(12) Uani 0.724(3) 1 d . U P A 1
O2A O -0.4617(5) -0.2400(6) -0.8836(4) 0.0207(8) Uani 0.724(3) 1 d . U P A 1
O3A O -0.4170(5) -0.6668(6) -1.4044(4) 0.0372(10) Uani 0.724(3) 1 d . U P A 1
O4A O -0.8312(5) -0.3762(7) -1.5427(3) 0.0348(9) Uani 0.724(3) 1 d . U P A 1
H4A H -0.758060 -0.304493 -1.554894 0.052 Uiso 0.724(3) 1 calc R U P A 1
N1A N -0.5393(5) -0.3979(7) -1.3559(4) 0.0247(8) Uani 0.724(3) 1 d . U P A 1
C1A C 0.0094(19) -0.2632(13) -0.8293(14) 0.025(2) Uani 0.724(3) 1 d . U P A 1
H1AA H 0.043710 -0.378414 -0.865475 0.037 Uiso 0.724(3) 1 calc R U P A 1
H1AB H 0.052682 -0.269047 -0.746752 0.037 Uiso 0.724(3) 1 calc R U P A 1
H1AC H 0.047842 -0.145184 -0.860156 0.037 Uiso 0.724(3) 1 calc R U P A 1
C2A C -0.6303(8) -0.2391(9) -0.8967(5) 0.0222(12) Uani 0.724(3) 1 d . U P A 1
H2AA H -0.674535 -0.120243 -0.936857 0.033 Uiso 0.724(3) 1 calc R U P A 1
H2AB H -0.655599 -0.242683 -0.821389 0.033 Uiso 0.724(3) 1 calc R U P A 1
H2AC H -0.676074 -0.353572 -0.940802 0.033 Uiso 0.724(3) 1 calc R U P A 1
C3A C -0.2394(12) -0.2508(8) -0.9628(8) 0.0216(11) Uani 0.724(3) 1 d . U P A 1
C4A C -0.4060(7) -0.2355(9) -0.9797(5) 0.0201(9) Uani 0.724(3) 1 d . U P A 1
C5A C -0.4966(6) -0.2200(8) -1.0899(4) 0.0232(9) Uani 0.724(3) 1 d . U P A 1
H5A H -0.608495 -0.208251 -1.102426 0.028 Uiso 0.724(3) 1 calc R U P A 1
C6A C -0.4248(6) -0.2217(8) -1.1831(4) 0.0227(9) Uani 0.724(3) 1 d . U P A 1
C7A C -0.2629(8) -0.2438(8) -1.1674(5) 0.0213(10) Uani 0.724(3) 1 d . U P A 1
C8A C -0.1707(14) -0.2566(9) -1.0559(10) 0.0212(12) Uani 0.724(3) 1 d . U P A 1
H8A H -0.058919 -0.269622 -1.044037 0.025 Uiso 0.724(3) 1 calc R U P A 1
C9A C -0.1832(8) -0.2486(9) -1.2676(6) 0.0257(11) Uani 0.724(3) 1 d . U P A 1
H9AA H -0.072419 -0.292330 -1.238992 0.031 Uiso 0.724(3) 1 calc R U P A 1
H9AB H -0.179123 -0.113328 -1.295644 0.031 Uiso 0.724(3) 1 calc R U P A 1
C10A C -0.2594(7) -0.3788(10) -1.3708(4) 0.0328(10) Uani 0.724(3) 1 d . U P A 1
H10A H -0.277122 -0.294232 -1.439171 0.039 Uiso 0.724(3) 1 calc R U P A 1
H10B H -0.178130 -0.475655 -1.379471 0.039 Uiso 0.724(3) 1 calc R U P A 1
C11A C -0.4118(7) -0.4908(8) -1.3768(4) 0.0266(10) Uani 0.724(3) 1 d . U P A 1
C12A C -0.5220(6) -0.2049(8) -1.3051(5) 0.0244(9) Uani 0.724(3) 1 d . U P A 1
H12A H -0.458486 -0.125346 -1.348371 0.029 Uiso 0.724(3) 1 calc R U P A 1
C13A C -0.6809(7) -0.1039(9) -1.3171(5) 0.0278(10) Uani 0.724(3) 1 d . U P A 1
H13A H -0.683136 0.020124 -1.282388 0.033 Uiso 0.724(3) 1 calc R U P A 1
C14A C -0.8175(7) -0.1803(10) -1.3739(5) 0.0316(10) Uani 0.724(3) 1 d . U P A 1
H14A H -0.911830 -0.105164 -1.384265 0.038 Uiso 0.724(3) 1 calc R U P A 1
C15A C -0.8248(7) -0.3822(10) -1.4216(5) 0.0291(10) Uani 0.724(3) 1 d . U P A 1
H15A H -0.924542 -0.444785 -1.410521 0.035 Uiso 0.724(3) 1 calc R U P A 1
C16A C -0.6856(7) -0.5029(9) -1.3576(5) 0.0272(10) Uani 0.724(3) 1 d . U P A 1
H16A H -0.696516 -0.526609 -1.278580 0.033 Uiso 0.724(3) 1 calc R U P A 1
H16B H -0.683833 -0.630589 -1.395613 0.033 Uiso 0.724(3) 1 calc R U P A 1
O1B O -0.161(3) -0.311(3) -0.852(2) 0.022(2) Uani 0.276(3) 1 d . U P A 2
O2B O -0.4608(16) -0.3245(17) -0.8811(11) 0.0251(18) Uani 0.276(3) 1 d . U P A 2
O3B O -0.4163(12) 0.105(2) -1.4041(8) 0.040(3) Uani 0.276(3) 1 d . U P A 2
O4B O -0.8319(12) -0.1834(18) -1.5408(8) 0.035(2) Uani 0.276(3) 1 d . U P A 2
H4B H -0.743412 -0.216859 -1.552240 0.053 Uiso 0.276(3) 1 calc R U P A 2
N1B N -0.5340(15) -0.157(2) -1.3562(11) 0.0278(15) Uani 0.276(3) 1 d . U P A 2
C1B C 0.002(5) -0.311(4) -0.830(4) 0.023(4) Uani 0.276(3) 1 d . U P A 2
H1BA H 0.038987 -0.192544 -0.861212 0.034 Uiso 0.276(3) 1 calc R U P A 2
H1BB H 0.038847 -0.425888 -0.864792 0.034 Uiso 0.276(3) 1 calc R U P A 2
H1BC H 0.045200 -0.314627 -0.746989 0.034 Uiso 0.276(3) 1 calc R U P A 2
C2B C -0.631(2) -0.327(3) -0.8979(16) 0.032(3) Uani 0.276(3) 1 d . U P A 2
H2BA H -0.669726 -0.460010 -0.917128 0.047 Uiso 0.276(3) 1 calc R U P A 2
H2BB H -0.677561 -0.238678 -0.960277 0.047 Uiso 0.276(3) 1 calc R U P A 2
H2BC H -0.660225 -0.285170 -0.827765 0.047 Uiso 0.276(3) 1 calc R U P A 2
C3B C -0.240(4) -0.301(3) -0.964(2) 0.0222(15) Uani 0.276(3) 1 d . U P A 2
C4B C -0.400(2) -0.319(3) -0.9812(14) 0.0249(15) Uani 0.276(3) 1 d . U P A 2
C5B C -0.4929(17) -0.348(2) -1.0889(11) 0.0261(15) Uani 0.276(3) 1 d . U P A 2
H5B H -0.604086 -0.365875 -1.099339 0.031 Uiso 0.276(3) 1 calc R U P A 2
C6B C -0.4236(16) -0.351(2) -1.1828(11) 0.0259(14) Uani 0.276(3) 1 d . U P A 2
C7B C -0.259(2) -0.316(2) -1.1669(16) 0.0248(15) Uani 0.276(3) 1 d . U P A 2
C8B C -0.170(4) -0.301(3) -1.058(3) 0.0218(17) Uani 0.276(3) 1 d . U P A 2
H8B H -0.057623 -0.291146 -1.045400 0.026 Uiso 0.276(3) 1 calc R U P A 2
C9B C -0.187(2) -0.318(3) -1.2716(17) 0.0269(17) Uani 0.276(3) 1 d . U P A 2
H9BA H -0.191050 -0.453704 -1.300025 0.032 Uiso 0.276(3) 1 calc R U P A 2
H9BB H -0.073951 -0.282048 -1.246172 0.032 Uiso 0.276(3) 1 calc R U P A 2
C10B C -0.2614(17) -0.185(2) -1.3733(11) 0.0302(17) Uani 0.276(3) 1 d . U P A 2
H10C H -0.177916 -0.092082 -1.382756 0.036 Uiso 0.276(3) 1 calc R U P A 2
H10D H -0.283376 -0.269062 -1.441999 0.036 Uiso 0.276(3) 1 calc R U P A 2
C11B C -0.4093(17) -0.067(2) -1.3767(11) 0.0293(19) Uani 0.276(3) 1 d . U P A 2
C12B C -0.5237(18) -0.362(3) -1.3047(13) 0.0257(13) Uani 0.276(3) 1 d . U P A 2
H12B H -0.462958 -0.443292 -1.348977 0.031 Uiso 0.276(3) 1 calc R U P A 2
C13B C -0.678(2) -0.455(3) -1.3156(14) 0.0287(17) Uani 0.276(3) 1 d . U P A 2
H13B H -0.682139 -0.579134 -1.280974 0.034 Uiso 0.276(3) 1 calc R U P A 2
C14B C -0.8123(19) -0.375(3) -1.3718(14) 0.0316(17) Uani 0.276(3) 1 d . U P A 2
H14B H -0.906807 -0.448819 -1.378766 0.038 Uiso 0.276(3) 1 calc R U P A 2
C15B C -0.826(2) -0.187(3) -1.4224(14) 0.0313(16) Uani 0.276(3) 1 d . U P A 2
H15B H -0.926405 -0.127136 -1.410842 0.038 Uiso 0.276(3) 1 calc R U P A 2
C16B C -0.689(2) -0.058(3) -1.3603(14) 0.0289(17) Uani 0.276(3) 1 d . U P A 2
H16C H -0.692136 0.068180 -1.400197 0.035 Uiso 0.276(3) 1 calc R U P A 2
H16D H -0.701352 -0.032677 -1.281714 0.035 Uiso 0.276(3) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3A O1A C1A 117.3(9) . . ?
C4A O2A C2A 117.2(4) . . ?
C15A O4A H4A 109.5 . . ?
C11A N1A C12A 119.9(5) . . ?
C11A N1A C16A 120.8(5) . . ?
C12A N1A C16A 117.7(5) . . ?
O1A C1A H1AA 109.5 . . ?
O1A C1A H1AB 109.5 . . ?
O1A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
O2A C2A H2AA 109.5 . . ?
O2A C2A H2AB 109.5 . . ?
O2A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
O1A C3A C4A 114.9(8) . . ?
O1A C3A C8A 125.4(9) . . ?
C8A C3A C4A 119.8(8) . . ?
O2A C4A C3A 115.1(6) . . ?
O2A C4A C5A 126.0(5) . . ?
C5A C4A C3A 118.9(6) . . ?
C4A C5A H5A 119.7 . . ?
C4A C5A C6A 120.6(5) . . ?
C6A C5A H5A 119.7 . . ?
C5A C6A C12A 121.6(4) . . ?
C7A C6A C5A 120.8(4) . . ?
C7A C6A C12A 117.6(4) . . ?
C6A C7A C8A 118.7(6) . . ?
C6A C7A C9A 121.5(5) . . ?
C8A C7A C9A 119.8(7) . . ?
C3A C8A C7A 121.2(9) . . ?
C3A C8A H8A 119.4 . . ?
C7A C8A H8A 119.4 . . ?
C7A C9A H9AA 107.9 . . ?
C7A C9A H9AB 107.9 . . ?
C7A C9A C10A 117.5(5) . . ?
H9AA C9A H9AB 107.2 . . ?
C10A C9A H9AA 107.9 . . ?
C10A C9A H9AB 107.9 . . ?
C9A C10A H10A 106.7 . . ?
C9A C10A H10B 106.7 . . ?
H10A C10A H10B 106.6 . . ?
C11A C10A C9A 122.6(5) . . ?
C11A C10A H10A 106.7 . . ?
C11A C10A H10B 106.7 . . ?
O3A C11A N1A 121.7(5) . . ?
O3A C11A C10A 118.7(5) . . ?
N1A C11A C10A 119.6(5) . . ?
N1A C12A C6A 108.6(5) . . ?
N1A C12A H12A 107.1 . . ?
N1A C12A C13A 111.7(4) . . ?
C6A C12A H12A 107.1 . . ?
C13A C12A C6A 114.7(4) . . ?
C13A C12A H12A 107.1 . . ?
C12A C13A H13A 118.3 . . ?
C14A C13A C12A 123.4(6) . . ?
C14A C13A H13A 118.3 . . ?
C13A C14A H14A 119.4 . . ?
C13A C14A C15A 121.1(6) . . ?
C15A C14A H14A 119.4 . . ?
O4A C15A C14A 110.4(6) . . ?
O4A C15A H15A 108.0 . . ?
O4A C15A C16A 111.8(5) . . ?
C14A C15A H15A 108.0 . . ?
C14A C15A C16A 110.4(5) . . ?
C16A C15A H15A 108.0 . . ?
N1A C16A C15A 109.1(5) . . ?
N1A C16A H16A 109.9 . . ?
N1A C16A H16B 109.9 . . ?
C15A C16A H16A 109.9 . . ?
C15A C16A H16B 109.9 . . ?
H16A C16A H16B 108.3 . . ?
C3B O1B C1B 117(3) . . ?
C4B O2B C2B 116.3(13) . . ?
C15B O4B H4B 109.5 . . ?
C11B N1B C12B 122.3(13) . . ?
C11B N1B C16B 123.3(14) . . ?
C16B N1B C12B 113.5(13) . . ?
O1B C1B H1BA 109.5 . . ?
O1B C1B H1BB 109.5 . . ?
O1B C1B H1BC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
O2B C2B H2BA 109.5 . . ?
O2B C2B H2BB 109.5 . . ?
O2B C2B H2BC 109.5 . . ?
H2BA C2B H2BB 109.5 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?
O1B C3B C8B 126(2) . . ?
C4B C3B O1B 114(2) . . ?
C4B C3B C8B 119(2) . . ?
C3B C4B O2B 115.6(17) . . ?
C3B C4B C5B 120.9(18) . . ?
C5B C4B O2B 123.3(15) . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B C6B 120.0(14) . . ?
C6B C5B H5B 120.0 . . ?
C5B C6B C7B 119.5(14) . . ?
C5B C6B C12B 121.7(13) . . ?
C7B C6B C12B 118.2(14) . . ?
C6B C7B C9B 118.3(16) . . ?
C8B C7B C6B 118(2) . . ?
C8B C7B C9B 123(2) . . ?
C3B C8B H8B 119.3 . . ?
C7B C8B C3B 121(3) . . ?
C7B C8B H8B 119.3 . . ?
C7B C9B H9BA 107.7 . . ?
C7B C9B H9BB 107.7 . . ?
C7B C9B C10B 118.4(15) . . ?
H9BA C9B H9BB 107.1 . . ?
C10B C9B H9BA 107.7 . . ?
C10B C9B H9BB 107.7 . . ?
C9B C10B H10C 106.7 . . ?
C9B C10B H10D 106.7 . . ?
H10C C10B H10D 106.6 . . ?
C11B C10B C9B 122.5(13) . . ?
C11B C10B H10C 106.7 . . ?
C11B C10B H10D 106.7 . . ?
O3B C11B N1B 120.9(14) . . ?
O3B C11B C10B 121.1(13) . . ?
N1B C11B C10B 117.9(14) . . ?
N1B C12B C6B 108.3(14) . . ?
N1B C12B H12B 106.7 . . ?
C6B C12B H12B 106.7 . . ?
C13B C12B N1B 113.5(13) . . ?
C13B C12B C6B 114.6(13) . . ?
C13B C12B H12B 106.7 . . ?
C12B C13B H13B 118.6 . . ?
C14B C13B C12B 122.8(17) . . ?
C14B C13B H13B 118.6 . . ?
C13B C14B H14B 117.5 . . ?
C13B C14B C15B 125.0(17) . . ?
C15B C14B H14B 117.5 . . ?
O4B C15B C14B 115.2(16) . . ?
O4B C15B H15B 107.4 . . ?
O4B C15B C16B 109.6(14) . . ?
C14B C15B H15B 107.4 . . ?
C14B C15B C16B 109.5(15) . . ?
C16B C15B H15B 107.4 . . ?
N1B C16B C15B 110.2(13) . . ?
N1B C16B H16C 109.6 . . ?
N1B C16B H16D 109.6 . . ?
C15B C16B H16C 109.6 . . ?
C15B C16B H16D 109.6 . . ?
H16C C16B H16D 108.1 . . ?
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
O1A C1A 1.426(17) . ?
O1A C3A 1.362(11) . ?
O2A C2A 1.433(8) . ?
O2A C4A 1.351(7) . ?
O3A C11A 1.250(7) . ?
O4A H4A 0.8400 . ?
O4A C15A 1.448(7) . ?
N1A C11A 1.346(7) . ?
N1A C12A 1.451(8) . ?
N1A C16A 1.453(7) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C3A C4A 1.414(12) . ?
C3A C8A 1.384(15) . ?
C4A C5A 1.385(7) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.400(7) . ?
C6A C7A 1.380(8) . ?
C6A C12A 1.523(7) . ?
C7A C8A 1.401(12) . ?
C7A C9A 1.519(9) . ?
C8A H8A 0.9500 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.550(8) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A C11A 1.515(8) . ?
C12A H12A 1.0000 . ?
C12A C13A 1.518(8) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.332(9) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.494(11) . ?
C15A H15A 1.0000 . ?
C15A C16A 1.520(8) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
O1B C1B 1.38(5) . ?
O1B C3B 1.37(3) . ?
O2B C2B 1.44(2) . ?
O2B C4B 1.42(2) . ?
O3B C11B 1.225(19) . ?
O4B H4B 0.8400 . ?
O4B C15B 1.41(2) . ?
N1B C11B 1.316(19) . ?
N1B C12B 1.53(2) . ?
N1B C16B 1.50(2) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
C2B H2BA 0.9800 . ?
C2B H2BB 0.9800 . ?
C2B H2BC 0.9800 . ?
C3B C4B 1.37(3) . ?
C3B C8B 1.39(4) . ?
C4B C5B 1.38(2) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.39(2) . ?
C6B C7B 1.41(2) . ?
C6B C12B 1.53(2) . ?
C7B C8B 1.37(4) . ?
C7B C9B 1.53(3) . ?
C8B H8B 0.9500 . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9B C10B 1.54(2) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C10B C11B 1.51(2) . ?
C12B H12B 1.0000 . ?
C12B C13B 1.46(2) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.33(2) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.42(3) . ?
C15B H15B 1.0000 . ?
C15B C16B 1.52(2) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
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
O1A C3A C4A O2A -2.8(7) . . . . ?
O1A C3A C4A C5A 178.0(5) . . . . ?
O1A C3A C8A C7A -178.8(6) . . . . ?
O2A C4A C5A C6A -178.4(5) . . . . ?
O4A C15A C16A N1A 70.9(6) . . . . ?
N1A C12A C13A C14A -3.9(9) . . . . ?
C1A O1A C3A C4A -176.5(5) . . . . ?
C1A O1A C3A C8A 3.6(8) . . . . ?
C2A O2A C4A C3A -175.6(5) . . . . ?
C2A O2A C4A C5A 3.5(9) . . . . ?
C3A C4A C5A C6A 0.7(9) . . . . ?
C4A C3A C8A C7A 1.3(8) . . . . ?
C4A C5A C6A C7A 1.7(9) . . . . ?
C4A C5A C6A C12A -180.0(5) . . . . ?
C5A C6A C7A C8A -2.5(9) . . . . ?
C5A C6A C7A C9A 179.2(5) . . . . ?
C5A C6A C12A N1A -101.1(6) . . . . ?
C5A C6A C12A C13A 24.7(7) . . . . ?
C6A C7A C8A C3A 1.1(9) . . . . ?
C6A C7A C9A C10A -46.3(8) . . . . ?
C6A C12A C13A C14A -128.1(6) . . . . ?
C7A C6A C12A N1A 77.3(6) . . . . ?
C7A C6A C12A C13A -156.9(5) . . . . ?
C7A C9A C10A C11A 3.0(9) . . . . ?
C8A C3A C4A O2A 177.1(5) . . . . ?
C8A C3A C4A C5A -2.1(8) . . . . ?
C8A C7A C9A C10A 135.5(6) . . . . ?
C9A C7A C8A C3A 179.4(5) . . . . ?
C9A C10A C11A O3A -131.9(6) . . . . ?
C9A C10A C11A N1A 50.1(8) . . . . ?
C11A N1A C12A C6A -67.7(6) . . . . ?
C11A N1A C12A C13A 164.8(5) . . . . ?
C11A N1A C16A C15A -136.0(5) . . . . ?
C12A N1A C11A O3A 169.2(5) . . . . ?
C12A N1A C11A C10A -12.8(8) . . . . ?
C12A N1A C16A C15A 58.3(7) . . . . ?
C12A C6A C7A C8A 179.1(5) . . . . ?
C12A C6A C7A C9A 0.8(8) . . . . ?
C12A C13A C14A C15A 5.6(10) . . . . ?
C13A C14A C15A O4A -101.0(7) . . . . ?
C13A C14A C15A C16A 23.3(9) . . . . ?
C14A C15A C16A N1A -52.5(6) . . . . ?
C16A N1A C11A O3A 3.9(7) . . . . ?
C16A N1A C11A C10A -178.1(5) . . . . ?
C16A N1A C12A C6A 98.1(5) . . . . ?
C16A N1A C12A C13A -29.4(7) . . . . ?
O1B C3B C4B O2B 6(2) . . . . ?
O1B C3B C4B C5B -167.9(17) . . . . ?
O1B C3B C8B C7B 171.4(18) . . . . ?
O2B C4B C5B C6B -176.5(15) . . . . ?
O4B C15B C16B N1B -73.8(18) . . . . ?
N1B C12B C13B C14B 4(2) . . . . ?
C1B O1B C3B C4B 174.5(18) . . . . ?
C1B O1B C3B C8B 4(3) . . . . ?
C2B O2B C4B C3B 175.1(15) . . . . ?
C2B O2B C4B C5B -11(2) . . . . ?
C3B C4B C5B C6B -3(3) . . . . ?
C4B C3B C8B C7B 1(3) . . . . ?
C4B C5B C6B C7B -2(2) . . . . ?
C4B C5B C6B C12B -173.7(16) . . . . ?
C5B C6B C7B C8B 7(2) . . . . ?
C5B C6B C7B C9B -179.2(15) . . . . ?
C5B C6B C12B N1B 101.0(16) . . . . ?
C5B C6B C12B C13B -27(2) . . . . ?
C6B C7B C8B C3B -6(3) . . . . ?
C6B C7B C9B C10B 54(2) . . . . ?
C6B C12B C13B C14B 129.5(17) . . . . ?
C7B C6B C12B N1B -70.3(18) . . . . ?
C7B C6B C12B C13B 162.0(16) . . . . ?
C7B C9B C10B C11B -5(2) . . . . ?
C8B C3B C4B O2B 177.7(15) . . . . ?
C8B C3B C4B C5B 4(3) . . . . ?
C8B C7B C9B C10B -132.8(19) . . . . ?
C9B C7B C8B C3B -179.8(16) . . . . ?
C9B C10B C11B O3B 132.9(16) . . . . ?
C9B C10B C11B N1B -51(2) . . . . ?
C11B N1B C12B C6B 66.4(18) . . . . ?
C11B N1B C12B C13B -165.2(13) . . . . ?
C11B N1B C16B C15B 136.3(15) . . . . ?
C12B N1B C11B O3B -170.5(14) . . . . ?
C12B N1B C11B C10B 14(2) . . . . ?
C12B N1B C16B C15B -54.6(18) . . . . ?
C12B C6B C7B C8B 178.3(17) . . . . ?
C12B C6B C7B C9B -8(2) . . . . ?
C12B C13B C14B C15B -4(3) . . . . ?
C13B C14B C15B O4B 98(2) . . . . ?
C13B C14B C15B C16B -26(3) . . . . ?
C14B C15B C16B N1B 53.5(19) . . . . ?
C16B N1B C11B O3B -2(2) . . . . ?
C16B N1B C11B C10B -178.1(13) . . . . ?
C16B N1B C12B C6B -102.9(14) . . . . ?
C16B N1B C12B C13B 25.5(19) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -1(3)
2 2(3)
