#------------------------------------------------------------------------------
#$Date: 2025-11-07 04:37:17 +0200 (Fri, 07 Nov 2025) $
#$Revision: 303222 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/12/7251235.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_7251235
loop_
_publ_author_name
'Dosanjh, Ramandeep'
'Patterson, Adam'
'Harris, Joe'
'Wilson, Claire'
'Gutmann, Matthias J.'
'Collier, Paul'
'Hyde, Tim'
'Johnson, Timothy'
'York, Andy'
'Parker, Stewart F.'
'Lennon, David'
_publ_section_title
;
 Spectroscopic investigations of a pharmaceutical solid form analogue:
 pyrimethanil L-tartrate hemi-cocrystal
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D5CP02802G
_journal_year                    2025
_chemical_formula_moiety         '4(C28 H32 N6 O6)'
_chemical_formula_sum            'C112 H128 N24 O24'
_chemical_formula_weight         2194.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2024-06-23
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-19 deposited with the CCDC.	2025-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   18.791(3)
_cell_length_b                   16.407(2)
_cell_length_c                   8.6453(15)
_cell_measurement_temperature    283.15
_cell_volume                     2665.4(7)
_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)'
_diffrn_ambient_temperature      283.15
_diffrn_measured_fraction_theta_full 0.667
_diffrn_measured_fraction_theta_max 0.160
_diffrn_radiation_type           neutrons
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_unetI/netI     0.1388
_diffrn_reflns_Laue_measured_fraction_full 0.667
_diffrn_reflns_Laue_measured_fraction_max 0.160
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18634
_diffrn_reflns_point_group_measured_fraction_full 0.634
_diffrn_reflns_point_group_measured_fraction_max 0.133
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         88.133
_diffrn_reflns_theta_min         8.926
_exptl_absorpt_coefficient_mu    0.045
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          4
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          1
_refine_diff_density_max         3.904
_refine_diff_density_min         -1.944
_refine_diff_density_rms         0.446
_refine_ls_abs_structure_details
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_extinction_coef       0.00013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         18634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0957
_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)+(0.1688P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2279
_refine_ls_wR_factor_ref         0.2343
_reflns_Friedel_coverage         0.553
_reflns_Friedel_fraction_full    0.590
_reflns_Friedel_fraction_max     0.102
_reflns_number_gt                17642
_reflns_number_total             18634
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cp02802g2.cif
_cod_data_source_block           pyrimethanilhemicocrystal_10k_sxd
_cod_database_code               7251235
_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.
;
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.839
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: -37.2(4)
 3.45(11) 0.76(4) 2.84(9) 0.72(3) 2.59(9) 0.95(4) 3.15(10) 1.08(4) 3.25(11)
 4.71(15) 3.24(11) 2.42(8) 4.16(13) 4.89(16)
2. Uiso/Uaniso restraints and constraints
Uanis(O1A) = Uanis(O2A)
Uanis(O1B) = Uanis(O2B)
Uiso(O3A) = Uiso(O3AB)
Uiso(H3AA) = Uiso(H3AB)
Uiso(H14A) = Uiso(H14B)
Uanis(C13A) = Uanis(C14A)
Uanis(C13B) = Uanis(C14B)
Uanis(N1A) = Uanis(N2A) = Uanis(N3A)
Uanis(N1B) = Uanis(N2B) = Uanis(N3B)
Uanis(C1A) = Uanis(C2A) = Uanis(C3A) = Uanis(C4A) = Uanis(C5A) = Uanis(C6A)
Uanis(C1B) = Uanis(C2B) = Uanis(C3B) = Uanis(C4B) = Uanis(C5B) = Uanis(C6B)
Uanis(C7A) = Uanis(C8A) = Uanis(C9A) = Uanis(C10A) = Uanis(C11A) = Uanis(C12A)
Uanis(C7B) = Uanis(C8B) = Uanis(C9B) = Uanis(C10B) = Uanis(C11B) = Uanis(C12B)
3. Others
 Sof(O3AB)=Sof(H3AB)=Sof(H14B)=1-FVAR(1)
 Sof(O3A)=Sof(H3AA)=Sof(H14A)=FVAR(1)
 Sof(H2B)=1-FVAR(2)
 Sof(H1B)=FVAR(2)
 Fixed Sof: H2A(0.5) H2AA(0.5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.4200(6) 0.8853(6) 0.5798(16) 0.0121(18) Uani 1 1 d . . . . .
O2A O 0.4415(6) 0.8606(6) 0.8293(17) 0.0121(18) Uani 1 1 d . . . . .
O3A O 0.5523(11) 0.9622(13) 0.851(3) 0.004(3) Uiso 0.51(2) 1 d . . P . .
H3AA H 0.542(3) 0.915(4) 0.915(9) 0.020(7) Uiso 0.51(2) 1 d . . P . .
O3AB O 0.5710(10) 0.9319(12) 0.796(3) 0.004(3) Uiso 0.49(2) 1 d . . P . .
H3AB H 0.550(4) 0.925(5) 0.899(10) 0.020(7) Uiso 0.49(2) 1 d . . P . .
N1A N 0.3766(3) 0.7216(4) 0.5762(10) 0.0075(9) Uani 1 1 d . . . . .
H1A H 0.3905(10) 0.7817(11) 0.576(3) 0.016(5) Uani 1 1 d . . . . .
N2A N 0.3398(4) 0.7528(4) 0.8202(11) 0.0075(9) Uani 1 1 d . . . . .
N3A N 0.3062(4) 0.6260(4) 0.7088(10) 0.0075(9) Uani 1 1 d . . . . .
C1A C 0.4224(5) 0.7248(5) 0.3200(14) 0.0075(8) Uani 1 1 d . . . . .
H1AA H 0.4240(12) 0.7905(11) 0.330(3) 0.021(5) Uani 1 1 d . . . . .
C2A C 0.4450(5) 0.6888(5) 0.1841(14) 0.0075(8) Uani 1 1 d . . . . .
H2AB H 0.4637(11) 0.7258(12) 0.091(3) 0.020(5) Uani 1 1 d . . . . .
C3A C 0.4433(5) 0.6035(5) 0.1682(15) 0.0075(8) Uani 1 1 d . . . . .
H3A H 0.4610(13) 0.5756(13) 0.063(3) 0.023(5) Uani 1 1 d . . . . .
C4A C 0.4185(5) 0.5567(5) 0.2921(14) 0.0075(8) Uani 1 1 d . . . . .
H4A H 0.4165(14) 0.4901(13) 0.281(3) 0.024(6) Uani 1 1 d . . . . .
C5A C 0.3945(5) 0.5928(5) 0.4286(15) 0.0075(8) Uani 1 1 d . . . . .
H5A H 0.3739(14) 0.5560(14) 0.522(3) 0.026(6) Uani 1 1 d . . . . .
C6A C 0.3968(5) 0.6777(5) 0.4425(14) 0.0075(8) Uani 1 1 d . . . . .
C7A C 0.3400(5) 0.6972(5) 0.7035(13) 0.0065(8) Uani 1 1 d . . . . .
C8A C 0.2678(5) 0.6102(5) 0.8360(14) 0.0065(8) Uani 1 1 d . . . . .
C9A C 0.2624(5) 0.6653(5) 0.9597(15) 0.0065(8) Uani 1 1 d . . . . .
H9A H 0.2316(12) 0.6522(12) 1.058(3) 0.022(5) Uani 1 1 d . . . . .
C10A C 0.3003(5) 0.7384(5) 0.9477(14) 0.0065(8) Uani 1 1 d . . . . .
C11A C 0.2292(5) 0.5303(5) 0.8404(15) 0.0065(8) Uani 1 1 d . . . . .
H11A H 0.1823(16) 0.5351(17) 0.772(6) 0.062(14) Uani 1 1 d . . . . .
H11B H 0.214(3) 0.513(2) 0.952(5) 0.095(18) Uani 1 1 d . . . . .
H11C H 0.2600(16) 0.4838(14) 0.796(5) 0.048(10) Uani 1 1 d . . . . .
C12A C 0.2978(5) 0.8045(5) 1.0667(15) 0.0065(8) Uani 1 1 d . . . . .
H12A H 0.3456(12) 0.8414(15) 1.063(4) 0.033(7) Uani 1 1 d . . . . .
H12B H 0.2913(17) 0.7777(15) 1.183(4) 0.038(7) Uani 1 1 d . . . . .
H12C H 0.2543(14) 0.8415(17) 1.045(4) 0.044(9) Uani 1 1 d . . . . .
C13A C 0.4539(5) 0.8965(6) 0.6996(15) 0.0104(16) Uani 1 1 d . . . . .
C14A C 0.5156(5) 0.9568(6) 0.7004(15) 0.0104(16) Uani 1 1 d . . . . .
H14A H 0.542(3) 0.949(4) 0.574(8) 0.016(6) Uiso 0.51(2) 1 d . . P . .
H14B H 0.547(4) 0.948(4) 0.605(8) 0.016(6) Uiso 0.49(2) 1 d . . P . .
O1B O 0.5761(5) 0.8761(6) 0.3498(15) 0.0059(15) Uani 1 1 d . . . . .
H1B H 0.610(3) 0.827(4) 0.334(5) 0.011(14) Uani 0.51(18) 1 d . . P . .
O2B O 0.5485(5) 0.8601(6) 0.1009(14) 0.0059(15) Uani 1 1 d . . . . .
O3B O 0.4294(5) 0.9505(6) 0.1308(17) 0.007(2) Uani 1 1 d . . . . .
H3B H 0.4479(14) 0.936(3) 0.041(4) 0.064(11) Uani 1 1 d . . . . .
N1B N 0.6172(3) 0.7098(4) 0.0901(9) 0.0050(8) Uani 1 1 d . . . . .
H1BA H 0.5949(12) 0.7684(11) 0.095(3) 0.022(5) Uani 1 1 d . . . . .
N2B N 0.6569(4) 0.7440(4) 0.3312(10) 0.0050(8) Uani 1 1 d . . . . .
N3B N 0.6907(4) 0.6173(4) 0.2200(9) 0.0050(8) Uani 1 1 d . . . . .
C1B C 0.5690(5) 0.7127(5) -0.1644(14) 0.0065(8) Uani 1 1 d . . . . .
H1BB H 0.5613(12) 0.7780(11) -0.148(3) 0.022(5) Uani 1 1 d . . . . .
C2B C 0.5483(5) 0.6758(5) -0.3028(14) 0.0065(8) Uani 1 1 d . . . . .
H2BA H 0.5240(13) 0.7131(13) -0.394(3) 0.026(6) Uani 1 1 d . . . . .
C3B C 0.5574(5) 0.5916(5) -0.3225(15) 0.0065(8) Uani 1 1 d . . . . .
H3BA H 0.5391(13) 0.5633(12) -0.428(3) 0.026(6) Uani 1 1 d . . . . .
C4B C 0.5871(5) 0.5457(5) -0.2043(13) 0.0065(8) Uani 1 1 d . . . . .
H4B H 0.5936(15) 0.4817(13) -0.219(3) 0.026(6) Uani 1 1 d . . . . .
C5B C 0.6087(5) 0.5820(5) -0.0655(14) 0.0065(8) Uani 1 1 d . . . . .
H5B H 0.6325(13) 0.5461(13) 0.025(3) 0.025(6) Uani 1 1 d . . . . .
C6B C 0.6000(5) 0.6664(5) -0.0453(14) 0.0065(8) Uani 1 1 d . . . . .
C7B C 0.6558(5) 0.6877(5) 0.2153(14) 0.0073(9) Uani 1 1 d . . . . .
C8B C 0.7292(5) 0.6009(5) 0.3472(15) 0.0073(9) Uani 1 1 d . . . . .
C9B C 0.7325(5) 0.6555(5) 0.4699(15) 0.0073(9) Uani 1 1 d . . . . .
H9B H 0.7640(12) 0.6421(12) 0.572(3) 0.022(5) Uani 1 1 d . . . . .
C10B C 0.6956(5) 0.7282(5) 0.4573(14) 0.0073(9) Uani 1 1 d . . . . .
C11B C 0.7686(6) 0.5215(5) 0.3480(15) 0.0073(9) Uani 1 1 d . . . . .
H11D H 0.7345(14) 0.4727(14) 0.312(5) 0.043(9) Uani 1 1 d . . . . .
H11E H 0.7941(17) 0.5090(17) 0.458(4) 0.046(8) Uani 1 1 d . . . . .
H11F H 0.8125(16) 0.5224(17) 0.264(4) 0.044(9) Uani 1 1 d . . . . .
C12B C 0.6977(5) 0.7929(5) 0.5795(15) 0.0073(9) Uani 1 1 d . . . . .
H12D H 0.7440(16) 0.827(2) 0.568(5) 0.055(11) Uani 1 1 d . . . . .
H12E H 0.699(2) 0.7678(16) 0.692(4) 0.044(8) Uani 1 1 d . . . . .
H12F H 0.6526(17) 0.8330(16) 0.575(4) 0.044(8) Uani 1 1 d . . . . .
C13B C 0.5396(5) 0.8931(5) 0.2280(13) 0.0050(14) Uani 1 1 d . . . . .
C14B C 0.4821(5) 0.9583(6) 0.2476(13) 0.0050(14) Uani 1 1 d . . . . .
H14C H 0.4562(10) 0.9480(12) 0.358(3) 0.016(5) Uani 1 1 d . . . . .
H2B H 0.625(4) 0.800(6) 0.331(8) 0.023(16) Uiso 0.49(18) 1 d . . P . .
H2A H 0.401(2) 0.817(2) 0.812(6) 0.011(8) Uiso 0.5 1 d . . P A 2
H2AA H 0.377(3) 0.804(3) 0.825(7) 0.014(9) Uiso 0.5 1 d . . P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
H H 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
N N 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
C C 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
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
H2A O2A C13A 109(3) . . ?
H3AA O3A C14A 111(5) . . ?
O3AB O3A H3AA 86(5) . . ?
O3AB O3A C14A 68(3) . . ?
H3AB O3A H3AA 8(9) . . ?
H3AB O3A O3AB 81(7) . . ?
H3AB O3A C14A 114(7) . . ?
O3A H3AA O3AB 40(3) . . ?
O3A O3AB H3AA 54(4) . . ?
O3A O3AB H3AB 48(6) . . ?
O3A O3AB C14A 80(3) . . ?
H3AA O3AB C14A 104(4) . . ?
H3AB O3AB H3AA 7(7) . . ?
H3AB O3AB C14A 106(5) . . ?
O3A H3AB O3AB 51(5) . . ?
H1A N1A C6A 114.9(16) . . ?
H1A N1A C7A 114.7(15) . . ?
C7A N1A C6A 130.4(7) . . ?
C10A N2A C7A 119.4(8) . . ?
H2AA N2A C7A 123(3) . . ?
H2AA N2A C10A 117(3) . . ?
C7A N3A C8A 117.1(9) . . ?
H1AA C1A C2A 119.0(17) . . ?
H1AA C1A C6A 120.1(17) . . ?
C2A C1A C6A 120.9(9) . . ?
C1A C2A C3A 120.1(10) . . ?
H2AB C2A C1A 119.9(15) . . ?
H2AB C2A C3A 120.0(16) . . ?
H3A C3A C2A 120.0(15) . . ?
H3A C3A C4A 121.3(15) . . ?
C4A C3A C2A 118.6(11) . . ?
H4A C4A C3A 119.4(17) . . ?
H4A C4A C5A 119.1(17) . . ?
C5A C4A C3A 121.5(9) . . ?
C4A C5A C6A 119.1(10) . . ?
H5A C5A C4A 120.8(15) . . ?
H5A C5A C6A 120.1(16) . . ?
C1A C6A N1A 115.5(8) . . ?
C1A C6A C5A 119.8(11) . . ?
C5A C6A N1A 124.7(10) . . ?
N1A C7A N2A 113.9(8) . . ?
N3A C7A N1A 121.9(9) . . ?
N3A C7A N2A 124.2(10) . . ?
N3A C8A C9A 122.6(8) . . ?
N3A C8A C11A 116.8(9) . . ?
C9A C8A C11A 120.6(10) . . ?
H9A C9A C8A 121.6(14) . . ?
H9A C9A C10A 121.1(16) . . ?
C10A C9A C8A 117.3(11) . . ?
N2A C10A C9A 119.4(10) . . ?
N2A C10A C12A 116.9(8) . . ?
C9A C10A C12A 123.7(11) . . ?
H11A C11A C8A 108.8(17) . . ?
H11B C11A C8A 113(2) . . ?
H11B C11A H11A 108(4) . . ?
H11C C11A C8A 111.5(18) . . ?
H11C C11A H11A 108(3) . . ?
H11C C11A H11B 107(4) . . ?
H12A C12A C10A 111.0(18) . . ?
H12A C12A H12B 110(3) . . ?
H12B C12A C10A 110.0(15) . . ?
H12C C12A C10A 109.0(19) . . ?
H12C C12A H12A 109(2) . . ?
H12C C12A H12B 108(3) . . ?
O1A C13A O2A 124.8(11) . . ?
O1A C13A C14A 119.7(11) . . ?
O2A C13A C14A 115.6(11) . . ?
O3A C14A C13A 113.5(12) . . ?
O3A C14A C14A 97.1(10) . 2_675 ?
O3AB C14A O3A 31.2(12) . . ?
O3AB C14A C13A 112.4(11) . . ?
O3AB C14A C14A 124.0(12) . 2_675 ?
C13A C14A C14A 108.0(10) . 2_675 ?
H14A C14A O3A 128(3) . . ?
H14A C14A O3AB 101(3) . . ?
H14A C14A C13A 104(3) . . ?
H14A C14A C14A 105(3) . 2_675 ?
H14B C14A O3A 117(4) . . ?
H14B C14A O3AB 90(4) . . ?
H14B C14A C13A 110(4) . . ?
H14B C14A C14A 111(4) . 2_675 ?
H14B C14A H14A 11(6) . . ?
H1B O1B C13B 113(3) . . ?
H2B H1B O1B 173(10) . . ?
H3B O3B C14B 111.9(19) . . ?
H1BA N1B C6B 114.0(16) . . ?
H1BA N1B C7B 115.2(17) . . ?
C7B N1B C6B 130.7(7) . . ?
C10B N2B C7B 118.5(8) . . ?
H2B N2B C7B 124(4) . . ?
H2B N2B C10B 117(4) . . ?
C7B N3B C8B 117.8(8) . . ?
H1BB C1B C2B 120.2(17) . . ?
H1BB C1B C6B 119.3(17) . . ?
C2B C1B C6B 120.5(8) . . ?
C1B C2B C3B 119.8(10) . . ?
H2BA C2B C1B 119.3(15) . . ?
H2BA C2B C3B 120.8(16) . . ?
H3BA C3B C2B 119.1(14) . . ?
H3BA C3B C4B 121.2(13) . . ?
C4B C3B C2B 119.6(11) . . ?
C3B C4B C5B 121.2(9) . . ?
H4B C4B C3B 119.7(19) . . ?
H4B C4B C5B 119.1(18) . . ?
C4B C5B C6B 119.5(10) . . ?
H5B C5B C4B 120.7(15) . . ?
H5B C5B C6B 119.8(17) . . ?
C1B C6B N1B 115.5(7) . . ?
C5B C6B N1B 125.1(10) . . ?
C5B C6B C1B 119.4(10) . . ?
N1B C7B N2B 114.5(8) . . ?
N3B C7B N1B 121.6(9) . . ?
N3B C7B N2B 123.9(10) . . ?
N3B C8B C9B 121.3(8) . . ?
N3B C8B C11B 116.3(10) . . ?
C9B C8B C11B 122.3(10) . . ?
H9B C9B C8B 121.0(14) . . ?
H9B C9B C10B 120.8(15) . . ?
C10B C9B C8B 118.2(11) . . ?
N2B C10B C9B 120.3(10) . . ?
N2B C10B C12B 116.9(8) . . ?
C9B C10B C12B 122.8(10) . . ?
H11D C11B C8B 110.6(16) . . ?
H11D C11B H11E 112(3) . . ?
H11D C11B H11F 106(3) . . ?
H11E C11B C8B 112.7(18) . . ?
H11E C11B H11F 104(3) . . ?
H11F C11B C8B 110.9(17) . . ?
H12D C12B C10B 110(2) . . ?
H12D C12B H12E 107(3) . . ?
H12D C12B H12F 109(3) . . ?
H12E C12B C10B 111.9(17) . . ?
H12E C12B H12F 107(3) . . ?
H12F C12B C10B 112.8(18) . . ?
O1B C13B C14B 116.0(9) . . ?
O2B C13B O1B 124.1(10) . . ?
O2B C13B C14B 120.0(10) . . ?
O3B C14B C13B 110.6(9) . . ?
O3B C14B C14B 112.8(8) . 2_675 ?
C14B C14B C13B 108.4(9) 2_675 . ?
H14C C14B O3B 107.4(14) . . ?
H14C C14B C13B 107.8(13) . . ?
H14C C14B C14B 109.7(12) . 2_675 ?
H1B H2B N2B 178(10) . . ?
H2AA H2A O2A 153(10) . . ?
H2A H2AA N2A 151(10) . . ?
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 C13A 1.230(17) . ?
O2A C13A 1.288(18) . ?
O2A H2A 1.06(4) . ?
O3A H3AA 0.97(6) . ?
O3A O3AB 0.77(3) . ?
O3A H3AB 0.75(9) . ?
O3A C14A 1.47(3) . ?
H3AA O3AB 1.20(7) . ?
O3AB H3AA 1.20(7) . ?
O3AB H3AB 0.98(9) . ?
O3AB C14A 1.39(2) . ?
N1A H1A 1.02(2) . ?
N1A C6A 1.414(14) . ?
N1A C7A 1.358(14) . ?
N2A C7A 1.360(13) . ?
N2A C10A 1.349(14) . ?
N2A H2AA 1.09(5) . ?
N3A C7A 1.330(12) . ?
N3A C8A 1.340(14) . ?
C1A H1AA 1.08(2) . ?
C1A C2A 1.382(16) . ?
C1A C6A 1.397(16) . ?
C2A H2AB 1.07(3) . ?
C2A C3A 1.406(13) . ?
C3A H3A 1.07(3) . ?
C3A C4A 1.398(15) . ?
C4A H4A 1.10(2) . ?
C4A C5A 1.395(16) . ?
C5A H5A 1.08(3) . ?
C5A C6A 1.398(13) . ?
C8A C9A 1.405(16) . ?
C8A C11A 1.498(13) . ?
C9A H9A 1.05(3) . ?
C9A C10A 1.399(13) . ?
C10A C12A 1.495(15) . ?
C11A H11A 1.07(3) . ?
C11A H11B 1.04(4) . ?
C11A H11C 1.03(3) . ?
C12A H12A 1.08(2) . ?
C12A H12B 1.11(4) . ?
C12A H12C 1.03(3) . ?
C13A C14A 1.525(13) . ?
C14A C14A 1.53(2) 2_675 ?
C14A H14A 1.21(7) . ?
C14A H14B 1.03(8) . ?
O1B H1B 1.03(8) . ?
O1B C13B 1.286(16) . ?
H1B H2B 0.53(6) . ?
O2B C13B 1.236(15) . ?
O3B H3B 0.88(4) . ?
O3B C14B 1.421(16) . ?
N1B H1BA 1.05(2) . ?
N1B C6B 1.408(14) . ?
N1B C7B 1.351(14) . ?
N2B C7B 1.363(13) . ?
N2B C10B 1.336(14) . ?
N2B H2B 1.10(11) . ?
N3B C7B 1.329(12) . ?
N3B C8B 1.343(14) . ?
C1B H1BB 1.09(2) . ?
C1B C2B 1.396(16) . ?
C1B C6B 1.407(15) . ?
C2B H2BA 1.10(3) . ?
C2B C3B 1.402(12) . ?
C3B H3BA 1.08(3) . ?
C3B C4B 1.387(15) . ?
C4B H4B 1.06(2) . ?
C4B C5B 1.400(16) . ?
C5B H5B 1.08(3) . ?
C5B C6B 1.404(13) . ?
C8B C9B 1.389(16) . ?
C8B C11B 1.499(13) . ?
C9B H9B 1.09(3) . ?
C9B C10B 1.384(13) . ?
C10B C12B 1.499(16) . ?
C11B H11D 1.07(3) . ?
C11B H11E 1.09(4) . ?
C11B H11F 1.10(3) . ?
C12B H12D 1.04(3) . ?
C12B H12E 1.05(4) . ?
C12B H12F 1.07(3) . ?
C13B C14B 1.529(13) . ?
C14B C14B 1.525(19) 2_675 ?
C14B H14C 1.09(3) . ?
H2B H1B 0.53(6) . ?
H2A H2AA 0.51(5) . ?
H2AA H2A 0.51(5) . ?
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 C13A C14A O3A -178.5(14) . . . . ?
O1A C13A C14A O3AB -144.6(15) . . . . ?
O1A C13A C14A C14A 75.0(11) . . . 2_675 ?
O1A C13A C14A H14A -36(3) . . . . ?
O1A C13A C14A H14B -46(4) . . . . ?
O2A C13A C14A O3A 1.6(16) . . . . ?
O2A C13A C14A O3AB 35.5(18) . . . . ?
O2A C13A C14A C14A -104.8(9) . . . 2_675 ?
O2A C13A C14A H14A 144(3) . . . . ?
O2A C13A C14A H14B 134(4) . . . . ?
O2A H2A H2AA N2A -161(9) . . . . ?
O3A H3AA O3AB H3AB 39(57) . . . . ?
O3A H3AA O3AB C14A -67(4) . . . . ?
O3A O3AB C14A C13A -99(2) . . . . ?
O3A O3AB C14A C14A 34(3) . . . 2_675 ?
O3A O3AB C14A H14A 151(4) . . . . ?
O3A O3AB C14A H14B 149(4) . . . . ?
H3AA O3A O3AB H3AB -6(10) . . . . ?
H3AA O3A O3AB C14A 115(4) . . . . ?
H3AA O3A H3AB O3AB 131(75) . . . . ?
H3AA O3A C14A O3AB -77(5) . . . . ?
H3AA O3A C14A C13A 18(5) . . . . ?
H3AA O3A C14A C14A 132(5) . . . 2_675 ?
H3AA O3A C14A H14A -113(6) . . . . ?
H3AA O3A C14A H14B -111(6) . . . . ?
H3AA O3AB H3AB O3A -137(62) . . . . ?
H3AA O3AB C14A O3A 49(4) . . . . ?
H3AA O3AB C14A C13A -50(4) . . . . ?
H3AA O3AB C14A C14A 83(4) . . . 2_675 ?
H3AA O3AB C14A H14A -160(5) . . . . ?
H3AA O3AB C14A H14B -162(5) . . . . ?
O3AB O3A C14A C13A 95(2) . . . . ?
O3AB O3A C14A C14A -152(2) . . . 2_675 ?
O3AB O3A C14A H14A -37(5) . . . . ?
O3AB O3A C14A H14B -35(5) . . . . ?
H3AB O3A H3AA O3AB -48(74) . . . . ?
H3AB O3A O3AB H3AA 6(10) . . . . ?
H3AB O3A O3AB C14A 121(6) . . . . ?
H3AB O3A C14A O3AB -68(7) . . . . ?
H3AB O3A C14A C13A 27(7) . . . . ?
H3AB O3A C14A C14A 140(6) . . . 2_675 ?
H3AB O3A C14A H14A -105(7) . . . . ?
H3AB O3A C14A H14B -103(8) . . . . ?
H3AB O3AB C14A O3A 42(6) . . . . ?
H3AB O3AB C14A C13A -57(5) . . . . ?
H3AB O3AB C14A C14A 76(5) . . . 2_675 ?
H3AB O3AB C14A H14A -167(6) . . . . ?
H3AB O3AB C14A H14B -169(6) . . . . ?
H1A N1A C6A C1A -9.7(18) . . . . ?
H1A N1A C6A C5A 168.5(16) . . . . ?
H1A N1A C7A N2A -11.5(18) . . . . ?
H1A N1A C7A N3A 166.5(15) . . . . ?
N2A C10A C12A H12A -27(2) . . . . ?
N2A C10A C12A H12B -149(2) . . . . ?
N2A C10A C12A H12C 92(2) . . . . ?
N3A C8A C9A H9A 179.4(18) . . . . ?
N3A C8A C9A C10A -1.4(14) . . . . ?
N3A C8A C11A H11A -78(3) . . . . ?
N3A C8A C11A H11B 161(4) . . . . ?
N3A C8A C11A H11C 41(3) . . . . ?
C1A C2A C3A H3A -179.8(18) . . . . ?
C1A C2A C3A C4A 0.0(15) . . . . ?
H1AA C1A C2A H2AB 0(2) . . . . ?
H1AA C1A C2A C3A -179.8(17) . . . . ?
H1AA C1A C6A N1A -2(2) . . . . ?
H1AA C1A C6A C5A 179.6(17) . . . . ?
C2A C1A C6A N1A 178.9(9) . . . . ?
C2A C1A C6A C5A 0.6(15) . . . . ?
C2A C3A C4A H4A 179.6(19) . . . . ?
C2A C3A C4A C5A 1.1(16) . . . . ?
H2AB C2A C3A H3A 0(3) . . . . ?
H2AB C2A C3A C4A -179.9(17) . . . . ?
C3A C4A C5A H5A 178.1(19) . . . . ?
C3A C4A C5A C6A -1.3(16) . . . . ?
H3A C3A C4A H4A -1(3) . . . . ?
H3A C3A C4A C5A -179.1(18) . . . . ?
C4A C5A C6A N1A -177.7(9) . . . . ?
C4A C5A C6A C1A 0.5(15) . . . . ?
H4A C4A C5A H5A 0(3) . . . . ?
H4A C4A C5A C6A -179.8(19) . . . . ?
H5A C5A C6A N1A 3(2) . . . . ?
H5A C5A C6A C1A -179.0(18) . . . . ?
C6A N1A C7A N2A 170.4(9) . . . . ?
C6A N1A C7A N3A -11.6(16) . . . . ?
C6A C1A C2A H2AB 179.1(17) . . . . ?
C6A C1A C2A C3A -0.8(15) . . . . ?
C7A N1A C6A C1A 168.4(9) . . . . ?
C7A N1A C6A C5A -13.4(17) . . . . ?
C7A N2A C10A C9A 2.1(13) . . . . ?
C7A N2A C10A C12A -175.6(8) . . . . ?
C7A N2A H2AA H2A -29(25) . . . . ?
C7A N3A C8A C9A 0.3(14) . . . . ?
C7A N3A C8A C11A 179.3(8) . . . . ?
C8A N3A C7A N1A -175.6(9) . . . . ?
C8A N3A C7A N2A 2.2(14) . . . . ?
C8A C9A C10A N2A 0.1(14) . . . . ?
C8A C9A C10A C12A 177.7(9) . . . . ?
C9A C8A C11A H11A 101(3) . . . . ?
C9A C8A C11A H11B -20(4) . . . . ?
C9A C8A C11A H11C -140(3) . . . . ?
C9A C10A C12A H12A 155(2) . . . . ?
C9A C10A C12A H12B 33(2) . . . . ?
C9A C10A C12A H12C -85(3) . . . . ?
H9A C9A C10A N2A 179.4(18) . . . . ?
H9A C9A C10A C12A -3(2) . . . . ?
C10A N2A C7A N1A 174.5(8) . . . . ?
C10A N2A C7A N3A -3.4(14) . . . . ?
C10A N2A H2AA H2A 141(23) . . . . ?
C11A C8A C9A H9A 0(2) . . . . ?
C11A C8A C9A C10A 179.6(9) . . . . ?
C13A O2A H2A H2AA -125(22) . . . . ?
C14A O3A H3AA O3AB 65(3) . . . . ?
C14A O3A O3AB H3AA -115(5) . . . . ?
C14A O3A O3AB H3AB -121(6) . . . . ?
C14A O3A H3AB O3AB 61(4) . . . . ?
C14A O3AB H3AB O3A -61(5) . . . . ?
O1B C13B C14B O3B -157.8(10) . . . . ?
O1B C13B C14B C14B 78.0(9) . . . 2_675 ?
O1B C13B C14B H14C -40.7(17) . . . . ?
H1B O1B C13B O2B -7(3) . . . . ?
H1B O1B C13B C14B 173(3) . . . . ?
O2B C13B C14B O3B 21.9(13) . . . . ?
O2B C13B C14B C14B -102.3(9) . . . 2_675 ?
O2B C13B C14B H14C 139.0(15) . . . . ?
H3B O3B C14B C13B -37(3) . . . . ?
H3B O3B C14B C14B 85(3) . . . 2_675 ?
H3B O3B C14B H14C -154(3) . . . . ?
H1BA N1B C6B C1B 12.7(18) . . . . ?
H1BA N1B C6B C5B -164.6(15) . . . . ?
H1BA N1B C7B N2B 2.6(18) . . . . ?
H1BA N1B C7B N3B -175.7(15) . . . . ?
N2B C10B C12B H12D -98(3) . . . . ?
N2B C10B C12B H12E 144(2) . . . . ?
N2B C10B C12B H12F 24(3) . . . . ?
N3B C8B C9B H9B -179.5(18) . . . . ?
N3B C8B C9B C10B -0.7(15) . . . . ?
N3B C8B C11B H11D -48(3) . . . . ?
N3B C8B C11B H11E -174(2) . . . . ?
N3B C8B C11B H11F 69(2) . . . . ?
C1B C2B C3B H3BA 177.4(17) . . . . ?
C1B C2B C3B C4B -0.3(14) . . . . ?
H1BB C1B C2B H2BA 0(3) . . . . ?
H1BB C1B C2B C3B -179.1(17) . . . . ?
H1BB C1B C6B N1B 1(2) . . . . ?
H1BB C1B C6B C5B 178.9(17) . . . . ?
C2B C1B C6B N1B -178.7(8) . . . . ?
C2B C1B C6B C5B -1.3(14) . . . . ?
C2B C3B C4B H4B 179(2) . . . . ?
C2B C3B C4B C5B -0.3(15) . . . . ?
H2BA C2B C3B H3BA -1(3) . . . . ?
H2BA C2B C3B C4B -178.9(18) . . . . ?
C3B C4B C5B H5B -179.0(18) . . . . ?
C3B C4B C5B C6B 0.1(15) . . . . ?
H3BA C3B C4B H4B 2(3) . . . . ?
H3BA C3B C4B C5B -177.9(18) . . . . ?
C4B C5B C6B N1B 177.8(9) . . . . ?
C4B C5B C6B C1B 0.7(15) . . . . ?
H4B C4B C5B H5B 1(3) . . . . ?
H4B C4B C5B C6B -180(2) . . . . ?
H5B C5B C6B N1B -3(2) . . . . ?
H5B C5B C6B C1B 179.8(18) . . . . ?
C6B N1B C7B N2B -175.2(9) . . . . ?
C6B N1B C7B N3B 6.6(16) . . . . ?
C6B C1B C2B H2BA 179.7(17) . . . . ?
C6B C1B C2B C3B 1.1(14) . . . . ?
C7B N1B C6B C1B -169.5(9) . . . . ?
C7B N1B C6B C5B 13.2(16) . . . . ?
C7B N2B C10B C9B -1.0(14) . . . . ?
C7B N2B C10B C12B 177.7(9) . . . . ?
C7B N3B C8B C9B 0.0(14) . . . . ?
C7B N3B C8B C11B -179.3(9) . . . . ?
C8B N3B C7B N1B 178.4(9) . . . . ?
C8B N3B C7B N2B 0.2(15) . . . . ?
C8B C9B C10B N2B 1.2(15) . . . . ?
C8B C9B C10B C12B -177.5(9) . . . . ?
C9B C8B C11B H11D 133(3) . . . . ?
C9B C8B C11B H11E 7(2) . . . . ?
C9B C8B C11B H11F -110(2) . . . . ?
C9B C10B C12B H12D 81(3) . . . . ?
C9B C10B C12B H12E -37(3) . . . . ?
C9B C10B C12B H12F -158(2) . . . . ?
H9B C9B C10B N2B 180.0(18) . . . . ?
H9B C9B C10B C12B 1(2) . . . . ?
C10B N2B C7B N1B -178.0(8) . . . . ?
C10B N2B C7B N3B 0.3(15) . . . . ?
C11B C8B C9B H9B 0(2) . . . . ?
C11B C8B C9B C10B 178.5(9) . . . . ?
H2B N2B C7B N1B 7(4) . . . . ?
H2B N2B C7B N3B -175(4) . . . . ?
H2B N2B C10B C9B 175(4) . . . . ?
H2B N2B C10B C12B -6(4) . . . . ?
H2A O2A C13A O1A 5(3) . . . . ?
H2A O2A C13A C14A -175(2) . . . . ?
H2AA N2A C7A N1A -16(3) . . . . ?
H2AA N2A C7A N3A 166(3) . . . . ?
H2AA N2A C10A C9A -168(3) . . . . ?
H2AA N2A C10A C12A 14(3) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -37.2(4)
2 3.45(11)
3 0.76(4)
4 2.84(9)
5 0.72(3)
6 2.59(9)
7 0.95(4)
8 3.15(10)
9 1.08(4)
10 3.25(11)
11 4.71(15)
12 3.24(11)
13 2.42(8)
14 4.16(13)
15 4.89(16)
