Shape sorting of two distinct amino acid residues at the multiple binding sites of a porous metal-macrocycle framework.
Tashiro, Shohei; Nakata, Kosuke; Hayashi, Ryunosuke; Shionoya, Mitsuhiko; Chemical science 16 (2025) 12303–12308; doi:10.1039/d5sc00795j

data_1574778
_publ_section_title
;
 Shape sorting of two distinct amino acid residues at the multiple binding
 sites of a porous metal-macrocycle framework.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              12303
_journal_page_last               12308
_journal_paper_doi               10.1039/d5sc00795j
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety
'4(C42 H42 Cl6 N6 Pd3), 0.681(C19 H17 N2 O4), 0.597(C9 H6 N), 0.596(C8 H13 N O5), 7.026(C2 H3 N), 3.153(O)'
_chemical_formula_sum            'C205.13 H211.99 Cl24 N33.58 O8.86 Pd12'
_chemical_formula_weight         5417.02
_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
_audit_creation_date             2023-02-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-04-01 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.1680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.3167(3)
_cell_length_b                   52.1830(10)
_cell_length_c                   19.5516(4)
_cell_measurement_reflns_used    79687
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      55.110
_cell_measurement_theta_min      6.020
_cell_volume                     14603.7(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_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    'SHELXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  RAPID
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       67
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            144504
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.011
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2975
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       plate
_exptl_crystal_F_000             5417
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.088
_refine_diff_density_min         -1.914
_refine_diff_density_rms         0.137
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.20(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2712
_refine_ls_number_reflns         66796
_refine_ls_number_restraints     1734
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0791
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1431P)^2^+15.7239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2171
_refine_ls_wR_factor_ref         0.2522
_reflns_Friedel_coverage         0.975
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                42228
_reflns_number_total             66796
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00795j2.cif
_cod_data_source_block           Z-Trp-Boc-Ser@MMF
_cod_depositor_comments
'Adding full bibliography for 1574776--1574779.cif.'
_cod_database_code               1574778
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.665
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.80(5)
 0.20(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C57-N9 = C62-N10 = C56-N9 = C63-N10
 1.5 with sigma of 0.01
 C70-N11 = C77-N12 = C71-N11 = C76-N12
 1.5 with sigma of 0.01
 N11-N12
 2.8 with sigma of 0.02
 N11-Pd6 = N12-Pd6
 2 with sigma of 0.02
 C5C-C6C = C5C-C7C = C5C-C8C
 1.53 with sigma of 0.02
 C6C-C7C = C7C-C8C = C8C-C6C
 2.5 with sigma of 0.02
 O5C-C6C = O5C-C7C = O5C-C8C
 2.43 with sigma of 0.02
 O1C-C1C
 1.45 with sigma of 0.02
 C2C-C1C
 1.45 with sigma of 0.02
 O5C-C5C
 1.45 with sigma of 0.02
 C1C-N1C
 2.5 with sigma of 0.02
 N1C-C4C = C4C-O5C
 1.35 with sigma of 0.02
 C4C-O4C
 1.22 with sigma of 0.02
 C4C-C5C
 2.43 with sigma of 0.02
 N1C-C2C
 1.45 with sigma of 0.02
 C3C-C2C
 1.5 with sigma of 0.02
 C2B-C9B
 1.51 with sigma of 0.02
 O3C-C3C = O2C-C3C
 1.35 with sigma of 0.02
 Cl24-C2C
 3.4 with sigma of 0.02
 N1C-C3C
 2.4 with sigma of 0.02
 O3C-O2C
 2.3 with sigma of 0.02
 N1B-C2B
 2.3 with sigma of 0.02
 O5C-O4C = O4C-N1C
 2.3 with sigma of 0.02
 N9-N10
 2.8 with sigma of 0.01
 N9-Pd5 = N10-Pd5
 2 with sigma of 0.01
 C155-N23 = C160-N24 = C154-N23 = C161-N24
 1.5 with sigma of 0.01
 N23-N24
 2.8 with sigma of 0.01
 N23-Pd12 = N24-Pd12
 2 with sigma of 0.01
 C10A-C11A
 1.53 with sigma of 0.02
 C11A-O1A
 1.22 with sigma of 0.02
 C11A-O2A
 1.35 with sigma of 0.02
 C10A-O1A = C10A-O2A
 2.42 with sigma of 0.02
 C8B-N1B
 1.4 with sigma of 0.02
 N1B-C1B
 1.4 with sigma of 0.02
 C2B-C3B
 1.4 with sigma of 0.02
 C1B-C2B
 1.4 with sigma of 0.02
 C154-C151
 1.5 with sigma of 0.02
 O4C-N1C \\sim O4C-O5C
 with sigma of 0.02
 O3A-N2A \\sim O3A-O4A
 with sigma of 0.02
4. Restrained planarity
 N1C, C4C, O4C, O5C
 with sigma of 0.1
 C6B, C1B, C2B, N1B, C3B, C9B, C8B, C4B, C7B
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
C10S \\sim C9S \\sim N5S: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
C70 \\sim N11 \\sim C71 \\sim C72 \\sim C73 \\sim C74 \\sim C75 \\sim C76 \\sim
N12 \\sim C77: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 1.7A
C18S \\sim C17S \\sim N9S: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 1.7A
C6C \\sim C5C \\sim C8C \\sim C7C: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 1.7A
O5C \\sim C4C \\sim O4C \\sim N1C \\sim C2C \\sim C1C \\sim O1C: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
O3C \\sim C3C \\sim O2C: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
O1A \\sim C11A \\sim O2A: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
C14A \\sim C15A \\sim C16A \\sim C17A \\sim C18A \\sim C19A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C2B \\sim C1B \\sim N1B \\sim C3B \\sim C9B \\sim C8B \\sim C4B \\sim C7B \\sim
C5B \\sim C6B: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 1.7A
N22 \\sim C147 \\sim C148 \\sim C153 \\sim C152 \\sim C151 \\sim C150 \\sim
C149 \\sim C154: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 1.7A
N22 \\sim C146 \\sim C145 \\sim C144 \\sim C143 \\sim C142 \\sim C141 \\sim
N21: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within
1.7A
C151 \\sim C154 \\sim N23: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 1.7A
C14S \\sim C13S \\sim N7S: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 1.7A
C160 \\sim C159 \\sim C158 \\sim C157 \\sim C156 \\sim C155: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C78 \\sim C83 \\sim C82 \\sim C81 \\sim C84 \\sim C80 \\sim C79: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C66 \\sim C65 \\sim C64 \\sim C69 \\sim C68 \\sim C67: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
Uanis(O3W) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C62) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O4W) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N9S) \\sim Ueq, Uanis(C17S) \\sim Ueq, Uanis(C18S) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(N8S) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(O2C) \\sim Ueq, Uanis(C3C) \\sim Ueq, Uanis(O3C) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C11A) \\sim Ueq, Uanis(O1A) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
6. Rigid body (RIGU) restrains
 N5S, C9S, C10S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C62, C57, C58, C59, C60, C61, N10
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N9S, C17S, C18S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N11, C71, C72, C73, C74, C75, C76, N12, C77
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N6S, C11S, C12S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C20S, C19S, N10S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C8C, C6C, C5C, C7C
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C146, C145, C144, C143, C142, C141, N21, N22
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N8S, C15S, C16S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O1C, C1C, C2C, N1C, C4C, O5C, O4C
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O2C, C3C, O3C
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C11A, O2A, O1A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C2A, C1A, N1A, C8A, C3A, C4A, C5A, C6A, C7A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C14A, C15A, C16A, C17A, C19A, C18A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C2B, C1B, N1B, C3B, C9B, C8B, C4B, C7B, C5B, C6B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C63, C64, C65, C66, C67, C68, C69, C70
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C165, C166, C167, C162, C163, C164
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C78, C83, C82, C81, C80, C79
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C161, N24, C160, C159, C158, C157, C156, C155, N23, C154
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C151, C152, C153, C148, C149, C150, C147
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C14S, C13S, N7S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O4A, O3A, C12A, N2A, C10A, C9A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C104, C99, C100, C101, C102, C103
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C6, C1, C2, C3, C4, C5
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C15, C16, C17, C18, C19, C20
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N3S, C5S, C6S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C8S, C7S, N4S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C113, C118, C117, C116, C115, C114
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C31, C30, C29, C34, C33, C32
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C78, C83, C82, C81, C80, C84
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
7. Same fragment restrains
{N2S, C3S, C4S} sigma for 1-2: 0.01, 1-3: 0.01
as in
{N3S, C5S, C6S}
{N2S, C3S, C4S} sigma for 1-2: 0.01, 1-3: 0.01
as in
{N7S, C13S, C14S}
{N2S, C3S, C4S} sigma for 1-2: 0.01, 1-3: 0.01
as in
{N6S, C11S, C12S}
{N2S, C3S, C4S} sigma for 1-2: 0.01, 1-3: 0.01
as in
{N8S, C15S, C16S}
{N2S, C3S, C4S} sigma for 1-2: 0.01, 1-3: 0.01
as in
{N9S, C17S, C18S}
{N2S, C3S, C4S} sigma for 1-2: 0.01, 1-3: 0.01
as in
{N4S, C7S, C8S}
{N2S, C3S, C4S} sigma for 1-2: 0.01, 1-3: 0.01
as in
{N10S, C19S, C20S}
{N2S, C3S, C4S} sigma for 1-2: 0.01, 1-3: 0.01
as in
{N5S, C9S, C10S}
8. Others
 Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(C3A)=Sof(C8A)=Sof(C7A)=Sof(H7AA)=Sof(C6A)=
 Sof(H6A)=Sof(C5A)=Sof(H5AA)=Sof(C4A)=Sof(H4AA)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=
 Sof(C10A)=Sof(H10D)=Sof(C12A)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(C14A)=
 Sof(C15A)=Sof(H15C)=Sof(C16A)=Sof(H16F)=Sof(C17A)=Sof(H17B)=Sof(C18A)=
 Sof(H18B)=Sof(C19A)=Sof(H19B)=Sof(C11A)=Sof(N1A)=Sof(H1AA)=Sof(N2A)=Sof(H2AA)=
 Sof(O3A)=Sof(O4A)=Sof(O1A)=Sof(O2A)=FVAR(1)
 Sof(N9S)=Sof(C17S)=Sof(C18S)=Sof(H18C)=Sof(H18D)=Sof(H18E)=Sof(O4W)=1-FVAR(2)
 Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(C3B)=Sof(C8B)=Sof(C7B)=Sof(H7BA)=Sof(C6B)=
 Sof(H6B)=Sof(C5B)=Sof(H5B)=Sof(C4B)=Sof(H4B)=Sof(C9B)=Sof(N1B)=Sof(H1BA)=
 FVAR(2)
 Sof(N10S)=Sof(C19S)=Sof(C20S)=Sof(H20A)=Sof(H20B)=Sof(H20C)=1-FVAR(3)
 Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(C4C)=Sof(C5C)=Sof(C6C)=Sof(H6CA)=Sof(H6CB)=
 Sof(H6CC)=Sof(C7C)=Sof(H7CA)=Sof(H7CB)=Sof(H7CC)=Sof(C8C)=Sof(H8CA)=Sof(H8CB)=
 Sof(H8CC)=Sof(N1C)=Sof(H1C)=Sof(O1C)=Sof(O4C)=Sof(O5C)=Sof(C2C)=Sof(H2C)=
 Sof(O2C)=Sof(C3C)=Sof(O3C)=0.8*FVAR(4)
 Sof(N4S)=Sof(C7S)=Sof(C8S)=Sof(H8SA)=Sof(H8SB)=Sof(H8SC)=FVAR(4)
 Sof(N5S)=Sof(C9S)=Sof(C10S)=Sof(H10E)=Sof(H10F)=Sof(H10G)=1-FVAR(5)
 Sof(N6S)=Sof(C11S)=Sof(C12S)=Sof(H12D)=Sof(H12E)=Sof(H12F)=FVAR(5)
 Fixed Sof: N8S(0.5) C15S(0.5) C16S(0.5) H16G(0.5) H16H(0.5) H16I(0.5)
 O5W(0.5) O3W(0.5) O2W(0.75)
9.a Ternary CH refined with riding coordinates:
 N2(H2), N1(H1), N6(H6), N5(H5), N4(H4), N3(H3), N7(H7), N8(H8), N9(H9A),
 N10(H10A), N11(H11), N12(H12A), N14(H14), N13(H13A), N18(H18A), N17(H17A),
 N16(H16A), N15(H15), N19(H19A), N20(H20), N21(H21), N22(H22), N23(H23A),
 N24(H24A), C10A(H10D), C2C(H2C)
9.b Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B), C35(H35A,H35B), C28(H28A,H28B), C21(H21A,H21B), C14(H14A,
 H14B), C7(H7A,H7B), C49(H49A,H49B), C56(H56A,H56B), C63(H63A,H63B), C70(H70A,
 H70B), C77(H77A,H77B), C84(H84A,H84B), C126(H12B,H12C), C119(H11A,H11B),
 C112(H11C,H11D), C105(H10B,H10C), C98(H98A,H98B), C91(H91A,H91B), C133(H13B,
 H13C), C140(H14C,H14D), C147(H14E,H14F), C154(H15A,H15B), C161(H16B,H16C),
 C168(H16D,H16E), C9A(H9AA,H9AB), C13A(H13D,H13E), C1C(H1CA,H1CB)
9.c Aromatic/amide H refined with riding coordinates:
 C5(H5A), C4(H4A), C3(H3A), C2(H2A), C38(H38), C40(H40), C41(H41), C37(H37),
 C33(H33), C32(H32), C31(H31), C30(H30), C23(H23), C24(H24), C26(H26), C27(H27),
  C19(H19), C18(H18), C17(H17), C16(H16), C10(H10), C12(H12), C13(H13), C9(H9),
 C44(H44), C45(H45), C46(H46), C47(H47), C51(H51), C55(H55), C54(H54), C52(H52),
  C58(H58), C59(H59), C60(H60), C61(H61), C65(H65), C69(H69), C68(H68),
 C66(H66), C72(H72), C73(H73), C74(H74), C75(H75), C83(H83), C79(H79), C80(H80),
  C82(H82), C89(H89), C88(H88), C87(H87), C86(H86), C124(H124), C122(H122),
 C121(H121), C125(H125), C117(H117), C116(H116), C115(H115), C114(H114),
 C110(H110), C108(H108), C107(H107), C111(H111), C103(H103), C102(H102),
 C101(H101), C100(H100), C96(H96), C94(H94), C93(H93), C97(H97), C128(H128),
 C129(H129), C130(H130), C131(H131), C139(H139), C135(H135), C136(H136),
 C138(H138), C142(H142), C143(H143), C144(H144), C145(H145), C152(H152),
 C150(H150), C149(H149), C153(H153), C156(H156), C157(H157), C158(H158),
 C159(H159), C167(H167), C163(H163), C164(H164), C166(H166), C1A(H1A),
 C7A(H7AA), C6A(H6A), C5A(H5AA), C4A(H4AA), C15A(H15C), C16A(H16F), C17A(H17B),
 C18A(H18B), C19A(H19B), N1A(H1AA), N2A(H2AA), C1B(H1B), C7B(H7BA), C6B(H6B),
 C5B(H5B), C4B(H4B), N1B(H1BA), N1C(H1C)
9.d Fitted hexagon refined as free rotating group:
 C20(C19,C18,C17,C16,C15), C57(C58,C59,C60,C61,C62), C71(C72,C73,C74,C75,C76),
 C152(C151,C150,C149,C148,C153), C155(C156,C157,C158,C159,C160), C167(C162,C163,
 C164,C165,C166), C3A(C8A,C7A,C6A,C5A,C4A), C14A(C15A,C16A,C17A,C18A,C19A),
 C3B(C8B,C7B,C6B,C5B,C4B)
9.e Idealised Me refined with riding coordinates:
 C6C(H6CA,H6CB,H6CC), C7C(H7CA,H7CB,H7CC), C8C(H8CA,H8CB,H8CC), C2S(H2SA,H2SB,
 H2SC), C12S(H12D,H12E,H12F), C18S(H18C,H18D,H18E), C20S(H20A,H20B,H20C),
 C10S(H10E,H10F,H10G)
9.f Idealised Me refined as rotating group:
 C4S(H4SA,H4SB,H4SC), C6S(H6SA,H6SB,H6SC), C14S(H14G,H14H,H14I), C16S(H16G,
 H16H,H16I), C8S(H8SA,H8SB,H8SC)
;
_shelx_res_checksum              84587
_olex2_submission_special_instructions 'No special instructions were received'