Interrogating the potential of helical aromatic foldamers for protein recognition
Kwon, Sunbum; Morozov, Vasily; Wang, Lingfei; Mandal, Pradeep Kumar; Chaignepain, Stéphane; Douat, Céline; Huc, Ivan; Organic & Biomolecular Chemistry  (2024) –; doi:10.1039/D4OB01436G

data_7160193
_publ_section_title
;
 Interrogating the potential of helical aromatic foldamers for protein
 recognition
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D4OB01436G
_journal_year                    2024
_chemical_formula_moiety
'0.25(C147 H109 N27 O33 S3), 0.25(C150 H116.5 N26.5 O33 S3), 0.25(C150 H102 N26 O34 S3), 0.25(C149 H105 N26 O33 S3), 0.25(C6 H12 O2)'
_chemical_formula_sum            'C150.5 H111.12 N26.38 O33.75 S3'
_chemical_formula_weight         2925.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2023-07-07 deposited with the CCDC.	2024-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.93(3)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   35.903(7)
_cell_length_b                   65.428(13)
_cell_length_c                   36.158(7)
_cell_measurement_reflns_used    486593
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.73
_cell_measurement_theta_min      0.56
_cell_volume                     84738(3)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       MXCUBE
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'MD2 with mini-kappa goniostat'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.800
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       66
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            311527
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        24.624
_diffrn_reflns_theta_max         24.624
_diffrn_reflns_theta_min         0.701
_diffrn_source                   'ID30b, ESRF, Grenoble'
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    0.917
_exptl_crystal_description       block
_exptl_crystal_F_000             24268
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.005
_refine_diff_density_max         1.635
_refine_diff_density_min         -1.330
_refine_diff_density_rms         0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.426
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     5266
_refine_ls_number_reflns         97123
_refine_ls_number_restraints     621
_refine_ls_restrained_S_all      2.448
_refine_ls_R_factor_all          0.2462
_refine_ls_R_factor_gt           0.2180
_refine_ls_shift/su_max          5.093
_refine_ls_shift/su_mean         0.138
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5360
_refine_ls_wR_factor_ref         0.5628
_reflns_Friedel_coverage         0.000
_reflns_number_gt                64735
_reflns_number_total             97123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01436g3.cif
_cod_data_source_block           sk102_sq
_cod_original_cell_volume        84738(30)
_cod_original_formula_sum        'C150.50 H111.12 N26.38 O33.75 S3'
_cod_database_code               7160193
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9AA-C323
 1.54 with sigma of 0.02
 C389-C59A
 1.54 with sigma of 0.02
 C699-C666
 1.54 with sigma of 0.02
 C666-C639
 1.54 with sigma of 0.02
 C550-C538
 1.54 with sigma of 0.02
 C580-C538
 1.54 with sigma of 0.02
 C560-C538
 1.54 with sigma of 0.02
 C5EA-C9AA
 1.54 with sigma of 0.02
 C8BA-C336
 1.54 with sigma of 0.02
 C654-C336
 1.54 with sigma of 0.02
 C344-C336
 1.54 with sigma of 0.02
 C413-C22
 1.54 with sigma of 0.02
 O6FA-C4GA = O7-C5EA
 1.43 with sigma of 0.02
 C5EA-C4GA
 2.5 with sigma of 0.02
 C757-C4EA = C658-C4EA
 1.54 with sigma of 0.02
 C633-C536
 2.5 with sigma of 0.02
 C629-C679
 2.5 with sigma of 0.02
 C550-C560
 2.5 with sigma of 0.02
 C550-C580
 2.5 with sigma of 0.02
 C560-C580
 2.5 with sigma of 0.02
 O667-C306
 1.26 with sigma of 0.02
 O78-C306
 1.35 with sigma of 0.02
 C455-C317 = C582-C455
 1.54 with sigma of 0.02
 C3BA-C279 = C3BA-C378 = C485-C3BA
 1.54 with sigma of 0.02
 O605-C582
 1.43 with sigma of 0.02
 C582-C455
 1.54 with sigma of 0.02
 C418-C165
 1.54 with sigma of 0.02
 C42-C16
 1.51 with sigma of 0.02
 C306-C195
 1.54 with sigma of 0.02
 C195-O667
 2.38 with sigma of 0.02
 C195-O78
 2.42 with sigma of 0.02
 O5HA-C194
 1.43 with sigma of 0.02
 C455-C194
 1.54 with sigma of 0.02
 C582-C194
 2.5 with sigma of 0.02
 C317-C582
 2.5 with sigma of 0.02
 C317-C194
 2.5 with sigma of 0.02
 C501-C0DA
 1.54 with sigma of 0.02
 O662-C639 = O651-C699
 1.43 with sigma of 0.02
 C658-C4EA = C757-C4EA
 1.54 with sigma of 0.02
 C560-C538 = C580-C538 = C550-C538
 1.54 with sigma of 0.02
 O25-C553
 1.43 with sigma of 0.02
 O150-C5GA
 1.43 with sigma of 0.02
 C759-C5GA
 1.54 with sigma of 0.02
 O8KA-C413
 1.23 with sigma of 0.02
 O426-C413
 1.34 with sigma of 0.02
 C553-C531
 1.54 with sigma of 0.02
 C455-C317 = C455-C194 = C582-C455
 1.54 with sigma of 0.02
 C4MA-C1BA = C4IA-C1BA
 1.54 with sigma of 0.02
 C395-C360 = C360-C106 = C772-C360
 1.54 with sigma of 0.02
 O628-C0A
 1.23 with sigma of 0.02
 C388-C0A
 1.54 with sigma of 0.02
 C505-C494
 1.54 with sigma of 0.02
 C505-C398
 1.54 with sigma of 0.02
 C505-C398 = C505-C3HA
 1.54 with sigma of 0.02
 C505-C494 = C505-C3HA = C505-C398
 1.54 with sigma of 0.02
 O717-C3HA = O620-C398
 1.43 with sigma of 0.02
 C398-C3HA
 2.5 with sigma of 0.02
 C398-C494
 2.5 with sigma of 0.02
 C494-C3HA
 2.5 with sigma of 0.02
 C441-C379 = C441-C0EA
 1.54 with sigma of 0.02
 C348-C210
 1.54 with sigma of 0.02
 O459-C679 = O612-C629
 1.43 with sigma of 0.02
 C428-C1O
 1.54 with sigma of 0.02
 S8-O88 \\sim S8-O157 \\sim S8-O3GA \\sim S1-O3AA \\sim S1-O7CA \\sim S1-O7BA
\\sim S4-O1FA \\sim S4-O42 ~
 S4-O10 \\sim S10-O84 \\sim S10-O33 \\sim S10-O5BA \\sim S9_$1-O164_$1 \\sim
S9_$1-O1_$1 \\sim S9_$1-
 O1BA_$1 \\sim S5_$1-O328_$1 \\sim S5_$1-O1KA_$1 \\sim S5_$1-O4BA_$1 \\sim
S7_$1-O161_$1 ~
 S7_$1-O45_$1 \\sim S7_$1-O9AA_$1 \\sim S2_$1-O3BA_$1 \\sim S2_$1-O6AA_$1 \\sim
S2_$1-O3DA_$1
 with sigma of 0.01
 S1-C150 \\sim S8-C142 \\sim S4-C11 \\sim S10-C8EA \\sim S5_$1-C9A_$1 \\sim
S9_$1-C19A_$1 \\sim S2_$1-
 C1IA_$1 \\sim S7_$1-C253_$1
 with sigma of 0.005
 C679-C525 \\sim C679-C633 \\sim C633-C629 \\sim C629-C536 \\sim C629-C592
 with sigma of 0.005
 O459-C679 \\sim O612-C629
 with sigma of 0.005
 O2DA-C0MA \\sim O5DA-C51 \\sim O101-C0IA \\sim O96-C504 \\sim O70-C400 \\sim
O171-C355
 with sigma of 0.01
 O31-C1F \\sim O102-C1M \\sim O145-C89A \\sim O2GA-C49A \\sim O117-C29A \\sim
O150-C79A
 with sigma of 0.01
 O128-C131 \\sim O24-C92 \\sim O25-C250 \\sim O165-C3KA \\sim O100-C236 \\sim
O68-C318
 with sigma of 0.01
 C8BA-C336 \\sim C654-C336 \\sim C344-C336 \\sim C550-C538 \\sim C560-C538
\\sim C580-C538 \\sim C666-
 C384 \\sim C699-C666 \\sim C666-C639 \\sim C9AA-C323 \\sim C9AA-C4GA \\sim
C9AA-C5EA
 with sigma of 0.01
 C8BA-C336 \\sim C344-C336 \\sim C654-C336 \\sim C550-C538 \\sim C580-C538
\\sim C560-C538 \\sim C666-
 C384 \\sim C699-C666 \\sim C666-C639 \\sim C9AA-C323 \\sim C9AA-C5EA \\sim
C9AA-C4GA
 with sigma of 0.01
 O14-O4EA \\sim O200-O17 \\sim O118-O634 \\sim O15-O0IA \\sim O426-O8KA \\sim
O83-O4DA
 with sigma of 0.01
 O8BA-O16 \\sim O563-O77 \\sim O75-O2BA \\sim O423-O40
 with sigma of 0.01
 C286-C110 \\sim C290-C101 \\sim C69A-C362 \\sim C59A-C389 \\sim
C6DA_$2-C146_$2 \\sim C2MA_$2-
 C223_$2 \\sim C466_$2-C329_$2 \\sim C348_$2-C210_$2
 with sigma of 0.01
 O5AA-C520 \\sim O91-C99A \\sim O158_$2-C278_$2 \\sim O104_$2-C221_$2
 with sigma of 0.01
 O4-C5IA \\sim O74-C207 \\sim O172-C197 \\sim O22-C245 \\sim O98-C82 \\sim
O174-C396
 with sigma of 0.01
 N704-C290 \\sim N21-C362 \\sim N771-C389 \\sim N153_$2-C146_$2 \\sim
N208_$2-C223_$2 ~
 N570_$2-C466_$2 \\sim N18_$2-C348_$2
 with sigma of 0.01
3. Restrained planarity
 C165, C418, O634, O118
 with sigma of 0.1
 O17, C4DA, O200, C373
 with sigma of 0.1
 C22, C413, O426, O8KA
 with sigma of 0.1
 O83, O4DA, C531, C553
 with sigma of 0.1
 O77, C0DA, C501, O563
 with sigma of 0.1
 O40, O423, C435, C656
 with sigma of 0.1
 C455, C582, O605, C194_$3
 with sigma of 0.05
 C195, O667, O78, C306
 with sigma of 0.1
 C385, C138, N109, C86, C23, C329, C466
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C6BA) = Uanis(C32) = Uanis(C424) = Uanis(C436)
Uanis(C7AA) = Uanis(C511) = Uanis(C3NA) = Uanis(C449) = Uanis(C353) = Uanis(C94)
Uanis(C222) = Uanis(C468) = Uanis(C483) = Uanis(C189) = Uanis(C554) =
Uanis(C397) = Uanis(C355) = Uanis(C224) = Uanis(C0KA)
Uanis(C71A) = Uanis(C76A) = Uanis(C75A) = Uanis(C74A) = Uanis(C73A) =
Uanis(C72A) = Uanis(C79A) = Uanis(C78A) = Uanis(C77A)
Uanis(C209) = Uanis(C349) = Uanis(C311) = Uanis(C594) = Uanis(C342) =
Uanis(C438) = Uanis(C519)
Uanis(O31) = Uanis(O77) = Uanis(O563)
Uanis(N12A) = Uanis(N771)
Uanis(C0A) = Uanis(O628)
Uanis(C250) = Uanis(C553) = Uanis(C531)
Uanis(C3KA) = Uanis(C4MA) = Uanis(C1BA) = Uanis(C4IA)
Uanis(C1D) = Uanis(C6) = Uanis(C115) = Uanis(C114) = Uanis(C113) = Uanis(C112)
= Uanis(C117) = Uanis(C118) = Uanis(C1F) = Uanis(C0DA) = Uanis(C501)
Uanis(C391) = Uanis(C407) = Uanis(C400) = Uanis(C2HA) = Uanis(C134) =
Uanis(C406) = Uanis(C403) = Uanis(C6HA) = Uanis(C454) = Uanis(C411)
Uanis(C187) = Uanis(C4AA) = Uanis(C4BA) = Uanis(C225) = Uanis(C254) =
Uanis(C84) = Uanis(C210) = Uanis(C9FA) = Uanis(C158)
Uanis(C214) = Uanis(C322) = Uanis(C53) = Uanis(C314) = Uanis(C230) =
Uanis(C201) = Uanis(C197) = Uanis(C263) = Uanis(C5JA)
Uanis(C1NA) = Uanis(C163) = Uanis(C302) = Uanis(C122) = Uanis(C65) = Uanis(C45)
= Uanis(C8) = Uanis(C245)
Uanis(C316) = Uanis(C140) = Uanis(C3EA) = Uanis(C107) = Uanis(C89) =
Uanis(C116) = Uanis(C110) = Uanis(C68) = Uanis(C43)
Uanis(C247) = Uanis(C539) = Uanis(C558) = Uanis(C544) = Uanis(C562) =
Uanis(C610) = Uanis(C611) = Uanis(C650)
Uanis(C47) = Uanis(C14) = Uanis(C312) = Uanis(C401) = Uanis(C8GA) = Uanis(C211)
= Uanis(C0AA) = Uanis(C71) = Uanis(C247)
Uanis(C31) = Uanis(C99) = Uanis(C63) = Uanis(C166) = Uanis(C217) = Uanis(C171)
= Uanis(C1IA) = Uanis(C176) = Uanis(C9BA)
5. Rigid body (RIGU) restrains
 C129, C325, C7GA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: N2AA(0.5) H2AA(0.5) H2AB(0.5) H2AC(0.5)
 Fixed Uiso: O70(0.12) O117(0.12) O150(0.12) O171(0.12) O7(0.12) C22(0.12)
 O40(0.12) C8BA(0.12) O96(0.12) C165(0.12) N21(0.12) O97(0.12) C195(0.18)
 C323(0.12) C336(0.12) C344(0.12) C360(0.12) C379(0.12) C384(0.12) C398(0.12)
 C413(0.12) O423(0.12) O426(0.12) C428(0.12) C435(0.12) C441(0.12) C455(0.16)
 O459(0.12) C466(0.12) C505(0.12) N521(0.12) C525(0.12) H52H(0.12) H52I(0.12)
 H52J(0.12) N527(0.12) C536(0.12) H53D(0.12) H53E(0.12) H53F(0.12) C538(0.12)
 O548(0.12) C550(0.12) C560(0.12) N570(0.12) C580(0.12) C582(0.16) O590(0.12)
 C592(0.12) H59A(0.12) H59B(0.12) H59C(0.12) O605(0.16) O612(0.12) O620(0.12)
 C629(0.12) C633(0.12) O634(0.12) C639(0.12) O651(0.12) C654(0.12) C656(0.12)
 C658(0.12) O662(0.12) C666(0.12) O667(0.18) C679(0.12) H679(0.12) C699(0.12)
 O717(0.12) C757(0.12) C759(0.12) C772(0.12) C9AA(0.12) C0EA(0.12) C5EA(0.12)
 O8KA(0.12) N18(0.12) C1O(0.12) O118(0.12) C4EA(0.12) C194(0.16) C106(0.12)
 O6FA(0.12) C4GA(0.12) C5GA(0.12) O78(0.18) C306(0.18) O5HA(0.16) C3HA(0.12)
7.a Ternary CH refined with riding coordinates:
 C32(H32), C48(H48), C3BA(H3BA), C5MA(H5MA), C336(H336), C455(H455),
 C505(H505), C538(H538), C666(H666), C679(H679), C9AA(H9AA)
7.b Secondary CH2 refined with riding coordinates:
 C22(H22D,H22E), C49(H49A,H49B), C8BA(H8BA,H8BB), C6BA(H6BA,H6BB), C146(H14B,
 H14C), C161(H16A,H16B), C4DA(H4DA,H4DB), C8AA(H8AA,H8AB), C0DA(H0DA,H0DB),
 C195(H19A,H19B), C209(H20A,H20B), C223(H22A,H22B), C279(H27D,H27E), C286(H28A,
 H28B), C290(H29A,H29B), C317(H31A,H31B), C323(H32A,H32B), C344(H34A,H34B),
 C348(H34D,H34E), C350(H35A,H35B), C362(H36D,H36E), C379(H37A,H37B), C384(H38B,
 H38C), C389(H38G,H38H), C395(H39A,H39B), C398(H39C,H39D), C418(H41A,H41B),
 C435(H43A,H43B), C441(H44A,H44B), C466(H46A,H46B), C494(H49C,H49D), C539(H53A,
 H53B), C550(H55A,H55B), C553(H55C,H55D), C582(H58D,H58E), C633(H63D,H63E),
 C639(H63B,H63C), C654(H65A,H65B), C658(H65C,H65D), C699(H69A,H69B), C757(H75A,
 H75B), C0EA(H0EA,H0EB), C5EA(H5EA,H5EB), C4EA(H4EA,H4EB), C194(H19C,H19D),
 C4GA(H4GA,H4GB), C3HA(H3HA,H3HB)
7.c Aromatic/amide H refined with riding coordinates:
 N27(H27), N39(H39), N43(H43), N1CA(H1CA), N51(H51), N52(H52), N55(H55),
 N56(H56), N58(H58), N60(H60), N62(H62), N82(H82), N83(H83), N3AA(H3AA),
 N11A(H11A), N92(H92), N95(H95), N21A(H21A), N105(H105), N108(H108), N110(H110),
  N111(H111), N1AA(H1AB), N118(H118), N121(H121), N127(H127), N129(H129),
 N131(H131), N15A(H15D), N13A(H13A), N143(H143), N148(H148), N149(H149),
 N159(H159), N163(H16C), N19A(H19E), N1A(H1A), C130(H130), C29(H29), C74(H74),
 C119(H119), N9A(H9A), C18(H18), C105(H10A), C169(H169), C0GA(H0GA), N7A(H7A),
 N5BA(H5BA), C52A(H52G), C53A(H53C), C54A(H54A), C58A(H58F), N3CA(H3CA),
 C1NA(H1NA), C163(H163), C302(H302), C8(H8), C9HA(H9HA), C1EA(H1EA), C79(H79),
 C9IA(H9IA), N5A(H5A), N57(H57), N0AA(H0AA), C141(H141), C234(H234), C170(H170),
  C2NA(H2NA), C58(H58G), C7IA(H7IA), C139(H139), C1JA(H1JA), N17A(H17A),
 C88(H88), C310(H310), C3DA(H3DA), C98(H98), C89(H89), C116(H116), C316(H316),
 C68(H68), C5AA(H5AA), C268(H268), C3MA(H3MA), C2KA(H2KA), N23A(H23A),
 C1MA(H1MA), C2IA(H2IA), C7NA(H7NA), C10(H10), N3A(H3A), C156(H156), C6JA(H6JA),
  C108(H10B), C4FA(H4FA), N9BA(H9BA), C217(H217), C166(H166), C63(H63),
 C176(H176), C9(H9), C24(H24), C6AA(H6AA), C180(H180), C36(H36), C126(H126),
 C1DA(H1DA), C2LA(H2LA), C1HA(H1HA), C356(H356), C185(H185), C93(H93),
 C239(H239), C335(H335), C381(H381), C205(H205), C4BA(H4BA), C225(H225),
 C254(H254), C9FA(H9FA), C1LA(H1LA), C8CA(H8CA), C174(H174), C1FA(H1FA),
 C123(H123), C129(H12B), C325(H325), C196(H196), C103(H103), C124(H124),
 C220(H220), C1AA(H1AA), C5DA(H5DA), C260(H260), C7CA(H7CA), C148(H14A),
 C62A(H62A), C63A(H63A), C64A(H64A), C68A(H68A), C94(H94), C353(H353),
 C449(H449), C3NA(H3NA), C511(H511), C5CA(H5CA), C282(H282), C6CA(H6CA),
 C269(H269), C9KA(H9KA), C313(H313), C6LA(H6LA), C1CA(H1CB), C6IA(H6IA),
 C458(H458), C242(H242), C248(H248), C326(H326), C446(H446), C345(H345),
 C351(H351), C17(H17), C1KA(H1KA), C7EA(H7EA), C26(H26), C112(H112), C113(H113),
  C114(H114), C118(H11B), C22A(H22C), C23A(H23B), C24A(H24D), C28A(H28C),
 C291(H291), C266(H266), C175(H175), C9GA(H9GA), C42A(H42D), C43A(H43F),
 C44A(H44C), C48A(H48A), C230(H230), C314(H314), C53(H53), C263(H263),
 C8GA(H8GA), C401(H401), C312(H312), C71(H71), C228(H228), C408(H408),
 C475(H475), C376(H376), C102(H102), C1N(H1N), C104(H104), C1L(H1L), C252(H252),
  C372(H372), C257(H257), C35(H35), C294(H294), C265(H265), C467(H467),
 C8JA(H8JA), C82A(H82A), C83A(H83A), C84A(H84A), C88A(H88A), C72A(H72A),
 C73A(H73A), C74A(H74A), C78A(H78A), C2A(H2A), C3A(H3AB), C4A(H4A), C8A(H8A),
 C307(H307), C204(H204), C488(H488), C23(H23), C9LA(H9LA), C8FA(H8FA),
 C451(H451), C530(H530), C299(H299), C519(H519), C438(H438), C342(H342),
 C594(H594), C311(H311), C92A(H92A), C93A(H93A), C94A(H94A), C98A(H98A),
 C32A(H32C), C33A(H33A), C34A(H34C), C38A(H38A), C411(H411), C6HA(H6HA),
 C454(H454), C407(H407), C414(H414), C409(H409), C492(H492), C394(H394),
 C483(H483), C189(H189), C554(H554), C224(H224), C12A(H12A), C13A(H13B),
 C14A(H14D), C18A(H18A), C650(H650), C611(H611), C610(H610), C562(H562),
 C544(H544)
7.d Fitted hexagon refined as free rotating group:
 C7AA(C94,C353,C449,C3NA,C511), C327(C9LA,C8FA,C451,C530,C299), C349(C519,C438,
 C342,C594,C311), C558(C650,C611,C610,C562,C544)
7.e Naphthalene refined as free rotating group:
 C5(C130,C29,C74,C7BA,C46,N73,C34,C119,C2MA), C15(C18,C105,C169,C38,C61,N37,
 C135,C0GA,C51), C51A(C52A,C53A,C54A,C55A,C56A,N12A,C57A,C58A,C59A), C44(C1NA,
 C163,C302,C122,C65,N38,C45,C8,C245), C4CA(C9HA,C1EA,C79,C90,C153,N85,C167,C9IA,
 C82), C62(C141,C234,C170,C91,C173,N125,C288,C2NA,C207), C64(C58,C7IA,C139,C4,
 C160,N54,C120,C1JA,C92), C2CA(C88,C310,C3DA,C0BA,C0CA,N107,C133,C98,C142),
 C107(C89,C116,C316,C140,C3EA,N123,C43,C68,C110), C109(C5AA,C268,C3MA,C3GA,C95,
 N78,C149,C2KA,C131), C144(C1MA,C2IA,C7NA,C3,C127,N46,C2AA,C10,C150), C159(C156,
 C6JA,C108,C7DA,C1,N66,C2,C4FA,C147), C171(C217,C166,C63,C99,C31,N48,C9BA,C176,
 C1IA), C177(C9,C24,C6AA,C2EA,C76,N76,C78,C180,C0MA), C20(C36,C126,C1DA,C6NA,
 C5KA,N81,C42,C2LA,C5IA), C1GA(C1HA,C356,C185,C81,C164,N41,C9EA,C93,C8EA),
 C28(C239,C335,C381,C238,C3LA,N137,C2JA,C205,C3KA), C4AA(C4BA,C225,C254,C84,
 C187,N124,C158,C9FA,C210), C7LA(C1LA,C8CA,C174,C136,C39,N53,C30,C1FA,C11),
 C3IA(C123,C129,C325,C7GA,C111,N106,C7HA,C196,C221), C66(C103,C124,C220,C73,C57,
 N114,C69,C1AA,C100), C77(C5DA,C260,C7CA,C155,C59,N71,C56,C148,C101), C61A(C62A,
 C63A,C64A,C65A,C66A,N14A,C67A,C68A,C69A), C8DA(C5CA,C282,C6CA,C246,C132,N136,
 C0NA,C269,C236), C0FA(C9KA,C313,C6LA,C190,C145,N50,C178,C1CA,C278), C125(C6IA,
 C458,C242,C259,C232,N170,C6EA,C248,C250), C7KA(C326,C446,C345,C365,C6MA,N67,
 C4KA,C351,C0IA), C8HA(C17,C1KA,C7EA,C72,C128,N69,C5BA,C26,C6DA), C1D(C112,C113,
 C114,C115,C6,N24A,C117,C118,C1F), C21A(C22A,C23A,C24A,C25A,C26A,N6A,C27A,C28A,
 C29A), C191(C291,C266,C175,C186,C2DA,N132,C235,C9GA,C253), C41A(C42A,C43A,C44A,
 C45A,C46A,N10A,C47A,C48A,C49A), C201(C230,C314,C53,C322,C214,N97,C5JA,C263,
 C197), C211(C8GA,C401,C312,C14,C47,N1,C0AA,C71,C247), C212(C228,C408,C475,C432,
 C206,N176,C227,C376,C520), C1E(C102,C1N,C104,C1B,C1I,N22A,C1J,C1L,C1M),
 C218(C252,C372,C257,C70,C7,N32,C5FA,C35,C396), C219(C294,C265,C467,C330,C4JA,
 N151,C152,C8JA,C318), C81A(C82A,C83A,C84A,C85A,C86A,N18A,C87A,C88A,C89A),
 C71A(C72A,C73A,C74A,C75A,C76A,N16A,C77A,C78A,C79A), C1A(C2A,C3A,C4A,C5A,C6A,
 N2A,C7A,C8A,C9A), C321(C307,C204,C488,C385,C138,N109,C86,C23,C329), C91A(C92A,
 C93A,C94A,C95A,C96A,N20A,C97A,C98A,C99A), C31A(C32A,C33A,C34A,C35A,C36A,N8A,
 C37A,C38A,C39A), C403(C411,C6HA,C454,C2HA,C134,N175,C391,C407,C400), C445(C414,
 C409,C492,C462,C477,N154,C364,C394,C504), C468(C483,C189,C554,C397,C222,N168,
 C0KA,C224,C355), C11A(C12A,C13A,C14A,C15A,C16A,N4A,C17A,C18A,C19A)
7.f Idealised Me refined as rotating group:
 N153(H15A,H15B,H15C), N21(H21B,H21C,H21D), C67(H67A,H67B,H67C), N208(H20C,
 H20D,H20E), C243(H24A,H24B,H24C), C258(H25A,H25B,H25C), C275(H27A,H27B,H27C),
 C368(H36A,H36B,H36C), C378(H37C,H37D,H37E), C388(H38D,H38E,H38F), C402(H40A,
 H40B,H40C), C424(H42A,H42B,H42C), C436(H43C,H43D,H43E), C479(H47A,H47B,H47C),
 C485(H48B,H48C,H48D), N521(H52D,H52E,H52F), C525(H52H,H52I,H52J), N527(H52A,
 H52B,H52C), C536(H53D,H53E,H53F), C560(H56A,H56B,H56C), N570(H57A,H57B,H57C),
 C580(H58A,H58B,H58C), C592(H59A,H59B,H59C), N704(H70A,H70B,H70C), N771(H77A,
 H77B,H77C), N18(H18B,H18C,H18D), N2AA(H2AA,H2AB,H2AC)
;
_olex2_submission_special_instructions 'No special instructions were received'