Anion-coordination-driven single-double helix switching and chiroptical molecular switch based on oligoureas
Li, Hongfei; Kou, Lei; Liang, Lin; Li, Boyang; Zhao, Wei; Yang, Xiao-Juan; Wu, Biao; Chemical Science  (2022) –; doi:10.1039/D2SC00876A

data_1566771
_publ_section_title
;
 Anion-coordination-driven single-double helix switching and chiroptical
 molecular switch based on oligoureas
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00876A
_journal_year                    2022
_chemical_formula_moiety
'2(C38 H38 N8 O4), 3(C4 H12 N), 3(C3 H6 O), O4 P, C2 H3 N, 0.5(H2 O)'
_chemical_formula_sum            'C99 H134 N20 O15.5 P'
_chemical_formula_weight         1883.26
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-24 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                98.630(3)
_cell_angle_beta                 90.112(3)
_cell_angle_gamma                101.910(3)
_cell_formula_units_Z            2
_cell_length_a                   13.8456(13)
_cell_length_b                   13.8504(12)
_cell_length_c                   26.594(2)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.96
_cell_measurement_theta_min      2.33
_cell_volume                     4930.7(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      149.98
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1269
_diffrn_reflns_av_unetI/netI     0.1295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            127862
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.412
_diffrn_reflns_theta_min         2.123
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5711
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1712 before and 0.1002 after correction.
The Ratio of minimum to maximum transmission is 0.7664.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1985
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 7084 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(7)
_refine_ls_extinction_coef       0.0113(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2472
_refine_ls_number_reflns         35990
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0726
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1083P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.2063
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                21784
_reflns_number_total             35990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00876a2.cif
_cod_data_source_block           complex4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C198 H239 N40 O31 P2'
_cod_original_formula_weight         3737.22
_cod_original_formula_moiety
'4(C38 H38 N8 O4), 5(C4 H12 N), C4 N, 4(C3 H6 O), C3 O, C3 H3 O, 2(O4 P), 2(C2 N), O'
_cod_original_formula_units_Z            1
_cod_original_cell_volume        4930.7(8)
_cod_database_code               1566771
_shelx_shelxl_version_number     2016/6
_exptl_absorpt_special_details   none
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C165-C166 = C165-C167 = C165-C168 = C166-C167 = C166-C168 = C167-C168
 2.5 with sigma of 0.02
 N36-C165 = N36-C166 = N36-C167 = N36-C168
 1.48 with sigma of 0.02
 O29-C190
 1.25 with sigma of 0.02
 C65-C64 = C193-C194 = C192-C193
 1.53 with sigma of 0.02
 C192-C193 = C193-C194
 1.53 with sigma of 0.02
 O30-C193
 1.25 with sigma of 0.02
 H140-C140
 1.53 with sigma of 0.02
 C136-C131 = C193-C194
 1.54 with sigma of 0.02
 C189-C190
 1.388 with sigma of 0.02
 C191-C190
 1.388 with sigma of 0.02
 C185-C184
 1.53 with sigma of 0.02
3. Rigid bond restraints
 N36, C165, C166, C167, C168, C189, C191, C190, O29, C192, C193, C194, O30,
 N39, C196, C195, C185, C184, C183, O27, C197, C198, N40, O31
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N36 \\sim C165 \\sim C166 \\sim C167 \\sim C168 \\sim C189 \\sim C191 \\sim
C190 \\sim O29 \\sim C192 \\sim C193 \\sim C194 \\sim O30 \\sim N39 \\sim C196
\\sim C195 \\sim C185 \\sim C184 \\sim C183 \\sim O27 \\sim C197 \\sim C198
\\sim N40 \\sim O31: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
Uanis(N36) \\sim Ueq, Uanis(C165) \\sim Ueq, Uanis(C166) \\sim Ueq, Uanis(C167)
\\sim Ueq, Uanis(C168) \\sim Ueq, Uanis(C189) \\sim Ueq, Uanis(C191) \\sim Ueq,
Uanis(C190) \\sim Ueq, Uanis(O29) \\sim Ueq, Uanis(C192) \\sim Ueq, Uanis(C193)
\\sim Ueq, Uanis(C194) \\sim Ueq, Uanis(O30) \\sim Ueq, Uanis(N39) \\sim Ueq,
Uanis(C196) \\sim Ueq, Uanis(C195) \\sim Ueq, Uanis(C185) \\sim Ueq,
Uanis(C184) \\sim Ueq, Uanis(C183) \\sim Ueq, Uanis(O27) \\sim Ueq, Uanis(C197)
\\sim Ueq, Uanis(C198) \\sim Ueq, Uanis(N40) \\sim Ueq, Uanis(O31) \\sim Ueq:
with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C166) = Uanis(C168)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C32(H32), C45(H45), C70(H70), C83(H83), C108(H108), C121(H121),
 C146(H146)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26), C27(H27),
  C28(H28), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), N1(H1A), N2(H2A),
 N3(H3A), N4(H4A), N5(H5A), N6(H6), N7(H7A), N8(H8), C39(H39), C40(H40),
 C41(H41), C42(H42), C43(H43), C49(H49), C50(H50), C51(H51), C52(H52), C56(H56),
  C57(H57), C58(H58), C59(H59), C63(H63), C64(H64), C65(H65), C66(H66),
 C72(H72), C73(H73), C74(H74), C75(H75), C76(H76), N9(H9), N10(H10), N11(H11A),
 N12(H12A), N13(H13A), N14(H14A), N15(H15), N16(H16), C77(H77), C78(H78),
 C79(H79), C80(H80), C81(H81), C87(H87), C88(H88), C89(H89), C90(H90), C94(H94),
  C95(H95), C96(H96), C97(H97), C101(H101), C102(H102), C103(H103), C104(H104),
 C110(H110), C111(H111), C112(H112), C113(H113), C114(H114), N17(H17),
 N18(H18A), N19(H19A), N20(H20A), N21(H21A), N22(H22), N23(H23), N24(H24),
 C115(H115), C116(H116), C117(H117), C118(H118), C119(H119), C125(H125),
 C126(H126), C127(H127), C128(H128), C132(H132), C133(H133), C134(H134),
 C135(H135), C139(H139), C140(H140), C141(H141), C142(H142), C148(H148),
 C149(H149), C150(H150), C151(H151), C152(H152), N25(H25A), N26(H26A),
 N27(H27A), N28(H28A), N29(H29), N30(H30), N31(H31), N32(H32A)
5.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C31(H31A,H31B,H31C), C46(H46A,H46B,H46C), C69(H69A,H69B,
 H69C), C84(H84A,H84B,H84C), C107(H10A,H10B,H10C), C122(H12B,H12C,H12D),
 C145(H14B,H14C,H14D), C153(H15A,H15B,H15C), C154(H15D,H15E,H15F), C155(H15G,
 H15H,H15I), C156(H15J,H15K,H15L), C157(H15M,H15N,H15O), C158(H15P,H15Q,H15R),
 C159(H15S,H15T,H15U), C160(H16A,H16B,H16C), C161(H16D,H16E,H16F), C162(H16G,
 H16H,H16I), C163(H16J,H16K,H16L), C164(H16M,H16N,H16O), C169(H16P,H16Q,H16R),
 C170(H17A,H17B,H17C), C171(H17D,H17E,H17F), C172(H17G,H17H,H17I), C173(H17J,
 H17K,H17L), C174(H17M,H17N,H17O), C175(H17P,H17Q,H17R), C176(H17S,H17T,H17U),
 C177(H17V,H17W,H17X), C179(H17Y,H,HA), C180(H18B,H18C,H18D), C182(H18E,H18F,
 H18G), C183(H18H,H18I,H18J), C185(H18K,H18L,H18M), C186(H18N,H18O,H18P),
 C188(H18Q,H18R,H18S), C194(H19B,H19C,H19D)
;
_olex2_submission_special_instructions 'No special instructions were received'