Regulating supramolecular interactions in dimeric macrocycles.
Fang, Pengwei; Chen, Muqing; Yin, Nan; Zhuang, Guilin; Chen, Tianyun; Zhang, Xinyu; Du, Pingwu; Chemical science 14 (2023) 5425–5430; doi:10.1039/d3sc00035d

data_1568968
_publ_section_title
;
 Regulating supramolecular interactions in dimeric macrocycles.
;
_journal_issue                   20
_journal_name_full               'Chemical science'
_journal_page_first              5425
_journal_page_last               5430
_journal_paper_doi               10.1039/d3sc00035d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C134 H97, 0.5(C60), 2(C6 H5 Cl)'
_chemical_formula_sum            'C176 H107 Cl2'
_chemical_formula_weight         2292.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-20 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.828(2)
_cell_angle_beta                 108.688(2)
_cell_angle_gamma                93.047(2)
_cell_formula_units_Z            2
_cell_length_a                   15.9267(3)
_cell_length_b                   20.9291(4)
_cell_length_c                   22.0491(5)
_cell_measurement_reflns_used    29419
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.1100
_cell_measurement_theta_min      2.8960
_cell_volume                     6948.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            84249
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.639
_diffrn_reflns_theta_min         2.934
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_description       Block
_exptl_crystal_F_000             2394
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.917
_refine_diff_density_min         -1.220
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1910
_refine_ls_number_reflns         25463
_refine_ls_number_restraints     891
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.1178
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1811P)^2^+20.4218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3410
_refine_ls_wR_factor_ref         0.3518
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20451
_reflns_number_total             25463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00035d2.cif
_cod_data_source_block           exp_9539_sq
_cod_depositor_comments
'Adding full bibliography for 1568967--1568969.cif.'
_cod_database_code               1568968
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, {H1FB,H1FC} of C1FA
 At 0.8 times of:
  H1FA of C1FA
 At 1.2 times of:
  H030 of C030, H034 of C034, H02Y of C02Y, H02Z of C02Z, H02N of C02N, H02L
  of C02L, H02W of C02W, H02M of C02M, H02S of C02S, H032 of C032, H02K of C02K,
   H02V of C02V, H03O of C03O, H03H of C03E, {H03D,H03E} of C035, H039 of C039,
  H03F of C03B, H03N of C03N, H03I of C03H, H036 of C036, H03G of C03D, H03K of
  C03K, H047 of C047, H03X of C03X, H04D of C04D, H03R of C03R, H010 of C010,
  H01A of C01A, H01G of C01G, H011 of C011, H012 of C012, H016 of C016, H00Y of
  C00Y, H019 of C019, H01B of C01B, H00Z of C00Z, H01D of C01D, H01S of C01S,
  H01T of C01T, H01K of C01K, H01L of C01L, H01X of C01X, H01M of C01M, H01J of
  C01J, H01P of C01P, H01R of C01R, H01W of C01W, H01Q of C01Q, H01Y of C01Y,
  H026 of C026, H02F of C02F, H02E of C02E, H02G of C02G, H022 of C022, H021 of
  C021, H02A of C02A, H024 of C024, H02B of C02B, H020 of C020, H023 of C023,
  H028 of C028, H02C of C02C, H02I of C02I, H02H of C02H, H02J of C02J, H7AA of
  C7AA, H5AA of C5AA, H0BA of C0BA, H4AA of C4AA, H2BA of C2BA, H3AA of C3AA,
  H9AA of C9AA, H2AA of C2AA, H8AA of C8AA, H8 of C8, H04H of C04H, H04P of
  C04P, H00D of C00D, H00E of C00E, H00J of C00J, H00P of C00P, H00R of C00R,
  H00S of C00S, H00U of C00U, H00I of C00I, H00G of C00G, H00Q of C00Q, H00W of
  C00W
2. Restrained distances
 C0DA-C7EA = C9EA-C0FA = C6FA-C7BA = C5CA-C6CA
 1.4 with sigma of 0.01
 C2CA-C3GA = C7FA-C8FA = C9FA-C6
 1.4 with sigma of 0.01
 C4CA-C1DA = C1DA-C8EA = C3-C4 = C6CA-C5GA
 1.4 with sigma of 0.01
 C1-C2
 1.4 with sigma of 0.01
 C0AA-C3BA \\sim C3BA-C4BA \\sim C4BA-C0AA
 with sigma of 0.02
 C5BA-C6DA \\sim C6DA-C1FA \\sim C1FA-C5BA
 with sigma of 0.02
 C1BA-C0AA \\sim C1BA-C3BA \\sim C1BA-C4BA
 with sigma of 0.02
 C1BA-C5BA \\sim C1BA-C6DA \\sim C1BA-C1FA
 with sigma of 0.02
 C2EA-C3DA \\sim C1EA-C4DA \\sim C3DA-C5DA \\sim C4DA-C2EA \\sim C5DA-C1EA
 with sigma of 0.02
 C2EA-C1EA \\sim C1EA-C3DA \\sim C3DA-C4DA \\sim C4DA-C5DA \\sim C5DA-C2EA
 with sigma of 0.02
 C1EA-C8CA \\sim C2EA-C6EA \\sim C8CA-C3EA \\sim C6EA-C9CA \\sim C3EA-C1EA
\\sim C9CA-C2EA
 with sigma of 0.02
 C1EA-C6EA \\sim C2EA-C3EA \\sim C8CA-C9CA
 with sigma of 0.02
 C0DA-C9EA \\sim C7EA-C0FA \\sim C9EA-C6FA \\sim C0FA-C7BA \\sim C6FA-C0DA
\\sim C7BA-C7EA
 with sigma of 0.02
 C0DA-C0FA \\sim C7EA-C6FA \\sim C9EA-C7BA
 with sigma of 0.02
 C0FA-C9FA \\sim C6-C5FA \\sim C9FA-C6FA \\sim C5FA-C0FA \\sim C6FA-C6
 with sigma of 0.02
 C0FA-C6 \\sim C6-C9FA \\sim C9FA-C5FA \\sim C5FA-C6FA \\sim C6FA-C0FA
 with sigma of 0.02
 C8FA-C8BA \\sim C7FA-C9BA \\sim C8BA-C0CA \\sim C9BA-C8FA \\sim C0CA-C7FA
 with sigma of 0.02
 C8FA-C7FA \\sim C7FA-C8BA \\sim C8BA-C9BA \\sim C9BA-C0CA \\sim C0CA-C8FA
 with sigma of 0.02
 C2CA-C7FA \\sim C3GA-C8FA \\sim C7FA-C9FA \\sim C8FA-C6 \\sim C9FA-C2CA \\sim
C6-C3GA
 with sigma of 0.02
 C2CA-C8FA \\sim C3GA-C9FA \\sim C7FA-C6
 with sigma of 0.02
 C3EA-C5EA \\sim C4EA-C1CA \\sim C5EA-C4CA \\sim C1CA-C6EA \\sim C4CA-C3EA
\\sim C6EA-C4EA
 with sigma of 0.02
 C3EA-C1CA \\sim C4EA-C4CA \\sim C5EA-C6EA
 with sigma of 0.02
 C0GA-C9DA \\sim C0EA-C8DA \\sim C9DA-C7DA \\sim C8DA-C0GA \\sim C7DA-C0EA
 with sigma of 0.02
 C0GA-C0EA \\sim C0EA-C9DA \\sim C9DA-C8DA \\sim C8DA-C7DA \\sim C7DA-C0GA
 with sigma of 0.02
 C5-C0GA \\sim C4-C0EA \\sim C0GA-C2GA \\sim C0EA-C1GA \\sim C2GA-C5 \\sim
C1GA-C4
 with sigma of 0.02
 C5-C0EA \\sim C4-C2GA \\sim C0GA-C1GA
 with sigma of 0.02
 C3CA-C2GA \\sim C1GA-C3GA \\sim C2GA-C2CA \\sim C3GA-C3CA \\sim C2CA-C1GA
 with sigma of 0.02
 C3CA-C1GA \\sim C1GA-C2GA \\sim C2GA-C3GA \\sim C3GA-C2CA \\sim C2CA-C3CA
 with sigma of 0.02
 C4GA-C2FA \\sim C4FA-C3FA \\sim C2FA-C2DA \\sim C3FA-C4GA \\sim C2DA-C4FA
 with sigma of 0.02
 C4GA-C4FA \\sim C4FA-C2FA \\sim C2FA-C3FA \\sim C3FA-C2DA \\sim C2DA-C4GA
 with sigma of 0.02
 C5FA-C7BA \\sim C6FA-C6BA \\sim C7BA-C4GA \\sim C6BA-C2DA \\sim C4GA-C5FA
\\sim C2DA-C6FA
 with sigma of 0.02
 C5FA-C6BA \\sim C6FA-C4GA \\sim C7BA-C2DA
 with sigma of 0.02
 C5GA-C3 \\sim C6CA-C4 \\sim C3-C5 \\sim C4-C5GA \\sim C5-C6CA
 with sigma of 0.02
 C5GA-C6CA \\sim C6CA-C3 \\sim C3-C4 \\sim C4-C5 \\sim C5-C5GA
 with sigma of 0.02
 C2-C5EA \\sim C7CA-C1CA \\sim C5EA-C5CA \\sim C1CA-C2 \\sim C5CA-C7CA
 with sigma of 0.02
 C2-C7CA \\sim C7CA-C5EA \\sim C5EA-C1CA \\sim C1CA-C5CA \\sim C5CA-C2
 with sigma of 0.02
3. Restrained planarity
 C5FA, C9FA, C6, C0FA, C6FA
 with sigma of 0.1
 C8FA, C9FA, C5FA, C2DA, C3FA, C0CA
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C5BA \\sim C4BA \\sim C6DA \\sim C3BA \\sim C1FA \\sim C0AA: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C9FA \\sim C2EA \\sim C8CA \\sim C1EA \\sim C5DA \\sim C6EA \\sim C8EA \\sim
C9CA \\sim C3DA \\sim C4DA \\sim C8DA \\sim C3EA \\sim C4CA \\sim C1DA \\sim
C7DA \\sim C03W \\sim C2FA \\sim C9BA \\sim C9DA \\sim C4EA \\sim C1CA \\sim C3
\\sim C0GA \\sim C03V \\sim C4FA \\sim C3FA \\sim C0CA \\sim C8BA \\sim C0EA
\\sim C5EA \\sim C5CA \\sim C6CA \\sim C4 \\sim C041 \\sim C4GA \\sim C2DA
\\sim C8FA \\sim C7FA \\sim C2GA \\sim C7CA \\sim C2 \\sim C5GA \\sim C5 \\sim
C03M \\sim C6BA \\sim C5FA \\sim C3GA \\sim C1GA \\sim C1 \\sim C14O \\sim C0DA
\\sim C7BA \\sim C6FA \\sim C6 \\sim C2CA \\sim C3CA \\sim C7EA \\sim C140
\\sim C0FA \\sim C9EA: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C8FA) \\sim Ueq, Uanis(C4EA) \\sim Ueq, Uanis(C7CA) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C5BA)=Sof(H5BA)=Sof(H5BB)=Sof(H5BC)=Sof(C6DA)=Sof(H6DA)=Sof(H6DB)=
 Sof(H6DC)=Sof(C1FA)=Sof(H1FA)=Sof(H1FB)=Sof(H1FC)=1-FVAR(1)
 Sof(C3BA)=Sof(H3BA)=Sof(H3BB)=Sof(H3BC)=Sof(C4BA)=Sof(H4BA)=Sof(H4BB)=
 Sof(H4BC)=Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(H0AC)=FVAR(1)
 Fixed Sof: C2EA(0.5) C8CA(0.5) C03M(0.5) C9CA(0.5) C03V(0.5) C03W(0.5)
 C5FA(0.5) C1EA(0.5) C041(0.5) C0CA(0.5) C4DA(0.5) C3FA(0.5) C2DA(0.5)
 C6EA(0.5) C7CA(0.5) C6BA(0.5) C5DA(0.5) C9BA(0.5) C8FA(0.5) C4GA(0.5)
 C3EA(0.5) C2FA(0.5) C4EA(0.5) C3DA(0.5) C6FA(0.5) C7BA(0.5) C5EA(0.5)
 C8DA(0.5) C4FA(0.5) C9FA(0.5) C9EA(0.5) C0FA(0.5) C9DA(0.5) C3CA(0.5)
 C2GA(0.5) C1GA(0.5) C1DA(0.5) C140(0.5) C0EA(0.5) C5CA(0.5) C1(0.5) C6CA(0.5)
 C3(0.5) C6(0.5) C8BA(0.5) C0GA(0.5) C7EA(0.5) C2(0.5) C1CA(0.5) C4(0.5)
 C2CA(0.5) C5GA(0.5) C3GA(0.5) C14O(0.5) C8EA(0.5) C7DA(0.5) C7FA(0.5)
 C0DA(0.5) C5(0.5) C4CA(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C035(H03D,H03E)
6.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00G(H00G), C00I(H00I), C00J(H00J), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00U(H00U), C00W(H00W), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C016(H016), C019(H019),
 C01A(H01A), C01B(H01B), C01D(H01D), C01G(H01G), C01J(H01J), C01K(H01K),
 C01L(H01L), C01M(H01M), C01P(H01P), C01Q(H01Q), C01R(H01R), C01S(H01S),
 C01T(H01T), C01W(H01W), C01X(H01X), C01Y(H01Y), C020(H020), C021(H021),
 C022(H022), C023(H023), C024(H024), C026(H026), C028(H028), C02A(H02A),
 C02B(H02B), C02C(H02C), C02E(H02E), C02F(H02F), C02G(H02G), C02H(H02H),
 C02I(H02I), C02J(H02J), C02K(H02K), C02L(H02L), C02M(H02M), C02N(H02N),
 C02S(H02S), C02V(H02V), C02W(H02W), C02Y(H02Y), C02Z(H02Z), C030(H030),
 C032(H032), C034(H034), C036(H036), C039(H039), C03B(H03F), C03D(H03G),
 C03E(H03H), C03H(H03I), C03K(H03K), C03N(H03N), C03O(H03O), C03R(H03R),
 C03X(H03X), C047(H047), C04D(H04D), C04H(H04H), C04P(H04P), C2BA(H2BA),
 C4AA(H4AA), C2AA(H2AA), C3AA(H3AA), C8(H8), C8AA(H8AA), C7AA(H7AA), C9AA(H9AA),
  C5AA(H5AA), C0BA(H0BA)
6.c Idealised Me refined as rotating group:
 C031(H03A,H03B,H03C), C03T(H03J,H03L,H03M), C03Y(H03P,H03Q,H03S), C3BA(H3BA,
 H3BB,H3BC), C4BA(H4BA,H4BB,H4BC), C5BA(H5BA,H5BB,H5BC), C0AA(H0AA,H0AB,H0AC),
 C6DA(H6DA,H6DB,H6DC), C1FA(H1FA,H1FB,H1FC)
;
_shelx_res_checksum              69506
_shelx_hkl_checksum              56692
_shelx_fab_checksum              10182
_olex2_submission_special_instructions 'No special instructions were received'