Ultramacrocyclization in water via external templation
Chen, Qiong; Lei, Ye; Wu, Guangcheng; Li, Qing; Pan, Yuanjiang; Li, Hao; Chemical Science 13 (2022) 798–803; doi:10.1039/D1SC06236K

data_1565914
_publ_section_title
;
 Ultramacrocyclization in water via external templation
;
_journal_issue                   3
_journal_name_full               'Chemical Science'
_journal_page_first              798
_journal_page_last               803
_journal_paper_doi               10.1039/D1SC06236K
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         '4(Cl), 2(C54 H52 N6 O7), 12(H2 O)'
_chemical_formula_sum            'C108 H128 Cl4 N12 O26'
_chemical_formula_weight         2152.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-08 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.412(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6939(9)
_cell_length_b                   19.0018(12)
_cell_length_c                   50.945(3)
_cell_measurement_reflns_used    8808
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.75
_cell_measurement_theta_min      3.46
_cell_volume                     13256.0(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1553
_diffrn_reflns_av_unetI/netI     0.1168
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            122205
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        48.177
_diffrn_reflns_theta_max         48.177
_diffrn_reflns_theta_min         2.807
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1701 before and 0.0919 after correction. The Ratio of minimum to maximum transmission is 0.5819. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_description       prism
_exptl_crystal_F_000             4544
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.015
_refine_diff_density_max         1.472
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     1414
_refine_ls_number_reflns         18873
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.2392
_refine_ls_R_factor_gt           0.1224
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+50.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3055
_refine_ls_wR_factor_ref         0.3812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5664
_reflns_number_total             18873
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06236k2.cif
_cod_data_source_block           200330cq_1_3_0m
_cod_depositor_comments
'Adding full bibliography for 1565914--1565917.cif.'
_cod_original_cell_volume        13256.0(15)
_cod_database_code               1565914
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. 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 O(H,H) groups
2. Restrained distances
 C89-C106 = C105-C104 = C36-C35 = C38-C37 = C40-C39 = C103-C102
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O13 \\sim C104 \\sim C105 \\sim O14 \\sim C106 \\sim C89 \\sim O11: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
O7 \\sim C40 \\sim C39 \\sim O6 \\sim C38 \\sim C37 \\sim O5 \\sim C36 \\sim
C35 \\sim O4: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) Cl3(0.5) Cl5(0.5) Cl6(0.5) Cl7(0.5)
5.a Free rotating group:
 O26(H26A,H26B), O15(H15A,H15B), O16(H16A,H16B), O17(H17C,H17D), O18(H18A,
 H18B), O19(H19A,H19B), O20(H20A,H20B), O21(H21A,H21B), O22(H22A,H22B),
 O23(H23A,H23B), O24(H24A,H24B), O25(H25A,H25B)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C17(H17A,H17B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,
 H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
 C40(H40A,H40B), C66(H66A,H66B), C71(H71A,H71B), C87(H87A,H87B), C88(H88A,H88B),
  C89(H89A,H89B), C102(H10A,H10B), C103(H10C,H10D), C104(H10E,H10F), C105(H10G,
 H10H), C106(H10I,H10J)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N6(H6), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C15(H15), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25),
  C27(H27), C30(H30), C31(H31), C42(H42), C43(H43), C45(H45), C46(H46),
 C47(H47), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53), C54(H54),
  N7(H7), N12(H12), C56(H56), C58(H58), C59(H59), C62(H62), C63(H63), C64(H64),
 C65(H65), C68(H68), C69(H69), C72(H72), C73(H73), C75(H75), C76(H76), C78(H78),
  C79(H79), C81(H81), C84(H84), C85(H85), C90(H90), C91(H91), C92(H92),
 C93(H93), C94(H94), C95(H95), C96(H96), C97(H97), C99(H99), C100(H100),
 C107(H107), C108(H108)
;
_shelx_res_checksum              87050
_shelx_hkl_checksum              12868
_shelx_fab_checksum              21958
_olex2_submission_special_instructions 'No special instructions were received'