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_1565917
_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
'2(Cl), C48 H46 N32 O16, C54 H52 N6 O7, 2(H2 O)'
_chemical_formula_sum            'C102 H102 Cl2 N38 O25'
_chemical_formula_weight         2331.11
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc28bvq6
_audit_creation_date             2021-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-12 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                107.441(3)
_cell_angle_beta                 93.266(3)
_cell_angle_gamma                104.627(3)
_cell_formula_units_Z            2
_cell_length_a                   14.5032(6)
_cell_length_b                   23.2785(10)
_cell_length_c                   23.8851(11)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.79
_cell_measurement_theta_min      2.85
_cell_volume                     7366.6(6)
_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      173.02
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0833
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            93616
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.148
_diffrn_reflns_theta_min         2.845
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1332 before and 0.0887 after correction. The Ratio of minimum to maximum transmission is 0.7323. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.051
_exptl_crystal_description       block
_exptl_crystal_F_000             2428
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.864
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1498
_refine_ls_number_reflns         27956
_refine_ls_number_restraints     76
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.2159
_refine_ls_R_factor_gt           0.1686
_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^)+(0.0500P)^2^+50.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3688
_refine_ls_wR_factor_ref         0.3908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15909
_reflns_number_total             27956
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06236k2.cif
_cod_data_source_block           210519cq_114c_0m
_cod_depositor_comments
'Adding full bibliography for 1565914--1565917.cif.'
_cod_database_code               1565917
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.963
_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
 O21-C100 = C101-C100 = O22-C101 = O22-C102 = O20-C85 = O20-C84 = C84-C83 =
 O19-C83 = O19-C82
 1.5 with sigma of 0.02
 H24D-H60A
 2.1 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C77 \\sim C87 \\sim C86 \\sim C80 \\sim C79 \\sim C78: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C83) \\sim Ueq, Uanis(C84) \\sim Ueq, Uanis(C85) \\sim Ueq, Uanis(O19)
\\sim Ueq, Uanis(O20) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
4.a Free rotating group:
 O23(H23A,H23B), O24(H24C,H24D)
4.b Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C10(H10), C16(H16), C18(H18), C20(H20), C21(H21),
 C28(H28), C30(H30), C34(H34), C35(H35), C42(H42), C44(H44), C48(H48), C49(H49)
4.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C9(H9A,H9B), C11(H11A,H11B), C14(H14A,H14B), C24(H24A,H24B),
 C26(H26A,H26B), C31(H31A,H31B), C33(H33A,H33B), C36(H36A,H36B), C39(H39A,H39B),
  C41(H41A,H41B), C45(H45A,H45B), C47(H47A,H47B), C50(H50A,H50B), C60(H60A,
 H60B), C65(H65A,H65B), C81(H81A,H81B), C82(H82A,H82B), C83(H83A,H83B),
 C84(H84A,H84B), C85(H85A,H85B), C100(H10A,H10B), C101(H10C,H10D), C102(H10E,
 H10F)
4.d Aromatic/amide H refined with riding coordinates:
 C19(H19), C22(H22), N32(H32), N0AA(H0AA), C52(H52), C54(H54), C55(H55),
 C58(H58), C59(H59), C62(H62), C63(H63), C66(H66), C67(H67), C69(H69), C70(H70),
  C72(H72), C73(H73), C75(H75), C87(H87), C86(H86), C79(H79), C78(H78),
 C88(H88), C89(H89), C90(H90), C91(H91), C92(H92), C93(H93), C94(H94), C95(H95),
  C97(H97), C98(H98), C103(H103), C104(H104)
4.e Fitted hexagon refined as free rotating group:
 C77(C87,C86,C80,C79,C78)
;
_shelx_res_checksum              21945
_shelx_hkl_checksum              77635
_shelx_fab_checksum              11747
_olex2_submission_special_instructions 'No special instructions were received'