Encapsulation of dihydrogenphosphate ions as a cyclic dimer to the cavities of site-specifically modified indolocarbazole-pyridine foldamers
Lee, Chaeeun; Lee, Hyemi; Lee, Seungwon; Jeon, Hae-Geun; Jeong, Kyu-Sung; Organic Chemistry Frontiers 6 (2019) 299–; doi:10.1039/C8QO01307A

data_1554570
_publ_section_title
;
 Encapsulation of dihydrogenphosphate ions as a cyclic dimer to the
 cavities of site-specifically modified indolocarbazole-pyridine foldamers
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              299
_journal_paper_doi               10.1039/C8QO01307A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         '2(H2 O4 P), C141 H127 N11 O2, 2(C16 H36 N)'
_chemical_formula_sum            'C173 H203 N13 O10 P2'
_chemical_formula_weight         2686.41
_chemical_name_systematic        Inverted_pyridine_heptamer
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-25 deposited with the CCDC.
2018-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.83(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.505(4)
_cell_length_b                   29.114(6)
_cell_length_c                   28.751(6)
_cell_measurement_reflns_used    400159
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.749
_cell_measurement_theta_min      0.401
_cell_volume                     17937(6)
_computing_cell_refinement       'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_data_collection       'PAL BL2D-SMDC Program (Shin et. al, 2016)'
_computing_data_reduction        'HKL3000sm (Otwinowski & Minor, 1997)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            94417
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         1.397
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.995
_exptl_crystal_description       block
_exptl_crystal_F_000             5768
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.044
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.00064(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     975
_refine_ls_number_reflns         24407
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1314
_refine_ls_R_factor_gt           0.0904
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1712P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2576
_refine_ls_wR_factor_ref         0.2822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13239
_reflns_number_total             24407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01307a2.cif
_cod_data_source_block           hm7merge_a
_cod_database_code               1554570
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.978
_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 C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C65-C63
 1.6 with sigma of 0.002
 C66-C63 \\sim C65-C63 \\sim C64-C63
 with sigma of 0.002
 C168-C67 \\sim C68-C67 \\sim C69-C67 \\sim C169-C67 \\sim C170-C67 \\sim
C70-C67
 with sigma of 0.002
 C64-C63 \\sim C165-C63 \\sim C65-C63 \\sim C166-C63 \\sim C66-C63 \\sim
C164-C63
 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C65) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C169) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C164) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C66) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C166) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C66) \\sim Ueq, Uanis(C164) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C165)
\\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C166) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C64(0.5) H64A(0.5) H64B(0.5) H64C(0.5) C65(0.5) H65A(0.5)
 H65B(0.5) H65C(0.5) C66(0.5) H66A(0.5) H66B(0.5) H66C(0.5) C68(0.75)
 H68A(0.75) H68B(0.75) H68C(0.75) C69(0.75) H69A(0.75) H69B(0.75) H69C(0.75)
 C70(0.75) H70A(0.75) H70B(0.75) H70C(0.75) C164(0.5) H16A(0.5) H16B(0.5)
 H16C(0.5) C165(0.5) H16D(0.5) H16E(0.5) H16F(0.5) C166(0.5) H16G(0.5)
 H16H(0.5) H16I(0.5) C168(0.25) H16J(0.25) H16K(0.25) H16L(0.25) C169(0.25)
 H16M(0.25) H16N(0.25) H16O(0.25) C170(0.25) H17A(0.25) H17B(0.25) H17C(0.25)
5.a Secondary CH2 refined with riding coordinates:
 C85(H85A,H85B), C86(H86A,H86B), C87(H87A,H87B), C89(H89A,H89B), C90(H90A,
 H90B), C91(H91A,H91B), C93(H93A,H93B), C94(H94A,H94B), C95(H95A,H95B),
 C97(H97A,H97B), C98(H98A,H98B), C99(H99A,H99B)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), N23(H23), N26(H26), C9(H9), C11(H11), C14(H14), C15(H15),
 C18(H18), C20(H20), C29(H29), C31(H31), C34(H34), C35(H35), C38(H38), C40(H40),
  C44(H44), C45(H45), C46(H46), C48(H48), C50(H50)
5.c Idealised Me refined as rotating group:
 C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C72(H72A,H72B,H72C), C73(H73A,H73B,
 H73C), C74(H74A,H74B,H74C), C76(H76A,H76B,H76C), C77(H77A,H77B,H77C), C78(H78A,
 H78B,H78C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C66(H66A,H66B,H66C),
 C68(H68A,H68B,H68C), C69(H69A,H69B,H69C), C70(H70A,H70B,H70C), C164(H16A,H16B,
 H16C), C165(H16D,H16E,H16F), C166(H16G,H16H,H16I), C168(H16J,H16K,H16L),
 C169(H16M,H16N,H16O), C170(H17A,H17B,H17C), C88(H88A,H88B,H88C), C92(H92A,H92B,
 H92C), C96(H96A,H96B,H96C), C100(H10A,H10B,H10C)
5.d Idealised tetrahedral OH refined as rotating group:
 O80(H80), O83(H83), O52(H52)
;
_shelx_res_checksum              28392
_shelx_hkl_checksum              57007
_shelx_fab_checksum              99877
_olex2_submission_special_instructions 'No special instructions were received'