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_1554569
_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), C140 H127 N11 O2, 2(C16 H36 N)'
_chemical_formula_sum            'C172 H203 N13 O10 P2'
_chemical_formula_weight         2674.40
_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_method           SHELXL-2017/1
_audit_update_record
;
2018-11-25 deposited with the CCDC.
2018-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.17(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.469(4)
_cell_length_b                   29.096(6)
_cell_length_c                   28.543(6)
_cell_measurement_reflns_used    394308
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.749
_cell_measurement_theta_min      0.401
_cell_volume                     17757(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_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.970
_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  0.0958
_diffrn_reflns_av_unetI/netI     0.1684
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            45276
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         28.500
_diffrn_reflns_theta_min         1.317
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_process_details   'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.000
_exptl_crystal_description       block
_exptl_crystal_F_000             5744
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00016(3)
_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   0.828
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     972
_refine_ls_number_reflns         22866
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      0.842
_refine_ls_R_factor_all          0.1761
_refine_ls_R_factor_gt           0.0712
_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^)+(0.0792P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1857
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8173
_reflns_number_total             22866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01307a2.cif
_cod_data_source_block           ce10_merge_a
_cod_database_code               1554569
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.985
_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
 C62-C65 \\sim C62-C164
 with sigma of 0.02
 C62-C64 \\sim C62-C163
 with sigma of 0.02
 C62-C63 \\sim C62-C165
 with sigma of 0.02
 C66-C69 \\sim C66-C169
 with sigma of 0.02
 C66-C67 \\sim C66-C167
 with sigma of 0.02
 C66-C68 \\sim C66-C168
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C164) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C163) \\sim Ueq, Uanis(C63)
\\sim Ueq, Uanis(C165) \\sim Ueq, Uanis(C65) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.01
4. Others
 Sof(C163)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C164)=Sof(H16G)=Sof(H16H)=
 Sof(H16I)=Sof(C165)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C63)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C64)=Sof(H2AD)=Sof(H2AE)=Sof(H2AF)=
 Sof(C65)=Sof(H02U)=Sof(H02S)=Sof(H02T)=FVAR(1)
 Sof(C167)=Sof(H16P)=Sof(H16Q)=Sof(H16R)=Sof(C168)=Sof(H16J)=Sof(H16K)=
 Sof(H16L)=Sof(C169)=Sof(H16M)=Sof(H16N)=Sof(H16O)=1-FVAR(2)
 Sof(C67)=Sof(H02Y)=Sof(HK)=Sof(HL)=Sof(C68)=Sof(H1AB)=Sof(H1AC)=Sof(H1AD)=
 Sof(C69)=Sof(H02V)=Sof(H02W)=Sof(H02X)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C84(H84A,H84B), C85(H85A,H85B), C86(H86A,H86B), C88(H88A,H88B), C89(H89A,
 H89B), C90(H90A,H90B), C92(H92B,H92A), C93(H93A,H93B), C94(H94A,H94B),
 C96(H96A,H96B), C97(H97A,H97B), C98(H98A,H98B)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), N23(H23), N26(H26), N48(H48), 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), C49(H49)
5.c Idealised Me refined as rotating group:
 C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C71(H71A,H71B,H71C), C72(H72A,H72B,
 H72C), C73(H73A,H73B,H73C), C75(H75A,H75B,H75C), C76(H76A,H76B,H76C), C77(H77A,
 H77B,H77C), C163(H16A,H16B,H16C), C164(H16G,H16H,H16I), C165(H16D,H16E,H16F),
 C167(H16P,H16Q,H16R), C168(H16J,H16K,H16L), C169(H16M,H16N,H16O), C87(H87A,
 H87B,H87C), C91(H91A,H91B,H91C), C95(H95A,H95B,H95C), C99(H99A,H99B,H99C),
 C63(H3AA,H3AB,H3AC), C64(H2AD,H2AE,H2AF), C65(H02U,H02S,H02T), C67(H02Y,HK,HL),
  C68(H1AB,H1AC,H1AD), C69(H02V,H02W,H02X)
5.d Idealised tetrahedral OH refined as rotating group:
 O80(H80), O81(H81), O59(H59)
;
_shelx_res_checksum              24193
_shelx_hkl_checksum              20624
_shelx_fab_checksum              83567