A chiral indolocarbazole foldamer displaying strong circular dichroism responsive to anion binding
Dan A Kim; Philjae Kang; Moon-Gun Choi; Kyu-Sung Jeong; Chem.Commun. 49 (2013) 9743–; doi:10.1039/c3cc45989f

data_7109905
_publ_section_title
;
 A chiral indolocarbazole foldamer displaying strong circular dichroism
 responsive to anion binding
;
_journal_name_full               Chem.Commun.
_journal_page_first              9743
_journal_paper_doi               10.1039/c3cc45989f
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'Cl, C116 H106 N8 O2, 2(C4 H8 O2), C16 H36 N'
_chemical_formula_sum            'C140 H158 Cl N9 O6'
_chemical_formula_weight         2098.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-09-02
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   37.1603(8)
_cell_length_b                   11.1559(3)
_cell_length_c                   15.1723(3)
_cell_measurement_reflns_used    9769
_cell_measurement_temperature    170
_cell_measurement_theta_max      78.43
_cell_measurement_theta_min      2.38
_cell_volume                     6289.8(2)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            60832
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.93
_diffrn_reflns_theta_min         2.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1067 before and 0.0727 after correction.
The Ratio of minimum to maximum transmission is 0.8475.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_description       block
_exptl_crystal_F_000             2252
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 3424 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.027(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     780
_refine_ls_number_reflns         12802
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0617
_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^)+(0.0986P)^2^+0.9960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1816
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.905
_reflns_number_gt                9178
_reflns_number_total             12802
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc45989f.txt
_cod_data_source_block           cu_dn1_0ma
_cod_database_code               7109905
_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
2. Uiso/Uaniso restraints and constraints
C65B \\sim C65A \\sim C63B \\sim C63A \\sim C64B \\sim C64A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
3. Others
 Sof(C73B)=Sof(H73A)=Sof(H73B)=Sof(H73C)=Sof(C71B)=Sof(H71A)=Sof(H71B)=
 Sof(H71C)=Sof(C72B)=Sof(H72A)=Sof(H72B)=Sof(H72C)=1-FVAR(1)
 Sof(C71A)=Sof(H71D)=Sof(H71E)=Sof(H71F)=Sof(C72A)=Sof(H72D)=Sof(H72E)=
 Sof(H72F)=Sof(C73A)=Sof(H73D)=Sof(H73E)=Sof(H73F)=FVAR(1)
 Sof(C65B)=Sof(H65D)=Sof(H65E)=Sof(H65F)=Sof(C64B)=Sof(H64A)=Sof(H64B)=
 Sof(H64C)=Sof(C63B)=Sof(H63D)=Sof(H63E)=Sof(H63F)=1-FVAR(2)
 Sof(C63A)=Sof(H63A)=Sof(H63B)=Sof(H63C)=Sof(C65A)=Sof(H65A)=Sof(H65B)=
 Sof(H65C)=Sof(C64A)=Sof(H64D)=Sof(H64E)=Sof(H64F)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C49(H49)
4.b Secondary CH2 refined with riding coordinates:
 C504(H50D,H50E), C611(H61A,H61B), C622(H62A,H62B), C621(H62C,H62D), C613(H61C,
 H61D), C612(H61E,H61F), C623(H62E,H62F)
4.c Aromatic/amide H refined with riding coordinates:
 N23(H23), N6(H6), N3(H3), C9(H9), C42(H42), N48(H48), C38(H38), C40(H40),
 C53(H53), C15(H15), C14(H14), C11(H11), C55(H55), C18(H18), C46(H46), C20(H20),
  C45(H45), C44(H44), C52(H52), C35(H35), C51(H51), C54(H54)
4.d Idealised Me refined as rotating group:
 C67(H67A,H67B,H67C), C68(H68A,H68B,H68C), C57(H57A,H57B,H57C), C69(H69A,H69B,
 H69C), C501(H50A,H50B,H50C), C505(H50F,H50G,H50H), C73B(H73A,H73B,H73C),
 C71B(H71A,H71B,H71C), C72B(H72A,H72B,H72C), C71A(H71D,H71E,H71F), C72A(H72D,
 H72E,H72F), C73A(H73D,H73E,H73F), C624(H62G,H62H,H62I), C614(H61G,H61H,H61I),
 C63A(H63A,H63B,H63C), C65A(H65A,H65B,H65C), C65B(H65D,H65E,H65F), C64B(H64A,
 H64B,H64C), C63B(H63D,H63E,H63F), C64A(H64D,H64E,H64F)
;
_shelxl_version_number           2013-3