Stereospecific control of the helical orientation of indolocarbazole–pyridine hybrid foldamers by rational modification of terminal chiral appendages
Kim, Junyoung; Jeon, Hae-Geun; Kang, Philjae; Jeong, Kyu-Sung; Chem. Commun.  (2017) –; doi:10.1039/C7CC03552G

data_7120198
_publ_section_title
;
 Stereospecific control of the helical orientation of
 indolocarbazole--pyridine hybrid foldamers by rational modification of
 terminal chiral appendages
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03552G
_journal_year                    2017
_chemical_formula_moiety         'C175 H149 N13 O4, 4(H2 O)'
_chemical_formula_sum            'C175 H157 N13 O8'
_chemical_formula_weight         2570.13
_chemical_name_systematic        'methoxy naphthyl IP heptamer'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc1nsdf8
_audit_creation_date             2016-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-04-07 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                76.253(3)
_cell_angle_beta                 73.468(3)
_cell_angle_gamma                68.847(3)
_cell_formula_units_Z            2
_cell_length_a                   18.4463(12)
_cell_length_b                   18.6186(12)
_cell_length_c                   27.4771(17)
_cell_measurement_reflns_used    9543
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.23
_cell_volume                     8340.5(9)
_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      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            272525
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.196
_diffrn_reflns_theta_min         2.064
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0733 before and 0.0677 after correction.
The Ratio of minimum to maximum transmission is 0.9312.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.023
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2724
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1805
_refine_ls_number_reflns         33145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0618
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.1867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                22703
_reflns_number_total             33145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc03552g2.cif
_cod_data_source_block           methoxy_naphthyl_heptamer
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               7120198
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O193(H19J,H19K), O194(H19L,H19M), O195(H19N,H19O), O196(H19P,H19Q)
2.b Ternary CH refined with riding coordinates:
 C126(H126), C149(H149)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), N23(H23), N26(H26), N43(H43), N46(H46), N63(H63), N66(H66),
 N125(H125), N148(H148), C9(H9), C11(H11), C14(H14), C15(H15), C18(H18),
 C20(H20), C29(H29), C31(H31), C34(H34), C35(H35), C38(H38), C40(H40), C49(H49),
  C51(H51), C54(H54), C55(H55), C58(H58), C60(H60), C69(H69), C71(H71),
 C74(H74), C75(H75), C78(H78), C80(H80), C84(H84), C85(H85), C86(H86), C90(H90),
  C91(H91), C92(H92), C96(H96), C97(H97), C98(H98), C116(H116), C121(H121),
 C122(H122), C128(H128), C129(H129), C130(H130), C132(H132), C133(H133),
 C134(H134), C135(H135), C139(H139), C144(H144), C145(H145), C151(H151),
 C152(H152), C153(H153), C155(H155), C156(H156), C157(H157), C158(H158)
2.d Idealised Me refined as rotating group:
 C120(H12A,H12B,H12C), C137(H13A,H13B,H13C), C143(H14A,H14B,H14C), C160(H16A,
 H16B,H16C), C162(H16D,H16E,H16F), C163(H16G,H16H,H16I), C164(H16J,H16K,H16L),
 C166(H16M,H16N,H16O), C167(H16P,H16Q,H16R), C168(H16S,H16T,H16U), C170(H17A,
 H17B,H17C), C171(H17D,H17E,H17F), C172(H17G,H17H,H17I), C174(H17J,H17K,H17L),
 C175(H17M,H17N,H17O), C176(H17P,H17Q,H17R), C178(H17S,H17T,H17U), C179(H17V,
 H17W,H17X), C180(H18A,H18B,H18C), C182(H18D,H18E,H18F), C183(H18G,H18H,H18I),
 C184(H18J,H18K,H18L), C186(H18M,H18N,H18O), C187(H18P,H18Q,H18R), C188(H18S,
 H18T,H18U), C190(H19A,H19B,H19C), C191(H19D,H19E,H19F), C192(H19G,H19H,H19I)
;
_shelx_fab_checksum              79997
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'