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_7120197
_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         'C165 H141 N13 O2, 4(H2 O)'
_chemical_formula_sum            'C165 H149 N13 O6'
_chemical_formula_weight         2409.96
_chemical_name_systematic        'phenyl IP foldamer'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc1nsdg9
_audit_creation_date             2016-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-04-07 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.73(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.792(5)
_cell_length_b                   30.143(6)
_cell_length_c                   39.026(8)
_cell_measurement_reflns_used    549071
_cell_measurement_temperature    100
_cell_measurement_theta_max      50.00
_cell_measurement_theta_min      0.57
_cell_volume                     30132(11)
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.630
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.1309
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            201941
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        22.210
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         1.439
_diffrn_source                   'Fixed gap multiple wiggler beamline'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.051
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   HKL3000
_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    1.062
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             10224
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     3443
_refine_ls_number_reflns         103706
_refine_ls_number_restraints     166
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.1836
_refine_ls_R_factor_gt           0.0809
_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^)+(0.1426P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2175
_refine_ls_wR_factor_ref         0.2637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                40633
_reflns_number_total             103706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc03552g2.cif
_cod_data_source_block           racemic_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               7120197
_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,H) groups
2. Restrained distances
 C309-C308 \\sim C409-C308
 with sigma of 0.001
 C409-C414 \\sim C309-C314 \\sim C313-C314 \\sim C312-C313 \\sim C413-C414
\\sim C413-C412 \\sim C311-
 C312 \\sim C412-C411 \\sim C410-C411 \\sim C311-C310 \\sim C309-C310 \\sim
C409-C410
 with sigma of 0.001
3. Restrained angles
 C309-C310-C311
 fixed at 120 with sigma of 0.02
 C309-C310-C311
 fixed at 120 with sigma of 0.02
 C309-C311-C312, C313-C314-C310
 fixed at 120 with sigma of 0.02
 C309-C310-C311
 fixed at 120 with sigma of 0.02
4. Restrained planarity
 C313, C309, C311, C310, C312, C314
 with sigma of 0.01
 C313, C309, C311, C310, C312, C314
 with sigma of 0.1
 C413, C414, C409, C410, C411, C412
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
Uanis(C412) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.001
Uanis(C311) \\sim Ueq, Uanis(C414) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.001
6. Rigid body (RIGU) restrains
 C409, C410, C411, C412, C413, C414, C313, C309, C311, C310, C312, C314
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.0001
7. Others
 Fixed Sof: H30A(0.5) H308(0.5) C409(0.5) C410(0.5) H410(0.5) C411(0.5)
 H411(0.5) C412(0.5) H412(0.5) C413(0.5) H413(0.5) C414(0.5) H414(0.5)
 C313(0.5) H313(0.5) C309(0.5) C311(0.5) H311(0.5) C310(0.5) H310(0.5)
 C312(0.5) H312(0.5) C314(0.5) H314(0.5)
8.a Free rotating group:
 O181(H18D,H18E), O182(H18F,H18G), O184(H18H,H18I), O183(H18J,H18K), O365(H36M,
 H36N), O366(H36O,H36P), O367(H36Q,H36R), O368(H36S,H36T)
8.b Ternary CH refined with riding coordinates:
 C124(H124), C141(H141), C308(H30A), C308(H308), C325(H325)
8.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), N23(H23), N26(H26), N43(H43), N46(H46), N63(H63), N66(H66),
 N123(H123), N140(H140), 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), C118(H118),
 C119(H119), C120(H120), C126(H126), C127(H127), C128(H128), C129(H129),
 C130(H130), C133(H133), C135(H135), C136(H136), C137(H137), C143(H143),
 C144(H144), C145(H145), C146(H146), C147(H147), N187(H187), N190(H190),
 N207(H207), N210(H210), N227(H227), N230(H230), N247(H247), N250(H250),
 N307(H307), N324(H324), C193(H193), C195(H195), C198(H198), C199(H199),
 C202(H202), C204(H204), C213(H213), C215(H215), C218(H218), C219(H219),
 C222(H222), C224(H224), C233(H233), C235(H235), C238(H238), C239(H239),
 C242(H242), C244(H244), C253(H253), C255(H255), C258(H258), C259(H259),
 C262(H262), C264(H264), C268(H268), C269(H269), C270(H270), C274(H274),
 C275(H275), C276(H276), C280(H280), C281(H281), C282(H282), C300(H300),
 C302(H302), C303(H303), C304(H304), C317(H317), C319(H319), C320(H320),
 C321(H321), C327(H327), C328(H328), C329(H329), C330(H330), C331(H331),
 C410(H410), C411(H411), C412(H412), C413(H413), C414(H414), C313(H313),
 C311(H311), C310(H310), C312(H312), C314(H314)
8.d Idealised Me refined as rotating group:
 C131(H13A,H13B,H13C), C148(H14A,H14B,H14C), C150(H15A,H15B,H15C), C151(H15D,
 H15E,H15F), C152(H15G,H15H,H15I), C154(H15J,H15K,H15L), C155(H15M,H15N,H15O),
 C156(H15P,H15Q,H15R), C158(H15S,H15T,H15U), C159(H15V,H15W,H15X), 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), C332(H33A,H33B,H33C), C334(H33D,H33E,H33F),
 C335(H33G,H33H,H33I), C336(H33J,H33K,H33L), C338(H33M,H33N,H33O), C339(H33P,
 H33Q,H33R), C340(H34A,H34B,H34C), C342(H34D,H34E,H34F), C343(H34G,H34H,H34I),
 C344(H34J,H34K,H34L), C346(H34M,H34N,H34O), C347(H34P,H34Q,H34R), C348(H34S,
 H34T,H34U), C350(H35A,H35B,H35C), C351(H35D,H35E,H35F), C352(H35G,H35H,H35I),
 C354(H35J,H35K,H35L), C355(H35M,H35N,H35O), C356(H35P,H35Q,H35R), C358(H35S,
 H35T,H35U), C359(H35V,H35W,H35X), C360(H36A,H36B,H36C), C362(H36D,H36E,H36F),
 C363(H36G,H36H,H36I), C364(H36J,H36K,H36L), C315(H31A,H31B,H31C)
;
_shelx_res_checksum              23783
_shelx_fab_checksum              84080
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'