Switching of inherent chirality driven by self-assembly
Hanna Jedrzejewska; Marcin Kwit; Agnieszka Szumna; Chem.Commun. 51 (2015) 13799–; doi:10.1039/C5cc05728K

data_7117703
_publ_section_title
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 Switching of inherent chirality driven by self-assembly
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_journal_name_full               Chem.Commun.
_journal_page_first              13799
_journal_paper_doi               10.1039/C5cc05728K
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C84 H96 N8 O12, 2.5(C4 H8 O2)'
_chemical_formula_sum            'C94 H116 N8 O17'
_chemical_formula_weight         1629.95
_chemical_name_systematic        S-2c
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-10 deposited with the CCDC.
2015-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 89.8645(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.7521(4)
_cell_length_b                   23.0271(4)
_cell_length_c                   25.3314(4)
_cell_measurement_reflns_used    21135
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      69.2650
_cell_measurement_theta_min      3.5080
_cell_volume                     10938.2(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXH-1997 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      99.97(15)
_diffrn_detector_area_resol_mean 16.2974
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            145750
_diffrn_reflns_theta_full        70.26
_diffrn_reflns_theta_max         70.26
_diffrn_reflns_theta_min         3.50
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60644
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    0.990
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3488
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2138
_refine_ls_number_reflns         37151
_refine_ls_number_restraints     142
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1081P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.1843
_reflns_number_gt                22523
_reflns_number_total             37151
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05728k3.cif
_cod_data_source_block           S-2c
_cod_original_cell_volume        10938.2(4)
_cod_database_code               7117703
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1S-C2S = C11S-C12S = C21S-C22S = C31S-C32S
 1.5 with sigma of 0.02
 C41S-C42S
 1.5 with sigma of 0.02
 C5S-C6S = C15S-C16S = C25S-C26S = C35S-C36S
 1.5 with sigma of 0.02
 C45S-C46S
 1.5 with sigma of 0.02
 C2S-O3S = C12S-O13S = C22S-O23S = C32S-O33S
 1.2 with sigma of 0.02
 C42S-O43S
 1.2 with sigma of 0.02
 C2S-O4S = C12S-O14S = C22S-O24S = C32S-O34S
 1.32 with sigma of 0.02
 C42S-O44S
 1.32 with sigma of 0.02
 O4S-C5S = O14S-C15S = O24S-C25S = O34S-C35S
 1.45 with sigma of 0.02
 O44S-C45S
 1.45 with sigma of 0.02
3. Restrained planarity
 C106, C307, C308, C312
 with sigma of 0.1
 C1S, C2S, O3S, O4S
 with sigma of 0.1
4. Rigid bond restraints
 C107, C108, C109, C110, C111, C112
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C307, C308, C309, C310, C311, C312
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C167, C168, C169, C170, C171, C172
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C79, C80, C81, C82
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C23, C24, C25, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C155, C156
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C41S, C42S, O43S, O44S, C45S, C46S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C11S, C12S, O13S, O14S, C15S, C16S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1S, C2S, O3S, O4S, C5S, C6S
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Uiso/Uaniso restraints and constraints
C307 \\sim C308 \\sim C309 \\sim C310 \\sim C311 \\sim C312: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
6. Others
 Sof(C307)=Sof(C308)=Sof(H308)=Sof(C309)=Sof(H309)=Sof(C310)=Sof(H310)=
 Sof(C311)=Sof(H311)=Sof(C312)=Sof(H312)=1-FVAR(1)
 Sof(C107)=Sof(C108)=Sof(H108)=Sof(C109)=Sof(H109)=Sof(C110)=Sof(H110)=
 Sof(C111)=Sof(H111)=Sof(C112)=Sof(H112)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C11(H11), C23(H23), C24(H24), C41(H41), C53(H53), C54(H54), C71(H71),
 C83(H83), C84(H84), C101(H101), C113(H113), C114(H114), C131(H131), C143(H143),
  C144(H144), C161(H161), C173(H173), C174(H174), C191(H191), C203(H203),
 C204(H204), C221(H221), C233(H233), C234(H234)
7.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C46(H46A,H46B), C76(H76A,H76B), C106(H10D,H10E), C136(H13D,
 H13E), C166(H16F,H16G), C196(H19D,H19E), C226(H22D,H22E), C5S(H5SA,H5SB),
 C15S(H15D,H15E), C25S(H25D,H25E), C35S(H35A,H35B), C45S(H45D,H45E)
7.c Me refined with riding coordinates:
 C15(H15A,H15B,H15C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C45(H45A,H45B,
 H45C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C75(H75A,H75B,H75C), C85(H85A,
 H85B,H85C), C86(H86A,H86B,H86C), C105(H10A,H10B,H10C), C115(H11A,H11B,H11C),
 C116(H11D,H11E,H11F), C135(H13A,H13B,H13C), C145(H14A,H14B,H14C), C146(H14D,
 H14E,H14F), C165(H16C,H16D,H16E), C175(H17A,H17B,H17C), C176(H17D,H17E,H17F),
 C195(H19A,H19B,H19C), C205(H20A,H20B,H20C), C206(H20D,H20E,H20F), C225(H22A,
 H22B,H22C), C235(H23A,H23B,H23C), C236(H23D,H23E,H23F), C1S(H1SA,H1SB,H1SC),
 C6S(H6SA,H6SB,H6SC), C11S(H11G,H11H,H11I), C16S(H16H,H16I,H16J), C21S(H21A,
 H21B,H21C), C26S(H26D,H26E,H26F), C31S(H31A,H31B,H31C), C36S(H36A,H36B,H36C),
 C41S(H41A,H41B,H41C), C46S(H46C,H46D,H46E)
7.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), N10(H10), N14(H14), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C32(H32), C39(H39), N40(H40), N44(H44), C48(H48), C49(H49), C50(H50),
  C51(H51), C52(H52), C62(H62), C69(H69), N70(H70), N74(H74), C78(H78),
 C79(H79), C80(H80), C81(H81), C82(H82), C92(H92), C99(H99), N100(H100),
 N104(H104), C108(H108), C109(H109), C110(H110), C111(H111), C112(H112),
 C308(H308), C309(H309), C310(H310), C311(H311), C312(H312), C122(H122),
 C129(H129), N130(H130), N134(H134), C138(H138), C139(H139), C140(H140),
 C141(H141), C142(H142), C152(H152), C159(H159), N160(H160), N164(H164),
 C168(H168), C169(H169), C170(H170), C171(H171), C172(H172), C182(H182),
 C189(H189), N190(H190), N194(H194), C198(H198), C199(H199), C200(H200),
 C201(H201), C202(H202), C212(H212), C219(H219), N220(H220), N224(H224),
 C228(H228), C229(H229), C230(H230), C231(H231), C232(H232)
7.e Fitted hexagon refined as free rotating group:
 C77(C78,C79,C80,C81,C82), C107(C108,C109,C110,C111,C112), C307(C308,C309,C310,
 C311,C312), C167(C168,C169,C170,C171,C172), C197(C198,C199,C200,C201,C202)
7.f Tetrahedral OH refined with riding coordinates:
 O7(H7), O37(H37), O67(H67), O97(H97), O127(H127), O157(H157), O187(H187),
 O217(H217)
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_olex2_submission_special_instructions 'No special instructions were received'