Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction.
Yang, Ling; Ma, Chunmiao; Kauffmann, Brice; Li, Dongyao; Gan, Quan; Organic & biomolecular chemistry 18 (2020) 6643–6650; doi:10.1039/d0ob01503b

data_7157666
_publ_section_title
;
 Absolute handedness control of oligoamide double helices by chiral
 oxazolylaniline induction.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6643
_journal_page_last               6650
_journal_paper_doi               10.1039/d0ob01503b
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C132 H128 F6 N18 O19, 2(C H Cl3)'
_chemical_formula_sum            'C134 H130 Cl6 F6 N18 O19'
_chemical_formula_weight         2623.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-06-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-16 deposited with the CCDC.	2020-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   35.445(7)
_cell_length_b                   36.434(7)
_cell_length_c                   45.806(9)
_cell_measurement_reflns_used    34000
_cell_measurement_temperature    100
_cell_measurement_theta_max      63.0000
_cell_measurement_theta_min      2.0000
_cell_volume                     59154(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.720
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            54007
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.595
_diffrn_reflns_theta_max         25.705
_diffrn_reflns_theta_min         1.447
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.730
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             21888
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 15086 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.51(12)
_refine_ls_extinction_coef       0.00133(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.291
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     3334
_refine_ls_number_reflns         53467
_refine_ls_number_restraints     325
_refine_ls_restrained_S_all      10.635
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.1057
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2866
_refine_ls_wR_factor_ref         0.3176
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                39105
_reflns_number_total             53467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01503b2.cif
_cod_data_source_block           c2221_sq_sq
_cod_depositor_comments          'Adding full bibliography for 7157666.cif.'
_cod_original_cell_volume        59154(21)
_cod_database_code               7157666
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.963
_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. Restrained distances
 C40-C62
 1.54 with sigma of 0.02
 C62-C10
 1.54 with sigma of 0.02
 C40-C10
 1.54 with sigma of 0.02
 C293-C15
 2.8 with sigma of 0.02
 C3AA-C15
 1.54 with sigma of 0.02
 C4AA-C15
 2.5 with sigma of 0.02
 C69-C20
 1.54 with sigma of 0.02
 O138-C281
 1.45 with sigma of 0.02
 C20-C0AA
 1.54 with sigma of 0.02
 C54-C1AA
 1.54 with sigma of 0.02
 C62-C40
 3 with sigma of 0.02
 C0BA-C71
 1.54 with sigma of 0.02
 C7AA-C2
 1.54 with sigma of 0.01
 C9-C2
 1.54 with sigma of 0.01
 C9-C7AA
 2.5 with sigma of 0.01
 C317-C228
 1.4 with sigma of 0.01
 C5AA-C317
 1.4 with sigma of 0.01
 C7-C5AA
 1.4 with sigma of 0.01
 C7-C28
 1.4 with sigma of 0.01
 C3-C28
 1.4 with sigma of 0.01
 C3-C228
 1.4 with sigma of 0.01
 C290-C13
 1.4 with sigma of 0.01
 C13-C304
 1.4 with sigma of 0.01
 H40A-H62B
 2.4 with sigma of 0.01
 H42C-H72B
 2.4 with sigma of 0.01
 C3-C317
 2.4 with sigma of 0.02
 C228-C5AA
 2.4 with sigma of 0.02
 C317-C7
 2.4 with sigma of 0.02
 C5AA-C28
 2.4 with sigma of 0.02
 C7-C3
 2.4 with sigma of 0.02
 C28-C228
 2.4 with sigma of 0.02
3. Restrained planarity
 C5AA, C7, C28, C3, C228, C317
 with sigma of 0.1
 C228, C317, C5AA, C7, C28, C3
 with sigma of 0.01
4. Rigid bond restraints
 C272, C279, C44, C305
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
O092 \\sim C276 \\sim C2 \\sim C9 \\sim C7AA: within 1.7A with sigma of 0.01
and sigma for terminal atoms of 0.02
Uanis(C291) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C306) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C293) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C44) \\sim Ueq, Uanis(C305) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C2AA) \\sim Ueq, Uanis(C35) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C22) \\sim Ueq, Uanis(C8AA) \\sim Ueq, Uanis(C9AA) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
6. Rigid body (RIGU) restrains
 C0AA, C20, C69, C306, O267
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C54, C1AA, C33, C289, O189
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C62, C40, C10, C291, O205, C157
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C0AA, C20, C69, C306, O267, C288
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C4AA, C15, C3AA, C293, O106
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 Cl7, C6BA, Cl0A, Cl4
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C15, C3AA, C4AA, C293, O106, C169
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C71, C0BA, C34, C17, O217, C206
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C15, C4AA, C3AA, C293, O106, C169
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C228, C3, C28, C7, C5AA, C317
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
7.a Ternary CH refined with riding coordinates:
 C191(H191), C203(H203), C277(H277), C279(H279), C285(H285), C299(H299),
 C301(H301), C312(H312), C313(H313), C316(H316), C319(H319), C2(H2), C5(H5),
 C10(H10), C20(H20), C1(H1), C1AA(H1AA), C1BA(H1BA), C3AA(H3AA), C6AA(H6AA),
 C0BA(H0BA), C6BA(H6BA)
7.b Secondary CH2 refined with riding coordinates:
 C246(H24A,H24B), C251(H25A,H25B), C266(H26A,H26B), C272(H27A,H27B), C274(H27C,
 H27D), C276(H27E,H27F), C281(H28G,H28H), C283(H28A,H28B), C287(H28C,H28D),
 C289(H28E,H28F), C291(H29A,H29B), C293(H29H,H29I), C294(H29C,H29D), C300(H30C,
 H30D), C306(H30A,H30B), C308(H30K,H30L), C314(H31D,H31E), C17(H17A,H17B)
7.c Aromatic/amide H refined with riding coordinates:
 N015(H015), N018(H018), N022(H022), N023(H023), N027(H027), N029(H029),
 N039(H039), N054(H054), N056(H056), C057(H057), N069(H069), N070(H070),
 C072(H072), C075(H075), N076(H076), N077(H077), C083(H083), C088(H088),
 C095(H095), C098(H098), N104(H104), N105(H105), C113(H113), C114(H114),
 C120(H120), C133(H133), C145(H145), C146(H146), C147(H147), C154(H154),
 N159(H159), C160(H160), C161(H161), N164(H164), C165(H165), C166(H166),
 C170(H170), C176(H176), C177(H177), C183(H183), C185(H185), C188(H188),
 N197(H197), C200(H200), C202(H202), C207(H207), C210(H210), C211(H211),
 C212(H212), C213(H213), C214(H214), C218(H218), C221(H221), C224(H224),
 C229(H229), C230(H230), C233(H233), C234(H234), C235(H235), C238(H238),
 C241(H241), C243(H243), C244(H244), C252(H252), C253(H253), C255(H255),
 C256(H256), C257(H257), C260(H260), C262(H262), C263(H263), C265(H265),
 C269(H269), C270(H270), C275(H275), C284(H284), C290(H290), C292(H292),
 C304(H304), C317(H317), C3(H3), C7(H7), C13(H13), C5AA(H5AA), C28(H28),
 C3BA(H3BA), C4BA(H4BA), C4(H4)
7.d Idealised Me refined as rotating group:
 C297(H29E,H29F,H29G), C302(H30E,H30F,H30G), C305(H30H,H30I,H30J), C309(H30M,
 H30N,H30O), C310(H31A,H31B,H31C), C315(H31F,H31G,H31H), C21(H21A,H21B,H21C),
 C25(H25C,H25D,H25E), C32(H32A,H32B,H32C), C40(H40A,H40B,H40C), C43(H43A,H43B,
 H43C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C55(H55A,H55B,H55C), C56(H56A,
 H56B,H56C), C69(H69A,H69B,H69C), C0AA(H0AA,H0AB,H0AC), C42(H42A,H42B,H42C),
 C44(H44A,H44B,H44C), C15(H15A,H15B,H15C), C35(H35A,H35B,H35C), C4AA(H4AA,H4AB,
 H4AC), C2AA(H2AA,H2AB,H2AC), C62(H62A,H62B,H62C), C9(H9A,H9B,H9C), C33(H33A,
 H33B,H33C), C7AA(H7AA,H7AB,H7AC), C54(H54A,H54B,H54C), C64(H64A,H64B,H64C),
 C72(H72A,H72B,H72C), C9AA(H9AA,H9AB,H9AC), C22(H22A,H22B,H22C), C8AA(H8AA,H8AB,
 H8AC), C34(H34A,H34B,H34C), C71(H71A,H71B,H71C), C2BA(H2BA,H2BB,H2BC),
 C5BA(H5BA,H5BB,H5BC), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              4326
_shelx_hkl_checksum              88120
_shelx_fab_checksum              15127
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'