Expanded Helicenes: A General Synthetic Strategy and Remarkable Supramolecular and Solid-State Behavior.
Kiel, Gavin R.; Patel, Sajan C.; Smith, Patrick W.; Levine, Daniel S.; Tilley, T. Don; Journal of the American Chemical Society 139 (2017) 18456–18459; doi:10.1021/jacs.7b10902

data_4131791
_publ_section_title
;
 Expanded Helicenes: A General Synthetic Strategy and Remarkable
 Supramolecular and Solid-State Behavior.
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18456
_journal_page_last               18459
_journal_paper_doi               10.1021/jacs.7b10902
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         '3.55(C H Cl3), 2(C96 H96 O10)'
_chemical_formula_sum            'C195.55 H195.55 Cl10.66 O20'
_chemical_formula_weight         3243.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.129(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.2934(8)
_cell_length_b                   19.8397(8)
_cell_length_c                   37.1735(13)
_cell_measurement_reflns_used    9587
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.56
_cell_measurement_theta_min      2.21
_cell_volume                     16911.4(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2 Bruker-AXS, Madison WI'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            118469
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.577
_diffrn_reflns_theta_max         25.577
_diffrn_reflns_theta_min         1.803
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1303 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.8556.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       needle
_exptl_crystal_F_000             6840
_refine_diff_density_max         1.313
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2126
_refine_ls_number_reflns         24356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0979
_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^)+(0.0491P)^2^+110.8571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2286
_refine_ls_wR_factor_ref         0.2418
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18675
_reflns_number_total             24356
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b10902_si_001.cif
_cod_data_source_block           gk545_mexi
_cod_database_code               4131791
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Cl14)=Sof(Cl15)=Sof(Cl13)=Sof(C196)=Sof(H196)=FVAR(1)
 Sof(Cl12)=Sof(Cl11)=Sof(Cl10)=Sof(C195)=Sof(H195)=FVAR(2)
 Sof(Cl6)=Sof(Cl5)=Sof(Cl4)=Sof(C193)=Sof(H193)=FVAR(3)
 Sof(Cl9)=Sof(Cl7)=Sof(Cl8)=Sof(C194)=Sof(H194)=FVAR(4)
 Sof(Cl2)=Sof(Cl3)=Sof(Cl1)=Sof(C192)=Sof(H192)=FVAR(5)
3.a Ternary CH refined with riding coordinates:
 C192(H192), C196(H196), C195(H195), C194(H194), C193(H193)
3.b Secondary CH2 refined with riding coordinates:
 C02V(H02A,H02B), C157(H15A,H15B), C90(H90A,H90B), C88(H88A,H88B), C168(H16A,
 H16B), C156(H15C,H15D), C61(H61A,H61B), C160(H16C,H16D), C169(H16E,H16F),
 C59(H59A,H59B), C184(H18A,H18B), C170(H17A,H17B), C89(H89A,H89B), C155(H15H,
 H15I), C185(H18C,H18D), C186(H18E,H18F), C172(H17C,H17D), C72(H72A,H72B),
 C64(H64A,H64B), C60(H60A,H60B), C75(H75A,H75B), C176(H17E,H17F), C92(H92A,
 H92B), C73(H73A,H73B), C76(H76A,H76B), C188(H18G,H18H), C74(H74A,H74B),
 C80(H80A,H80B)
3.c Aromatic/amide H refined with riding coordinates:
 C143(H143), C39(H39), C140(H140), C47(H47), C134(H134), C137(H137), C36(H36),
 C146(H146), C42(H42), C109(H109), C50(H50), C29(H29), C114(H114), C9(H9),
 C104(H104), C2(H2), C45(H45), C4(H4), C14(H14), C24(H24), C119(H119), C34(H34),
  C131(H131), C99(H99), C19(H19), C148(H148), C1(H1), C52(H52), C149(H149),
 C97(H97), C124(H124), C33(H33), C96(H96), C31(H31), C53(H53), C129(H129),
 C32(H32), C126(H126), C128(H128), C127(H127)
3.d Idealised Me refined as rotating group:
 C91(H91A,H91B,H91C), C154(H15E,H15F,H15G), C58(H58A,H58B,H58C), C162(H16G,
 H16H,H16I), C83(H83A,H83B,H83C), C163(H16J,H16K,H16L), C178(H17G,H17H,H17I),
 C187(H18I,H18J,H18K), C159(H15J,H15K,H15L), C179(H17J,H17K,H17L), C82(H82A,
 H82B,H82C), C95(H95A,H95B,H95C), C189(H18L,H18M,H18N), C63(H63A,H63B,H63C),
 C177(H17M,H17N,H17O), C174(H17P,H17Q,H17R), C77(H77A,H77B,H77C), C190(H19A,
 H19B,H19C), C65(H65A,H65B,H65C), C78(H78A,H78B,H78C), C94(H94A,H94B,H94C),
 C67(H67A,H67B,H67C), C66(H66A,H66B,H66C), C173(H17S,H17T,H17U), C191(H19D,H19E,
 H19F), C62(H62A,H62B,H62C), C175(H17V,H17W,H17X), C161(H16M,H16N,H16O),
 C158(H15M,H15N,H15O), C93(H93A,H93B,H93C), C81(H81A,H81B,H81C), C79(H79A,H79B,
 H79C)
;
_shelx_res_checksum              6701
_shelx_hkl_checksum              73853
_olex2_date_sample_data_collection 2016-11-05
_olex2_date_sample_submission    2016-11-04
_olex2_submission_original_sample_id 'Compound 3c'
_olex2_submission_special_instructions 'No special instructions were received'