A Route to Enantiopure ( O-Methyl)<sub>6</sub>-2,6-Helic[6]arenes: Synthesis of Hexabromo-Substituted 2,6-Helic[6]arene Derivatives and Their Suzuki-Miyaura Coupling Reactions.
Wang, Jia-Qi; Li, Jing; Zhang, Geng-Wu; Chen, Chuan-Feng; The Journal of organic chemistry 83 (2018) 11532–11540; doi:10.1021/acs.joc.8b01437

data_4035190
_publ_section_title
;
 A Route to Enantiopure ( O-Methyl)<sub>6</sub>-2,6-Helic[6]arenes:
 Synthesis of Hexabromo-Substituted 2,6-Helic[6]arene Derivatives and
 Their Suzuki-Miyaura Coupling Reactions.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11532
_journal_page_last               11540
_journal_paper_doi               10.1021/acs.joc.8b01437
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C H Cl3, C99 H66 O6'
_chemical_formula_sum            'C100 H67 Cl3 O6'
_chemical_formula_weight         1470.88
_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   mixed
_audit_creation_date             2017-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.057(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.8710(8)
_cell_length_b                   16.1571(4)
_cell_length_c                   22.4581(7)
_cell_measurement_reflns_used    19141
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.8770
_cell_measurement_theta_min      1.8180
_cell_volume                     8580.2(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            55374
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.526
_diffrn_source                   Confocal
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_description       block
_exptl_crystal_F_000             3064
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1025
_refine_ls_number_reflns         15118
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.0745
_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^)+(0.0926P)^2^+0.4643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.2121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8596
_reflns_number_total             15118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01437_si_004.cif
_cod_data_source_block           mx5882a
_cod_database_code               4035190
_shelx_shelxl_version_number     2016/6
_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 O(H) groups
2. Restrained distances
 C78A-C73 = C78A-C77A = C78-C73 = C78-C77 = C77A-C76A = C77-C76 = C76A-C75A =
 C76-C75 = C75A-C74A = C75-C74 = C74A-C73 = C74-C73
 1.38 with sigma of 0.01
 O4-C57 = O3-C72 = O5-C25 = O2-C90 = O1-C1 = O6-C39
 1.37 with sigma of 0.001
3. Restrained planarity
 C76, C77, C78, C73, C74, C75
 with sigma of 0.001
 C76A, C77A, C78A, C73, C74A, C75A
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
C78A \\sim C78 \\sim C77A \\sim C77 \\sim C76A \\sim C76 \\sim C75A \\sim C75
\\sim C74A \\sim C74: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
Uanis(C78A) \\sim Ueq, Uanis(C78) \\sim Ueq, Uanis(C77A) \\sim Ueq, Uanis(C77)
\\sim Ueq, Uanis(C76A) \\sim Ueq, Uanis(C76) \\sim Ueq, Uanis(C75A) \\sim Ueq,
Uanis(C75) \\sim Ueq, Uanis(C74A) \\sim Ueq, Uanis(C74) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Sof(C78A)=Sof(H78A)=Sof(C77A)=Sof(H77A)=Sof(C76A)=Sof(H76A)=Sof(C75A)=
 Sof(H75A)=Sof(C74A)=Sof(H74A)=1-FVAR(1)
 Sof(C74)=Sof(H74)=Sof(C75)=Sof(H75)=Sof(C76)=Sof(H76)=Sof(C77)=Sof(H77)=
 Sof(C78)=Sof(H78)=FVAR(1)
 Fixed X: C77(0.34227)
 Fixed Y: C77(0.734539)
 Fixed Z: C77(0.8873)
6.a Riding coordinates:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5), O6(H6)
6.b Ternary CH refined with riding coordinates:
 C100(H100), C13(H13), C20(H20), C46(H46), C49(H49), C79(H79), C82(H82)
6.c Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C66(H66A,H66B), C99(H99A,H99B)
6.d Aromatic/amide H refined with riding coordinates:
 C3(H3A), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C23(H23), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
  C35(H35), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C50(H50),
 C51(H51), C52(H52), C53(H53), C59(H59), C61(H61), C62(H62), C63(H63), C64(H64),
  C65(H65), C68(H68), C74(H74), C75(H75), C76(H76), C77(H77), C78(H78),
 C84(H84), C85(H85), C86(H86), C87(H87), C92(H92), C94(H94), C95(H95), C96(H96),
  C97(H97), C98(H98), C78A(H78A), C77A(H77A), C76A(H76A), C75A(H75A), C74A(H74A)
;
_shelx_res_checksum              8058
_shelx_hkl_checksum              63140
_shelx_fab_checksum              22780
_olex2_submission_special_instructions 'No special instructions were received'