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_4035187
_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         'C69 H48 Br6 O6, 6(C2 H3 N)'
_chemical_formula_sum            'C81 H66 Br6 N6 O6'
_chemical_formula_weight         1698.85
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.158(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9132(8)
_cell_length_b                   15.6470(7)
_cell_length_c                   25.9036(9)
_cell_measurement_reflns_used    9743
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.8340
_cell_measurement_theta_min      2.3100
_cell_volume                     8069.4(6)
_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)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1058
_diffrn_reflns_av_unetI/netI     0.1128
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            53513
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.269
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    3.038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.7767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             3408
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.372
_exptl_crystal_size_min          0.243
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     904
_refine_ls_number_reflns         14171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0697
_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^)+(0.0671P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8458
_reflns_number_total             14171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01437_si_003.cif
_cod_data_source_block           sa5101b_pl
_cod_database_code               4035187
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C31(H31), C34(H34), C53(H53), C56(H56)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C45(H45A,H45B), C67(H67A,H67B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C14(H14), C15(H15), C16(H16), C20(H20), C25(H25), C37(H37),
 C38(H38), C39(H39), C40(H40), C41(H41), C51(H51), C58(H58), C59(H59), C60(H60),
  C61(H61), C63(H63)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C30(H30A,H30B,H30C), C44(H44A,H44B,
 H44C), C52(H52A,H52B,H52C), C68(H68A,H68B,H68C), C71(H71A,H71B,H71C), C72(H72A,
 H72B,H72C), C81(H81A,H81B,H81C), C74(H74A,H74B,H74C), C76(H76A,H76B,H76C),
 C78(H78A,H78B,H78C)
;
_shelx_res_checksum              27401
_shelx_hkl_checksum              35340
_shelx_fab_checksum              30795
_olex2_submission_special_instructions 'No special instructions were received'