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_4035188
_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_absolute_configuration ad
_chemical_formula_moiety         'C63 H34 Br6 O6'
_chemical_formula_sum            'C63 H34 Br6 O6'
_chemical_formula_weight         1366.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0266(4)
_cell_length_b                   24.2582(11)
_cell_length_c                   26.2224(10)
_cell_measurement_reflns_used    11111
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.3550
_cell_measurement_theta_min      1.5560
_cell_volume                     7014.1(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, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1390
_diffrn_reflns_av_unetI/netI     0.1793
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            46897
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.766
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    3.475
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       rod
_exptl_crystal_F_000             2680
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.855
_refine_diff_density_min         -1.024
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 2057 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     680
_refine_ls_number_reflns         16110
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.1645
_refine_ls_R_factor_gt           0.0737
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0702P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1865
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                7696
_reflns_number_total             16110
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01437_si_005.cif
_cod_data_source_block           a_pl_sq
_cod_database_code               4035188
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.891
_shelx_estimated_absorpt_t_min   0.244
_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. Rigid bond restraints
 C14, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Riding coordinates:
 O3(H3), O5(H5)
3.b Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C28(H28), C31(H31), C49(H49), C52(H52)
3.c Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C42(H42A,H42B), C63(H63A,H63B)
3.d Aromatic/amide H refined with riding coordinates:
 C6(H6A), C13(H13), C15(H15), C20(H20), C27(H27), C33(H33), C34(H34), C35(H35),
  C36(H36), C41(H41), C48(H48), C54(H54), C55(H55), C56(H56), C57(H57), C59(H59)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O4(H4), O6(H6)
;
_shelx_res_checksum              95087
_shelx_hkl_checksum              65387
_shelx_fab_checksum              38339
_olex2_submission_special_instructions 'No special instructions were received'