Regioselective Synthesis of Methylene-Bridged Naphthalene Oligomers and Their Host-Guest Chemistry.
Pan, San-Jiang; Ye, Gang; Jia, Fei; He, Zhenfeng; Ke, Hua; Yao, Huan; Fan, Zhi; Jiang, Wei; The Journal of organic chemistry 82 (2017) 9570–9575; doi:10.1021/acs.joc.7b01579

data_4032768
_publ_section_title
;
 Regioselective Synthesis of Methylene-Bridged Naphthalene Oligomers and
 Their Host-Guest Chemistry.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9570
_journal_page_last               9575
_journal_paper_doi               10.1021/acs.joc.7b01579
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C56 H72 O6'
_chemical_formula_sum            'C56 H72 O6'
_chemical_formula_weight         841.13
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.262(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.2454(8)
_cell_length_b                   7.4219(3)
_cell_length_c                   18.7073(7)
_cell_measurement_reflns_used    3707
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      58.77
_cell_measurement_theta_min      2.85
_cell_volume                     2309.51(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10051
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        59.024
_diffrn_reflns_theta_max         59.024
_diffrn_reflns_theta_min         2.848
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0727 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.8908. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0855P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1478
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2290
_reflns_number_total             3299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01579_si_004.cif
_cod_data_source_block           11n
_cod_depositor_comments
'Adding full bibliography for 4032768--4032770.cif.'
_cod_database_code               4032768
_shelx_shelxl_version_number     2014/7
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C19(H19A,H19B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'