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_4032770
_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         'C35 H30 O3'
_chemical_formula_sum            'C35 H30 O3'
_chemical_formula_weight         498.59
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.427(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1982(5)
_cell_length_b                   8.0127(3)
_cell_length_c                   19.7384(7)
_cell_measurement_reflns_used    4956
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      62.33
_cell_measurement_theta_min      4.51
_cell_volume                     2545.77(15)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0467
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11641
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        62.421
_diffrn_reflns_theta_max         62.421
_diffrn_reflns_theta_min         2.745
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.6436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0844 before and 0.0537 after correction. The Ratio of minimum to maximum transmission is 0.8556. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0589
_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^)+(0.0569P)^2^+2.9207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2963
_reflns_number_total             4024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01579_si_002.cif
_cod_data_source_block           p21c
_cod_depositor_comments
'Adding full bibliography for 4032768--4032770.cif.'
_cod_database_code               4032770
_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:
 C12(H12A,H12B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C15(H15), C16(H16),
 C18(H18), C20(H20), C21(H21), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32),
  C33(H33)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C23(H23A,H23B,H23C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              93855
_shelx_hkl_checksum              28682
_olex2_submission_special_instructions 'No special instructions were received'