Selective Catalytic Synthesis of Unsymmetrical Ethers from the Dehydrative Etherification of Two Different Alcohols
Kim, Junghwa; Lee, Dong-Hwan; Kalutharage, Nishantha; Yi, Chae S.; ACS Catalysis 4 (2014) 3881–; doi:10.1021/cs5012537

data_4512058
_publ_section_title
;
 Selective Catalytic Synthesis of Unsymmetrical Ethers from the
 Dehydrative Etherification of Two Different Alcohols
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              3881
_journal_paper_doi               10.1021/cs5012537
_journal_volume                  4
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C35 H54 O2'
_chemical_formula_sum            'C35 H54 O2'
_chemical_formula_weight         506.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.300(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.0622(3)
_cell_length_b                   9.18339(18)
_cell_length_c                   13.6306(3)
_cell_measurement_reflns_used    7608
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4210
_cell_measurement_theta_min      3.6500
_cell_volume                     1505.64(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0824565000
_diffrn_orient_matrix_UB_12      0.0413954000
_diffrn_orient_matrix_UB_13      -0.0764204000
_diffrn_orient_matrix_UB_21      -0.0343982000
_diffrn_orient_matrix_UB_22      0.1610423000
_diffrn_orient_matrix_UB_23      0.0076466000
_diffrn_orient_matrix_UB_31      0.0916217000
_diffrn_orient_matrix_UB_32      0.0228674000
_diffrn_orient_matrix_UB_33      0.0833928000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15140
_diffrn_reflns_theta_full        72.00
_diffrn_reflns_theta_max         73.66
_diffrn_reflns_theta_min         3.25
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.6896
_exptl_crystal_size_mid          0.1863
_exptl_crystal_size_min          0.0598
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5725
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.3880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                5130
_reflns_number_total             5725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs5012537_si_003.cif
_cod_data_source_block           yi2m
_cod_depositor_comments
'Adding full bibliography for 4512057--4512058.cif.'
_cod_original_cell_volume        1505.63(5)
_cod_database_code               4512058
_chemical_oxdiff_formula         'C25 H56 O2'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C3(H3), C8(H8), C9(H9), C14(H14), C17(H17), C20(H20), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,
 H12B), C15(H15A,H15B), C16(H16A,H16B), C22(H22A,H22B), C23(H23A,H23B),
 C24(H24A,H24B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C30(H30), C31(H31), C33(H33), C34(H34)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C35(H35A,H35B,H35C)
;