Glaser–Eglinton–Hay sp–sp coupling and macrocyclization: construction of a new class of polyether macrocycles having a 1,3-diyne unit
Naveen, Naveen; Babu, Srinivasarao Arulananda; Kaur, Gurpreet; Aslam, Nayyar Ahmad; Karanam, Maheswararao; RSC Adv. 4 (2014) 18904–; doi:10.1039/C4RA02174F

data_7235610
_publ_section_title
;
 Glaser--Eglinton--Hay sp--sp coupling and macrocyclization: construction
 of a new class of polyether macrocycles having a 1,3-diyne unit
;
_journal_issue                   36
_journal_name_full               'RSC Adv.'
_journal_page_first              18904
_journal_paper_doi               10.1039/C4RA02174F
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C22 H20 O4'
_chemical_formula_sum            'C22 H20 O4'
_chemical_formula_weight         348.38
_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_Int_Tables_number      14
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-02-20
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.222(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.4674(16)
_cell_length_b                   22.482(2)
_cell_length_c                   9.5117(9)
_cell_measurement_temperature    298(2)
_cell_volume                     3735.2(6)
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26640
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.166
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0605 before and 0.0395 after correction.
        The Ratio of minimum to maximum transmission is 0.8491.
        The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0070(5)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         6589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+4.0681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                4331
_reflns_number_total             6589
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra02174f2.cif
_cod_data_source_block           5a_sci64
_cod_database_code               7235610
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1A(0.079) H1B(0.079) H6A(0.068) H6B(0.068) H7A(0.067) H7B(0.067)
 H9(0.073) H10(0.081) H11(0.082) H12(0.075) H14A(0.068) H14B(0.068) H15A(0.066)
 H15B(0.066) H17(0.071) H18(0.08) H19(0.085) H20(0.079) H22A(0.076) H22B(0.076)
 H23(0.088) H24(0.078) H26A(0.075) H26B(0.075) H27A(0.08) H27B(0.08)
 H30A(0.073) H30B(0.073) H31A(0.07) H31B(0.07) H32(0.095) H33(0.089)
 H35A(0.082) H35B(0.082) H36A(0.083) H36B(0.083) H41(0.08) H42(0.092)
 H43(0.098) H44(0.09)
 Fixed X: H1A(1.3035) H1B(1.231) H6A(1.0114) H6B(0.9935) H7A(0.8531)
 H7B(0.9377) H9(0.8366) H10(0.8059) H11(0.8297) H12(0.8852) H14A(0.957)
 H14B(0.8717) H15A(0.9244) H15B(0.9337) H17(0.9746) H18(1.0444) H19(1.1753)
 H20(1.2375) H22A(1.1927) H22B(1.1532) H23(0.5416) H24(0.4732) H26A(0.4312)
 H26B(0.4209) H27A(0.3694) H27B(0.4549) H30A(0.4408) H30B(0.3558) H31A(0.4948)
 H31B(0.511) H32(0.6743) H33(0.736) H35A(0.6518) H35B(0.6906) H36A(0.7315)
 H36B(0.8035) H41(0.3403) H42(0.3061) H43(0.3275) H44(0.3804)
 Fixed Y: H1A(0.8063) H1B(0.8107) H6A(0.7074) H6B(0.7756) H7A(0.7656)
 H7B(0.7868) H9(0.8014) H10(0.8893) H11(0.9782) H12(0.9788) H14A(0.9679)
 H14B(0.9552) H15A(0.8866) H15B(0.9547) H17(0.9009) H18(0.8863) H19(0.8838)
 H20(0.8956) H22A(0.9574) H22B(0.9002) H23(0.8848) H24(0.8986) H26A(0.9567)
 H26B(0.8888) H27A(0.9585) H27B(0.9708) H30A(0.7905) H30B(0.7694) H31A(0.7745)
 H31B(0.7063) H32(0.8849) H33(0.9014) H35A(0.905) H35B(0.9618) H36A(0.8152)
 H36B(0.8117) H41(0.8031) H42(0.8903) H43(0.9793) H44(0.9818)
 Fixed Z: H1A(-0.0143) H1B(-0.1115) H6A(0.5145) H6B(0.5242) H7A(0.2577)
 H7B(0.238) H9(0.5575) H10(0.6684) H11(0.5545) H12(0.3351) H14A(0.1377)
 H14B(0.094) H15A(-0.0784) H15B(-0.1126) H17(-0.3031) H18(-0.5064) H19(-0.4973)
 H20(-0.2877) H22A(-0.0123) H22B(0.0478) H23(1.4301) H24(1.2269) H26A(1.0378)
 H26B(1.0015) H27A(0.8306) H27B(0.7889) H30A(0.6864) H30B(0.6708) H31A(0.4006)
 H31B(0.4168) H32(1.4254) H33(1.2154) H35A(0.8796) H35B(0.9432) H36A(1.0397)
 H36B(0.9422) H41(0.3635) H42(0.2531) H43(0.3659) H44(0.5886)
;