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#$Date: 2019-11-23 11:52:19 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233177 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/56/7235622.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7235622
loop_
_publ_author_name
'Naveen, Naveen'
'Babu, Srinivasarao Arulananda'
'Kaur, Gurpreet'
'Aslam, Nayyar Ahmad'
'Karanam, Maheswararao'
_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         'C24 H26 O5 S'
_chemical_formula_sum            'C24 H26 O5 S'
_chemical_formula_weight         426.51
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-06T15:55:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5532(5)
_cell_length_b                   24.2453(13)
_cell_length_c                   9.5232(4)
_cell_measurement_reflns_used    794
_cell_measurement_temperature    298
_cell_measurement_theta_max      20.12
_cell_measurement_theta_min      3.02
_cell_volume                     2205.77(19)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_solution
;
        XS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9531
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.99
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         1.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0654 before and 0.0581 after correction.
        The Ratio of minimum to maximum transmission is 0.9147.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0084(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1507
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0462P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                906
_reflns_number_total             1973
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra02174f2.cif
_cod_data_source_block           nm1066
_cod_database_code               7235622
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
S1 S -0.14497(16) 0.75 0.13826(13) 0.0752(5) Uani 1 d
O1 O -0.1108(2) 0.87794(9) 0.2647(2) 0.0720(8) Uani 1 d
O2 O 0.1194(2) 0.85866(8) 0.62517(19) 0.0478(6) Uani 1 d
O3 O 0.1959(3) 0.75 0.7332(3) 0.0478(8) Uani 1 d
C1 C 0.1063(4) 0.77895(14) 0.1042(3) 0.0717(12) Uani 1 d
H1 H 0.187 0.8 0.0933 0.086 Uiso 1 calc
C2 C -0.0219(4) 0.80113(16) 0.1215(3) 0.0624(10) Uani 1 d
C3 C -0.0597(5) 0.86055(16) 0.1305(4) 0.0825(13) Uani 1 d
H3A H 0.0223 0.8823 0.1073 0.099 Uiso 1 calc
H3B H -0.1306 0.8683 0.0604 0.099 Uiso 1 calc
C4 C -0.0099(3) 0.87108(13) 0.3723(3) 0.0574(10) Uani 1 d
H4A H 0.0821 0.8809 0.3373 0.069 Uiso 1 calc
H4B H -0.0075 0.8328 0.402 0.069 Uiso 1 calc
C5 C -0.0474(3) 0.90734(12) 0.4948(3) 0.0435(8) Uani 1 d
C6 C -0.1449(4) 0.94920(14) 0.4841(4) 0.0593(10) Uani 1 d
H6 H -0.1927 0.9543 0.4 0.071 Uiso 1 calc
C7 C -0.1727(4) 0.98379(15) 0.5968(4) 0.0681(11) Uani 1 d
H7 H -0.2393 1.0116 0.5887 0.082 Uiso 1 calc
C8 C -0.1010(4) 0.97657(15) 0.7204(4) 0.0646(11) Uani 1 d
H8 H -0.1189 0.9999 0.7958 0.077 Uiso 1 calc
C9 C -0.0033(3) 0.93548(13) 0.7342(3) 0.0516(9) Uani 1 d
H9 H 0.0449 0.931 0.8183 0.062 Uiso 1 calc
C10 C 0.0232(3) 0.90063(12) 0.6219(3) 0.0421(8) Uani 1 d
C11 C 0.1832(3) 0.84697(12) 0.7578(3) 0.0468(9) Uani 1 d
H11A H 0.1115 0.8392 0.8271 0.056 Uiso 1 calc
H11B H 0.2363 0.8788 0.7893 0.056 Uiso 1 calc
C12 C 0.2780(3) 0.79845(12) 0.7434(3) 0.0483(8) Uani 1 d
H12A H 0.3354 0.8024 0.66 0.058 Uiso 1 calc
H12B H 0.3393 0.7961 0.8243 0.058 Uiso 1 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 S1 C2 92.5(3) . 7_575
C4 O1 C3 112.3(3) . .
C10 O2 C11 116.9(2) . .
C12 O3 C12 112.2(3) 7_575 .
C1 C1 H1 123.2 7_575 .
C2 C1 C1 113.5(2) . 7_575
C2 C1 H1 123.2 . .
C1 C2 S1 110.2(3) . .
C1 C2 C3 127.9(4) . .
C3 C2 S1 121.9(3) . .
O1 C3 C2 114.8(3) . .
O1 C3 H3A 108.6 . .
O1 C3 H3B 108.6 . .
C2 C3 H3A 108.6 . .
C2 C3 H3B 108.6 . .
H3A C3 H3B 107.5 . .
O1 C4 H4A 109.8 . .
O1 C4 H4B 109.8 . .
O1 C4 C5 109.3(3) . .
H4A C4 H4B 108.3 . .
C5 C4 H4A 109.8 . .
C5 C4 H4B 109.8 . .
C6 C5 C4 122.2(3) . .
C6 C5 C10 118.4(3) . .
C10 C5 C4 119.3(3) . .
C5 C6 H6 119.5 . .
C5 C6 C7 121.1(3) . .
C7 C6 H6 119.5 . .
C6 C7 H7 120.3 . .
C8 C7 C6 119.4(3) . .
C8 C7 H7 120.3 . .
C7 C8 H8 119.5 . .
C9 C8 C7 121.0(3) . .
C9 C8 H8 119.5 . .
C8 C9 H9 120.2 . .
C8 C9 C10 119.5(3) . .
C10 C9 H9 120.2 . .
O2 C10 C5 115.5(3) . .
O2 C10 C9 123.9(3) . .
C9 C10 C5 120.7(3) . .
O2 C11 H11A 109.8 . .
O2 C11 H11B 109.8 . .
O2 C11 C12 109.5(2) . .
H11A C11 H11B 108.2 . .
C12 C11 H11A 109.8 . .
C12 C11 H11B 109.8 . .
O3 C12 C11 109.0(2) . .
O3 C12 H12A 109.9 . .
O3 C12 H12B 109.9 . .
C11 C12 H12A 109.9 . .
C11 C12 H12B 109.9 . .
H12A C12 H12B 108.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.716(4) .
S1 C2 1.716(4) 7_575
O1 C3 1.432(4) .
O1 C4 1.417(3) .
O2 C10 1.372(3) .
O2 C11 1.431(3) .
O3 C12 1.415(3) 7_575
O3 C12 1.416(3) .
C1 C1 1.404(7) 7_575
C1 H1 0.93 .
C1 C2 1.347(4) .
C2 C3 1.488(5) .
C3 H3A 0.97 .
C3 H3B 0.97 .
C4 H4A 0.97 .
C4 H4B 0.97 .
C4 C5 1.504(4) .
C5 C6 1.381(4) .
C5 C10 1.396(4) .
C6 H6 0.93 .
C6 C7 1.388(4) .
C7 H7 0.93 .
C7 C8 1.373(4) .
C8 H8 0.93 .
C8 C9 1.372(4) .
C9 H9 0.93 .
C9 C10 1.386(4) .
C11 H11A 0.97 .
C11 H11B 0.97 .
C11 C12 1.490(4) .
C12 H12A 0.97 .
C12 H12B 0.97 .
