#------------------------------------------------------------------------------ #$Date: 2013-12-28 14:58:47 +0100 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/33/2003390.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2003390 loop_ _publ_author_name 'Pilati, T.' _publ_section_title ; Five 3,3'-Bridged 2,2'-Dithiophenes ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 690 _journal_page_last 697 _journal_volume 51 _journal_year 1995 _chemical_compound_source ; chemical synthesis (Sannicol\'o, 1994). ; _chemical_formula_sum 'C14 H16 O3 S2' _chemical_formula_weight 296.40 _chemical_name_systematic ; 4,6,7,9,10,12-hexahydrodithieno[3,2-c;2',3'-e][1,4,7]trioxacyclotridecine ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90.00 _cell_angle_beta 102.46(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.999(1) _cell_length_b 12.060(2) _cell_length_c 14.930(2) _cell_measurement_radiation 'Mo K\a' _cell_measurement_reflns_used 25 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 17.9 _cell_measurement_theta_min 9.8 _cell_measurement_wavelength 0.70930 _cell_volume 1406.3(4) _computing_cell_refinement SDP _computing_data_collection 'SDP (Frenz, 1983)' _computing_data_reduction SDP _computing_molecular_graphics 'ORTEP (Johnson, 1976)' _computing_publication_material 'PARST (Nardelli, 1983)' _computing_structure_refinement SDP _computing_structure_solution 'MULTAN (Main et al., 1982)' _diffrn_ambient_temperature 295(2) _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method '\q/2\q scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine focus Philips Mo tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2842 _diffrn_reflns_reduction_process ; START-SDP ; _diffrn_reflns_theta_max 26.0 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 360 _diffrn_standards_number 1 _exptl_absorpt_coefficient_mu 0.3629 _exptl_crystal_density_diffrn 1.3999 _exptl_crystal_description ; prism ; _exptl_crystal_F_000 624.0 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.40 _refine_diff_density_min >-0.40 _refine_ls_extinction_coef 1.4(2)x10^-7^ _refine_ls_extinction_method 'Stout & Jensen (1968) ' _refine_ls_goodness_of_fit_obs 2.024 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full-matrix _refine_ls_number_constraints 0 _refine_ls_number_parameters 237 _refine_ls_number_reflns 2087 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.035 _refine_ls_shift/esd_max 0.24 _refine_ls_shift/esd_mean 0.04 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'w = 2F~o~Lp/[\s^2^(I~o~) + (0.02I~o~)^2^]^1/2^' _refine_ls_wR_factor_obs 0.046 _reflns_number_observed 2087 _reflns_number_total 2842 _reflns_observed_criterion 'I~o~ > 2\s(I~o~)' _[local]_cod_data_source_file na1119.cif _[local]_cod_data_source_block V _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_cell_measurement_temperature' value 'room temperature' was changed to '295(2)' - the room/ambient temperature average [293;298] in Kelvins(K) was taken. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_cell_measurement_temperature' value 'room temperature' was changed to '295(2)' - the room/ambient temperature average [293;298] in Kelvins(K) was taken. '_diffrn_ambient_temperature' value 'room temperature' was changed to '295(2)' - the room/ambient temperature average [293;298] in Kelvins(K) was taken. '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1406.34(35) _cod_database_code 2003390 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 S1 0.0494(2) -0.0040(3) 0.0157(2) 0.0453(3) 0.0088(3) 0.0505(2) S7 0.0538(3) -0.0107(3) 0.0060(2) 0.0547(3) -0.0103(3) 0.0492(3) O12 0.0437(7) -0.0051(7) 0.0110(6) 0.059(1) 0.0000(8) 0.0543(8) O15 0.0759(9) 0.0115(9) 0.0264(7) 0.059(1) 0.0058(8) 0.0651(9) O18 0.0602(9) -0.0215(8) -0.0007(7) 0.0597(9) 0.0152(8) 0.0481(8) C2 0.047(1) 0.002(1) 0.0160(8) 0.065(1) 0.006(1) 0.042(1) C3 0.044(1) 0.004(1) 0.0086(8) 0.048(1) -0.003(1) 0.038(1) C4 0.0360(9) 0.0021(9) 0.0067(7) 0.042(1) 0.0019(9) 0.0332(9) C5 0.0350(9) 0.0011(9) 0.0066(7) 0.042(1) 0.0054(9) 0.0361(9) C6 0.045(1) -0.001(1) 0.0068(8) 0.035(1) -0.0001(9) 0.038(1) C8 0.082(2) -0.012(1) 0.011(1) 0.051(1) -0.012(1) 0.042(1) C9 0.073(1) 0.001(1) 0.0249(9) 0.048(1) -0.004(1) 0.048(1) C10 0.050(1) 0.002(1) 0.0134(8) 0.039(1) 0.0028(9) 0.043(1) C11 0.047(1) 0.006(1) 0.0126(9) 0.065(2) 0.007(1) 0.049(1) C13 0.041(1) 0.002(1) 0.012(1) 0.067(2) -0.010(1) 0.087(2) C14 0.050(1) 0.011(1) -0.002(1) 0.067(2) -0.008(1) 0.078(2) C16 0.050(1) -0.004(1) 0.020(1) 0.049(1) 0.003(1) 0.068(1) C17 0.050(1) -0.003(1) 0.014(1) 0.045(1) 0.010(1) 0.061(1) C19 0.059(1) -0.003(1) 0.0051(9) 0.041(1) 0.003(1) 0.039(1) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_attached_atom _atom_site_type_symbol S1 -0.22770(7) 0.12441(5) 0.20634(4) 0.0477(2) aniso . S S7 -0.30744(8) 0.12454(5) -0.03069(4) 0.0534(2) aniso . S O12 0.2434(2) 0.2946(1) 0.01204(9) 0.0523(5) aniso . O O15 0.3168(2) 0.5138(1) 0.0878(1) 0.0648(5) aniso . O O18 0.0479(2) 0.4812(1) 0.1920(1) 0.0579(5) aniso . O C2 -0.2132(3) 0.2227(2) 0.2900(1) 0.0503(7) aniso . C C3 -0.1534(3) 0.3194(2) 0.2653(1) 0.0437(6) aniso . C C4 -0.1168(2) 0.3169(2) 0.1752(1) 0.0372(6) aniso . C C5 -0.1485(2) 0.2147(2) 0.1357(1) 0.0378(6) aniso . C C6 -0.1302(3) 0.1759(2) 0.0451(1) 0.0397(7) aniso . C C8 -0.1906(3) 0.0975(2) -0.1113(2) 0.0587(8) aniso . C C9 -0.0258(3) 0.1249(2) -0.0814(2) 0.0548(8) aniso . C C10 0.0125(3) 0.1700(2) 0.0089(1) 0.0435(6) aniso . C C11 0.1884(3) 0.2032(2) 0.0578(1) 0.0535(8) aniso . C C13 0.4098(3) 0.3358(2) 0.0540(2) 0.0650(9) aniso . C C14 0.4060(3) 0.4169(3) 0.1267(2) 0.0673(9) aniso . C C16 0.2793(3) 0.5872(2) 0.1543(2) 0.0544(8) aniso . C C17 0.0943(3) 0.5850(2) 0.1578(2) 0.0521(7) aniso . C C19 -0.0651(3) 0.4171(2) 0.1288(1) 0.0470(7) aniso . C H2 -0.2430(30) 0.2070(20) 0.3460(10) 0.172(19) iso C2 H H3 -0.1350(20) 0.3830(20) 0.3020(10) 0.117(16) iso C3 H H8 -0.2440(30) 0.0680(20) -0.1670(10) 0.192(20) iso C8 H H9 0.0550(30) 0.1150(20) -0.1150(10) 0.206(22) iso C9 H H111 0.1890(20) 0.2230(20) 0.1210(10) 0.174(20) iso C11 H H112 0.2630(30) 0.1460(20) 0.0590(10) 0.210(23) iso C11 H H131 0.4830(30) 0.2730(20) 0.0830(20) 0.265(25) iso C13 H H132 0.4590(40) 0.3960(30) 0.0120(20) 0.424(39) iso C13 H H141 0.3280(30) 0.3710(20) 0.1720(20) 0.331(32) iso C14 H H142 0.5300(30) 0.4380(20) 0.1580(20) 0.264(26) iso C14 H H161 0.3580(30) 0.5710(20) 0.2170(10) 0.208(22) iso C16 H H162 0.3140(30) 0.6630(20) 0.1400(10) 0.223(23) iso C16 H H171 0.0760(30) 0.6420(20) 0.2020(10) 0.208(22) iso C17 H H172 0.0280(30) 0.6010(20) 0.0980(20) 0.221(23) iso C17 H H191 -0.1640(30) 0.4630(20) 0.1000(20) 0.235(23) iso C19 H H192 -0.0040(30) 0.3960(20) 0.0770(20) 0.263(25) iso C19 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag S Sulphur ;International Tables for X-ray Crystallography (1974, Vol. IV, Tables 2.2A, 2.3.1 and 2.2C) ; 0.110 0.124 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 3 4 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 S1 C5 91.90(10) yes C6 S7 C8 91.90(10) yes C11 O12 C13 114.5(2) no C14 O15 C16 113.1(2) no C17 O18 C19 115.1(2) no S1 C2 H2 121.0(10) no S1 C2 C3 112.00(10) yes C3 C2 H2 127.0(10) no C2 C3 H3 125.0(10) no C2 C3 C4 113.3(2) yes C4 C3 H3 122.0(10) no C3 C4 C19 123.3(2) yes C3 C4 C5 111.5(2) yes C5 C4 C19 125.0(2) yes S1 C5 C4 111.30(10) yes C4 C5 C6 129.7(2) yes S1 C5 C6 118.9(2) yes S7 C6 C5 119.2(2) yes C5 C6 C10 129.7(2) yes S7 C6 C10 111.10(10) yes S7 C8 H8 120(2) no S7 C8 C9 111.6(2) yes C9 C8 H8 129.0(10) no C8 C9 H9 123.0(10) no C8 C9 C10 113.9(2) yes C10 C9 H9 123.0(10) no C6 C10 C9 111.5(2) yes C9 C10 C11 123.6(2) yes C6 C10 C11 124.9(2) yes O12 C11 C10 109.3(2) no C10 C11 H112 111.0(10) no C10 C11 H111 110.0(10) no O12 C11 H112 109.0(10) no O12 C11 H111 110.0(10) no H111 C11 H112 108(2) no O12 C13 H132 113(2) no O12 C13 H131 109.0(10) no O12 C13 C14 112.9(2) no H131 C13 H132 120(2) no C14 C13 H132 93(2) no C14 C13 H131 107(2) no O15 C14 C13 109.5(2) no C13 C14 H142 109.0(10) no C13 C14 H141 102.0(10) no O15 C14 H142 109.0(10) no O15 C14 H141 110.0(10) no H141 C14 H142 116(2) no O15 C16 H162 108.0(10) no O15 C16 H161 110.0(10) no O15 C16 C17 112.1(2) no H161 C16 H162 103(2) no C17 C16 H162 110.0(10) no C17 C16 H161 112.0(10) no O18 C17 C16 111.3(2) no C16 C17 H172 109(2) no C16 C17 H171 108.0(10) no O18 C17 H172 112(2) no O18 C17 H171 106.0(10) no H171 C17 H172 111(2) no O18 C19 C4 109.80(10) no C4 C19 H192 112.0(10) no C4 C19 H191 112.0(10) no O18 C19 H192 108.0(10) no O18 C19 H191 109.0(10) no H191 C19 H192 106(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C2 1.708(2) yes S1 C5 1.729(2) yes S7 C6 1.727(2) yes S7 C8 1.707(3) yes O12 C11 1.416(2) yes O12 C13 1.432(2) yes O15 C14 1.426(3) yes O15 C16 1.410(3) yes O18 C17 1.431(2) yes O18 C19 1.392(2) yes C2 C3 1.342(3) yes C2 H2 0.940(10) no C3 C4 1.437(2) yes C3 H3 0.94(2) no C4 C5 1.366(3) yes C4 C19 1.495(3) yes C5 C6 1.468(2) yes C6 C10 1.366(3) yes C8 C9 1.339(3) yes C8 H8 0.920(10) no C9 C10 1.424(3) yes C9 H9 0.91(2) no C10 C11 1.493(3) yes C11 H111 0.970(10) no C11 H112 0.91(2) no C13 C14 1.466(4) yes C13 H131 1.00(2) no C13 H132 1.09(3) no C14 H141 1.16(2) no C14 H142 1.03(2) no C16 C17 1.492(3) yes C16 H161 1.030(10) no C16 H162 0.99(2) no C17 H171 0.99(2) no C17 H172 0.95(2) no C19 H191 0.99(2) no C19 H192 1.03(3) no _journal_paper_doi 10.1107/S0108270194010516