#------------------------------------------------------------------------------ #$Date: 2020-05-13 06:35:40 +0300 (Wed, 13 May 2020) $ #$Revision: 252014 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157501.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_7157501 loop_ _publ_author_name 'Liu, Jing' 'Wang, Shi-Meng' 'Qin, Hua-Li' _publ_section_title ; Light Induced [2+2] Cycloadditions for Construction of Cyclobutane-Fused Pyridinyl Sulfonyl Fluorides ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00814A _journal_year 2020 _chemical_formula_sum 'C8 H12 F N O4 S' _chemical_formula_weight 237.25 _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _audit_update_record ; 2019-09-16 deposited with the CCDC. 2020-05-12 downloaded from the CCDC. ; _cell_angle_alpha 79.6510(10) _cell_angle_beta 81.793(2) _cell_angle_gamma 80.0050(10) _cell_formula_units_Z 2 _cell_length_a 6.9928(5) _cell_length_b 7.7011(6) _cell_length_c 10.3093(9) _cell_measurement_reflns_used 1609 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 28.209 _cell_measurement_theta_min 2.732 _cell_volume 534.28(7) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2675 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 2.72 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_T_max 0.8961 _exptl_absorpt_correction_T_min 0.8648 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_meas 0 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.36 _refine_diff_density_max 0.254 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 1849 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0402 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.2393P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1065 _refine_ls_wR_factor_ref 0.1132 _reflns_number_gt 1528 _reflns_number_total 1849 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d0ob00814a2.cif _cod_data_source_block 190909f _cod_depositor_comments ; The following automatic conversions were performed: data item '_symmetry_cell_setting' value 'Triclinic' was changed to 'triclinic' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M P-1 _cod_database_code 7157501 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.7129(3) 0.0568(3) 0.0332(2) 0.0935(6) Uani 1 1 d . . . N1 N 0.0590(3) 0.4696(2) 0.27935(18) 0.0401(4) Uani 1 1 d . . . O1 O -0.2202(2) 0.4403(2) 0.41821(17) 0.0525(5) Uani 1 1 d . . . O2 O 0.8158(3) 0.0726(3) 0.2416(2) 0.0657(5) Uani 1 1 d . . . O3 O 0.7016(3) 0.3427(2) 0.09646(19) 0.0633(5) Uani 1 1 d . . . O4 O 0.5485(3) 0.2835(2) 0.6467(2) 0.0661(5) Uani 1 1 d . . . H4C H 0.6322 0.3163 0.5828 0.079 Uiso 1 1 d R . . H4D H 0.4425 0.3556 0.6390 0.079 Uiso 1 1 d R . . S1 S 0.68363(9) 0.15978(8) 0.14579(7) 0.0518(2) Uani 1 1 d . . . C1 C -0.0449(3) 0.3851(3) 0.3837(2) 0.0385(5) Uani 1 1 d . . . C2 C 0.0566(3) 0.2236(3) 0.4617(2) 0.0429(5) Uani 1 1 d . . . H2 H -0.0170 0.1591 0.5298 0.052 Uiso 1 1 calc R . . C3 C 0.2460(3) 0.1661(3) 0.4399(2) 0.0447(5) Uani 1 1 d . . . H3 H 0.3007 0.0657 0.4946 0.054 Uiso 1 1 calc R . . C4 C 0.3743(3) 0.2574(3) 0.3305(2) 0.0377(5) Uani 1 1 d . . . H4 H 0.4808 0.3017 0.3607 0.045 Uiso 1 1 calc R . . C5 C 0.2583(3) 0.3964(3) 0.2316(2) 0.0378(5) Uani 1 1 d . . . H5 H 0.3336 0.4935 0.1938 0.045 Uiso 1 1 calc R . . C6 C 0.2848(3) 0.2596(3) 0.1353(2) 0.0464(6) Uani 1 1 d . . . H6A H 0.3343 0.3052 0.0451 0.056 Uiso 1 1 calc R . . H6B H 0.1697 0.2044 0.1369 0.056 Uiso 1 1 calc R . . C7 C 0.4427(3) 0.1419(3) 0.2169(2) 0.0406(5) Uani 1 1 d . . . H7 H 0.4195 0.0179 0.2434 0.049 Uiso 1 1 calc R . . C8 C -0.0317(4) 0.6313(3) 0.1995(3) 0.0612(7) Uani 1 1 d . . . H8A H -0.1577 0.6720 0.2436 0.092 Uiso 1 1 calc R . . H8B H -0.0468 0.6055 0.1141 0.092 Uiso 1 1 calc R . . H8C H 0.0496 0.7225 0.1883 0.092 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0838(13) 0.1142(16) 0.0909(13) -0.0551(12) 0.0183(10) -0.0214(11) N1 0.0392(10) 0.0339(9) 0.0420(10) 0.0004(8) 0.0000(8) -0.0017(8) O1 0.0413(9) 0.0498(10) 0.0590(11) -0.0037(8) 0.0066(8) -0.0020(7) O2 0.0416(10) 0.0690(12) 0.0800(13) 0.0024(10) -0.0147(9) 0.0014(8) O3 0.0595(11) 0.0497(10) 0.0738(13) 0.0072(9) 0.0085(9) -0.0205(8) O4 0.0578(11) 0.0535(11) 0.0755(13) 0.0093(9) 0.0022(9) -0.0052(9) S1 0.0393(3) 0.0516(4) 0.0599(4) -0.0058(3) 0.0064(3) -0.0069(3) C1 0.0391(12) 0.0350(11) 0.0420(12) -0.0077(10) -0.0011(9) -0.0082(9) C2 0.0472(13) 0.0377(12) 0.0410(12) -0.0001(10) 0.0039(10) -0.0121(10) C3 0.0488(13) 0.0404(12) 0.0413(12) 0.0041(10) -0.0065(10) -0.0067(10) C4 0.0357(11) 0.0389(12) 0.0396(12) -0.0038(9) -0.0053(9) -0.0104(9) C5 0.0366(11) 0.0367(11) 0.0383(12) -0.0009(9) -0.0003(9) -0.0092(9) C6 0.0399(12) 0.0569(14) 0.0438(13) -0.0111(11) -0.0058(10) -0.0071(10) C7 0.0375(11) 0.0346(11) 0.0490(13) -0.0041(10) 0.0004(10) -0.0108(9) C8 0.0625(17) 0.0485(14) 0.0574(16) 0.0094(12) 0.0023(13) 0.0076(12) 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 _geom_angle_publ_flag C1 N1 C5 122.35(18) . . ? C1 N1 C8 120.51(19) . . ? C5 N1 C8 116.83(18) . . ? H4C O4 H4D 108.0 . . ? O3 S1 O2 114.53(12) . . ? O3 S1 F1 109.86(13) . . ? O2 S1 F1 109.00(13) . . ? O3 S1 C7 110.03(11) . . ? O2 S1 C7 108.84(11) . . ? F1 S1 C7 104.05(11) . . ? O1 C1 N1 122.4(2) . . ? O1 C1 C2 119.8(2) . . ? N1 C1 C2 117.81(19) . . ? C3 C2 C1 123.6(2) . . ? C3 C2 H2 118.2 . . ? C1 C2 H2 118.2 . . ? C2 C3 C4 122.0(2) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C3 C4 C5 112.97(18) . . ? C3 C4 C7 111.36(17) . . ? C5 C4 C7 88.32(15) . . ? C3 C4 H4 113.9 . . ? C5 C4 H4 113.9 . . ? C7 C4 H4 113.9 . . ? N1 C5 C4 117.18(17) . . ? N1 C5 C6 117.73(18) . . ? C4 C5 C6 90.17(16) . . ? N1 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C5 C6 C7 89.07(16) . . ? C5 C6 H6A 113.8 . . ? C7 C6 H6A 113.8 . . ? C5 C6 H6B 113.8 . . ? C7 C6 H6B 113.8 . . ? H6A C6 H6B 111.0 . . ? C6 C7 C4 89.21(16) . . ? C6 C7 S1 114.04(16) . . ? C4 C7 S1 112.42(14) . . ? C6 C7 H7 113.0 . . ? C4 C7 H7 113.0 . . ? S1 C7 H7 113.0 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 S1 1.4917(19) . ? N1 C1 1.341(3) . ? N1 C5 1.461(3) . ? N1 C8 1.462(3) . ? O1 C1 1.248(3) . ? O2 S1 1.4451(19) . ? O3 S1 1.4297(18) . ? O4 H4C 0.8500 . ? O4 H4D 0.8500 . ? S1 C7 1.757(2) . ? C1 C2 1.481(3) . ? C2 C3 1.322(3) . ? C2 H2 0.9300 . ? C3 C4 1.489(3) . ? C3 H3 0.9300 . ? C4 C5 1.544(3) . ? C4 C7 1.568(3) . ? C4 H4 0.9800 . ? C5 C6 1.544(3) . ? C5 H5 0.9800 . ? C6 C7 1.547(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 O1 -174.2(2) . . . . ? C8 N1 C1 O1 -0.9(3) . . . . ? C5 N1 C1 C2 7.6(3) . . . . ? C8 N1 C1 C2 -179.1(2) . . . . ? O1 C1 C2 C3 -173.2(2) . . . . ? N1 C1 C2 C3 5.0(3) . . . . ? C1 C2 C3 C4 -1.9(4) . . . . ? C2 C3 C4 C5 -11.8(3) . . . . ? C2 C3 C4 C7 -109.3(2) . . . . ? C1 N1 C5 C4 -21.6(3) . . . . ? C8 N1 C5 C4 164.8(2) . . . . ? C1 N1 C5 C6 84.2(3) . . . . ? C8 N1 C5 C6 -89.4(3) . . . . ? C3 C4 C5 N1 22.6(3) . . . . ? C7 C4 C5 N1 135.16(18) . . . . ? C3 C4 C5 C6 -99.0(2) . . . . ? C7 C4 C5 C6 13.51(15) . . . . ? N1 C5 C6 C7 -134.87(19) . . . . ? C4 C5 C6 C7 -13.69(16) . . . . ? C5 C6 C7 C4 13.49(16) . . . . ? C5 C6 C7 S1 -100.81(16) . . . . ? C3 C4 C7 C6 100.6(2) . . . . ? C5 C4 C7 C6 -13.49(16) . . . . ? C3 C4 C7 S1 -143.64(17) . . . . ? C5 C4 C7 S1 102.30(16) . . . . ? O3 S1 C7 C6 42.77(19) . . . . ? O2 S1 C7 C6 169.02(16) . . . . ? F1 S1 C7 C6 -74.87(18) . . . . ? O3 S1 C7 C4 -56.89(18) . . . . ? O2 S1 C7 C4 69.36(18) . . . . ? F1 S1 C7 C4 -174.53(16) . . . . ?