#------------------------------------------------------------------------------ #$Date: 2019-11-28 21:02:53 +0200 (Thu, 28 Nov 2019) $ #$Revision: 244612 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/92/7239238.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_7239238 loop_ _publ_author_name 'Kapdi, Anant R.' 'Karbelkar, Amruta' 'Naik, Minal' 'Pednekar, Suhas' 'Fischer, Christian' 'Schulzke, Carola' 'Tromp, Moniek' _publ_section_title ; Efficient synthesis of coumarin-based tetra and pentacyclic rings using phospha-palladacycles ; _journal_issue 43 _journal_name_full 'RSC Advances' _journal_page_first 20905 _journal_paper_doi 10.1039/c3ra43821j _journal_volume 3 _journal_year 2013 _chemical_formula_sum 'C12 H7 F O3' _chemical_formula_weight 218.18 _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 _cell_angle_alpha 74.65(3) _cell_angle_beta 80.31(3) _cell_angle_gamma 82.76(3) _cell_formula_units_Z 2 _cell_length_a 7.1648(14) _cell_length_b 7.7947(16) _cell_length_c 8.6050(17) _cell_measurement_reflns_used 5030 _cell_measurement_temperature 170(2) _cell_measurement_theta_max 58.5 _cell_measurement_theta_min 6.4 _cell_volume 455.13(17) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 170(2) _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _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 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 5030 _diffrn_reflns_theta_full 29.25 _diffrn_reflns_theta_max 29.25 _diffrn_reflns_theta_min 3.19 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_correction_T_min 0.9086 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'face indexed' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_description platelet _exptl_crystal_F_000 224 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.314 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 2442 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0486 _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^)+(0.0814P)^2^+0.0618P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1293 _refine_ls_wR_factor_ref 0.1425 _reflns_number_gt 1762 _reflns_number_total 2442 _reflns_threshold_expression >2\s(I) _iucr_refine_instructions_details ; TITL MNB75 in P-1 CELL 0.71073 7.1648 7.7947 8.6050 74.651 80.308 82.757 ZERR 2.00 0.0014 0.0016 0.0017 0.030 0.030 0.030 LATT 1 SFAC C H O F UNIT 24 14 6 2 MERG 2 FMAP 2 ACTA PLAN -5 L.S. 24 TEMP -103.00 WGHT 0.081400 0.061800 FVAR 1.48315 C1 1 0.081809 0.035370 0.725927 11.00000 0.02632 0.03701 = 0.03561 -0.00059 0.00352 -0.01015 AFIX 137 H1A 2 -0.051747 0.057753 0.708622 11.00000 -1.50000 H1B 2 0.093229 0.051102 0.833122 11.00000 -1.50000 H1C 2 0.128103 -0.087025 0.720631 11.00000 -1.50000 AFIX 0 C2 1 0.196472 0.162788 0.598033 11.00000 0.02012 0.03322 = 0.03166 -0.00683 0.00213 -0.00733 C3 1 0.127949 0.295129 0.480991 11.00000 0.01928 0.03332 = 0.03177 -0.00494 0.00062 -0.00608 AFIX 43 H3 2 -0.003866 0.317033 0.472469 11.00000 -1.20000 AFIX 0 C4 1 0.264189 0.398882 0.372123 11.00000 0.02304 0.02850 = 0.02624 -0.00345 -0.00007 -0.00478 C5 1 0.395066 0.600581 0.169863 11.00000 0.02579 0.02916 = 0.02689 -0.00544 0.00094 -0.00600 C6 1 0.417561 0.740322 0.033876 11.00000 0.03668 0.03292 = 0.03072 -0.00411 -0.00205 -0.00486 AFIX 43 H6 2 0.312052 0.805821 -0.014638 11.00000 -1.20000 AFIX 0 C7 1 0.602658 0.780492 -0.028653 11.00000 0.04433 0.03051 = 0.02939 -0.00295 0.00340 -0.01195 AFIX 43 H7 2 0.627801 0.876406 -0.121856 11.00000 -1.20000 AFIX 0 C8 1 0.750456 0.678652 0.046824 11.00000 0.03051 0.03531 = 0.03221 -0.00717 0.00726 -0.01426 C9 1 0.729510 0.540219 0.184168 11.00000 0.02648 0.03174 = 0.03119 -0.00630 0.00282 -0.01059 AFIX 43 H9 2 0.835274 0.475724 0.232951 11.00000 -1.20000 AFIX 0 C10 1 0.543661 0.500549 0.247194 11.00000 0.02574 0.02771 = 0.02580 -0.00610 0.00238 -0.00724 C11 1 0.454570 0.369636 0.380540 11.00000 0.02016 0.02836 = 0.02797 -0.00592 0.00218 -0.00640 C12 1 0.525102 0.231569 0.507309 11.00000 0.02037 0.02890 = 0.02892 -0.00731 0.00215 -0.00683 O1 3 0.222180 0.537996 0.246804 11.00000 0.02325 0.03313 = 0.03028 -0.00021 -0.00069 -0.00375 O2 3 0.686095 0.191470 0.535484 11.00000 0.02092 0.03732 = 0.03791 -0.00478 -0.00256 -0.00315 O3 3 0.385800 0.131259 0.612057 11.00000 0.02064 0.03121 = 0.03067 -0.00202 0.00079 -0.00683 F1 4 0.929315 0.719432 -0.020015 11.00000 0.03649 0.04891 = 0.04526 -0.00123 0.01104 -0.02115 HKLF 4 REM test in P-1 REM R1 = 0.0486 for 1762 Fo > 4sig(Fo) and 0.0687 for all 2442 data REM 146 parameters refined using 0 restraints END WGHT 0.0811 0.0625 REM Highest difference peak 0.314, deepest hole -0.289, 1-sigma level 0.055 Q1 1 0.2005 0.3455 0.4252 11.00000 0.05 0.31 Q2 1 0.5186 0.4340 0.3234 11.00000 0.05 0.31 Q3 1 0.7405 0.6055 0.1159 11.00000 0.05 0.26 Q4 1 0.3746 0.3857 0.3929 11.00000 0.05 0.26 Q5 1 0.1382 0.0993 0.6640 11.00000 0.05 0.25 ; _cod_data_source_file c3ra43821j.txt _cod_data_source_block MNB75 _cod_original_cell_volume 455.13(16) _cod_original_sg_symbol_H-M P-1 _cod_database_code 7239238 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 C1 C 0.0818(2) 0.0354(2) 0.7259(2) 0.0349(4) Uani 1 1 d . H1A H -0.0517 0.0578 0.7086 0.052 Uiso 1 1 calc R H1B H 0.0932 0.0511 0.8331 0.052 Uiso 1 1 calc R H1C H 0.1281 -0.0870 0.7206 0.052 Uiso 1 1 calc R C2 C 0.1965(2) 0.1628(2) 0.59803(19) 0.0288(3) Uani 1 1 d . C3 C 0.1279(2) 0.2951(2) 0.48099(19) 0.0289(3) Uani 1 1 d . H3 H -0.0039 0.3170 0.4725 0.035 Uiso 1 1 calc R C4 C 0.2642(2) 0.3989(2) 0.37212(18) 0.0268(3) Uani 1 1 d . C5 C 0.3951(2) 0.6006(2) 0.16986(19) 0.0278(3) Uani 1 1 d . C6 C 0.4176(2) 0.7403(2) 0.0339(2) 0.0343(4) Uani 1 1 d . H6 H 0.3121 0.8058 -0.0146 0.041 Uiso 1 1 calc R C7 C 0.6027(3) 0.7805(2) -0.0287(2) 0.0359(4) Uani 1 1 d . H7 H 0.6278 0.8764 -0.1219 0.043 Uiso 1 1 calc R C8 C 0.7505(2) 0.6787(2) 0.0468(2) 0.0333(4) Uani 1 1 d . C9 C 0.7295(2) 0.5402(2) 0.18417(19) 0.0302(3) Uani 1 1 d . H9 H 0.8353 0.4757 0.2330 0.036 Uiso 1 1 calc R C10 C 0.5437(2) 0.5005(2) 0.24719(18) 0.0268(3) Uani 1 1 d . C11 C 0.45457(19) 0.3696(2) 0.38054(18) 0.0260(3) Uani 1 1 d . C12 C 0.5251(2) 0.2316(2) 0.50731(18) 0.0263(3) Uani 1 1 d . O1 O 0.22218(15) 0.53800(15) 0.24680(13) 0.0306(3) Uani 1 1 d . O2 O 0.68609(14) 0.19147(16) 0.53548(14) 0.0331(3) Uani 1 1 d . O3 O 0.38580(14) 0.13126(15) 0.61206(13) 0.0287(3) Uani 1 1 d . F1 F 0.92931(15) 0.71943(16) -0.02002(14) 0.0460(3) Uani 1 1 d . 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 C1 0.0263(7) 0.0370(9) 0.0356(8) -0.0006(7) 0.0035(6) -0.0102(6) C2 0.0201(6) 0.0332(8) 0.0317(8) -0.0068(6) 0.0021(5) -0.0073(5) C3 0.0193(6) 0.0333(8) 0.0318(8) -0.0049(6) 0.0006(5) -0.0061(5) C4 0.0230(7) 0.0285(8) 0.0262(7) -0.0035(6) -0.0001(5) -0.0048(5) C5 0.0258(7) 0.0292(8) 0.0269(7) -0.0054(6) 0.0009(5) -0.0060(5) C6 0.0367(8) 0.0329(8) 0.0307(8) -0.0041(7) -0.0020(6) -0.0049(7) C7 0.0443(9) 0.0305(8) 0.0294(8) -0.0030(6) 0.0034(7) -0.0119(7) C8 0.0305(8) 0.0353(9) 0.0322(8) -0.0072(7) 0.0073(6) -0.0143(6) C9 0.0265(7) 0.0317(8) 0.0312(8) -0.0063(6) 0.0028(6) -0.0106(6) C10 0.0257(7) 0.0277(7) 0.0258(7) -0.0061(6) 0.0024(5) -0.0072(5) C11 0.0202(6) 0.0284(7) 0.0280(7) -0.0059(6) 0.0022(5) -0.0064(5) C12 0.0204(6) 0.0289(8) 0.0289(8) -0.0073(6) 0.0021(5) -0.0068(5) O1 0.0233(5) 0.0331(6) 0.0303(6) -0.0002(4) -0.0007(4) -0.0038(4) O2 0.0209(5) 0.0373(6) 0.0379(6) -0.0048(5) -0.0026(4) -0.0032(4) O3 0.0206(5) 0.0312(6) 0.0307(6) -0.0020(4) 0.0008(4) -0.0068(4) F1 0.0365(6) 0.0489(7) 0.0453(6) -0.0012(5) 0.0110(4) -0.0212(5) 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C3 C2 O3 122.60(13) C3 C2 C1 125.65(14) O3 C2 C1 111.74(14) C2 C3 C4 115.58(13) O1 C4 C11 112.43(13) O1 C4 C3 124.06(13) C11 C4 C3 123.51(15) C6 C5 O1 124.67(15) C6 C5 C10 124.53(15) O1 C5 C10 110.79(13) C5 C6 C7 116.34(17) C8 C7 C6 119.01(16) F1 C8 C9 117.61(16) F1 C8 C7 117.24(15) C9 C8 C7 125.15(15) C8 C9 C10 115.77(16) C9 C10 C5 119.19(14) C9 C10 C11 135.63(15) C5 C10 C11 105.16(13) C4 C11 C12 120.39(13) C4 C11 C10 106.14(14) C12 C11 C10 133.46(13) O2 C12 O3 116.68(14) O2 C12 C11 129.03(14) O3 C12 C11 114.30(12) C4 O1 C5 105.47(12) C2 O3 C12 123.58(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.482(2) C2 C3 1.345(2) C2 O3 1.3676(18) C3 C4 1.405(2) C4 O1 1.3554(19) C4 C11 1.365(2) C5 C6 1.374(2) C5 O1 1.3842(17) C5 C10 1.392(2) C6 C7 1.386(2) C7 C8 1.386(3) C8 F1 1.3534(17) C8 C9 1.375(2) C9 C10 1.3909(19) C10 C11 1.436(2) C11 C12 1.425(2) C12 O2 1.2042(18) C12 O3 1.3931(17)