Electronic Supplementary Material for CrystEngComm This Journal is © The Royal SOciety of Chemistry 2003 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_year ? _journal_page_first ? loop_ _publ_author_name 'J. Narasimha Moorthy' 'P. Venkatakrishnan' 'Ashutosh S. Singh' _publ_contact_author_name 'Dr Narasimha Moorthy' _publ_contact_author_address ; Dr Narasimha Moorthy Department of Chemistry Indian Institute of Technology Kanpur Uttar Pradesh 208016 INDIA ; _publ_contact_author_email MOORTHY@IITK.AC.IN _publ_section_title ; Molecular Self-Assembly: 4-Formylcoumarins as Versatile Skeletons for Complementary Multi-Point Association via Weak (C-H***O, C-H***F and C-X***O==C) Interactions ; data_4-formylcoumarin _database_code_depnum_ccdc_archive 'CCDC 213047' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-formylcoumarin ; _chemical_name_common 4-formylcoumarin _chemical_melting_point 152 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 O3' _chemical_formula_weight 174.15 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.8240(10) _cell_length_b 9.1080(10) _cell_length_c 22.252(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.263(5) _cell_angle_gamma 90.00 _cell_volume 774.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1 _cell_measurement_theta_max 15 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 'not measured' _exptl_absorpt_correction_T_max 'not measured' _exptl_absorpt_process_details none _exptl_special_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method theta-2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1213 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 22.47 _reflns_number_total 1001 _reflns_number_gt 547 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD 4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD 4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'X CAD4 (Harms & Wocaldo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond, 2.1c' _computing_publication_material 'WINGX Publication routines (Farrugia, 1999) ' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.1009P)^2^+0.1127P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.016(6) _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1001 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1192 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1762 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O1 O 0.7715(7) 0.7628(3) 0.29416(11) 0.0509(9) Uani 1 1 d . . . O2 O 0.5079(9) 0.6430(3) 0.22170(13) 0.0713(10) Uani 1 1 d . . . O3 O 1.2422(9) 0.3320(3) 0.41802(14) 0.0807(12) Uani 1 1 d . . . C2 C 0.6729(11) 0.6332(4) 0.26817(17) 0.0503(12) Uani 1 1 d . . . C3 C 0.7733(10) 0.5022(4) 0.29912(17) 0.0494(11) Uani 1 1 d . . . H3A H 0.7137 0.4125 0.2818 0.059 Uiso 1 1 calc R . . C4 C 0.9479(10) 0.5016(4) 0.35155(17) 0.0444(11) Uani 1 1 d . . . C5 C 1.1977(10) 0.6573(5) 0.43696(17) 0.0514(12) Uani 1 1 d . . . H5A H 1.2636 0.5747 0.4590 0.062 Uiso 1 1 calc R . . C6 C 1.2595(11) 0.7942(5) 0.45997(17) 0.0601(13) Uani 1 1 d . . . H6A H 1.3633 0.8038 0.4980 0.072 Uiso 1 1 calc R . . C7 C 1.1712(11) 0.9168(5) 0.42805(19) 0.0630(13) Uani 1 1 d . . . H7A H 1.2219 1.0088 0.4441 0.076 Uiso 1 1 calc R . . C8 C 1.0080(11) 0.9065(4) 0.37243(18) 0.0541(12) Uani 1 1 d . . . H8A H 0.9455 0.9899 0.3506 0.065 Uiso 1 1 calc R . . C9 C 1.0357(9) 0.6410(4) 0.38037(16) 0.0422(11) Uani 1 1 d . . . C10 C 0.9412(9) 0.7683(4) 0.35044(15) 0.0413(10) Uani 1 1 d . . . C11 C 1.0424(12) 0.3556(4) 0.3772(2) 0.0599(13) Uani 1 1 d . . . H11A H 0.9345 0.2742 0.3596 0.072 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 O1 0.071(2) 0.0350(16) 0.0466(17) 0.0032(12) -0.0107(14) 0.0033(14) O2 0.098(2) 0.053(2) 0.061(2) -0.0001(15) -0.0311(17) 0.0099(17) O3 0.101(3) 0.065(2) 0.075(2) 0.0208(17) -0.027(2) 0.0110(19) C2 0.060(3) 0.042(3) 0.048(3) -0.004(2) -0.011(2) 0.003(2) C3 0.060(3) 0.033(2) 0.055(3) 0.0007(18) -0.003(2) 0.0006(19) C4 0.047(3) 0.040(2) 0.047(2) 0.0056(18) -0.002(2) 0.0033(19) C5 0.051(3) 0.057(3) 0.046(2) 0.0058(19) -0.004(2) 0.001(2) C6 0.054(3) 0.077(3) 0.049(3) -0.009(2) -0.011(2) -0.010(2) C7 0.072(3) 0.047(3) 0.069(3) -0.017(2) -0.010(2) -0.011(2) C8 0.066(3) 0.035(2) 0.061(3) 0.002(2) -0.002(2) -0.001(2) C9 0.045(3) 0.035(2) 0.046(2) 0.0025(18) 0.0006(19) -0.0014(18) C10 0.040(2) 0.045(2) 0.039(2) -0.0022(18) 0.0001(18) -0.0018(18) C11 0.070(3) 0.039(3) 0.070(3) 0.006(2) -0.001(3) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 C2 1.364(4) . ? O1 C10 1.399(4) . ? O2 C2 1.203(4) . ? O3 C11 1.193(5) . ? C2 C3 1.426(5) . ? C3 C4 1.331(5) . ? C4 C9 1.458(5) . ? C4 C11 1.489(5) . ? C5 C6 1.367(6) . ? C5 C9 1.399(5) . ? C6 C7 1.361(6) . ? C7 C8 1.377(5) . ? C8 C10 1.373(5) . ? C9 C10 1.381(5) . ? 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 C2 O1 C10 122.0(3) . . ? O2 C2 O1 115.8(3) . . ? O2 C2 C3 127.4(4) . . ? O1 C2 C3 116.8(3) . . ? C4 C3 C2 123.4(4) . . ? C3 C4 C9 119.2(3) . . ? C3 C4 C11 116.9(4) . . ? C9 C4 C11 123.9(3) . . ? C6 C5 C9 120.3(4) . . ? C7 C6 C5 120.9(4) . . ? C6 C7 C8 121.0(4) . . ? C10 C8 C7 117.4(4) . . ? C10 C9 C5 116.8(4) . . ? C10 C9 C4 117.6(3) . . ? C5 C9 C4 125.6(4) . . ? C8 C10 C9 123.6(3) . . ? C8 C10 O1 115.5(3) . . ? C9 C10 O1 120.9(3) . . ? O3 C11 C4 126.7(4) . . ? 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 C10 O1 C2 O2 175.1(4) . . . . ? C10 O1 C2 C3 -4.4(5) . . . . ? O2 C2 C3 C4 -177.9(4) . . . . ? O1 C2 C3 C4 1.5(6) . . . . ? C2 C3 C4 C9 1.7(6) . . . . ? C2 C3 C4 C11 -178.3(4) . . . . ? C9 C5 C6 C7 -1.2(6) . . . . ? C5 C6 C7 C8 1.9(7) . . . . ? C6 C7 C8 C10 -0.5(6) . . . . ? C6 C5 C9 C10 -0.7(6) . . . . ? C6 C5 C9 C4 -178.4(4) . . . . ? C3 C4 C9 C10 -2.0(5) . . . . ? C11 C4 C9 C10 177.9(4) . . . . ? C3 C4 C9 C5 175.7(4) . . . . ? C11 C4 C9 C5 -4.4(6) . . . . ? C7 C8 C10 C9 -1.5(6) . . . . ? C7 C8 C10 O1 179.3(3) . . . . ? C5 C9 C10 C8 2.1(5) . . . . ? C4 C9 C10 C8 -180.0(4) . . . . ? C5 C9 C10 O1 -178.7(3) . . . . ? C4 C9 C10 O1 -0.8(5) . . . . ? C2 O1 C10 C8 -176.6(3) . . . . ? C2 O1 C10 C9 4.1(5) . . . . ? C3 C4 C11 O3 167.4(4) . . . . ? C9 C4 C11 O3 -12.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 22.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.303 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.065 #======END data_6-chloro-4-formylcoumarin _database_code_depnum_ccdc_archive 'CCDC 213048' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-Chloro-4-formylcoumarin ; _chemical_name_common 6-Chloro-4-formylcoumarin _chemical_melting_point 184 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H5 Cl O3' _chemical_formula_weight 208.59 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.0980(10) _cell_length_b 8.5800(10) _cell_length_c 14.328(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.913(5) _cell_angle_gamma 90.00 _cell_volume 864.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1 _cell_measurement_theta_max 15 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.603 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.414 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 'not measured' _exptl_absorpt_correction_T_max 'not measured' _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method omega/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1268 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 22.47 _reflns_number_total 1122 _reflns_number_gt 914 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'CAD 4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD 4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'X CAD4 (Harms & Wocaldo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond, 2.1c' _computing_publication_material 'WINGX Publication routines (Farrugia, 1999) ' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.2975P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0061(17) _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1122 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0756 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Cl1 Cl 0.14132(9) -0.09384(8) 0.25381(4) 0.0643(3) Uani 1 1 d . . . O1 O 0.2866(2) -0.10161(17) 0.66498(10) 0.0481(4) Uani 1 1 d . . . O2 O 0.3720(2) 0.0037(2) 0.80434(11) 0.0606(5) Uani 1 1 d . . . O3 O 0.3075(3) 0.3805(2) 0.45919(12) 0.0746(6) Uani 1 1 d . . . C2 C 0.3444(3) 0.0240(3) 0.72055(16) 0.0446(6) Uani 1 1 d . . . C3 C 0.3654(3) 0.1688(3) 0.67188(14) 0.0427(6) Uani 1 1 d . . . H3 H 0.4065 0.2563 0.7073 0.051 Uiso 1 1 calc R . . C4 C 0.3286(3) 0.1830(2) 0.57789(14) 0.0372(5) Uani 1 1 d . . . C5 C 0.2325(3) 0.0452(2) 0.42214(14) 0.0401(5) Uani 1 1 d . . . H5 H 0.2429 0.1361 0.3879 0.048 Uiso 1 1 calc R . . C6 C 0.1804(3) -0.0919(3) 0.37639(15) 0.0434(6) Uani 1 1 d . . . C7 C 0.1629(3) -0.2293(3) 0.42488(16) 0.0483(6) Uani 1 1 d . . . H7 H 0.1279 -0.3209 0.3923 0.058 Uiso 1 1 calc R . . C8 C 0.1978(3) -0.2292(3) 0.52147(16) 0.0473(6) Uani 1 1 d . . . H8 H 0.1852 -0.3204 0.5551 0.057 Uiso 1 1 calc R . . C9 C 0.2699(3) 0.0475(2) 0.52083(14) 0.0352(5) Uani 1 1 d . . . C10 C 0.2520(3) -0.0920(2) 0.56811(14) 0.0383(5) Uani 1 1 d . . . C11 C 0.3501(3) 0.3416(3) 0.53874(17) 0.0491(6) Uani 1 1 d . . . H11 H 0.4020 0.4177 0.5808 0.059 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 Cl1 0.0778(5) 0.0718(5) 0.0405(4) -0.0109(3) -0.0018(3) 0.0063(4) O1 0.0669(11) 0.0374(9) 0.0392(9) 0.0044(7) 0.0053(7) 0.0004(7) O2 0.0829(13) 0.0607(11) 0.0357(10) 0.0053(8) -0.0006(8) 0.0039(9) O3 0.1237(17) 0.0448(11) 0.0514(12) 0.0113(8) -0.0016(10) -0.0107(10) C2 0.0485(13) 0.0440(14) 0.0408(14) -0.0006(11) 0.0045(10) 0.0068(11) C3 0.0465(13) 0.0376(13) 0.0431(13) -0.0032(10) 0.0028(10) 0.0011(10) C4 0.0380(12) 0.0342(12) 0.0398(12) -0.0004(9) 0.0072(9) 0.0037(9) C5 0.0407(12) 0.0390(13) 0.0407(13) 0.0037(10) 0.0061(9) 0.0065(10) C6 0.0404(13) 0.0488(15) 0.0403(13) -0.0065(11) 0.0027(9) 0.0076(11) C7 0.0496(14) 0.0397(14) 0.0549(15) -0.0100(11) 0.0050(11) 0.0019(11) C8 0.0564(14) 0.0318(13) 0.0541(14) 0.0011(11) 0.0092(11) 0.0003(11) C9 0.0326(11) 0.0336(12) 0.0393(12) 0.0000(9) 0.0051(9) 0.0050(9) C10 0.0401(12) 0.0365(12) 0.0384(12) 0.0024(10) 0.0053(9) 0.0067(10) C11 0.0637(16) 0.0357(13) 0.0484(15) -0.0030(11) 0.0091(12) -0.0048(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl1 C6 1.740(2) . ? O1 C2 1.369(3) . ? O1 C10 1.378(2) . ? O2 C2 1.202(2) . ? O3 C11 1.186(3) . ? C2 C3 1.442(3) . ? C3 C4 1.342(3) . ? C4 C9 1.449(3) . ? C4 C11 1.487(3) . ? C5 C6 1.372(3) . ? C5 C9 1.402(3) . ? C6 C7 1.383(3) . ? C7 C8 1.372(3) . ? C8 C10 1.382(3) . ? C9 C10 1.390(3) . ? 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 C2 O1 C10 122.42(17) . . ? O2 C2 O1 117.5(2) . . ? O2 C2 C3 126.5(2) . . ? O1 C2 C3 116.08(18) . . ? C4 C3 C2 123.0(2) . . ? C3 C4 C9 119.65(19) . . ? C3 C4 C11 116.47(19) . . ? C9 C4 C11 123.88(18) . . ? C6 C5 C9 119.7(2) . . ? C5 C6 C7 121.8(2) . . ? C5 C6 Cl1 119.05(18) . . ? C7 C6 Cl1 119.08(17) . . ? C8 C7 C6 119.3(2) . . ? C7 C8 C10 119.2(2) . . ? C10 C9 C5 117.52(19) . . ? C10 C9 C4 117.03(18) . . ? C5 C9 C4 125.45(19) . . ? O1 C10 C8 115.80(19) . . ? O1 C10 C9 121.80(19) . . ? C8 C10 C9 122.40(19) . . ? O3 C11 C4 126.5(2) . . ? 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 C10 O1 C2 O2 -179.56(19) . . . . ? C10 O1 C2 C3 0.6(3) . . . . ? O2 C2 C3 C4 -178.8(2) . . . . ? O1 C2 C3 C4 1.0(3) . . . . ? C2 C3 C4 C9 -1.8(3) . . . . ? C2 C3 C4 C11 177.7(2) . . . . ? C9 C5 C6 C7 0.2(3) . . . . ? C9 C5 C6 Cl1 -178.13(15) . . . . ? C5 C6 C7 C8 0.2(3) . . . . ? Cl1 C6 C7 C8 178.52(16) . . . . ? C6 C7 C8 C10 -0.8(3) . . . . ? C6 C5 C9 C10 0.0(3) . . . . ? C6 C5 C9 C4 179.09(19) . . . . ? C3 C4 C9 C10 1.0(3) . . . . ? C11 C4 C9 C10 -178.47(19) . . . . ? C3 C4 C9 C5 -178.0(2) . . . . ? C11 C4 C9 C5 2.4(3) . . . . ? C2 O1 C10 C8 178.85(18) . . . . ? C2 O1 C10 C9 -1.4(3) . . . . ? C7 C8 C10 O1 -179.28(18) . . . . ? C7 C8 C10 C9 1.0(3) . . . . ? C5 C9 C10 O1 179.69(17) . . . . ? C4 C9 C10 O1 0.5(3) . . . . ? C5 C9 C10 C8 -0.6(3) . . . . ? C4 C9 C10 C8 -179.73(19) . . . . ? C3 C4 C11 O3 -172.6(2) . . . . ? C9 C4 C11 O3 7.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 22.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.150 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.037 #======END data_7-Chloro-4-formylcoumarin _database_code_depnum_ccdc_archive 'CCDC 213049' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-Chloro-4-formylcoumarin ; _chemical_name_common 7-Chloro-4-formylcoumarin _chemical_melting_point 214 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H5 Cl O3' _chemical_formula_weight 208.59 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.984(2) _cell_length_b 5.9390(10) _cell_length_c 18.452(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.333(5) _cell_angle_gamma 90.00 _cell_volume 857.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1 _cell_measurement_theta_max 15 _exptl_crystal_description cubic _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.417 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 'not measured' _exptl_absorpt_correction_T_max 'not measured' _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method omega/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1273 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.1390 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 22.46 _reflns_number_total 1118 _reflns_number_gt 571 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD 4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD 4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'X CAD4 (Harms & Wocaldo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond, 2.1c' _computing_publication_material 'WINGX Publication routines(Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.1171P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1118 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1763 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Cl1 Cl 0.6227(3) -0.1256(3) 0.28839(9) 0.0600(7) Uani 1 1 d . . . O1 O 0.6374(6) -0.2960(7) 0.5548(2) 0.0472(13) Uani 1 1 d . . . O2 O 0.6290(6) -0.4009(8) 0.6680(2) 0.0592(15) Uani 1 1 d . . . O3 O 0.9799(7) 0.4320(9) 0.6120(2) 0.0629(16) Uani 1 1 d . . . C2 C 0.6776(9) -0.2626(14) 0.6309(3) 0.0443(19) Uani 1 1 d . . . C3 C 0.7771(8) -0.0640(12) 0.6547(3) 0.0425(19) Uani 1 1 d . . . H3 H 0.8093 -0.0380 0.7053 0.051 Uiso 1 1 calc R . . C4 C 0.8254(8) 0.0832(12) 0.6092(3) 0.0368(18) Uani 1 1 d . . . C5 C 0.8165(8) 0.1897(12) 0.4752(4) 0.046(2) Uani 1 1 d . . . H5 H 0.8759 0.3226 0.4888 0.055 Uiso 1 1 calc R . . C6 C 0.7675(8) 0.1339(12) 0.4019(3) 0.0453(19) Uani 1 1 d . . . H6 H 0.7930 0.2297 0.3657 0.054 Uiso 1 1 calc R . . C7 C 0.6814(8) -0.0620(12) 0.3822(3) 0.0372(18) Uani 1 1 d . . . C8 C 0.6371(8) -0.2071(10) 0.4321(3) 0.0372(18) Uani 1 1 d . . . H8 H 0.5774 -0.3393 0.4176 0.045 Uiso 1 1 calc R . . C9 C 0.7770(8) 0.0471(11) 0.5290(3) 0.0349(18) Uani 1 1 d . . . C10 C 0.6858(8) -0.1472(13) 0.5057(3) 0.0355(18) Uani 1 1 d . . . C11 C 0.9277(10) 0.2748(14) 0.6426(4) 0.054(2) Uani 1 1 d . . . H11 H 0.9561 0.2755 0.6939 0.064 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 Cl1 0.0777(14) 0.0745(14) 0.0272(9) -0.0005(10) 0.0092(8) 0.0005(13) O1 0.060(3) 0.042(3) 0.037(3) 0.000(2) 0.004(2) -0.008(3) O2 0.082(4) 0.058(4) 0.038(3) 0.014(3) 0.013(3) -0.017(3) O3 0.066(4) 0.065(4) 0.060(3) 0.010(3) 0.016(3) -0.014(3) C2 0.045(5) 0.056(5) 0.030(4) 0.001(4) 0.001(3) 0.006(5) C3 0.044(5) 0.049(5) 0.032(4) -0.010(4) 0.001(3) -0.002(4) C4 0.033(4) 0.044(5) 0.034(4) -0.002(4) 0.009(3) 0.006(4) C5 0.041(5) 0.046(6) 0.054(4) 0.007(4) 0.016(4) -0.004(4) C6 0.045(5) 0.052(5) 0.039(4) 0.013(4) 0.009(3) -0.006(5) C7 0.044(5) 0.036(5) 0.032(4) -0.003(4) 0.006(3) -0.002(4) C8 0.038(4) 0.034(4) 0.039(4) 0.005(4) 0.004(3) -0.002(4) C9 0.035(4) 0.033(5) 0.035(4) -0.006(3) 0.004(3) -0.002(4) C10 0.030(4) 0.048(5) 0.030(4) 0.011(4) 0.009(3) 0.002(4) C11 0.050(5) 0.064(5) 0.044(4) -0.013(5) 0.002(4) 0.005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl1 C7 1.743(6) . ? O1 C10 1.375(7) . ? O1 C2 1.391(7) . ? O2 C2 1.183(8) . ? O3 C11 1.207(8) . ? C2 C3 1.442(9) . ? C3 C4 1.322(8) . ? C4 C11 1.464(9) . ? C4 C9 1.470(8) . ? C5 C6 1.373(8) . ? C5 C9 1.387(8) . ? C6 C7 1.364(8) . ? C7 C8 1.357(8) . ? C8 C10 1.383(8) . ? C9 C10 1.387(8) . ? 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 C10 O1 C2 122.3(5) . . ? O2 C2 O1 116.7(7) . . ? O2 C2 C3 127.9(6) . . ? O1 C2 C3 115.4(6) . . ? C4 C3 C2 124.0(6) . . ? C3 C4 C11 117.1(6) . . ? C3 C4 C9 119.5(7) . . ? C11 C4 C9 123.5(6) . . ? C6 C5 C9 119.8(7) . . ? C7 C6 C5 119.9(6) . . ? C8 C7 C6 123.1(6) . . ? C8 C7 Cl1 118.7(5) . . ? C6 C7 Cl1 118.2(5) . . ? C7 C8 C10 116.2(6) . . ? C5 C9 C10 117.7(6) . . ? C5 C9 C4 125.4(6) . . ? C10 C9 C4 116.8(6) . . ? O1 C10 C8 114.9(6) . . ? O1 C10 C9 121.9(6) . . ? C8 C10 C9 123.2(6) . . ? O3 C11 C4 128.3(7) . . ? 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 C10 O1 C2 O2 179.7(6) . . . . ? C10 O1 C2 C3 -1.5(8) . . . . ? O2 C2 C3 C4 -179.6(7) . . . . ? O1 C2 C3 C4 1.8(9) . . . . ? C2 C3 C4 C11 -179.4(6) . . . . ? C2 C3 C4 C9 -0.1(9) . . . . ? C9 C5 C6 C7 -0.5(10) . . . . ? C5 C6 C7 C8 1.3(10) . . . . ? C5 C6 C7 Cl1 -179.8(5) . . . . ? C6 C7 C8 C10 -0.6(9) . . . . ? Cl1 C7 C8 C10 -179.5(5) . . . . ? C6 C5 C9 C10 -1.0(9) . . . . ? C6 C5 C9 C4 178.3(6) . . . . ? C3 C4 C9 C5 178.8(6) . . . . ? C11 C4 C9 C5 -1.9(10) . . . . ? C3 C4 C9 C10 -1.9(9) . . . . ? C11 C4 C9 C10 177.4(6) . . . . ? C2 O1 C10 C8 179.3(6) . . . . ? C2 O1 C10 C9 -0.4(9) . . . . ? C7 C8 C10 O1 179.3(5) . . . . ? C7 C8 C10 C9 -1.0(9) . . . . ? C5 C9 C10 O1 -178.5(6) . . . . ? C4 C9 C10 O1 2.1(9) . . . . ? C5 C9 C10 C8 1.8(9) . . . . ? C4 C9 C10 C8 -177.6(6) . . . . ? C3 C4 C11 O3 -177.1(8) . . . . ? C9 C4 C11 O3 3.6(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.235 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.061 #======END data_7-Bromo-4-Formylcoumarin _database_code_depnum_ccdc_archive 'CCDC 213050' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-bromo-4-formylcoumarin ; _chemical_name_common 7-bromo-4-formylcoumarin _chemical_melting_point 206 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H5 Br O3' _chemical_formula_weight 253.05 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1220(10) _cell_length_b 10.2160(10) _cell_length_c 10.709(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.753(5) _cell_angle_gamma 90.00 _cell_volume 887.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1 _cell_measurement_theta_max 15 _exptl_crystal_description cubic _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.894 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 4.604 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 'not measured' _exptl_absorpt_correction_T_max 'not measured' _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-nonius CAD4' _diffrn_measurement_method omega/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1290 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 22.47 _reflns_number_total 1151 _reflns_number_gt 881 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD 4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD 4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'X CAD4 (Harms & Wocaldo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond, 2.1c' _computing_publication_material 'WINGX Publication routines(Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.3247P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0046(14) _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1151 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Br1 Br 0.35186(9) -0.30188(6) 0.13154(6) 0.0472(3) Uani 1 1 d . . . O1 O 0.0873(5) 0.0297(4) -0.1756(3) 0.0367(10) Uani 1 1 d . . . O2 O -0.0367(6) 0.1491(5) -0.3222(4) 0.0510(12) Uani 1 1 d . . . O3 O 0.3383(6) 0.3903(5) 0.1025(5) 0.0574(14) Uani 1 1 d . . . C2 C 0.0452(8) 0.1485(6) -0.2257(6) 0.0382(15) Uani 1 1 d . . . C3 C 0.1070(8) 0.2623(7) -0.1563(6) 0.0411(16) Uani 1 1 d . . . H3 H 0.0792 0.3452 -0.1863 0.049 Uiso 1 1 calc R . . C4 C 0.2020(7) 0.2528(6) -0.0513(5) 0.0328(14) Uani 1 1 d . . . C5 C 0.3428(7) 0.1020(6) 0.1068(5) 0.0378(16) Uani 1 1 d . . . H5 H 0.3864 0.1721 0.1528 0.045 Uiso 1 1 calc R . . C6 C 0.3755(7) -0.0253(6) 0.1466(5) 0.0363(15) Uani 1 1 d . . . H6 H 0.4412 -0.0403 0.2187 0.044 Uiso 1 1 calc R . . C7 C 0.3113(7) -0.1274(6) 0.0798(6) 0.0319(14) Uani 1 1 d . . . C8 C 0.2148(7) -0.1101(5) -0.0276(5) 0.0315(14) Uani 1 1 d . . . H8 H 0.1716 -0.1811 -0.0726 0.038 Uiso 1 1 calc R . . C9 C 0.2456(7) 0.1252(6) -0.0012(5) 0.0312(14) Uani 1 1 d . . . C10 C 0.1839(7) 0.0186(6) -0.0668(5) 0.0287(13) Uani 1 1 d . . . C11 C 0.2573(8) 0.3774(6) 0.0077(6) 0.0418(16) Uani 1 1 d . . . H11 H 0.2252 0.4538 -0.0339 0.050 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 Br1 0.0534(5) 0.0255(5) 0.0614(5) 0.0093(3) -0.0096(3) 0.0064(3) O1 0.047(3) 0.025(2) 0.036(2) 0.0015(18) -0.011(2) 0.004(2) O2 0.061(3) 0.044(3) 0.046(3) 0.004(2) -0.019(2) 0.009(2) O3 0.070(3) 0.028(3) 0.073(3) -0.010(2) -0.017(3) -0.005(2) C2 0.040(4) 0.032(4) 0.042(4) 0.003(3) 0.001(3) 0.001(3) C3 0.045(4) 0.030(4) 0.048(4) 0.010(3) -0.001(3) 0.001(3) C4 0.034(3) 0.023(3) 0.042(4) 0.001(3) 0.006(3) -0.002(3) C5 0.038(4) 0.032(4) 0.043(4) -0.006(3) -0.007(3) 0.000(3) C6 0.037(4) 0.031(4) 0.039(4) 0.003(3) -0.014(3) 0.001(3) C7 0.035(4) 0.016(3) 0.045(3) 0.002(3) 0.004(3) 0.002(3) C8 0.035(3) 0.018(3) 0.041(3) -0.003(3) -0.007(3) 0.002(3) C9 0.033(3) 0.024(4) 0.036(3) -0.003(3) 0.001(3) 0.003(3) C10 0.025(3) 0.029(3) 0.032(3) 0.001(3) -0.002(3) 0.002(3) C11 0.047(4) 0.021(4) 0.057(4) 0.000(3) 0.005(4) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Br1 C7 1.891(6) . ? O1 C2 1.364(7) . ? O1 C10 1.378(7) . ? O2 C2 1.202(7) . ? O3 C11 1.191(7) . ? C2 C3 1.456(9) . ? C3 C4 1.337(9) . ? C4 C9 1.447(9) . ? C4 C11 1.481(9) . ? C5 C9 1.389(8) . ? C5 C6 1.390(9) . ? C6 C7 1.355(9) . ? C7 C8 1.372(8) . ? C8 C10 1.399(8) . ? C9 C10 1.377(8) . ? 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 C2 O1 C10 121.9(5) . . ? O2 C2 O1 117.4(6) . . ? O2 C2 C3 126.8(6) . . ? O1 C2 C3 115.8(5) . . ? C4 C3 C2 122.9(6) . . ? C3 C4 C9 119.9(6) . . ? C3 C4 C11 116.6(6) . . ? C9 C4 C11 123.6(5) . . ? C9 C5 C6 120.5(6) . . ? C7 C6 C5 119.7(5) . . ? C6 C7 C8 122.2(5) . . ? C6 C7 Br1 120.9(5) . . ? C8 C7 Br1 116.8(4) . . ? C7 C8 C10 117.3(5) . . ? C10 C9 C5 117.9(5) . . ? C10 C9 C4 116.6(5) . . ? C5 C9 C4 125.5(6) . . ? C9 C10 O1 123.0(5) . . ? C9 C10 C8 122.3(5) . . ? O1 C10 C8 114.7(5) . . ? O3 C11 C4 127.1(6) . . ? 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 C10 O1 C2 O2 178.5(5) . . . . ? C10 O1 C2 C3 -0.7(8) . . . . ? O2 C2 C3 C4 -177.8(7) . . . . ? O1 C2 C3 C4 1.3(9) . . . . ? C2 C3 C4 C9 -0.9(9) . . . . ? C2 C3 C4 C11 179.1(5) . . . . ? C9 C5 C6 C7 -0.3(9) . . . . ? C5 C6 C7 C8 0.5(9) . . . . ? C5 C6 C7 Br1 -179.6(4) . . . . ? C6 C7 C8 C10 -0.1(9) . . . . ? Br1 C7 C8 C10 -180.0(4) . . . . ? C6 C5 C9 C10 -0.2(9) . . . . ? C6 C5 C9 C4 179.5(6) . . . . ? C3 C4 C9 C10 -0.2(9) . . . . ? C11 C4 C9 C10 179.8(5) . . . . ? C3 C4 C9 C5 -179.9(6) . . . . ? C11 C4 C9 C5 0.1(9) . . . . ? C5 C9 C10 O1 -179.4(5) . . . . ? C4 C9 C10 O1 0.8(8) . . . . ? C5 C9 C10 C8 0.6(9) . . . . ? C4 C9 C10 C8 -179.1(5) . . . . ? C2 O1 C10 C9 -0.3(8) . . . . ? C2 O1 C10 C8 179.6(5) . . . . ? C7 C8 C10 C9 -0.5(9) . . . . ? C7 C8 C10 O1 179.6(5) . . . . ? C3 C4 C11 O3 177.9(6) . . . . ? C9 C4 C11 O3 -2.1(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.752 _refine_diff_density_min -0.565 _refine_diff_density_rms 0.111 #======END data_6fluoro-4-formylcoumarin _database_code_depnum_ccdc_archive 'CCDC 213051' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-Fluoro-4-formylcoumarin ; _chemical_name_common 6-Fluoro-4-formylcoumarin _chemical_melting_point 144 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H5 F O3' _chemical_formula_weight 192.14 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.115(2) _cell_length_b 8.082(2) _cell_length_c 16.330(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.230(10) _cell_angle_gamma 90.00 _cell_volume 804.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1 _cell_measurement_theta_max 15 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 'not measured' _exptl_absorpt_correction_T_max 'not measured' _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method omega/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1439 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 23.99 _reflns_number_total 1260 _reflns_number_gt 742 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD 4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD 4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'X CAD4 (Harms & Wocaldo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond, 2.1c' _computing_publication_material 'WINGX Publication routines (Farrugia, 1999) ' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.1015P)^2^+0.1045P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.004(6) _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1260 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1088 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1782 _refine_ls_wR_factor_gt 0.1563 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 C9 C 0.0406(5) 0.2266(4) 0.4253(2) 0.0364(9) Uani 1 1 d . . . C4 C 0.0374(5) 0.1798(4) 0.3399(2) 0.0376(9) Uani 1 1 d . . . C10 C -0.1341(5) 0.1772(4) 0.4697(2) 0.0401(9) Uani 1 1 d . . . C3 C -0.1287(6) 0.0858(4) 0.3068(2) 0.0440(9) Uani 1 1 d . . . H3A H -0.1274 0.0539 0.2521 0.053 Uiso 1 1 calc R . . C2 C -0.3074(6) 0.0331(5) 0.3528(3) 0.0484(10) Uani 1 1 d . . . C5 C 0.2082(6) 0.3185(4) 0.4688(2) 0.0424(9) Uani 1 1 d . . . H5A H 0.3286 0.3559 0.4425 0.051 Uiso 1 1 calc R . . C8 C -0.1479(6) 0.2125(5) 0.5511(2) 0.0473(10) Uani 1 1 d . . . H8A H -0.2674 0.1764 0.5783 0.057 Uiso 1 1 calc R . . C11 C 0.2073(6) 0.2244(5) 0.2845(2) 0.0480(10) Uani 1 1 d . . . H11A H 0.1950 0.1778 0.2323 0.058 Uiso 1 1 calc R . . C6 C 0.1907(6) 0.3511(5) 0.5493(2) 0.0471(10) Uani 1 1 d . . . C7 C 0.0183(6) 0.3025(5) 0.5924(2) 0.0528(11) Uani 1 1 d . . . H7A H 0.0128 0.3291 0.6476 0.063 Uiso 1 1 calc R . . O1 O -0.3049(4) 0.0842(3) 0.43267(16) 0.0487(8) Uani 1 1 d . . . O2 O -0.4598(4) -0.0516(4) 0.32708(19) 0.0674(9) Uani 1 1 d . . . O3 O 0.3604(5) 0.3151(4) 0.30012(18) 0.0658(9) Uani 1 1 d . . . F1 F 0.3529(4) 0.4402(3) 0.59095(15) 0.0716(8) 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 C9 0.0361(19) 0.0276(17) 0.046(2) 0.0059(16) 0.0065(16) 0.0027(14) C4 0.0338(19) 0.0347(19) 0.044(2) 0.0083(16) 0.0042(15) 0.0028(15) C10 0.0363(19) 0.0324(19) 0.052(2) 0.0041(17) 0.0051(16) 0.0009(16) C3 0.044(2) 0.041(2) 0.047(2) -0.0014(18) 0.0050(16) 0.0018(17) C2 0.043(2) 0.041(2) 0.061(3) -0.0012(19) -0.0001(18) 0.0002(18) C5 0.0390(19) 0.039(2) 0.049(2) 0.0041(17) 0.0064(16) -0.0025(16) C8 0.045(2) 0.052(2) 0.046(2) 0.0019(18) 0.0147(18) -0.0004(18) C11 0.049(2) 0.049(2) 0.047(2) 0.0104(18) 0.0095(18) 0.0053(19) C6 0.048(2) 0.044(2) 0.048(2) -0.0043(19) -0.0018(18) -0.0060(18) C7 0.056(2) 0.058(3) 0.045(2) 0.0005(19) 0.0071(19) 0.003(2) O1 0.0367(14) 0.0498(16) 0.0604(17) -0.0018(14) 0.0096(12) -0.0113(12) O2 0.0530(17) 0.0661(19) 0.083(2) -0.0126(17) 0.0007(15) -0.0192(15) O3 0.0552(18) 0.074(2) 0.070(2) 0.0113(16) 0.0124(15) -0.0180(16) F1 0.0688(16) 0.0788(17) 0.0660(16) -0.0099(14) -0.0030(12) -0.0268(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C9 C10 1.393(5) . ? C9 C5 1.414(5) . ? C9 C4 1.443(5) . ? C4 C3 1.349(5) . ? C4 C11 1.472(5) . ? C10 C8 1.367(5) . ? C10 O1 1.389(4) . ? C3 C2 1.435(5) . ? C2 O2 1.207(4) . ? C2 O1 1.368(5) . ? C5 C6 1.353(5) . ? C8 C7 1.384(5) . ? C11 O3 1.201(5) . ? C6 F1 1.365(4) . ? C6 C7 1.367(5) . ? 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 C10 C9 C5 116.3(3) . . ? C10 C9 C4 118.2(3) . . ? C5 C9 C4 125.5(3) . . ? C3 C4 C9 119.4(3) . . ? C3 C4 C11 115.9(4) . . ? C9 C4 C11 124.7(3) . . ? C8 C10 O1 116.0(3) . . ? C8 C10 C9 123.4(3) . . ? O1 C10 C9 120.6(3) . . ? C4 C3 C2 122.5(4) . . ? O2 C2 O1 117.2(4) . . ? O2 C2 C3 125.8(4) . . ? O1 C2 C3 117.0(3) . . ? C6 C5 C9 119.0(3) . . ? C10 C8 C7 119.2(4) . . ? O3 C11 C4 126.4(4) . . ? C5 C6 F1 118.7(3) . . ? C5 C6 C7 124.2(3) . . ? F1 C6 C7 117.1(3) . . ? C6 C7 C8 117.8(4) . . ? C2 O1 C10 122.3(3) . . ? 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 C10 C9 C4 C3 -2.3(5) . . . . ? C5 C9 C4 C3 177.2(3) . . . . ? C10 C9 C4 C11 179.0(3) . . . . ? C5 C9 C4 C11 -1.5(5) . . . . ? C5 C9 C10 C8 -0.4(5) . . . . ? C4 C9 C10 C8 179.2(3) . . . . ? C5 C9 C10 O1 -179.0(3) . . . . ? C4 C9 C10 O1 0.6(5) . . . . ? C9 C4 C3 C2 1.6(5) . . . . ? C11 C4 C3 C2 -179.6(3) . . . . ? C4 C3 C2 O2 -179.5(4) . . . . ? C4 C3 C2 O1 0.8(5) . . . . ? C10 C9 C5 C6 0.6(5) . . . . ? C4 C9 C5 C6 -179.0(3) . . . . ? O1 C10 C8 C7 179.0(3) . . . . ? C9 C10 C8 C7 0.4(6) . . . . ? C3 C4 C11 O3 175.0(4) . . . . ? C9 C4 C11 O3 -6.3(6) . . . . ? C9 C5 C6 F1 -179.8(3) . . . . ? C9 C5 C6 C7 -0.8(6) . . . . ? C5 C6 C7 C8 0.8(6) . . . . ? F1 C6 C7 C8 179.8(3) . . . . ? C10 C8 C7 C6 -0.5(6) . . . . ? O2 C2 O1 C10 177.7(3) . . . . ? C3 C2 O1 C10 -2.6(5) . . . . ? C8 C10 O1 C2 -176.8(3) . . . . ? C9 C10 O1 C2 1.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.230 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.063 #======END data_7-fluoro-4-formylcoumarin _database_code_depnum_ccdc_archive 'CCDC 213052' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-Fluoro-4-formylcoumarin ; _chemical_name_common 7-Fluoro-4-formylcoumarin _chemical_melting_point 170 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H5 F O3' _chemical_formula_weight 192.14 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7460(10) _cell_length_b 8.5520(10) _cell_length_c 9.212(2) _cell_angle_alpha 113.792(3) _cell_angle_beta 102.163(3) _cell_angle_gamma 93.126(3) _cell_volume 399.95(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1 _cell_measurement_theta_max 15 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 'not measured' _exptl_absorpt_correction_T_max 'not measured' _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'omega/2theta ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1401 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 23.99 _reflns_number_total 1260 _reflns_number_gt 671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD 4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD 4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocaldo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond, 2.1c' _computing_publication_material 'WINGX Publication routines (Farrugia, 1999) ' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0895P)^2^+0.0286P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(11) _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1260 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1256 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1611 _refine_ls_wR_factor_gt 0.1391 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.6760(4) 0.5895(3) 0.9463(3) 0.0706(9) Uani 1 1 d . . . O1 O 0.1599(4) 0.3303(3) 0.4218(3) 0.0462(8) Uani 1 1 d . . . O2 O -0.0914(4) 0.2243(4) 0.1782(3) 0.0589(9) Uani 1 1 d . . . O3 O 0.7851(5) -0.0746(4) 0.2977(3) 0.0628(9) Uani 1 1 d . . . C2 C 0.0952(6) 0.2146(5) 0.2621(5) 0.0456(11) Uani 1 1 d . . . C3 C 0.2520(6) 0.0909(5) 0.2064(5) 0.0446(10) Uani 1 1 d . . . H3A H 0.2098 0.0094 0.0976 0.054 Uiso 1 1 calc R . . C4 C 0.4590(6) 0.0891(5) 0.3068(4) 0.0371(9) Uani 1 1 d . . . C5 C 0.7403(6) 0.2307(5) 0.5935(5) 0.0454(11) Uani 1 1 d . . . H5A H 0.8491 0.1545 0.5632 0.054 Uiso 1 1 calc R . . C6 C 0.7897(7) 0.3537(5) 0.7489(5) 0.0485(11) Uani 1 1 d . . . H6A H 0.9300 0.3627 0.8257 0.058 Uiso 1 1 calc R . . C7 C 0.6258(7) 0.4660(5) 0.7910(4) 0.0449(10) Uani 1 1 d . . . C8 C 0.4158(7) 0.4584(5) 0.6832(5) 0.0452(10) Uani 1 1 d . . . H8A H 0.3086 0.5355 0.7151 0.054 Uiso 1 1 calc R . . C9 C 0.5261(6) 0.2145(5) 0.4745(5) 0.0373(10) Uani 1 1 d . . . C10 C 0.3723(6) 0.3345(5) 0.5297(5) 0.0391(10) Uani 1 1 d . . . C11 C 0.5977(7) -0.0501(5) 0.2300(5) 0.0489(11) Uani 1 1 d . . . H11A H 0.5334 -0.1247 0.1201 0.059 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 0.0565(16) 0.0740(19) 0.0586(18) 0.0121(15) 0.0006(13) 0.0126(13) O1 0.0227(13) 0.0524(17) 0.0562(17) 0.0178(14) 0.0031(12) 0.0168(12) O2 0.0290(16) 0.068(2) 0.0680(19) 0.0260(16) -0.0073(14) 0.0187(13) O3 0.0343(16) 0.068(2) 0.080(2) 0.0256(17) 0.0087(15) 0.0311(14) C2 0.026(2) 0.050(3) 0.056(3) 0.021(2) 0.004(2) 0.0122(18) C3 0.0302(19) 0.047(2) 0.047(2) 0.0130(19) 0.0040(18) 0.0107(17) C4 0.0249(19) 0.042(2) 0.045(2) 0.0180(19) 0.0095(17) 0.0119(17) C5 0.0236(19) 0.057(3) 0.057(3) 0.028(2) 0.0038(19) 0.0132(18) C6 0.028(2) 0.055(2) 0.047(3) 0.013(2) -0.0039(18) 0.0085(18) C7 0.043(2) 0.038(2) 0.040(2) 0.006(2) 0.0050(18) 0.0059(19) C8 0.039(2) 0.045(2) 0.051(3) 0.017(2) 0.0140(18) 0.0148(18) C9 0.0233(18) 0.039(2) 0.054(2) 0.025(2) 0.0093(17) 0.0090(16) C10 0.0221(18) 0.045(2) 0.052(2) 0.023(2) 0.0040(18) 0.0102(17) C11 0.035(2) 0.050(2) 0.059(3) 0.019(2) 0.013(2) 0.0153(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C7 1.349(4) . ? O1 C2 1.355(4) . ? O1 C10 1.391(4) . ? O2 C2 1.210(4) . ? O3 C11 1.200(4) . ? C2 C3 1.434(5) . ? C3 C4 1.349(4) . ? C4 C9 1.433(5) . ? C4 C11 1.488(5) . ? C5 C6 1.348(5) . ? C5 C9 1.423(5) . ? C6 C7 1.382(5) . ? C7 C8 1.371(5) . ? C8 C10 1.341(5) . ? C9 C10 1.400(5) . ? 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 C2 O1 C10 122.5(3) . . ? O2 C2 O1 117.0(3) . . ? O2 C2 C3 125.4(4) . . ? O1 C2 C3 117.6(3) . . ? C4 C3 C2 122.1(4) . . ? C3 C4 C9 119.4(4) . . ? C3 C4 C11 115.1(3) . . ? C9 C4 C11 125.5(3) . . ? C6 C5 C9 121.7(4) . . ? C5 C6 C7 118.1(4) . . ? F1 C7 C8 118.5(4) . . ? F1 C7 C6 118.1(3) . . ? C8 C7 C6 123.5(4) . . ? C10 C8 C7 116.9(4) . . ? C10 C9 C5 115.6(4) . . ? C10 C9 C4 118.7(3) . . ? C5 C9 C4 125.7(4) . . ? C8 C10 O1 116.0(3) . . ? C8 C10 C9 124.3(3) . . ? O1 C10 C9 119.8(3) . . ? O3 C11 C4 125.7(4) . . ? 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 C10 O1 C2 O2 -178.7(3) . . . . ? C10 O1 C2 C3 1.4(5) . . . . ? O2 C2 C3 C4 179.3(4) . . . . ? O1 C2 C3 C4 -0.9(6) . . . . ? C2 C3 C4 C9 -0.2(6) . . . . ? C2 C3 C4 C11 178.7(4) . . . . ? C9 C5 C6 C7 -0.2(6) . . . . ? C5 C6 C7 F1 -179.7(3) . . . . ? C5 C6 C7 C8 0.2(6) . . . . ? F1 C7 C8 C10 179.7(3) . . . . ? C6 C7 C8 C10 -0.2(6) . . . . ? C6 C5 C9 C10 0.2(5) . . . . ? C6 C5 C9 C4 179.6(4) . . . . ? C3 C4 C9 C10 0.7(5) . . . . ? C11 C4 C9 C10 -178.1(3) . . . . ? C3 C4 C9 C5 -178.7(4) . . . . ? C11 C4 C9 C5 2.5(6) . . . . ? C7 C8 C10 O1 -179.3(3) . . . . ? C7 C8 C10 C9 0.2(6) . . . . ? C2 O1 C10 C8 178.6(4) . . . . ? C2 O1 C10 C9 -0.9(5) . . . . ? C5 C9 C10 C8 -0.2(5) . . . . ? C4 C9 C10 C8 -179.6(4) . . . . ? C5 C9 C10 O1 179.2(3) . . . . ? C4 C9 C10 O1 -0.2(5) . . . . ? C3 C4 C11 O3 -179.8(4) . . . . ? C9 C4 C11 O3 -1.0(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.266 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.073