# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Itzia Padilla-Martinez' _publ_contact_author_email IPADILLAMAR@IPN.MX _publ_section_title ; Competition between OH***O hydrogen bonding and multicentered halogen-dipole interactions on intramolecular three centered hydrogen bonding formation in ethanol amides derived from 3-acyl coumarins ; loop_ _publ_author_name 'Itzia Padilla-Martinez' 'Efren V Garcia-Baez' 'N Alejandra Mancilla-Margalli' ; F.J.Martinez-Martinez ; 'Luis M Morin-Sanchez' 'Ana L Peraza-Campos' ; R.J.Santos-Contreras ; # Attachment '1a.cif' data_baesevx _database_code_depnum_ccdc_archive 'CCDC 704502' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common N-(2-hydroxyethyl)-2-oxo-2H-chromene-3-carboxamide _chemical_melting_point ? _chemical_formula_moiety 'C12 H11 N O4' _chemical_formula_sum 'C12 H11 N O4' _chemical_formula_weight 233.22 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 17.372(4) _cell_length_b 5.1248(13) _cell_length_c 11.968(3) _cell_angle_alpha 90 _cell_angle_beta 103.925(4) _cell_angle_gamma 90 _cell_volume 1034.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 200 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 5 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 10189 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2027 _reflns_number_gt 1641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997) and WINGX-2003 (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^)+(0.0683P)^2^+0.3079P] 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 2027 _refine_ls_number_parameters 154 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.373 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.36410(9) 0.5683(3) 0.93429(14) 1.000 0.0170(5) . . O2 O Uani 0.29743(10) 0.8874(3) 0.98714(15) 1.000 0.0215(6) . . O11 O Uani 0.11651(10) 0.8071(4) 0.68320(14) 1.000 0.0204(5) . . O15 O Uani 0.14687(10) 1.4318(4) 0.99491(15) 1.000 0.0274(6) . . N12 N Uani 0.15321(12) 1.0188(4) 0.85176(17) 1.000 0.0181(7) . . C2 C Uani 0.29830(14) 0.7251(5) 0.9143(2) 1.000 0.0168(7) . . C3 C Uani 0.23823(14) 0.6816(5) 0.8077(2) 1.000 0.0164(7) . . C4 C Uani 0.24874(14) 0.4939(5) 0.7346(2) 1.000 0.0164(7) . . C5 C Uani 0.33052(14) 0.1326(5) 0.6853(2) 1.000 0.0177(7) . . C6 C Uani 0.39792(14) -0.0171(5) 0.7148(2) 1.000 0.0187(8) . . C7 C Uani 0.45381(14) 0.0317(5) 0.8171(2) 1.000 0.0179(7) . . C8 C Uani 0.44247(14) 0.2285(5) 0.8901(2) 1.000 0.0179(7) . . C9 C Uani 0.37441(14) 0.3751(5) 0.8597(2) 1.000 0.0151(7) . . C10 C Uani 0.31737(14) 0.3327(5) 0.7576(2) 1.000 0.0156(7) . . C11 C Uani 0.16444(14) 0.8426(5) 0.7767(2) 1.000 0.0169(7) . . C13 C Uani 0.08418(14) 1.1860(5) 0.8316(2) 1.000 0.0199(8) . . C14 C Uani 0.07535(15) 1.3011(6) 0.9428(2) 1.000 0.0248(8) . . H4 H Uiso 0.20910 0.46790 0.66540 1.000 0.0200 calc R H5 H Uiso 0.29250 0.09980 0.61510 1.000 0.0210 calc R H6 H Uiso 0.40630 -0.15370 0.66540 1.000 0.0220 calc R H7 H Uiso 0.50040 -0.07200 0.83710 1.000 0.0210 calc R H8 H Uiso 0.48090 0.26200 0.95980 1.000 0.0210 calc R H12 H Uiso 0.18940 1.03530 0.91700 1.000 0.0220 calc R H13A H Uiso 0.03720 1.08580 0.79660 1.000 0.0240 calc R H13B H Uiso 0.08960 1.32480 0.77890 1.000 0.0240 calc R H14A H Uiso 0.03130 1.42290 0.92870 1.000 0.0300 calc R H14B H Uiso 0.06490 1.16440 0.99330 1.000 0.0300 calc R H15 H Uiso 0.14100 1.51460 1.05290 1.000 0.0410 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 0.0172(9) 0.0192(9) 0.0124(9) -0.0015(7) -0.0006(7) 0.0021(7) O2 0.0233(10) 0.0233(10) 0.0151(9) -0.0044(8) -0.0006(7) 0.0029(7) O11 0.0166(9) 0.0288(10) 0.0139(9) -0.0010(7) -0.0003(7) 0.0025(7) O15 0.0195(10) 0.0388(12) 0.0215(10) -0.0121(9) 0.0005(8) -0.0011(8) N12 0.0155(11) 0.0218(12) 0.0146(11) -0.0016(8) -0.0010(8) 0.0019(8) C2 0.0167(12) 0.0188(13) 0.0145(12) 0.0020(10) 0.0030(10) -0.0011(10) C3 0.0165(12) 0.0185(13) 0.0138(12) 0.0026(10) 0.0031(10) -0.0015(10) C4 0.0139(12) 0.0232(13) 0.0106(12) 0.0008(10) 0.0002(9) -0.0039(10) C5 0.0171(12) 0.0246(14) 0.0104(11) 0.0000(10) 0.0013(9) -0.0029(10) C6 0.0192(13) 0.0209(14) 0.0169(13) -0.0012(10) 0.0062(10) -0.0004(10) C7 0.0143(12) 0.0200(13) 0.0189(13) 0.0040(10) 0.0031(10) 0.0015(10) C8 0.0161(12) 0.0227(14) 0.0128(12) 0.0028(10) -0.0005(9) -0.0020(10) C9 0.0170(12) 0.0175(13) 0.0110(12) 0.0008(10) 0.0035(9) -0.0030(10) C10 0.0144(12) 0.0193(13) 0.0132(12) 0.0020(10) 0.0036(9) -0.0019(9) C11 0.0161(12) 0.0204(13) 0.0142(12) 0.0024(10) 0.0038(10) -0.0031(10) C13 0.0135(12) 0.0235(14) 0.0206(14) -0.0027(11) 0.0002(10) 0.0008(10) C14 0.0162(13) 0.0351(16) 0.0220(14) -0.0058(12) 0.0025(11) 0.0018(11) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.370(3) . . yes O1 C9 1.373(3) . . yes O2 C2 1.208(3) . . yes O11 C11 1.237(3) . . yes O15 C14 1.417(3) . . yes O15 H15 0.8400 . . no N12 C13 1.446(3) . . yes N12 C11 1.321(3) . . yes N12 H12 0.8800 . . no C2 C3 1.458(3) . . no C3 C4 1.342(4) . . no C3 C11 1.494(4) . . no C4 C10 1.422(4) . . no C5 C10 1.396(4) . . no C5 C6 1.373(4) . . no C6 C7 1.390(3) . . no C7 C8 1.379(4) . . no C8 C9 1.374(4) . . no C9 C10 1.393(3) . . no C13 C14 1.497(3) . . no C4 H4 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C8 H8 0.9500 . . no C13 H13A 0.9700 . . no C13 H13B 0.9700 . . no C14 H14A 0.9700 . . no C14 H14B 0.9700 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C9 122.89(19) . . . yes C14 O15 H15 110.00 . . . no C11 N12 C13 123.0(2) . . . yes C11 N12 H12 119.00 . . . no C13 N12 H12 119.00 . . . no O2 C2 C3 127.3(2) . . . yes O1 C2 O2 115.6(2) . . . yes O1 C2 C3 117.0(2) . . . yes C2 C3 C4 119.9(2) . . . no C2 C3 C11 121.6(2) . . . no C4 C3 C11 118.5(2) . . . no C3 C4 C10 122.0(2) . . . no C6 C5 C10 120.5(2) . . . no C5 C6 C7 119.8(2) . . . no C6 C7 C8 120.9(2) . . . no C7 C8 C9 118.5(2) . . . no O1 C9 C8 117.4(2) . . . yes O1 C9 C10 120.4(2) . . . yes C8 C9 C10 122.2(2) . . . no C4 C10 C5 124.2(2) . . . no C4 C10 C9 117.8(2) . . . no C5 C10 C9 118.1(2) . . . no O11 C11 C3 119.6(2) . . . yes O11 C11 N12 122.6(2) . . . yes N12 C11 C3 117.8(2) . . . yes N12 C13 C14 110.1(2) . . . yes O15 C14 C13 108.1(2) . . . yes C3 C4 H4 119.00 . . . no C10 C4 H4 119.00 . . . no C6 C5 H5 120.00 . . . no C10 C5 H5 120.00 . . . no C5 C6 H6 120.00 . . . no C7 C6 H6 120.00 . . . no C6 C7 H7 120.00 . . . no C8 C7 H7 120.00 . . . no C7 C8 H8 121.00 . . . no C9 C8 H8 121.00 . . . no N12 C13 H13A 110.00 . . . no N12 C13 H13B 110.00 . . . no C14 C13 H13A 110.00 . . . no C14 C13 H13B 110.00 . . . no H13A C13 H13B 108.00 . . . no O15 C14 H14A 110.00 . . . no O15 C14 H14B 110.00 . . . no C13 C14 H14A 110.00 . . . no C13 C14 H14B 110.00 . . . no H14A C14 H14B 108.00 . . . no 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 C9 O1 C2 O2 -179.7(2) . . . . no C9 O1 C2 C3 -0.8(3) . . . . no C2 O1 C9 C8 -179.1(2) . . . . no C2 O1 C9 C10 0.9(3) . . . . no C13 N12 C11 O11 -0.1(4) . . . . no C11 N12 C13 C14 162.3(2) . . . . no C13 N12 C11 C3 -180.0(2) . . . . no O1 C2 C3 C11 -179.5(2) . . . . no O1 C2 C3 C4 0.3(3) . . . . no O2 C2 C3 C11 -0.7(4) . . . . no O2 C2 C3 C4 179.1(3) . . . . no C2 C3 C11 O11 176.9(2) . . . . no C2 C3 C11 N12 -3.2(4) . . . . no C4 C3 C11 O11 -2.8(4) . . . . no C4 C3 C11 N12 177.1(2) . . . . no C11 C3 C4 C10 179.9(2) . . . . no C2 C3 C4 C10 0.1(4) . . . . no C3 C4 C10 C9 0.0(4) . . . . no C3 C4 C10 C5 179.0(2) . . . . no C6 C5 C10 C9 0.0(4) . . . . no C10 C5 C6 C7 -0.4(4) . . . . no C6 C5 C10 C4 -178.9(2) . . . . no C5 C6 C7 C8 0.3(4) . . . . no C6 C7 C8 C9 0.3(4) . . . . no C7 C8 C9 C10 -0.6(4) . . . . no C7 C8 C9 O1 179.4(2) . . . . no O1 C9 C10 C4 -0.5(4) . . . . no O1 C9 C10 C5 -179.5(2) . . . . no C8 C9 C10 C4 179.5(2) . . . . no C8 C9 C10 C5 0.5(4) . . . . no N12 C13 C14 O15 55.6(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C7 3.330(3) . 1_565 no O1 C5 3.357(3) . 4_555 no O1 C6 3.277(3) . 4_555 no O2 C9 3.368(3) . 1_565 no O2 C5 3.369(3) . 4_565 no O2 N12 2.721(3) . . no O2 C4 3.326(3) . 4_565 no O11 O15 2.778(3) . 4_574 no O11 C14 3.311(3) . 2_546 no O15 C2 3.366(3) . 1_565 no O15 N12 2.742(3) . . no O15 O11 2.778(3) . 4_575 no O15 C3 3.300(3) . 1_565 no O1 H5 2.8800 . 4_555 no O1 H6 2.7200 . 4_555 no O1 H8 2.8200 . 3_667 no O2 H12 2.0100 . . no O2 H6 2.7600 . 4_555 no O11 H15 1.9400 . 4_574 no O11 H4 2.4100 . . no O11 H13A 2.5800 . . no O11 H13B 2.8100 . 1_545 no O11 H14A 2.6600 . 2_546 no O15 H12 2.4200 . . no O15 H4 2.9100 . 4_565 no O15 H5 2.6000 . 4_565 no N12 O2 2.721(3) . . no N12 O15 2.742(3) . . no N12 C4 3.431(3) . 1_565 no C2 O15 3.366(3) . 1_545 no C2 C5 3.595(4) . 1_565 no C2 C6 3.526(4) . 1_565 no C2 C7 3.554(4) . 1_565 no C3 C5 3.345(4) . 1_565 no C3 C6 3.578(4) . 1_565 no C3 O15 3.300(3) . 1_545 no C4 O2 3.326(3) . 4_564 no C4 N12 3.431(3) . 1_545 no C5 C2 3.595(4) . 1_545 no C5 C3 3.345(4) . 1_545 no C5 O1 3.357(3) . 4_554 no C5 O2 3.369(3) . 4_564 no C6 C3 3.578(4) . 1_545 no C6 C8 3.555(4) . 2_646 no C6 C7 3.550(4) . 2_646 no C6 C2 3.526(4) . 1_545 no C6 O1 3.277(3) . 4_554 no C7 C6 3.550(4) . 2_656 no C7 O1 3.330(3) . 1_545 no C7 C2 3.554(4) . 1_545 no C8 C6 3.555(4) . 2_656 no C9 O2 3.368(3) . 1_545 no C14 O11 3.311(3) . 2_556 no C2 H12 2.4800 . . no C2 H5 2.9500 . 4_555 no C4 H13B 3.0600 . 1_545 no C6 H7 3.0400 . 2_656 no C7 H7 2.9800 . 2_656 no C7 H6 2.8800 . 2_656 no C7 H8 3.0400 . 3_657 no C8 H6 2.9200 . 2_656 no C11 H15 2.7100 . 4_574 no C11 H13B 2.9600 . 1_545 no C13 H13A 3.0700 . 2_556 no C14 H14A 3.0300 . 3_587 no H4 O11 2.4100 . . no H4 H5 2.5400 . . no H4 O15 2.9100 . 4_564 no H5 H4 2.5400 . . no H5 O1 2.8800 . 4_554 no H5 O15 2.6000 . 4_564 no H5 C2 2.9500 . 4_554 no H6 C7 2.8800 . 2_646 no H6 C8 2.9200 . 2_646 no H6 O1 2.7200 . 4_554 no H6 O2 2.7600 . 4_554 no H7 C6 3.0400 . 2_646 no H7 C7 2.9800 . 2_646 no H7 H8 2.5700 . 3_657 no H8 O1 2.8200 . 3_667 no H8 C7 3.0400 . 3_657 no H8 H7 2.5700 . 3_657 no H12 O2 2.0100 . . no H12 O15 2.4200 . . no H12 C2 2.4800 . . no H13A O11 2.5800 . . no H13A C13 3.0700 . 2_546 no H13A H13B 2.5500 . 2_546 no H13B O11 2.8100 . 1_565 no H13B C4 3.0600 . 1_565 no H13B C11 2.9600 . 1_565 no H13B H13A 2.5500 . 2_556 no H14A O11 2.6600 . 2_556 no H14A C14 3.0300 . 3_587 no H14A H14A 2.3700 . 3_587 no H15 O11 1.9400 . 4_575 no H15 C11 2.7100 . 4_575 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N12 H12 O2 0.8800 2.0100 2.721(3) 137.00 . yes N12 H12 O15 0.8800 2.4200 2.742(3) 102.00 . yes O15 H15 O11 0.8400 1.9400 2.778(3) 174.00 4_575 yes C4 H4 O11 0.9500 2.4100 2.748(3) 100.00 . yes C5 H5 O15 0.9500 2.6000 3.461(3) 151.00 4_564 yes _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.340 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.059 # Attachment '2a.cif' data_m3mendm _database_code_depnum_ccdc_archive 'CCDC 704503' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(2-hydroxyethyl)-6-nitro-2-oxo-2H-chromene-3-carboxamide hydrate ; _chemical_name_common ;N-(2-hydroxyethyl)-6-nitro-2-oxo-2H-chromene-3-carboxamide hydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 N2 O7' _chemical_formula_sum 'C12 H12 N2 O7' _chemical_formula_weight 296.24 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.0399(13) _cell_length_b 8.901(2) _cell_length_c 14.031(4) _cell_angle_alpha 94.044(4) _cell_angle_beta 91.533(4) _cell_angle_gamma 90.092(4) _cell_volume 627.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 600 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_min 0.8614 _exptl_absorpt_correction_T_max 0.8620 _exptl_absorpt_correction_T_ave 0.8617 _exptl_crystal_size_rad 0.2000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6037 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2179 _reflns_number_gt 1958 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0493P)^2^+0.2307P] 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 0.030(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2179 _refine_ls_number_parameters 191 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1304 _refine_ls_wR_factor_gt 0.1267 _refine_ls_goodness_of_fit_ref 1.243 _refine_ls_restrained_S_all 1.243 _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 0.7677(3) 0.86941(17) 0.98598(10) 0.0385(4) Uani 1 1 d . . . O2 O 0.8695(3) 0.88110(18) 0.83642(11) 0.0452(4) Uani 1 1 d . . . O6A O 1.1000(4) 0.5949(2) 1.36723(12) 0.0674(6) Uani 1 1 d . . . O6B O 0.7707(4) 0.7309(3) 1.41295(13) 0.0722(6) Uani 1 1 d . . . O11 O 1.4982(3) 0.57416(18) 0.86833(10) 0.0437(4) Uani 1 1 d . . . O15 O 1.2785(3) 0.86295(19) 0.58827(11) 0.0495(5) Uani 1 1 d D . . H15 H 1.4238 0.9090 0.5960 0.074 Uiso 1 1 d RD . . N6 N 0.9184(4) 0.6800(2) 1.35167(14) 0.0469(5) Uani 1 1 d . . . N12 N 1.2769(4) 0.7093(2) 0.76323(12) 0.0392(5) Uani 1 1 d D . . H12 H 1.1431 0.7703 0.7536 0.047 Uiso 1 1 calc RD . . C2 C 0.9218(4) 0.8241(2) 0.90976(15) 0.0327(5) Uani 1 1 d . . . C3 C 1.1332(4) 0.7162(2) 0.92680(14) 0.0303(5) Uani 1 1 d . . . C4 C 1.1684(4) 0.6651(2) 1.01405(14) 0.0317(5) Uani 1 1 d . . . H4 H 1.3060 0.5948 1.0244 0.038 Uiso 1 1 calc R . . C5 C 1.0396(4) 0.6676(2) 1.18429(15) 0.0348(5) Uani 1 1 d . . . H5 H 1.1747 0.5977 1.1986 0.042 Uiso 1 1 calc R . . C6 C 0.8748(4) 0.7256(2) 1.25404(15) 0.0367(5) Uani 1 1 d . . . C7 C 0.6712(4) 0.8255(3) 1.23569(17) 0.0419(6) Uani 1 1 d . . . H7 H 0.5583 0.8612 1.2854 0.050 Uiso 1 1 calc R . . C8 C 0.6346(4) 0.8720(3) 1.14544(16) 0.0410(6) Uani 1 1 d . . . H8 H 0.4969 0.9404 1.1314 0.049 Uiso 1 1 calc R . . C9 C 0.8032(4) 0.8169(2) 1.07503(15) 0.0329(5) Uani 1 1 d . . . C10 C 1.0036(4) 0.7140(2) 1.09196(14) 0.0311(5) Uani 1 1 d . . . C11 C 1.3181(4) 0.6613(2) 0.84969(14) 0.0317(5) Uani 1 1 d . . . C13 C 1.4456(5) 0.6646(3) 0.68388(15) 0.0422(6) Uani 1 1 d . . . H13A H 1.4747 0.5567 0.6818 0.051 Uiso 1 1 calc R . . H13B H 1.6166 0.7143 0.6934 0.051 Uiso 1 1 calc R . . C14 C 1.3212(5) 0.7051(3) 0.59069(16) 0.0447(6) Uani 1 1 d . . . H14A H 1.4355 0.6715 0.5389 0.054 Uiso 1 1 calc R . . H14B H 1.1526 0.6528 0.5806 0.054 Uiso 1 1 calc R . . O8 O 0.7627(3) 1.0139(2) 0.59881(12) 0.0526(5) Uani 1 1 d D . . H8A H 0.7701 1.0529 0.5460 0.079 Uiso 1 1 d RD . . H8B H 0.9091 0.9689 0.6011 0.079 Uiso 1 1 d RD . . 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 0.0349(8) 0.0415(9) 0.0395(9) 0.0045(7) 0.0015(6) 0.0151(7) O2 0.0441(10) 0.0507(10) 0.0423(9) 0.0148(8) -0.0001(7) 0.0178(7) O6A 0.0802(14) 0.0851(15) 0.0383(10) 0.0121(9) 0.0055(9) 0.0262(12) O6B 0.0707(13) 0.1059(17) 0.0407(10) 0.0009(10) 0.0247(10) 0.0100(12) O11 0.0444(9) 0.0524(10) 0.0355(8) 0.0107(7) 0.0061(7) 0.0227(8) O15 0.0468(10) 0.0556(11) 0.0481(10) 0.0184(8) -0.0017(8) 0.0026(8) N6 0.0491(12) 0.0566(13) 0.0347(11) -0.0017(9) 0.0092(9) -0.0034(10) N12 0.0377(10) 0.0500(12) 0.0308(10) 0.0093(8) 0.0013(8) 0.0147(8) C2 0.0305(11) 0.0313(11) 0.0364(12) 0.0023(9) -0.0013(9) 0.0020(9) C3 0.0271(11) 0.0291(11) 0.0347(11) 0.0020(8) -0.0012(8) 0.0033(8) C4 0.0271(11) 0.0331(12) 0.0349(11) 0.0018(9) 0.0013(8) 0.0073(8) C5 0.0330(11) 0.0372(12) 0.0342(12) 0.0008(9) 0.0026(9) 0.0022(9) C6 0.0360(12) 0.0410(13) 0.0325(11) -0.0022(9) 0.0058(9) -0.0052(9) C7 0.0365(12) 0.0449(14) 0.0431(13) -0.0101(10) 0.0115(10) 0.0007(10) C8 0.0319(12) 0.0410(13) 0.0492(14) -0.0040(10) 0.0030(10) 0.0082(10) C9 0.0289(11) 0.0313(11) 0.0379(12) -0.0003(9) -0.0006(9) 0.0012(8) C10 0.0276(11) 0.0316(11) 0.0336(11) -0.0008(9) 0.0018(8) 0.0008(8) C11 0.0306(11) 0.0334(11) 0.0314(11) 0.0050(8) -0.0007(8) 0.0037(9) C13 0.0418(13) 0.0520(14) 0.0333(12) 0.0059(10) 0.0065(10) 0.0086(11) C14 0.0491(14) 0.0535(15) 0.0319(12) 0.0057(10) 0.0038(10) 0.0014(11) O8 0.0488(10) 0.0626(11) 0.0478(10) 0.0114(8) 0.0058(8) 0.0058(8) _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 C9 1.372(3) . ? O1 C2 1.376(3) . ? O2 C2 1.202(3) . ? O6A N6 1.213(3) . ? O6B N6 1.216(3) . ? O11 C11 1.230(2) . ? O15 C14 1.424(3) . ? O15 H15 0.8394 . ? N6 C6 1.467(3) . ? N12 C11 1.326(3) . ? N12 C13 1.453(3) . ? N12 H12 0.8800 . ? C2 C3 1.462(3) . ? C3 C4 1.343(3) . ? C3 C11 1.503(3) . ? C4 C10 1.434(3) . ? C4 H4 0.9500 . ? C5 C6 1.374(3) . ? C5 C10 1.395(3) . ? C5 H5 0.9500 . ? C6 C7 1.390(3) . ? C7 C8 1.368(3) . ? C7 H7 0.9500 . ? C8 C9 1.384(3) . ? C8 H8 0.9500 . ? C9 C10 1.391(3) . ? C13 C14 1.502(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? O8 H8A 0.8417 . ? O8 H8B 0.8411 . ? 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 C9 O1 C2 123.01(16) . . ? C14 O15 H15 109.8 . . ? O6A N6 O6B 123.6(2) . . ? O6A N6 C6 118.64(19) . . ? O6B N6 C6 117.8(2) . . ? C11 N12 C13 122.12(18) . . ? C11 N12 H12 118.9 . . ? C13 N12 H12 118.9 . . ? O2 C2 O1 115.54(18) . . ? O2 C2 C3 127.2(2) . . ? O1 C2 C3 117.23(18) . . ? C4 C3 C2 119.74(19) . . ? C4 C3 C11 118.22(18) . . ? C2 C3 C11 122.04(18) . . ? C3 C4 C10 121.69(19) . . ? C3 C4 H4 119.2 . . ? C10 C4 H4 119.2 . . ? C6 C5 C10 118.3(2) . . ? C6 C5 H5 120.8 . . ? C10 C5 H5 120.8 . . ? C5 C6 C7 122.7(2) . . ? C5 C6 N6 118.1(2) . . ? C7 C6 N6 119.21(19) . . ? C8 C7 C6 119.5(2) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 118.4(2) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? O1 C9 C8 117.10(18) . . ? O1 C9 C10 120.20(18) . . ? C8 C9 C10 122.7(2) . . ? C9 C10 C5 118.46(19) . . ? C9 C10 C4 118.12(19) . . ? C5 C10 C4 123.38(19) . . ? O11 C11 N12 122.74(19) . . ? O11 C11 C3 119.62(18) . . ? N12 C11 C3 117.64(18) . . ? N12 C13 C14 110.95(19) . . ? N12 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? N12 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? O15 C14 C13 112.25(19) . . ? O15 C14 H14A 109.2 . . ? C13 C14 H14A 109.2 . . ? O15 C14 H14B 109.2 . . ? C13 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? H8A O8 H8B 101.6 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.202 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.042 # Attachment '3a.cif' data_aca1 _database_code_depnum_ccdc_archive 'CCDC 704504' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(2-hydroxyethyl)-6-methoxy-2-oxo-2H-chromene-3-carboxamide ; _chemical_name_common N-(2-hydroxyethyl)-6-methoxy-2-oxo-2H-chromene-3-carboxamide _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N O5' _chemical_formula_sum 'C13 H13 N O5' _chemical_formula_weight 263.24 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 6.8051(14) _cell_length_b 24.947(5) _cell_length_c 8.097(3) _cell_angle_alpha 90 _cell_angle_beta 123.45(2) _cell_angle_gamma 90 _cell_volume 1146.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 200 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 5 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 24974 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 35.91 _reflns_number_total 4881 _reflns_number_gt 4105 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997) and WINGX-2003 (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^)+(0.0664P)^2^+0.2343P] 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 4881 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1138 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.46713(9) 0.00688(2) 0.19746(8) 1.000 0.0141(1) . . O2 O Uani 0.57549(10) 0.07733(2) 0.10554(9) 1.000 0.0172(1) . . O11 O Uani 0.07512(10) 0.17443(2) 0.11568(9) 1.000 0.0177(1) . . O15 O Uani 0.60497(11) 0.20199(3) -0.10856(9) 1.000 0.0206(2) . . O16 O Uani -0.07256(10) -0.09594(2) 0.41542(9) 1.000 0.0177(1) . . N12 N Uani 0.33983(11) 0.16966(2) 0.02894(10) 1.000 0.0150(2) . . C2 C Uani 0.43864(12) 0.05956(3) 0.14437(10) 1.000 0.0128(2) . . C3 C Uani 0.25159(11) 0.08947(3) 0.14237(10) 1.000 0.0115(2) . . C4 C Uani 0.11272(12) 0.06417(3) 0.19044(10) 1.000 0.0121(2) . . C5 C Uani 0.01387(12) -0.01910(3) 0.30203(10) 1.000 0.0128(2) . . C6 C Uani 0.06371(12) -0.07264(3) 0.35935(10) 1.000 0.0130(2) . . C7 C Uani 0.24298(12) -0.09930(3) 0.35627(11) 1.000 0.0146(2) . . C8 C Uani 0.37558(12) -0.07240(3) 0.29923(11) 1.000 0.0147(2) . . C9 C Uani 0.32828(11) -0.01877(3) 0.24747(10) 1.000 0.0122(2) . . C10 C Uani 0.14820(11) 0.00853(3) 0.24650(10) 1.000 0.0114(2) . . C11 C Uani 0.21390(12) 0.14827(3) 0.09305(10) 1.000 0.0125(2) . . C13 C Uani 0.33675(13) 0.22610(3) -0.01731(11) 1.000 0.0148(2) . . C14 C Uani 0.56873(13) 0.23910(3) 0.00568(12) 1.000 0.0179(2) . . C17 C Uani -0.00806(15) -0.14853(3) 0.49884(12) 1.000 0.0182(2) . . H4 H Uiso -0.00970 0.08350 0.18690 1.000 0.0140 calc R H5 H Uiso -0.11060 -0.00140 0.30060 1.000 0.0150 calc R H7 H Uiso 0.27420 -0.13600 0.39340 1.000 0.0180 calc R H8 H Uiso 0.49620 -0.09050 0.29580 1.000 0.0180 calc R H12 H Uiso 0.43110 0.14810 0.01360 1.000 0.0180 calc R H13A H Uiso 0.31780 0.24810 0.07190 1.000 0.0180 calc R H13B H Uiso 0.20630 0.23330 -0.15180 1.000 0.0180 calc R H14A H Uiso 0.56470 0.27530 -0.03940 1.000 0.0220 calc R H14B H Uiso 0.69690 0.23660 0.14390 1.000 0.0220 calc R H15 H Uiso 0.74710 0.19260 -0.04460 1.000 0.0310 calc R H17A H Uiso -0.11750 -0.16060 0.53230 1.000 0.0270 calc R H17B H Uiso 0.15010 -0.14780 0.61740 1.000 0.0270 calc R H17C H Uiso -0.01300 -0.17300 0.40340 1.000 0.0270 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 0.0132(2) 0.0115(2) 0.0205(2) 0.0019(2) 0.0112(2) 0.0017(2) O2 0.0166(2) 0.0143(2) 0.0264(3) 0.0015(2) 0.0154(2) 0.0008(2) O11 0.0186(2) 0.0138(2) 0.0252(3) 0.0001(2) 0.0149(2) 0.0027(2) O15 0.0197(3) 0.0232(3) 0.0217(3) 0.0021(2) 0.0132(2) 0.0041(2) O16 0.0199(2) 0.0149(2) 0.0242(3) 0.0044(2) 0.0158(2) 0.0007(2) N12 0.0183(3) 0.0108(2) 0.0206(3) 0.0013(2) 0.0137(2) 0.0015(2) C2 0.0121(3) 0.0116(3) 0.0144(3) -0.0001(2) 0.0072(2) 0.0007(2) C3 0.0112(2) 0.0107(3) 0.0125(3) -0.0008(2) 0.0065(2) 0.0007(2) C4 0.0118(2) 0.0121(3) 0.0121(3) -0.0007(2) 0.0065(2) 0.0007(2) C5 0.0128(3) 0.0131(3) 0.0135(3) 0.0000(2) 0.0079(2) 0.0008(2) C6 0.0132(3) 0.0135(3) 0.0129(3) 0.0008(2) 0.0076(2) -0.0006(2) C7 0.0146(3) 0.0128(3) 0.0163(3) 0.0026(2) 0.0084(2) 0.0022(2) C8 0.0138(3) 0.0132(3) 0.0177(3) 0.0022(2) 0.0091(2) 0.0026(2) C9 0.0108(2) 0.0129(3) 0.0128(3) 0.0006(2) 0.0065(2) 0.0003(2) C10 0.0111(2) 0.0115(3) 0.0112(3) -0.0004(2) 0.0059(2) 0.0002(2) C11 0.0125(3) 0.0116(3) 0.0124(3) -0.0007(2) 0.0063(2) 0.0002(2) C13 0.0169(3) 0.0107(3) 0.0174(3) 0.0008(2) 0.0098(2) 0.0007(2) C14 0.0180(3) 0.0149(3) 0.0213(3) 0.0006(2) 0.0111(3) -0.0011(2) C17 0.0243(3) 0.0131(3) 0.0194(3) 0.0006(2) 0.0134(3) -0.0026(2) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.3630(10) . . yes O1 C9 1.3741(12) . . yes O2 C2 1.2188(13) . . yes O11 C11 1.2418(12) . . yes O15 C14 1.4230(12) . . yes O16 C6 1.3668(13) . . yes O16 C17 1.4294(11) . . yes O15 H15 0.8400 . . no N12 C13 1.4541(11) . . yes N12 C11 1.3338(13) . . yes N12 H12 0.8800 . . no C2 C3 1.4678(13) . . no C3 C4 1.3596(13) . . no C3 C11 1.5047(12) . . no C4 C10 1.4388(12) . . no C5 C10 1.4022(13) . . no C5 C6 1.3932(12) . . no C6 C7 1.4017(14) . . no C7 C8 1.3919(14) . . no C8 C9 1.3858(12) . . no C9 C10 1.3982(13) . . no C13 C14 1.5192(15) . . no C4 H4 0.9500 . . no C5 H5 0.9500 . . no C7 H7 0.9500 . . no C8 H8 0.9500 . . no C13 H13A 0.9700 . . no C13 H13B 0.9700 . . no C14 H14A 0.9700 . . no C14 H14B 0.9700 . . no C17 H17A 0.9700 . . no C17 H17B 0.9700 . . no C17 H17C 0.9700 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C9 122.73(7) . . . yes C6 O16 C17 117.35(8) . . . yes C14 O15 H15 109.00 . . . no C11 N12 C13 124.50(8) . . . yes C11 N12 H12 118.00 . . . no C13 N12 H12 118.00 . . . no O1 C2 O2 115.85(8) . . . yes O1 C2 C3 117.73(8) . . . yes O2 C2 C3 126.41(7) . . . yes C4 C3 C11 119.00(8) . . . no C2 C3 C4 119.75(7) . . . no C2 C3 C11 121.23(8) . . . no C3 C4 C10 121.06(8) . . . no C6 C5 C10 119.74(8) . . . no O16 C6 C5 115.67(8) . . . yes C5 C6 C7 120.23(8) . . . no O16 C6 C7 124.10(7) . . . yes C6 C7 C8 120.46(7) . . . no C7 C8 C9 118.74(8) . . . no O1 C9 C8 117.12(8) . . . yes O1 C9 C10 120.96(7) . . . yes C8 C9 C10 121.92(8) . . . no C4 C10 C5 123.35(8) . . . no C4 C10 C9 117.76(8) . . . no C5 C10 C9 118.88(7) . . . no O11 C11 C3 120.36(8) . . . yes O11 C11 N12 123.45(7) . . . yes N12 C11 C3 116.18(8) . . . yes N12 C13 C14 107.98(7) . . . yes O15 C14 C13 108.79(7) . . . yes C3 C4 H4 120.00 . . . no C10 C4 H4 119.00 . . . no C6 C5 H5 120.00 . . . no C10 C5 H5 120.00 . . . no C6 C7 H7 120.00 . . . no C8 C7 H7 120.00 . . . no C7 C8 H8 121.00 . . . no C9 C8 H8 121.00 . . . no N12 C13 H13A 110.00 . . . no N12 C13 H13B 110.00 . . . no C14 C13 H13A 110.00 . . . no C14 C13 H13B 110.00 . . . no H13A C13 H13B 108.00 . . . no O15 C14 H14A 110.00 . . . no O15 C14 H14B 110.00 . . . no C13 C14 H14A 110.00 . . . no C13 C14 H14B 110.00 . . . no H14A C14 H14B 108.00 . . . no O16 C17 H17A 109.00 . . . no O16 C17 H17B 110.00 . . . no O16 C17 H17C 110.00 . . . no H17A C17 H17B 109.00 . . . no H17A C17 H17C 109.00 . . . no H17B C17 H17C 109.00 . . . no 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 C9 O1 C2 O2 179.31(7) . . . . no C9 O1 C2 C3 0.29(10) . . . . no C2 O1 C9 C8 -179.83(7) . . . . no C2 O1 C9 C10 -0.11(11) . . . . no C17 O16 C6 C7 8.05(10) . . . . no C17 O16 C6 C5 -172.28(7) . . . . no C11 N12 C13 C14 154.94(8) . . . . no C13 N12 C11 O11 1.79(12) . . . . no C13 N12 C11 C3 -176.99(7) . . . . no O2 C2 C3 C4 -179.63(7) . . . . no O1 C2 C3 C4 -0.72(10) . . . . no O2 C2 C3 C11 -1.24(11) . . . . no O1 C2 C3 C11 177.67(6) . . . . no C11 C3 C4 C10 -177.46(6) . . . . no C2 C3 C11 O11 -171.06(7) . . . . no C2 C3 C4 C10 0.97(10) . . . . no C2 C3 C11 N12 7.76(10) . . . . no C4 C3 C11 N12 -173.83(7) . . . . no C4 C3 C11 O11 7.35(11) . . . . no C3 C4 C10 C5 178.40(7) . . . . no C3 C4 C10 C9 -0.78(10) . . . . no C10 C5 C6 O16 178.51(7) . . . . no C10 C5 C6 C7 -1.80(11) . . . . no C6 C5 C10 C9 0.86(10) . . . . no C6 C5 C10 C4 -178.30(7) . . . . no O16 C6 C7 C8 -179.26(7) . . . . no C5 C6 C7 C8 1.08(11) . . . . no C6 C7 C8 C9 0.58(11) . . . . no C7 C8 C9 C10 -1.55(11) . . . . no C7 C8 C9 O1 178.18(7) . . . . no O1 C9 C10 C4 0.33(10) . . . . no O1 C9 C10 C5 -178.88(7) . . . . no C8 C9 C10 C4 -179.96(7) . . . . no C8 C9 C10 C5 0.83(11) . . . . no N12 C13 C14 O15 52.75(8) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C5 3.3922(17) . 1_655 no O1 O2 3.1196(14) . 3_655 no O2 O1 3.1196(14) . 3_655 no O2 N12 2.6768(13) . . no O2 C4 3.3430(17) . 1_655 no O2 C17 3.4185(16) . 3_656 no O11 O15 2.7571(15) . 1_455 no O15 O11 2.7571(15) . 1_655 no O15 C13 3.2930(16) . 4_554 no O15 C14 3.3358(16) . 4_554 no O15 N12 2.7130(15) . . no O16 C8 3.3821(17) . 1_455 no O1 H5 2.5200 . 1_655 no O2 H12 1.9600 . . no O2 H4 2.5300 . 1_655 no O2 H17B 2.6400 . 3_656 no O2 H5 2.6800 . 1_655 no O11 H13B 2.7900 . 4_555 no O11 H4 2.4900 . . no O11 H13A 2.6200 . . no O11 H17A 2.7200 . 3_556 no O11 H15 1.9200 . 1_455 no O15 H12 2.3400 . . no O15 H13A 2.5500 . 4_554 no O15 H14B 2.8500 . 4_554 no O16 H8 2.5400 . 1_455 no N12 O2 2.6768(13) . . no N12 O15 2.7130(15) . . no N12 H17C 2.9400 . 3_555 no C2 C6 3.5666(17) . 3_656 no C2 C7 3.5168(16) . 3_656 no C2 C5 3.3609(16) . 3_555 no C3 C7 3.5649(17) . 3_555 no C3 C5 3.4824(16) . 3_555 no C3 C6 3.4167(16) . 3_555 no C4 O2 3.3430(17) . 1_455 no C4 C9 3.3363(16) . 3_555 no C4 C10 3.4689(16) . 3_555 no C4 C8 3.5043(17) . 3_555 no C5 C5 3.4480(17) . 3_556 no C5 C3 3.4824(16) . 3_555 no C5 O1 3.3922(17) . 1_455 no C5 C2 3.3609(16) . 3_555 no C6 C2 3.5666(17) . 3_656 no C6 C3 3.4167(16) . 3_555 no C6 C11 3.5942(17) . 3_555 no C7 C2 3.5168(16) . 3_656 no C7 C11 3.4533(17) . 3_555 no C7 C3 3.5649(17) . 3_555 no C8 C4 3.5043(17) . 3_555 no C8 O16 3.3821(17) . 1_655 no C9 C10 3.5042(16) . 3_555 no C9 C4 3.3363(16) . 3_555 no C9 C9 3.5393(16) . 3_656 no C10 C10 3.3627(16) . 3_555 no C10 C4 3.4689(16) . 3_555 no C10 C9 3.5042(16) . 3_555 no C11 C7 3.4533(17) . 3_555 no C11 C6 3.5942(17) . 3_555 no C13 O15 3.2930(16) . 4_555 no C14 O15 3.3358(16) . 4_555 no C17 O2 3.4185(16) . 3_656 no C2 H5 3.0100 . 1_655 no C2 H12 2.4400 . . no C5 H5 2.9500 . 3_556 no C7 H17C 2.7000 . . no C7 H17B 2.7900 . . no C11 H15 2.9400 . 1_455 no C13 H17C 2.9600 . 3_555 no C14 H13A 2.9600 . 4_554 no C17 H7 2.5100 . . no C17 H4 2.9600 . 3_556 no H4 O2 2.5300 . 1_455 no H4 O11 2.4900 . . no H4 H5 2.5500 . . no H4 C17 2.9600 . 3_556 no H5 O1 2.5200 . 1_455 no H5 O2 2.6800 . 1_455 no H5 C2 3.0100 . 1_455 no H5 H4 2.5500 . . no H5 C5 2.9500 . 3_556 no H7 C17 2.5100 . . no H7 H17B 2.4000 . . no H7 H17C 2.2000 . . no H7 H14A 2.4600 . 2_645 no H8 O16 2.5400 . 1_655 no H12 O2 1.9600 . . no H12 O15 2.3400 . . no H12 C2 2.4400 . . no H13A O11 2.6200 . . no H13A H17A 2.5500 . 2_555 no H13A O15 2.5500 . 4_555 no H13A C14 2.9600 . 4_555 no H13B H17C 2.2800 . 3_555 no H13B O11 2.7900 . 4_554 no H14A H7 2.4600 . 2_655 no H14B O15 2.8500 . 4_555 no H15 O11 1.9200 . 1_655 no H15 C11 2.9400 . 1_655 no H17A H13A 2.5500 . 2_545 no H17A O11 2.7200 . 3_556 no H17B C7 2.7900 . . no H17B H7 2.4000 . . no H17B O2 2.6400 . 3_656 no H17C C7 2.7000 . . no H17C H7 2.2000 . . no H17C N12 2.9400 . 3_555 no H17C C13 2.9600 . 3_555 no H17C H13B 2.2800 . 3_555 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N12 H12 O2 0.8800 1.9600 2.6768(13) 138.00 . yes N12 H12 O15 0.8800 2.3400 2.7130(15) 106.00 . yes O15 H15 O11 0.8400 1.9200 2.7571(15) 176.00 1_655 yes C4 H4 O2 0.9500 2.5300 3.3430(17) 144.00 1_455 yes C5 H5 O1 0.9500 2.5200 3.3922(17) 153.00 1_455 yes C8 H8 O16 0.9500 2.5400 3.3821(17) 148.00 1_655 yes C13 H13A O15 0.9700 2.5500 3.2930(16) 134.00 4_555 yes _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.557 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.061 # Attachment '4a.cif' data_alfrdosm _database_code_depnum_ccdc_archive 'CCDC 704505' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-chloro-N-(2-hydroxyethyl)-2-oxo-2H-chromene-3-carboxamide ; _chemical_name_common 6-chloro-N-(2-hydroxyethyl)-2-oxo-2H-chromene-3-carboxamide _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Cl N O4' _chemical_formula_sum 'C12 H10 Cl N O4' _chemical_formula_weight 267.66 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' 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_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 5.3567(5) _cell_length_b 22.078(2) _cell_length_c 9.3087(8) _cell_angle_alpha 90 _cell_angle_beta 91.873(2) _cell_angle_gamma 90 _cell_volume 1100.29(17) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 200 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description square _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.353 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 5 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 12432 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 28.33 _reflns_number_total 2629 _reflns_number_gt 2545 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997) and WINGX-2003 (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^)+(0.0423P)^2^+0.7991P] 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 2629 _refine_ls_number_parameters 163 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0925 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.389 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl6 Cl Uani 0.15686(8) 0.57294(2) 1.43324(5) 1.000 0.0167(1) . . O1 O Uani 0.7891(2) 0.56025(6) 0.93404(14) 1.000 0.0148(3) . . O2 O Uani 0.8896(3) 0.58165(6) 0.71390(15) 1.000 0.0194(4) . . O11 O Uani 0.2833(3) 0.70410(6) 0.67517(15) 1.000 0.0204(4) . . O15 O Uani 0.9461(3) 0.77576(6) 0.52313(15) 1.000 0.0198(4) . . N12 N Uani 0.6292(3) 0.66960(7) 0.56692(17) 1.000 0.0153(4) . . C2 C Uani 0.7435(3) 0.59099(8) 0.80783(19) 1.000 0.0138(5) . . C3 C Uani 0.5264(3) 0.63106(8) 0.80085(19) 1.000 0.0129(5) . . C4 C Uani 0.3740(3) 0.63433(8) 0.91307(19) 1.000 0.0134(5) . . C5 C Uani 0.2720(3) 0.60340(8) 1.16218(19) 1.000 0.0140(5) . . C6 C Uani 0.3388(3) 0.57013(8) 1.2825(2) 1.000 0.0140(5) . . C7 C Uani 0.5519(3) 0.53377(8) 1.2873(2) 1.000 0.0156(5) . . C8 C Uani 0.7024(3) 0.53054(8) 1.1697(2) 1.000 0.0157(5) . . C9 C Uani 0.6360(3) 0.56425(8) 1.0488(2) 1.000 0.0133(5) . . C10 C Uani 0.4240(3) 0.60070(8) 1.04214(19) 1.000 0.0128(5) . . C11 C Uani 0.4689(3) 0.67116(8) 0.67327(19) 1.000 0.0140(5) . . C13 C Uani 0.6098(4) 0.70915(9) 0.4419(2) 1.000 0.0174(5) . . C14 C Uani 0.8608(3) 0.73684(8) 0.4106(2) 1.000 0.0165(5) . . H4 H Uiso 0.23030 0.65950 0.90620 1.000 0.0160 calc R H5 H Uiso 0.12580 0.62780 1.16040 1.000 0.0170 calc R H7 H Uiso 0.59370 0.51120 1.37150 1.000 0.0190 calc R H8 H Uiso 0.84770 0.50580 1.17170 1.000 0.0190 calc R H12 H Uiso 0.75280 0.64340 0.57250 1.000 0.0180 calc R H13A H Uiso 0.49030 0.74110 0.45930 1.000 0.0210 calc R H13B H Uiso 0.54960 0.68610 0.35910 1.000 0.0210 calc R H14A H Uiso 0.98190 0.70480 0.39810 1.000 0.0200 calc R H14B H Uiso 0.84690 0.75960 0.32160 1.000 0.0200 calc R H15 H Uiso 1.05140 0.75740 0.57590 1.000 0.0300 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 Cl6 0.0180(2) 0.0197(2) 0.0127(2) 0.0011(2) 0.0033(2) 0.0008(2) O1 0.0140(6) 0.0171(6) 0.0135(6) 0.0029(5) 0.0025(5) 0.0036(5) O2 0.0194(7) 0.0211(7) 0.0180(7) 0.0047(5) 0.0068(5) 0.0053(5) O11 0.0204(7) 0.0238(7) 0.0169(7) 0.0046(5) 0.0005(5) 0.0077(5) O15 0.0190(7) 0.0169(6) 0.0230(7) 0.0026(5) -0.0045(5) -0.0024(5) N12 0.0154(7) 0.0153(7) 0.0153(7) 0.0037(6) 0.0008(6) 0.0003(6) C2 0.0143(8) 0.0127(8) 0.0144(8) 0.0017(6) 0.0005(6) -0.0005(6) C3 0.0140(8) 0.0113(8) 0.0133(8) 0.0006(6) -0.0011(6) 0.0000(6) C4 0.0135(8) 0.0118(8) 0.0147(8) -0.0001(6) -0.0005(6) 0.0012(6) C5 0.0139(8) 0.0136(8) 0.0144(8) -0.0006(6) 0.0010(6) 0.0001(6) C6 0.0152(8) 0.0141(8) 0.0128(8) -0.0013(6) 0.0025(6) -0.0020(6) C7 0.0174(9) 0.0155(8) 0.0137(8) 0.0022(6) -0.0013(7) -0.0009(7) C8 0.0128(8) 0.0161(8) 0.0181(9) 0.0005(7) -0.0007(7) 0.0014(7) C9 0.0129(8) 0.0132(8) 0.0138(8) -0.0009(6) 0.0019(6) -0.0011(6) C10 0.0134(8) 0.0115(8) 0.0135(8) -0.0009(6) -0.0003(6) -0.0009(6) C11 0.0163(8) 0.0130(8) 0.0126(8) -0.0007(6) -0.0019(6) -0.0018(6) C13 0.0188(9) 0.0198(9) 0.0135(9) 0.0052(7) -0.0016(7) -0.0020(7) C14 0.0182(9) 0.0166(9) 0.0147(9) 0.0034(7) 0.0024(7) -0.0001(7) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl6 C6 1.7355(18) . . yes O1 C2 1.372(2) . . yes O1 C9 1.371(2) . . yes O2 C2 1.210(2) . . yes O11 C11 1.232(2) . . yes O15 C14 1.419(2) . . yes O15 H15 0.8400 . . no N12 C13 1.456(2) . . yes N12 C11 1.332(2) . . yes N12 H12 0.8800 . . no C2 C3 1.461(2) . . no C3 C4 1.349(2) . . no C3 C11 1.505(2) . . no C4 C10 1.430(2) . . no C5 C10 1.405(2) . . no C5 C6 1.377(3) . . no C6 C7 1.395(2) . . no C7 C8 1.382(3) . . no C8 C9 1.386(3) . . no C9 C10 1.392(2) . . no C13 C14 1.514(3) . . no C4 H4 0.9500 . . no C5 H5 0.9500 . . no C7 H7 0.9500 . . no C8 H8 0.9500 . . no C13 H13A 0.9700 . . no C13 H13B 0.9700 . . no C14 H14A 0.9700 . . no C14 H14B 0.9700 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C9 122.77(13) . . . yes C14 O15 H15 109.00 . . . no C11 N12 C13 123.21(16) . . . yes C11 N12 H12 118.00 . . . no C13 N12 H12 118.00 . . . no O1 C2 O2 115.68(15) . . . yes O1 C2 C3 117.19(14) . . . yes O2 C2 C3 127.14(17) . . . yes C4 C3 C11 117.79(15) . . . no C2 C3 C4 119.94(16) . . . no C2 C3 C11 122.23(15) . . . no C3 C4 C10 121.43(16) . . . no C6 C5 C10 118.84(15) . . . no Cl6 C6 C5 120.05(13) . . . yes C5 C6 C7 121.58(16) . . . no Cl6 C6 C7 118.37(14) . . . yes C6 C7 C8 120.14(17) . . . no C7 C8 C9 118.33(15) . . . no O1 C9 C8 117.00(15) . . . yes O1 C9 C10 120.71(16) . . . yes C8 C9 C10 122.28(16) . . . no C4 C10 C5 123.27(15) . . . no C4 C10 C9 117.89(16) . . . no C5 C10 C9 118.84(16) . . . no O11 C11 C3 118.70(15) . . . yes O11 C11 N12 124.46(17) . . . yes N12 C11 C3 116.81(15) . . . yes N12 C13 C14 110.82(16) . . . yes O15 C14 C13 111.66(15) . . . yes C3 C4 H4 119.00 . . . no C10 C4 H4 119.00 . . . no C6 C5 H5 121.00 . . . no C10 C5 H5 121.00 . . . no C6 C7 H7 120.00 . . . no C8 C7 H7 120.00 . . . no C7 C8 H8 121.00 . . . no C9 C8 H8 121.00 . . . no N12 C13 H13A 109.00 . . . no N12 C13 H13B 109.00 . . . no C14 C13 H13A 109.00 . . . no C14 C13 H13B 109.00 . . . no H13A C13 H13B 108.00 . . . no O15 C14 H14A 109.00 . . . no O15 C14 H14B 109.00 . . . no C13 C14 H14A 109.00 . . . no C13 C14 H14B 109.00 . . . no H14A C14 H14B 108.00 . . . no 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 C9 O1 C2 O2 -177.62(16) . . . . no C9 O1 C2 C3 2.4(2) . . . . no C2 O1 C9 C10 -0.3(2) . . . . no C2 O1 C9 C8 179.58(15) . . . . no C11 N12 C13 C14 133.28(18) . . . . no C13 N12 C11 O11 2.9(3) . . . . no C13 N12 C11 C3 -175.03(16) . . . . no O2 C2 C3 C4 176.78(18) . . . . no O2 C2 C3 C11 -5.3(3) . . . . no O1 C2 C3 C11 174.74(15) . . . . no O1 C2 C3 C4 -3.2(2) . . . . no C4 C3 C11 N12 176.52(16) . . . . no C2 C3 C4 C10 2.0(3) . . . . no C4 C3 C11 O11 -1.6(2) . . . . no C11 C3 C4 C10 -175.98(16) . . . . no C2 C3 C11 N12 -1.5(2) . . . . no C2 C3 C11 O11 -179.55(16) . . . . no C3 C4 C10 C5 179.15(17) . . . . no C3 C4 C10 C9 0.0(3) . . . . no C6 C5 C10 C9 0.3(3) . . . . no C10 C5 C6 Cl6 179.42(13) . . . . no C10 C5 C6 C7 -0.4(3) . . . . no C6 C5 C10 C4 -178.78(17) . . . . no Cl6 C6 C7 C8 -179.68(14) . . . . no C5 C6 C7 C8 0.1(3) . . . . no C6 C7 C8 C9 0.2(3) . . . . no C7 C8 C9 C10 -0.3(3) . . . . no C7 C8 C9 O1 179.84(15) . . . . no O1 C9 C10 C4 -1.0(2) . . . . no O1 C9 C10 C5 179.90(15) . . . . no C8 C9 C10 C4 179.15(16) . . . . no C8 C9 C10 C5 0.0(3) . . . . no N12 C13 C14 O15 -64.72(19) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl6 O2 3.0260(15) . 1_456 no Cl6 C7 3.5787(17) . 1_455 no Cl6 C8 3.5257(18) . 1_455 no Cl6 C11 3.4992(18) . 1_556 no Cl6 H12 2.9900 . 1_456 no Cl6 H14A 3.0700 . 1_456 no Cl6 H7 2.9000 . 3_668 no O1 C7 3.412(2) . 3_667 no O2 C4 3.348(2) . 1_655 no O2 Cl6 3.0260(15) . 1_654 no O2 N12 2.732(2) . . no O11 C14 3.368(2) . 1_455 no O11 O15 2.757(2) . 1_455 no O15 C5 3.420(2) . 4_664 no O15 O11 2.757(2) . 1_655 no O15 N12 2.930(2) . . no O15 C4 3.225(2) . 4_664 no O1 H8 2.6500 . 3_767 no O2 H8 2.6000 . 3_767 no O2 H12 2.0200 . . no O11 H13A 2.4700 . . no O11 H15 1.9300 . 1_455 no O11 H14B 2.8600 . 4_465 no O11 H4 2.3900 . . no O15 H4 2.3800 . 4_664 no O15 H5 2.6500 . 4_664 no N12 O2 2.732(2) . . no N12 O15 2.930(2) . . no C2 C7 3.284(2) . 3_667 no C3 C14 3.555(2) . 4_565 no C4 O2 3.348(2) . 1_455 no C4 O15 3.225(2) . 4_465 no C5 O15 3.420(2) . 4_465 no C5 C8 3.452(2) . 1_455 no C7 C2 3.284(2) . 3_667 no C7 O1 3.412(2) . 3_667 no C7 Cl6 3.5787(17) . 1_655 no C8 C9 3.400(3) . 3_667 no C8 C10 3.557(3) . 3_667 no C8 C5 3.452(2) . 1_655 no C8 Cl6 3.5257(18) . 1_655 no C9 C8 3.400(3) . 3_667 no C9 C9 3.303(2) . 3_667 no C10 C8 3.557(3) . 3_667 no C11 Cl6 3.4992(18) . 1_554 no C14 O11 3.368(2) . 1_655 no C14 C3 3.555(2) . 4_564 no C2 H8 3.0600 . 3_767 no C2 H12 2.4800 . . no C3 H14B 2.9600 . 4_565 no C4 H13A 2.8500 . 4_565 no C5 H13B 2.9500 . 1_556 no C6 H13B 2.8800 . 1_556 no C11 H14B 2.8600 . 4_565 no C11 H15 3.0500 . 1_455 no C14 H4 3.0300 . 4_664 no H4 O11 2.3900 . . no H4 H5 2.5500 . . no H4 O15 2.3800 . 4_465 no H4 C14 3.0300 . 4_465 no H5 H4 2.5500 . . no H5 O15 2.6500 . 4_465 no H7 Cl6 2.9000 . 3_668 no H8 O1 2.6500 . 3_767 no H8 O2 2.6000 . 3_767 no H8 C2 3.0600 . 3_767 no H12 Cl6 2.9900 . 1_654 no H12 O2 2.0200 . . no H12 C2 2.4800 . . no H12 H14A 2.4700 . . no H13A O11 2.4700 . . no H13A C4 2.8500 . 4_564 no H13B C5 2.9500 . 1_554 no H13B C6 2.8800 . 1_554 no H14A Cl6 3.0700 . 1_654 no H14A H12 2.4700 . . no H14B O11 2.8600 . 4_664 no H14B C3 2.9600 . 4_564 no H14B C11 2.8600 . 4_564 no H14B H15 2.6000 . 4_564 no H15 O11 1.9300 . 1_655 no H15 C11 3.0500 . 1_655 no H15 H14B 2.6000 . 4_565 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N12 H12 O2 0.8800 2.0200 2.732(2) 138.00 . yes O15 H15 O11 0.8400 1.9300 2.757(2) 170.00 1_655 yes C4 H4 O11 0.9500 2.3900 2.728(2) 100.00 . yes C4 H4 O15 0.9500 2.3800 3.225(2) 148.00 4_465 yes C8 H8 O2 0.9500 2.6000 3.454(2) 150.00 3_767 yes C13 H13A O11 0.9700 2.4700 2.835(2) 102.00 . yes _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.438 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.062 # Attachment '5a.cif' data_r2garcix _database_code_depnum_ccdc_archive 'CCDC 704506' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Br N O4' _chemical_formula_weight 312.12 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 8.2813(7) _cell_length_b 25.012(2) _cell_length_c 5.5283(5) _cell_angle_alpha 90 _cell_angle_beta 94.459(2) _cell_angle_gamma 90 _cell_volume 1141.62(17) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 200 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.816 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_min 0.1454 _exptl_absorpt_correction_T_max 0.1686 _exptl_absorpt_correction_T_ave 0.1571 _exptl_absorpt_coefficient_mu 3.607 _exptl_crystal_size_rad 0.4000 _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 5 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 10984 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2018 _reflns_number_gt 1913 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997) and WINGX-2003 (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^)+(0.0311P)^2^+6.1451P] 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 2018 _refine_ls_number_parameters 163 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.560 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Br6 Br Uani 0.44282(9) 0.70332(3) 0.64458(13) 1.000 0.0290(2) . . O1 O Uani 0.3657(5) 0.50752(19) 1.2522(8) 1.000 0.0231(14) . . O2 O Uani 0.2651(6) 0.42828(19) 1.3233(8) 1.000 0.0253(16) . . O11 O Uani -0.0346(5) 0.43362(18) 0.6765(8) 1.000 0.0205(12) . . O15 O Uani 0.1637(6) 0.2740(2) 0.7612(10) 1.000 0.0296(17) . . N12 N Uani 0.0688(7) 0.3787(2) 0.9727(10) 1.000 0.0209(17) . . C2 C Uani 0.2672(8) 0.4658(3) 1.1842(12) 1.000 0.0208(19) . . C3 C Uani 0.1745(8) 0.4696(3) 0.9469(11) 1.000 0.0205(19) . . C4 C Uani 0.1890(8) 0.5134(3) 0.8073(12) 1.000 0.0199(19) . . C5 C Uani 0.3104(8) 0.6023(3) 0.7453(12) 1.000 0.0210(19) . . C6 C Uani 0.4161(8) 0.6410(3) 0.8345(12) 1.000 0.023(2) . . C7 C Uani 0.5042(8) 0.6362(3) 1.0576(12) 1.000 0.024(2) . . C8 C Uani 0.4864(8) 0.5910(3) 1.1968(12) 1.000 0.0261(19) . . C9 C Uani 0.3800(8) 0.5519(3) 1.1095(12) 1.000 0.020(2) . . C10 C Uani 0.2922(8) 0.5564(3) 0.8845(12) 1.000 0.021(2) . . C11 C Uani 0.0596(8) 0.4257(3) 0.8573(11) 1.000 0.0178(17) . . C13 C Uani -0.0353(8) 0.3349(3) 0.8938(13) 1.000 0.025(2) . . C14 C Uani 0.0225(9) 0.3046(3) 0.6827(14) 1.000 0.029(2) . . H3 H Uiso 0.12890 0.51550 0.65410 1.000 0.0240 calc R H4 H Uiso 0.25090 0.60660 0.59250 1.000 0.0250 calc R H5 H Uiso 0.57620 0.66390 1.11430 1.000 0.0290 calc R H7 H Uiso 0.54620 0.58690 1.34950 1.000 0.0310 calc R H12 H Uiso 0.13940 0.37450 1.09870 1.000 0.0250 calc R H13A H Uiso -0.14300 0.34860 0.84890 1.000 0.0300 calc R H13B H Uiso -0.04330 0.31040 1.02840 1.000 0.0300 calc R H14A H Uiso -0.06240 0.28090 0.61600 1.000 0.0340 calc R H14B H Uiso 0.04850 0.32940 0.55660 1.000 0.0340 calc R H15 H Uiso 0.19520 0.25670 0.64320 1.000 0.0450 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 Br6 0.0337(4) 0.0256(4) 0.0273(4) -0.0055(3) 0.0002(3) -0.0061(3) O1 0.024(2) 0.028(3) 0.016(2) -0.004(2) -0.0058(19) 0.005(2) O2 0.030(3) 0.030(3) 0.015(2) 0.002(2) -0.003(2) 0.009(2) O11 0.019(2) 0.025(2) 0.016(2) 0.0051(19) -0.0080(19) -0.0012(19) O15 0.023(3) 0.027(3) 0.038(3) -0.004(2) -0.003(2) 0.006(2) N12 0.021(3) 0.023(3) 0.018(3) 0.003(2) -0.002(2) 0.006(2) C2 0.020(3) 0.024(4) 0.018(3) 0.001(3) -0.001(3) 0.010(3) C3 0.023(3) 0.023(4) 0.015(3) -0.001(3) -0.001(3) 0.006(3) C4 0.020(3) 0.023(4) 0.016(3) -0.003(3) -0.003(3) 0.003(3) C5 0.026(4) 0.019(3) 0.017(3) -0.002(3) -0.004(3) 0.005(3) C6 0.023(4) 0.023(4) 0.022(3) 0.002(3) 0.003(3) 0.000(3) C7 0.016(3) 0.035(4) 0.021(4) -0.013(3) 0.001(3) 0.000(3) C8 0.019(3) 0.041(4) 0.017(3) -0.010(3) -0.006(3) 0.011(3) C9 0.024(4) 0.021(4) 0.016(3) 0.000(3) 0.002(3) 0.010(3) C10 0.023(4) 0.024(4) 0.016(3) -0.008(3) -0.001(3) 0.005(3) C11 0.019(3) 0.021(3) 0.014(3) 0.000(3) 0.005(3) 0.006(3) C13 0.019(3) 0.024(4) 0.032(4) 0.009(3) 0.003(3) 0.003(3) C14 0.029(4) 0.017(4) 0.038(4) 0.001(3) -0.009(3) 0.000(3) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br6 C6 1.902(7) . . yes O1 C2 1.359(8) . . yes O1 C9 1.372(9) . . yes O2 C2 1.214(9) . . yes O11 C11 1.235(8) . . yes O15 C14 1.436(9) . . yes O15 H15 0.8400 . . no N12 C13 1.441(9) . . yes N12 C11 1.337(9) . . yes N12 H12 0.8800 . . no C2 C3 1.471(9) . . no C3 C4 1.351(10) . . no C3 C11 1.511(10) . . no C4 C10 1.419(10) . . no C5 C10 1.397(10) . . no C5 C6 1.371(10) . . no C6 C7 1.389(9) . . no C7 C8 1.382(10) . . no C8 C9 1.378(10) . . no C9 C10 1.396(9) . . no C13 C14 1.501(10) . . no C4 H3 0.9500 . . no C5 H4 0.9500 . . no C7 H5 0.9500 . . no C8 H7 0.9500 . . no C13 H13A 0.9700 . . no C13 H13B 0.9700 . . no C14 H14A 0.9700 . . no C14 H14B 0.9700 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C9 122.6(5) . . . yes C14 O15 H15 110.00 . . . no C11 N12 C13 120.9(6) . . . yes C11 N12 H12 119.00 . . . no C13 N12 H12 120.00 . . . no O1 C2 O2 117.1(6) . . . yes O1 C2 C3 117.2(6) . . . yes O2 C2 C3 125.6(7) . . . yes C4 C3 C11 118.9(6) . . . no C2 C3 C4 119.9(6) . . . no C2 C3 C11 121.2(6) . . . no C3 C4 C10 121.4(6) . . . no C6 C5 C10 118.4(6) . . . no Br6 C6 C5 118.6(5) . . . yes C5 C6 C7 122.4(7) . . . no Br6 C6 C7 119.1(5) . . . yes C6 C7 C8 119.6(7) . . . no C7 C8 C9 118.6(6) . . . no O1 C9 C8 117.0(6) . . . yes O1 C9 C10 121.0(6) . . . yes C8 C9 C10 122.0(7) . . . no C4 C10 C5 123.1(6) . . . no C4 C10 C9 117.8(6) . . . no C5 C10 C9 119.1(6) . . . no O11 C11 C3 119.4(6) . . . yes O11 C11 N12 122.4(6) . . . yes N12 C11 C3 118.1(6) . . . yes N12 C13 C14 113.6(6) . . . yes O15 C14 C13 109.6(6) . . . yes C3 C4 H3 119.00 . . . no C10 C4 H3 119.00 . . . no C6 C5 H4 121.00 . . . no C10 C5 H4 121.00 . . . no C6 C7 H5 120.00 . . . no C8 C7 H5 120.00 . . . no C7 C8 H7 121.00 . . . no C9 C8 H7 121.00 . . . no N12 C13 H13A 109.00 . . . no N12 C13 H13B 109.00 . . . no C14 C13 H13A 109.00 . . . no C14 C13 H13B 109.00 . . . no H13A C13 H13B 108.00 . . . no O15 C14 H14A 110.00 . . . no O15 C14 H14B 110.00 . . . no C13 C14 H14A 110.00 . . . no C13 C14 H14B 110.00 . . . no H14A C14 H14B 108.00 . . . no 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 C9 O1 C2 O2 179.2(6) . . . . no C9 O1 C2 C3 0.2(9) . . . . no C2 O1 C9 C10 0.2(9) . . . . no C2 O1 C9 C8 -178.7(6) . . . . no C11 N12 C13 C14 81.0(8) . . . . no C13 N12 C11 O11 -1.6(10) . . . . no C13 N12 C11 C3 -178.9(6) . . . . no O2 C2 C3 C4 -179.2(7) . . . . no O2 C2 C3 C11 2.2(11) . . . . no O1 C2 C3 C11 -178.9(6) . . . . no O1 C2 C3 C4 -0.3(10) . . . . no C4 C3 C11 N12 167.5(6) . . . . no C2 C3 C4 C10 -0.1(10) . . . . no C4 C3 C11 O11 -9.9(10) . . . . no C11 C3 C4 C10 178.6(6) . . . . no C2 C3 C11 N12 -13.9(9) . . . . no C2 C3 C11 O11 168.8(6) . . . . no C3 C4 C10 C5 180.0(7) . . . . no C3 C4 C10 C9 0.6(10) . . . . no C6 C5 C10 C9 0.9(10) . . . . no C10 C5 C6 Br6 179.5(5) . . . . no C10 C5 C6 C7 -0.4(10) . . . . no C6 C5 C10 C4 -178.6(7) . . . . no Br6 C6 C7 C8 -179.7(5) . . . . no C5 C6 C7 C8 0.1(10) . . . . no C6 C7 C8 C9 -0.4(10) . . . . no C7 C8 C9 C10 0.9(10) . . . . no C7 C8 C9 O1 179.8(6) . . . . no O1 C9 C10 C4 -0.6(10) . . . . no O1 C9 C10 C5 180.0(6) . . . . no C8 C9 C10 C4 178.3(6) . . . . no C8 C9 C10 C5 -1.2(10) . . . . no N12 C13 C14 O15 71.5(7) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Br6 C7 3.723(7) . 1_554 no Br6 Br6 3.6185(11) . 4_564 no Br6 Br6 3.6185(11) . 4_565 no O1 O11 3.164(6) . 3_567 no O1 C9 3.361(8) . 3_667 no O1 C10 3.389(8) . 3_667 no O2 N12 2.729(7) . . no O2 C8 3.265(8) . 3_668 no O2 C6 3.330(8) . 3_667 no O2 C7 3.363(8) . 3_667 no O11 C10 3.363(8) . 3_567 no O11 C4 3.164(8) . 3_566 no O11 C14 3.261(9) . . no O11 C9 3.200(8) . 3_567 no O11 C2 3.296(8) . 3_567 no O11 O1 3.164(6) . 3_567 no O11 C5 3.261(8) . 3_566 no O15 O15 3.014(8) . 4_554 no O15 C14 3.330(9) . 4_555 no O15 N12 2.998(7) . . no O15 O15 3.014(8) . 4_555 no O2 H12 2.0600 . . no O2 H7 2.3300 . 3_668 no O11 H3 2.3100 . 3_566 no O11 H14B 2.7900 . . no O11 H3 2.4600 . . no O11 H4 2.4500 . 3_566 no O11 H13A 2.5200 . . no O15 H5 2.7000 . 3_667 no O15 H15 2.2400 . 4_555 no N12 O2 2.729(7) . . no N12 O15 2.998(7) . . no C2 C8 3.360(10) . 3_667 no C2 O11 3.296(8) . 3_567 no C2 C7 3.503(10) . 3_667 no C2 C9 3.479(9) . 3_667 no C3 C8 3.341(10) . 3_667 no C3 C3 3.358(10) . 3_567 no C3 C4 3.424(9) . 3_567 no C3 C11 3.481(10) . 3_567 no C4 C3 3.424(9) . 3_567 no C4 O11 3.164(8) . 3_566 no C4 C11 3.254(10) . 3_567 no C5 C13 3.514(10) . 3_567 no C5 C8 3.477(9) . 1_554 no C5 O11 3.261(8) . 3_566 no C6 O2 3.330(8) . 3_667 no C7 O2 3.363(8) . 3_667 no C7 C2 3.503(10) . 3_667 no C7 Br6 3.723(7) . 1_556 no C8 O2 3.265(8) . 3_668 no C8 C5 3.477(9) . 1_556 no C8 C3 3.341(10) . 3_667 no C8 C2 3.360(10) . 3_667 no C9 C9 3.540(10) . 3_667 no C9 O11 3.200(8) . 3_567 no C9 O1 3.361(8) . 3_667 no C9 C2 3.479(9) . 3_667 no C10 O11 3.363(8) . 3_567 no C10 C11 3.372(9) . 3_567 no C10 O1 3.389(8) . 3_667 no C11 C10 3.372(9) . 3_567 no C11 C3 3.481(10) . 3_567 no C11 C4 3.254(10) . 3_567 no C13 C5 3.514(10) . 3_567 no C14 O11 3.261(9) . . no C14 O15 3.330(9) . 4_554 no C2 H12 2.5500 . . no C5 H7 3.0700 . 1_554 no C5 H13A 2.9900 . 3_567 no C6 H13A 2.9800 . 3_567 no C7 H13A 3.1000 . 3_567 no C8 H4 3.0700 . 1_556 no C11 H14B 2.9200 . . no C14 H13B 3.0400 . 4_554 no H3 O11 2.4600 . . no H3 H4 2.5300 . . no H3 O11 2.3100 . 3_566 no H4 C8 3.0700 . 1_554 no H4 H3 2.5300 . . no H4 O11 2.4500 . 3_566 no H5 O15 2.7000 . 3_667 no H7 C5 3.0700 . 1_556 no H7 O2 2.3300 . 3_668 no H12 O2 2.0600 . . no H12 C2 2.5500 . . no H13A O11 2.5200 . . no H13A C5 2.9900 . 3_567 no H13A C6 2.9800 . 3_567 no H13A C7 3.1000 . 3_567 no H13B C14 3.0400 . 4_555 no H13B H14A 2.3400 . 4_555 no H14A H13B 2.3400 . 4_554 no H14B O11 2.7900 . . no H14B C11 2.9200 . . no H15 O15 2.2400 . 4_554 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N12 H12 O2 0.8800 2.0600 2.729(7) 132.00 . yes O15 H15 O15 0.8400 2.2400 3.014(8) 152.00 4_554 yes C4 H3 O11 0.9500 2.3100 3.164(8) 149.00 3_566 yes C5 H4 O11 0.9500 2.4500 3.261(8) 143.00 3_566 yes C8 H7 O2 0.9500 2.3300 3.265(8) 168.00 3_668 yes _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.601 _refine_diff_density_min -0.791 _refine_diff_density_rms 0.108