# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Srinivasulu Aitipamula' _publ_contact_author_email 'SRINIVASULU AITIPAMULA@ICES.A-STAR.EDU.SG' _publ_section_title ; Conformational and enantiotropic polymorphism of a 1:1 cocrystal involving ethenzamide and ethylmalonic acid ; loop_ _publ_author_name 'Srinivasulu Aitipamula' 'Pui Shan Chow' 'Reginald B. H. Tan' # Attachment 'C004491A_CIF_revised.cif' data_EA+EMA-Form-I _database_code_depnum_ccdc_archive 'CCDC 752465' #TrackingRef 'C004491A_CIF_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Form I cocrystal of ethenzamide with ethylmalonic acid' ; _chemical_name_common "'Form I cocrystal of ethenzamide with ethylmalonic acid'" _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 N O2, C5 H8 O4' _chemical_formula_sum 'C14 H19 N O6' _chemical_formula_weight 297.30 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 7.6928(15) _cell_length_b 8.8062(18) _cell_length_c 11.575(2) _cell_angle_alpha 93.04(3) _cell_angle_beta 108.70(3) _cell_angle_gamma 91.72(3) _cell_volume 740.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1913 _cell_measurement_theta_min 2.3189 _cell_measurement_theta_max 30.9873 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9554 _exptl_absorpt_correction_T_max 0.9774 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10488 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3635 _reflns_number_gt 3484 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0602P)^2^+0.1987P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3635 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.001 _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 O4 O 0.19681(12) 0.12131(10) 1.18363(8) 0.02602(19) Uani 1 1 d . . . O6 O 0.25466(12) -0.04124(9) 0.94446(8) 0.0268(2) Uani 1 1 d . . . O3 O 0.04593(13) 0.33607(10) 1.13851(8) 0.0292(2) Uani 1 1 d . . . O5 O 0.43374(11) 0.16887(9) 1.02383(8) 0.02582(19) Uani 1 1 d . . . O1 O 0.69481(13) 0.40231(10) 0.39339(8) 0.0300(2) Uani 1 1 d . . . O2 O 0.70561(14) 0.81286(10) 0.59005(8) 0.0319(2) Uani 1 1 d . . . C7 C 0.70594(16) 0.68358(14) 0.53953(11) 0.0244(2) Uani 1 1 d . . . C1 C 0.60551(15) 0.65737(13) 0.40562(10) 0.0239(2) Uani 1 1 d . . . C12 C 0.28150(15) 0.10236(12) 0.98408(10) 0.0212(2) Uani 1 1 d . . . C6 C 0.50985(16) 0.77908(14) 0.34796(11) 0.0267(2) Uani 1 1 d . . . H6 H 0.5105 0.8710 0.3950 0.032 Uiso 1 1 calc R . . N1 N 0.79404(16) 0.57134(13) 0.60187(10) 0.0300(2) Uani 1 1 d . . . C10 C 0.11366(15) 0.22369(13) 1.10891(10) 0.0220(2) Uani 1 1 d . . . C11 C 0.10915(15) 0.18419(12) 0.97805(10) 0.0214(2) Uani 1 1 d . . . H11 H 0.0005 0.1129 0.9373 0.026 Uiso 1 1 calc R . . C13 C 0.09389(16) 0.32400(13) 0.90259(11) 0.0257(2) Uani 1 1 d . . . H13A H -0.0120 0.3821 0.9075 0.031 Uiso 1 1 calc R . . H13B H 0.2064 0.3910 0.9373 0.031 Uiso 1 1 calc R . . C2 C 0.60201(16) 0.52096(14) 0.33516(11) 0.0254(2) Uani 1 1 d . . . C3 C 0.50564(17) 0.51123(15) 0.20991(11) 0.0287(3) Uani 1 1 d . . . H3 H 0.5037 0.4198 0.1620 0.034 Uiso 1 1 calc R . . C4 C 0.41282(17) 0.63493(16) 0.15555(11) 0.0306(3) Uani 1 1 d . . . H4 H 0.3476 0.6274 0.0704 0.037 Uiso 1 1 calc R . . C8 C 0.70186(19) 0.26360(15) 0.32306(12) 0.0318(3) Uani 1 1 d . . . H8A H 0.7635 0.2839 0.2620 0.038 Uiso 1 1 calc R . . H8B H 0.5762 0.2201 0.2795 0.038 Uiso 1 1 calc R . . C5 C 0.41389(18) 0.76940(15) 0.22382(12) 0.0302(3) Uani 1 1 d . . . H5 H 0.3498 0.8536 0.1861 0.036 Uiso 1 1 calc R . . C14 C 0.06891(18) 0.27830(16) 0.76927(11) 0.0313(3) Uani 1 1 d . . . H14A H 0.1742 0.2215 0.7642 0.047 Uiso 1 1 calc R . . H14B H 0.0606 0.3699 0.7236 0.047 Uiso 1 1 calc R . . H14C H -0.0441 0.2141 0.7342 0.047 Uiso 1 1 calc R . . C9 C 0.8087(2) 0.15486(16) 0.41235(14) 0.0377(3) Uani 1 1 d . . . H9A H 0.9313 0.2008 0.4567 0.057 Uiso 1 1 calc R . . H9B H 0.8205 0.0599 0.3679 0.057 Uiso 1 1 calc R . . H9C H 0.7440 0.1331 0.4705 0.057 Uiso 1 1 calc R . . H10 H 0.371(3) -0.080(2) 0.9586(17) 0.047(5) Uiso 1 1 d . . . H2 H 0.854(3) 0.591(2) 0.6829(18) 0.044(5) Uiso 1 1 d . . . H1 H 0.790(3) 0.479(2) 0.5651(17) 0.042(5) Uiso 1 1 d . . . H7 H 0.222(3) 0.153(3) 1.268(2) 0.074(7) Uiso 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 O4 0.0325(4) 0.0232(4) 0.0215(4) 0.0015(3) 0.0069(3) 0.0082(3) O6 0.0238(4) 0.0210(4) 0.0332(5) -0.0040(3) 0.0067(3) 0.0039(3) O3 0.0359(5) 0.0242(4) 0.0270(4) -0.0009(3) 0.0093(4) 0.0100(3) O5 0.0225(4) 0.0232(4) 0.0303(4) -0.0016(3) 0.0069(3) 0.0022(3) O1 0.0364(5) 0.0247(4) 0.0267(4) -0.0026(3) 0.0076(4) 0.0039(4) O2 0.0432(5) 0.0260(4) 0.0238(4) -0.0013(3) 0.0074(4) 0.0047(4) C7 0.0250(5) 0.0260(5) 0.0235(5) 0.0001(4) 0.0100(4) 0.0001(4) C1 0.0225(5) 0.0266(6) 0.0230(5) 0.0000(4) 0.0085(4) -0.0003(4) C12 0.0237(5) 0.0208(5) 0.0189(5) 0.0018(4) 0.0061(4) 0.0043(4) C6 0.0260(5) 0.0287(6) 0.0258(6) 0.0004(5) 0.0093(4) 0.0013(4) N1 0.0365(6) 0.0261(5) 0.0238(5) -0.0023(4) 0.0053(4) 0.0037(4) C10 0.0220(5) 0.0197(5) 0.0233(5) -0.0003(4) 0.0062(4) 0.0020(4) C11 0.0210(5) 0.0202(5) 0.0217(5) 0.0001(4) 0.0049(4) 0.0035(4) C13 0.0259(5) 0.0233(5) 0.0273(6) 0.0038(4) 0.0071(4) 0.0049(4) C2 0.0248(5) 0.0258(6) 0.0262(6) -0.0001(5) 0.0095(4) -0.0011(4) C3 0.0284(6) 0.0304(6) 0.0266(6) -0.0040(5) 0.0090(5) -0.0028(5) C4 0.0286(6) 0.0375(7) 0.0232(6) 0.0005(5) 0.0055(5) -0.0020(5) C8 0.0356(7) 0.0264(6) 0.0332(6) -0.0066(5) 0.0121(5) 0.0005(5) C5 0.0284(6) 0.0328(6) 0.0284(6) 0.0038(5) 0.0072(5) 0.0037(5) C14 0.0301(6) 0.0380(7) 0.0262(6) 0.0075(5) 0.0087(5) 0.0048(5) C9 0.0402(7) 0.0281(6) 0.0432(8) -0.0018(6) 0.0119(6) 0.0034(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 O4 C10 1.3162(14) . ? O4 H7 0.96(3) . ? O6 C12 1.3092(14) . ? O6 H10 0.94(2) . ? O3 C10 1.2156(14) . ? O5 C12 1.2292(15) . ? O1 C2 1.3663(16) . ? O1 C8 1.4438(15) . ? O2 C7 1.2524(15) . ? C7 N1 1.3263(17) . ? C7 C1 1.4954(17) . ? C1 C6 1.3943(17) . ? C1 C2 1.4102(17) . ? C12 C11 1.5118(15) . ? C6 C5 1.3856(18) . ? C6 H6 0.9500 . ? N1 H2 0.91(2) . ? N1 H1 0.889(19) . ? C10 C11 1.5253(16) . ? C11 C13 1.5328(16) . ? C11 H11 1.0000 . ? C13 C14 1.5230(18) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C2 C3 1.3973(18) . ? C3 C4 1.3870(19) . ? C3 H3 0.9500 . ? C4 C5 1.3866(19) . ? C4 H4 0.9500 . ? C8 C9 1.506(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C5 H5 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? 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 O4 H7 113.4(14) . . ? C12 O6 H10 106.8(12) . . ? C2 O1 C8 119.37(10) . . ? O2 C7 N1 121.49(11) . . ? O2 C7 C1 118.60(11) . . ? N1 C7 C1 119.91(11) . . ? C6 C1 C2 118.67(11) . . ? C6 C1 C7 116.31(11) . . ? C2 C1 C7 125.01(11) . . ? O5 C12 O6 123.90(11) . . ? O5 C12 C11 121.05(10) . . ? O6 C12 C11 115.05(10) . . ? C5 C6 C1 121.67(12) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? C7 N1 H2 117.6(12) . . ? C7 N1 H1 120.4(12) . . ? H2 N1 H1 121.9(16) . . ? O3 C10 O4 124.98(11) . . ? O3 C10 C11 123.11(10) . . ? O4 C10 C11 111.91(9) . . ? C12 C11 C10 107.68(9) . . ? C12 C11 C13 110.71(10) . . ? C10 C11 C13 113.04(10) . . ? C12 C11 H11 108.4 . . ? C10 C11 H11 108.4 . . ? C13 C11 H11 108.4 . . ? C14 C13 C11 111.38(10) . . ? C14 C13 H13A 109.4 . . ? C11 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? C11 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? O1 C2 C3 122.42(11) . . ? O1 C2 C1 117.89(10) . . ? C3 C2 C1 119.69(12) . . ? C4 C3 C2 120.04(12) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.93(12) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? O1 C8 C9 106.75(11) . . ? O1 C8 H8A 110.4 . . ? C9 C8 H8A 110.4 . . ? O1 C8 H8B 110.4 . . ? C9 C8 H8B 110.4 . . ? H8A C8 H8B 108.6 . . ? C6 C5 C4 119.00(12) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.300 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.045 #====END data_EA+EMA-Form-II _database_code_depnum_ccdc_archive 'CCDC 752466' #TrackingRef 'Dr.Srinivasulu_CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Form II of ethenzamide and ethylmalonic acid cocrystal' ; _chemical_name_common "'Form II of ethenzamide and ethylmalonic acid cocrystal'" _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 N O2, C5 H8 O4' _chemical_formula_sum 'C14 H19 N O6' _chemical_formula_weight 297.30 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_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 14.501(3) _cell_length_b 7.6438(15) _cell_length_c 14.323(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.45(3) _cell_angle_gamma 90.00 _cell_volume 1506.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3946 _cell_measurement_theta_min 2.6647 _cell_measurement_theta_max 30.8624 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11739 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3718 _reflns_number_gt 3308 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0885P)^2^+0.8049P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3718 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1071 _refine_ls_R_factor_gt 0.0962 _refine_ls_wR_factor_ref 0.2345 _refine_ls_wR_factor_gt 0.2261 _refine_ls_goodness_of_fit_ref 1.286 _refine_ls_restrained_S_all 1.286 _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 O3 O 1.01536(14) 0.7840(3) 1.01239(17) 0.0424(5) Uani 1 1 d . . . O5 O 0.71013(13) 0.5578(3) 0.89936(15) 0.0392(5) Uani 1 1 d . . . O1 O 0.63707(13) 0.2364(2) 1.03669(15) 0.0359(5) Uani 1 1 d . . . O2 O 0.33727(14) 0.2474(3) 0.90402(15) 0.0404(5) Uani 1 1 d . . . N1 N 0.45908(18) 0.3185(3) 1.04102(18) 0.0336(5) Uani 1 1 d . . . O4 O 0.89161(14) 0.9317(3) 0.90874(16) 0.0408(5) Uani 1 1 d D . . O6 O 0.80349(15) 0.7028(3) 1.03197(16) 0.0423(5) Uani 1 1 d . . . C7 C 0.42556(19) 0.2443(3) 0.95284(19) 0.0307(5) Uani 1 1 d . . . C6 C 0.4504(2) 0.0659(3) 0.8200(2) 0.0343(6) Uani 1 1 d . . . H6 H 0.3816 0.0670 0.7920 0.041 Uiso 1 1 calc R . . C11 C 0.87617(18) 0.6244(3) 0.9113(2) 0.0333(6) Uani 1 1 d . . . H11 H 0.9171 0.5218 0.9426 0.040 Uiso 1 1 calc R . . C1 C 0.49379(19) 0.1536(3) 0.90876(19) 0.0309(6) Uani 1 1 d . . . C4 C 0.6063(2) -0.0235(4) 0.8127(2) 0.0395(6) Uani 1 1 d . . . H4 H 0.6445 -0.0849 0.7805 0.047 Uiso 1 1 calc R . . C10 C 0.93450(19) 0.7877(3) 0.9495(2) 0.0338(6) Uani 1 1 d . . . C5 C 0.5057(2) -0.0227(4) 0.7718(2) 0.0379(6) Uani 1 1 d . . . H5 H 0.4752 -0.0820 0.7117 0.045 Uiso 1 1 calc R . . C12 C 0.78674(19) 0.6251(3) 0.9458(2) 0.0334(6) Uani 1 1 d . . . C2 C 0.59607(19) 0.1514(3) 0.9490(2) 0.0329(6) Uani 1 1 d . . . C3 C 0.6513(2) 0.0641(4) 0.8997(2) 0.0361(6) Uani 1 1 d . . . H3 H 0.7203 0.0646 0.9260 0.043 Uiso 1 1 calc R . . C8 C 0.74079(19) 0.2245(4) 1.0843(2) 0.0378(6) Uani 1 1 d . . . H8A H 0.7761 0.2748 1.0417 0.045 Uiso 1 1 calc R . . H8B H 0.7607 0.1008 1.0980 0.045 Uiso 1 1 calc R . . C9 C 0.7632(2) 0.3266(4) 1.1793(2) 0.0432(7) Uani 1 1 d . . . H9C H 0.7448 0.4493 1.1645 0.065 Uiso 1 1 calc R . . H9B H 0.8330 0.3194 1.2150 0.065 Uiso 1 1 calc R . . H9A H 0.7265 0.2773 1.2200 0.065 Uiso 1 1 calc R . . C13 C 0.8511(2) 0.6042(4) 0.8000(2) 0.0404(7) Uani 1 1 d . . . H13B H 0.8127 0.7067 0.7671 0.048 Uiso 1 1 calc R . . H13A H 0.8104 0.4985 0.7784 0.048 Uiso 1 1 calc R . . C14 C 0.9424(2) 0.5886(5) 0.7684(3) 0.0515(8) Uani 1 1 d . . . H14A H 0.9808 0.6962 0.7858 0.077 Uiso 1 1 calc R . . H14B H 0.9233 0.5706 0.6971 0.077 Uiso 1 1 calc R . . H14C H 0.9815 0.4890 0.8021 0.077 Uiso 1 1 calc R . . H1 H 0.523(2) 0.320(4) 1.076(2) 0.035(8) Uiso 1 1 d . . . H10 H 0.747(3) 0.711(6) 1.051(3) 0.078(13) Uiso 1 1 d . . . H2 H 0.412(3) 0.364(5) 1.062(3) 0.051(10) Uiso 1 1 d . . . H7 H 0.930(3) 1.026(5) 0.937(4) 0.106(17) Uiso 1 1 d 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 O3 0.0307(10) 0.0330(10) 0.0550(14) -0.0025(9) 0.0015(9) 0.0010(8) O5 0.0312(9) 0.0414(11) 0.0438(12) -0.0044(9) 0.0102(8) -0.0065(8) O1 0.0310(9) 0.0382(10) 0.0372(11) 0.0000(8) 0.0089(8) 0.0022(7) O2 0.0339(10) 0.0500(12) 0.0349(11) -0.0004(9) 0.0074(8) 0.0067(8) N1 0.0306(11) 0.0332(12) 0.0363(13) -0.0033(10) 0.0098(10) -0.0002(9) O4 0.0356(10) 0.0309(10) 0.0501(13) 0.0018(9) 0.0053(9) 0.0006(8) O6 0.0347(10) 0.0520(13) 0.0391(12) -0.0113(9) 0.0103(9) -0.0028(9) C7 0.0349(13) 0.0280(12) 0.0292(13) 0.0041(10) 0.0102(11) 0.0021(10) C6 0.0391(14) 0.0295(13) 0.0350(14) 0.0047(11) 0.0129(12) 0.0030(11) C11 0.0289(12) 0.0270(12) 0.0428(15) -0.0032(11) 0.0095(11) -0.0004(9) C1 0.0362(13) 0.0263(12) 0.0316(13) 0.0053(10) 0.0126(11) 0.0033(10) C4 0.0479(16) 0.0335(14) 0.0432(16) 0.0048(12) 0.0231(13) 0.0063(12) C10 0.0304(12) 0.0295(13) 0.0420(15) -0.0014(11) 0.0123(11) 0.0003(10) C5 0.0479(16) 0.0316(13) 0.0342(14) 0.0034(11) 0.0129(12) 0.0037(12) C12 0.0332(13) 0.0299(13) 0.0359(14) -0.0011(11) 0.0094(11) -0.0008(10) C2 0.0366(13) 0.0280(13) 0.0341(14) 0.0036(10) 0.0114(11) 0.0010(10) C3 0.0363(13) 0.0348(14) 0.0407(15) 0.0051(11) 0.0170(12) 0.0043(11) C8 0.0300(13) 0.0379(15) 0.0446(16) 0.0056(12) 0.0106(12) 0.0028(11) C9 0.0376(15) 0.0416(16) 0.0477(18) 0.0008(13) 0.0095(13) 0.0015(12) C13 0.0371(14) 0.0438(16) 0.0412(16) -0.0075(13) 0.0139(12) -0.0029(12) C14 0.0484(17) 0.058(2) 0.055(2) -0.0095(16) 0.0260(16) -0.0031(15) _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 O3 C10 1.232(3) . ? O5 C12 1.214(3) . ? O1 C2 1.372(3) . ? O1 C8 1.444(3) . ? O2 C7 1.250(3) . ? N1 C7 1.328(4) . ? N1 H1 0.90(3) . ? N1 H2 0.90(4) . ? O4 C10 1.307(3) . ? O4 H7 0.92(2) . ? O6 C12 1.321(3) . ? O6 H10 0.94(5) . ? C7 C1 1.501(4) . ? C6 C5 1.389(4) . ? C6 C1 1.398(4) . ? C6 H6 0.9500 . ? C11 C10 1.510(4) . ? C11 C13 1.527(4) . ? C11 C12 1.527(4) . ? C11 H11 1.0000 . ? C1 C2 1.411(4) . ? C4 C3 1.383(4) . ? C4 C5 1.388(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C2 C3 1.395(4) . ? C3 H3 0.9500 . ? C8 C9 1.512(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9C 0.9800 . ? C9 H9B 0.9800 . ? C9 H9A 0.9800 . ? C13 C14 1.533(4) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C8 119.2(2) . . ? C7 N1 H1 122(2) . . ? C7 N1 H2 113(2) . . ? H1 N1 H2 125(3) . . ? C10 O4 H7 109(3) . . ? C12 O6 H10 112(3) . . ? O2 C7 N1 121.7(2) . . ? O2 C7 C1 117.9(2) . . ? N1 C7 C1 120.4(2) . . ? C5 C6 C1 121.4(3) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? C10 C11 C13 112.5(2) . . ? C10 C11 C12 108.4(2) . . ? C13 C11 C12 113.1(2) . . ? C10 C11 H11 107.5 . . ? C13 C11 H11 107.5 . . ? C12 C11 H11 107.5 . . ? C6 C1 C2 118.5(2) . . ? C6 C1 C7 115.9(2) . . ? C2 C1 C7 125.5(2) . . ? C3 C4 C5 120.8(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? O3 C10 O4 123.6(2) . . ? O3 C10 C11 122.7(2) . . ? O4 C10 C11 113.7(2) . . ? C4 C5 C6 119.2(3) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? O5 C12 O6 124.6(3) . . ? O5 C12 C11 123.0(2) . . ? O6 C12 C11 112.3(2) . . ? O1 C2 C3 122.6(2) . . ? O1 C2 C1 117.6(2) . . ? C3 C2 C1 119.8(3) . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? O1 C8 C9 106.7(2) . . ? O1 C8 H8A 110.4 . . ? C9 C8 H8A 110.4 . . ? O1 C8 H8B 110.4 . . ? C9 C8 H8B 110.4 . . ? H8A C8 H8B 108.6 . . ? C8 C9 H9C 109.5 . . ? C8 C9 H9B 109.5 . . ? H9C C9 H9B 109.5 . . ? C8 C9 H9A 109.5 . . ? H9C C9 H9A 109.5 . . ? H9B C9 H9A 109.5 . . ? C11 C13 C14 111.9(3) . . ? C11 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? C11 C13 H13A 109.2 . . ? C14 C13 H13A 109.2 . . ? H13B C13 H13A 107.9 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.423 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.085 #====END #====END data_EA+EMA-Form-II _database_code_depnum_ccdc_archive 'CCDC 775334' #TrackingRef 'C004491A_CIF_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Form II of ethenzamide and ethylmalonic acid cocrystal' ; _chemical_name_common ; 'Form II cocrystal of 1:1 ethenzamide and ethylmalonic acid cocrystal' ; _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 N O2, C5 H8 O4' _chemical_formula_sum 'C14 H19 N O6' _chemical_formula_weight 297.30 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_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 14.463(3) _cell_length_b 7.6366(15) _cell_length_c 14.296(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.42(3) _cell_angle_gamma 90.00 _cell_volume 1498.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3798 _cell_measurement_theta_min 2.4219 _cell_measurement_theta_max 31.0096 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9602 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10980 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3692 _reflns_number_gt 3310 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0582P)^2^+0.5071P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3692 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1456 _refine_ls_wR_factor_gt 0.1403 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _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 O5 O 0.48439(8) 0.21592(16) 0.48768(10) 0.0370(3) Uani 1 1 d . . . O3 O 0.78990(8) 0.44198(17) 0.60070(9) 0.0344(3) Uani 1 1 d . . . O1 O 0.86289(8) 0.76369(16) 0.46324(9) 0.0314(3) Uani 1 1 d . . . O2 O 1.16306(9) 0.75253(18) 0.59583(9) 0.0361(3) Uani 1 1 d . . . O4 O 0.69626(9) 0.29750(19) 0.46809(9) 0.0373(3) Uani 1 1 d . . . N1 N 1.04104(11) 0.6816(2) 0.45917(11) 0.0298(3) Uani 1 1 d . . . O6 O 0.60819(9) 0.06807(17) 0.59128(10) 0.0360(3) Uani 1 1 d . . . C7 C 1.07419(11) 0.7558(2) 0.54713(12) 0.0268(3) Uani 1 1 d . . . C10 C 0.71330(11) 0.3752(2) 0.55399(12) 0.0278(3) Uani 1 1 d . . . C6 C 1.04941(13) 0.9345(2) 0.67983(12) 0.0305(4) Uani 1 1 d . . . H6 H 1.1184 0.9337 0.7077 0.037 Uiso 1 1 calc R . . C1 C 1.00599(12) 0.8463(2) 0.59099(12) 0.0273(3) Uani 1 1 d . . . C11 C 0.62364(11) 0.3756(2) 0.58838(12) 0.0285(3) Uani 1 1 d . . . H11 H 0.5826 0.4783 0.5571 0.034 Uiso 1 1 calc R . . C12 C 0.56526(12) 0.2122(2) 0.55059(13) 0.0292(3) Uani 1 1 d . . . C4 C 0.89356(14) 1.0232(2) 0.68783(13) 0.0352(4) Uani 1 1 d . . . H4 H 0.8553 1.0833 0.7207 0.042 Uiso 1 1 calc R . . C5 C 0.99430(14) 1.0229(2) 0.72815(13) 0.0342(4) Uani 1 1 d . . . H5 H 1.0251 1.0826 0.7882 0.041 Uiso 1 1 calc R . . C2 C 0.90341(12) 0.8488(2) 0.55069(12) 0.0288(4) Uani 1 1 d . . . C3 C 0.84820(13) 0.9367(2) 0.60013(13) 0.0325(4) Uani 1 1 d . . . H3 H 0.7791 0.9372 0.5735 0.039 Uiso 1 1 calc R . . C8 C 0.75905(12) 0.7755(2) 0.41603(14) 0.0334(4) Uani 1 1 d . . . H8A H 0.7390 0.8993 0.4025 0.040 Uiso 1 1 calc R . . H8B H 0.7239 0.7247 0.4588 0.040 Uiso 1 1 calc R . . C9 C 0.73663(13) 0.6742(3) 0.32111(15) 0.0396(4) Uani 1 1 d . . . H9A H 0.7732 0.7241 0.2803 0.059 Uiso 1 1 calc R . . H9B H 0.6666 0.6809 0.2855 0.059 Uiso 1 1 calc R . . H9C H 0.7555 0.5514 0.3357 0.059 Uiso 1 1 calc R . . C13 C 0.64876(13) 0.3949(3) 0.70008(13) 0.0352(4) Uani 1 1 d . . . H13A H 0.6871 0.2919 0.7327 0.042 Uiso 1 1 calc R . . H13B H 0.6897 0.5004 0.7219 0.042 Uiso 1 1 calc R . . C14 C 0.55773(15) 0.4106(3) 0.73192(16) 0.0462(5) Uani 1 1 d . . . H14A H 0.5193 0.5120 0.6994 0.069 Uiso 1 1 calc R . . H14B H 0.5770 0.4260 0.8036 0.069 Uiso 1 1 calc R . . H14C H 0.5185 0.3041 0.7132 0.069 Uiso 1 1 calc R . . H1 H 0.9758(17) 0.687(3) 0.4265(16) 0.043(6) Uiso 1 1 d . . . H2 H 1.0851(17) 0.629(3) 0.4348(16) 0.049(6) Uiso 1 1 d . . . H10 H 0.570(2) -0.039(4) 0.561(2) 0.084(9) Uiso 1 1 d . . . H7 H 0.757(2) 0.288(4) 0.449(2) 0.079(9) Uiso 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 O5 0.0264(6) 0.0285(6) 0.0481(8) -0.0026(6) 0.0003(5) -0.0004(5) O3 0.0266(6) 0.0379(7) 0.0380(7) -0.0066(5) 0.0092(5) -0.0059(5) O1 0.0263(6) 0.0350(7) 0.0316(6) 0.0000(5) 0.0073(5) 0.0011(5) O2 0.0288(6) 0.0480(8) 0.0295(6) -0.0017(5) 0.0061(5) 0.0066(5) O4 0.0300(6) 0.0475(8) 0.0334(6) -0.0102(6) 0.0085(5) -0.0038(5) N1 0.0283(7) 0.0306(8) 0.0307(7) -0.0027(6) 0.0093(6) -0.0004(6) O6 0.0315(6) 0.0257(6) 0.0447(7) 0.0007(5) 0.0032(5) -0.0004(5) C7 0.0280(7) 0.0250(8) 0.0277(8) 0.0052(6) 0.0094(6) 0.0018(6) C10 0.0284(7) 0.0235(8) 0.0298(8) 0.0005(6) 0.0065(6) 0.0000(6) C6 0.0360(8) 0.0262(8) 0.0291(8) 0.0061(7) 0.0101(7) 0.0048(7) C1 0.0322(8) 0.0237(8) 0.0271(8) 0.0063(6) 0.0110(6) 0.0029(6) C11 0.0244(7) 0.0245(8) 0.0351(9) -0.0011(7) 0.0071(6) -0.0003(6) C12 0.0267(7) 0.0261(8) 0.0336(8) -0.0008(7) 0.0081(6) 0.0010(6) C4 0.0451(10) 0.0297(9) 0.0363(9) 0.0049(7) 0.0207(8) 0.0067(7) C5 0.0440(10) 0.0287(9) 0.0303(8) 0.0018(7) 0.0125(7) 0.0044(7) C2 0.0322(8) 0.0256(8) 0.0295(8) 0.0051(6) 0.0111(7) 0.0023(6) C3 0.0328(8) 0.0309(9) 0.0368(9) 0.0052(7) 0.0151(7) 0.0040(7) C8 0.0254(8) 0.0340(9) 0.0394(9) 0.0045(7) 0.0083(7) 0.0033(6) C9 0.0330(9) 0.0376(10) 0.0442(11) 0.0004(8) 0.0064(8) 0.0007(7) C13 0.0321(8) 0.0376(10) 0.0364(9) -0.0080(8) 0.0114(7) -0.0047(7) C14 0.0413(10) 0.0528(13) 0.0502(12) -0.0084(10) 0.0227(9) -0.0030(9) _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 O5 C12 1.230(2) . ? O3 C10 1.2107(19) . ? O1 C2 1.366(2) . ? O1 C8 1.4418(19) . ? O2 C7 1.254(2) . ? O4 C10 1.315(2) . ? O4 H7 1.00(3) . ? N1 C7 1.324(2) . ? N1 H1 0.91(2) . ? N1 H2 0.91(2) . ? O6 C12 1.306(2) . ? O6 H10 1.01(3) . ? C7 C1 1.495(2) . ? C10 C11 1.525(2) . ? C6 C5 1.384(2) . ? C6 C1 1.399(2) . ? C6 H6 0.9500 . ? C1 C2 1.412(2) . ? C11 C12 1.508(2) . ? C11 C13 1.529(2) . ? C11 H11 1.0000 . ? C4 C3 1.385(3) . ? C4 C5 1.387(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C2 C3 1.394(2) . ? C3 H3 0.9500 . ? C8 C9 1.506(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C13 C14 1.528(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C8 118.75(13) . . ? C10 O4 H7 111.2(16) . . ? C7 N1 H1 118.3(14) . . ? C7 N1 H2 117.8(14) . . ? H1 N1 H2 124.0(19) . . ? C12 O6 H10 111.8(17) . . ? O2 C7 N1 121.26(16) . . ? O2 C7 C1 118.23(15) . . ? N1 C7 C1 120.51(15) . . ? O3 C10 O4 125.02(16) . . ? O3 C10 C11 122.99(15) . . ? O4 C10 C11 111.97(14) . . ? C5 C6 C1 121.58(16) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? C6 C1 C2 118.47(15) . . ? C6 C1 C7 115.90(15) . . ? C2 C1 C7 125.63(15) . . ? C12 C11 C10 108.66(14) . . ? C12 C11 C13 112.06(15) . . ? C10 C11 C13 113.03(13) . . ? C12 C11 H11 107.6 . . ? C10 C11 H11 107.6 . . ? C13 C11 H11 107.6 . . ? O5 C12 O6 123.62(15) . . ? O5 C12 C11 122.55(15) . . ? O6 C12 C11 113.83(14) . . ? C3 C4 C5 120.67(17) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 119.22(16) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? O1 C2 C3 122.97(15) . . ? O1 C2 C1 117.31(15) . . ? C3 C2 C1 119.72(16) . . ? C4 C3 C2 120.34(16) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? O1 C8 C9 106.60(14) . . ? O1 C8 H8A 110.4 . . ? C9 C8 H8A 110.4 . . ? O1 C8 H8B 110.4 . . ? C9 C8 H8B 110.4 . . ? H8A C8 H8B 108.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C14 C13 C11 112.09(15) . . ? C14 C13 H13A 109.2 . . ? C11 C13 H13A 109.2 . . ? C14 C13 H13B 109.2 . . ? C11 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.208 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.047 #====END