# 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 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Mikelis Veidis' _publ_contact_author_email VEIDIS@LU.LV _publ_section_title ; Nicotinamide fumaric acid cocrystals: diversity of stoichiometry ; _publ_contact_author_address ; Department of Chemistry, University of Latvia, Kr. Valdemara 48, Riga, LV-1013, Latvia. ; _publ_contact_author_fax '+371 737 8736' _publ_contact_author_phone '+371 737 8718' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures have been sent by mail. ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name ? loop_ _publ_author_name 'Mikelis Veidis' 'Liana Orola' #======END data_2 _database_code_depnum_ccdc_archive 'CCDC 686162' _audit_creation_method CRYSTALS_ver_12.82 _chemical_name_systematic 'nicotinamide fumaric acid 2:1' _chemical_melting_point ? _cell_length_a 5.592(3) _cell_length_b 12.044(1) _cell_length_c 13.131(5) _cell_angle_alpha 90 _cell_angle_beta 96.00(5) _cell_angle_gamma 90 _cell_volume 879.5(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C16 H16 N4 O6 # Dc = 1.36 Fooo = 376.00 Mu = 9.02 M = 180.16 # Found Formula = C16 H16 N4 O6 # Dc = 1.36 FOOO = 376.00 Mu = 9.02 M = 180.16 _chemical_formula_sum 'C16 H16 N4 O6' _chemical_formula_moiety 'C16 H16 N4 O6' _chemical_compound_source ? _chemical_formula_weight 360.33 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 295 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.22 _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.902 # Sheldrick geometric approximatio 0.82 0.94 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w/2\q _computing_data_collection 'CAD4 Express, (Straver, 1992)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_cell_refinement 'CAD4 Express, (Straver, 1992)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _diffrn_standards_interval_time 60 _diffrn_standards_interval_count ? _diffrn_standards_number 2 _diffrn_standards_decay_% 2 _diffrn_ambient_temperature 295 _diffrn_reflns_number 1604 _reflns_number_total 1386 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 1604 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1600 _diffrn_reflns_theta_min 4.995 _diffrn_reflns_theta_max 67.924 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 67.924 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.22 _refine_diff_density_max 0.30 _refine_ls_number_reflns 1386 _refine_ls_number_restraints 0 _refine_ls_number_parameters 119 #_refine_ls_R_factor_ref 0.0527 _refine_ls_wR_factor_ref 0.0673 _refine_ls_goodness_of_fit_ref 1.1029 #_reflns_number_all 1587 _refine_ls_R_factor_all 0.0580 _refine_ls_wR_factor_all 0.0786 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 1386 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_gt 0.0673 _refine_ls_shift/su_max 0.000324 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.99 1.83 2.14 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O11 O 0.2701(2) 0.05773(10) 0.64942(8) 0.0599 1.0000 Uani . . . . . . O10 O 0.0734(2) 0.13499(10) 0.51146(8) 0.0610 1.0000 Uani . . . . . . O2 O -0.7515(2) 0.41112(11) 0.48895(9) 0.0680 1.0000 Uani . . . . . . N6 N -0.1955(2) 0.23210(11) 0.63037(10) 0.0546 1.0000 Uani . . . . . . N1 N -0.8444(3) 0.49175(13) 0.63406(11) 0.0636 1.0000 Uani . . . . . . C4 C -0.5293(3) 0.35315(11) 0.64177(11) 0.0460 1.0000 Uani . . . . . . C9 C -0.5167(3) 0.33311(13) 0.74646(11) 0.0537 1.0000 Uani . . . . . . C3 C -0.7178(3) 0.42192(12) 0.58239(11) 0.0517 1.0000 Uani . . . . . . C13 C 0.4022(3) 0.02650(13) 0.48485(11) 0.0518 1.0000 Uani . . . . . . C7 C -0.1867(3) 0.21269(13) 0.73081(13) 0.0568 1.0000 Uani . . . . . . C12 C 0.2426(3) 0.07389(12) 0.55789(11) 0.0473 1.0000 Uani . . . . . . C5 C -0.3625(3) 0.30083(13) 0.58767(11) 0.0521 1.0000 Uani . . . . . . C8 C -0.3439(3) 0.26141(14) 0.79134(12) 0.0593 1.0000 Uani . . . . . . H13 H 0.3584 0.0357 0.4120 0.0645 1.0000 Uiso R . . . . . H7 H -0.0665 0.1621 0.7602 0.0675 1.0000 Uiso R . . . . . H5 H -0.3722 0.3156 0.5151 0.0629 1.0000 Uiso R . . . . . H8 H -0.3317 0.2477 0.8642 0.0710 1.0000 Uiso R . . . . . H1 H -0.8063 0.5008 0.7017 0.0748 1.0000 Uiso R . . . . . H9 H -0.6232 0.3692 0.7875 0.0654 1.0000 Uiso R . . . . . H2 H -0.9671 0.5279 0.5991 0.0764 1.0000 Uiso R . . . . . H10 H 0.0003 0.1648 0.5610 0.0935 1.0000 Uiso 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 O11 0.0689(7) 0.0694(8) 0.0423(6) 0.0061(5) 0.0101(5) 0.0144(5) O10 0.0706(8) 0.0712(7) 0.0436(6) 0.0081(5) 0.0170(5) 0.0241(6) O2 0.0827(9) 0.0772(8) 0.0403(7) -0.0114(5) -0.0106(5) 0.0294(6) N6 0.0594(8) 0.0583(8) 0.0464(8) -0.0009(5) 0.0064(5) 0.0155(6) N1 0.0722(9) 0.0716(9) 0.0444(7) -0.0115(6) -0.0063(6) 0.0296(7) C4 0.0520(8) 0.0468(7) 0.0384(7) -0.0048(6) 0.0006(6) 0.0071(6) C9 0.0688(10) 0.0543(8) 0.0384(7) -0.0041(6) 0.0075(6) 0.0125(7) C3 0.0605(9) 0.0540(8) 0.0388(8) -0.0062(6) -0.0034(6) 0.0105(7) C13 0.0593(9) 0.0574(9) 0.0400(8) 0.0031(6) 0.0110(6) 0.0071(6) C7 0.066(1) 0.0553(9) 0.0478(8) -0.0005(6) 0.0003(7) 0.0146(7) C12 0.0536(8) 0.0490(8) 0.0407(8) 0.0017(5) 0.0121(6) 0.0010(6) C5 0.0629(9) 0.0557(8) 0.0382(7) 0.0005(6) 0.0076(6) 0.0108(7) C8 0.0813(11) 0.0592(9) 0.0369(8) 0.0011(6) 0.0043(7) 0.0158(7) _refine_ls_extinction_coef 240(30) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _oxford_refine_ls_scale 4.33(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O11 . C12 . 1.2114(18) yes O10 . C12 . 1.2993(18) yes O10 . H10 . 0.880 no O2 . C3 . 1.2286(19) yes N6 . C7 . 1.335(2) yes N6 . C5 . 1.327(2) yes N1 . C3 . 1.330(2) yes N1 . H1 . 0.899 no N1 . H2 . 0.898 no C4 . C9 . 1.390(2) yes C4 . C3 . 1.495(2) yes C4 . C5 . 1.382(2) yes C9 . C8 . 1.381(2) yes C9 . H9 . 0.949 no C13 . C13 2_656 1.293(3) yes C13 . C12 . 1.490(2) yes C13 . H13 . 0.969 no C7 . C8 . 1.377(3) yes C7 . H7 . 0.957 no C5 . H5 . 0.965 no C8 . H8 . 0.966 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C12 . O10 . H10 . 104.8 no C7 . N6 . C5 . 118.56(13) yes C3 . N1 . H1 . 119.8 no C3 . N1 . H2 . 117.7 no H1 . N1 . H2 . 122.4 no C9 . C4 . C3 . 124.90(14) yes C9 . C4 . C5 . 117.51(14) yes C3 . C4 . C5 . 117.50(14) yes C4 . C9 . C8 . 119.44(14) yes C4 . C9 . H9 . 120.8 no C8 . C9 . H9 . 119.8 no C4 . C3 . N1 . 117.92(14) yes C4 . C3 . O2 . 119.23(14) yes N1 . C3 . O2 . 122.84(14) yes C13 2_656 C13 . C12 . 122.37(18) yes C13 2_656 C13 . H13 . 118.6 no C12 . C13 . H13 . 119.0 no N6 . C7 . C8 . 122.39(15) yes N6 . C7 . H7 . 117.5 no C8 . C7 . H7 . 120.1 no C13 . C12 . O10 . 111.76(13) yes C13 . C12 . O11 . 123.67(14) yes O10 . C12 . O11 . 124.57(14) yes C4 . C5 . N6 . 123.37(14) yes C4 . C5 . H5 . 116.9 no N6 . C5 . H5 . 119.8 no C9 . C8 . C7 . 118.73(15) yes C9 . C8 . H8 . 120.2 no C7 . C8 . H8 . 121.0 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 . H1 . O11 3_456 165.4 0.899 2.061 2.940(2) yes N1 . H2 . O2 2_366 172.2 0.898 1.993 2.885(3) yes O10 . H10 . N6 . 164.7 0.880 1.701 2.561(2) yes _chemical_name_common 'nicotinamide fumaric acid 2:1' # Attachment 'nic-fa.cif' # Supplementary Material (ESI) for Chemical Communications data_1 _database_code_depnum_ccdc_archive 'CCDC 689435' _audit_creation_method CRYSTALS_ver_12.82 _chemical_name_systematic 'nicotinamide fumaric acid 1:1' _chemical_melting_point ? _cell_length_a 5.550(1) _cell_length_b 13.792(1) _cell_length_c 14.360(2) _cell_angle_alpha 90 _cell_angle_beta 93.41(1) _cell_angle_gamma 90 _cell_volume 1097.2(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C10 H10 N2 O5 # Dc = 1.44 Fooo = 496.00 Mu = 10.10 M = 238.20 # Found Formula = C10 H10 N2 O5 # Dc = 1.44 FOOO = 496.00 Mu = 10.10 M = 238.20 _chemical_formula_sum 'C10 H10 N2 O5' _chemical_formula_moiety 'C10 H10 N2 O5' _chemical_compound_source ? _chemical_formula_weight 238.20 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 293 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.010 # Sheldrick geometric approximatio 0.82 0.82 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w/2\q _computing_data_collection 'CAD4 Express, (Straver, 1992)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_cell_refinement 'CAD4 Express, (Straver, 1992)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _diffrn_standards_interval_time 60 _diffrn_standards_interval_count ? _diffrn_standards_number 2 _diffrn_standards_decay_% 3.00 _diffrn_ambient_temperature 293 _diffrn_reflns_number 2247 _reflns_number_total 1931 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 1931 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1996 _diffrn_reflns_theta_min 4.449 _diffrn_reflns_theta_max 67.931 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 56.383 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -6 _reflns_limit_h_max 5 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.15 _refine_diff_density_max 0.16 _refine_ls_number_reflns 1634 _refine_ls_number_restraints 0 _refine_ls_number_parameters 155 #_refine_ls_R_factor_ref 0.0329 _refine_ls_wR_factor_ref 0.0579 _refine_ls_goodness_of_fit_ref 1.0483 #_reflns_number_all 1923 _refine_ls_R_factor_all 0.0394 _refine_ls_wR_factor_all 0.0582 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 1634 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_gt 0.0579 _refine_ls_shift/su_max 0.000500 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 91.8 123. 53.1 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens H2 H -0.5466 0.9795 0.6037 0.0594 1.0000 Uiso . . . . . . H7 H 0.4615 1.0800 0.8789 0.0556 1.0000 Uiso . . . . . . H8 H 0.2079 1.1915 0.7999 0.0593 1.0000 Uiso . . . . . . H9 H -0.1296 1.1354 0.7099 0.0522 1.0000 Uiso . . . . . . H17 H 1.4361 0.7026 1.1359 0.0800 1.0000 Uiso . . . . . . H13 H 0.7943 0.6437 0.9606 0.0530 1.0000 Uiso . . . . . . H14 H 1.0045 0.8174 1.0133 0.0498 1.0000 Uiso . . . . . . H10 H 0.5009 0.8902 0.8932 0.0764 1.0000 Uiso . . . . . . N1 N -0.4225(3) 1.00610(10) 0.63409(10) 0.0506 1.0000 Uani . . . . . . O2 O -0.3150(2) 0.85973(7) 0.69005(9) 0.0496 1.0000 Uani . . . . . . C3 C -0.2788(3) 0.94805(11) 0.68502(10) 0.0370 1.0000 Uani . . . . . . C4 C -0.0681(3) 0.99211(10) 0.73919(10) 0.0351 1.0000 Uani . . . . . . C5 C 0.0913(3) 0.93145(11) 0.78856(11) 0.0399 1.0000 Uani . . . . . . N6 N 0.2834(2) 0.96426(9) 0.83971(9) 0.0434 1.0000 Uani . . . . . . C7 C 0.3227(3) 1.05956(12) 0.84267(12) 0.0465 1.0000 Uani . . . . . . C8 C 0.1742(3) 1.12509(11) 0.79597(13) 0.0497 1.0000 Uani . . . . . . C9 C -0.0255(3) 1.09084(11) 0.74334(12) 0.0444 1.0000 Uani . . . . . . O17 O 1.3306(2) 0.73961(8) 1.10821(9) 0.0554 1.0000 Uani . . . . . . O11 O 0.4328(2) 0.72704(8) 0.87189(9) 0.0532 1.0000 Uani . . . . . . C12 C 0.5996(3) 0.76769(11) 0.91452(11) 0.0398 1.0000 Uani . . . . . . C13 C 0.7997(3) 0.71157(12) 0.96203(12) 0.0437 1.0000 Uani . . . . . . C14 C 0.9865(3) 0.75074(11) 1.00742(11) 0.0413 1.0000 Uani . . . . . . C15 C 1.1737(3) 0.68893(12) 1.05573(11) 0.0411 1.0000 Uani . . . . . . O16 O 1.1796(2) 0.60219(9) 1.04808(9) 0.0574 1.0000 Uani . . . . . . O10 O 0.6197(2) 0.86101(8) 0.92398(9) 0.0517 1.0000 Uani . . . . . . H5 H 0.0679 0.8621 0.7864 0.0493 1.0000 Uiso . . . . . . H1 H -0.3914 1.0774 0.6306 0.0586 1.0000 Uiso . . . . . . 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 N1 0.0442(9) 0.0345(7) 0.0695(9) 0.0081(6) -0.0262(7) -0.0067(6) O2 0.0460(7) 0.0286(5) 0.0710(8) 0.0002(5) -0.0237(6) -0.0037(5) C3 0.0338(8) 0.0304(7) 0.0457(8) 0.0001(6) -0.0070(6) -0.0002(6) C4 0.0318(9) 0.0302(7) 0.0423(8) -0.0010(6) -0.0065(6) -0.0009(6) C5 0.0380(9) 0.0289(7) 0.0511(9) -0.0004(6) -0.0105(7) -0.0001(6) N6 0.0395(8) 0.0358(7) 0.0527(8) -0.0006(6) -0.0157(6) 0.0011(6) C7 0.0410(10) 0.0390(9) 0.0574(10) -0.0078(7) -0.0158(8) -0.0032(7) C8 0.0500(10) 0.0283(8) 0.0685(11) -0.0047(8) -0.0164(8) -0.0027(7) C9 0.0419(10) 0.0314(8) 0.0577(10) 0.0004(7) -0.0154(7) 0.0032(7) O17 0.0469(8) 0.0399(6) 0.0755(8) -0.0015(6) -0.0299(6) 0.0036(5) O11 0.0417(7) 0.0421(7) 0.0725(8) -0.0015(6) -0.0241(6) -0.0051(5) C12 0.0354(9) 0.0371(8) 0.0455(8) 0.0009(6) -0.0084(7) -0.0029(7) C13 0.0391(9) 0.0358(8) 0.0547(9) 0.0021(7) -0.0095(7) 0.0027(7) C14 0.0367(9) 0.0362(8) 0.0498(9) 0.0018(7) -0.0083(7) 0.0030(7) C15 0.0329(9) 0.0384(9) 0.0507(9) 0.0008(7) -0.0078(7) 0.0012(6) O16 0.0484(8) 0.0382(7) 0.0819(9) -0.0018(6) -0.0264(6) 0.0053(5) O10 0.0463(7) 0.0353(6) 0.0695(8) 0.0027(5) -0.0285(6) 0.0003(5) _refine_ls_extinction_coef 67.9(17) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _oxford_refine_ls_scale 2.60(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag H2 . N1 . 0.874 no H7 . C7 . 0.947 no H8 . C8 . 0.936 no H9 . C9 . 0.954 no H17 . O17 . 0.857 no H13 . C13 . 0.937 no H14 . C14 . 0.928 no H10 . O10 . 0.870 no N1 . C3 . 1.3200(19) yes N1 . H1 . 1.000 no O2 . C3 . 1.2374(18) yes C3 . C4 . 1.495(2) yes C4 . C5 . 1.382(2) yes C4 . C9 . 1.383(2) yes C5 . N6 . 1.3369(19) yes C5 . H5 . 0.966 no N6 . C7 . 1.333(2) yes C7 . C8 . 1.371(2) yes C8 . C9 . 1.387(2) yes O17 . C15 . 1.3177(19) yes O11 . C12 . 1.2163(18) yes C12 . C13 . 1.486(2) yes C12 . O10 . 1.2983(19) yes C13 . C14 . 1.308(2) yes C14 . C15 . 1.484(2) yes C15 . O16 . 1.2020(19) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H2 . N1 . C3 . 117.0 no H2 . N1 . H1 . 121.4 no C3 . N1 . H1 . 121.6 no N1 . C3 . O2 . 122.31(14) yes N1 . C3 . C4 . 118.04(13) yes O2 . C3 . C4 . 119.64(13) yes C3 . C4 . C5 . 118.56(13) yes C3 . C4 . C9 . 123.32(14) yes C5 . C4 . C9 . 118.12(14) yes C4 . C5 . N6 . 122.83(14) yes C4 . C5 . H5 . 120.2 no N6 . C5 . H5 . 117.0 no C5 . N6 . C7 . 118.36(13) yes H7 . C7 . N6 . 116.0 no H7 . C7 . C8 . 121.2 no N6 . C7 . C8 . 122.83(14) yes H8 . C8 . C7 . 120.2 no H8 . C8 . C9 . 121.1 no C7 . C8 . C9 . 118.66(14) yes H9 . C9 . C8 . 119.7 no H9 . C9 . C4 . 121.1 no C8 . C9 . C4 . 119.21(14) yes H17 . O17 . C15 . 111.1 no O11 . C12 . C13 . 121.13(15) yes O11 . C12 . O10 . 124.57(15) yes C13 . C12 . O10 . 114.29(13) yes C12 . C13 . H13 . 119.2 no C12 . C13 . C14 . 124.21(15) yes H13 . C13 . C14 . 116.6 no H14 . C14 . C13 . 122.1 no H14 . C14 . C15 . 117.3 no C13 . C14 . C15 . 120.53(14) yes C14 . C15 . O17 . 112.53(13) yes C14 . C15 . O16 . 123.44(14) yes O17 . C15 . O16 . 124.03(15) yes H10 . O10 . C12 . 110.4 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 . H2 . O16 4_364 169.9 0.874 2.018 2.882(2) yes O17 . H17 . O2 4_765 171.4 0.857 1.767 2.618(2) yes O10 . H10 . N6 . 171.2 0.870 1.726 2.590(2) yes N1 . H1 . O11 3_556 163.5 1.000 2.077 3.049(2) yes _chemical_name_common 'nicotinamide fumaric acid 1:1'