# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Bruce Foxman' _publ_contact_author_address ; Department of Chemistry Brandeis University 415 South Street MS 015; Edison-Lecks 211 Waltham MA 02454-9110 USA ; _publ_contact_author_email FOXMAN1@BRANDEIS.EDU _publ_section_title ; Conformational Polymorphism of Methacrylamide ; loop_ _publ_author_name 'Bruce Foxman' 'Volker Enkelmann' 'Evan R. Guggenheim' 'Chengyun Guo' 'Magali B. Hickey' data_CRYSTALS_cif_4 _database_code_depnum_ccdc_archive 'CCDC 258650' _audit_creation_date 04-10-01 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title 'foxi methacrylamide mono 120K 05-04' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.0920(5) _cell_length_b 6.0470(4) _cell_length_c 9.4610(5) _cell_angle_alpha 90 _cell_angle_beta 113.1620(13) _cell_angle_gamma 90 _cell_volume 478.23(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? 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 0.0033 0.0016 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' O 0.0106 0.0060 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' N 0.0061 0.0033 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' _cell_formula_units_Z 4 # Given Formula = C4 H7 N1 O1 # Dc = 1.18 Fooo = 184.00 Mu = 0.86 M = 85.11 # Found Formula = C4 H7 N1 O1 # Dc = 1.18 FOOO = 184.00 Mu = 0.86 M = 85.11 _chemical_formula_sum 'C4 H7 N1 O1' _chemical_formula_moiety 'C4 H7 N1 O1' _chemical_compound_source ? _chemical_formula_weight 85.11 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.45 _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 184 _exptl_absorpt_coefficient_mu 0.086 # Sheldrick geometric approximatio 0.97 0.99 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9746 _exptl_absorpt_correction_T_max 0.9889 _diffrn_measurement_device_type Unknown _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _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 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 7057 _reflns_number_total 1251 _diffrn_reflns_av_R_equivalents 0.043 # Number of reflections with Friedels Law is 1251 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1272 _diffrn_reflns_theta_min 4.104 _diffrn_reflns_theta_max 28.999 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.549 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -12 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _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 -0.18 _refine_diff_density_max 0.14 _refine_ls_number_reflns 602 _refine_ls_number_restraints 12 _refine_ls_number_parameters 83 #_refine_ls_R_factor_ref 0.0408 _refine_ls_wR_factor_ref 0.0812 _refine_ls_goodness_of_fit_ref 1.0291 #_reflns_number_all 1251 _refine_ls_R_factor_all 0.1187 _refine_ls_wR_factor_all 0.0990 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 602 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_gt 0.0812 _refine_ls_shift/su_max 0.000185 # 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 mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.344E-01 0.200E-01 0.00 0.00 0.00 0.333 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 O1 O 0.66728(16) 0.1956(3) 0.04026(16) 0.0304 1.0000 Uani . . . . . . N1 N 0.4358(2) 0.1855(4) -0.1680(2) 0.0260 1.0000 Uani . . . . . . C1 C 0.5779(2) 0.2765(4) -0.0855(2) 0.0212 1.0000 Uani . . . . . . C2 C 0.6261(2) 0.4760(4) -0.1492(2) 0.0215 1.0000 Uani . . . . . . C3 C 0.7737(3) 0.5554(5) -0.0749(3) 0.0361 1.0000 Uani . . . . . . C4 C 0.5090(3) 0.5827(5) -0.2921(3) 0.0350 1.0000 Uani . . . . . . H31 H 0.807(3) 0.685(5) -0.112(3) 0.053(9) 1.0000 Uiso . . . . . . H32 H 0.849(2) 0.479(4) 0.018(3) 0.037(7) 1.0000 Uiso . . . . . . H41 H 0.562(3) 0.709(5) -0.322(3) 0.046(8) 1.0000 Uiso . . . . . . H42 H 0.466(3) 0.475(5) -0.380(3) 0.047(7) 1.0000 Uiso . . . . . . H43 H 0.419(3) 0.640(5) -0.267(3) 0.078(11) 1.0000 Uiso . . . . . . H11 H 0.369(3) 0.244(5) -0.257(3) 0.051(8) 1.0000 Uiso . . . . . . H12 H 0.405(2) 0.061(4) -0.126(3) 0.033(7) 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 O1 0.0255(7) 0.0320(11) 0.0217(8) 0.0060(8) -0.0034(6) -0.0062(8) N1 0.0233(9) 0.0281(12) 0.0183(9) 0.0062(8) -0.0007(7) -0.0051(9) C1 0.0220(10) 0.0207(13) 0.0191(10) -0.0012(9) 0.0062(7) -0.0019(10) C2 0.0243(9) 0.0188(12) 0.0214(9) -0.0003(9) 0.0090(7) 0.0007(10) C3 0.0346(12) 0.0344(18) 0.0316(13) 0.0079(12) 0.0048(10) -0.0113(13) C4 0.0320(13) 0.0352(17) 0.0326(14) 0.0135(13) 0.0072(10) -0.0042(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 8.4(5) 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 O1 . C1 . 1.247(2) yes N1 . C1 . 1.337(2) yes N1 . H11 . 0.89(3) no N1 . H12 . 0.94(3) no C1 . C2 . 1.490(3) yes C2 . C3 . 1.335(3) yes C2 . C4 . 1.498(3) yes C3 . H31 . 0.96(3) no C3 . H32 . 0.99(2) no C4 . H41 . 1.00(3) no C4 . H42 . 1.01(3) no C4 . H43 . 1.00(3) 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 C1 . N1 . H11 . 121.9(18) no C1 . N1 . H12 . 117.3(12) no H11 . N1 . H12 . 121(2) no N1 . C1 . O1 . 120.9(2) yes N1 . C1 . C2 . 117.88(18) yes O1 . C1 . C2 . 121.24(17) yes C1 . C2 . C3 . 118.3(2) yes C1 . C2 . C4 . 119.72(19) yes C3 . C2 . C4 . 122.0(3) yes C2 . C3 . H31 . 120.0(15) no C2 . C3 . H32 . 120.0(14) no H31 . C3 . H32 . 120.1(19) no C2 . C4 . H41 . 109.5(13) no C2 . C4 . H42 . 112.1(14) no H41 . C4 . H42 . 109(2) no C2 . C4 . H43 . 106.9(18) no H41 . C4 . H43 . 109(2) no H42 . C4 . H43 . 109(2) no data_CRYSTALS_cif_1 _database_code_depnum_ccdc_archive 'CCDC 260952' _audit_creation_date 04-09-30 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title KKMETHA _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.934(7) _cell_length_b 10.242(5) _cell_length_c 16.436(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 998.9(13) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-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 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' 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' 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' _cell_formula_units_Z 8 # Given Formula = C4 H7 N1 O1 # Dc = 1.13 Fooo = 368.00 Mu = 6.74 M = 85.11 # Found Formula = C4 H7 N1 O1 # Dc = 1.13 FOOO = 368.00 Mu = 6.74 M = 85.11 _chemical_formula_sum 'C4 H7 N1 O1' _chemical_formula_moiety 'C4 H7 N1 O1' _chemical_compound_source ? _chemical_formula_weight 85.11 _cell_measurement_reflns_used 11 _cell_measurement_theta_min 9 _cell_measurement_theta_max 23 _cell_measurement_temperature 294 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.132 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.674 # Sheldrick geometric approximatio 0.75 0.91 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; Azimutal absorption correction (North et al, 1968) ; _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_T_max 0.91 _diffrn_measurement_device_type Unknown _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_method \w/2\q _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _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 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time 7200 _diffrn_standards_interval_count ? _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 294 _diffrn_reflns_number 1651 _reflns_number_total 843 _diffrn_reflns_av_R_equivalents 0.017 # Number of reflections with Friedels Law is 843 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 803 _diffrn_reflns_theta_min 5.383 _diffrn_reflns_theta_max 64.916 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 64.916 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min 0 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _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 -0.10 _refine_diff_density_max 0.10 _refine_ls_number_reflns 314 _refine_ls_number_restraints 0 _refine_ls_number_parameters 56 #_refine_ls_R_factor_ref 0.0435 _refine_ls_wR_factor_ref 0.1023 _refine_ls_goodness_of_fit_ref 1.0995 #_reflns_number_all 843 _refine_ls_R_factor_all 0.1533 _refine_ls_wR_factor_all 0.1462 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 314 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_gt 0.1023 _refine_ls_shift/su_max 0.000069 # 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 ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.447E-01 0.655 0.00 0.00 0.00 0.333 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. North, A.C.T., Phillips, D.C. and Mathews, F.S., (1968), Acta Cryst, A24, 351-359 Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 O1 O 0.2161(6) -0.0826(3) 0.4389(2) 0.0879 1.0000 Uani . . . . . . N1 N 0.1617(6) 0.1329(3) 0.4462(3) 0.0803 1.0000 Uani . . . . . . C1 C 0.2732(9) 0.0296(4) 0.4192(3) 0.0679 1.0000 Uani . . . . . . C2 C 0.4679(9) 0.0506(4) 0.3654(3) 0.0682 1.0000 Uani . . . . . . C3 C 0.5244(11) 0.1708(5) 0.3357(4) 0.1302 1.0000 Uani . . . . . . C4 C 0.5941(11) -0.0614(5) 0.3420(4) 0.1218 1.0000 Uani . . . . . . H31 H 0.4366 0.2450 0.3497 0.1565 1.0000 Uiso . . . . . . H32 H 0.6516 0.1801 0.3011 0.1565 1.0000 Uiso . . . . . . H41 H 0.7145 -0.0355 0.3076 0.1459 1.0000 Uiso . . . . . . H42 H 0.6530 -0.1027 0.3892 0.1459 1.0000 Uiso . . . . . . H43 H 0.4988 -0.1205 0.3138 0.1459 1.0000 Uiso . . . . . . H11 H 0.0354 0.1217 0.4810 0.0963 1.0000 Uiso . . . . . . H12 H 0.2081 0.2182 0.4307 0.0963 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 O1 0.103(3) 0.0400(15) 0.121(3) 0.0030(17) 0.028(3) -0.0008(18) N1 0.090(3) 0.0406(19) 0.111(4) 0.001(2) 0.028(3) -0.002(2) C1 0.071(3) 0.049(2) 0.084(4) -0.005(3) 0.002(4) 0.000(3) C2 0.074(4) 0.058(3) 0.073(4) -0.003(3) 0.001(3) -0.001(3) C3 0.140(6) 0.067(3) 0.184(7) 0.002(4) 0.078(5) -0.019(4) C4 0.125(5) 0.082(3) 0.158(6) 0.004(4) 0.043(5) 0.019(4) _refine_ls_extinction_coef 31(6) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _oxford_refine_ls_scale 1.41(3) 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 O1 . C1 . 1.241(5) yes N1 . C1 . 1.324(5) yes N1 . H11 . 0.950 no N1 . H12 . 0.950 no C1 . C2 . 1.470(6) yes C2 . C3 . 1.366(6) yes C2 . C4 . 1.422(6) yes C3 . H31 . 0.950 no C3 . H32 . 0.950 no C4 . H41 . 0.950 no C4 . H42 . 0.950 no C4 . H43 . 0.950 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 C1 . N1 . H11 . 119.994 no C1 . N1 . H12 . 120.006 no H11 . N1 . H12 . 119.999 no N1 . C1 . O1 . 121.1(5) yes N1 . C1 . C2 . 118.5(4) yes O1 . C1 . C2 . 120.4(4) yes C1 . C2 . C3 . 122.6(5) yes C1 . C2 . C4 . 117.3(4) yes C3 . C2 . C4 . 120.1(5) yes C2 . C3 . H31 . 120.006 no C2 . C3 . H32 . 119.982 no H31 . C3 . H32 . 120.012 no C2 . C4 . H41 . 109.424 no C2 . C4 . H42 . 109.427 no H41 . C4 . H42 . 109.524 no C2 . C4 . H43 . 109.421 no H41 . C4 . H43 . 109.513 no H42 . C4 . H43 . 109.518 no data_CRYSTALS_cif_2 _database_code_depnum_ccdc_archive 'CCDC 260953' _audit_creation_date 04-09-30 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title KROD _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.3652(17) _cell_length_b 6.0863(15) _cell_length_c 9.743(3) _cell_angle_alpha 90 _cell_angle_beta 115.30(2) _cell_angle_gamma 90 _cell_volume 502.1(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? 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 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' 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' 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' _cell_formula_units_Z 4 # Given Formula = C4 H7 N1 O1 # Dc = 1.13 Fooo = 184.00 Mu = 6.70 M = 85.11 # Found Formula = C4 H7 N1 O1 # Dc = 1.13 FOOO = 184.00 Mu = 6.70 M = 85.11 _chemical_formula_sum 'C4 H7 N1 O1' _chemical_formula_moiety 'C4 H7 N1 O1' _chemical_compound_source ? _chemical_formula_weight 85.11 _cell_measurement_reflns_used 12 _cell_measurement_theta_min 9 _cell_measurement_theta_max 16 _cell_measurement_temperature 294 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_max 0.58 _exptl_crystal_density_diffrn 1.126 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 184 _exptl_absorpt_coefficient_mu 0.670 # Sheldrick geometric approximatio 0.82 0.95 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; Azimutal absorption correction (North et al, 1968) ; _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.95 _diffrn_measurement_device_type Unknown _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_method \w/2\q _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _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 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time 7200 _diffrn_standards_interval_count ? _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 294 _diffrn_reflns_number 1086 _reflns_number_total 1027 _diffrn_reflns_av_R_equivalents 0.021 # Number of reflections with Friedels Law is 1027 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1022 _diffrn_reflns_theta_min 5.486 _diffrn_reflns_theta_max 74.164 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.164 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min 0 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min -12 _reflns_limit_l_max 10 _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 -0.12 _refine_diff_density_max 0.12 _refine_ls_number_reflns 559 _refine_ls_number_restraints 0 _refine_ls_number_parameters 56 #_refine_ls_R_factor_ref 0.0525 _refine_ls_wR_factor_ref 0.1261 _refine_ls_goodness_of_fit_ref 1.0778 #_reflns_number_all 1027 _refine_ls_R_factor_all 0.1043 _refine_ls_wR_factor_all 0.1584 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 559 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_gt 0.1261 _refine_ls_shift/su_max 0.000078 # 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 ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.522E-01 0.228 0.00 0.00 0.00 0.333 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. North, A.C.T., Phillips, D.C. and Mathews, F.S., (1968), Acta Cryst, A24, 351-359 Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 O1 O 0.6637(2) 0.1947(4) 0.0366(2) 0.0922 1.0000 Uani . . . . . . N1 N 0.4341(3) 0.1823(4) -0.1685(3) 0.0836 1.0000 Uani . . . . . . C1 C 0.5740(3) 0.2714(5) -0.0875(3) 0.0682 1.0000 Uani . . . . . . C2 C 0.6211(3) 0.4661(5) -0.1506(3) 0.0732 1.0000 Uani . . . . . . C3 C 0.7684(5) 0.5523(8) -0.0686(4) 0.1265 1.0000 Uani . . . . . . C4 C 0.5174(5) 0.5596(8) -0.2891(5) 0.1305 1.0000 Uani . . . . . . H31 H 0.8022 0.6767 -0.1058 0.1367 1.0000 Uiso . . . . . . H32 H 0.8367 0.4877 0.0254 0.1367 1.0000 Uiso . . . . . . H41 H 0.5670 0.6818 -0.3116 0.1431 1.0000 Uiso . . . . . . H42 H 0.4908 0.4533 -0.3676 0.1431 1.0000 Uiso . . . . . . H43 H 0.4242 0.6072 -0.2819 0.1431 1.0000 Uiso . . . . . . H11 H 0.3666 0.2429 -0.2643 0.0884 1.0000 Uiso . . . . . . H12 H 0.4010 0.0577 -0.1308 0.0884 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 O1 0.0720(13) 0.1046(19) 0.0624(12) 0.0132(12) -0.0071(10) -0.0180(12) N1 0.0645(15) 0.091(2) 0.0656(14) 0.0148(13) -0.0008(12) -0.0114(13) C1 0.0585(15) 0.077(2) 0.0557(14) -0.0014(16) 0.0117(13) -0.0005(16) C2 0.0696(18) 0.076(2) 0.0658(16) -0.0003(17) 0.0213(15) -0.0012(17) C3 0.099(3) 0.141(4) 0.102(3) 0.025(3) 0.007(2) -0.048(3) C4 0.101(3) 0.136(4) 0.120(3) 0.048(3) 0.015(2) -0.016(3) _refine_ls_extinction_coef 38(7) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _oxford_refine_ls_scale 3.10(12) 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 O1 . C1 . 1.232(3) yes N1 . C1 . 1.323(3) yes N1 . H11 . 0.950 no N1 . H12 . 0.950 no C1 . C2 . 1.487(4) yes C2 . C3 . 1.368(4) yes C2 . C4 . 1.403(5) yes C3 . H31 . 0.950 no C3 . H32 . 0.950 no C4 . H41 . 0.950 no C4 . H42 . 0.950 no C4 . H43 . 0.950 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 C1 . N1 . H11 . 120.000 no C1 . N1 . H12 . 120.000 no H11 . N1 . H12 . 120.000 no N1 . C1 . O1 . 121.1(3) yes N1 . C1 . C2 . 118.3(2) yes O1 . C1 . C2 . 120.6(3) yes C1 . C2 . C3 . 117.8(3) yes C1 . C2 . C4 . 121.0(3) yes C3 . C2 . C4 . 121.1(3) yes C2 . C3 . H31 . 119.998 no C2 . C3 . H32 . 120.000 no H31 . C3 . H32 . 120.002 no C2 . C4 . H41 . 109.465 no C2 . C4 . H42 . 109.471 no H41 . C4 . H42 . 109.485 no C2 . C4 . H43 . 109.459 no H41 . C4 . H43 . 109.469 no H42 . C4 . H43 . 109.478 no data_CRYSTALS_cif_3 _database_code_depnum_ccdc_archive 'CCDC 260954' _audit_creation_date 04-10-01 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title 'foxi methacrylamide 120K ortho Kr#2 05-04' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.7200(4) _cell_length_b 10.1600(5) _cell_length_c 16.2410(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 943.85(9) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-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 0.0033 0.0016 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' O 0.0106 0.0060 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' N 0.0061 0.0033 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' _cell_formula_units_Z 8 # Given Formula = C4 H8 N1 O1 # Dc = 1.21 Fooo = 368.00 Mu = 0.87 M = 86.11 # Found Formula = C4 H7 N1 O1 # Dc = 1.20 FOOO = 368.00 Mu = 0.87 M = 85.11 _chemical_formula_sum 'C4 H7 N1 O1' _chemical_formula_moiety 'C4 H7 N1 O1' _chemical_compound_source ? _chemical_formula_weight 85.11 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.087 # Sheldrick geometric approximatio 0.98 1.00 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9828 _exptl_absorpt_correction_T_max 0.9957 _diffrn_measurement_device_type Unknown _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _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 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 11758 _reflns_number_total 1223 _diffrn_reflns_av_R_equivalents 0.054 # Number of reflections with Friedels Law is 1223 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1253 _diffrn_reflns_theta_min 4.011 _diffrn_reflns_theta_max 28.984 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.955 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min 0 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _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 -0.30 _refine_diff_density_max 0.27 _refine_ls_number_reflns 726 _refine_ls_number_restraints 12 _refine_ls_number_parameters 83 #_refine_ls_R_factor_ref 0.0548 _refine_ls_wR_factor_ref 0.1416 _refine_ls_goodness_of_fit_ref 1.1108 #_reflns_number_all 1222 _refine_ls_R_factor_all 0.0960 _refine_ls_wR_factor_all 0.1544 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 726 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_gt 0.1416 _refine_ls_shift/su_max 0.000067 # 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 mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.781E-01 0.420 0.00 0.00 0.00 0.333 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 O1 O 0.2393(4) -0.06670(15) 0.44124(12) 0.0246 1.0000 Uani . . . . . . N1 N 0.1421(5) 0.14787(19) 0.44733(17) 0.0231 1.0000 Uani . . . . . . C1 C 0.2763(5) 0.0501(2) 0.42013(16) 0.0176 1.0000 Uani . . . . . . C2 C 0.4747(5) 0.0789(2) 0.36298(16) 0.0180 1.0000 Uani . . . . . . C3 C 0.5092(6) 0.1965(3) 0.32958(19) 0.0266 1.0000 Uani . . . . . . C4 C 0.6314(6) -0.0361(3) 0.3434(2) 0.0263 1.0000 Uani . . . . . . H11 H 0.169(7) 0.229(4) 0.436(2) 0.049(11) 1.0000 Uiso . . . . . . H12 H 0.026(7) 0.127(3) 0.482(2) 0.028(9) 1.0000 Uiso . . . . . . H31 H 0.405(7) 0.270(3) 0.343(2) 0.037(10) 1.0000 Uiso . . . . . . H32 H 0.639(7) 0.210(3) 0.291(2) 0.027(9) 1.0000 Uiso . . . . . . H41 H 0.755(9) -0.008(4) 0.307(2) 0.048(11) 1.0000 Uiso . . . . . . H42 H 0.700(6) -0.072(3) 0.395(2) 0.032(9) 1.0000 Uiso . . . . . . H43 H 0.537(7) -0.106(4) 0.316(2) 0.040(10) 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 O1 0.0272(11) 0.0086(7) 0.0381(11) 0.0008(7) 0.0061(11) -0.0003(7) N1 0.0222(12) 0.0084(8) 0.0388(15) 0.0005(8) 0.0081(12) 0.0004(9) C1 0.0181(12) 0.0118(9) 0.0227(11) -0.0018(9) -0.0009(11) -0.0009(9) C2 0.0170(12) 0.0152(10) 0.0217(11) -0.0022(9) -0.0017(11) -0.0016(9) C3 0.0292(15) 0.0180(12) 0.0327(15) 0.0017(10) 0.0088(14) -0.0021(11) C4 0.0251(15) 0.0198(11) 0.0340(15) 0.0008(11) 0.0055(14) 0.0059(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.85(16) 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 O1 . C1 . 1.253(2) yes N1 . C1 . 1.331(3) yes N1 . H11 . 0.86(4) no N1 . H12 . 0.90(4) no C1 . C2 . 1.495(4) yes C2 . C3 . 1.327(3) yes C2 . C4 . 1.506(4) yes C3 . H31 . 0.98(4) no C3 . H32 . 0.98(3) no C4 . H41 . 0.97(5) no C4 . H42 . 0.99(4) no C4 . H43 . 1.00(4) 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 C1 . N1 . H11 . 123(3) no C1 . N1 . H12 . 117.4(19) no H11 . N1 . H12 . 119(3) no N1 . C1 . O1 . 121.2(2) yes N1 . C1 . C2 . 119.9(2) yes O1 . C1 . C2 . 118.9(2) yes C1 . C2 . C3 . 122.9(2) yes C1 . C2 . C4 . 115.6(2) yes C3 . C2 . C4 . 121.6(3) yes C2 . C3 . H31 . 120(2) no C2 . C3 . H32 . 119.9(18) no H31 . C3 . H32 . 120(3) no C2 . C4 . H41 . 110(2) no C2 . C4 . H42 . 109.9(19) no H41 . C4 . H42 . 109(3) no C2 . C4 . H43 . 109(2) no H41 . C4 . H43 . 109(3) no H42 . C4 . H43 . 109(3) no