Audit Creation Method SHELXL-97

data_lco37

_audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-benzyl-5-methoxymethyl-3-methyl-1H-pyrrole- 2-carboxylic acid benzyl ester ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 N O3' _chemical_formula_weight 349.41 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 P21/c

loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2'

_cell_length_a 14.607(9) _cell_length_b 5.136(2) _cell_length_c 25.832(17) _cell_angle_alpha 90.00 _cell_angle_beta 108.14(5) _cell_angle_gamma 90.00 _cell_volume 1841.6(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.37 _cell_measurement_theta_max 17.16

_exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type 'psi-scan' _exptl_absorpt_correction_T_min 0.800 _exptl_absorpt_correction_T_max 0.958 _exptl_absorpt_process_details ?

_exptl_special_details ; ? ;

_diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method 'profile data from \w-2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 180 _diffrn_standards_decay_% 1 _diffrn_reflns_number 9903 _diffrn_reflns_av_R_equivalents 0.1074 _diffrn_reflns_av_sigmaI/netI 0.0870 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.48 _reflns_number_total 3424 _reflns_number_gt 1694 _reflns_threshold_expression I>2\s(I)

_computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction 'PLATON (Spek, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0453P)^2^+4.4509P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3424 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1738 _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.2159 _refine_ls_wR_factor_gt 0.1794 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 N1 N 0.1596(3) 1.0156(8) 0.03483(15) 0.0459(10) Uani 1 1 d . . . H1 H 0.1035 1.0566 0.0366 0.055 Uiso 1 1 calc R . . C1 C 0.1768(3) 0.8293(9) 0.00098(18) 0.0411(11) Uani 1 1 d . . . C2 C 0.2763(3) 0.8219(10) 0.00989(18) 0.0436(11) Uani 1 1 d . . . C3 C 0.3172(3) 1.0114(10) 0.05031(19) 0.0443(12) Uani 1 1 d . . . C4 C 0.2426(4) 1.1249(10) 0.06479(19) 0.0471(12) Uani 1 1 d . . . C5 C 0.0972(3) 0.6893(9) -0.03352(18) 0.0428(12) Uani 1 1 d . . . O1 O 0.0131(2) 0.7370(7) -0.03713(13) 0.0526(9) Uani 1 1 d . . . O2 O 0.1197(2) 0.4960(7) -0.06213(12) 0.0480(8) Uani 1 1 d . . . C6 C 0.0391(3) 0.3454(10) -0.0956(2) 0.0512(13) Uani 1 1 d . . . H6A H -0.0091 0.4617 -0.1184 0.061 Uiso 1 1 calc R . . H6B H 0.0099 0.2496 -0.0724 0.061 Uiso 1 1 calc R . . C7 C 0.0718(4) 0.1604(9) -0.13044(19) 0.0454(12) Uani 1 1 d . . . C8 C 0.0042(4) -0.0081(11) -0.1633(2) 0.0582(14) Uani 1 1 d . . . H8 H -0.0591 -0.0032 -0.1626 0.070 Uiso 1 1 calc R . . C9 C 0.0298(5) -0.1832(11) -0.1970(2) 0.0677(16) Uani 1 1 d . . . H9 H -0.0162 -0.2950 -0.2189 0.081 Uiso 1 1 calc R . . C10 C 0.1232(5) -0.1927(11) -0.1983(2) 0.0670(16) Uani 1 1 d . . . H10 H 0.1408 -0.3117 -0.2206 0.080 Uiso 1 1 calc R . . C11 C 0.1893(4) -0.0258(12) -0.1665(2) 0.0670(16) Uani 1 1 d . . . H11 H 0.2522 -0.0298 -0.1679 0.080 Uiso 1 1 calc R . . C12 C 0.1652(4) 0.1498(11) -0.1323(2) 0.0593(14) Uani 1 1 d . . . H12 H 0.2118 0.2606 -0.1106 0.071 Uiso 1 1 calc R . . C13 C 0.3293(3) 0.6572(11) -0.0184(2) 0.0591(14) Uani 1 1 d . . . H13A H 0.3155 0.4771 -0.0143 0.089 Uiso 1 1 calc R . . H13B H 0.3973 0.6870 -0.0029 0.089 Uiso 1 1 calc R . . H13C H 0.3095 0.7010 -0.0564 0.089 Uiso 1 1 calc R . . C14 C 0.4228(3) 1.0729(10) 0.0735(2) 0.0536(14) Uani 1 1 d . . . H14A H 0.4300 1.2424 0.0908 0.064 Uiso 1 1 calc R . . H14B H 0.4504 1.0829 0.0439 0.064 Uiso 1 1 calc R . . C15 C 0.4787(3) 0.8741(10) 0.1146(2) 0.0484(12) Uani 1 1 d . . . C16 C 0.5569(4) 0.7451(12) 0.1072(2) 0.0643(16) Uani 1 1 d . . . H16 H 0.5757 0.7808 0.0767 0.077 Uiso 1 1 calc R . . C17 C 0.6075(4) 0.5626(13) 0.1451(3) 0.0726(18) Uani 1 1 d . . . H17 H 0.6593 0.4753 0.1394 0.087 Uiso 1 1 calc R . . C18 C 0.5822(4) 0.5110(13) 0.1898(3) 0.0712(17) Uani 1 1 d . . . H18 H 0.6166 0.3894 0.2151 0.085 Uiso 1 1 calc R . . C19 C 0.5050(4) 0.6395(13) 0.1978(2) 0.0715(17) Uani 1 1 d . . . H19 H 0.4873 0.6050 0.2287 0.086 Uiso 1 1 calc R . . C20 C 0.4540(4) 0.8186(12) 0.1604(2) 0.0617(15) Uani 1 1 d . . . H20 H 0.4018 0.9034 0.1662 0.074 Uiso 1 1 calc R . . C21 C 0.2429(4) 1.3308(11) 0.1052(2) 0.0573(14) Uani 1 1 d . . . H21A H 0.3002 1.4372 0.1117 0.069 Uiso 1 1 calc R . . H21B H 0.1870 1.4422 0.0910 0.069 Uiso 1 1 calc R . . O3 O 0.2410(3) 1.2185(9) 0.15379(16) 0.0868(14) Uani 1 1 d . . . C22 C 0.2392(5) 1.4045(16) 0.1941(2) 0.100(3) Uani 1 1 d . . . H22A H 0.2485 1.3179 0.2282 0.150 Uiso 1 1 calc R . . H22B H 0.1782 1.4922 0.1834 0.150 Uiso 1 1 calc R . . H23C H 0.2898 1.5292 0.1978 0.150 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.046(2) 0.044(2) 0.050(2) -0.003(2) 0.0165(19) 0.002(2) C1 0.038(2) 0.039(3) 0.046(3) -0.005(2) 0.011(2) 0.004(2) C2 0.044(3) 0.044(3) 0.045(3) 0.002(3) 0.017(2) 0.004(2) C3 0.041(3) 0.041(3) 0.051(3) 0.007(3) 0.015(2) 0.000(2) C4 0.051(3) 0.044(3) 0.044(3) -0.002(3) 0.012(2) -0.001(3) C5 0.048(3) 0.039(3) 0.043(3) 0.000(2) 0.016(2) 0.008(2) O1 0.0384(18) 0.052(2) 0.069(2) -0.0126(19) 0.0191(16) 0.0012(17) O2 0.0413(17) 0.045(2) 0.055(2) -0.0116(18) 0.0111(15) 0.0008(17) C6 0.050(3) 0.046(3) 0.056(3) -0.007(3) 0.016(2) -0.004(3) C7 0.058(3) 0.032(3) 0.045(3) 0.000(2) 0.014(2) 0.000(2) C8 0.068(3) 0.053(3) 0.055(3) -0.004(3) 0.020(3) -0.008(3) C9 0.088(4) 0.051(4) 0.061(4) -0.008(3) 0.018(3) -0.011(3) C10 0.096(5) 0.048(3) 0.059(4) -0.002(3) 0.027(3) 0.012(4) C11 0.064(4) 0.061(4) 0.076(4) -0.012(4) 0.023(3) 0.009(3) C12 0.066(4) 0.047(3) 0.065(4) -0.014(3) 0.021(3) 0.000(3) C13 0.050(3) 0.057(3) 0.074(4) -0.007(3) 0.026(3) 0.006(3) C14 0.044(3) 0.051(3) 0.063(3) 0.006(3) 0.012(2) -0.007(2) C15 0.040(3) 0.045(3) 0.055(3) -0.003(3) 0.008(2) -0.007(2) C16 0.053(3) 0.077(4) 0.067(4) 0.008(3) 0.026(3) 0.003(3) C17 0.053(3) 0.076(5) 0.089(5) 0.011(4) 0.022(3) 0.014(3) C18 0.059(4) 0.069(4) 0.078(4) 0.012(4) 0.010(3) 0.010(3) C19 0.075(4) 0.085(5) 0.055(3) 0.011(4) 0.021(3) 0.008(4) C20 0.055(3) 0.072(4) 0.058(3) -0.006(3) 0.019(3) 0.008(3) C21 0.059(3) 0.058(4) 0.051(3) -0.008(3) 0.012(3) -0.008(3) O3 0.112(3) 0.092(3) 0.063(3) -0.010(3) 0.036(2) 0.010(3) C22 0.097(5) 0.144(7) 0.062(4) -0.030(5) 0.028(4) 0.004(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 N1 C4 1.342(6) . ? N1 C1 1.372(6) . ? N1 H1 0.8600 . ? C1 C2 1.400(6) . ? C1 C5 1.421(6) . ? C2 C3 1.416(7) . ? C2 C13 1.484(6) . ? C3 C4 1.386(6) . ? C3 C14 1.504(6) . ? C4 C21 1.485(7) . ? C5 O1 1.227(5) . ? C5 O2 1.338(5) . ? O2 C6 1.448(5) . ? C6 C7 1.486(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C12 1.381(7) . ? C7 C8 1.386(7) . ? C8 C9 1.382(7) . ? C8 H8 0.9300 . ? C9 C10 1.375(8) . ? C9 H9 0.9300 . ? C10 C11 1.359(8) . ? C10 H10 0.9300 . ? C11 C12 1.383(7) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.516(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C20 1.368(7) . ? C15 C16 1.385(7) . ? C16 C17 1.389(8) . ? C16 H16 0.9300 . ? C17 C18 1.344(8) . ? C17 H17 0.9300 . ? C18 C19 1.377(8) . ? C18 H18 0.9300 . ? C19 C20 1.373(8) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 O3 1.389(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? O3 C22 1.418(7) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H23C 0.9600 . ? 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 C4 N1 C1 110.3(4) . . ? C4 N1 H1 124.8 . . ? C1 N1 H1 124.8 . . ? N1 C1 C2 107.5(4) . . ? N1 C1 C5 118.4(4) . . ? C2 C1 C5 134.0(4) . . ? C1 C2 C3 106.3(4) . . ? C1 C2 C13 127.5(4) . . ? C3 C2 C13 126.2(4) . . ? C4 C3 C2 107.6(4) . . ? C4 C3 C14 126.8(5) . . ? C2 C3 C14 125.6(4) . . ? N1 C4 C3 108.3(4) . . ? N1 C4 C21 120.5(4) . . ? C3 C4 C21 131.2(5) . . ? O1 C5 O2 121.2(4) . . ? O1 C5 C1 123.5(4) . . ? O2 C5 C1 115.3(4) . . ? C5 O2 C6 115.6(3) . . ? O2 C6 C7 110.4(4) . . ? O2 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? O2 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C12 C7 C8 118.5(5) . . ? C12 C7 C6 123.6(4) . . ? C8 C7 C6 117.9(5) . . ? C9 C8 C7 120.7(5) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C10 C9 C8 120.3(6) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 119.1(5) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 121.5(6) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C7 C12 C11 119.9(5) . . ? C7 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C3 C14 C15 113.6(4) . . ? C3 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? C3 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C20 C15 C16 118.1(5) . . ? C20 C15 C14 121.1(5) . . ? C16 C15 C14 120.8(5) . . ? C15 C16 C17 120.4(5) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 120.6(6) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 119.5(6) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C20 C19 C18 120.4(5) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C15 C20 C19 121.1(5) . . ? C15 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? O3 C21 C4 110.1(5) . . ? O3 C21 H21A 109.6 . . ? C4 C21 H21A 109.6 . . ? O3 C21 H21B 109.6 . . ? C4 C21 H21B 109.6 . . ? H21A C21 H21B 108.2 . . ? C21 O3 C22 113.1(5) . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H23C 109.5 . . ? H22A C22 H23C 109.5 . . ? H22B C22 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 -0.4(5) . . . . ? C4 N1 C1 C5 179.2(4) . . . . ? N1 C1 C2 C3 0.0(5) . . . . ? C5 C1 C2 C3 -179.5(5) . . . . ? N1 C1 C2 C13 -177.9(5) . . . . ? C5 C1 C2 C13 2.6(9) . . . . ? C1 C2 C3 C4 0.4(5) . . . . ? C13 C2 C3 C4 178.3(5) . . . . ? C1 C2 C3 C14 179.6(4) . . . . ? C13 C2 C3 C14 -2.5(8) . . . . ? C1 N1 C4 C3 0.7(5) . . . . ? C1 N1 C4 C21 -179.2(4) . . . . ? C2 C3 C4 N1 -0.7(5) . . . . ? C14 C3 C4 N1 -179.8(4) . . . . ? C2 C3 C4 C21 179.2(5) . . . . ? C14 C3 C4 C21 0.1(9) . . . . ? N1 C1 C5 O1 4.6(7) . . . . ? C2 C1 C5 O1 -176.0(5) . . . . ? N1 C1 C5 O2 -174.7(4) . . . . ? C2 C1 C5 O2 4.7(8) . . . . ? O1 C5 O2 C6 -1.9(6) . . . . ? C1 C5 O2 C6 177.4(4) . . . . ? C5 O2 C6 C7 172.8(4) . . . . ? O2 C6 C7 C12 -3.8(7) . . . . ? O2 C6 C7 C8 177.0(4) . . . . ? C12 C7 C8 C9 0.2(8) . . . . ? C6 C7 C8 C9 179.4(5) . . . . ? C7 C8 C9 C10 0.1(8) . . . . ? C8 C9 C10 C11 -0.8(9) . . . . ? C9 C10 C11 C12 1.1(9) . . . . ? C8 C7 C12 C11 0.1(8) . . . . ? C6 C7 C12 C11 -179.0(5) . . . . ? C10 C11 C12 C7 -0.8(9) . . . . ? C4 C3 C14 C15 101.9(6) . . . . ? C2 C3 C14 C15 -77.0(6) . . . . ? C3 C14 C15 C20 -57.7(7) . . . . ? C3 C14 C15 C16 122.9(5) . . . . ? C20 C15 C16 C17 0.8(8) . . . . ? C14 C15 C16 C17 -179.8(5) . . . . ? C15 C16 C17 C18 -0.9(9) . . . . ? C16 C17 C18 C19 0.4(10) . . . . ? C17 C18 C19 C20 0.2(10) . . . . ? C16 C15 C20 C19 -0.2(8) . . . . ? C14 C15 C20 C19 -179.6(5) . . . . ? C18 C19 C20 C15 -0.3(9) . . . . ? N1 C4 C21 O3 83.2(6) . . . . ? C3 C4 C21 O3 -96.6(6) . . . . ? C4 C21 O3 C22 -178.9(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.86 2.01 2.842(5) 162.2 3_575

_diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.230 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.053