#------------------------------------------------------------------------------ #$Date: 2016-06-01 10:27:03 +0100 (Wed, 01 Jun 2016) $ #$Revision: 183218 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/00/3500036.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_3500036 loop_ _publ_author_name 'Juergen Lange' _journal_name_full 'Personal communication to COD' _journal_year 2016 _chemical_formula_sum 'C19 H20 Cu N2 O2' _chemical_formula_weight 371.91 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 112.990(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.746(3) _cell_length_b 17.215(5) _cell_length_c 11.360(4) _cell_measurement_reflns_used 44 _cell_measurement_temperature 299(2) _cell_measurement_theta_max 29.6 _cell_measurement_theta_min 23.0 _cell_volume 1754.6(10) _computing_cell_refinement 'Stoe DIF4' _computing_data_collection 'Stoe DIF4' _computing_data_reduction 'Stoe X-STEP' _computing_molecular_graphics PLUTO _computing_publication_material SHELXL-93 _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 299(2) _diffrn_measurement_device 'Stoe Stadi-4 4-circle-diffractometer' _diffrn_measurement_method 'Profile fitted scan 2\q/\w=1/1' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0134 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_max 2 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4043 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.28 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 180 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.257 _exptl_absorpt_correction_T_max 0.675 _exptl_absorpt_correction_T_min 0.648 _exptl_absorpt_correction_type numerical _exptl_crystal_colour black _exptl_crystal_density_diffrn 1.408 _exptl_crystal_description block _exptl_crystal_F_000 772 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_special_details ; ? ; _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. ; _refine_diff_density_max 0.261 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef 0.0042(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_all 1.125 _refine_ls_goodness_of_fit_obs 1.085 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 3070 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.219 _refine_ls_restrained_S_obs 1.085 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_obs 0.0303 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+1.4687P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0885 _refine_ls_wR_factor_obs 0.0739 _refine_special_details ; Refinement on F^2^ for ALL reflections except for 20 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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. ; _reflns_number_observed 2733 _reflns_number_total 3090 _reflns_observed_criterion >2sigma(I) _cod_data_source_file E81.CIF _cod_data_source_block e81 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to the built-in table from CIF Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+1.4687P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+1.4687P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 4609 2016-04-01 06:22:49Z antanas ; _cod_original_sg_symbol_H-M P21/n _cod_database_code 3500036 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 Cu1 0.0313(2) 0.0380(2) 0.0410(2) 0.00258(13) 0.00574(13) -0.00300(12) O2 0.0510(11) 0.0487(11) 0.0419(10) 0.0049(9) 0.0009(8) -0.0130(9) C3 0.0408(13) 0.0418(14) 0.0413(13) 0.0008(11) 0.0157(11) 0.0046(11) C4 0.054(2) 0.058(2) 0.0406(14) -0.0031(13) 0.0143(12) 0.0022(14) C5 0.068(2) 0.075(2) 0.042(2) 0.0096(15) 0.0212(15) 0.014(2) C6 0.075(2) 0.063(2) 0.063(2) 0.023(2) 0.037(2) 0.010(2) C7 0.050(2) 0.048(2) 0.063(2) 0.0061(14) 0.0292(14) 0.0011(13) C8 0.0371(12) 0.0404(13) 0.0463(14) 0.0013(11) 0.0215(11) 0.0033(11) C9 0.0312(12) 0.0374(13) 0.054(2) -0.0040(12) 0.0182(11) -0.0026(10) N10 0.0303(10) 0.0385(11) 0.0422(11) -0.0027(9) 0.0091(9) 0.0004(8) C11 0.0344(13) 0.0463(15) 0.0450(14) -0.0069(12) 0.0065(11) -0.0039(11) C12 0.0290(12) 0.057(2) 0.054(2) -0.0004(13) 0.0064(11) -0.0010(12) C13 0.042(2) 0.076(2) 0.115(3) -0.007(2) 0.034(2) -0.006(2) C14 0.062(2) 0.084(2) 0.060(2) 0.004(2) -0.006(2) 0.002(2) C15 0.0337(13) 0.049(2) 0.067(2) 0.0013(14) 0.0126(13) 0.0068(12) N16 0.0308(10) 0.0400(12) 0.0512(13) 0.0019(10) 0.0068(9) 0.0020(9) C17 0.0443(14) 0.0393(14) 0.0472(15) 0.0059(12) 0.0047(12) 0.0049(12) C18 0.0480(15) 0.0372(14) 0.0438(14) 0.0016(11) 0.0111(12) -0.0036(11) C19 0.071(2) 0.055(2) 0.050(2) 0.0105(14) 0.0102(15) -0.007(2) C20 0.087(3) 0.068(2) 0.062(2) 0.013(2) 0.028(2) -0.021(2) C21 0.066(2) 0.071(2) 0.072(2) 0.000(2) 0.031(2) -0.023(2) C22 0.044(2) 0.058(2) 0.062(2) 0.0022(15) 0.0159(14) -0.0129(13) C23 0.0434(14) 0.0371(13) 0.0415(14) -0.0037(11) 0.0131(11) -0.0063(11) O24 0.0335(9) 0.0526(11) 0.0451(10) 0.0094(9) 0.0043(8) -0.0067(8) 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 0.45396(3) 0.14975(2) 0.49306(3) 0.03932(13) Uani 1 d . . O2 O 0.5632(2) 0.12024(11) 0.6651(2) 0.0525(5) Uani 1 d . . C3 C 0.5403(3) 0.06010(15) 0.7251(2) 0.0414(6) Uani 1 d . . C4 C 0.6327(3) 0.0501(2) 0.8556(3) 0.0521(7) Uani 1 d . . H4 H 0.7028(3) 0.0880(2) 0.8971(3) 0.063 Uiso 1 calc R . C5 C 0.6216(4) -0.0138(2) 0.9223(3) 0.0615(8) Uani 1 d . . H5 H 0.6845(4) -0.0190(2) 1.0079(3) 0.074 Uiso 1 calc R . C6 C 0.5172(4) -0.0714(2) 0.8633(3) 0.0641(9) Uani 1 d . . H6 H 0.5111(4) -0.1153(2) 0.9087(3) 0.077 Uiso 1 calc R . C7 C 0.4242(3) -0.0629(2) 0.7388(3) 0.0513(7) Uani 1 d . . H7 H 0.3541(3) -0.1013(2) 0.6998(3) 0.062 Uiso 1 calc R . C8 C 0.4312(3) 0.00283(14) 0.6670(2) 0.0397(6) Uani 1 d . . C9 C 0.3277(3) 0.00662(14) 0.5354(3) 0.0405(6) Uani 1 d . . H9 H 0.2642(3) -0.03556(14) 0.5038(3) 0.049 Uiso 1 calc R . N10 N 0.3152(2) 0.06283(12) 0.4580(2) 0.0385(5) Uani 1 d . . C11 C 0.2115(3) 0.0564(2) 0.3242(2) 0.0447(6) Uani 1 d . . H11A H 0.1625(3) 0.0062(2) 0.3117(2) 0.054 Uiso 1 calc R . H11B H 0.2680(3) 0.0581(2) 0.2704(2) 0.054 Uiso 1 calc R . C12 C 0.0919(3) 0.1200(2) 0.2803(3) 0.0498(7) Uani 1 d . . C13 C -0.0376(3) 0.1003(2) 0.3193(4) 0.0770(10) Uani 1 d . . H13A H -0.1068(15) 0.1428(7) 0.2976(23) 0.108 Uiso 1 calc R . H13B H 0.0000(5) 0.0913(15) 0.4098(6) 0.108 Uiso 1 calc R . H13C H -0.0872(18) 0.0544(9) 0.2749(19) 0.108 Uiso 1 calc R . C14 C 0.0361(4) 0.1246(2) 0.1345(3) 0.0778(10) Uani 1 d . . H14A H 0.1141(10) 0.1445(14) 0.1111(3) 0.109 Uiso 1 calc R . H14B H -0.0486(18) 0.1586(12) 0.1023(4) 0.109 Uiso 1 calc R . H14C H 0.0079(27) 0.0737(3) 0.0986(4) 0.109 Uiso 1 calc R . C15 C 0.1546(3) 0.1993(2) 0.3390(3) 0.0523(7) Uani 1 d . . H15A H 0.0948(3) 0.2400(2) 0.2835(3) 0.063 Uiso 1 calc R . H15B H 0.1457(3) 0.2041(2) 0.4208(3) 0.063 Uiso 1 calc R . N16 N 0.3117(2) 0.21107(12) 0.3583(2) 0.0435(5) Uani 1 d . . C17 C 0.3448(3) 0.2616(2) 0.2902(3) 0.0476(6) Uani 1 d . . H17 H 0.2662(3) 0.2876(2) 0.2280(3) 0.057 Uiso 1 calc R . C18 C 0.4931(3) 0.28113(15) 0.3023(2) 0.0451(6) Uani 1 d . . C19 C 0.5068(4) 0.3341(2) 0.2138(3) 0.0627(8) Uani 1 d . . H19 H 0.4211(4) 0.3538(2) 0.1500(3) 0.075 Uiso 1 calc R . C20 C 0.6430(4) 0.3577(2) 0.2191(3) 0.0730(10) Uani 1 d . . H20 H 0.6500(4) 0.3926(2) 0.1592(3) 0.088 Uiso 1 calc R . C21 C 0.7704(4) 0.3288(2) 0.3147(3) 0.0682(9) Uani 1 d . . H21 H 0.8636(4) 0.3448(2) 0.3193(3) 0.082 Uiso 1 calc R . C22 C 0.7609(3) 0.2772(2) 0.4025(3) 0.0564(7) Uani 1 d . . H22 H 0.8483(3) 0.2585(2) 0.4655(3) 0.068 Uiso 1 calc R . C23 C 0.6233(3) 0.25132(14) 0.4007(2) 0.0418(6) Uani 1 d . . O24 O 0.6227(2) 0.20241(11) 0.4886(2) 0.0471(4) Uani 1 d . . 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' Cu Cu 0.3201 1.2651 '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' 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 O2 Cu1 O24 90.70(8) . . O2 Cu1 N16 154.93(9) . . O24 Cu1 N16 94.55(8) . . O2 Cu1 N10 94.03(8) . . O24 Cu1 N10 154.25(9) . . N16 Cu1 N10 91.81(9) . . C3 O2 Cu1 127.6(2) . . O2 C3 C8 124.1(2) . . O2 C3 C4 118.4(2) . . C8 C3 C4 117.4(2) . . C5 C4 C3 121.7(3) . . C4 C5 C6 120.6(3) . . C7 C6 C5 119.4(3) . . C6 C7 C8 121.7(3) . . C3 C8 C7 119.2(2) . . C3 C8 C9 123.2(2) . . C7 C8 C9 117.6(2) . . N10 C9 C8 125.9(2) . . C9 N10 C11 119.8(2) . . C9 N10 Cu1 124.6(2) . . C11 N10 Cu1 114.3(2) . . N10 C11 C12 114.4(2) . . C13 C12 C14 109.9(3) . . C13 C12 C11 110.8(3) . . C14 C12 C11 107.0(2) . . C13 C12 C15 107.8(3) . . C14 C12 C15 109.6(3) . . C11 C12 C15 111.7(2) . . N16 C15 C12 113.7(2) . . C17 N16 C15 119.6(2) . . C17 N16 Cu1 125.1(2) . . C15 N16 Cu1 115.2(2) . . N16 C17 C18 125.5(2) . . C19 C18 C23 119.6(3) . . C19 C18 C17 117.3(3) . . C23 C18 C17 123.1(2) . . C20 C19 C18 121.7(3) . . C19 C20 C21 119.0(3) . . C22 C21 C20 120.7(3) . . C21 C22 C23 122.2(3) . . O24 C23 C22 118.8(2) . . O24 C23 C18 124.4(2) . . C22 C23 C18 116.8(2) . . C23 O24 Cu1 126.2(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cu1 O2 1.894(2) . Cu1 O24 1.896(2) . Cu1 N16 1.930(2) . Cu1 N10 1.951(2) . O2 C3 1.305(3) . C3 C8 1.411(4) . C3 C4 1.412(4) . C4 C5 1.364(4) . C5 C6 1.391(5) . C6 C7 1.357(4) . C7 C8 1.411(4) . C8 C9 1.442(4) . C9 N10 1.281(3) . N10 C11 1.464(3) . C11 C12 1.533(4) . C12 C13 1.530(4) . C12 C14 1.531(4) . C12 C15 1.537(4) . C15 N16 1.473(3) . N16 C17 1.285(3) . C17 C18 1.437(4) . C18 C19 1.402(4) . C18 C23 1.420(4) . C19 C20 1.367(5) . C20 C21 1.384(5) . C21 C22 1.365(4) . C22 C23 1.406(4) . C23 O24 1.308(3) . 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 O24 Cu1 O2 C3 -154.0(2) . . . . N16 Cu1 O2 C3 103.7(3) . . . . N10 Cu1 O2 C3 0.7(2) . . . . Cu1 O2 C3 C8 3.7(4) . . . . Cu1 O2 C3 C4 -178.0(2) . . . . O2 C3 C4 C5 -175.8(3) . . . . C8 C3 C4 C5 2.6(4) . . . . C3 C4 C5 C6 -0.5(5) . . . . C4 C5 C6 C7 -1.0(5) . . . . C5 C6 C7 C8 0.4(5) . . . . O2 C3 C8 C7 175.1(2) . . . . C4 C3 C8 C7 -3.1(3) . . . . O2 C3 C8 C9 -3.1(4) . . . . C4 C3 C8 C9 178.7(2) . . . . C6 C7 C8 C3 1.8(4) . . . . C6 C7 C8 C9 -180.0(3) . . . . C3 C8 C9 N10 -4.3(4) . . . . C7 C8 C9 N10 177.5(2) . . . . C8 C9 N10 C11 175.9(2) . . . . C8 C9 N10 Cu1 9.6(3) . . . . O2 Cu1 N10 C9 -7.1(2) . . . . O24 Cu1 N10 C9 92.9(3) . . . . N16 Cu1 N10 C9 -162.7(2) . . . . O2 Cu1 N10 C11 -174.1(2) . . . . O24 Cu1 N10 C11 -74.1(2) . . . . N16 Cu1 N10 C11 30.3(2) . . . . C9 N10 C11 C12 121.6(3) . . . . Cu1 N10 C11 C12 -70.8(2) . . . . N10 C11 C12 C13 -82.1(3) . . . . N10 C11 C12 C14 158.1(2) . . . . N10 C11 C12 C15 38.1(3) . . . . C13 C12 C15 N16 155.2(3) . . . . C14 C12 C15 N16 -85.2(3) . . . . C11 C12 C15 N16 33.2(3) . . . . C12 C15 N16 C17 111.5(3) . . . . C12 C15 N16 Cu1 -70.9(3) . . . . O2 Cu1 N16 C17 108.3(3) . . . . O24 Cu1 N16 C17 6.8(2) . . . . N10 Cu1 N16 C17 -148.2(2) . . . . O2 Cu1 N16 C15 -69.1(3) . . . . O24 Cu1 N16 C15 -170.6(2) . . . . N10 Cu1 N16 C15 34.4(2) . . . . C15 N16 C17 C18 177.4(3) . . . . Cu1 N16 C17 C18 0.1(4) . . . . N16 C17 C18 C19 176.0(3) . . . . N16 C17 C18 C23 -6.1(4) . . . . C23 C18 C19 C20 0.5(5) . . . . C17 C18 C19 C20 178.6(3) . . . . C18 C19 C20 C21 -0.5(5) . . . . C19 C20 C21 C22 0.4(6) . . . . C20 C21 C22 C23 -0.3(5) . . . . C21 C22 C23 O24 -179.3(3) . . . . C21 C22 C23 C18 0.3(4) . . . . C19 C18 C23 O24 179.2(3) . . . . C17 C18 C23 O24 1.3(4) . . . . C19 C18 C23 C22 -0.4(4) . . . . C17 C18 C23 C22 -178.4(3) . . . . C22 C23 O24 Cu1 -171.5(2) . . . . C18 C23 O24 Cu1 8.9(4) . . . . O2 Cu1 O24 C23 -166.7(2) . . . . N16 Cu1 O24 C23 -11.3(2) . . . . N10 Cu1 O24 C23 92.5(3) . . . . _cod_database_fobs_code 3500036