data_SCHNOV _audit_update_record ; 2016-03-02 # Formatted by publCIF ; # publcif _publ_body_element loop start loop_ _publ_body_element _publ_body_title _publ_body_contents section ; Introduction ; ; ; section ; Experimental ; ; ; subsection ; Synthesis and crystallization ; ; ; subsection ; Refinement ; ; Crystal data, data collection and structure refinement details are summarized in Table 1. ; section ; Results and discussion ; ; ; # publcif _publ_body_element loop end _audit_creation_method SHELXL-2013 _chemical_name_systematic ? _chemical_name_common 'compound 2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H6 Cl4 Cu2 N2' _chemical_formula_weight 350.99 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' 'Cl' 'Cl' 0.1484 0.1585 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.7990(8) _cell_length_b 7.9080(16) _cell_length_c 18.075(4) _cell_angle_alpha 90 _cell_angle_beta 89.94(3) _cell_angle_gamma 90 _cell_volume 543.02(19) _cell_formula_units_Z 2 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 512 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 26.73 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 2.147 _exptl_crystal_F_000 340 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.750 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.020 _exptl_absorpt_coefficient_mu 4.847 _shelx_estimated_absorpt_T_min 0.122 _shelx_estimated_absorpt_T_max 0.909 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.11067 _exptl_absorpt_correction_T_max 0.49496 _exptl_absorpt_process_details ; Platon MULABS semi-empirical method using multiple scanned reflections ; _exptl_special_details ? _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'Bruker Nonius FR591 rotating anode' _diffrn_measurement_device_type 'Bruker Nonius KappaCCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3334 _diffrn_reflns_av_unetI/netI 0.1149 _diffrn_reflns_av_R_equivalents 0.1491 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.576 _diffrn_reflns_theta_max 27.574 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_point_group_measured_fraction_full 0.995 _reflns_number_total 1213 _reflns_number_gt 969 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Bruker AXS Collect (2009)' _computing_cell_refinement ; Denzo/Scalepack (HKL Research, Inc., 1997) ; _computing_data_reduction ; Denzo/Scalepack (HKL Research, Inc., 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material 'Ortep 3v2' _refine_special_details ; Refined as a 2-component twin. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1254P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 1213 _refine_ls_number_parameters 57 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0959 _refine_ls_R_factor_gt 0.0747 _refine_ls_wR_factor_ref 0.2093 _refine_ls_wR_factor_gt 0.1936 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.3315(4) 0.57655(13) 0.42033(8) 0.0308(4) Uani 1 1 d . . . . . Cl1 Cl 0.3075(8) 0.3283(3) 0.48574(13) 0.0320(6) Uani 1 1 d . . . . . N1 N 0.355(3) 0.8041(11) 0.3767(5) 0.036(2) Uani 1 1 d . . . . . C1 C 0.429(3) 0.9329(12) 0.3540(7) 0.034(3) Uani 1 1 d . . . . . C2 C 0.531(4) 1.0977(12) 0.3236(8) 0.038(3) Uani 1 1 d . . . . . H2A H 0.6802 1.0809 0.2800 0.058 Uiso 1 1 calc R U . . . H2B H 0.6615 1.1616 0.3611 0.058 Uiso 1 1 calc R U . . . H2C H 0.3194 1.1608 0.3095 0.058 Uiso 1 1 calc R U . . . Cl2 Cl -0.0731(7) 0.4883(3) 0.33933(14) 0.0324(6) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0355(8) 0.0268(6) 0.0301(6) 0.0027(5) -0.0040(7) -0.0037(5) Cl1 0.0367(14) 0.0266(10) 0.0327(12) 0.0017(8) -0.0048(13) -0.0039(11) N1 0.042(6) 0.034(5) 0.032(5) 0.008(4) -0.003(5) -0.009(5) C1 0.035(6) 0.030(5) 0.037(6) 0.000(4) -0.012(5) -0.002(4) C2 0.044(7) 0.025(5) 0.046(6) -0.009(5) -0.004(6) 0.005(5) Cl2 0.0333(13) 0.0341(12) 0.0299(11) 0.0007(10) -0.0040(11) -0.0032(11) _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 Cu1 N1 1.967(8) . ? Cu1 Cl2 2.236(3) . ? Cu1 Cl1 2.293(3) . ? Cu1 Cl1 2.310(3) 3_666 ? Cl1 Cu1 2.310(3) 3_666 ? N1 C1 1.133(13) . ? C1 C2 1.467(15) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 Cl2 93.1(3) . . ? N1 Cu1 Cl1 172.6(3) . . ? Cl2 Cu1 Cl1 92.48(10) . . ? N1 Cu1 Cl1 88.3(3) . 3_666 ? Cl2 Cu1 Cl1 172.89(14) . 3_666 ? Cl1 Cu1 Cl1 85.59(10) . 3_666 ? Cu1 Cl1 Cu1 94.41(10) . 3_666 ? C1 N1 Cu1 168.0(11) . . ? N1 C1 C2 178.8(14) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? _refine_diff_density_max 1.877 _refine_diff_density_min -1.361 _refine_diff_density_rms 0.281 _shelxl_version_number 2013-4 _shelx_res_file ; TITL sch12109r in P2(1)/c CELL 0.71073 3.7990 7.9080 18.0750 90.000 89.937 90.000 ZERR 2.00 0.0008 0.0016 0.0036 0.000 0.030 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N CL CU UNIT 8 12 4 8 4 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! L.S. 4 BOND $H FMAP 2 PLAN 9 ACTA TEMP -83.15 SIZE 0.75x0.05x0.02 TWIN 1 0 0 0 -1 0 0 0 -1 WGHT 0.125400 BASF 0.45519 FVAR 0.63117 CU1 5 0.331519 0.576550 0.420331 11.00000 0.03546 0.02681 = 0.03013 0.00268 -0.00397 -0.00370 CL1 4 0.307523 0.328313 0.485743 11.00000 0.03668 0.02661 = 0.03274 0.00169 -0.00478 -0.00390 N1 3 0.354580 0.804134 0.376667 11.00000 0.04184 0.03440 = 0.03170 0.00825 -0.00265 -0.00898 C1 1 0.429007 0.932870 0.353987 11.00000 0.03451 0.03010 = 0.03744 0.00000 -0.01230 -0.00164 C2 1 0.530981 1.097734 0.323601 11.00000 0.04448 0.02453 = 0.04636 -0.00860 -0.00438 0.00468 AFIX 137 H2A 2 0.680219 1.080942 0.279957 11.00000 -1.50000 H2B 2 0.661493 1.161641 0.361060 11.00000 -1.50000 H2C 2 0.319372 1.160780 0.309483 11.00000 -1.50000 AFIX 0 CL2 4 -0.073089 0.488263 0.339331 11.00000 0.03325 0.03415 = 0.02985 0.00074 -0.00401 -0.00323 REM ##### HKLF 4 REM sch12109r in P2(1)/c REM R1 = 0.0747 for 969 Fo > 4sig(Fo) and 0.0959 for all 1213 data REM 57 parameters refined using 0 restraints END WGHT 0.1252 0.0000 REM Highest difference peak 1.877, deepest hole -1.361, 1-sigma level 0.281 Q1 1 0.3936 0.5747 0.4612 11.00000 0.05 1.88 Q2 1 0.3178 0.5500 0.3773 11.00000 0.05 1.23 Q3 1 0.2925 0.3744 0.5260 11.00000 0.05 1.19 Q4 1 0.2361 0.6575 0.4689 11.00000 0.05 1.06 Q5 1 0.2884 0.3750 0.4378 11.00000 0.05 0.97 Q6 1 0.2880 0.7623 0.4278 11.00000 0.05 0.89 Q7 1 -0.3208 0.4842 0.3405 11.00000 0.05 0.89 Q8 1 0.3287 0.9458 0.4500 11.00000 0.05 0.78 Q9 1 0.1069 1.0991 0.2445 11.00000 0.05 0.77 ; _shelx_res_checksum 29565 _shelx_hkl_file ; -4 -6 -1 -20.01 22.13 -4 -6 0 -16.14 18.83 -4 -5 -7 25.45 18.72 -4 -5 -6 1.03 18.02 -4 -5 -4 0.48 16.41 -4 -5 -4 19.03 16.98 -4 -5 -3 76.86 16.80 -4 -5 -2 77.57 21.44 -4 -5 -2 100.14 20.30 -4 -5 -1 101.88 23.13 -4 -5 -1 68.03 21.37 -4 -5 0 192.19 26.75 -4 -4 -10 45.93 24.12 -4 -4 -9 10.01 21.13 -4 -4 -8 28.59 22.01 -4 -4 -7 1.09 17.38 -4 -4 -6 27.53 17.84 -4 -4 -4 10.29 14.21 -4 -4 -4 18.40 16.79 -4 -4 -3 67.87 15.58 -4 -4 -2 123.40 18.34 -4 -4 -2 85.27 20.94 -4 -4 -1 394.68 38.37 -4 -4 -1 432.24 37.21 -4 -4 0 12.83 15.07 -4 -3 -11 25.82 25.25 -4 -3 -10 30.06 19.47 -4 -3 -9 49.95 22.97 -4 -3 -8 83.36 21.14 -4 -3 -5 -1.14 17.17 -4 -3 -4 48.95 14.67 4 -3 3 0.61 18.80 -4 -3 -3 -1.74 16.28 -4 -3 -3 18.41 13.24 -4 -3 -2 96.00 16.13 4 -3 2 29.67 19.01 -4 -3 -1 55.18 14.01 4 -3 1 55.05 19.40 4 -3 0 118.37 20.71 -4 -3 0 115.68 22.60 -4 -2 -12 47.67 24.18 -4 -2 -11 6.76 24.59 -4 -2 -10 27.92 21.11 -4 -2 -9 37.89 27.35 -4 -2 -8 181.07 30.12 -4 -2 -7 172.09 27.99 -4 -2 -5 177.16 26.42 -4 -2 -4 174.69 15.84 4 -2 3 19.35 21.12 -4 -2 -3 89.19 19.54 -4 -2 -3 76.79 11.80 -4 -2 -2 11.05 8.66 4 -2 2 24.66 18.37 -4 -2 -2 39.32 17.23 -4 -2 -1 18.95 10.79 4 -2 1 30.11 19.90 -4 -2 0 52.42 19.22 4 -2 0 5.70 19.37 -4 -1 -13 57.31 27.80 -4 -1 -12 3.12 23.71 -4 -1 -11 30.01 22.37 -4 -1 -10 21.37 27.86 -4 -1 -9 57.29 22.84 -4 -1 -8 72.06 21.51 -4 -1 -7 59.19 21.29 -4 -1 -6 152.51 25.73 -4 -1 -5 252.70 34.63 -4 -1 -4 74.24 20.05 -4 -1 -3 185.63 24.64 -4 -1 -3 178.12 14.22 -4 -1 -2 26.04 8.08 -4 -1 -1 55.87 18.26 4 -1 1 10.03 20.07 -4 0 -13 12.29 22.75 -4 0 -12 17.86 23.61 -4 0 -11 -0.66 27.54 -4 0 -10 29.38 21.38 -4 0 -9 -16.17 21.57 -4 0 -8 208.97 31.50 -4 0 -7 25.42 24.09 -4 0 -6 149.82 27.38 -4 0 -3 -15.14 17.04 -4 0 -2 23.84 6.54 -4 0 0 73.21 18.28 -4 0 3 5.88 44.41 -4 0 5 36.99 20.88 -4 0 6 86.94 25.95 -4 0 7 -20.50 24.61 -4 0 8 184.47 29.36 -4 0 9 21.98 24.74 -4 0 10 0.00 24.08 -4 0 11 11.73 23.46 -4 0 12 33.26 26.35 -4 0 13 12.57 27.94 -4 1 3 174.41 23.89 -4 1 5 223.99 29.70 -4 1 6 162.71 25.10 -4 1 7 67.77 21.56 -4 1 8 104.34 26.84 -4 1 9 110.32 25.73 -4 1 10 -5.70 22.80 -4 1 11 2.15 29.36 -4 1 12 17.25 28.76 -4 1 13 34.57 25.24 -4 2 5 227.77 32.33 -4 2 6 16.27 24.06 -4 2 7 123.70 27.22 -4 2 8 218.34 32.24 -4 2 9 101.14 25.82 -4 2 10 18.93 27.28 -4 3 3 -2.78 22.21 -4 4 1 294.01 36.23 -4 4 2 108.36 23.88 -3 -8 -3 46.48 20.42 -3 -8 -2 162.09 26.08 -3 -8 -2 116.76 24.31 -3 -8 -1 79.41 23.02 -3 -8 -1 62.67 23.27 -3 -8 0 151.30 25.49 -3 -7 -9 16.29 16.84 -3 -7 -8 11.99 13.63 -3 -7 -7 175.56 23.46 -3 -7 -6 21.95 17.58 -3 -7 -6 67.35 22.77 -3 -7 -5 119.80 22.02 -3 -7 -5 124.01 21.94 -3 -7 -4 3.76 16.66 -3 -7 -4 1.12 17.88 -3 -7 -3 -6.42 19.81 -3 -7 -3 17.07 18.79 -3 -7 -2 36.03 18.64 -3 -7 -1 143.54 23.60 -3 -7 0 39.18 15.14 -3 -7 0 83.29 21.33 -3 -6 -12 56.46 17.49 -3 -6 -11 10.02 15.03 -3 -6 -10 -10.14 14.66 -3 -6 -9 36.12 14.74 -3 -6 -8 160.40 25.37 -3 -6 -7 -3.91 16.74 -3 -6 -6 482.07 41.82 -3 -6 -6 573.78 45.89 -3 -6 -5 0.00 16.15 -3 -6 -5 -16.01 16.02 -3 -6 -4 178.99 24.65 -3 -6 -4 172.73 23.03 -3 -6 -3 29.30 18.06 -3 -6 -3 19.93 17.33 -3 -6 -2 67.25 21.92 -3 -6 -2 90.21 19.23 -3 -6 -1 -2.28 19.39 -3 -6 0 34.45 19.46 -3 -5 -14 34.12 16.32 -3 -5 -13 57.56 17.10 -3 -5 -12 -3.97 14.76 -3 -5 -11 30.72 18.58 -3 -5 -10 11.70 18.72 3 -5 10 -28.80 20.80 -3 -5 -9 12.85 14.61 3 -5 9 5.35 20.74 -3 -5 -8 20.25 14.48 3 -5 8 8.72 24.81 3 -5 7 93.68 29.86 3 -5 6 -0.68 20.37 -3 -5 -6 48.54 15.09 -3 -5 -6 30.05 17.04 -3 -5 -5 471.80 37.98 3 -5 5 252.27 33.23 -3 -5 -5 333.34 31.05 -3 -5 -4 356.64 29.30 3 -5 4 172.05 28.66 -3 -5 -4 297.27 29.30 -3 -5 -3 37.90 14.62 3 -5 3 64.08 20.56 -3 -5 -3 46.48 20.14 -3 -5 -2 146.38 22.20 3 -5 2 96.49 21.66 -3 -5 -2 177.21 20.48 3 -5 1 97.45 19.08 -3 -5 -1 170.70 22.53 -3 -5 -1 148.60 22.71 -3 -5 0 -12.51 16.90 3 -5 0 12.48 14.98 -3 -5 0 9.77 12.83 -3 -4 -16 0.00 14.52 -3 -4 -15 255.36 32.38 -3 -4 -13 53.96 16.40 -3 -4 -12 48.88 15.79 -3 -4 -11 -13.11 13.72 3 -4 10 17.61 22.55 -3 -4 -10 18.11 15.10 3 -4 9 56.63 24.15 -3 -4 -9 56.87 17.02 3 -4 8 7.80 24.81 -3 -4 -8 39.09 17.48 -3 -4 -7 23.32 14.96 3 -4 7 23.33 23.34 -3 -4 -6 75.62 15.38 -3 -4 -6 51.54 18.42 3 -4 6 39.36 22.53 3 -4 5 155.38 25.55 -3 -4 -5 211.74 25.48 -3 -4 -5 319.15 24.53 -3 -4 -4 76.41 17.91 3 -4 4 60.60 22.11 -3 -4 -4 79.94 13.21 -3 -4 -3 717.15 48.79 -3 -4 -3 633.45 45.04 3 -4 3 458.16 43.62 3 -4 2 104.08 18.92 -3 -4 -2 132.40 21.22 -3 -4 -2 147.04 18.02 -3 -4 -1 171.36 21.33 3 -4 1 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