 
data_joer083 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C11 H13 Cl Fe N2' 
_chemical_formula_weight          264.53 
  
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' 
 'Fe'  'Fe'   0.3463   0.8444 
 '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' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            19 
_space_group_name_H-M_alt         'P 21 21 21' 
_space_group_name_Hall            'P 2ac 2ab' 
  
_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+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
  
_cell_length_a                    8.943(5) 
_cell_length_b                    10.923(6) 
_cell_length_c                    11.682(6) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      1141.2(11) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     979 
_cell_measurement_theta_min       2.55 
_cell_measurement_theta_max       28.21 
  
_exptl_crystal_description        Plate 
_exptl_crystal_colour             Orange 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.540 
_exptl_crystal_F_000              544 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.276 
_exptl_crystal_size_mid           0.232 
_exptl_crystal_size_min           0.090 
_exptl_absorpt_coefficient_mu     1.522 
_shelx_estimated_absorpt_T_min    0.679 
_shelx_estimated_absorpt_T_max    0.875 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6311   
_exptl_absorpt_correction_T_max   0.7457 
_exptl_absorpt_process_details    'APEX3 (Bruker, 2015)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       200(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker AXS APEX diffractometer' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.33 
_diffrn_reflns_number             15679 
_diffrn_reflns_av_unetI/netI      0.0210 
_diffrn_reflns_av_R_equivalents   0.0327 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          2.553 
_diffrn_reflns_theta_max          28.288 
_diffrn_reflns_theta_full         25.000 
_diffrn_measured_fraction_theta_max   0.999 
_diffrn_measured_fraction_theta_full  1.000 
_diffrn_reflns_Laue_measured_fraction_max    0.999 
_diffrn_reflns_Laue_measured_fraction_full   1.000 
_diffrn_reflns_point_group_measured_fraction_max   0.999 
_diffrn_reflns_point_group_measured_fraction_full  1.000 
_reflns_number_total              2834 
_reflns_number_gt                 2778 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.731 
_reflns_Friedel_fraction_max      0.998 
_reflns_Friedel_fraction_full     1.000 
  
_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 SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'Bruker SHELXTL' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0373P)²+0.2005P] where P=(Fo²+2Fc²)/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_abs_structure_details 
; 
 Flack x determined using 1158 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    -0.031(8) 
_chemical_absolute_configuration  ? 
_refine_ls_number_reflns          2834 
_refine_ls_number_parameters      136 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0237 
_refine_ls_R_factor_gt            0.0231 
_refine_ls_wR_factor_ref          0.0612 
_refine_ls_wR_factor_gt           0.0603 
_refine_ls_goodness_of_fit_ref    1.020 
_refine_ls_restrained_S_all       1.020 
_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_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 
Fe Fe 0.77249(3) 0.39255(3) 0.16991(3) 0.02840(10) Uani 1 1 d . . . . . 
Cl Cl 0.17403(6) 0.41817(5) 0.50537(5) 0.03203(13) Uani 1 1 d . . . . . 
N1 N 0.3666(2) 0.4275(2) 0.25567(18) 0.0365(5) Uani 1 1 d . . . . . 
H1A H 0.2990 0.4514 0.3056 0.044 Uiso 1 1 calc R U . . . 
H1B H 0.3661 0.4576 0.1858 0.044 Uiso 1 1 calc R U . . . 
N2 N 0.4682(2) 0.3019(2) 0.39040(17) 0.0322(4) Uani 1 1 d . . . . . 
H2A H 0.4001 0.3264 0.4397 0.039 Uiso 1 1 calc R U . . . 
H2B H 0.5358 0.2477 0.4111 0.039 Uiso 1 1 calc R U . . . 
C1 C 0.5791(3) 0.3041(2) 0.20332(19) 0.0273(4) Uani 1 1 d . . . . . 
C2 C 0.5872(3) 0.3355(2) 0.0842(2) 0.0354(5) Uani 1 1 d . . . . . 
H2C H 0.5154 0.3886 0.0414 0.042 Uiso 1 1 calc R U . . . 
C3 C 0.7150(4) 0.2766(3) 0.0383(2) 0.0446(6) Uani 1 1 d . . . . . 
H3A H 0.7507 0.2832 -0.0426 0.054 Uiso 1 1 calc R U . . . 
C4 C 0.7872(4) 0.2107(2) 0.1267(2) 0.0432(6) Uani 1 1 d . . . . . 
H4A H 0.8819 0.1628 0.1186 0.052 Uiso 1 1 calc R U . . . 
C5 C 0.7056(3) 0.2272(2) 0.2296(2) 0.0335(5) Uani 1 1 d . . . . . 
H5A H 0.7303 0.1912 0.3060 0.040 Uiso 1 1 calc R U . . . 
C6 C 0.7700(5) 0.5636(3) 0.2413(3) 0.0572(8) Uani 1 1 d . . . . . 
H6A H 0.6799 0.6064 0.2725 0.069 Uiso 1 1 calc R U . . . 
C7 C 0.8216(5) 0.5702(3) 0.1279(3) 0.0619(10) Uani 1 1 d . . . . . 
H7A H 0.7760 0.6189 0.0644 0.074 Uiso 1 1 calc R U . . . 
C8 C 0.9505(5) 0.4966(4) 0.1208(5) 0.0803(13) Uani 1 1 d . . . . . 
H8A H 1.0129 0.4837 0.0508 0.096 Uiso 1 1 calc R U . . . 
C9 C 0.9764(4) 0.4458(5) 0.2284(5) 0.0849(15) Uani 1 1 d . . . . . 
H9A H 1.0610 0.3900 0.2487 0.102 Uiso 1 1 calc R U . . . 
C10 C 0.8657(5) 0.4870(4) 0.3034(3) 0.0689(11) Uani 1 1 d . . . . . 
H10A H 0.8569 0.4660 0.3864 0.083 Uiso 1 1 calc R U . . . 
C11 C 0.4689(2) 0.3462(2) 0.2856(2) 0.0271(4) Uani 1 1 d . . . . . 
  
  
_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 
Fe C1 2.019(2) . ? 
Fe C5 2.026(2) . ? 
Fe C2 2.034(3) . ? 
Fe C9 2.033(4) . ? 
Fe C8 2.038(3) . ? 
Fe C6 2.046(3) . ? 
Fe C10 2.047(3) . ? 
Fe C7 2.049(3) . ? 
Fe C4 2.054(3) . ? 
Fe C3 2.058(3) . ? 
N1 C11 1.322(3) . ? 
N2 C11 1.317(3) . ? 
C1 C2 1.435(3) . ? 
C1 C5 1.442(3) . ? 
C1 C11 1.452(3) . ? 
C2 C3 1.418(4) . ? 
C3 C4 1.415(4) . ? 
C4 C5 1.417(3) . ? 
C6 C10 1.399(5) . ? 
C6 C7 1.405(5) . ? 
C7 C8 1.407(6) . ? 
C8 C9 1.394(7) . ? 
C9 C10 1.397(7) . ? 
  
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 
C1 Fe C5 41.76(10) . . ? 
C1 Fe C2 41.46(10) . . ? 
C5 Fe C2 69.86(11) . . ? 
C1 Fe C9 147.21(17) . . ? 
C5 Fe C9 113.85(16) . . ? 
C2 Fe C9 169.80(19) . . ? 
C1 Fe C8 171.93(17) . . ? 
C5 Fe C8 145.54(17) . . ? 
C2 Fe C8 131.95(18) . . ? 
C9 Fe C8 40.0(2) . . ? 
C1 Fe C6 110.41(13) . . ? 
C5 Fe C6 132.08(13) . . ? 
C2 Fe C6 118.13(14) . . ? 
C9 Fe C6 67.15(19) . . ? 
C8 Fe C6 67.31(18) . . ? 
C1 Fe C10 116.29(14) . . ? 
C5 Fe C10 107.90(13) . . ? 
C2 Fe C10 149.45(15) . . ? 
C9 Fe C10 40.0(2) . . ? 
C8 Fe C10 67.38(19) . . ? 
C6 Fe C10 39.98(15) . . ? 
C1 Fe C7 133.08(14) . . ? 
C5 Fe C7 171.75(13) . . ? 
C2 Fe C7 110.31(14) . . ? 
C9 Fe C7 67.48(18) . . ? 
C8 Fe C7 40.28(18) . . ? 
C6 Fe C7 40.11(15) . . ? 
C10 Fe C7 67.51(16) . . ? 
C1 Fe C4 68.84(11) . . ? 
C5 Fe C4 40.64(10) . . ? 
C2 Fe C4 68.57(12) . . ? 
C9 Fe C4 107.58(18) . . ? 
C8 Fe C4 114.87(16) . . ? 
C6 Fe C4 169.73(13) . . ? 
C10 Fe C4 130.44(15) . . ? 
C7 Fe C4 147.53(14) . . ? 
C1 Fe C3 68.65(11) . . ? 
C5 Fe C3 68.59(11) . . ? 
C2 Fe C3 40.54(11) . . ? 
C9 Fe C3 130.64(19) . . ? 
C8 Fe C3 109.13(18) . . ? 
C6 Fe C3 149.77(14) . . ? 
C10 Fe C3 168.89(16) . . ? 
C7 Fe C3 117.24(14) . . ? 
C4 Fe C3 40.27(11) . . ? 
C2 C1 C5 107.8(2) . . ? 
C2 C1 C11 126.9(2) . . ? 
C5 C1 C11 125.2(2) . . ? 
C2 C1 Fe 69.81(14) . . ? 
C5 C1 Fe 69.38(14) . . ? 
C11 C1 Fe 123.91(16) . . ? 
C3 C2 C1 107.4(2) . . ? 
C3 C2 Fe 70.63(16) . . ? 
C1 C2 Fe 68.73(14) . . ? 
C4 C3 C2 108.8(2) . . ? 
C4 C3 Fe 69.73(16) . . ? 
C2 C3 Fe 68.83(14) . . ? 
C3 C4 C5 108.7(2) . . ? 
C3 C4 Fe 70.00(15) . . ? 
C5 C4 Fe 68.63(13) . . ? 
C4 C5 C1 107.3(2) . . ? 
C4 C5 Fe 70.73(14) . . ? 
C1 C5 Fe 68.86(13) . . ? 
C10 C6 C7 108.5(4) . . ? 
C10 C6 Fe 70.0(2) . . ? 
C7 C6 Fe 70.06(19) . . ? 
C8 C7 C6 107.2(4) . . ? 
C8 C7 Fe 69.45(19) . . ? 
C6 C7 Fe 69.82(17) . . ? 
C9 C8 C7 108.1(4) . . ? 
C9 C8 Fe 69.8(2) . . ? 
C7 C8 Fe 70.3(2) . . ? 
C8 C9 C10 108.6(4) . . ? 
C8 C9 Fe 70.2(2) . . ? 
C10 C9 Fe 70.5(2) . . ? 
C9 C10 C6 107.6(4) . . ? 
C9 C10 Fe 69.4(2) . . ? 
C6 C10 Fe 69.97(19) . . ? 
N1 C11 N2 119.3(2) . . ? 
N1 C11 C1 120.5(2) . . ? 
N2 C11 C1 120.1(2) . . ? 
  
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 
C5 C1 C2 C3 1.1(3) . . . . ? 
C11 C1 C2 C3 178.2(2) . . . . ? 
Fe C1 C2 C3 60.32(19) . . . . ? 
C5 C1 C2 Fe -59.17(17) . . . . ? 
C11 C1 C2 Fe 117.9(2) . . . . ? 
C1 C2 C3 C4 -0.7(3) . . . . ? 
Fe C2 C3 C4 58.4(2) . . . . ? 
C1 C2 C3 Fe -59.11(17) . . . . ? 
C2 C3 C4 C5 0.0(3) . . . . ? 
Fe C3 C4 C5 57.8(2) . . . . ? 
C2 C3 C4 Fe -57.9(2) . . . . ? 
C3 C4 C5 C1 0.7(3) . . . . ? 
Fe C4 C5 C1 59.40(16) . . . . ? 
C3 C4 C5 Fe -58.7(2) . . . . ? 
C2 C1 C5 C4 -1.2(3) . . . . ? 
C11 C1 C5 C4 -178.3(2) . . . . ? 
Fe C1 C5 C4 -60.60(18) . . . . ? 
C2 C1 C5 Fe 59.44(16) . . . . ? 
C11 C1 C5 Fe -117.7(2) . . . . ? 
C10 C6 C7 C8 0.1(4) . . . . ? 
Fe C6 C7 C8 -59.6(3) . . . . ? 
C10 C6 C7 Fe 59.7(2) . . . . ? 
C6 C7 C8 C9 0.1(4) . . . . ? 
Fe C7 C8 C9 -59.8(3) . . . . ? 
C6 C7 C8 Fe 59.9(2) . . . . ? 
C7 C8 C9 C10 -0.3(5) . . . . ? 
Fe C8 C9 C10 -60.3(3) . . . . ? 
C7 C8 C9 Fe 60.1(3) . . . . ? 
C8 C9 C10 C6 0.3(4) . . . . ? 
Fe C9 C10 C6 -59.8(2) . . . . ? 
C8 C9 C10 Fe 60.1(3) . . . . ? 
C7 C6 C10 C9 -0.2(4) . . . . ? 
Fe C6 C10 C9 59.5(3) . . . . ? 
C7 C6 C10 Fe -59.7(2) . . . . ? 
C2 C1 C11 N1 -4.2(4) . . . . ? 
C5 C1 C11 N1 172.3(2) . . . . ? 
Fe C1 C11 N1 84.9(3) . . . . ? 
C2 C1 C11 N2 174.5(2) . . . . ? 
C5 C1 C11 N2 -8.9(3) . . . . ? 
Fe C1 C11 N2 -96.4(2) . . . . ? 
  
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 H1A Cl  0.88 2.61 3.389(3) 147.6 . 
N1 H1B Cl  0.88 2.53 3.395(3) 166.7 2_564 
N2 H2A Cl  0.88 2.38 3.215(2) 157.8 . 
N2 H2B Cl  0.88 2.40 3.263(2) 166.7 4_556 
  
_refine_diff_density_max    0.275 
_refine_diff_density_min   -0.261 
_refine_diff_density_rms    0.050 
  
  
  
