data_321_a
_audit_creation_date               2024-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C14 H16 Cl2 Fe N6, Cl, 2(C H4 O)'
_chemical_formula_sum              'C16 H24 Cl3 Fe N6 O2'
_chemical_formula_weight           494.61
_chemical_melting_point            ?
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'
 'Cl' 'Cl' 0.1484 0.1585 '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'
 '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'

_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.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     8.8010(4)
_cell_length_b                     11.4073(6)
_cell_length_c                     11.5391(4)
_cell_angle_alpha                  94.090(2)
_cell_angle_beta                   107.3930(10)
_cell_angle_gamma                  100.823(2)
_cell_volume                       1075.76(8)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      3780
_cell_measurement_temperature      193(2)
_cell_measurement_theta_max        49.99
_cell_measurement_theta_min        2.69
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      1.098
_exptl_absorpt_correction_T_max    ?
_exptl_absorpt_correction_T_min    ?
_exptl_absorpt_correction_type     ?
_exptl_absorpt_process_details     ?
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              blue
_exptl_crystal_colour_primary      blue
_exptl_crystal_density_diffrn      1.527
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               510
_exptl_crystal_size_max            0.14
_exptl_crystal_size_mid            0.13
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0349
_diffrn_reflns_av_unetI/netI       0.0448
_diffrn_reflns_Laue_measured_fraction_full  0.996
_diffrn_reflns_Laue_measured_fraction_max  0.996
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -9
_diffrn_reflns_limit_k_max         10
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         13
_diffrn_reflns_limit_l_min         -13
_diffrn_reflns_number              8296
_diffrn_reflns_point_group_measured_fraction_full  0.996
_diffrn_reflns_point_group_measured_fraction_max  0.996
_diffrn_reflns_theta_full          24.995
_diffrn_reflns_theta_max           24.995
_diffrn_reflns_theta_min           1.835
_diffrn_ambient_temperature        193.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.996
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3134
_reflns_number_total               3780
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         ?
_computing_data_collection         ?
_computing_data_reduction          ?
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max           0.768
_refine_diff_density_min           -0.788
_refine_diff_density_rms           0.080
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.095
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       257
_refine_ls_number_reflns           3780
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0588
_refine_ls_R_factor_gt             0.0467
_refine_ls_restrained_S_all        1.095
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0559P)²+1.5467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1204
_refine_ls_wR_factor_ref           0.1282
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C7(H7A,H7B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), C4(H4), C10(H10), C9(H9), C1(H1), C14(H14), C3(H3A), C2(H2),
 C13(H13)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2A)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       iterative
_atom_sites_solution_secondary     ?
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
 Fe1 Fe 0.73557(6) 0.20296(4) 0.86738(4) 0.02526(17) Uani 1 1 d . . . . .
 Cl1 Cl 0.92537(10) 0.34931(8) 1.01230(8) 0.0313(2) Uani 1 1 d . . . . .
 Cl2 Cl 0.73602(13) 0.05069(9) 0.97926(9) 0.0414(3) Uani 1 1 d . . . . .
 Cl3 Cl 0.23631(14) 0.42443(10) 0.51910(9) 0.0455(3) Uani 1 1 d . . . . .
 N4 N 0.5472(3) 0.0989(3) 0.7156(3) 0.0270(6) Uani 1 1 d . . . . .
 N1 N 0.5457(3) 0.2852(3) 0.8938(3) 0.0289(7) Uani 1 1 d . . . . .
 N2 N 0.7009(3) 0.3372(2) 0.7263(2) 0.0241(6) Uani 1 1 d . . . . .
 N3 N 0.3687(4) 0.0816(3) 0.5327(3) 0.0299(7) Uani 1 1 d . . . . .
 H3 H 0.315643 0.099607 0.460952 0.036 Uiso 1 1 calc R . . . .
 N5 N 0.9008(4) 0.1826(3) 0.7731(3) 0.0296(7) Uani 1 1 d . . . . .
 O1 O 0.2069(5) 0.1938(3) 0.3503(3) 0.0554(8) Uani 1 1 d . . . . .
 H1A H 0.202845 0.257002 0.390220 0.083 Uiso 1 1 calc GR . . . .
 N6 N 1.0402(4) 0.2491(3) 0.6519(3) 0.0394(8) Uani 1 1 d . . . . .
 H6 H 1.077928 0.295649 0.604482 0.047 Uiso 1 1 calc R . . . .
 C8 C 0.4971(4) 0.1534(3) 0.6179(3) 0.0244(7) Uani 1 1 d . . . . .
 C5 C 0.5231(4) 0.3843(3) 0.8413(3) 0.0274(8) Uani 1 1 d . . . . .
 C11 C 0.8639(4) 0.3794(3) 0.7122(3) 0.0298(8) Uani 1 1 d . . . . .
 H11A H 0.933953 0.441312 0.781527 0.036 Uiso 1 1 calc R . . . .
 H11B H 0.853109 0.414598 0.634874 0.036 Uiso 1 1 calc R . . . .
 C7 C 0.5794(4) 0.2765(3) 0.6061(3) 0.0275(8) Uani 1 1 d . . . . .
 H7A H 0.496713 0.325138 0.577944 0.033 Uiso 1 1 calc R . . . .
 H7B H 0.635683 0.270919 0.544008 0.033 Uiso 1 1 calc R . . . .
 C12 C 0.9353(4) 0.2714(3) 0.7103(3) 0.0298(8) Uani 1 1 d . . . . .
 C4 C 0.3989(4) 0.4385(4) 0.8505(3) 0.0372(9) Uani 1 1 d . . . . .
 H4 H 0.383155 0.508701 0.812961 0.045 Uiso 1 1 calc R . . . .
 C10 C 0.4447(4) -0.0137(3) 0.6916(3) 0.0306(8) Uani 1 1 d . . . . .
 H10 H 0.450485 -0.072778 0.745855 0.037 Uiso 1 1 calc R . . . .
 C6 C 0.6440(4) 0.4360(3) 0.7797(3) 0.0297(8) Uani 1 1 d . . . . .
 H6A H 0.592158 0.481080 0.714270 0.036 Uiso 1 1 calc R . . . .
 H6B H 0.738122 0.492637 0.840228 0.036 Uiso 1 1 calc R . . . .
 C9 C 0.3340(4) -0.0265(3) 0.5778(3) 0.0328(8) Uani 1 1 d . . . . .
 H9 H 0.250131 -0.095343 0.537370 0.039 Uiso 1 1 calc R . . . .
 C1 C 0.4413(5) 0.2408(4) 0.9525(3) 0.0382(10) Uani 1 1 d . . . . .
 H1 H 0.453198 0.169504 0.988827 0.046 Uiso 1 1 calc R . . . .
 C14 C 0.9897(5) 0.0979(4) 0.7559(4) 0.0443(10) Uani 1 1 d . . . . .
 H14 H 0.989742 0.024614 0.790100 0.053 Uiso 1 1 calc R . . . .
 C3 C 0.3007(5) 0.3921(5) 0.9123(4) 0.0508(12) Uani 1 1 d . . . . .
 H3A H 0.216501 0.430007 0.920676 0.061 Uiso 1 1 calc R . . . .
 C16 C 0.2777(8) 0.6916(4) 0.6348(5) 0.0727(19) Uani 1 1 d . . . . .
 H16A H 0.201638 0.663460 0.551843 0.109 Uiso 1 1 calc GR . . . .
 H16B H 0.348033 0.634440 0.658822 0.109 Uiso 1 1 calc GR . . . .
 H16C H 0.345021 0.770957 0.636473 0.109 Uiso 1 1 calc GR . . . .
 C2 C 0.3220(5) 0.2933(5) 0.9615(4) 0.0513(12) Uani 1 1 d . . . . .
 H2 H 0.251003 0.259109 1.003968 0.062 Uiso 1 1 calc R . . . .
 C13 C 1.0787(5) 0.1391(4) 0.6798(4) 0.0515(12) Uani 1 1 d . . . . .
 H13 H 1.150757 0.100277 0.652503 0.062 Uiso 1 1 calc R . . . .
 C15 C 0.2436(7) 0.2219(5) 0.2430(4) 0.0618(14) Uani 1 1 d . . . . .
 H15A H 0.241786 0.147535 0.194048 0.093 Uiso 1 1 calc GR . . . .
 H15B H 0.352287 0.275017 0.265726 0.093 Uiso 1 1 calc GR . . . .
 H15C H 0.162299 0.262641 0.194978 0.093 Uiso 1 1 calc GR . . . .
 O2 O 0.1908(8) 0.7000(5) 0.7157(6) 0.1193(18) Uani 1 1 d . . . . .
 H2A H 0.195002 0.641796 0.756294 0.179 Uiso 1 1 calc GR . . . .


_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
 Fe1 Cl1 2.2931(10) . ?
 Fe1 Cl2 2.2367(10) . ?
 Fe1 N4 2.110(3) . ?
 Fe1 N1 2.148(3) . ?
 Fe1 N2 2.308(3) . ?
 Fe1 N5 2.095(3) . ?
 N4 C8 1.326(4) . ?
 N4 C10 1.380(4) . ?
 N1 C5 1.341(5) . ?
 N1 C1 1.344(5) . ?
 N2 C11 1.486(4) . ?
 N2 C7 1.498(4) . ?
 N2 C6 1.483(4) . ?
 N3 H3 0.8800 . ?
 N3 C8 1.337(4) . ?
 N3 C9 1.390(5) . ?
 N5 C12 1.329(5) . ?
 N5 C14 1.391(5) . ?
 O1 H1A 0.8400 . ?
 O1 C15 1.413(5) . ?
 N6 H6 0.8800 . ?
 N6 C12 1.345(5) . ?
 N6 C13 1.395(6) . ?
 C8 C7 1.490(5) . ?
 C5 C4 1.379(5) . ?
 C5 C6 1.503(5) . ?
 C11 H11A 0.9900 . ?
 C11 H11B 0.9900 . ?
 C11 C12 1.486(5) . ?
 C7 H7A 0.9900 . ?
 C7 H7B 0.9900 . ?
 C4 H4 0.9500 . ?
 C4 C3 1.336(6) . ?
 C10 H10 0.9500 . ?
 C10 C9 1.360(5) . ?
 C6 H6A 0.9900 . ?
 C6 H6B 0.9900 . ?
 C9 H9 0.9500 . ?
 C1 H1 0.9500 . ?
 C1 C2 1.328(6) . ?
 C14 H14 0.9500 . ?
 C14 C13 1.391(7) . ?
 C3 H3A 0.9500 . ?
 C3 C2 1.317(7) . ?
 C16 H16A 0.9800 . ?
 C16 H16B 0.9800 . ?
 C16 H16C 0.9800 . ?
 C16 O2 1.380(7) . ?
 C2 H2 0.9500 . ?
 C13 H13 0.9500 . ?
 C15 H15A 0.9800 . ?
 C15 H15B 0.9800 . ?
 C15 H15C 0.9800 . ?
 O2 H2A 0.8400 . ?

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
 Cl1 Fe1 N2 90.90(7) . . ?
 Cl2 Fe1 Cl1 98.79(4) . . ?
 Cl2 Fe1 N2 170.30(8) . . ?
 N4 Fe1 Cl1 168.06(9) . . ?
 N4 Fe1 Cl2 92.56(8) . . ?
 N4 Fe1 N1 84.16(11) . . ?
 N4 Fe1 N2 77.74(11) . . ?
 N1 Fe1 Cl1 89.43(8) . . ?
 N1 Fe1 Cl2 104.36(8) . . ?
 N1 Fe1 N2 75.12(11) . . ?
 N5 Fe1 Cl1 92.23(9) . . ?
 N5 Fe1 Cl2 104.77(9) . . ?
 N5 Fe1 N4 88.41(11) . . ?
 N5 Fe1 N1 150.21(12) . . ?
 N5 Fe1 N2 75.11(11) . . ?
 C8 N4 Fe1 116.7(2) . . ?
 C8 N4 C10 106.5(3) . . ?
 C10 N4 Fe1 136.5(2) . . ?
 C5 N1 Fe1 117.5(2) . . ?
 C5 N1 C1 117.3(3) . . ?
 C1 N1 Fe1 125.1(3) . . ?
 C11 N2 Fe1 105.9(2) . . ?
 C11 N2 C7 110.4(3) . . ?
 C7 N2 Fe1 110.5(2) . . ?
 C6 N2 Fe1 106.27(19) . . ?
 C6 N2 C11 112.2(3) . . ?
 C6 N2 C7 111.3(3) . . ?
 C8 N3 H3 126.2 . . ?
 C8 N3 C9 107.7(3) . . ?
 C9 N3 H3 126.2 . . ?
 C12 N5 Fe1 115.8(2) . . ?
 C12 N5 C14 106.9(3) . . ?
 C14 N5 Fe1 137.2(3) . . ?
 C15 O1 H1A 109.5 . . ?
 C12 N6 H6 126.1 . . ?
 C12 N6 C13 107.8(3) . . ?
 C13 N6 H6 126.1 . . ?
 N4 C8 N3 110.8(3) . . ?
 N4 C8 C7 123.3(3) . . ?
 N3 C8 C7 125.9(3) . . ?
 N1 C5 C4 120.4(4) . . ?
 N1 C5 C6 117.0(3) . . ?
 C4 C5 C6 122.6(3) . . ?
 N2 C11 H11A 110.5 . . ?
 N2 C11 H11B 110.5 . . ?
 N2 C11 C12 106.1(3) . . ?
 H11A C11 H11B 108.7 . . ?
 C12 C11 H11A 110.5 . . ?
 C12 C11 H11B 110.5 . . ?
 N2 C7 H7A 109.5 . . ?
 N2 C7 H7B 109.5 . . ?
 C8 C7 N2 110.9(3) . . ?
 C8 C7 H7A 109.5 . . ?
 C8 C7 H7B 109.5 . . ?
 H7A C7 H7B 108.1 . . ?
 N5 C12 N6 111.2(3) . . ?
 N5 C12 C11 120.9(3) . . ?
 N6 C12 C11 127.8(3) . . ?
 C5 C4 H4 120.1 . . ?
 C3 C4 C5 119.9(4) . . ?
 C3 C4 H4 120.1 . . ?
 N4 C10 H10 125.5 . . ?
 C9 C10 N4 109.1(3) . . ?
 C9 C10 H10 125.5 . . ?
 N2 C6 C5 109.6(3) . . ?
 N2 C6 H6A 109.7 . . ?
 N2 C6 H6B 109.7 . . ?
 C5 C6 H6A 109.7 . . ?
 C5 C6 H6B 109.7 . . ?
 H6A C6 H6B 108.2 . . ?
 N3 C9 H9 127.0 . . ?
 C10 C9 N3 105.9(3) . . ?
 C10 C9 H9 127.0 . . ?
 N1 C1 H1 118.9 . . ?
 C2 C1 N1 122.2(4) . . ?
 C2 C1 H1 118.9 . . ?
 N5 C14 H14 125.9 . . ?
 C13 C14 N5 108.2(4) . . ?
 C13 C14 H14 125.9 . . ?
 C4 C3 H3A 120.4 . . ?
 C2 C3 C4 119.3(4) . . ?
 C2 C3 H3A 120.4 . . ?
 H16A C16 H16B 109.5 . . ?
 H16A C16 H16C 109.5 . . ?
 H16B C16 H16C 109.5 . . ?
 O2 C16 H16A 109.5 . . ?
 O2 C16 H16B 109.5 . . ?
 O2 C16 H16C 109.5 . . ?
 C1 C2 H2 119.5 . . ?
 C3 C2 C1 121.0(4) . . ?
 C3 C2 H2 119.5 . . ?
 N6 C13 H13 127.1 . . ?
 C14 C13 N6 105.8(4) . . ?
 C14 C13 H13 127.1 . . ?
 O1 C15 H15A 109.5 . . ?
 O1 C15 H15B 109.5 . . ?
 O1 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?
 C16 O2 H2A 109.5 . . ?

_olex2_submission_special_instructions  'No special instructions were received'
