#------------------------------------------------------------------------------
#$Date: 2024-04-06 02:42:49 +0300 (Sat, 06 Apr 2024) $
#$Revision: 291118 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023022.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023022
loop_
_publ_author_name
'Sghyar, Riham'
'Bentama, Abdeslem'
'Haoudi, Amal'
'Mazzah, Ahmed'
'Mague, Joel T.'
'Hökelek, Tuncer'
'El Hadrami, El Mestafa'
'Sebbar, Nada Kheira'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (Z)-N-{chloro-[(4-ferrocenylphen-yl)imino]-meth-yl}-4-ferrocenylaniline
 N,N-di-methyl-formamide monosolvate.
;
_journal_coeditor_code           OX2002
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              262
_journal_page_last               266
_journal_paper_doi               10.1107/S2056989024001002
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          '[Fe2 (C5 H5)2 (C23 H17 Cl N2)]'
_chemical_formula_moiety         'C33 H27 Cl Fe2 N2, C3 H7 N O'
_chemical_formula_sum            'C36 H34 Cl Fe2 N3 O'
_chemical_formula_weight         671.81
_chemical_name_systematic
;
(Z)-N-[Chloro[(4-ferrocenylphenyl)imino]methyl]-\
4-ferrocenylaniline N,N-dimethylformamide monosolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_cell_angle_alpha                95.099(2)
_cell_angle_beta                 99.963(2)
_cell_angle_gamma                96.414(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0175(10)
_cell_length_b                   11.3134(14)
_cell_length_c                   17.408(2)
_cell_measurement_reflns_used    9233
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.593
_cell_measurement_theta_min      2.288
_cell_volume                     1536.0(3)
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2021)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL-2019/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'Bruker D8 QUEST PHOTON 3 diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 3 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19205
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.593
_diffrn_reflns_theta_min         2.287
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.066
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.847
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         9949
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0465
_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)+(0.0573P)²+0.8875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                7143
_reflns_number_total             9949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ox2002sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023022.cif.'
_cod_database_code               2023022
_cod_database_fobs_code          2023022
_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.
;
_shelx_estimated_absorpt_t_min   0.709
_shelx_estimated_absorpt_t_max   0.965
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe1 1.37373(4) 0.63325(3) 0.87322(2) 0.02325(8) Uani d 1 . .
Fe Fe2 0.07704(4) 0.90503(3) 0.14060(2) 0.02200(8) Uani d 1 . .
Cl Cl1 0.81676(8) 0.78250(5) 0.48737(4) 0.03526(14) Uani d 1 . .
N N1 0.7405(2) 0.55410(16) 0.51322(11) 0.0235(4) Uani d 1 . .
H H1 0.695(6) 0.4785(19) 0.492(3) 0.028 Uiso d 0.5 A 1
N N2 0.5880(2) 0.60294(17) 0.40311(11) 0.0250(4) Uani d 1 . .
H H1B 0.545(7) 0.5247(16) 0.401(3) 0.030 Uiso d 0.5 B 2
C C1 1.6276(3) 0.6844(3) 0.8766(2) 0.0520(9) Uani d 1 . .
H H1A 1.719399 0.631160 0.882788 0.062 Uiso calc 1 . .
C C2 1.5318(4) 0.7073(3) 0.8050(2) 0.0458(7) Uani d 1 . .
H H2 1.543702 0.673373 0.751491 0.055 Uiso calc 1 . .
C C3 1.4175(3) 0.7870(2) 0.82208(16) 0.0360(6) Uani d 1 . .
H H3 1.333001 0.818748 0.782517 0.043 Uiso calc 1 . .
C C4 1.4400(3) 0.8136(2) 0.90388(17) 0.0360(6) Uani d 1 . .
H H4 1.375259 0.867808 0.932501 0.043 Uiso calc 1 . .
C C5 1.5711(4) 0.7501(3) 0.93865(19) 0.0453(7) Uani d 1 . .
H H5 1.616204 0.751766 0.996066 0.054 Uiso calc 1 . .
C C6 1.1536(3) 0.53288(19) 0.81168(13) 0.0218(4) Uani d 1 . .
C C7 1.2867(3) 0.45906(19) 0.82827(13) 0.0233(4) Uani d 1 . .
H H7 1.334693 0.410700 0.788454 0.028 Uiso calc 1 . .
C C8 1.3395(3) 0.4672(2) 0.91084(14) 0.0286(5) Uani d 1 . .
H H8 1.431207 0.425495 0.939174 0.034 Uiso calc 1 . .
C C9 1.2413(3) 0.5455(2) 0.94644(14) 0.0290(5) Uani d 1 . .
H H9 1.251227 0.568080 1.004055 0.035 Uiso calc 1 . .
C C10 1.1260(3) 0.5865(2) 0.88539(13) 0.0249(4) Uani d 1 . .
H H10 1.041297 0.643043 0.892816 0.030 Uiso calc 1 . .
C C11 1.0568(3) 0.54542(19) 0.73328(12) 0.0213(4) Uani d 1 . .
C C12 1.0447(3) 0.4563(2) 0.67087(13) 0.0233(4) Uani d 1 . .
H H12 1.105904 0.389711 0.678342 0.028 Uiso calc 1 . .
C C13 0.9452(3) 0.4631(2) 0.59827(13) 0.0241(4) Uani d 1 . .
H H13 0.939304 0.401614 0.556665 0.029 Uiso calc 1 . .
C C14 0.8535(3) 0.56001(19) 0.58587(13) 0.0223(4) Uani d 1 . .
C C15 0.8653(3) 0.65036(19) 0.64720(13) 0.0243(4) Uani d 1 . .
H H15 0.804354 0.717018 0.639563 0.029 Uiso calc 1 . .
C C16 0.9662(3) 0.64274(19) 0.71946(13) 0.0238(4) Uani d 1 . .
H H16 0.974038 0.705219 0.760665 0.029 Uiso calc 1 . .
C C17 0.7107(3) 0.64420(19) 0.46750(13) 0.0224(4) Uani d 1 . .
C C18 0.5173(3) 0.65737(19) 0.33737(13) 0.0215(4) Uani d 1 . .
C C19 0.3789(3) 0.5892(2) 0.28742(14) 0.0260(4) Uani d 1 . .
H H19 0.339475 0.511829 0.299358 0.031 Uiso calc 1 . .
C C20 0.2979(3) 0.6318(2) 0.22089(13) 0.0255(4) Uani d 1 . .
H H20 0.203611 0.583399 0.187916 0.031 Uiso calc 1 . .
C C21 0.3523(3) 0.74514(18) 0.20122(13) 0.0209(4) Uani d 1 . .
C C22 0.4938(3) 0.8110(2) 0.25035(14) 0.0267(5) Uani d 1 . .
H H22 0.535424 0.887311 0.237483 0.032 Uiso calc 1 . .
C C23 0.5765(3) 0.7693(2) 0.31754(14) 0.0272(5) Uani d 1 . .
H H23 0.672821 0.816635 0.349791 0.033 Uiso calc 1 . .
C C24 0.2600(3) 0.79388(19) 0.13310(13) 0.0216(4) Uani d 1 . .
C C25 0.0994(3) 0.7426(2) 0.08542(14) 0.0255(4) Uani d 1 . .
H H25 0.033179 0.664561 0.091133 0.031 Uiso calc 1 . .
C C26 0.0495(3) 0.8218(2) 0.02916(14) 0.0277(5) Uani d 1 . .
H H26 -0.057611 0.809202 -0.011338 0.033 Uiso calc 1 . .
C C27 0.1775(3) 0.9230(2) 0.04117(14) 0.0270(5) Uani d 1 . .
H H27 0.175995 0.993803 0.010649 0.032 Uiso calc 1 . .
C C28 0.3065(3) 0.9062(2) 0.10470(13) 0.0252(4) Uani d 1 . .
H H28 0.411516 0.963704 0.126666 0.030 Uiso calc 1 . .
C C29 -0.1556(3) 0.9466(2) 0.15862(16) 0.0346(5) Uani d 1 . .
H H29 -0.265962 0.926545 0.120477 0.041 Uiso calc 1 . .
C C30 -0.0392(3) 1.0524(2) 0.16516(15) 0.0325(5) Uani d 1 . .
H H30 -0.052690 1.120135 0.132317 0.039 Uiso calc 1 . .
C C31 0.1004(4) 1.0450(2) 0.22600(15) 0.0339(5) Uani d 1 . .
H H31 0.202644 1.106623 0.243602 0.041 Uiso calc 1 . .
C C32 0.0705(4) 0.9344(3) 0.25732(15) 0.0364(6) Uani d 1 . .
H H32 0.147494 0.904772 0.300942 0.044 Uiso calc 1 . .
C C33 -0.0878(4) 0.8739(3) 0.21588(17) 0.0379(6) Uani d 1 . .
H H33 -0.142146 0.793681 0.224987 0.045 Uiso calc 1 . .
O O1 0.5848(2) 0.33700(16) 0.41848(12) 0.0377(4) Uani d 1 . .
N N3 0.6722(3) 0.15580(18) 0.39189(13) 0.0327(5) Uani d 1 . .
C C34 0.6909(3) 0.2730(2) 0.40136(16) 0.0350(6) Uani d 1 . .
H H34 0.797002 0.312878 0.394321 0.042 Uiso calc 1 . .
C C35 0.8031(3) 0.0875(2) 0.37001(17) 0.0354(6) Uani d 1 . .
H H35A 0.831326 0.032017 0.408975 0.053 Uiso calc 1 . .
H H35B 0.905549 0.142311 0.367938 0.053 Uiso calc 1 . .
H H35C 0.760721 0.042240 0.318342 0.053 Uiso calc 1 . .
C C36 0.5091(5) 0.0882(3) 0.3964(3) 0.0859(16) Uani d 1 . .
H H36A 0.528889 0.023536 0.429413 0.129 Uiso calc 1 . .
H H36B 0.450962 0.054033 0.343533 0.129 Uiso calc 1 . .
H H36C 0.437852 0.141506 0.419112 0.129 Uiso calc 1 . .
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'
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Fe1 C2 . . 40.28(14) ?
C1 Fe1 C3 . . 67.51(12) ?
C2 Fe1 C3 . . 40.15(12) ?
C1 Fe1 C5 . . 40.74(14) ?
C2 Fe1 C5 . . 68.17(13) ?
C3 Fe1 C5 . . 67.77(11) ?
C1 Fe1 C4 . . 68.04(12) ?
C2 Fe1 C4 . . 67.86(11) ?
C3 Fe1 C4 . . 40.13(11) ?
C5 Fe1 C4 . . 40.54(12) ?
C1 Fe1 C9 . . 133.24(13) ?
C2 Fe1 C9 . . 172.21(12) ?
C3 Fe1 C9 . . 146.77(11) ?
C5 Fe1 C9 . . 109.48(11) ?
C4 Fe1 C9 . . 115.59(11) ?
C1 Fe1 C8 . . 109.76(11) ?
C2 Fe1 C8 . . 132.96(12) ?
C3 Fe1 C8 . . 171.90(11) ?
C5 Fe1 C8 . . 115.58(11) ?
C4 Fe1 C8 . . 146.98(11) ?
C9 Fe1 C8 . . 40.54(10) ?
C1 Fe1 C10 . . 172.56(13) ?
C2 Fe1 C10 . . 146.10(12) ?
C3 Fe1 C10 . . 115.30(10) ?
C5 Fe1 C10 . . 132.83(12) ?
C4 Fe1 C10 . . 109.28(10) ?
C9 Fe1 C10 . . 40.83(9) ?
C8 Fe1 C10 . . 68.41(10) ?
C1 Fe1 C7 . . 115.15(11) ?
C2 Fe1 C7 . . 109.26(11) ?
C3 Fe1 C7 . . 132.87(10) ?
C5 Fe1 C7 . . 146.57(11) ?
C4 Fe1 C7 . . 171.80(10) ?
C9 Fe1 C7 . . 68.31(10) ?
C8 Fe1 C7 . . 40.45(9) ?
C10 Fe1 C7 . . 68.51(9) ?
C1 Fe1 C6 . . 146.01(12) ?
C2 Fe1 C6 . . 114.71(11) ?
C3 Fe1 C6 . . 109.19(10) ?
C5 Fe1 C6 . . 171.99(12) ?
C4 Fe1 C6 . . 132.48(10) ?
C9 Fe1 C6 . . 68.68(9) ?
C8 Fe1 C6 . . 68.48(9) ?
C10 Fe1 C6 . . 40.84(9) ?
C7 Fe1 C6 . . 40.83(9) ?
C25 Fe2 C32 . . 123.61(10) ?
C25 Fe2 C33 . . 106.62(11) ?
C32 Fe2 C33 . . 40.56(12) ?
C25 Fe2 C28 . . 68.76(9) ?
C32 Fe2 C28 . . 119.74(11) ?
C33 Fe2 C28 . . 154.51(11) ?
C25 Fe2 C31 . . 160.99(10) ?
C32 Fe2 C31 . . 40.72(11) ?
C33 Fe2 C31 . . 68.25(11) ?
C28 Fe2 C31 . . 107.53(10) ?
C25 Fe2 C29 . . 120.65(10) ?
C32 Fe2 C29 . . 68.48(11) ?
C33 Fe2 C29 . . 40.78(11) ?
C28 Fe2 C29 . . 163.14(10) ?
C31 Fe2 C29 . . 68.25(11) ?
C25 Fe2 C26 . . 40.80(9) ?
C32 Fe2 C26 . . 161.42(11) ?
C33 Fe2 C26 . . 125.31(11) ?
C28 Fe2 C26 . . 68.49(9) ?
C31 Fe2 C26 . . 156.89(10) ?
C29 Fe2 C26 . . 108.59(10) ?
C25 Fe2 C30 . . 156.43(10) ?
C32 Fe2 C30 . . 68.44(10) ?
C33 Fe2 C30 . . 68.33(11) ?
C28 Fe2 C30 . . 125.81(10) ?
C31 Fe2 C30 . . 40.55(10) ?
C29 Fe2 C30 . . 40.53(11) ?
C26 Fe2 C30 . . 122.09(10) ?
C25 Fe2 C27 . . 68.68(10) ?
C32 Fe2 C27 . . 155.59(11) ?
C33 Fe2 C27 . . 163.08(11) ?
C28 Fe2 C27 . . 40.62(9) ?
C31 Fe2 C27 . . 121.45(11) ?
C29 Fe2 C27 . . 126.45(10) ?
C26 Fe2 C27 . . 40.72(9) ?
C30 Fe2 C27 . . 109.09(10) ?
C25 Fe2 C24 . . 41.13(9) ?
C32 Fe2 C24 . . 105.37(10) ?
C33 Fe2 C24 . . 118.80(10) ?
C28 Fe2 C24 . . 41.16(8) ?
C31 Fe2 C24 . . 123.86(10) ?
C29 Fe2 C24 . . 154.87(10) ?
C26 Fe2 C24 . . 69.09(9) ?
C30 Fe2 C24 . . 161.86(10) ?
C27 Fe2 C24 . . 69.09(9) ?
C17 N1 C14 . . 128.02(18) ?
C17 N1 H1 . . 117(3) ?
C14 N1 H1 . . 114(3) ?
C17 N2 C18 . . 132.46(19) ?
C17 N2 H1B . . 114(3) ?
C18 N2 H1B . . 113(3) ?
C2 C1 C5 . . 108.2(3) ?
C2 C1 Fe1 . . 69.94(15) ?
C5 C1 Fe1 . . 69.83(16) ?
C2 C1 H1A . . 125.9 ?
C5 C1 H1A . . 125.9 ?
Fe1 C1 H1A . . 125.9 ?
C3 C2 C1 . . 107.8(3) ?
C3 C2 Fe1 . . 70.00(15) ?
C1 C2 Fe1 . . 69.79(17) ?
C3 C2 H2 . . 126.1 ?
C1 C2 H2 . . 126.1 ?
Fe1 C2 H2 . . 126.1 ?
C2 C3 C4 . . 108.8(3) ?
C2 C3 Fe1 . . 69.85(16) ?
C4 C3 Fe1 . . 70.02(15) ?
C2 C3 H3 . . 125.6 ?
C4 C3 H3 . . 125.6 ?
Fe1 C3 H3 . . 125.6 ?
C3 C4 C5 . . 107.8(3) ?
C3 C4 Fe1 . . 69.85(14) ?
C5 C4 Fe1 . . 69.69(15) ?
C3 C4 H4 . . 126.1 ?
C5 C4 H4 . . 126.1 ?
Fe1 C4 H4 . . 126.1 ?
C4 C5 C1 . . 107.3(3) ?
C4 C5 Fe1 . . 69.77(14) ?
C1 C5 Fe1 . . 69.44(15) ?
C4 C5 H5 . . 126.4 ?
C1 C5 H5 . . 126.4 ?
Fe1 C5 H5 . . 126.4 ?
C10 C6 C7 . . 107.30(19) ?
C10 C6 C11 . . 126.6(2) ?
C7 C6 C11 . . 126.0(2) ?
C10 C6 Fe1 . . 69.26(12) ?
C7 C6 Fe1 . . 69.39(12) ?
C11 C6 Fe1 . . 129.10(15) ?
C8 C7 C6 . . 108.2(2) ?
C8 C7 Fe1 . . 69.64(13) ?
C6 C7 Fe1 . . 69.79(12) ?
C8 C7 H7 . . 125.9 ?
C6 C7 H7 . . 125.9 ?
Fe1 C7 H7 . . 125.9 ?
C7 C8 C9 . . 108.5(2) ?
C7 C8 Fe1 . . 69.91(13) ?
C9 C8 Fe1 . . 69.71(14) ?
C7 C8 H8 . . 125.8 ?
C9 C8 H8 . . 125.8 ?
Fe1 C8 H8 . . 125.8 ?
C8 C9 C10 . . 107.9(2) ?
C8 C9 Fe1 . . 69.75(14) ?
C10 C9 Fe1 . . 69.61(13) ?
C8 C9 H9 . . 126.0 ?
C10 C9 H9 . . 126.0 ?
Fe1 C9 H9 . . 126.0 ?
C9 C10 C6 . . 108.1(2) ?
C9 C10 Fe1 . . 69.56(13) ?
C6 C10 Fe1 . . 69.91(12) ?
C9 C10 H10 . . 126.0 ?
C6 C10 H10 . . 126.0 ?
Fe1 C10 H10 . . 126.0 ?
C12 C11 C16 . . 117.50(19) ?
C12 C11 C6 . . 120.7(2) ?
C16 C11 C6 . . 121.8(2) ?
C13 C12 C11 . . 121.3(2) ?
C13 C12 H12 . . 119.4 ?
C11 C12 H12 . . 119.4 ?
C12 C13 C14 . . 120.5(2) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 119.1(2) ?
C15 C14 N1 . . 123.6(2) ?
C13 C14 N1 . . 117.03(19) ?
C16 C15 C14 . . 119.9(2) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C15 C16 C11 . . 121.8(2) ?
C15 C16 H16 . . 119.1 ?
C11 C16 H16 . . 119.1 ?
N1 C17 N2 . . 109.99(19) ?
N1 C17 Cl1 . . 123.90(17) ?
N2 C17 Cl1 . . 126.07(17) ?
C19 C18 C23 . . 118.5(2) ?
C19 C18 N2 . . 115.36(19) ?
C23 C18 N2 . . 126.1(2) ?
C20 C19 C18 . . 121.3(2) ?
C20 C19 H19 . . 119.4 ?
C18 C19 H19 . . 119.4 ?
C19 C20 C21 . . 121.1(2) ?
C19 C20 H20 . . 119.5 ?
C21 C20 H20 . . 119.5 ?
C22 C21 C20 . . 117.1(2) ?
C22 C21 C24 . . 121.61(19) ?
C20 C21 C24 . . 121.25(19) ?
C23 C22 C21 . . 122.4(2) ?
C23 C22 H22 . . 118.8 ?
C21 C22 H22 . . 118.8 ?
C22 C23 C18 . . 119.6(2) ?
C22 C23 H23 . . 120.2 ?
C18 C23 H23 . . 120.2 ?
C25 C24 C28 . . 106.56(19) ?
C25 C24 C21 . . 126.56(19) ?
C28 C24 C21 . . 126.74(19) ?
C25 C24 Fe2 . . 68.99(12) ?
C28 C24 Fe2 . . 69.14(12) ?
C21 C24 Fe2 . . 123.44(15) ?
C26 C25 C24 . . 108.57(19) ?
C26 C25 Fe2 . . 69.84(13) ?
C24 C25 Fe2 . . 69.87(12) ?
C26 C25 H25 . . 125.7 ?
C24 C25 H25 . . 125.7 ?
Fe2 C25 H25 . . 125.7 ?
C25 C26 C27 . . 108.1(2) ?
C25 C26 Fe2 . . 69.37(13) ?
C27 C26 Fe2 . . 69.78(13) ?
C25 C26 H26 . . 125.9 ?
C27 C26 H26 . . 125.9 ?
Fe2 C26 H26 . . 125.9 ?
C28 C27 C26 . . 107.9(2) ?
C28 C27 Fe2 . . 69.47(13) ?
C26 C27 Fe2 . . 69.50(13) ?
C28 C27 H27 . . 126.0 ?
C26 C27 H27 . . 126.0 ?
Fe2 C27 H27 . . 126.0 ?
C27 C28 C24 . . 108.8(2) ?
C27 C28 Fe2 . . 69.91(13) ?
C24 C28 Fe2 . . 69.71(12) ?
C27 C28 H28 . . 125.6 ?
C24 C28 H28 . . 125.6 ?
Fe2 C28 H28 . . 125.6 ?
C30 C29 C33 . . 107.9(2) ?
C30 C29 Fe2 . . 69.92(14) ?
C33 C29 Fe2 . . 69.55(14) ?
C30 C29 H29 . . 126.0 ?
C33 C29 H29 . . 126.0 ?
Fe2 C29 H29 . . 126.0 ?
C29 C30 C31 . . 107.9(2) ?
C29 C30 Fe2 . . 69.55(14) ?
C31 C30 Fe2 . . 69.53(14) ?
C29 C30 H30 . . 126.0 ?
C31 C30 H30 . . 126.0 ?
Fe2 C30 H30 . . 126.0 ?
C30 C31 C32 . . 108.2(2) ?
C30 C31 Fe2 . . 69.92(14) ?
C32 C31 Fe2 . . 69.56(14) ?
C30 C31 H31 . . 125.9 ?
C32 C31 H31 . . 125.9 ?
Fe2 C31 H31 . . 125.9 ?
C33 C32 C31 . . 107.8(2) ?
C33 C32 Fe2 . . 69.75(15) ?
C31 C32 Fe2 . . 69.72(14) ?
C33 C32 H32 . . 126.1 ?
C31 C32 H32 . . 126.1 ?
Fe2 C32 H32 . . 126.1 ?
C32 C33 C29 . . 108.1(2) ?
C32 C33 Fe2 . . 69.70(15) ?
C29 C33 Fe2 . . 69.67(14) ?
C32 C33 H33 . . 125.9 ?
C29 C33 H33 . . 125.9 ?
Fe2 C33 H33 . . 125.9 ?
C34 N3 C35 . . 123.0(2) ?
C34 N3 C36 . . 120.0(2) ?
C35 N3 C36 . . 116.8(2) ?
O1 C34 N3 . . 126.7(2) ?
O1 C34 H34 . . 116.6 ?
N3 C34 H34 . . 116.6 ?
N3 C35 H35A . . 109.5 ?
N3 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
N3 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
N3 C36 H36A . . 109.5 ?
N3 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
N3 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Fe1 C1 . 2.042(3) ?
Fe1 C2 . 2.044(3) ?
Fe1 C3 . 2.046(2) ?
Fe1 C5 . 2.047(3) ?
Fe1 C4 . 2.048(2) ?
Fe1 C9 . 2.048(2) ?
Fe1 C8 . 2.049(2) ?
Fe1 C10 . 2.049(2) ?
Fe1 C7 . 2.053(2) ?
Fe1 C6 . 2.058(2) ?
Fe2 C25 . 2.038(2) ?
Fe2 C32 . 2.040(3) ?
Fe2 C33 . 2.041(3) ?
Fe2 C28 . 2.042(2) ?
Fe2 C31 . 2.042(2) ?
Fe2 C29 . 2.043(2) ?
Fe2 C26 . 2.044(2) ?
Fe2 C30 . 2.047(2) ?
Fe2 C27 . 2.048(2) ?
Fe2 C24 . 2.050(2) ?
Cl1 C17 . 1.672(2) ?
N1 C17 . 1.365(3) ?
N1 C14 . 1.414(3) ?
N1 H1 . 0.908(10) ?
N2 C17 . 1.366(3) ?
N2 C18 . 1.410(3) ?
N2 H1B . 0.909(10) ?
C1 C2 . 1.407(5) ?
C1 C5 . 1.423(5) ?
C1 H1A . 1.0000 ?
C2 C3 . 1.404(4) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.405(4) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.419(4) ?
C4 H4 . 1.0000 ?
C5 H5 . 1.0000 ?
C6 C10 . 1.433(3) ?
C6 C7 . 1.434(3) ?
C6 C11 . 1.475(3) ?
C7 C8 . 1.418(3) ?
C7 H7 . 1.0000 ?
C8 C9 . 1.420(4) ?
C8 H8 . 1.0000 ?
C9 C10 . 1.429(3) ?
C9 H9 . 1.0000 ?
C10 H10 . 1.0000 ?
C11 C12 . 1.398(3) ?
C11 C16 . 1.401(3) ?
C12 C13 . 1.386(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.398(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.394(3) ?
C15 C16 . 1.388(3) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C18 C19 . 1.392(3) ?
C18 C23 . 1.396(3) ?
C19 C20 . 1.380(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.399(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.391(3) ?
C21 C24 . 1.470(3) ?
C22 C23 . 1.389(3) ?
C22 H22 . 0.9500 ?
C23 H23 . 0.9500 ?
C24 C25 . 1.436(3) ?
C24 C28 . 1.438(3) ?
C25 C26 . 1.423(3) ?
C25 H25 . 1.0000 ?
C26 C27 . 1.424(3) ?
C26 H26 . 1.0000 ?
C27 C28 . 1.419(3) ?
C27 H27 . 1.0000 ?
C28 H28 . 1.0000 ?
C29 C30 . 1.417(4) ?
C29 C33 . 1.423(4) ?
C29 H29 . 1.0000 ?
C30 C31 . 1.417(4) ?
C30 H30 . 1.0000 ?
C31 C32 . 1.420(4) ?
C31 H31 . 1.0000 ?
C32 C33 . 1.414(4) ?
C32 H32 . 1.0000 ?
C33 H33 . 1.0000 ?
O1 C34 . 1.234(3) ?
N3 C34 . 1.310(3) ?
N3 C35 . 1.452(3) ?
N3 C36 . 1.457(4) ?
C34 H34 . 0.9500 ?
C35 H35A . 0.9800 ?
C35 H35B . 0.9800 ?
C35 H35C . 0.9800 ?
C36 H36A . 0.9800 ?
C36 H36B . 0.9800 ?
C36 H36C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 . 0.908(10) 1.981(18) 2.862(3) 163(5) yes
C7 H7 Cg6 2_766 1.00 2.63 3.569(3) 157 y
C19 H19 Cg5 2_666 0.95 2.63 3.286(3) 126 y
C23 H23 Cl1 . 0.95 2.55 3.219(2) 127 yes
C25 H25 Cg2 2_666 1.00 2.94 3.913(3) 163 y
C34 H34 Cg5 2_766 0.95 2.71 3.632(3) 164 y
C35 H35C Cg4 1_645 0.98 2.97 3.624(3) 125 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 C1 C2 C3 . . . . 0.4(3) ?
Fe1 C1 C2 C3 . . . . 59.91(18) ?
C5 C1 C2 Fe1 . . . . -59.55(19) ?
C1 C2 C3 C4 . . . . -0.4(3) ?
Fe1 C2 C3 C4 . . . . 59.35(18) ?
C1 C2 C3 Fe1 . . . . -59.77(18) ?
C2 C3 C4 C5 . . . . 0.3(3) ?
Fe1 C3 C4 C5 . . . . 59.57(17) ?
C2 C3 C4 Fe1 . . . . -59.25(18) ?
C3 C4 C5 C1 . . . . -0.1(3) ?
Fe1 C4 C5 C1 . . . . 59.57(18) ?
C3 C4 C5 Fe1 . . . . -59.67(17) ?
C2 C1 C5 C4 . . . . -0.2(3) ?
Fe1 C1 C5 C4 . . . . -59.78(18) ?
C2 C1 C5 Fe1 . . . . 59.62(18) ?
C10 C6 C7 C8 . . . . 0.1(2) ?
C11 C6 C7 C8 . . . . -176.8(2) ?
Fe1 C6 C7 C8 . . . . 59.21(15) ?
C10 C6 C7 Fe1 . . . . -59.10(14) ?
C11 C6 C7 Fe1 . . . . 124.0(2) ?
C6 C7 C8 C9 . . . . -0.1(3) ?
Fe1 C7 C8 C9 . . . . 59.25(16) ?
C6 C7 C8 Fe1 . . . . -59.31(15) ?
C7 C8 C9 C10 . . . . 0.0(3) ?
Fe1 C8 C9 C10 . . . . 59.35(16) ?
C7 C8 C9 Fe1 . . . . -59.37(16) ?
C8 C9 C10 C6 . . . . 0.1(3) ?
Fe1 C9 C10 C6 . . . . 59.53(15) ?
C8 C9 C10 Fe1 . . . . -59.44(16) ?
C7 C6 C10 C9 . . . . -0.1(2) ?
C11 C6 C10 C9 . . . . 176.7(2) ?
Fe1 C6 C10 C9 . . . . -59.31(15) ?
C7 C6 C10 Fe1 . . . . 59.19(14) ?
C11 C6 C10 Fe1 . . . . -124.0(2) ?
C10 C6 C11 C12 . . . . -153.8(2) ?
C7 C6 C11 C12 . . . . 22.5(3) ?
Fe1 C6 C11 C12 . . . . 114.2(2) ?
C10 C6 C11 C16 . . . . 22.6(3) ?
C7 C6 C11 C16 . . . . -161.1(2) ?
Fe1 C6 C11 C16 . . . . -69.4(3) ?
C16 C11 C12 C13 . . . . -0.8(3) ?
C6 C11 C12 C13 . . . . 175.8(2) ?
C11 C12 C13 C14 . . . . -0.2(3) ?
C12 C13 C14 C15 . . . . 0.8(3) ?
C12 C13 C14 N1 . . . . -173.2(2) ?
C17 N1 C14 C15 . . . . 46.0(3) ?
C17 N1 C14 C13 . . . . -140.3(2) ?
C13 C14 C15 C16 . . . . -0.4(3) ?
N1 C14 C15 C16 . . . . 173.2(2) ?
C14 C15 C16 C11 . . . . -0.6(3) ?
C12 C11 C16 C15 . . . . 1.2(3) ?
C6 C11 C16 C15 . . . . -175.3(2) ?
C14 N1 C17 N2 . . . . -177.9(2) ?
C14 N1 C17 Cl1 . . . . 4.2(3) ?
C18 N2 C17 N1 . . . . -177.0(2) ?
C18 N2 C17 Cl1 . . . . 0.8(4) ?
C17 N2 C18 C19 . . . . -173.0(2) ?
C17 N2 C18 C23 . . . . 9.1(4) ?
C23 C18 C19 C20 . . . . -1.9(3) ?
N2 C18 C19 C20 . . . . -179.9(2) ?
C18 C19 C20 C21 . . . . 0.1(4) ?
C19 C20 C21 C22 . . . . 1.7(3) ?
C19 C20 C21 C24 . . . . -176.2(2) ?
C20 C21 C22 C23 . . . . -1.8(3) ?
C24 C21 C22 C23 . . . . 176.1(2) ?
C21 C22 C23 C18 . . . . 0.0(4) ?
C19 C18 C23 C22 . . . . 1.8(3) ?
N2 C18 C23 C22 . . . . 179.6(2) ?
C22 C21 C24 C25 . . . . -170.1(2) ?
C20 C21 C24 C25 . . . . 7.7(3) ?
C22 C21 C24 C28 . . . . 5.0(3) ?
C20 C21 C24 C28 . . . . -177.1(2) ?
C22 C21 C24 Fe2 . . . . -82.7(2) ?
C20 C21 C24 Fe2 . . . . 95.1(2) ?
C28 C24 C25 C26 . . . . 0.1(3) ?
C21 C24 C25 C26 . . . . 176.1(2) ?
Fe2 C24 C25 C26 . . . . 59.31(16) ?
C28 C24 C25 Fe2 . . . . -59.19(15) ?
C21 C24 C25 Fe2 . . . . 116.8(2) ?
C24 C25 C26 C27 . . . . -0.1(3) ?
Fe2 C25 C26 C27 . . . . 59.21(17) ?
C24 C25 C26 Fe2 . . . . -59.33(16) ?
C25 C26 C27 C28 . . . . 0.1(3) ?
Fe2 C26 C27 C28 . . . . 59.03(16) ?
C25 C26 C27 Fe2 . . . . -58.95(16) ?
C26 C27 C28 C24 . . . . 0.0(3) ?
Fe2 C27 C28 C24 . . . . 59.04(16) ?
C26 C27 C28 Fe2 . . . . -59.04(17) ?
C25 C24 C28 C27 . . . . -0.1(3) ?
C21 C24 C28 C27 . . . . -176.0(2) ?
Fe2 C24 C28 C27 . . . . -59.17(16) ?
C25 C24 C28 Fe2 . . . . 59.10(15) ?
C21 C24 C28 Fe2 . . . . -116.8(2) ?
C33 C29 C30 C31 . . . . 0.2(3) ?
Fe2 C29 C30 C31 . . . . -59.14(18) ?
C33 C29 C30 Fe2 . . . . 59.39(17) ?
C29 C30 C31 C32 . . . . -0.1(3) ?
Fe2 C30 C31 C32 . . . . -59.22(17) ?
C29 C30 C31 Fe2 . . . . 59.16(17) ?
C30 C31 C32 C33 . . . . -0.1(3) ?
Fe2 C31 C32 C33 . . . . -59.58(18) ?
C30 C31 C32 Fe2 . . . . 59.45(17) ?
C31 C32 C33 C29 . . . . 0.3(3) ?
Fe2 C32 C33 C29 . . . . -59.28(18) ?
C31 C32 C33 Fe2 . . . . 59.56(18) ?
C30 C29 C33 C32 . . . . -0.3(3) ?
Fe2 C29 C33 C32 . . . . 59.29(18) ?
C30 C29 C33 Fe2 . . . . -59.62(18) ?
C35 N3 C34 O1 . . . . 178.6(3) ?
C36 N3 C34 O1 . . . . 4.2(5) ?
