#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/20/4302016.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_4302016
loop_
_publ_author_name
'Edward C. Weintrob'
'Daniel Tofan'
'John E. Bercaw'
_publ_contact_author
;       Michael W. Day
        Beckman Institute
        California Institute of Technology
        Pasadena, CA  91125
        USA
;
_publ_contact_author_email       mikeday@caltech.edu
_publ_contact_author_fax         '(818) 449 4159'
_publ_contact_author_phone       '(818) 395 2734'
_publ_section_title
;
Synthesis and Characterization of Iron Derivatives Having a Pyridine-Linked
Bis(anilide) Pincer Ligand
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3808
_journal_page_last               3813
_journal_paper_doi               10.1021/ic900083s
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C39 H41 Fe N3 O'
_chemical_formula_sum            'C39 H41 Fe N3 O'
_chemical_formula_weight         623.60
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.247(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5396(6)
_cell_length_b                   13.5644(6)
_cell_length_c                   16.6014(7)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.69
_cell_measurement_theta_min      2.48
_cell_volume                     3240.3(2)
_computing_cell_refinement       'Bruker SAINT-Plus v7.34A'
_computing_data_collection       'Bruker APEX2 v2.1-0'
_computing_data_reduction        'Bruker SAINT-Plus v7.34A'
_computing_molecular_graphics    'Bruker XP v5.1'
_computing_publication_material  'Bruker XCIF v6.12'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker KAPPA APEX II'
_diffrn_measurement_method       'ω scans; 17 settings'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            97719
_diffrn_reflns_theta_full        36.53
_diffrn_reflns_theta_max         36.53
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Dark red'
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         2.279
_refine_diff_density_min         -1.067
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.823
_refine_ls_hydrogen_treatment    Riding
_refine_ls_matrix_type           'Full matrix'
_refine_ls_number_parameters     403
_refine_ls_number_reflns         14879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.823
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/s²(Fo²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                10317
_reflns_number_total             14879
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic900083s_si_002_2.cif
_cod_data_source_block           '[2]Fe(THF)'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_weighting_scheme' value 'Sigma' changed to
'sigma' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct methods' was changed to
'direct'.

'_atom_sites_solution_secondary' value 'Difference Fourier map' was
changed to 'difmap'.

'_atom_sites_solution_hydrogens' value 'Geometric positions' was
changed to 'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4302016
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.228104(12) 0.216813(14) 0.851732(11) 0.01948(5) Uani 1 1 d . . .
O1 O 0.20858(6) 0.29103(6) 0.73869(5) 0.0237(2) Uani 1 1 d . . .
N1 N 0.17732(7) 0.08604(8) 0.83163(6) 0.0205(2) Uani 1 1 d . . .
N2 N 0.11603(6) 0.27502(8) 0.89542(6) 0.0174(2) Uani 1 1 d . . .
N3 N 0.31875(6) 0.28471(8) 0.92820(6) 0.0187(2) Uani 1 1 d . . .
C1 C 0.08979(8) 0.08894(9) 0.78458(7) 0.0208(3) Uani 1 1 d . . .
C2 C 0.06405(9) 0.02037(10) 0.72217(8) 0.0249(3) Uani 1 1 d . . .
H2 H 0.1054 -0.0319 0.7145 0.030 Uiso 1 1 calc R . .
C3 C -0.01976(10) 0.02698(11) 0.67164(8) 0.0300(3) Uani 1 1 d . . .
H3 H -0.0356 -0.0213 0.6305 0.036 Uiso 1 1 calc R . .
C4 C -0.08086(9) 0.10267(11) 0.68004(8) 0.0303(3) Uani 1 1 d . . .
H4 H -0.1373 0.1085 0.6436 0.036 Uiso 1 1 calc R . .
C5 C -0.05903(9) 0.16958(10) 0.74183(8) 0.0267(3) Uani 1 1 d . . .
H5 H -0.1014 0.2215 0.7479 0.032 Uiso 1 1 calc R . .
C6 C 0.02442(8) 0.16353(10) 0.79663(8) 0.0206(3) Uani 1 1 d . . .
C7 C 0.03292(8) 0.23013(9) 0.86822(7) 0.0199(3) Uani 1 1 d . . .
C8 C -0.04438(8) 0.24700(10) 0.90646(8) 0.0238(3) Uani 1 1 d . . .
H8 H -0.1022 0.2171 0.8864 0.029 Uiso 1 1 calc R . .
C9 C -0.03649(9) 0.30754(10) 0.97379(8) 0.0260(3) Uani 1 1 d . . .
H9 H -0.0885 0.3178 1.0015 0.031 Uiso 1 1 calc R . .
C10 C 0.04665(8) 0.35300(10) 1.00076(8) 0.0232(3) Uani 1 1 d . . .
H10 H 0.0522 0.3942 1.0475 0.028 Uiso 1 1 calc R . .
C11 C 0.12341(8) 0.33885(9) 0.95962(7) 0.0183(3) Uani 1 1 d . . .
C12 C 0.21006(8) 0.39464(9) 0.98523(7) 0.0186(3) Uani 1 1 d . . .
C13 C 0.20092(9) 0.48378(10) 1.02627(8) 0.0239(3) Uani 1 1 d . . .
H13 H 0.1401 0.5059 1.0315 0.029 Uiso 1 1 calc R . .
C14 C 0.27479(9) 0.54097(10) 1.05934(8) 0.0294(3) Uani 1 1 d . . .
H14 H 0.2651 0.6014 1.0859 0.035 Uiso 1 1 calc R . .
C15 C 0.36368(9) 0.50826(10) 1.05295(8) 0.0292(3) Uani 1 1 d . . .
H15 H 0.4159 0.5453 1.0771 0.035 Uiso 1 1 calc R . .
C16 C 0.37686(9) 0.42308(10) 1.01209(8) 0.0239(3) Uani 1 1 d . . .
H16 H 0.4386 0.4018 1.0096 0.029 Uiso 1 1 calc R . .
C17 C 0.30233(8) 0.36524(9) 0.97340(7) 0.0191(3) Uani 1 1 d . . .
C18 C 0.22257(9) -0.00666(10) 0.84224(8) 0.0228(3) Uani 1 1 d . . .
C19 C 0.18442(9) -0.08290(10) 0.88402(8) 0.0275(3) Uani 1 1 d . . .
C20 C 0.22994(10) -0.17339(11) 0.89327(9) 0.0343(3) Uani 1 1 d . . .
H20 H 0.2027 -0.2253 0.9202 0.041 Uiso 1 1 calc R . .
C21 C 0.31328(10) -0.19049(11) 0.86476(9) 0.0356(4) Uani 1 1 d . . .
C22 C 0.35207(10) -0.11276(11) 0.82739(9) 0.0307(3) Uani 1 1 d . . .
H22 H 0.4107 -0.1222 0.8096 0.037 Uiso 1 1 calc R . .
C23 C 0.30893(9) -0.02145(10) 0.81478(8) 0.0248(3) Uani 1 1 d . . .
C24 C 0.09554(10) -0.06657(11) 0.91914(9) 0.0369(4) Uani 1 1 d . . .
H24A H 0.0426 -0.0693 0.8754 0.055 Uiso 1 1 calc R . .
H24B H 0.0974 -0.0018 0.9455 0.055 Uiso 1 1 calc R . .
H24C H 0.0888 -0.1180 0.9593 0.055 Uiso 1 1 calc R . .
C25 C 0.36155(12) -0.28998(11) 0.87529(11) 0.0491(4) Uani 1 1 d . . .
H25A H 0.3644 -0.3118 0.9319 0.074 Uiso 1 1 calc R . .
H25B H 0.4247 -0.2840 0.8617 0.074 Uiso 1 1 calc R . .
H25C H 0.3267 -0.3383 0.8391 0.074 Uiso 1 1 calc R . .
C26 C 0.35305(9) 0.05879(10) 0.77076(9) 0.0303(3) Uani 1 1 d . . .
H26A H 0.4083 0.0328 0.7505 0.046 Uiso 1 1 calc R . .
H26B H 0.3711 0.1135 0.8082 0.046 Uiso 1 1 calc R . .
H26C H 0.3085 0.0823 0.7249 0.046 Uiso 1 1 calc R . .
C27 C 0.41289(8) 0.25688(10) 0.92213(8) 0.0220(3) Uani 1 1 d . . .
C28 C 0.46073(8) 0.30146(10) 0.86422(8) 0.0253(3) Uani 1 1 d . . .
C29 C 0.54842(9) 0.26470(11) 0.85489(9) 0.0313(3) Uani 1 1 d . . .
H29 H 0.5816 0.2947 0.8161 0.038 Uiso 1 1 calc R . .
C30 C 0.58838(9) 0.18638(11) 0.90012(10) 0.0353(4) Uani 1 1 d . . .
C31 C 0.54057(10) 0.14492(11) 0.95742(10) 0.0348(4) Uani 1 1 d . . .
H31 H 0.5682 0.0920 0.9898 0.042 Uiso 1 1 calc R . .
C32 C 0.45300(9) 0.17824(10) 0.96938(9) 0.0278(3) Uani 1 1 d . . .
C33 C 0.41944(9) 0.38703(11) 0.81299(9) 0.0316(3) Uani 1 1 d . . .
H33A H 0.4667 0.4154 0.7833 0.047 Uiso 1 1 calc R . .
H33B H 0.3980 0.4374 0.8483 0.047 Uiso 1 1 calc R . .
H33C H 0.3668 0.3638 0.7741 0.047 Uiso 1 1 calc R . .
C34 C 0.68388(11) 0.14969(13) 0.88720(12) 0.0571(5) Uani 1 1 d . . .
H34A H 0.7257 0.2060 0.8852 0.086 Uiso 1 1 calc R . .
H34B H 0.6789 0.1132 0.8358 0.086 Uiso 1 1 calc R . .
H34C H 0.7087 0.1062 0.9323 0.086 Uiso 1 1 calc R . .
C35 C 0.40251(10) 0.13124(11) 1.03225(10) 0.0380(4) Uani 1 1 d . . .
H35A H 0.3483 0.0952 1.0051 0.057 Uiso 1 1 calc R . .
H35B H 0.3820 0.1824 1.0674 0.057 Uiso 1 1 calc R . .
H35C H 0.4442 0.0854 1.0653 0.057 Uiso 1 1 calc R . .
C36 C 0.20895(10) 0.25483(11) 0.65696(8) 0.0316(3) Uani 1 1 d . . .
H36A H 0.1728 0.1929 0.6482 0.038 Uiso 1 1 calc R . .
H36B H 0.2733 0.2421 0.6467 0.038 Uiso 1 1 calc R . .
C37 C 0.16399(10) 0.33646(11) 0.60093(8) 0.0329(3) Uani 1 1 d . . .
H37A H 0.1950 0.3432 0.5519 0.039 Uiso 1 1 calc R . .
H37B H 0.0970 0.3235 0.5840 0.039 Uiso 1 1 calc R . .
C38 C 0.17865(10) 0.42741(11) 0.65397(9) 0.0341(3) Uani 1 1 d . . .
H38A H 0.2419 0.4547 0.6547 0.041 Uiso 1 1 calc R . .
H38B H 0.1323 0.4791 0.6356 0.041 Uiso 1 1 calc R . .
C39 C 0.16526(10) 0.38711(10) 0.73584(9) 0.0305(3) Uani 1 1 d . . .
H39A H 0.1957 0.4298 0.7802 0.037 Uiso 1 1 calc R . .
H39B H 0.0984 0.3815 0.7407 0.037 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 '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'
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
N3 Fe1 N1 139.52(4) . . yes
N3 Fe1 N2 94.97(4) . . yes
N1 Fe1 N2 96.44(4) . . yes
N3 Fe1 O1 110.45(4) . . yes
N1 Fe1 O1 106.54(4) . . yes
N2 Fe1 O1 96.85(4) . . yes
C36 O1 C39 109.65(10) . . ?
C36 O1 Fe1 130.90(8) . . ?
C39 O1 Fe1 117.46(7) . . ?
C1 N1 C18 117.65(10) . . ?
C1 N1 Fe1 111.48(8) . . ?
C18 N1 Fe1 129.32(8) . . ?
C11 N2 C7 120.38(10) . . ?
C11 N2 Fe1 123.15(8) . . ?
C7 N2 Fe1 115.05(8) . . ?
C17 N3 C27 119.46(10) . . ?
C17 N3 Fe1 125.95(8) . . ?
C27 N3 Fe1 113.35(8) . . ?
N1 C1 C2 121.35(12) . . ?
N1 C1 C6 121.06(11) . . ?
C2 C1 C6 117.57(11) . . ?
C3 C2 C1 121.66(13) . . ?
C4 C3 C2 120.85(13) . . ?
C5 C4 C3 119.03(13) . . ?
C4 C5 C6 121.93(13) . . ?
C5 C6 C1 118.76(12) . . ?
C5 C6 C7 116.50(12) . . ?
C1 C6 C7 124.43(11) . . ?
N2 C7 C8 120.67(11) . . ?
N2 C7 C6 120.17(10) . . ?
C8 C7 C6 119.16(11) . . ?
C9 C8 C7 119.39(12) . . ?
C10 C9 C8 119.92(12) . . ?
C9 C10 C11 120.29(12) . . ?
N2 C11 C10 119.20(11) . . ?
N2 C11 C12 121.14(10) . . ?
C10 C11 C12 119.64(11) . . ?
C13 C12 C17 117.37(11) . . ?
C13 C12 C11 116.38(11) . . ?
C17 C12 C11 126.24(11) . . ?
C14 C13 C12 123.88(12) . . ?
C13 C14 C15 118.24(12) . . ?
C16 C15 C14 120.50(12) . . ?
C15 C16 C17 122.76(12) . . ?
N3 C17 C16 120.67(11) . . ?
N3 C17 C12 122.43(11) . . ?
C16 C17 C12 116.89(11) . . ?
C19 C18 C23 119.24(12) . . ?
C19 C18 N1 120.38(11) . . ?
C23 C18 N1 120.30(12) . . ?
C20 C19 C18 119.27(13) . . ?
C20 C19 C24 120.45(13) . . ?
C18 C19 C24 120.28(12) . . ?
C21 C20 C19 122.43(14) . . ?
C20 C21 C22 117.34(14) . . ?
C20 C21 C25 121.52(15) . . ?
C22 C21 C25 121.13(14) . . ?
C21 C22 C23 122.83(13) . . ?
C22 C23 C18 118.77(13) . . ?
C22 C23 C26 120.19(12) . . ?
C18 C23 C26 121.02(12) . . ?
C32 C27 C28 120.32(11) . . ?
C32 C27 N3 119.01(11) . . ?
C28 C27 N3 120.39(12) . . ?
C29 C28 C27 118.17(13) . . ?
C29 C28 C33 120.43(13) . . ?
C27 C28 C33 121.40(11) . . ?
C30 C29 C28 122.26(14) . . ?
C31 C30 C29 118.40(13) . . ?
C31 C30 C34 121.75(15) . . ?
C29 C30 C34 119.83(15) . . ?
C30 C31 C32 121.93(14) . . ?
C31 C32 C27 118.90(13) . . ?
C31 C32 C35 120.65(13) . . ?
C27 C32 C35 120.45(12) . . ?
O1 C36 C37 105.45(11) . . ?
C38 C37 C36 102.94(11) . . ?
C39 C38 C37 101.77(11) . . ?
O1 C39 C38 104.19(11) . . ?
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 N3 1.9278(10) . yes
Fe1 N1 1.9319(10) . yes
Fe1 N2 2.0356(10) . yes
Fe1 O1 2.1126(9) . yes
O1 C36 1.4435(15) . ?
O1 C39 1.4453(15) . ?
N1 C1 1.3950(15) . ?
N1 C18 1.4184(16) . ?
N2 C11 1.3654(15) . ?
N2 C7 1.3706(14) . ?
N3 C17 1.3656(15) . ?
N3 C27 1.4373(15) . ?
C1 C2 1.4027(17) . ?
C1 C6 1.4218(17) . ?
C2 C3 1.3797(18) . ?
C3 C4 1.378(2) . ?
C4 C5 1.3723(19) . ?
C5 C6 1.4106(17) . ?
C6 C7 1.4838(17) . ?
C7 C8 1.3868(17) . ?
C8 C9 1.3786(18) . ?
C9 C10 1.3735(18) . ?
C10 C11 1.4028(16) . ?
C11 C12 1.4788(16) . ?
C12 C13 1.4036(17) . ?
C12 C17 1.4398(16) . ?
C13 C14 1.3738(18) . ?
C14 C15 1.3849(18) . ?
C15 C16 1.3671(18) . ?
C16 C17 1.4151(16) . ?
C18 C19 1.4030(18) . ?
C18 C23 1.4103(17) . ?
C19 C20 1.3926(19) . ?
C19 C24 1.5084(19) . ?
C20 C21 1.382(2) . ?
C21 C22 1.384(2) . ?
C21 C25 1.520(2) . ?
C22 C23 1.3905(19) . ?
C23 C26 1.5049(18) . ?
C27 C32 1.4007(18) . ?
C27 C28 1.4020(18) . ?
C28 C29 1.3982(18) . ?
C28 C33 1.5114(19) . ?
C29 C30 1.380(2) . ?
C30 C31 1.376(2) . ?
C30 C34 1.5190(19) . ?
C31 C32 1.3919(18) . ?
C32 C35 1.502(2) . ?
C36 C37 1.5311(19) . ?
C37 C38 1.513(2) . ?
C38 C39 1.5034(19) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139126639
