#------------------------------------------------------------------------------
#$Date: 2022-09-08 01:00:01 +0300 (Thu, 08 Sep 2022) $
#$Revision: 277713 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/06/7130684.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_7130684
loop_
_publ_author_name
'Shen, Chang'
'Dagnaw, Wasihun Menberu'
'Fong, Ching Wai'
'Lau, Kai Chung'
'Chow, Cheuk-Fai'
_publ_section_title
;
 Selective functionalization of C(sp3)--H bonds: catalytic chlorination
 and bromination by IronIII-acacen-halide under ambient condition
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02924C
_journal_year                    2022
_chemical_formula_sum            'C12 H18 Br Fe N2 O2'
_chemical_formula_weight         358.04
_chemical_name_systematic        FeIII(acacen)(Br)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-07-24 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.458(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3529(16)
_cell_length_b                   24.649(5)
_cell_length_c                   8.2656(14)
_cell_measurement_reflns_used    196
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.70
_cell_measurement_theta_min      2.64
_cell_volume                     1468.2(5)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            25004
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.926
_diffrn_reflns_theta_min         3.275
_exptl_absorpt_coefficient_mu    3.744
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2015)'
_exptl_crystal_colour            dark_brown
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0360
_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)+(0.0407P)²+0.9209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2900
_reflns_number_total             3508
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02924c2.cif
_cod_data_source_block           SCFe-2B
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7130684
_shelx_shelxl_version_number     2017/1
_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   0.316
_shelx_estimated_absorpt_t_max   0.400
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_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
Br1 Br 0.23515(5) 0.55830(2) 0.03126(4) 0.05493(12) Uani 1 1 d . . . . .
O1 O 0.3078(3) 0.64370(9) 0.3747(2) 0.0570(6) Uani 1 1 d . . . . .
Fe1 Fe 0.41625(5) 0.62787(2) 0.18722(4) 0.03707(11) Uani 1 1 d . . . . .
N1 N 0.6167(4) 0.58446(10) 0.3443(3) 0.0501(6) Uani 1 1 d . . . . .
C1 C 0.2068(6) 0.64298(18) 0.6279(5) 0.0769(11) Uani 1 1 d . . . . .
H1A H 0.209628 0.681850 0.635431 0.115 Uiso 1 1 calc R U . . .
H1B H 0.241579 0.627664 0.736391 0.115 Uiso 1 1 calc R U . . .
H1C H 0.083699 0.631312 0.578466 0.115 Uiso 1 1 calc R U . . .
N2 N 0.6376(4) 0.63851(10) 0.0750(3) 0.0524(6) Uani 1 1 d . . . . .
O2 O 0.3229(3) 0.69620(8) 0.0934(3) 0.0516(5) Uani 1 1 d . . . . .
C2 C 0.3412(5) 0.62429(13) 0.5229(4) 0.0524(7) Uani 1 1 d . . . . .
C3 C 0.4843(5) 0.59076(14) 0.5845(4) 0.0616(9) Uani 1 1 d . . . . .
H3 H 0.494665 0.579402 0.693207 0.074 Uiso 1 1 calc R U . . .
C4 C 0.6194(5) 0.57147(12) 0.4979(4) 0.0544(8) Uani 1 1 d . . . . .
C5 C 0.7712(6) 0.53520(17) 0.5941(6) 0.0845(13) Uani 1 1 d . . . . .
H5A H 0.760513 0.499486 0.546790 0.127 Uiso 1 1 calc R U . . .
H5B H 0.758207 0.533201 0.707189 0.127 Uiso 1 1 calc R U . . .
H5C H 0.890527 0.550081 0.588694 0.127 Uiso 1 1 calc R U . . .
C6 C 0.7590(7) 0.56510(19) 0.2573(6) 0.0869(14) Uani 1 1 d . . . . .
H6A H 0.755738 0.525763 0.254294 0.104 Uiso 1 1 calc R U . A 1
H6AB H 0.879907 0.575899 0.318997 0.104 Uiso 1 1 calc R U . A 1
C7 C 0.736(2) 0.5867(5) 0.079(2) 0.054(3) Uani 0.42(3) 1 d . . P B 1
H7A H 0.856528 0.591952 0.049559 0.065 Uiso 0.42(3) 1 calc R U P B 1
H7AB H 0.665337 0.561284 0.001059 0.065 Uiso 0.42(3) 1 calc R U P B 1
C7' C 0.7993(17) 0.6009(5) 0.1468(19) 0.068(3) Uani 0.58(3) 1 d . . P B 2
H7'1 H 0.836555 0.581211 0.057224 0.082 Uiso 0.58(3) 1 calc R U P B 2
H7'2 H 0.903870 0.622876 0.199615 0.082 Uiso 0.58(3) 1 calc R U P B 2
C8 C 0.8432(6) 0.6791(2) -0.0935(6) 0.0966(15) Uani 1 1 d . . . . .
H8A H 0.850016 0.646719 -0.156766 0.145 Uiso 1 1 calc R U . . .
H8B H 0.949499 0.680997 -0.005023 0.145 Uiso 1 1 calc R U . . .
H8C H 0.840893 0.710239 -0.163505 0.145 Uiso 1 1 calc R U . . .
C9 C 0.6671(5) 0.67782(14) -0.0226(4) 0.0550(8) Uani 1 1 d . . . . .
C10 C 0.5427(5) 0.72104(14) -0.0639(4) 0.0605(9) Uani 1 1 d . . . . .
H10 H 0.573482 0.747316 -0.134633 0.073 Uiso 1 1 calc R U . . .
C11 C 0.3811(5) 0.72809(11) -0.0100(4) 0.0504(7) Uani 1 1 d . . . . .
C12 C 0.2551(6) 0.77541(14) -0.0686(5) 0.0761(12) Uani 1 1 d . . . . .
H12A H 0.323373 0.802751 -0.114078 0.114 Uiso 1 1 calc R U . . .
H12B H 0.208942 0.790301 0.022672 0.114 Uiso 1 1 calc R U . . .
H12C H 0.152939 0.763311 -0.151875 0.114 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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'
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
C2 O1 Fe1 131.2(2) . . ?
O1 Fe1 O2 88.61(9) . . ?
O1 Fe1 N2 146.80(11) . . ?
O2 Fe1 N2 87.54(10) . . ?
O1 Fe1 N1 87.51(10) . . ?
O2 Fe1 N1 149.61(10) . . ?
N2 Fe1 N1 79.53(11) . . ?
O1 Fe1 Br1 107.80(8) . . ?
O2 Fe1 Br1 107.17(7) . . ?
N2 Fe1 Br1 104.84(8) . . ?
N1 Fe1 Br1 102.70(7) . . ?
C4 N1 C6 121.6(3) . . ?
C4 N1 Fe1 127.6(2) . . ?
C6 N1 Fe1 110.6(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 N2 C7 121.1(5) . . ?
C9 N2 C7' 118.5(5) . . ?
C9 N2 Fe1 128.3(2) . . ?
C7 N2 Fe1 108.3(5) . . ?
C7' N2 Fe1 111.9(4) . . ?
C11 O2 Fe1 131.3(2) . . ?
O1 C2 C3 124.7(3) . . ?
O1 C2 C1 114.1(3) . . ?
C3 C2 C1 121.2(3) . . ?
C2 C3 C4 125.8(3) . . ?
C2 C3 H3 117.1 . . ?
C4 C3 H3 117.1 . . ?
N1 C4 C3 122.1(3) . . ?
N1 C4 C5 121.2(4) . . ?
C3 C4 C5 116.6(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7' C6 N1 113.3(5) . . ?
N1 C6 C7 113.9(4) . . ?
N1 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
N1 C6 H6AB 108.8 . . ?
C7 C6 H6AB 108.8 . . ?
H6A C6 H6AB 107.7 . . ?
N2 C7 C6 106.1(8) . . ?
N2 C7 H7A 110.5 . . ?
C6 C7 H7A 110.5 . . ?
N2 C7 H7AB 110.5 . . ?
C6 C7 H7AB 110.5 . . ?
H7A C7 H7AB 108.7 . . ?
C6 C7' N2 113.7(7) . . ?
C6 C7' H7'1 108.8 . . ?
N2 C7' H7'1 108.8 . . ?
C6 C7' H7'2 108.8 . . ?
N2 C7' H7'2 108.8 . . ?
H7'1 C7' H7'2 107.7 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 122.3(3) . . ?
N2 C9 C8 120.7(3) . . ?
C10 C9 C8 117.0(3) . . ?
C11 C10 C9 126.0(3) . . ?
C11 C10 H10 117.0 . . ?
C9 C10 H10 117.0 . . ?
O2 C11 C10 124.3(3) . . ?
O2 C11 C12 114.8(3) . . ?
C10 C11 C12 120.9(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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
Br1 Fe1 2.3862(6) . ?
O1 C2 1.292(4) . ?
O1 Fe1 1.918(2) . ?
Fe1 O2 1.9229(19) . ?
Fe1 N2 2.044(3) . ?
Fe1 N1 2.060(2) . ?
N1 C4 1.306(4) . ?
N1 C6 1.463(5) . ?
C1 C2 1.511(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C9 1.306(4) . ?
N2 C7 1.466(10) . ?
N2 C7' 1.531(10) . ?
O2 C11 1.294(4) . ?
C2 C3 1.355(5) . ?
C3 C4 1.417(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.525(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7' 1.345(10) . ?
C6 C7 1.548(15) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C7' H7'1 0.9700 . ?
C7' H7'2 0.9700 . ?
C8 C9 1.524(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.401(5) . ?
C10 C11 1.361(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.509(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
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
Fe1 O1 C2 C3 8.3(5) . . . . ?
Fe1 O1 C2 C1 -172.7(2) . . . . ?
O1 C2 C3 C4 -0.1(6) . . . . ?
C1 C2 C3 C4 -179.0(3) . . . . ?
C6 N1 C4 C3 178.8(4) . . . . ?
Fe1 N1 C4 C3 -5.8(5) . . . . ?
C6 N1 C4 C5 -0.2(5) . . . . ?
Fe1 N1 C4 C5 175.2(3) . . . . ?
C2 C3 C4 N1 -0.7(5) . . . . ?
C2 C3 C4 C5 178.4(4) . . . . ?
C4 N1 C6 C7' -146.4(9) . . . . ?
Fe1 N1 C6 C7' 37.6(10) . . . . ?
C4 N1 C6 C7 -177.7(9) . . . . ?
Fe1 N1 C6 C7 6.2(9) . . . . ?
C9 N2 C7 C6 148.5(6) . . . . ?
Fe1 N2 C7 C6 -47.2(13) . . . . ?
N1 C6 C7 N2 26.5(14) . . . . ?
N1 C6 C7' N2 -28.1(15) . . . . ?
C9 N2 C7' C6 174.2(9) . . . . ?
Fe1 N2 C7' C6 5.9(15) . . . . ?
C7 N2 C9 C10 161.8(11) . . . . ?
C7' N2 C9 C10 -165.3(8) . . . . ?
Fe1 N2 C9 C10 0.8(5) . . . . ?
C7 N2 C9 C8 -19.7(11) . . . . ?
C7' N2 C9 C8 13.2(9) . . . . ?
Fe1 N2 C9 C8 179.3(3) . . . . ?
N2 C9 C10 C11 0.4(6) . . . . ?
C8 C9 C10 C11 -178.2(4) . . . . ?
Fe1 O2 C11 C10 -7.0(5) . . . . ?
Fe1 O2 C11 C12 173.2(2) . . . . ?
C9 C10 C11 O2 2.6(6) . . . . ?
C9 C10 C11 C12 -177.7(3) . . . . ?
