#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:16:36 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178776 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/30/4103076.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_4103076
loop_
_publ_author_name
'Toby Wai-Shan Chow'
'Ella Lai-Ming Wong'
'Zhen Guo'
'Yungen Liu'
'Jie-Sheng Huang'
'Chi-Ming Che'
_publ_section_title
;
 cis-Dihydroxylation of Alkenes with Oxone Catalyzed by Iron Complexes of
 a Macrocyclic Tetraaza Ligand and Reaction Mechanism by ESI-MS
 Spectrometry and DFT Calculations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13229
_journal_page_last               13239
_journal_paper_doi               10.1021/ja100967g
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C16 H20 Cl2 Fe N4, C2 H3 N, Cl O4'
_chemical_formula_sum            'C18 H23 Cl3 Fe N5 O4'
_chemical_formula_weight         535.61
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.806(3)
_cell_length_b                   9.909(2)
_cell_length_c                   16.903(4)
_cell_measurement_reflns_used    13113
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      1.91
_cell_volume                     2312.4(9)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction
'SAINT & CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω
_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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13113
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         1.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1100
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0433P)²+1.2605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                1933
_reflns_number_total             2325
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja100967g_si_002_2.cif
_cod_data_source_block           complex1_ClO4
_cod_database_code               4103076
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
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
C1 C 0.88184(17) 0.8743(2) 0.47480(13) 0.0511(5) Uani 1 1 d .
H1A H 0.9509 0.8582 0.4700 0.061 Uiso 1 1 calc R
H1B H 0.8725 0.9469 0.5125 0.061 Uiso 1 1 calc R
C2 C 0.84253(15) 0.9169(2) 0.39577(12) 0.0429(5) Uani 1 1 d .
C3 C 0.89329(17) 0.9885(2) 0.33924(14) 0.0552(6) Uani 1 1 d .
H3 H 0.9573 1.0136 0.3480 0.066 Uiso 1 1 calc R
C4 C 0.84719(18) 1.0219(3) 0.26966(14) 0.0626(7) Uani 1 1 d .
H4 H 0.8801 1.0705 0.2310 0.075 Uiso 1 1 calc R
C5 C 0.75245(18) 0.9835(2) 0.25721(14) 0.0577(6) Uani 1 1 d .
H5 H 0.7214 1.0032 0.2098 0.069 Uiso 1 1 calc R
C6 C 0.70472(15) 0.9150(2) 0.31671(12) 0.0439(5) Uani 1 1 d .
C7 C 0.59955(16) 0.8741(2) 0.31433(14) 0.0538(6) Uani 1 1 d .
H7A H 0.5602 0.9474 0.3347 0.065 Uiso 1 1 calc R
H7B H 0.5806 0.8584 0.2598 0.065 Uiso 1 1 calc R
C8 C 0.8437(3) 0.7500 0.59345(19) 0.0678(10) Uani 1 2 d S
H8A H 0.8136 0.8296 0.6146 0.102 Uiso 0.50 1 calc PR
H8B H 0.9110 0.7490 0.6076 0.102 Uiso 1 2 calc SR
H8C H 0.8124 0.6714 0.6147 0.102 Uiso 0.50 1 calc PR
C10 C 0.4760(2) 0.7500 0.3841(2) 0.0588(9) Uani 1 2 d S
H10A H 0.4619 0.8293 0.4147 0.088 Uiso 0.50 1 calc PR
H10B H 0.4621 0.6711 0.4151 0.088 Uiso 0.50 1 calc PR
H10C H 0.4367 0.7496 0.3373 0.088 Uiso 1 2 calc SR
C11 C 0.9111(3) 0.7500 0.8321(2) 0.0648(9) Uani 1 2 d S
C12 C 0.8598(4) 0.7500 0.9071(2) 0.0886(14) Uani 1 2 d S
H12A H 0.8592 0.8397 0.9285 0.133 Uiso 0.50 1 calc PR
H12B H 0.8919 0.6903 0.9434 0.133 Uiso 0.50 1 calc PR
H12C H 0.7945 0.7200 0.8989 0.133 Uiso 0.50 1 calc PR
Cl1 Cl 0.62324(5) 0.92297(6) 0.53629(4) 0.0658(2) Uani 1 1 d .
Cl2 Cl 0.15438(6) 0.7500 0.42484(5) 0.0542(2) Uani 1 2 d S
Fe1 Fe 0.68108(3) 0.7500 0.46517(2) 0.03872(14) Uani 1 2 d S
N1 N 0.74953(12) 0.88444(16) 0.38440(9) 0.0390(4) Uani 1 1 d .
N2 N 0.83423(18) 0.7500 0.50531(14) 0.0431(6) Uani 1 2 d S
N3 N 0.58032(17) 0.7500 0.36150(14) 0.0418(5) Uani 1 2 d S
N4 N 0.9501(3) 0.7500 0.7740(2) 0.0950(12) Uani 1 2 d S
O1 O 0.11180(18) 0.8658(2) 0.39000(13) 0.0963(7) Uani 1 1 d .
O2 O 0.2543(2) 0.7500 0.4102(2) 0.1187(13) Uani 1 2 d S
O3 O 0.1322(3) 0.7500 0.50684(17) 0.1018(11) Uani 1 2 d S
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'
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
N2 C1 C2 112.42(18) . .
N2 C1 H1A 109.1 . .
C2 C1 H1A 109.1 . .
N2 C1 H1B 109.1 . .
C2 C1 H1B 109.1 . .
H1A C1 H1B 107.9 . .
N1 C2 C3 120.75(19) . .
N1 C2 C1 113.99(18) . .
C3 C2 C1 125.2(2) . .
C4 C3 C2 118.7(2) . .
C4 C3 H3 120.7 . .
C2 C3 H3 120.7 . .
C3 C4 C5 120.2(2) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C4 C5 C6 118.5(2) . .
C4 C5 H5 120.7 . .
C6 C5 H5 120.7 . .
N1 C6 C5 121.0(2) . .
N1 C6 C7 114.07(18) . .
C5 C6 C7 124.91(19) . .
N3 C7 C6 112.30(18) . .
N3 C7 H7A 109.1 . .
C6 C7 H7A 109.1 . .
N3 C7 H7B 109.1 . .
C6 C7 H7B 109.1 . .
H7A C7 H7B 107.9 . .
N2 C8 H8A 109.5 . .
N2 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N2 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N3 C10 H10A 109.5 . .
N3 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
N3 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N4 C11 C12 179.5(5) . .
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 . .
O2 Cl2 O1 109.56(14) . 8_575
O2 Cl2 O1 109.56(14) . .
O1 Cl2 O1 108.1(2) 8_575 .
O2 Cl2 O3 112.6(2) . .
O1 Cl2 O3 108.43(12) 8_575 .
O1 Cl2 O3 108.43(12) . .
N1 Fe1 N1 77.48(9) 8_575 .
N1 Fe1 N2 76.89(7) 8_575 .
N1 Fe1 N2 76.89(7) . .
N1 Fe1 N3 76.92(7) 8_575 .
N1 Fe1 N3 76.92(7) . .
N2 Fe1 N3 146.23(9) . .
N1 Fe1 Cl1 168.81(5) 8_575 .
N1 Fe1 Cl1 91.35(5) . .
N2 Fe1 Cl1 100.10(5) . .
N3 Fe1 Cl1 101.46(5) . .
N1 Fe1 Cl1 91.35(5) 8_575 8_575
N1 Fe1 Cl1 168.81(5) . 8_575
N2 Fe1 Cl1 100.10(5) . 8_575
N3 Fe1 Cl1 101.46(5) . 8_575
Cl1 Fe1 Cl1 99.81(4) . 8_575
C6 N1 C2 120.87(17) . .
C6 N1 Fe1 119.06(13) . .
C2 N1 Fe1 118.99(13) . .
C1 N2 C1 111.7(2) 8_575 .
C1 N2 C8 107.86(16) 8_575 .
C1 N2 C8 107.86(16) . .
C1 N2 Fe1 108.35(13) 8_575 .
C1 N2 Fe1 108.35(13) . .
C8 N2 Fe1 112.8(2) . .
C7 N3 C7 111.3(2) 8_575 .
C7 N3 C10 108.04(16) 8_575 .
C7 N3 C10 108.04(16) . .
C7 N3 Fe1 107.97(13) 8_575 .
C7 N3 Fe1 107.97(13) . .
C10 N3 Fe1 113.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.488(3) .
C1 C2 1.503(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 N1 1.338(3) .
C2 C3 1.381(3) .
C3 C4 1.378(3) .
C3 H3 0.9300 .
C4 C5 1.378(3) .
C4 H4 0.9300 .
C5 C6 1.381(3) .
C5 H5 0.9300 .
C6 N1 1.336(2) .
C6 C7 1.508(3) .
C7 N3 1.489(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 N2 1.496(4) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C10 N3 1.491(4) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 N4 1.119(5) .
C11 C12 1.451(6) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
Cl1 Fe1 2.2407(7) .
Cl2 O2 1.402(3) .
Cl2 O1 1.417(2) 8_575
Cl2 O1 1.417(2) .
Cl2 O3 1.419(3) .
Fe1 N1 2.1288(16) 8_575
Fe1 N1 2.1288(16) .
Fe1 N2 2.221(3) .
Fe1 N3 2.237(2) .
Fe1 Cl1 2.2407(7) 8_575
N2 C1 1.488(3) 8_575
N3 C7 1.489(3) 8_575
