#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:03:25 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179949 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/44/7024470.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_7024470
loop_
_publ_author_name
'Tang, Jinkui'
'Nayak, Sanjit'
'Costa, José Sánchez'
'Robertazzi, Arturo'
'Pievo, Roberta'
'Mutikainen, Ilpo'
'Roubeau, Olivier'
'Teat, Simon J.'
'Gamez, Patrick'
'Reedijk, Jan'
_publ_section_title
;
 Manganese(III)-mediated cyclodimerization of a hydrazinyl derivative
 generating an unprecedented 1,2,3,5,6-substituted leuco-verdazyl ring.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1361
_journal_page_last               1365
_journal_paper_doi               10.1039/b917410a
_journal_volume                  39
_journal_year                    2010
_chemical_formula_sum            'C24 H20 Mn N6 O2'
_chemical_formula_weight         479.40
_chemical_name_systematic
;
?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                   20.661(2)
_cell_length_b                   8.9103(10)
_cell_length_c                   11.1550(12)
_cell_measurement_reflns_used    4155
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.26
_cell_measurement_theta_min      3.36
_cell_volume                     2053.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'ALS beamline 11.3.1'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.77490
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14462
_diffrn_reflns_theta_full        33.56
_diffrn_reflns_theta_max         33.56
_diffrn_reflns_theta_min         3.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.922
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0814P)²+0.4477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                2596
_reflns_number_total             3113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b917410a.txt
_cod_data_source_block           jk233
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7024470
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, 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
Mn1 Mn 0.5000 -0.05508(4) 0.2500 0.01939(12) Uani 1 2 d S
N1 N 0.45011(6) -0.22856(16) 0.36386(12) 0.0228(3) Uani 1 1 d .
C2 C 0.39301(8) -0.2931(2) 0.33714(16) 0.0294(3) Uani 1 1 d .
H2A H 0.3734 -0.2693 0.2625 0.035 Uiso 1 1 calc R
C3 C 0.36178(8) -0.3909(2) 0.41134(18) 0.0320(4) Uani 1 1 d .
H3A H 0.3214 -0.4338 0.3891 0.038 Uiso 1 1 calc R
C4 C 0.39061(9) -0.42606(19) 0.52039(17) 0.0298(4) Uani 1 1 d .
H4A H 0.3700 -0.4939 0.5739 0.036 Uiso 1 1 calc R
C5 C 0.44872(8) -0.36278(19) 0.55046(15) 0.0262(3) Uani 1 1 d .
H5A H 0.4692 -0.3862 0.6243 0.031 Uiso 1 1 calc R
C6 C 0.47719(7) -0.26231(17) 0.46904(14) 0.0212(3) Uani 1 1 d .
N7 N 0.53516(6) -0.19730(15) 0.49615(12) 0.0224(3) Uani 1 1 d .
H7A H 0.5559 -0.2197 0.5627 0.027 Uiso 1 1 calc R
N8 N 0.55996(6) -0.09553(15) 0.41586(11) 0.0196(2) Uani 1 1 d .
C9 C 0.61450(7) -0.03603(17) 0.44609(14) 0.0209(3) Uani 1 1 d .
H9A H 0.6324 -0.0654 0.5209 0.025 Uiso 1 1 calc R
C10 C 0.65040(7) 0.07074(17) 0.37645(14) 0.0202(3) Uani 1 1 d .
C11 C 0.71115(7) 0.11208(19) 0.42241(15) 0.0250(3) Uani 1 1 d .
H11A H 0.7259 0.0662 0.4942 0.030 Uiso 1 1 calc R
C12 C 0.74975(8) 0.2161(2) 0.36742(16) 0.0293(3) Uani 1 1 d .
H12A H 0.7907 0.2419 0.4003 0.035 Uiso 1 1 calc R
C13 C 0.72794(9) 0.2832(2) 0.26274(16) 0.0297(4) Uani 1 1 d .
H13A H 0.7541 0.3561 0.2237 0.036 Uiso 1 1 calc R
C14 C 0.66871(8) 0.24509(19) 0.21496(15) 0.0258(3) Uani 1 1 d .
H14A H 0.6550 0.2923 0.1430 0.031 Uiso 1 1 calc R
C15 C 0.62781(8) 0.13845(18) 0.26928(14) 0.0209(3) Uani 1 1 d .
O16 O 0.57104(6) 0.10930(14) 0.22294(10) 0.0239(2) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0020 '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 -0.0031 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0041 0.0074 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.2237 0.8587 '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
O16 Mn1 O16 91.30(7) . 3_655
O16 Mn1 N1 94.47(5) . 3_655
O16 Mn1 N1 151.91(5) 3_655 3_655
O16 Mn1 N1 151.91(5) . .
O16 Mn1 N1 94.47(5) 3_655 .
N1 Mn1 N1 93.24(7) 3_655 .
O16 Mn1 N8 81.09(4) . .
O16 Mn1 N8 112.22(5) 3_655 .
N1 Mn1 N8 95.83(5) 3_655 .
N1 Mn1 N8 71.27(5) . .
O16 Mn1 N8 112.22(5) . 3_655
O16 Mn1 N8 81.09(4) 3_655 3_655
N1 Mn1 N8 71.27(5) 3_655 3_655
N1 Mn1 N8 95.83(5) . 3_655
N8 Mn1 N8 161.61(7) . 3_655
C6 N1 C2 117.78(14) . .
C6 N1 Mn1 117.32(10) . .
C2 N1 Mn1 124.75(11) . .
N1 C2 C3 123.60(17) . .
N1 C2 H2A 118.2 . .
C3 C2 H2A 118.2 . .
C2 C3 C4 118.17(16) . .
C2 C3 H3A 120.9 . .
C4 C3 H3A 120.9 . .
C5 C4 C3 119.85(16) . .
C5 C4 H4A 120.1 . .
C3 C4 H4A 120.1 . .
C4 C5 C6 118.15(16) . .
C4 C5 H5A 120.9 . .
C6 C5 H5A 120.9 . .
N1 C6 N7 117.87(14) . .
N1 C6 C5 122.45(14) . .
N7 C6 C5 119.67(14) . .
C6 N7 N8 117.59(12) . .
C6 N7 H7A 121.2 . .
N8 N7 H7A 121.2 . .
C9 N8 N7 115.25(13) . .
C9 N8 Mn1 128.93(11) . .
N7 N8 Mn1 115.81(9) . .
N8 C9 C10 125.63(14) . .
N8 C9 H9A 117.2 . .
C10 C9 H9A 117.2 . .
C11 C10 C15 119.35(14) . .
C11 C10 C9 115.98(14) . .
C15 C10 C9 124.63(13) . .
C12 C11 C10 122.33(15) . .
C12 C11 H11A 118.8 . .
C10 C11 H11A 118.8 . .
C11 C12 C13 118.70(15) . .
C11 C12 H12A 120.6 . .
C13 C12 H12A 120.6 . .
C14 C13 C12 120.52(16) . .
C14 C13 H13A 119.7 . .
C12 C13 H13A 119.7 . .
C13 C14 C15 122.20(16) . .
C13 C14 H14A 118.9 . .
C15 C14 H14A 118.9 . .
O16 C15 C14 120.12(14) . .
O16 C15 C10 122.95(14) . .
C14 C15 C10 116.89(14) . .
C15 O16 Mn1 135.24(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O16 2.0954(12) .
Mn1 O16 2.0954(12) 3_655
Mn1 N1 2.2505(14) 3_655
Mn1 N1 2.2505(14) .
Mn1 N8 2.2556(13) .
Mn1 N8 2.2556(13) 3_655
N1 C6 1.334(2) .
N1 C2 1.346(2) .
C2 C3 1.364(3) .
C2 H2A 0.9500 .
C3 C4 1.390(3) .
C3 H3A 0.9500 .
C4 C5 1.368(2) .
C4 H4A 0.9500 .
C5 C6 1.404(2) .
C5 H5A 0.9500 .
C6 N7 1.364(2) .
N7 N8 1.3737(18) .
N7 H7A 0.8800 .
N8 C9 1.2902(18) .
C9 C10 1.435(2) .
C9 H9A 0.9500 .
C10 C11 1.405(2) .
C10 C15 1.418(2) .
C11 C12 1.368(2) .
C11 H11A 0.9500 .
C12 C13 1.387(3) .
C12 H12A 0.9500 .
C13 C14 1.378(2) .
C13 H13A 0.9500 .
C14 C15 1.409(2) .
C14 H14A 0.9500 .
C15 O16 1.3079(18) .
