#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/58/7105829.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_7105829
loop_
_publ_author_name
'Daiki Kuzuhara'
'Hiroko Yamada'
'ZhaoLi Xue'
'Tetsuo Okujima'
'Shigeki Mori'
'Zhen Shen'
'Hidemitsu Uno'
_publ_section_title
;
 New synthesis of meso-free-[14]triphyrin(2.1.1) by McMurry coupling and
 its derivatization to Mn(I) and Re(I) complexes
;
_journal_name_full               Chem.Commun.
_journal_page_first              722
_journal_paper_doi               10.1039/c0cc04286b
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C33 H38 Mn N3 O3 '
_chemical_formula_sum            'C33 H38 Mn N3 O3'
_chemical_formula_weight         579.62
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.781(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.844(2)
_cell_length_b                   15.867(3)
_cell_length_c                   17.615(4)
_cell_measurement_reflns_used    8824
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1
_cell_measurement_theta_min      2.3
_cell_volume                     2986.8(10)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8.2'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'VariMax 50 kV 24 mA Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            48856
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6835
_refine_ls_number_restraints     128
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0485
_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)+(0.0447P)²+2.0940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                6371
_reflns_number_total             6835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC04286B.TXT
_cod_data_source_block           '__kuzuhara'
_cod_original_cell_volume        2986.8(11)
_cod_original_formula_sum        'C33 H38 Mn N3 O3 '
_cod_database_code               7105829
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
Mn1 Mn 0.35190(3) 0.646721(17) 0.679461(15) 0.01311(9) Uani 1 1 d . . .
O1 O 0.18604(14) 0.54009(9) 0.75702(9) 0.0260(3) Uani 1 1 d . . .
O2 O 0.11863(14) 0.72592(11) 0.59824(9) 0.0340(4) Uani 1 1 d . . .
O3 O 0.33999(15) 0.76636(9) 0.80616(8) 0.0270(3) Uani 1 1 d . . .
N1 N 0.36936(14) 0.57059(9) 0.59102(8) 0.0146(3) Uani 1 1 d . . .
N2 N 0.46626(14) 0.71668(9) 0.62894(8) 0.0137(3) Uani 1 1 d . A .
N3 N 0.51489(14) 0.59618(9) 0.72909(8) 0.0142(3) Uani 1 1 d . A .
C1 C 0.35718(17) 0.48584(11) 0.58833(10) 0.0155(4) Uani 1 1 d . . .
C2 C 0.31562(18) 0.45947(12) 0.50853(11) 0.0177(4) Uani 1 1 d . A .
C3 C 0.31208(17) 0.53014(12) 0.46427(10) 0.0165(4) Uani 1 1 d D . .
C4 C 0.34973(17) 0.60028(11) 0.51669(10) 0.0148(4) Uani 1 1 d . A .
C5 C 0.38041(17) 0.68262(11) 0.49845(10) 0.0154(4) Uani 1 1 d . . .
H5 H 0.3543 0.7025 0.4474 0.019 Uiso 1 1 calc R A .
C6 C 0.44862(17) 0.73709(11) 0.55320(10) 0.0150(4) Uani 1 1 d . A .
C7 C 0.53623(17) 0.80446(11) 0.54166(10) 0.0162(4) Uani 1 1 d . . .
C8 C 0.61212(17) 0.81671(11) 0.61146(11) 0.0162(4) Uani 1 1 d . A .
C9 C 0.57020(17) 0.75693(11) 0.66501(10) 0.0148(3) Uani 1 1 d . . .
C10 C 0.63572(17) 0.72558(11) 0.73519(10) 0.0155(4) Uani 1 1 d . A .
H10 H 0.6969 0.7603 0.7650 0.019 Uiso 1 1 calc R . .
C11 C 0.61396(17) 0.64500(11) 0.76263(10) 0.0149(4) Uani 1 1 d . . .
C12 C 0.69825(17) 0.59397(12) 0.81732(10) 0.0169(4) Uani 1 1 d . A .
C13 C 0.65163(17) 0.51363(12) 0.81112(10) 0.0171(4) Uani 1 1 d . . .
C14 C 0.53749(17) 0.51601(11) 0.75348(10) 0.0150(4) Uani 1 1 d . A .
C15 C 0.47041(17) 0.44470(12) 0.72245(10) 0.0167(4) Uani 1 1 d . . .
H15 H 0.4795 0.3969 0.7554 0.020 Uiso 1 1 calc R A .
C16 C 0.39284(17) 0.43165(12) 0.65182(11) 0.0177(4) Uani 1 1 d . A .
H16 H 0.3579 0.3767 0.6453 0.021 Uiso 1 1 calc R . .
C17 C 0.2852(2) 0.37130(12) 0.48154(12) 0.0236(4) Uani 1 1 d . . .
H17A H 0.1956 0.3609 0.4793 0.035 Uiso 1 1 calc R A .
H17B H 0.3333 0.3315 0.5175 0.035 Uiso 1 1 calc R . .
H17C H 0.3069 0.3637 0.4302 0.035 Uiso 1 1 calc R . .
C18 C 0.27442(19) 0.53548(13) 0.37863(11) 0.0213(4) Uani 0.799(5) 1 d PDU A 1
H18A H 0.3081 0.4861 0.3546 0.026 Uiso 0.799(5) 1 calc PR A 1
H18B H 0.3115 0.5868 0.3597 0.026 Uiso 0.799(5) 1 calc PR A 1
C19 C 0.1307(2) 0.53825(19) 0.35385(14) 0.0215(6) Uani 0.799(5) 1 d PDU A 1
H19A H 0.1101 0.5351 0.2970 0.026 Uiso 0.799(5) 1 calc PR A 1
H19B H 0.0934 0.4885 0.3752 0.026 Uiso 0.799(5) 1 calc PR A 1
C20 C 0.0738(2) 0.61780(17) 0.38117(17) 0.0273(7) Uani 0.799(5) 1 d PDU A 1
H20A H 0.1123 0.6675 0.3605 0.033 Uiso 0.799(5) 1 calc PR A 1
H20B H 0.0937 0.6205 0.4381 0.033 Uiso 0.799(5) 1 calc PR A 1
C21 C -0.0680(4) 0.6221(3) 0.3562(4) 0.0376(11) Uani 0.799(5) 1 d PDU A 1
H21A H -0.0884 0.6204 0.2999 0.056 Uiso 0.799(5) 1 calc PR A 1
H21B H -0.0995 0.6747 0.3750 0.056 Uiso 0.799(5) 1 calc PR A 1
H21C H -0.1070 0.5740 0.3778 0.056 Uiso 0.799(5) 1 calc PR A 1
C18A C 0.27442(19) 0.53548(13) 0.37863(11) 0.0213(4) Uani 0.201(5) 1 d PD A 2
H18C H 0.2578 0.4782 0.3570 0.026 Uiso 0.201(5) 1 calc PR A 2
H18D H 0.3434 0.5604 0.3558 0.026 Uiso 0.201(5) 1 calc PR A 2
C19A C 0.1525(9) 0.5918(8) 0.3574(6) 0.027(3) Uani 0.201(5) 1 d PDU A 2
H19C H 0.1644 0.6469 0.3840 0.032 Uiso 0.201(5) 1 calc PR A 2
H19D H 0.1337 0.6019 0.3011 0.032 Uiso 0.201(5) 1 calc PR A 2
C20A C 0.0460(10) 0.5428(7) 0.3838(7) 0.033(3) Uani 0.201(5) 1 d PDU A 2
H20C H 0.0285 0.4911 0.3524 0.040 Uiso 0.201(5) 1 calc PR A 2
H20D H 0.0714 0.5258 0.4382 0.040 Uiso 0.201(5) 1 calc PR A 2
C21A C -0.0724(18) 0.5966(16) 0.3758(18) 0.053(6) Uani 0.201(5) 1 d PDU A 2
H21D H -0.0516 0.6522 0.3987 0.079 Uiso 0.201(5) 1 calc PR A 2
H21E H -0.1337 0.5689 0.4024 0.079 Uiso 0.201(5) 1 calc PR A 2
H21F H -0.1079 0.6031 0.3211 0.079 Uiso 0.201(5) 1 calc PR A 2
C22 C 0.54343(18) 0.84627(12) 0.46626(11) 0.0185(4) Uani 1 1 d . A .
H22A H 0.5522 0.8024 0.4276 0.022 Uiso 1 1 calc R . .
H22B H 0.6192 0.8822 0.4724 0.022 Uiso 1 1 calc R . .
C23 C 0.42894(19) 0.90042(13) 0.43622(12) 0.0240(4) Uani 1 1 d . . .
H23A H 0.3540 0.8648 0.4274 0.036 Uiso 1 1 calc R A .
H23B H 0.4400 0.9273 0.3877 0.036 Uiso 1 1 calc R . .
H23C H 0.4193 0.9439 0.4743 0.036 Uiso 1 1 calc R . .
C24 C 0.72483(18) 0.87224(12) 0.63028(11) 0.0204(4) Uani 1 1 d . . .
H24A H 0.7338 0.8899 0.6848 0.025 Uiso 1 1 calc R A .
H24B H 0.7116 0.9236 0.5980 0.025 Uiso 1 1 calc R . .
C25 C 0.8461(2) 0.82946(15) 0.61738(14) 0.0305(5) Uani 1 1 d . A .
H25A H 0.8596 0.7782 0.6488 0.046 Uiso 1 1 calc R . .
H25B H 0.9166 0.8681 0.6323 0.046 Uiso 1 1 calc R . .
H25C H 0.8399 0.8147 0.5628 0.046 Uiso 1 1 calc R . .
C26 C 0.81466(18) 0.62481(13) 0.86789(11) 0.0200(4) Uani 1 1 d . . .
H26A H 0.8300 0.5895 0.9149 0.024 Uiso 1 1 calc R A .
H26B H 0.8001 0.6832 0.8841 0.024 Uiso 1 1 calc R . .
C27 C 0.93258(19) 0.62390(15) 0.83093(12) 0.0254(4) Uani 1 1 d . A .
H27A H 0.9456 0.5663 0.8123 0.031 Uiso 1 1 calc R . .
H27B H 0.9202 0.6621 0.7858 0.031 Uiso 1 1 calc R . .
C28 C 1.0493(2) 0.65120(14) 0.88653(13) 0.0277(5) Uani 1 1 d . . .
H28A H 1.1186 0.6592 0.8572 0.033 Uiso 1 1 calc R A .
H28B H 1.0327 0.7063 0.9092 0.033 Uiso 1 1 calc R . .
C29 C 1.0904(2) 0.5893(2) 0.95094(16) 0.0503(8) Uani 1 1 d . A .
H29A H 1.0236 0.5826 0.9816 0.075 Uiso 1 1 calc R . .
H29B H 1.1660 0.6105 0.9839 0.075 Uiso 1 1 calc R . .
H29C H 1.1083 0.5347 0.9291 0.075 Uiso 1 1 calc R . .
C30 C 0.7081(2) 0.43530(13) 0.84993(12) 0.0242(4) Uani 1 1 d . A .
H30A H 0.7356 0.3982 0.8116 0.036 Uiso 1 1 calc R . .
H30B H 0.6456 0.4061 0.8744 0.036 Uiso 1 1 calc R . .
H30C H 0.7801 0.4504 0.8891 0.036 Uiso 1 1 calc R . .
C31 C 0.25348(18) 0.57772(12) 0.72589(11) 0.0181(4) Uani 1 1 d . . .
C32 C 0.20977(19) 0.69506(12) 0.62784(11) 0.0200(4) Uani 1 1 d . . .
C33 C 0.34752(17) 0.71957(12) 0.75702(10) 0.0171(4) 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 0.0033 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'
Mn Mn 0.3368 0.7283 '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
C33 Mn1 C31 87.25(8) . . ?
C33 Mn1 C32 88.81(8) . . ?
C31 Mn1 C32 88.08(9) . . ?
C33 Mn1 N2 94.62(7) . . ?
C31 Mn1 N2 176.73(7) . . ?
C32 Mn1 N2 94.64(8) . . ?
C33 Mn1 N3 93.50(7) . . ?
C31 Mn1 N3 96.00(7) . . ?
C32 Mn1 N3 175.39(7) . . ?
N2 Mn1 N3 81.21(6) . . ?
C33 Mn1 N1 175.22(8) . . ?
C31 Mn1 N1 97.29(7) . . ?
C32 Mn1 N1 92.83(7) . . ?
N2 Mn1 N1 80.78(6) . . ?
N3 Mn1 N1 84.56(6) . . ?
C1 N1 C4 108.02(15) . . ?
C1 N1 Mn1 127.24(13) . . ?
C4 N1 Mn1 120.94(12) . . ?
C6 N2 C9 108.41(15) . . ?
C6 N2 Mn1 125.54(12) . . ?
C9 N2 Mn1 125.90(12) . . ?
C14 N3 C11 107.92(15) . . ?
C14 N3 Mn1 127.94(13) . . ?
C11 N3 Mn1 122.00(12) . . ?
N1 C1 C16 124.50(17) . . ?
N1 C1 C2 109.32(16) . . ?
C16 C1 C2 125.83(17) . . ?
C3 C2 C1 106.78(16) . . ?
C3 C2 C17 127.19(17) . . ?
C1 C2 C17 126.03(17) . . ?
C2 C3 C4 106.73(16) . . ?
C2 C3 C18 126.85(17) . . ?
C4 C3 C18 126.41(17) . . ?
N1 C4 C5 122.33(16) . . ?
N1 C4 C3 108.84(16) . . ?
C5 C4 C3 128.23(17) . . ?
C4 C5 C6 122.27(16) . . ?
N2 C6 C5 119.85(16) . . ?
N2 C6 C7 108.93(16) . . ?
C5 C6 C7 129.03(16) . . ?
C8 C7 C6 106.44(16) . . ?
C8 C7 C22 128.16(18) . . ?
C6 C7 C22 125.30(17) . . ?
C7 C8 C9 106.32(16) . . ?
C7 C8 C24 128.63(17) . . ?
C9 C8 C24 124.75(17) . . ?
N2 C9 C10 120.02(16) . . ?
N2 C9 C8 109.13(15) . . ?
C10 C9 C8 129.00(17) . . ?
C11 C10 C9 122.41(17) . . ?
N3 C11 C10 122.09(16) . . ?
N3 C11 C12 109.16(16) . . ?
C10 C11 C12 127.75(17) . . ?
C13 C12 C11 106.45(16) . . ?
C13 C12 C26 127.89(17) . . ?
C11 C12 C26 125.63(17) . . ?
C12 C13 C14 106.80(16) . . ?
C12 C13 C30 128.26(17) . . ?
C14 C13 C30 124.79(17) . . ?
N3 C14 C15 125.48(16) . . ?
N3 C14 C13 109.36(16) . . ?
C15 C14 C13 124.80(16) . . ?
C16 C15 C14 131.38(17) . . ?
C15 C16 C1 131.24(18) . . ?
C3 C18 C19 112.06(17) . . ?
C20 C19 C18 112.2(2) . . ?
C19 C20 C21 112.9(3) . . ?
C21A C20A C19A 110.8(12) . . ?
C7 C22 C23 113.21(16) . . ?
C8 C24 C25 113.31(17) . . ?
C12 C26 C27 115.12(16) . . ?
C28 C27 C26 112.71(17) . . ?
C29 C28 C27 113.9(2) . . ?
O1 C31 Mn1 174.14(17) . . ?
O2 C32 Mn1 177.13(17) . . ?
O3 C33 Mn1 177.49(17) . . ?
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
Mn1 C33 1.7964(19) . ?
Mn1 C31 1.817(2) . ?
Mn1 C32 1.821(2) . ?
Mn1 N2 1.9841(16) . ?
Mn1 N3 2.0015(16) . ?
Mn1 N1 2.0056(15) . ?
O1 C31 1.152(2) . ?
O2 C32 1.146(2) . ?
O3 C33 1.154(2) . ?
N1 C1 1.351(2) . ?
N1 C4 1.374(2) . ?
N2 C6 1.355(2) . ?
N2 C9 1.356(2) . ?
N3 C14 1.352(2) . ?
N3 C11 1.374(2) . ?
C1 C16 1.412(3) . ?
C1 C2 1.463(2) . ?
C2 C3 1.362(3) . ?
C2 C17 1.496(3) . ?
C3 C4 1.459(2) . ?
C3 C18 1.497(3) . ?
C4 C5 1.399(3) . ?
C5 C6 1.408(3) . ?
C6 C7 1.467(3) . ?
C7 C8 1.372(3) . ?
C7 C22 1.499(3) . ?
C8 C9 1.463(3) . ?
C8 C24 1.497(3) . ?
C9 C10 1.408(2) . ?
C10 C11 1.401(3) . ?
C11 C12 1.456(2) . ?
C12 C13 1.369(3) . ?
C12 C26 1.498(3) . ?
C13 C14 1.462(3) . ?
C13 C30 1.498(3) . ?
C14 C15 1.405(3) . ?
C15 C16 1.394(3) . ?
C18 C19 1.546(3) . ?
C19 C20 1.519(4) . ?
C20 C21 1.527(5) . ?
C19A C20A 1.528(13) . ?
C20A C21A 1.528(15) . ?
C22 C23 1.529(3) . ?
C24 C25 1.531(3) . ?
C26 C27 1.530(3) . ?
C27 C28 1.525(3) . ?
C28 C29 1.509(3) . ?
