#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:08:37 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179441 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/38/4333854.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_4333854
loop_
_publ_author_name
'Hamid Khaledi'
'Marilyn M. Olmstead'
'Hapipah Mohd Ali'
'Noel F. Thomas'
_publ_section_title
;
 Indolenine meso-Substituted Dibenzotetraaza[14]annulene and Its
 Coordination Chemistry toward the Transition Metal Ions MnIII, FeIII,
 CoII, NiII, CuII, and PdII
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1926
_journal_page_last               1941
_journal_paper_doi               10.1021/ic302150j
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C38 H34 N6, 2(C H Cl3)'
_chemical_formula_sum            'C40 H36 Cl6 N6'
_chemical_formula_weight         813.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 105.868(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.9871(2)
_cell_length_b                   19.6913(2)
_cell_length_c                   12.3598(2)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.80
_cell_measurement_theta_min      2.73
_cell_volume                     1869.83(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17098
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_T_max  0.9067
_exptl_absorpt_correction_T_min  0.8526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       Block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0336
_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)+(0.0436P)²+1.3837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0885
_reflns_number_gt                3738
_reflns_number_total             4076
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302150j_si_002_02.cif
_cod_data_source_block           LH2.2CHCl3
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4333854
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 1.19984(15) 0.18507(6) 0.72496(10) 0.0148(2) Uani 1 1 d .
N2 N 0.82713(15) 0.04319(6) 0.87377(10) 0.0136(2) Uani 1 1 d .
H2N H 0.909(2) 0.0344(9) 0.9278(16) 0.016 Uiso 1 1 d .
N3 N 1.16970(15) 0.06109(6) 0.98265(10) 0.0140(2) Uani 1 1 d .
C1 C 1.18907(18) 0.22156(7) 0.62507(11) 0.0137(3) Uani 1 1 d .
C2 C 1.31898(19) 0.26162(7) 0.60213(12) 0.0163(3) Uani 1 1 d .
H2 H 1.4291 0.2667 0.6556 0.020 Uiso 1 1 calc R
C3 C 1.28199(19) 0.29409(7) 0.49786(13) 0.0177(3) Uani 1 1 d .
H3 H 1.3683 0.3217 0.4800 0.021 Uiso 1 1 calc R
C4 C 1.1202(2) 0.28666(7) 0.41949(12) 0.0173(3) Uani 1 1 d .
H4 H 1.0978 0.3092 0.3491 0.021 Uiso 1 1 calc R
C5 C 0.99027(19) 0.24627(7) 0.44342(12) 0.0157(3) Uani 1 1 d .
H5 H 0.8798 0.2413 0.3902 0.019 Uiso 1 1 calc R
C6 C 1.02710(18) 0.21377(7) 0.54657(11) 0.0131(3) Uani 1 1 d .
C7 C 0.91815(17) 0.16740(7) 0.59751(11) 0.0132(3) Uani 1 1 d .
C8 C 0.75067(18) 0.20449(8) 0.60311(12) 0.0180(3) Uani 1 1 d .
H8A H 0.6740 0.2102 0.5269 0.027 Uiso 1 1 calc R
H8B H 0.7808 0.2491 0.6380 0.027 Uiso 1 1 calc R
H8C H 0.6909 0.1777 0.6480 0.027 Uiso 1 1 calc R
C9 C 0.87713(19) 0.10100(7) 0.52910(12) 0.0171(3) Uani 1 1 d .
H9A H 0.7929 0.1103 0.4565 0.026 Uiso 1 1 calc R
H9B H 0.8280 0.0677 0.5709 0.026 Uiso 1 1 calc R
H9C H 0.9844 0.0828 0.5165 0.026 Uiso 1 1 calc R
C10 C 1.05028(18) 0.15497(7) 0.71327(11) 0.0134(3) Uani 1 1 d .
C11 C 1.02268(18) 0.11228(7) 0.80350(11) 0.0138(3) Uani 1 1 d .
C12 C 0.86236(18) 0.08282(7) 0.79499(11) 0.0139(3) Uani 1 1 d .
H12 H 0.7712 0.0913 0.7287 0.017 Uiso 1 1 calc R
C13 C 0.67001(17) 0.00819(7) 0.86291(11) 0.0136(3) Uani 1 1 d .
C14 C 0.51594(18) 0.02705(7) 0.78335(12) 0.0158(3) Uani 1 1 d .
H14 H 0.5152 0.0653 0.7364 0.019 Uiso 1 1 calc R
C15 C 0.36441(18) -0.00975(8) 0.77258(12) 0.0177(3) Uani 1 1 d .
H15 H 0.2603 0.0030 0.7180 0.021 Uiso 1 1 calc R
C16 C 0.36506(19) -0.06541(8) 0.84177(13) 0.0191(3) Uani 1 1 d .
H16 H 0.2617 -0.0911 0.8340 0.023 Uiso 1 1 calc R
C17 C 0.51650(19) -0.08349(8) 0.92216(12) 0.0174(3) Uani 1 1 d .
H17 H 0.5155 -0.1216 0.9691 0.021 Uiso 1 1 calc R
C18 C 0.67066(18) -0.04681(7) 0.93567(11) 0.0136(3) Uani 1 1 d .
C19 C 1.17344(18) 0.09836(7) 0.89709(11) 0.0137(3) Uani 1 1 d .
H19 H 1.2816 0.1178 0.8955 0.016 Uiso 1 1 calc R
Cl1 Cl 1.43448(6) 0.15825(3) 0.32338(4) 0.03303(12) Uani 1 1 d .
Cl2 Cl 1.09937(5) 0.09293(3) 0.28491(4) 0.03628(13) Uani 1 1 d .
Cl3 Cl 1.36792(6) 0.06776(2) 0.49098(4) 0.03257(12) Uani 1 1 d .
C20 C 1.2773(2) 0.12816(8) 0.38694(13) 0.0215(3) Uani 1 1 d .
H20 H 1.234(3) 0.1652(10) 0.4238(17) 0.026 Uiso 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'
N N 0.0061 0.0033 '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'
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_3
_geom_angle_publ_flag
C10 N1 C1 107.42(12) . ?
C12 N2 C13 125.24(12) . y
C12 N2 H2N 115.9(13) . ?
C13 N2 H2N 118.1(13) . ?
C19 N3 C18 118.42(12) 3_757 y
C2 C1 C6 121.38(13) . ?
C2 C1 N1 126.59(13) . ?
C6 C1 N1 112.03(12) . ?
C1 C2 C3 117.77(13) . ?
C1 C2 H2 121.1 . ?
C3 C2 H2 121.1 . ?
C4 C3 C2 121.01(13) . ?
C4 C3 H3 119.5 . ?
C2 C3 H3 119.5 . ?
C3 C4 C5 120.79(13) . ?
C3 C4 H4 119.6 . ?
C5 C4 H4 119.6 . ?
C6 C5 C4 118.26(13) . ?
C6 C5 H5 120.9 . ?
C4 C5 H5 120.9 . ?
C5 C6 C1 120.80(13) . ?
C5 C6 C7 131.38(13) . ?
C1 C6 C7 107.83(11) . ?
C6 C7 C8 109.74(11) . ?
C6 C7 C9 110.10(11) . ?
C8 C7 C9 111.66(11) . ?
C6 C7 C10 98.97(10) . ?
C8 C7 C10 114.46(11) . ?
C9 C7 C10 111.19(11) . ?
C7 C8 H8A 109.5 . ?
C7 C8 H8B 109.5 . ?
H8A C8 H8B 109.5 . ?
C7 C8 H8C 109.5 . ?
H8A C8 H8C 109.5 . ?
H8B C8 H8C 109.5 . ?
C7 C9 H9A 109.5 . ?
C7 C9 H9B 109.5 . ?
H9A C9 H9B 109.5 . ?
C7 C9 H9C 109.5 . ?
H9A C9 H9C 109.5 . ?
H9B C9 H9C 109.5 . ?
N1 C10 C11 120.09(12) . ?
N1 C10 C7 113.73(12) . ?
C11 C10 C7 126.14(12) . ?
C12 C11 C19 122.08(12) . y
C12 C11 C10 120.87(12) . ?
C19 C11 C10 116.89(12) . ?
N2 C12 C11 124.36(13) . y
N2 C12 H12 117.8 . ?
C11 C12 H12 117.8 . ?
C14 C13 N2 121.85(13) . ?
C14 C13 C18 120.16(13) . ?
N2 C13 C18 117.98(12) . y
C15 C14 C13 120.40(13) . ?
C15 C14 H14 119.8 . ?
C13 C14 H14 119.8 . ?
C14 C15 C16 119.82(13) . ?
C14 C15 H15 120.1 . ?
C16 C15 H15 120.1 . ?
C17 C16 C15 119.98(13) . ?
C17 C16 H16 120.0 . ?
C15 C16 H16 120.0 . ?
C16 C17 C18 121.38(14) . ?
C16 C17 H17 119.3 . ?
C18 C17 H17 119.3 . ?
C17 C18 C13 118.19(13) . ?
C17 C18 N3 124.93(13) 3_757 ?
C13 C18 N3 116.88(12) 3_757 y
N3 C19 C11 124.02(13) . y
N3 C19 H19 118.0 . ?
C11 C19 H19 118.0 . ?
Cl3 C20 Cl1 110.73(8) . ?
Cl3 C20 Cl2 110.34(9) . ?
Cl1 C20 Cl2 110.34(9) . ?
Cl3 C20 H20 107.0(12) . ?
Cl1 C20 H20 110.2(11) . ?
Cl2 C20 H20 108.1(12) . ?
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
N1 C10 1.3056(18) . y
N1 C1 1.4107(18) . ?
N2 C12 1.3365(18) . y
N2 C13 1.4056(17) . y
N2 H2N 0.817(19) . ?
N3 C19 1.2942(18) . y
N3 C18 1.4213(18) 3_757 y
C1 C2 1.3929(19) . ?
C1 C6 1.3972(19) . ?
C2 C3 1.396(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3843(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.5123(18) . ?
C7 C8 1.5421(19) . ?
C7 C9 1.5428(19) . ?
C7 C10 1.5476(18) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.4606(19) . y
C11 C12 1.3834(19) . y
C11 C19 1.4496(19) . y
C12 H12 0.9500 . ?
C13 C14 1.3991(19) . ?
C13 C18 1.4069(19) . ?
C14 C15 1.385(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3976(19) . ?
C17 H17 0.9500 . ?
C18 N3 1.4213(18) 3_757 ?
C19 H19 0.9500 . ?
Cl1 C20 1.7563(17) . ?
Cl2 C20 1.7637(16) . ?
Cl3 C20 1.7559(16) . ?
C20 H20 0.97(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N N3 0.817(19) 2.071(18) 2.7218(17) 136.4(17) .
N2 H2N N3 0.817(19) 2.354(18) 2.7095(17) 107.1(15) 3_757
C5 H5 N1 0.95 2.60 3.3278(19) 134.2 4_565
C17 H17 Cg 0.95 2.82 3.6179(17) 143 2_646
C20 H20 Cg 0.97(2) 2.32(2) 3.2867(17) 175.1(17) .
#BEGIN Loops that were not found in dictionaries:
loop_
_shelx_res_file
;
TITL LH2.2CHCl3 in P2(1)/n
CELL 0.71073   7.9871  19.6913  12.3598  90.000 105.868  90.000
ZERR    2.00   0.0002   0.0002   0.0002   0.000   0.002   0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C  H  N  Cl
UNIT 80  72 12  12
OMIT -2 54
L.S. 8
ACTA 54
BOND $H
SIZE 0.20 0.25 0.33
TEMP -173
WGHT    0.043600    1.383700
FVAR       0.13022
N1    3    1.199836    0.185073    0.724964    11.00000    0.01556    0.01596 =
         0.01245    0.00099    0.00288   -0.00254
N2    3    0.827132    0.043187    0.873774    11.00000    0.01196    0.01566 =
         0.01220    0.00167    0.00153   -0.00127
H2N   2    0.909368    0.034402    0.927843    11.00000   -1.20000
N3    3    1.169698    0.061092    0.982654    11.00000    0.01333    0.01525 =
         0.01285    0.00098    0.00240   -0.00039
C1    1    1.189066    0.221561    0.625068    11.00000    0.01608    0.01280 =
         0.01272    0.00019    0.00460    0.00028
C2    1    1.318980    0.261620    0.602130    11.00000    0.01674    0.01569 =
         0.01695    0.00014    0.00562   -0.00177
AFIX  43
H2    2    1.429067    0.266673    0.655647    11.00000   -1.20000
AFIX   0
C3    1    1.281987    0.294092    0.497863    11.00000    0.02095    0.01424 =
         0.02118    0.00166    0.01122   -0.00022
AFIX  43
H3    2    1.368335    0.321675    0.480016    11.00000   -1.20000
AFIX   0
C4    1    1.120194    0.286656    0.419495    11.00000    0.02517    0.01381 =
         0.01477    0.00346    0.00880    0.00472
AFIX  43
H4    2    1.097778    0.309234    0.349053    11.00000   -1.20000
AFIX   0
C5    1    0.990270    0.246270    0.443423    11.00000    0.01820    0.01445 =
         0.01380    0.00025    0.00351    0.00356
AFIX  43
H5    2    0.879826    0.241331    0.390250    11.00000   -1.20000
AFIX   0
C6    1    1.027101    0.213766    0.546569    11.00000    0.01496    0.01110 =
         0.01411   -0.00140    0.00527    0.00060
C7    1    0.918149    0.167401    0.597512    11.00000    0.01312    0.01425 =
         0.01112    0.00069    0.00160   -0.00094
C8    1    0.750670    0.204487    0.603112    11.00000    0.01484    0.01978 =
         0.01916    0.00167    0.00452    0.00181
AFIX  33
H8A   2    0.673967    0.210226    0.526869    11.00000   -1.50000
H8B   2    0.780760    0.249144    0.638009    11.00000   -1.50000
H8C   2    0.690851    0.177658    0.648015    11.00000   -1.50000
AFIX   0
C9    1    0.877127    0.100999    0.529104    11.00000    0.01955    0.01620 =
         0.01477   -0.00196    0.00321   -0.00279
AFIX  33
H9A   2    0.792924    0.110279    0.456531    11.00000   -1.50000
H9B   2    0.827985    0.067737    0.570875    11.00000   -1.50000
H9C   2    0.984416    0.082804    0.516455    11.00000   -1.50000
AFIX   0
C10   1    1.050284    0.154969    0.713272    11.00000    0.01403    0.01376 =
         0.01203   -0.00132    0.00308    0.00005
C11   1    1.022685    0.112276    0.803497    11.00000    0.01527    0.01443 =
         0.01149    0.00021    0.00346    0.00005
C12   1    0.862357    0.082820    0.794992    11.00000    0.01514    0.01363 =
         0.01225    0.00079    0.00237    0.00046
AFIX  43
H12   2    0.771226    0.091329    0.728738    11.00000   -1.20000
AFIX   0
C13   1    0.670006    0.008193    0.862912    11.00000    0.01327    0.01514 =
         0.01279   -0.00178    0.00437   -0.00083
C14   1    0.515938    0.027053    0.783352    11.00000    0.01556    0.01672 =
         0.01478    0.00275    0.00347    0.00111
AFIX  43
H14   2    0.515220    0.065325    0.736430    11.00000   -1.20000
AFIX   0
C15   1    0.364408   -0.009749    0.772582    11.00000    0.01304    0.02197 =
         0.01649    0.00113    0.00146    0.00177
AFIX  43
H15   2    0.260337    0.003044    0.718033    11.00000   -1.20000
AFIX   0
C16   1    0.365061   -0.065414    0.841771    11.00000    0.01297    0.02314 =
         0.02061    0.00121    0.00377   -0.00441
AFIX  43
H16   2    0.261704   -0.091072    0.833962    11.00000   -1.20000
AFIX   0
C17   1    0.516497   -0.083495    0.922165    11.00000    0.01587    0.01910 =
         0.01709    0.00328    0.00410   -0.00285
AFIX  43
H17   2    0.515516   -0.121621    0.969086    11.00000   -1.20000
AFIX   0
C18   1    0.670664   -0.046814    0.935669    11.00000    0.01351    0.01552 =
         0.01219   -0.00034    0.00399    0.00023
C19   1    1.173440    0.098359    0.897092    11.00000    0.01360    0.01403 =
         0.01373   -0.00067    0.00413   -0.00143
AFIX  43
H19   2    1.281625    0.117787    0.895527    11.00000   -1.20000
AFIX   0
CL1   4    1.434479    0.158247    0.323380    11.00000    0.02721    0.04799 =
         0.02379    0.00406    0.00680    0.00403
CL2   4    1.099367    0.092927    0.284907    11.00000    0.02071    0.04987 =
         0.03156   -0.01620   -0.00420    0.00480
CL3   4    1.367919    0.067757    0.490984    11.00000    0.02953    0.02442 =
         0.03654    0.00873   -0.00317    0.00088
C20   1    1.277257    0.128157    0.386943    11.00000    0.02114    0.02155 =
         0.01882   -0.00270    0.00025    0.00555
H20   2    1.233999    0.165196    0.423815    11.00000   -1.20000
 
HKLF 4
 
REM  hamid1517_0m in P2(1)/n
REM R1 =  0.0336 for   3738 Fo > 4sig(Fo)  and  0.0366 for all   4076 data
REM    241 parameters refined using      0 restraints
 
END  
     
WGHT      0.0437      1.3826 
REM Highest difference peak  0.518,  deepest hole -0.439,  1-sigma level  0.056
Q1    1   1.1413  0.1167  0.2409  11.00000  0.05    0.52
Q2    1   0.7171  0.2320  0.5346  11.00000  0.05    0.38
Q3    1   0.6513  0.1725  0.6055  11.00000  0.05    0.35
Q4    1   1.0894  0.1042  0.8480  11.00000  0.05    0.35
;
#END Loops that were not found in dictionaries
