#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:08:37 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179441 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/38/4333855.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_4333855
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 H36 N6, 2(Cl)'
_chemical_formula_sum            'C38 H36 Cl2 N6'
_chemical_formula_weight         647.63
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.606(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6659(3)
_cell_length_b                   14.5944(7)
_cell_length_c                   16.4058(8)
_cell_measurement_reflns_used    2450
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.79
_cell_volume                     1568.77(13)
_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      90(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12542
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3758
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0406
_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)+(0.0483P)²+0.6725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                2815
_reflns_number_total             3758
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302150j_si_002_03.cif
_cod_data_source_block           LH4.2Cl
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4333855
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
N1 N 1.1828(2) 0.45437(10) 0.17919(9) 0.0145(3) Uani 1 1 d D
H1N H 1.273(3) 0.4979(12) 0.1957(12) 0.017 Uiso 1 1 d D
N2 N 0.8521(2) 0.43089(9) 0.41727(9) 0.0138(3) Uani 1 1 d .
N3 N 1.1945(2) 0.53288(10) 0.42490(9) 0.0134(3) Uani 1 1 d D
H3N H 1.097(3) 0.5110(13) 0.4475(11) 0.016 Uiso 1 1 d D
C1 C 1.1465(3) 0.42196(11) 0.09650(10) 0.0144(4) Uani 1 1 d .
C2 C 1.2443(3) 0.44748(12) 0.03231(11) 0.0163(4) Uani 1 1 d .
H2 H 1.3581 0.4878 0.0409 0.020 Uiso 1 1 calc R
C3 C 1.1662(3) 0.41068(12) -0.04545(11) 0.0184(4) Uani 1 1 d .
H3 H 1.2297 0.4250 -0.0912 0.022 Uiso 1 1 calc R
C4 C 0.9962(3) 0.35310(12) -0.05709(11) 0.0188(4) Uani 1 1 d .
H4 H 0.9428 0.3308 -0.1111 0.023 Uiso 1 1 calc R
C5 C 0.9037(3) 0.32769(12) 0.00858(11) 0.0170(4) Uani 1 1 d .
H5 H 0.7894 0.2876 0.0004 0.020 Uiso 1 1 calc R
C6 C 0.9827(3) 0.36238(11) 0.08657(10) 0.0145(3) Uani 1 1 d .
C7 C 0.9148(3) 0.34922(11) 0.16890(10) 0.0143(4) Uani 1 1 d .
C8 C 0.6823(3) 0.36511(13) 0.15985(11) 0.0200(4) Uani 1 1 d .
H8A H 0.6555 0.4306 0.1654 0.030 Uiso 1 1 calc R
H8B H 0.6307 0.3311 0.2032 0.030 Uiso 1 1 calc R
H8C H 0.6132 0.3437 0.1052 0.030 Uiso 1 1 calc R
C9 C 0.9752(3) 0.25150(12) 0.20153(11) 0.0213(4) Uani 1 1 d .
H9A H 0.9064 0.2061 0.1620 0.032 Uiso 1 1 calc R
H9B H 0.9341 0.2427 0.2554 0.032 Uiso 1 1 calc R
H9C H 1.1234 0.2439 0.2078 0.032 Uiso 1 1 calc R
C10 C 1.0518(3) 0.41984(11) 0.22295(10) 0.0144(4) Uani 1 1 d .
C11 C 1.0448(3) 0.44497(11) 0.30623(10) 0.0133(3) Uani 1 1 d .
C12 C 0.8864(3) 0.40764(11) 0.34530(11) 0.0153(4) Uani 1 1 d .
H12 H 0.8002 0.3622 0.3157 0.018 Uiso 1 1 calc R
C13 C 0.6820(3) 0.39096(11) 0.44516(10) 0.0129(3) Uani 1 1 d .
C14 C 0.5356(3) 0.33474(12) 0.39685(11) 0.0166(4) Uani 1 1 d .
H14 H 0.5467 0.3216 0.3411 0.020 Uiso 1 1 calc R
C15 C 0.3757(3) 0.29827(12) 0.42904(11) 0.0173(4) Uani 1 1 d .
H15 H 0.2788 0.2600 0.3954 0.021 Uiso 1 1 calc R
C16 C 0.3552(3) 0.31708(12) 0.51014(11) 0.0177(4) Uani 1 1 d .
H16 H 0.2445 0.2918 0.5318 0.021 Uiso 1 1 calc R
C17 C 0.4966(3) 0.37280(11) 0.55939(11) 0.0166(4) Uani 1 1 d .
H17 H 0.4835 0.3857 0.6149 0.020 Uiso 1 1 calc R
C18 C 0.6585(3) 0.40979(11) 0.52695(10) 0.0131(3) Uani 1 1 d .
C19 C 1.1924(3) 0.50569(11) 0.34844(10) 0.0136(3) Uani 1 1 d .
H19 H 1.2950 0.5280 0.3204 0.016 Uiso 1 1 calc R
Cl1 Cl 1.50399(8) 0.60596(3) 0.21963(3) 0.02476(13) 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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C1 112.23(14) . . ?
C10 N1 H1N 125.8(13) . . ?
C1 N1 H1N 121.5(13) . . ?
C12 N2 C13 118.23(14) . . y
C19 N3 C18 126.63(15) . 3_766 y
C19 N3 H3N 114.9(13) . . ?
C18 N3 H3N 118.5(13) 3_766 . ?
C6 C1 C2 123.42(16) . . ?
C6 C1 N1 108.37(15) . . ?
C2 C1 N1 128.09(16) . . ?
C1 C2 C3 116.29(17) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
C2 C3 C4 120.96(17) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 121.40(16) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C6 C5 C4 118.13(17) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C1 C6 C5 119.74(17) . . ?
C1 C6 C7 109.53(14) . . ?
C5 C6 C7 130.70(16) . . ?
C6 C7 C10 100.68(14) . . ?
C6 C7 C8 110.74(14) . . ?
C10 C7 C8 115.55(14) . . ?
C6 C7 C9 108.87(14) . . ?
C10 C7 C9 109.09(13) . . ?
C8 C7 C9 111.30(15) . . ?
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 124.20(15) . . ?
N1 C10 C7 108.73(14) . . ?
C11 C10 C7 127.07(16) . . ?
C19 C11 C10 119.41(16) . . ?
C19 C11 C12 121.51(15) . . y
C10 C11 C12 119.07(15) . . ?
N2 C12 C11 125.22(15) . . y
N2 C12 H12 117.4 . . ?
C11 C12 H12 117.4 . . ?
C14 C13 C18 117.71(16) . . ?
C14 C13 N2 124.76(15) . . ?
C18 C13 N2 117.52(14) . . y
C15 C14 C13 121.01(16) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.59(16) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.84(17) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 119.66(16) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 121.18(15) . . ?
C17 C18 N3 121.38(15) . 3_766 ?
C13 C18 N3 117.44(15) . 3_766 y
N3 C19 C11 122.94(16) . . y
N3 C19 H19 118.5 . . ?
C11 C19 H19 118.5 . . ?
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
N1 C10 1.328(2) . y
N1 C1 1.415(2) . ?
N1 H1N 0.882(15) . ?
N2 C12 1.289(2) . y
N2 C13 1.423(2) . y
N3 C19 1.313(2) . y
N3 C18 1.414(2) 3_766 y
N3 H3N 0.865(15) . ?
C1 C6 1.382(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.394(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.514(2) . ?
C7 C10 1.544(2) . ?
C7 C8 1.547(2) . ?
C7 C9 1.550(2) . ?
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 1.424(2) . y
C11 C19 1.408(2) . y
C11 C12 1.440(2) . y
C12 H12 0.9500 . ?
C13 C14 1.403(2) . ?
C13 C18 1.407(2) . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(2) . ?
C17 H17 0.9500 . ?
C18 N3 1.414(2) 3_766 ?
C19 H19 0.9500 . ?
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
N1 H1N Cl1 0.882(15) 2.189(15) 3.0653(15) 172.3(18) .
N3 H3N N2 0.865(15) 1.996(17) 2.709(2) 138.9(17) .
N3 H3N N2 0.865(15) 2.341(19) 2.716(2) 106.4(15) 3_766
C19 H19 Cl1 0.95 2.61 3.5408(18) 166.5 .
C17 H17 Cl1 0.95 2.70 3.6394(18) 168.7 3_766
#BEGIN Loops that were not found in dictionaries:
loop_
_shelx_res_file
;
TITL LH4.2Cl in P2(1)/c
CELL 0.71073   6.6659  14.5944  16.4058  90.000 100.606  90.000
ZERR    2.00   0.0003   0.0007   0.0008   0.000   0.001   0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C  H  N  Cl
UNIT 76  72  12  4
L.S. 12
ACTA 54
BOND $H
SIZE 0.15 0.09 0.06
DFIX 0.88 N1 H1N N3 H3N
TEMP -183
WGHT    0.048300    0.672500
FVAR       0.14600
N1    3    1.182779    0.454369    0.179190    11.00000    0.01392    0.01676 =
         0.01295   -0.00256    0.00317   -0.00181
H1N   2    1.272724    0.497925    0.195687    11.00000   -1.20000
N2    3    0.852058    0.430893    0.417269    11.00000    0.01452    0.01402 =
         0.01289   -0.00004    0.00295   -0.00208
N3    3    1.194494    0.532875    0.424904    11.00000    0.01269    0.01514 =
         0.01280   -0.00096    0.00373   -0.00247
H3N   2    1.097197    0.510984    0.447479    11.00000   -1.20000
C1    1    1.146527    0.421961    0.096501    11.00000    0.01504    0.01492 =
         0.01272   -0.00070    0.00108    0.00560
C2    1    1.244293    0.447479    0.032305    11.00000    0.01475    0.01809 =
         0.01660    0.00087    0.00451    0.00388
AFIX  43
H2    2    1.358126    0.487797    0.040880    11.00000   -1.20000
AFIX   0
C3    1    1.166217    0.410678   -0.045452    11.00000    0.02319    0.01990 =
         0.01321    0.00252    0.00592    0.00964
AFIX  43
H3    2    1.229650    0.425002   -0.091195    11.00000   -1.20000
AFIX   0
C4    1    0.996244    0.353105   -0.057087    11.00000    0.02575    0.01752 =
         0.01164   -0.00307   -0.00042    0.00876
AFIX  43
H4    2    0.942778    0.330839   -0.111135    11.00000   -1.20000
AFIX   0
C5    1    0.903684    0.327691    0.008576    11.00000    0.01949    0.01382 =
         0.01664   -0.00231    0.00091    0.00338
AFIX  43
H5    2    0.789384    0.287643    0.000352    11.00000   -1.20000
AFIX   0
C6    1    0.982664    0.362381    0.086572    11.00000    0.01681    0.01228 =
         0.01419    0.00002    0.00239    0.00448
C7    1    0.914780    0.349223    0.168899    11.00000    0.01595    0.01480 =
         0.01142   -0.00202    0.00037   -0.00146
C8    1    0.682250    0.365108    0.159847    11.00000    0.01390    0.02868 =
         0.01729   -0.00514    0.00267   -0.00312
AFIX 137
H8A   2    0.655523    0.430632    0.165379    11.00000   -1.50000
H8B   2    0.630696    0.331076    0.203191    11.00000   -1.50000
H8C   2    0.613241    0.343679    0.105236    11.00000   -1.50000
AFIX   0
C9    1    0.975242    0.251499    0.201526    11.00000    0.03122    0.01682 =
         0.01523    0.00007    0.00244   -0.00144
AFIX 137
H9A   2    0.906440    0.206095    0.162004    11.00000   -1.50000
H9B   2    0.934126    0.242720    0.255352    11.00000   -1.50000
H9C   2    1.123378    0.243911    0.207847    11.00000   -1.50000
AFIX   0
C10   1    1.051801    0.419842    0.222948    11.00000    0.01200    0.01484 =
         0.01559   -0.00032    0.00065    0.00106
C11   1    1.044849    0.444971    0.306231    11.00000    0.01317    0.01428 =
         0.01246   -0.00173    0.00209   -0.00062
C12   1    0.886392    0.407640    0.345296    11.00000    0.01427    0.01576 =
         0.01535   -0.00289    0.00142   -0.00325
AFIX  43
H12   2    0.800245    0.362236    0.315658    11.00000   -1.20000
AFIX   0
C13   1    0.682004    0.390961    0.445160    11.00000    0.01236    0.01211 =
         0.01395    0.00166    0.00195   -0.00002
C14   1    0.535610    0.334745    0.396850    11.00000    0.01946    0.01800 =
         0.01203   -0.00120    0.00200   -0.00248
AFIX  43
H14   2    0.546718    0.321583    0.341144    11.00000   -1.20000
AFIX   0
C15   1    0.375673    0.298267    0.429035    11.00000    0.01598    0.01672 =
         0.01777   -0.00016   -0.00086   -0.00408
AFIX  43
H15   2    0.278768    0.259961    0.395441    11.00000   -1.20000
AFIX   0
C16   1    0.355165    0.317080    0.510137    11.00000    0.01542    0.01991 =
         0.01823    0.00255    0.00425   -0.00396
AFIX  43
H16   2    0.244508    0.291824    0.531782    11.00000   -1.20000
AFIX   0
C17   1    0.496599    0.372803    0.559386    11.00000    0.01856    0.01711 =
         0.01440   -0.00119    0.00373   -0.00352
AFIX  43
H17   2    0.483455    0.385749    0.614909    11.00000   -1.20000
AFIX   0
C18   1    0.658458    0.409792    0.526952    11.00000    0.01347    0.01049 =
         0.01465   -0.00061    0.00051   -0.00137
C19   1    1.192376    0.505694    0.348438    11.00000    0.01357    0.01374 =
         0.01362    0.00080    0.00317    0.00093
AFIX  43
H19   2    1.295010    0.528016    0.320353    11.00000   -1.20000
AFIX   0
CL1   4    1.503987    0.605955    0.219625    11.00000    0.02790    0.02900 =
         0.01894   -0.00291    0.00837   -0.01149
 
HKLF 4
 
REM  sad in P2(1)/c
REM R1 =  0.0406 for   2815 Fo > 4sig(Fo)  and  0.0627 for all   3758 data
REM    216 parameters refined using      2 restraints
 
END  
     
WGHT      0.0483      0.6725 
REM Highest difference peak  0.448,  deepest hole -0.398,  1-sigma level  0.057
Q1    1   1.5523  0.5409  0.2324  11.00000  0.05    0.45
Q2    1   1.3666  0.6597  0.2317  11.00000  0.05    0.38
Q3    1   0.6630  0.4078  0.4816  11.00000  0.05    0.30
Q4    1   0.5895  0.3787  0.4202  11.00000  0.05    0.28
;
#END Loops that were not found in dictionaries
