#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:17:18 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179239 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/59/4315934.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_4315934
loop_
_publ_author_name
'Saovalak Sripothongnak'
'Christopher J. Ziegler'
_publ_section_title
;
 Lithium Complexes of N-Confused Porphyrin
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5789
_journal_page_last               5791
_journal_paper_doi               10.1021/ic1005659
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C44 H29 Li N4'
_chemical_formula_weight         620.65
_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                 114.863(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.618(6)
_cell_length_b                   17.109(8)
_cell_length_c                   14.865(7)
_cell_measurement_reflns_used    2358
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.76
_cell_measurement_theta_min      2.66
_cell_volume                     3142(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0917
_diffrn_reflns_av_sigmaI/netI    0.0914
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25981
_diffrn_reflns_theta_full        27.25
_diffrn_reflns_theta_max         27.25
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_correction_T_min  0.9923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS; Sheldrick, 2000 [Sheldrick, G. M. (2000)]'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         6972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0777
_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)+(0.0380P)²+1.3058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1588
_reflns_number_gt                4529
_reflns_number_total             6972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic1005659_si_001_1.cif
_cod_data_source_block           1Li
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4315934
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1542(2) 0.04698(16) 0.6068(2) 0.0322(6) Uani 1 1 d . . .
C2 C -0.2634(2) 0.06085(17) 0.5963(2) 0.0328(6) Uani 1 1 d . . .
C3 C -0.2980(2) 0.12734(17) 0.5436(2) 0.0339(7) Uani 1 1 d . . .
C4 C -0.2101(2) 0.15584(16) 0.5216(2) 0.0319(6) Uani 1 1 d . . .
C5 C -0.2165(2) 0.22500(16) 0.4656(2) 0.0315(6) Uani 1 1 d . . .
C6 C -0.1305(2) 0.26054(16) 0.4538(2) 0.0320(6) Uani 1 1 d . . .
C7 C -0.1367(2) 0.33449(17) 0.4032(2) 0.0348(7) Uani 1 1 d . . .
C8 C -0.0353(2) 0.35310(17) 0.4175(2) 0.0352(7) Uani 1 1 d . . .
C9 C 0.0351(2) 0.29070(16) 0.4767(2) 0.0323(6) Uani 1 1 d . . .
C10 C 0.1484(2) 0.29001(16) 0.5127(2) 0.0317(6) Uani 1 1 d . . .
C11 C 0.2175(2) 0.22919(16) 0.5709(2) 0.0320(6) Uani 1 1 d . . .
C12 C 0.3351(2) 0.23137(18) 0.6069(2) 0.0360(7) Uani 1 1 d . . .
C13 C 0.3731(2) 0.16328(17) 0.6527(2) 0.0354(7) Uani 1 1 d . . .
C14 C 0.2799(2) 0.11765(16) 0.64602(19) 0.0316(6) Uani 1 1 d . . .
C15 C 0.2838(2) 0.04210(16) 0.68096(19) 0.0305(6) Uani 1 1 d . . .
C16 C 0.1898(2) 0.00522(16) 0.68218(19) 0.0313(6) Uani 1 1 d . . .
C17 C 0.0721(2) -0.09162(15) 0.66492(18) 0.0261(6) Uani 1 1 d . . .
H17 H 0.0414 -0.1424 0.6580 0.031 Uiso 1 1 calc R . .
C18 C 0.0961(2) 0.03748(18) 0.6821(2) 0.0332(7) Uani 1 1 d . . .
C19 C 0.0212(2) -0.02229(16) 0.6684(2) 0.0326(6) Uani 1 1 d . . .
C20 C -0.0907(2) -0.01777(16) 0.6524(2) 0.0314(6) Uani 1 1 d . . .
C21 C -0.3260(2) 0.26320(16) 0.4152(2) 0.0333(7) Uani 1 1 d . . .
C22 C -0.3921(3) 0.24847(19) 0.3159(3) 0.0445(8) Uani 1 1 d . . .
C23 C -0.4931(3) 0.28314(19) 0.2697(3) 0.0490(9) Uani 1 1 d . . .
C24 C -0.5301(2) 0.33248(19) 0.3214(3) 0.0452(8) Uani 1 1 d . . .
C25 C -0.4661(3) 0.3471(2) 0.4202(3) 0.0476(8) Uani 1 1 d . . .
C26 C -0.3640(2) 0.31273(19) 0.4664(3) 0.0435(8) Uani 1 1 d . . .
C27 C 0.2008(2) 0.35823(16) 0.4865(2) 0.0342(7) Uani 1 1 d . . .
C28 C 0.1883(2) 0.36956(18) 0.3897(2) 0.0378(7) Uani 1 1 d . . .
C29 C 0.2395(3) 0.43076(19) 0.3661(3) 0.0431(8) Uani 1 1 d . . .
C30 C 0.3032(2) 0.48252(19) 0.4385(3) 0.0436(8) Uani 1 1 d . . .
C31 C 0.3149(2) 0.47324(18) 0.5348(2) 0.0411(7) Uani 1 1 d . . .
C32 C 0.2642(2) 0.41136(18) 0.5586(2) 0.0374(7) Uani 1 1 d . . .
C33 C 0.3851(2) -0.00422(16) 0.7154(2) 0.0322(6) Uani 1 1 d . . .
C34 C 0.4428(2) -0.01180(17) 0.6573(2) 0.0339(7) Uani 1 1 d . . .
C35 C 0.5359(2) -0.05631(18) 0.6887(3) 0.0402(7) Uani 1 1 d . . .
C36 C 0.5752(2) -0.09270(18) 0.7803(2) 0.0423(8) Uani 1 1 d . . .
C37 C 0.5201(2) -0.08619(18) 0.8395(2) 0.0408(7) Uani 1 1 d . . .
C38 C 0.4248(2) -0.04325(17) 0.8074(2) 0.0349(7) Uani 1 1 d . . .
C39 C -0.1362(2) -0.08621(16) 0.6826(2) 0.0316(6) Uani 1 1 d . . .
C40 C -0.2346(2) -0.12030(17) 0.6203(2) 0.0333(7) Uani 1 1 d . . .
C41 C -0.2748(2) -0.18442(17) 0.6509(2) 0.0381(7) Uani 1 1 d . . .
C42 C -0.2174(2) -0.21583(19) 0.7446(2) 0.0408(7) Uani 1 1 d . . .
C43 C -0.1176(2) -0.18441(18) 0.8059(2) 0.0400(7) Uani 1 1 d . . .
C44 C -0.0783(2) -0.12039(18) 0.7756(2) 0.0366(7) Uani 1 1 d . . .
H2 H -0.303(2) 0.0269(15) 0.6239(19) 0.029(7) Uiso 1 1 d . . .
H3 H -0.370(2) 0.1545(15) 0.5221(19) 0.030(7) Uiso 1 1 d . . .
H7 H -0.204(2) 0.3619(18) 0.368(2) 0.050(9) Uiso 1 1 d . . .
H8 H -0.012(2) 0.4007(19) 0.396(2) 0.054(9) Uiso 1 1 d . . .
H12 H 0.375(2) 0.2725(17) 0.597(2) 0.037(8) Uiso 1 1 d . . .
H13 H 0.448(3) 0.1428(18) 0.682(2) 0.054(9) Uiso 1 1 d . . .
H18 H 0.087(2) 0.0936(18) 0.697(2) 0.050(9) Uiso 1 1 d . . .
H22 H -0.364(2) 0.2175(19) 0.281(2) 0.054(10) Uiso 1 1 d . . .
H23 H -0.534(3) 0.2707(18) 0.203(2) 0.056(10) Uiso 1 1 d . . .
H24 H -0.601(3) 0.3579(19) 0.292(2) 0.060(10) Uiso 1 1 d . . .
H25 H -0.491(2) 0.3809(18) 0.461(2) 0.049(9) Uiso 1 1 d . . .
H26 H -0.314(2) 0.3241(18) 0.541(2) 0.055(9) Uiso 1 1 d . . .
H28 H 0.147(2) 0.3349(18) 0.337(2) 0.051(9) Uiso 1 1 d . . .
H29 H 0.232(2) 0.4381(16) 0.301(2) 0.036(8) Uiso 1 1 d . . .
H30 H 0.338(2) 0.5272(17) 0.425(2) 0.044(8) Uiso 1 1 d . . .
H31 H 0.362(2) 0.5105(17) 0.586(2) 0.046(9) Uiso 1 1 d . . .
H32 H 0.273(2) 0.4039(17) 0.627(2) 0.046(9) Uiso 1 1 d . . .
H34 H 0.419(2) 0.0147(17) 0.593(2) 0.044(8) Uiso 1 1 d . . .
H35 H 0.574(2) -0.0610(16) 0.646(2) 0.038(8) Uiso 1 1 d . . .
H36 H 0.637(2) -0.1271(16) 0.800(2) 0.037(8) Uiso 1 1 d . . .
H37 H 0.547(2) -0.1122(18) 0.905(2) 0.052(9) Uiso 1 1 d . . .
H38 H 0.380(2) -0.0406(15) 0.8456(19) 0.031(7) Uiso 1 1 d . . .
H40 H -0.271(2) -0.1012(16) 0.553(2) 0.038(8) Uiso 1 1 d . . .
H41 H -0.345(2) -0.2085(16) 0.606(2) 0.036(8) Uiso 1 1 d . . .
H42 H -0.242(2) -0.2619(18) 0.764(2) 0.046(9) Uiso 1 1 d . . .
H43 H -0.076(2) -0.2071(16) 0.874(2) 0.042(8) Uiso 1 1 d . . .
H44 H -0.013(2) -0.0969(16) 0.816(2) 0.033(8) Uiso 1 1 d . . .
Li1 Li 0.0254(4) 0.1361(3) 0.5604(4) 0.0466(13) Uani 1 1 d . . .
N1 N -0.12269(17) 0.10756(13) 0.56209(17) 0.0327(5) Uani 1 1 d . . .
N2 N -0.02493(17) 0.23445(13) 0.49549(17) 0.0331(6) Uani 1 1 d . . .
N3 N 0.18608(17) 0.16093(13) 0.59635(17) 0.0330(5) Uani 1 1 d . . .
N4 N 0.1724(2) -0.07533(15) 0.67302(18) 0.0446(7) Uani 1 1 d . . .
H4N H 0.2197 -0.1102 0.6726 0.053 Uiso 1 1 calc R . .
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'
Li Li -0.0003 0.0001 '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'
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
N1 C1 C20 124.9(3) . . ?
N1 C1 C2 109.6(2) . . ?
C20 C1 C2 125.6(3) . . ?
C3 C2 C1 107.1(3) . . ?
C2 C3 C4 107.1(3) . . ?
N1 C4 C5 126.0(3) . . ?
N1 C4 C3 110.3(2) . . ?
C5 C4 C3 123.7(2) . . ?
C6 C5 C4 125.8(2) . . ?
C6 C5 C21 117.1(2) . . ?
C4 C5 C21 117.1(2) . . ?
N2 C6 C5 125.1(2) . . ?
N2 C6 C7 109.7(2) . . ?
C5 C6 C7 125.1(2) . . ?
C8 C7 C6 107.0(3) . . ?
C7 C8 C9 107.1(3) . . ?
N2 C9 C10 124.9(2) . . ?
N2 C9 C8 109.9(2) . . ?
C10 C9 C8 125.1(3) . . ?
C9 C10 C11 125.2(3) . . ?
C9 C10 C27 117.4(2) . . ?
C11 C10 C27 117.4(2) . . ?
N3 C11 C10 126.5(2) . . ?
N3 C11 C12 110.3(2) . . ?
C10 C11 C12 123.1(3) . . ?
C13 C12 C11 107.2(3) . . ?
C12 C13 C14 106.9(3) . . ?
C15 C14 N3 125.3(2) . . ?
C15 C14 C13 125.4(2) . . ?
N3 C14 C13 109.3(2) . . ?
C14 C15 C16 121.5(2) . . ?
C14 C15 C33 120.7(2) . . ?
C16 C15 C33 117.8(2) . . ?
C18 C16 N4 105.9(2) . . ?
C18 C16 C15 130.5(3) . . ?
N4 C16 C15 123.3(2) . . ?
N4 C17 C19 108.9(2) . . ?
C16 C18 C19 108.9(3) . . ?
C16 C18 Li1 111.3(2) . . ?
C19 C18 Li1 111.9(2) . . ?
C17 C19 C18 106.6(2) . . ?
C17 C19 C20 123.4(2) . . ?
C18 C19 C20 129.9(3) . . ?
C1 C20 C19 121.3(3) . . ?
C1 C20 C39 121.6(2) . . ?
C19 C20 C39 117.1(2) . . ?
C26 C21 C22 118.1(3) . . ?
C26 C21 C5 121.0(3) . . ?
C22 C21 C5 120.9(3) . . ?
C23 C22 C21 120.9(3) . . ?
C24 C23 C22 120.4(3) . . ?
C23 C24 C25 119.4(3) . . ?
C24 C25 C26 120.0(3) . . ?
C21 C26 C25 121.0(3) . . ?
C28 C27 C32 118.1(3) . . ?
C28 C27 C10 120.8(3) . . ?
C32 C27 C10 121.1(3) . . ?
C29 C28 C27 120.9(3) . . ?
C28 C29 C30 120.4(3) . . ?
C31 C30 C29 119.6(3) . . ?
C30 C31 C32 119.9(3) . . ?
C31 C32 C27 121.1(3) . . ?
C34 C33 C38 118.1(3) . . ?
C34 C33 C15 121.3(2) . . ?
C38 C33 C15 120.6(3) . . ?
C35 C34 C33 121.1(3) . . ?
C34 C35 C36 120.1(3) . . ?
C37 C36 C35 120.1(3) . . ?
C36 C37 C38 120.2(3) . . ?
C37 C38 C33 120.3(3) . . ?
C40 C39 C44 117.7(3) . . ?
C40 C39 C20 122.5(2) . . ?
C44 C39 C20 119.7(2) . . ?
C41 C40 C39 121.0(3) . . ?
C40 C41 C42 120.2(3) . . ?
C41 C42 C43 119.5(3) . . ?
C44 C43 C42 120.1(3) . . ?
C43 C44 C39 121.4(3) . . ?
N2 Li1 N3 93.8(2) . . ?
N2 Li1 N1 94.0(2) . . ?
N3 Li1 N1 165.7(3) . . ?
N2 Li1 C18 163.0(3) . . ?
N3 Li1 C18 84.4(2) . . ?
N1 Li1 C18 84.7(2) . . ?
C4 N1 C1 106.0(2) . . ?
C4 N1 Li1 121.4(2) . . ?
C1 N1 Li1 132.4(2) . . ?
C9 N2 C6 106.3(2) . . ?
C9 N2 Li1 127.1(2) . . ?
C6 N2 Li1 126.5(2) . . ?
C11 N3 C14 106.3(2) . . ?
C11 N3 Li1 122.1(2) . . ?
C14 N3 Li1 131.7(2) . . ?
C17 N4 C16 109.7(2) . . ?
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
C1 N1 1.393(3) . ?
C1 C20 1.393(4) . ?
C1 C2 1.448(4) . ?
C2 C3 1.349(4) . ?
C3 C4 1.453(4) . ?
C4 N1 1.363(3) . ?
C4 C5 1.428(4) . ?
C5 C6 1.395(4) . ?
C5 C21 1.507(4) . ?
C6 N2 1.379(3) . ?
C6 C7 1.456(4) . ?
C7 C8 1.343(4) . ?
C8 C9 1.457(4) . ?
C9 N2 1.366(3) . ?
C9 C10 1.405(4) . ?
C10 C11 1.425(4) . ?
C10 C27 1.502(4) . ?
C11 N3 1.352(3) . ?
C11 C12 1.459(4) . ?
C12 C13 1.339(4) . ?
C13 C14 1.458(4) . ?
C14 C15 1.386(4) . ?
C14 N3 1.390(3) . ?
C15 C16 1.433(4) . ?
C15 C33 1.484(4) . ?
C16 C18 1.390(4) . ?
C16 N4 1.395(4) . ?
C17 N4 1.349(3) . ?
C17 C19 1.386(4) . ?
C18 C19 1.398(4) . ?
C18 Li1 2.363(6) . ?
C19 C20 1.442(4) . ?
C20 C39 1.479(4) . ?
C21 C26 1.378(4) . ?
C21 C22 1.391(4) . ?
C22 C23 1.385(4) . ?
C23 C24 1.373(5) . ?
C24 C25 1.379(5) . ?
C25 C26 1.397(4) . ?
C27 C28 1.390(4) . ?
C27 C32 1.393(4) . ?
C28 C29 1.382(4) . ?
C29 C30 1.383(5) . ?
C30 C31 1.382(4) . ?
C31 C32 1.388(4) . ?
C33 C34 1.397(4) . ?
C33 C38 1.410(4) . ?
C34 C35 1.381(4) . ?
C35 C36 1.384(4) . ?
C36 C37 1.380(5) . ?
C37 C38 1.389(4) . ?
C39 C40 1.396(4) . ?
C39 C44 1.400(4) . ?
C40 C41 1.385(4) . ?
C41 C42 1.387(4) . ?
C42 C43 1.387(4) . ?
C43 C44 1.376(4) . ?
Li1 N2 1.916(6) . ?
Li1 N3 2.067(6) . ?
Li1 N1 2.085(6) . ?
