#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/37/4323730.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_4323730
loop_
_publ_author_name
'Mathias O. Senge'
'Werner W. Kalisch'
_publ_section_title
;
 Synthesis and Structural Characterization of Nonplanar
 Tetraphenylporphyrins and Their Metal Complexes with Graded Degrees of
 β-Ethyl Substitution
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6103
_journal_page_last               6116
_journal_paper_doi               10.1021/ic970765g
_journal_volume                  36
_journal_year                    1997
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C48 H38 N4'
_chemical_formula_structural     'C48 H38 N4'
_chemical_formula_sum            'C48 H38 N4'
_chemical_formula_weight         670.82
_chemical_name_common            DEtTPP
_chemical_name_systematic
; 
 2,3-Diethyl-5,10,15,20-tetraphenylporphyrin 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 109.65(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.333(12)
_cell_length_b                   20.664(14)
_cell_length_c                   10.180(6)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     3632(4)
_computing_cell_refinement       'Siemens P3'
_computing_data_collection       'Siemens P3'
_computing_data_reduction        'XDISK, Shelxtl-Plus, Siemens, 1994'
_computing_molecular_graphics    'XP, Shelxtl-Plus, Siemens, 1994'
_computing_publication_material  'XCIF, Shelxtl-Plus, Siemens, 1994'
_computing_structure_refinement  'XL-94 (Sheldrick, 1994)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130(2)
_diffrn_measurement_device       'Siemens R3m/V'
_diffrn_measurement_method       '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  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5627
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    N/A
_exptl_crystal_description       'irregular shape'
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.52
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3.78(407)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.792
_refine_ls_goodness_of_fit_obs   0.753
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         4412
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.791
_refine_ls_restrained_S_obs      0.753
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_obs          0.0515
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1184P)²+6.4631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1598
_refine_ls_wR_factor_obs         0.1374
_reflns_number_observed          3664
_reflns_number_total             4412
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic970765g_01.cif
_cod_data_source_block           ms234
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/d' 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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1184P)^2^+6.4631P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1184P)^2^+6.4631P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3631.9(40)
_cod_database_code               4323730
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N21 N 0.3238(2) 0.11001(15) 0.3985(3) 0.0275(6) Uani 1 d . .
H21A H 0.3539(2) 0.14512(15) 0.4055(3) 0.080 Uiso 1 d R .
N22 N 0.3042(2) 0.25230(15) 0.3859(3) 0.0282(7) Uani 1 d . .
N23 N 0.4578(2) 0.27906(15) 0.3848(3) 0.0283(7) Uani 1 d . .
H23A H 0.4298(2) 0.24409(15) 0.3905(3) 0.080 Uiso 1 d R .
N24 N 0.4827(2) 0.13927(15) 0.4133(3) 0.0281(6) Uani 1 d . .
C1 C 0.3491(2) 0.0470(2) 0.4019(4) 0.0261(7) Uani 1 d . .
C2 C 0.2831(2) 0.0060(2) 0.3869(4) 0.0265(7) Uani 1 d . .
C2A C 0.2785(2) -0.0669(2) 0.3960(4) 0.0329(8) Uani 1 d . .
H2AA H 0.3198(2) -0.0861(2) 0.3713(4) 0.080 Uiso 1 d R .
H2AB H 0.2303(2) -0.0820(2) 0.3310(4) 0.080 Uiso 1 d R .
C2B C 0.2849(3) -0.0888(2) 0.5429(5) 0.0439(10) Uani 1 d . .
H2BA H 0.2821(3) -0.1351(2) 0.5464(5) 0.080 Uiso 1 d R .
H2BB H 0.3335(3) -0.0744(2) 0.6077(5) 0.080 Uiso 1 d R .
H2BC H 0.2432(3) -0.0701(2) 0.5671(5) 0.080 Uiso 1 d R .
C3 C 0.2198(2) 0.0452(2) 0.3716(4) 0.0280(7) Uani 1 d . .
C3A C 0.1387(2) 0.0191(2) 0.3341(4) 0.0311(8) Uani 1 d . .
H3AA H 0.1081(2) 0.0480(2) 0.3682(4) 0.080 Uiso 1 d R .
H3AB H 0.1400(2) -0.0222(2) 0.3779(4) 0.080 Uiso 1 d R .
C3B C 0.1016(2) 0.0121(2) 0.1760(5) 0.0446(11) Uani 1 d . .
H3BA H 0.0500(2) -0.0046(2) 0.1538(5) 0.080 Uiso 1 d R .
H3BB H 0.0997(2) 0.0536(2) 0.1326(5) 0.080 Uiso 1 d R .
H3BC H 0.1320(2) -0.0172(2) 0.1424(5) 0.080 Uiso 1 d R .
C4 C 0.2462(2) 0.1118(2) 0.3820(4) 0.0263(7) Uani 1 d . .
C5 C 0.2044(2) 0.1689(2) 0.3804(4) 0.0272(7) Uani 1 d . .
C5A C 0.1217(2) 0.1638(2) 0.3735(4) 0.0266(7) Uani 1 d . .
C5B C 0.0618(2) 0.1748(2) 0.2472(4) 0.0321(8) Uani 1 d . .
H5BA H 0.0742(2) 0.1869(2) 0.1661(4) 0.080 Uiso 1 d R .
C5C C -0.0151(2) 0.1691(2) 0.2401(5) 0.0384(9) Uani 1 d . .
H5CA H -0.0556(2) 0.1759(2) 0.1526(5) 0.080 Uiso 1 d R .
C5D C -0.0328(2) 0.1531(2) 0.3578(5) 0.0380(9) Uani 1 d . .
H5DA H -0.0859(2) 0.1484(2) 0.3520(5) 0.080 Uiso 1 d R .
C5E C 0.0258(3) 0.1443(2) 0.4839(5) 0.0382(9) Uani 1 d . .
H5EA H 0.0136(3) 0.1345(2) 0.5663(5) 0.080 Uiso 1 d R .
C5F C 0.1027(2) 0.1494(2) 0.4915(4) 0.0318(8) Uani 1 d . .
H5FA H 0.1432(2) 0.1433(2) 0.5794(4) 0.080 Uiso 1 d R .
C6 C 0.2331(2) 0.2327(2) 0.3892(4) 0.0281(7) Uani 1 d . .
C7 C 0.1858(2) 0.2884(2) 0.3973(4) 0.0341(8) Uani 1 d . .
H7A H 0.1346(2) 0.2869(2) 0.4031(4) 0.080 Uiso 1 d R .
C8 C 0.2282(2) 0.3414(2) 0.3962(5) 0.0354(9) Uani 1 d . .
H8A H 0.2126(2) 0.3855(2) 0.3990(5) 0.080 Uiso 1 d R .
C9 C 0.3012(2) 0.3189(2) 0.3865(4) 0.0292(8) Uani 1 d . .
C10 C 0.3592(2) 0.3612(2) 0.3759(4) 0.0285(8) Uani 1 d . .
C10A C 0.3403(2) 0.4319(2) 0.3665(4) 0.0333(8) Uani 1 d . .
C10B C 0.2832(3) 0.4571(2) 0.2502(5) 0.0472(11) Uani 1 d . .
H10A H 0.2586(3) 0.4290(2) 0.1728(5) 0.080 Uiso 1 d R .
C10C C 0.2612(3) 0.5214(2) 0.2443(7) 0.0582(14) Uani 1 d . .
H10B H 0.2215(3) 0.5376(2) 0.1629(7) 0.080 Uiso 1 d R .
C10D C 0.2962(3) 0.5619(2) 0.3531(7) 0.059(2) Uani 1 d . .
H10C H 0.2812(3) 0.6066(2) 0.3490(7) 0.080 Uiso 1 d R .
C10E C 0.3535(3) 0.5381(2) 0.4690(7) 0.0560(14) Uani 1 d . .
H10D H 0.3776(3) 0.5666(2) 0.5459(7) 0.080 Uiso 1 d R .
C10F C 0.3758(3) 0.4733(2) 0.4771(5) 0.0427(10) Uani 1 d . .
H10E H 0.4155(3) 0.4574(2) 0.5586(5) 0.080 Uiso 1 d R .
C11 C 0.4310(2) 0.3418(2) 0.3727(4) 0.0287(8) Uani 1 d . .
C12 C 0.4934(2) 0.3813(2) 0.3623(4) 0.0321(8) Uani 1 d . .
H12A H 0.4924(2) 0.4275(2) 0.3521(4) 0.080 Uiso 1 d R .
C13 C 0.5543(2) 0.3423(2) 0.3712(4) 0.0314(8) Uani 1 d . .
H13A H 0.6037(2) 0.3559(2) 0.3678(4) 0.080 Uiso 1 d R .
C14 C 0.5325(2) 0.2772(2) 0.3850(4) 0.0292(8) Uani 1 d . .
C15 C 0.5787(2) 0.2214(2) 0.4017(4) 0.0277(7) Uani 1 d . .
C15A C 0.6605(2) 0.2309(2) 0.4049(4) 0.0292(8) Uani 1 d . .
C15B C 0.7220(2) 0.2255(2) 0.5294(4) 0.0351(9) Uani 1 d . .
H15A H 0.7123(2) 0.2155(2) 0.6141(4) 0.080 Uiso 1 d R .
C15C C 0.7975(2) 0.2347(2) 0.5321(5) 0.0425(10) Uani 1 d . .
H15B H 0.8396(2) 0.2314(2) 0.6189(5) 0.080 Uiso 1 d R .
C15D C 0.8128(2) 0.2482(2) 0.4117(5) 0.0391(10) Uani 1 d . .
H15C H 0.8652(2) 0.2543(2) 0.4145(5) 0.080 Uiso 1 d R .
C15E C 0.7521(3) 0.2532(2) 0.2861(5) 0.0426(10) Uani 1 d . .
H15D H 0.7621(3) 0.2630(2) 0.2015(5) 0.080 Uiso 1 d R .
C15F C 0.6762(2) 0.2438(2) 0.2829(4) 0.0379(9) Uani 1 d . .
H15E H 0.6342(2) 0.2466(2) 0.1959(4) 0.080 Uiso 1 d R .
C16 C 0.5550(2) 0.1580(2) 0.4159(4) 0.0298(8) Uani 1 d . .
C17 C 0.6053(2) 0.1024(2) 0.4271(5) 0.0347(8) Uani 1 d . .
H17A H 0.6584(2) 0.1031(2) 0.4314(5) 0.080 Uiso 1 d R .
C18 C 0.5628(2) 0.0499(2) 0.4302(5) 0.0363(9) Uani 1 d . .
H18A H 0.5798(2) 0.0057(2) 0.4385(5) 0.080 Uiso 1 d R .
C19 C 0.4859(2) 0.0732(2) 0.4209(4) 0.0299(8) Uani 1 d . .
C20 C 0.4249(2) 0.0299(2) 0.4133(4) 0.0284(7) Uani 1 d . .
C20A C 0.4459(2) -0.0404(2) 0.4126(4) 0.0274(7) Uani 1 d . .
C20B C 0.4388(3) -0.0710(2) 0.2872(4) 0.0378(9) Uani 1 d . .
H20A H 0.4188(3) -0.0473(2) 0.2014(4) 0.080 Uiso 1 d R .
C20C C 0.4609(3) -0.1348(2) 0.2853(5) 0.0439(10) Uani 1 d . .
H20B H 0.4557(3) -0.1553(2) 0.1980(5) 0.080 Uiso 1 d R .
C20D C 0.4907(3) -0.1690(2) 0.4086(6) 0.0417(10) Uani 1 d . .
H20C H 0.5058(3) -0.2134(2) 0.4071(6) 0.080 Uiso 1 d R .
C20E C 0.4982(3) -0.1390(2) 0.5339(5) 0.0434(10) Uani 1 d . .
H20D H 0.5179(3) -0.1628(2) 0.6195(5) 0.080 Uiso 1 d R .
C20F C 0.4771(2) -0.0747(2) 0.5366(4) 0.0381(9) Uani 1 d . .
H20E H 0.4841(2) -0.0536(2) 0.6240(4) 0.080 Uiso 1 d 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'
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
C4 N21 C1 110.8(3) . . ?
C9 N22 C6 104.8(3) . . ?
C14 N23 C11 110.8(3) . . ?
C19 N24 C16 105.0(3) . . ?
N21 C1 C20 123.9(3) . . ?
N21 C1 C2 106.8(3) . . ?
C20 C1 C2 129.3(3) . . ?
C3 C2 C1 108.0(3) . . ?
C3 C2 C2A 122.0(3) . . ?
C1 C2 C2A 129.8(3) . . ?
C2 C2A C2B 111.5(3) . . ?
C2 C3 C4 107.6(3) . . ?
C2 C3 C3A 122.6(3) . . ?
C4 C3 C3A 129.4(3) . . ?
C3 C3A C3B 110.6(3) . . ?
N21 C4 C5 124.2(3) . . ?
N21 C4 C3 106.7(3) . . ?
C5 C4 C3 129.0(3) . . ?
C4 C5 C6 126.4(3) . . ?
C4 C5 C5A 118.8(3) . . ?
C6 C5 C5A 114.7(3) . . ?
C5F C5A C5B 118.8(3) . . ?
C5F C5A C5 121.2(3) . . ?
C5B C5A C5 120.0(3) . . ?
C5C C5B C5A 120.1(4) . . ?
C5B C5C C5D 120.3(4) . . ?
C5E C5D C5C 120.1(4) . . ?
C5D C5E C5F 120.0(4) . . ?
C5A C5F C5E 120.8(4) . . ?
N22 C6 C5 127.6(3) . . ?
N22 C6 C7 110.8(3) . . ?
C5 C6 C7 121.6(3) . . ?
C8 C7 C6 106.5(4) . . ?
C7 C8 C9 106.8(3) . . ?
N22 C9 C10 126.1(4) . . ?
N22 C9 C8 111.0(3) . . ?
C10 C9 C8 122.9(4) . . ?
C11 C10 C9 124.6(4) . . ?
C11 C10 C10A 118.8(3) . . ?
C9 C10 C10A 116.5(3) . . ?
C10B C10A C10F 118.3(4) . . ?
C10B C10A C10 120.7(4) . . ?
C10F C10A C10 120.9(4) . . ?
C10C C10B C10A 121.4(5) . . ?
C10D C10C C10B 120.2(5) . . ?
C10C C10D C10E 119.4(4) . . ?
C10F C10E C10D 121.1(5) . . ?
C10E C10F C10A 119.7(5) . . ?
N23 C11 C10 125.8(3) . . ?
N23 C11 C12 105.8(3) . . ?
C10 C11 C12 128.4(4) . . ?
C13 C12 C11 108.4(4) . . ?
C12 C13 C14 108.4(4) . . ?
N23 C14 C15 125.8(3) . . ?
N23 C14 C13 106.7(3) . . ?
C15 C14 C13 127.4(4) . . ?
C16 C15 C14 125.6(3) . . ?
C16 C15 C15A 117.5(3) . . ?
C14 C15 C15A 116.9(3) . . ?
C15B C15A C15F 118.8(4) . . ?
C15B C15A C15 120.5(3) . . ?
C15F C15A C15 120.7(3) . . ?
C15A C15B C15C 120.3(4) . . ?
C15D C15C C15B 120.7(4) . . ?
C15C C15D C15E 119.7(4) . . ?
C15F C15E C15D 119.7(4) . . ?
C15E C15F C15A 120.6(4) . . ?
N24 C16 C15 126.4(3) . . ?
N24 C16 C17 111.2(3) . . ?
C15 C16 C17 122.3(4) . . ?
C18 C17 C16 106.4(4) . . ?
C17 C18 C19 106.7(4) . . ?
N24 C19 C20 127.6(4) . . ?
N24 C19 C18 110.7(3) . . ?
C20 C19 C18 121.5(4) . . ?
C1 C20 C19 126.0(3) . . ?
C1 C20 C20A 119.6(3) . . ?
C19 C20 C20A 114.3(3) . . ?
C20F C20A C20B 119.0(3) . . ?
C20F C20A C20 121.0(3) . . ?
C20B C20A C20 119.8(3) . . ?
C20C C20B C20A 120.6(4) . . ?
C20B C20C C20D 120.2(4) . . ?
C20C C20D C20E 119.7(4) . . ?
C20F C20E C20D 120.4(4) . . ?
C20E C20F C20A 120.1(4) . . ?
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
N21 C4 1.375(5) . ?
N21 C1 1.378(5) . ?
N22 C9 1.377(5) . ?
N22 C6 1.375(5) . ?
N23 C14 1.368(5) . ?
N23 C11 1.377(5) . ?
N24 C19 1.368(5) . ?
N24 C16 1.372(5) . ?
C1 C20 1.400(5) . ?
C1 C2 1.443(5) . ?
C2 C3 1.380(5) . ?
C2 C2A 1.514(5) . ?
C2A C2B 1.528(6) . ?
C3 C4 1.451(5) . ?
C3 C3A 1.507(5) . ?
C3A C3B 1.529(6) . ?
C4 C5 1.403(5) . ?
C5 C6 1.412(5) . ?
C5 C5A 1.499(5) . ?
C5A C5F 1.390(5) . ?
C5A C5B 1.400(5) . ?
C5B C5C 1.392(6) . ?
C5C C5D 1.382(7) . ?
C5D C5E 1.381(6) . ?
C5E C5F 1.389(6) . ?
C6 C7 1.460(5) . ?
C7 C8 1.345(6) . ?
C8 C9 1.452(5) . ?
C9 C10 1.408(5) . ?
C10 C11 1.387(5) . ?
C10 C10A 1.498(5) . ?
C10A C10B 1.390(6) . ?
C10A C10F 1.389(6) . ?
C10B C10C 1.385(7) . ?
C10C C10D 1.365(8) . ?
C10D C10E 1.380(9) . ?
C10E C10F 1.394(6) . ?
C11 C12 1.438(5) . ?
C12 C13 1.357(6) . ?
C13 C14 1.424(5) . ?
C14 C15 1.407(5) . ?
C15 C16 1.402(5) . ?
C15 C15A 1.502(5) . ?
C15A C15B 1.389(5) . ?
C15A C15F 1.391(6) . ?
C15B C15C 1.387(6) . ?
C15C C15D 1.376(7) . ?
C15D C15E 1.388(7) . ?
C15E C15F 1.395(6) . ?
C16 C17 1.454(6) . ?
C17 C18 1.342(6) . ?
C18 C19 1.462(6) . ?
C19 C20 1.415(5) . ?
C20 C20A 1.504(5) . ?
C20A C20F 1.391(5) . ?
C20A C20B 1.390(6) . ?
C20B C20C 1.382(6) . ?
C20C C20D 1.383(7) . ?
C20D C20E 1.383(7) . ?
C20E C20F 1.386(6) . ?
loop_
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1 ChemSpider 29320075
