#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/67/2216730.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2216730
loop_
_publ_author_name
'P. Bhyrappa'
'K. Karunanithi'
'B. Varghese'
_publ_section_title
;
 2,3,12,13-Tetramethyl-5,10,15,20-tetraphenylporphyrin
;
_journal_coeditor_code           RK2056
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4755
_journal_page_last               o4755
_journal_paper_doi               10.1107/S1600536807058242
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C48 H38 N4'
_chemical_formula_moiety         'C48 H38 N4'
_chemical_formula_sum            'C48 H38 N4'
_chemical_formula_weight         670.82
_chemical_name_common            Porphyrin
_chemical_name_systematic
;
2,3,12,13-Tetramethyl-5,10,15,20-tetraphenylporphyrin
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.4630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.5507(3)
_cell_length_b                   6.70940(10)
_cell_length_c                   19.4638(4)
_cell_measurement_reflns_used    5867
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.39
_cell_measurement_theta_min      3.1
_cell_volume                     1727.89(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'XPREP (Sheldrick, 2003)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,  2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker Kappa APEX2'
_diffrn_measurement_method       'ω-- and φ--scan'
_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  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            26484
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.41
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0760
_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)+(0.0472P)²+2.1167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1648
_reflns_number_gt                3353
_reflns_number_total             5108
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            rk2056.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_sites_solution_hydrogens' value 'Geom' changed to 'geom' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_atom_sites_solution_secondary' value 'Difmap' changed to
'difmap' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'Constr' changed to
'constr' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_matrix_type' value 'Full' changed to 'full'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_weighting_scheme' value 'Calc' changed to 'calc'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'Geom' changed to 'geom'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_atom_sites_solution_secondary' value 'Difmap' changed
to 'difmap' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'Constr' changed
to 'constr' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_matrix_type' value 'Full' changed to 'full'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_weighting_scheme' value 'Calc' changed to
'calc' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2216730
_cod_database_fobs_code          2216730
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.12260(12) 0.7865(2) 0.02441(8) 0.0196(4) Uani d . 1
H H1 0.0765 0.8767 0.0161 0.023 Uiso calc R 1
N N2 -0.07612(12) 0.8566(2) 0.06079(8) 0.0195(4) Uani d . 1
C C1 0.22546(15) 0.9211(3) -0.05388(10) 0.0200(4) Uani d . 1
C C2 0.20639(15) 0.7816(3) -0.00481(10) 0.0195(4) Uani d . 1
C C3 0.26399(15) 0.6072(3) 0.02301(10) 0.0214(4) Uani d . 1
C C4 0.21183(15) 0.5106(3) 0.06600(10) 0.0208(4) Uani d . 1
C C5 0.12308(15) 0.6273(3) 0.06860(10) 0.0195(4) Uani d . 1
C C6 0.05040(15) 0.5931(3) 0.10860(10) 0.0194(4) Uani d . 1
C C7 -0.04024(15) 0.6994(3) 0.10417(10) 0.0200(4) Uani d . 1
C C8 -0.10803(16) 0.6560(3) 0.15066(11) 0.0242(4) Uani d . 1
H H8 -0.1000 0.5566 0.1847 0.029 Uiso calc R 1
C C9 -0.18473(16) 0.7874(3) 0.13498(11) 0.0248(5) Uani d . 1
H H9 -0.2402 0.7956 0.1559 0.030 Uiso calc R 1
C C10 -0.16427(15) 0.9134(3) 0.07928(10) 0.0202(4) Uani d . 1
C C11 0.39915(16) 0.9993(3) -0.07463(12) 0.0291(5) Uani d . 1
H H11 0.4059 1.1002 -0.0412 0.035 Uiso calc R 1
C C12 0.47621(18) 0.9645(4) -0.10983(13) 0.0365(6) Uani d . 1
H H12 0.5341 1.0430 -0.1001 0.044 Uiso calc R 1
C C13 0.46756(19) 0.8153(4) -0.15890(13) 0.0384(6) Uani d . 1
H H13 0.5199 0.7916 -0.1819 0.046 Uiso calc R 1
C C14 0.3811(2) 0.7004(4) -0.17410(13) 0.0408(6) Uani d . 1
H H14 0.3751 0.5989 -0.2073 0.049 Uiso calc R 1
C C15 0.30327(18) 0.7368(4) -0.13965(12) 0.0327(5) Uani d . 1
H H15 0.2445 0.6611 -0.1507 0.039 Uiso calc R 1
C C16 0.31201(15) 0.8843(3) -0.08904(11) 0.0219(4) Uani d . 1
C C17 0.07279(15) 0.4411(3) 0.16629(10) 0.0197(4) Uani d . 1
C C18 0.02474(17) 0.2577(3) 0.16021(12) 0.0286(5) Uani d . 1
H H18 -0.0191 0.2231 0.1182 0.034 Uiso calc R 1
C C19 0.04162(19) 0.1250(3) 0.21637(12) 0.0337(5) Uani d . 1
H H19 0.0090 0.0022 0.2119 0.040 Uiso calc R 1
C C20 0.10670(18) 0.1752(3) 0.27879(12) 0.0316(5) Uani d . 1
H H20 0.1171 0.0875 0.3167 0.038 Uiso calc R 1
C C21 0.15666(17) 0.3576(3) 0.28479(11) 0.0279(5) Uani d . 1
H H21 0.2018 0.3905 0.3264 0.034 Uiso calc R 1
C C22 0.13942(15) 0.4895(3) 0.22923(11) 0.0228(4) Uani d . 1
H H22 0.1725 0.6118 0.2337 0.027 Uiso calc R 1
C C23 0.36781(17) 0.5402(3) 0.01099(12) 0.0286(5) Uani d . 1
H H23A 0.4000 0.4556 0.0490 0.043 Uiso calc R 1
H H23B 0.4093 0.6551 0.0090 0.043 Uiso calc R 1
H H23C 0.3587 0.4682 -0.0325 0.043 Uiso calc R 1
C C24 0.23962(17) 0.3052(3) 0.09900(11) 0.0247(4) Uani d . 1
H H24A 0.2922 0.2474 0.0794 0.037 Uiso calc R 1
H H24B 0.1812 0.2203 0.0893 0.037 Uiso calc R 1
H H24C 0.2628 0.3192 0.1490 0.037 Uiso calc R 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C5 N1 C2 . . 110.38(16)
C5 N1 H1 . . 124.8
C2 N1 H1 . . 124.8
C7 N2 C10 . . 105.35(16)
C2 C1 C10 . 3_575 125.76(18)
C2 C1 C16 . . 118.59(17)
C10 C1 C16 3_575 . 115.34(17)
N1 C2 C1 . . 123.78(17)
N1 C2 C3 . . 106.97(17)
C1 C2 C3 . . 129.22(18)
C4 C3 C2 . . 107.69(17)
C4 C3 C23 . . 124.25(18)
C2 C3 C23 . . 128.01(18)
C3 C4 C5 . . 107.95(17)
C3 C4 C24 . . 124.69(18)
C5 C4 C24 . . 127.12(18)
N1 C5 C6 . . 124.65(18)
N1 C5 C4 . . 106.94(17)
C6 C5 C4 . . 128.40(18)
C5 C6 C7 . . 126.31(18)
C5 C6 C17 . . 118.39(18)
C7 C6 C17 . . 115.09(17)
N2 C7 C6 . . 128.03(18)
N2 C7 C8 . . 110.49(17)
C6 C7 C8 . . 121.43(18)
C9 C8 C7 . . 106.77(18)
C9 C8 H8 . . 126.6
C7 C8 H8 . . 126.6
C8 C9 C10 . . 106.79(18)
C8 C9 H9 . . 126.6
C10 C9 H9 . . 126.6
N2 C10 C1 . 3_575 127.27(18)
N2 C10 C9 . . 110.60(17)
C1 C10 C9 3_575 . 121.95(18)
C12 C11 C16 . . 120.4(2)
C12 C11 H11 . . 119.8
C16 C11 H11 . . 119.8
C13 C12 C11 . . 120.4(2)
C13 C12 H12 . . 119.8
C11 C12 H12 . . 119.8
C12 C13 C14 . . 119.9(2)
C12 C13 H13 . . 120.1
C14 C13 H13 . . 120.1
C13 C14 C15 . . 119.8(2)
C13 C14 H14 . . 120.1
C15 C14 H14 . . 120.1
C16 C15 C14 . . 120.8(2)
C16 C15 H15 . . 119.6
C14 C15 H15 . . 119.6
C15 C16 C11 . . 118.7(2)
C15 C16 C1 . . 119.15(19)
C11 C16 C1 . . 122.10(19)
C18 C17 C22 . . 119.04(19)
C18 C17 C6 . . 121.66(18)
C22 C17 C6 . . 119.20(18)
C17 C18 C19 . . 120.5(2)
C17 C18 H18 . . 119.8
C19 C18 H18 . . 119.8
C20 C19 C18 . . 120.1(2)
C20 C19 H19 . . 120.0
C18 C19 H19 . . 120.0
C19 C20 C21 . . 119.7(2)
C19 C20 H20 . . 120.1
C21 C20 H20 . . 120.1
C22 C21 C20 . . 120.1(2)
C22 C21 H21 . . 119.9
C20 C21 H21 . . 119.9
C21 C22 C17 . . 120.5(2)
C21 C22 H22 . . 119.7
C17 C22 H22 . . 119.7
C3 C23 H23A . . 109.5
C3 C23 H23B . . 109.5
H23A C23 H23B . . 109.5
C3 C23 H23C . . 109.5
H23A C23 H23C . . 109.5
H23B C23 H23C . . 109.5
C4 C24 H24A . . 109.5
C4 C24 H24B . . 109.5
H24A C24 H24B . . 109.5
C4 C24 H24C . . 109.5
H24A C24 H24C . . 109.5
H24B C24 H24C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C5 . 1.370(2)
N1 C2 . 1.376(3)
N1 H1 . 0.8600
N2 C7 . 1.372(3)
N2 C10 . 1.374(3)
C1 C2 . 1.401(3)
C1 C10 3_575 1.410(3)
C1 C16 . 1.500(3)
C2 C3 . 1.445(3)
C3 C4 . 1.369(3)
C3 C23 . 1.542(3)
C4 C5 . 1.445(3)
C4 C24 . 1.533(3)
C5 C6 . 1.400(3)
C6 C7 . 1.407(3)
C6 C17 . 1.498(3)
C7 C8 . 1.451(3)
C8 C9 . 1.347(3)
C8 H8 . 0.9300
C9 C10 . 1.448(3)
C9 H9 . 0.9300
C10 C1 3_575 1.410(3)
C11 C12 . 1.387(3)
C11 C16 . 1.387(3)
C11 H11 . 0.9300
C12 C13 . 1.371(4)
C12 H12 . 0.9300
C13 C14 . 1.380(4)
C13 H13 . 0.9300
C14 C15 . 1.388(3)
C14 H14 . 0.9300
C15 C16 . 1.383(3)
C15 H15 . 0.9300
C17 C18 . 1.385(3)
C17 C22 . 1.394(3)
C18 C19 . 1.390(3)
C18 H18 . 0.9300
C19 C20 . 1.380(3)
C19 H19 . 0.9300
C20 C21 . 1.391(3)
C20 H20 . 0.9300
C21 C22 . 1.378(3)
C21 H21 . 0.9300
C22 H22 . 0.9300
C23 H23A . 0.9600
C23 H23B . 0.9600
C23 H23C . 0.9600
C24 H24A . 0.9600
C24 H24B . 0.9600
C24 H24C . 0.9600
