#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/52/2015244.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_2015244
loop_
_publ_author_name
'Sankar Muniappan'
'Sophia Liptsman'
'Israel Goldberg'
_publ_section_title
;
 Clathrate solvates of tetrakis(4-methoxycarbonylphenyl)porphyrin and
 its zinc(II)--pyridine complex, in which the porphyrin host structures
 are stabilized by porphyrin--porphyrin stacking and
 C---H···O attractions
;
_journal_coeditor_code           GD3004
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m140
_journal_page_last               m143
_journal_paper_doi               10.1107/S010827010600641X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C52 H38 N4 O8 , 1.904 C6 H5 N O2'
_chemical_formula_moiety         'C52 H38 N4 O8 , 1.904 C6 H5 N O2'
_chemical_formula_sum            'C63.42 H47.52 N5.9 O11.81'
_chemical_formula_weight         1081.27
_chemical_name_common
;
Tetrakis(4-methoxycarbonylphenyl)porphyrin
;
_chemical_name_systematic
;
Tetramethyl 4,4',4'',4'''-porphyrin-5,10,15,20-tetrabenzoate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 100.2918(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   32.6249(8)
_cell_length_b                   7.0657(2)
_cell_length_c                   23.5160(8)
_cell_measurement_reflns_used    5804
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      1.41
_cell_volume                     5333.6(3)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        DENZO
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and MERCURY (Bruno et al.,
2002)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean '56 microns'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1° φ'
_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  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20139
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         2.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2255.4
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         6404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0569
_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)+(0.0865P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                3904
_reflns_number_total             6404
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3004.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C63.42 H47.52 N5.90 O11.81'
_cod_database_code               2015244
_cod_database_fobs_code          2015244
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'
'-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_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
C C1 0.01794(6) 0.8569(2) 0.57609(8) 0.0225(4) Uani d . 1
C C2 0.05179(6) 0.9743(2) 0.60418(8) 0.0268(4) Uani d . 1
H H2 0.0498 1.0753 0.6302 0.032 Uiso calc R 1
C C3 0.08700(6) 0.9141(3) 0.58675(8) 0.0267(4) Uani d . 1
H H3 0.1142 0.9654 0.5980 0.032 Uiso calc R 1
C C4 0.07533(6) 0.7559(2) 0.54757(8) 0.0219(4) Uani d . 1
C C5 0.10327(6) 0.6434(2) 0.52340(8) 0.0214(4) Uani d . 1
C C6 0.09243(6) 0.4807(2) 0.48956(8) 0.0225(4) Uani d . 1
C C7 0.12050(6) 0.3752(2) 0.46072(8) 0.0263(4) Uani d . 1
H H7 0.1494 0.3992 0.4627 0.032 Uiso calc R 1
C C8 0.09816(6) 0.2353(2) 0.43024(8) 0.0253(4) Uani d . 1
H H8 0.1085 0.1434 0.4070 0.030 Uiso calc R 1
C C9 0.05584(6) 0.2511(2) 0.43945(8) 0.0218(4) Uani d . 1
C C10 0.02313(6) 0.1327(2) 0.41470(7) 0.0209(4) Uani d . 1
N N21 0.03333(5) 0.7275(2) 0.54152(6) 0.0219(3) Uani d . 1
H H21 0.0187 0.6419 0.5194 0.026 Uiso calc PR 0.42(3)
N N22 0.05349(5) 0.40154(19) 0.47576(6) 0.0213(3) Uani d . 1
H H22 0.0310 0.4403 0.4880 0.026 Uiso calc PR 0.58(3)
C C25 0.14841(6) 0.6943(2) 0.53676(8) 0.0234(4) Uani d . 1
C C26 0.16281(6) 0.8703(2) 0.52233(8) 0.0262(4) Uani d . 1
H H26 0.1437 0.9602 0.5028 0.031 Uiso calc R 1
C C27 0.20474(6) 0.9158(3) 0.53610(8) 0.0282(4) Uani d . 1
H H27 0.2141 1.0366 0.5261 0.034 Uiso calc R 1
C C28 0.23312(6) 0.7851(3) 0.56453(8) 0.0269(4) Uani d . 1
C C29 0.21900(6) 0.6082(3) 0.57865(9) 0.0302(5) Uani d . 1
H H29 0.2382 0.5180 0.5979 0.036 Uiso calc R 1
C C30 0.17714(6) 0.5630(3) 0.56483(8) 0.0286(4) Uani d . 1
H H30 0.1678 0.4417 0.5745 0.034 Uiso calc R 1
C C31 0.27768(6) 0.8404(3) 0.58030(9) 0.0312(5) Uani d . 1
O O32 0.29167(4) 0.98904(19) 0.56696(6) 0.0371(4) Uani d . 1
O O33 0.30050(4) 0.7072(2) 0.61223(6) 0.0391(4) Uani d . 1
C C34 0.34423(6) 0.7499(3) 0.63104(10) 0.0427(6) Uani d . 1
H H34A 0.3579 0.7594 0.5973 0.064 Uiso calc R 1
H H34B 0.3573 0.6488 0.6565 0.064 Uiso calc R 1
H H34C 0.3470 0.8704 0.6520 0.064 Uiso calc R 1
C C35 0.03307(6) -0.0104(2) 0.37180(8) 0.0215(4) Uani d . 1
C C36 0.03409(6) -0.2035(2) 0.38326(8) 0.0251(4) Uani d . 1
H H36 0.0274 -0.2487 0.4185 0.030 Uiso calc R 1
C C37 0.04484(6) -0.3303(2) 0.34361(8) 0.0265(4) Uani d . 1
H H37 0.0457 -0.4619 0.3520 0.032 Uiso calc R 1
C C38 0.05444(6) -0.2671(2) 0.29147(8) 0.0224(4) Uani d . 1
C C39 0.05297(6) -0.0736(2) 0.27937(8) 0.0256(4) Uani d . 1
H H39 0.0592 -0.0286 0.2438 0.031 Uiso calc R 1
C C40 0.04238(6) 0.0523(2) 0.31945(8) 0.0256(4) Uani d . 1
H H40 0.0415 0.1839 0.3111 0.031 Uiso calc R 1
C C41 0.06699(6) -0.4071(3) 0.25037(8) 0.0273(4) Uani d . 1
O O42 0.07392(6) -0.57220(19) 0.26153(7) 0.0516(5) Uani d . 1
O O43 0.07053(5) -0.33006(17) 0.19992(6) 0.0337(4) Uani d . 1
C C44 0.08314(8) -0.4569(3) 0.15782(9) 0.0414(6) Uani d . 1
H H44A 0.1118 -0.4989 0.1715 0.062 Uiso calc R 1
H H44B 0.0815 -0.3906 0.1209 0.062 Uiso calc R 1
H H44C 0.0646 -0.5670 0.1525 0.062 Uiso calc R 1
C C45 0.23717(10) 0.2379(3) 0.22574(10) 0.0476(7) Uani d P 0.952(3)
H H45 0.2539 0.2300 0.1967 0.057 Uiso calc PR 0.952(3)
C C46 0.19467(10) 0.2266(3) 0.21152(12) 0.0536(8) Uani d P 0.952(3)
H H46 0.1817 0.2119 0.1722 0.064 Uiso calc PR 0.952(3)
C C47 0.17029(10) 0.2366(3) 0.25463(14) 0.0597(8) Uani d P 0.952(3)
H H47 0.1408 0.2262 0.2449 0.072 Uiso calc PR 0.952(3)
C C48 0.18949(13) 0.2618(4) 0.31166(13) 0.0663(10) Uani d P 0.952(3)
H H48 0.1730 0.2704 0.3410 0.080 Uiso calc PR 0.952(3)
C C49 0.23192(12) 0.2744(3) 0.32625(12) 0.0608(9) Uani d P 0.952(3)
H H49 0.2450 0.2921 0.3653 0.073 Uiso calc PR 0.952(3)
C C50 0.25522(10) 0.2611(3) 0.28302(11) 0.0482(7) Uani d P 0.952(3)
N N51 0.30073(9) 0.2699(3) 0.29829(11) 0.0588(7) Uani d P 0.952(3)
O O52 0.32147(7) 0.2423(3) 0.26037(10) 0.0733(7) Uani d P 0.952(3)
O O53 0.31635(8) 0.3072(3) 0.34878(8) 0.0768(8) Uani d P 0.952(3)
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'
O O 0.0106 0.0060 '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
N21 C1 C10 . 5_566 126.00(16)
N21 C1 C2 . . 108.78(16)
C10 C1 C2 5_566 . 125.13(16)
C3 C2 C1 . . 107.57(16)
C3 C2 H2 . . 126.2
C1 C2 H2 . . 126.2
C2 C3 C4 . . 106.99(17)
C2 C3 H3 . . 126.5
C4 C3 H3 . . 126.5
N21 C4 C5 . . 125.87(16)
N21 C4 C3 . . 108.84(16)
C5 C4 C3 . . 125.15(17)
C4 C5 C6 . . 125.15(17)
C4 C5 C25 . . 117.76(15)
C6 C5 C25 . . 117.02(16)
N22 C6 C5 . . 126.53(16)
N22 C6 C7 . . 108.48(15)
C5 C6 C7 . . 124.90(17)
C8 C7 C6 . . 107.41(17)
C8 C7 H7 . . 126.3
C6 C7 H7 . . 126.3
C7 C8 C9 . . 107.69(16)
C7 C8 H8 . . 126.2
C9 C8 H8 . . 126.2
N22 C9 C10 . . 126.74(17)
N22 C9 C8 . . 108.35(15)
C10 C9 C8 . . 124.90(16)
C1 C10 C9 5_566 . 125.86(16)
C1 C10 C35 5_566 . 117.84(15)
C9 C10 C35 . . 116.20(16)
C4 N21 C1 . . 107.80(14)
C4 N21 H21 . . 126.1
C1 N21 H21 . . 126.1
C6 N22 C9 . . 108.06(15)
C6 N22 H22 . . 126.0
C9 N22 H22 . . 126.0
C26 C25 C30 . . 118.74(17)
C26 C25 C5 . . 121.75(16)
C30 C25 C5 . . 119.51(16)
C27 C26 C25 . . 120.81(17)
C27 C26 H26 . . 119.6
C25 C26 H26 . . 119.6
C26 C27 C28 . . 120.15(17)
C26 C27 H27 . . 119.9
C28 C27 H27 . . 119.9
C27 C28 C29 . . 119.35(18)
C27 C28 C31 . . 118.83(17)
C29 C28 C31 . . 121.80(18)
C30 C29 C28 . . 120.40(18)
C30 C29 H29 . . 119.8
C28 C29 H29 . . 119.8
C29 C30 C25 . . 120.55(17)
C29 C30 H30 . . 119.7
C25 C30 H30 . . 119.7
O32 C31 O33 . . 123.81(19)
O32 C31 C28 . . 124.16(19)
O33 C31 C28 . . 112.02(17)
C31 O33 C34 . . 116.27(16)
O33 C34 H34A . . 109.5
O33 C34 H34B . . 109.5
H34A C34 H34B . . 109.5
O33 C34 H34C . . 109.5
H34A C34 H34C . . 109.5
H34B C34 H34C . . 109.5
C36 C35 C40 . . 118.84(16)
C36 C35 C10 . . 122.03(16)
C40 C35 C10 . . 119.12(15)
C37 C36 C35 . . 120.35(17)
C37 C36 H36 . . 119.8
C35 C36 H36 . . 119.8
C36 C37 C38 . . 120.67(16)
C36 C37 H37 . . 119.7
C38 C37 H37 . . 119.7
C37 C38 C39 . . 119.28(16)
C37 C38 C41 . . 119.27(15)
C39 C38 C41 . . 121.44(16)
C40 C39 C38 . . 119.64(18)
C40 C39 H39 . . 120.2
C38 C39 H39 . . 120.2
C39 C40 C35 . . 121.22(16)
C39 C40 H40 . . 119.4
C35 C40 H40 . . 119.4
O42 C41 O43 . . 123.15(18)
O42 C41 C38 . . 124.24(18)
O43 C41 C38 . . 112.61(15)
C41 O43 C44 . . 115.92(15)
O43 C44 H44A . . 109.5
O43 C44 H44B . . 109.5
H44A C44 H44B . . 109.5
O43 C44 H44C . . 109.5
H44A C44 H44C . . 109.5
H44B C44 H44C . . 109.5
C46 C45 C50 . . 118.8(3)
C46 C45 H45 . . 120.6
C50 C45 H45 . . 120.6
C45 C46 C47 . . 120.2(3)
C45 C46 H46 . . 119.9
C47 C46 H46 . . 119.9
C48 C47 C46 . . 119.4(3)
C48 C47 H47 . . 120.3
C46 C47 H47 . . 120.3
C49 C48 C47 . . 120.8(3)
C49 C48 H48 . . 119.6
C47 C48 H48 . . 119.6
C48 C49 C50 . . 118.5(3)
C48 C49 H49 . . 120.7
C50 C49 H49 . . 120.7
C49 C50 C45 . . 122.2(3)
C49 C50 N51 . . 119.0(3)
C45 C50 N51 . . 118.8(3)
O52 N51 O53 . . 123.1(3)
O52 N51 C50 . . 118.8(2)
O53 N51 C50 . . 118.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N21 . 1.376(2)
C1 C10 5_566 1.397(3)
C1 C2 . 1.443(3)
C2 C3 . 1.355(3)
C2 H2 . 0.9500
C3 C4 . 1.455(2)
C3 H3 . 0.9500
C4 N21 . 1.367(2)
C4 C5 . 1.404(3)
C5 C6 . 1.407(2)
C5 C25 . 1.494(3)
C6 N22 . 1.373(2)
C6 C7 . 1.441(3)
C7 C8 . 1.355(3)
C7 H7 . 0.9500
C8 C9 . 1.440(3)
C8 H8 . 0.9500
C9 N22 . 1.374(2)
C9 C10 . 1.398(2)
C10 C1 5_566 1.397(3)
C10 C35 . 1.504(2)
N21 H21 . 0.8800
N22 H22 . 0.8800
C25 C26 . 1.393(3)
C25 C30 . 1.398(3)
C26 C27 . 1.386(3)
C26 H26 . 0.9500
C27 C28 . 1.392(3)
C27 H27 . 0.9500
C28 C29 . 1.393(3)
C28 C31 . 1.487(3)
C29 C30 . 1.383(3)
C29 H29 . 0.9500
C30 H30 . 0.9500
C31 O32 . 1.209(2)
C31 O33 . 1.343(2)
O33 C34 . 1.448(2)
C34 H34A . 0.9800
C34 H34B . 0.9800
C34 H34C . 0.9800
C35 C36 . 1.390(2)
C35 C40 . 1.392(3)
C36 C37 . 1.383(3)
C36 H36 . 0.9500
C37 C38 . 1.392(3)
C37 H37 . 0.9500
C38 C39 . 1.395(2)
C38 C41 . 1.491(3)
C39 C40 . 1.384(3)
C39 H39 . 0.9500
C40 H40 . 0.9500
C41 O42 . 1.208(2)
C41 O43 . 1.329(2)
O43 C44 . 1.448(2)
C44 H44A . 0.9800
C44 H44B . 0.9800
C44 H44C . 0.9800
C45 C46 . 1.369(4)
C45 C50 . 1.380(4)
C45 H45 . 0.9500
C46 C47 . 1.398(4)
C46 H46 . 0.9500
C47 C48 . 1.387(4)
C47 H47 . 0.9500
C48 C49 . 1.368(5)
C48 H48 . 0.9500
C49 C50 . 1.377(4)
C49 H49 . 0.9500
C50 N51 . 1.465(4)
N51 O52 . 1.228(3)
N51 O53 . 1.234(3)
