#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:01:11 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179551 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/20/4502039.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_4502039
loop_
_publ_author_name
'Lipstman, Sophia'
'Goldberg, Israel'
_publ_section_title
;
 Versatile Molecular Recognition Features of Tetra(3-pyridyl)porphyrin in
 Crystal Engineering
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4596
_journal_paper_doi               10.1021/cg1008973
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C40 H26 N8'
_chemical_formula_sum            'C40 H26 N8'
_chemical_formula_weight         618.69
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/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                 101.1398(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.1947(6)
_cell_length_b                   6.2755(2)
_cell_length_c                   16.4169(8)
_cell_measurement_reflns_used    3518
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.53
_cell_volume                     1535.93(11)
_computing_cell_refinement       Denzo
_computing_data_collection       'Collect, Nonius B.V.'
_computing_data_reduction        'Denzo & Scalepack'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1 deg. 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  0.0810
_diffrn_reflns_av_sigmaI/netI    0.0966
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11570
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1430
_refine_ls_R_factor_gt           0.0667
_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)+(0.0657P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                1914
_reflns_number_total             3606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg1008973_si_001.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               4502039
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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
C1 C 0.50703(15) 0.1810(3) -0.17235(15) 0.0293(5) Uani 1 1 d .
C2 C 0.46383(16) 0.3368(3) -0.23223(15) 0.0320(6) Uani 1 1 d .
H2 H 0.4733 0.3553 -0.2873 0.038 Uiso 1 1 calc R
C3 C 0.40791(16) 0.4500(3) -0.19488(15) 0.0340(6) Uani 1 1 d .
H3 H 0.3702 0.5634 -0.2188 0.041 Uiso 1 1 calc R
C4 C 0.41573(15) 0.3674(3) -0.11176(14) 0.0302(6) Uani 1 1 d .
C5 C 0.36427(15) 0.4381(3) -0.05458(14) 0.0288(5) Uani 1 1 d .
C6 C 0.36574(15) 0.3523(3) 0.02424(15) 0.0298(5) Uani 1 1 d .
C7 C 0.31547(16) 0.4277(3) 0.08409(15) 0.0330(6) Uani 1 1 d .
H7 H 0.2763 0.5470 0.0778 0.040 Uiso 1 1 calc R
C8 C 0.33417(16) 0.2975(3) 0.15126(15) 0.0326(6) Uani 1 1 d .
H8 H 0.3094 0.3086 0.2000 0.039 Uiso 1 1 calc R
C9 C 0.39741(15) 0.1407(3) 0.13615(14) 0.0296(5) Uani 1 1 d .
C10 C 0.43341(15) -0.0238(3) 0.18985(14) 0.0296(5) Uani 1 1 d .
N11 N 0.47690(12) 0.2030(3) -0.09903(12) 0.0299(5) Uani 1 1 d .
N12 N 0.41478(12) 0.1795(3) 0.05832(12) 0.0294(5) Uani 1 1 d .
H12 H 0.4484 0.0840 0.0300 0.035 Uiso 1 1 d R
C13 C 0.29617(16) 0.6073(3) -0.08295(14) 0.0303(5) Uani 1 1 d .
C14 C 0.20493(16) 0.5617(4) -0.09078(15) 0.0336(6) Uani 1 1 d .
H14 H 0.1891 0.4242 -0.0741 0.040 Uiso 1 1 calc R
N15 N 0.13828(14) 0.6966(3) -0.11986(13) 0.0373(5) Uani 1 1 d .
C16 C 0.16261(18) 0.8888(4) -0.14306(16) 0.0401(6) Uani 1 1 d .
H16 H 0.1166 0.9880 -0.1643 0.048 Uiso 1 1 calc R
C17 C 0.25043(17) 0.9513(4) -0.13792(15) 0.0384(6) Uani 1 1 d .
H17 H 0.2641 1.0899 -0.1552 0.046 Uiso 1 1 calc R
C18 C 0.31864(17) 0.8086(3) -0.10718(15) 0.0357(6) Uani 1 1 d .
H18 H 0.3797 0.8482 -0.1028 0.043 Uiso 1 1 calc R
C19 C 0.40683(15) -0.0286(3) 0.27271(15) 0.0307(5) Uani 1 1 d .
C20 C 0.35891(17) -0.1972(4) 0.29649(17) 0.0414(7) Uani 1 1 d .
H20 H 0.3442 -0.3116 0.2584 0.050 Uiso 1 1 calc R
N21 N 0.33173(17) -0.2113(4) 0.36887(15) 0.0544(7) Uani 1 1 d .
C22 C 0.3534(2) -0.0480(5) 0.42144(17) 0.0534(8) Uani 1 1 d .
H22 H 0.3343 -0.0533 0.4732 0.064 Uiso 1 1 calc R
C23 C 0.40153(19) 0.1266(4) 0.40504(16) 0.0471(7) Uani 1 1 d .
H23 H 0.4159 0.2376 0.4447 0.056 Uiso 1 1 calc R
C24 C 0.42860(17) 0.1372(4) 0.32963(15) 0.0383(6) Uani 1 1 d .
H24 H 0.4618 0.2565 0.3166 0.046 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'
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
N11 C1 C10 125.8(2) . 3_655
N11 C1 C2 110.01(19) . .
C10 C1 C2 124.0(2) 3_655 .
C3 C2 C1 106.9(2) . .
C3 C2 H2 126.6 . .
C1 C2 H2 126.6 . .
C2 C3 C4 107.3(2) . .
C2 C3 H3 126.3 . .
C4 C3 H3 126.3 . .
N11 C4 C5 125.6(2) . .
N11 C4 C3 110.03(19) . .
C5 C4 C3 124.3(2) . .
C6 C5 C4 125.8(2) . .
C6 C5 C13 116.67(19) . .
C4 C5 C13 117.3(2) . .
N12 C6 C5 126.3(2) . .
N12 C6 C7 107.5(2) . .
C5 C6 C7 126.2(2) . .
C8 C7 C6 107.6(2) . .
C8 C7 H7 126.2 . .
C6 C7 H7 126.2 . .
C7 C8 C9 108.4(2) . .
C7 C8 H8 125.8 . .
C9 C8 H8 125.8 . .
N12 C9 C10 126.5(2) . .
N12 C9 C8 107.17(19) . .
C10 C9 C8 126.3(2) . .
C9 C10 C1 125.3(2) . 3_655
C9 C10 C19 116.60(19) . .
C1 C10 C19 118.1(2) 3_655 .
C1 N11 C4 105.74(18) . .
C6 N12 C9 109.40(18) . .
C6 N12 H12 126.3 . .
C9 N12 H12 123.6 . .
C18 C13 C14 117.1(2) . .
C18 C13 C5 122.9(2) . .
C14 C13 C5 119.9(2) . .
N15 C14 C13 125.0(2) . .
N15 C14 H14 117.5 . .
C13 C14 H14 117.5 . .
C14 N15 C16 116.2(2) . .
N15 C16 C17 123.8(2) . .
N15 C16 H16 118.1 . .
C17 C16 H16 118.1 . .
C16 C17 C18 119.0(2) . .
C16 C17 H17 120.5 . .
C18 C17 H17 120.5 . .
C13 C18 C17 118.9(2) . .
C13 C18 H18 120.5 . .
C17 C18 H18 120.5 . .
C20 C19 C24 116.8(2) . .
C20 C19 C10 121.5(2) . .
C24 C19 C10 121.6(2) . .
N21 C20 C19 124.9(2) . .
N21 C20 H20 117.5 . .
C19 C20 H20 117.5 . .
C20 N21 C22 116.3(2) . .
N21 C22 C23 124.0(2) . .
N21 C22 H22 118.0 . .
C23 C22 H22 118.0 . .
C22 C23 C24 118.5(3) . .
C22 C23 H23 120.8 . .
C24 C23 H23 120.8 . .
C23 C24 C19 119.5(2) . .
C23 C24 H24 120.3 . .
C19 C24 H24 120.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N11 1.375(3) .
C1 C10 1.406(3) 3_655
C1 C2 1.450(3) .
C2 C3 1.343(3) .
C2 H2 0.9500 .
C3 C4 1.443(3) .
C3 H3 0.9500 .
C4 N11 1.377(3) .
C4 C5 1.405(3) .
C5 C6 1.398(3) .
C5 C13 1.493(3) .
C6 N12 1.373(3) .
C6 C7 1.436(3) .
C7 C8 1.358(3) .
C7 H7 0.9500 .
C8 C9 1.430(3) .
C8 H8 0.9500 .
C9 N12 1.375(3) .
C9 C10 1.398(3) .
C10 C1 1.406(3) 3_655
C10 C19 1.492(3) .
N12 H12 0.9632 .
C13 C18 1.386(3) .
C13 C14 1.397(3) .
C14 N15 1.336(3) .
C14 H14 0.9500 .
N15 C16 1.338(3) .
C16 C17 1.378(3) .
C16 H16 0.9500 .
C17 C18 1.389(3) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C19 C20 1.383(3) .
C19 C24 1.395(3) .
C20 N21 1.334(3) .
C20 H20 0.9500 .
N21 C22 1.340(3) .
C22 C23 1.372(4) .
C22 H22 0.9500 .
C23 C24 1.380(3) .
C23 H23 0.9500 .
C24 H24 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
C7 H7 N21 0.95 2.51 3.376(3) 151 2_565
