#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:01:11 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179551 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/20/4502041.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_4502041
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 H24 Cu N8'
_chemical_formula_sum            'C40 H24 Cu N8'
_chemical_formula_weight         680.21
_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                 108.6867(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0346(2)
_cell_length_b                   16.5760(3)
_cell_length_c                   14.3933(2)
_cell_measurement_reflns_used    6448
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.21
_cell_volume                     2945.90(8)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0740
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22098
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  0.9616
_exptl_absorpt_correction_T_min  0.8908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1396
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         6926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0601P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                4550
_reflns_number_total             6926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg1008973_si_001.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4502041
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
Cu Cu 0.46017(3) 0.14892(2) 0.91284(2) 0.01650(11) Uani 1 1 d .
C1 C 0.2674(2) 0.25021(16) 0.91902(19) 0.0184(6) Uani 1 1 d .
C2 C 0.1507(2) 0.24965(18) 0.88693(19) 0.0207(6) Uani 1 1 d .
H2 H 0.1049 0.2927 0.8924 0.025 Uiso 1 1 calc R
C3 C 0.1187(2) 0.17579(17) 0.84732(19) 0.0202(6) Uani 1 1 d .
H3 H 0.0462 0.1578 0.8185 0.024 Uiso 1 1 calc R
C4 C 0.2149(2) 0.13002(17) 0.85714(18) 0.0180(6) Uani 1 1 d .
C5 C 0.2164(2) 0.04789(17) 0.83536(18) 0.0176(6) Uani 1 1 d .
C6 C 0.3112(2) 0.00421(17) 0.84434(19) 0.0173(6) Uani 1 1 d .
C7 C 0.3146(2) -0.08162(16) 0.82849(19) 0.0186(6) Uani 1 1 d .
H7 H 0.2558 -0.1183 0.8163 0.022 Uiso 1 1 calc R
C8 C 0.4178(2) -0.09964(16) 0.83439(18) 0.0177(6) Uani 1 1 d .
H8 H 0.4452 -0.1514 0.8266 0.021 Uiso 1 1 calc R
C9 C 0.4784(2) -0.02506(16) 0.85478(18) 0.0168(6) Uani 1 1 d .
C10 C 0.5876(2) -0.01799(16) 0.86214(18) 0.0174(6) Uani 1 1 d .
C11 C 0.6511(2) 0.05018(16) 0.89858(18) 0.0170(6) Uani 1 1 d .
C12 C 0.7654(2) 0.05598(17) 0.91385(19) 0.0204(6) Uani 1 1 d .
H12 H 0.8084 0.0184 0.8929 0.024 Uiso 1 1 calc R
C13 C 0.7999(2) 0.12525(17) 0.96382(19) 0.0200(6) Uani 1 1 d .
H13 H 0.8723 0.1446 0.9872 0.024 Uiso 1 1 calc R
C14 C 0.7054(2) 0.16406(16) 0.97460(18) 0.0174(6) Uani 1 1 d .
C15 C 0.7080(2) 0.23676(16) 1.02658(18) 0.0173(6) Uani 1 1 d .
C16 C 0.6152(2) 0.27684(16) 1.03035(19) 0.0182(6) Uani 1 1 d .
C17 C 0.6163(2) 0.35485(16) 1.07575(19) 0.0196(6) Uani 1 1 d .
H17 H 0.6786 0.3851 1.1107 0.023 Uiso 1 1 calc R
C18 C 0.5122(2) 0.37651(17) 1.0591(2) 0.0209(6) Uani 1 1 d .
H18 H 0.4874 0.4252 1.0796 0.025 Uiso 1 1 calc R
C19 C 0.4454(2) 0.31192(17) 1.00440(19) 0.0187(6) Uani 1 1 d .
C20 C 0.3320(2) 0.31310(17) 0.97163(18) 0.0176(6) Uani 1 1 d .
N21 N 0.30567(19) 0.17729(13) 0.89763(15) 0.0170(5) Uani 1 1 d .
N22 N 0.41307(19) 0.03706(14) 0.86486(16) 0.0180(5) Uani 1 1 d .
N23 N 0.61467(19) 0.11888(13) 0.93311(15) 0.0163(5) Uani 1 1 d .
N24 N 0.50958(18) 0.25155(13) 0.98740(15) 0.0173(5) Uani 1 1 d .
C25 C 0.1120(2) 0.00202(16) 0.80317(19) 0.0178(6) Uani 1 1 d .
C26 C 0.0448(2) -0.00189(17) 0.8619(2) 0.0214(6) Uani 1 1 d .
H26 H 0.0656 0.0282 0.9212 0.026 Uiso 1 1 calc R
N27 N -0.0466(2) -0.04505(15) 0.84027(17) 0.0250(6) Uani 1 1 d .
C28 C -0.0744(3) -0.08686(18) 0.7562(2) 0.0269(7) Uani 1 1 d .
H28 H -0.1391 -0.1179 0.7392 0.032 Uiso 1 1 calc R
C29 C -0.0139(3) -0.08715(18) 0.6928(2) 0.0262(7) Uani 1 1 d .
H29 H -0.0367 -0.1180 0.6342 0.031 Uiso 1 1 calc R
C30 C 0.0800(2) -0.04206(16) 0.7159(2) 0.0211(6) Uani 1 1 d .
H30 H 0.1222 -0.0410 0.6730 0.025 Uiso 1 1 calc R
C31 C 0.6364(2) -0.08941(17) 0.82824(19) 0.0189(6) Uani 1 1 d .
C32 C 0.5902(2) -0.11641(17) 0.7328(2) 0.0215(6) Uani 1 1 d .
H32 H 0.5315 -0.0862 0.6911 0.026 Uiso 1 1 calc R
N33 N 0.6221(2) -0.18200(15) 0.69504(17) 0.0254(6) Uani 1 1 d .
C34 C 0.7054(3) -0.22291(18) 0.7551(2) 0.0263(7) Uani 1 1 d .
H34 H 0.7292 -0.2701 0.7307 0.032 Uiso 1 1 calc R
C35 C 0.7589(3) -0.20024(17) 0.8510(2) 0.0238(7) Uani 1 1 d .
H35 H 0.8185 -0.2308 0.8907 0.029 Uiso 1 1 calc R
C36 C 0.7241(2) -0.13237(17) 0.8879(2) 0.0205(6) Uani 1 1 d .
H36 H 0.7598 -0.1153 0.9533 0.025 Uiso 1 1 calc R
C37 C 0.8157(2) 0.27087(16) 1.08378(19) 0.0178(6) Uani 1 1 d .
C38 C 0.8439(2) 0.27839(16) 1.18523(19) 0.0176(6) Uani 1 1 d .
H38 H 0.7923 0.2618 1.2153 0.021 Uiso 1 1 calc R
N39 N 0.93883(19) 0.30739(14) 1.24355(16) 0.0193(5) Uani 1 1 d .
C40 C 1.0111(2) 0.32970(17) 1.2000(2) 0.0216(6) Uani 1 1 d .
H40 H 1.0791 0.3499 1.2398 0.026 Uiso 1 1 calc R
C41 C 0.9914(2) 0.32477(17) 1.0995(2) 0.0219(6) Uani 1 1 d .
H41 H 1.0448 0.3414 1.0715 0.026 Uiso 1 1 calc R
C42 C 0.8925(2) 0.29524(16) 1.0408(2) 0.0193(6) Uani 1 1 d .
H42 H 0.8771 0.2916 0.9718 0.023 Uiso 1 1 calc R
C43 C 0.2762(2) 0.38340(17) 0.9992(2) 0.0192(6) Uani 1 1 d .
C44 C 0.2067(3) 0.43263(17) 0.9288(2) 0.0242(7) Uani 1 1 d .
H44 H 0.1985 0.4228 0.8618 0.029 Uiso 1 1 calc R
N45 N 0.1496(2) 0.49410(17) 0.9508(2) 0.0366(7) Uani 1 1 d .
C46 C 0.1633(3) 0.50671(19) 1.0472(2) 0.0304(8) Uani 1 1 d .
H46 H 0.1234 0.5491 1.0640 0.037 Uiso 1 1 calc R
C47 C 0.2307(2) 0.46219(17) 1.1211(2) 0.0212(6) Uani 1 1 d .
H47 H 0.2382 0.4735 1.1877 0.025 Uiso 1 1 calc R
C48 C 0.2875(3) 0.40080(17) 1.0970(2) 0.0238(7) Uani 1 1 d .
H48 H 0.3354 0.3693 1.1476 0.029 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'
Cu Cu 0.3201 1.2651 '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_3
N23 Cu N24 89.85(9) .
N23 Cu N22 90.16(9) .
N24 Cu N22 168.43(9) .
N23 Cu N21 177.79(9) .
N24 Cu N21 89.92(9) .
N22 Cu N21 89.61(9) .
N23 Cu N39 90.39(8) 4_565
N24 Cu N39 101.22(8) 4_565
N22 Cu N39 90.35(8) 4_565
N21 Cu N39 91.81(8) 4_565
N21 C1 C20 125.1(3) .
N21 C1 C2 110.1(2) .
C20 C1 C2 124.6(3) .
C3 C2 C1 106.9(3) .
C3 C2 H2 126.5 .
C1 C2 H2 126.5 .
C2 C3 C4 107.1(3) .
C2 C3 H3 126.4 .
C4 C3 H3 126.4 .
N21 C4 C5 125.1(3) .
N21 C4 C3 110.2(2) .
C5 C4 C3 124.6(3) .
C4 C5 C6 123.9(3) .
C4 C5 C25 119.1(3) .
C6 C5 C25 116.9(2) .
N22 C6 C5 125.2(3) .
N22 C6 C7 110.3(2) .
C5 C6 C7 124.4(3) .
C8 C7 C6 106.7(3) .
C8 C7 H7 126.6 .
C6 C7 H7 126.6 .
C7 C8 C9 106.9(2) .
C7 C8 H8 126.5 .
C9 C8 H8 126.5 .
N22 C9 C10 125.4(3) .
N22 C9 C8 110.3(2) .
C10 C9 C8 124.3(3) .
C9 C10 C11 124.1(3) .
C9 C10 C31 115.9(2) .
C11 C10 C31 119.9(3) .
N23 C11 C10 124.7(3) .
N23 C11 C12 110.3(2) .
C10 C11 C12 124.8(3) .
C13 C12 C11 106.8(3) .
C13 C12 H12 126.6 .
C11 C12 H12 126.6 .
C12 C13 C14 106.6(3) .
C12 C13 H13 126.7 .
C14 C13 H13 126.7 .
N23 C14 C15 124.7(3) .
N23 C14 C13 111.0(2) .
C15 C14 C13 124.2(3) .
C16 C15 C14 123.6(3) .
C16 C15 C37 118.2(2) .
C14 C15 C37 118.2(2) .
N24 C16 C15 126.1(3) .
N24 C16 C17 109.7(2) .
C15 C16 C17 124.0(3) .
C18 C17 C16 107.1(3) .
C18 C17 H17 126.4 .
C16 C17 H17 126.4 .
C17 C18 C19 107.2(3) .
C17 C18 H18 126.4 .
C19 C18 H18 126.4 .
N24 C19 C20 125.9(2) .
N24 C19 C18 110.0(3) .
C20 C19 C18 124.1(3) .
C1 C20 C19 124.0(3) .
C1 C20 C43 117.7(3) .
C19 C20 C43 118.2(2) .
C1 N21 C4 105.6(2) .
C1 N21 Cu 127.01(19) .
C4 N21 Cu 127.26(19) .
C9 N22 C6 105.6(2) .
C9 N22 Cu 126.75(19) .
C6 N22 Cu 127.41(19) .
C14 N23 C11 105.0(2) .
C14 N23 Cu 128.11(18) .
C11 N23 Cu 126.58(18) .
C19 N24 C16 106.0(2) .
C19 N24 Cu 127.10(19) .
C16 N24 Cu 126.89(19) .
C30 C25 C26 117.0(3) .
C30 C25 C5 121.7(3) .
C26 C25 C5 121.3(2) .
N27 C26 C25 124.5(3) .
N27 C26 H26 117.7 .
C25 C26 H26 117.7 .
C26 N27 C28 116.7(3) .
N27 C28 C29 123.4(3) .
N27 C28 H28 118.3 .
C29 C28 H28 118.3 .
C30 C29 C28 119.2(3) .
C30 C29 H29 120.4 .
C28 C29 H29 120.4 .
C29 C30 C25 119.1(3) .
C29 C30 H30 120.4 .
C25 C30 H30 120.4 .
C32 C31 C36 117.3(3) .
C32 C31 C10 118.9(3) .
C36 C31 C10 123.8(2) .
N33 C32 C31 124.9(3) .
N33 C32 H32 117.6 .
C31 C32 H32 117.6 .
C34 N33 C32 116.3(2) .
N33 C34 C35 123.6(3) .
N33 C34 H34 118.2 .
C35 C34 H34 118.2 .
C36 C35 C34 118.8(3) .
C36 C35 H35 120.6 .
C34 C35 H35 120.6 .
C35 C36 C31 119.1(3) .
C35 C36 H36 120.4 .
C31 C36 H36 120.4 .
C38 C37 C42 117.0(3) .
C38 C37 C15 119.8(2) .
C42 C37 C15 123.2(2) .
N39 C38 C37 124.6(3) .
N39 C38 H38 117.7 .
C37 C38 H38 117.7 .
C40 N39 C38 116.8(2) .
C40 N39 Cu 120.44(18) 4_666
C38 N39 Cu 120.78(19) 4_666
N39 C40 C41 123.3(3) .
N39 C40 H40 118.4 .
C41 C40 H40 118.4 .
C42 C41 C40 118.8(3) .
C42 C41 H41 120.6 .
C40 C41 H41 120.6 .
C41 C42 C37 119.5(3) .
C41 C42 H42 120.3 .
C37 C42 H42 120.3 .
C44 C43 C48 116.6(3) .
C44 C43 C20 121.7(2) .
C48 C43 C20 121.7(2) .
N45 C44 C43 123.3(3) .
N45 C44 H44 118.3 .
C43 C44 H44 118.3 .
C46 N45 C44 116.9(3) .
N45 C46 C47 123.8(3) .
N45 C46 H46 118.1 .
C47 C46 H46 118.1 .
C46 C47 C48 118.1(3) .
C46 C47 H47 120.9 .
C48 C47 H47 120.9 .
C47 C48 C43 121.3(3) .
C47 C48 H48 119.4 .
C43 C48 H48 119.4 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu N23 2.003(2) .
Cu N24 2.004(2) .
Cu N22 2.005(2) .
Cu N21 2.010(2) .
Cu N39 2.471(2) 4_565
C1 N21 1.380(3) .
C1 C20 1.400(4) .
C1 C2 1.441(4) .
C2 C3 1.359(4) .
C2 H2 0.9500 .
C3 C4 1.433(4) .
C3 H3 0.9500 .
C4 N21 1.383(4) .
C4 C5 1.399(4) .
C5 C6 1.402(4) .
C5 C25 1.497(4) .
C6 N22 1.377(4) .
C6 C7 1.444(4) .
C7 C8 1.353(4) .
C7 H7 0.9500 .
C8 C9 1.445(4) .
C8 H8 0.9500 .
C9 N22 1.373(3) .
C9 C10 1.399(4) .
C10 C11 1.399(4) .
C10 C31 1.498(4) .
C11 N23 1.386(3) .
C11 C12 1.438(4) .
C12 C13 1.353(4) .
C12 H12 0.9500 .
C13 C14 1.441(4) .
C13 H13 0.9500 .
C14 N23 1.365(4) .
C14 C15 1.413(4) .
C15 C16 1.396(4) .
C15 C37 1.493(4) .
C16 N24 1.381(4) .
C16 C17 1.447(4) .
C17 C18 1.349(4) .
C17 H17 0.9500 .
C18 C19 1.444(4) .
C18 H18 0.9500 .
C19 N24 1.376(3) .
C19 C20 1.400(4) .
C20 C43 1.493(4) .
C25 C30 1.396(4) .
C25 C26 1.400(4) .
C26 N27 1.338(4) .
C26 H26 0.9500 .
N27 C28 1.339(4) .
C28 C29 1.384(4) .
C28 H28 0.9500 .
C29 C30 1.380(4) .
C29 H29 0.9500 .
C30 H30 0.9500 .
C31 C32 1.385(4) .
C31 C36 1.386(4) .
C32 N33 1.340(4) .
C32 H32 0.9500 .
N33 C34 1.336(4) .
C34 C35 1.383(4) .
C34 H34 0.9500 .
C35 C36 1.381(4) .
C35 H35 0.9500 .
C36 H36 0.9500 .
C37 C38 1.393(4) .
C37 C42 1.394(4) .
C38 N39 1.342(3) .
C38 H38 0.9500 .
N39 C40 1.340(4) .
N39 Cu 2.471(2) 4_666
C40 C41 1.388(4) .
C40 H40 0.9500 .
C41 C42 1.384(4) .
C41 H41 0.9500 .
C42 H42 0.9500 .
C43 C44 1.388(4) .
C43 C48 1.398(4) .
C44 N45 1.358(4) .
C44 H44 0.9500 .
N45 C46 1.357(4) .
C46 C47 1.360(4) .
C46 H46 0.9500 .
C47 C48 1.367(4) .
C47 H47 0.9500 .
C48 H48 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
C12 H12 N27 0.95 2.48 3.405(4) 164 1_655
C42 H42 N33 0.95 2.44 3.360(4) 162 2_656
