#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:56:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180364 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/33/7203301.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_7203301
loop_
_publ_author_name
'George, Sumod'
'Lipstman, Sophia'
'Muniappan, Sankar'
'Goldberg, Israel'
_publ_section_title
;
 Porphyrin network solids: examples of supramolecular isomerism,
 noncentrosymmetric architectures and competing solvation
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              417
_journal_paper_doi               10.1039/b601889k
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C48 H30 N4 O8, 2(C6 H5 N O2)'
_chemical_formula_sum            'C60 H40 N6 O12'
_chemical_formula_weight         1036.98
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 108.359(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.4629(5)
_cell_length_b                   16.4777(8)
_cell_length_c                   10.6768(5)
_cell_measurement_reflns_used    4629
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      1.41
_cell_volume                     2414.94(19)
_computing_cell_refinement       Denzo
_computing_data_collection       'Collect, Nonius B.V.'
_computing_data_reduction        Denzo
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean '56 microns'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1 deg. Phi & Omega 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  0.0922
_diffrn_reflns_av_sigmaI/netI    0.1335
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13900
_diffrn_reflns_theta_full        25.60
_diffrn_reflns_theta_max         25.60
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4517
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0435P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                2201
_reflns_number_total             4517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b601889k.txt
_cod_data_source_block           Compound-1
_cod_original_cell_volume        2414.94(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7203301
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0877(2) 0.66226(19) 0.4694(3) 0.0263(8) Uani 1 1 d . . .
C2 C 0.0636(2) 0.74039(19) 0.4046(3) 0.0302(8) Uani 1 1 d . . .
H2 H 0.1083 0.7816 0.3998 0.036 Uiso 1 1 calc R . .
C3 C -0.0337(2) 0.74331(19) 0.3527(3) 0.0310(8) Uani 1 1 d . . .
H3 H -0.0712 0.7867 0.3035 0.037 Uiso 1 1 calc R . .
C4 C -0.0705(2) 0.66739(18) 0.3863(3) 0.0251(8) Uani 1 1 d . . .
C5 C -0.1705(2) 0.64735(18) 0.3470(3) 0.0241(7) Uani 1 1 d . . .
C6 C -0.2084(2) 0.57149(19) 0.3628(3) 0.0257(8) Uani 1 1 d . . .
C7 C 0.3084(2) 0.45254(19) 0.6741(3) 0.0291(8) Uani 1 1 d . . .
H7 H 0.3632 0.4190 0.7142 0.035 Uiso 1 1 calc R . .
C8 C 0.3109(2) 0.5319(2) 0.6414(3) 0.0298(8) Uani 1 1 d . . .
H8 H 0.3682 0.5636 0.6551 0.036 Uiso 1 1 calc R . .
C9 C 0.2137(2) 0.56011(19) 0.5832(3) 0.0249(8) Uani 1 1 d . . .
C10 C 0.1840(2) 0.63693(18) 0.5331(3) 0.0236(7) Uani 1 1 d . . .
N11 N 0.00448(16) 0.61810(14) 0.4559(2) 0.0245(6) Uani 1 1 d . . .
N12 N 0.15386(16) 0.49539(15) 0.5817(2) 0.0245(6) Uani 1 1 d . . .
H12 H 0.0882 0.4917 0.5541 0.029 Uiso 1 1 d R . .
C13 C -0.24074(19) 0.71292(19) 0.2795(3) 0.0264(8) Uani 1 1 d . . .
C14 C -0.3004(2) 0.70444(19) 0.1487(3) 0.0280(8) Uani 1 1 d . . .
H14 H -0.3006 0.6548 0.1034 0.034 Uiso 1 1 calc R . .
C15 C -0.3590(2) 0.7680(2) 0.0847(3) 0.0315(8) Uani 1 1 d . . .
H15 H -0.3982 0.7621 -0.0047 0.038 Uiso 1 1 calc R . .
C16 C -0.3608(2) 0.84054(19) 0.1508(3) 0.0273(8) Uani 1 1 d . . .
C17 C -0.3046(2) 0.84888(19) 0.2829(3) 0.0310(8) Uani 1 1 d . . .
H17 H -0.3068 0.8977 0.3293 0.037 Uiso 1 1 calc R . .
C18 C -0.2455(2) 0.78507(19) 0.3458(3) 0.0294(8) Uani 1 1 d . . .
H18 H -0.2075 0.7906 0.4359 0.035 Uiso 1 1 calc R . .
C19 C -0.4208(2) 0.9101(2) 0.0829(3) 0.0306(8) Uani 1 1 d . . .
O20 O -0.47829(15) 0.89853(14) -0.0348(2) 0.0366(6) Uani 1 1 d D . .
H20 H -0.5164(19) 0.9443(13) -0.077(3) 0.044 Uiso 1 1 d D . .
O21 O -0.41220(17) 0.97738(14) 0.1411(2) 0.0455(7) Uani 1 1 d . . .
C22 C 0.2614(2) 0.69938(19) 0.5431(3) 0.0253(8) Uani 1 1 d . . .
C23 C 0.2697(2) 0.7657(2) 0.6276(3) 0.0332(8) Uani 1 1 d . . .
H23 H 0.2323 0.7676 0.6864 0.040 Uiso 1 1 calc R . .
C24 C 0.3326(2) 0.8288(2) 0.6254(3) 0.0338(9) Uani 1 1 d . . .
H24 H 0.3387 0.8736 0.6834 0.041 Uiso 1 1 calc R . .
C25 C 0.3867(2) 0.82688(19) 0.5389(3) 0.0275(8) Uani 1 1 d . . .
C26 C 0.3818(2) 0.75997(19) 0.4595(3) 0.0310(8) Uani 1 1 d . . .
H26 H 0.4209 0.7576 0.4028 0.037 Uiso 1 1 calc R . .
C27 C 0.3199(2) 0.69613(19) 0.4623(3) 0.0327(8) Uani 1 1 d . . .
H27 H 0.3176 0.6498 0.4084 0.039 Uiso 1 1 calc R . .
C28 C 0.4436(2) 0.8997(2) 0.5278(4) 0.0300(8) Uani 1 1 d . . .
O29 O 0.48270(15) 0.89973(14) 0.4350(3) 0.0390(6) Uani 1 1 d D . .
H29 H 0.511(2) 0.9513(11) 0.429(3) 0.047 Uiso 1 1 d D . .
O30 O 0.45042(16) 0.95849(15) 0.6051(2) 0.0436(7) Uani 1 1 d . . .
C31 C 0.0232(3) 0.0703(2) 0.3889(4) 0.0482(10) Uani 1 1 d . . .
H31 H 0.0671 0.1085 0.4433 0.058 Uiso 1 1 calc R . .
C32 C -0.0759(3) 0.0829(2) 0.3504(4) 0.0572(12) Uani 1 1 d . . .
H32 H -0.1009 0.1305 0.3782 0.069 Uiso 1 1 calc R . .
C33 C -0.1395(3) 0.0273(3) 0.2720(4) 0.0528(11) Uani 1 1 d . . .
H33 H -0.2078 0.0358 0.2487 0.063 Uiso 1 1 calc R . .
C34 C -0.1035(3) -0.0412(2) 0.2272(3) 0.0420(9) Uani 1 1 d . . .
H34 H -0.1473 -0.0787 0.1712 0.050 Uiso 1 1 calc R . .
C35 C -0.0043(2) -0.0549(2) 0.2639(3) 0.0343(8) Uani 1 1 d . . .
H35 H 0.0211 -0.1013 0.2334 0.041 Uiso 1 1 calc R . .
C36 C 0.0569(2) 0.0007(2) 0.3462(3) 0.0371(9) Uani 1 1 d . . .
N37 N 0.1618(2) -0.0159(2) 0.3909(3) 0.0462(8) Uani 1 1 d . . .
O38 O 0.19064(17) -0.08144(17) 0.3613(3) 0.0521(8) Uani 1 1 d . . .
O39 O 0.2165(2) 0.03657(18) 0.4579(3) 0.0669(9) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N11 C1 C10 126.5(3) . . ?
N11 C1 C2 110.4(2) . . ?
C10 C1 C2 123.1(3) . . ?
C3 C2 C1 106.9(3) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
C2 C3 C4 106.7(3) . . ?
C2 C3 H3 126.7 . . ?
C4 C3 H3 126.7 . . ?
N11 C4 C5 125.7(3) . . ?
N11 C4 C3 110.8(2) . . ?
C5 C4 C3 123.4(3) . . ?
C6 C5 C4 125.3(3) . . ?
C6 C5 C13 118.0(2) . . ?
C4 C5 C13 116.7(3) . . ?
N12 C6 C5 125.1(3) 3_566 . ?
N12 C6 C7 106.8(3) 3_566 3_566 ?
C5 C6 C7 128.0(3) . 3_566 ?
C8 C7 C6 107.6(3) . 3_566 ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 3_566 . ?
C7 C8 C9 108.9(3) . . ?
C7 C8 H8 125.6 . . ?
C9 C8 H8 125.6 . . ?
N12 C9 C10 126.0(3) . . ?
N12 C9 C8 106.5(3) . . ?
C10 C9 C8 127.4(3) . . ?
C9 C10 C1 126.5(3) . . ?
C9 C10 C22 117.7(2) . . ?
C1 C10 C22 115.7(3) . . ?
C1 N11 C4 105.1(2) . . ?
C9 N12 C6 110.1(2) . 3_566 ?
C9 N12 H12 130.7 . . ?
C6 N12 H12 119.1 3_566 . ?
C18 C13 C14 118.6(3) . . ?
C18 C13 C5 120.2(3) . . ?
C14 C13 C5 121.2(3) . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 C19 121.2(3) . . ?
C17 C16 C19 118.9(3) . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C13 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
O21 C19 O20 123.2(3) . . ?
O21 C19 C16 119.2(3) . . ?
O20 C19 C16 117.5(3) . . ?
C19 O20 H20 116(2) . . ?
C27 C22 C23 119.1(3) . . ?
C27 C22 C10 121.1(3) . . ?
C23 C22 C10 119.6(3) . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 119.8(3) . . ?
C26 C25 C28 121.4(3) . . ?
C24 C25 C28 118.6(3) . . ?
C25 C26 C27 120.1(3) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C22 C27 C26 120.6(3) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
O30 C28 O29 122.9(3) . . ?
O30 C28 C25 120.2(3) . . ?
O29 C28 C25 116.9(3) . . ?
C28 O29 H29 111(2) . . ?
C36 C31 C32 118.0(4) . . ?
C36 C31 H31 121.0 . . ?
C32 C31 H31 121.0 . . ?
C33 C32 C31 120.9(4) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C32 C33 C34 119.9(4) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 120.2(4) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C36 118.2(3) . . ?
C34 C35 H35 120.9 . . ?
C36 C35 H35 120.9 . . ?
C31 C36 C35 122.7(4) . . ?
C31 C36 N37 119.0(3) . . ?
C35 C36 N37 118.3(3) . . ?
O38 N37 O39 123.6(3) . . ?
O38 N37 C36 118.6(3) . . ?
O39 N37 C36 117.8(3) . . ?
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
C1 N11 1.374(4) . ?
C1 C10 1.407(4) . ?
C1 C2 1.451(4) . ?
C2 C3 1.341(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.448(4) . ?
C3 H3 0.9500 . ?
C4 N11 1.371(4) . ?
C4 C5 1.411(4) . ?
C5 C6 1.396(4) . ?
C5 C13 1.503(4) . ?
C6 N12 1.376(4) 3_566 ?
C6 C7 1.431(4) 3_566 ?
C7 C8 1.358(4) . ?
C7 C6 1.431(4) 3_566 ?
C7 H7 0.9500 . ?
C8 C9 1.425(4) . ?
C8 H8 0.9500 . ?
C9 N12 1.370(4) . ?
C9 C10 1.389(4) . ?
C10 C22 1.499(4) . ?
N12 C6 1.376(4) 3_566 ?
N12 H12 0.9036 . ?
C13 C18 1.397(4) . ?
C13 C14 1.398(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(4) . ?
C16 C19 1.482(4) . ?
C17 C18 1.388(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 O21 1.257(4) . ?
C19 O20 1.284(4) . ?
O20 H20 0.960(10) . ?
C22 C27 1.387(4) . ?
C22 C23 1.398(4) . ?
C23 C24 1.387(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.379(4) . ?
C25 C28 1.480(4) . ?
C26 C27 1.388(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 O30 1.256(4) . ?
C28 O29 1.286(4) . ?
O29 H29 0.956(10) . ?
C31 C36 1.379(5) . ?
C31 C32 1.377(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.378(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.380(5) . ?
C35 H35 0.9500 . ?
C36 N37 1.466(4) . ?
N37 O38 1.234(4) . ?
N37 O39 1.236(4) . ?
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
O20 H20 O21 0.960(10) 1.659(11) 2.616(3) 175(3) 3_475
O29 H29 O30 0.956(10) 1.665(12) 2.615(3) 171(3) 3_676
