#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:48:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178445 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/66/4026641.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_4026641
loop_
_publ_author_name
'Felipe Reviriego'
'Pilar Navarro'
'Vicente J. Arán'
'Maria Luisa Jimeno'
'Enrique García-España'
'Julio Latorre'
'Maria J. R. Yunta'
_publ_section_title
;
 Hydrogen-Bond-Mediated Self-Assembly of 26-Membered Diaza Tetraester
 Crowns of 3,5-Disubstituted 1H-Pyrazole. Dimerization Study in the Solid
 State and in CDCl3 Solution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8223
_journal_page_last               8231
_journal_paper_doi               10.1021/jo2012835
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C20 H26 N6 O8, C2 H3 N'
_chemical_formula_sum            'C22 H29 N7 O8'
_chemical_formula_weight         519.52
_chemical_name_common            pzmet
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.1070(2)
_cell_length_b                   13.1070(2)
_cell_length_c                   30.3510(7)
_cell_measurement_temperature    293(2)
_cell_volume                     5214.10(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            5223
_diffrn_reflns_theta_full        26.72
_diffrn_reflns_theta_max         26.72
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             2268
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.016
_refine_diff_density_min         -0.006
_refine_diff_density_rms         0.003
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1231P)²+0.0022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.2266
_reflns_number_gt                1824
_reflns_number_total             2784
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo2012835_si_002.cif
_cod_data_source_block           pznoxxx
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               4026641
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'
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
O1 O 0.58173(16) 0.38686(16) 0.11062(7) 0.0806(16) Uani 1 1 d . A 1
O2 O 0.44908(15) 0.44696(15) 0.07116(7) 0.0758(16) Uani 1 1 d . A 1
O3 O 0.63201(18) 0.81202(17) -0.00410(7) 0.0874(16) Uani 1 1 d . B 1
O4 O 0.24794(18) 0.65603(16) 0.04639(8) 0.0875(16) Uani 1 1 d . . 1
N1 N 0.6760(2) 0.5791(2) 0.10179(9) 0.0787(16) Uani 1 1 d . A 1
H1 H 0.704(3) 0.541(3) 0.1229(12) 0.082(9) Uiso 1 1 d . C 1
N2 N 0.7155(2) 0.66665(19) 0.08797(9) 0.0808(16) Uani 1 1 d . A 1
N3 N 0.22419(19) 0.44718(18) 0.08489(9) 0.0772(16) Uani 1 1 d . A 1
C3 C 0.5935(2) 0.5501(2) 0.07831(10) 0.0725(16) Uani 1 1 d . A 1
C4 C 0.5782(2) 0.6242(2) 0.04679(9) 0.0757(16) Uani 1 1 d . A 1
H4 H 0.5273 0.6266 0.0255 0.075(8) Uiso 1 1 calc R A 1
C5 C 0.6563(2) 0.6952(2) 0.05395(9) 0.0737(16) Uani 1 1 d . A 1
C6 C 0.5428(2) 0.4526(2) 0.08878(10) 0.0723(16) Uani 1 1 d . A 1
C7 C 0.3912(2) 0.3571(2) 0.08326(12) 0.0804(16) Uani 1 1 d . A 1
H7A H 0.3872 0.3525 0.1148 0.096 Uiso 1 1 d R A 1
H7B H 0.4254 0.2980 0.0719 0.096 Uiso 1 1 d R A 1
C8 C 0.2864(2) 0.3673(2) 0.06401(11) 0.0813(16) Uani 1 1 d . A 1
H8A H 0.2951 0.3837 0.0334 0.098 Uiso 1 1 d R A 1
H8B H 0.2522 0.3028 0.0666 0.098 Uiso 1 1 d R A 1
C9 C 0.1620(3) 0.4031(3) 0.12077(14) 0.1000(18) Uani 1 1 d . A 1
H9A H 0.1222 0.4555 0.1346 0.120 Uiso 1 1 d R A 1
H9B H 0.1175 0.3518 0.1090 0.120 Uiso 1 1 d R A 1
H9C H 0.2069 0.3728 0.1421 0.120 Uiso 1 1 d R A 1
C10 C 0.1593(2) 0.4982(2) 0.05295(12) 0.0873(17) Uani 1 1 d . A 1
H10A H 0.1112 0.5403 0.0684 0.105 Uiso 1 1 d R A 1
H10B H 0.1232 0.4478 0.0361 0.105 Uiso 1 1 d R A 1
C11 C 0.2168(3) 0.5664(2) 0.02188(12) 0.0918(17) Uani 1 1 d . A 1
H11A H 0.1740 0.5850 -0.0025 0.110 Uiso 1 1 d R A 1
H11B H 0.2752 0.5296 0.0112 0.110 Uiso 1 1 d R A 1
C12 C 0.6770(2) 0.7886(2) 0.02877(10) 0.0758(16) Uani 1 1 d . . 1
N20 N 0.0000 0.7500 -0.03166(19) 0.206(4) Uiso 1 2 d SG . 1
C20 C 0.0079(3) 0.7607(3) 0.00607(19) 0.137(3) Uiso 0.50 1 d PG . 1
C30 C 0.0177(7) 0.7741(7) 0.05351(19) 0.111(3) Uiso 0.50 1 d PG . 1
H30A H -0.0489 0.7773 0.0666 0.167 Uiso 0.50 1 d PG . 1
H30B H 0.0539 0.8363 0.0595 0.167 Uiso 0.50 1 d PG . 1
H30C H 0.0547 0.7175 0.0657 0.167 Uiso 0.50 1 d PG . 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'
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
C6 O2 C7 115.0(2) . .
C12 O4 C11 116.3(3) 2_665 .
N2 N1 C3 112.9(3) . .
N2 N1 H1 123(2) . .
C3 N1 H1 124(2) . .
N1 N2 C5 105.0(2) . .
C10 N3 C8 111.4(2) . .
C10 N3 C9 110.4(3) . .
C8 N3 C9 110.2(3) . .
N1 C3 C4 106.5(3) . .
N1 C3 C6 119.4(3) . .
C4 C3 C6 134.0(3) . .
C3 C4 C5 104.7(3) . .
C3 C4 H4 127.6 . .
C5 C4 H4 127.6 . .
N2 C5 C4 110.9(3) . .
N2 C5 C12 121.7(3) . .
C4 C5 C12 127.4(3) . .
O1 C6 O2 124.8(3) . .
O1 C6 C3 123.2(3) . .
O2 C6 C3 112.0(2) . .
O2 C7 C8 108.0(2) . .
O2 C7 H7A 109.4 . .
C8 C7 H7A 110.2 . .
O2 C7 H7B 108.7 . .
C8 C7 H7B 111.1 . .
H7A C7 H7B 109.5 . .
N3 C8 C7 113.8(3) . .
N3 C8 H8A 108.8 . .
C7 C8 H8A 106.7 . .
N3 C8 H8B 109.4 . .
C7 C8 H8B 108.5 . .
H8A C8 H8B 109.5 . .
N3 C9 H9A 110.1 . .
N3 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N3 C9 H9C 108.7 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N3 C10 C11 113.5(3) . .
N3 C10 H10A 108.9 . .
C11 C10 H10A 107.0 . .
N3 C10 H10B 109.1 . .
C11 C10 H10B 108.8 . .
H10A C10 H10B 109.5 . .
O4 C11 C10 107.6(3) . .
O4 C11 H11A 110.8 . .
C10 C11 H11A 110.0 . .
O4 C11 H11B 110.8 . .
C10 C11 H11B 108.2 . .
H11A C11 H11B 109.5 . .
O3 C12 O4 123.8(3) . 2_665
O3 C12 C5 123.8(3) . .
O4 C12 C5 112.4(3) 2_665 .
C20 N20 C20 17.3(3) 2_565 .
C20 C20 N20 81.4 2_565 .
C20 C20 C30 98.6 2_565 .
N20 C20 C30 180.0(7) . .
C20 C20 C30 68.5(5) 2_565 2_565
N20 C20 C30 149.9(5) . 2_565
C30 C20 C30 30.1(5) . 2_565
C30 C30 C20 81.4 2_565 .
C30 C30 C20 68.5(2) 2_565 2_565
C20 C30 C20 12.8(2) . 2_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.201(4) .
O2 C6 1.341(3) .
O2 C7 1.448(4) .
O3 C12 1.199(4) .
O4 C12 1.334(4) 2_665
O4 C11 1.449(4) .
N1 N2 1.327(3) .
N1 C3 1.350(4) .
N1 H1 0.89(4) .
N2 C5 1.344(4) .
N3 C10 1.453(4) .
N3 C8 1.471(4) .
N3 C9 1.477(5) .
C3 C4 1.379(4) .
C3 C6 1.476(4) .
C4 C5 1.400(4) .
C4 H4 0.9300 .
C5 C12 1.469(4) .
C7 C8 1.499(4) .
C7 H7A 0.9599 .
C7 H7B 0.9600 .
C8 H8A 0.9602 .
C8 H8B 0.9600 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9599 .
C10 C11 1.503(5) .
C10 H10A 0.9599 .
C10 H10B 0.9601 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C12 O4 1.334(4) 2_665
N20 C20 1.1583(10) 2_565
N20 C20 1.1583 .
C20 C20 0.347(7) 2_565
C20 C30 1.4563 .
C20 C30 1.547(6) 2_565
C30 C30 0.784(15) 2_565
C30 C20 1.547(2) 2_565
C30 H30A 0.9600 .
C30 H30B 0.9600 .
C30 H30C 0.9600 .
