#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/07/7150739.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_7150739
loop_
_publ_author_name
'Reviriego, Felipe'
'Sanz, Ana'
'Navarro, Pilar'
'Latorre, Julio'
'García-España, Enrique'
'Liu-Gonzalez, Malva'
_publ_section_title
;
 Self-assembly of 3,5-bis(ethoxycarbonyl)pyrazolate anions and ammonium
 cations of β-phenylethylamine or homoveratrylamine into
 hetero-double-stranded helical structures
;
_journal_issue                   16
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3212
_journal_page_last               3214
_journal_paper_doi               10.1039/b911053d
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C10 H16 N O2, C9 H11 N2 O4'
_chemical_formula_sum            'C19 H27 N3 O6'
_chemical_formula_weight         393.44
_chemical_name_common            'Compound ege4v09'
_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                 99.289(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1760(5)
_cell_length_b                   5.4360(2)
_cell_length_c                   29.7130(10)
_cell_measurement_reflns_used    3901
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      0.998
_cell_volume                     2100.28(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 19)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97(Altomare & Al., 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0637
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            6300
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flat
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0513
_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)+(0.1101P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1827
_reflns_number_gt                1827
_reflns_number_total             3791
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b911053d.txt
_cod_data_source_block           ege4
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7150739
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O6A O 0.14831(13) -0.0757(4) 0.19326(6) 0.0879(7) Uani 1 1 d . . .
O6B O 0.07698(15) -0.2143(4) 0.25157(8) 0.0946(7) Uani 1 1 d . . .
O7A O -0.09759(14) 0.6700(4) 0.11288(6) 0.0798(6) Uani 1 1 d . . .
O7B O -0.22781(16) 0.7110(4) 0.15260(7) 0.0977(7) Uani 1 1 d . . .
O15 O 0.29073(17) -0.1729(4) 0.00013(7) 0.1016(7) Uani 1 1 d . . .
O16 O 0.23013(17) 0.1825(5) 0.04566(8) 0.1059(8) Uani 1 1 d . . .
N1 N -0.08264(15) 0.1327(4) 0.22834(7) 0.0678(6) Uani 1 1 d . . .
N2 N -0.14352(15) 0.3140(4) 0.20854(7) 0.0663(6) Uani 1 1 d . . .
N3 N 0.65192(14) 0.2176(4) 0.22504(6) 0.0638(6) Uani 1 1 d . . .
H3A H 0.7124 0.2556 0.2172 0.096 Uiso 1 1 calc R . .
H3B H 0.6615 0.1173 0.2490 0.096 Uiso 1 1 calc R . .
H3C H 0.6209 0.3543 0.2321 0.096 Uiso 1 1 calc R . .
C3 C -0.09952(18) 0.4073(5) 0.17377(8) 0.0608(7) Uani 1 1 d . . .
C4 C -0.00923(18) 0.2823(5) 0.17128(8) 0.0656(7) Uani 1 1 d . . .
H4 H 0.0362 0.3079 0.1508 0.079 Uiso 1 1 calc R . .
C5 C -0.00175(17) 0.1121(5) 0.20573(8) 0.0614(7) Uani 1 1 d . . .
C6 C 0.07608(19) -0.0758(6) 0.22000(10) 0.0725(8) Uani 1 1 d . . .
C7 C -0.1497(2) 0.6098(6) 0.14646(9) 0.0702(8) Uani 1 1 d . . .
C8 C 0.2299(2) -0.2587(7) 0.20361(12) 0.1011(11) Uani 1 1 d . . .
H8A H 0.2601 -0.2499 0.2356 0.121 Uiso 1 1 calc R . .
H8B H 0.2022 -0.4227 0.1973 0.121 Uiso 1 1 calc R . .
C9 C 0.3070(3) -0.2070(7) 0.17537(13) 0.1177(13) Uani 1 1 d . . .
H9A H 0.2766 -0.2174 0.1438 0.177 Uiso 1 1 calc R . .
H9B H 0.3618 -0.3248 0.1817 0.177 Uiso 1 1 calc R . .
H9C H 0.3339 -0.0445 0.1819 0.177 Uiso 1 1 calc R . .
C10 C -0.1347(2) 0.8744(6) 0.08434(10) 0.0879(9) Uani 1 1 d . . .
H10A H -0.1427 1.0180 0.1028 0.106 Uiso 1 1 calc R . .
H10B H -0.2009 0.8354 0.0664 0.106 Uiso 1 1 calc R . .
C11 C -0.0577(3) 0.9236(9) 0.05393(13) 0.1324(15) Uani 1 1 d . . .
H11A H 0.0090 0.9437 0.0720 0.199 Uiso 1 1 calc R . .
H11B H -0.0762 1.0710 0.0368 0.199 Uiso 1 1 calc R . .
H11C H -0.0563 0.7878 0.0334 0.199 Uiso 1 1 calc R . .
C12 C 0.5671(2) 0.2549(6) 0.14567(10) 0.0948(10) Uani 1 1 d . . .
H12A H 0.6318 0.2942 0.1358 0.114 Uiso 1 1 calc R . .
H12B H 0.5365 0.4075 0.1538 0.114 Uiso 1 1 calc R . .
C13 C 0.58661(19) 0.0930(6) 0.18614(9) 0.0730(8) Uani 1 1 d . . .
H13A H 0.6206 -0.0559 0.1785 0.088 Uiso 1 1 calc R . .
H13B H 0.5216 0.0465 0.1951 0.088 Uiso 1 1 calc R . .
C15 C 0.3206(3) -0.3699(7) -0.02656(11) 0.1127(12) Uani 1 1 d . . .
H15A H 0.3833 -0.3276 -0.0372 0.169 Uiso 1 1 calc R . .
H15B H 0.2675 -0.3989 -0.0522 0.169 Uiso 1 1 calc R . .
H15C H 0.3310 -0.5160 -0.0082 0.169 Uiso 1 1 calc R . .
C16 C 0.1904(3) 0.3712(8) 0.07066(14) 0.1245(14) Uani 1 1 d . . .
H16A H 0.1965 0.3233 0.1021 0.187 Uiso 1 1 calc R . .
H16B H 0.1192 0.3981 0.0584 0.187 Uiso 1 1 calc R . .
H16C H 0.2283 0.5202 0.0684 0.187 Uiso 1 1 calc R . .
C20 C 0.4955(2) 0.1332(6) 0.10651(9) 0.0804(9) Uani 1 1 d . . .
C21 C 0.5253(2) -0.0658(7) 0.08317(12) 0.0945(10) Uani 1 1 d . . .
H21 H 0.5910 -0.1303 0.0916 0.113 Uiso 1 1 calc R . .
C22 C 0.4591(3) -0.1727(6) 0.04720(11) 0.0921(10) Uani 1 1 d . . .
H22 H 0.4816 -0.3046 0.0315 0.110 Uiso 1 1 calc R . .
C23 C 0.3621(2) -0.0859(6) 0.03494(9) 0.0756(8) Uani 1 1 d . . .
C24 C 0.3294(2) 0.1092(6) 0.05935(9) 0.0777(8) Uani 1 1 d . . .
C25 C 0.3959(2) 0.2183(6) 0.09423(9) 0.0785(8) Uani 1 1 d . . .
H25 H 0.3735 0.3511 0.1097 0.094 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'
O O 0.0106 0.0060 '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
C6 O6A C8 116.5(2) . . ?
C7 O7A C10 117.5(2) . . ?
C23 O15 C15 117.6(3) . . ?
C24 O16 C16 118.2(3) . . ?
N2 N1 C5 107.8(2) . . ?
N1 N2 C3 107.94(19) . . ?
C13 N3 H3A 109.5 . . ?
C13 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C13 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
N2 C3 C4 109.4(2) . . ?
N2 C3 C7 119.5(2) . . ?
C4 C3 C7 131.1(2) . . ?
C5 C4 C3 104.5(2) . . ?
C5 C4 H4 127.7 . . ?
C3 C4 H4 127.7 . . ?
N1 C5 C4 110.3(2) . . ?
N1 C5 C6 119.1(2) . . ?
C4 C5 C6 130.6(2) . . ?
O6B C6 O6A 123.1(3) . . ?
O6B C6 C5 125.6(2) . . ?
O6A C6 C5 111.2(3) . . ?
O7B C7 O7A 123.6(3) . . ?
O7B C7 C3 125.5(3) . . ?
O7A C7 C3 110.9(2) . . ?
C9 C8 O6A 107.9(3) . . ?
C9 C8 H8A 110.1 . . ?
O6A C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
O6A C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O7A C10 C11 107.3(3) . . ?
O7A C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
O7A C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C20 111.6(3) . . ?
C13 C12 H12A 109.3 . . ?
C20 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C20 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 N3 111.3(2) . . ?
C12 C13 H13A 109.4 . . ?
N3 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
N3 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O15 C15 H15A 109.5 . . ?
O15 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O15 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O16 C16 H16A 109.5 . . ?
O16 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O16 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 C20 C25 117.8(3) . . ?
C21 C20 C12 122.3(3) . . ?
C25 C20 C12 119.9(3) . . ?
C20 C21 C22 121.3(3) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 O15 126.0(3) . . ?
C22 C23 C24 118.8(3) . . ?
O15 C23 C24 115.2(3) . . ?
O16 C24 C25 124.1(3) . . ?
O16 C24 C23 115.4(3) . . ?
C25 C24 C23 120.5(3) . . ?
C24 C25 C20 121.0(3) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?
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
O6A C6 1.334(3) . ?
O6A C8 1.461(4) . ?
O6B C6 1.202(3) . ?
O7A C7 1.340(3) . ?
O7A C10 1.435(3) . ?
O7B C7 1.206(3) . ?
O15 C23 1.365(3) . ?
O15 C15 1.425(4) . ?
O16 C24 1.365(3) . ?
O16 C16 1.416(4) . ?
N1 N2 1.345(3) . ?
N1 C5 1.353(3) . ?
N2 C3 1.362(3) . ?
N3 C13 1.488(3) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
C3 C4 1.382(3) . ?
C3 C7 1.461(4) . ?
C4 C5 1.372(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.461(4) . ?
C8 C9 1.446(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.487(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.479(4) . ?
C12 C20 1.525(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C20 C21 1.376(4) . ?
C20 C25 1.384(4) . ?
C21 C22 1.393(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.356(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.392(4) . ?
C24 C25 1.379(4) . ?
C25 H25 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C3 -0.5(3) . . . . ?
N1 N2 C3 C4 0.3(3) . . . . ?
N1 N2 C3 C7 -179.6(2) . . . . ?
N2 C3 C4 C5 0.1(3) . . . . ?
C7 C3 C4 C5 179.9(3) . . . . ?
N2 N1 C5 C4 0.6(3) . . . . ?
N2 N1 C5 C6 -179.1(2) . . . . ?
C3 C4 C5 N1 -0.4(3) . . . . ?
C3 C4 C5 C6 179.2(3) . . . . ?
C8 O6A C6 O6B 1.1(4) . . . . ?
C8 O6A C6 C5 -179.0(3) . . . . ?
N1 C5 C6 O6B -2.1(4) . . . . ?
C4 C5 C6 O6B 178.3(3) . . . . ?
N1 C5 C6 O6A 178.0(2) . . . . ?
C4 C5 C6 O6A -1.6(4) . . . . ?
C10 O7A C7 O7B 3.2(4) . . . . ?
C10 O7A C7 C3 -177.1(2) . . . . ?
N2 C3 C7 O7B 2.2(4) . . . . ?
C4 C3 C7 O7B -177.6(3) . . . . ?
N2 C3 C7 O7A -177.5(2) . . . . ?
C4 C3 C7 O7A 2.7(4) . . . . ?
C6 O6A C8 C9 -172.2(3) . . . . ?
C7 O7A C10 C11 173.1(3) . . . . ?
C20 C12 C13 N3 -177.0(2) . . . . ?
C13 C12 C20 C21 -69.1(4) . . . . ?
C13 C12 C20 C25 109.1(3) . . . . ?
C25 C20 C21 C22 2.5(5) . . . . ?
C12 C20 C21 C22 -179.4(3) . . . . ?
C20 C21 C22 C23 -1.6(5) . . . . ?
C21 C22 C23 O15 179.2(3) . . . . ?
C21 C22 C23 C24 -0.9(5) . . . . ?
C15 O15 C23 C22 -1.2(5) . . . . ?
C15 O15 C23 C24 178.9(3) . . . . ?
C16 O16 C24 C25 -4.4(5) . . . . ?
C16 O16 C24 C23 176.6(3) . . . . ?
C22 C23 C24 O16 -178.5(3) . . . . ?
O15 C23 C24 O16 1.3(4) . . . . ?
C22 C23 C24 C25 2.5(4) . . . . ?
O15 C23 C24 C25 -177.7(3) . . . . ?
O16 C24 C25 C20 179.6(3) . . . . ?
C23 C24 C25 C20 -1.6(4) . . . . ?
C21 C20 C25 C24 -0.9(4) . . . . ?
C12 C20 C25 C24 -179.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653399
