#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/31/7103164.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_7103164
loop_
_publ_author_name
'Piepenbrock, Marc-Oliver M'
'Lloyd, Gareth O'
'Clarke, Nigel'
'Steed, Jonathan W'
_publ_section_title
;
 Gelation is crucially dependent on functional group orientation and
 may be tuned by anion binding.
;
_journal_issue                   23
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2644
_journal_page_last               2646
_journal_paper_doi               10.1039/b804259d
_journal_year                    2008
_chemical_formula_moiety         'C20 H26 N4 O2'
_chemical_formula_sum            'C20 H26 N4 O2'
_chemical_formula_weight         354.45
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 107.849(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.1914(14)
_cell_length_b                   4.6342(6)
_cell_length_c                   17.341(2)
_cell_measurement_reflns_used    972
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      23.422
_cell_measurement_theta_min      2.435
_cell_volume                     932.57(19)
_computing_cell_refinement       Saint
_computing_data_collection       Smart
_computing_data_reduction        Saint
_computing_molecular_graphics    Xseed
_computing_publication_material  Xseed
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  6K
_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  0.2294
_diffrn_reflns_av_sigmaI/netI    0.2359
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7921
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.896
_refine_ls_R_factor_all          0.1602
_refine_ls_R_factor_gt           0.0972
_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)+(0.1017P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2219
_refine_ls_wR_factor_ref         0.2549
_reflns_number_gt                2170
_reflns_number_total             4407
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b804259d.txt
_cod_data_source_block           z:\xraydata\gareth\07srv312\work\xm
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7103164
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.3310(3) 0.7341(8) 0.9876(2) 0.0257(9) Uani 1 1 d . . .
O2 O 0.5828(4) 0.2218(8) 1.3136(2) 0.0285(9) Uani 1 1 d . . .
N3 N 0.4026(4) 0.3069(9) 1.0450(2) 0.0231(10) Uani 1 1 d . . .
H3 H 0.3973 0.1178 1.0407 0.028 Uiso 1 1 calc R . .
C4 C 0.5798(4) 0.4866(11) 1.3142(3) 0.0186(10) Uani 1 1 d . . .
N5 N 0.2727(4) 0.3178(10) 0.9184(2) 0.0231(9) Uani 1 1 d . . .
H5 H 0.2844 0.1308 0.9168 0.028 Uiso 1 1 calc R . .
N6 N 0.6437(4) 0.6497(10) 1.3755(2) 0.0253(10) Uani 1 1 d . . .
H6 H 0.6344 0.8382 1.3728 0.030 Uiso 1 1 calc R . .
N7 N 0.5071(4) 0.6404(10) 1.2525(2) 0.0228(10) Uani 1 1 d . . .
H7 H 0.5084 0.8300 1.2552 0.027 Uiso 1 1 calc R . .
C8 C 0.3348(4) 0.4716(12) 0.9845(3) 0.0200(11) Uani 1 1 d . . .
C9 C 0.1876(4) 0.4560(12) 0.8505(3) 0.0228(11) Uani 1 1 d . . .
H9 H 0.2116 0.6618 0.8492 0.027 Uiso 1 1 calc R . .
C10 C 0.7286(4) 0.5248(11) 1.4471(3) 0.0218(11) Uani 1 1 d . . .
H10 H 0.6965 0.3402 1.4609 0.026 Uiso 1 1 calc R . .
C11 C 0.7435(4) 0.7339(11) 1.5170(3) 0.0207(10) Uani 1 1 d . . .
C12 C 0.0681(5) 0.4575(12) 0.8584(3) 0.0237(12) Uani 1 1 d . . .
C13 C 0.4836(5) 0.4329(12) 1.1167(3) 0.0233(11) Uani 1 1 d . . .
H13A H 0.5155 0.6126 1.1013 0.028 Uiso 1 1 calc R . .
H13B H 0.5484 0.2970 1.1387 0.028 Uiso 1 1 calc R . .
C14 C 0.6464(5) 0.8095(12) 1.5399(3) 0.0255(12) Uani 1 1 d . . .
H14 H 0.5737 0.7260 1.5126 0.031 Uiso 1 1 calc R . .
C15 C 0.4278(4) 0.5016(12) 1.1827(3) 0.0242(11) Uani 1 1 d . . .
H15A H 0.3606 0.6294 1.1598 0.029 Uiso 1 1 calc R . .
H15B H 0.3995 0.3203 1.2001 0.029 Uiso 1 1 calc R . .
C16 C -0.0739(5) 0.3034(13) 0.9208(3) 0.0359(14) Uani 1 1 d . . .
H16 H -0.0943 0.1831 0.9586 0.043 Uiso 1 1 calc R . .
C17 C 0.0362(5) 0.2873(12) 0.9144(3) 0.0277(12) Uani 1 1 d . . .
H17 H 0.0907 0.1591 0.9485 0.033 Uiso 1 1 calc R . .
C18 C 0.8396(5) 0.4568(14) 1.4282(3) 0.0318(13) Uani 1 1 d . . .
H18A H 0.8235 0.3204 1.3829 0.048 Uiso 1 1 calc R . .
H18B H 0.8952 0.3710 1.4761 0.048 Uiso 1 1 calc R . .
H18C H 0.8717 0.6350 1.4136 0.048 Uiso 1 1 calc R . .
C19 C 0.6559(5) 1.0048(15) 1.6019(3) 0.0375(14) Uani 1 1 d . . .
H19 H 0.5893 1.0552 1.6164 0.045 Uiso 1 1 calc R . .
C20 C 0.1906(5) 0.3167(13) 0.7713(3) 0.0295(12) Uani 1 1 d . . .
H20A H 0.2696 0.3208 0.7683 0.044 Uiso 1 1 calc R . .
H20B H 0.1398 0.4237 0.7254 0.044 Uiso 1 1 calc R . .
H20C H 0.1643 0.1163 0.7694 0.044 Uiso 1 1 calc R . .
C21 C 0.8486(5) 0.8527(12) 1.5602(3) 0.0282(12) Uani 1 1 d . . .
H21 H 0.9160 0.7977 1.5473 0.034 Uiso 1 1 calc R . .
C22 C -0.0154(5) 0.6386(13) 0.8092(3) 0.0340(13) Uani 1 1 d . . .
H22 H 0.0035 0.7536 0.7698 0.041 Uiso 1 1 calc R . .
C23 C 0.8577(6) 1.0517(14) 1.6222(3) 0.0367(15) Uani 1 1 d . . .
H23 H 0.9302 1.1349 1.6501 0.044 Uiso 1 1 calc R . .
C24 C 0.7605(6) 1.1273(14) 1.6429(3) 0.0373(14) Uani 1 1 d . . .
H24 H 0.7659 1.2626 1.6850 0.045 Uiso 1 1 calc R . .
C25 C -0.1536(5) 0.4877(14) 0.8742(4) 0.0359(14) Uani 1 1 d . . .
H25 H -0.2278 0.5019 0.8810 0.043 Uiso 1 1 calc R . .
C26 C -0.1257(5) 0.6558(13) 0.8162(4) 0.0342(14) Uani 1 1 d . . .
H26 H -0.1814 0.7805 0.7818 0.041 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
C8 N3 C13 122.0(5) . . ?
C8 N3 H3 119.0 . . ?
C13 N3 H3 119.0 . . ?
O2 C4 N6 123.9(5) . . ?
O2 C4 N7 122.0(5) . . ?
N6 C4 N7 114.0(4) . . ?
C8 N5 C9 121.6(5) . . ?
C8 N5 H5 119.2 . . ?
C9 N5 H5 119.2 . . ?
C4 N6 C10 122.3(4) . . ?
C4 N6 H6 118.8 . . ?
C10 N6 H6 118.8 . . ?
C4 N7 C15 122.1(4) . . ?
C4 N7 H7 119.0 . . ?
C15 N7 H7 119.0 . . ?
O1 C8 N3 123.4(5) . . ?
O1 C8 N5 122.6(5) . . ?
N3 C8 N5 113.9(5) . . ?
N5 C9 C12 113.4(4) . . ?
N5 C9 C20 109.5(4) . . ?
C12 C9 C20 112.0(4) . . ?
N5 C9 H9 107.2 . . ?
C12 C9 H9 107.2 . . ?
C20 C9 H9 107.2 . . ?
N6 C10 C18 110.1(4) . . ?
N6 C10 C11 107.7(4) . . ?
C18 C10 C11 114.1(5) . . ?
N6 C10 H10 108.3 . . ?
C18 C10 H10 108.3 . . ?
C11 C10 H10 108.3 . . ?
C21 C11 C14 118.0(5) . . ?
C21 C11 C10 123.3(5) . . ?
C14 C11 C10 118.7(4) . . ?
C22 C12 C17 117.4(5) . . ?
C22 C12 C9 119.6(5) . . ?
C17 C12 C9 123.0(5) . . ?
N3 C13 C15 112.4(4) . . ?
N3 C13 H13A 109.1 . . ?
C15 C13 H13A 109.1 . . ?
N3 C13 H13B 109.1 . . ?
C15 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C19 C14 C11 120.4(5) . . ?
C19 C14 H14 119.8 . . ?
C11 C14 H14 119.8 . . ?
N7 C15 C13 112.4(4) . . ?
N7 C15 H15A 109.1 . . ?
C13 C15 H15A 109.1 . . ?
N7 C15 H15B 109.1 . . ?
C13 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C25 C16 C17 121.4(6) . . ?
C25 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C12 120.6(5) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C14 121.0(6) . . ?
C24 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C21 C23 121.4(5) . . ?
C11 C21 H21 119.3 . . ?
C23 C21 H21 119.3 . . ?
C26 C22 C12 121.8(6) . . ?
C26 C22 H22 119.1 . . ?
C12 C22 H22 119.1 . . ?
C24 C23 C21 119.7(5) . . ?
C24 C23 H23 120.1 . . ?
C21 C23 H23 120.1 . . ?
C19 C24 C23 119.5(6) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C16 C25 C26 119.5(6) . . ?
C16 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C22 C26 C25 119.2(6) . . ?
C22 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
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
O1 C8 1.219(6) . ?
O2 C4 1.228(6) . ?
N3 C8 1.354(6) . ?
N3 C13 1.453(6) . ?
N3 H3 0.8800 . ?
C4 N6 1.342(7) . ?
C4 N7 1.362(6) . ?
N5 C8 1.365(6) . ?
N5 C9 1.458(6) . ?
N5 H5 0.8800 . ?
N6 C10 1.469(6) . ?
N6 H6 0.8800 . ?
N7 C15 1.448(6) . ?
N7 H7 0.8800 . ?
C9 C12 1.505(7) . ?
C9 C20 1.528(7) . ?
C9 H9 1.0000 . ?
C10 C18 1.519(7) . ?
C10 C11 1.519(7) . ?
C10 H10 1.0000 . ?
C11 C21 1.385(7) . ?
C11 C14 1.403(8) . ?
C12 C22 1.392(8) . ?
C12 C17 1.396(7) . ?
C13 C15 1.533(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.383(8) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C25 1.359(9) . ?
C16 C17 1.383(9) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.378(9) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C23 1.395(8) . ?
C21 H21 0.9500 . ?
C22 C26 1.388(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(9) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.395(9) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
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
O2 C4 N6 C10 3.1(8) . . . . ?
N7 C4 N6 C10 -179.0(4) . . . . ?
O2 C4 N7 C15 0.7(8) . . . . ?
N6 C4 N7 C15 -177.3(4) . . . . ?
C13 N3 C8 O1 -4.8(7) . . . . ?
C13 N3 C8 N5 173.6(5) . . . . ?
C9 N5 C8 O1 -7.1(7) . . . . ?
C9 N5 C8 N3 174.5(4) . . . . ?
C8 N5 C9 C12 -91.1(6) . . . . ?
C8 N5 C9 C20 142.9(5) . . . . ?
C4 N6 C10 C18 80.4(6) . . . . ?
C4 N6 C10 C11 -154.7(5) . . . . ?
N6 C10 C11 C21 -122.6(5) . . . . ?
C18 C10 C11 C21 -0.1(7) . . . . ?
N6 C10 C11 C14 58.0(6) . . . . ?
C18 C10 C11 C14 -179.5(4) . . . . ?
N5 C9 C12 C22 164.8(5) . . . . ?
C20 C9 C12 C22 -70.7(7) . . . . ?
N5 C9 C12 C17 -14.2(7) . . . . ?
C20 C9 C12 C17 110.4(6) . . . . ?
C8 N3 C13 C15 86.6(6) . . . . ?
C21 C11 C14 C19 2.2(7) . . . . ?
C10 C11 C14 C19 -178.3(5) . . . . ?
C4 N7 C15 C13 -85.9(6) . . . . ?
N3 C13 C15 N7 -177.1(5) . . . . ?
C25 C16 C17 C12 -1.1(9) . . . . ?
C22 C12 C17 C16 -0.9(8) . . . . ?
C9 C12 C17 C16 178.1(5) . . . . ?
C11 C14 C19 C24 -0.5(9) . . . . ?
C14 C11 C21 C23 -2.8(8) . . . . ?
C10 C11 C21 C23 177.8(5) . . . . ?
C17 C12 C22 C26 1.4(8) . . . . ?
C9 C12 C22 C26 -177.7(5) . . . . ?
C11 C21 C23 C24 1.7(8) . . . . ?
C14 C19 C24 C23 -0.6(9) . . . . ?
C21 C23 C24 C19 0.0(9) . . . . ?
C17 C16 C25 C26 2.7(9) . . . . ?
C12 C22 C26 C25 0.2(9) . . . . ?
C16 C25 C26 C22 -2.2(9) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24747115
