#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:13:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178773 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/27/4102786.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_4102786
loop_
_publ_author_name
'José Berná'
'Mateo Alajarín'
'Raúl-Angel Orenes'
_publ_section_title
;
 Azodicarboxamides as Template Binding Motifs for the Building of
 Hydrogen-Bonded Molecular Shuttles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10741
_journal_page_last               10747
_journal_paper_doi               10.1021/ja101151t
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C62 H60 N8 O8'
_chemical_formula_weight         1045.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.513(2)
_cell_angle_beta                 73.874(2)
_cell_angle_gamma                64.295(2)
_cell_formula_units_Z            1
_cell_length_a                   10.2051(5)
_cell_length_b                   11.3570(6)
_cell_length_c                   13.8730(7)
_cell_measurement_reflns_used    5138
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.24
_cell_volume                     1334.45(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω-scan
_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    0.0328
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15582
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.8959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    'NH and OH free, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         6003
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0422
_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)+(0.0458P)²+0.4737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                5054
_reflns_number_total             6003
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja101151t_si_002.cif
_cod_data_source_block           ppnns
_cod_database_code               4102786
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.91817(12) 0.56929(11) 0.33261(8) 0.0169(2) Uani 1 1 d .
H01 H 0.8449(18) 0.6167(17) 0.3716(13) 0.028(4) Uiso 1 1 d .
N2 N 1.05693(11) 0.49640(10) 0.46787(8) 0.0169(2) Uani 1 1 d .
O1 O 1.15341(10) 0.41178(9) 0.32602(7) 0.0222(2) Uani 1 1 d .
C1 C 0.80737(15) 0.75190(13) 0.06265(10) 0.0196(3) Uani 1 1 d .
C2 C 0.91097(17) 0.69926(14) -0.01516(11) 0.0259(3) Uani 1 1 d .
H2 H 1.0117 0.6553 -0.0062 0.031 Uiso 1 1 calc R
C3 C 0.8686(2) 0.71034(16) -0.10600(12) 0.0342(4) Uani 1 1 d .
H3 H 0.9405 0.6749 -0.1590 0.041 Uiso 1 1 calc R
C4 C 0.7227(2) 0.77246(18) -0.11948(12) 0.0390(4) Uani 1 1 d .
H4 H 0.6939 0.7792 -0.1814 0.047 Uiso 1 1 calc R
C5 C 0.61803(19) 0.82509(18) -0.04267(13) 0.0372(4) Uani 1 1 d .
H5 H 0.5173 0.8683 -0.0519 0.045 Uiso 1 1 calc R
C6 C 0.66040(16) 0.81468(15) 0.04801(11) 0.0265(3) Uani 1 1 d .
H6 H 0.5881 0.8509 0.1006 0.032 Uiso 1 1 calc R
C11 C 0.96914(14) 0.79196(13) 0.14845(9) 0.0179(3) Uani 1 1 d .
C12 C 1.11935(15) 0.71678(14) 0.13225(10) 0.0228(3) Uani 1 1 d .
H12 H 1.1526 0.6246 0.1323 0.027 Uiso 1 1 calc R
C13 C 1.22088(16) 0.77586(16) 0.11606(11) 0.0293(3) Uani 1 1 d .
H13 H 1.3230 0.7240 0.1043 0.035 Uiso 1 1 calc R
C14 C 1.17438(18) 0.90941(17) 0.11702(12) 0.0326(4) Uani 1 1 d .
H14 H 1.2440 0.9496 0.1055 0.039 Uiso 1 1 calc R
C15 C 1.02572(19) 0.98387(16) 0.13485(12) 0.0318(3) Uani 1 1 d .
H15 H 0.9928 1.0754 0.1363 0.038 Uiso 1 1 calc R
C16 C 0.92487(16) 0.92553(14) 0.15054(11) 0.0249(3) Uani 1 1 d .
H16 H 0.8230 0.9777 0.1630 0.030 Uiso 1 1 calc R
C21 C 0.85130(14) 0.73592(13) 0.16440(10) 0.0176(3) Uani 1 1 d .
H21 H 0.7618 0.7899 0.2044 0.021 Uiso 1 1 calc R
C22 C 0.89251(14) 0.58614(13) 0.22944(10) 0.0182(3) Uani 1 1 d .
H22A H 0.8121 0.5555 0.2368 0.022 Uiso 1 1 calc R
H22B H 0.9823 0.5291 0.1931 0.022 Uiso 1 1 calc R
C23 C 1.04464(14) 0.48760(13) 0.36809(10) 0.0167(3) Uani 1 1 d .
N3 N 0.62798(12) 0.86340(11) 0.61495(9) 0.0181(2) Uani 1 1 d .
H03 H 0.6909(18) 0.7815(17) 0.6164(12) 0.025(4) Uiso 1 1 d .
N4 N 0.64967(12) 0.41729(12) 0.59521(9) 0.0213(2) Uani 1 1 d .
H04 H 0.6988(19) 0.4712(18) 0.5799(14) 0.037(5) Uiso 1 1 d .
O3 O 0.41127(10) 0.99038(9) 0.69101(8) 0.0236(2) Uani 1 1 d .
O4 O 0.46802(11) 0.34660(10) 0.69951(8) 0.0257(2) Uani 1 1 d .
C31 C 0.46588(13) 0.75201(13) 0.72760(10) 0.0169(3) Uani 1 1 d .
C32 C 0.38708(14) 0.73265(14) 0.82793(10) 0.0207(3) Uani 1 1 d .
H32 H 0.3516 0.8013 0.8626 0.025 Uiso 1 1 calc R
C33 C 0.36053(15) 0.61286(15) 0.87722(11) 0.0245(3) Uani 1 1 d .
H33 H 0.3080 0.5993 0.9461 0.029 Uiso 1 1 calc R
C34 C 0.40986(14) 0.51315(14) 0.82697(10) 0.0211(3) Uani 1 1 d .
H34 H 0.3898 0.4321 0.8608 0.025 Uiso 1 1 calc R
C35 C 0.48929(13) 0.53156(13) 0.72632(10) 0.0172(3) Uani 1 1 d .
C36 C 0.51628(13) 0.65150(13) 0.67689(10) 0.0165(3) Uani 1 1 d .
H36 H 0.5693 0.6649 0.6082 0.020 Uiso 1 1 calc R
C37 C 0.53591(14) 0.42365(13) 0.67279(10) 0.0184(3) Uani 1 1 d .
C38 C 0.68998(15) 0.33067(16) 0.52782(13) 0.0292(3) Uani 1 1 d .
H38A H 0.6564 0.3888 0.4594 0.035 Uiso 1 1 calc R
H38B H 0.6367 0.2674 0.5594 0.035 Uiso 1 1 calc R
C39 C 0.49840(14) 0.87978(13) 0.67592(10) 0.0164(3) Uani 1 1 d .
C40 C 0.68680(14) 0.97215(13) 0.56477(11) 0.0202(3) Uani 1 1 d .
H40A H 0.6673 1.0247 0.6139 0.024 Uiso 1 1 calc R
H40B H 0.6395 1.0352 0.5020 0.024 Uiso 1 1 calc R
C41 C 0.84987(14) 0.90594(13) 0.53420(10) 0.0176(3) Uani 1 1 d .
C42 C 0.94471(14) 0.86350(13) 0.60570(10) 0.0194(3) Uani 1 1 d .
H42 H 0.9081 0.8877 0.6694 0.023 Uiso 1 1 calc R
C43 C 1.09222(14) 0.78614(13) 0.58480(10) 0.0200(3) Uani 1 1 d .
H43 H 1.1557 0.7563 0.6348 0.024 Uiso 1 1 calc R
C44 C 1.14807(14) 0.75184(13) 0.49083(10) 0.0188(3) Uani 1 1 d .
C45 C 1.05454(14) 0.79854(13) 0.41753(10) 0.0194(3) Uani 1 1 d .
H45 H 1.0922 0.7786 0.3522 0.023 Uiso 1 1 calc R
C46 C 0.90612(14) 0.87428(13) 0.43940(10) 0.0194(3) Uani 1 1 d .
H46 H 0.8426 0.9046 0.3893 0.023 Uiso 1 1 calc R
O5 O 0.35972(10) 0.26444(10) 0.58292(8) 0.0207(2) Uani 1 1 d D
H05A H 0.378(2) 0.1753(16) 0.6121(15) 0.046(5) Uiso 1 1 d D
H05B H 0.401(2) 0.2829(19) 0.6219(14) 0.046(5) Uiso 1 1 d 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'
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
C23 N1 C22 122.56(11) . .
N2 N2 C23 112.87(13) 2_766 .
C2 C1 C6 118.57(13) . .
C2 C1 C21 121.25(12) . .
C6 C1 C21 120.12(12) . .
C3 C2 C1 120.62(14) . .
C4 C3 C2 120.26(15) . .
C3 C4 C5 119.87(14) . .
C4 C5 C6 119.92(15) . .
C5 C6 C1 120.76(15) . .
C16 C11 C12 118.03(12) . .
C16 C11 C21 118.30(12) . .
C12 C11 C21 123.66(12) . .
C13 C12 C11 120.44(13) . .
C14 C13 C12 120.54(14) . .
C15 C14 C13 119.37(14) . .
C16 C15 C14 120.14(14) . .
C15 C16 C11 121.45(14) . .
C11 C21 C1 113.62(10) . .
C11 C21 C22 113.35(11) . .
C1 C21 C22 108.60(10) . .
N1 C22 C21 110.37(10) . .
O1 C23 N1 128.29(12) . .
O1 C23 N2 116.69(11) . .
N1 C23 N2 114.92(11) . .
C39 N3 C40 123.54(11) . .
C37 N4 C38 121.98(12) . .
C32 C31 C36 119.73(12) . .
C32 C31 C39 119.69(11) . .
C36 C31 C39 120.57(11) . .
C33 C32 C31 119.87(12) . .
C34 C33 C32 120.55(12) . .
C33 C34 C35 119.98(12) . .
C36 C35 C34 119.52(12) . .
C36 C35 C37 121.98(11) . .
C34 C35 C37 118.42(11) . .
C35 C36 C31 120.33(12) . .
O4 C37 N4 122.72(12) . .
O4 C37 C35 119.74(12) . .
N4 C37 C35 117.53(11) . .
N4 C38 C44 114.97(11) . 2_766
O3 C39 N3 123.52(12) . .
O3 C39 C31 121.70(11) . .
N3 C39 C31 114.77(11) . .
N3 C40 C41 107.61(10) . .
C42 C41 C46 119.10(12) . .
C42 C41 C40 119.62(12) . .
C46 C41 C40 120.97(12) . .
C43 C42 C41 120.53(12) . .
C42 C43 C44 120.38(12) . .
C45 C44 C43 119.16(12) . .
C45 C44 C38 123.05(12) . 2_766
C43 C44 C38 117.75(12) . 2_766
C44 C45 C46 120.31(12) . .
C45 C46 C41 120.44(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C23 1.3223(16) .
N1 C22 1.4554(16) .
N2 N2 1.244(2) 2_766
N2 C23 1.4665(17) .
O1 C23 1.2220(15) .
C1 C2 1.390(2) .
C1 C6 1.3909(19) .
C1 C21 1.5231(18) .
C2 C3 1.389(2) .
C3 C4 1.377(3) .
C4 C5 1.383(3) .
C5 C6 1.390(2) .
C11 C16 1.3915(19) .
C11 C12 1.3940(18) .
C11 C21 1.5209(18) .
C12 C13 1.392(2) .
C13 C14 1.383(2) .
C14 C15 1.382(2) .
C15 C16 1.381(2) .
C21 C22 1.5331(18) .
N3 C39 1.3339(16) .
N3 C40 1.4668(16) .
N4 C37 1.3423(17) .
N4 C38 1.4559(17) .
O3 C39 1.2379(15) .
O4 C37 1.2364(15) .
C31 C32 1.3928(18) .
C31 C36 1.3930(18) .
C31 C39 1.5011(17) .
C32 C33 1.3882(19) .
C33 C34 1.3823(19) .
C34 C35 1.3981(18) .
C35 C36 1.3921(18) .
C35 C37 1.4981(18) .
C38 C44 1.5078(18) 2_766
C40 C41 1.5068(17) .
C41 C42 1.3898(18) .
C41 C46 1.3915(18) .
C42 C43 1.3853(18) .
C43 C44 1.3938(18) .
C44 C45 1.3896(19) .
C44 C38 1.5078(18) 2_766
C45 C46 1.3899(18) .
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
N3 H03 O1 0.868(17) 2.091(17) 2.9166(15) 158.5(15) 2_766
N4 H04 N2 0.886(18) 2.547(18) 3.3398(16) 149.4(15) 2_766
O5 H05A O3 0.895(16) 1.905(16) 2.7949(14) 172.7(18) 1_545
N1 H01 O5 0.884(17) 2.007(17) 2.8480(15) 158.6(15) 2_666
C36 H36 O5 0.95 2.47 3.3908(16) 164.6 2_666
O5 H05B O4 0.891(16) 1.890(16) 2.7752(14) 172.1(18) .
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_4
C6 C1 C2 C3 0.6(2) . .
C21 C1 C2 C3 177.68(13) . .
C1 C2 C3 C4 -0.7(2) . .
C2 C3 C4 C5 0.6(2) . .
C3 C4 C5 C6 -0.2(2) . .
C4 C5 C6 C1 0.1(2) . .
C2 C1 C6 C5 -0.3(2) . .
C21 C1 C6 C5 -177.39(13) . .
C16 C11 C12 C13 -1.62(19) . .
C21 C11 C12 C13 178.67(12) . .
C11 C12 C13 C14 0.8(2) . .
C12 C13 C14 C15 0.4(2) . .
C13 C14 C15 C16 -0.6(2) . .
C14 C15 C16 C11 -0.3(2) . .
C12 C11 C16 C15 1.4(2) . .
C21 C11 C16 C15 -178.87(13) . .
C16 C11 C21 C1 93.35(14) . .
C12 C11 C21 C1 -86.93(15) . .
C16 C11 C21 C22 -142.04(12) . .
C12 C11 C21 C22 37.67(17) . .
C2 C1 C21 C11 56.22(16) . .
C6 C1 C21 C11 -126.73(13) . .
C2 C1 C21 C22 -70.90(15) . .
C6 C1 C21 C22 106.15(14) . .
C23 N1 C22 C21 -121.27(13) . .
C11 C21 C22 N1 59.55(14) . .
C1 C21 C22 N1 -173.17(10) . .
C22 N1 C23 O1 -3.4(2) . .
C22 N1 C23 N2 172.67(10) . .
N2 N2 C23 O1 -141.35(14) 2_766 .
N2 N2 C23 N1 42.07(17) 2_766 .
C36 C31 C32 C33 0.67(19) . .
C39 C31 C32 C33 -178.09(12) . .
C31 C32 C33 C34 -0.9(2) . .
C32 C33 C34 C35 1.1(2) . .
C33 C34 C35 C36 -0.91(19) . .
C33 C34 C35 C37 -177.69(12) . .
C34 C35 C36 C31 0.65(18) . .
C37 C35 C36 C31 177.31(11) . .
C32 C31 C36 C35 -0.53(18) . .
C39 C31 C36 C35 178.22(11) . .
C38 N4 C37 O4 8.0(2) . .
C38 N4 C37 C35 -170.61(12) . .
C36 C35 C37 O4 -153.41(12) . .
C34 C35 C37 O4 23.29(18) . .
C36 C35 C37 N4 25.21(18) . .
C34 C35 C37 N4 -158.09(12) . .
C37 N4 C38 C44 -134.34(14) . 2_766
C40 N3 C39 O3 4.5(2) . .
C40 N3 C39 C31 -174.39(11) . .
C32 C31 C39 O3 -33.82(18) . .
C36 C31 C39 O3 147.43(13) . .
C32 C31 C39 N3 145.12(12) . .
C36 C31 C39 N3 -33.63(17) . .
C39 N3 C40 C41 161.33(12) . .
N3 C40 C41 C42 -87.73(14) . .
N3 C40 C41 C46 85.83(14) . .
C46 C41 C42 C43 -2.52(19) . .
C40 C41 C42 C43 171.17(12) . .
C41 C42 C43 C44 1.14(19) . .
C42 C43 C44 C45 1.29(19) . .
C42 C43 C44 C38 179.05(12) . 2_766
C43 C44 C45 C46 -2.33(19) . .
C38 C44 C45 C46 -179.97(12) 2_766 .
C44 C45 C46 C41 0.95(19) . .
C42 C41 C46 C45 1.48(19) . .
C40 C41 C46 C45 -172.12(11) . .
