#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:27:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178783 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/37/4103757.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_4103757
loop_
_publ_author_name
'Zhong Li'
'Frank W. Fowler'
'Joseph W. Lauher'
_publ_section_title
;
 Weak Interactions Dominating the Supramolecular Self-Assembly in a Salt:
 A Designed Single-Crystal-to-Single-Crystal Topochemical Polymerization
 of a Terminal Aryldiacetylene
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              634
_journal_page_last               643
_journal_paper_doi               10.1021/ja806663h
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C12 H26 N4 O6'
_chemical_formula_weight         322.37
_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                70.093(4)
_cell_angle_beta                 69.558(4)
_cell_angle_gamma                66.216(3)
_cell_formula_units_Z            2
_cell_length_a                   9.962(2)
_cell_length_b                   9.965(2)
_cell_length_c                   10.064(2)
_cell_measurement_temperature    273(2)
_cell_volume                     833.1(3)
_computing_cell_refinement       'Bruker SMART'
_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      273(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4907
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_crystal_size_max          .7
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .3
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.063
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0734
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1374P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2305
_reflns_number_gt                1828
_reflns_number_total             4012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806663h_si_004.cif
_cod_data_source_block           jlj
_cod_database_code               4103757
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
O3 O 0.4352(2) 0.3761(2) 0.4711(2) 0.0531(6) Uani 1 1 d .
O6 O -0.0735(2) 0.4603(2) 0.3895(2) 0.0531(6) Uani 1 1 d .
O4 O 0.3841(3) 0.1285(2) 0.1733(2) 0.0595(7) Uani 1 1 d .
N1 N 0.6706(3) 0.3893(3) 0.4030(3) 0.0426(6) Uani 1 1 d .
H1 H 0.7269 0.4354 0.4039 0.051 Uiso 1 1 calc R
N2 N 0.1690(3) 0.4109(3) 0.3839(2) 0.0428(6) Uani 1 1 d .
H2 H 0.2282 0.4150 0.4264 0.051 Uiso 1 1 calc R
O1 O 0.7212(3) 0.1840(3) 0.1499(2) 0.0677(7) Uani 1 1 d .
O5 O 0.3243(3) 0.1058(2) 0.4110(2) 0.0647(7) Uani 1 1 d .
C3 C 0.5250(3) 0.4336(3) 0.4662(3) 0.0387(7) Uani 1 1 d .
C6 C 0.0216(3) 0.4636(3) 0.4367(3) 0.0383(7) Uani 1 1 d .
C2 C 0.7372(3) 0.2666(3) 0.3327(3) 0.0441(7) Uani 1 1 d .
H2A H 0.7100 0.1801 0.4005 0.053 Uiso 1 1 calc R
H2B H 0.8465 0.2397 0.3097 0.053 Uiso 1 1 calc R
N3 N 0.4483(3) 0.7173(3) 0.0588(3) 0.0534(7) Uani 1 1 d .
H3A H 0.4965 0.6254 0.1043 0.080 Uiso 1 1 calc R
H3B H 0.5155 0.7620 -0.0025 0.080 Uiso 1 1 calc R
H3C H 0.3939 0.7102 0.0092 0.080 Uiso 1 1 calc R
C5 C 0.2351(4) 0.3465(3) 0.2576(3) 0.0502(8) Uani 1 1 d .
H5A H 0.3039 0.3989 0.1873 0.060 Uiso 1 1 calc R
H5B H 0.1548 0.3659 0.2134 0.060 Uiso 1 1 calc R
C4 C 0.3197(3) 0.1805(3) 0.2851(3) 0.0459(8) Uani 1 1 d .
O2 O 0.6330(3) 0.4270(3) 0.1324(3) 0.0759(8) Uani 1 1 d .
C1 C 0.6906(4) 0.2985(4) 0.1941(3) 0.0479(8) Uani 1 1 d .
C8 C 0.2087(6) 0.7969(8) 0.2334(6) 0.119(2) Uani 1 1 d .
H8A H 0.2203 0.6952 0.2930 0.143 Uiso 1 1 calc R
H8B H 0.1618 0.8089 0.1584 0.143 Uiso 1 1 calc R
C7 C 0.3471(5) 0.8072(6) 0.1671(5) 0.0967(15) Uani 1 1 d .
H7A H 0.3990 0.7810 0.2425 0.116 Uiso 1 1 calc R
H7B H 0.3354 0.9124 0.1191 0.116 Uiso 1 1 calc R
C9 C 0.0998(5) 0.9032(5) 0.3277(5) 0.0853(13) Uani 1 1 d .
H9A H 0.1497 0.9080 0.3913 0.128 Uiso 1 1 calc R
H9B H 0.0154 0.8681 0.3849 0.128 Uiso 1 1 calc R
H9C H 0.0643 1.0018 0.2674 0.128 Uiso 1 1 calc R
N4 N 0.3564(3) 0.0702(3) 0.6846(3) 0.0569(7) Uani 1 1 d .
H4A H 0.3253 -0.0099 0.7275 0.085 Uiso 1 1 calc R
H4B H 0.4571 0.0404 0.6606 0.085 Uiso 1 1 calc R
H4C H 0.3224 0.1201 0.6047 0.085 Uiso 1 1 calc R
C10 C 0.2973(4) 0.1704(4) 0.7863(4) 0.0621(10) Uani 1 1 d .
H10A H 0.3505 0.1235 0.8634 0.074 Uiso 1 1 calc R
H10B H 0.3172 0.2648 0.7343 0.074 Uiso 1 1 calc R
C11 C 0.1342(4) 0.2017(4) 0.8514(4) 0.0707(11) Uani 1 1 d .
H11A H 0.1137 0.1075 0.9031 0.085 Uiso 1 1 calc R
H11B H 0.0805 0.2500 0.7747 0.085 Uiso 1 1 calc R
C12 C 0.0768(5) 0.3035(5) 0.9566(5) 0.0864(13) Uani 1 1 d .
H12A H 0.1223 0.2516 1.0378 0.130 Uiso 1 1 calc R
H12B H -0.0312 0.3292 0.9910 0.130 Uiso 1 1 calc R
H12C H 0.1033 0.3938 0.9073 0.130 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_3
C3 N1 C2 121.6(2) .
C6 N2 C5 122.7(3) .
O3 C3 N1 124.5(3) .
O3 C3 C3 121.6(3) 2_666
N1 C3 C3 113.9(3) 2_666
O6 C6 N2 125.0(3) .
O6 C6 C6 121.8(3) 2_566
N2 C6 C6 113.2(3) 2_566
N1 C2 C1 114.5(3) .
N2 C5 C4 116.0(2) .
O5 C4 O4 124.8(3) .
O5 C4 C5 120.1(3) .
O4 C4 C5 115.1(3) .
O2 C1 O1 124.9(3) .
O2 C1 C2 120.5(3) .
O1 C1 C2 114.5(3) .
C7 C8 C9 119.2(5) .
C8 C7 N3 119.6(4) .
C11 C10 N4 112.4(3) .
C10 C11 C12 111.2(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C3 1.223(3) .
O6 C6 1.214(3) .
O4 C4 1.253(4) .
N1 C3 1.316(4) .
N1 C2 1.430(3) .
N2 C6 1.318(4) .
N2 C5 1.446(3) .
O1 C1 1.250(4) .
O5 C4 1.237(4) .
C3 C3 1.519(5) 2_666
C6 C6 1.526(5) 2_566
C2 C1 1.515(4) .
N3 C7 1.476(5) .
C5 C4 1.500(4) .
O2 C1 1.212(4) .
C8 C7 1.335(6) .
C8 C9 1.496(6) .
N4 C10 1.480(4) .
C10 C11 1.468(5) .
C11 C12 1.522(5) .
