#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:27:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178783 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/37/4103759.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_4103759
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            'C11 H21 N3 O6'
_chemical_formula_weight         291.31
_chemical_name_common            '(pentylNH3)2og.H2og '
_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                74.787(4)
_cell_angle_beta                 81.591(4)
_cell_angle_gamma                77.922(4)
_cell_formula_units_Z            2
_cell_length_a                   5.0096(10)
_cell_length_b                   11.818(2)
_cell_length_c                   14.202(3)
_cell_measurement_temperature    273(2)
_cell_volume                     789.7(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 0.925
_diffrn_measured_fraction_theta_max 0.925
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4705
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.030(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0687
_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)+(0.1701P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.1976
_reflns_number_gt                1694
_reflns_number_total             3558
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806663h_si_006.cif
_cod_data_source_block           pentylammonium
_cod_original_cell_volume        789.6(3)
_cod_database_code               4103759
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
O1 O 0.1801(3) 0.06813(18) 0.04847(16) 0.0673(6) Uani 1 1 d .
N1 N 0.6070(4) 0.08182(19) 0.07259(16) 0.0524(6) Uani 1 1 d .
H1 H 0.7806 0.0586 0.0614 0.063 Uiso 1 1 calc R
O2 O 0.4379(4) 0.32389(19) -0.00917(16) 0.0728(7) Uani 1 1 d .
O3 O 0.1687(5) 0.34192(19) 0.12561(18) 0.0875(8) Uani 1 1 d .
C1 C 0.4324(5) 0.0414(2) 0.03347(18) 0.0466(6) Uani 1 1 d .
C2 C 0.5060(6) 0.1651(2) 0.1344(2) 0.0570(7) Uani 1 1 d .
H2A H 0.6586 0.1769 0.1634 0.068 Uiso 1 1 calc R
H2B H 0.3785 0.1312 0.1872 0.068 Uiso 1 1 calc R
C3 C 0.3623(5) 0.2859(2) 0.0777(2) 0.0565(7) Uani 1 1 d .
O6 O 0.1134(4) 0.74061(19) 0.71711(17) 0.0721(7) Uani 1 1 d .
O4 O 0.1789(4) 0.5786(2) 0.53722(18) 0.0800(7) Uani 1 1 d .
N2 N 0.6023(4) 0.6024(2) 0.55471(17) 0.0607(7) Uani 1 1 d .
H2 H 0.7765 0.5804 0.5440 0.073 Uiso 1 1 calc R
C6 C 0.3185(6) 0.6573(3) 0.6981(2) 0.0619(8) Uani 1 1 d .
C5 C 0.4957(6) 0.6971(3) 0.6050(2) 0.0654(8) Uani 1 1 d .
H5A H 0.3892 0.7629 0.5616 0.078 Uiso 1 1 calc R
H5B H 0.6480 0.7258 0.6204 0.078 Uiso 1 1 calc R
C4 C 0.4308(5) 0.5498(3) 0.5252(2) 0.0578(7) Uani 1 1 d .
O5 O 0.3629(6) 0.5587(3) 0.7511(2) 0.1082(10) Uani 1 1 d .
N3 N 1.0690(5) 0.5930(2) 0.10749(19) 0.0704(7) Uani 1 1 d .
H3A H 0.9080 0.6176 0.0826 0.106 Uiso 1 1 calc R
H3B H 1.1145 0.5142 0.1174 0.106 Uiso 1 1 calc R
H3C H 1.1967 0.6270 0.0658 0.106 Uiso 1 1 calc R
C8 C 0.9983(14) 0.7466(4) 0.1985(4) 0.1385(19) Uani 1 1 d .
H8A H 0.8260 0.7814 0.1702 0.166 Uiso 1 1 calc R
H8B H 1.1405 0.7822 0.1537 0.166 Uiso 1 1 calc R
C7 C 1.0494(10) 0.6265(4) 0.2007(3) 0.1050(13) Uani 1 1 d .
H7A H 0.9049 0.5908 0.2440 0.126 Uiso 1 1 calc R
H7B H 1.2199 0.5910 0.2300 0.126 Uiso 1 1 calc R
C9 C 0.9827(15) 0.7841(6) 0.2939(4) 0.147(2) Uani 1 1 d .
H9A H 0.8306 0.7523 0.3353 0.176 Uiso 1 1 calc R
H9B H 1.1472 0.7405 0.3243 0.176 Uiso 1 1 calc R
C11 C 0.936(2) 0.9287(5) 0.3931(4) 0.205(4) Uani 1 1 d .
H11A H 0.9125 0.8623 0.4476 0.307 Uiso 1 1 calc R
H11B H 0.7806 0.9918 0.3949 0.307 Uiso 1 1 calc R
H11C H 1.0997 0.9566 0.3969 0.307 Uiso 1 1 calc R
C10 C 0.957(3) 0.8918(7) 0.3027(5) 0.237(5) Uani 1 1 d .
H10A H 0.7955 0.9358 0.2706 0.285 Uiso 1 1 calc R
H10B H 1.1121 0.9227 0.2626 0.285 Uiso 1 1 calc R
H3 H 0.005(9) 0.705(4) 0.787(3) 0.121(14) Uiso 1 1 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_3
C1 N1 C2 120.2(2) .
O1 C1 N1 123.6(2) .
O1 C1 C1 121.9(3) 2_655
N1 C1 C1 114.5(2) 2_655
N1 C2 C3 112.5(2) .
O2 C3 O3 123.8(3) .
O2 C3 C2 119.8(2) .
O3 C3 C2 116.4(3) .
C4 N2 C5 120.0(2) .
O5 C6 O6 123.2(3) .
O5 C6 C5 123.0(3) .
O6 C6 C5 113.8(3) .
N2 C5 C6 112.7(3) .
O4 C4 N2 123.0(2) .
O4 C4 C4 122.3(3) 2_666
N2 C4 C4 114.8(3) 2_666
C7 C8 C9 118.8(5) .
C8 C7 N3 117.5(4) .
C10 C9 C8 126.0(6) .
C9 C10 C11 126.5(7) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.238(3) .
N1 C1 1.326(3) .
N1 C2 1.453(3) .
O2 C3 1.229(3) .
O3 C3 1.271(3) .
C1 C1 1.531(4) 2_655
C2 C3 1.530(4) .
O6 C6 1.317(3) .
O4 C4 1.235(3) .
N2 C4 1.330(3) .
N2 C5 1.451(3) .
C6 O5 1.205(4) .
C6 C5 1.504(4) .
C4 C4 1.527(5) 2_666
N3 C7 1.462(5) .
C8 C7 1.381(6) .
C8 C9 1.520(7) .
C9 C10 1.289(8) .
C11 C10 1.444(8) .
