#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:27:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178783 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/37/4103755.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_4103755
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            'C8 H22 N4 O8'
_chemical_formula_weight         302.30
_chemical_name_common            '(methylNH3)2og.2H2O '
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 97.758(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9089(16)
_cell_length_b                   7.6850(9)
_cell_length_c                   14.2279(16)
_cell_measurement_temperature    273(2)
_cell_volume                     1506.9(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6436
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.064
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0594
_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)+(0.1226P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                1628
_reflns_number_total             2171
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806663h_si_002.cif
_cod_data_source_block           methylammonium
_cod_database_code               4103755
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O3 O 0.61470(10) 0.15270(19) 0.28130(11) 0.0470(5) Uani 1 1 d .
N2 N 0.13687(12) 0.1435(2) 0.29015(13) 0.0428(5) Uani 1 1 d .
H2 H 0.1514 0.2513 0.3005 0.051 Uiso 1 1 calc R
O6 O -0.11091(10) 0.01331(19) 0.21248(11) 0.0459(5) Uani 1 1 d .
N1 N 0.36422(12) 0.0214(2) 0.22388(13) 0.0433(5) Uani 1 1 d .
H1 H 0.3511 -0.0878 0.2186 0.052 Uiso 1 1 calc R
O1 O 0.30457(12) 0.2873(2) 0.25221(14) 0.0636(6) Uani 1 1 d .
O2 O 0.19549(11) -0.1218(2) 0.25906(12) 0.0541(5) Uani 1 1 d .
C4 C 0.20366(15) 0.0365(3) 0.26607(15) 0.0392(6) Uani 1 1 d .
N3 N 0.80164(15) 1.0766(3) 0.37803(17) 0.0505(6) Uani 1 1 d .
O5 O 0.00382(12) 0.1135(2) 0.13174(12) 0.0589(6) Uani 1 1 d .
C3 C 0.29708(15) 0.1284(3) 0.24712(16) 0.0418(6) Uani 1 1 d .
C6 C -0.02667(16) 0.0706(3) 0.20619(17) 0.0399(6) Uani 1 1 d .
C5 C 0.04028(15) 0.0845(3) 0.29958(16) 0.0423(6) Uani 1 1 d .
H5A H 0.0117 0.1641 0.3409 0.051 Uiso 1 1 calc R
H5B H 0.0447 -0.0288 0.3299 0.051 Uiso 1 1 calc R
C2 C 0.45873(15) 0.0807(3) 0.20707(17) 0.0455(6) Uani 1 1 d .
H2A H 0.4513 0.1917 0.1744 0.055 Uiso 1 1 calc R
H2B H 0.4845 -0.0014 0.1651 0.055 Uiso 1 1 calc R
O4 O 0.50687(15) 0.0733(4) 0.37304(13) 0.0948(8) Uani 1 1 d .
C1 C 0.53167(16) 0.1021(3) 0.29504(17) 0.0450(6) Uani 1 1 d .
C7 C 0.8284(2) 0.9384(5) 0.4462(2) 0.0839(10) Uani 1 1 d .
H7A H 0.8970 0.9426 0.4667 0.126 Uiso 1 1 calc R
H7B H 0.8117 0.8279 0.4170 0.126 Uiso 1 1 calc R
H7C H 0.7942 0.9535 0.4999 0.126 Uiso 1 1 calc R
O7 O 0.36535(17) 0.9191(3) 0.46350(18) 0.0814(7) Uani 1 1 d .
N4 N 0.70466(13) 0.0982(3) 0.11384(14) 0.0526(6) Uani 1 1 d .
H4A H 0.6728 0.0878 0.1638 0.079 Uiso 1 1 calc R
H4B H 0.6966 0.2053 0.0903 0.079 Uiso 1 1 calc R
H4C H 0.7675 0.0785 0.1316 0.079 Uiso 1 1 calc R
C8 C 0.6669(2) -0.0280(5) 0.0414(2) 0.0874(10) Uani 1 1 d .
H8A H 0.7044 -0.0228 -0.0104 0.131 Uiso 1 1 calc R
H8B H 0.6004 -0.0014 0.0188 0.131 Uiso 1 1 calc R
H8C H 0.6711 -0.1428 0.0682 0.131 Uiso 1 1 calc R
H5N H 0.8168(18) 1.175(4) 0.3990(18) 0.053(8) Uiso 1 1 d .
H4N H 0.729(2) 1.092(4) 0.355(2) 0.080(8) Uiso 1 1 d .
H6N H 0.8270(18) 1.058(3) 0.3262(19) 0.057(8) Uiso 1 1 d .
O8 O 0.87733(19) 0.3857(4) 0.46691(19) 0.0857(8) Uani 1 1 d .
H1O8 H 0.895(3) 0.461(5) 0.422(3) 0.131(15) Uiso 1 1 d .
H2O8 H 0.920(3) 0.385(5) 0.521(3) 0.110(13) Uiso 1 1 d .
H2O7 H 0.416(4) 0.903(6) 0.523(4) 0.156(18) Uiso 1 1 d .
H1O7 H 0.398(2) 0.971(4) 0.425(2) 0.087(11) 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
C4 N2 C5 121.68(19)
C3 N1 C2 122.46(19)
O2 C4 N2 125.41(19)
O2 C4 C3 120.96(19)
N2 C4 C3 113.6(2)
O1 C3 N1 125.3(2)
O1 C3 C4 121.0(2)
N1 C3 C4 113.7(2)
O5 C6 O6 125.5(2)
O5 C6 C5 119.29(19)
O6 C6 C5 115.23(19)
N2 C5 C6 114.17(18)
N1 C2 C1 115.00(19)
O4 C1 O3 124.9(2)
O4 C1 C2 119.4(2)
O3 C1 C2 115.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C1 1.259(3)
N2 C4 1.320(3)
N2 C5 1.441(3)
O6 C6 1.266(3)
N1 C3 1.320(3)
N1 C2 1.441(3)
O1 C3 1.227(3)
O2 C4 1.224(3)
C4 C3 1.535(3)
N3 C7 1.452(4)
O5 C6 1.238(3)
C6 C5 1.520(3)
C2 C1 1.510(3)
O4 C1 1.226(3)
N4 C8 1.461(4)
