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#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/99/1519960.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_1519960
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 Hexamethyleneiminium adipate
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              556
_journal_year                    2008
_chemical_formula_sum            'C12 H23 N O4'
_chemical_formula_weight         245.31
_chemical_name_systematic
;
adipic acid & hexamethyleneimine
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 115.478(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8261(10)
_cell_length_b                   11.0607(10)
_cell_length_c                   9.6798(9)
_cell_measurement_reflns_used    2755
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1336.3(2)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10127
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1536
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0438
_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)+(0.0302P)²+1.0785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                1348
_reflns_number_total             1536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-556.cif
_cod_data_source_block           07skc0010cc
_cod_depositor_comments
;
Citation :
Callear, Samantha K. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/556)

More at:
http://ecrystals.chem.soton.ac.uk/556/
;
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               1519960
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1345(2) 0.8542(3) 0.0512(3) 0.0243(6) Uani 1 1 d . . .
C2 C 0.2101(3) 0.8470(3) 0.2178(3) 0.0269(6) Uani 1 1 d . . .
H2A H 0.1766 0.8871 0.2778 0.032 Uiso 1 1 calc R . .
H2B H 0.2761 0.8923 0.2352 0.032 Uiso 1 1 calc R . .
C3 C 0.2409(2) 0.7183(3) 0.2776(3) 0.0233(6) Uani 1 1 d . . .
H3A H 0.2715 0.6761 0.2151 0.028 Uiso 1 1 calc R . .
H3B H 0.1760 0.6738 0.2669 0.028 Uiso 1 1 calc R . .
C4 C 0.3226(2) 0.7174(3) 0.4452(3) 0.0250(6) Uani 1 1 d . . .
H4A H 0.3864 0.7644 0.4558 0.030 Uiso 1 1 calc R . .
H4B H 0.2911 0.7577 0.5075 0.030 Uiso 1 1 calc R . .
C5 C 0.3574(2) 0.5909(3) 0.5065(3) 0.0235(6) Uani 1 1 d . . .
H5A H 0.2928 0.5425 0.4883 0.028 Uiso 1 1 calc R . .
H5B H 0.3931 0.5529 0.4481 0.028 Uiso 1 1 calc R . .
C6 C 0.4325(2) 0.5857(2) 0.6750(3) 0.0211(6) Uani 1 1 d . . .
O1A O 0.11315(18) 0.96739(17) 0.0026(2) 0.0334(6) Uani 1 1 d . . .
H1 H 0.0681 0.9679 -0.0895 0.050(12) Uiso 1 1 calc R . .
O1B O 0.09722(19) 0.76757(19) -0.0307(2) 0.0374(6) Uani 1 1 d . . .
O6A O 0.47976(18) 0.48500(19) 0.7245(2) 0.0317(5) Uani 1 1 d . . .
O6B O 0.44357(19) 0.67504(19) 0.7574(2) 0.0364(6) Uani 1 1 d . . .
C22 C -0.0722(3) 1.2876(3) 0.0824(4) 0.0300(7) Uani 1 1 d . . .
H22A H -0.0413 1.3209 0.1876 0.036 Uiso 1 1 calc R . .
H22B H -0.1375 1.2418 0.0673 0.036 Uiso 1 1 calc R . .
C23 C -0.1028(2) 1.3910(3) -0.0308(4) 0.0304(7) Uani 1 1 d . . .
H23A H -0.1683 1.4295 -0.0339 0.036 Uiso 1 1 calc R . .
H23B H -0.1210 1.3571 -0.1338 0.036 Uiso 1 1 calc R . .
C24 C -0.0180(3) 1.4888(3) 0.0013(4) 0.0339(7) Uani 1 1 d . . .
H24A H -0.0448 1.5475 -0.0842 0.041 Uiso 1 1 calc R . .
H24B H -0.0090 1.5326 0.0953 0.041 Uiso 1 1 calc R . .
C25 C 0.0914(3) 1.4438(3) 0.0217(4) 0.0326(7) Uani 1 1 d . . .
H25A H 0.1367 1.5143 0.0255 0.039 Uiso 1 1 calc R . .
H25B H 0.0824 1.3945 -0.0685 0.039 Uiso 1 1 calc R . .
C26 C 0.1493(2) 1.3681(3) 0.1661(4) 0.0305(7) Uani 1 1 d . . .
H26A H 0.2274 1.3784 0.2011 0.037 Uiso 1 1 calc R . .
H26B H 0.1310 1.4006 0.2472 0.037 Uiso 1 1 calc R . .
C27 C 0.1241(2) 1.2341(3) 0.1493(3) 0.0272(6) Uani 1 1 d . . .
H27A H 0.1622 1.1968 0.0937 0.033 Uiso 1 1 calc R . .
H27B H 0.1531 1.1976 0.2526 0.033 Uiso 1 1 calc R . .
N21 N 0.00720(19) 1.2026(2) 0.0670(3) 0.0249(5) Uani 1 1 d . . .
H21A H -0.0096 1.1954 -0.0355 0.026(8) Uiso 1 1 calc R . .
H21B H -0.0023 1.1277 0.1006 0.052(12) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
O1B C1 O1A 123.3(3) . .
O1B C1 C2 124.5(2) . .
O1A C1 C2 112.2(2) . .
C1 C2 C3 114.1(2) . .
C1 C2 H2A 108.7 . .
C3 C2 H2A 108.7 . .
C1 C2 H2B 108.7 . .
C3 C2 H2B 108.7 . .
H2A C2 H2B 107.6 . .
C2 C3 C4 111.6(2) . .
C2 C3 H3A 109.3 . .
C4 C3 H3A 109.3 . .
C2 C3 H3B 109.3 . .
C4 C3 H3B 109.3 . .
H3A C3 H3B 108.0 . .
C5 C4 C3 112.8(2) . .
C5 C4 H4A 109.0 . .
C3 C4 H4A 109.0 . .
C5 C4 H4B 109.0 . .
C3 C4 H4B 109.0 . .
H4A C4 H4B 107.8 . .
C6 C5 C4 114.4(2) . .
C6 C5 H5A 108.7 . .
C4 C5 H5A 108.7 . .
C6 C5 H5B 108.7 . .
C4 C5 H5B 108.7 . .
H5A C5 H5B 107.6 . .
O6B C6 O6A 123.6(3) . .
O6B C6 C5 120.1(2) . .
O6A C6 C5 116.3(2) . .
C1 O1A H1 109.5 . .
N21 C22 C23 112.9(3) . .
N21 C22 H22A 109.0 . .
C23 C22 H22A 109.0 . .
N21 C22 H22B 109.0 . .
C23 C22 H22B 109.0 . .
H22A C22 H22B 107.8 . .
C22 C23 C24 115.9(3) . .
C22 C23 H23A 108.3 . .
C24 C23 H23A 108.3 . .
C22 C23 H23B 108.3 . .
C24 C23 H23B 108.3 . .
H23A C23 H23B 107.4 . .
C25 C24 C23 115.3(3) . .
C25 C24 H24A 108.4 . .
C23 C24 H24A 108.4 . .
C25 C24 H24B 108.4 . .
C23 C24 H24B 108.4 . .
H24A C24 H24B 107.5 . .
C24 C25 C26 113.4(3) . .
C24 C25 H25A 108.9 . .
C26 C25 H25A 108.9 . .
C24 C25 H25B 108.9 . .
C26 C25 H25B 108.9 . .
H25A C25 H25B 107.7 . .
C27 C26 C25 115.6(3) . .
C27 C26 H26A 108.4 . .
C25 C26 H26A 108.4 . .
C27 C26 H26B 108.4 . .
C25 C26 H26B 108.4 . .
H26A C26 H26B 107.4 . .
N21 C27 C26 115.4(2) . .
N21 C27 H27A 108.4 . .
C26 C27 H27A 108.4 . .
N21 C27 H27B 108.4 . .
C26 C27 H27B 108.4 . .
H27A C27 H27B 107.5 . .
C22 N21 C27 117.9(2) . .
C22 N21 H21A 107.8 . .
C27 N21 H21A 107.8 . .
C22 N21 H21B 107.8 . .
C27 N21 H21B 107.8 . .
H21A N21 H21B 107.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1B 1.208(3) .
C1 O1A 1.325(3) .
C1 C2 1.500(4) .
C2 C3 1.526(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.527(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.515(4) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.511(4) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 O6B 1.238(3) .
C6 O6A 1.276(3) .
O1A H1 0.8400 .
C22 N21 1.500(4) .
C22 C23 1.513(4) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.526(4) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.523(5) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 C26 1.527(4) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C26 C27 1.515(4) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 N21 1.504(4) .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
N21 H21A 0.9200 .
N21 H21B 0.9200 .
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
O1A H1 O6A 0.84 1.70 2.533(3) 173.9 3_454
N21 H21A O6B 0.92 1.84 2.753(3) 174.1 3_454
N21 H21B O6A 0.92 1.82 2.697(3) 158.6 4_464
