#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:32:20 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179534 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/03/4500399.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_4500399
loop_
_publ_author_name
'Lemmerer, Andreas'
_publ_section_title
;
 Two-Dimensional Hydrogen-Bonding Patterns in a Series of Salts of
 Terephthalic Acid and the Cyclic Amines CnH2n−1NH2,n= 3, 4, 5, 6,
 7, 8, and 12
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              583
_journal_paper_doi               10.1021/cg101503x
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C8 H4 O4, 2(C4 H10 N), H2 O'
_chemical_formula_sum            'C16 H26 N2 O5'
_chemical_formula_weight         326.39
_chemical_name_systematic
;
 bis(cyclobutylammonium).(terephthalate).(H2O)
;
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2010-10-19T14:47:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                104.202(6)
_cell_angle_beta                 101.783(7)
_cell_angle_gamma                106.211(7)
_cell_formula_units_Z            2
_cell_length_a                   7.484(2)
_cell_length_b                   11.332(4)
_cell_length_c                   11.999(4)
_cell_measurement_reflns_used    870
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.22
_cell_volume                     905.7(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10891
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         1.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.5
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4355
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1175P)²+0.0147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.197
_refine_ls_wR_factor_ref         0.2229
_reflns_number_gt                2571
_reflns_number_total             4355
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg101503x_si_001.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4500399
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
C1 C 0.9871(4) 0.1237(2) 0.5206(2) 0.0282(6) Uani 1 1 d .
C2 C 0.8551(4) 0.0278(2) 0.5452(2) 0.0335(6) Uani 1 1 d .
H2 H 0.7555 0.0465 0.5764 0.04 Uiso 1 1 calc R
C3 C 1.1327(4) 0.0957(2) 0.4755(2) 0.0345(6) Uani 1 1 d .
H3 H 1.2241 0.161 0.4587 0.041 Uiso 1 1 calc R
C4 C 0.9731(4) 0.2579(2) 0.5440(2) 0.0307(6) Uani 1 1 d .
O1 O 0.8295(3) 0.27503(17) 0.57691(16) 0.0360(5) Uani 1 1 d .
O2 O 1.1026(3) 0.34374(17) 0.52700(18) 0.0410(5) Uani 1 1 d .
C5 C 0.9714(3) 0.8679(2) 0.9756(2) 0.0264(5) Uani 1 1 d .
C6 C 0.9712(3) 0.9233(2) 0.8840(2) 0.0285(6) Uani 1 1 d .
H6 H 0.9519 0.8709 0.8045 0.034 Uiso 1 1 calc R
C7 C 1.0009(4) 0.9452(2) 1.0920(2) 0.0295(6) Uani 1 1 d .
H7 H 1.002 0.9084 1.1551 0.035 Uiso 1 1 calc R
C8 C 0.9381(4) 0.7240(2) 0.9492(2) 0.0304(6) Uani 1 1 d .
O3 O 0.9253(3) 0.65974(16) 0.84329(17) 0.0365(5) Uani 1 1 d .
O4 O 0.9200(3) 0.67653(18) 1.03165(18) 0.0516(6) Uani 1 1 d .
C9 C 0.6711(5) 0.3519(3) 0.8459(4) 0.0659(11) Uani 1 1 d .
H9 H 0.6903 0.3987 0.9321 0.079 Uiso 1 1 calc R
C10 C 0.4880(7) 0.3450(5) 0.7748(6) 0.113(2) Uani 1 1 d .
H10A H 0.4786 0.331 0.6888 0.136 Uiso 1 1 calc R
H10B H 0.4461 0.4182 0.8081 0.136 Uiso 1 1 calc R
C11 C 0.3913(5) 0.2199(4) 0.8024(4) 0.0735(11) Uani 1 1 d .
H11A H 0.3471 0.235 0.8753 0.088 Uiso 1 1 calc R
H11B H 0.2884 0.1508 0.7331 0.088 Uiso 1 1 calc R
C12 C 0.5850(6) 0.2053(3) 0.8220(4) 0.0724(11) Uani 1 1 d .
H12A H 0.6035 0.1517 0.7495 0.087 Uiso 1 1 calc R
H12B H 0.6239 0.1776 0.8925 0.087 Uiso 1 1 calc R
N1 N 0.8504(3) 0.4025(2) 0.8146(2) 0.0341(5) Uani 1 1 d .
H1A H 0.8312 0.3636 0.7351 0.051 Uiso 1 1 calc R
H1B H 0.9483 0.3856 0.8591 0.051 Uiso 1 1 calc R
H1C H 0.8828 0.4898 0.8303 0.051 Uiso 1 1 calc R
C13 C 0.7123(4) 0.3011(2) 0.2970(2) 0.0301(6) Uani 1 1 d .
H13 H 0.8512 0.3125 0.3008 0.036 Uiso 1 1 calc R
C14 C 0.5926(4) 0.1563(3) 0.2636(3) 0.0432(7) Uani 1 1 d .
H14A H 0.475 0.1394 0.2913 0.052 Uiso 1 1 calc R
H14B H 0.6701 0.103 0.2853 0.052 Uiso 1 1 calc R
C15 C 0.5532(4) 0.1518(3) 0.1313(3) 0.0478(8) Uani 1 1 d .
H15A H 0.4166 0.1024 0.0819 0.057 Uiso 1 1 calc R
H15B H 0.6449 0.1238 0.0916 0.057 Uiso 1 1 calc R
C16 C 0.6024(4) 0.3003(3) 0.1747(3) 0.0419(7) Uani 1 1 d .
H16A H 0.6861 0.3471 0.1339 0.05 Uiso 1 1 calc R
H16B H 0.4877 0.3273 0.1752 0.05 Uiso 1 1 calc R
N2 N 0.7019(3) 0.3900(2) 0.4076(2) 0.0275(5) Uani 1 1 d .
H2A H 0.582(5) 0.389(3) 0.399(3) 0.041 Uiso 1 1 d .
H2B H 0.779(4) 0.472(3) 0.420(3) 0.041 Uiso 1 1 d .
H2C H 0.743(4) 0.364(3) 0.478(3) 0.041 Uiso 1 1 d .
O1W O 0.3201(3) 0.3815(2) 0.37404(19) 0.0456(5) Uani 1 1 d D
H1W H 0.258(4) 0.360(3) 0.421(2) 0.055 Uiso 1 1 d D
H2W H 0.245(4) 0.364(3) 0.3041(13) 0.055 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.03
0 -1 0 0.03
0 0 1 0.09
0 0 -1 0.09
-1 0 2 0.14
1 0 0 0.21
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
C2 C1 C3 119.4(2) . .
C2 C1 C4 120.0(2) . .
C3 C1 C4 120.6(2) . .
C1 C2 C3 120.5(2) . 2_756
C1 C2 H2 119.8 . .
C3 C2 H2 119.8 2_756 .
C1 C3 C2 120.2(2) . 2_756
C1 C3 H3 119.9 . .
C2 C3 H3 119.9 2_756 .
O2 C4 O1 124.6(2) . .
O2 C4 C1 117.8(2) . .
O1 C4 C1 117.7(2) . .
C7 C5 C6 119.4(2) . .
C7 C5 C8 119.9(2) . .
C6 C5 C8 120.7(2) . .
C7 C6 C5 120.6(2) 2_777 .
C7 C6 H6 119.7 2_777 .
C5 C6 H6 119.7 . .
C5 C7 C6 120.0(2) . 2_777
C5 C7 H7 120 . .
C6 C7 H7 120 2_777 .
O4 C8 O3 124.6(2) . .
O4 C8 C5 118.1(2) . .
O3 C8 C5 117.2(2) . .
C10 C9 N1 120.8(4) . .
C10 C9 C12 88.3(3) . .
N1 C9 C12 118.3(3) . .
C10 C9 H9 109.2 . .
N1 C9 H9 109.2 . .
C12 C9 H9 109.2 . .
C9 C10 C11 88.5(3) . .
C9 C10 H10A 113.9 . .
C11 C10 H10A 113.9 . .
C9 C10 H10B 113.9 . .
C11 C10 H10B 113.9 . .
H10A C10 H10B 111.1 . .
C12 C11 C10 85.8(3) . .
C12 C11 H11A 114.3 . .
C10 C11 H11A 114.3 . .
C12 C11 H11B 114.3 . .
C10 C11 H11B 114.3 . .
H11A C11 H11B 111.5 . .
C11 C12 C9 87.1(3) . .
C11 C12 H12A 114.1 . .
C9 C12 H12A 114.1 . .
C11 C12 H12B 114.1 . .
C9 C12 H12B 114.1 . .
H12A C12 H12B 111.3 . .
C9 N1 H1A 109.5 . .
C9 N1 H1B 109.5 . .
H1A N1 H1B 109.5 . .
C9 N1 H1C 109.5 . .
H1A N1 H1C 109.5 . .
H1B N1 H1C 109.5 . .
N2 C13 C16 118.9(2) . .
N2 C13 C14 116.8(2) . .
C16 C13 C14 89.2(2) . .
N2 C13 H13 110.1 . .
C16 C13 H13 110.1 . .
C14 C13 H13 110.1 . .
C13 C14 C15 87.0(2) . .
C13 C14 H14A 114.1 . .
C15 C14 H14A 114.1 . .
C13 C14 H14B 114.1 . .
C15 C14 H14B 114.1 . .
H14A C14 H14B 111.3 . .
C14 C15 C16 88.5(2) . .
C14 C15 H15A 113.9 . .
C16 C15 H15A 113.9 . .
C14 C15 H15B 113.9 . .
C16 C15 H15B 113.9 . .
H15A C15 H15B 111.1 . .
C13 C16 C15 87.3(2) . .
C13 C16 H16A 114.1 . .
C15 C16 H16A 114.1 . .
C13 C16 H16B 114.1 . .
C15 C16 H16B 114.1 . .
H16A C16 H16B 111.3 . .
C13 N2 H2A 110(2) . .
C13 N2 H2B 109.9(18) . .
H2A N2 H2B 108(3) . .
C13 N2 H2C 111.0(16) . .
H2A N2 H2C 109(2) . .
H2B N2 H2C 109(2) . .
H1W O1W H2W 112(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.386(4) .
C1 C3 1.389(4) .
C1 C4 1.515(3) .
C2 C3 1.393(3) 2_756
C2 H2 0.95 .
C3 C2 1.393(3) 2_756
C3 H3 0.95 .
C4 O2 1.257(3) .
C4 O1 1.265(3) .
C5 C7 1.390(3) .
C5 C6 1.393(3) .
C5 C8 1.519(3) .
C6 C7 1.392(3) 2_777
C6 H6 0.95 .
C7 C6 1.392(3) 2_777
C7 H7 0.95 .
C8 O4 1.249(3) .
C8 O3 1.270(3) .
C9 C10 1.428(6) .
C9 N1 1.466(4) .
C9 C12 1.533(5) .
C9 H9 1 .
C10 C11 1.549(6) .
C10 H10A 0.99 .
C10 H10B 0.99 .
C11 C12 1.483(5) .
C11 H11A 0.99 .
C11 H11B 0.99 .
C12 H12A 0.99 .
C12 H12B 0.99 .
N1 H1A 0.91 .
N1 H1B 0.91 .
N1 H1C 0.91 .
C13 N2 1.488(3) .
C13 C16 1.525(4) .
C13 C14 1.538(4) .
C13 H13 1 .
C14 C15 1.539(4) .
C14 H14A 0.99 .
C14 H14B 0.99 .
C15 C16 1.544(4) .
C15 H15A 0.99 .
C15 H15B 0.99 .
C16 H16A 0.99 .
C16 H16B 0.99 .
N2 H2A 0.88(3) .
N2 H2B 0.90(3) .
N2 H2C 0.98(3) .
O1W H1W 0.843(10) .
O1W H2W 0.849(10) .
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
N1 H1A O1 0.91 1.91 2.814(3) 170.3 .
N1 H1B O4 0.91 1.87 2.745(3) 160.5 2_767
N1 H1C O3 0.91 1.82 2.729(3) 172.7 .
N2 H2A O1W 0.88(3) 1.90(3) 2.774(3) 178(3) .
N2 H2B O2 0.90(3) 1.91(3) 2.786(3) 164(3) 2_766
N2 H2C O1 0.98(3) 1.87(3) 2.818(3) 163(2) .
O1W H1W O2 0.84(1) 1.90(1) 2.724(3) 167(3) 1_455
O1W H2W O3 0.85(1) 1.87(1) 2.713(3) 174(3) 2_666
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_4
C3 C1 C2 C3 -0.3(4) 2_756
C4 C1 C2 C3 -179.7(2) 2_756
C2 C1 C3 C2 0.3(4) 2_756
C4 C1 C3 C2 179.7(2) 2_756
C2 C1 C4 O2 175.9(2) .
C3 C1 C4 O2 -3.5(4) .
C2 C1 C4 O1 -5.5(4) .
C3 C1 C4 O1 175.1(2) .
C7 C5 C6 C7 -0.4(4) 2_777
C8 C5 C6 C7 179.1(2) 2_777
C6 C5 C7 C6 0.4(4) 2_777
C8 C5 C7 C6 -179.1(2) 2_777
C7 C5 C8 O4 6.6(3) .
C6 C5 C8 O4 -172.9(2) .
C7 C5 C8 O3 -175.3(2) .
C6 C5 C8 O3 5.2(3) .
N1 C9 C10 C11 146.0(3) .
C12 C9 C10 C11 23.6(4) .
C9 C10 C11 C12 -24.5(4) .
C10 C11 C12 C9 22.8(4) .
C10 C9 C12 C11 -24.8(4) .
N1 C9 C12 C11 -149.3(4) .
N2 C13 C14 C15 143.5(2) .
C16 C13 C14 C15 21.3(2) .
C13 C14 C15 C16 -21.0(2) .
N2 C13 C16 C15 -141.6(2) .
C14 C13 C16 C15 -21.2(2) .
C14 C15 C16 C13 21.2(2) .
