#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:41:09 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179671 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/24/4512449.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_4512449
loop_
_publ_author_name
'Tang, Yuanyuan'
'Sun, Zhihua'
'Ji, Chengmin'
'Li, Lina'
'Zhang, Shuquan'
'Chen, Tianliang'
'Luo, Junhua'
_publ_section_title
;
 Hydrogen-Bonded Displacive-Type Ferroelastic Phase Transition in a New
 Entangled Supramolecular Compound
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              457
_journal_paper_doi               10.1021/cg501529f
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         '2(C8 H20 N), C4 H4 O4, C4 H2 O4'
_chemical_formula_sum            'C24 H46 N2 O8'
_chemical_formula_weight         490.63
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_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                100.258(3)
_cell_angle_beta                 90.572(4)
_cell_angle_gamma                93.606(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0851(5)
_cell_length_b                   12.8719(4)
_cell_length_c                   12.9349(6)
_cell_measurement_temperature    216(2)
_cell_volume                     1485.17(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      216(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18025
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
_exptl_special_details 
;
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         6028
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0780
_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)+(0.1159P)²+0.7498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2230
_refine_ls_wR_factor_ref         0.2459
_reflns_number_gt                4270
_reflns_number_total             6028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501529f_si_003.cif
_cod_data_source_block           f:\216k
_cod_depositor_comments
'Adding full bibliography for 4512449--4512450.cif.'
_cod_database_code               4512449
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
N5 N 0.0440(2) 0.65846(16) 0.48421(18) 0.0529(5) Uani 1 1 d .
H5A H 0.1206 0.6173 0.4896 0.064 Uiso 1 1 calc R
H5B H -0.0404 0.6156 0.4768 0.064 Uiso 1 1 calc R
O30 O 0.1297(2) 0.98486(19) 0.33106(16) 0.0682(6) Uani 1 1 d .
O17 O -0.2728(2) 0.65730(17) 0.4629(2) 0.0798(7) Uani 1 1 d .
C27 C -0.0454(3) 0.97866(19) 0.4609(2) 0.0485(6) Uani 1 1 d .
H27 H -0.1396 0.9527 0.4775 0.058 Uiso 1 1 calc R
O16 O -0.2159(2) 0.50126(16) 0.4814(2) 0.0791(7) Uani 1 1 d .
C4 C 0.0375(3) 0.7372(2) 0.5831(2) 0.0587(7) Uani 1 1 d .
H4A H -0.0450 0.7817 0.5781 0.070 Uiso 1 1 calc R
H4B H 0.1287 0.7830 0.5924 0.070 Uiso 1 1 calc R
C6 C 0.0624(3) 0.7064(2) 0.3890(2) 0.0556(7) Uani 1 1 d .
H6A H 0.1420 0.7624 0.4018 0.067 Uiso 1 1 calc R
H6B H -0.0287 0.7388 0.3748 0.067 Uiso 1 1 calc R
C28 C -0.0084(3) 0.9690(2) 0.3489(2) 0.0507(6) Uani 1 1 d .
C14 C -0.3100(3) 0.5665(2) 0.4776(2) 0.0579(7) Uani 1 1 d .
C15 C -0.4739(3) 0.5435(2) 0.4878(2) 0.0608(7) Uani 1 1 d .
H15 H -0.5391 0.5943 0.4760 0.073 Uiso 1 1 calc R
O29 O -0.1015(2) 0.9485(3) 0.28147(18) 0.1030(10) Uani 1 1 d .
C3 C 0.0179(4) 0.6838(2) 0.6763(2) 0.0717(8) Uani 1 1 d .
H3A H 0.1014 0.6402 0.6816 0.086 Uiso 1 1 calc R
H3B H -0.0721 0.6368 0.6659 0.086 Uiso 1 1 calc R
C7 C 0.0975(4) 0.6270(3) 0.2951(3) 0.0751(9) Uani 1 1 d .
H7A H 0.0130 0.5755 0.2774 0.090 Uiso 1 1 calc R
H7B H 0.1820 0.5889 0.3120 0.090 Uiso 1 1 calc R
C8 C 0.1332(5) 0.6788(3) 0.2009(3) 0.0975(12) Uani 1 1 d .
H8A H 0.0470 0.7145 0.1826 0.117 Uiso 1 1 calc R
H8B H 0.2146 0.7327 0.2200 0.117 Uiso 1 1 calc R
C2 C 0.0077(5) 0.7618(3) 0.7783(3) 0.0950(12) Uani 1 1 d .
H2A H 0.0955 0.8110 0.7869 0.114 Uiso 1 1 calc R
H2B H -0.0786 0.8030 0.7743 0.114 Uiso 1 1 calc R
C9 C 0.1750(7) 0.6015(5) 0.1070(4) 0.139(2) Uani 1 1 d .
H9A H 0.1942 0.6383 0.0488 0.209 Uiso 1 1 calc R
H9B H 0.0949 0.5478 0.0877 0.209 Uiso 1 1 calc R
H9C H 0.2630 0.5683 0.1236 0.209 Uiso 1 1 calc R
C1 C -0.0046(9) 0.7084(4) 0.8729(3) 0.158(3) Uani 1 1 d .
H1A H -0.1008 0.6710 0.8720 0.237 Uiso 1 1 calc R
H1B H 0.0076 0.7613 0.9364 0.237 Uiso 1 1 calc R
H1C H 0.0716 0.6586 0.8710 0.237 Uiso 1 1 calc R
N22 N 0.4676(2) 0.01549(18) 0.83863(16) 0.0547(6) Uani 1 1 d .
H22A H 0.3956 0.0083 0.8857 0.066 Uiso 1 1 calc R
H22B H 0.5553 0.0270 0.8748 0.066 Uiso 1 1 calc R
O13 O 0.3737(2) 0.16595(16) 0.51389(19) 0.0685(6) Uani 1 1 d .
O34 O 0.7734(2) 0.0413(2) 0.85196(17) 0.0732(6) Uani 1 1 d .
C10 C 0.5459(3) 0.04062(19) 0.51652(19) 0.0482(6) Uani 1 1 d .
H10 H 0.6416 0.0271 0.5364 0.058 Uiso 1 1 calc R
C11 C 0.5113(3) 0.1524(2) 0.5252(2) 0.0490(6) Uani 1 1 d .
C31 C 0.9734(3) 0.0131(2) 0.95768(19) 0.0513(6) Uani 1 1 d .
H31 H 1.0391 0.0240 0.9044 0.062 Uiso 1 1 calc R
C32 C 0.8141(3) 0.0266(2) 0.9406(2) 0.0559(7) Uani 1 1 d .
C21 C 0.4700(3) -0.0852(2) 0.7623(2) 0.0622(7) Uani 1 1 d .
H21A H 0.5492 -0.0790 0.7125 0.075 Uiso 1 1 calc R
H21B H 0.3763 -0.0981 0.7225 0.075 Uiso 1 1 calc R
O12 O 0.6064(2) 0.22317(17) 0.5400(3) 0.1018(10) Uani 1 1 d .
C23 C 0.4422(3) 0.1094(2) 0.7911(2) 0.0598(7) Uani 1 1 d .
H23A H 0.3586 0.0926 0.7412 0.072 Uiso 1 1 calc R
H23B H 0.5295 0.1267 0.7520 0.072 Uiso 1 1 calc R
O33 O 0.7253(2) 0.0238(2) 1.01189(18) 0.0904(8) Uani 1 1 d .
C20 C 0.4935(4) -0.1768(3) 0.8162(2) 0.0753(9) Uani 1 1 d .
H20A H 0.4126 -0.1840 0.8645 0.090 Uiso 1 1 calc R
H20B H 0.5855 -0.1624 0.8580 0.090 Uiso 1 1 calc R
C24 C 0.4113(5) 0.2029(3) 0.8712(3) 0.0858(10) Uani 1 1 d .
H24A H 0.4986 0.2244 0.9168 0.103 Uiso 1 1 calc R
H24B H 0.3300 0.1839 0.9149 0.103 Uiso 1 1 calc R
C25 C 0.3704(6) 0.2952(3) 0.8196(4) 0.1099(14) Uani 1 1 d .
H25A H 0.4560 0.3188 0.7823 0.132 Uiso 1 1 calc R
H25B H 0.2910 0.2705 0.7675 0.132 Uiso 1 1 calc R
C19 C 0.5013(6) -0.2799(3) 0.7394(3) 0.1032(14) Uani 1 1 d .
H19A H 0.5846 -0.2737 0.6929 0.124 Uiso 1 1 calc R
H19B H 0.4109 -0.2929 0.6958 0.124 Uiso 1 1 calc R
C18 C 0.5193(9) -0.3735(4) 0.7942(4) 0.166(3) Uani 1 1 d .
H18A H 0.5273 -0.4370 0.7421 0.249 Uiso 1 1 calc R
H18B H 0.4343 -0.3826 0.8373 0.249 Uiso 1 1 calc R
H18C H 0.6078 -0.3606 0.8384 0.249 Uiso 1 1 calc R
C26 C 0.3221(8) 0.3859(4) 0.8946(5) 0.154(2) Uani 1 1 d .
H26A H 0.2950 0.4408 0.8568 0.230 Uiso 1 1 calc R
H26B H 0.4019 0.4134 0.9443 0.230 Uiso 1 1 calc R
H26C H 0.2375 0.3634 0.9322 0.230 Uiso 1 1 calc R
H2 H 0.356(4) 0.236(3) 0.510(3) 0.104(13) Uiso 1 1 d .
H5 H 0.149(5) 0.983(3) 0.257(4) 0.121(15) 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_1
C6 N5 C4 113.8(2) .
C27 C27 C28 124.1(3) 2_576
N5 C4 C3 111.3(2) .
N5 C6 C7 112.1(2) .
O29 C28 O30 123.7(3) .
O29 C28 C27 121.3(2) .
O30 C28 C27 115.0(2) .
O16 C14 O17 120.5(3) .
O16 C14 C15 124.3(3) .
O17 C14 C15 115.2(2) .
C15 C15 C14 121.6(3) 2_466
C4 C3 C2 112.6(3) .
C6 C7 C8 111.8(3) .
C9 C8 C7 112.9(4) .
C1 C2 C3 112.8(3) .
C23 N22 C21 114.7(2) .
C10 C10 C11 125.1(3) 2_656
O12 C11 O13 124.1(2) .
O12 C11 C10 121.7(2) .
O13 C11 C10 114.3(2) .
C31 C31 C32 123.5(3) 2_757
O33 C32 O34 121.2(3) .
O33 C32 C31 121.0(3) .
O34 C32 C31 117.9(2) .
N22 C21 C20 111.6(2) .
N22 C23 C24 112.2(2) .
C21 C20 C19 112.5(3) .
C23 C24 C25 111.2(3) .
C26 C25 C24 113.6(4) .
C20 C19 C18 112.5(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N5 C6 1.478(4) .
N5 C4 1.488(3) .
O30 C28 1.289(3) .
O17 C14 1.243(3) .
C27 C27 1.316(5) 2_576
C27 C28 1.476(4) .
O16 C14 1.242(3) .
C4 C3 1.497(4) .
C6 C7 1.492(4) .
C28 O29 1.192(3) .
C14 C15 1.512(4) .
C15 C15 1.281(6) 2_466
C3 C2 1.516(5) .
C7 C8 1.518(5) .
C8 C9 1.495(6) .
C2 C1 1.508(6) .
N22 C23 1.480(4) .
N22 C21 1.484(4) .
O13 C11 1.284(3) .
O34 C32 1.251(3) .
C10 C10 1.302(5) 2_656
C10 C11 1.477(4) .
C11 O12 1.204(3) .
C31 C31 1.299(5) 2_757
C31 C32 1.488(4) .
C32 O33 1.236(3) .
C21 C20 1.498(4) .
C23 C24 1.485(5) .
C20 C19 1.516(5) .
C24 C25 1.526(5) .
C25 C26 1.472(7) .
C19 C18 1.519(6) .
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
N5 H5B O17 0.91 2.22 2.888(3) 129.3 .
N5 H5B O16 0.91 2.11 3.007(3) 168.6 .
N22 H22B O34 0.91 2.01 2.776(3) 141.2 .
N22 H22B O33 0.91 2.35 3.208(3) 157.7 .
N5 H5A O16 0.91 1.89 2.753(3) 156.8 2_566
N22 H22A O33 0.91 1.82 2.715(3) 168.9 2_657
O13 H2 O17 0.94(4) 1.59(4) 2.476(3) 156(4) 2_566
O30 H5 O34 0.97(5) 1.57(5) 2.508(3) 159(4) 2_666
