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#$Date: 2019-12-26 21:23:31 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246103 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/17/2311770.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2311770
loop_
_publ_author_name
'Chia, Tze Shyang'
'Quah, Ching Kheng'
_publ_section_title
;
 Temperature-induced order-disorder structural phase transitions of
 two-dimensional isostructural hexamethylenetetramine co-crystals.
;
_journal_issue                   'Pt 5'
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              879
_journal_page_last               890
_journal_paper_doi               10.1107/S2052520617009520
_journal_volume                  73
_journal_year                    2017
_chemical_formula_moiety         'C6 H12 N4, 2(C7 H6 O2)'
_chemical_formula_sum            'C20 H24 N4 O4'
_chemical_formula_weight         384.43
_chemical_name_systematic
;
Hexamethylenetetramine bis(benzoic acid)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           42
_space_group_name_Hall           'F 2 -2'
_space_group_name_H-M_alt        'F m m 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1464(11)
_cell_length_b                   27.166(3)
_cell_length_c                   7.1898(8)
_cell_measurement_reflns_used    1825
_cell_measurement_temperature    280.0(1)
_cell_measurement_theta_max      23.35
_cell_measurement_theta_min      3.00
_cell_volume                     1981.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      280.0(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX Duo CCD area detector'
_diffrn_measurement_method       'φ and ω 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  0.0182
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4852
_diffrn_reflns_point_group_measured_fraction_full 0.871
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.499
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9365
_exptl_absorpt_correction_T_min  0.8185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.756
_exptl_crystal_size_mid          0.389
_exptl_crystal_size_min          0.208
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1044
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0557P)²+1.0060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.568
_reflns_Friedel_fraction_full    0.717
_reflns_Friedel_fraction_max     0.670
_reflns_number_gt                837
_reflns_number_total             1044
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            gw5053sup1.cif
_cod_data_source_block           1533071
_cod_database_code               2311770
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.981
_exptl_absorpt_special_details
; 
The crystal was placed in the cold stream of an Oxford Cryosystems 
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating 
at 280.0 (1) K.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x, -y, z'
'-x, y, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x, -y+1/2, z+1/2'
'-x, y+1/2, z+1/2'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+1/2, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4182(7) 0.3876(3) 0.8081(9) 0.0930(19) Uani 0.5 1 d D . P A -1
H1O1 H 0.450(14) 0.401(4) 0.902(11) 0.24(8) Uiso 0.5 1 d D . P B -1
O2 O 0.6266(7) 0.3959(3) 0.7257(13) 0.135(3) Uani 0.5 1 d . . P A -1
C4 C 0.5241(7) 0.37906(19) 0.7022(9) 0.063(2) Uani 0.5 1 d . . P A -1
C5 C 0.4939(10) 0.34680(11) 0.5389(5) 0.0648(12) Uani 0.5 1 d G . P A -1
C6 C 0.3655(9) 0.3335(2) 0.4940(9) 0.088(3) Uani 0.5 1 d G . P A -1
H6A H 0.2958 0.3442 0.5677 0.106 Uiso 0.5 1 calc R U P A -1
C7 C 0.3414(7) 0.3042(3) 0.3392(10) 0.115(3) Uani 0.5 1 d G . P A -1
H7A H 0.2555 0.2953 0.3093 0.138 Uiso 0.5 1 calc R U P A -1
C8 C 0.4456(8) 0.28822(16) 0.2292(6) 0.121(4) Uani 0.5 1 d G . P A -1
H8A H 0.4294 0.2686 0.1257 0.145 Uiso 0.5 1 calc R U P A -1
C9 C 0.5740(7) 0.3015(3) 0.2740(9) 0.108(3) Uani 0.5 1 d G . P A -1
H9A H 0.6437 0.2909 0.2004 0.129 Uiso 0.5 1 calc R U P A -1
C10 C 0.5982(8) 0.3308(3) 0.4288(9) 0.088(3) Uani 0.5 1 d G . P A -1
H10A H 0.6841 0.3398 0.4588 0.106 Uiso 0.5 1 calc R U P A -1
N1 N 0.5000 0.45617(11) 1.0543(4) 0.0836(11) Uani 1 2 d S T P . .
N2 N 0.6185(3) 0.5000 1.2901(5) 0.0974(13) Uani 1 2 d S T P . .
C1 C 0.6164(4) 0.45733(16) 1.1739(5) 0.1245(17) Uani 1 1 d . . . . .
H1A H 0.6175 0.4281 1.2513 0.149 Uiso 1 1 calc R U . . .
H1B H 0.6950 0.4569 1.0972 0.149 Uiso 1 1 calc R U . . .
C2 C 0.5000 0.5000 0.9387(7) 0.0632(12) Uani 1 4 d S T P . .
H2A H 0.4211 0.5000 0.8626 0.076 Uiso 1 2 d R U P . .
C3 C 0.5000 0.5000 1.4046(8) 0.0878(18) Uani 1 4 d S T P . .
H3A H 0.5000 0.5301 1.4770 0.105 Uiso 1 2 d R U P . .
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
_geom_angle_site_symmetry_3
C4 O1 H1O1 103(10) . .
O2 C4 O1 125.1(7) . .
O2 C4 C5 122.2(7) . .
O1 C4 C5 112.6(7) . .
C6 C5 C10 120.0 . .
C6 C5 C4 121.7(6) . .
C10 C5 C4 118.3(6) . .
C7 C6 C5 120.0 . .
C7 C6 H6A 120.0 . .
C5 C6 H6A 120.0 . .
C6 C7 C8 120.0 . .
C6 C7 H7A 120.0 . .
C8 C7 H7A 120.0 . .
C9 C8 C7 120.0 . .
C9 C8 H8A 120.0 . .
C7 C8 H8A 120.0 . .
C8 C9 C10 120.0 . .
C8 C9 H9A 120.0 . .
C10 C9 H9A 120.0 . .
C9 C10 C5 120.0 . .
C9 C10 H10A 120.0 . .
C5 C10 H10A 120.0 . .
C2 N1 C1 108.6(3) . 4_655
C2 N1 C1 108.6(3) . .
C1 N1 C1 107.8(3) 4_655 .
C1 N2 C1 108.4(4) 3_565 .
C1 N2 C3 108.5(3) 3_565 .
C1 N2 C3 108.5(3) . .
N2 C1 N1 112.0(3) . .
N2 C1 H1A 109.2 . .
N1 C1 H1A 109.2 . .
N2 C1 H1B 109.2 . .
N1 C1 H1B 109.2 . .
H1A C1 H1B 107.9 . .
N1 C2 N1 110.2(4) . 2_665
N1 C2 H2A 108.8 . .
N1 C2 H2A 108.8 2_665 .
N2 C3 N2 111.2(4) . 2_665
N2 C3 H3A 107.6 . .
N2 C3 H3A 107.6 2_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.337(10) .
O1 H1O1 0.83(3) .
O2 C4 1.148(11) .
C4 C5 1.497(7) .
C5 C6 1.3900 .
C5 C10 1.3900 .
C6 C7 1.3900 .
C6 H6A 0.9300 .
C7 C8 1.3900 .
C7 H7A 0.9300 .
C8 C9 1.3900 .
C8 H8A 0.9300 .
C9 C10 1.3900 .
C9 H9A 0.9300 .
C10 H10A 0.9300 .
N1 C2 1.452(4) .
N1 C1 1.461(4) 4_655
N1 C1 1.461(4) .
N2 C1 1.429(4) 3_565
N2 C1 1.429(4) .
N2 C3 1.457(5) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 N1 1.452(4) 2_665
C2 H2A 0.9700 .
C3 N2 1.457(5) 2_665
C3 H3A 0.9700 .
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_publ_flag
O1 H1O1 N1 0.83(11) 1.92(10) 2.700(8) 155(11) yes
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_1
_geom_torsion_site_symmetry_4
O2 C4 C5 C6 -168.9(9) . .
O1 C4 C5 C6 7.8(8) . .
O2 C4 C5 C10 9.9(10) . .
O1 C4 C5 C10 -173.3(6) . .
C10 C5 C6 C7 0.0 . .
C4 C5 C6 C7 178.8(4) . .
C5 C6 C7 C8 0.0 . .
C6 C7 C8 C9 0.0 . .
C7 C8 C9 C10 0.0 . .
C8 C9 C10 C5 0.0 . .
C6 C5 C10 C9 0.0 . .
C4 C5 C10 C9 -178.9(3) . .
C1 N2 C1 N1 -58.7(6) 3_565 .
C3 N2 C1 N1 59.0(4) . .
C2 N1 C1 N2 59.2(4) . .
C1 N1 C1 N2 -58.3(5) 4_655 .
C1 N1 C2 N1 58.49(19) 4_655 2_665
C1 N1 C2 N1 -58.50(19) . 2_665
C1 N2 C3 N2 58.8(2) 3_565 2_665
C1 N2 C3 N2 -58.8(2) . 2_665
