Order-disorder phase transition induced by proton transfer in a co-crystal of 2,4-dichlorobenzoic Acid and Trimethylamine N- oxide
D'Vries, Richard Fernando; Moreno-Fuquen, Rodolfo; Camps, Ihosvany; Ayala, Alejandro P.; Kennedy, Alan; Reinheimer, Eric W.; Ellena, Javier A.; CrystEngComm  (2017) –; doi:10.1039/C7CE00835J

data_7228393
_publ_section_title
;
 Order-disorder phase transition induced by proton transfer in a
 co-crystal of 2,4-dichlorobenzoic Acid and Trimethylamine N- oxide
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00835J
_journal_year                    2017
_chemical_formula_moiety         'C7 H3 Cl1.98 O2, C3 H10 N O'
_chemical_formula_sum            'C10 H13 Cl1.98 N O3'
_chemical_formula_weight         265.40
_chemical_melting_point          413
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-04-19 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.12852(10)
_cell_length_b                   7.92362(7)
_cell_length_c                   25.81707(18)
_cell_measurement_reflns_used    30156
_cell_measurement_temperature    99.98(18)
_cell_measurement_theta_max      73.8740
_cell_measurement_theta_min      4.9700
_cell_volume                     2481.07(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41t (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2387
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -96.00  -2.00   1.00    1.00    --  -42.35 125.00  60.00   94
  2  \w   -112.00 -16.00   1.00    1.00    --  -42.35 -57.00 -60.00   96
  3  \w     23.00  97.00   1.00    1.00    --   42.35-125.00-150.00   74
  4  \w     83.00 178.00   1.00    2.00    --  106.34  30.00-150.00   95
  5  \w     26.00 109.00   1.00    2.00    --  106.34 -95.00-120.00   83
  6  \w     32.00 130.00   1.00    2.00    --  106.34 -30.00-150.00   98
  7  \w     94.00 178.00   1.00    2.00    --  106.34 125.00 120.00   84
  8  \w     35.00 121.00   1.00    2.00    --  106.34-125.00  90.00   86
  9  \w     35.00 130.00   1.00    2.00    --  106.34 -45.00  30.00   95
 10  \w   -113.00 -58.00   1.00    1.00    --  -42.35-148.00 137.00   55
 11  \w   -112.00 -16.00   1.00    1.00    --  -42.35 -57.00-180.00   96
 12  \w   -112.00 -16.00   1.00    1.00    --  -42.35 -57.00  60.00   96
 13  \w     83.00 178.00   1.00    2.00    --  106.34  30.00 -90.00   95
 14  \w     61.00 178.00   1.00    2.00    --  106.34  15.00 120.00  117
 15  \w     75.00 178.00   1.00    2.00    --  106.34  77.00 -60.00  103
 16  \w     82.00 178.00   1.00    2.00    --  106.34  45.00  30.00   96
 17  \w     82.00 178.00   1.00    2.00    --  106.34  45.00 150.00   96
 18  \w     83.00 178.00   1.00    2.00    --  106.34  30.00   0.00   95
 19  \w   -116.00 -11.00   1.00    1.00    --  -42.35 -77.00-120.00  105
 20  \w   -116.00 -11.00   1.00    1.00    --  -42.35 -77.00   0.00  105
 21  \w    -65.00  30.00   1.00    1.00    --  -42.35  38.00  30.00   95
 22  \w     75.00 178.00   1.00    2.00    --  106.34  77.00 -90.00  103
 23  \w     75.00 178.00   1.00    2.00    --  106.34  77.00  90.00  103
 24  \w     79.00 177.00   1.00    2.00    --  106.34  61.00-150.00   98
 25  \w     75.00 178.00   1.00    2.00    --  106.34  77.00 -30.00  103
 26  \w     79.00 177.00   1.00    2.00    --  106.34  61.00  60.00   98
 27  \w     26.00 109.00   1.00    2.00    --  106.34 -95.00 150.00   83
 28  \w   -116.00 -11.00   1.00    1.00    --  -42.35 -77.00 150.00  105
 29  \w   -116.00 -11.00   1.00    1.00    --  -42.35 -77.00 -90.00  105
 30  \w   -116.00 -11.00   1.00    1.00    --  -42.35 -77.00  60.00  105
 31  \w     75.00 134.00   1.00    2.00    --  106.34  77.00-120.00   59
 32  \w     75.00 178.00   1.00    2.00    --  106.34  77.00 150.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0394093000
_diffrn_orient_matrix_UB_12      -0.0213002000
_diffrn_orient_matrix_UB_13      0.0563594000
_diffrn_orient_matrix_UB_21      0.1003503000
_diffrn_orient_matrix_UB_22      -0.1016455000
_diffrn_orient_matrix_UB_23      -0.0191000000
_diffrn_orient_matrix_UB_31      0.0671679000
_diffrn_orient_matrix_UB_32      0.1643380000
_diffrn_orient_matrix_UB_33      -0.0044956000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            43582
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.071
_diffrn_reflns_theta_min         5.004
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.626
_exptl_absorpt_correction_T_max  0.645
_exptl_absorpt_correction_T_min  0.353
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41t (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       block
_exptl_crystal_F_000             1101
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00048(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0269
_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/[\s^2^(Fo^2^)+(0.0290P)^2^+1.5560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0697
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2473
_reflns_number_total             2505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00835j2.cif
_cod_data_source_block           TMAO24DCB_100K
_cod_original_cell_volume        2481.07(4)
_cod_database_code               7228393
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C20 H26 Cl4 N2 O6'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Cl1B(0.58094) Cl1A(0.39881)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              8194
_olex2_date_sample_data_collection 2016-02-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.641