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_7228394
_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 Cl2 O2, C3 H10 N O'
_chemical_formula_sum            'C10 H13 Cl2 N O3'
_chemical_formula_weight         266.11
_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                   12.16200(10)
_cell_length_b                   7.94030(10)
_cell_length_c                   25.8738(2)
_cell_measurement_reflns_used    28976
_cell_measurement_temperature    150(10)
_cell_measurement_theta_max      73.7470
_cell_measurement_theta_min      4.0010
_cell_volume                     2498.63(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(10)
_diffrn_detector_area_resol_mean 5.2387
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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      -0.0401807000
_diffrn_orient_matrix_UB_12      0.0255179000
_diffrn_orient_matrix_UB_13      0.0559284000
_diffrn_orient_matrix_UB_21      -0.0989781000
_diffrn_orient_matrix_UB_22      0.1018579000
_diffrn_orient_matrix_UB_23      -0.0200879000
_diffrn_orient_matrix_UB_31      -0.0681052000
_diffrn_orient_matrix_UB_32      -0.1630971000
_diffrn_orient_matrix_UB_33      -0.0037800000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_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            44199
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.013
_diffrn_reflns_theta_min         3.416
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.634
_exptl_absorpt_correction_T_max  0.644
_exptl_absorpt_correction_T_min  0.356
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.2c (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    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_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         0.370
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00052(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+1.3557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0781
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2476
_reflns_number_total             2527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00835j2.cif
_cod_data_source_block           TMANO24DCB150K
_cod_database_code               7228394
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.96
_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: O3B(0.5) O2B(0.5) O3A(0.5) O2A(0.5)
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), C9(H9a,H9b,H9c), C10(H10a,H10b,H10c)
;
_olex2_submission_special_instructions 'No special instructions were received'