Intermolecular interactions and solubility behavior of multicomponent crystal forms of 2,4-D: design, structure analysis, and solid-state characterization
Fang, Lan; Xiao, Yuntian; Zhang, Chengtian; Gao, Zhenguo; Wu, Songgu; Gong, Junbo; Rohani, Sohrab; CrystEngComm 23 (2021) 7615–7627; doi:10.1039/D1CE01080H

data_7243609
_publ_section_title
;
 Intermolecular interactions and solubility behavior of multicomponent
 crystal forms of 2,4-D: design, structure analysis, and solid-state
 characterization
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              7615
_journal_page_last               7627
_journal_paper_doi               10.1039/D1CE01080H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C8 H5 Cl2 O3, C5 H7 N2'
_chemical_formula_sum            'C13 H12 Cl2 N2 O3'
_chemical_formula_weight         315.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-06 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.245(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1527(7)
_cell_length_b                   5.1499(3)
_cell_length_c                   24.1986(12)
_cell_measurement_reflns_used    5069
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.3160
_cell_measurement_theta_min      1.9480
_cell_volume                     1386.04(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_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   -120.00  60.00   1.00    3.00    --  -30.00  45.00   0.00  180
  2  \w   -120.00  30.00   1.00    3.00    --  -30.00  45.00  90.00  150
  3  \w   -120.00   0.00   1.00    3.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0567521000
_diffrn_orient_matrix_UB_12      0.0307653000
_diffrn_orient_matrix_UB_13      0.0136181000
_diffrn_orient_matrix_UB_21      0.0253543000
_diffrn_orient_matrix_UB_22      0.0070096000
_diffrn_orient_matrix_UB_23      -0.0259817000
_diffrn_orient_matrix_UB_31      -0.0143638000
_diffrn_orient_matrix_UB_32      0.1340420000
_diffrn_orient_matrix_UB_33      -0.0017789000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            16031
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.607
_diffrn_reflns_theta_min         1.688
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.0063(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         5108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0616
_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^)+(0.0516P)^2^+0.6953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1488
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3363
_reflns_number_total             5108
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01080h2.cif
_cod_data_source_block           r20210102b
_cod_depositor_comments
'Adding full bibliography for 7243608--7243612.cif.'
_cod_database_code               7243609
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.919
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), N2(H2A), C10(H10), C11(H11), C12(H12), C13(H13)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_shelx_res_checksum              16006
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.742