Using Halogen•••Halogen Interactions or C/N‒H•••Cl Hydrogen Bonding to Direct Crystal Packing in Tetrachlorophthalic Acid with N‒heterocyclic Compounds
Hu, Yanjing; Li, Zhiqiang; Zhao, Yiran; Yang, Yu; Liu, Faqian; Wang, Lei; RSC Adv.  (2014) –; doi:10.1039/C4RA15392H

data_7219195
_publ_section_title
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 Using Halogen&#x2022;&#x2022;&#x2022;Halogen Interactions or
 C/N--H&#x2022;&#x2022;&#x2022;Cl Hydrogen Bonding to Direct Crystal
 Packing in Tetrachlorophthalic Acid with N--heterocyclic Compounds
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_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA15392H
_journal_year                    2014
_chemical_formula_moiety         'C8 Cl4 O4, C16 H20 N4, 2(H2 O)'
_chemical_formula_sum            'C24 H24 Cl4 N4 O6'
_chemical_formula_weight         606.27
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_audit_update_record
;
2014-11-28 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.590(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6127(5)
_cell_length_b                   23.7989(9)
_cell_length_c                   9.5324(4)
_cell_measurement_reflns_used    2120
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8030
_cell_measurement_theta_min      3.0310
_cell_volume                     2829.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -50.00   12.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184  -38.0000   60.0000 62

  2 omega  -95.00   31.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184  -19.0000  150.0000 126
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0124318000
_diffrn_orient_matrix_UB_12      0.0266880000
_diffrn_orient_matrix_UB_13      0.0263648000
_diffrn_orient_matrix_UB_21      0.0524438000
_diffrn_orient_matrix_UB_22      0.0017885000
_diffrn_orient_matrix_UB_23      0.0388472000
_diffrn_orient_matrix_UB_31      0.0181896000
_diffrn_orient_matrix_UB_32      0.0131493000
_diffrn_orient_matrix_UB_33      -0.0587958000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6437
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.65
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       octahedral
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0607
_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/[\s^2^(Fo^2^)+(0.0506P)^2^+4.4516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1551
_reflns_number_gt                2057
_reflns_number_total             2925
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra15392h2.cif
_cod_data_source_block           compound7
_cod_original_cell_volume        2829.23(19)
_cod_database_code               7219195
_chemical_oxdiff_formula         'C1 O1 N1 Cd1'
_reflns_odcompleteness_completeness 99.90
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C19(H19)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'