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_7219189
_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 H Cl4 O4, C8 H2 Cl4 O4, C12 H9 N2, C H4 O'
_chemical_formula_sum            'C29 H16 Cl8 N2 O9'
_chemical_formula_weight         820.04
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.20 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                 111.758(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.1486(4)
_cell_length_b                   8.7692(2)
_cell_length_c                   22.0638(5)
_cell_measurement_temperature    293(2)
_cell_volume                     3261.26(14)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17101
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.42
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         6740
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0421P)^2^+1.3431P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                5291
_reflns_number_total             6740
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra15392h2.cif
_cod_data_source_block           compound1
_cod_original_cell_volume        3261.26(13)
_cod_database_code               7219189
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N2-H2
 0.82 with sigma of 0.01
 O9-H9
 0.85 with sigma of 0.02
 O1-H1
 0.85 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C56(H56)
3.b Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C)
3.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
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_olex2_submission_special_instructions 'No special instructions were received'