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_7219192
_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, C4 H6 N3'
_chemical_formula_sum            'C12 H7 Cl4 N3 O4'
_chemical_formula_weight         399.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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.
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_cell_angle_alpha                90.00
_cell_angle_beta                 106.969(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.614(3)
_cell_length_b                   11.255(2)
_cell_length_c                   10.900(2)
_cell_measurement_reflns_used    9642
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.294
_cell_measurement_theta_min      2.475
_cell_volume                     1480.1(5)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1676
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14714
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.69
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_type   none
_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    1.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0960P)^2^+0.5287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1498
_reflns_number_gt                2324
_reflns_number_total             2590
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra15392h2.cif
_cod_data_source_block           compound4
_cod_database_code               7219192
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C33(H33), C36(H36), C38(H38)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
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_olex2_submission_special_instructions 'No special instructions were received'