Supramolecular heterosynthon assemblies of ortho-phenylenediamine with substituted aromatic carboxylic acids
Mishra, Risha; Pallepogu, Raghavaiah; Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 74 (2018) 32–; doi:10.1107/S2052520617014299

data_2021916
_publ_section_title
;
 Supramolecular heterosynthon assemblies of ortho-phenylenediamine with
 substituted aromatic carboxylic acids
;
_journal_coeditor_code           EB5067
_journal_issue                   1
_journal_name_full
'Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials'
_journal_page_first              32
_journal_paper_doi               10.1107/S2052520617014299
_journal_volume                  74
_journal_year                    2018
_chemical_formula_moiety         'C7 H6 O3, C7 H5 O3, C6 H9 N2, C6 H8 N2'
_chemical_formula_sum            'C26 H28 N4 O6'
_chemical_formula_weight         492.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                72.196(4)
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_cell_formula_units_Z            4
_cell_length_a                   9.9374(5)
_cell_length_b                   14.3212(6)
_cell_length_c                   18.2929(11)
_cell_measurement_reflns_used    5251
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.6120
_cell_measurement_theta_min      4.5330
_cell_volume                     2437.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
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_diffrn_detector_area_resol_mean 16.3291
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_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
  1 omega   22.00  103.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227   57.0000    0.0000 81

  2 omega   54.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227    0.0000  -90.0000 39

  3 omega   51.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227   77.0000 -120.0000 51

  4 omega   46.00  172.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -90.0000 126

  5 omega   77.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 37

  6 omega   60.00  123.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -74.0000   36.0000 63

  7 omega   56.00  101.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 45

  8 omega   56.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 53

  9 omega   59.00   92.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 33

 10 omega   45.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 46

 11 omega   48.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 43

 12 omega   42.00   70.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 28

 13 omega   39.00   88.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 49

 14 omega   41.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 15 omega   92.00  170.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 78

 16 omega   45.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227  -99.0000    0.0000 26

 17 omega   18.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227 -125.0000   90.0000 54

 18 omega   17.00   75.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227  -99.0000  150.0000 58

 19 omega    2.00   54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227  -37.0000   30.0000 52

 20 omega   -9.00   18.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227    0.0000  -90.0000 27

 21 omega   23.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227  -37.0000 -180.0000 26

 22 omega   44.00   83.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 39

 23 omega   45.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 61

 24 omega   40.00   74.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 34

 25 omega   38.00   63.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 25

 26 omega   19.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227   77.0000 -120.0000 26

 27 omega   12.00  103.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227   77.0000  -90.0000 91

 28 omega  -31.00   55.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8227  -37.0000  120.0000 86
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_22      -0.0134722000
_diffrn_orient_matrix_UB_23      -0.0726945000
_diffrn_orient_matrix_UB_31      -0.0722655000
_diffrn_orient_matrix_UB_32      -0.0905809000
_diffrn_orient_matrix_UB_33      0.0505309000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15886
_diffrn_reflns_point_group_measured_fraction_full 0.996
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.207
_diffrn_reflns_theta_min         3.507
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       plate
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_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.2110P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
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_cod_data_source_file            eb5067sup1.cif
_cod_data_source_block           OPDPHB
_cod_database_code               2021916
_shelxl_version_number           2012-9
_chemical_oxdiff_formula         'C13 H14 N2 O3'
_chemical_oxdiff_usercomment     'OPDA PABA2'
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N2A(H2AB), N2B(H2BB), N1C(H1CB), N2C(H2CB), N1D(H1DB)
2.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C3B(H3B), C4B(H4B), C5B(H5B),
 C6B(H6B), C8A(H8A), C9A(H9A), C11A(H11A), C12A(H12A), C3C(H3C), C4C(H4C),
 C5C(H5C), C6C(H6C), C3D(H3D), C4D(H4D), C5D(H5D), C6D(H6D), C8D(H8D), C9D(H9D),
  C11D(H11D), C12D(H12D), C8C(H8C), C9C(H9C), C11C(H11C), C12C(H12C), C8B(H8B),
 C9B(H9B), C11B(H11B), C12B(H12B)
2.c Idealised Me refined as rotating group:
 N1A(H1AA,H1AB,H1AC), N1B(H1BA,H1BB,H1BC)
2.d Idealised tetrahedral OH refined as rotating group:
 O2A(H2A), O3A(H3AA), O2D(H2D), O3D(H3DA), O3C(H3CA), O3B(H3BA)
;
_olex2_submission_special_instructions 'No special instructions were received'