Incorporation of Dyes into Hydrogen-Bond Networks: The Structures and Properties of Guanidinium Sulfonate Derivatives Containing Ethyl Orange and 4-Aminoazobenzene-4‘-sulfonate
Burke, Nichola J.; Burrows, Andrew D.; Mahon, Mary F.; Warren, John E.; Crystal Growth & Design 6 (2006) 546–; doi:10.1021/cg050499e

data_4504723
_publ_section_title
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 Incorporation of Dyes into Hydrogen-Bond Networks:&#x2009; The Structures
 and Properties of Guanidinium Sulfonate Derivatives Containing Ethyl
 Orange and 4-Aminoazobenzene-4&#x2018;-sulfonate
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_journal_issue                   2
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              546
_journal_paper_doi               10.1021/cg050499e
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C14 H18 N6 O3 S'
_chemical_formula_weight         350.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.687(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.8581(7)
_cell_length_b                   31.583(3)
_cell_length_c                   11.7241(10)
_cell_measurement_reflns_used    2406
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      '19.791 ?'
_cell_measurement_theta_min      2.468
_cell_volume                     3276.4(5)
_computing_cell_refinement       'local programs'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.786
_diffrn_measured_fraction_theta_max 0.786
_diffrn_measurement_device_type  'Bruker SMART CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.67780
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_sigmaI/netI    0.1233
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7066
_diffrn_reflns_theta_full        23.42
_diffrn_reflns_theta_max         23.42
_diffrn_reflns_theta_min         3.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            'Dark orange/red'
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plates
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0715
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0890P)^2^+0.2990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1643
_refine_ls_wR_factor_ref         0.1826
_reflns_number_gt                2373
_reflns_number_total             3766
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050499esi20050926_121833.cif
_cod_data_source_block           c:\compound_7\bath110
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4504723