Water-soluble β-aminobisulfonate building blocks for pH and Cu2+indicators
Cardona, Maria A.; Kveder, Marina; Baisch, Ulrich; Probert, Michael R.; Magri, David C.; RSC Adv. 6 (2016) 84712–; doi:10.1039/C6RA17791C

data_7226483
_publ_section_title
;
 Water-soluble \b-aminobisulfonate building blocks for pH and
 Cu2+indicators
;
_journal_issue                   88
_journal_name_full               'RSC Adv.'
_journal_page_first              84712
_journal_paper_doi               10.1039/C6RA17791C
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C44 H72 Br0.12 K9 N4 O37 S8, 0.88(Br1)'
_chemical_formula_sum            'C44 H72 Br K9 N4 O37 S8'
_chemical_formula_weight         1937.34
_chemical_name_systematic        'phenyl beta-aminobisulfonate'
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-09 deposited with the CCDC.
2016-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.8278(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9837(3)
_cell_length_b                   13.1145(2)
_cell_length_c                   32.7662(6)
_cell_measurement_reflns_used    22673
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.1150
_cell_measurement_theta_min      2.7330
_cell_volume                     7534.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -61.00 -35.00   1.00    4.00    --  -41.72 143.00 -36.00   26
  2  \w    -96.00 -70.00   1.00    4.00    --  -41.72 125.00 120.00   26
  3  \w    -55.00 -18.00   1.00    4.00    --  -41.72 125.00 120.00   37
  4  \w    -32.00  69.00   1.00    4.00    --   41.72 -57.00-120.00  101
  5  \w     28.00 118.00   1.00    4.00    --   41.72  38.00  30.00   90
  6  \w     65.00  90.00   1.00    4.00    --   41.72 137.00  57.00   25
  7  \w    -19.00  54.00   1.00    4.00    --   41.72 -38.00  30.00   73
  8  \w     35.00  78.00   1.00   16.00    --   92.50 -92.00 166.12   43
  9  \w     79.00 129.00   1.00   16.00    --   92.50 -93.00 122.77   50
 10  \w     14.00  40.00   1.00   16.00    --   92.50 -93.00-133.90   26
 11  \w     76.00 122.00   1.00   16.00    --   92.50 -61.00 150.00   46
 12  \w     68.00 105.00   1.00   16.00    --   92.50  77.00 120.00   37
 13  \w     65.00  90.00   1.00   16.00    --   92.50  30.00  30.00   25
 14  \w     70.00 111.00   1.00   16.00    --   92.50 -93.00  55.86   41
 15  \w     78.00 115.00   1.00   16.00    --   92.50  30.00   0.00   37
 16  \w     53.00  93.00   1.00   16.00    --   92.50 -61.00 -60.00   40
 17  \w     46.00 102.00   1.00   16.00    --   92.50 -92.00-107.00   56
 18  \w     18.00  68.00   1.00   16.00    --   92.50 -30.00 -30.00   50
 19  \w     15.00  40.00   1.00   16.00    --   92.50 -30.00-150.00   25
 20  \w     29.00  85.00   1.00   16.00    --   92.50-125.00-180.00   56
 21  \w     19.00  65.00   1.00   16.00    --   92.50 -30.00 150.00   46
 22  \w     18.00  64.00   1.00   16.00    --   92.50 -61.00 150.00   46
 23  \w     75.00 101.00   1.00   16.00    --   92.50  45.00  60.00   26
 24  \w     10.00  67.00   1.00   16.00    --   92.50 -94.00  90.00   57
 25  \w     29.00  61.00   1.00   16.00    --   92.50 -30.00 -90.00   32
 26  \w    125.00 170.00   1.00   16.00    --   92.50  77.00 120.00   45
 27  \w     89.00 132.00   1.00   16.00    --   92.50 -92.00  -3.69   43
 28  \w    106.00 167.00   1.00   16.00    --   92.50  30.00  30.00   61
 29  \w     41.00  74.00   1.00   16.00    --   92.50 -45.00-150.00   33
 30  \w     63.00 169.00   1.00   16.00    --   92.50  30.00 -30.00  106
 31  \w    129.00 168.00   1.00   16.00    --   92.50  77.00   0.00   39
 32  \w     83.00 109.00   1.00   16.00    --   92.50  77.00   0.00   26
 33  \w     85.00 111.00   1.00   16.00    --   92.50  45.00 -90.00   26
 34  \w     23.00  65.00   1.00   16.00    --   92.50 -45.00 -90.00   42
 35  \w     92.00 117.00   1.00   16.00    --   92.50 -92.00 166.12   25
 36  \w     24.00  71.00   1.00   16.00    --   92.50 -45.00 -30.00   47
 37  \w     63.00  90.00   1.00   16.00    --   92.50  61.00 120.00   27
 38  \w     50.00  79.00   1.00   16.00    --   92.50 -61.00  60.00   29
 39  \w     24.00  50.00   1.00   16.00    --   92.50-125.00-120.00   26
 40  \w     65.00  90.00   1.00   16.00    --   92.50-125.00-120.00   25
 41  \w     82.00 107.00   1.00   16.00    --   92.50 -93.00-133.90   25
 42  \w     87.00 124.00   1.00   16.00    --   92.50 -67.00 -48.43   37
 43  \w     15.00  40.00   1.00   16.00    --   92.50 -30.00-120.00   25
 44  \w     38.00  64.00   1.00   16.00    --   92.50 -45.00  60.00   26
 45  \w     41.00  66.00   1.00   16.00    --   92.50 -45.00  90.00   25
 46  \w     38.00  75.00   1.00   16.00    --   92.50 -45.00 150.00   37
 47  \w     50.00 131.00   1.00   16.00    --   92.50 -93.00 -74.81   81
 48  \w    131.00 157.00   1.00   16.00    --   92.50  45.00  60.00   26
 49  \w    150.00 176.00   1.00   16.00    --   92.50  15.00 -60.00   26
 50  \w     26.00  68.00   1.00   16.00    --   92.50 -15.00-120.00   42
 51  \w      9.00  42.00   1.00   16.00    --   92.50 -93.00 -74.81   33
 52  \w   -120.00  -8.00   1.00    4.00    --  -41.72 -77.00-150.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0140918000
_diffrn_orient_matrix_UB_12      0.0515009000
_diffrn_orient_matrix_UB_13      0.0433014000
_diffrn_orient_matrix_UB_21      0.0122779000
_diffrn_orient_matrix_UB_22      -0.1053654000
_diffrn_orient_matrix_UB_23      0.0212333000
_diffrn_orient_matrix_UB_31      0.0858303000
_diffrn_orient_matrix_UB_32      0.0066692000
_diffrn_orient_matrix_UB_33      0.0008328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1612
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            103432
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.343
_diffrn_reflns_theta_max         66.343
_diffrn_reflns_theta_min         2.520
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.075
_exptl_absorpt_correction_T_max  0.646
_exptl_absorpt_correction_T_min  0.296
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.708
_exptl_crystal_description       plate
_exptl_crystal_F_000             3976
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.101
_refine_diff_density_max         4.266
_refine_diff_density_min         -1.368
_refine_diff_density_rms         0.379
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.536
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     946
_refine_ls_number_reflns         13155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.536
_refine_ls_R_factor_all          0.1636
_refine_ls_R_factor_gt           0.1480
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3662
_refine_ls_wR_factor_ref         0.3843
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10366
_reflns_number_total             13155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra17791c2.cif
_cod_data_source_block           dcm006cu_may2016
_cod_database_code               7226483
_chemical_oxdiff_formula         'C44 H60 N4 O37 S17'
_reflns_odcompleteness_completeness 98.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.81
_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. Uiso/Uaniso restraints and constraints
Uanis(Br1) = Uanis(Br1A)
Uanis(K2) = Uanis(K2A)
3. Others
 Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
 Sof(K2A)=1-FVAR(2)
 Sof(K2)=FVAR(2)
4.a Rotating group:
 O102(H10A,H10B), O105(H10C,H10D), O100(H10E,H10F), O103(H10G,H10H), O107(H10I,
 H10J), O108(H10K,H10L)
4.b Secondary CH2 refined with riding coordinates:
 C82(H82A,H82B), C88(H88A,H88B), C40(H40A,H40B), C19(H19A,H19B), C61(H61A,
 H61B), C62(H62A,H62B), C67(H67A,H67B), C83(H83A,H83B), C20(H20A,H20B),
 C47(H47A,H47B), C89(H89A,H89B), C41(H41A,H41B), C46(H46A,H46B), C25(H25A,H25B),
  C26(H26A,H26B), C68(H68A,H68B)
4.c Aromatic/amide H refined with riding coordinates:
 C36(H36), C33(H33), C13(H13), C57(H57), C56(H56), C75(H75), C76(H76),
 C34(H34), C55(H55), C78(H78), C54(H54), C15(H15), C14(H14), C12(H12), C35(H35),
  C77(H77)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C60(H60A,H60B,H60C), C81(H81A,H81B,H81C), C39(H39A,H39B,
 H39C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2014-06-17
_olex2_submission_original_sample_id dcm006Cu
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.784
_solvent_exptl_crystal_recrystallization_method 'methanol and water'