Bis(4-carboxylpyrazol-1-yl)acetic acid: a scorpionate ligand for complexes with improved water solubility.
Tzegai, Wintana; Reil, Michaela; Burzlaff, Nicolai; Dalton transactions (Cambridge, England : 2003) 51 (2022) 6839–6845; doi:10.1039/d2dt00848c

data_7710170
_publ_section_title
;
 Bis(4-carboxylpyrazol-1-yl)acetic acid: a scorpionate ligand for
 complexes with improved water solubility.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6839
_journal_page_last               6845
_journal_paper_doi               10.1039/d2dt00848c
_journal_volume                  51
_journal_year                    2022
_chemical_formula_moiety         'C10 H8 N4 O6, 1(C4 H8 O)'
_chemical_formula_sum            'C14 H16 N4 O7'
_chemical_formula_weight         352.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-03-16 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.252(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8518(3)
_cell_length_b                   15.4697(4)
_cell_length_c                   13.9712(2)
_cell_measurement_reflns_used    5473
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      72.2610
_cell_measurement_theta_min      4.2740
_cell_volume                     3371.36(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2903
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -116.00 -17.00   1.00    3.00    --  -41.48 -38.00 -90.00   99
  2  \w    -87.00  -6.00   1.00    3.00    --  -41.48 125.00  60.00   81
  3  \w     31.00 112.00   1.00    9.00    --  104.33-125.00 -90.00   81
  4  \w     31.00 130.00   1.00    9.00    --  104.33 -45.00 -60.00   99
  5  \w     97.00 178.00   1.00    9.00    --  104.33 125.00  90.00   81
  6  \w    103.00 178.00   1.00    9.00    --  104.33  77.00 -30.00   75
  7  \w    103.00 178.00   1.00    9.00    --  104.33  77.00  30.00   75
  8  \w     28.00 137.00   1.00    9.00    --  104.33 -77.00 -90.00  109
  9  \w     76.00 178.00   1.00    9.00    --  104.33  30.00-180.00  102
 10  \w   -116.00 -65.00   1.00    3.00    --  -41.48 -38.00   0.00   51
 11  \w     13.00 114.00   1.00    3.00    --   41.48  57.00 120.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0501663000
_diffrn_orient_matrix_UB_12      -0.0852200000
_diffrn_orient_matrix_UB_13      -0.0205984000
_diffrn_orient_matrix_UB_21      -0.0719660000
_diffrn_orient_matrix_UB_22      0.0366210000
_diffrn_orient_matrix_UB_23      0.0493080000
_diffrn_orient_matrix_UB_31      -0.0454852000
_diffrn_orient_matrix_UB_32      0.0360955000
_diffrn_orient_matrix_UB_33      -0.0984805000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9810
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.726
_diffrn_reflns_theta_min         4.025
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.492
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     296
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+4.7913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1345
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2949
_reflns_number_total             3302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00848c2.cif
_cod_data_source_block           buni210204a
_cod_original_cell_volume        3371.35(12)
_cod_database_code               7710170
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C14H12N4O7
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.669
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C32-C31 = C32-C33
 1.44 with sigma of 0.02
 C31-O3 = C34-C33
 1.53 with sigma of 0.02
 O3-C34
 1.54 with sigma of 0.02
 O5-C51 = O5-C54
 1.44 with sigma of 0.02
 C51-C52 = C53-C54
 1.53 with sigma of 0.02
 C52-C53
 1.54 with sigma of 0.02
 C32-O3 = C32-C34 = C31-C34 = O3-C33
 2.38 with sigma of 0.04
 O5-C52 = O5-C53 = C51-C53 = C52-C54
 2.38 with sigma of 0.04
 O3-C33 \\sim C31-C34
 with sigma of 0.04
 C32-O3 \\sim C32-C34
 with sigma of 0.04
 C31-O3 \\sim O3-C34 \\sim C34-C33
 with sigma of 0.02
 C32-C31 \\sim C32-C33
 with sigma of 0.02
 C51-C52 \\sim C52-C53 \\sim C53-C54
 with sigma of 0.02
 O5-C52 \\sim O5-C53
 with sigma of 0.04
 O5-C51 \\sim O5-C54
 with sigma of 0.02
 C52-C54 \\sim C51-C53
 with sigma of 0.04
3. Rigid bond restraints
 C44, O4, C41, C42, C43
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1, O2, C2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1, C2, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2, C2, O1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C32 \\sim C31 \\sim O3 \\sim C34 \\sim C33: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
O5 \\sim C51 \\sim C52 \\sim C53 \\sim C54: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C44 \\sim O4 \\sim C41 \\sim C42 \\sim C43: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
O1 \\sim C2 \\sim O2: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
Uanis(O5) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53)
\\sim Ueq, Uanis(C54) \\sim Ueq: with sigma of 0.05 and sigma for terminal
atoms of 0.1
Uanis(C32) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C34)
\\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(C51) \\sim Ueq,
Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C54) \\sim Ueq: with sigma of
0.05 and sigma for terminal atoms of 0.1
Uanis(C44) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42)
\\sim Ueq, Uanis(C43) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C53) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(O5)
\\sim Ueq, Uanis(C54) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
5. Rigid body (RIGU) restrains
 C32, C31, O3, C34, C33
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O5, C51, C52, C53, C54
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 1*[Sof(C32)+Sof(H32a)+Sof(H32b)+Sof(C31)+Sof(H31a)+Sof(H31b)+Sof(O3)+Sof(C34)+
 Sof(H34a)+Sof(H34b)+Sof(C33)+Sof(H33a)+Sof(H33b)]+1*[Sof(O5)+Sof(C51)+
 Sof(H51a)+Sof(H51b)+Sof(C52)+Sof(H52a)+Sof(H52b)+Sof(C53)+Sof(H53a)+Sof(H53b)+
 Sof(C54)+Sof(H54a)+Sof(H54b)]+1*[Sof(C44)+Sof(H44a)+Sof(H44b)+Sof(O4)+Sof(C41)+
 Sof(H41a)+Sof(H41b)+Sof(C42)+Sof(H42a)+Sof(H42b)+Sof(C43)+Sof(H43a)+Sof(H43b)]=
 1 with esd of 0.001
 Sof(C32)=Sof(H32a)=Sof(H32b)=Sof(C31)=Sof(H31a)=Sof(H31b)=Sof(O3)=Sof(C34)=
 Sof(H34a)=Sof(H34b)=Sof(C33)=Sof(H33a)=Sof(H33b)=FVAR(1)
 Sof(O5)=Sof(C51)=Sof(H51a)=Sof(H51b)=Sof(C52)=Sof(H52a)=Sof(H52b)=Sof(C53)=
 Sof(H53a)=Sof(H53b)=Sof(C54)=Sof(H54a)=Sof(H54b)=FVAR(2)
 Sof(C44)=Sof(H44a)=Sof(H44b)=Sof(O4)=Sof(C41)=Sof(H41a)=Sof(H41b)=Sof(C42)=
 Sof(H42a)=Sof(H42b)=Sof(C43)=Sof(H43a)=Sof(H43b)=FVAR(3)
 Sof(H1)=1-FVAR(4)
 Sof(H2)=FVAR(4)
7.a Ternary CH refined with riding coordinates:
 C1(H1a)
7.b Secondary CH2 refined with riding coordinates:
 C32(H32a,H32b), C31(H31a,H31b), C34(H34a,H34b), C33(H33a,H33b), C51(H51a,
 H51b), C52(H52a,H52b), C53(H53a,H53b), C54(H54a,H54b), C44(H44a,H44b),
 C41(H41a,H41b), C42(H42a,H42b), C43(H43a,H43b)
7.c Aromatic/amide H refined with riding coordinates:
 C22(H22)
;
_shelx_res_checksum              89928
_olex2_date_sample_data_collection 2021-02-04
_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 1.343
_oxdiff_exptl_absorpt_empirical_full_min 0.787