#------------------------------------------------------------------------------
#$Date: 2022-05-04 01:50:10 +0300 (Wed, 04 May 2022) $
#$Revision: 274857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/01/7710171.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7710171
loop_
_publ_author_name
'Tzegai, Wintana'
'Reil, Michaela'
'Burzlaff, Nicolai'
_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         'C13 H7 Mn N4 O9'
_chemical_formula_sum            'C13 H7 Mn N4 O9'
_chemical_formula_weight         418.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-14
_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                 107.404(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9306(5)
_cell_length_b                   5.6066(2)
_cell_length_c                   20.6630(8)
_cell_measurement_reflns_used    2064
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      72.3240
_cell_measurement_theta_min      3.2100
_cell_volume                     1650.51(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.72a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.72a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.72a (Rigaku OD, 2020)'
_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      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2903
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  34.00   1.00    8.22    --  -40.61  38.00-180.00   99
  2  ω   -115.00 -16.00   1.00    8.22    --  -40.61 -38.00   0.00   99
  3  ω      6.00  82.00   1.00    8.22    --   40.61 -99.00 -60.00   76
  4  ω     22.00 106.00   1.00   32.91    --  104.57 -94.00 -60.00   84
  5  ω     79.00 178.00   1.00   32.91    --  104.57  45.00-150.00   99
  6  ω     32.00 130.00   1.00   32.91    --  104.57 -45.00-120.00   98
  7  ω    103.00 178.00   1.00   32.91    --  104.57  77.00 -30.00   75
  8  ω     28.00 109.00   1.00   32.91    --  104.57-111.00-120.00   81
  9  ω    104.00 178.00   1.00   32.91    --  104.57 111.00-120.00   74
 10  ω   -113.00 -12.00   1.00    8.22    --  -40.61 -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       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1079782000
_diffrn_orient_matrix_UB_12      -0.0120367000
_diffrn_orient_matrix_UB_13      -0.0224052000
_diffrn_orient_matrix_UB_21      0.0045111000
_diffrn_orient_matrix_UB_22      -0.2737003000
_diffrn_orient_matrix_UB_23      -0.0048447000
_diffrn_orient_matrix_UB_31      0.0015837000
_diffrn_orient_matrix_UB_32      -0.0213253000
_diffrn_orient_matrix_UB_33      0.0746935000
_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  0.0516
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7946
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.278
_diffrn_reflns_theta_min         3.238
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.72a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0415
_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/[σ²(Fo²)+(0.0382P)²+0.4141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2540
_reflns_number_total             3171
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt00848c2.cif
_cod_data_source_block           buni210308a
_cod_database_code               7710171
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Mn Br Cl'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.810
_shelx_estimated_absorpt_t_min   0.518
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C24(H24), C22(H22)
2.c Idealised tetrahedral OH refined as rotating group:
 O11(H11), O21(H21)
;
_olex2_date_sample_data_collection 2021-03-08
_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 1.207
_oxdiff_exptl_absorpt_empirical_full_min 0.844
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.47317(3) 0.57119(9) 0.32798(2) 0.01929(13) Uani 1 1 d . . . . .
O1 O 0.55739(14) 0.8118(4) 0.29806(10) 0.0218(4) Uani 1 1 d . . . . .
O2 O 0.66813(14) 0.8802(4) 0.24745(11) 0.0246(5) Uani 1 1 d . . . . .
O5 O 0.30211(15) 0.8484(4) 0.26123(13) 0.0326(5) Uani 1 1 d . . . . .
O4 O 0.35804(17) 0.2159(4) 0.37244(12) 0.0338(5) Uani 1 1 d . . . . .
N12 N 0.65695(16) 0.3653(4) 0.33163(12) 0.0198(5) Uani 1 1 d . . . . .
N22 N 0.54795(16) 0.3730(4) 0.22141(12) 0.0196(5) Uani 1 1 d . . . . .
O3 O 0.49315(18) 0.7909(5) 0.46097(12) 0.0391(6) Uani 1 1 d . . . . .
N21 N 0.46770(16) 0.3978(4) 0.23949(12) 0.0209(5) Uani 1 1 d . . . . .
N11 N 0.59332(17) 0.3796(5) 0.36770(12) 0.0213(5) Uani 1 1 d . . . . .
O12 O 0.83533(19) -0.1434(6) 0.45700(14) 0.0547(9) Uani 1 1 d . . . . .
O11 O 0.7279(2) -0.1038(6) 0.51287(15) 0.0565(9) Uani 1 1 d . . . . .
H11 H 0.758412 -0.211532 0.536101 0.085 Uiso 1 1 calc R U . . .
O21 O 0.4391(2) -0.0559(7) 0.05122(15) 0.0581(9) Uani 1 1 d . . . . .
H21 H 0.405094 -0.131678 0.019323 0.087 Uiso 1 1 calc R U . . .
O22 O 0.3062(2) -0.0224(6) 0.08073(16) 0.0604(10) Uani 1 1 d . . . . .
C2 C 0.61943(19) 0.7486(5) 0.27070(15) 0.0196(6) Uani 1 1 d . . . . .
C1 C 0.63375(19) 0.4768(5) 0.26536(14) 0.0187(6) Uani 1 1 d . . . . .
H1 H 0.684943 0.448953 0.245661 0.022 Uiso 1 1 calc R U . . .
C14 C 0.7283(2) 0.2201(6) 0.36142(15) 0.0237(6) Uani 1 1 d . . . . .
H14 H 0.779064 0.183153 0.345961 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6271(2) 0.2398(6) 0.42088(15) 0.0254(6) Uani 1 1 d . . . . .
H12 H 0.598625 0.214004 0.454588 0.031 Uiso 1 1 calc R U . . .
C24 C 0.5334(2) 0.2424(6) 0.16492(15) 0.0255(6) Uani 1 1 d . . . . .
H24 H 0.577841 0.201707 0.143497 0.031 Uiso 1 1 calc R U . . .
C22 C 0.4022(2) 0.2809(6) 0.19295(16) 0.0270(7) Uani 1 1 d . . . . .
H22 H 0.339868 0.267491 0.192312 0.032 Uiso 1 1 calc R U . . .
C13 C 0.7120(2) 0.1357(6) 0.41953(16) 0.0291(7) Uani 1 1 d . . . . .
C3 C 0.4863(2) 0.7162(6) 0.40900(17) 0.0254(7) Uani 1 1 d . . . . .
C4 C 0.4021(2) 0.3513(6) 0.35398(16) 0.0248(6) Uani 1 1 d . . . . .
C5 C 0.3692(2) 0.7435(6) 0.28715(16) 0.0250(7) Uani 1 1 d . . . . .
C23 C 0.4399(2) 0.1800(7) 0.14463(17) 0.0324(7) Uani 1 1 d . . . . .
C16 C 0.7647(2) -0.0479(8) 0.46509(18) 0.0390(9) Uani 1 1 d . . . . .
C26 C 0.3891(3) 0.0255(8) 0.08913(19) 0.0414(9) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N21 Mn1 O1 84.72(9) . . ?
N11 Mn1 O1 85.61(9) . . ?
N11 Mn1 N21 84.54(10) . . ?
C3 Mn1 O1 94.37(12) . . ?
C3 Mn1 N21 175.95(12) . . ?
C3 Mn1 N11 91.46(12) . . ?
C4 Mn1 O1 177.90(11) . . ?
C4 Mn1 N21 94.08(12) . . ?
C4 Mn1 N11 92.56(12) . . ?
C4 Mn1 C3 86.71(14) . . ?
C5 Mn1 O1 91.50(11) . . ?
C5 Mn1 N21 92.15(12) . . ?
C5 Mn1 N11 175.79(11) . . ?
C5 Mn1 C3 91.82(14) . . ?
C5 Mn1 C4 90.27(14) . . ?
C2 O1 Mn1 122.82(19) . . ?
N11 N12 C1 118.6(2) . . ?
C14 N12 N11 111.8(2) . . ?
C14 N12 C1 129.1(2) . . ?
N21 N22 C1 118.1(2) . . ?
C24 N22 N21 111.5(2) . . ?
C24 N22 C1 130.3(2) . . ?
N22 N21 Mn1 119.23(18) . . ?
C22 N21 Mn1 135.0(2) . . ?
C22 N21 N22 105.6(2) . . ?
N12 N11 Mn1 118.67(18) . . ?
C12 N11 Mn1 135.9(2) . . ?
C12 N11 N12 105.2(2) . . ?
C16 O11 H11 109.5 . . ?
C26 O21 H21 109.5 . . ?
O1 C2 C1 116.2(2) . . ?
O2 C2 O1 126.9(3) . . ?
O2 C2 C1 116.9(2) . . ?
N12 C1 N22 109.6(2) . . ?
N12 C1 C2 110.9(2) . . ?
N12 C1 H1 109.2 . . ?
N22 C1 C2 108.9(2) . . ?
N22 C1 H1 109.2 . . ?
C2 C1 H1 109.2 . . ?
N12 C14 H14 126.7 . . ?
N12 C14 C13 106.7(3) . . ?
C13 C14 H14 126.7 . . ?
N11 C12 H12 124.7 . . ?
N11 C12 C13 110.7(3) . . ?
C13 C12 H12 124.7 . . ?
N22 C24 H24 126.6 . . ?
N22 C24 C23 106.9(3) . . ?
C23 C24 H24 126.6 . . ?
N21 C22 H22 124.7 . . ?
N21 C22 C23 110.5(3) . . ?
C23 C22 H22 124.7 . . ?
C14 C13 C12 105.7(3) . . ?
C14 C13 C16 127.1(3) . . ?
C12 C13 C16 126.7(3) . . ?
O3 C3 Mn1 175.1(3) . . ?
O4 C4 Mn1 177.8(3) . . ?
O5 C5 Mn1 178.5(3) . . ?
C24 C23 C22 105.5(3) . . ?
C24 C23 C26 129.3(3) . . ?
C22 C23 C26 125.1(3) . . ?
O12 C16 O11 124.6(3) . . ?
O12 C16 C13 122.4(3) . . ?
O11 C16 C13 112.9(3) . . ?
O21 C26 C23 114.9(3) . . ?
O22 C26 O21 124.6(3) . . ?
O22 C26 C23 120.5(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.061(2) . ?
Mn1 N21 2.051(2) . ?
Mn1 N11 2.041(3) . ?
Mn1 C3 1.818(3) . ?
Mn1 C4 1.809(3) . ?
Mn1 C5 1.809(3) . ?
O1 C2 1.271(3) . ?
O2 C2 1.230(3) . ?
O5 C5 1.147(4) . ?
O4 C4 1.143(4) . ?
N12 N11 1.374(3) . ?
N12 C1 1.450(4) . ?
N12 C14 1.336(4) . ?
N22 N21 1.365(3) . ?
N22 C1 1.452(4) . ?
N22 C24 1.339(4) . ?
O3 C3 1.128(4) . ?
N21 C22 1.322(4) . ?
N11 C12 1.321(4) . ?
O12 C16 1.237(4) . ?
O11 H11 0.8200 . ?
O11 C16 1.305(4) . ?
O21 H21 0.8200 . ?
O21 C26 1.315(4) . ?
O22 C26 1.226(4) . ?
C2 C1 1.547(4) . ?
C1 H1 0.9800 . ?
C14 H14 0.9300 . ?
C14 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.403(4) . ?
C24 H24 0.9300 . ?
C24 C23 1.377(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.403(4) . ?
C13 C16 1.457(5) . ?
C23 C26 1.456(5) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O1 C2 O2 174.9(2) . . . . ?
Mn1 O1 C2 C1 -4.2(4) . . . . ?
Mn1 N21 C22 C23 -175.2(2) . . . . ?
Mn1 N11 C12 C13 174.4(2) . . . . ?
O1 C2 C1 N12 -57.0(3) . . . . ?
O1 C2 C1 N22 63.6(3) . . . . ?
O2 C2 C1 N12 123.9(3) . . . . ?
O2 C2 C1 N22 -115.5(3) . . . . ?
N12 N11 C12 C13 0.1(4) . . . . ?
N12 C14 C13 C12 0.4(4) . . . . ?
N12 C14 C13 C16 172.8(4) . . . . ?
N22 N21 C22 C23 0.0(4) . . . . ?
N22 C24 C23 C22 -0.4(4) . . . . ?
N22 C24 C23 C26 -175.3(4) . . . . ?
N21 N22 C1 N12 62.0(3) . . . . ?
N21 N22 C1 C2 -59.5(3) . . . . ?
N21 N22 C24 C23 0.4(4) . . . . ?
N21 C22 C23 C24 0.2(4) . . . . ?
N21 C22 C23 C26 175.4(4) . . . . ?
N11 N12 C1 N22 -59.4(3) . . . . ?
N11 N12 C1 C2 60.9(3) . . . . ?
N11 N12 C14 C13 -0.3(4) . . . . ?
N11 C12 C13 C14 -0.3(4) . . . . ?
N11 C12 C13 C16 -172.8(4) . . . . ?
C1 N12 N11 Mn1 -3.1(3) . . . . ?
C1 N12 N11 C12 172.4(3) . . . . ?
C1 N12 C14 C13 -171.5(3) . . . . ?
C1 N22 N21 Mn1 -1.5(3) . . . . ?
C1 N22 N21 C22 -177.7(3) . . . . ?
C1 N22 C24 C23 177.4(3) . . . . ?
C14 N12 N11 Mn1 -175.3(2) . . . . ?
C14 N12 N11 C12 0.2(3) . . . . ?
C14 N12 C1 N22 111.3(3) . . . . ?
C14 N12 C1 C2 -128.5(3) . . . . ?
C14 C13 C16 O12 3.2(7) . . . . ?
C14 C13 C16 O11 -174.6(4) . . . . ?
C12 C13 C16 O12 174.2(4) . . . . ?
C12 C13 C16 O11 -3.7(6) . . . . ?
C24 N22 N21 Mn1 175.9(2) . . . . ?
C24 N22 N21 C22 -0.3(3) . . . . ?
C24 N22 C1 N12 -114.8(3) . . . . ?
C24 N22 C1 C2 123.7(3) . . . . ?
C24 C23 C26 O21 -3.7(7) . . . . ?
C24 C23 C26 O22 175.5(4) . . . . ?
C22 C23 C26 O21 -177.7(4) . . . . ?
C22 C23 C26 O22 1.5(7) . . . . ?
