Vinyl-pyrazole as a biomimetic acetaldehyde surrogate.
Steiner, Lorenz; Ćorović, Miljan Z; Dupé, Antoine; Mösch-Zanetti, Nadia C; Chemical communications (Cambridge, England) 60 (2024) 6873–6876; doi:10.1039/d4cc01305k

data_7133131
_publ_section_title
;
 Vinyl-pyrazole as a biomimetic acetaldehyde surrogate.
;
_journal_issue                   54
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6873
_journal_page_last               6876
_journal_paper_doi               10.1039/d4cc01305k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C21 H29 N6 O4 W2, Br, C H Cl3'
_chemical_formula_sum            'C22 H30 Br Cl3 N6 O4 W2'
_chemical_formula_weight         996.48
_chemical_name_systematic
'(mu-3,5-dimethylpyrazolyl)-bis((mu2-hydroxo)-(3,5-dimethyl-1H-pyrazole,N)-(eta2-ethyne)-carbonyl)-di-tungsten bromide chloroform 1:1 solvate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-13
_audit_creation_method
;
Olex2 1.5-ac6-019
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_audit_update_record
;
2024-05-13 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.85700(10)
_cell_length_b                   15.9287(3)
_cell_length_c                   12.3215(2)
_cell_measurement_reflns_used    30210
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      33.4320
_cell_measurement_theta_min      2.0860
_cell_volume                     1542.06(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-019 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-019 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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    -23.00  57.00   0.50    2.00    --   13.37 -99.00  90.00  160
  2  \w     42.00  90.00   0.50    2.00    --   13.37 178.00 120.00   96
  3  \w     39.00  92.00   0.50    2.00    --   13.37-178.00 -30.00  106
  4  \w    -39.00  63.00   0.50    2.00    --  -15.09  57.00   0.00  204
  5  \w    -93.00   9.00   0.50    2.00    --  -15.09 -57.00  90.00  204
  6  \w    -46.00  56.00   0.50    2.00    --  -15.09  77.00 -30.00  204
  7  \w    -93.00   9.00   0.50    2.00    --  -15.09 -57.00-150.00  204
  8  \w    -23.00  28.00   0.50    2.00    --  -15.09 -99.00  60.00  102
  9  \w    -69.00   5.00   0.50    2.00    --   13.37 -19.00 150.00  148
 10  \w    -23.00  57.00   0.50    2.00    --   13.37 -99.00-120.00  160
 11  \w    -23.00   6.00   0.50    2.00    --   13.37 -99.00 120.00   58
 12  \w    -93.00   9.00   0.50    2.00    --  -15.09 -57.00 -30.00  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0790687000
_diffrn_orient_matrix_UB_12      -0.0159031000
_diffrn_orient_matrix_UB_13      0.0187739000
_diffrn_orient_matrix_UB_21      0.0211040000
_diffrn_orient_matrix_UB_22      -0.0402009000
_diffrn_orient_matrix_UB_23      -0.0207602000
_diffrn_orient_matrix_UB_31      0.0381301000
_diffrn_orient_matrix_UB_32      -0.0106858000
_diffrn_orient_matrix_UB_33      0.0502926000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            48614
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.501
_diffrn_reflns_theta_min         2.090
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    9.047
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.415
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
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            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_description       block
_exptl_crystal_F_000             940
_exptl_crystal_recrystallization_method 'recrystallized in chloroform'
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.051
_refine_diff_density_max         1.330
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.505(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         5144
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0218P)^2^+1.2202P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0471
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4558
_reflns_number_total             5144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01305k2.cif
_cod_data_source_block           ad07_2
_cod_depositor_comments
'Adding full bibliography for 7133129--7133132.cif.'
_cod_database_code               7133131
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C22 H29 N6 O4 Cl3 Br1 W2 '
_chemical_oxdiff_usercomment     LST363
_shelx_estimated_absorpt_t_max   0.655
_shelx_estimated_absorpt_t_min   0.320
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.495(14)
 0.505(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C12-Cl1 = C12-Cl3 = C12-Cl2
 1.78 with sigma of 0.02
 N2-H21
 0.88 with sigma of 0.0001
 C12-Cl1 \\sim C12-Cl3 \\sim C12-Cl2
 with sigma of 0.02
 Cl1-Cl3 \\sim Cl3-Cl2 \\sim Cl2-Cl1
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
Cl1 \\sim Cl2 \\sim Cl3 \\sim C12: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 Cl1, Cl2, Cl3, C12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) Cl3(0.5) C12(0.5) H12(0.5)
7.a Ternary CH refined with riding coordinates:
 C12(H12)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C11(H111)
7.c Idealised Me refined as rotating group:
 C4(H41,H42,H43), C8(H81,H82,H83), C9(H91,H92,H93)
;
_shelx_res_checksum              80
_shelx_hkl_checksum              50359
_olex2_date_sample_data_collection 2023-12-22
_olex2_date_sample_submission    2023-12-21
_olex2_exptl_crystal_mounting_method 'mounted on a glass fiber'
_olex2_submission_original_sample_id LST363
_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 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.750