#------------------------------------------------------------------------------
#$Date: 2024-07-05 16:39:09 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/31/7133129.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_7133129
loop_
_publ_author_name
'Steiner, Lorenz'
'Ćorović, Miljan Z'
'Dupé, Antoine'
'Mösch-Zanetti, Nadia C'
_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         'C13 H16 Br2 N4 O3 W'
_chemical_formula_sum            'C13 H16 Br2 N4 O3 W'
_chemical_formula_weight         619.97
_chemical_name_systematic
tricarbonyl-dibromo-bis(3,5-dimethyl-1H-pyrazole)-tungsten
_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   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                 91.105(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5949(2)
_cell_length_b                   14.4051(3)
_cell_length_c                   11.7972(3)
_cell_measurement_reflns_used    60547
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      33.1300
_cell_measurement_theta_min      2.2000
_cell_volume                     1800.16(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_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(10)
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.59   4.41   1.00   20.00    --  -21.24 -73.76-154.25  104
  2  ω    -99.59   4.41   1.00   20.00    --  -21.24 -73.76 -34.25  104
  3  ω    -53.58  19.42   1.00   20.00    --  -21.24  88.88-152.23   73
  4  ω    -53.58  19.42   1.00   20.00    --  -21.24  88.88 -32.23   73
  5  ω    -53.58  19.42   1.00   20.00    --  -21.24  88.88  87.77   73
  6  ω    -99.59   4.41   1.00   20.00    --  -21.24 -73.76  25.75  104
  7  ω    -99.59   4.41   1.00   20.00    --  -21.24 -73.76 145.75  104
  8  ω    -53.58  19.42   1.00   20.00    --  -21.24  88.88 -92.23   73
  9  φ     -9.83 350.17   1.00   20.00  58.62 -21.24  30.17    --   360
 10  ω    -53.58  19.42   1.00   20.00    --  -21.24  88.88  27.77   73
 11  ω    -53.58  19.42   1.00   20.00    --  -21.24  88.88 147.77   73
 12  ω    306.42 307.42   1.00   20.00    --  -21.24  88.88 147.77    1
 13  φ   -332.86  27.14   1.00   20.00   7.24 -21.24 -77.15    --   360
 14  ω    -99.59   4.41   1.00   20.00    --  -21.24 -73.76 -94.25  104
 15  ω    -99.59   4.41   1.00   20.00    --  -21.24 -73.76  85.75  104
 16  φ   -350.17   9.83   1.00   20.00  -7.37 -21.24 -30.17    --   360
 17  ω    -85.59  20.41   1.00   20.00    --   -6.24 -73.76 115.75  106
;
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1121
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            95310
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.232
_diffrn_source                   'Incoatec microfocus sealed tube'
_exptl_absorpt_coefficient_mu    10.874
_exptl_absorpt_correction_T_max  0.02646
_exptl_absorpt_correction_T_min  0.00914
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.288
_exptl_crystal_description       plate
_exptl_crystal_F_000             1160
_exptl_crystal_recrystallization_method 'recrystallized in DCM / heptane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         3.696
_refine_diff_density_min         -1.029
_refine_diff_density_rms         0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0343
_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/[σ²(Fo²)+(0.0524P)²+1.1396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3787
_reflns_number_total             4465
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc01305k2.cif
_cod_data_source_block           lst216_1
_cod_depositor_comments
'Adding full bibliography for 7133129--7133132.cif.'
_cod_database_code               7133129
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C13H16Br2N4O3W
_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   0.381
_shelx_estimated_absorpt_t_min   0.198
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2 = N4-H4
 0.88 with sigma of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11)
3.b Idealised Me refined as rotating group:
 C4(H41,H42,H43), C8(H81,H82,H83), C9(H91,H92,H93), C13(H131,H132,H133)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.827
_oxdiff_exptl_absorpt_empirical_full_min 0.262
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
W1 W 0.62270(2) 0.63908(2) 0.68970(2) 0.02936(8) Uani 1 1 d . . . . .
Br1 Br 0.53536(5) 0.58306(4) 0.88580(4) 0.03502(12) Uani 1 1 d . . . . .
Br2 Br 0.39673(5) 0.59332(3) 0.60004(4) 0.03247(12) Uani 1 1 d . . . . .
C1 C 0.7638(5) 0.6749(4) 0.7927(4) 0.0346(11) Uani 1 1 d . . . . .
O1 O 0.8482(4) 0.6907(3) 0.8528(4) 0.0445(9) Uani 1 1 d . . . . .
C2 C 0.7830(5) 0.5998(4) 0.6192(5) 0.0395(12) Uani 1 1 d . . . . .
O2 O 0.8782(4) 0.5794(3) 0.5791(4) 0.0537(11) Uani 1 1 d . . . . .
C3 C 0.6362(5) 0.5022(4) 0.6905(4) 0.0335(11) Uani 1 1 d . . . . .
O3 O 0.6361(4) 0.4213(3) 0.6913(3) 0.0429(9) Uani 1 1 d . . . . .
N1 N 0.5302(4) 0.7761(3) 0.7223(3) 0.0321(9) Uani 1 1 d . . . . .
N2 N 0.4571(4) 0.8162(3) 0.6374(4) 0.0357(10) Uani 1 1 d D . . . .
H2 H 0.437(5) 0.783(2) 0.577(2) 0.031(14) Uiso 1 1 d D . . . .
C4 C 0.5985(6) 0.8254(4) 0.9187(5) 0.0425(13) Uani 1 1 d . . . . .
H41 H 0.568195 0.768049 0.953512 0.064 Uiso 1 1 calc R U . . .
H42 H 0.580819 0.878092 0.968509 0.064 Uiso 1 1 calc R U . . .
H43 H 0.689662 0.820944 0.907300 0.064 Uiso 1 1 calc R U . . .
C5 C 0.5325(5) 0.8395(4) 0.8067(5) 0.0353(11) Uani 1 1 d . . . . .
C6 C 0.4613(6) 0.9176(4) 0.7743(5) 0.0425(13) Uani 1 1 d . . . . .
H6 H 0.447177 0.971526 0.818608 0.051 Uiso 1 1 calc R U . . .
C7 C 0.4155(5) 0.9010(4) 0.6653(5) 0.0401(12) Uani 1 1 d . . . . .
C8 C 0.3406(6) 0.9602(4) 0.5847(6) 0.0526(16) Uani 1 1 d . . . . .
H81 H 0.394984 1.008891 0.554231 0.079 Uiso 1 1 calc R U . . .
H82 H 0.270297 0.988786 0.624628 0.079 Uiso 1 1 calc R U . . .
H83 H 0.307527 0.921781 0.522364 0.079 Uiso 1 1 calc R U . . .
N3 N 0.6424(4) 0.7090(3) 0.5223(3) 0.0319(9) Uani 1 1 d . . . . .
N4 N 0.6044(4) 0.6670(3) 0.4229(4) 0.0337(9) Uani 1 1 d D . . . .
H4 H 0.573(5) 0.6104(13) 0.419(5) 0.044(18) Uiso 1 1 d D . . . .
C9 C 0.7711(6) 0.8457(4) 0.5766(5) 0.0404(13) Uani 1 1 d . . . . .
H91 H 0.705099 0.880903 0.614608 0.061 Uiso 1 1 calc R U . . .
H92 H 0.828416 0.888702 0.538960 0.061 Uiso 1 1 calc R U . . .
H93 H 0.818687 0.808858 0.632709 0.061 Uiso 1 1 calc R U . . .
C10 C 0.7119(5) 0.7824(3) 0.4904(4) 0.0301(10) Uani 1 1 d . . . . .
C11 C 0.7163(5) 0.7867(4) 0.3723(4) 0.0333(10) Uani 1 1 d . . . . .
H11 H 0.759285 0.831531 0.328390 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6459(5) 0.7130(4) 0.3321(4) 0.0346(11) Uani 1 1 d . . . . .
C13 C 0.6107(6) 0.6855(5) 0.2133(5) 0.0467(14) Uani 1 1 d . . . . .
H131 H 0.610253 0.617636 0.207210 0.070 Uiso 1 1 calc R U . . .
H132 H 0.672346 0.711206 0.160965 0.070 Uiso 1 1 calc R U . . .
H133 H 0.526550 0.709612 0.193935 0.070 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -0.8490 6.8722 '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
Br1 W1 Br2 86.849(17) . . ?
C1 W1 Br1 79.30(15) . . ?
C1 W1 Br2 164.95(16) . . ?
C1 W1 C2 71.9(2) . . ?
C1 W1 N1 89.58(18) . . ?
C1 W1 N3 110.13(18) . . ?
C2 W1 Br1 126.70(15) . . ?
C2 W1 Br2 121.90(17) . . ?
C2 W1 N1 134.7(2) . . ?
C2 W1 N3 70.30(19) . . ?
C3 W1 Br1 73.55(14) . . ?
C3 W1 Br2 79.67(14) . . ?
C3 W1 C1 101.8(2) . . ?
C3 W1 C2 69.9(2) . . ?
C3 W1 N1 155.46(19) . . ?
C3 W1 N3 116.52(18) . . ?
N1 W1 Br1 87.54(11) . . ?
N1 W1 Br2 83.91(10) . . ?
N3 W1 Br1 162.99(11) . . ?
N3 W1 Br2 81.92(11) . . ?
N3 W1 N1 78.63(16) . . ?
O1 C1 W1 176.2(5) . . ?
O2 C2 W1 177.9(6) . . ?
O3 C3 W1 175.8(5) . . ?
N2 N1 W1 119.1(3) . . ?
C5 N1 W1 136.1(3) . . ?
C5 N1 N2 104.7(4) . . ?
N1 N2 H2 118(3) . . ?
C7 N2 N1 112.7(4) . . ?
C7 N2 H2 129(3) . . ?
H41 C4 H42 109.5 . . ?
H41 C4 H43 109.5 . . ?
H42 C4 H43 109.5 . . ?
C5 C4 H41 109.5 . . ?
C5 C4 H42 109.5 . . ?
C5 C4 H43 109.5 . . ?
N1 C5 C4 124.1(5) . . ?
N1 C5 C6 109.8(5) . . ?
C6 C5 C4 126.1(5) . . ?
C5 C6 H6 126.5 . . ?
C7 C6 C5 106.9(5) . . ?
C7 C6 H6 126.5 . . ?
N2 C7 C6 105.9(5) . . ?
N2 C7 C8 122.5(5) . . ?
C6 C7 C8 131.6(5) . . ?
C7 C8 H81 109.5 . . ?
C7 C8 H82 109.5 . . ?
C7 C8 H83 109.5 . . ?
H81 C8 H82 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
N4 N3 W1 121.8(3) . . ?
C10 N3 W1 131.5(3) . . ?
C10 N3 N4 105.1(4) . . ?
N3 N4 H4 124(4) . . ?
C12 N4 N3 111.8(4) . . ?
C12 N4 H4 123(4) . . ?
H91 C9 H92 109.5 . . ?
H91 C9 H93 109.5 . . ?
H92 C9 H93 109.5 . . ?
C10 C9 H91 109.5 . . ?
C10 C9 H92 109.5 . . ?
C10 C9 H93 109.5 . . ?
N3 C10 C9 120.9(5) . . ?
N3 C10 C11 110.0(4) . . ?
C11 C10 C9 129.1(5) . . ?
C10 C11 H11 126.8 . . ?
C12 C11 C10 106.3(5) . . ?
C12 C11 H11 126.8 . . ?
N4 C12 C11 106.8(4) . . ?
N4 C12 C13 122.6(5) . . ?
C11 C12 C13 130.5(5) . . ?
C12 C13 H131 109.5 . . ?
C12 C13 H132 109.5 . . ?
C12 C13 H133 109.5 . . ?
H131 C13 H132 109.5 . . ?
H131 C13 H133 109.5 . . ?
H132 C13 H133 109.5 . . ?
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
W1 Br1 2.6347(5) . ?
W1 Br2 2.6810(5) . ?
W1 C1 1.976(5) . ?
W1 C2 1.988(6) . ?
W1 C3 1.976(6) . ?
W1 N1 2.240(4) . ?
W1 N3 2.230(4) . ?
C1 O1 1.154(6) . ?
C2 O2 1.160(7) . ?
C3 O3 1.166(7) . ?
N1 N2 1.380(5) . ?
N1 C5 1.351(7) . ?
N2 H2 0.8800(10) . ?
N2 C7 1.342(7) . ?
C4 H41 0.9800 . ?
C4 H42 0.9800 . ?
C4 H43 0.9800 . ?
C4 C5 1.497(7) . ?
C5 C6 1.403(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(8) . ?
C7 C8 1.494(8) . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
N3 N4 1.372(6) . ?
N3 C10 1.347(6) . ?
N4 H4 0.8800(10) . ?
N4 C12 1.341(7) . ?
C9 H91 0.9800 . ?
C9 H92 0.9800 . ?
C9 H93 0.9800 . ?
C9 C10 1.495(7) . ?
C10 C11 1.397(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(7) . ?
C12 C13 1.496(7) . ?
C13 H131 0.9800 . ?
C13 H132 0.9800 . ?
C13 H133 0.9800 . ?
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
W1 N1 N2 C7 -175.2(4) . . . . ?
W1 N1 C5 C4 -7.0(9) . . . . ?
W1 N1 C5 C6 174.8(4) . . . . ?
W1 N3 N4 C12 -168.3(4) . . . . ?
W1 N3 C10 C9 -14.3(7) . . . . ?
W1 N3 C10 C11 165.9(4) . . . . ?
N1 N2 C7 C6 -0.9(7) . . . . ?
N1 N2 C7 C8 176.6(5) . . . . ?
N1 C5 C6 C7 -0.8(7) . . . . ?
N2 N1 C5 C4 178.4(5) . . . . ?
N2 N1 C5 C6 0.2(6) . . . . ?
C4 C5 C6 C7 -178.9(6) . . . . ?
C5 N1 N2 C7 0.5(6) . . . . ?
C5 C6 C7 N2 1.0(7) . . . . ?
C5 C6 C7 C8 -176.2(7) . . . . ?
N3 N4 C12 C11 1.4(6) . . . . ?
N3 N4 C12 C13 -175.9(5) . . . . ?
N3 C10 C11 C12 0.3(6) . . . . ?
N4 N3 C10 C9 -179.6(5) . . . . ?
N4 N3 C10 C11 0.5(6) . . . . ?
C9 C10 C11 C12 -179.5(5) . . . . ?
C10 N3 N4 C12 -1.2(6) . . . . ?
C10 C11 C12 N4 -1.0(6) . . . . ?
C10 C11 C12 C13 176.0(6) . . . . ?
