#------------------------------------------------------------------------------
#$Date: 2021-07-15 12:51:38 +0300 (Thu, 15 Jul 2021) $
#$Revision: 267559 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/41/1564172.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_1564172
loop_
_publ_author_name
'Bruno, Sofia M.'
'Amarante, Tatiana R.'
'Almeida Paz, Filipe A.'
'Pillinger, Martyn'
'Valente, Anabela A.'
'Gonçalves, Isabel S.'
_publ_section_title
;
 Oxidation of sulfides in aqueous media catalyzed by
 pyrazole-oxidoperoxido-molybdenum(VI) complexes
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119814
_journal_paper_doi               10.1016/j.ica.2020.119814
_journal_volume                  511
_journal_year                    2020
_chemical_formula_moiety         'C6 H8 Mo N4 O5'
_chemical_formula_sum            'C6 H8 Mo N4 O5'
_chemical_formula_weight         312.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                93.620(2)
_cell_angle_beta                 103.842(2)
_cell_angle_gamma                98.215(2)
_cell_formula_units_Z            4
_cell_length_a                   8.4202(6)
_cell_length_b                   9.3491(6)
_cell_length_c                   14.3933(9)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      29.20
_cell_measurement_theta_min      2.53
_cell_volume                     1083.27(12)
_computing_cell_refinement       'SAINT V8.37a   (Bruker, 2015)'
_computing_data_collection       'APEX3 2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37a   (Bruker, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 QUEST '
_diffrn_measurement_method       'ω / φ scans'
_diffrn_radiation_monochromator  'Multi-layer X-ray mirror'
_diffrn_radiation_source         'Sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12968
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_min         3.568
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
  SADABS-2016/2
  Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_description       Block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_transmission_factor_max   0.0976
_exptl_transmission_factor_min   0.0650
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0196
_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/[σ²(Fo²)+(0.0239P)²+0.3386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0515
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5455
_reflns_number_total             5798
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-511-119814.cif
_cod_data_source_block           1
_cod_database_code               1564172
_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_min   0.847
_shelx_estimated_absorpt_t_max   0.919
_exptl_absorpt_special_details
;
?
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Mo1 Mo 0.23167(2) 0.33123(2) 0.50448(2) 0.01616(4) Uani 1 1 d . . . . .
Mo2 Mo 0.39972(2) 0.10379(2) 0.15422(2) 0.02107(4) Uani 1 1 d . . . . .
O1 O 0.29878(13) 0.38643(11) 0.40906(7) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.33783(13) 0.49852(11) 0.59900(7) 0.0217(2) Uani 1 1 d . . . . .
O3 O 0.16192(13) 0.50292(11) 0.55224(8) 0.0235(2) Uani 1 1 d . . . . .
O4 O 0.11743(13) 0.13402(11) 0.45911(8) 0.0257(2) Uani 1 1 d . . . . .
O5 O 0.00439(13) 0.24262(12) 0.45010(8) 0.0262(2) Uani 1 1 d . . . . .
O6 O 0.43487(16) -0.06778(12) 0.16182(10) 0.0347(3) Uani 1 1 d . . . . .
O7 O 0.36545(14) 0.11796(12) 0.01579(8) 0.0289(2) Uani 1 1 d . . . . .
O8 O 0.20867(14) 0.08137(13) 0.04456(8) 0.0315(2) Uani 1 1 d . . . . .
O9 O 0.44225(14) 0.17977(12) 0.28801(8) 0.0277(2) Uani 1 1 d . . . . .
O10 O 0.26452(14) 0.13155(12) 0.24256(8) 0.0293(2) Uani 1 1 d . . . . .
N1 N 0.18691(15) 0.24481(13) 0.64845(9) 0.0209(2) Uani 1 1 d . . . . .
N2 N 0.09915(16) 0.11280(13) 0.64987(9) 0.0248(2) Uani 1 1 d . . . . .
H2 H 0.058272 0.049314 0.598916 0.030 Uiso 1 1 calc R U . . .
N3 N 0.45338(15) 0.23564(12) 0.54958(9) 0.0200(2) Uani 1 1 d . . . . .
N4 N 0.58675(15) 0.27604(13) 0.51484(9) 0.0235(2) Uani 1 1 d . . . . .
H4 H 0.592138 0.341654 0.473991 0.028 Uiso 1 1 calc R U . . .
N5 N 0.37818(16) 0.35539(13) 0.14244(9) 0.0239(2) Uani 1 1 d . . . . .
N6 N 0.35972(17) 0.44208(14) 0.21625(9) 0.0260(3) Uani 1 1 d . . . . .
H6 H 0.364353 0.415334 0.274245 0.031 Uiso 1 1 calc R U . . .
N7 N 0.65799(16) 0.18709(14) 0.16702(9) 0.0241(2) Uani 1 1 d . . . . .
N8 N 0.74135(16) 0.14299(14) 0.10386(9) 0.0262(3) Uani 1 1 d . . . . .
H8 H 0.699221 0.075864 0.055069 0.031 Uiso 1 1 calc R U . . .
C1 C 0.2263(2) 0.30498(18) 0.73911(11) 0.0311(3) Uani 1 1 d . . . . .
H1 H 0.289201 0.398866 0.760909 0.037 Uiso 1 1 calc R U . . .
C2 C 0.1622(3) 0.2110(2) 0.79753(13) 0.0410(4) Uani 1 1 d . . . . .
H2A H 0.172476 0.227803 0.864657 0.049 Uiso 1 1 calc R U . . .
C3 C 0.0817(2) 0.0899(2) 0.73777(13) 0.0347(4) Uani 1 1 d . . . . .
H3 H 0.023989 0.005178 0.755391 0.042 Uiso 1 1 calc R U . . .
C4 C 0.49483(19) 0.13365(16) 0.60811(11) 0.0254(3) Uani 1 1 d . . . . .
H4A H 0.424697 0.084635 0.642898 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6543(2) 0.10982(18) 0.61070(12) 0.0300(3) Uani 1 1 d . . . . .
H5 H 0.713258 0.043262 0.646271 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7092(2) 0.20339(18) 0.55058(13) 0.0304(3) Uani 1 1 d . . . . .
H6A H 0.815057 0.214209 0.537040 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3633(3) 0.43591(18) 0.06925(12) 0.0384(4) Uani 1 1 d . . . . .
H7 H 0.370518 0.403773 0.006681 0.046 Uiso 1 1 calc R U . . .
C8 C 0.3354(3) 0.5744(2) 0.09648(15) 0.0490(5) Uani 1 1 d . . . . .
H8A H 0.320978 0.652321 0.057648 0.059 Uiso 1 1 calc R U . . .
C9 C 0.3336(2) 0.57338(18) 0.19095(14) 0.0376(4) Uani 1 1 d . . . . .
H9 H 0.316786 0.651407 0.231168 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7640(2) 0.28963(19) 0.22928(12) 0.0332(3) Uani 1 1 d . . . . .
H10 H 0.739232 0.340600 0.281902 0.040 Uiso 1 1 calc R U . . .
C11 C 0.9157(2) 0.3108(2) 0.20585(15) 0.0395(4) Uani 1 1 d . . . . .
H11 H 1.012220 0.377241 0.238320 0.047 Uiso 1 1 calc R U . . .
C12 C 0.8968(2) 0.21547(19) 0.12575(13) 0.0328(3) Uani 1 1 d . . . . .
H12 H 0.978996 0.203249 0.092110 0.039 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'
Mo Mo -1.6832 0.6857 '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
O1 Mo1 O5 104.16(5) . .
O1 Mo1 O3 102.47(5) . .
O5 Mo1 O3 90.84(5) . .
O1 Mo1 O4 103.09(5) . .
O5 Mo1 O4 44.89(4) . .
O3 Mo1 O4 133.10(5) . .
O1 Mo1 O2 99.51(5) . .
O5 Mo1 O2 133.48(4) . .
O3 Mo1 O2 44.75(4) . .
O4 Mo1 O2 156.65(5) . .
O1 Mo1 N3 89.00(5) . .
O5 Mo1 N3 130.91(5) . .
O3 Mo1 N3 132.77(5) . .
O4 Mo1 N3 86.23(5) . .
O2 Mo1 N3 88.41(4) . .
O1 Mo1 N1 169.60(5) . .
O5 Mo1 N1 84.33(4) . .
O3 Mo1 N1 83.12(4) . .
O4 Mo1 N1 78.54(4) . .
O2 Mo1 N1 78.17(4) . .
N3 Mo1 N1 80.83(4) . .
O6 Mo2 O10 104.67(6) . .
O6 Mo2 O9 102.89(6) . .
O10 Mo2 O9 44.80(5) . .
O6 Mo2 O8 101.99(6) . .
O10 Mo2 O8 91.56(5) . .
O9 Mo2 O8 134.01(5) . .
O6 Mo2 O7 101.26(6) . .
O10 Mo2 O7 132.89(5) . .
O9 Mo2 O7 155.01(5) . .
O8 Mo2 O7 44.49(5) . .
O6 Mo2 N7 92.79(6) . .
O10 Mo2 N7 129.84(5) . .
O9 Mo2 N7 85.83(5) . .
O8 Mo2 N7 130.66(5) . .
O7 Mo2 N7 86.68(5) . .
O6 Mo2 N5 174.17(5) . .
O10 Mo2 N5 79.86(4) . .
O9 Mo2 N5 77.63(4) . .
O8 Mo2 N5 81.35(5) . .
O7 Mo2 N5 77.69(4) . .
N7 Mo2 N5 81.43(5) . .
O3 O2 Mo1 66.44(5) . .
O2 O3 Mo1 68.81(5) . .
O5 O4 Mo1 66.80(6) . .
O4 O5 Mo1 68.31(6) . .
O8 O7 Mo2 67.11(6) . .
O7 O8 Mo2 68.40(6) . .
O10 O9 Mo2 67.13(6) . .
O9 O10 Mo2 68.07(6) . .
C1 N1 N2 104.98(12) . .
C1 N1 Mo1 132.78(10) . .
N2 N1 Mo1 122.15(9) . .
C3 N2 N1 111.95(13) . .
C3 N2 H2 124.0 . .
N1 N2 H2 124.0 . .
C4 N3 N4 105.70(11) . .
C4 N3 Mo1 133.79(10) . .
N4 N3 Mo1 120.49(9) . .
C6 N4 N3 111.10(12) . .
C6 N4 H4 124.4 . .
N3 N4 H4 124.4 . .
C7 N5 N6 105.00(13) . .
C7 N5 Mo2 132.51(11) . .
N6 N5 Mo2 122.12(9) . .
C9 N6 N5 111.99(13) . .
C9 N6 H6 124.0 . .
N5 N6 H6 124.0 . .
C10 N7 N8 106.23(13) . .
C10 N7 Mo2 131.01(11) . .
N8 N7 Mo2 122.69(10) . .
C12 N8 N7 110.72(13) . .
C12 N8 H8 124.6 . .
N7 N8 H8 124.6 . .
N1 C1 C2 110.59(15) . .
N1 C1 H1 124.7 . .
C2 C1 H1 124.7 . .
C3 C2 C1 105.31(15) . .
C3 C2 H2A 127.3 . .
C1 C2 H2A 127.3 . .
N2 C3 C2 107.16(15) . .
N2 C3 H3 126.4 . .
C2 C3 H3 126.4 . .
N3 C4 C5 110.40(13) . .
N3 C4 H4A 124.8 . .
C5 C4 H4A 124.8 . .
C6 C5 C4 105.19(13) . .
C6 C5 H5 127.4 . .
C4 C5 H5 127.4 . .
N4 C6 C5 107.60(14) . .
N4 C6 H6A 126.2 . .
C5 C6 H6A 126.2 . .
N5 C7 C8 110.88(16) . .
N5 C7 H7 124.6 . .
C8 C7 H7 124.6 . .
C9 C8 C7 105.02(16) . .
C9 C8 H8A 127.5 . .
C7 C8 H8A 127.5 . .
N6 C9 C8 107.11(15) . .
N6 C9 H9 126.4 . .
C8 C9 H9 126.4 . .
N7 C10 C11 110.03(15) . .
N7 C10 H10 125.0 . .
C11 C10 H10 125.0 . .
C12 C11 C10 105.55(15) . .
C12 C11 H11 127.2 . .
C10 C11 H11 127.2 . .
N8 C12 C11 107.47(15) . .
N8 C12 H12 126.3 . .
C11 C12 H12 126.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mo1 O1 1.6881(10) .
Mo1 O5 1.9260(11) .
Mo1 O3 1.9280(10) .
Mo1 O4 1.9472(10) .
Mo1 O2 1.9611(10) .
Mo1 N3 2.1623(12) .
Mo1 N1 2.3636(12) .
Mo2 O6 1.6777(11) .
Mo2 O10 1.9275(11) .
Mo2 O9 1.9406(11) .
Mo2 O8 1.9417(12) .
Mo2 O7 1.9596(11) .
Mo2 N7 2.1623(13) .
Mo2 N5 2.3984(12) .
O2 O3 1.4807(14) .
O4 O5 1.4789(15) .
O7 O8 1.4770(16) .
O9 O10 1.4739(16) .
N1 C1 1.3327(19) .
N1 N2 1.3489(16) .
N2 C3 1.335(2) .
N2 H2 0.8800 .
N3 C4 1.3404(18) .
N3 N4 1.3511(16) .
N4 C6 1.3339(19) .
N4 H4 0.8800 .
N5 C7 1.325(2) .
N5 N6 1.3476(16) .
N6 C9 1.335(2) .
N6 H6 0.8800 .
N7 C10 1.335(2) .
N7 N8 1.3527(17) .
N8 C12 1.339(2) .
N8 H8 0.8800 .
C1 C2 1.394(2) .
C1 H1 0.9500 .
C2 C3 1.364(3) .
C2 H2A 0.9500 .
C3 H3 0.9500 .
C4 C5 1.385(2) .
C4 H4A 0.9500 .
C5 C6 1.378(2) .
C5 H5 0.9500 .
C6 H6A 0.9500 .
C7 C8 1.397(3) .
C7 H7 0.9500 .
C8 C9 1.364(3) .
C8 H8A 0.9500 .
C9 H9 0.9500 .
C10 C11 1.388(2) .
C10 H10 0.9500 .
C11 C12 1.375(3) .
C11 H11 0.9500 .
C12 H12 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O4 0.88 2.34 2.8042(17) 112.8 . yes
N2 H2 O4 0.88 2.08 2.8430(16) 144.5 2_556 yes
N4 H4 O2 0.88 1.98 2.8428(16) 165.7 2_666 yes
N4 H4 O3 0.88 2.48 3.1082(16) 129.3 2_666 yes
N6 H6 O1 0.88 2.16 3.0038(17) 159.6 . yes
N6 H6 O9 0.88 2.39 2.8333(17) 111.3 . yes
N8 H8 O7 0.88 1.96 2.7979(17) 158.8 2_655 yes
N8 H8 O8 0.88 2.33 3.0425(17) 138.6 2_655 yes
C3 H3 O10 0.95 2.59 3.407(2) 144.9 2_556 yes
C5 H5 O9 0.95 2.65 3.2485(19) 121.5 2_656 yes
C5 H5 O10 0.95 2.35 3.2206(19) 151.5 2_656 yes
C6 H6A O5 0.95 2.25 3.1512(19) 158.5 1_655 yes
C10 H10 O2 0.95 2.47 3.4129(19) 171.0 2_666 yes
C10 H10 O3 0.95 2.61 3.4619(19) 150.0 2_666 yes
C12 H12 O8 0.95 2.58 3.472(2) 156.0 1_655 yes
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
C1 N1 N2 C3 0.56(18) . . . .
Mo1 N1 N2 C3 -176.48(11) . . . .
C4 N3 N4 C6 -0.54(17) . . . .
Mo1 N3 N4 C6 -179.26(11) . . . .
C7 N5 N6 C9 0.1(2) . . . .
Mo2 N5 N6 C9 -173.66(12) . . . .
C10 N7 N8 C12 0.22(18) . . . .
Mo2 N7 N8 C12 177.42(11) . . . .
N2 N1 C1 C2 -0.4(2) . . . .
Mo1 N1 C1 C2 176.20(12) . . . .
N1 C1 C2 C3 0.1(2) . . . .
N1 N2 C3 C2 -0.5(2) . . . .
C1 C2 C3 N2 0.3(2) . . . .
N4 N3 C4 C5 0.20(18) . . . .
Mo1 N3 C4 C5 178.68(11) . . . .
N3 C4 C5 C6 0.2(2) . . . .
N3 N4 C6 C5 0.7(2) . . . .
C4 C5 C6 N4 -0.5(2) . . . .
N6 N5 C7 C8 0.1(2) . . . .
Mo2 N5 C7 C8 172.94(14) . . . .
N5 C7 C8 C9 -0.3(3) . . . .
N5 N6 C9 C8 -0.3(2) . . . .
C7 C8 C9 N6 0.3(2) . . . .
N8 N7 C10 C11 -0.1(2) . . . .
Mo2 N7 C10 C11 -176.98(12) . . . .
N7 C10 C11 C12 0.0(2) . . . .
N7 N8 C12 C11 -0.3(2) . . . .
C10 C11 C12 N8 0.2(2) . . . .
