#------------------------------------------------------------------------------
#$Date: 2022-01-18 11:07:29 +0200 (Tue, 18 Jan 2022) $
#$Revision: 272097 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/60/1566011.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_1566011
loop_
_publ_author_name
'Yang, Shuang'
'Li, Gong'
'Yang, Yujie'
'Zhu, Mengdi'
'Fu, Yuejiao'
'Xing, Na'
'Shi, Lei'
_publ_section_title
;
 Styrene selective oxidation to benzaldehyde catalyzed by acylhydrazone Mo
 complexes: Reaction parameter effects and kinetics
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              120643
_journal_paper_doi               10.1016/j.ica.2021.120643
_journal_volume                  529
_journal_year                    2022
_chemical_formula_sum            'C16 H13 Br Cl2 Mo N2 O5'
_chemical_formula_weight         560.03
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.0870(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8585(12)
_cell_length_b                   8.0415(8)
_cell_length_c                   17.6091(12)
_cell_measurement_reflns_used    3525
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.6
_cell_measurement_theta_min      2.3
_cell_volume                     1961.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11244
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    3.008
_exptl_absorpt_correction_T_max  0.5574
_exptl_absorpt_correction_T_min  0.4972
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.135
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0306P)²+3.0120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                2793
_reflns_number_total             3657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2022-529-120643.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1566011
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mo1 Mo 0.57241(2) 0.74844(5) 0.348037(17) 0.02898(11) Uani 1 1 d . . .
N1 N 0.5236(2) 0.7325(4) 0.46850(17) 0.0275(7) Uani 1 1 d . . .
N2 N 0.4314(2) 0.6652(4) 0.47713(17) 0.0300(7) Uani 1 1 d . . .
O1 O 0.69563(18) 0.7757(4) 0.40106(15) 0.0380(7) Uani 1 1 d . . .
O2 O 0.43919(18) 0.6532(4) 0.34687(14) 0.0360(7) Uani 1 1 d . . .
O3 O 0.6027(2) 0.6924(4) 0.25953(15) 0.0424(7) Uani 1 1 d . . .
O4 O 0.5398(2) 0.9503(4) 0.34141(17) 0.0521(8) Uani 1 1 d . . .
O5 O 0.6060(2) 0.4734(3) 0.37842(14) 0.0374(7) Uani 1 1 d D . .
Br1 Br -0.00926(4) 0.32746(10) 0.36444(4) 0.0876(2) Uani 1 1 d . . .
C1 C 0.6627(3) 0.8639(5) 0.5280(2) 0.0295(9) Uani 1 1 d . . .
C2 C 0.7226(3) 0.8504(5) 0.4658(2) 0.0314(9) Uani 1 1 d . . .
C3 C 0.8165(3) 0.9118(6) 0.4732(2) 0.0377(10) Uani 1 1 d . . .
C4 C 0.8507(3) 0.9883(6) 0.5389(3) 0.0465(11) Uani 1 1 d . . .
H4 H 0.9131 1.0309 0.5423 0.056 Uiso 1 1 calc R . .
C5 C 0.7904(3) 1.0008(6) 0.5996(2) 0.0415(11) Uani 1 1 d . . .
C6 C 0.6984(3) 0.9397(5) 0.5951(2) 0.0380(10) Uani 1 1 d . . .
H6 H 0.6592 0.9485 0.6367 0.046 Uiso 1 1 calc R . .
C7 C 0.5666(3) 0.7942(5) 0.5277(2) 0.0315(9) Uani 1 1 d . . .
H7 H 0.5341 0.7941 0.5730 0.038 Uiso 1 1 calc R . .
C8 C 0.3940(3) 0.6295(5) 0.4096(2) 0.0290(9) Uani 1 1 d . . .
C9 C 0.2964(3) 0.5559(5) 0.4008(2) 0.0299(9) Uani 1 1 d . . .
C10 C 0.2708(3) 0.4761(5) 0.3333(2) 0.0401(10) Uani 1 1 d . . .
H10 H 0.3151 0.4679 0.2950 0.048 Uiso 1 1 calc R . .
C11 C 0.1799(3) 0.4090(6) 0.3227(3) 0.0476(12) Uani 1 1 d . . .
H11 H 0.1624 0.3558 0.2773 0.057 Uiso 1 1 calc R . .
C12 C 0.1158(3) 0.4212(6) 0.3794(3) 0.0497(12) Uani 1 1 d . . .
C13 C 0.1396(3) 0.4978(7) 0.4465(3) 0.0580(14) Uani 1 1 d . . .
H13 H 0.0951 0.5043 0.4847 0.070 Uiso 1 1 calc R . .
C14 C 0.2306(3) 0.5656(6) 0.4570(2) 0.0461(11) Uani 1 1 d . . .
H14 H 0.2474 0.6183 0.5026 0.055 Uiso 1 1 calc R . .
C15 C 0.6260(3) 0.3415(6) 0.3253(2) 0.0491(12) Uani 1 1 d . . .
H15A H 0.6345 0.3889 0.2754 0.059 Uiso 1 1 calc R . .
H15B H 0.5714 0.2663 0.3219 0.059 Uiso 1 1 calc R . .
C16 C 0.7129(4) 0.2482(7) 0.3486(3) 0.0707(16) Uani 1 1 d . . .
H16A H 0.7665 0.3233 0.3548 0.106 Uiso 1 1 calc R . .
H16B H 0.7266 0.1672 0.3104 0.106 Uiso 1 1 calc R . .
H16C H 0.7026 0.1928 0.3959 0.106 Uiso 1 1 calc R . .
Cl1 Cl 0.89220(8) 0.8866(2) 0.39842(7) 0.0673(4) Uani 1 1 d . . .
Cl2 Cl 0.83636(9) 1.0879(2) 0.68338(7) 0.0687(4) Uani 1 1 d . . .
H5 H 0.594(4) 0.441(7) 0.4230(13) 0.080 Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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
O4 Mo1 O3 105.51(15) . .
O4 Mo1 O1 98.88(14) . .
O3 Mo1 O1 103.41(12) . .
O4 Mo1 O2 97.04(14) . .
O3 Mo1 O2 98.55(12) . .
O1 Mo1 O2 148.22(11) . .
O4 Mo1 N1 91.77(13) . .
O3 Mo1 N1 161.11(13) . .
O1 Mo1 N1 80.88(11) . .
O2 Mo1 N1 71.28(10) . .
O4 Mo1 O5 169.82(12) . .
O3 Mo1 O5 84.50(12) . .
O1 Mo1 O5 80.22(11) . .
O2 Mo1 O5 79.31(11) . .
N1 Mo1 O5 78.07(10) . .
C7 N1 N2 117.4(3) . .
C7 N1 Mo1 126.7(3) . .
N2 N1 Mo1 115.5(2) . .
C8 N2 N1 108.5(3) . .
C2 O1 Mo1 133.0(2) . .
C8 O2 Mo1 121.3(2) . .
C15 O5 Mo1 126.3(2) . .
C15 O5 H5 115(4) . .
Mo1 O5 H5 118(4) . .
C2 C1 C6 119.4(3) . .
C2 C1 C7 122.6(3) . .
C6 C1 C7 117.9(3) . .
O1 C2 C3 118.2(3) . .
O1 C2 C1 123.3(3) . .
C3 C2 C1 118.5(3) . .
C4 C3 C2 121.9(4) . .
C4 C3 Cl1 119.5(3) . .
C2 C3 Cl1 118.6(3) . .
C3 C4 C5 118.8(4) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
C6 C5 C4 121.1(4) . .
C6 C5 Cl2 120.5(3) . .
C4 C5 Cl2 118.3(3) . .
C5 C6 C1 120.3(4) . .
C5 C6 H6 119.8 . .
C1 C6 H6 119.8 . .
N1 C7 C1 123.7(3) . .
N1 C7 H7 118.2 . .
C1 C7 H7 118.2 . .
O2 C8 N2 123.4(3) . .
O2 C8 C9 115.9(3) . .
N2 C8 C9 120.8(3) . .
C14 C9 C10 119.3(4) . .
C14 C9 C8 122.1(4) . .
C10 C9 C8 118.6(4) . .
C11 C10 C9 120.1(4) . .
C11 C10 H10 119.9 . .
C9 C10 H10 119.9 . .
C12 C11 C10 119.3(4) . .
C12 C11 H11 120.4 . .
C10 C11 H11 120.4 . .
C13 C12 C11 121.7(4) . .
C13 C12 Br1 119.4(4) . .
C11 C12 Br1 119.0(4) . .
C12 C13 C14 119.1(4) . .
C12 C13 H13 120.5 . .
C14 C13 H13 120.5 . .
C9 C14 C13 120.6(4) . .
C9 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
O5 C15 C16 111.7(4) . .
O5 C15 H15A 109.3 . .
C16 C15 H15A 109.3 . .
O5 C15 H15B 109.3 . .
C16 C15 H15B 109.3 . .
H15A C15 H15B 107.9 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mo1 O4 1.688(3) .
Mo1 O3 1.690(3) .
Mo1 O1 1.929(3) .
Mo1 O2 1.998(2) .
Mo1 N1 2.253(3) .
Mo1 O5 2.319(3) .
N1 C7 1.282(5) .
N1 N2 1.401(4) .
N2 C8 1.312(5) .
O1 C2 1.330(4) .
O2 C8 1.303(4) .
O5 C15 1.447(5) .
O5 H5 0.849(10) .
Br1 C12 1.900(4) .
C1 C2 1.402(5) .
C1 C6 1.404(5) .
C1 C7 1.445(5) .
C2 C3 1.394(5) .
C3 C4 1.378(6) .
C3 Cl1 1.726(4) .
C4 C5 1.384(6) .
C4 H4 0.9300 .
C5 C6 1.366(6) .
C5 Cl2 1.733(4) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.480(5) .
C9 C14 1.372(5) .
C9 C10 1.387(5) .
C10 C11 1.377(6) .
C10 H10 0.9300 .
C11 C12 1.364(6) .
C11 H11 0.9300 .
C12 C13 1.362(6) .
C13 C14 1.380(6) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 C16 1.465(7) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
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
O5 H5 N2 0.849(10) 1.999(13) 2.842(4) 173(5) 3_666
