# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1967536'
loop_
_audit_author_name
_audit_author_address
'Filipe Almeida Paz'
;University of Aveiro CICECO Aveiro Institute of Materials
Portugal
;
_audit_update_record             
;
2019-11-22 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;

#=============================================================================
_audit_creation_method           'SHELXL-2018/3, manual editing plus enCIFer'
_audit_creation_date             '22 November 2019'
_shelx_SHELXL_version_number     2018/3
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 Mo N4 O3, H2 O'
_chemical_formula_sum            'C6 H8 Mo N4 O4'
_chemical_formula_weight         296.10

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'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   18.363(5)
_cell_length_b                   3.8300(9)
_cell_length_c                   14.745(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1037.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2780
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      25.14

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   0.0819
_exptl_transmission_factor_max   0.1480
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.266
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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.
;

#=============================================================================
# EXPERIMENTAL DATA
#============================================================================= 

_exptl_absorpt_special_details   
;
?
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Sealed tube'
_diffrn_radiation_monochromator  'Multi-layer X-ray mirror'
_diffrn_measurement_device_type  'Bruker D8 QUEST '
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5653
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.544
_diffrn_reflns_theta_max         25.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             966
_reflns_number_gt                664
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.981

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 2016.9-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37a   (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.37a   (Bruker, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015b)'


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²+1.0332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         966
_refine_ls_number_parameters     76
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.000000 0.1636(4) 0.51415(2) 0.0490(7) Uani 1 2 d S T P . .
O1 O 0.000000 0.721(3) 0.5352(14) 0.058(6) Uani 1 2 d S T P . .
O2 O 0.0751(6) 0.222(3) 0.4427(10) 0.053(3) Uani 1 1 d . . . . .
N1 N 0.0725(10) 0.249(4) 0.6433(13) 0.053(4) Uani 1 1 d . . . . .
C1 C 0.0383(9) 0.341(4) 0.7148(11) 0.048(4) Uani 1 1 d . . . . .
N3 N 0.0881(8) 0.429(3) 0.7781(13) 0.056(4) Uani 1 1 d . . . . .
H3 H 0.077605 0.500777 0.833232 0.067 Uiso 1 1 calc R U . . .
C2 C 0.1583(11) 0.391(4) 0.7439(15) 0.063(4) Uani 1 1 d . . . . .
H2 H 0.203509 0.433756 0.773189 0.075 Uiso 1 1 calc R U . . .
C3 C 0.1457(11) 0.275(4) 0.6573(16) 0.062(4) Uani 1 1 d . . . . .
H3A H 0.182261 0.221144 0.613869 0.074 Uiso 1 1 calc R U . . .
O1W O 0.217(5) -0.11(2) 0.467(5) 0.12(3) Uiso 0.25 1 d . . P . .
O2W O 0.220(4) 0.12(2) 0.433(5) 0.12(2) Uiso 0.25 1 d . . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Mo1 O1 1.722(13) 1_545 ?
Mo1 O2 1.750(11) . ?
Mo1 O2 1.750(11) 4 ?
Mo1 O1 2.158(12) . ?
Mo1 N1 2.346(19) 4 ?
Mo1 N1 2.346(19) . ?
N1 C1 1.28(2) . ?
N1 C3 1.36(3) . ?
C1 N3 1.35(2) . ?
C1 C1 1.40(3) 4 ?
N3 C2 1.39(2) . ?
N3 H3 0.8800 . ?
C2 C3 1.37(3) . ?
C2 H2 0.9500 . ?
C3 H3A 0.9500 . ?
O1W O2W 0.99(9) . ?
O1W O2W 1.65(10) 8_545 ?

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
O1 Mo1 O2 103.5(6) 1_545 . ?
O1 Mo1 O2 103.5(6) 1_545 4 ?
O2 Mo1 O2 104.0(10) . 4 ?
O1 Mo1 O1 161.3(12) 1_545 . ?
O2 Mo1 O1 87.8(5) . . ?
O2 Mo1 O1 87.8(5) 4 . ?
O1 Mo1 N1 89.5(7) 1_545 4 ?
O2 Mo1 N1 156.6(6) . 4 ?
O2 Mo1 N1 91.4(7) 4 4 ?
O1 Mo1 N1 75.2(6) . 4 ?
O1 Mo1 N1 89.5(7) 1_545 . ?
O2 Mo1 N1 91.4(7) . . ?
O2 Mo1 N1 156.6(6) 4 . ?
O1 Mo1 N1 75.2(6) . . ?
N1 Mo1 N1 69.1(9) 4 . ?
Mo1 O1 Mo1 161.3(12) 1_565 . ?
C1 N1 C3 109.9(17) . . ?
C1 N1 Mo1 115.4(13) . . ?
C3 N1 Mo1 133.8(14) . . ?
N1 C1 N3 107.8(17) . . ?
N1 C1 C1 119.5(12) . 4 ?
N3 C1 C1 132.7(10) . 4 ?
C1 N3 C2 110.6(18) . . ?
C1 N3 H3 124.7 . . ?
C2 N3 H3 124.7 . . ?
C3 C2 N3 102.4(18) . . ?
C3 C2 H2 128.8 . . ?
N3 C2 H2 128.8 . . ?
N1 C3 C2 109.3(19) . . ?
N1 C3 H3A 125.3 . . ?
C2 C3 H3A 125.3 . . ?
O2W O1W O2W 112(8) . 8_545 ?
O1W O2W O1W 116(9) . 8 ?

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
C3 N1 C1 N3 -0.1(18) . . . . ?
Mo1 N1 C1 N3 -171.0(9) . . . . ?
C3 N1 C1 C1 178.7(9) . . . 4 ?
Mo1 N1 C1 C1 7.9(13) . . . 4 ?
N1 C1 N3 C2 0.1(18) . . . . ?
C1 C1 N3 C2 -178.5(8) 4 . . . ?
C1 N3 C2 C3 0.0(18) . . . . ?
C1 N1 C3 C2 0(2) . . . . ?
Mo1 N1 C3 C2 168.6(12) . . . . ?
N3 C2 C3 N1 0.0(19) . . . . ?
O2W O1W O2W O1W -79(13) 8_545 . . 8 ?

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
N3 H3 O2 0.88 1.93 2.78(2) 161.6 3_565 yes
C3 H3A O1W 0.95 2.59 3.43(8) 147.7 . yes

_refine_diff_density_max         0.999
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.148



