# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_x1inh
_database_code_depnum_ccdc_archive 'CCDC 1968801'
loop_
_audit_author_name
_audit_author_address
'Renata Diniz'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2019-11-28 deposited with the CCDC.	2020-05-05 downloaded from the CCDC.
;

_audit_creation_date             2019-11-25T10:49:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C11 H12 Cl N5 O'
_chemical_formula_weight         265.71
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.3066(4)
_cell_length_b                   17.7428(11)
_cell_length_c                   8.1657(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.475(7)
_cell_angle_gamma                90
_cell_volume                     609.22(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1775
_cell_measurement_theta_min      2.568
_cell_measurement_theta_max      30.636

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_color             'ligh yellow'
_exptl_crystal_size_max          0.538
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.117
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             276
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0755
0 -1 0 0.1518
0 1 0 0.1043
1 0 1 0.1796
-2 2 1 0.2599
-1 -2 1 0.2503
0 0 -1 0.0411


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.8942
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4186
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0024715
_diffrn_orient_matrix_ub_12      0.0062042
_diffrn_orient_matrix_ub_13      -0.08546
_diffrn_orient_matrix_ub_21      -0.1527282
_diffrn_orient_matrix_ub_22      -0.0165955
_diffrn_orient_matrix_ub_23      -0.0242536
_diffrn_orient_matrix_ub_31      -0.0711546
_diffrn_orient_matrix_ub_32      0.0358338
_diffrn_orient_matrix_ub_33      0.0036073
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_number            7384
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.296
_diffrn_reflns_theta_max         32.828
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.93
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.93
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.869
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.806
_reflns_Friedel_coverage         0.82
_reflns_number_total             3951
_reflns_number_gt                2841
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3951
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 965 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(5)
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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
Cl Cl 0.5478(2) 1.01665(5) -0.05284(9) 0.0433(2) Uani 1 1 d . . . . .
N1 N -0.0954(5) 1.02044(17) 0.5260(3) 0.0296(5) Uani 1 1 d . . . . .
N2 N -0.0775(6) 1.11592(13) 0.3628(3) 0.0326(6) Uani 1 1 d . . . . .
H2N H -0.024637 1.149678 0.271774 0.039 Uiso 1 1 d R U . . .
N3 N 0.2400(7) 0.93296(14) 0.3124(3) 0.0328(6) Uani 1 1 d . . . . .
N4 N 0.3883(6) 0.89817(13) 0.2001(3) 0.0328(6) Uani 1 1 d . . . . .
H4N H 0.450357 0.927259 0.11184 0.039 Uiso 1 1 d R U . . .
N5 N 0.8713(8) 0.70652(16) -0.1338(4) 0.0447(7) Uani 1 1 d . . . . .
O1 O 0.4777(7) 0.79385(13) 0.3647(3) 0.0484(7) Uani 1 1 d . . . . .
C1 C -0.2368(8) 1.08038(19) 0.5874(4) 0.0384(7) Uani 1 1 d . . . . .
H1 H -0.325076 1.080025 0.681752 0.046 Uiso 1 1 calc R U . . .
C2 C -0.2245(8) 1.13951(19) 0.4868(4) 0.0388(8) Uani 1 1 d . . . . .
H2 H -0.30164 1.187688 0.498936 0.047 Uiso 1 1 calc R U . . .
C3 C -0.0008(7) 1.04312(15) 0.3882(3) 0.0275(6) Uani 1 1 d . . . . .
C4 C 0.1591(7) 1.00108(15) 0.2785(4) 0.0303(6) Uani 1 1 d . . . . .
H4 H 0.225375 1.025561 0.193327 0.036 Uiso 1 1 d R U . . .
C5 C 0.4927(8) 0.82617(16) 0.2351(4) 0.0327(6) Uani 1 1 d . . . . .
C6 C 0.6268(8) 0.78831(16) 0.1008(4) 0.0321(7) Uani 1 1 d . . . . .
C7 C 0.6187(11) 0.81698(19) -0.0573(4) 0.0503(10) Uani 1 1 d . . . . .
H7 H 0.532061 0.864295 -0.087344 0.06 Uiso 1 1 calc R U . . .
C8 C 0.7410(11) 0.77445(19) -0.1699(5) 0.0545(11) Uani 1 1 d . . . . .
H8 H 0.732293 0.794063 -0.276455 0.065 Uiso 1 1 calc R U . . .
C9 C 0.8776(9) 0.67931(19) 0.0167(5) 0.0443(8) Uani 1 1 d . . . . .
H9 H 0.967595 0.632082 0.044066 0.053 Uiso 1 1 calc R U . . .
C10 C 0.7563(9) 0.71787(18) 0.1360(4) 0.0400(8) Uani 1 1 d . . . . .
H10 H 0.762303 0.696105 0.240221 0.048 Uiso 1 1 calc R U . . .
C11 C -0.0627(9) 0.94536(18) 0.6044(4) 0.0401(8) Uani 1 1 d . . . . .
H11A H -0.153041 0.945983 0.702083 0.06 Uiso 1 1 calc R U . . .
H11B H -0.172227 0.908853 0.525969 0.06 Uiso 1 1 calc R U . . .
H11C H 0.158397 0.932258 0.636332 0.06 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
N1 C3 1.338(3) . ?
N1 C1 1.373(4) . ?
N1 C11 1.472(4) . ?
N2 C3 1.338(3) . ?
N2 C2 1.371(4) . ?
N2 H2N 1.0177 . ?
N3 C4 1.272(4) . ?
N3 N4 1.372(3) . ?
N4 C5 1.364(4) . ?
N4 H4N 0.97 . ?
N5 C9 1.315(5) . ?
N5 C8 1.335(4) . ?
O1 C5 1.217(4) . ?
C1 C2 1.340(5) . ?
C1 H1 0.93 . ?
C2 H2 0.93 . ?
C3 C4 1.449(4) . ?
C4 H4 0.9163 . ?
C5 C6 1.504(4) . ?
C6 C10 1.373(4) . ?
C6 C7 1.380(4) . ?
C7 C8 1.379(5) . ?
C7 H7 0.93 . ?
C8 H8 0.93 . ?
C9 C10 1.382(5) . ?
C9 H9 0.93 . ?
C10 H10 0.93 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?

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
C3 N1 C1 108.3(3) . . ?
C3 N1 C11 128.3(3) . . ?
C1 N1 C11 123.4(2) . . ?
C3 N2 C2 108.5(3) . . ?
C3 N2 H2N 126.5 . . ?
C2 N2 H2N 124.9 . . ?
C4 N3 N4 115.3(2) . . ?
C5 N4 N3 117.5(2) . . ?
C5 N4 H4N 121.5 . . ?
N3 N4 H4N 120 . . ?
C9 N5 C8 117.4(3) . . ?
C2 C1 N1 107.6(3) . . ?
C2 C1 H1 126.2 . . ?
N1 C1 H1 126.2 . . ?
C1 C2 N2 107.4(3) . . ?
C1 C2 H2 126.3 . . ?
N2 C2 H2 126.3 . . ?
N2 C3 N1 108.1(3) . . ?
N2 C3 C4 122.4(3) . . ?
N1 C3 C4 129.5(3) . . ?
N3 C4 C3 120.0(3) . . ?
N3 C4 H4 120 . . ?
C3 C4 H4 119.5 . . ?
O1 C5 N4 123.1(3) . . ?
O1 C5 C6 121.6(3) . . ?
N4 C5 C6 115.3(2) . . ?
C10 C6 C7 117.3(3) . . ?
C10 C6 C5 117.1(3) . . ?
C7 C6 C5 125.5(3) . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
N5 C8 C7 123.3(3) . . ?
N5 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
N5 C9 C10 122.8(3) . . ?
N5 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C6 C10 C9 120.1(3) . . ?
C6 C10 H10 120 . . ?
C9 C10 H10 120 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C4 N3 N4 C5 177.0(3) . . . . ?
C3 N1 C1 C2 -0.5(4) . . . . ?
C11 N1 C1 C2 179.7(3) . . . . ?
N1 C1 C2 N2 0.4(4) . . . . ?
C3 N2 C2 C1 -0.1(4) . . . . ?
C2 N2 C3 N1 -0.2(3) . . . . ?
C2 N2 C3 C4 -179.9(3) . . . . ?
C1 N1 C3 N2 0.5(3) . . . . ?
C11 N1 C3 N2 -179.8(3) . . . . ?
C1 N1 C3 C4 -179.9(3) . . . . ?
C11 N1 C3 C4 -0.2(5) . . . . ?
N4 N3 C4 C3 179.7(3) . . . . ?
N2 C3 C4 N3 176.8(3) . . . . ?
N1 C3 C4 N3 -2.8(5) . . . . ?
N3 N4 C5 O1 -4.7(5) . . . . ?
N3 N4 C5 C6 174.7(3) . . . . ?
O1 C5 C6 C10 -5.3(5) . . . . ?
N4 C5 C6 C10 175.3(3) . . . . ?
O1 C5 C6 C7 171.8(4) . . . . ?
N4 C5 C6 C7 -7.6(5) . . . . ?
C10 C6 C7 C8 -0.4(6) . . . . ?
C5 C6 C7 C8 -177.6(4) . . . . ?
C9 N5 C8 C7 0.9(6) . . . . ?
C6 C7 C8 N5 -0.7(7) . . . . ?
C8 N5 C9 C10 0.0(6) . . . . ?
C7 C6 C10 C9 1.3(5) . . . . ?
C5 C6 C10 C9 178.7(3) . . . . ?
N5 C9 C10 C6 -1.1(6) . . . . ?

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N2 H2N N5 1.0200 1.7400 2.754(4) 171.00 2_655 yes
N4 H4N Cl 0.9700 2.1800 3.126(3) 165.00 . yes
C1 H1 Cl 0.9300 2.6000 3.456(3) 153.00 1_456 yes
C2 H2 O1 0.9300 2.3900 3.276(4) 158.00 2_556 yes
C4 H4 Cl 0.9200 2.6800 3.487(3) 147.00 . yes
C7 H7 Cl 0.9300 2.7200 3.557(4) 151.00 . yes
C10 H10 O1 0.9300 2.4700 2.777(4) 100.00 . yes



