# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_mo_pit4_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1990802'
loop_
_audit_author_name
_audit_author_address
'Maria Clara Ramalho Freitas'
;Universidade Federal Rural do Rio de Janeiro
Brazil
;
_audit_update_record             
;
2020-06-05 deposited with the CCDC.	2020-06-11 downloaded from the CCDC.
;
_audit_creation_date             2020-06-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N2 O S, H2 O'
_chemical_formula_sum            'C12 H12 N2 O2 S'
_chemical_formula_weight         248.30
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   4.8356(8)
_cell_length_b                   19.976(4)
_cell_length_c                   12.518(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.013(5)
_cell_angle_gamma                90
_cell_volume                     1204.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1582
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      20.72
_cell_measurement_temperature    293
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  20.72
_exptl_absorpt_correction_T_min  3.27
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.544
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.068
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2339
_diffrn_reflns_av_unetI/netI     0.1089
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16061
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.613
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1114
_reflns_number_total             2119
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Apex3 (Bruker, 2012)'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0076(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.1608
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0166P)²+0.9379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1226
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C10-C11B \\sim C12-C11A
 with sigma of 0.001
 C10-S1A \\sim C12-S1B
 with sigma of 0.001
 C11A-S1A \\sim C11B-S1B
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
S1A \\sim S1B \\sim C11A \\sim C11B \\sim C12 \\sim C9 \\sim C10: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Others
 Sof(H12A)=Sof(H10A)=Sof(S1B)=Sof(C11B)=Sof(H11B)=1-FVAR(1)
 Sof(H12)=Sof(H10)=Sof(C11A)=Sof(H11A)=Sof(S1A)=FVAR(1)
5.a Free rotating group:
 O2(H2B,H2C)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C12(H12A), C10(H10), C10(H10A), C11A(H11A), C11B(H11B), N2(H2),
 C7(H7), C2(H2A), C6(H6), C3(H3), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C12 C 1.0625(8) 0.1444(2) 0.7157(3) 0.0493(11) Uani 1 1 d D U . . .
H12 H 1.006813 0.164480 0.777318 0.059 Uiso 0.743(5) 1 calc R U P A 1
H12A H 1.003074 0.165629 0.775720 0.059 Uiso 0.257(5) 1 calc R U P A 2
C9 C 0.9600(7) 0.16167(18) 0.6116(3) 0.0328(9) Uani 1 1 d . U . . .
C10 C 1.0761(8) 0.1228(2) 0.5370(3) 0.0529(12) Uani 1 1 d D U . . .
H10 H 1.033140 0.127628 0.463565 0.063 Uiso 0.743(5) 1 calc R U P A 1
H10A H 1.034917 0.125210 0.463163 0.063 Uiso 0.257(5) 1 calc R U P A 2
C11A C 1.249(4) 0.0957(9) 0.7158(11) 0.055(3) Uani 0.743(5) 1 d D U P A 1
H11A H 1.342985 0.079156 0.778151 0.066 Uiso 0.743(5) 1 calc R U P A 1
S1A S 1.3013(7) 0.06600(18) 0.5900(2) 0.0594(8) Uani 0.743(5) 1 d D U P A 1
S1B S 1.298(3) 0.0832(7) 0.7256(10) 0.060(3) Uani 0.257(5) 1 d D U P A 2
C11B C 1.257(7) 0.0812(15) 0.5876(18) 0.066(10) Uani 0.257(5) 1 d D U P A 2
H11B H 1.358626 0.051554 0.549343 0.079 Uiso 0.257(5) 1 calc R U P A 2
O1 O 0.7113(5) 0.23018(14) 0.48258(19) 0.0468(8) Uani 1 1 d . . . . .
N2 N 0.6192(5) 0.24226(14) 0.6553(2) 0.0306(7) Uani 1 1 d . . . . .
H2 H 0.654169 0.230320 0.721132 0.037 Uiso 1 1 calc R U . . .
N1 N 0.4227(5) 0.29085(15) 0.6274(2) 0.0324(8) Uani 1 1 d . . . . .
O2 O 0.6948(6) 0.22247(18) 0.88353(18) 0.0613(9) Uani 1 1 d G . . . .
H2B H 0.832298 0.228402 0.929651 0.092 Uiso 1 1 d G U . . .
H2C H 0.554294 0.233489 0.915893 0.092 Uiso 1 1 d G U . . .
C8 C 0.7541(7) 0.21415(18) 0.5778(3) 0.0321(9) Uani 1 1 d . . . . .
C1 C 0.0975(7) 0.36860(18) 0.6888(3) 0.0319(9) Uani 1 1 d . . . . .
C7 C 0.3061(7) 0.31618(18) 0.7056(3) 0.0345(9) Uani 1 1 d . . . . .
H7 H 0.355292 0.300827 0.774777 0.041 Uiso 1 1 calc R U . . .
C2 C -0.0248(7) 0.39395(19) 0.7757(3) 0.0406(10) Uani 1 1 d . . . . .
H2A H 0.025955 0.376991 0.843823 0.049 Uiso 1 1 calc R U . . .
C6 C 0.0147(8) 0.3935(2) 0.5877(3) 0.0451(11) Uani 1 1 d . . . . .
H6 H 0.093214 0.376787 0.527888 0.054 Uiso 1 1 calc R U . . .
C3 C -0.2225(8) 0.4444(2) 0.7632(3) 0.0471(11) Uani 1 1 d . . . . .
H3 H -0.300917 0.461812 0.822461 0.057 Uiso 1 1 calc R U . . .
C5 C -0.1846(9) 0.4432(2) 0.5757(4) 0.0572(12) Uani 1 1 d . . . . .
H5 H -0.240230 0.459752 0.507824 0.069 Uiso 1 1 calc R U . . .
C4 C -0.3001(8) 0.4680(2) 0.6630(4) 0.0553(12) Uani 1 1 d . . . . .
H4 H -0.433737 0.501440 0.653982 0.066 Uiso 1 1 calc R U . . .


_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
C12 H12 0.9300 . ?
C12 H12A 0.9300 . ?
C12 C9 1.397(5) . ?
C12 C11A 1.325(11) . ?
C12 S1B 1.669(5) . ?
C9 C10 1.371(5) . ?
C9 C8 1.482(5) . ?
C10 H10 0.9300 . ?
C10 H10A 0.9300 . ?
C10 S1A 1.669(5) . ?
C10 C11B 1.325(11) . ?
C11A H11A 0.9300 . ?
C11A S1A 1.723(11) . ?
S1B C11B 1.723(11) . ?
C11B H11B 0.9300 . ?
O1 C8 1.234(4) . ?
N2 H2 0.8600 . ?
N2 N1 1.382(3) . ?
N2 C8 1.340(4) . ?
N1 C7 1.276(4) . ?
O2 H2B 0.8500 . ?
O2 H2C 0.8498 . ?
C1 C7 1.456(5) . ?
C1 C2 1.379(5) . ?
C1 C6 1.387(5) . ?
C7 H7 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C3 1.388(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.382(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.362(5) . ?
C4 H4 0.9300 . ?

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
C9 C12 H12 124.2 . . ?
C9 C12 H12A 122.1 . . ?
C9 C12 S1B 115.8(5) . . ?
C11A C12 H12 124.2 . . ?
C11A C12 C9 111.6(7) . . ?
S1B C12 H12A 122.1 . . ?
C12 C9 C8 128.0(3) . . ?
C10 C9 C12 111.2(4) . . ?
C10 C9 C8 120.7(4) . . ?
C9 C10 H10 123.0 . . ?
C9 C10 H10A 125.6 . . ?
C9 C10 S1A 114.0(3) . . ?
S1A C10 H10 123.0 . . ?
C11B C10 C9 108.8(11) . . ?
C11B C10 H10A 125.6 . . ?
C12 C11A H11A 123.0 . . ?
C12 C11A S1A 114.0(9) . . ?
S1A C11A H11A 123.0 . . ?
C10 S1A C11A 89.2(5) . . ?
C12 S1B C11B 85.6(9) . . ?
C10 C11B S1B 118.6(15) . . ?
C10 C11B H11B 120.7 . . ?
S1B C11B H11B 120.7 . . ?
N1 N2 H2 120.7 . . ?
C8 N2 H2 120.7 . . ?
C8 N2 N1 118.6(3) . . ?
C7 N1 N2 115.2(3) . . ?
H2B O2 H2C 104.5 . . ?
O1 C8 C9 120.7(3) . . ?
O1 C8 N2 122.7(3) . . ?
N2 C8 C9 116.6(3) . . ?
C2 C1 C7 119.3(3) . . ?
C2 C1 C6 118.6(3) . . ?
C6 C1 C7 122.0(3) . . ?
N1 C7 C1 121.5(3) . . ?
N1 C7 H7 119.3 . . ?
C1 C7 H7 119.3 . . ?
C1 C2 H2A 119.5 . . ?
C1 C2 C3 121.0(4) . . ?
C3 C2 H2A 119.5 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 H6 120.0 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.4 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 119.8 . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?

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
C12 C9 C10 S1A 0.6(5) . . . . ?
C12 C9 C10 C11B -1(2) . . . . ?
C12 C9 C8 O1 169.9(4) . . . . ?
C12 C9 C8 N2 -10.4(5) . . . . ?
C12 C11A S1A C10 2.2(14) . . . . ?
C12 S1B C11B C10 -1(3) . . . . ?
C9 C12 C11A S1A -2.3(17) . . . . ?
C9 C12 S1B C11B 0.0(18) . . . . ?
C9 C10 S1A C11A -1.5(8) . . . . ?
C9 C10 C11B S1B 1(3) . . . . ?
C10 C9 C8 O1 -10.0(5) . . . . ?
C10 C9 C8 N2 169.7(3) . . . . ?
C11A C12 C9 C10 1.1(11) . . . . ?
C11A C12 C9 C8 -178.8(11) . . . . ?
S1B C12 C9 C10 0.8(9) . . . . ?
S1B C12 C9 C8 -179.1(8) . . . . ?
O1 C8 N2 H2 -179.5 . . . . ?
N2 N1 C7 C1 179.1(3) . . . . ?
N1 N2 C8 C9 -179.2(3) . . . . ?
N1 N2 C8 O1 0.5(5) . . . . ?
C8 C9 C10 S1A -179.5(3) . . . . ?
C8 C9 C10 C11B 178.6(19) . . . . ?
C8 N2 N1 C7 -178.9(3) . . . . ?
C1 C2 C3 C4 1.4(6) . . . . ?
C1 C6 C5 C4 0.1(6) . . . . ?
C7 C1 C2 C3 179.4(3) . . . . ?
C7 C1 C6 C5 179.8(4) . . . . ?
C2 C1 C7 N1 179.3(3) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C6 C1 C7 N1 0.2(5) . . . . ?
C6 C1 C2 C3 -1.4(5) . . . . ?
C6 C5 C4 C3 -0.1(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_pif4_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1990803'
loop_
_audit_author_name
_audit_author_address
'Maria Clara Ramalho Freitas'
;Universidade Federal Rural do Rio de Janeiro
Brazil
;
_audit_update_record             
;
2020-06-05 deposited with the CCDC.	2020-06-11 downloaded from the CCDC.
;
_audit_creation_date             2020-06-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
claraqui@gmail.com
_audit_contact_letter            
;
Please consider this CIF for submission to the Cambridge Crystallographic
Data Centre. I certify that all authors have seen and approved of this
submission, that all have made significant scientific contributions to the
work reported, and that all share responsibility and accountability for
the results.

This CIF  is submitted as a personal communication

This CIF is submitted as part of a journal submission
<Insert Journal details here>

<Insert NAME here>
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N2 O2'
_chemical_formula_sum            'C12 H10 N2 O2'
_chemical_formula_weight         214.22
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   11.3370(10)
_cell_length_b                   4.9540(4)
_cell_length_c                   19.4646(16)
_cell_angle_alpha                90
_cell_angle_beta                 104.141(5)
_cell_angle_gamma                90
_cell_volume                     1060.07(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3084
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      24.34
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.393
_exptl_crystal_size_min          0.174
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1634
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23399
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.355
_diffrn_reflns_theta_min         2.158
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'Photon 100 detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture diffractometer'
_diffrn_measurement_device_type  bruker
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Quazar multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1223
_reflns_number_total             1928
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Apex3 (Bruker, 2012)'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.2843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1337
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C6(H6), C10(H10), C5(H5), C2(H2), C11(H11), C12(H12), C4(H4),
 C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O2 O 0.91129(15) 1.0625(4) 0.41125(9) 0.0578(6) Uani 1 1 d . . . . .
N1 N 0.87668(17) 0.7508(4) 0.48658(10) 0.0477(6) Uani 1 1 d . . . . .
H1 H 0.945742 0.787540 0.514925 0.057 Uiso 1 1 calc R U . . .
N2 N 0.80350(17) 0.5617(4) 0.50668(10) 0.0439(5) Uani 1 1 d . . . . .
O1 O 0.56768(17) 0.6104(4) 0.30566(10) 0.0727(7) Uani 1 1 d . . . . .
C1 C 0.7792(2) 0.2479(5) 0.59568(12) 0.0404(6) Uani 1 1 d . . . . .
C9 C 0.7329(2) 0.8088(5) 0.37098(12) 0.0392(6) Uani 1 1 d . . . . .
C7 C 0.8481(2) 0.4467(5) 0.56606(12) 0.0430(6) Uani 1 1 d . . . . .
H7 H 0.926507 0.490742 0.591135 0.052 Uiso 1 1 calc R U . . .
C8 C 0.8445(2) 0.8809(5) 0.42417(12) 0.0416(6) Uani 1 1 d . . . . .
C6 C 0.8368(2) 0.1020(5) 0.65499(13) 0.0476(7) Uani 1 1 d . . . . .
H6 H 0.919031 0.130562 0.675315 0.057 Uiso 1 1 calc R U . . .
C10 C 0.6905(2) 0.9544(6) 0.30649(13) 0.0536(7) Uani 1 1 d . . . . .
H10 H 0.725399 1.108833 0.292773 0.064 Uiso 1 1 calc R U . . .
C5 C 0.7735(3) -0.0856(5) 0.68428(14) 0.0542(7) Uani 1 1 d . . . . .
H5 H 0.813386 -0.182687 0.724074 0.065 Uiso 1 1 calc R U . . .
C2 C 0.6568(2) 0.2047(6) 0.56715(14) 0.0581(8) Uani 1 1 d . . . . .
H2 H 0.616261 0.303478 0.527808 0.070 Uiso 1 1 calc R U . . .
C11 C 0.5922(2) 0.8291(6) 0.26982(15) 0.0610(8) Uani 1 1 d . . . . .
H11 H 0.546344 0.883481 0.225612 0.073 Uiso 1 1 calc R U . . .
C12 C 0.6547(2) 0.6041(6) 0.36721(14) 0.0626(8) Uani 1 1 d . . . . .
H12 H 0.659537 0.474225 0.402298 0.075 Uiso 1 1 calc R U . . .
C4 C 0.6527(3) -0.1299(5) 0.65533(15) 0.0596(8) Uani 1 1 d . . . . .
H4 H 0.610245 -0.257159 0.674982 0.072 Uiso 1 1 calc R U . . .
C3 C 0.5941(3) 0.0171(6) 0.59637(16) 0.0672(9) Uani 1 1 d . . . . .
H3 H 0.511788 -0.011346 0.576377 0.081 Uiso 1 1 calc R U . . .


_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
O2 C8 1.241(3) . ?
N1 H1 0.8600 . ?
N1 N2 1.370(2) . ?
N1 C8 1.345(3) . ?
N2 C7 1.277(3) . ?
O1 C11 1.354(3) . ?
O1 C12 1.354(3) . ?
C1 C7 1.460(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.380(3) . ?
C9 C8 1.470(3) . ?
C9 C10 1.426(3) . ?
C9 C12 1.337(3) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.380(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.322(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.365(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.384(4) . ?
C3 H3 0.9300 . ?

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
N2 N1 H1 118.8 . . ?
C8 N1 H1 118.8 . . ?
C8 N1 N2 122.4(2) . . ?
C7 N2 N1 115.5(2) . . ?
C11 O1 C12 106.1(2) . . ?
C6 C1 C7 119.5(2) . . ?
C2 C1 C7 121.9(2) . . ?
C2 C1 C6 118.6(2) . . ?
C10 C9 C8 123.0(2) . . ?
C12 C9 C8 131.9(2) . . ?
C12 C9 C10 105.0(2) . . ?
N2 C7 C1 121.8(2) . . ?
N2 C7 H7 119.1 . . ?
C1 C7 H7 119.1 . . ?
O2 C8 N1 119.1(2) . . ?
O2 C8 C9 119.8(2) . . ?
N1 C8 C9 121.1(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C9 C10 H10 126.4 . . ?
C11 C10 C9 107.2(2) . . ?
C11 C10 H10 126.4 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
O1 C11 H11 124.8 . . ?
C10 C11 O1 110.5(2) . . ?
C10 C11 H11 124.8 . . ?
O1 C12 H12 124.4 . . ?
C9 C12 O1 111.2(2) . . ?
C9 C12 H12 124.4 . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?

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
N1 H1 O2 0.86 2.03 2.873(3) 167.9 3_776 yes
C12 H12 N2 0.93 2.32 2.832(3) 114.7 . 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
_geom_torsion_publ_flag
O2 C8 N1 H1 -4.8 . . . . ?
N1 N2 C7 C1 177.81(19) . . . . ?
N2 N1 C8 O2 175.2(2) . . . . ?
N2 N1 C8 C9 -5.6(3) . . . . ?
C1 C6 C5 C4 -0.2(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C9 C10 C11 O1 -0.4(3) . . . . ?
C7 C1 C6 C5 179.5(2) . . . . ?
C7 C1 C2 C3 -179.7(2) . . . . ?
C8 N1 N2 C7 177.2(2) . . . . ?
C8 C9 C10 C11 177.0(2) . . . . ?
C8 C9 C12 O1 -176.3(2) . . . . ?
C6 C1 C7 N2 171.1(2) . . . . ?
C6 C1 C2 C3 -1.2(4) . . . . ?
C6 C5 C4 C3 -0.4(4) . . . . ?
C10 C9 C8 O2 -5.8(4) . . . . ?
C10 C9 C8 N1 175.1(2) . . . . ?
C10 C9 C12 O1 0.2(3) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?
C2 C1 C7 N2 -10.4(4) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C11 O1 C12 C9 -0.4(3) . . . . ?
C12 O1 C11 C10 0.5(3) . . . . ?
C12 C9 C8 O2 170.2(3) . . . . ?
C12 C9 C8 N1 -8.9(4) . . . . ?
C12 C9 C10 C11 0.1(3) . . . . ?


_olex2_submission_original_sample_id pif4
_olex2_submission_special_instructions 'No special instructions were received'
