# 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 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1873130'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2018-10-13 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        N-(butylcarbamothioyl)-4-methoxybenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 N2 O2 S'
_chemical_formula_weight         266.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.3789(3)
_cell_length_b                   23.7392(13)
_cell_length_c                   9.2761(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.122(5)
_cell_angle_gamma                90
_cell_volume                     1390.59(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1177
_cell_measurement_theta_min      4.0270
_cell_measurement_theta_max      25.2910
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_T_min  0.94195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.919
_oxdiff_exptl_absorpt_empirical_full_max 1.055
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            5746
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.226
_diffrn_reflns_theta_max         28.752
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3009
_reflns_number_gt                1932
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3009
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_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
C1 C -0.2264(3) 0.33508(10) 0.5560(2) 0.0458(6) Uani 1 1 d . . . . .
C2 C -0.1679(3) 0.39064(10) 0.5446(3) 0.0454(6) Uani 1 1 d . . . . .
C3 C 0.0002(3) 0.40472(10) 0.4742(2) 0.0422(5) Uani 1 1 d . . . . .
C4 C 0.1141(3) 0.36323(9) 0.4136(2) 0.0388(5) Uani 1 1 d . . . . .
C5 C 0.0524(3) 0.30791(10) 0.4251(3) 0.0500(6) Uani 1 1 d . . . . .
C6 C -0.1155(4) 0.29343(11) 0.4959(3) 0.0539(6) Uani 1 1 d . . . . .
C7 C -0.4602(5) 0.26971(14) 0.6465(5) 0.0732(9) Uani 1 1 d . . . . .
C8 C 0.2922(3) 0.37499(10) 0.3314(2) 0.0419(5) Uani 1 1 d . . . . .
C9 C 0.5283(3) 0.45184(10) 0.2670(2) 0.0406(5) Uani 1 1 d . . . . .
C10 C 0.7650(4) 0.43660(12) 0.0842(3) 0.0526(7) Uani 1 1 d . . . . .
C11 C 0.8586(4) 0.38630(11) 0.0176(3) 0.0480(6) Uani 1 1 d . . . . .
C12 C 1.0431(4) 0.40325(12) -0.0612(3) 0.0538(6) Uani 1 1 d . . . . .
C13 C 1.1563(5) 0.35335(14) -0.1155(4) 0.0632(8) Uani 1 1 d . . . . .
N1 N 0.3773(3) 0.42801(9) 0.3434(2) 0.0441(5) Uani 1 1 d . . . . .
N2 N 0.6034(3) 0.41909(9) 0.1714(2) 0.0483(5) Uani 1 1 d . . . . .
O1 O -0.3943(2) 0.32594(8) 0.62877(19) 0.0635(5) Uani 1 1 d . . . . .
O2 O 0.3581(2) 0.33915(7) 0.25431(18) 0.0581(5) Uani 1 1 d . . . . .
S S 0.60031(9) 0.51858(3) 0.29942(7) 0.0551(2) Uani 1 1 d . . . . .
H1N H 0.347(3) 0.4487(10) 0.404(2) 0.041(7) Uiso 1 1 d . . . . .
H2 H -0.243(3) 0.4178(11) 0.585(2) 0.063(7) Uiso 1 1 d . . . . .
H2N H 0.555(4) 0.3866(11) 0.167(3) 0.056(8) Uiso 1 1 d . . . . .
H3 H 0.032(3) 0.4431(10) 0.468(2) 0.040(6) Uiso 1 1 d . . . . .
H5 H 0.122(3) 0.2793(11) 0.380(3) 0.063(7) Uiso 1 1 d . . . . .
H6 H -0.150(3) 0.2570(10) 0.505(2) 0.051(6) Uiso 1 1 d . . . . .
H7A H -0.499(4) 0.2523(13) 0.553(3) 0.089(11) Uiso 1 1 d . . . . .
H7B H -0.584(4) 0.2737(13) 0.696(3) 0.089(9) Uiso 1 1 d . . . . .
H7C H -0.344(4) 0.2475(13) 0.699(3) 0.091(10) Uiso 1 1 d . . . . .
H10A H 0.878(4) 0.4582(13) 0.150(3) 0.088(9) Uiso 1 1 d . . . . .
H10B H 0.707(3) 0.4616(11) 0.018(3) 0.059(8) Uiso 1 1 d . . . . .
H11A H 0.906(3) 0.3594(10) 0.088(3) 0.053(7) Uiso 1 1 d . . . . .
H11B H 0.756(3) 0.3653(10) -0.053(3) 0.058(7) Uiso 1 1 d . . . . .
H12A H 0.992(3) 0.4294(11) -0.137(3) 0.056(7) Uiso 1 1 d . . . . .
H12B H 1.143(4) 0.4274(12) 0.003(3) 0.071(8) Uiso 1 1 d . . . . .
H13A H 1.220(4) 0.3301(12) -0.040(3) 0.065(8) Uiso 1 1 d . . . . .
H13B H 1.067(4) 0.3311(13) -0.181(3) 0.081(10) Uiso 1 1 d . . . . .
H13C H 1.272(5) 0.3641(13) -0.164(3) 0.097(10) Uiso 1 1 d . . . . .


_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
C1 O1 1.361(2) . ?
C1 C6 1.378(3) . ?
C1 C2 1.379(3) . ?
C2 C3 1.373(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.379(3) . ?
C4 C8 1.482(3) . ?
C5 C6 1.377(3) . ?
C7 O1 1.416(3) . ?
C8 O2 1.224(2) . ?
C8 N1 1.369(3) . ?
C9 N2 1.319(3) . ?
C9 N1 1.394(3) . ?
C9 S 1.665(2) . ?
C10 N2 1.458(3) . ?
C10 C11 1.506(3) . ?
C11 C12 1.525(3) . ?
C12 C13 1.510(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
_geom_angle_publ_flag
O1 C1 C6 124.8(2) . . ?
O1 C1 C2 115.5(2) . . ?
C6 C1 C2 119.7(2) . . ?
C3 C2 C1 120.5(2) . . ?
C2 C3 C4 120.5(2) . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 C8 117.83(19) . . ?
C3 C4 C8 123.9(2) . . ?
C6 C5 C4 121.6(2) . . ?
C1 C6 C5 119.5(2) . . ?
O2 C8 N1 121.45(19) . . ?
O2 C8 C4 121.4(2) . . ?
N1 C8 C4 117.09(18) . . ?
N2 C9 N1 116.4(2) . . ?
N2 C9 S 124.42(17) . . ?
N1 C9 S 119.14(16) . . ?
N2 C10 C11 110.7(2) . . ?
C10 C11 C12 111.4(2) . . ?
C13 C12 C11 113.0(3) . . ?
C8 N1 C9 128.77(19) . . ?
C9 N2 C10 123.9(2) . . ?
C1 O1 C7 118.4(2) . . ?

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
O1 C1 C2 C3 179.58(19) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C2 C3 C4 C8 177.69(19) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C8 C4 C5 C6 -178.1(2) . . . . ?
O1 C1 C6 C5 -179.8(2) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C5 C4 C8 O2 13.0(3) . . . . ?
C3 C4 C8 O2 -164.2(2) . . . . ?
C5 C4 C8 N1 -168.2(2) . . . . ?
C3 C4 C8 N1 14.7(3) . . . . ?
N2 C10 C11 C12 -174.2(2) . . . . ?
C10 C11 C12 C13 173.8(3) . . . . ?
O2 C8 N1 C9 6.3(3) . . . . ?
C4 C8 N1 C9 -172.52(19) . . . . ?
N2 C9 N1 C8 -1.2(3) . . . . ?
S C9 N1 C8 178.18(18) . . . . ?
N1 C9 N2 C10 -178.7(2) . . . . ?
S C9 N2 C10 2.0(3) . . . . ?
C11 C10 N2 C9 164.5(2) . . . . ?
C6 C1 O1 C7 0.8(4) . . . . ?
C2 C1 O1 C7 -179.0(3) . . . . ?

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
N1 H1N S 0.79(2) 2.84(2) 3.531(2) 148(2) 3_666
C2 H2 S 0.92(2) 3.05(2) 3.934(2) 162.5(19) 3_566
N2 H2N O2 0.83(2) 1.95(2) 2.642(3) 140(2) .

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2207838'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2022-09-16 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        N-(butylcarbamoyl)-4-methoxybenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 N2 O3'
_chemical_formula_weight         250.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.8639(2)
_cell_length_b                   15.2441(7)
_cell_length_c                   18.5621(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.637(4)
_cell_angle_gamma                90
_cell_volume                     1367.08(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1755
_cell_measurement_theta_min      4.1630
_cell_measurement_theta_max      22.9050
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_T_min  0.83834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.868
_oxdiff_exptl_absorpt_empirical_full_max 1.171
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            12946
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.468
_diffrn_reflns_theta_max         29.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3159
_reflns_number_gt                1672
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
'The butyl group of showed librational disorder. This group was refined with anisotropic displacement parameters and restraining the C-C distances to be equal to one another.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1201P)²+0.4652P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3159
_refine_ls_number_parameters     165
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2587
_refine_ls_wR_factor_gt          0.2118
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
# start Validation Reply Form
_vrf_PLAT220_shelx               
;
PROBLEM: NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        8.1 Ratio 
RESPONSE: Possible due to severe librational disorder of the terminal butyl 
group 
;
_vrf_PLAT230_shelx               
;
PROBLEM: Hirshfeld Test Diff for    C10      --C11      .       10.3 s.u.  
RESPONSE: Possible due to severe librational disorder of the terminal butyl 
group 
;
# end Validation Reply Form 
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
C1 C 0.8807(6) 0.3606(2) 0.73083(16) 0.0612(8) Uani 1 1 d . . . . .
C2 C 0.7581(8) 0.4112(3) 0.77975(18) 0.0824(11) Uani 1 1 d . . . . .
H2 H 0.8036 0.4021 0.8292 0.099 Uiso 1 1 calc R U . . .
C3 C 0.5698(7) 0.4749(3) 0.75622(17) 0.0771(10) Uani 1 1 d . . . . .
H3 H 0.4909 0.5091 0.7899 0.093 Uiso 1 1 calc R U . . .
C4 C 0.4957(6) 0.48892(19) 0.68281(14) 0.0543(7) Uani 1 1 d . . . . .
C5 C 0.6179(6) 0.4374(2) 0.63473(15) 0.0586(8) Uani 1 1 d . . . . .
H5 H 0.5692 0.4455 0.5852 0.070 Uiso 1 1 calc R U . . .
C6 C 0.8111(6) 0.3741(2) 0.65792(16) 0.0604(8) Uani 1 1 d . . . . .
H6 H 0.8935 0.3408 0.6243 0.073 Uiso 1 1 calc R U . . .
C7 C 1.1887(8) 0.2433(3) 0.7118(2) 0.0865(11) Uani 1 1 d . . . . .
H7A H 1.0470 0.2088 0.6849 0.130 Uiso 1 1 calc R U . . .
H7B H 1.3192 0.2053 0.7391 0.130 Uiso 1 1 calc R U . . .
H7C H 1.2822 0.2778 0.6788 0.130 Uiso 1 1 calc R U . . .
C8 C 0.2925(6) 0.5594(2) 0.66196(15) 0.0573(7) Uani 1 1 d . . . . .
C9 C -0.0538(6) 0.61153(19) 0.56238(15) 0.0551(7) Uani 1 1 d . . . . .
C10 C -0.3496(7) 0.7369(2) 0.57424(19) 0.0747(10) Uani 1 1 d D . . . .
H10A H -0.4252 0.7629 0.6154 0.090 Uiso 1 1 calc R U . . .
H10B H -0.4948 0.7025 0.5473 0.090 Uiso 1 1 calc R U . . .
C11 C -0.2631(13) 0.8081(4) 0.5267(4) 0.173(3) Uani 1 1 d D . . . .
H11A H -0.1452 0.8480 0.5571 0.207 Uiso 1 1 calc R U . . .
H11B H -0.1493 0.7817 0.4930 0.207 Uiso 1 1 calc R U . . .
C12 C -0.460(3) 0.8571(7) 0.4873(6) 0.299(7) Uani 1 1 d D . . . .
H12A H -0.5617 0.8907 0.5199 0.359 Uiso 1 1 calc R U . . .
H12B H -0.5902 0.8186 0.4591 0.359 Uiso 1 1 calc R U . . .
C13 C -0.333(4) 0.9189(6) 0.4369(5) 0.439(14) Uani 1 1 d D . . . .
H13A H -0.1446 0.9022 0.4339 0.658 Uiso 1 1 calc R U . . .
H13B H -0.3384 0.9777 0.4552 0.658 Uiso 1 1 calc R U . . .
H13C H -0.4357 0.9161 0.3896 0.658 Uiso 1 1 calc R U . . .
N1 N 0.1562(5) 0.55633(16) 0.59311(12) 0.0555(6) Uani 1 1 d . . . . .
H1 H 0.2063 0.5154 0.5656 0.067 Uiso 1 1 calc R U . . .
N2 N -0.1238(5) 0.67951(17) 0.60033(13) 0.0635(7) Uani 1 1 d . . . . .
H2A H -0.0320 0.6900 0.6419 0.076 Uiso 1 1 calc R U . . .
O1 O 1.0668(5) 0.29978(16) 0.75993(12) 0.0783(7) Uani 1 1 d . . . . .
O2 O 0.2498(5) 0.61778(16) 0.70440(12) 0.0794(8) Uani 1 1 d . . . . .
O3 O -0.1671(5) 0.59358(16) 0.50136(11) 0.0771(7) Uani 1 1 d . . . . .


_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
C1 O1 1.363(4) . ?
C1 C2 1.378(5) . ?
C1 C6 1.372(4) . ?
C2 C3 1.371(5) . ?
C3 C4 1.385(4) . ?
C4 C5 1.374(4) . ?
C4 C8 1.481(4) . ?
C5 C6 1.381(4) . ?
C7 O1 1.419(4) . ?
C8 O2 1.222(3) . ?
C8 N1 1.371(3) . ?
C9 O3 1.232(3) . ?
C9 N2 1.320(4) . ?
C9 N1 1.393(4) . ?
C10 N2 1.443(4) . ?
C10 C11 1.490(7) . ?
C11 C12 1.361(10) . ?
C12 C13 1.509(12) . ?

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 C1 C2 116.0(3) . . ?
O1 C1 C6 124.7(3) . . ?
C2 C1 C6 119.3(3) . . ?
C1 C2 C3 120.7(3) . . ?
C2 C3 C4 120.7(3) . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 C8 124.8(2) . . ?
C3 C4 C8 117.3(3) . . ?
C6 C5 C4 121.8(3) . . ?
C5 C6 C1 119.6(3) . . ?
O2 C8 N1 121.8(3) . . ?
O2 C8 C4 121.2(2) . . ?
N1 C8 C4 117.1(2) . . ?
O3 C9 N2 123.3(3) . . ?
O3 C9 N1 118.1(3) . . ?
N2 C9 N1 118.5(2) . . ?
N2 C10 C11 112.6(3) . . ?
C12 C11 C10 119.3(7) . . ?
C11 C12 C13 111.2(13) . . ?
C8 N1 C9 127.8(2) . . ?
C9 N2 C10 122.0(3) . . ?
C1 O1 C7 118.0(2) . . ?

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
O1 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C2 C3 C4 C8 -179.6(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C8 C4 C5 C6 178.4(3) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
O1 C1 C6 C5 179.6(3) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C5 C4 C8 O2 -159.4(3) . . . . ?
C3 C4 C8 O2 19.8(4) . . . . ?
C5 C4 C8 N1 20.4(4) . . . . ?
C3 C4 C8 N1 -160.5(3) . . . . ?
N2 C10 C11 C12 167.8(8) . . . . ?
C10 C11 C12 C13 -173.9(8) . . . . ?
O2 C8 N1 C9 -4.3(5) . . . . ?
C4 C8 N1 C9 176.0(3) . . . . ?
O3 C9 N1 C8 -173.9(3) . . . . ?
N2 C9 N1 C8 5.2(4) . . . . ?
O3 C9 N2 C10 2.7(5) . . . . ?
N1 C9 N2 C10 -176.3(3) . . . . ?
C11 C10 N2 C9 -85.9(5) . . . . ?
C2 C1 O1 C7 177.1(3) . . . . ?
C6 C1 O1 C7 -3.1(5) . . . . ?

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
C7 H7B O2 0.96 2.60 3.544(4) 167.3 2_746
N1 H1 O3 0.86 2.07 2.885(3) 157.9 3_566
N2 H2A O1 0.86 2.49 3.162(3) 135.0 2_656
N2 H2A O2 0.86 2.02 2.666(3) 131.5 .

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
