# 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_s2079
_audit_block_doi                 10.5517/ccdc.csd.cc217l85
_database_code_depnum_ccdc_archive 'CCDC 1884126'
loop_
_audit_author_name
_audit_author_address
'Ulrich Floerke'
;University of Paderborn
Germany
;
_audit_update_record             
;
2018-12-08 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 Br N3 O2'
_chemical_formula_sum            'C18 H16 Br N3 O2'
_chemical_formula_weight         386.25

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'
Br Br -0.2901 2.4595 '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                   14.1326(15)
_cell_length_b                   6.1144(6)
_cell_length_c                   20.190(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.055(2)
_cell_angle_gamma                90
_cell_volume                     1676.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4327
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.78

_exptl_crystal_description       prism
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    2.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min  0.4099
_exptl_absorpt_correction_T_max  0.6651

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            15171
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.499
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3987
_reflns_number_gt                3323
_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       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'

_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)+(0.0515P)²+0.2466P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3987
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.13667(2) 0.44958(4) 0.59498(2) 0.04162(10) Uani 1 1 d . . . . .
O1 O 0.36843(11) 0.5561(2) 0.65868(7) 0.0328(3) Uani 1 1 d . . . . .
O2 O 0.62104(9) 0.6037(2) 0.57532(7) 0.0239(3) Uani 1 1 d . . . . .
N1 N 0.41978(12) 0.4337(3) 0.56845(9) 0.0252(3) Uani 1 1 d . . . . .
H1 H 0.4121(18) 0.428(4) 0.5310(14) 0.036(7) Uiso 1 1 d . . . . .
N2 N 0.67354(11) 0.3262(3) 0.65635(7) 0.0234(3) Uani 1 1 d . . . . .
N3 N 0.62638(12) 0.1781(3) 0.69014(8) 0.0248(3) Uani 1 1 d . . . . .
C1 C 0.35910(14) 0.5480(3) 0.59646(9) 0.0249(4) Uani 1 1 d . . . . .
C2 C 0.28107(13) 0.6795(3) 0.54666(9) 0.0239(4) Uani 1 1 d . . . . .
C3 C 0.18163(14) 0.6654(3) 0.54324(10) 0.0286(4) Uani 1 1 d . . . . .
C4 C 0.11270(15) 0.8037(4) 0.50144(11) 0.0348(5) Uani 1 1 d . . . . .
H4A H 0.0448 0.7889 0.4988 0.042 Uiso 1 1 calc R U . . .
C5 C 0.14377(17) 0.9638(4) 0.46354(12) 0.0364(5) Uani 1 1 d . . . . .
H5A H 0.0970 1.0606 0.4353 0.044 Uiso 1 1 calc R U . . .
C6 C 0.24269(16) 0.9838(3) 0.46648(11) 0.0312(4) Uani 1 1 d . . . . .
H6A H 0.2639 1.0943 0.4407 0.037 Uiso 1 1 calc R U . . .
C7 C 0.30999(14) 0.8414(3) 0.50728(9) 0.0265(4) Uani 1 1 d . . . . .
H7A H 0.3775 0.8537 0.5086 0.032 Uiso 1 1 calc R U . . .
C8 C 0.51053(13) 0.3496(3) 0.60877(9) 0.0237(4) Uani 1 1 d . . . . .
C9 C 0.60263(14) 0.4451(3) 0.60804(9) 0.0223(4) Uani 1 1 d . . . . .
C10 C 0.67693(18) -0.0332(3) 0.70820(10) 0.0320(5) Uani 1 1 d . . . . .
H10A H 0.6456 -0.1158 0.7380 0.048 Uiso 1 1 calc R U . . .
H10B H 0.7463 -0.0076 0.7326 0.048 Uiso 1 1 calc R U . . .
H10C H 0.6726 -0.1169 0.6661 0.048 Uiso 1 1 calc R U . . .
C11 C 0.52806(14) 0.1894(3) 0.65792(9) 0.0264(4) Uani 1 1 d . . . . .
C12 C 0.45733(18) 0.0419(4) 0.67835(12) 0.0388(5) Uani 1 1 d . . . . .
H12A H 0.4695 -0.1095 0.6671 0.058 Uiso 1 1 calc R U . . .
H12B H 0.3899 0.0834 0.6534 0.058 Uiso 1 1 calc R U . . .
H12C H 0.4659 0.0547 0.7281 0.058 Uiso 1 1 calc R U . . .
C13 C 0.76658(14) 0.4116(3) 0.69343(10) 0.0239(4) Uani 1 1 d . . . . .
C14 C 0.79356(15) 0.4138(3) 0.76554(10) 0.0281(4) Uani 1 1 d . . . . .
H14A H 0.7505 0.3573 0.7901 0.034 Uiso 1 1 calc R U . . .
C15 C 0.88472(17) 0.5003(3) 0.80047(12) 0.0356(5) Uani 1 1 d . . . . .
H15A H 0.9047 0.5003 0.8494 0.043 Uiso 1 1 calc R U . . .
C16 C 0.94657(17) 0.5863(3) 0.76485(14) 0.0413(6) Uani 1 1 d . . . . .
H16A H 1.0083 0.6469 0.7892 0.050 Uiso 1 1 calc R U . . .
C17 C 0.91837(16) 0.5840(3) 0.69350(13) 0.0374(5) Uani 1 1 d . . . . .
H17A H 0.9608 0.6448 0.6692 0.045 Uiso 1 1 calc R U . . .
C18 C 0.82873(15) 0.4940(3) 0.65695(11) 0.0290(4) Uani 1 1 d . . . . .
H18A H 0.8105 0.4889 0.6080 0.035 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
Br1 C3 1.898(2) . ?
O1 C1 1.227(2) . ?
O2 C9 1.241(2) . ?
N1 C1 1.346(3) . ?
N1 C8 1.412(2) . ?
N1 H1 0.74(3) . ?
N2 C9 1.394(2) . ?
N2 N3 1.407(2) . ?
N2 C13 1.420(2) . ?
N3 C11 1.363(2) . ?
N3 C10 1.473(2) . ?
C1 C2 1.504(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.400(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.387(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.381(3) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 C11 1.367(3) . ?
C8 C9 1.431(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.487(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.388(3) . ?
C13 C14 1.399(3) . ?
C14 C15 1.391(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.380(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?

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
C1 N1 C8 121.97(17) . . ?
C1 N1 H1 122(2) . . ?
C8 N1 H1 115(2) . . ?
C9 N2 N3 109.24(14) . . ?
C9 N2 C13 123.95(15) . . ?
N3 N2 C13 118.33(14) . . ?
C11 N3 N2 107.03(14) . . ?
C11 N3 C10 121.55(16) . . ?
N2 N3 C10 114.98(16) . . ?
O1 C1 N1 123.39(19) . . ?
O1 C1 C2 120.94(18) . . ?
N1 C1 C2 115.56(16) . . ?
C3 C2 C7 117.75(18) . . ?
C3 C2 C1 122.97(17) . . ?
C7 C2 C1 118.87(16) . . ?
C4 C3 C2 121.52(18) . . ?
C4 C3 Br1 118.24(15) . . ?
C2 C3 Br1 120.22(15) . . ?
C3 C4 C5 119.35(19) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
C6 C7 C2 121.57(18) . . ?
C6 C7 H7A 119.2 . . ?
C2 C7 H7A 119.2 . . ?
C11 C8 N1 129.25(18) . . ?
C11 C8 C9 108.50(16) . . ?
N1 C8 C9 121.94(16) . . ?
O2 C9 N2 124.34(17) . . ?
O2 C9 C8 130.55(17) . . ?
N2 C9 C8 105.06(15) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C8 109.80(17) . . ?
N3 C11 C12 120.77(17) . . ?
C8 C11 C12 129.43(19) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 121.23(18) . . ?
C18 C13 N2 118.90(17) . . ?
C14 C13 N2 119.87(17) . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 H14A 120.7 . . ?
C13 C14 H14A 120.7 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C16 C17 C18 120.9(2) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
C13 C18 C17 118.6(2) . . ?
C13 C18 H18A 120.7 . . ?
C17 C18 H18A 120.7 . . ?

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
C9 N2 N3 C11 6.28(18) . . . . ?
C13 N2 N3 C11 155.62(16) . . . . ?
C9 N2 N3 C10 144.56(16) . . . . ?
C13 N2 N3 C10 -66.1(2) . . . . ?
C8 N1 C1 O1 -13.0(3) . . . . ?
C8 N1 C1 C2 163.30(16) . . . . ?
O1 C1 C2 C3 -55.7(3) . . . . ?
N1 C1 C2 C3 127.9(2) . . . . ?
O1 C1 C2 C7 116.8(2) . . . . ?
N1 C1 C2 C7 -59.6(2) . . . . ?
C7 C2 C3 C4 1.2(3) . . . . ?
C1 C2 C3 C4 173.77(18) . . . . ?
C7 C2 C3 Br1 179.84(13) . . . . ?
C1 C2 C3 Br1 -7.6(3) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
Br1 C3 C4 C5 179.51(16) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C2 -1.1(3) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C1 C2 C7 C6 -172.64(18) . . . . ?
C1 N1 C8 C11 66.7(3) . . . . ?
C1 N1 C8 C9 -106.1(2) . . . . ?
N3 N2 C9 O2 172.06(17) . . . . ?
C13 N2 C9 O2 24.8(3) . . . . ?
N3 N2 C9 C8 -5.48(18) . . . . ?
C13 N2 C9 C8 -152.71(17) . . . . ?
C11 C8 C9 O2 -174.60(19) . . . . ?
N1 C8 C9 O2 -0.5(3) . . . . ?
C11 C8 C9 N2 2.7(2) . . . . ?
N1 C8 C9 N2 176.87(16) . . . . ?
N2 N3 C11 C8 -4.5(2) . . . . ?
C10 N3 C11 C8 -139.44(17) . . . . ?
N2 N3 C11 C12 176.10(17) . . . . ?
C10 N3 C11 C12 41.2(3) . . . . ?
N1 C8 C11 N3 -172.46(18) . . . . ?
C9 C8 C11 N3 1.1(2) . . . . ?
N1 C8 C11 C12 6.9(3) . . . . ?
C9 C8 C11 C12 -179.5(2) . . . . ?
C9 N2 C13 C18 -57.3(2) . . . . ?
N3 N2 C13 C18 158.19(16) . . . . ?
C9 N2 C13 C14 122.00(19) . . . . ?
N3 N2 C13 C14 -22.5(2) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
N2 C13 C14 C15 -179.39(17) . . . . ?
C13 C14 C15 C16 1.3(3) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C14 C13 C18 C17 -1.4(3) . . . . ?
N2 C13 C18 C17 177.88(17) . . . . ?
C16 C17 C18 C13 1.8(3) . . . . ?

_refine_diff_density_max         0.642
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.071

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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 2008322'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad de La Plata
Argentina
;
_audit_update_record             
;
2020-07-18 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2-chloro-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Cl N3 O2'
_chemical_formula_weight         341.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   13.9852(11)
_cell_length_b                   6.2373(4)
_cell_length_c                   20.2255(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.334(7)
_cell_angle_gamma                90
_cell_volume                     1701.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1516
_cell_measurement_theta_min      4.5390
_cell_measurement_theta_max      69.8380
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.81882
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_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            6646
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.534
_diffrn_reflns_theta_max         72.347
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3303
_reflns_number_gt                2219
_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, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0717P)²+0.2432P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3303
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.004
_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 0.76750(17) 0.0751(4) 0.19371(12) 0.0557(6) Uani 1 1 d . . . . .
C2 C 0.8308(2) -0.0077(5) 0.15828(16) 0.0707(7) Uani 1 1 d . . . . .
C3 C 0.9194(3) -0.1005(6) 0.1955(2) 0.0953(11) Uani 1 1 d . . . . .
C4 C 0.9432(3) -0.1048(6) 0.2659(2) 0.1042(13) Uani 1 1 d . . . . .
C5 C 0.8806(3) -0.0199(6) 0.30013(19) 0.0899(11) Uani 1 1 d . . . . .
C6 C 0.7915(2) 0.0705(5) 0.26506(13) 0.0685(7) Uani 1 1 d . . . . .
C7 C 0.60419(17) 0.0464(4) 0.10812(10) 0.0512(5) Uani 1 1 d . . . . .
C8 C 0.51225(18) 0.1453(4) 0.10824(10) 0.0552(6) Uani 1 1 d . . . . .
C9 C 0.52950(19) 0.3040(4) 0.15631(11) 0.0605(6) Uani 1 1 d . . . . .
C10 C 0.6815(3) 0.5151(5) 0.20799(15) 0.0756(9) Uani 1 1 d . . . . .
C11 C 0.4585(3) 0.4502(7) 0.17593(19) 0.0927(12) Uani 1 1 d . . . . .
C12 C 0.36014(18) -0.0516(4) 0.09639(11) 0.0570(6) Uani 1 1 d . . . . .
C13 C 0.28085(18) -0.1764(4) 0.04667(11) 0.0568(6) Uani 1 1 d . . . . .
C14 C 0.1807(2) -0.1540(5) 0.04302(13) 0.0724(7) Uani 1 1 d . . . . .
C15 C 0.1109(2) -0.2868(7) 0.00072(18) 0.0910(10) Uani 1 1 d . . . . .
C16 C 0.1402(3) -0.4443(6) -0.03632(18) 0.0916(10) Uani 1 1 d . . . . .
C17 C 0.2385(3) -0.4719(5) -0.03304(16) 0.0801(9) Uani 1 1 d . . . . .
C18 C 0.3079(2) -0.3370(5) 0.00760(12) 0.0643(7) Uani 1 1 d . . . . .
N1 N 0.67534(14) 0.1625(3) 0.15582(8) 0.0555(5) Uani 1 1 d . . . . .
N2 N 0.62828(15) 0.3113(3) 0.18857(9) 0.0590(5) Uani 1 1 d . . . . .
N3 N 0.42018(15) 0.0655(4) 0.06828(9) 0.0585(5) Uani 1 1 d . . . . .
O1 O 0.62223(12) -0.1104(3) 0.07595(7) 0.0586(4) Uani 1 1 d . . . . .
O2 O 0.37094(15) -0.0674(3) 0.15782(8) 0.0794(6) Uani 1 1 d . . . . .
Cl1 Cl 0.14277(7) 0.04288(18) 0.09109(5) 0.1131(4) Uani 1 1 d . . . . .
H2 H 0.817(2) 0.003(4) 0.1075(15) 0.079(8) Uiso 1 1 d . . . . .
H3 H 0.963(2) -0.150(5) 0.1701(15) 0.085(10) Uiso 1 1 d . . . . .
H3N H 0.4103(17) 0.077(4) 0.0231(13) 0.057(7) Uiso 1 1 d . . . . .
H4 H 1.003(3) -0.171(7) 0.288(2) 0.149(15) Uiso 1 1 d . . . . .
H5 H 0.896(2) -0.021(5) 0.3515(17) 0.105(11) Uiso 1 1 d . . . . .
H6 H 0.745(2) 0.129(5) 0.2869(13) 0.073(9) Uiso 1 1 d . . . . .
H10A H 0.681(2) 0.606(5) 0.1672(15) 0.087(9) Uiso 1 1 d . . . . .
H10B H 0.751(3) 0.489(6) 0.238(2) 0.131(14) Uiso 1 1 d . . . . .
H10C H 0.645(3) 0.588(6) 0.2311(18) 0.112(13) Uiso 1 1 d . . . . .
H11A H 0.390(2) 0.420(5) 0.1534(16) 0.091(10) Uiso 1 1 d . . . . .
H11B H 0.462(3) 0.454(7) 0.222(2) 0.131(14) Uiso 1 1 d . . . . .
H11C H 0.472(3) 0.589(7) 0.1610(19) 0.119(15) Uiso 1 1 d . . . . .
H15 H 0.047(3) -0.260(5) 0.0040(16) 0.100(11) Uiso 1 1 d . . . . .
H16 H 0.092(3) -0.542(6) -0.0641(17) 0.112(12) Uiso 1 1 d . . . . .
H17 H 0.257(2) -0.582(5) -0.0560(15) 0.091(10) Uiso 1 1 d . . . . .
H18 H 0.3824(19) -0.360(4) 0.0099(12) 0.069(7) 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 C2 1.378(4) . ?
C1 C6 1.393(3) . ?
C1 N1 1.422(3) . ?
C2 C3 1.395(4) . ?
C3 C4 1.374(5) . ?
C4 C5 1.358(6) . ?
C5 C6 1.381(4) . ?
C7 O1 1.237(3) . ?
C7 N1 1.392(3) . ?
C7 C8 1.427(3) . ?
C8 C9 1.364(3) . ?
C8 N3 1.417(3) . ?
C9 N2 1.364(3) . ?
C9 C11 1.478(4) . ?
C10 N2 1.473(3) . ?
C12 O2 1.215(3) . ?
C12 N3 1.347(3) . ?
C12 C13 1.502(3) . ?
C13 C18 1.389(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.389(4) . ?
C14 Cl1 1.735(3) . ?
C15 C16 1.363(5) . ?
C16 C17 1.369(5) . ?
C17 C18 1.380(4) . ?
N1 N2 1.401(3) . ?

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
C2 C1 C6 121.3(3) . . ?
C2 C1 N1 118.6(2) . . ?
C6 C1 N1 120.1(2) . . ?
C1 C2 C3 118.4(3) . . ?
C4 C3 C2 120.4(4) . . ?
C5 C4 C3 120.5(3) . . ?
C4 C5 C6 120.9(3) . . ?
C5 C6 C1 118.5(3) . . ?
O1 C7 N1 124.6(2) . . ?
O1 C7 C8 130.7(2) . . ?
N1 C7 C8 104.68(19) . . ?
C9 C8 N3 128.6(2) . . ?
C9 C8 C7 109.0(2) . . ?
N3 C8 C7 122.1(2) . . ?
N2 C9 C8 109.3(2) . . ?
N2 C9 C11 121.3(2) . . ?
C8 C9 C11 129.4(3) . . ?
O2 C12 N3 123.6(2) . . ?
O2 C12 C13 120.8(2) . . ?
N3 C12 C13 115.51(19) . . ?
C18 C13 C14 117.7(2) . . ?
C18 C13 C12 119.4(2) . . ?
C14 C13 C12 122.6(2) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 Cl1 119.8(3) . . ?
C13 C14 Cl1 119.7(2) . . ?
C16 C15 C14 120.2(3) . . ?
C15 C16 C17 120.5(3) . . ?
C16 C17 C18 119.5(3) . . ?
C17 C18 C13 121.5(3) . . ?
C7 N1 N2 109.46(18) . . ?
C7 N1 C1 123.65(19) . . ?
N2 N1 C1 118.09(17) . . ?
C9 N2 N1 107.14(17) . . ?
C9 N2 C10 122.2(2) . . ?
N1 N2 C10 115.5(2) . . ?
C12 N3 C8 121.57(18) . . ?

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
C6 C1 C2 C3 1.1(4) . . . . ?
N1 C1 C2 C3 -177.6(3) . . . . ?
C1 C2 C3 C4 -1.3(5) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
N1 C1 C6 C5 178.6(2) . . . . ?
O1 C7 C8 C9 175.3(2) . . . . ?
N1 C7 C8 C9 -2.9(3) . . . . ?
O1 C7 C8 N3 1.4(4) . . . . ?
N1 C7 C8 N3 -176.8(2) . . . . ?
N3 C8 C9 N2 172.3(2) . . . . ?
C7 C8 C9 N2 -1.1(3) . . . . ?
N3 C8 C9 C11 -6.1(5) . . . . ?
C7 C8 C9 C11 -179.5(3) . . . . ?
O2 C12 C13 C18 -113.0(3) . . . . ?
N3 C12 C13 C18 63.2(3) . . . . ?
O2 C12 C13 C14 59.9(3) . . . . ?
N3 C12 C13 C14 -123.8(3) . . . . ?
C18 C13 C14 C15 -1.0(4) . . . . ?
C12 C13 C14 C15 -174.1(3) . . . . ?
C18 C13 C14 Cl1 179.63(19) . . . . ?
C12 C13 C14 Cl1 6.6(3) . . . . ?
C13 C14 C15 C16 1.7(5) . . . . ?
Cl1 C14 C15 C16 -178.9(3) . . . . ?
C14 C15 C16 C17 -0.9(5) . . . . ?
C15 C16 C17 C18 -0.7(5) . . . . ?
C16 C17 C18 C13 1.5(4) . . . . ?
C14 C13 C18 C17 -0.6(4) . . . . ?
C12 C13 C18 C17 172.7(2) . . . . ?
O1 C7 N1 N2 -172.6(2) . . . . ?
C8 C7 N1 N2 5.7(2) . . . . ?
O1 C7 N1 C1 -26.0(3) . . . . ?
C8 C7 N1 C1 152.3(2) . . . . ?
C2 C1 N1 C7 58.6(3) . . . . ?
C6 C1 N1 C7 -120.1(3) . . . . ?
C2 C1 N1 N2 -157.4(2) . . . . ?
C6 C1 N1 N2 23.9(3) . . . . ?
C8 C9 N2 N1 4.6(3) . . . . ?
C11 C9 N2 N1 -176.8(3) . . . . ?
C8 C9 N2 C10 141.2(2) . . . . ?
C11 C9 N2 C10 -40.2(4) . . . . ?
C7 N1 N2 C9 -6.5(2) . . . . ?
C1 N1 N2 C9 -155.2(2) . . . . ?
C7 N1 N2 C10 -146.4(2) . . . . ?
C1 N1 N2 C10 64.9(3) . . . . ?
O2 C12 N3 C8 12.8(4) . . . . ?
C13 C12 N3 C8 -163.3(2) . . . . ?
C9 C8 N3 C12 -70.6(3) . . . . ?
C7 C8 N3 C12 102.1(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
_geom_hbond_publ_flag
N3 H3N O1 0.89(2) 1.95(2) 2.833(2) 175(2) 3_655 yes
C10 H10A O1 1.00(3) 2.53(3) 3.479(3) 158(2) 1_565 yes
C10 H10C O2 0.90(4) 2.51(4) 3.037(4) 118(3) 2_655 yes
C11 H11C O2 0.96(4) 2.56(4) 3.233(4) 128(3) 1_565 yes

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Aqueous ethanol'
