# Electronic Supplementary Material (ESI) for RSC Sustainability.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_106
_audit_block_doi                 10.5517/ccdc.csd.cc13j5xq
_database_code_depnum_ccdc_archive 'CCDC 1028453'
_audit_update_record             
;
2014-10-10 deposited with the CCDC.	2024-04-18 downloaded from the CCDC.
;
_audit_creation_date             2014-10-09
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H12 Cl N3'
_chemical_formula_sum            'C15 H12 Cl N3'
_chemical_formula_weight         269.73
_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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   5.7050(8)
_cell_length_b                   8.6478(12)
_cell_length_c                   26.865(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.946(2)
_cell_angle_gamma                90.00
_cell_volume                     1325.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6984
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.25
_cell_measurement_theta_min      2.47
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.9597
_exptl_absorpt_correction_T_min  0.8879
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14670
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.52
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2320
_reflns_number_total             2695
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0542P)²+0.5225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1239
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.06701(13) 0.11521(8) 0.43094(2) 0.0854(3) Uani 1 1 d . . .
N1 N -0.3088(3) -0.17845(17) 0.20922(5) 0.0467(4) Uani 1 1 d . . .
N2 N -0.5434(3) -0.1646(2) 0.21115(6) 0.0571(4) Uani 1 1 d . . .
N3 N -0.6109(3) -0.0809(2) 0.17244(6) 0.0526(4) Uani 1 1 d . . .
C1 C -0.0026(3) 0.0111(2) 0.37717(6) 0.0499(4) Uani 1 1 d . . .
C2 C 0.1516(3) -0.0975(3) 0.36029(8) 0.0577(5) Uani 1 1 d . . .
H2 H 0.2925 -0.1153 0.3772 0.069 Uiso 1 1 calc R . .
C3 C 0.0950(3) -0.1805(2) 0.31765(7) 0.0537(5) Uani 1 1 d . . .
H3 H 0.2009 -0.2526 0.3056 0.064 Uiso 1 1 calc R . .
C4 C -0.1162(3) -0.15793(19) 0.29274(6) 0.0422(4) Uani 1 1 d . . .
C5 C -0.2683(3) -0.0469(2) 0.31062(7) 0.0498(4) Uani 1 1 d . . .
H5 H -0.4102 -0.0293 0.2940 0.060 Uiso 1 1 calc R . .
C6 C -0.2123(4) 0.0380(2) 0.35284(7) 0.0542(5) Uani 1 1 d . . .
H6 H -0.3153 0.1124 0.3646 0.065 Uiso 1 1 calc R . .
C7 C -0.1773(4) -0.2590(2) 0.24857(7) 0.0558(5) Uani 1 1 d . . .
H7A H -0.0336 -0.2995 0.2348 0.067 Uiso 1 1 calc R . .
H7B H -0.2693 -0.3462 0.2599 0.067 Uiso 1 1 calc R . .
C8 C -0.2256(3) -0.1038(2) 0.16959(6) 0.0449(4) Uani 1 1 d . . .
H8 H -0.0699 -0.0954 0.1602 0.054 Uiso 1 1 calc R . .
C9 C -0.4190(3) -0.0423(2) 0.14569(6) 0.0406(4) Uani 1 1 d . . .
C10 C -0.4340(3) 0.0521(2) 0.10015(6) 0.0418(4) Uani 1 1 d . . .
C11 C -0.2516(3) 0.0504(2) 0.06644(7) 0.0511(4) Uani 1 1 d . . .
H11 H -0.1226 -0.0132 0.0722 0.061 Uiso 1 1 calc R . .
C12 C -0.2608(4) 0.1427(3) 0.02443(7) 0.0618(5) Uani 1 1 d . . .
H12 H -0.1379 0.1408 0.0021 0.074 Uiso 1 1 calc R . .
C13 C -0.4507(4) 0.2376(3) 0.01537(8) 0.0639(5) Uani 1 1 d . . .
H13 H -0.4560 0.2998 -0.0129 0.077 Uiso 1 1 calc R . .
C14 C -0.6326(4) 0.2399(3) 0.04842(8) 0.0619(5) Uani 1 1 d . . .
H14 H -0.7612 0.3037 0.0424 0.074 Uiso 1 1 calc R . .
C15 C -0.6253(3) 0.1478(2) 0.09050(7) 0.0529(5) Uani 1 1 d . . .
H15 H -0.7493 0.1499 0.1125 0.063 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.1169(6) 0.0799(4) 0.0587(4) -0.0159(3) -0.0208(3) -0.0114(4)
N1 0.0538(9) 0.0471(8) 0.0392(7) -0.0040(6) 0.0028(6) -0.0050(7)
N2 0.0549(9) 0.0687(11) 0.0479(9) -0.0022(8) 0.0075(7) -0.0181(8)
N3 0.0413(8) 0.0683(10) 0.0482(9) -0.0061(7) 0.0051(6) -0.0111(7)
C1 0.0620(11) 0.0470(10) 0.0406(9) 0.0031(7) -0.0029(8) -0.0082(8)
C2 0.0476(10) 0.0700(13) 0.0554(11) 0.0054(10) -0.0061(8) 0.0014(9)
C3 0.0504(10) 0.0570(11) 0.0541(10) 0.0048(9) 0.0076(8) 0.0119(9)
C4 0.0520(9) 0.0370(8) 0.0378(8) 0.0061(7) 0.0055(7) 0.0002(7)
C5 0.0498(10) 0.0515(10) 0.0480(10) -0.0001(8) -0.0058(8) 0.0099(8)
C6 0.0655(12) 0.0477(10) 0.0495(10) -0.0044(8) -0.0004(9) 0.0122(9)
C7 0.0798(13) 0.0416(10) 0.0459(10) 0.0002(8) 0.0001(9) 0.0038(9)
C8 0.0426(9) 0.0501(10) 0.0423(9) -0.0029(7) 0.0057(7) -0.0016(7)
C9 0.0354(8) 0.0471(9) 0.0395(8) -0.0096(7) 0.0029(6) -0.0055(7)
C10 0.0365(8) 0.0489(9) 0.0399(8) -0.0079(7) -0.0021(6) -0.0043(7)
C11 0.0438(9) 0.0582(11) 0.0514(10) 0.0011(8) 0.0058(8) 0.0063(8)
C12 0.0587(12) 0.0770(14) 0.0500(11) 0.0053(10) 0.0102(9) -0.0001(10)
C13 0.0684(13) 0.0745(14) 0.0486(11) 0.0083(10) -0.0100(9) 0.0025(11)
C14 0.0528(11) 0.0740(14) 0.0584(12) -0.0016(10) -0.0155(9) 0.0136(10)
C15 0.0387(9) 0.0712(13) 0.0486(10) -0.0094(9) -0.0023(7) 0.0039(8)

_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
Cl1 C1 1.7422(18) . ?
N1 N2 1.346(2) . ?
N1 C7 1.463(2) . ?
N1 C8 1.339(2) . ?
N2 N3 1.319(2) . ?
N3 C9 1.361(2) . ?
C1 C2 1.369(3) . ?
C1 C6 1.374(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C4 C5 1.385(2) . ?
C4 C7 1.510(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9300 . ?
C8 C9 1.375(2) . ?
C9 C10 1.472(2) . ?
C10 C11 1.391(2) . ?
C10 C15 1.391(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 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 C7 120.87(15) . . ?
C8 N1 N2 110.71(15) . . ?
C8 N1 C7 128.34(16) . . ?
N3 N2 N1 107.20(14) . . ?
N2 N3 C9 108.94(15) . . ?
C2 C1 Cl1 119.35(15) . . ?
C2 C1 C6 121.19(17) . . ?
C6 C1 Cl1 119.45(15) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.15(18) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.09(17) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.42(16) . . ?
C3 C4 C7 119.12(16) . . ?
C5 C4 C7 122.41(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.95(17) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.18(17) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 C4 113.63(15) . . ?
N1 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C4 C7 H7A 108.8 . . ?
C4 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 H8 127.3 . . ?
N1 C8 C9 105.42(15) . . ?
C9 C8 H8 127.3 . . ?
N3 C9 C8 107.74(15) . . ?
N3 C9 C10 122.62(15) . . ?
C8 C9 C10 129.63(15) . . ?
C11 C10 C9 120.13(15) . . ?
C11 C10 C15 118.55(17) . . ?
C15 C10 C9 121.29(15) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.46(18) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.48(18) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.56(19) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.42(19) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.54(18) . . ?
C14 C15 H15 119.7 . . ?

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
Cl1 C1 C2 C3 179.69(15) . . . . ?
Cl1 C1 C6 C5 -178.89(15) . . . . ?
N1 N2 N3 C9 0.4(2) . . . . ?
N1 C8 C9 N3 0.78(19) . . . . ?
N1 C8 C9 C10 179.60(16) . . . . ?
N2 N1 C7 C4 -84.8(2) . . . . ?
N2 N1 C8 C9 -0.57(19) . . . . ?
N2 N3 C9 C8 -0.7(2) . . . . ?
N2 N3 C9 C10 -179.66(15) . . . . ?
N3 C9 C10 C11 -160.72(17) . . . . ?
N3 C9 C10 C15 21.2(3) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C2 C3 C4 C7 -175.71(18) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C3 C4 C7 N1 -144.85(17) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C5 C4 C7 N1 37.8(2) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C7 N1 N2 N3 176.96(15) . . . . ?
C7 N1 C8 C9 -177.10(16) . . . . ?
C7 C4 C5 C6 176.44(18) . . . . ?
C8 N1 N2 N3 0.1(2) . . . . ?
C8 N1 C7 C4 91.4(2) . . . . ?
C8 C9 C10 C11 20.6(3) . . . . ?
C8 C9 C10 C15 -157.42(18) . . . . ?
C9 C10 C11 C12 -177.78(18) . . . . ?
C9 C10 C15 C14 177.66(17) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C10 C15 C14 -0.4(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?

