# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_RXN70_JMrework
_database_code_depnum_ccdc_archive 'CCDC 2152626'
loop_
_audit_author_name
_audit_author_address
'John McAdam'
;University of Otago
New Zealand
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        6-chloro-[1,2,4]triazolo[3,4-a]phthalazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H5 Cl N4'
_chemical_formula_sum            'C9 H5 Cl N4'
_chemical_formula_weight         204.62

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'
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                   8.7825(4)
_cell_length_b                   16.4044(7)
_cell_length_c                   11.3954(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.420(4)
_cell_angle_gamma                90
_cell_volume                     1631.46(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    101(1)
_cell_measurement_reflns_used    3160
_cell_measurement_theta_min      5.0200
_cell_measurement_theta_max      72.4540

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    3.798
_shelx_estimated_absorpt_T_min   0.548
_shelx_estimated_absorpt_T_max   0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68925
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      101(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1725
_diffrn_reflns_number            6440
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.745
_diffrn_reflns_theta_max         72.885
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3144
_reflns_number_gt                2614
_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 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
SHELXL-2019/2 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010), WINGX (Farrugia 2012)
;
_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)+(0.0841P)²+0.7333P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3144
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
Cl1 Cl 0.82372(7) 1.10677(3) 0.41827(5) 0.0238(2) Uani 1 1 d . . . . .
C110 C 0.7551(3) 1.03586(15) 0.5109(2) 0.0190(5) Uani 1 1 d . . . . .
N12 N 0.8091(2) 0.96363(12) 0.50012(17) 0.0184(4) Uani 1 1 d . . . . .
N11 N 0.7494(2) 0.90715(12) 0.57123(18) 0.0179(4) Uani 1 1 d . . . . .
C12 C 0.7794(3) 0.82588(15) 0.5751(2) 0.0209(5) Uani 1 1 d . . . . .
H12 H 0.850066 0.799807 0.532991 0.025 Uiso 1 1 calc R U . . .
N13 N 0.6947(2) 0.78977(13) 0.64632(19) 0.0226(5) Uani 1 1 d . . . . .
N14 N 0.6050(2) 0.84892(13) 0.69378(19) 0.0217(5) Uani 1 1 d . . . . .
C13 C 0.6402(3) 0.91904(15) 0.6471(2) 0.0184(5) Uani 1 1 d . . . . .
C14 C 0.5847(3) 1.00083(15) 0.6598(2) 0.0182(5) Uani 1 1 d . . . . .
C15 C 0.4769(3) 1.02144(16) 0.7366(2) 0.0209(5) Uani 1 1 d . . . . .
H15 H 0.437499 0.981713 0.783044 0.025 Uiso 1 1 calc R U . . .
C16 C 0.4297(3) 1.10160(15) 0.7425(2) 0.0228(5) Uani 1 1 d . . . . .
H16 H 0.359088 1.115662 0.794074 0.027 Uiso 1 1 calc R U . . .
C17 C 0.4862(3) 1.16181(16) 0.6723(2) 0.0228(5) Uani 1 1 d . . . . .
H17 H 0.452874 1.215388 0.677351 0.027 Uiso 1 1 calc R U . . .
C18 C 0.5913(3) 1.14195(15) 0.5955(2) 0.0217(5) Uani 1 1 d . . . . .
H18 H 0.627727 1.181953 0.548012 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6431(3) 1.06152(15) 0.5893(2) 0.0177(5) Uani 1 1 d . . . . .
Cl2 Cl 0.61792(7) 0.35680(4) 0.54731(6) 0.0258(2) Uani 1 1 d . . . . .
C210 C 0.7227(3) 0.42670(15) 0.4772(2) 0.0194(5) Uani 1 1 d . . . . .
N22 N 0.7061(2) 0.50089(12) 0.51086(18) 0.0189(4) Uani 1 1 d . . . . .
N21 N 0.7923(2) 0.55581(12) 0.45556(18) 0.0182(4) Uani 1 1 d . . . . .
C22 C 0.7988(3) 0.63789(14) 0.4740(2) 0.0194(5) Uani 1 1 d . . . . .
H22 H 0.741791 0.666328 0.524508 0.023 Uiso 1 1 calc R U . . .
N23 N 0.8968(2) 0.67055(13) 0.41027(18) 0.0213(5) Uani 1 1 d . . . . .
N24 N 0.9591(2) 0.60848(12) 0.34670(18) 0.0202(5) Uani 1 1 d . . . . .
C23 C 0.8937(3) 0.54026(15) 0.3755(2) 0.0177(5) Uani 1 1 d . . . . .
C24 C 0.9108(3) 0.45687(15) 0.3391(2) 0.0176(5) Uani 1 1 d . . . . .
C25 C 1.0098(3) 0.43261(16) 0.2580(2) 0.0214(5) Uani 1 1 d . . . . .
H25 H 1.071382 0.470805 0.225741 0.026 Uiso 1 1 calc R U . . .
C26 C 1.0157(3) 0.35157(15) 0.2259(2) 0.0219(5) Uani 1 1 d . . . . .
H26 H 1.081859 0.335372 0.172017 0.026 Uiso 1 1 calc R U . . .
C27 C 0.9238(3) 0.29394(15) 0.2733(2) 0.0223(5) Uani 1 1 d . . . . .
H27 H 0.928005 0.239712 0.250080 0.027 Uiso 1 1 calc R U . . .
C28 C 0.8264(3) 0.31662(15) 0.3546(2) 0.0217(5) Uani 1 1 d . . . . .
H28 H 0.765388 0.277748 0.386039 0.026 Uiso 1 1 calc R U . . .
C29 C 0.8195(3) 0.39857(15) 0.3899(2) 0.0181(5) 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
Cl1 C110 1.724(2) . ?
C110 N12 1.287(3) . ?
C110 C19 1.462(3) . ?
N12 N11 1.373(3) . ?
N11 C12 1.359(3) . ?
N11 C13 1.374(3) . ?
C12 N13 1.303(3) . ?
C12 H12 0.9300 . ?
N13 N14 1.396(3) . ?
N14 C13 1.319(3) . ?
C13 C14 1.440(3) . ?
C14 C15 1.401(3) . ?
C14 C19 1.412(3) . ?
C15 C16 1.383(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.400(3) . ?
C18 H18 0.9300 . ?
Cl2 C210 1.722(3) . ?
C210 N22 1.289(3) . ?
C210 C29 1.455(3) . ?
N22 N21 1.374(3) . ?
N21 C22 1.363(3) . ?
N21 C23 1.368(3) . ?
C22 N23 1.301(3) . ?
C22 H22 0.9300 . ?
N23 N24 1.396(3) . ?
N24 C23 1.316(3) . ?
C23 C24 1.442(3) . ?
C24 C25 1.396(3) . ?
C24 C29 1.412(3) . ?
C25 C26 1.381(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.391(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.380(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.406(3) . ?
C28 H28 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
N12 C110 C19 127.1(2) . . ?
N12 C110 Cl1 113.89(19) . . ?
C19 C110 Cl1 118.99(18) . . ?
C110 N12 N11 113.3(2) . . ?
C12 N11 N12 126.6(2) . . ?
C12 N11 C13 105.4(2) . . ?
N12 N11 C13 127.9(2) . . ?
N13 C12 N11 110.1(2) . . ?
N13 C12 H12 124.9 . . ?
N11 C12 H12 124.9 . . ?
C12 N13 N14 108.1(2) . . ?
C13 N14 N13 106.4(2) . . ?
N14 C13 N11 110.0(2) . . ?
N14 C13 C14 132.4(2) . . ?
N11 C13 C14 117.6(2) . . ?
C15 C14 C19 120.0(2) . . ?
C15 C14 C13 123.2(2) . . ?
C19 C14 C13 116.8(2) . . ?
C16 C15 C14 119.1(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 121.2(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 119.7(2) . . ?
C18 C19 C110 123.2(2) . . ?
C14 C19 C110 117.2(2) . . ?
N22 C210 C29 126.7(2) . . ?
N22 C210 Cl2 114.00(19) . . ?
C29 C210 Cl2 119.33(18) . . ?
C210 N22 N21 113.3(2) . . ?
C22 N21 C23 105.5(2) . . ?
C22 N21 N22 126.4(2) . . ?
C23 N21 N22 128.1(2) . . ?
N23 C22 N21 109.9(2) . . ?
N23 C22 H22 125.1 . . ?
N21 C22 H22 125.1 . . ?
C22 N23 N24 108.1(2) . . ?
C23 N24 N23 106.5(2) . . ?
N24 C23 N21 110.0(2) . . ?
N24 C23 C24 132.3(2) . . ?
N21 C23 C24 117.7(2) . . ?
C25 C24 C29 120.1(2) . . ?
C25 C24 C23 123.6(2) . . ?
C29 C24 C23 116.3(2) . . ?
C26 C25 C24 119.6(2) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 120.7(2) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C26 120.5(2) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 119.9(2) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C24 C29 C28 119.1(2) . . ?
C24 C29 C210 117.9(2) . . ?
C28 C29 C210 123.1(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
C19 C110 N12 N11 0.8(4) . . . . ?
Cl1 C110 N12 N11 -177.78(16) . . . . ?
C110 N12 N11 C12 176.9(2) . . . . ?
C110 N12 N11 C13 1.7(3) . . . . ?
N12 N11 C12 N13 -175.4(2) . . . . ?
C13 N11 C12 N13 0.7(3) . . . . ?
N11 C12 N13 N14 -0.7(3) . . . . ?
C12 N13 N14 C13 0.5(3) . . . . ?
N13 N14 C13 N11 0.0(3) . . . . ?
N13 N14 C13 C14 178.8(2) . . . . ?
C12 N11 C13 N14 -0.4(3) . . . . ?
N12 N11 C13 N14 175.6(2) . . . . ?
C12 N11 C13 C14 -179.4(2) . . . . ?
N12 N11 C13 C14 -3.4(3) . . . . ?
N14 C13 C14 C15 3.1(4) . . . . ?
N11 C13 C14 C15 -178.2(2) . . . . ?
N14 C13 C14 C19 -176.2(3) . . . . ?
N11 C13 C14 C19 2.6(3) . . . . ?
C19 C14 C15 C16 -0.4(3) . . . . ?
C13 C14 C15 C16 -179.6(2) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C14 1.4(4) . . . . ?
C17 C18 C19 C110 -179.5(2) . . . . ?
C15 C14 C19 C18 -0.7(3) . . . . ?
C13 C14 C19 C18 178.6(2) . . . . ?
C15 C14 C19 C110 -179.9(2) . . . . ?
C13 C14 C19 C110 -0.6(3) . . . . ?
N12 C110 C19 C18 179.7(2) . . . . ?
Cl1 C110 C19 C18 -1.9(3) . . . . ?
N12 C110 C19 C14 -1.2(4) . . . . ?
Cl1 C110 C19 C14 177.27(17) . . . . ?
C29 C210 N22 N21 -0.3(3) . . . . ?
Cl2 C210 N22 N21 179.00(15) . . . . ?
C210 N22 N21 C22 -179.4(2) . . . . ?
C210 N22 N21 C23 -2.6(3) . . . . ?
C23 N21 C22 N23 0.0(3) . . . . ?
N22 N21 C22 N23 177.4(2) . . . . ?
N21 C22 N23 N24 -0.1(3) . . . . ?
C22 N23 N24 C23 0.3(3) . . . . ?
N23 N24 C23 N21 -0.3(3) . . . . ?
N23 N24 C23 C24 180.0(2) . . . . ?
C22 N21 C23 N24 0.2(3) . . . . ?
N22 N21 C23 N24 -177.1(2) . . . . ?
C22 N21 C23 C24 180.0(2) . . . . ?
N22 N21 C23 C24 2.6(4) . . . . ?
N24 C23 C24 C25 -0.4(4) . . . . ?
N21 C23 C24 C25 179.8(2) . . . . ?
N24 C23 C24 C29 -180.0(2) . . . . ?
N21 C23 C24 C29 0.3(3) . . . . ?
C29 C24 C25 C26 1.3(4) . . . . ?
C23 C24 C25 C26 -178.3(2) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C25 C26 C27 C28 -0.9(4) . . . . ?
C26 C27 C28 C29 0.1(4) . . . . ?
C25 C24 C29 C28 -2.0(3) . . . . ?
C23 C24 C29 C28 177.6(2) . . . . ?
C25 C24 C29 C210 177.7(2) . . . . ?
C23 C24 C29 C210 -2.7(3) . . . . ?
C27 C28 C29 C24 1.3(4) . . . . ?
C27 C28 C29 C210 -178.4(2) . . . . ?
N22 C210 C29 C24 3.0(4) . . . . ?
Cl2 C210 C29 C24 -176.34(17) . . . . ?
N22 C210 C29 C28 -177.3(2) . . . . ?
Cl2 C210 C29 C28 3.4(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
C12 H12 N23 0.93 2.60 3.394(3) 143.9 . yes
C22 H22 N13 0.93 2.52 3.362(3) 151.5 . yes

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_wingx_JM_rxn34
_database_code_depnum_ccdc_archive 'CCDC 2152622'
loop_
_audit_author_name
_audit_author_address
'John McAdam'
;University of Otago
New Zealand
;
_audit_update_record             
;
2022-05-08 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        
;
6-chloro-3-methyl-[1,2,4]triazolo[3,4-a]phthalazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H7 Cl N4'
_chemical_formula_sum            'C10 H7 Cl N4'
_chemical_formula_weight         218.65

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'
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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.80820(10)
_cell_length_b                   7.36850(10)
_cell_length_c                   14.2931(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.213(2)
_cell_angle_gamma                90
_cell_volume                     927.66(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    8555
_cell_measurement_theta_min      5.8610
_cell_measurement_theta_max      72.6750

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    3.379
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3449
_diffrn_reflns_number            16468
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.891
_diffrn_reflns_theta_max         72.827
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1833
_reflns_number_gt                1679
_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 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
SHELXL-2019/2 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010), WINGX (Farrugia 2012)
;
_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)+(0.0323P)²+0.5541P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1833
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
Cl1 Cl 0.25918(4) 0.17880(4) 0.55217(2) 0.01794(11) Uani 1 1 d . . . . .
N2 N 0.61366(13) 0.38976(15) 0.65956(8) 0.0140(2) Uani 1 1 d . . . . .
N1 N 0.47020(13) 0.32005(15) 0.64950(8) 0.0142(2) Uani 1 1 d . . . . .
N4 N 0.84472(13) 0.48371(16) 0.62830(8) 0.0187(3) Uani 1 1 d . . . . .
N3 N 0.81090(14) 0.52179(17) 0.72185(8) 0.0194(3) Uani 1 1 d . . . . .
C3 C 0.72383(15) 0.40491(18) 0.59242(10) 0.0151(3) Uani 1 1 d . . . . .
C4 C 0.68973(16) 0.33791(18) 0.50001(10) 0.0148(3) Uani 1 1 d . . . . .
C9 C 0.54323(15) 0.26340(18) 0.48630(9) 0.0145(3) Uani 1 1 d . . . . .
C2 C 0.67272(16) 0.46476(18) 0.73923(9) 0.0160(3) Uani 1 1 d . . . . .
C8 C 0.50231(16) 0.19749(18) 0.39758(10) 0.0172(3) Uani 1 1 d . . . . .
H8 H 0.406801 0.146946 0.387849 0.021 Uiso 1 1 calc R U . . .
C5 C 0.79209(16) 0.34793(19) 0.42550(10) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.888432 0.396712 0.434462 0.022 Uiso 1 1 calc R U . . .
C10 C 0.44134(15) 0.26194(18) 0.56626(9) 0.0142(3) Uani 1 1 d . . . . .
C7 C 0.60473(17) 0.2081(2) 0.32476(10) 0.0196(3) Uani 1 1 d . . . . .
H7 H 0.577813 0.163989 0.266043 0.024 Uiso 1 1 calc R U . . .
C1 C 0.59000(17) 0.4737(2) 0.82929(10) 0.0199(3) Uani 1 1 d . . . . .
H1A H 0.584849 0.354581 0.856346 0.030 Uiso 1 1 calc R U . . .
H1B H 0.489072 0.518371 0.818493 0.030 Uiso 1 1 calc R U . . .
H1C H 0.642516 0.553785 0.871332 0.030 Uiso 1 1 calc R U . . .
C6 C 0.74838(17) 0.2845(2) 0.33848(10) 0.0205(3) Uani 1 1 d . . . . .
H6 H 0.815288 0.292776 0.288474 0.025 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
Cl1 C10 1.7285(13) . ?
N2 C2 1.3668(17) . ?
N2 N1 1.3711(16) . ?
N2 C3 1.3719(18) . ?
N1 C10 1.2889(18) . ?
N4 C3 1.3152(18) . ?
N4 N3 1.3995(17) . ?
N3 C2 1.3122(19) . ?
C3 C4 1.4407(19) . ?
C4 C5 1.400(2) . ?
C4 C9 1.4153(19) . ?
C9 C8 1.4037(19) . ?
C9 C10 1.4558(19) . ?
C2 C1 1.483(2) . ?
C8 C7 1.382(2) . ?
C8 H8 0.9300 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C7 C6 1.398(2) . ?
C7 H7 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 H6 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
C2 N2 N1 125.92(11) . . ?
C2 N2 C3 106.37(11) . . ?
N1 N2 C3 127.67(11) . . ?
C10 N1 N2 113.57(11) . . ?
C3 N4 N3 106.63(11) . . ?
C2 N3 N4 108.51(11) . . ?
N4 C3 N2 109.69(12) . . ?
N4 C3 C4 132.41(13) . . ?
N2 C3 C4 117.89(12) . . ?
C5 C4 C9 120.31(13) . . ?
C5 C4 C3 123.14(13) . . ?
C9 C4 C3 116.53(12) . . ?
C8 C9 C4 119.35(13) . . ?
C8 C9 C10 123.34(12) . . ?
C4 C9 C10 117.30(12) . . ?
N3 C2 N2 108.80(12) . . ?
N3 C2 C1 127.53(13) . . ?
N2 C2 C1 123.66(13) . . ?
C7 C8 C9 119.64(13) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C6 C5 C4 119.26(13) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N1 C10 C9 127.02(12) . . ?
N1 C10 Cl1 113.90(10) . . ?
C9 C10 Cl1 119.07(10) . . ?
C8 C7 C6 120.68(13) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C6 C7 120.75(13) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 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
C2 N2 N1 C10 178.17(12) . . . . ?
C3 N2 N1 C10 0.80(19) . . . . ?
C3 N4 N3 C2 0.26(15) . . . . ?
N3 N4 C3 N2 -0.38(15) . . . . ?
N3 N4 C3 C4 178.94(14) . . . . ?
C2 N2 C3 N4 0.36(15) . . . . ?
N1 N2 C3 N4 178.14(12) . . . . ?
C2 N2 C3 C4 -179.07(11) . . . . ?
N1 N2 C3 C4 -1.29(19) . . . . ?
N4 C3 C4 C5 -0.1(2) . . . . ?
N2 C3 C4 C5 179.15(12) . . . . ?
N4 C3 C4 C9 -178.57(14) . . . . ?
N2 C3 C4 C9 0.70(18) . . . . ?
C5 C4 C9 C8 0.83(19) . . . . ?
C3 C4 C9 C8 179.33(12) . . . . ?
C5 C4 C9 C10 -178.34(12) . . . . ?
C3 C4 C9 C10 0.16(18) . . . . ?
N4 N3 C2 N2 -0.04(15) . . . . ?
N4 N3 C2 C1 178.92(13) . . . . ?
N1 N2 C2 N3 -178.02(12) . . . . ?
C3 N2 C2 N3 -0.19(15) . . . . ?
N1 N2 C2 C1 3.0(2) . . . . ?
C3 N2 C2 C1 -179.19(13) . . . . ?
C4 C9 C8 C7 -0.7(2) . . . . ?
C10 C9 C8 C7 178.38(12) . . . . ?
C9 C4 C5 C6 0.1(2) . . . . ?
C3 C4 C5 C6 -178.31(13) . . . . ?
N2 N1 C10 C9 0.25(19) . . . . ?
N2 N1 C10 Cl1 -178.52(8) . . . . ?
C8 C9 C10 N1 -179.83(13) . . . . ?
C4 C9 C10 N1 -0.7(2) . . . . ?
C8 C9 C10 Cl1 -1.11(18) . . . . ?
C4 C9 C10 Cl1 178.02(10) . . . . ?
C9 C8 C7 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 -1.1(2) . . . . ?
C8 C7 C6 C5 1.2(2) . . . . ?

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
C6 H6 N1 0.93 2.55 3.4272(19) 156.7 4_665 yes
C5 H5 N4 0.93 2.67 3.5188(19) 152.3 3_766 yes

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.050

