# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

data_2-cl
_audit_creation_date               2019-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C15 H18 Cl N5 O3'
_chemical_formula_sum              'C15 H18 Cl N5 O3'
_chemical_formula_weight           351.79
_chemical_absolute_configuration   ad
_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' 0.0181 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'
 'Cl' 'Cl' 0.3639 0.7018 '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'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             5
_space_group_name_H-M_alt          'I 1 2 1'
_space_group_name_Hall             'I 2y'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z'
 'x+1/2, y+1/2, z+1/2'
 '-x+1/2, y+1/2, -z+1/2'

_cell_length_a                     11.5414(2)
_cell_length_b                     7.33570(10)
_cell_length_c                     19.5853(3)
_cell_angle_alpha                  90
_cell_angle_beta                   100.033(2)
_cell_angle_gamma                  90
_cell_volume                       1632.82(4)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      2826
_cell_measurement_temperature      100.00(10)
_cell_measurement_theta_max        73.4370
_cell_measurement_theta_min        4.5850
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      2.297
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.93223
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.431
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               736
_exptl_crystal_size_max            0.12
_exptl_crystal_size_mid            0.11
_exptl_crystal_size_min            0.08
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0145
_diffrn_reflns_av_unetI/netI       0.0201
_diffrn_reflns_Laue_measured_fraction_full  0.996
_diffrn_reflns_Laue_measured_fraction_max  0.971
_diffrn_reflns_limit_h_max         14
_diffrn_reflns_limit_h_min         -14
_diffrn_reflns_limit_k_max         8
_diffrn_reflns_limit_k_min         -9
_diffrn_reflns_limit_l_max         15
_diffrn_reflns_limit_l_min         -23
_diffrn_reflns_number              3141
_diffrn_reflns_point_group_measured_fraction_full  0.730
_diffrn_reflns_point_group_measured_fraction_max  0.701
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           73.533
_diffrn_reflns_theta_min           4.157
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100.00(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   5.2684
_diffrn_detector_type              AtlasS2
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -28.00  69.00   1.00    1.00    --   40.98 -57.00  30.00   97
  2  ω     64.00  89.00   1.00    1.00    --   40.98-125.00 -90.00   25
  3  ω     70.00 116.00   1.00    1.00    --  106.95-125.00 -90.00   46
  4  ω     37.00 132.00   1.00    1.00    --  106.95 -45.00 -30.00   95
  5  ω     97.00 148.00   1.00    1.00    --  106.95  45.00 -60.00   51
  6  ω     96.00 121.00   1.00    1.00    --  106.95 125.00 -30.00   25
  7  ω    113.00 175.00   1.00    1.00    --  106.95 125.00  90.00   62
  8  ω    115.00 174.00   1.00    1.00    --  106.95  45.00 150.00   59
  9  ω     64.00 115.00   1.00    1.00    --   40.98  38.00 120.00   51
 10  ω     25.00 104.00   1.00    1.00    --  106.95 -95.00 150.00   79
 11  ω      1.00  50.00   1.00    1.00    --   40.98 -99.00   0.00   49
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0723969000
_diffrn_orient_matrix_UB_12        0.1741157000
_diffrn_orient_matrix_UB_13        0.0063222000
_diffrn_orient_matrix_UB_21        0.1087788000
_diffrn_orient_matrix_UB_22        0.1175667000
_diffrn_orient_matrix_UB_23        -0.0043921000
_diffrn_orient_matrix_UB_31        -0.0354821000
_diffrn_orient_matrix_UB_32        0.0076963000
_diffrn_orient_matrix_UB_33        -0.0795179000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage           0.333
_reflns_Friedel_fraction_full      0.414
_reflns_Friedel_fraction_max       0.381
_reflns_number_gt                  2291
_reflns_number_total               2300
_reflns_odcompleteness_completeness  99.75
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       66.97
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection         'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction          'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max           0.220
_refine_diff_density_min           -0.234
_refine_diff_density_rms           0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 565 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.046(10)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       228
_refine_ls_number_reflns           2300
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0264
_refine_ls_R_factor_gt             0.0263
_refine_ls_restrained_S_all        1.045
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0472P)²+0.5170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0696
_refine_ls_wR_factor_ref           0.0696
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       direct
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Cl1 Cl 0.84314(4) 0.43764(8) 0.39099(2) 0.02327(14) Uani 1 1 d . . . . .
 O1 O 0.38023(14) 0.2379(2) 0.36439(8) 0.0207(3) Uani 1 1 d . . . . .
 O2 O 0.36058(14) 0.3907(2) 0.46118(7) 0.0217(3) Uani 1 1 d . . . . .
 O3 O 0.36114(13) 0.7829(2) 0.45261(8) 0.0202(3) Uani 1 1 d . . . . .
 N4 N 0.41718(14) 0.5515(3) 0.29787(8) 0.0148(3) Uani 1 1 d . . . . .
 N5 N 0.42874(14) 0.5431(3) 0.18455(8) 0.0168(4) Uani 1 1 d . . . . .
 N3 N 0.61966(14) 0.4853(3) 0.34843(8) 0.0168(4) Uani 1 1 d . . . . .
 N2 N 0.74310(14) 0.4536(3) 0.26194(8) 0.0175(3) Uani 1 1 d . . . . .
 N1 N 0.67797(14) 0.4560(3) 0.14412(8) 0.0189(4) Uani 1 1 d . . . . .
 C4 C 0.53239(17) 0.5112(3) 0.29378(10) 0.0154(4) Uani 1 1 d . . . . .
 C3 C 0.53859(17) 0.5070(3) 0.22419(10) 0.0153(4) Uani 1 1 d . . . . .
 C10 C 0.37363(17) 0.3785(3) 0.39513(10) 0.0156(4) Uani 1 1 d . . . . .
 C5 C 0.36007(18) 0.5682(3) 0.23028(10) 0.0165(4) Uani 1 1 d . . . . .
 H5 H 0.280311 0.594650 0.218309 0.020 Uiso 1 1 calc R . . . .
 C2 C 0.65238(17) 0.4716(3) 0.20770(10) 0.0164(4) Uani 1 1 d . . . . .
 C6 C 0.37169(17) 0.5680(3) 0.36269(10) 0.0149(4) Uani 1 1 d . . . . .
 C1 C 0.71950(16) 0.4611(3) 0.32525(10) 0.0172(4) Uani 1 1 d . . . . .
 C7 C 0.24451(17) 0.6469(3) 0.35220(10) 0.0165(4) Uani 1 1 d . . . . .
 H7 H 0.237484 0.741199 0.316290 0.020 Uiso 1 1 calc R . . . .
 C12 C 0.14542(17) 0.5143(3) 0.33310(10) 0.0187(4) Uani 1 1 d . . . . .
 H12 H 0.143688 0.412922 0.361430 0.022 Uiso 1 1 calc R . . . .
 C14 C 0.80033(17) 0.4326(4) 0.13498(11) 0.0226(4) Uani 1 1 d . . . . .
 H14A H 0.840127 0.547926 0.140913 0.034 Uiso 1 1 calc GR . . . .
 H14B H 0.802144 0.386845 0.089253 0.034 Uiso 1 1 calc GR . . . .
 H14C H 0.838932 0.347709 0.168768 0.034 Uiso 1 1 calc GR . . . .
 C15 C 0.58902(18) 0.4594(4) 0.08132(10) 0.0231(5) Uani 1 1 d . . . . .
 H15A H 0.514788 0.495526 0.092772 0.035 Uiso 1 1 calc GR . . . .
 H15B H 0.581830 0.340130 0.060850 0.035 Uiso 1 1 calc GR . . . .
 H15C H 0.611914 0.544835 0.048990 0.035 Uiso 1 1 calc GR . . . .
 C9 C 0.43967(18) 0.7148(3) 0.41016(11) 0.0179(4) Uani 1 1 d . . . . .
 H9A H 0.508750 0.662012 0.438606 0.022 Uiso 1 1 calc R . . . .
 H9B H 0.464725 0.812242 0.382593 0.022 Uiso 1 1 calc R . . . .
 C8 C 0.24264(19) 0.7399(3) 0.42227(11) 0.0205(5) Uani 1 1 d . . . . .
 H8A H 0.195693 0.850210 0.415541 0.025 Uiso 1 1 calc R . . . .
 H8B H 0.208388 0.658944 0.452493 0.025 Uiso 1 1 calc R . . . .
 C13 C 0.06038(19) 0.5312(4) 0.27885(11) 0.0225(5) Uani 1 1 d . . . . .
 C11 C 0.3432(2) 0.2199(4) 0.49542(12) 0.0280(5) Uani 1 1 d . . . . .
 H11A H 0.263771 0.178809 0.480632 0.042 Uiso 1 1 calc GR . . . .
 H11B H 0.357380 0.237776 0.544726 0.042 Uiso 1 1 calc GR . . . .
 H11C H 0.396791 0.130083 0.483527 0.042 Uiso 1 1 calc GR . . . .
 H13A H -0.004(3) 0.443(5) 0.2689(14) 0.033(7) Uiso 1 1 d . . . . .
 H13B H 0.057(3) 0.633(5) 0.2480(16) 0.038(9) 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
 Cl1 C1 1.7560(19) . ?
 O1 C10 1.203(3) . ?
 O2 C10 1.331(2) . ?
 O2 C11 1.452(3) . ?
 O3 C9 1.423(3) . ?
 O3 C8 1.428(3) . ?
 N4 C4 1.378(2) . ?
 N4 C5 1.377(3) . ?
 N4 C6 1.461(2) . ?
 N5 C3 1.392(3) . ?
 N5 C5 1.308(3) . ?
 N3 C4 1.349(3) . ?
 N3 C1 1.322(2) . ?
 N2 C2 1.362(3) . ?
 N2 C1 1.316(2) . ?
 N1 C2 1.334(3) . ?
 N1 C14 1.464(2) . ?
 N1 C15 1.459(2) . ?
 C4 C3 1.378(3) . ?
 C3 C2 1.430(3) . ?
 C10 C6 1.527(3) . ?
 C5 H5 0.9300 . ?
 C6 C7 1.558(3) . ?
 C6 C9 1.544(3) . ?
 C7 H7 0.9800 . ?
 C7 C12 1.498(3) . ?
 C7 C8 1.536(3) . ?
 C12 H12 0.9300 . ?
 C12 C13 1.321(3) . ?
 C14 H14A 0.9600 . ?
 C14 H14B 0.9600 . ?
 C14 H14C 0.9600 . ?
 C15 H15A 0.9600 . ?
 C15 H15B 0.9600 . ?
 C15 H15C 0.9600 . ?
 C9 H9A 0.9700 . ?
 C9 H9B 0.9700 . ?
 C8 H8A 0.9700 . ?
 C8 H8B 0.9700 . ?
 C13 H13A 0.98(3) . ?
 C13 H13B 0.96(4) . ?
 C11 H11A 0.9600 . ?
 C11 H11B 0.9600 . ?
 C11 H11C 0.9600 . ?

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
 C10 O2 C11 116.03(17) . . ?
 C9 O3 C8 109.91(16) . . ?
 C4 N4 C6 124.38(16) . . ?
 C5 N4 C4 105.56(15) . . ?
 C5 N4 C6 130.06(16) . . ?
 C5 N5 C3 104.26(16) . . ?
 C1 N3 C4 108.74(16) . . ?
 C1 N2 C2 118.27(16) . . ?
 C2 N1 C14 119.96(16) . . ?
 C2 N1 C15 123.23(16) . . ?
 C15 N1 C14 116.80(16) . . ?
 N3 C4 N4 125.36(17) . . ?
 N3 C4 C3 128.42(18) . . ?
 C3 C4 N4 106.21(17) . . ?
 N5 C3 C2 133.78(18) . . ?
 C4 C3 N5 110.39(17) . . ?
 C4 C3 C2 115.82(18) . . ?
 O1 C10 O2 124.9(2) . . ?
 O1 C10 C6 124.74(17) . . ?
 O2 C10 C6 110.30(17) . . ?
 N4 C5 H5 123.2 . . ?
 N5 C5 N4 113.58(17) . . ?
 N5 C5 H5 123.2 . . ?
 N2 C2 C3 116.95(17) . . ?
 N1 C2 N2 117.04(16) . . ?
 N1 C2 C3 126.01(18) . . ?
 N4 C6 C10 107.74(17) . . ?
 N4 C6 C7 112.90(16) . . ?
 N4 C6 C9 111.05(16) . . ?
 C10 C6 C7 109.76(16) . . ?
 C10 C6 C9 114.53(16) . . ?
 C9 C6 C7 100.88(17) . . ?
 N3 C1 Cl1 114.01(14) . . ?
 N2 C1 Cl1 114.30(14) . . ?
 N2 C1 N3 131.68(18) . . ?
 C6 C7 H7 108.4 . . ?
 C12 C7 C6 116.91(19) . . ?
 C12 C7 H7 108.4 . . ?
 C12 C7 C8 112.50(17) . . ?
 C8 C7 C6 101.93(16) . . ?
 C8 C7 H7 108.4 . . ?
 C7 C12 H12 117.7 . . ?
 C13 C12 C7 124.6(2) . . ?
 C13 C12 H12 117.7 . . ?
 N1 C14 H14A 109.5 . . ?
 N1 C14 H14B 109.5 . . ?
 N1 C14 H14C 109.5 . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?
 N1 C15 H15A 109.5 . . ?
 N1 C15 H15B 109.5 . . ?
 N1 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?
 O3 C9 C6 106.75(16) . . ?
 O3 C9 H9A 110.4 . . ?
 O3 C9 H9B 110.4 . . ?
 C6 C9 H9A 110.4 . . ?
 C6 C9 H9B 110.4 . . ?
 H9A C9 H9B 108.6 . . ?
 O3 C8 C7 107.96(16) . . ?
 O3 C8 H8A 110.1 . . ?
 O3 C8 H8B 110.1 . . ?
 C7 C8 H8A 110.1 . . ?
 C7 C8 H8B 110.1 . . ?
 H8A C8 H8B 108.4 . . ?
 C12 C13 H13A 122.1(18) . . ?
 C12 C13 H13B 121.8(19) . . ?
 H13A C13 H13B 116(3) . . ?
 O2 C11 H11A 109.5 . . ?
 O2 C11 H11B 109.5 . . ?
 O2 C11 H11C 109.5 . . ?
 H11A C11 H11B 109.5 . . ?
 H11A C11 H11C 109.5 . . ?
 H11B C11 H11C 109.5 . . ?


_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  1.194
_oxdiff_exptl_absorpt_empirical_full_min  0.862
