# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mo_ch240_0m
_database_code_depnum_ccdc_archive 'CCDC 1537492'
_audit_update_record             
;
2017-03-12 deposited with the CCDC.
2017-06-29 downloaded from the CCDC.
;
_audit_creation_date             2015-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 Cl N4 O'
_chemical_formula_sum            'C12 H13 Cl N4 O'
_chemical_formula_weight         264.71
_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'
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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6687(9)
_cell_length_b                   9.7813(11)
_cell_length_c                   9.8658(11)
_cell_angle_alpha                116.485(3)
_cell_angle_beta                 91.631(3)
_cell_angle_gamma                102.325(3)
_cell_volume                     640.60(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5585
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0398 before and 0.0349 after correction.
The Ratio of minimum to maximum transmission is 0.9100.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11582
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.330
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2620
_reflns_number_total             2935
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.027
_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)+(0.0323P)²+0.4205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0857
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(Cl1A)
3. Others
 Sof(H7)=Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=Sof(H5)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C7(H7), C6(H6), C5(H5)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_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 0.16688(6) 0.35055(5) -0.05030(5) 0.02760(12) Uani 0.8396(8) 1 d . . P A
1
O1 O 0.69275(12) 0.96542(11) 0.46745(11) 0.0212(2) Uani 1 1 d . . . . .
N4 N 0.67841(14) 0.74058(12) 0.60173(12) 0.0140(2) Uani 1 1 d . . . . .
N1 N 0.39059(14) 0.69843(13) 0.53614(13) 0.0177(2) Uani 1 1 d . . . . .
N3 N 0.58919(14) 0.67405(14) 0.68190(13) 0.0183(2) Uani 1 1 d . . . . .
N2 N 0.41784(15) 0.65037(14) 0.64287(13) 0.0196(2) Uani 1 1 d . . . . .
C1 C 0.55319(16) 0.75409(14) 0.51238(14) 0.0144(2) Uani 1 1 d . . . . .
C2 C 0.58341(16) 0.83835(15) 0.41599(15) 0.0159(3) Uani 1 1 d . . . . .
C8 C 0.37733(17) 0.60677(16) 0.18984(15) 0.0184(3) Uani 1 1 d . . . . .
H8 H 0.3756 0.5419 0.2386 0.022 Uiso 1 1 calc R . . . .
C9 C 0.88188(16) 0.77865(15) 0.61865(15) 0.0160(3) Uani 1 1 d . . . . .
C3 C 0.47272(17) 0.76502(16) 0.26347(15) 0.0177(3) Uani 1 1 d . . . . .
C10 C 0.93823(17) 0.73221(16) 0.46007(15) 0.0193(3) Uani 1 1 d . . . . .
H10A H 0.8739 0.6228 0.3905 0.029 Uiso 1 1 calc GR . . . .
H10B H 1.0684 0.7419 0.4666 0.029 Uiso 1 1 calc GR . . . .
H10C H 0.9086 0.8021 0.4213 0.029 Uiso 1 1 calc GR . . . .
C4 C 0.4740(2) 0.85998(17) 0.19112(16) 0.0243(3) Uani 1 1 d . . . . .
H4 H 0.5390 0.9678 0.2414 0.029 Uiso 1 1 calc R . . . .
C11 C 0.95416(18) 0.95492(16) 0.72680(16) 0.0225(3) Uani 1 1 d . . . . .
H11A H 0.9059 1.0157 0.6854 0.034 Uiso 1 1 calc GR . . . .
H11B H 1.0861 0.9833 0.7369 0.034 Uiso 1 1 calc GR . . . .
H11C H 0.9168 0.9788 0.8274 0.034 Uiso 1 1 calc GR . . . .
C12 C 0.94393(18) 0.68004(18) 0.68541(17) 0.0225(3) Uani 1 1 d . . . . .
H12A H 0.9099 0.7114 0.7881 0.034 Uiso 1 1 calc GR . . . .
H12B H 1.0752 0.6975 0.6915 0.034 Uiso 1 1 calc GR . . . .
H12C H 0.8865 0.5680 0.6195 0.034 Uiso 1 1 calc GR . . . .
C7 C 0.28486(19) 0.54576(17) 0.04394(15) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.2199 0.4379 -0.0072 0.027 Uiso 0.1604(8) 1 calc R . P A 2
C6 C 0.2851(2) 0.63867(19) -0.02895(16) 0.0288(3) Uani 1 1 d . . . . .
H6 H 0.2210 0.5951 -0.1288 0.035 Uiso 1 1 calc R . . . .
C5 C 0.3799(2) 0.79572(19) 0.04607(18) 0.0323(4) Uani 1 1 d . . . . .
H5 H 0.3804 0.8603 -0.0029 0.039 Uiso 0.8396(8) 1 calc R . P A 1
Cl1A Cl 0.3412(3) 0.9140(3) -0.0253(2) 0.02760(12) Uani 0.1604(8) 1 d . . P A 2


_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 C7 1.7205(15) . ?
O1 C2 1.2140(16) . ?
N4 N3 1.3480(14) . ?
N4 C1 1.3515(16) . ?
N4 C9 1.5109(15) . ?
N1 N2 1.3581(16) . ?
N1 C1 1.3217(16) . ?
N3 N2 1.3002(16) . ?
C1 C2 1.5058(17) . ?
C2 C3 1.4846(18) . ?
C8 H8 0.9500 . ?
C8 C3 1.3936(19) . ?
C8 C7 1.3878(19) . ?
C9 C10 1.5262(18) . ?
C9 C11 1.5284(18) . ?
C9 C12 1.5281(18) . ?
C3 C4 1.4002(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C5 1.381(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.384(2) . ?
C5 H5 0.9500 . ?
C5 Cl1A 1.668(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
N3 N4 C1 107.18(10) . . ?
N3 N4 C9 120.10(10) . . ?
C1 N4 C9 132.66(10) . . ?
C1 N1 N2 105.58(10) . . ?
N2 N3 N4 107.29(10) . . ?
N3 N2 N1 110.66(10) . . ?
N4 C1 C2 127.78(11) . . ?
N1 C1 N4 109.28(11) . . ?
N1 C1 C2 122.41(11) . . ?
O1 C2 C1 119.02(12) . . ?
O1 C2 C3 122.52(12) . . ?
C3 C2 C1 118.41(11) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C3 118.70(13) . . ?
N4 C9 C10 108.24(10) . . ?
N4 C9 C11 107.94(10) . . ?
N4 C9 C12 107.85(10) . . ?
C10 C9 C11 112.36(11) . . ?
C10 C9 C12 109.49(11) . . ?
C12 C9 C11 110.81(11) . . ?
C8 C3 C2 122.51(12) . . ?
C8 C3 C4 120.31(12) . . ?
C4 C3 C2 117.12(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.53(14) . . ?
C5 C4 H4 120.2 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C7 Cl1 119.79(11) . . ?
C8 C7 H7 119.2 . . ?
C8 C7 C6 121.53(14) . . ?
C6 C7 Cl1 118.68(11) . . ?
C6 C7 H7 119.2 . . ?
C7 C6 H6 120.5 . . ?
C5 C6 C7 119.00(14) . . ?
C5 C6 H6 120.5 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 Cl1A 119.85(15) . . ?
C6 C5 C4 120.93(14) . . ?
C6 C5 H5 119.5 . . ?
C6 C5 Cl1A 117.86(14) . . ?

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 C7 C6 C5 -179.88(12) . . . . ?
O1 C2 C3 C8 165.58(12) . . . . ?
O1 C2 C3 C4 -11.43(19) . . . . ?
N4 N3 N2 N1 0.71(14) . . . . ?
N4 C1 C2 O1 -41.32(19) . . . . ?
N4 C1 C2 C3 140.95(13) . . . . ?
N1 C1 C2 O1 129.41(13) . . . . ?
N1 C1 C2 C3 -48.32(17) . . . . ?
N3 N4 C1 N1 0.25(14) . . . . ?
N3 N4 C1 C2 171.97(12) . . . . ?
N3 N4 C9 C10 137.93(11) . . . . ?
N3 N4 C9 C11 -100.21(13) . . . . ?
N3 N4 C9 C12 19.56(15) . . . . ?
N2 N1 C1 N4 0.17(14) . . . . ?
N2 N1 C1 C2 -172.08(11) . . . . ?
C1 N4 N3 N2 -0.58(14) . . . . ?
C1 N4 C9 C10 -39.08(18) . . . . ?
C1 N4 C9 C11 82.77(16) . . . . ?
C1 N4 C9 C12 -157.45(13) . . . . ?
C1 N1 N2 N3 -0.55(14) . . . . ?
C1 C2 C3 C8 -16.78(18) . . . . ?
C1 C2 C3 C4 166.22(11) . . . . ?
C2 C3 C4 C5 177.07(13) . . . . ?
C8 C3 C4 C5 0.0(2) . . . . ?
C8 C7 C6 C5 0.0(2) . . . . ?
C9 N4 N3 N2 -178.29(11) . . . . ?
C9 N4 C1 N1 177.55(12) . . . . ?
C9 N4 C1 C2 -10.7(2) . . . . ?
C3 C8 C7 Cl1 179.65(10) . . . . ?
C3 C8 C7 C6 -0.3(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C3 C4 C5 Cl1A 166.17(14) . . . . ?
C7 C8 C3 C2 -176.67(12) . . . . ?
C7 C8 C3 C4 0.25(19) . . . . ?
C7 C6 C5 C4 0.2(2) . . . . ?
C7 C6 C5 Cl1A -166.44(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
