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

####################################################################### 
# 
# 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_18071z
_database_code_depnum_ccdc_archive 'CCDC 1880131'
loop_
_audit_author_name
_audit_author_address
'Victor Young'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2018-11-20 deposited with the CCDC.	2019-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            18071z
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 Cl N4, C3 H3 O2, C3 H4 O2'
_chemical_formula_sum            'C18 H21 Cl N4 O4'
_chemical_formula_weight         392.84

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.6312(4)
_cell_length_b                   12.1271(7)
_cell_length_c                   12.3925(7)
_cell_angle_alpha                97.657(2)
_cell_angle_beta                 95.471(2)
_cell_angle_gamma                102.874(2)
_cell_volume                     954.76(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2998
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      30.55

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_exptl_special_details           'Dr. N. Duggirala / Prof. R. Suryanarayanan'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   micro-focus
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15122
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.602
_diffrn_reflns_theta_max         30.574
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5797
_reflns_number_gt                4775
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0424P)²+0.5537P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5797
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_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 0.80119(17) 0.71639(9) 0.65618(9) 0.0145(2) Uani 1 1 d . . . . .
C2 C 0.87678(17) 0.63241(9) 0.58901(9) 0.0146(2) Uani 1 1 d . . . . .
N1 N 0.78162(15) 0.58311(8) 0.48751(8) 0.01546(18) Uani 1 1 d . . . . .
C3 C 0.60971(17) 0.61358(9) 0.45046(9) 0.0150(2) Uani 1 1 d . . . . .
N2 N 0.52810(15) 0.69019(8) 0.51132(8) 0.01601(18) Uani 1 1 d . . . . .
H2A H 0.408(3) 0.7106(16) 0.4799(15) 0.036(5) Uiso 1 1 d . . . . .
C4 C 0.62307(17) 0.74220(9) 0.61419(9) 0.0150(2) Uani 1 1 d . . . . .
N3 N 1.04659(16) 0.60063(9) 0.62619(8) 0.0182(2) Uani 1 1 d . . . . .
H3A H 1.087(3) 0.5447(14) 0.5884(13) 0.022 Uiso 1 1 d . U . . .
H3B H 1.108(3) 0.6243(14) 0.6953(14) 0.022 Uiso 1 1 d . U . . .
N4 N 0.50990(16) 0.56699(9) 0.35051(8) 0.01819(19) Uani 1 1 d . . . . .
H4A H 0.566(3) 0.5220(14) 0.3101(14) 0.022 Uiso 1 1 d . U . . .
H4B H 0.390(3) 0.5868(14) 0.3282(13) 0.022 Uiso 1 1 d . U . . .
C5 C 0.52022(18) 0.82693(10) 0.67201(10) 0.0188(2) Uani 1 1 d . . . . .
H5A H 0.5652 0.8378 0.7520 0.023 Uiso 1 1 calc R U . . .
H5B H 0.3671 0.7963 0.6593 0.023 Uiso 1 1 calc R U . . .
C6 C 0.5744(2) 0.94244(11) 0.63209(11) 0.0258(3) Uani 1 1 d . . . . .
H6A H 0.5034 0.9953 0.6710 0.039 Uiso 1 1 calc R U . . .
H6B H 0.5290 0.9321 0.5530 0.039 Uiso 1 1 calc R U . . .
H6C H 0.7256 0.9741 0.6466 0.039 Uiso 1 1 calc R U . . .
C7 C 0.91546(17) 0.77101(10) 0.76627(9) 0.0157(2) Uani 1 1 d . . . . .
C8 C 0.8907(2) 0.71488(11) 0.85682(10) 0.0228(2) Uani 1 1 d . . . . .
H8 H 0.7985 0.6412 0.8482 0.027 Uiso 1 1 calc R U . . .
C9 C 0.9990(2) 0.76513(13) 0.95978(11) 0.0274(3) Uani 1 1 d . . . . .
H9 H 0.9814 0.7265 1.0213 0.033 Uiso 1 1 calc R U . . .
C10 C 1.1326(2) 0.87218(13) 0.97060(11) 0.0270(3) Uani 1 1 d . . . . .
C11 C 1.1613(2) 0.93009(12) 0.88254(12) 0.0285(3) Uani 1 1 d . . . . .
H11 H 1.2538 1.0037 0.8917 0.034 Uiso 1 1 calc R U . . .
C12 C 1.05232(19) 0.87868(11) 0.77995(11) 0.0223(2) Uani 1 1 d . . . . .
H12 H 1.0715 0.9175 0.7186 0.027 Uiso 1 1 calc R U . . .
Cl1 Cl 1.26879(6) 0.93483(4) 1.09926(3) 0.04437(13) Uani 1 1 d . . . . .
O1 O 0.21601(15) 0.77182(8) 0.43045(8) 0.0270(2) Uani 1 1 d . . . . .
O2 O 0.12532(14) 0.63710(8) 0.28201(8) 0.0249(2) Uani 1 1 d . . . . .
C13 C 0.10142(18) 0.72529(11) 0.34336(11) 0.0203(2) Uani 1 1 d . . . . .
C14 C -0.0780(2) 0.77419(12) 0.30760(12) 0.0249(3) Uani 1 1 d . . . . .
H14 H -0.1530 0.7464 0.2364 0.030 Uiso 1 1 calc R U . . .
C15 C -0.1355(2) 0.85453(12) 0.37164(14) 0.0302(3) Uani 1 1 d . . . . .
H15A H -0.0623 0.8834 0.4431 0.036 Uiso 1 1 calc R U . . .
H15B H -0.2500 0.8835 0.3463 0.036 Uiso 1 1 calc R U . . .
O3 O -0.10874(16) 0.54533(9) 0.10801(8) 0.0298(2) Uani 1 1 d . . . . .
H3C H -0.030(3) 0.5777(16) 0.1820(16) 0.036 Uiso 1 1 d . U . . .
O4 O -0.32873(15) 0.41934(8) 0.18500(8) 0.0255(2) Uani 1 1 d . . . . .
C16 C -0.2632(2) 0.45607(12) 0.10420(10) 0.0230(2) Uani 1 1 d . . . . .
C17 C -0.3504(2) 0.40255(14) -0.01100(11) 0.0300(3) Uani 1 1 d . . . . .
H17 H -0.3087 0.4422 -0.0694 0.036 Uiso 1 1 calc R U . . .
C18 C -0.4828(2) 0.30242(15) -0.03374(13) 0.0357(3) Uani 1 1 d . . . . .
H18A H -0.5257 0.2619 0.0239 0.043 Uiso 1 1 calc R U . . .
H18B H -0.5360 0.2702 -0.1079 0.043 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
C1 C4 1.3619(15) . ?
C1 C2 1.4362(15) . ?
C1 C7 1.4875(15) . ?
C2 N3 1.3306(14) . ?
C2 N1 1.3483(14) . ?
N1 C3 1.3342(14) . ?
C3 N4 1.3349(14) . ?
C3 N2 1.3564(14) . ?
N2 C4 1.3694(14) . ?
N2 H2A 0.952(19) . ?
C4 C5 1.4979(15) . ?
N3 H3A 0.879(17) . ?
N3 H3B 0.893(17) . ?
N4 H4A 0.860(17) . ?
N4 H4B 0.908(17) . ?
C5 C6 1.5266(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.3922(17) . ?
C7 C12 1.3932(16) . ?
C8 C9 1.3922(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(2) . ?
C10 Cl1 1.7412(13) . ?
C11 C12 1.3928(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
O1 C13 1.2453(15) . ?
O2 C13 1.2763(16) . ?
C13 C14 1.4992(17) . ?
C14 C15 1.320(2) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
O3 C16 1.3062(17) . ?
O3 H3C 0.995(19) . ?
O4 C16 1.2269(17) . ?
C16 C17 1.4907(17) . ?
C17 C18 1.308(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9500 . ?
C18 H18B 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
C4 C1 C2 116.91(10) . . ?
C4 C1 C7 122.75(10) . . ?
C2 C1 C7 120.33(10) . . ?
N3 C2 N1 117.52(10) . . ?
N3 C2 C1 120.12(10) . . ?
N1 C2 C1 122.36(10) . . ?
C3 N1 C2 117.73(9) . . ?
N1 C3 N4 119.91(10) . . ?
N1 C3 N2 122.50(10) . . ?
N4 C3 N2 117.58(10) . . ?
C3 N2 C4 120.82(10) . . ?
C3 N2 H2A 118.9(11) . . ?
C4 N2 H2A 120.1(11) . . ?
C1 C4 N2 119.64(10) . . ?
C1 C4 C5 124.67(10) . . ?
N2 C4 C5 115.68(10) . . ?
C2 N3 H3A 120.8(11) . . ?
C2 N3 H3B 121.5(10) . . ?
H3A N3 H3B 116.5(15) . . ?
C3 N4 H4A 117.7(11) . . ?
C3 N4 H4B 118.3(10) . . ?
H4A N4 H4B 123.9(15) . . ?
C4 C5 C6 111.76(10) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 118.87(11) . . ?
C8 C7 C1 120.78(10) . . ?
C12 C7 C1 120.34(11) . . ?
C7 C8 C9 120.99(12) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 118.66(13) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 121.88(12) . . ?
C11 C10 Cl1 119.45(11) . . ?
C9 C10 Cl1 118.67(11) . . ?
C10 C11 C12 118.85(12) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C7 120.75(12) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
O1 C13 O2 124.17(11) . . ?
O1 C13 C14 118.68(12) . . ?
O2 C13 C14 117.15(11) . . ?
C15 C14 C13 122.29(13) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C16 O3 H3C 115.6(11) . . ?
O4 C16 O3 124.64(12) . . ?
O4 C16 C17 123.58(13) . . ?
O3 C16 C17 111.78(12) . . ?
C18 C17 C16 121.68(15) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?

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
C4 C1 C2 N3 -178.06(10) . . . . ?
C7 C1 C2 N3 1.85(16) . . . . ?
C4 C1 C2 N1 2.02(16) . . . . ?
C7 C1 C2 N1 -178.08(10) . . . . ?
N3 C2 N1 C3 179.12(10) . . . . ?
C1 C2 N1 C3 -0.95(16) . . . . ?
C2 N1 C3 N4 -179.92(10) . . . . ?
C2 N1 C3 N2 -0.81(16) . . . . ?
N1 C3 N2 C4 1.47(17) . . . . ?
N4 C3 N2 C4 -179.41(10) . . . . ?
C2 C1 C4 N2 -1.34(16) . . . . ?
C7 C1 C4 N2 178.76(10) . . . . ?
C2 C1 C4 C5 179.73(10) . . . . ?
C7 C1 C4 C5 -0.17(18) . . . . ?
C3 N2 C4 C1 -0.29(16) . . . . ?
C3 N2 C4 C5 178.73(10) . . . . ?
C1 C4 C5 C6 99.30(14) . . . . ?
N2 C4 C5 C6 -79.66(13) . . . . ?
C4 C1 C7 C8 99.30(14) . . . . ?
C2 C1 C7 C8 -80.60(14) . . . . ?
C4 C1 C7 C12 -81.85(15) . . . . ?
C2 C1 C7 C12 98.25(13) . . . . ?
C12 C7 C8 C9 0.44(19) . . . . ?
C1 C7 C8 C9 179.30(11) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C8 C9 C10 Cl1 -179.78(10) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
Cl1 C10 C11 C12 179.63(10) . . . . ?
C10 C11 C12 C7 0.4(2) . . . . ?
C8 C7 C12 C11 -0.60(18) . . . . ?
C1 C7 C12 C11 -179.46(11) . . . . ?
O1 C13 C14 C15 -9.2(2) . . . . ?
O2 C13 C14 C15 170.19(13) . . . . ?
O4 C16 C17 C18 -10.4(2) . . . . ?
O3 C16 C17 C18 168.99(13) . . . . ?

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
N2 H2A O1 0.952(19) 1.712(19) 2.6550(13) 169.8(17) .
N3 H3A N1 0.879(17) 2.101(17) 2.9747(14) 172.8(15) 2_766
N3 H3B O4 0.893(17) 2.183(17) 2.9244(14) 140.1(14) 2_666
N4 H4A O4 0.860(17) 2.126(17) 2.9751(14) 169.1(15) 1_655
N4 H4B O2 0.908(17) 2.041(17) 2.9484(14) 177.9(15) .
O3 H3C O2 0.995(19) 1.517(19) 2.5000(14) 168.5(18) .

_refine_diff_density_max         0.646
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6

