# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_20190325-xiayi-zyh-716
_database_code_depnum_ccdc_archive 'CCDC 1905957'
loop_
_audit_author_name
_audit_author_address
'Yanhua Zhang'
;Chongqing University
China
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2020-11-17 downloaded from the CCDC.
;
_audit_creation_date             2019-03-25
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H13 Cl N4 O'
_chemical_formula_sum            'C11 H13 Cl N4 O'
_chemical_formula_weight         252.70
_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 0.0033 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'

_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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   4.4944(6)
_cell_length_b                   5.4263(7)
_cell_length_c                   12.2978(16)
_cell_angle_alpha                97.735(11)
_cell_angle_beta                 94.192(11)
_cell_angle_gamma                92.200(11)
_cell_volume                     296.04(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    528
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      3.9180
_cell_measurement_theta_max      22.6840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_min  0.31624
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             132
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2050
_diffrn_reflns_point_group_measured_fraction_full 0.611
_diffrn_reflns_point_group_measured_fraction_max 0.511
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.948
_diffrn_reflns_theta_min         3.794
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.200
_reflns_Friedel_fraction_full    0.224
_reflns_Friedel_fraction_max     0.170
_reflns_number_gt                1203
_reflns_number_total             1604
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_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     158
_refine_ls_number_reflns         1604
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.044
_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)+(0.0529P)²+0.0062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1135
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C1(H1B,H1C)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C11(H11), C7(H7), C8(H8)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 -0.4004(3) 0.8335(2) 0.09751(13) 0.0789(5) Uani 1 1 d . . . . .
N2 N 0.3510(8) 0.5634(7) 0.4737(3) 0.0440(9) Uani 1 1 d . . . . .
O1 O 1.4005(7) 0.0985(6) 0.8128(3) 0.0637(10) Uani 1 1 d . . . . .
H1 H 1.5408 0.1891 0.8005 0.096 Uiso 1 1 calc GR . . . .
N1 N 0.9034(8) 0.3959(7) 0.7750(3) 0.0433(9) Uani 1 1 d . . . . .
H1A H 0.991(11) 0.318(10) 0.725(4) 0.052 Uiso 1 1 d R . . . .
N3 N 0.4711(10) 0.3388(8) 0.4682(4) 0.0623(12) Uani 1 1 d . . . . .
C6 C 0.1595(9) 0.6245(8) 0.3846(4) 0.0430(11) Uani 1 1 d . . . . .
N4 N 0.6424(10) 0.3377(8) 0.5594(4) 0.0626(12) Uani 1 1 d . . . . .
C5 C 0.4529(10) 0.7056(8) 0.5690(4) 0.0474(11) Uani 1 1 d . . . . .
H5 H 0.4070 0.8689 0.5924 0.057 Uiso 1 1 calc R . . . .
C3 C 0.8171(10) 0.6221(8) 0.7303(4) 0.0441(10) Uani 1 1 d . . . . .
H3A H 0.9953 0.7201 0.7201 0.053 Uiso 1 1 calc R . . . .
H3B H 0.7031 0.7213 0.7826 0.053 Uiso 1 1 calc R . . . .
C4 C 0.6356(9) 0.5623(8) 0.6237(4) 0.0451(11) Uani 1 1 d . . . . .
C10 C -0.0369(11) 0.5336(9) 0.1961(4) 0.0596(14) Uani 1 1 d . . . . .
H10 H -0.0529 0.4312 0.1287 0.072 Uiso 1 1 calc R . . . .
C9 C -0.1909(10) 0.7486(9) 0.2102(4) 0.0514(12) Uani 1 1 d . . . . .
C2 C 1.1144(10) 0.4531(8) 0.8721(4) 0.0490(11) Uani 1 1 d . . . . .
H2A H 1.0118 0.5296 0.9338 0.059 Uiso 1 1 calc R . . . .
H2B H 1.2703 0.5704 0.8577 0.059 Uiso 1 1 calc R . . . .
C11 C 0.1422(11) 0.4726(9) 0.2842(4) 0.0550(13) Uani 1 1 d . . . . .
H11 H 0.2508 0.3297 0.2759 0.066 Uiso 1 1 calc R . . . .
C7 C -0.0043(10) 0.8345(9) 0.3979(4) 0.0485(11) Uani 1 1 d . . . . .
H7 H 0.0028 0.9341 0.4659 0.058 Uiso 1 1 calc R . . . .
C8 C -0.1779(10) 0.8948(9) 0.3098(4) 0.0521(12) Uani 1 1 d . . . . .
H8 H -0.2878 1.0370 0.3181 0.062 Uiso 1 1 calc R . . . .
C1 C 1.2519(11) 0.2177(9) 0.9006(4) 0.0571(13) Uani 1 1 d . . . . .
H1B H 1.3926 0.2585 0.9648 0.069 Uiso 1 1 calc R . . . .
H1C H 1.0965 0.1050 0.9190 0.069 Uiso 1 1 calc R . . . .


_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 C9 1.742(5) . ?
N2 N3 1.347(5) . ?
N2 C6 1.426(5) . ?
N2 C5 1.352(6) . ?
O1 H1 0.8200 . ?
O1 C1 1.408(6) . ?
N1 H1A 0.83(5) . ?
N1 C3 1.465(5) . ?
N1 C2 1.460(5) . ?
N3 N4 1.315(6) . ?
C6 C11 1.385(6) . ?
C6 C7 1.378(6) . ?
N4 C4 1.363(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.356(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.483(6) . ?
C10 H10 0.9300 . ?
C10 C9 1.377(6) . ?
C10 C11 1.386(7) . ?
C9 C8 1.362(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.512(6) . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.372(7) . ?
C8 H8 0.9300 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?

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 N2 C6 120.6(4) . . ?
N3 N2 C5 109.7(4) . . ?
C5 N2 C6 129.7(4) . . ?
C1 O1 H1 109.5 . . ?
C3 N1 H1A 104(4) . . ?
C2 N1 H1A 108(3) . . ?
C2 N1 C3 111.5(4) . . ?
N4 N3 N2 107.3(4) . . ?
C11 C6 N2 119.4(4) . . ?
C7 C6 N2 120.3(4) . . ?
C7 C6 C11 120.3(4) . . ?
N3 N4 C4 109.4(4) . . ?
N2 C5 H5 126.9 . . ?
N2 C5 C4 106.2(4) . . ?
C4 C5 H5 126.9 . . ?
N1 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
N1 C3 C4 111.5(4) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
N4 C4 C3 122.1(4) . . ?
C5 C4 N4 107.5(4) . . ?
C5 C4 C3 130.3(4) . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.7(5) . . ?
C11 C10 H10 120.6 . . ?
C10 C9 Cl1 118.7(4) . . ?
C8 C9 Cl1 120.3(4) . . ?
C8 C9 C10 121.1(4) . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
N1 C2 C1 110.1(4) . . ?
H2A C2 H2B 108.2 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C6 C11 C10 120.0(4) . . ?
C6 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.2(5) . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
O1 C1 C2 111.6(4) . . ?
O1 C1 H1B 109.3 . . ?
O1 C1 H1C 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C2 C1 H1C 109.3 . . ?
H1B C1 H1C 108.0 . . ?

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
Cl1 C9 C8 C7 -177.5(4) . . . . ?
N2 N3 N4 C4 -0.5(6) . . . . ?
N2 C6 C11 C10 -178.3(4) . . . . ?
N2 C6 C7 C8 177.4(4) . . . . ?
N2 C5 C4 N4 0.7(5) . . . . ?
N2 C5 C4 C3 177.7(4) . . . . ?
N1 C3 C4 N4 -21.6(6) . . . . ?
N1 C3 C4 C5 161.8(4) . . . . ?
N1 C2 C1 O1 58.5(5) . . . . ?
N3 N2 C6 C11 -12.4(6) . . . . ?
N3 N2 C6 C7 168.4(5) . . . . ?
N3 N2 C5 C4 -1.1(5) . . . . ?
N3 N4 C4 C5 -0.1(6) . . . . ?
N3 N4 C4 C3 -177.4(4) . . . . ?
C6 N2 N3 N4 178.2(3) . . . . ?
C6 N2 C5 C4 -177.9(4) . . . . ?
C6 C7 C8 C9 0.5(7) . . . . ?
C5 N2 N3 N4 1.0(6) . . . . ?
C5 N2 C6 C11 164.2(5) . . . . ?
C5 N2 C6 C7 -15.1(6) . . . . ?
C3 N1 C2 C1 -167.2(4) . . . . ?
C10 C9 C8 C7 1.7(7) . . . . ?
C9 C10 C11 C6 1.2(7) . . . . ?
C2 N1 C3 C4 172.4(3) . . . . ?
C11 C6 C7 C8 -1.8(7) . . . . ?
C11 C10 C9 Cl1 176.7(4) . . . . ?
C11 C10 C9 C8 -2.5(7) . . . . ?
C7 C6 C11 C10 1.0(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
