# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_ltl-20210329
_database_code_depnum_ccdc_archive 'CCDC 2083882'
loop_
_audit_author_name
_audit_author_address
'Li-Qing Ren'
;Southwest University
China
;
_audit_update_record             
;
2021-05-15 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2021-03-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H17 Cl N4 O4'
_chemical_formula_sum            'C18 H17 Cl N4 O4'
_chemical_formula_weight         388.80
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'C1 H1 O1 N1 Cl1'
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      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                   9.5440(4)
_cell_length_b                   9.6083(3)
_cell_length_c                   10.9794(4)
_cell_angle_alpha                100.755(3)
_cell_angle_beta                 109.708(4)
_cell_angle_gamma                99.226(3)
_cell_volume                     903.66(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8948
_cell_measurement_temperature    290.3(2)
_cell_measurement_theta_max      71.7720
_cell_measurement_theta_min      4.4250
_shelx_estimated_absorpt_T_max   0.554
_shelx_estimated_absorpt_T_min   0.463
_exptl_absorpt_coefficient_mu    2.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16127
_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_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16234
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.346
_diffrn_reflns_theta_min         4.429
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.3(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -19.00   1.00    1.00    --  -35.72 -57.00 -30.00   84
  2  ω    -90.00  -3.00   1.00    1.00    --  -35.72 126.00  90.00   87
  3  ω    -62.00  32.00   1.00    1.00    --  -35.72  77.00  30.00   94
  4  ω    -32.00  52.00   1.00    1.00    --   35.72 -57.00-180.00   84
  5  ω     24.00  90.00   1.00    1.00    --   35.72-126.00   0.00   66
  6  ω     19.00 103.00   1.00    1.00    --   35.72  57.00 -90.00   84
  7  ω     19.00 103.00   1.00    1.00    --   35.72  57.00 -60.00   84
  8  ω    -32.00  52.00   1.00    1.00    --   35.72 -57.00  60.00   84
  9  ω    101.00 178.00   1.00    1.00    --  107.97 112.00  60.00   77
 10  ω     79.00 178.00   1.00    1.00    --  107.97  19.00  62.00   99
 11  ω     40.00 125.00   1.00    1.00    --  107.97 -45.00 150.00   85
 12  ω     38.00 112.00   1.00    1.00    --  107.97-112.00-180.00   74
 13  ω     41.00 126.00   1.00    1.00    --  107.97 -61.00 -30.00   85
 14  ω     40.00 125.00   1.00    1.00    --  107.97 -45.00-120.00   85
 15  ω     38.00 112.00   1.00    1.00    --  107.97-112.00   0.00   74
 16  ω     87.00 178.00   1.00    1.00    --  107.97  30.00 120.00   91
 17  ω     90.00 175.00   1.00    1.00    --  107.97  61.00 150.00   85
 18  ω    101.00 178.00   1.00    1.00    --  107.97 112.00 -30.00   77
 19  ω     91.00 176.00   1.00    1.00    --  107.97  45.00  60.00   85
 20  ω     38.00 112.00   1.00    1.00    --  107.97-112.00-120.00   74
 21  ω     39.00 110.00   1.00    1.00    --  107.97 -95.00  60.00   71
 22  ω     40.00 125.00   1.00    1.00    --  107.97 -45.00  60.00   85
 23  ω     39.00 110.00   1.00    1.00    --  107.97 -95.00 -90.00   71
 24  ω      9.00 103.00   1.00    1.00    --   35.72  77.00-180.00   94
 25  ω      9.00 103.00   1.00    1.00    --   35.72  77.00 120.00   94
 26  ω    -33.00  55.00   1.00    1.00    --   35.72 -38.00 -90.00   88
 27  ω      9.00 103.00   1.00    1.00    --   35.72  77.00  60.00   94
 28  ω      9.00 103.00   1.00    1.00    --   35.72  77.00 -30.00   94
 29  ω     17.00 105.00   1.00    1.00    --   35.72  38.00  90.00   88
 30  ω     70.00 178.00   1.00    1.00    --  107.97  15.00 -90.00  108
 31  ω     81.00 176.00   1.00    1.00    --  107.97  77.00 120.00   95
 32  ω     81.00 176.00   1.00    1.00    --  107.97  77.00-150.00   95
 33  ω     87.00 178.00   1.00    1.00    --  107.97  30.00 -60.00   91
 34  ω     81.00 176.00   1.00    1.00    --  107.97  77.00 -30.00   95
 35  ω     90.00 175.00   1.00    1.00    --  107.97  61.00-180.00   85
 36  ω     81.00 176.00   1.00    1.00    --  107.97  77.00-120.00   95
 37  ω     81.00 176.00   1.00    1.00    --  107.97  77.00  60.00   95
 38  ω     91.00 176.00   1.00    1.00    --  107.97  45.00-180.00   85
 39  ω     81.00 176.00   1.00    1.00    --  107.97  77.00   0.00   95
 40  ω     81.00 176.00   1.00    1.00    --  107.97  77.00 -60.00   95
 41  ω     87.00 178.00   1.00    1.00    --  107.97  30.00 -30.00   91
 42  ω   -107.00  -6.00   1.00    1.00    --  -35.72 -19.00 -30.00  101
 43  ω   -107.00  -6.00   1.00    1.00    --  -35.72 -19.00 150.00  101
 44  ω      9.00 103.00   1.00    1.00    --   35.72  77.00 -90.00   94
 45  ω      9.00 103.00   1.00    1.00    --   35.72  77.00  90.00   94
 46  ω      1.00  75.00   1.00    1.00    --   35.72 -99.00 -90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0137349000
_diffrn_orient_matrix_UB_12      0.1656592000
_diffrn_orient_matrix_UB_13      0.0381203000
_diffrn_orient_matrix_UB_21      0.1568499000
_diffrn_orient_matrix_UB_22      0.0284953000
_diffrn_orient_matrix_UB_23      -0.0136365000
_diffrn_orient_matrix_UB_31      -0.0801716000
_diffrn_orient_matrix_UB_32      -0.0053397000
_diffrn_orient_matrix_UB_33      -0.1489042000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3225
_reflns_number_total             3502
_reflns_odcompleteness_completeness 99.97
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.024
_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)+(0.0990P)²+0.1994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1512
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C12(H12), C15(H15),
 C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.13157(7) 0.13219(5) 0.47521(5) 0.0627(2) Uani 1 1 d . . . . .
O1 O 0.51327(19) 1.08569(16) 0.62117(16) 0.0619(4) Uani 1 1 d . . . . .
O2 O 0.6075(2) 1.26064(19) 0.79936(18) 0.0778(5) Uani 1 1 d . . . . .
O3 O 0.44684(19) 1.27837(17) 1.16036(16) 0.0637(4) Uani 1 1 d . . . . .
O4 O 0.2846(2) 1.0965(2) 1.16148(18) 0.0753(5) Uani 1 1 d . . . . .
N1 N 0.22187(16) 0.71105(14) 0.54806(14) 0.0387(3) Uani 1 1 d . . . . .
N2 N 0.31329(17) 0.85192(15) 0.60239(15) 0.0403(3) Uani 1 1 d . . . . .
H2 H 0.3636 0.8900 0.5600 0.048 Uiso 1 1 calc R . . . .
N3 N 0.51952(18) 1.14312(16) 0.73325(17) 0.0457(4) Uani 1 1 d . . . . .
N4 N 0.3586(2) 1.15836(19) 1.10682(17) 0.0499(4) Uani 1 1 d . . . . .
C1 C 0.2337(3) 0.4433(2) 0.8950(2) 0.0559(5) Uani 1 1 d . . . . .
H1 H 0.3131 0.5250 0.9164 0.067 Uiso 1 1 calc R . . . .
C2 C 0.1699(3) 0.4241(3) 0.9877(2) 0.0714(7) Uani 1 1 d . . . . .
H2A H 0.2060 0.4922 1.0703 0.086 Uiso 1 1 calc R . . . .
C3 C 0.0528(3) 0.3041(3) 0.9576(3) 0.0696(6) Uani 1 1 d . . . . .
H3 H 0.0092 0.2904 1.0199 0.084 Uiso 1 1 calc R . . . .
C4 C 0.0003(3) 0.2046(2) 0.8356(2) 0.0592(5) Uani 1 1 d . . . . .
H4 H -0.0792 0.1234 0.8153 0.071 Uiso 1 1 calc R . . . .
C5 C 0.0639(2) 0.2234(2) 0.7426(2) 0.0480(4) Uani 1 1 d . . . . .
H5 H 0.0270 0.1547 0.6602 0.058 Uiso 1 1 calc R . . . .
C6 C 0.1830(2) 0.34417(18) 0.77025(18) 0.0405(4) Uani 1 1 d . . . . .
C7 C 0.25633(19) 0.37850(18) 0.67773(18) 0.0421(4) Uani 1 1 d . . . . .
H7 H 0.3240 0.4702 0.7098 0.050 Uiso 1 1 calc R . . . .
C8 C 0.24700(19) 0.30718(18) 0.55837(18) 0.0398(4) Uani 1 1 d . . . . .
C9 C 0.3323(2) 0.3674(2) 0.4802(2) 0.0465(4) Uani 1 1 d . . . . .
H9A H 0.3938 0.3015 0.4612 0.056 Uiso 1 1 calc R . . . .
H9B H 0.4019 0.4604 0.5350 0.056 Uiso 1 1 calc R . . . .
C10 C 0.2295(2) 0.38933(19) 0.34896(18) 0.0434(4) Uani 1 1 d . . . . .
H10A H 0.1637 0.2955 0.2921 0.052 Uiso 1 1 calc R . . . .
H10B H 0.2931 0.4260 0.3036 0.052 Uiso 1 1 calc R . . . .
C11 C 0.1294(2) 0.49461(18) 0.36588(17) 0.0397(4) Uani 1 1 d . . . . .
H11A H 0.0578 0.4934 0.2783 0.048 Uiso 1 1 calc R . . . .
H11B H 0.0703 0.4618 0.4162 0.048 Uiso 1 1 calc R . . . .
C12 C 0.2217(2) 0.64667(18) 0.43646(17) 0.0386(4) Uani 1 1 d . . . . .
H12 H 0.2805 0.6953 0.3977 0.046 Uiso 1 1 calc R . . . .
C13 C 0.32302(18) 0.92880(17) 0.72152(17) 0.0360(4) Uani 1 1 d . . . . .
C14 C 0.42046(19) 1.07072(17) 0.78878(17) 0.0367(4) Uani 1 1 d . . . . .
C15 C 0.42888(19) 1.14557(18) 0.91283(18) 0.0392(4) Uani 1 1 d . . . . .
H15 H 0.4929 1.2386 0.9543 0.047 Uiso 1 1 calc R . . . .
C16 C 0.3427(2) 1.08180(19) 0.97356(17) 0.0403(4) Uani 1 1 d . . . . .
C17 C 0.2441(2) 0.9434(2) 0.9112(2) 0.0474(4) Uani 1 1 d . . . . .
H17 H 0.1845 0.9019 0.9530 0.057 Uiso 1 1 calc R . . . .
C18 C 0.2350(2) 0.86923(19) 0.78944(19) 0.0448(4) Uani 1 1 d . . . . .
H18 H 0.1693 0.7768 0.7495 0.054 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 C8 1.7404(17) . ?
O1 N3 1.228(2) . ?
O2 N3 1.219(2) . ?
O3 N4 1.219(2) . ?
O4 N4 1.224(2) . ?
N1 N2 1.3850(19) . ?
N1 C12 1.265(2) . ?
N2 C13 1.342(2) . ?
N3 C14 1.444(2) . ?
N4 C16 1.455(2) . ?
C1 C2 1.375(3) . ?
C1 C6 1.392(3) . ?
C2 C3 1.373(4) . ?
C3 C4 1.370(3) . ?
C4 C5 1.377(3) . ?
C5 C6 1.394(3) . ?
C6 C7 1.470(3) . ?
C7 C8 1.327(3) . ?
C8 C9 1.497(2) . ?
C9 C10 1.519(3) . ?
C10 C11 1.527(2) . ?
C11 C12 1.489(2) . ?
C13 C14 1.423(2) . ?
C13 C18 1.420(2) . ?
C14 C15 1.386(2) . ?
C15 C16 1.363(3) . ?
C16 C17 1.395(3) . ?
C17 C18 1.360(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
C12 N1 N2 115.11(14) . . ?
C13 N2 N1 119.72(14) . . ?
O1 N3 C14 119.64(15) . . ?
O2 N3 O1 121.58(17) . . ?
O2 N3 C14 118.78(16) . . ?
O3 N4 O4 122.94(18) . . ?
O3 N4 C16 119.28(17) . . ?
O4 N4 C16 117.75(17) . . ?
C2 C1 C6 121.9(2) . . ?
C3 C2 C1 119.7(2) . . ?
C4 C3 C2 119.7(2) . . ?
C3 C4 C5 120.7(2) . . ?
C4 C5 C6 120.86(19) . . ?
C1 C6 C5 117.06(18) . . ?
C1 C6 C7 117.13(17) . . ?
C5 C6 C7 125.78(17) . . ?
C8 C7 C6 133.95(16) . . ?
C7 C8 Cl1 123.05(14) . . ?
C7 C8 C9 124.30(16) . . ?
C9 C8 Cl1 112.65(14) . . ?
C8 C9 C10 113.96(15) . . ?
C9 C10 C11 113.82(14) . . ?
C12 C11 C10 112.18(14) . . ?
N1 C12 C11 121.32(15) . . ?
N2 C13 C14 123.77(15) . . ?
N2 C13 C18 120.48(15) . . ?
C18 C13 C14 115.74(15) . . ?
C13 C14 N3 121.79(15) . . ?
C15 C14 N3 116.23(15) . . ?
C15 C14 C13 121.96(16) . . ?
C16 C15 C14 119.50(16) . . ?
C15 C16 N4 118.93(16) . . ?
C15 C16 C17 120.79(16) . . ?
C17 C16 N4 120.25(17) . . ?
C18 C17 C16 120.12(17) . . ?
C17 C18 C13 121.88(16) . . ?

_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 4.850
_oxdiff_exptl_absorpt_empirical_full_min 0.495
####################################################################### 
# 
# 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_ltl-2021-04-07
_database_code_depnum_ccdc_archive 'CCDC 2083883'
loop_
_audit_author_name
_audit_author_address
'Li-Qing Ren'
;Southwest University
China
;
_audit_update_record             
;
2021-05-15 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2021-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H17 Cl N4 O4'
_chemical_formula_sum            'C18 H17 Cl N4 O4'
_chemical_formula_weight         388.80
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'C1 H1 O1 N1 Cl1'
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      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                   7.5823(2)
_cell_length_b                   11.0627(3)
_cell_length_c                   11.5599(4)
_cell_angle_alpha                104.955(3)
_cell_angle_beta                 101.519(3)
_cell_angle_gamma                98.541(2)
_cell_volume                     897.21(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9688
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      71.6690
_cell_measurement_theta_min      4.0780
_shelx_estimated_absorpt_T_max   0.524
_shelx_estimated_absorpt_T_min   0.469
_exptl_absorpt_coefficient_mu    2.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24471
_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_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.34
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16174
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.814
_diffrn_reflns_theta_min         4.087
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -17.00   1.00    1.00    --  -35.97 -38.00 120.00   88
  2  ω    -53.00  31.00   1.00    1.00    --  -35.97  57.00 -90.00   84
  3  ω    -90.00  -3.00   1.00    1.00    --  -35.97 126.00 -90.00   87
  4  ω      9.00 104.00   1.00    1.00    --   35.97  77.00-180.00   95
  5  ω    -32.00  63.00   1.00    1.00    --   35.97 -77.00  30.00   95
  6  ω     19.00 103.00   1.00    1.00    --   35.97  57.00 -60.00   84
  7  ω     24.00  90.00   1.00    1.00    --   35.97-126.00-180.00   66
  8  ω    -31.00  53.00   1.00    1.00    --   35.97 -57.00  60.00   84
  9  ω     39.00 110.00   1.00    1.00    --  107.97 -95.00-150.00   71
 10  ω     38.00 112.00   1.00    1.00    --  107.97-112.00  90.00   74
 11  ω     40.00 125.00   1.00    1.00    --  107.97 -45.00-180.00   85
 12  ω     90.00 175.00   1.00    1.00    --  107.97  61.00 150.00   85
 13  ω     40.00 135.00   1.00    1.00    --  107.97 -77.00 -60.00   95
 14  ω    101.00 178.00   1.00    1.00    --  107.97 112.00  90.00   77
 15  ω     40.00 125.00   1.00    1.00    --  107.97 -45.00  90.00   85
 16  ω     38.00 112.00   1.00    1.00    --  107.97-112.00 -30.00   74
 17  ω     40.00 125.00   1.00    1.00    --  107.97 -45.00 -60.00   85
 18  ω     40.00 125.00   1.00    1.00    --  107.97 -45.00  30.00   85
 19  ω     41.00 126.00   1.00    1.00    --  107.97 -61.00 150.00   85
 20  ω     39.00 110.00   1.00    1.00    --  107.97 -95.00 120.00   71
 21  ω     39.00 177.00   1.00    1.00    --  107.97   0.00 -60.00  138
 22  ω   -104.00  -9.00   1.00    1.00    --  -35.97 -77.00  30.00   95
 23  ω   -104.00  -9.00   1.00    1.00    --  -35.97 -77.00 -90.00   95
 24  ω     19.00 103.00   1.00    1.00    --   35.97  57.00 120.00   84
 25  ω     19.00 103.00   1.00    1.00    --   35.97  57.00 -90.00   84
 26  ω     19.00 103.00   1.00    1.00    --   35.97  57.00  30.00   84
 27  ω    -33.00  55.00   1.00    1.00    --   35.97 -38.00 120.00   88
 28  ω     70.00 178.00   1.00    1.00    --  107.97  15.00  60.00  108
 29  ω     81.00 176.00   1.00    1.00    --  107.97  77.00 120.00   95
 30  ω     81.00 176.00   1.00    1.00    --  107.97  77.00  60.00   95
 31  ω     81.00 176.00   1.00    1.00    --  107.97  77.00 -90.00   95
 32  ω     81.00 176.00   1.00    1.00    --  107.97  77.00-180.00   95
 33  ω     87.00 178.00   1.00    1.00    --  107.97  30.00 120.00   91
 34  ω     81.00 176.00   1.00    1.00    --  107.97  77.00-150.00   95
 35  ω     81.00 176.00   1.00    1.00    --  107.97  77.00-120.00   95
 36  ω     81.00 176.00   1.00    1.00    --  107.97  77.00 -30.00   95
 37  ω     81.00 176.00   1.00    1.00    --  107.97  77.00  30.00   95
 38  ω     91.00 176.00   1.00    1.00    --  107.97  45.00-180.00   85
 39  ω     91.00 176.00   1.00    1.00    --  107.97  45.00 -30.00   85
 40  ω   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00  60.00   84
 41  ω      9.00 104.00   1.00    1.00    --   35.97  77.00 120.00   95
 42  ω     15.00 102.00   1.00    1.00    --   35.97  66.00  48.00   87
 43  ω     17.00 105.00   1.00    1.00    --   35.97  38.00-120.00   88
 44  ω     17.00 105.00   1.00    1.00    --   35.97  38.00 120.00   88
 45  ω      9.00 104.00   1.00    1.00    --   35.97  77.00 -60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0986838000
_diffrn_orient_matrix_UB_12      0.0103299000
_diffrn_orient_matrix_UB_13      -0.1024316000
_diffrn_orient_matrix_UB_21      0.0054086000
_diffrn_orient_matrix_UB_22      0.1448602000
_diffrn_orient_matrix_UB_23      0.0339184000
_diffrn_orient_matrix_UB_31      0.1877180000
_diffrn_orient_matrix_UB_32      0.0256141000
_diffrn_orient_matrix_UB_33      0.0929723000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3288
_reflns_number_total             3484
_reflns_odcompleteness_completeness 100.00
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0057(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0523
_refine_ls_restrained_S_all      1.043
_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)+(0.0919P)²+0.3489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1477
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C12(H12), C15(H15),
 C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -0.37792(8) -0.18944(5) -0.10605(5) 0.0506(2) Uani 1 1 d . . . . .
O1 O 0.1534(2) 0.59502(13) 0.05683(12) 0.0448(4) Uani 1 1 d . . . . .
O2 O 0.2825(2) 0.79516(14) 0.11343(14) 0.0528(4) Uani 1 1 d . . . . .
O3 O 0.7148(2) 0.99323(14) 0.49112(16) 0.0516(4) Uani 1 1 d . . . . .
O4 O 0.7226(3) 0.91415(17) 0.64347(17) 0.0671(5) Uani 1 1 d . . . . .
N1 N 0.0973(2) 0.37308(14) 0.27031(14) 0.0305(3) Uani 1 1 d . . . . .
N2 N 0.1523(2) 0.47136(14) 0.22278(14) 0.0305(3) Uani 1 1 d . . . . .
H2 H 0.1084 0.4648 0.1463 0.037 Uiso 1 1 calc R . . . .
N3 N 0.2505(2) 0.69299(15) 0.13607(14) 0.0329(4) Uani 1 1 d . . . . .
N4 N 0.6652(2) 0.90828(16) 0.53539(18) 0.0415(4) Uani 1 1 d . . . . .
C1 C -0.0760(2) -0.23166(17) 0.28932(18) 0.0326(4) Uani 1 1 d . . . . .
H1 H -0.0198 -0.1544 0.2818 0.039 Uiso 1 1 calc R . . . .
C2 C -0.0291(3) -0.25879(19) 0.40027(19) 0.0354(4) Uani 1 1 d . . . . .
H2A H 0.0574 -0.1993 0.4669 0.042 Uiso 1 1 calc R . . . .
C3 C -0.1101(3) -0.37438(19) 0.4133(2) 0.0392(4) Uani 1 1 d . . . . .
H3 H -0.0792 -0.3917 0.4885 0.047 Uiso 1 1 calc R . . . .
C4 C -0.2365(3) -0.46306(18) 0.3137(2) 0.0398(5) Uani 1 1 d . . . . .
H4 H -0.2900 -0.5408 0.3217 0.048 Uiso 1 1 calc R . . . .
C5 C -0.2843(3) -0.43715(17) 0.2022(2) 0.0369(4) Uani 1 1 d . . . . .
H5 H -0.3683 -0.4984 0.1356 0.044 Uiso 1 1 calc R . . . .
C6 C -0.2076(2) -0.31936(16) 0.18797(18) 0.0316(4) Uani 1 1 d . . . . .
C7 C -0.2689(3) -0.29658(17) 0.06809(19) 0.0351(4) Uani 1 1 d . . . . .
H7 H -0.2889 -0.3662 -0.0018 0.042 Uiso 1 1 calc R . . . .
C8 C -0.2990(3) -0.18695(18) 0.04866(18) 0.0344(4) Uani 1 1 d . . . . .
C9 C -0.2813(3) -0.05953(17) 0.13891(18) 0.0328(4) Uani 1 1 d . . . . .
H9A H -0.2526 -0.0675 0.2219 0.039 Uiso 1 1 calc R . . . .
H9B H -0.3989 -0.0341 0.1253 0.039 Uiso 1 1 calc R . . . .
C10 C -0.1337(3) 0.04564(17) 0.13036(18) 0.0349(4) Uani 1 1 d . . . . .
H10A H -0.1653 0.0578 0.0492 0.042 Uiso 1 1 calc R . . . .
H10B H -0.0164 0.0194 0.1403 0.042 Uiso 1 1 calc R . . . .
C11 C -0.1151(3) 0.17268(17) 0.22971(18) 0.0349(4) Uani 1 1 d . . . . .
H11A H -0.2359 0.1819 0.2419 0.042 Uiso 1 1 calc R . . . .
H11B H -0.0390 0.1712 0.3073 0.042 Uiso 1 1 calc R . . . .
C12 C -0.0319(3) 0.28437(18) 0.19500(17) 0.0359(4) Uani 1 1 d . . . . .
H12 H -0.0758 0.2894 0.1157 0.043 Uiso 1 1 calc R . . . .
C13 C 0.2752(2) 0.57732(15) 0.29742(16) 0.0261(4) Uani 1 1 d . . . . .
C14 C 0.3271(2) 0.68632(16) 0.25803(16) 0.0260(4) Uani 1 1 d . . . . .
C15 C 0.4538(2) 0.79407(16) 0.33703(17) 0.0287(4) Uani 1 1 d . . . . .
H15 H 0.4860 0.8645 0.3099 0.034 Uiso 1 1 calc R . . . .
C16 C 0.5306(2) 0.79582(16) 0.45473(17) 0.0304(4) Uani 1 1 d . . . . .
C17 C 0.4822(3) 0.69175(18) 0.49850(18) 0.0327(4) Uani 1 1 d . . . . .
H17 H 0.5347 0.6949 0.5794 0.039 Uiso 1 1 calc R . . . .
C18 C 0.3574(2) 0.58585(17) 0.42103(17) 0.0308(4) Uani 1 1 d . . . . .
H18 H 0.3254 0.5171 0.4505 0.037 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 C8 1.761(2) . ?
O1 N3 1.240(2) . ?
O2 N3 1.225(2) . ?
O3 N4 1.228(2) . ?
O4 N4 1.219(3) . ?
N1 N2 1.3868(18) . ?
N1 C12 1.270(2) . ?
N2 C13 1.349(2) . ?
N3 C14 1.439(2) . ?
N4 C16 1.450(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.403(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.410(2) . ?
C6 C7 1.469(3) . ?
C7 C8 1.333(3) . ?
C8 C9 1.491(3) . ?
C9 C10 1.527(2) . ?
C10 C11 1.535(3) . ?
C11 C12 1.487(2) . ?
C13 C14 1.425(2) . ?
C13 C18 1.413(3) . ?
C14 C15 1.388(2) . ?
C15 C16 1.363(3) . ?
C16 C17 1.402(2) . ?
C17 C18 1.364(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
C12 N1 N2 113.70(15) . . ?
C13 N2 N1 119.48(15) . . ?
O1 N3 C14 118.95(14) . . ?
O2 N3 O1 121.84(16) . . ?
O2 N3 C14 119.21(16) . . ?
O3 N4 C16 118.03(18) . . ?
O4 N4 O3 123.35(18) . . ?
O4 N4 C16 118.62(17) . . ?
C2 C1 C6 120.72(16) . . ?
C1 C2 C3 120.63(19) . . ?
C4 C3 C2 119.46(19) . . ?
C3 C4 C5 120.45(17) . . ?
C4 C5 C6 121.03(19) . . ?
C1 C6 C5 117.67(18) . . ?
C1 C6 C7 124.18(16) . . ?
C5 C6 C7 118.15(17) . . ?
C8 C7 C6 127.06(18) . . ?
C7 C8 Cl1 116.91(15) . . ?
C7 C8 C9 130.00(18) . . ?
C9 C8 Cl1 113.07(14) . . ?
C8 C9 C10 113.88(15) . . ?
C9 C10 C11 111.47(15) . . ?
C12 C11 C10 111.93(15) . . ?
N1 C12 C11 122.05(17) . . ?
N2 C13 C14 122.69(16) . . ?
N2 C13 C18 120.81(15) . . ?
C18 C13 C14 116.50(15) . . ?
C13 C14 N3 122.70(15) . . ?
C15 C14 N3 115.92(14) . . ?
C15 C14 C13 121.37(16) . . ?
C16 C15 C14 119.41(15) . . ?
C15 C16 N4 118.70(16) . . ?
C15 C16 C17 121.42(17) . . ?
C17 C16 N4 119.88(17) . . ?
C18 C17 C16 119.24(17) . . ?
C17 C18 C13 122.05(15) . . ?

_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 2.384
_oxdiff_exptl_absorpt_empirical_full_min 0.594
