# 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_hkx-20180205
_database_code_depnum_ccdc_archive 'CCDC 1939340'
loop_
_audit_author_name
_audit_author_address
HKX
;Henan Normal University
China
;
_audit_update_record             
;
2019-07-09 deposited with the CCDC.	2019-10-18 downloaded from the CCDC.
;
_audit_creation_date             2018-02-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5467)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 Br N2 O6'
_chemical_formula_sum            'C20 H19 Br N2 O6'
_chemical_formula_weight         463.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 O1 N1 Br1'
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'
Br Br -0.6763 1.2805 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.74390(10)
_cell_length_b                   12.3456(2)
_cell_length_c                   18.3547(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1981.37(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16821
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.4850
_cell_measurement_theta_min      4.2810
_shelx_estimated_absorpt_T_max   0.785
_shelx_estimated_absorpt_T_min   0.377
_exptl_absorpt_coefficient_mu    3.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29703
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.666
_diffrn_reflns_theta_min         4.316
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    --  -36.21 -57.00 -60.00   84
  2  ω      1.00  75.00   1.00    1.00    --   36.21 -99.00 150.00   74
  3  ω    -35.00  66.00   1.00    1.00    --   36.21 -19.00 -90.00  101
  4  ω     19.00 103.00   1.00    1.00    --   36.21  57.00  90.00   84
  5  ω    -31.00  63.00   1.00    1.00    --   36.21 -77.00 -60.00   94
  6  ω    -31.00  53.00   1.00    1.00    --   36.21 -57.00-139.00   84
  7  ω     16.00 103.00   1.00    1.00    --   36.21  66.00-159.00   87
  8  ω     88.00 178.00   1.00    1.42    --  109.31  30.00 150.00   90
  9  ω     89.00 176.00   1.00    1.42    --  109.31  66.00-159.00   87
 10  ω     40.00 109.00   1.00    1.42    --  109.31 -95.00 150.00   69
 11  ω     40.00 109.00   1.00    1.42    --  109.31 -95.00  60.00   69
 12  ω     40.00 109.00   1.00    1.42    --  109.31 -95.00-150.00   69
 13  ω     41.00 127.00   1.00    1.42    --  109.31 -45.00 150.00   86
 14  ω     40.00 109.00   1.00    1.42    --  109.31 -95.00  30.00   69
 15  ω     40.00 109.00   1.00    1.42    --  109.31 -95.00 -60.00   69
 16  ω     88.00 178.00   1.00    1.42    --  109.31  30.00  60.00   90
 17  ω    -53.00  31.00   1.00    1.00    --  -36.21  57.00  90.00   84
 18  ω    -31.00  53.00   1.00    1.00    --   36.21 -57.00 120.00   84
 19  ω     19.00 103.00   1.00    1.00    --   36.21  57.00 150.00   84
 20  ω      9.00 104.00   1.00    1.00    --   36.21  77.00   0.00   95
 21  ω     23.00  90.00   1.00    1.00    --   36.21-125.00  60.00   67
 22  ω      9.00 104.00   1.00    1.00    --   36.21  77.00 -90.00   95
 23  ω    -30.00  57.00   1.00    1.00    --   36.21 -66.00  66.00   87
 24  ω     17.00 105.00   1.00    1.00    --   36.21  38.00  30.00   88
 25  ω     83.00 177.00   1.00    1.42    --  109.31  77.00 -60.00   94
 26  ω     83.00 177.00   1.00    1.42    --  109.31  77.00 150.00   94
 27  ω     92.00 178.00   1.00    1.42    --  109.31  45.00   0.00   86
 28  ω     83.00 177.00   1.00    1.42    --  109.31  77.00  90.00   94
 29  ω     83.00 177.00   1.00    1.42    --  109.31  77.00-120.00   94
 30  ω     88.00 178.00   1.00    1.42    --  109.31  30.00  90.00   90
 31  ω     71.00 178.00   1.00    1.42    --  109.31  15.00 -30.00  107
 32  ω     91.00 176.00   1.00    1.42    --  109.31  61.00-180.00   85
 33  ω   -104.00  -9.00   1.00    1.00    --  -36.21 -77.00  90.00   95
 34  ω      9.00 104.00   1.00    1.00    --   36.21  77.00-150.00   95
 35  ω      9.00 104.00   1.00    1.00    --   36.21  77.00  90.00   95
 36  ω     23.00  90.00   1.00    1.00    --   36.21-125.00 -60.00   67
 37  ω     17.00 105.00   1.00    1.00    --   36.21  38.00-180.00   88
 38  ω    -31.00  63.00   1.00    1.00    --   36.21 -77.00  30.00   94
 39  ω     23.00  90.00   1.00    1.00    --   36.21-125.00-150.00   67
 40  ω      7.00 108.00   1.00    1.00    --   36.21  19.00  30.00  101
 41  ω     83.00 177.00   1.00    1.42    --  109.31  77.00-150.00   94
;
_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      0.1432631000
_diffrn_orient_matrix_UB_12      0.0656133000
_diffrn_orient_matrix_UB_13      0.0211870000
_diffrn_orient_matrix_UB_21      0.0965781000
_diffrn_orient_matrix_UB_22      -0.0678466000
_diffrn_orient_matrix_UB_23      -0.0532844000
_diffrn_orient_matrix_UB_31      -0.0344924000
_diffrn_orient_matrix_UB_32      0.0816976000
_diffrn_orient_matrix_UB_33      -0.0612522000
_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         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3792
_reflns_number_total             3907
_reflns_odcompleteness_completeness 99.95
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1567 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.034(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.3982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0657
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C2(H2), C28(H28), C16(H16), C27(H27), C25(H25)
2.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C22(H22a,H22b,H22c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Br29 Br 0.28448(5) -0.20497(3) 0.60614(2) 0.06614(14) Uani 1 1 d . . . . .
O21 O 0.4508(3) 0.23973(16) 0.33394(10) 0.0444(5) Uani 1 1 d . . . . .
O13 O 0.5774(2) 0.47605(18) 0.28120(10) 0.0436(5) Uani 1 1 d . . . . .
N1 N 0.3982(2) 0.40282(16) 0.38649(11) 0.0312(4) Uani 1 1 d . . . . .
O19 O 0.7288(3) 0.15354(18) 0.41362(13) 0.0555(6) Uani 1 1 d . . . . .
O20 O 0.6508(3) 0.30405(19) 0.55754(11) 0.0514(5) Uani 1 1 d . . . . .
N5 N 0.5397(3) 0.27188(18) 0.44868(12) 0.0363(5) Uani 1 1 d . . . . .
O15 O 0.4125(3) 0.4266(2) 0.19425(10) 0.0563(6) Uani 1 1 d . . . . .
O7 O 0.0703(3) 0.4271(2) 0.26829(15) 0.0654(7) Uani 1 1 d . . . . .
C6 C 0.4613(3) 0.3001(2) 0.38542(13) 0.0346(5) Uani 1 1 d . . . . .
C9 C 0.3229(3) 0.4369(2) 0.31762(12) 0.0333(5) Uani 1 1 d . . . . .
C18 C 0.6132(3) 0.1646(2) 0.44712(15) 0.0393(6) Uani 1 1 d . . . . .
C23 C 0.5337(3) 0.0779(2) 0.48785(14) 0.0352(6) Uani 1 1 d . . . . .
C24 C 0.5715(3) -0.0292(2) 0.47189(15) 0.0396(6) Uani 1 1 d . . . . .
H24 H 0.646703 -0.044064 0.437500 0.048 Uiso 1 1 calc R . . . .
C4 C 0.5721(3) 0.3398(2) 0.50787(14) 0.0377(6) Uani 1 1 d . . . . .
C2 C 0.4295(3) 0.4739(2) 0.44279(13) 0.0345(5) Uani 1 1 d . . . . .
H2 H 0.392170 0.544199 0.439217 0.041 Uiso 1 1 calc R . . . .
C12 C 0.4425(3) 0.4439(2) 0.25671(14) 0.0368(6) Uani 1 1 d . . . . .
C10 C 0.2396(3) 0.5478(2) 0.32390(14) 0.0366(6) Uani 1 1 d . . . . .
H10 H 0.186625 0.549389 0.370952 0.044 Uiso 1 1 calc R . . . .
C3 C 0.5105(3) 0.4473(2) 0.50239(14) 0.0371(6) Uani 1 1 d . . . . .
C28 C 0.4237(3) 0.0997(2) 0.54087(15) 0.0402(6) Uani 1 1 d . . . . .
H28 H 0.398261 0.170966 0.551896 0.048 Uiso 1 1 calc R . . . .
C8 C 0.1900(3) 0.3613(3) 0.29607(15) 0.0436(7) Uani 1 1 d . . . . .
H8A H 0.223483 0.310094 0.259288 0.052 Uiso 1 1 calc R . . . .
H8B H 0.154695 0.321009 0.338220 0.052 Uiso 1 1 calc R . . . .
C16 C 0.3303(4) 0.6501(3) 0.31736(18) 0.0466(7) Uani 1 1 d . . . . .
H16 H 0.395889 0.657126 0.277753 0.056 Uiso 1 1 calc R . . . .
C27 C 0.3524(3) 0.0155(2) 0.57705(16) 0.0432(6) Uani 1 1 d . . . . .
H27 H 0.280770 0.029757 0.613251 0.052 Uiso 1 1 calc R . . . .
C26 C 0.3884(3) -0.0899(2) 0.55903(15) 0.0413(6) Uani 1 1 d . . . . .
C25 C 0.4980(4) -0.1133(2) 0.50678(15) 0.0434(7) Uani 1 1 d . . . . .
H25 H 0.521685 -0.184736 0.495420 0.052 Uiso 1 1 calc R . . . .
C11 C 0.1189(4) 0.5366(3) 0.26465(18) 0.0521(8) Uani 1 1 d . . . . .
H11A H 0.033939 0.585360 0.273589 0.063 Uiso 1 1 calc R . . . .
H11B H 0.162033 0.552723 0.217180 0.063 Uiso 1 1 calc R . . . .
C14 C 0.6928(4) 0.5003(3) 0.22649(18) 0.0560(8) Uani 1 1 d . . . . .
H14A H 0.645274 0.505094 0.179449 0.084 Uiso 1 1 calc GR . . . .
H14B H 0.768247 0.443871 0.226002 0.084 Uiso 1 1 calc GR . . . .
H14C H 0.740981 0.568119 0.237922 0.084 Uiso 1 1 calc GR . . . .
C22 C 0.5429(4) 0.5256(3) 0.56282(16) 0.0545(8) Uani 1 1 d . . . . .
H22A H 0.504414 0.496996 0.607856 0.082 Uiso 1 1 calc GR . . . .
H22B H 0.493705 0.593471 0.552556 0.082 Uiso 1 1 calc GR . . . .
H22C H 0.651252 0.536652 0.566745 0.082 Uiso 1 1 calc GR . . . .
C17 C 0.3232(6) 0.7301(3) 0.3638(2) 0.0688(11) Uani 1 1 d . . . . .
H17A H 0.385(5) 0.797(4) 0.355(2) 0.077(12) Uiso 1 1 d . . . . .
H17B H 0.255(6) 0.724(4) 0.413(3) 0.114(17) 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
Br29 C26 1.895(3) . ?
O21 C6 1.207(3) . ?
O13 C12 1.323(3) . ?
O13 C14 1.455(3) . ?
N1 C6 1.383(3) . ?
N1 C9 1.486(3) . ?
N1 C2 1.383(3) . ?
O19 C18 1.191(4) . ?
O20 C4 1.224(3) . ?
N5 C6 1.393(3) . ?
N5 C18 1.473(3) . ?
N5 C4 1.401(3) . ?
O15 C12 1.195(3) . ?
O7 C8 1.419(4) . ?
O7 C11 1.419(4) . ?
C9 C12 1.533(3) . ?
C9 C10 1.555(4) . ?
C9 C8 1.543(4) . ?
C18 C23 1.479(4) . ?
C23 C24 1.394(4) . ?
C23 C28 1.394(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(4) . ?
C4 C3 1.436(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.344(4) . ?
C10 H10 0.9800 . ?
C10 C16 1.496(4) . ?
C10 C11 1.521(4) . ?
C3 C22 1.499(4) . ?
C28 H28 0.9300 . ?
C28 C27 1.382(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.307(5) . ?
C27 H27 0.9300 . ?
C27 C26 1.379(4) . ?
C26 C25 1.386(4) . ?
C25 H25 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C17 H17A 1.00(4) . ?
C17 H17B 1.08(5) . ?

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 O13 C14 116.5(2) . . ?
C6 N1 C9 115.1(2) . . ?
C2 N1 C6 120.9(2) . . ?
C2 N1 C9 122.9(2) . . ?
C6 N5 C18 115.1(2) . . ?
C6 N5 C4 126.6(2) . . ?
C4 N5 C18 117.7(2) . . ?
C11 O7 C8 110.0(2) . . ?
O21 C6 N1 123.2(2) . . ?
O21 C6 N5 122.4(2) . . ?
N1 C6 N5 114.5(2) . . ?
N1 C9 C12 109.5(2) . . ?
N1 C9 C10 113.2(2) . . ?
N1 C9 C8 112.4(2) . . ?
C12 C9 C10 108.9(2) . . ?
C12 C9 C8 111.1(2) . . ?
C8 C9 C10 101.5(2) . . ?
O19 C18 N5 118.9(3) . . ?
O19 C18 C23 125.3(3) . . ?
N5 C18 C23 115.8(2) . . ?
C24 C23 C18 117.9(2) . . ?
C24 C23 C28 119.5(3) . . ?
C28 C23 C18 122.5(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(3) . . ?
C25 C24 H24 119.8 . . ?
O20 C4 N5 118.4(3) . . ?
O20 C4 C3 126.6(3) . . ?
N5 C4 C3 115.0(2) . . ?
N1 C2 H2 118.1 . . ?
C3 C2 N1 123.9(3) . . ?
C3 C2 H2 118.1 . . ?
O13 C12 C9 112.2(2) . . ?
O15 C12 O13 125.1(3) . . ?
O15 C12 C9 122.7(3) . . ?
C9 C10 H10 107.7 . . ?
C16 C10 C9 119.2(2) . . ?
C16 C10 H10 107.7 . . ?
C16 C10 C11 112.8(2) . . ?
C11 C10 C9 101.1(2) . . ?
C11 C10 H10 107.7 . . ?
C4 C3 C22 118.3(2) . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 C22 123.0(3) . . ?
C23 C28 H28 120.0 . . ?
C27 C28 C23 120.1(3) . . ?
C27 C28 H28 120.0 . . ?
O7 C8 C9 107.5(2) . . ?
O7 C8 H8A 110.2 . . ?
O7 C8 H8B 110.2 . . ?
C9 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C10 C16 H16 118.0 . . ?
C17 C16 C10 124.1(3) . . ?
C17 C16 H16 118.0 . . ?
C28 C27 H27 120.3 . . ?
C26 C27 C28 119.4(3) . . ?
C26 C27 H27 120.3 . . ?
C27 C26 Br29 119.2(2) . . ?
C27 C26 C25 121.3(3) . . ?
C25 C26 Br29 119.4(2) . . ?
C24 C25 C26 119.2(3) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
O7 C11 C10 105.1(2) . . ?
O7 C11 H11A 110.7 . . ?
O7 C11 H11B 110.7 . . ?
C10 C11 H11A 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C22 H22A 109.5 . . ?
C3 C22 H22B 109.5 . . ?
C3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C17 H17A 119(2) . . ?
C16 C17 H17B 121(3) . . ?
H17A C17 H17B 120(4) . . ?

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
Br29 C26 C25 C24 179.0(2) . . . . ?
N1 C9 C12 O13 -33.9(3) . . . . ?
N1 C9 C12 O15 149.3(3) . . . . ?
N1 C9 C10 C16 81.4(3) . . . . ?
N1 C9 C10 C11 -154.5(2) . . . . ?
N1 C9 C8 O7 140.4(2) . . . . ?
N1 C2 C3 C4 1.5(4) . . . . ?
N1 C2 C3 C22 -179.9(3) . . . . ?
O19 C18 C23 C24 -17.3(4) . . . . ?
O19 C18 C23 C28 162.7(3) . . . . ?
O20 C4 C3 C2 178.2(3) . . . . ?
O20 C4 C3 C22 -0.3(5) . . . . ?
N5 C18 C23 C24 162.1(2) . . . . ?
N5 C18 C23 C28 -17.9(4) . . . . ?
N5 C4 C3 C2 -0.2(4) . . . . ?
N5 C4 C3 C22 -178.7(3) . . . . ?
C6 N1 C9 C12 -64.1(3) . . . . ?
C6 N1 C9 C10 174.1(2) . . . . ?
C6 N1 C9 C8 59.9(3) . . . . ?
C6 N1 C2 C3 -5.6(4) . . . . ?
C6 N5 C18 O19 76.2(3) . . . . ?
C6 N5 C18 C23 -103.2(3) . . . . ?
C6 N5 C4 O20 -175.5(3) . . . . ?
C6 N5 C4 C3 3.1(4) . . . . ?
C9 N1 C6 O21 -3.3(4) . . . . ?
C9 N1 C6 N5 176.2(2) . . . . ?
C9 N1 C2 C3 -173.2(2) . . . . ?
C9 C10 C16 C17 -129.8(4) . . . . ?
C9 C10 C11 O7 38.2(3) . . . . ?
C18 N5 C6 O21 2.0(4) . . . . ?
C18 N5 C6 N1 -177.5(2) . . . . ?
C18 N5 C4 O20 -5.0(4) . . . . ?
C18 N5 C4 C3 173.5(2) . . . . ?
C18 C23 C24 C25 -178.3(3) . . . . ?
C18 C23 C28 C27 179.7(3) . . . . ?
C23 C24 C25 C26 -1.3(4) . . . . ?
C23 C28 C27 C26 -1.5(4) . . . . ?
C24 C23 C28 C27 -0.3(4) . . . . ?
C4 N5 C6 O21 172.7(3) . . . . ?
C4 N5 C6 N1 -6.7(4) . . . . ?
C4 N5 C18 O19 -95.4(3) . . . . ?
C4 N5 C18 C23 85.2(3) . . . . ?
C2 N1 C6 O21 -171.8(3) . . . . ?
C2 N1 C6 N5 7.7(3) . . . . ?
C2 N1 C9 C12 104.2(3) . . . . ?
C2 N1 C9 C10 -17.6(3) . . . . ?
C2 N1 C9 C8 -131.8(3) . . . . ?
C12 C9 C10 C16 -40.7(3) . . . . ?
C12 C9 C10 C11 83.5(3) . . . . ?
C12 C9 C8 O7 -96.5(3) . . . . ?
C10 C9 C12 O13 90.4(3) . . . . ?
C10 C9 C12 O15 -86.4(3) . . . . ?
C10 C9 C8 O7 19.2(3) . . . . ?
C28 C23 C24 C25 1.7(4) . . . . ?
C28 C27 C26 Br29 -177.6(2) . . . . ?
C28 C27 C26 C25 1.9(4) . . . . ?
C8 O7 C11 C10 -27.5(3) . . . . ?
C8 C9 C12 O13 -158.6(2) . . . . ?
C8 C9 C12 O15 24.6(4) . . . . ?
C8 C9 C10 C16 -158.0(2) . . . . ?
C8 C9 C10 C11 -33.8(3) . . . . ?
C16 C10 C11 O7 166.6(3) . . . . ?
C27 C26 C25 C24 -0.5(4) . . . . ?
C11 O7 C8 C9 4.6(3) . . . . ?
C11 C10 C16 C17 111.9(4) . . . . ?
C14 O13 C12 O15 5.3(5) . . . . ?
C14 O13 C12 C9 -171.4(2) . . . . ?

_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 3.806
_oxdiff_exptl_absorpt_empirical_full_min 0.603
####################################################################### 
# 
# 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_2-cl
_database_code_depnum_ccdc_archive 'CCDC 1942058'
loop_
_audit_author_name
_audit_author_address
HKX
;Henan Normal University
China
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-10-18 downloaded from the CCDC.
;
_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
_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
