# Electronic Supplementary Material (ESI) for ChemComm.
# 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_exp_6177
_audit_block_doi                 10.5517/ccdc.csd.cc22bkqq
_database_code_depnum_ccdc_archive 'CCDC 1916783'
loop_
_audit_author_name
_audit_author_address
'Liu Xiaobing'
;Huaqiao university
China
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;
_audit_creation_date             2018-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         '0.67(C17 H15 Cl N2 O)'
_chemical_formula_sum            'C11.333 H10 Cl0.667 N1.333 O0.667'
_chemical_formula_weight         199.18
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.9754(7)
_cell_length_b                   14.0802(15)
_cell_length_c                   10.6923(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.036(6)
_cell_angle_gamma                90
_cell_volume                     1501.5(2)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2163
_cell_measurement_theta_max      26.6440
_cell_measurement_theta_min      4.0050
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3215
_exptl_crystal_F_000             624.8289
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7345
_diffrn_reflns_theta_full        24.9998
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.54
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9970
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0107958000
_diffrn_orient_matrix_UB_12      -0.0046806000
_diffrn_orient_matrix_UB_13      0.0654697000
_diffrn_orient_matrix_UB_21      0.0017682000
_diffrn_orient_matrix_UB_22      -0.0501221000
_exptl_crystal_description       block
_cell_measurement_temperature    298
_diffrn_ambient_temperature      298
_diffrn_orient_matrix_UB_23      -0.0065286000
_diffrn_orient_matrix_UB_31      0.0702513000
_diffrn_orient_matrix_UB_32      0.0019967000
_diffrn_orient_matrix_UB_33      -0.0086511000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2001
_reflns_number_total             2636
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.3013
_refine_diff_density_min         -0.3502
_refine_diff_density_rms         0.0850
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.7516
_refine_ls_goodness_of_fit_ref   0.9498
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2636
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      0.9498
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1485
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00E(H00E), C009(H009), C008(H008), C00H(H00H), C00L(H00m),
 C00K(H00l), C00J(H00k), C00B(H00B)
2.b Idealised Me refined as rotating group:
 C00F(H00a,H00c,H00d), C00I(H00f,H00i,H00j)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Cl00 Cl 0.04151(6) 0.70745(6) 0.95289(6) 0.0665(3) Uani 1.000000 .
N002 N 0.53523(16) 0.60188(13) 0.68751(15) 0.0366(4) Uani 1.000000 .
N003 N 0.54075(16) 0.62129(13) 0.55899(15) 0.0374(5) Uani 1.000000 .
O004 O 0.67555(16) 0.53712(16) 0.83961(15) 0.0683(6) Uani 1.000000 .
C005 C 0.4187(2) 0.62786(15) 0.75245(19) 0.0349(5) Uani 1.000000 .
C006 C 0.68876(19) 0.60689(16) 0.38674(19) 0.0359(5) Uani 1.000000 .
C007 C 0.65650(19) 0.59497(15) 0.51966(19) 0.0346(5) Uani 1.000000 .
C008 C 0.2043(2) 0.70560(16) 0.7539(2) 0.0410(6) Uani 1.000000 .
C009 C 0.3190(2) 0.68080(16) 0.69202(19) 0.0380(5) Uani 1.000000 .
C00A C 0.74500(19) 0.55345(16) 0.62258(19) 0.0375(5) Uani 1.000000 .
C00B C 0.5947(2) 0.64762(17) 0.3043(2) 0.0422(6) Uani 1.000000 .
C00C C 0.1885(2) 0.67734(17) 0.8760(2) 0.0413(6) Uani 1.000000 .
C00D C 0.6521(2) 0.56189(17) 0.7325(2) 0.0409(6) Uani 1.000000 .
C00E C 0.4014(2) 0.60073(18) 0.8762(2) 0.0453(6) Uani 1.000000 .
C00F C 0.7786(2) 0.44800(18) 0.6044(2) 0.0513(7) Uani 1.000000 .
C00G C 0.2864(2) 0.62551(19) 0.9371(2) 0.0495(6) Uani 1.000000 .
C00H C 0.8105(2) 0.5779(2) 0.3384(2) 0.0511(6) Uani 1.000000 .
C00I C 0.8716(2) 0.61269(19) 0.6527(2) 0.0520(7) Uani 1.000000 .
C00J C 0.6221(2) 0.65675(19) 0.1797(2) 0.0505(6) Uani 1.000000 .
C00K C 0.7434(2) 0.62677(19) 0.1330(2) 0.0533(7) Uani 1.000000 .
C00L C 0.8374(2) 0.5882(2) 0.2127(2) 0.0597(7) Uani 1.000000 .
H00G H 0.2747(2) 0.60718(19) 1.0197(2) 0.0594(8) Uiso 1.000000 R
H00E H 0.4677(2) 0.56585(18) 0.9178(2) 0.0544(7) Uiso 1.000000 R
H009 H 0.3299(2) 0.69952(16) 0.60941(19) 0.0456(6) Uiso 1.000000 R
H008 H 0.1380(2) 0.74120(16) 0.7136(2) 0.0492(7) Uiso 1.000000 R
H00H H 0.8750(2) 0.5511(2) 0.3915(2) 0.0613(8) Uiso 1.000000 R
H00m H 0.9197(2) 0.5688(2) 0.1822(2) 0.0717(9) Uiso 1.000000 R
H00l H 0.7608(2) 0.63278(19) 0.0482(2) 0.0640(8) Uiso 1.000000 R
H00k H 0.5583(2) 0.68346(19) 0.1259(2) 0.0605(8) Uiso 1.000000 R
H00B H 0.5130(2) 0.66868(17) 0.3343(2) 0.0506(7) Uiso 1.000000 R
H00a H 0.6989(4) 0.4141(3) 0.5800(15) 0.0769(10) Uiso 1.000000 GR
H00c H 0.8443(12) 0.4417(2) 0.5404(10) 0.0769(10) Uiso 1.000000 GR
H00d H 0.8137(15) 0.4223(3) 0.6814(4) 0.0769(10) Uiso 1.000000 GR
H00f H 0.9323(7) 0.6085(9) 0.5843(7) 0.0780(10) Uiso 1.000000 GR
H00i H 0.8467(3) 0.6778(3) 0.6652(15) 0.0780(10) Uiso 1.000000 GR
H00j H 0.9144(9) 0.5887(8) 0.7273(9) 0.0780(10) Uiso 1.000000 GR


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
Cl00 C00C 1.746(2) . ?
N002 N003 1.403(2) . ?
N002 C005 1.413(2) . ?
N002 C00D 1.374(3) . ?
N003 C007 1.290(3) . ?
O004 C00D 1.216(2) . ?
C005 C009 1.393(3) . ?
C005 C00E 1.391(3) . ?
C006 C007 1.472(3) . ?
C006 C00B 1.398(3) . ?
C006 C00H 1.390(3) . ?
C007 C00A 1.516(3) . ?
C008 C009 1.377(3) . ?
C008 C00C 1.376(3) . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?
C00A C00D 1.515(3) . ?
C00A C00F 1.535(3) . ?
C00A C00I 1.542(3) . ?
C00B C00J 1.371(3) . ?
C00B H00B 0.9300 . ?
C00C C00G 1.374(3) . ?
C00E C00G 1.375(3) . ?
C00E H00E 0.9300 . ?
C00F H00a 0.9600 . ?
C00F H00c 0.9600 . ?
C00F H00d 0.9600 . ?
C00G H00G 0.9300 . ?
C00H C00L 1.383(3) . ?
C00H H00H 0.9300 . ?
C00I H00f 0.9600 . ?
C00I H00i 0.9600 . ?
C00I H00j 0.9600 . ?
C00J C00K 1.383(3) . ?
C00J H00k 0.9300 . ?
C00K C00L 1.368(4) . ?
C00K H00l 0.9300 . ?
C00L H00m 0.9300 . ?

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
C005 N002 N003 118.56(15) . . ?
C00D N002 N003 112.02(16) . . ?
C00D N002 C005 129.38(17) . . ?
C007 N003 N002 108.33(15) . . ?
C009 C005 N002 119.84(18) . . ?
C00E C005 N002 120.89(19) . . ?
C00E C005 C009 119.3(2) . . ?
C00B C006 C007 119.96(18) . . ?
C00H C006 C007 122.22(18) . . ?
C00H C006 C00B 117.8(2) . . ?
C006 C007 N003 119.63(17) . . ?
C00A C007 N003 112.77(18) . . ?
C00A C007 C006 127.60(18) . . ?
C00C C008 C009 119.5(2) . . ?
H008 C008 C009 120.23(12) . . ?
H008 C008 C00C 120.23(13) . . ?
C008 C009 C005 120.34(19) . . ?
H009 C009 C005 119.83(12) . . ?
H009 C009 C008 119.83(12) . . ?
C00D C00A C007 100.17(16) . . ?
C00F C00A C007 114.00(18) . . ?
C00F C00A C00D 108.20(19) . . ?
C00I C00A C007 114.01(19) . . ?
C00I C00A C00D 107.80(18) . . ?
C00I C00A C00F 111.69(18) . . ?
C00J C00B C006 120.5(2) . . ?
H00B C00B C006 119.73(13) . . ?
H00B C00B C00J 119.73(14) . . ?
C008 C00C Cl00 119.19(18) . . ?
C00G C00C Cl00 120.03(17) . . ?
C00G C00C C008 120.8(2) . . ?
O004 C00D N002 126.5(2) . . ?
C00A C00D N002 106.72(17) . . ?
C00A C00D O004 126.74(19) . . ?
C00G C00E C005 120.0(2) . . ?
H00E C00E C005 120.02(13) . . ?
H00E C00E C00G 120.02(13) . . ?
H00a C00F C00A 109.5 . . ?
H00c C00F C00A 109.5 . . ?
H00c C00F H00a 109.5 . . ?
H00d C00F C00A 109.5 . . ?
H00d C00F H00a 109.5 . . ?
H00d C00F H00c 109.5 . . ?
C00E C00G C00C 120.1(2) . . ?
H00G C00G C00C 119.94(13) . . ?
H00G C00G C00E 119.94(13) . . ?
C00L C00H C006 121.1(2) . . ?
H00H C00H C006 119.44(13) . . ?
H00H C00H C00L 119.44(15) . . ?
H00f C00I C00A 109.5 . . ?
H00i C00I C00A 109.5 . . ?
H00i C00I H00f 109.5 . . ?
H00j C00I C00A 109.5 . . ?
H00j C00I H00f 109.5 . . ?
H00j C00I H00i 109.5 . . ?
C00K C00J C00B 120.9(2) . . ?
H00k C00J C00B 119.56(14) . . ?
H00k C00J C00K 119.56(14) . . ?
C00L C00K C00J 119.4(2) . . ?
H00l C00K C00J 120.30(14) . . ?
H00l C00K C00L 120.30(14) . . ?
C00K C00L C00H 120.2(2) . . ?
H00m C00L C00H 119.88(15) . . ?
H00m C00L C00K 119.88(14) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.501
_oxdiff_exptl_absorpt_empirical_full_min 0.746
####################################################################### 
# 
# 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_exp_6020
_audit_block_doi                 10.5517/ccdc.csd.cc20zy65
_database_code_depnum_ccdc_archive 'CCDC 1876777'
loop_
_audit_author_name
_audit_author_address
'Yao Zhou'
;Huaqiao University
China
;
_audit_update_record             
;
2018-11-02 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;
_audit_creation_date             2018-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_formula_moiety         'C18 H17 N3 O4'
_chemical_formula_sum            'C18 H17 N3 O4'
_chemical_formula_weight         339.35
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   5.9361(7)
_cell_length_b                   26.091(3)
_cell_length_c                   10.7999(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.444(11)
_cell_angle_gamma                90
_cell_volume                     1654.6(3)
_cell_formula_units_Z            4
_exptl_crystal_description       block
_cell_measurement_temperature    298
_diffrn_ambient_temperature      298
_cell_measurement_reflns_used    1728
_cell_measurement_theta_max      26.0170
_cell_measurement_theta_min      3.8670
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3622
_exptl_crystal_F_000             712.3781
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7744
_diffrn_reflns_theta_full        24.9991
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.56
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  71.00   1.00    9.00    --   15.65   0.00 -30.00   83
  2  ω     -6.00  20.00   1.00    9.00    --  -16.43 -99.00-120.00   26
  3  ω    -13.00  31.00   1.00    9.00    --   15.65 -57.00 -30.00   44
  4  ω    -24.00  15.00   1.00    9.00    --  -16.43 -99.00  60.00   39
  5  ω     49.00  74.00   1.00    9.00    --   15.65 178.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0221301000
_diffrn_orient_matrix_UB_12      -0.0266134000
_diffrn_orient_matrix_UB_13      0.0041456000
_diffrn_orient_matrix_UB_21      0.0569587000
_diffrn_orient_matrix_UB_22      -0.0045942000
_diffrn_orient_matrix_UB_23      -0.0522054000
_diffrn_orient_matrix_UB_31      0.1041875000
_diffrn_orient_matrix_UB_32      -0.0031839000
_diffrn_orient_matrix_UB_33      0.0408107000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -7
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              -5
_reflns_number_gt                2078
_reflns_number_total             2898
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.3181
_refine_diff_density_min         -0.3807
_refine_diff_density_rms         0.0669
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.7285
_refine_ls_goodness_of_fit_ref   1.0831
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.0831
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.5823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1542
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00N(H00a,H00b,H00c), C00P(H00f,H00n,H00p)
2.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O001 O 0.3949(3) 0.46471(7) 0.7748(2) 0.0541(5) Uani 1.000000 .
H001 H 0.3409(6) 0.49363(9) 0.765(3) 0.0812(8) Uiso 1.000000 GR
N002 N 0.3741(3) 0.34550(8) 0.78526(19) 0.0394(5) Uani 1.000000 .
N003 N 0.3015(3) 0.38327(8) 0.69711(19) 0.0413(5) Uani 1.000000 .
O004 O 0.6954(4) 0.42550(10) 0.19561(19) 0.0740(7) Uani 1.000000 .
N005 N 0.7456(4) 0.39179(11) 0.2738(2) 0.0598(7) Uani 1.000000 .
C006 C 0.3641(4) 0.32224(10) 0.9968(2) 0.0383(6) Uani 1.000000 .
C007 C 0.3043(4) 0.35666(9) 0.8887(2) 0.0352(6) Uani 1.000000 .
O008 O -0.0191(4) 0.49624(10) 0.6656(3) 0.0859(8) Uani 1.000000 .
C009 C 0.4106(4) 0.38519(10) 0.5912(2) 0.0393(6) Uani 1.000000 .
C00A C 0.2174(4) 0.42817(10) 0.7557(2) 0.0402(6) Uani 1.000000 .
C00B C 0.1611(4) 0.40519(10) 0.8818(2) 0.0384(6) Uani 1.000000 .
O00C O 0.8897(5) 0.35993(12) 0.2642(3) 0.1044(10) Uani 1.000000 .
C00D C 0.2528(5) 0.32334(12) 1.1000(2) 0.0527(8) Uani 1.000000 .
H00D H 0.1349(5) 0.34660(12) 1.1026(2) 0.0633(9) Uiso 1.000000 R
C00E C 0.5625(4) 0.34676(11) 0.5685(2) 0.0445(7) Uani 1.000000 .
H00E H 0.5904(4) 0.31947(11) 0.6241(2) 0.0535(8) Uiso 1.000000 R
C00F C 0.6273(4) 0.38934(11) 0.3822(2) 0.0462(7) Uani 1.000000 .
C00G C 0.5394(5) 0.28682(11) 0.9972(3) 0.0533(7) Uani 1.000000 .
H00G H 0.6165(5) 0.28474(11) 0.9284(3) 0.0640(9) Uiso 1.000000 R
C00H C 0.4723(5) 0.42669(12) 0.4000(2) 0.0539(8) Uani 1.000000 .
H00H H 0.4400(5) 0.45296(12) 0.3419(2) 0.0647(9) Uiso 1.000000 R
C00I C 0.6709(5) 0.34887(12) 0.4651(2) 0.0508(7) Uani 1.000000 .
H00I H 0.7730(5) 0.32329(12) 0.4506(2) 0.0610(9) Uiso 1.000000 R
C00J C 0.3136(6) 0.29030(13) 1.2001(3) 0.0634(9) Uani 1.000000 .
H00J H 0.2348(6) 0.29140(13) 1.2684(3) 0.0761(10) Uiso 1.000000 R
C00K C 0.3658(5) 0.42486(12) 0.5043(3) 0.0527(8) Uani 1.000000 .
H00K H 0.2623(5) 0.45037(12) 0.5172(3) 0.0632(9) Uiso 1.000000 R
C00L C 0.4858(6) 0.25668(13) 1.1995(3) 0.0655(9) Uani 1.000000 .
H00L H 0.5269(6) 0.23489(13) 1.2672(3) 0.0786(11) Uiso 1.000000 R
C00M C 0.0082(5) 0.45055(14) 0.6766(3) 0.0580(8) Uani 1.000000 .
H00M H -0.1016(5) 0.42855(14) 0.6357(3) 0.0696(10) Uiso 1.000000 R
C00N C 0.2260(6) 0.44314(12) 0.9900(3) 0.0602(8) Uani 1.000000 .
H00a H 0.172(3) 0.4306(4) 1.0638(6) 0.0903(12) Uiso 1.000000 GR
H00b H 0.3887(6) 0.4467(6) 1.0063(13) 0.0903(12) Uiso 1.000000 GR
H00c H 0.158(3) 0.4759(2) 0.9677(8) 0.0903(12) Uiso 1.000000 GR
C00O C 0.6003(5) 0.25495(13) 1.0974(3) 0.0690(9) Uani 1.000000 .
H00O H 0.7198(5) 0.23197(13) 1.0965(3) 0.0828(11) Uiso 1.000000 R
C00P C -0.0930(4) 0.39062(14) 0.8719(3) 0.0626(9) Uani 1.000000 .
H00f H -0.1331(10) 0.3679(7) 0.8023(13) 0.0940(14) Uiso 1.000000 GR
H00n H -0.1193(8) 0.3739(8) 0.9476(9) 0.0940(14) Uiso 1.000000 GR
H00p H -0.1845(5) 0.42104(15) 0.860(2) 0.0940(14) Uiso 1.000000 GR


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
O001 H001 0.8200 . ?
O001 C00A 1.413(3) . ?
N002 N003 1.394(3) . ?
N002 C007 1.281(3) . ?
N003 C009 1.396(3) . ?
N003 C00A 1.454(3) . ?
O004 N005 1.225(3) . ?
N005 O00C 1.208(3) . ?
N005 C00F 1.452(3) . ?
C006 C007 1.475(3) . ?
C006 C00D 1.376(4) . ?
C006 C00G 1.392(4) . ?
C007 C00B 1.521(3) . ?
O008 C00M 1.206(4) . ?
C009 C00E 1.394(3) . ?
C009 C00K 1.397(4) . ?
C00A C00B 1.568(3) . ?
C00A C00M 1.517(4) . ?
C00B C00N 1.538(4) . ?
C00B C00P 1.544(3) . ?
C00D H00D 0.9300 . ?
C00D C00J 1.389(4) . ?
C00E H00E 0.9300 . ?
C00E C00I 1.370(4) . ?
C00F C00H 1.373(4) . ?
C00F C00I 1.384(4) . ?
C00G H00G 0.9300 . ?
C00G C00O 1.370(4) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.371(4) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00L 1.348(4) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00O 1.379(4) . ?
C00M H00M 0.9300 . ?
C00N H00a 0.9600 . ?
C00N H00b 0.9600 . ?
C00N H00c 0.9600 . ?
C00O H00O 0.9300 . ?
C00P H00f 0.9600 . ?
C00P H00n 0.9600 . ?
C00P H00p 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
C00A O001 H001 109.5 . . ?
C007 N002 N003 109.2(2) . . ?
C009 N003 N002 116.8(2) . . ?
C00A N003 N002 111.34(19) . . ?
C00A N003 C009 123.9(2) . . ?
O00C N005 O004 122.6(3) . . ?
C00F N005 O004 119.3(3) . . ?
C00F N005 O00C 118.1(3) . . ?
C00D C006 C007 122.7(2) . . ?
C00G C006 C007 120.0(2) . . ?
C00G C006 C00D 117.3(2) . . ?
C006 C007 N002 118.8(2) . . ?
C00B C007 N002 113.3(2) . . ?
C00B C007 C006 127.9(2) . . ?
C00E C009 N003 120.5(2) . . ?
C00K C009 N003 120.8(2) . . ?
C00K C009 C00E 118.6(2) . . ?
N003 C00A O001 108.10(19) . . ?
C00B C00A O001 112.4(2) . . ?
C00B C00A N003 101.5(2) . . ?
C00M C00A O001 110.7(2) . . ?
C00M C00A N003 111.7(2) . . ?
C00M C00A C00B 112.0(2) . . ?
C00A C00B C007 99.94(18) . . ?
C00N C00B C007 115.0(2) . . ?
C00N C00B C00A 110.6(2) . . ?
C00P C00B C007 109.4(2) . . ?
C00P C00B C00A 111.4(2) . . ?
C00P C00B C00N 110.1(2) . . ?
H00D C00D C006 119.45(15) . . ?
C00J C00D C006 121.1(3) . . ?
C00J C00D H00D 119.45(18) . . ?
H00E C00E C009 119.74(15) . . ?
C00I C00E C009 120.5(3) . . ?
C00I C00E H00E 119.74(17) . . ?
C00H C00F N005 119.7(3) . . ?
C00I C00F N005 119.2(3) . . ?
C00I C00F C00H 121.1(2) . . ?
H00G C00G C006 119.48(16) . . ?
C00O C00G C006 121.0(3) . . ?
C00O C00G H00G 119.48(19) . . ?
H00H C00H C00F 120.34(16) . . ?
C00K C00H C00F 119.3(3) . . ?
C00K C00H H00H 120.34(17) . . ?
C00F C00I C00E 119.5(3) . . ?
H00I C00I C00E 120.25(17) . . ?
H00I C00I C00F 120.25(16) . . ?
H00J C00J C00D 119.65(18) . . ?
C00L C00J C00D 120.7(3) . . ?
C00L C00J H00J 119.65(19) . . ?
C00H C00K C009 120.8(3) . . ?
H00K C00K C009 119.58(15) . . ?
H00K C00K C00H 119.58(17) . . ?
H00L C00L C00J 120.36(19) . . ?
C00O C00L C00J 119.3(3) . . ?
C00O C00L H00L 120.36(18) . . ?
C00A C00M O008 121.5(3) . . ?
H00M C00M O008 119.23(19) . . ?
H00M C00M C00A 119.23(17) . . ?
H00a C00N C00B 109.5 . . ?
H00b C00N C00B 109.5 . . ?
H00b C00N H00a 109.5 . . ?
H00c C00N C00B 109.5 . . ?
H00c C00N H00a 109.5 . . ?
H00c C00N H00b 109.5 . . ?
C00L C00O C00G 120.5(3) . . ?
H00O C00O C00G 119.74(19) . . ?
H00O C00O C00L 119.74(18) . . ?
H00f C00P C00B 109.5 . . ?
H00n C00P C00B 109.5 . . ?
H00n C00P H00f 109.5 . . ?
H00p C00P C00B 109.5 . . ?
H00p C00P H00f 109.5 . . ?
H00p C00P H00n 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 1.526
_oxdiff_exptl_absorpt_empirical_full_min 0.503
####################################################################### 
# 
# 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_exp_6464
_audit_block_doi                 10.5517/ccdc.csd.cc22bkww
_database_code_depnum_ccdc_archive 'CCDC 1916788'
loop_
_audit_author_name
_audit_author_address
'Liu Xiaobing'
;Huaqiao university
China
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;
_audit_creation_date             2019-03-12
_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         'C18 H19 Cl N2'
_chemical_formula_sum            'C18 H19 Cl N2'
_chemical_formula_weight         298.80
_chemical_absolute_configuration unk
_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'

_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                   8.2526(9)
_cell_length_b                   9.1103(10)
_cell_length_c                   21.0646(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1583.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1234
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.5310
_cell_measurement_theta_min      4.4140
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5349
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.783
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.259
_diffrn_reflns_theta_min         3.469
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  21.00   1.00    6.00    --   15.49 -57.00-180.00   59
  2  ω     -8.00  18.00   1.00    6.00    --  -16.28 -99.00-180.00   26
  3  ω    -82.00 -15.00   1.00    6.00    --  -16.28 -57.00 120.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0661480000
_diffrn_orient_matrix_UB_12      -0.0496509000
_diffrn_orient_matrix_UB_13      -0.0006603000
_diffrn_orient_matrix_UB_21      -0.0545511000
_diffrn_orient_matrix_UB_22      0.0599405000
_diffrn_orient_matrix_UB_23      -0.0023798000
_diffrn_orient_matrix_UB_31      0.0052144000
_diffrn_orient_matrix_UB_32      -0.0032425000
_diffrn_orient_matrix_UB_33      -0.0335823000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.557
_reflns_Friedel_fraction_full    0.861
_reflns_Friedel_fraction_max     0.655
_reflns_number_gt                2179
_reflns_number_total             3381
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 547 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.52(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.010
_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)+(0.0328P)²+0.0932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1062
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.45847(16) -0.14897(12) 0.57802(5) 0.0760(4) Uani 1 1 d . . . . .
N1 N 0.4657(4) 0.3313(3) 0.38989(12) 0.0437(7) Uani 1 1 d . . . . .
N2 N 0.3538(3) 0.3292(3) 0.34114(12) 0.0428(8) Uani 1 1 d . . . . .
C1 C 0.4618(4) 0.2195(4) 0.43411(14) 0.0399(8) Uani 1 1 d . . . . .
C2 C 0.3730(4) 0.0919(4) 0.42374(16) 0.0453(9) Uani 1 1 d . . . . .
H2 H 0.314146 0.081893 0.386336 0.054 Uiso 1 1 calc R . . . .
C3 C 0.3706(5) -0.0193(4) 0.46764(16) 0.0500(10) Uani 1 1 d . . . . .
H3 H 0.308885 -0.103086 0.460388 0.060 Uiso 1 1 calc R . . . .
C4 C 0.4601(5) -0.0060(4) 0.52251(16) 0.0501(10) Uani 1 1 d . . . . .
C5 C 0.5488(5) 0.1173(5) 0.53385(16) 0.0566(11) Uani 1 1 d . . . . .
H5 H 0.607455 0.125927 0.571365 0.068 Uiso 1 1 calc R . . . .
C6 C 0.5520(5) 0.2292(4) 0.49006(16) 0.0516(10) Uani 1 1 d . . . . .
H6 H 0.614665 0.312163 0.497767 0.062 Uiso 1 1 calc R . . . .
C7 C 0.5308(5) 0.4803(4) 0.39928(15) 0.0438(9) Uani 1 1 d . . . . .
H7 H 0.646550 0.474642 0.409410 0.053 Uiso 1 1 calc R . . . .
C8 C 0.4423(6) 0.5615(4) 0.45164(15) 0.0616(11) Uani 1 1 d . . . . .
H8A H 0.331029 0.574955 0.439733 0.092 Uiso 1 1 calc GR . . . .
H8B H 0.492181 0.655444 0.458193 0.092 Uiso 1 1 calc GR . . . .
H8C H 0.447695 0.505379 0.490172 0.092 Uiso 1 1 calc GR . . . .
C9 C 0.5083(4) 0.5441(4) 0.33163(15) 0.0424(9) Uani 1 1 d . . . . .
C10 C 0.4761(6) 0.7092(4) 0.33160(18) 0.0633(13) Uani 1 1 d . . . . .
H10A H 0.478274 0.745230 0.288775 0.095 Uiso 1 1 calc GR . . . .
H10B H 0.558067 0.758067 0.356085 0.095 Uiso 1 1 calc GR . . . .
H10C H 0.371648 0.728214 0.349926 0.095 Uiso 1 1 calc GR . . . .
C11 C 0.6594(5) 0.5103(5) 0.29187(16) 0.0591(12) Uani 1 1 d . . . . .
H11A H 0.684175 0.407605 0.294844 0.089 Uiso 1 1 calc GR . . . .
H11B H 0.749248 0.566590 0.307525 0.089 Uiso 1 1 calc GR . . . .
H11C H 0.639303 0.535634 0.248330 0.089 Uiso 1 1 calc GR . . . .
C12 C 0.3694(4) 0.4484(4) 0.30881(14) 0.0398(9) Uani 1 1 d . . . . .
C13 C 0.2606(4) 0.4726(4) 0.25410(15) 0.0404(9) Uani 1 1 d . . . . .
C14 C 0.2976(5) 0.5655(5) 0.20467(16) 0.0566(11) Uani 1 1 d . . . . .
H14 H 0.393641 0.618743 0.205920 0.068 Uiso 1 1 calc R . . . .
C15 C 0.1955(6) 0.5814(6) 0.15334(18) 0.0680(13) Uani 1 1 d . . . . .
H15 H 0.223671 0.643805 0.120202 0.082 Uiso 1 1 calc R . . . .
C16 C 0.0540(6) 0.5058(5) 0.15120(18) 0.0663(13) Uani 1 1 d . . . . .
H16 H -0.015502 0.517193 0.116793 0.080 Uiso 1 1 calc R . . . .
C17 C 0.0133(5) 0.4125(5) 0.19991(17) 0.0648(12) Uani 1 1 d . . . . .
H17 H -0.083211 0.359865 0.198203 0.078 Uiso 1 1 calc R . . . .
C18 C 0.1152(5) 0.3966(5) 0.25129(16) 0.0542(11) Uani 1 1 d . . . . .
H18 H 0.086151 0.334436 0.284389 0.065 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 C4 1.750(3) . ?
N1 N2 1.381(4) . ?
N1 C1 1.381(4) . ?
N1 C7 1.473(4) . ?
N2 C12 1.288(4) . ?
C1 C2 1.391(5) . ?
C1 C6 1.397(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(5) . ?
C4 C5 1.362(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.516(5) . ?
C7 C9 1.550(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.528(5) . ?
C9 C11 1.533(5) . ?
C9 C12 1.518(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.478(5) . ?
C13 C14 1.376(5) . ?
C13 C18 1.387(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.357(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(5) . ?
C18 H18 0.9300 . ?

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
N2 N1 C7 110.9(3) . . ?
C1 N1 N2 118.4(3) . . ?
C1 N1 C7 126.7(3) . . ?
C12 N2 N1 108.3(3) . . ?
N1 C1 C2 121.5(3) . . ?
N1 C1 C6 120.7(3) . . ?
C2 C1 C6 117.8(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 Cl1 119.4(3) . . ?
C5 C4 Cl1 120.1(3) . . ?
C5 C4 C3 120.5(3) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.6(4) . . ?
C5 C6 H6 119.7 . . ?
N1 C7 H7 109.7 . . ?
N1 C7 C8 111.8(3) . . ?
N1 C7 C9 100.3(2) . . ?
C8 C7 H7 109.7 . . ?
C8 C7 C9 115.3(3) . . ?
C9 C7 H7 109.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 113.0(3) . . ?
C10 C9 C11 109.8(3) . . ?
C11 C9 C7 109.2(3) . . ?
C12 C9 C7 99.5(3) . . ?
C12 C9 C10 115.7(3) . . ?
C12 C9 C11 109.0(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C9 113.1(3) . . ?
N2 C12 C13 118.5(3) . . ?
C13 C12 C9 128.3(3) . . ?
C14 C13 C12 123.2(3) . . ?
C14 C13 C18 117.8(3) . . ?
C18 C13 C12 119.0(3) . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.5(4) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.9(4) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(4) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(4) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.6(4) . . ?
C17 C18 H18 119.7 . . ?

_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 1.044
_oxdiff_exptl_absorpt_empirical_full_min 0.954
