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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_as-zhou
_database_code_depnum_ccdc_archive 'CCDC 1974689'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-02-24 downloaded from the CCDC.
;
_audit_creation_date             2019-04-29
_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 H13 Cl N2 O'
_chemical_formula_sum            'C15 H13 Cl N2 O'
_chemical_formula_weight         272.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3479(5)
_cell_length_b                   10.0774(5)
_cell_length_c                   11.9461(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.694(4)
_cell_angle_gamma                90
_cell_volume                     1350.43(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2715
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9490
_cell_measurement_theta_min      2.6580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81147
_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    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6037
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.657
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  38.00   1.00    2.00    --  -11.59  77.00 -90.00   77
  2  ω      1.00  84.00   1.00    2.00    --   11.74  77.00 150.00   83
  3  ω    -20.00  20.00   1.00    2.00    --   11.74  77.00 120.00   40
;
_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      -0.0074073000
_diffrn_orient_matrix_UB_12      -0.0686273000
_diffrn_orient_matrix_UB_13      -0.0120008000
_diffrn_orient_matrix_UB_21      -0.0620468000
_diffrn_orient_matrix_UB_22      0.0099540000
_diffrn_orient_matrix_UB_23      -0.0165365000
_diffrn_orient_matrix_UB_31      0.0095286000
_diffrn_orient_matrix_UB_32      0.0117747000
_diffrn_orient_matrix_UB_33      -0.0565527000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1982
_reflns_number_total             2370
_reflns_odcompleteness_completeness 99.90
_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 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.900
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.070
_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)+(0.0544P)²+0.9693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1220
_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 Riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.58660(6) 0.62205(7) 0.24657(5) 0.0362(2) Uani 1 1 d . . . . .
O1 O -0.02440(14) 0.58825(15) 0.13124(13) 0.0224(4) Uani 1 1 d . . . . .
N1 N -0.09270(15) 0.79908(18) 0.15464(15) 0.0179(4) Uani 1 1 d . . . . .
H1 H -0.082020 0.801185 0.227454 0.021 Uiso 1 1 d R . . . .
N2 N -0.02436(17) 0.6946(2) -0.10553(16) 0.0178(4) Uani 1 1 d . . . . .
C1 C -0.14659(18) 0.8667(2) -0.02881(18) 0.0160(5) Uani 1 1 d . . . . .
C2 C -0.18570(19) 0.9546(2) -0.11386(19) 0.0216(5) Uani 1 1 d . . . . .
H2 H -0.188323 0.930311 -0.191029 0.026 Uiso 1 1 calc R . . . .
C3 C -0.2216(2) 1.0809(2) -0.0844(2) 0.0246(5) Uani 1 1 d . . . . .
H3 H -0.248202 1.143808 -0.141896 0.030 Uiso 1 1 calc R . . . .
C4 C -0.2186(2) 1.1144(2) 0.0284(2) 0.0239(5) Uani 1 1 d . . . . .
H4 H -0.247403 1.198919 0.046932 0.029 Uiso 1 1 calc R . . . .
C5 C -0.17457(19) 1.0280(2) 0.1152(2) 0.0207(5) Uani 1 1 d . . . . .
H5 H -0.169422 1.053191 0.192412 0.025 Uiso 1 1 calc R . . . .
C6 C -0.13865(18) 0.9043(2) 0.08485(18) 0.0162(5) Uani 1 1 d . . . . .
C7 C -0.07051(18) 0.6915(2) 0.09376(18) 0.0168(5) Uani 1 1 d . . . . .
C8 C -0.11372(18) 0.7217(2) -0.03316(18) 0.0161(5) Uani 1 1 d . . . . .
C9 C -0.2238(2) 0.6337(2) -0.07450(19) 0.0199(5) Uani 1 1 d . . . . .
H9A H -0.261543 0.665822 -0.149777 0.024 Uiso 1 1 calc R . . . .
H9B H -0.196397 0.541726 -0.084004 0.024 Uiso 1 1 calc R . . . .
C10 C -0.31660(19) 0.6317(2) 0.00345(19) 0.0184(5) Uani 1 1 d . . . . .
C11 C -0.3284(2) 0.5208(2) 0.0703(2) 0.0230(5) Uani 1 1 d . . . . .
H11 H -0.278439 0.446088 0.065188 0.028 Uiso 1 1 calc R . . . .
C12 C -0.4118(2) 0.5169(2) 0.1444(2) 0.0253(5) Uani 1 1 d . . . . .
H12 H -0.419963 0.439919 0.188488 0.030 Uiso 1 1 calc R . . . .
C13 C -0.4823(2) 0.6268(2) 0.1529(2) 0.0247(6) Uani 1 1 d . . . . .
C14 C -0.4735(2) 0.7384(2) 0.0878(2) 0.0267(6) Uani 1 1 d . . . . .
H14 H -0.522777 0.813344 0.094349 0.032 Uiso 1 1 calc R . . . .
C15 C -0.39154(19) 0.7397(2) 0.0126(2) 0.0230(5) Uani 1 1 d . . . . .
H15 H -0.386328 0.815542 -0.033562 0.028 Uiso 1 1 calc R . . . .
H2A H -0.002(2) 0.615(3) -0.098(2) 0.017(6) Uiso 1 1 d . . . . .
H2B H 0.037(2) 0.752(3) -0.087(2) 0.020(6) 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 C13 1.748(2) . ?
O1 C7 1.219(3) . ?
N1 H1 0.8601 . ?
N1 C6 1.400(3) . ?
N1 C7 1.350(3) . ?
N2 C8 1.454(3) . ?
N2 H2A 0.84(3) . ?
N2 H2B 0.91(3) . ?
C1 C2 1.370(3) . ?
C1 C6 1.399(3) . ?
C1 C8 1.512(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(3) . ?
C7 C8 1.551(3) . ?
C8 C9 1.551(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.507(3) . ?
C10 C11 1.392(3) . ?
C10 C15 1.395(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(3) . ?
C13 C14 1.379(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 H1 124.5 . . ?
C7 N1 H1 123.7 . . ?
C7 N1 C6 111.73(17) . . ?
C8 N2 H2A 109.7(16) . . ?
C8 N2 H2B 108.2(15) . . ?
H2A N2 H2B 112(2) . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 C8 130.8(2) . . ?
C6 C1 C8 108.35(18) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.8(2) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 121.3 . . ?
C6 C5 C4 117.3(2) . . ?
C6 C5 H5 121.3 . . ?
C1 C6 N1 109.67(18) . . ?
C5 C6 N1 128.9(2) . . ?
C5 C6 C1 121.5(2) . . ?
O1 C7 N1 126.3(2) . . ?
O1 C7 C8 125.49(19) . . ?
N1 C7 C8 108.20(18) . . ?
N2 C8 C1 113.57(18) . . ?
N2 C8 C7 113.48(17) . . ?
N2 C8 C9 107.71(17) . . ?
C1 C8 C7 101.47(17) . . ?
C1 C8 C9 111.87(17) . . ?
C7 C8 C9 108.66(17) . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.55(17) . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 C15 117.9(2) . . ?
C15 C10 C9 121.9(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(2) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 Cl1 118.77(19) . . ?
C12 C13 C14 121.4(2) . . ?
C14 C13 Cl1 119.83(19) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.3(2) . . ?
C14 C15 H15 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C13 C14 C15 -178.98(18) . . . . ?
O1 C7 C8 N2 -50.8(3) . . . . ?
O1 C7 C8 C1 -173.0(2) . . . . ?
O1 C7 C8 C9 69.0(3) . . . . ?
N1 C7 C8 N2 129.15(19) . . . . ?
N1 C7 C8 C1 6.9(2) . . . . ?
N1 C7 C8 C9 -111.07(19) . . . . ?
N2 C8 C9 C10 169.91(18) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 C8 C9 C10 -64.6(2) . . . . ?
C2 C1 C6 N1 -177.93(18) . . . . ?
C2 C1 C6 C5 2.9(3) . . . . ?
C2 C1 C8 N2 54.4(3) . . . . ?
C2 C1 C8 C7 176.5(2) . . . . ?
C2 C1 C8 C9 -67.8(3) . . . . ?
C2 C3 C4 C5 3.4(3) . . . . ?
C3 C4 C5 C6 -2.9(3) . . . . ?
C4 C5 C6 N1 -179.2(2) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C6 N1 C7 O1 175.7(2) . . . . ?
C6 N1 C7 C8 -4.2(2) . . . . ?
C6 C1 C2 C3 -2.4(3) . . . . ?
C6 C1 C8 N2 -129.49(19) . . . . ?
C6 C1 C8 C7 -7.3(2) . . . . ?
C6 C1 C8 C9 108.3(2) . . . . ?
C7 N1 C6 C1 -0.8(2) . . . . ?
C7 N1 C6 C5 178.3(2) . . . . ?
C7 C8 C9 C10 46.6(2) . . . . ?
C8 C1 C2 C3 173.4(2) . . . . ?
C8 C1 C6 N1 5.5(2) . . . . ?
C8 C1 C6 C5 -173.68(19) . . . . ?
C8 C9 C10 C11 -105.5(2) . . . . ?
C8 C9 C10 C15 73.5(3) . . . . ?
C9 C10 C11 C12 178.9(2) . . . . ?
C9 C10 C15 C14 -177.5(2) . . . . ?
C10 C11 C12 C13 -1.3(3) . . . . ?
C11 C10 C15 C14 1.5(3) . . . . ?
C11 C12 C13 Cl1 -179.74(17) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C10 -1.3(3) . . . . ?
C15 C10 C11 C12 -0.2(3) . . . . ?

_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 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.669
####################################################################### 
# 
# 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_as-11
_database_code_depnum_ccdc_archive 'CCDC 1974693'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-02-24 downloaded from the CCDC.
;
_audit_creation_date             2019-04-29
_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         'C16 H15 Cl N2 O'
_chemical_formula_sum            'C16 H15 Cl N2 O'
_chemical_formula_weight         286.75
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.8233(13)
_cell_length_b                   10.2114(7)
_cell_length_c                   12.0326(13)
_cell_angle_alpha                90
_cell_angle_beta                 116.906(13)
_cell_angle_gamma                90
_cell_volume                     1405.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2341
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9310
_cell_measurement_theta_min      2.6890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54222
_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    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5918
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.674
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  37.00   1.00    4.00    --   11.74 -57.00-150.00   97
  2  ω    -15.00  77.00   1.00    4.00    --   11.74  57.00   0.00   92
;
_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      -0.0031270000
_diffrn_orient_matrix_UB_12      0.0436623000
_diffrn_orient_matrix_UB_13      0.0441944000
_diffrn_orient_matrix_UB_21      -0.0615055000
_diffrn_orient_matrix_UB_22      -0.0088801000
_diffrn_orient_matrix_UB_23      -0.0271239000
_diffrn_orient_matrix_UB_31      0.0077977000
_diffrn_orient_matrix_UB_32      -0.0533382000
_diffrn_orient_matrix_UB_33      0.0407812000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2021
_reflns_number_total             2474
_reflns_odcompleteness_completeness 99.90
_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 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.022
_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)+(0.0393P)²+0.8848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C15(H15), C5(H5), C12(H12), C11(H11), C14(H14)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.18086(5) 0.21140(5) 0.58198(5) 0.02383(18) Uani 1 1 d . . . . .
O1 O 0.09538(13) 0.92522(14) 0.45186(13) 0.0195(4) Uani 1 1 d . . . . .
N1 N 0.11598(15) 0.70109(16) 0.44456(16) 0.0155(4) Uani 1 1 d . . . . .
H1 H 0.102671 0.693381 0.368105 0.019 Uiso 1 1 calc R . . . .
N2 N 0.07426(18) 0.8471(2) 0.68436(17) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.13961(18) 0.5954(2) 0.52779(19) 0.0142(5) Uani 1 1 d . . . . .
C10 C 0.36625(19) 0.8045(2) 0.67474(19) 0.0174(5) Uani 1 1 d . . . . .
C8 C 0.11695(18) 0.8171(2) 0.50094(19) 0.0152(5) Uani 1 1 d . . . . .
C3 C 0.14670(18) 0.4641(2) 0.5055(2) 0.0171(5) Uani 1 1 d . . . . .
H3 H 0.135661 0.433683 0.428039 0.021 Uiso 1 1 calc R . . . .
C1 C 0.15691(18) 0.6424(2) 0.64371(19) 0.0152(5) Uani 1 1 d . . . . .
C6 C 0.17946(18) 0.5554(2) 0.7401(2) 0.0183(5) Uani 1 1 d . . . . .
H6 H 0.190141 0.585690 0.817487 0.022 Uiso 1 1 calc R . . . .
C7 C 0.15387(18) 0.7900(2) 0.63996(19) 0.0152(5) Uani 1 1 d . . . . .
C15 C 0.39188(19) 0.8789(2) 0.5931(2) 0.0210(5) Uani 1 1 d . . . . .
H15 H 0.356001 0.959849 0.566263 0.025 Uiso 1 1 calc R . . . .
C9 C 0.27702(19) 0.8494(2) 0.7165(2) 0.0184(5) Uani 1 1 d . . . . .
H9A H 0.271067 0.944116 0.710341 0.022 Uiso 1 1 calc R . . . .
H9B H 0.304631 0.826212 0.803416 0.022 Uiso 1 1 calc R . . . .
C5 C 0.18595(19) 0.4223(2) 0.7200(2) 0.0199(5) Uani 1 1 d . . . . .
H5 H 0.200091 0.362576 0.783594 0.024 Uiso 1 1 calc R . . . .
C4 C 0.17124(18) 0.3793(2) 0.6048(2) 0.0182(5) Uani 1 1 d . . . . .
C13 C 0.52481(19) 0.7134(2) 0.5877(2) 0.0212(5) Uani 1 1 d . . . . .
C12 C 0.49939(19) 0.6392(2) 0.6692(2) 0.0215(5) Uani 1 1 d . . . . .
H12 H 0.535008 0.558038 0.695444 0.026 Uiso 1 1 calc R . . . .
C11 C 0.42208(19) 0.6836(2) 0.7122(2) 0.0206(5) Uani 1 1 d . . . . .
H11 H 0.407139 0.631938 0.767060 0.025 Uiso 1 1 calc R . . . .
C14 C 0.4701(2) 0.8341(2) 0.5513(2) 0.0225(5) Uani 1 1 d . . . . .
H14 H 0.486209 0.886166 0.497548 0.027 Uiso 1 1 calc R . . . .
C16 C 0.6085(2) 0.6635(2) 0.5409(2) 0.0296(6) Uani 1 1 d . . . . .
H16A H 0.685715 0.657884 0.609184 0.044 Uiso 1 1 calc GR . . . .
H16B H 0.609188 0.722640 0.479192 0.044 Uiso 1 1 calc GR . . . .
H16C H 0.584002 0.578382 0.504647 0.044 Uiso 1 1 calc GR . . . .
H2A H 0.066(2) 0.929(3) 0.666(2) 0.024(7) Uiso 1 1 d . . . . .
H2B H 0.003(3) 0.811(3) 0.644(3) 0.038(8) 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 C4 1.750(2) . ?
O1 C8 1.224(2) . ?
N1 H1 0.8600 . ?
N1 C2 1.409(3) . ?
N1 C8 1.362(3) . ?
N2 C7 1.470(3) . ?
N2 H2A 0.86(3) . ?
N2 H2B 0.90(3) . ?
C2 C3 1.379(3) . ?
C2 C1 1.395(3) . ?
C10 C15 1.393(3) . ?
C10 C9 1.514(3) . ?
C10 C11 1.396(3) . ?
C8 C7 1.543(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(3) . ?
C1 C6 1.384(3) . ?
C1 C7 1.507(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.390(3) . ?
C7 C9 1.547(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.388(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.383(3) . ?
C13 C12 1.390(3) . ?
C13 C14 1.387(3) . ?
C13 C16 1.509(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.386(3) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C2 N1 H1 124.4 . . ?
C8 N1 H1 124.4 . . ?
C8 N1 C2 111.19(18) . . ?
C7 N2 H2A 108.0(17) . . ?
C7 N2 H2B 110.1(17) . . ?
H2A N2 H2B 106(2) . . ?
C3 C2 N1 128.2(2) . . ?
C3 C2 C1 122.35(19) . . ?
C1 C2 N1 109.44(18) . . ?
C15 C10 C9 121.57(19) . . ?
C15 C10 C11 117.4(2) . . ?
C11 C10 C9 121.0(2) . . ?
O1 C8 N1 126.5(2) . . ?
O1 C8 C7 125.19(19) . . ?
N1 C8 C7 108.25(17) . . ?
C2 C3 H3 121.7 . . ?
C2 C3 C4 116.5(2) . . ?
C4 C3 H3 121.7 . . ?
C2 C1 C7 108.91(17) . . ?
C6 C1 C2 119.7(2) . . ?
C6 C1 C7 131.26(19) . . ?
C1 C6 H6 120.4 . . ?
C1 C6 C5 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
N2 C7 C8 113.57(17) . . ?
N2 C7 C1 113.48(18) . . ?
N2 C7 C9 108.52(17) . . ?
C8 C7 C9 107.72(17) . . ?
C1 C7 C8 101.70(16) . . ?
C1 C7 C9 111.64(17) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C10 C9 C7 113.89(17) . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C7 C9 H9A 108.8 . . ?
C7 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C3 C4 Cl1 118.62(17) . . ?
C5 C4 Cl1 118.76(17) . . ?
C5 C4 C3 122.6(2) . . ?
C12 C13 C16 120.9(2) . . ?
C14 C13 C12 117.4(2) . . ?
C14 C13 C16 121.7(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C15 C14 H14 119.2 . . ?
C13 C14 C15 121.6(2) . . ?
C13 C14 H14 119.2 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 1.341
_oxdiff_exptl_absorpt_empirical_full_min 0.556
