# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

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

data_mo_d8v19794_0m
_database_code_depnum_ccdc_archive 'CCDC 1948537'
loop_
_audit_author_name
_audit_author_address
'wang yuhong'
;ECNU
China
;
_audit_update_record             
;
2019-08-21 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 Cl N O2'
_chemical_formula_weight         171.58

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.5231(5)
_cell_length_b                   3.82670(10)
_cell_length_c                   23.9744(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.4320(10)
_cell_angle_gamma                90
_cell_volume                     1421.58(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4202
_cell_measurement_theta_min      5.258
_cell_measurement_theta_max      54.956

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.477
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6943
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.702
_diffrn_reflns_theta_max         25.980
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1377
_reflns_number_gt                1232
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.8735P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1377
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.09976(3) 0.05166(12) 0.29280(2) 0.04943(18) Uani 1 1 d . . . . .
O1 O 0.47942(7) 0.3219(4) 0.43834(5) 0.0523(3) Uani 1 1 d . . . . .
O2 O 0.38450(8) 0.5722(4) 0.49163(5) 0.0515(3) Uani 1 1 d . . . . .
H2 H 0.4283 0.6055 0.5117 0.077 Uiso 1 1 calc R U . . .
N1 N 0.42139(9) 0.0664(4) 0.33845(6) 0.0506(4) Uani 1 1 d . . . . .
H1A H 0.4256 -0.0345 0.3067 0.061 Uiso 1 1 calc R U . . .
H1B H 0.4671 0.1107 0.3593 0.061 Uiso 1 1 calc R U . . .
C1 C 0.34255(9) 0.1557(4) 0.35564(6) 0.0342(3) Uani 1 1 d . . . . .
C2 C 0.26918(10) 0.0803(4) 0.32075(6) 0.0368(4) Uani 1 1 d . . . . .
H2A H 0.2752 -0.0260 0.2863 0.044 Uiso 1 1 calc R U . . .
C3 C 0.18880(10) 0.1626(4) 0.33720(6) 0.0358(3) Uani 1 1 d . . . . .
C4 C 0.17560(10) 0.3240(4) 0.38780(6) 0.0405(4) Uani 1 1 d . . . . .
H4 H 0.1204 0.3774 0.3982 0.049 Uiso 1 1 calc R U . . .
C5 C 0.24709(10) 0.4017(4) 0.42192(6) 0.0384(4) Uani 1 1 d . . . . .
H5 H 0.2397 0.5117 0.4559 0.046 Uiso 1 1 calc R U . . .
C6 C 0.33103(9) 0.3213(4) 0.40738(6) 0.0336(3) Uani 1 1 d . . . . .
C7 C 0.40441(10) 0.4033(4) 0.44631(6) 0.0377(4) Uani 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 C3 1.7457(15) . ?
O1 C7 1.2313(19) . ?
O2 C7 1.3167(19) . ?
O2 H2 0.8200 . ?
N1 C1 1.358(2) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C1 C2 1.402(2) . ?
C1 C6 1.414(2) . ?
C2 C3 1.368(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.387(2) . ?
C4 C5 1.371(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.463(2) . ?

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
C7 O2 H2 109.5 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N1 C1 C2 118.79(14) . . ?
N1 C1 C6 122.87(13) . . ?
C2 C1 C6 118.35(13) . . ?
C3 C2 C1 120.20(14) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 122.66(14) . . ?
C2 C3 Cl1 118.09(12) . . ?
C4 C3 Cl1 119.24(12) . . ?
C5 C4 C3 117.49(14) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C4 C5 C6 122.32(14) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 118.98(13) . . ?
C5 C6 C7 119.58(14) . . ?
C1 C6 C7 121.43(13) . . ?
O1 C7 O2 121.54(14) . . ?
O1 C7 C6 123.65(14) . . ?
O2 C7 C6 114.81(13) . . ?

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
N1 C1 C2 C3 179.10(14) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C1 C2 C3 Cl1 -178.32(11) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
Cl1 C3 C4 C5 178.96(12) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C4 C5 C6 C7 -178.44(14) . . . . ?
N1 C1 C6 C5 -179.53(15) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
N1 C1 C6 C7 -0.8(2) . . . . ?
C2 C1 C6 C7 179.07(14) . . . . ?
C5 C6 C7 O1 175.30(15) . . . . ?
C1 C6 C7 O1 -3.4(2) . . . . ?
C5 C6 C7 O2 -4.3(2) . . . . ?
C1 C6 C7 O2 176.92(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O1 0.86 2.06 2.6916(18) 129.9 .
N1 H1A Cl1 0.86 2.87 3.7100(15) 165.8 4_545
O2 H2 O1 0.82 1.83 2.6497(16) 175.2 5_666
N1 H1B O1 0.86 2.06 2.6916(18) 129.9 .
N1 H1A Cl1 0.86 2.87 3.7100(15) 165.8 4_545
O2 H2 O1 0.82 1.83 2.6497(16) 175.2 5_666

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_741
_database_code_depnum_ccdc_archive 'CCDC 1991082'
loop_
_audit_author_name
_audit_author_address
zfh
;ECNU
China
;
_audit_update_record             
;
2020-03-18 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_audit_creation_date             2019-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H26 N2 O4'
_chemical_formula_sum            'C17 H26 N2 O4'
_chemical_formula_weight         322.40
_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'
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                   7.90480(10)
_cell_length_b                   11.22760(10)
_cell_length_c                   19.3205(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1714.73(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28585
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1190
_cell_measurement_theta_min      4.5450
_shelx_estimated_absorpt_T_max   0.801
_shelx_estimated_absorpt_T_min   0.751
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (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    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41359
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.538
_diffrn_reflns_theta_min         4.555
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  31.00   1.00    1.00    --    0.00  77.00 -82.00   60
  2  ω     65.00 113.00   1.00    1.00    --   95.80  77.00 -82.00   48
  3  ω     38.00 126.00   1.00    1.00    --   95.80 -77.00 151.00   88
  4  ω      8.00  36.00   1.00    1.00    --   95.80 -77.00 151.00   28
  5  ω     36.00  85.00   1.00    1.00    --    0.00  77.00 -82.00   49
  6  ω     14.00  89.00   1.00    1.00    --    0.00  38.00   0.00   75
  7  ω     46.00  78.00   1.00    1.00    --    0.00  57.00-120.00   32
  8  ω    -84.00 -59.00   1.00    1.00    --    0.00 -77.00 151.00   25
  9  ω    -17.00  12.00   1.00    1.00    --    0.00  57.00   0.00   29
 10  ω    -84.00  20.00   1.00    1.00    --    0.00 -57.00  60.00  104
 11  ω    -18.00  15.00   1.00    1.00    --    0.00  38.00-150.00   33
 12  ω     36.00  61.00   1.00    1.00    --    0.00  57.00   0.00   25
 13  ω     17.00  87.00   1.00    1.00    --    0.00  38.00  90.00   70
 14  ω    -22.00  88.00   1.00    1.00    --    0.00  57.00 150.00  110
 15  ω    -19.00   6.00   1.00    1.00    --    0.00  38.00  90.00   25
 16  ω    -33.00  27.00   1.00    1.00    --    0.00 -77.00 151.00   60
 17  ω    -23.00  40.00   1.00    1.00    --    0.00  57.00-120.00   63
 18  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 19  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 20  ω     71.00  97.00   1.00    1.00    --   95.80  61.00 120.00   26
 21  ω     63.00  88.00   1.00    1.00    --   95.80  82.00   0.00   25
 22  ω     72.00 184.00   1.00    1.00    --   95.80  56.00 -94.02  112
 23  ω     71.00 164.00   1.00    1.00    --   95.80  61.00 150.00   93
 24  ω    111.00 185.00   1.00    1.00    --   95.80  82.00-120.00   74
 25  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 26  ω    144.00 179.00   1.00    1.00    --   95.80  77.00  17.74   35
 27  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 28  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 29  ω    113.00 139.00   1.00    1.00    --   95.80  77.00  60.00   26
 30  ω     68.00 171.00   1.00    1.00    --   95.80  70.00-123.30  103
 31  ω     65.00 105.00   1.00    1.00    --   95.80  77.00  -5.61   40
 32  ω     65.00 107.00   1.00    1.00    --   95.80  77.00-180.00   42
 33  ω    101.00 127.00   1.00    1.00    --   95.80  82.00-150.00   26
 34  ω     73.00 138.00   1.00    1.00    --   95.80  61.00  90.00   65
 35  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  17.74   25
 36  ω     71.00 110.00   1.00    1.00    --   95.80  59.00 166.93   39
 37  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 38  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 39  ω     73.00 185.00   1.00    1.00    --   95.80  53.00  -5.60  112
 40  ω    150.00 179.00   1.00    1.00    --   95.80  82.00 -30.00   29
 41  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 42  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 43  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 44  ω     74.00 107.00   1.00    1.00    --   95.80  49.00  61.49   33
 45  ω    113.00 184.00   1.00    1.00    --   95.80  49.00  61.49   71
 46  ω     71.00 112.00   1.00    1.00    --   95.80  61.00  60.00   41
 47  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 48  ω    157.00 182.00   1.00    1.00    --   95.80  77.00 -60.00   25
 49  ω     23.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00  105
 50  ω     64.00  90.00   1.00    1.00    --   95.80  82.00 -60.00   26
 51  ω    148.00 177.00   1.00    1.00    --   95.80  82.00 150.00   29
 52  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 150.00   25
 53  ω     12.00  38.00   1.00    1.00    --   95.80 -82.00-120.00   26
 54  ω     56.00 126.00   1.00    1.00    --   95.80 -82.00-120.00   70
 55  ω     75.00 179.00   1.00    1.00    --   95.80  45.00 -30.00  104
 56  ω     78.00 105.00   1.00    1.00    --   95.80  45.00 150.00   27
 57  ω    122.00 148.00   1.00    1.00    --   95.80  45.00 150.00   26
 58  ω     75.00 100.00   1.00    1.00    --   95.80  52.00 110.64   25
 59  ω      6.00  50.00   1.00    1.00    --   95.80 -82.00  90.00   44
 60  ω     58.00 125.00   1.00    1.00    --   95.80 -82.00  90.00   67
 61  ω    145.00 170.00   1.00    1.00    --   95.80  72.00 -96.83   25
 62  ω     69.00 157.00   1.00    1.00    --   95.80  66.00-150.04   88
 63  ω    138.00 183.00   1.00    1.00    --   95.80  82.00  90.00   45
 64  ω     67.00  92.00   1.00    1.00    --   95.80  72.00 -96.83   25
 65  ω    116.00 183.00   1.00    1.00    --   95.80  61.00 120.00   67
 66  ω     79.00 126.00   1.00    1.00    --   95.80 -82.00   0.00   47
 67  ω     63.00 183.00   1.00    1.00    --   95.80  82.00 160.27  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1362294000
_diffrn_orient_matrix_UB_12      0.0238668000
_diffrn_orient_matrix_UB_13      -0.0552716000
_diffrn_orient_matrix_UB_21      -0.0493223000
_diffrn_orient_matrix_UB_22      -0.1161824000
_diffrn_orient_matrix_UB_23      -0.0372863000
_diffrn_orient_matrix_UB_31      -0.1304696000
_diffrn_orient_matrix_UB_32      0.0690094000
_diffrn_orient_matrix_UB_33      -0.0436633000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3405
_reflns_number_total             3463
_reflns_odcompleteness_completeness 99.94
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (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 (Sheldrick, 2015)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_coef       0.0070(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.037
_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)+(0.0392P)²+0.2686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0712
_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), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.81531(17) 0.81640(11) 0.31083(6) 0.0266(3) Uani 1 1 d . . . . .
O2 O 0.78500(18) 0.76269(12) 0.20370(6) 0.0303(3) Uani 1 1 d . . . . .
O3 O 0.73469(13) 0.50730(9) 0.43285(5) 0.0145(2) Uani 1 1 d . . . . .
O4 O 0.89139(14) 0.55073(11) 0.33235(5) 0.0192(3) Uani 1 1 d . . . . .
N1 N 0.74300(18) 0.76037(12) 0.26501(7) 0.0192(3) Uani 1 1 d . . . . .
N2 N 0.82475(15) 0.54551(11) 0.49555(6) 0.0128(3) Uani 1 1 d . . . . .
C1 C 0.5939(2) 0.68880(14) 0.28341(7) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.4514(2) 0.70558(14) 0.24246(8) 0.0190(3) Uani 1 1 d . . . . .
H2 H 0.453398 0.758685 0.205523 0.023 Uiso 1 1 calc R . . . .
C3 C 0.3066(2) 0.64182(15) 0.25769(8) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.209091 0.652776 0.231486 0.025 Uiso 1 1 calc R . . . .
C4 C 0.3071(2) 0.56138(15) 0.31221(8) 0.0206(3) Uani 1 1 d . . . . .
H4 H 0.209711 0.518350 0.322437 0.025 Uiso 1 1 calc R . . . .
C5 C 0.4527(2) 0.54468(14) 0.35175(8) 0.0180(3) Uani 1 1 d . . . . .
H5 H 0.451571 0.489267 0.387529 0.022 Uiso 1 1 calc R . . . .
C6 C 0.59944(19) 0.60902(13) 0.33887(7) 0.0149(3) Uani 1 1 d . . . . .
C7 C 0.76404(18) 0.58912(13) 0.37878(7) 0.0147(3) Uani 1 1 d . . . . .
H7 H 0.799297 0.665136 0.399121 0.018 Uiso 1 1 calc R . . . .
C8 C 0.69189(19) 0.58165(13) 0.54654(7) 0.0156(3) Uani 1 1 d . . . . .
C9 C 0.7860(2) 0.61817(13) 0.61293(7) 0.0172(3) Uani 1 1 d . . . . .
H9A H 0.851140 0.689669 0.603803 0.021 Uiso 1 1 calc R . . . .
H9B H 0.703759 0.636877 0.648575 0.021 Uiso 1 1 calc R . . . .
C10 C 0.9040(2) 0.52160(14) 0.63952(7) 0.0178(3) Uani 1 1 d . . . . .
H10A H 0.839245 0.451571 0.652255 0.021 Uiso 1 1 calc R . . . .
H10B H 0.963482 0.549719 0.680291 0.021 Uiso 1 1 calc R . . . .
C11 C 1.0304(2) 0.49003(14) 0.58311(8) 0.0171(3) Uani 1 1 d . . . . .
H11A H 1.103351 0.426764 0.599768 0.020 Uiso 1 1 calc R . . . .
H11B H 1.100821 0.558962 0.573845 0.020 Uiso 1 1 calc R . . . .
C12 C 0.94673(19) 0.44971(13) 0.51502(7) 0.0148(3) Uani 1 1 d . . . . .
C13 C 0.5546(2) 0.48834(15) 0.56236(8) 0.0202(3) Uani 1 1 d . . . . .
H13A H 0.513963 0.454714 0.519808 0.030 Uiso 1 1 calc GR . . . .
H13B H 0.462520 0.525703 0.586434 0.030 Uiso 1 1 calc GR . . . .
H13C H 0.601564 0.426416 0.590722 0.030 Uiso 1 1 calc GR . . . .
C14 C 0.6054(2) 0.69301(15) 0.51769(8) 0.0211(3) Uani 1 1 d . . . . .
H14A H 0.689742 0.749079 0.502984 0.032 Uiso 1 1 calc GR . . . .
H14B H 0.536403 0.728429 0.553022 0.032 Uiso 1 1 calc GR . . . .
H14C H 0.535783 0.671376 0.478965 0.032 Uiso 1 1 calc GR . . . .
C15 C 0.8712(2) 0.32410(13) 0.52213(9) 0.0205(3) Uani 1 1 d . . . . .
H15A H 0.804201 0.319918 0.563499 0.031 Uiso 1 1 calc GR . . . .
H15B H 0.960972 0.266675 0.524610 0.031 Uiso 1 1 calc GR . . . .
H15C H 0.801242 0.307271 0.482701 0.031 Uiso 1 1 calc GR . . . .
C16 C 1.0853(2) 0.44657(15) 0.45967(8) 0.0179(3) Uani 1 1 d . . . . .
H16A H 1.041700 0.410317 0.418362 0.027 Uiso 1 1 calc GR . . . .
H16B H 1.179708 0.401094 0.476386 0.027 Uiso 1 1 calc GR . . . .
H16C H 1.121452 0.526330 0.449570 0.027 Uiso 1 1 calc GR . . . .
C17 C 0.8539(2) 0.44033(17) 0.29845(9) 0.0263(4) Uani 1 1 d . . . . .
H17A H 0.946469 0.418732 0.268832 0.039 Uiso 1 1 calc GR . . . .
H17B H 0.752977 0.449058 0.271288 0.039 Uiso 1 1 calc GR . . . .
H17C H 0.837171 0.379218 0.332525 0.039 Uiso 1 1 calc GR . . . .


_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
O1 N1 1.2272(17) . ?
O2 N1 1.2304(18) . ?
O3 N2 1.4691(14) . ?
O3 C7 1.4104(17) . ?
O4 C7 1.4157(18) . ?
O4 C17 1.433(2) . ?
N1 C1 1.470(2) . ?
N2 C8 1.4960(18) . ?
N2 C12 1.4927(19) . ?
C1 C2 1.389(2) . ?
C1 C6 1.397(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(2) . ?
C6 C7 1.529(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.538(2) . ?
C8 C13 1.539(2) . ?
C8 C14 1.530(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.520(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.520(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.540(2) . ?
C12 C15 1.538(2) . ?
C12 C16 1.531(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C7 O3 N2 109.93(10) . . ?
C7 O4 C17 113.96(12) . . ?
O1 N1 O2 123.91(14) . . ?
O1 N1 C1 118.63(12) . . ?
O2 N1 C1 117.43(13) . . ?
O3 N2 C8 106.38(10) . . ?
O3 N2 C12 108.08(10) . . ?
C12 N2 C8 118.88(11) . . ?
C2 C1 N1 115.99(13) . . ?
C2 C1 C6 123.30(14) . . ?
C6 C1 N1 120.70(14) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.70(14) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.76(15) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.40(15) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.42(15) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 120.48(13) . . ?
C5 C6 C1 116.40(14) . . ?
C5 C6 C7 122.97(13) . . ?
O3 C7 O4 112.83(12) . . ?
O3 C7 C6 109.20(12) . . ?
O3 C7 H7 108.5 . . ?
O4 C7 C6 109.27(11) . . ?
O4 C7 H7 108.5 . . ?
C6 C7 H7 108.5 . . ?
N2 C8 C9 106.38(12) . . ?
N2 C8 C13 116.18(12) . . ?
N2 C8 C14 107.18(12) . . ?
C9 C8 C13 110.90(12) . . ?
C14 C8 C9 107.58(12) . . ?
C14 C8 C13 108.26(13) . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 C8 112.87(13) . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
C9 C10 C11 109.10(12) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C10 C11 C12 113.50(13) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
N2 C12 C11 106.30(12) . . ?
N2 C12 C15 115.63(12) . . ?
N2 C12 C16 107.62(12) . . ?
C15 C12 C11 111.11(13) . . ?
C16 C12 C11 107.22(12) . . ?
C16 C12 C15 108.60(12) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 4.179
_oxdiff_exptl_absorpt_empirical_full_min 0.310
