# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_25_3
_database_code_depnum_ccdc_archive 'CCDC 2104616'
loop_
_audit_author_name
_audit_author_address
'Mengping Guo'
;Yichun University
China
;
_audit_update_record             
;
2021-08-21 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;
_audit_creation_date             2018-12-12
_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         'C9 H11 N O2 S'
_chemical_formula_sum            'C9 H11 N O2 S'
_chemical_formula_weight         197.25
_chemical_absolute_configuration ?
_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'
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'
S S 0.1246 0.1234 '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                   5.2907(9)
_cell_length_b                   14.516(2)
_cell_length_c                   23.891(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1834.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1745
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.7820
_cell_measurement_theta_min      2.8070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27825
_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    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5577
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.208
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -33.00   1.00    6.00    --  -11.59 -37.00 120.00   53
  2  ω      5.00  85.00   1.00    6.00    --   11.74  37.00 -90.00   80
;
_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      0.0345314000
_diffrn_orient_matrix_UB_12      0.0307732000
_diffrn_orient_matrix_UB_13      -0.0217693000
_diffrn_orient_matrix_UB_21      0.0313469000
_diffrn_orient_matrix_UB_22      -0.0379956000
_diffrn_orient_matrix_UB_23      -0.0173526000
_diffrn_orient_matrix_UB_31      -0.1256574000
_diffrn_orient_matrix_UB_32      -0.0009349000
_diffrn_orient_matrix_UB_33      -0.0102704000
_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         0.635
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                2801
_reflns_number_total             3123
_reflns_odcompleteness_completeness 99.82
_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         0.375
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.036
_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)+(0.0492P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1111
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6AA(H6AA,H6AB), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C1AA(H1AA), C3(H3), C4AA(H4AA), C6(H6), C2AA(H2AA), C5AA(H5AA)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N0AA(H0AA,H0AB)
2.d Idealised Me refined as rotating group:
 C8AA(H8AA,H8AB,H8AC), C9(H9A,H9B,H9C)
;
_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
S1B S 0.2366(2) 0.65633(7) 0.99104(4) 0.0174(3) Uani 1 1 d . . . . .
S1 S 0.7746(3) 0.52077(8) 0.16169(4) 0.0193(3) Uani 1 1 d . . . . .
O1 O 0.2405(7) 0.68410(18) 0.74337(10) 0.0159(7) Uani 1 1 d . . . . .
O0AA O 0.7525(6) 0.59984(19) 0.40546(11) 0.0169(6) Uani 1 1 d . . . . .
O1AA O 0.3321(6) 0.6185(2) 0.52048(13) 0.0254(9) Uani 1 1 d . . . . .
O2 O -0.1433(6) 0.7236(2) 0.62442(13) 0.0197(8) Uani 1 1 d . . . . .
N1 N 0.7501(8) 0.6504(2) 0.51280(14) 0.0220(9) Uani 1 1 d . . . . .
H1A H 0.760729 0.671350 0.546402 0.026 Uiso 1 1 calc R . . . .
H1B H 0.881793 0.649397 0.491715 0.026 Uiso 1 1 calc R . . . .
N0AA N 0.2463(8) 0.6613(2) 0.63460(14) 0.0191(8) Uani 1 1 d . . . . .
H0AA H 0.263976 0.651101 0.599358 0.023 Uiso 1 1 calc R . . . .
H0AB H 0.365004 0.646456 0.657486 0.023 Uiso 1 1 calc R . . . .
C1 C 0.2381(10) 0.6837(3) 0.80108(16) 0.0136(9) Uani 1 1 d . . . . .
C5 C 0.4432(9) 0.6282(3) 0.88428(18) 0.0151(10) Uani 1 1 d . . . . .
H5 H 0.576020 0.596549 0.901029 0.018 Uiso 1 1 calc R . . . .
C2 C 0.0538(9) 0.7254(3) 0.83328(18) 0.0149(10) Uani 1 1 d . . . . .
H2 H -0.074450 0.759163 0.816363 0.018 Uiso 1 1 calc R . . . .
C1AA C 0.5619(9) 0.5310(3) 0.32247(18) 0.0150(10) Uani 1 1 d . . . . .
H1AA H 0.428551 0.507000 0.343214 0.018 Uiso 1 1 calc R . . . .
C3 C 0.0617(9) 0.7164(3) 0.89098(18) 0.0158(10) Uani 1 1 d . . . . .
H3 H -0.064012 0.743542 0.912602 0.019 Uiso 1 1 calc R . . . .
C7AA C 0.5322(9) 0.6200(3) 0.49366(18) 0.0169(10) Uani 1 1 d . . . . .
C3AA C 0.7728(10) 0.5501(3) 0.23362(17) 0.0139(10) Uani 1 1 d . . . . .
C4 C 0.2549(10) 0.6672(3) 0.91723(16) 0.0148(9) Uani 1 1 d . . . . .
C4AA C 0.9591(9) 0.6026(3) 0.26055(18) 0.0159(10) Uani 1 1 d . . . . .
H4AA H 1.092531 0.626713 0.239898 0.019 Uiso 1 1 calc R . . . .
C0AA C 0.7482(10) 0.5818(3) 0.34881(16) 0.0139(9) Uani 1 1 d . . . . .
C6AA C 0.5223(9) 0.5823(3) 0.43477(17) 0.0155(10) Uani 1 1 d . . . . .
H6AA H 0.492382 0.516388 0.436135 0.019 Uiso 1 1 calc R . . . .
H6AB H 0.382823 0.610510 0.414767 0.019 Uiso 1 1 calc R . . . .
C6 C 0.4334(9) 0.6363(3) 0.82684(18) 0.0167(11) Uani 1 1 d . . . . .
H6 H 0.559485 0.609604 0.805098 0.020 Uiso 1 1 calc R . . . .
C8 C 0.0368(9) 0.6999(3) 0.65360(18) 0.0148(10) Uani 1 1 d . . . . .
C2AA C 0.5732(8) 0.5159(3) 0.26534(18) 0.0142(10) Uani 1 1 d . . . . .
H2AA H 0.445649 0.482422 0.247903 0.017 Uiso 1 1 calc R . . . .
C5AA C 0.9465(9) 0.6187(3) 0.31746(18) 0.0161(10) Uani 1 1 d . . . . .
H5AA H 1.070019 0.654173 0.334879 0.019 Uiso 1 1 calc R . . . .
C7 C 0.0206(9) 0.7168(3) 0.71565(17) 0.0155(10) Uani 1 1 d . . . . .
H7A H 0.001677 0.782272 0.722547 0.019 Uiso 1 1 calc R . . . .
H7B H -0.127052 0.685741 0.730601 0.019 Uiso 1 1 calc R . . . .
C8AA C 1.0308(9) 0.5864(3) 0.13289(19) 0.0247(11) Uani 1 1 d . . . . .
H8AA H 1.045058 0.573805 0.093569 0.037 Uiso 1 1 calc GR . . . .
H8AB H 1.185430 0.569628 0.151301 0.037 Uiso 1 1 calc GR . . . .
H8AC H 0.999168 0.650885 0.138391 0.037 Uiso 1 1 calc GR . . . .
C9 C 0.5086(9) 0.5870(3) 1.00803(19) 0.0232(11) Uani 1 1 d . . . . .
H9A H 0.497428 0.528968 0.988888 0.035 Uiso 1 1 calc GR . . . .
H9B H 0.513769 0.576515 1.047693 0.035 Uiso 1 1 calc GR . . . .
H9C H 0.659478 0.618493 0.996566 0.035 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
S1B C4 1.773(4) . ?
S1B C9 1.803(5) . ?
S1 C3AA 1.771(4) . ?
S1 C8AA 1.794(5) . ?
O1 C1 1.379(4) . ?
O1 C7 1.420(6) . ?
O0AA C0AA 1.379(4) . ?
O0AA C6AA 1.428(5) . ?
O1AA C7AA 1.238(5) . ?
O2 C8 1.230(5) . ?
N1 C7AA 1.317(6) . ?
N0AA C8 1.322(6) . ?
C1 C2 1.381(6) . ?
C1 C6 1.385(7) . ?
C5 C4 1.391(6) . ?
C5 C6 1.378(6) . ?
C2 C3 1.385(6) . ?
C1AA C0AA 1.383(6) . ?
C1AA C2AA 1.384(6) . ?
C3 C4 1.395(6) . ?
C7AA C6AA 1.511(6) . ?
C3AA C4AA 1.402(6) . ?
C3AA C2AA 1.392(6) . ?
C4AA C5AA 1.381(6) . ?
C0AA C5AA 1.396(6) . ?
C8 C7 1.505(6) . ?

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
C4 S1B C9 103.3(2) . . ?
C3AA S1 C8AA 104.4(2) . . ?
C1 O1 C7 117.4(4) . . ?
C0AA O0AA C6AA 115.7(3) . . ?
O1 C1 C2 124.1(4) . . ?
O1 C1 C6 116.1(4) . . ?
C2 C1 C6 119.8(4) . . ?
C6 C5 C4 120.1(4) . . ?
C1 C2 C3 119.5(4) . . ?
C0AA C1AA C2AA 120.2(4) . . ?
C2 C3 C4 121.2(4) . . ?
O1AA C7AA N1 125.1(4) . . ?
O1AA C7AA C6AA 116.5(4) . . ?
N1 C7AA C6AA 118.4(4) . . ?
C4AA C3AA S1 124.9(4) . . ?
C2AA C3AA S1 116.5(3) . . ?
C2AA C3AA C4AA 118.5(4) . . ?
C5 C4 S1B 124.5(3) . . ?
C5 C4 C3 118.6(4) . . ?
C3 C4 S1B 116.9(4) . . ?
C5AA C4AA C3AA 120.7(4) . . ?
O0AA C0AA C1AA 124.0(4) . . ?
O0AA C0AA C5AA 116.2(4) . . ?
C1AA C0AA C5AA 119.8(4) . . ?
O0AA C6AA C7AA 111.3(4) . . ?
C5 C6 C1 120.8(4) . . ?
O2 C8 N0AA 125.0(4) . . ?
O2 C8 C7 117.9(4) . . ?
N0AA C8 C7 117.1(4) . . ?
C1AA C2AA C3AA 120.9(4) . . ?
C4AA C5AA C0AA 119.9(4) . . ?
O1 C7 C8 111.0(3) . . ?

_olex2_date_sample_data_collection 2018-12-12
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.583
_oxdiff_exptl_absorpt_empirical_full_min 0.539
####################################################################### 
# 
# 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_1_3
_database_code_depnum_ccdc_archive 'CCDC 2104618'
loop_
_audit_author_name
_audit_author_address
'Mengping Guo'
;Yichun University
China
;
_audit_update_record             
;
2021-08-21 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;
_audit_creation_date             2018-12-12
_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         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1970(4)
_cell_length_b                   9.2995(6)
_cell_length_c                   13.4406(8)
_cell_angle_alpha                93.647(5)
_cell_angle_beta                 95.000(5)
_cell_angle_gamma                103.040(5)
_cell_volume                     748.95(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      29.3150
_cell_measurement_theta_min      2.5870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37762
_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             320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6792
_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         2.256
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(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    -40.00  61.00   1.00    1.01    --  -11.74  57.00 -30.00  101
  2  ω    -85.00  16.00   1.00    1.01    --  -11.74 -57.00-180.00  101
  3  ω    -21.00  88.00   1.00    1.01    --   11.90  77.00  90.00  109
  4  ω    -85.00 -41.00   1.00    1.01    --  -11.74 -57.00 -60.00   44
  5  ω    -20.00  25.00   1.00    1.01    --   11.90 -99.00  90.00   45
;
_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      0.0416516000
_diffrn_orient_matrix_UB_12      -0.0640211000
_diffrn_orient_matrix_UB_13      0.0073117000
_diffrn_orient_matrix_UB_21      -0.0787141000
_diffrn_orient_matrix_UB_22      -0.0402668000
_diffrn_orient_matrix_UB_23      -0.0391738000
_diffrn_orient_matrix_UB_31      0.0776188000
_diffrn_orient_matrix_UB_32      0.0213291000
_diffrn_orient_matrix_UB_33      -0.0352007000
_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                2298
_reflns_number_total             2634
_reflns_odcompleteness_completeness 99.97
_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         0.160
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2634
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+0.1528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1058
_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,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7B(H7BA,H7BB), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C6B(H6B), C4(H4), C6(H6), C1(H1), C2B(H2B), C3(H3), C5B(H5B), C2(H2),
 C4B(H4B), C3B(H3B)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N1B(H1BA,H1BB)
;
_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 0.41639(17) 0.70750(11) 0.28521(7) 0.0226(3) Uani 1 1 d . . . . .
O1B O 0.39892(17) 0.19122(11) 0.27846(7) 0.0221(3) Uani 1 1 d . . . . .
O2 O 0.22085(17) 0.43785(12) 0.45012(8) 0.0260(3) Uani 1 1 d . . . . .
O2B O 0.28539(18) 0.09927(12) 0.52280(7) 0.0293(3) Uani 1 1 d . . . . .
N1 N 0.1244(2) 0.65229(14) 0.41896(9) 0.0244(3) Uani 1 1 d . . . . .
H1A H 0.016777 0.636044 0.456137 0.029 Uiso 1 1 calc R . . . .
H1B H 0.151298 0.731901 0.388394 0.029 Uiso 1 1 calc R . . . .
N1B N 0.0814(2) 0.03085(15) 0.37207(9) 0.0276(3) Uani 1 1 d . . . . .
H1BA H -0.032998 -0.016107 0.398199 0.033 Uiso 1 1 calc R . . . .
H1BB H 0.076875 0.034046 0.308132 0.033 Uiso 1 1 calc R . . . .
C5 C 0.5895(2) 0.76046(16) 0.22970(10) 0.0192(3) Uani 1 1 d . . . . .
C1B C 0.5662(3) 0.25142(16) 0.22166(10) 0.0195(3) Uani 1 1 d . . . . .
C6B C 0.7907(3) 0.29189(16) 0.25716(11) 0.0219(4) Uani 1 1 d . . . . .
H6B H 0.836764 0.283818 0.323881 0.026 Uiso 1 1 calc R . . . .
C8 C 0.2490(2) 0.55451(17) 0.40875(10) 0.0210(3) Uani 1 1 d . . . . .
C4 C 0.5788(3) 0.88842(16) 0.18298(11) 0.0224(4) Uani 1 1 d . . . . .
H4 H 0.461018 0.933344 0.190988 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7649(3) 0.69306(16) 0.21729(10) 0.0218(3) Uani 1 1 d . . . . .
H6 H 0.771900 0.607085 0.247910 0.026 Uiso 1 1 calc R . . . .
C1 C 0.9299(3) 0.75526(17) 0.15871(11) 0.0243(4) Uani 1 1 d . . . . .
H1 H 1.047793 0.710494 0.150481 0.029 Uiso 1 1 calc R . . . .
C2B C 0.4972(3) 0.26910(17) 0.12257(11) 0.0237(4) Uani 1 1 d . . . . .
H2B H 0.346453 0.244096 0.099480 0.028 Uiso 1 1 calc R . . . .
C3 C 0.7440(3) 0.94855(17) 0.12461(11) 0.0245(4) Uani 1 1 d . . . . .
H3 H 0.736395 1.033789 0.093194 0.029 Uiso 1 1 calc R . . . .
C8B C 0.2651(3) 0.09849(16) 0.43052(11) 0.0223(4) Uani 1 1 d . . . . .
C7B C 0.4640(3) 0.17396(17) 0.38067(10) 0.0223(4) Uani 1 1 d . . . . .
H7BA H 0.529657 0.270369 0.415849 0.027 Uiso 1 1 calc R . . . .
H7BB H 0.575206 0.115381 0.383931 0.027 Uiso 1 1 calc R . . . .
C7 C 0.4414(3) 0.59138(16) 0.34627(10) 0.0212(3) Uani 1 1 d . . . . .
H7A H 0.579897 0.621819 0.389840 0.025 Uiso 1 1 calc R . . . .
H7B H 0.447737 0.504117 0.304102 0.025 Uiso 1 1 calc R . . . .
C5B C 0.9454(3) 0.34466(17) 0.19133(11) 0.0255(4) Uani 1 1 d . . . . .
H5B H 1.096238 0.369744 0.214212 0.031 Uiso 1 1 calc R . . . .
C2 C 0.9212(3) 0.88259(17) 0.11256(11) 0.0250(4) Uani 1 1 d . . . . .
H2 H 1.032789 0.923788 0.073806 0.030 Uiso 1 1 calc R . . . .
C4B C 0.8794(3) 0.36051(17) 0.09269(11) 0.0275(4) Uani 1 1 d . . . . .
H4B H 0.984799 0.395273 0.049366 0.033 Uiso 1 1 calc R . . . .
C3B C 0.6537(3) 0.32398(17) 0.05870(11) 0.0270(4) Uani 1 1 d . . . . .
H3B H 0.607689 0.336494 -0.007264 0.032 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
O1 C5 1.3777(18) . ?
O1 C7 1.4247(17) . ?
O1B C1B 1.3790(18) . ?
O1B C7B 1.4270(17) . ?
O2 C8 1.2348(18) . ?
O2B C8B 1.2351(17) . ?
N1 C8 1.3270(19) . ?
N1B C8B 1.3295(19) . ?
C5 C4 1.392(2) . ?
C5 C6 1.388(2) . ?
C1B C6B 1.389(2) . ?
C1B C2B 1.394(2) . ?
C6B C5B 1.391(2) . ?
C8 C7 1.507(2) . ?
C4 C3 1.383(2) . ?
C6 C1 1.390(2) . ?
C1 C2 1.381(2) . ?
C2B C3B 1.384(2) . ?
C3 C2 1.389(2) . ?
C8B C7B 1.508(2) . ?
C5B C4B 1.380(2) . ?
C4B C3B 1.391(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
C5 O1 C7 116.55(11) . . ?
C1B O1B C7B 116.82(11) . . ?
O1 C5 C4 115.77(13) . . ?
O1 C5 C6 124.17(13) . . ?
C6 C5 C4 120.05(14) . . ?
O1B C1B C6B 124.16(13) . . ?
O1B C1B C2B 115.50(13) . . ?
C6B C1B C2B 120.34(14) . . ?
C1B C6B C5B 118.93(14) . . ?
O2 C8 N1 123.82(14) . . ?
O2 C8 C7 118.28(13) . . ?
N1 C8 C7 117.85(13) . . ?
C3 C4 C5 119.81(14) . . ?
C5 C6 C1 119.39(14) . . ?
C2 C1 C6 120.92(14) . . ?
C3B C2B C1B 119.76(15) . . ?
C4 C3 C2 120.51(14) . . ?
O2B C8B N1B 124.09(14) . . ?
O2B C8B C7B 117.99(13) . . ?
N1B C8B C7B 117.87(13) . . ?
O1B C7B C8B 110.33(12) . . ?
O1 C7 C8 110.30(12) . . ?
C4B C5B C6B 121.25(15) . . ?
C1 C2 C3 119.31(14) . . ?
C5B C4B C3B 119.33(15) . . ?
C2B C3B C4B 120.33(14) . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.355
_oxdiff_exptl_absorpt_empirical_full_min 0.629
