# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_r20211103d
_database_code_depnum_ccdc_archive 'CCDC 2216574'
loop_
_audit_author_name
_audit_author_address
'Zhonghua Li'
;Tianjin University
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_audit_creation_date             2022-09-21
_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        Methyl-2-amino-5-methoxybenzoate
_chemical_formula_moiety         'C9 H11 N O3'
_chemical_formula_sum            'C9 H11 N O3'
_chemical_formula_weight         181.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H11NO3
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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   29.7023(15)
_cell_length_b                   29.7023(15)
_cell_length_c                   5.3577(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4093.4(5)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    3791
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.2450
_cell_measurement_theta_min      2.3540
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10582
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         2.375
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    8.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00   0.00   1.00    8.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0226147000
_diffrn_orient_matrix_UB_12      -0.0023626000
_diffrn_orient_matrix_UB_13      0.0037293000
_diffrn_orient_matrix_UB_21      0.0157496000
_diffrn_orient_matrix_UB_22      0.0274499000
_diffrn_orient_matrix_UB_23      -0.0048791000
_diffrn_orient_matrix_UB_31      -0.0000273000
_diffrn_orient_matrix_UB_32      0.0010892000
_diffrn_orient_matrix_UB_33      0.1322252000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1432
_reflns_number_total             1865
_reflns_odcompleteness_completeness 99.84
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.169
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+2.3370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1071
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C6(H6)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_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
O3 O 0.46756(5) 0.77306(4) 0.9622(2) 0.0369(3) Uani 1 1 d . . . . .
O1 O 0.62746(4) 0.90135(4) 0.1784(2) 0.0347(3) Uani 1 1 d . . . . .
O2 O 0.59043(4) 0.81603(4) 0.2539(2) 0.0315(3) Uani 1 1 d . . . . .
N1 N 0.60014(6) 0.95803(6) 0.4743(3) 0.0397(4) Uani 1 1 d . . . . .
C9 C 0.46169(7) 0.72481(6) 0.8800(4) 0.0392(5) Uani 1 1 d . . . . .
H9A H 0.448413 0.717936 0.708549 0.059 Uiso 1 1 calc GR . . . .
H9B H 0.437163 0.696825 0.989498 0.059 Uiso 1 1 calc GR . . . .
H9C H 0.495470 0.726464 0.885358 0.059 Uiso 1 1 calc GR . . . .
C5 C 0.50201(6) 0.81648(6) 0.8296(3) 0.0280(4) Uani 1 1 d . . . . .
C4 C 0.50656(6) 0.86335(6) 0.9124(3) 0.0306(4) Uani 1 1 d . . . . .
H4 H 0.486932 0.863322 1.052497 0.037 Uiso 1 1 calc R . . . .
C3 C 0.53881(6) 0.90892(6) 0.7942(3) 0.0304(4) Uani 1 1 d . . . . .
H3 H 0.541005 0.940119 0.853244 0.036 Uiso 1 1 calc R . . . .
C2 C 0.56904(6) 0.91114(6) 0.5866(3) 0.0281(4) Uani 1 1 d . . . . .
C1 C 0.56474(6) 0.86387(6) 0.5050(3) 0.0252(4) Uani 1 1 d . . . . .
C6 C 0.53048(6) 0.81686(6) 0.6279(3) 0.0263(4) Uani 1 1 d . . . . .
H6 H 0.527166 0.785124 0.569798 0.032 Uiso 1 1 calc R . . . .
C7 C 0.59689(6) 0.86353(6) 0.2987(3) 0.0264(4) Uani 1 1 d . . . . .
C8 C 0.62153(7) 0.81335(7) 0.0549(3) 0.0350(4) Uani 1 1 d . . . . .
H8A H 0.613531 0.825214 -0.100783 0.053 Uiso 1 1 calc GR . . . .
H8B H 0.613793 0.777373 0.035198 0.053 Uiso 1 1 calc GR . . . .
H8C H 0.658443 0.835642 0.094868 0.053 Uiso 1 1 calc GR . . . .
H1A H 0.6029(8) 0.9856(8) 0.544(4) 0.051(6) Uiso 1 1 d . . . . .
H1B H 0.6202(8) 0.9600(8) 0.345(4) 0.057(7) 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
O3 C9 1.424(2) . ?
O3 C5 1.3766(19) . ?
O1 C7 1.2173(18) . ?
O2 C7 1.3470(19) . ?
O2 C8 1.4385(19) . ?
N1 C2 1.367(2) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.89(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C5 C4 1.402(2) . ?
C5 C6 1.369(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.362(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.410(2) . ?
C2 C1 1.414(2) . ?
C1 C6 1.414(2) . ?
C1 C7 1.464(2) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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 O3 C9 116.28(13) . . ?
C7 O2 C8 115.52(13) . . ?
C2 N1 H1A 118.1(14) . . ?
C2 N1 H1B 119.7(14) . . ?
H1A N1 H1B 122(2) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C5 C4 115.12(14) . . ?
C6 C5 O3 125.58(14) . . ?
C6 C5 C4 119.29(15) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.70(15) . . ?
C3 C4 H4 119.7 . . ?
C4 C3 H3 119.1 . . ?
C4 C3 C2 121.89(15) . . ?
C2 C3 H3 119.1 . . ?
N1 C2 C3 119.00(15) . . ?
N1 C2 C1 123.71(16) . . ?
C3 C2 C1 117.28(14) . . ?
C2 C1 C7 120.33(14) . . ?
C6 C1 C2 119.98(14) . . ?
C6 C1 C7 119.65(14) . . ?
C5 C6 C1 120.84(14) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 O2 121.48(14) . . ?
O1 C7 C1 125.55(15) . . ?
O2 C7 C1 112.95(13) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
O3 C5 C4 C3 -179.00(15) . . . . ?
O3 C5 C6 C1 179.83(14) . . . . ?
N1 C2 C1 C6 -178.20(15) . . . . ?
N1 C2 C1 C7 3.8(2) . . . . ?
C9 O3 C5 C4 179.23(15) . . . . ?
C9 O3 C5 C6 0.2(2) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C4 C3 C2 N1 179.16(16) . . . . ?
C4 C3 C2 C1 -0.1(2) . . . . ?
C3 C2 C1 C6 1.1(2) . . . . ?
C3 C2 C1 C7 -176.90(14) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
C2 C1 C7 O1 -2.5(2) . . . . ?
C2 C1 C7 O2 176.20(13) . . . . ?
C6 C5 C4 C3 0.1(2) . . . . ?
C6 C1 C7 O1 179.54(15) . . . . ?
C6 C1 C7 O2 -1.8(2) . . . . ?
C7 C1 C6 C5 176.54(15) . . . . ?
C8 O2 C7 O1 -0.5(2) . . . . ?
C8 O2 C7 C1 -179.27(13) . . . . ?

_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 1.699
_oxdiff_exptl_absorpt_empirical_full_min 0.769
####################################################################### 
# 
# 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_r20211122b
_database_code_depnum_ccdc_archive 'CCDC 2216575'
loop_
_audit_author_name
_audit_author_address
'Zhonghua Li'
;Tianjin University
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_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        'Methyl 2-amino-5-methylbenzoate'
_chemical_formula_moiety         'C9 H11 N O2'
_chemical_formula_sum            'C9 H11 N O2'
_chemical_formula_weight         165.19
_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   27.6948(15)
_cell_length_b                   27.6948(15)
_cell_length_c                   5.9072(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3923.8(5)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    5074
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.2230
_cell_measurement_theta_min      2.5210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13491
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.833
_diffrn_reflns_theta_min         2.548
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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   -115.00  65.00   0.25    8.00    --  -25.00  45.00   0.00  720
  2  ω   -115.00  35.00   0.25    8.00    --  -25.00  45.00  90.00  600
  3  ω   -115.00  10.00   0.25    8.00    --  -25.00  45.00 180.00  500
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0196272000
_diffrn_orient_matrix_UB_12      -0.0093005000
_diffrn_orient_matrix_UB_13      -0.0065225000
_diffrn_orient_matrix_UB_21      -0.0220980000
_diffrn_orient_matrix_UB_22      -0.0279613000
_diffrn_orient_matrix_UB_23      -0.0074630000
_diffrn_orient_matrix_UB_31      0.0003531000
_diffrn_orient_matrix_UB_32      0.0022781000
_diffrn_orient_matrix_UB_33      -0.1197406000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1500
_reflns_number_total             2082
_reflns_odcompleteness_completeness 94.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.90
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.251
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.044
_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)+(0.0525P)²+2.8058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1302
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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
O1 O 0.42838(5) 0.39097(5) 0.3960(2) 0.0382(3) Uani 1 1 d . . . . .
O2 O 0.52088(5) 0.44266(5) 0.4167(2) 0.0362(3) Uani 1 1 d . . . . .
N1 N 0.37522(7) 0.31054(7) 0.7086(3) 0.0397(4) Uani 1 1 d . . . . .
H1A H 0.3466(9) 0.2855(9) 0.785(3) 0.043(6) Uiso 1 1 d . . . . .
H1B H 0.3712(9) 0.3244(9) 0.582(4) 0.052(7) Uiso 1 1 d . . . . .
C1 C 0.47594(7) 0.37276(6) 0.6890(3) 0.0279(4) Uani 1 1 d . . . . .
C2 C 0.42741(7) 0.33041(6) 0.7922(3) 0.0291(4) Uani 1 1 d . . . . .
C3 C 0.43428(7) 0.30777(7) 0.9936(3) 0.0333(4) Uani 1 1 d . . . . .
H3 H 0.402284 0.279573 1.069172 0.040 Uiso 1 1 calc R . . . .
C4 C 0.48573(7) 0.32520(7) 1.0838(3) 0.0338(4) Uani 1 1 d . . . . .
H4 H 0.488547 0.308941 1.221123 0.041 Uiso 1 1 calc R . . . .
C5 C 0.53424(7) 0.36608(7) 0.9807(3) 0.0335(4) Uani 1 1 d . . . . .
C6 C 0.52823(7) 0.38916(7) 0.7846(3) 0.0305(4) Uani 1 1 d . . . . .
H6 H 0.560679 0.417248 0.711088 0.037 Uiso 1 1 calc R . . . .
C7 C 0.47175(7) 0.40141(6) 0.4892(3) 0.0296(4) Uani 1 1 d . . . . .
C8 C 0.51888(9) 0.47345(8) 0.2243(3) 0.0433(5) Uani 1 1 d . . . . .
H8A H 0.502093 0.448100 0.095587 0.065 Uiso 1 1 calc GR . . . .
H8B H 0.556787 0.502552 0.184642 0.065 Uiso 1 1 calc GR . . . .
H8C H 0.496398 0.490668 0.261491 0.065 Uiso 1 1 calc GR . . . .
C9 C 0.59050(8) 0.38391(9) 1.0814(4) 0.0491(5) Uani 1 1 d . . . . .
H9A H 0.600943 0.355609 1.049390 0.074 Uiso 1 1 calc GR . . . .
H9B H 0.589062 0.388185 1.245494 0.074 Uiso 1 1 calc GR . . . .
H9C H 0.618199 0.419568 1.014879 0.074 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 C7 1.2172(19) . ?
O2 C7 1.3361(19) . ?
O2 C8 1.439(2) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.87(2) . ?
N1 C2 1.357(2) . ?
C1 C2 1.406(2) . ?
C1 C6 1.402(2) . ?
C1 C7 1.459(2) . ?
C2 C3 1.401(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.364(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(2) . ?
C5 C6 1.372(2) . ?
C5 C9 1.502(2) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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 C8 115.81(14) . . ?
H1A N1 H1B 122.0(19) . . ?
C2 N1 H1A 119.5(13) . . ?
C2 N1 H1B 118.5(14) . . ?
C2 C1 C7 120.12(15) . . ?
C6 C1 C2 119.81(15) . . ?
C6 C1 C7 120.01(15) . . ?
N1 C2 C1 124.11(16) . . ?
N1 C2 C3 118.87(16) . . ?
C3 C2 C1 117.02(15) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.66(16) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 122.00(16) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C9 121.00(16) . . ?
C6 C5 C4 117.10(16) . . ?
C6 C5 C9 121.90(16) . . ?
C1 C6 H6 118.8 . . ?
C5 C6 C1 122.37(16) . . ?
C5 C6 H6 118.8 . . ?
O1 C7 O2 121.35(15) . . ?
O1 C7 C1 125.02(15) . . ?
O2 C7 C1 113.60(14) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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 C2 C3 C4 178.71(16) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
C2 C1 C7 O1 -1.6(2) . . . . ?
C2 C1 C7 O2 176.52(14) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 C9 -178.99(17) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C6 C1 C2 N1 -177.86(16) . . . . ?
C6 C1 C2 C3 2.0(2) . . . . ?
C6 C1 C7 O1 -178.71(16) . . . . ?
C6 C1 C7 O2 -0.6(2) . . . . ?
C7 C1 C2 N1 5.0(2) . . . . ?
C7 C1 C2 C3 -175.07(14) . . . . ?
C7 C1 C6 C5 175.72(15) . . . . ?
C8 O2 C7 O1 0.2(2) . . . . ?
C8 O2 C7 C1 -178.05(14) . . . . ?
C9 C5 C6 C1 179.89(16) . . . . ?

_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 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.725
