# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_cc1
_audit_block_doi                 10.5517/ccdc.csd.cc26mh8m
_database_code_depnum_ccdc_archive 'CCDC 2044520'
loop_
_audit_author_name
_audit_author_address
'Qian Cai'
;Jinan University
China
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;
_audit_creation_date             2019-09-05
_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         'C13 H13 N O2'
_chemical_formula_sum            'C13 H13 N O2'
_chemical_formula_weight         215.24
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.8556(3)
_cell_length_b                   6.92143(19)
_cell_length_c                   9.4280(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.887(4)
_cell_angle_gamma                90
_cell_volume                     536.22(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5299
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      73.2880
_cell_measurement_theta_min      4.9880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43697
_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    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.13
_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  0.0465
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7302
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.351
_diffrn_reflns_theta_min         5.056
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_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 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00   0.00   1.00    1.00    --  -40.73 -19.00 -90.00  121
  2  ω   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00   0.00  100
  3  ω      8.00 117.00   1.00    1.00    --   40.73  77.00  60.00  109
  4  ω     23.00  97.00   1.00    1.00    --   40.73-125.00-180.00   74
  5  ω      1.00  82.00   1.00    1.00    --   40.73 -99.00 -60.00   81
  6  ω    -34.00  65.00   1.00    1.00    --   40.73 -37.00 150.00   99
  7  ω     31.00 135.00   1.00    1.00    --  106.95 -30.00 -30.00  104
  8  ω     81.00 178.00   1.00    1.00    --  106.95  45.00  60.00   97
  9  ω     34.00 133.00   1.00    1.00    --  106.95 -45.00 120.00   99
 10  ω     74.00 178.00   1.00    1.00    --  106.95  77.00  30.00  104
 11  ω     81.00 171.00   1.00    1.00    --  106.95  45.00  30.00   90
 12  ω     81.00 108.00   1.00    1.00    --  106.95  61.00 -30.00   27
 13  ω     74.00 101.00   1.00    1.00    --  106.95  77.00   0.00   27
 14  ω     35.00 121.00   1.00    1.00    --  106.95-125.00-180.00   86
 15  ω    152.00 178.00   1.00    1.00    --  106.95  61.00 -60.00   26
 16  ω     85.00 112.00   1.00    1.00    --  106.95  45.00 -30.00   27
 17  ω     78.00 107.00   1.00    1.00    --  106.95  61.00 -60.00   29
 18  ω     74.00 101.00   1.00    1.00    --  106.95  77.00 -30.00   27
 19  ω     78.00 114.00   1.00    1.00    --  106.95  61.00  30.00   36
 20  ω    124.00 176.00   1.00    1.00    --  106.95  30.00 -60.00   52
 21  ω     81.00 123.00   1.00    1.00    --  106.95  61.00   0.00   42
 22  ω     95.00 170.00   1.00    1.00    --  106.95 125.00 -30.00   75
 23  ω     50.00 139.00   1.00    1.00    --  106.95 -77.00 -30.00   89
 24  ω     78.00 104.00   1.00    1.00    --  106.95  61.00   0.00   26
 25  ω    153.00 178.00   1.00    1.00    --  106.95   0.00 -30.00   25
 26  ω   -118.00  -9.00   1.00    1.00    --  -41.48 -77.00 120.00  109
 27  ω   -115.00 -13.00   1.00    1.00    --  -41.48 -57.00 -90.00  102
 28  ω   -115.00 -13.00   1.00    1.00    --  -41.48 -57.00 150.00  102
 29  ω   -118.00  -9.00   1.00    1.00    --  -41.48 -77.00-120.00  109
 30  ω   -118.00  -9.00   1.00    1.00    --  -41.48 -77.00 -90.00  109
 31  ω    -33.00  66.00   1.00    1.00    --   41.48 -37.00 -30.00   99
 32  ω     17.00 116.00   1.00    1.00    --   41.48  37.00-150.00   99
 33  ω     74.00 173.00   1.00    1.00    --  106.95  77.00-150.00   99
;
_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      0.1305269000
_diffrn_orient_matrix_UB_12      -0.1177409000
_diffrn_orient_matrix_UB_13      0.1250066000
_diffrn_orient_matrix_UB_21      -0.1092033000
_diffrn_orient_matrix_UB_22      -0.0045988000
_diffrn_orient_matrix_UB_23      0.0945549000
_diffrn_orient_matrix_UB_31      -0.0785302000
_diffrn_orient_matrix_UB_32      -0.1889194000
_diffrn_orient_matrix_UB_33      -0.0801640000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.909
_reflns_number_gt                2015
_reflns_number_total             2055
_reflns_odcompleteness_completeness 100.00
_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 1.171.38.43f (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 849 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.054
_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)+(0.0697P)²+0.0933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1086
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.6623(2) -0.7567(3) -0.39638(18) 0.0305(4) Uani 1 1 d . . . . .
O2 O -0.89855(19) -0.4094(3) -0.26145(17) 0.0314(4) Uani 1 1 d . . . . .
N1 N -0.6398(2) -0.4207(3) -0.07759(18) 0.0225(4) Uani 1 1 d . . . . .
C9 C -0.7095(3) -0.5942(4) -0.4375(3) 0.0227(5) Uani 1 1 d . . . . .
C1 C -0.4839(3) -0.4189(3) -0.2240(2) 0.0215(4) Uani 1 1 d . . . . .
C7 C -0.7515(3) -0.4150(4) -0.2236(2) 0.0229(4) Uani 1 1 d . . . . .
C6 C -0.4799(3) -0.4227(4) -0.0739(2) 0.0214(4) Uani 1 1 d . . . . .
C2 C -0.3399(3) -0.4202(4) -0.2492(2) 0.0239(4) Uani 1 1 d . . . . .
H2 H -0.341105 -0.417531 -0.348221 0.029 Uiso 1 1 calc R . . . .
C5 C -0.3357(3) -0.4262(4) 0.0519(2) 0.0254(4) Uani 1 1 d . . . . .
H5 H -0.334751 -0.427513 0.150834 0.030 Uiso 1 1 calc R . . . .
C8 C -0.6572(2) -0.4143(4) -0.3328(2) 0.0218(4) Uani 1 1 d . . . . .
C13 C -0.6816(3) -0.4218(5) 0.0575(2) 0.0267(5) Uani 1 1 d . . . . .
H13A H -0.654929 -0.545348 0.106920 0.040 Uiso 1 1 calc GR . . . .
H13B H -0.796045 -0.398235 0.028236 0.040 Uiso 1 1 calc GR . . . .
H13C H -0.621372 -0.322652 0.126710 0.040 Uiso 1 1 calc GR . . . .
C3 C -0.1926(3) -0.4257(4) -0.1240(2) 0.0279(5) Uani 1 1 d . . . . .
H3 H -0.094899 -0.428104 -0.139577 0.034 Uiso 1 1 calc R . . . .
C4 C -0.1915(3) -0.4276(4) 0.0241(2) 0.0283(5) Uani 1 1 d . . . . .
H4 H -0.092447 -0.429865 0.106442 0.034 Uiso 1 1 calc R . . . .
C11 C -0.8612(4) -0.3224(4) -0.5787(3) 0.0309(6) Uani 1 1 d . . . . .
H11A H -0.957686 -0.312795 -0.553576 0.037 Uiso 1 1 calc R . . . .
H11B H -0.879415 -0.251274 -0.672282 0.037 Uiso 1 1 calc R . . . .
C12 C -0.7110(3) -0.2456(4) -0.4475(3) 0.0274(5) Uani 1 1 d . . . . .
H12A H -0.738384 -0.132849 -0.400902 0.033 Uiso 1 1 calc R . . . .
H12B H -0.625523 -0.211371 -0.483963 0.033 Uiso 1 1 calc R . . . .
C10 C -0.8201(3) -0.5326(4) -0.5953(3) 0.0313(6) Uani 1 1 d . . . . .
H10A H -0.917969 -0.610959 -0.631126 0.038 Uiso 1 1 calc R . . . .
H10B H -0.765466 -0.544533 -0.666893 0.038 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 C9 1.212(3) . ?
O2 C7 1.216(3) . ?
N1 C7 1.364(3) . ?
N1 C6 1.403(3) . ?
N1 C13 1.453(2) . ?
C9 C8 1.548(3) . ?
C9 C10 1.506(3) . ?
C1 C6 1.403(3) . ?
C1 C2 1.382(3) . ?
C1 C8 1.495(3) . ?
C7 C8 1.549(3) . ?
C6 C5 1.381(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.396(3) . ?
C8 C12 1.541(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.394(3) . ?
C4 H4 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.535(4) . ?
C11 C10 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 N1 C6 111.76(15) . . ?
C7 N1 C13 124.03(18) . . ?
C6 N1 C13 124.21(16) . . ?
O1 C9 C8 123.8(2) . . ?
O1 C9 C10 126.8(2) . . ?
C10 C9 C8 109.38(19) . . ?
C6 C1 C8 109.04(18) . . ?
C2 C1 C6 119.70(19) . . ?
C2 C1 C8 131.25(17) . . ?
O2 C7 N1 126.25(18) . . ?
O2 C7 C8 126.08(17) . . ?
N1 C7 C8 107.67(17) . . ?
C1 C6 N1 109.20(17) . . ?
C5 C6 N1 128.55(17) . . ?
C5 C6 C1 122.2(2) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.13(18) . . ?
C3 C2 H2 120.4 . . ?
C6 C5 H5 121.4 . . ?
C6 C5 C4 117.21(18) . . ?
C4 C5 H5 121.4 . . ?
C9 C8 C7 108.28(19) . . ?
C1 C8 C9 114.01(19) . . ?
C1 C8 C7 102.33(15) . . ?
C1 C8 C12 117.9(2) . . ?
C12 C8 C9 102.77(15) . . ?
C12 C8 C7 111.51(19) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.53(19) . . ?
C3 C4 H4 119.2 . . ?
H11A C11 H11B 108.9 . . ?
C12 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C10 C11 C12 104.2(2) . . ?
C8 C12 H12A 110.8 . . ?
C8 C12 H12B 110.8 . . ?
C11 C12 C8 104.6(2) . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C9 C10 C11 105.2(2) . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C11 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?

_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 2.587
_oxdiff_exptl_absorpt_empirical_full_min 0.419
####################################################################### 
# 
# 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_cai1129
_audit_block_doi                 10.5517/ccdc.csd.cc26mh9n
_database_code_depnum_ccdc_archive 'CCDC 2044521'
loop_
_audit_author_name
_audit_author_address
'Qian Cai'
;Jinan University
China
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;
_audit_creation_date             2019-12-04
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N O4'
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24
_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                   6.94293(12)
_cell_length_b                   9.02763(16)
_cell_length_c                   18.0531(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1131.54(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3720
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3810
_cell_measurement_theta_min      2.4350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64735
_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    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4173
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.547
_diffrn_reflns_theta_min         5.479
_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 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00  60.00  109
  2  ω      1.00  82.00   1.00    1.00    --   40.98 -99.00  90.00   81
  3  ω    -19.00  50.00   1.00    1.00    --   40.98 -38.00-120.00   69
  4  ω     49.00  76.00   1.00    1.00    --  106.95 -45.00  90.00   27
  5  ω     83.00 178.00   1.00    1.00    --  106.95  30.00  90.00   95
  6  ω     59.00 120.00   1.00    1.00    --  106.95-125.00 -90.00   61
  7  ω    108.00 142.00   1.00    1.00    --  106.95 125.00-180.00   34
  8  ω    106.00 169.00   1.00    1.00    --  106.95 125.00  90.00   63
  9  ω     80.00 133.00   1.00    1.00    --  106.95 -45.00  90.00   53
 10  ω    125.00 174.00   1.00    1.00    --  106.95 125.00-150.00   49
;
_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      0.0055692000
_diffrn_orient_matrix_UB_12      0.1306830000
_diffrn_orient_matrix_UB_13      -0.0548629000
_diffrn_orient_matrix_UB_21      -0.0230609000
_diffrn_orient_matrix_UB_22      0.1093542000
_diffrn_orient_matrix_UB_23      0.0648884000
_diffrn_orient_matrix_UB_31      0.2205816000
_diffrn_orient_matrix_UB_32      0.0082235000
_diffrn_orient_matrix_UB_33      0.0082654000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                2186
_reflns_number_total             2201
_reflns_odcompleteness_completeness 99.84
_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 1.171.38.43f (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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 861 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.050
_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)+(0.0513P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0824
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.3704(2) 0.78584(14) 0.60269(7) 0.0212(3) Uani 1 1 d . . . . .
O2 O 0.13856(18) 0.63199(15) 0.56739(8) 0.0231(3) Uani 1 1 d . . . . .
O1 O 0.4543(2) 0.46418(15) 0.70736(7) 0.0283(3) Uani 1 1 d . . . . .
O4 O 0.4706(2) 0.39325(17) 0.31213(7) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.4472(2) 0.29225(15) 0.61307(8) 0.0159(3) Uani 1 1 d . . . . .
C11 C 0.3061(3) 0.65289(19) 0.58094(10) 0.0170(4) Uani 1 1 d . . . . .
C3 C 0.4638(3) 0.44114(18) 0.51018(9) 0.0153(3) Uani 1 1 d . . . . .
C4 C 0.4526(2) 0.29463(19) 0.53514(9) 0.0154(3) Uani 1 1 d . . . . .
C6 C 0.4568(3) 0.2083(2) 0.41076(10) 0.0208(4) Uani 1 1 d . . . . .
H6 H 0.455110 0.130714 0.376877 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4513(3) 0.15804(19) 0.65748(10) 0.0199(4) Uani 1 1 d . . . . .
H12A H 0.355300 0.090280 0.639719 0.030 Uiso 1 1 calc R U . . .
H12B H 0.425298 0.182269 0.708275 0.030 Uiso 1 1 calc R U . . .
H12C H 0.576169 0.112896 0.653772 0.030 Uiso 1 1 calc R U . . .
C5 C 0.4506(3) 0.1774(2) 0.48661(10) 0.0191(4) Uani 1 1 d . . . . .
H5 H 0.445313 0.080307 0.503715 0.023 Uiso 1 1 calc R U . . .
C1 C 0.4554(3) 0.43124(19) 0.64176(10) 0.0178(4) Uani 1 1 d . . . . .
C2 C 0.4720(3) 0.54164(18) 0.57652(9) 0.0158(3) Uani 1 1 d . . . . .
C9 C 0.6517(3) 0.6400(2) 0.58424(11) 0.0197(4) Uani 1 1 d . . . . .
H9A H 0.746236 0.594088 0.616484 0.024 Uiso 1 1 calc R U . . .
H9B H 0.710249 0.658167 0.536306 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4655(3) 0.3538(2) 0.38530(9) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.4724(3) 0.47260(19) 0.43561(10) 0.0182(4) Uani 1 1 d . . . . .
H8 H 0.482489 0.569782 0.418966 0.022 Uiso 1 1 calc R U . . .
C10 C 0.5760(3) 0.7835(2) 0.61795(11) 0.0213(4) Uani 1 1 d . . . . .
H10A H 0.599364 0.785421 0.670918 0.026 Uiso 1 1 calc R U . . .
H10B H 0.638762 0.868460 0.595611 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4594(4) 0.2757(3) 0.25878(11) 0.0342(5) Uani 1 1 d . . . . .
H13A H 0.467866 0.316290 0.209738 0.051 Uiso 1 1 calc R U . . .
H13B H 0.339058 0.224489 0.264321 0.051 Uiso 1 1 calc R U . . .
H13C H 0.563717 0.207701 0.266599 0.051 Uiso 1 1 calc R U . . .


_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 C11 1.339(2) . ?
O3 C10 1.454(2) . ?
O2 C11 1.204(2) . ?
O1 C1 1.221(2) . ?
O4 C7 1.369(2) . ?
O4 C13 1.435(3) . ?
N1 C4 1.408(2) . ?
N1 C12 1.453(2) . ?
N1 C1 1.359(2) . ?
C11 C2 1.530(2) . ?
C3 C4 1.399(2) . ?
C3 C2 1.504(2) . ?
C3 C8 1.377(2) . ?
C4 C5 1.374(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.398(3) . ?
C6 C7 1.393(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C5 H5 0.9300 . ?
C1 C2 1.547(2) . ?
C2 C9 1.538(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.525(2) . ?
C7 C8 1.407(2) . ?
C8 H8 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C11 O3 C10 111.69(14) . . ?
C7 O4 C13 116.97(16) . . ?
C4 N1 C12 124.31(14) . . ?
C1 N1 C4 111.46(14) . . ?
C1 N1 C12 123.98(14) . . ?
O3 C11 C2 110.66(14) . . ?
O2 C11 O3 121.46(16) . . ?
O2 C11 C2 127.87(16) . . ?
C4 C3 C2 108.42(14) . . ?
C8 C3 C4 120.80(16) . . ?
C8 C3 C2 130.74(15) . . ?
C3 C4 N1 109.74(15) . . ?
C5 C4 N1 128.71(17) . . ?
C5 C4 C3 121.55(16) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.85(16) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C5 C6 118.07(16) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
O1 C1 N1 126.47(16) . . ?
O1 C1 C2 125.59(16) . . ?
N1 C1 C2 107.92(14) . . ?
C11 C2 C1 109.09(14) . . ?
C11 C2 C9 103.12(13) . . ?
C3 C2 C11 114.16(15) . . ?
C3 C2 C1 102.41(13) . . ?
C3 C2 C9 116.81(15) . . ?
C9 C2 C1 111.31(15) . . ?
C2 C9 H9A 110.9 . . ?
C2 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 C2 104.28(14) . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
O4 C7 C6 124.43(17) . . ?
O4 C7 C8 115.06(16) . . ?
C6 C7 C8 120.51(16) . . ?
C3 C8 C7 118.19(16) . . ?
C3 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
O3 C10 C9 105.98(14) . . ?
O3 C10 H10A 110.5 . . ?
O3 C10 H10B 110.5 . . ?
C9 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 C11 C2 C3 -138.80(16) . . . . ?
O3 C11 C2 C1 107.34(16) . . . . ?
O3 C11 C2 C9 -11.06(18) . . . . ?
O2 C11 C2 C3 40.9(3) . . . . ?
O2 C11 C2 C1 -72.9(2) . . . . ?
O2 C11 C2 C9 168.69(19) . . . . ?
O1 C1 C2 C11 -58.2(2) . . . . ?
O1 C1 C2 C3 -179.5(2) . . . . ?
O1 C1 C2 C9 55.0(2) . . . . ?
O4 C7 C8 C3 178.69(17) . . . . ?
N1 C4 C5 C6 179.87(18) . . . . ?
N1 C1 C2 C11 123.33(16) . . . . ?
N1 C1 C2 C3 2.03(19) . . . . ?
N1 C1 C2 C9 -123.53(17) . . . . ?
C11 O3 C10 C9 14.4(2) . . . . ?
C11 C2 C9 C10 18.68(17) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C3 C2 C9 C10 144.74(15) . . . . ?
C4 N1 C1 O1 -179.62(19) . . . . ?
C4 N1 C1 C2 -1.1(2) . . . . ?
C4 C3 C2 C11 -119.98(16) . . . . ?
C4 C3 C2 C1 -2.22(19) . . . . ?
C4 C3 C2 C9 119.65(17) . . . . ?
C4 C3 C8 C7 1.3(3) . . . . ?
C6 C7 C8 C3 -2.1(3) . . . . ?
C12 N1 C4 C3 -174.75(16) . . . . ?
C12 N1 C4 C5 4.4(3) . . . . ?
C12 N1 C1 O1 -5.2(3) . . . . ?
C12 N1 C1 C2 173.30(16) . . . . ?
C5 C6 C7 O4 -179.53(17) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
C1 N1 C4 C3 -0.3(2) . . . . ?
C1 N1 C4 C5 178.81(18) . . . . ?
C1 C2 C9 C10 -98.16(17) . . . . ?
C2 C3 C4 N1 1.7(2) . . . . ?
C2 C3 C4 C5 -177.51(16) . . . . ?
C2 C3 C8 C7 178.57(18) . . . . ?
C2 C9 C10 O3 -20.36(19) . . . . ?
C7 C6 C5 C4 0.2(3) . . . . ?
C8 C3 C4 N1 179.50(17) . . . . ?
C8 C3 C4 C5 0.3(3) . . . . ?
C8 C3 C2 C11 62.5(3) . . . . ?
C8 C3 C2 C1 -179.7(2) . . . . ?
C8 C3 C2 C9 -57.8(3) . . . . ?
C10 O3 C11 O2 178.28(17) . . . . ?
C10 O3 C11 C2 -2.0(2) . . . . ?
C13 O4 C7 C6 2.3(3) . . . . ?
C13 O4 C7 C8 -178.62(17) . . . . ?

_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 1.746
_oxdiff_exptl_absorpt_empirical_full_min 0.636
####################################################################### 
# 
# 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_zhou-1-58
_audit_block_doi                 10.5517/ccdc.csd.cc26mhbp
_database_code_depnum_ccdc_archive 'CCDC 2044522'
loop_
_audit_author_name
_audit_author_address
'Qian Cai'
;Jinan University
China
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 N2 O2'
_chemical_formula_sum            'C13 H14 N2 O2'
_chemical_formula_weight         230.26
_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                   6.9560(2)
_cell_length_b                   8.4636(3)
_cell_length_c                   19.6496(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1156.83(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7797
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4830
_cell_measurement_theta_min      2.2070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79451
_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    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_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  0.0387
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10363
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.661
_diffrn_reflns_theta_min         4.500
_diffrn_ambient_temperature      293(2)
_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 0.991
_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 -16.00   1.00    1.00    --  -40.98 -38.00 150.00   99
  2  ω     23.00  97.00   1.00    1.00    --   40.98-125.00  30.00   74
  3  ω     16.00 115.00   1.00    1.00    --   40.98  38.00  30.00   99
  4  ω     81.00 178.00   1.00    1.00    --  106.95  45.00  90.00   97
  5  ω     34.00 133.00   1.00    1.00    --  106.95 -45.00 -60.00   99
  6  ω     94.00 178.00   1.00    1.00    --  106.95 125.00 -30.00   84
  7  ω     94.00 178.00   1.00    1.00    --  106.95 125.00  30.00   84
  8  ω    101.00 178.00   1.00    1.00    --  106.95  94.00 -69.00   77
  9  ω     34.00 133.00   1.00    1.00    --  106.95 -45.00 120.00   99
 10  ω   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00 -90.00  100
 11  ω   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00  90.00  109
 12  ω     74.00 178.00   1.00    1.00    --  106.95  77.00-120.00  104
 13  ω     54.00 178.00   1.00    1.00    --  106.95  15.00   0.00  124
 14  ω     25.00 109.00   1.00    1.00    --  106.95 -95.00 -30.00   84
 15  ω     79.00 178.00   1.00    1.00    --  106.95  30.00-180.00   99
 16  ω    -69.00  32.00   1.00    1.00    --  -40.98  57.00 -60.00  101
 17  ω      1.00  82.00   1.00    1.00    --   40.98 -99.00 150.00   81
;
_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      -0.0588678000
_diffrn_orient_matrix_UB_12      -0.0941738000
_diffrn_orient_matrix_UB_13      0.0638272000
_diffrn_orient_matrix_UB_21      -0.0619750000
_diffrn_orient_matrix_UB_22      -0.1394510000
_diffrn_orient_matrix_UB_23      -0.0453380000
_diffrn_orient_matrix_UB_31      0.2042519000
_diffrn_orient_matrix_UB_32      -0.0693182000
_diffrn_orient_matrix_UB_33      0.0046764000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2235
_reflns_number_total             2300
_reflns_odcompleteness_completeness 100.00
_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 1.171.38.43f (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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 881 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.055
_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)+(0.0591P)²+0.1410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.0993
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_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
O2 O 0.52262(19) 0.5024(2) 0.35972(8) 0.0478(4) Uani 1 1 d . . . . .
O1 O 0.1911(3) 0.1976(2) 0.33170(8) 0.0569(4) Uani 1 1 d . . . . .
N1 N 0.1931(2) 0.22553(17) 0.44771(8) 0.0353(4) Uani 1 1 d . . . . .
N2 N 0.2893(3) 0.6528(2) 0.30922(9) 0.0467(5) Uani 1 1 d . . . . .
C11 C 0.3551(3) 0.5377(2) 0.34977(9) 0.0353(4) Uani 1 1 d . . . . .
C6 C 0.1833(3) 0.4937(2) 0.46025(9) 0.0330(4) Uani 1 1 d . . . . .
C1 C 0.1908(3) 0.3499(2) 0.49498(9) 0.0321(4) Uani 1 1 d . . . . .
C7 C 0.1813(3) 0.4607(2) 0.38487(9) 0.0343(4) Uani 1 1 d . . . . .
C8 C 0.1905(3) 0.2801(2) 0.38264(9) 0.0374(4) Uani 1 1 d . . . . .
C2 C 0.1923(3) 0.3420(2) 0.56505(10) 0.0423(4) Uani 1 1 d . . . . .
H2 H 0.195135 0.245629 0.587734 0.051 Uiso 1 1 calc R U . . .
C5 C 0.1794(3) 0.6331(2) 0.49624(11) 0.0424(4) Uani 1 1 d . . . . .
H5 H 0.174526 0.729473 0.473584 0.051 Uiso 1 1 calc R U . . .
C13 C 0.1920(3) 0.0588(2) 0.46504(12) 0.0443(5) Uani 1 1 d . . . . .
H13A H 0.314407 0.029883 0.483839 0.066 Uiso 1 1 calc R U . . .
H13B H 0.167962 -0.002520 0.424824 0.066 Uiso 1 1 calc R U . . .
H13C H 0.092833 0.038768 0.497909 0.066 Uiso 1 1 calc R U . . .
C4 C 0.1827(4) 0.6279(3) 0.56705(12) 0.0516(5) Uani 1 1 d . . . . .
H4 H 0.180364 0.721323 0.591926 0.062 Uiso 1 1 calc R U . . .
C3 C 0.1895(3) 0.4847(3) 0.60044(10) 0.0511(5) Uani 1 1 d . . . . .
H3 H 0.192316 0.483262 0.647755 0.061 Uiso 1 1 calc R U . . .
C9 C 0.0086(3) 0.5249(3) 0.34412(12) 0.0491(6) Uani 1 1 d . . . . .
H9A H -0.031994 0.449504 0.309835 0.059 Uiso 1 1 calc R U . . .
H9B H -0.099006 0.547265 0.373989 0.059 Uiso 1 1 calc R U . . .
C10 C 0.0828(4) 0.6754(3) 0.31128(13) 0.0560(6) Uani 1 1 d . . . . .
H10A H 0.030792 0.688181 0.265812 0.067 Uiso 1 1 calc R U . . .
H10B H 0.049386 0.767266 0.338316 0.067 Uiso 1 1 calc R U . . .
C12 C 0.4132(4) 0.7615(4) 0.27249(13) 0.0674(8) Uani 1 1 d . . . . .
H12A H 0.402228 0.865107 0.291993 0.101 Uiso 1 1 calc R U . . .
H12B H 0.375119 0.765000 0.225556 0.101 Uiso 1 1 calc R U . . .
H12C H 0.544058 0.726247 0.275655 0.101 Uiso 1 1 calc R U . . .


_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
O2 C11 1.218(2) . ?
O1 C8 1.221(2) . ?
N1 C1 1.404(2) . ?
N1 C8 1.359(2) . ?
N1 C13 1.452(2) . ?
N2 C11 1.339(3) . ?
N2 C10 1.450(3) . ?
N2 C12 1.453(3) . ?
C11 C7 1.537(3) . ?
C6 C1 1.396(2) . ?
C6 C7 1.507(2) . ?
C6 C5 1.376(3) . ?
C1 C2 1.378(3) . ?
C7 C8 1.531(3) . ?
C7 C9 1.542(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.392(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.518(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C1 N1 C13 125.00(16) . . ?
C8 N1 C1 111.55(14) . . ?
C8 N1 C13 123.42(16) . . ?
C11 N2 C10 114.72(18) . . ?
C11 N2 C12 123.6(2) . . ?
C10 N2 C12 121.2(2) . . ?
O2 C11 N2 126.91(19) . . ?
O2 C11 C7 125.20(18) . . ?
N2 C11 C7 107.83(15) . . ?
C1 C6 C7 108.61(15) . . ?
C5 C6 C1 119.79(17) . . ?
C5 C6 C7 131.60(17) . . ?
C6 C1 N1 109.30(15) . . ?
C2 C1 N1 128.63(16) . . ?
C2 C1 C6 122.06(17) . . ?
C11 C7 C9 103.32(14) . . ?
C6 C7 C11 110.79(15) . . ?
C6 C7 C8 102.29(14) . . ?
C6 C7 C9 116.87(17) . . ?
C8 C7 C11 112.20(16) . . ?
C8 C7 C9 111.68(18) . . ?
O1 C8 N1 125.23(19) . . ?
O1 C8 C7 126.52(18) . . ?
N1 C8 C7 108.24(15) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.16(18) . . ?
C3 C2 H2 121.4 . . ?
C6 C5 H5 120.5 . . ?
C6 C5 C4 119.10(18) . . ?
C4 C5 H5 120.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.26(19) . . ?
C3 C4 H4 119.9 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.63(19) . . ?
C4 C3 H3 119.2 . . ?
C7 C9 H9A 110.8 . . ?
C7 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 C7 104.57(17) . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
N2 C10 C9 103.75(19) . . ?
N2 C10 H10A 111.0 . . ?
N2 C10 H10B 111.0 . . ?
C9 C10 H10A 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O2 C11 C7 C6 64.8(2) . . . . ?
O2 C11 C7 C8 -48.9(3) . . . . ?
O2 C11 C7 C9 -169.3(2) . . . . ?
N1 C1 C2 C3 180.0(2) . . . . ?
N2 C11 C7 C6 -112.77(18) . . . . ?
N2 C11 C7 C8 133.61(18) . . . . ?
N2 C11 C7 C9 13.2(2) . . . . ?
C11 N2 C10 C9 -16.4(3) . . . . ?
C11 C7 C8 O1 -61.7(3) . . . . ?
C11 C7 C8 N1 119.80(17) . . . . ?
C11 C7 C9 C10 -22.3(2) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C6 C7 C8 O1 179.6(2) . . . . ?
C6 C7 C8 N1 1.0(2) . . . . ?
C6 C7 C9 C10 99.7(2) . . . . ?
C6 C5 C4 C3 -0.1(4) . . . . ?
C1 N1 C8 O1 -179.8(2) . . . . ?
C1 N1 C8 C7 -1.3(2) . . . . ?
C1 C6 C7 C11 -120.22(17) . . . . ?
C1 C6 C7 C8 -0.5(2) . . . . ?
C1 C6 C7 C9 121.82(19) . . . . ?
C1 C6 C5 C4 -0.1(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C7 C6 C1 N1 -0.2(2) . . . . ?
C7 C6 C1 C2 -179.34(19) . . . . ?
C7 C6 C5 C4 -180.0(2) . . . . ?
C7 C9 C10 N2 23.3(3) . . . . ?
C8 N1 C1 C6 1.0(2) . . . . ?
C8 N1 C1 C2 180.0(2) . . . . ?
C8 C7 C9 C10 -143.04(19) . . . . ?
C5 C6 C1 N1 179.85(19) . . . . ?
C5 C6 C1 C2 0.8(3) . . . . ?
C5 C6 C7 C11 59.7(3) . . . . ?
C5 C6 C7 C8 179.4(2) . . . . ?
C5 C6 C7 C9 -58.3(3) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C13 N1 C1 C6 -177.12(18) . . . . ?
C13 N1 C1 C2 1.9(3) . . . . ?
C13 N1 C8 O1 -1.7(3) . . . . ?
C13 N1 C8 C7 176.86(19) . . . . ?
C9 C7 C8 O1 53.8(3) . . . . ?
C9 C7 C8 N1 -124.73(18) . . . . ?
C10 N2 C11 O2 -175.6(2) . . . . ?
C10 N2 C11 C7 1.9(3) . . . . ?
C12 N2 C11 O2 -3.4(4) . . . . ?
C12 N2 C11 C7 174.1(2) . . . . ?
C12 N2 C10 C9 171.2(2) . . . . ?

_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 3.934
_oxdiff_exptl_absorpt_empirical_full_min 0.425
