# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_luyi_0510_auto
_database_code_depnum_ccdc_archive 'CCDC 2191963'
loop_
_audit_author_name
_audit_author_address
'Dong Tang'
;Agricultural Resource and Environment Institute of Ningxia Academy of Agriculture and Forestry Scien
China
;
_audit_update_record             
;
2022-07-22 deposited with the CCDC.	2022-09-28 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 N2 O2'
_chemical_formula_sum            'C14 H18 N2 O2'
_chemical_formula_weight         246.30
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1933(4)
_cell_length_b                   17.2296(12)
_cell_length_c                   11.4006(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.909(6)
_cell_angle_gamma                90
_cell_volume                     1351.88(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3572
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.1420
_cell_measurement_theta_min      4.8060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7150
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.009
_diffrn_reflns_theta_min         4.798
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     89.00 135.00   0.50    0.73    --  107.75 108.00 126.00   92
  2  ω    140.00 166.00   0.50    0.73    --  107.75 108.00 126.00   52
  3  ω     35.00 119.00   0.50    0.18    --   47.20  57.00-150.00  168
  4  ω     73.00 104.00   0.50    0.73    --  107.75-108.00  29.00   62
  5  ω     16.00  80.00   0.50    0.18    --   47.20-108.00  29.00  128
  6  ω    -52.00 -27.00   0.50    0.73    -- -100.00  77.00  90.00   50
  7  ω   -108.00 -69.00   0.50    0.73    -- -100.00  77.00  90.00   78
  8  ω    -64.00 -39.00   0.50    0.73    -- -100.00  57.00  90.00   50
  9  ω    -63.00 -27.00   0.50    0.73    -- -100.00  57.00 -30.00   72
 10  ω    -60.00 -33.00   0.50    0.73    -- -100.00  57.00 -60.00   54
 11  ω    -69.00 -28.00   0.50    0.73    -- -100.00  57.00-120.00   82
 12  ω   -110.00 -31.00   0.50    0.73    -- -100.00 125.00-150.00  158
 13  ω   -106.00 -48.00   0.50    0.73    -- -100.00 108.00 126.00  116
 14  ω    -72.00 -47.00   0.50    0.18    --  -47.20 108.00 126.00   50
 15  ω   -123.00 -89.00   0.50    0.73    -- -100.00 -19.00 -60.00   68
 16  ω   -167.00-128.00   0.50    0.73    -- -100.00 -19.00 -60.00   78
 17  ω   -147.00-121.00   0.50    0.73    -- -100.00-108.00  29.00   52
 18  ω   -171.00-134.00   0.50    0.73    -- -100.00 -77.00  60.00   74
 19  ω   -116.00 -89.00   0.50    0.73    -- -100.00 -77.00  60.00   54
 20  ω    -21.00  22.00   0.50    0.18    --   47.20 -19.00 -90.00   86
 21  ω    -20.00   0.50   0.50    0.18    --   47.20 -37.00 150.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1598853000
_diffrn_orient_matrix_UB_12      -0.0180413000
_diffrn_orient_matrix_UB_13      -0.1197234000
_diffrn_orient_matrix_UB_21      -0.0041144000
_diffrn_orient_matrix_UB_22      -0.0852393000
_diffrn_orient_matrix_UB_23      0.0406856000
_diffrn_orient_matrix_UB_31      -0.1562821000
_diffrn_orient_matrix_UB_32      0.0206018000
_diffrn_orient_matrix_UB_33      0.0627699000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2207
_reflns_number_total             2588
_reflns_odcompleteness_completeness 98.30
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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         0.357
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2588
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0622
_refine_ls_restrained_S_all      1.078
_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)+(0.1126P)²+0.1279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1738
_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), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 0.36147(16) 0.66769(7) 0.61702(10) 0.0397(3) Uani 1 1 d . . . . .
O2 O 0.39254(17) 0.53925(7) 0.64746(10) 0.0457(4) Uani 1 1 d . . . . .
N1 N 0.1459(2) 0.67252(9) 0.43409(12) 0.0438(4) Uani 1 1 d . . . . .
N2 N 0.1822(2) 0.59351(9) 0.46716(13) 0.0433(4) Uani 1 1 d . . . . .
C1 C 0.2696(2) 0.79745(11) 0.53413(13) 0.0386(4) Uani 1 1 d . . . . .
C2 C 0.4042(2) 0.83156(11) 0.63476(15) 0.0420(4) Uani 1 1 d . . . . .
H2 H 0.484137 0.799925 0.697697 0.050 Uiso 1 1 calc R . . . .
C3 C 0.4208(3) 0.91125(12) 0.64246(17) 0.0483(4) Uani 1 1 d . . . . .
H3 H 0.512541 0.934289 0.710897 0.058 Uiso 1 1 calc R . . . .
C4 C 0.3051(3) 0.95802(12) 0.55149(17) 0.0513(5) Uani 1 1 d . . . . .
H4 H 0.318035 1.012871 0.557146 0.062 Uiso 1 1 calc R . . . .
C5 C 0.1694(3) 0.92426(12) 0.45159(17) 0.0508(5) Uani 1 1 d . . . . .
H5 H 0.088925 0.956203 0.389362 0.061 Uiso 1 1 calc R . . . .
C6 C 0.1518(2) 0.84480(12) 0.44277(15) 0.0454(4) Uani 1 1 d . . . . .
H6 H 0.059255 0.822042 0.374401 0.055 Uiso 1 1 calc R . . . .
C7 C 0.2516(2) 0.71375(11) 0.52303(13) 0.0377(4) Uani 1 1 d . . . . .
C8 C 0.3081(2) 0.59579(10) 0.57434(15) 0.0388(4) Uani 1 1 d . . . . .
C9 C 0.3308(3) 0.46109(10) 0.60154(16) 0.0439(4) Uani 1 1 d . . . . .
H9A H 0.348900 0.453856 0.519406 0.053 Uiso 1 1 calc R . . . .
H9B H 0.191641 0.453489 0.594658 0.053 Uiso 1 1 calc R . . . .
C10 C 0.4523(2) 0.40377(10) 0.69025(16) 0.0428(4) Uani 1 1 d . . . . .
H10A H 0.434844 0.412198 0.772291 0.051 Uiso 1 1 calc R . . . .
H10B H 0.591123 0.412236 0.696864 0.051 Uiso 1 1 calc R . . . .
C11 C 0.3966(2) 0.32047(11) 0.64950(15) 0.0420(4) Uani 1 1 d . . . . .
H11A H 0.257864 0.312278 0.643242 0.050 Uiso 1 1 calc R . . . .
H11B H 0.412677 0.312563 0.566980 0.050 Uiso 1 1 calc R . . . .
C12 C 0.5179(2) 0.26076(11) 0.73674(15) 0.0426(4) Uani 1 1 d . . . . .
H12A H 0.509307 0.271399 0.820342 0.051 Uiso 1 1 calc R . . . .
H12B H 0.655496 0.266980 0.738488 0.051 Uiso 1 1 calc R . . . .
C13 C 0.4573(3) 0.17713(11) 0.70368(16) 0.0441(4) Uani 1 1 d . . . . .
H13A H 0.318531 0.170894 0.699049 0.053 Uiso 1 1 calc R . . . .
H13B H 0.471550 0.165305 0.621756 0.053 Uiso 1 1 calc R . . . .
C14 C 0.5773(3) 0.11991(12) 0.79614(18) 0.0530(5) Uani 1 1 d . . . . .
H14A H 0.527681 0.067273 0.774284 0.080 Uiso 1 1 calc GR . . . .
H14B H 0.568559 0.132854 0.878078 0.080 Uiso 1 1 calc GR . . . .
H14C H 0.713243 0.122632 0.795833 0.080 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 1.3820(19) . ?
O1 C8 1.345(2) . ?
O2 C8 1.311(2) . ?
O2 C9 1.466(2) . ?
N1 N2 1.416(2) . ?
N1 C7 1.289(2) . ?
N2 C8 1.292(2) . ?
C1 C2 1.398(2) . ?
C1 C6 1.398(2) . ?
C1 C7 1.450(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.393(3) . ?
C5 C6 1.376(3) . ?
C9 C10 1.499(2) . ?
C10 C11 1.526(2) . ?
C11 C12 1.518(2) . ?
C12 C13 1.521(3) . ?
C13 C14 1.516(3) . ?

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
C8 O1 C7 102.10(12) . . ?
C8 O2 C9 114.79(13) . . ?
C7 N1 N2 107.42(14) . . ?
C8 N2 N1 104.28(14) . . ?
C2 C1 C6 119.42(18) . . ?
C2 C1 C7 120.84(16) . . ?
C6 C1 C7 119.74(16) . . ?
C3 C2 C1 119.83(17) . . ?
C2 C3 C4 120.67(18) . . ?
C3 C4 C5 119.67(19) . . ?
C6 C5 C4 120.20(18) . . ?
C5 C6 C1 120.20(17) . . ?
O1 C7 C1 119.16(14) . . ?
N1 C7 O1 111.51(16) . . ?
N1 C7 C1 129.32(15) . . ?
O2 C8 O1 115.05(14) . . ?
N2 C8 O1 114.69(16) . . ?
N2 C8 O2 130.26(16) . . ?
O2 C9 C10 107.92(13) . . ?
C9 C10 C11 111.37(14) . . ?
C12 C11 C10 112.84(14) . . ?
C11 C12 C13 114.28(15) . . ?
C14 C13 C12 112.31(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.786
_oxdiff_exptl_absorpt_empirical_full_min 0.379
