# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_lmh1229
_database_code_depnum_ccdc_archive 'CCDC 2305738'
loop_
_audit_author_name
_audit_author_address
Yulei
;Qufu Normal University
China
;
_audit_update_record             
;
2023-11-04 deposited with the CCDC.	2023-12-28 downloaded from the CCDC.
;
_audit_creation_date             2023-11-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C7 H7 N O)'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.764(3)
_cell_length_b                   6.1667(13)
_cell_length_c                   28.554(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.238(16)
_cell_angle_gamma                90
_cell_volume                     2588.8(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1228
_cell_measurement_temperature    298
_cell_measurement_theta_max      20.9880
_cell_measurement_theta_min      2.8400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9347
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.466
_diffrn_reflns_theta_min         2.771
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  17.00   0.50   12.00    --  -10.00  20.00-112.00  130
  2  ω    -34.00  65.00   0.50   12.00    --  -10.00  55.00-180.00  198
  3  ω    -67.00  47.00   0.50   12.00    --  -10.00  55.00 150.00  228
  4  ω     47.00  72.00   0.50   12.00    --  -10.00  20.00-112.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0137856000
_diffrn_orient_matrix_UB_12      0.0359595000
_diffrn_orient_matrix_UB_13      -0.0218325000
_diffrn_orient_matrix_UB_21      -0.0449515000
_diffrn_orient_matrix_UB_22      -0.0148853000
_diffrn_orient_matrix_UB_23      -0.0105577000
_diffrn_orient_matrix_UB_31      -0.0108240000
_diffrn_orient_matrix_UB_32      0.1082640000
_diffrn_orient_matrix_UB_33      0.0058212000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed 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                1401
_reflns_number_total             3041
_reflns_odcompleteness_completeness 99.90
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      0.980
_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)+(0.0663P)²+0.0796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1482
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N002(H002), N004(H004), C007(H007), C008(H008), C009(H009), C00A(H00A),
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I)
;
_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
O001 O 0.52592(11) 0.2134(2) 0.40005(5) 0.0915(5) Uani 1 1 d . . . . .
N002 N 0.39009(10) 0.1912(2) 0.61872(5) 0.0635(4) Uani 1 1 d . . . . .
H002 H 0.411737 0.065504 0.612997 0.076 Uiso 1 1 calc R U . . .
O003 O 0.37524(11) 0.2570(3) 0.54142(5) 0.0978(5) Uani 1 1 d . . . . .
N004 N 0.43115(11) 0.3480(3) 0.45159(5) 0.0703(5) Uani 1 1 d . . . . .
H004 H 0.414105 0.324402 0.479137 0.084 Uiso 1 1 calc R U . . .
C005 C 0.39153(12) 0.5285(3) 0.42767(6) 0.0568(5) Uani 1 1 d . . . . .
C006 C 0.38398(12) 0.2402(3) 0.66659(6) 0.0575(5) Uani 1 1 d . . . . .
C007 C 0.40113(13) 0.5722(3) 0.38117(6) 0.0678(5) Uani 1 1 d . . . . .
H007 H 0.435086 0.480372 0.363754 0.081 Uiso 1 1 calc R U . . .
C008 C 0.41407(14) 0.0877(3) 0.69908(7) 0.0750(6) Uani 1 1 d . . . . .
H008 H 0.438185 -0.041806 0.689082 0.090 Uiso 1 1 calc R U . . .
C009 C 0.36714(14) 0.3120(4) 0.58194(7) 0.0772(6) Uani 1 1 d . . . . .
H009 H 0.343097 0.448619 0.586919 0.093 Uiso 1 1 calc R U . . .
C00A C 0.34038(14) 0.6661(3) 0.45283(7) 0.0719(6) Uani 1 1 d . . . . .
H00A H 0.333261 0.637189 0.484254 0.086 Uiso 1 1 calc R U . . .
C00B C 0.49160(16) 0.2089(3) 0.43714(7) 0.0798(6) Uani 1 1 d . . . . .
H00B H 0.509482 0.096272 0.457588 0.096 Uiso 1 1 calc R U . . .
C00C C 0.36003(15) 0.7528(4) 0.36071(7) 0.0821(6) Uani 1 1 d . . . . .
H00C H 0.366276 0.782057 0.329216 0.098 Uiso 1 1 calc R U . . .
C00D C 0.34936(16) 0.4303(4) 0.68190(8) 0.0867(7) Uani 1 1 d . . . . .
H00D H 0.329542 0.537503 0.660456 0.104 Uiso 1 1 calc R U . . .
C00E C 0.30020(15) 0.8447(4) 0.43161(8) 0.0884(7) Uani 1 1 d . . . . .
H00E H 0.265551 0.936303 0.448699 0.106 Uiso 1 1 calc R U . . .
C00F C 0.40926(17) 0.1228(4) 0.74616(7) 0.0908(7) Uani 1 1 d . . . . .
H00F H 0.430429 0.017637 0.767800 0.109 Uiso 1 1 calc R U . . .
C00G C 0.31033(15) 0.8901(4) 0.38557(8) 0.0885(7) Uani 1 1 d . . . . .
H00G H 0.283657 1.013077 0.371403 0.106 Uiso 1 1 calc R U . . .
C00H C 0.37395(18) 0.3093(5) 0.76128(8) 0.0950(7) Uani 1 1 d . . . . .
H00H H 0.370213 0.332559 0.793226 0.114 Uiso 1 1 calc R U . . .
C00I C 0.34400(18) 0.4622(4) 0.72953(9) 0.1003(8) Uani 1 1 d . . . . .
H00I H 0.319470 0.590530 0.739889 0.120 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
O001 C00B 1.215(2) . ?
N002 H002 0.8600 . ?
N002 C006 1.411(2) . ?
N002 C009 1.307(2) . ?
O003 C009 1.222(2) . ?
N004 H004 0.8600 . ?
N004 C005 1.405(2) . ?
N004 C00B 1.330(3) . ?
C005 C007 1.375(2) . ?
C005 C00A 1.380(2) . ?
C006 C008 1.366(2) . ?
C006 C00D 1.367(3) . ?
C007 H007 0.9300 . ?
C007 C00C 1.373(3) . ?
C008 H008 0.9300 . ?
C008 C00F 1.370(3) . ?
C009 H009 0.9300 . ?
C00A H00A 0.9300 . ?
C00A C00E 1.366(3) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00G 1.362(3) . ?
C00D H00D 0.9300 . ?
C00D C00I 1.383(3) . ?
C00E H00E 0.9300 . ?
C00E C00G 1.365(3) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.350(3) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00H C00I 1.354(3) . ?
C00I H00I 0.9300 . ?

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
C006 N002 H002 115.8 . . ?
C009 N002 H002 115.8 . . ?
C009 N002 C006 128.46(17) . . ?
C005 N004 H004 115.8 . . ?
C00B N004 H004 115.8 . . ?
C00B N004 C005 128.42(16) . . ?
C007 C005 N004 123.33(16) . . ?
C007 C005 C00A 119.47(17) . . ?
C00A C005 N004 117.20(16) . . ?
C008 C006 N002 117.73(16) . . ?
C008 C006 C00D 118.75(17) . . ?
C00D C006 N002 123.53(17) . . ?
C005 C007 H007 120.4 . . ?
C00C C007 C005 119.29(18) . . ?
C00C C007 H007 120.4 . . ?
C006 C008 H008 119.5 . . ?
C006 C008 C00F 121.00(19) . . ?
C00F C008 H008 119.5 . . ?
N002 C009 H009 117.9 . . ?
O003 C009 N002 124.2(2) . . ?
O003 C009 H009 117.9 . . ?
C005 C00A H00A 120.0 . . ?
C00E C00A C005 120.03(17) . . ?
C00E C00A H00A 120.0 . . ?
O001 C00B N004 126.89(19) . . ?
O001 C00B H00B 116.6 . . ?
N004 C00B H00B 116.6 . . ?
C007 C00C H00C 119.3 . . ?
C00G C00C C007 121.38(19) . . ?
C00G C00C H00C 119.3 . . ?
C006 C00D H00D 120.2 . . ?
C006 C00D C00I 119.5(2) . . ?
C00I C00D H00D 120.2 . . ?
C00A C00E H00E 119.6 . . ?
C00G C00E C00A 120.75(19) . . ?
C00G C00E H00E 119.6 . . ?
C008 C00F H00F 119.8 . . ?
C00H C00F C008 120.3(2) . . ?
C00H C00F H00F 119.8 . . ?
C00C C00G C00E 119.1(2) . . ?
C00C C00G H00G 120.5 . . ?
C00E C00G H00G 120.5 . . ?
C00F C00H H00H 120.3 . . ?
C00F C00H C00I 119.4(2) . . ?
C00I C00H H00H 120.3 . . ?
C00D C00I H00I 119.5 . . ?
C00H C00I C00D 121.0(2) . . ?
C00H C00I H00I 119.5 . . ?

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
N002 C006 C008 C00F -179.20(18) . . . . ?
N002 C006 C00D C00I 178.44(19) . . . . ?
N004 C005 C007 C00C -179.90(18) . . . . ?
N004 C005 C00A C00E 179.90(19) . . . . ?
C005 N004 C00B O001 1.3(4) . . . . ?
C005 C007 C00C C00G 0.3(3) . . . . ?
C005 C00A C00E C00G -0.3(3) . . . . ?
C006 N002 C009 O003 179.57(18) . . . . ?
C006 C008 C00F C00H 0.4(3) . . . . ?
C006 C00D C00I C00H 1.1(4) . . . . ?
C007 C005 C00A C00E -0.4(3) . . . . ?
C007 C00C C00G C00E -1.0(3) . . . . ?
C008 C006 C00D C00I -1.2(3) . . . . ?
C008 C00F C00H C00I -0.5(4) . . . . ?
C009 N002 C006 C008 -178.82(19) . . . . ?
C009 N002 C006 C00D 1.5(3) . . . . ?
C00A C005 C007 C00C 0.4(3) . . . . ?
C00A C00E C00G C00C 1.0(4) . . . . ?
C00B N004 C005 C007 9.4(3) . . . . ?
C00B N004 C005 C00A -170.9(2) . . . . ?
C00D C006 C008 C00F 0.5(3) . . . . ?
C00F C00H C00I C00D -0.2(4) . . . . ?

_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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.776
