# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_exp_1475
_database_code_depnum_ccdc_archive 'CCDC 2042131'
loop_
_audit_author_name
_audit_author_address
Kim 'Yonsei University'
_audit_update_record             
;
2020-11-03 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;
_audit_creation_date             2020-10-30
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 N4 O4'
_chemical_formula_sum            'C18 H18 N4 O4'
_chemical_formula_weight         354.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H18N4O4
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.1364(14)
_cell_length_b                   19.9122(18)
_cell_length_c                   8.5927(11)
_cell_angle_alpha                90
_cell_angle_beta                 107.324(13)
_cell_angle_gamma                90
_cell_volume                     1819.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1517
_cell_measurement_temperature    293.5(4)
_cell_measurement_theta_max      22.7720
_cell_measurement_theta_min      2.8350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            dark
_exptl_crystal_colour_modifier   dark
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8628
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.485
_diffrn_reflns_theta_min         2.172
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.5(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  91.00   1.00   53.59    --   11.67  19.00-120.00  109
  2  ω    -27.00  34.00   1.00   53.59    --   11.67 -38.00  30.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0426265000
_diffrn_orient_matrix_UB_12      0.0263811000
_diffrn_orient_matrix_UB_13      -0.0343060000
_diffrn_orient_matrix_UB_21      -0.0458636000
_diffrn_orient_matrix_UB_22      -0.0147648000
_diffrn_orient_matrix_UB_23      0.0312172000
_diffrn_orient_matrix_UB_31      0.0233596000
_diffrn_orient_matrix_UB_32      0.0188358000
_diffrn_orient_matrix_UB_33      0.0728960000
_diffrn_oxdiff_ac3_digest_frames 
;
01d0ff79de5fbd2cddff3544631e8596b3000279554
;
_diffrn_oxdiff_ac3_digest_hkl    
;
0162a1b4d6fe3855d15b1c5445ccde7e81b292
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1997
_reflns_number_total             4277
_reflns_odcompleteness_completeness 99.92
_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 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    
;
%$getVar(olex2_reference_short)%
;
_computing_publication_material  
;
%$getVar(olex2_reference_short)%
;
_computing_structure_refinement  
;
%$getVar(refinement_reference_short)%
;
_computing_structure_solution    
;
%$getVar(solution_reference_short)%
;
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0001(11)
_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   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1698
_refine_ls_R_factor_gt           0.0793
_refine_ls_restrained_S_all      1.075
_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)+(0.0602P)²+0.5978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1673
_refine_ls_wR_factor_ref         0.2083
_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:
 C00K(H00A,H00B), C00P(H00K,H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J),
 C00L(H00L), C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00O(H00C,H00F,H00G), C00Q(H00O,H00P,H00Q)
;
_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
O001 O 0.8458(3) 0.17574(12) 0.4448(3) 0.0790(8) Uani 1 1 d . . . . .
O002 O 0.5239(2) 0.49560(11) 0.3175(3) 0.0841(8) Uani 1 1 d . . . . .
N003 N 0.5240(3) 0.20086(12) 0.2016(3) 0.0561(7) Uani 1 1 d . . . . .
O004 O 1.0782(3) 0.42958(14) 0.7282(3) 0.0873(8) Uani 1 1 d . . . . .
O005 O 0.7717(3) 0.22384(14) 0.1997(3) 0.0919(9) Uani 1 1 d . . . . .
C006 C 0.4843(3) 0.26547(14) 0.1529(4) 0.0551(8) Uani 1 1 d . . . . .
N007 N 0.4039(3) 0.40319(14) 0.0810(4) 0.0822(10) Uani 1 1 d . . . . .
N008 N 0.3697(3) 0.46282(16) 0.0518(4) 0.0822(10) Uani 1 1 d . . . . .
C009 C 0.5462(3) 0.32300(15) 0.2384(4) 0.0578(8) Uani 1 1 d . . . . .
H009 H 0.617898 0.314458 0.324828 0.069 Uiso 1 1 calc R . . . .
C00A C 0.5148(3) 0.38812(15) 0.2107(4) 0.0567(8) Uani 1 1 d . . . . .
C00B C 0.5796(3) 0.44254(15) 0.3165(4) 0.0597(9) Uani 1 1 d . . . . .
C00C C 0.7103(3) 0.43432(14) 0.4221(4) 0.0579(8) Uani 1 1 d . . . . .
C00D C 0.9267(3) 0.40204(16) 0.4674(4) 0.0659(9) Uani 1 1 d . . . . .
H00D H 0.988065 0.382058 0.429360 0.079 Uiso 1 1 calc R . . . .
C00E C 0.8034(3) 0.40404(16) 0.3693(4) 0.0623(9) Uani 1 1 d . . . . .
H00E H 0.782471 0.384769 0.266086 0.075 Uiso 1 1 calc R . . . .
C00F C 0.7551(4) 0.19687(16) 0.3157(5) 0.0653(9) Uani 1 1 d . . . . .
C00G C 0.9590(3) 0.42948(17) 0.6209(4) 0.0672(9) Uani 1 1 d . . . . .
C00H C 0.7448(4) 0.46290(17) 0.5770(4) 0.0688(10) Uani 1 1 d . . . . .
H00H H 0.684144 0.484349 0.613795 0.083 Uiso 1 1 calc R . . . .
C00I C 0.4497(4) 0.15643(18) 0.1005(5) 0.0729(10) Uani 1 1 d . . . . .
H00I H 0.457983 0.109986 0.108526 0.088 Uiso 1 1 calc R . . . .
C00J C 0.3798(3) 0.25759(17) 0.0144(4) 0.0653(9) Uani 1 1 d . . . . .
H00J H 0.331691 0.291968 -0.046894 0.078 Uiso 1 1 calc R . . . .
C00K C 0.6298(3) 0.18274(16) 0.3404(4) 0.0685(10) Uani 1 1 d . . . . .
H00A H 0.624687 0.135239 0.362622 0.082 Uiso 1 1 calc R . . . .
H00B H 0.623900 0.207344 0.435236 0.082 Uiso 1 1 calc R . . . .
C00L C 0.8670(4) 0.45998(18) 0.6768(4) 0.0759(11) Uani 1 1 d . . . . .
H00L H 0.888115 0.478292 0.781021 0.091 Uiso 1 1 calc R . . . .
N00M N 0.3236(4) 0.51226(17) 0.0027(4) 0.1194(16) Uani 1 1 d . . . . .
C00N C 0.3613(4) 0.18970(19) -0.0144(5) 0.0771(11) Uani 1 1 d . . . . .
H00N H 0.298341 0.170264 -0.098844 0.092 Uiso 1 1 calc R . . . .
C00O C 1.1748(4) 0.3982(2) 0.6752(5) 0.0950(13) Uani 1 1 d . . . . .
H00C H 1.182389 0.420661 0.579757 0.142 Uiso 1 1 calc GR . . . .
H00F H 1.153512 0.351882 0.649888 0.142 Uiso 1 1 calc GR . . . .
H00G H 1.253294 0.400833 0.760346 0.142 Uiso 1 1 calc GR . . . .
C00P C 0.9738(4) 0.1932(2) 0.4508(5) 0.0988(14) Uani 1 1 d . . . . .
H00K H 0.992830 0.175435 0.355697 0.119 Uiso 1 1 calc R . . . .
H00M H 0.983049 0.241650 0.450942 0.119 Uiso 1 1 calc R . . . .
C00Q C 1.0584(5) 0.1655(4) 0.5958(7) 0.186(3) Uani 1 1 d . . . . .
H00O H 1.048017 0.117614 0.595511 0.279 Uiso 1 1 calc GR . . . .
H00P H 1.040584 0.184220 0.689477 0.279 Uiso 1 1 calc GR . . . .
H00Q H 1.143395 0.175991 0.599767 0.279 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
O001 C00F 1.326(4) . ?
O001 C00P 1.454(5) . ?
O002 C00B 1.227(3) . ?
N003 C006 1.384(4) . ?
N003 C00I 1.339(4) . ?
N003 C00K 1.451(4) . ?
O004 C00G 1.372(4) . ?
O004 C00O 1.431(5) . ?
O005 C00F 1.195(4) . ?
C006 C009 1.423(4) . ?
C006 C00J 1.404(5) . ?
N007 N008 1.250(4) . ?
N007 C00A 1.427(4) . ?
N008 N00M 1.132(4) . ?
C009 H009 0.9300 . ?
C009 C00A 1.346(4) . ?
C00A C00B 1.460(4) . ?
C00B C00C 1.477(5) . ?
C00C C00E 1.388(4) . ?
C00C C00H 1.392(4) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.381(5) . ?
C00D C00G 1.373(5) . ?
C00E H00E 0.9300 . ?
C00F C00K 1.499(5) . ?
C00G C00L 1.393(5) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.377(5) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.343(5) . ?
C00J H00J 0.9300 . ?
C00J C00N 1.379(5) . ?
C00K H00A 0.9700 . ?
C00K H00B 0.9700 . ?
C00L H00L 0.9300 . ?
C00N H00N 0.9300 . ?
C00O H00C 0.9600 . ?
C00O H00F 0.9600 . ?
C00O H00G 0.9600 . ?
C00P H00K 0.9700 . ?
C00P H00M 0.9700 . ?
C00P C00Q 1.430(6) . ?
C00Q H00O 0.9600 . ?
C00Q H00P 0.9600 . ?
C00Q H00Q 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
C00F O001 C00P 116.6(3) . . ?
C006 N003 C00K 126.0(3) . . ?
C00I N003 C006 109.8(3) . . ?
C00I N003 C00K 124.2(3) . . ?
C00G O004 C00O 117.0(3) . . ?
N003 C006 C009 122.0(3) . . ?
N003 C006 C00J 105.2(3) . . ?
C00J C006 C009 132.8(3) . . ?
N008 N007 C00A 119.9(3) . . ?
N00M N008 N007 168.1(4) . . ?
C006 C009 H009 115.7 . . ?
C00A C009 C006 128.6(3) . . ?
C00A C009 H009 115.7 . . ?
N007 C00A C00B 118.9(3) . . ?
C009 C00A N007 117.4(3) . . ?
C009 C00A C00B 123.4(3) . . ?
O002 C00B C00A 119.1(3) . . ?
O002 C00B C00C 119.9(3) . . ?
C00A C00B C00C 121.0(3) . . ?
C00E C00C C00B 122.9(3) . . ?
C00E C00C C00H 118.0(3) . . ?
C00H C00C C00B 118.9(3) . . ?
C00E C00D H00D 119.9 . . ?
C00G C00D H00D 119.9 . . ?
C00G C00D C00E 120.2(3) . . ?
C00C C00E H00E 119.4 . . ?
C00D C00E C00C 121.1(3) . . ?
C00D C00E H00E 119.4 . . ?
O001 C00F C00K 109.3(3) . . ?
O005 C00F O001 124.9(4) . . ?
O005 C00F C00K 125.8(3) . . ?
O004 C00G C00D 124.7(4) . . ?
O004 C00G C00L 115.6(3) . . ?
C00D C00G C00L 119.7(3) . . ?
C00C C00H H00H 119.4 . . ?
C00L C00H C00C 121.2(3) . . ?
C00L C00H H00H 119.4 . . ?
N003 C00I H00I 125.5 . . ?
N003 C00I C00N 109.1(3) . . ?
C00N C00I H00I 125.5 . . ?
C006 C00J H00J 126.2 . . ?
C00N C00J C006 107.7(3) . . ?
C00N C00J H00J 126.2 . . ?
N003 C00K C00F 113.6(3) . . ?
N003 C00K H00A 108.9 . . ?
N003 C00K H00B 108.9 . . ?
C00F C00K H00A 108.9 . . ?
C00F C00K H00B 108.9 . . ?
H00A C00K H00B 107.7 . . ?
C00G C00L H00L 120.1 . . ?
C00H C00L C00G 119.7(3) . . ?
C00H C00L H00L 120.1 . . ?
C00I C00N C00J 108.3(3) . . ?
C00I C00N H00N 125.8 . . ?
C00J C00N H00N 125.8 . . ?
O004 C00O H00C 109.5 . . ?
O004 C00O H00F 109.5 . . ?
O004 C00O H00G 109.5 . . ?
H00C C00O H00F 109.5 . . ?
H00C C00O H00G 109.5 . . ?
H00F C00O H00G 109.5 . . ?
O001 C00P H00K 109.9 . . ?
O001 C00P H00M 109.9 . . ?
H00K C00P H00M 108.3 . . ?
C00Q C00P O001 108.9(4) . . ?
C00Q C00P H00K 109.9 . . ?
C00Q C00P H00M 109.9 . . ?
C00P C00Q H00O 109.5 . . ?
C00P C00Q H00P 109.5 . . ?
C00P C00Q H00Q 109.5 . . ?
H00O C00Q H00P 109.5 . . ?
H00O C00Q H00Q 109.5 . . ?
H00P C00Q H00Q 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
O001 C00F C00K N003 -176.9(3) . . . . ?
O002 C00B C00C C00E -137.3(3) . . . . ?
O002 C00B C00C C00H 37.3(5) . . . . ?
N003 C006 C009 C00A -176.2(3) . . . . ?
N003 C006 C00J C00N -0.1(4) . . . . ?
N003 C00I C00N C00J 0.0(4) . . . . ?
O004 C00G C00L C00H 179.4(3) . . . . ?
O005 C00F C00K N003 4.2(5) . . . . ?
C006 N003 C00I C00N -0.1(4) . . . . ?
C006 N003 C00K C00F -72.3(4) . . . . ?
C006 C009 C00A N007 1.2(5) . . . . ?
C006 C009 C00A C00B 174.2(3) . . . . ?
C006 C00J C00N C00I 0.1(4) . . . . ?
N007 C00A C00B O002 16.9(5) . . . . ?
N007 C00A C00B C00C -163.4(3) . . . . ?
N008 N007 C00A C009 179.0(3) . . . . ?
N008 N007 C00A C00B 5.6(5) . . . . ?
C009 C006 C00J C00N -179.9(3) . . . . ?
C009 C00A C00B O002 -156.0(3) . . . . ?
C009 C00A C00B C00C 23.7(5) . . . . ?
C00A N007 N008 N00M 173(2) . . . . ?
C00A C00B C00C C00E 43.0(5) . . . . ?
C00A C00B C00C C00H -142.4(3) . . . . ?
C00B C00C C00E C00D 174.8(3) . . . . ?
C00B C00C C00H C00L -176.3(3) . . . . ?
C00C C00H C00L C00G 1.7(5) . . . . ?
C00D C00G C00L C00H -0.6(5) . . . . ?
C00E C00C C00H C00L -1.5(5) . . . . ?
C00E C00D C00G O004 179.4(3) . . . . ?
C00E C00D C00G C00L -0.7(5) . . . . ?
C00F O001 C00P C00Q -179.0(4) . . . . ?
C00G C00D C00E C00C 0.9(5) . . . . ?
C00H C00C C00E C00D 0.2(5) . . . . ?
C00I N003 C006 C009 180.0(3) . . . . ?
C00I N003 C006 C00J 0.1(4) . . . . ?
C00I N003 C00K C00F 107.6(4) . . . . ?
C00J C006 C009 C00A 3.5(6) . . . . ?
C00K N003 C006 C009 -0.1(5) . . . . ?
C00K N003 C006 C00J -180.0(3) . . . . ?
C00K N003 C00I C00N -180.0(3) . . . . ?
C00O O004 C00G C00D -0.6(5) . . . . ?
C00O O004 C00G C00L 179.5(3) . . . . ?
C00P O001 C00F O005 6.6(5) . . . . ?
C00P O001 C00F C00K -172.4(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 15.1 0.0 ?
2 0.000 0.500 0.000 15.1 0.0 ?

_shelx_SHELXL_version_number     2018/3
_olex2_date_sample_data_collection 2020-10-29
_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 1.181
_oxdiff_exptl_absorpt_empirical_full_min 0.820
####################################################################### 
# 
# 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_exp_1472
_database_code_depnum_ccdc_archive 'CCDC 2042132'
loop_
_audit_author_name
_audit_author_address
Kim
;Yonsei University
South Korea
;
_audit_update_record             
;
2020-11-03 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;
_audit_creation_date             2020-10-29
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 N2 O3'
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H18N203
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           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                   10.3803(6)
_cell_length_b                   7.9121(4)
_cell_length_c                   19.5926(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.061(5)
_cell_angle_gamma                90
_cell_volume                     1560.93(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3818
_cell_measurement_temperature    293.60(13)
_cell_measurement_theta_max      28.8390
_cell_measurement_theta_min      3.2610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             656
_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  0.0162
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7154
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.677
_diffrn_reflns_theta_min         2.143
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.60(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  49.00   1.00   38.03    --   11.83 -19.00-120.00  113
  2  ω     15.00  76.00   1.00   38.03    --   11.83  77.00   0.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0205569000
_diffrn_orient_matrix_UB_12      0.0118463000
_diffrn_orient_matrix_UB_13      0.0369329000
_diffrn_orient_matrix_UB_21      -0.0553658000
_diffrn_orient_matrix_UB_22      0.0535720000
_diffrn_orient_matrix_UB_23      -0.0013824000
_diffrn_orient_matrix_UB_31      -0.0384057000
_diffrn_orient_matrix_UB_32      -0.0709165000
_diffrn_orient_matrix_UB_33      0.0051238000
_diffrn_oxdiff_ac3_digest_frames 
;
0171a67c16971cba68eaeefb315c5db1ca000277733
;
_diffrn_oxdiff_ac3_digest_hkl    
;
0144ebb41dd8f639bcce4119a3dd12c6d5a05a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3091
_reflns_number_total             3710
_reflns_odcompleteness_completeness 99.91
_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 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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         0.214
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0057(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.3820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1179
_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:
 C009(H00A,H00B), C00J(H00G,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I),
 C00K(H00K), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00M(H00M,H00N,H00O), C00N(H00P,H00Q,H00R)
;
_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 0.34657(9) 0.70699(13) 0.52828(5) 0.0423(2) Uani 1 1 d . . . . .
O002 O 0.59268(11) 0.71970(16) 0.20493(5) 0.0534(3) Uani 1 1 d . . . . .
N003 N 0.57744(11) 0.71650(14) 0.67620(5) 0.0356(3) Uani 1 1 d . . . . .
N004 N 0.56131(10) 0.73024(15) 0.51923(5) 0.0357(3) Uani 1 1 d . . . . .
O005 O 0.90411(10) 0.6601(2) 0.52479(6) 0.0663(4) Uani 1 1 d . . . . .
C006 C 0.47761(12) 0.68339(17) 0.55295(6) 0.0345(3) Uani 1 1 d . . . . .
C007 C 0.69853(12) 0.72295(17) 0.54946(7) 0.0351(3) Uani 1 1 d . . . . .
C008 C 0.64690(13) 0.71095(18) 0.27570(7) 0.0390(3) Uani 1 1 d . . . . .
C009 C 0.50883(13) 0.59762(17) 0.62352(6) 0.0378(3) Uani 1 1 d . . . . .
H00A H 0.427375 0.560242 0.634740 0.045 Uiso 1 1 calc R . . . .
H00B H 0.564367 0.499451 0.622629 0.045 Uiso 1 1 calc R . . . .
C00A C 0.73598(12) 0.70856(17) 0.42236(7) 0.0360(3) Uani 1 1 d . . . . .
C00B C 0.69750(13) 0.78728(17) 0.67420(7) 0.0379(3) Uani 1 1 d . . . . .
C00C C 0.62807(14) 0.80884(17) 0.38884(7) 0.0390(3) Uani 1 1 d . . . . .
H00C H 0.585537 0.875638 0.415729 0.047 Uiso 1 1 calc R . . . .
C00D C 0.75632(13) 0.61329(18) 0.30754(7) 0.0392(3) Uani 1 1 d . . . . .
H00D H 0.799602 0.548277 0.280413 0.047 Uiso 1 1 calc R . . . .
C00E C 0.75899(13) 0.75820(18) 0.61736(7) 0.0382(3) Uani 1 1 d . . . . .
H00E H 0.851208 0.764198 0.628280 0.046 Uiso 1 1 calc R . . . .
C00F C 0.80017(12) 0.61408(18) 0.38036(7) 0.0386(3) Uani 1 1 d . . . . .
H00F H 0.874144 0.550050 0.401672 0.046 Uiso 1 1 calc R . . . .
C00G C 0.78770(13) 0.69612(19) 0.50031(7) 0.0407(3) Uani 1 1 d . . . . .
C00H C 0.58385(14) 0.81014(18) 0.31653(7) 0.0418(3) Uani 1 1 d . . . . .
H00H H 0.511876 0.877285 0.295033 0.050 Uiso 1 1 calc R . . . .
C00I C 0.54594(16) 0.75948(19) 0.73739(7) 0.0455(3) Uani 1 1 d . . . . .
H00I H 0.470489 0.725475 0.751358 0.055 Uiso 1 1 calc R . . . .
C00J C 0.30323(13) 0.7986(2) 0.46287(7) 0.0447(3) Uani 1 1 d . . . . .
H00G H 0.321975 0.733774 0.424373 0.054 Uiso 1 1 calc R . . . .
H00J H 0.349291 0.905983 0.465656 0.054 Uiso 1 1 calc R . . . .
C00K C 0.74014(17) 0.8785(2) 0.73611(7) 0.0507(4) Uani 1 1 d . . . . .
H00K H 0.818575 0.940085 0.749397 0.061 Uiso 1 1 calc R . . . .
C00L C 0.64464(17) 0.8615(2) 0.77482(8) 0.0535(4) Uani 1 1 d . . . . .
H00L H 0.647443 0.910670 0.818274 0.064 Uiso 1 1 calc R . . . .
C00M C 0.65250(17) 0.6260(3) 0.15882(8) 0.0595(4) Uani 1 1 d . . . . .
H00M H 0.603521 0.643665 0.111090 0.089 Uiso 1 1 calc GR . . . .
H00N H 0.651911 0.507967 0.170052 0.089 Uiso 1 1 calc GR . . . .
H00O H 0.742449 0.663227 0.164213 0.089 Uiso 1 1 calc GR . . . .
C00N C 0.15714(15) 0.8267(3) 0.45108(10) 0.0624(5) Uani 1 1 d . . . . .
H00P H 0.123727 0.879434 0.406134 0.094 Uiso 1 1 calc GR . . . .
H00Q H 0.140399 0.898539 0.487458 0.094 Uiso 1 1 calc GR . . . .
H00R H 0.113412 0.720113 0.452077 0.094 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
O001 C006 1.3414(15) . ?
O001 C00J 1.4457(16) . ?
O002 C008 1.3656(16) . ?
O002 C00M 1.4226(19) . ?
N003 C009 1.4492(17) . ?
N003 C00B 1.3755(17) . ?
N003 C00I 1.3602(17) . ?
N004 C006 1.2679(16) . ?
N004 C007 1.4047(16) . ?
O005 C00G 1.2205(16) . ?
C006 C009 1.5032(17) . ?
C007 C00E 1.3548(18) . ?
C007 C00G 1.5040(19) . ?
C008 C00D 1.3900(19) . ?
C008 C00H 1.392(2) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C00A C00C 1.3993(19) . ?
C00A C00F 1.3951(19) . ?
C00A C00G 1.4940(18) . ?
C00B C00E 1.4304(19) . ?
C00B C00K 1.3884(19) . ?
C00C H00C 0.9300 . ?
C00C C00H 1.3791(19) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.3883(19) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00L 1.369(2) . ?
C00J H00G 0.9700 . ?
C00J H00J 0.9700 . ?
C00J C00N 1.494(2) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.393(2) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9600 . ?
C00M H00N 0.9600 . ?
C00M H00O 0.9600 . ?
C00N H00P 0.9600 . ?
C00N H00Q 0.9600 . ?
C00N H00R 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
C006 O001 C00J 117.33(10) . . ?
C008 O002 C00M 118.85(12) . . ?
C00B N003 C009 122.40(11) . . ?
C00I N003 C009 127.46(12) . . ?
C00I N003 C00B 109.68(12) . . ?
C006 N004 C007 121.42(11) . . ?
O001 C006 C009 111.55(11) . . ?
N004 C006 O001 122.34(11) . . ?
N004 C006 C009 126.11(12) . . ?
N004 C007 C00G 117.04(11) . . ?
C00E C007 N004 125.86(12) . . ?
C00E C007 C00G 116.58(11) . . ?
O002 C008 C00D 125.04(12) . . ?
O002 C008 C00H 114.80(12) . . ?
C00D C008 C00H 120.16(12) . . ?
N003 C009 C006 108.72(10) . . ?
N003 C009 H00A 109.9 . . ?
N003 C009 H00B 109.9 . . ?
C006 C009 H00A 109.9 . . ?
C006 C009 H00B 109.9 . . ?
H00A C009 H00B 108.3 . . ?
C00C C00A C00G 124.41(12) . . ?
C00F C00A C00C 118.00(12) . . ?
C00F C00A C00G 117.59(12) . . ?
N003 C00B C00E 122.38(12) . . ?
N003 C00B C00K 106.59(13) . . ?
C00K C00B C00E 131.00(14) . . ?
C00A C00C H00C 119.5 . . ?
C00H C00C C00A 121.01(13) . . ?
C00H C00C H00C 119.5 . . ?
C008 C00D H00D 120.4 . . ?
C00F C00D C008 119.13(12) . . ?
C00F C00D H00D 120.4 . . ?
C007 C00E C00B 127.57(12) . . ?
C007 C00E H00E 116.2 . . ?
C00B C00E H00E 116.2 . . ?
C00A C00F H00F 119.2 . . ?
C00D C00F C00A 121.62(12) . . ?
C00D C00F H00F 119.2 . . ?
O005 C00G C007 119.07(12) . . ?
O005 C00G C00A 119.51(12) . . ?
C00A C00G C007 121.40(11) . . ?
C008 C00H H00H 120.0 . . ?
C00C C00H C008 120.03(13) . . ?
C00C C00H H00H 120.0 . . ?
N003 C00I H00I 125.9 . . ?
N003 C00I C00L 108.10(14) . . ?
C00L C00I H00I 125.9 . . ?
O001 C00J H00G 110.3 . . ?
O001 C00J H00J 110.3 . . ?
O001 C00J C00N 107.28(12) . . ?
H00G C00J H00J 108.5 . . ?
C00N C00J H00G 110.3 . . ?
C00N C00J H00J 110.3 . . ?
C00B C00K H00K 126.0 . . ?
C00B C00K C00L 107.90(14) . . ?
C00L C00K H00K 126.0 . . ?
C00I C00L C00K 107.71(13) . . ?
C00I C00L H00L 126.1 . . ?
C00K C00L H00L 126.1 . . ?
O002 C00M H00M 109.5 . . ?
O002 C00M H00N 109.5 . . ?
O002 C00M H00O 109.5 . . ?
H00M C00M H00N 109.5 . . ?
H00M C00M H00O 109.5 . . ?
H00N C00M H00O 109.5 . . ?
C00J C00N H00P 109.5 . . ?
C00J C00N H00Q 109.5 . . ?
C00J C00N H00R 109.5 . . ?
H00P C00N H00Q 109.5 . . ?
H00P C00N H00R 109.5 . . ?
H00Q C00N H00R 109.5 . . ?

_olex2_date_sample_data_collection 2020-10-28
_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 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.676
