# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_4a
_database_code_depnum_ccdc_archive 'CCDC 2184335'
loop_
_audit_author_name
_audit_author_address
'Tetsuaki Fujihara'
;Kyoto University
Japan
;
_audit_update_record             
;
2022-07-06 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H22 N2 O2'
_chemical_formula_moiety         'C15 H22 N2 O2'
_chemical_formula_weight         262.35
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.960(4)
_cell_length_b                   11.510(6)
_cell_length_c                   32.253(18)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2955(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5931
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136.00
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.471
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            22156
_diffrn_reflns_av_R_equivalents  0.1364
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         3.175
_diffrn_reflns_theta_full        27.490
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       41
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3383
_reflns_number_gt                2274
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.0982
_refine_ls_wR_factor_ref         0.2789
_refine_ls_wR_factor_gt          0.2513
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3383
_refine_ls_number_parameters     172
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1259P)²+2.3284P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.50
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2321(3) 0.4496(2) 0.15911(7) 0.0321(6) Uani 1 1 d . . .
O2 O 0.6683(3) 0.2109(2) 0.16241(7) 0.0323(6) Uani 1 1 d . . .
N14 N 0.1077(4) 0.3479(2) 0.20995(8) 0.0279(7) Uani 1 1 d . . .
N15 N 0.7140(3) 0.0347(3) 0.13412(9) 0.0279(7) Uani 1 1 d . . .
C3 C 0.2459(4) 0.2770(3) 0.08293(10) 0.0240(7) Uani 1 1 d . . .
C4 C 0.1176(5) 0.1978(3) 0.07561(11) 0.0343(9) Uani 1 1 d . . .
H4 H 0.1073 0.1333 0.0928 0.041 Uiso 1 1 calc R . .
C5 C 0.0042(5) 0.2123(4) 0.04323(12) 0.0434(10) Uani 1 1 d . . .
H5 H -0.0813 0.1584 0.0393 0.052 Uiso 1 1 calc R . .
C6 C 0.0182(5) 0.3062(4) 0.01705(11) 0.0417(10) Uani 1 1 d . . .
H6 H -0.0568 0.3158 -0.0048 0.050 Uiso 1 1 calc R . .
C7 C 0.1446(5) 0.3859(4) 0.02351(11) 0.0380(10) Uani 1 1 d . . .
H7 H 0.1545 0.4497 0.0060 0.046 Uiso 1 1 calc R . .
C8 C 0.2581(5) 0.3715(3) 0.05622(10) 0.0298(8) Uani 1 1 d . . .
H8 H 0.3430 0.4260 0.0602 0.036 Uiso 1 1 calc R . .
C9 C 0.3708(4) 0.2589(3) 0.11785(10) 0.0243(7) Uani 1 1 d . . .
H9 H 0.4439 0.3272 0.1193 0.029 Uiso 1 1 calc R . .
C10 C 0.2846(4) 0.2439(3) 0.15989(10) 0.0249(7) Uani 1 1 d . . .
H10A H 0.1985 0.1846 0.1575 0.030 Uiso 1 1 calc R . .
H10B H 0.3667 0.2169 0.1799 0.030 Uiso 1 1 calc R . .
C11 C 0.4800(4) 0.1523(3) 0.10787(10) 0.0262(7) Uani 1 1 d . . .
H11A H 0.4102 0.0833 0.1090 0.031 Uiso 1 1 calc R . .
H11B H 0.5219 0.1596 0.0797 0.031 Uiso 1 1 calc R . .
C12 C 0.6282(4) 0.1362(3) 0.13701(10) 0.0235(7) Uani 1 1 d . . .
C13 C 0.2051(4) 0.3548(3) 0.17587(10) 0.0234(7) Uani 1 1 d . . .
C16 C 0.0288(5) 0.4532(4) 0.22565(12) 0.0400(10) Uani 1 1 d . . .
H16A H -0.0363 0.4349 0.2499 0.048 Uiso 1 1 calc R . .
H16B H -0.0434 0.4852 0.2047 0.048 Uiso 1 1 calc R . .
H16C H 0.1139 0.5088 0.2327 0.048 Uiso 1 1 calc R . .
C18 C 0.0687(5) 0.2411(4) 0.23234(12) 0.0385(9) Uani 1 1 d . . .
H18A H -0.0029 0.2586 0.2555 0.046 Uiso 1 1 calc R . .
H18B H 0.1709 0.2065 0.2422 0.046 Uiso 1 1 calc R . .
H18C H 0.0125 0.1879 0.2141 0.046 Uiso 1 1 calc R . .
C19 C 0.8549(5) 0.0136(4) 0.16183(11) 0.0357(9) Uani 1 1 d . . .
H19A H 0.9023 -0.0614 0.1560 0.043 Uiso 1 1 calc R . .
H19B H 0.8166 0.0158 0.1900 0.043 Uiso 1 1 calc R . .
H19C H 0.9388 0.0724 0.1577 0.043 Uiso 1 1 calc R . .
C20 C 0.6807(5) -0.0553(3) 0.10365(12) 0.0372(9) Uani 1 1 d . . .
H20A H 0.7574 -0.1187 0.1077 0.045 Uiso 1 1 calc R . .
H20B H 0.6952 -0.0242 0.0763 0.045 Uiso 1 1 calc R . .
H20C H 0.5675 -0.0827 0.1068 0.045 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b46'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b46'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C13 1.237(4) . ?
O2 C12 1.230(4) . ?
N14 C13 1.348(4) . ?
N14 C16 1.456(5) . ?
N14 C18 1.459(5) . ?
N15 C12 1.356(4) . ?
N15 C20 1.453(4) . ?
N15 C19 1.454(4) . ?
C3 C4 1.389(5) . ?
C3 C8 1.391(5) . ?
C3 C9 1.517(4) . ?
C4 C5 1.390(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.399(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.529(4) . ?
C9 C11 1.537(5) . ?
C9 H9 0.9800 . ?
C10 C13 1.515(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.520(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C13 N14 C16 118.9(3) . . ?
C13 N14 C18 125.1(3) . . ?
C16 N14 C18 115.9(3) . . ?
C12 N15 C20 124.7(3) . . ?
C12 N15 C19 119.4(3) . . ?
C20 N15 C19 115.9(3) . . ?
C4 C3 C8 117.4(3) . . ?
C4 C3 C9 121.2(3) . . ?
C8 C3 C9 121.4(3) . . ?
C3 C4 C5 121.7(4) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 119.3(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C3 C8 C7 120.9(4) . . ?
C3 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C3 C9 C10 112.3(3) . . ?
C3 C9 C11 109.0(3) . . ?
C10 C9 C11 110.4(3) . . ?
C3 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C11 C9 H9 108.3 . . ?
C13 C10 C9 113.2(3) . . ?
C13 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C13 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C9 114.0(3) . . ?
C12 C11 H11A 108.8 . . ?
C9 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C9 C11 H11B 108.8 . . ?
H11A C11 H11B 107.6 . . ?
O2 C12 N15 121.1(3) . . ?
O2 C12 C11 121.9(3) . . ?
N15 C12 C11 117.0(3) . . ?
O1 C13 N14 120.5(3) . . ?
O1 C13 C10 121.5(3) . . ?
N14 C13 C10 117.9(3) . . ?
N14 C16 H16A 109.5 . . ?
N14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N14 C18 H18A 109.5 . . ?
N14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N15 C19 H19A 109.5 . . ?
N15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N15 C20 H20A 109.5 . . ?
N15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C8 C3 C4 C5 -0.7(5) . . . . ?
C9 C3 C4 C5 -178.8(3) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C4 C5 C6 C7 -0.6(6) . . . . ?
C5 C6 C7 C8 0.2(6) . . . . ?
C4 C3 C8 C7 0.3(5) . . . . ?
C9 C3 C8 C7 178.4(3) . . . . ?
C6 C7 C8 C3 -0.1(5) . . . . ?
C4 C3 C9 C10 -55.4(4) . . . . ?
C8 C3 C9 C10 126.6(3) . . . . ?
C4 C3 C9 C11 67.3(4) . . . . ?
C8 C3 C9 C11 -110.7(4) . . . . ?
C3 C9 C10 C13 -70.3(4) . . . . ?
C11 C9 C10 C13 167.8(3) . . . . ?
C3 C9 C11 C12 170.7(3) . . . . ?
C10 C9 C11 C12 -65.4(4) . . . . ?
C20 N15 C12 O2 -176.7(3) . . . . ?
C19 N15 C12 O2 0.6(5) . . . . ?
C20 N15 C12 C11 4.0(5) . . . . ?
C19 N15 C12 C11 -178.7(3) . . . . ?
C9 C11 C12 O2 -9.3(5) . . . . ?
C9 C11 C12 N15 170.0(3) . . . . ?
C16 N14 C13 O1 2.6(5) . . . . ?
C18 N14 C13 O1 -179.5(3) . . . . ?
C16 N14 C13 C10 -179.5(3) . . . . ?
C18 N14 C13 C10 -1.6(5) . . . . ?
C9 C10 C13 O1 -10.5(4) . . . . ?
C9 C10 C13 N14 171.6(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
