# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_-1point6degC
_database_code_depnum_ccdc_archive 'CCDC 2291942'
loop_
_audit_author_name
_audit_author_address
'Shodai Hasebe'
;Waseda University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_-1point6degC        
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: This is because we input the calibrated true temperature manually after measurement. Note that the temperature difference between the default temperature (293K) and the true temperature is <40K.
;
# Added during the CSD deposition process: Thursday 31 August 2023 06:53 AM
# end Validation Reply Form

_audit_creation_date             2022-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0499(6)
_cell_length_b                   10.3177(9)
_cell_length_c                   16.6641(15)
_cell_angle_alpha                101.437(7)
_cell_angle_beta                 92.135(6)
_cell_angle_gamma                101.786(7)
_cell_volume                     994.76(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8120
_cell_measurement_temperature    271.55
_cell_measurement_theta_max      68
_cell_measurement_theta_min      4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.6504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR(Rigaku,1995)
_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    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11063
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.236
_diffrn_reflns_theta_min         4.478
_diffrn_ambient_temperature      271.55
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2199
_reflns_number_total             3551
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3551
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.098
_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)+(0.0693P)²+0.2353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.1885
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C00H \\sim C2 \\sim C00R \\sim C1: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C00H \\sim C00Q \\sim C00P \\sim C00O: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 C00H, C2, C00R, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00Q, C00H, C00P, C00O
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C00R)=Sof(H00Y)=Sof(H)=Sof(HA)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=
 Sof(H2A)=Sof(H2B)=Sof(H2C)=1-FVAR(1)
 Sof(C00O)=Sof(H00P)=Sof(H00Q)=Sof(H00R)=Sof(C00P)=Sof(H00S)=Sof(H00T)=
 Sof(H00U)=Sof(C00Q)=Sof(H00V)=Sof(H00W)=Sof(H00X)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00D(H00D), C00E(H00E), C00G(H00G), C00J(H00J),
 C00K(H00K)
5.b Idealised Me refined as rotating group:
 C00L(H00B,H00C,H00F), C00M(H00H,H00I,H00L), C00N(H00M,H00N,H00O), C00O(H00P,
 H00Q,H00R), C00P(H00S,H00T,H00U), C00Q(H00V,H00W,H00X), C00R(H00Y,H,HA),
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
5.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 0.6517(3) 0.60423(18) 0.68438(12) 0.0680(6) Uani 1 1 d . . . . .
H001 H 0.7309 0.5608 0.6561 0.102 Uiso 1 1 calc R U . . .
N002 N 0.8123(4) 0.3956(2) 0.61930(13) 0.0602(6) Uani 1 1 d . . . . .
N003 N 0.8465(6) 0.0119(3) 0.39797(16) 0.0760(8) Uani 1 1 d . . . . .
O004 O 0.6447(5) -0.0305(2) 0.40151(15) 0.1054(9) Uani 1 1 d . . . . .
O005 O 0.9624(5) -0.0461(2) 0.35115(15) 0.1043(8) Uani 1 1 d . . . . .
C006 C 0.5570(5) 0.3922(3) 0.72606(15) 0.0535(7) Uani 1 1 d . . . . .
C007 C 0.3073(4) 0.3652(3) 0.83436(15) 0.0530(7) Uani 1 1 d . . . . .
C008 C 0.5403(4) 0.5280(3) 0.73408(15) 0.0535(7) Uani 1 1 d . . . . .
C009 C 0.6944(5) 0.3311(3) 0.66695(16) 0.0583(7) Uani 1 1 d . . . . .
H009 H 0.6974 0.2404 0.6633 0.070 Uiso 1 1 calc R U . . .
C00A C 0.4389(4) 0.3142(3) 0.77630(15) 0.0557(7) Uani 1 1 d . . . . .
H00A H 0.4497 0.2242 0.7702 0.067 Uiso 1 1 calc R U . . .
C00B C 0.9320(5) 0.3254(3) 0.56022(16) 0.0563(7) Uani 1 1 d . . . . .
C00C C 0.4055(5) 0.5849(2) 0.79172(15) 0.0541(7) Uani 1 1 d . . . . .
C00D C 0.2948(4) 0.5012(3) 0.83988(15) 0.0556(7) Uani 1 1 d . . . . .
H00D H 0.2056 0.5377 0.8787 0.067 Uiso 1 1 calc R U . . .
C00E C 0.8316(5) 0.2016(3) 0.51011(16) 0.0580(7) Uani 1 1 d . . . . .
H00E H 0.6826 0.1603 0.5152 0.070 Uiso 1 1 calc R U . . .
C00F C 0.9576(5) 0.1413(3) 0.45259(16) 0.0588(7) Uani 1 1 d . . . . .
C00G C 1.1543(5) 0.3851(3) 0.55057(17) 0.0630(8) Uani 1 1 d . . . . .
H00G H 1.2215 0.4692 0.5831 0.076 Uiso 1 1 calc R U . . .
C00H C 0.1775(5) 0.2829(3) 0.89101(16) 0.0581(7) Uani 1 1 d . U . . .
C00I C 0.3828(5) 0.7328(3) 0.80095(17) 0.0608(7) Uani 1 1 d . . . . .
C00J C 1.1783(5) 0.1974(3) 0.44325(17) 0.0664(8) Uani 1 1 d . . . . .
H00J H 1.2597 0.1536 0.4044 0.080 Uiso 1 1 calc R U . . .
C00K C 1.2758(5) 0.3208(3) 0.49336(18) 0.0693(8) Uani 1 1 d . . . . .
H00K H 1.4254 0.3611 0.4884 0.083 Uiso 1 1 calc R U . . .
C00L C 0.6149(5) 0.8296(3) 0.8233(2) 0.0802(10) Uani 1 1 d . . . . .
H00B H 0.6801 0.8173 0.8740 0.120 Uiso 1 1 calc R U . . .
H00C H 0.5973 0.9214 0.8296 0.120 Uiso 1 1 calc R U . . .
H00F H 0.7127 0.8107 0.7805 0.120 Uiso 1 1 calc R U . . .
C00M C 0.2770(5) 0.7534(3) 0.72040(19) 0.0798(9) Uani 1 1 d . . . . .
H00H H 0.3734 0.7342 0.6771 0.120 Uiso 1 1 calc R U . . .
H00I H 0.2607 0.8455 0.7270 0.120 Uiso 1 1 calc R U . . .
H00L H 0.1309 0.6935 0.7068 0.120 Uiso 1 1 calc R U . . .
C00N C 0.2278(6) 0.7696(3) 0.8684(2) 0.0872(11) Uani 1 1 d . . . . .
H00M H 0.0813 0.7099 0.8555 0.131 Uiso 1 1 calc R U . . .
H00N H 0.2127 0.8614 0.8719 0.131 Uiso 1 1 calc R U . . .
H00O H 0.2921 0.7608 0.9200 0.131 Uiso 1 1 calc R U . . .
C00O C 0.2238(8) 0.1413(4) 0.8796(3) 0.0910(15) Uani 0.858(4) 1 d . U P A 1
H00P H 0.1778 0.0934 0.8241 0.136 Uiso 0.858(4) 1 calc R U P A 1
H00Q H 0.1399 0.0937 0.9167 0.136 Uiso 0.858(4) 1 calc R U P A 1
H00R H 0.3827 0.1475 0.8910 0.136 Uiso 0.858(4) 1 calc R U P A 1
C00P C 0.2458(8) 0.3544(4) 0.9805(2) 0.0866(14) Uani 0.858(4) 1 d . U P A 1
H00S H 0.4045 0.3606 0.9926 0.130 Uiso 0.858(4) 1 calc R U P A 1
H00T H 0.1602 0.3037 1.0158 0.130 Uiso 0.858(4) 1 calc R U P A 1
H00U H 0.2156 0.4437 0.9894 0.130 Uiso 0.858(4) 1 calc R U P A 1
C00Q C -0.0757(6) 0.2696(5) 0.8733(3) 0.0942(15) Uani 0.858(4) 1 d . U P A 1
H00V H -0.1088 0.3582 0.8806 0.141 Uiso 0.858(4) 1 calc R U P A 1
H00W H -0.1571 0.2210 0.9105 0.141 Uiso 0.858(4) 1 calc R U P A 1
H00X H -0.1210 0.2214 0.8178 0.141 Uiso 0.858(4) 1 calc R U P A 1
C00R C 0.008(4) 0.149(2) 0.8335(13) 0.075(6) Uani 0.142(4) 1 d . U P A 2
H00Y H -0.0849 0.1764 0.7951 0.112 Uiso 0.142(4) 1 calc R U P A 2
H H -0.0862 0.1003 0.8677 0.112 Uiso 0.142(4) 1 calc R U P A 2
HA H 0.0973 0.0907 0.8041 0.112 Uiso 0.142(4) 1 calc R U P A 2
C1 C 0.349(4) 0.227(3) 0.9405(15) 0.076(6) Uani 0.142(4) 1 d . U P A 2
H1A H 0.4225 0.1694 0.9029 0.114 Uiso 0.142(4) 1 calc R U P A 2
H1B H 0.2697 0.1764 0.9770 0.114 Uiso 0.142(4) 1 calc R U P A 2
H1C H 0.4613 0.3015 0.9718 0.114 Uiso 0.142(4) 1 calc R U P A 2
C2 C 0.022(5) 0.354(3) 0.9449(18) 0.090(7) Uani 0.142(4) 1 d . U P A 2
H2A H 0.1087 0.4367 0.9784 0.135 Uiso 0.142(4) 1 calc R U P A 2
H2B H -0.0490 0.2962 0.9794 0.135 Uiso 0.142(4) 1 calc R U P A 2
H2C H -0.0925 0.3743 0.9107 0.135 Uiso 0.142(4) 1 calc R U P A 2


_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 H001 0.8200 . ?
O001 C008 1.357(3) . ?
N002 C009 1.280(3) . ?
N002 C00B 1.415(3) . ?
N003 O004 1.218(3) . ?
N003 O005 1.219(3) . ?
N003 C00F 1.473(4) . ?
C006 C008 1.405(3) . ?
C006 C009 1.445(3) . ?
C006 C00A 1.392(3) . ?
C007 C00A 1.369(3) . ?
C007 C00D 1.405(3) . ?
C007 C00H 1.526(3) . ?
C008 C00C 1.401(3) . ?
C009 H009 0.9300 . ?
C00A H00A 0.9300 . ?
C00B C00E 1.385(4) . ?
C00B C00G 1.390(4) . ?
C00C C00D 1.385(3) . ?
C00C C00I 1.538(3) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00F 1.378(4) . ?
C00F C00J 1.370(4) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.374(4) . ?
C00H C00O 1.520(4) . ?
C00H C00P 1.527(4) . ?
C00H C00Q 1.522(5) . ?
C00H C00R 1.65(2) . ?
C00H C1 1.57(2) . ?
C00H C2 1.52(2) . ?
C00I C00L 1.533(4) . ?
C00I C00M 1.536(4) . ?
C00I C00N 1.530(4) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.379(4) . ?
C00K H00K 0.9300 . ?
C00L H00B 0.9600 . ?
C00L H00C 0.9600 . ?
C00L H00F 0.9600 . ?
C00M H00H 0.9600 . ?
C00M H00I 0.9600 . ?
C00M H00L 0.9600 . ?
C00N H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?
C00O H00P 0.9600 . ?
C00O H00Q 0.9600 . ?
C00O H00R 0.9600 . ?
C00P H00S 0.9600 . ?
C00P H00T 0.9600 . ?
C00P H00U 0.9600 . ?
C00Q H00V 0.9600 . ?
C00Q H00W 0.9600 . ?
C00Q H00X 0.9600 . ?
C00R H00Y 0.9600 . ?
C00R H 0.9600 . ?
C00R HA 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
C008 O001 H001 109.5 . . ?
C009 N002 C00B 119.3(2) . . ?
O004 N003 O005 123.8(3) . . ?
O004 N003 C00F 118.5(3) . . ?
O005 N003 C00F 117.8(3) . . ?
C008 C006 C009 121.7(2) . . ?
C00A C006 C008 119.4(2) . . ?
C00A C006 C009 118.9(2) . . ?
C00A C007 C00D 116.3(2) . . ?
C00A C007 C00H 123.7(2) . . ?
C00D C007 C00H 120.1(2) . . ?
O001 C008 C006 119.8(2) . . ?
O001 C008 C00C 119.5(2) . . ?
C00C C008 C006 120.7(2) . . ?
N002 C009 C006 123.3(2) . . ?
N002 C009 H009 118.3 . . ?
C006 C009 H009 118.3 . . ?
C006 C00A H00A 118.9 . . ?
C007 C00A C006 122.3(2) . . ?
C007 C00A H00A 118.9 . . ?
C00E C00B N002 121.9(3) . . ?
C00E C00B C00G 119.3(3) . . ?
C00G C00B N002 118.7(3) . . ?
C008 C00C C00I 121.6(2) . . ?
C00D C00C C008 116.5(2) . . ?
C00D C00C C00I 121.9(2) . . ?
C007 C00D H00D 117.6 . . ?
C00C C00D C007 124.8(2) . . ?
C00C C00D H00D 117.6 . . ?
C00B C00E H00E 120.8 . . ?
C00F C00E C00B 118.5(3) . . ?
C00F C00E H00E 120.8 . . ?
C00E C00F N003 117.9(3) . . ?
C00J C00F N003 119.1(3) . . ?
C00J C00F C00E 123.0(3) . . ?
C00B C00G H00G 119.7 . . ?
C00K C00G C00B 120.5(3) . . ?
C00K C00G H00G 119.7 . . ?
C007 C00H C00P 109.8(2) . . ?
C007 C00H C00R 108.2(7) . . ?
C007 C00H C1 108.8(8) . . ?
C00O C00H C007 112.4(2) . . ?
C00O C00H C00P 107.9(3) . . ?
C00O C00H C00Q 108.1(3) . . ?
C00Q C00H C007 109.5(2) . . ?
C00Q C00H C00P 109.0(3) . . ?
C1 C00H C00R 105.7(13) . . ?
C2 C00H C007 115.2(9) . . ?
C2 C00H C00R 104.8(15) . . ?
C2 C00H C1 113.5(15) . . ?
C00L C00I C00C 110.6(2) . . ?
C00L C00I C00M 109.6(2) . . ?
C00M C00I C00C 110.0(2) . . ?
C00N C00I C00C 111.0(2) . . ?
C00N C00I C00L 108.2(3) . . ?
C00N C00I C00M 107.4(2) . . ?
C00F C00J H00J 121.1 . . ?
C00F C00J C00K 117.9(3) . . ?
C00K C00J H00J 121.1 . . ?
C00G C00K C00J 120.8(3) . . ?
C00G C00K H00K 119.6 . . ?
C00J C00K H00K 119.6 . . ?
C00I C00L H00B 109.5 . . ?
C00I C00L H00C 109.5 . . ?
C00I C00L H00F 109.5 . . ?
H00B C00L H00C 109.5 . . ?
H00B C00L H00F 109.5 . . ?
H00C C00L H00F 109.5 . . ?
C00I C00M H00H 109.5 . . ?
C00I C00M H00I 109.5 . . ?
C00I C00M H00L 109.5 . . ?
H00H C00M H00I 109.5 . . ?
H00H C00M H00L 109.5 . . ?
H00I C00M H00L 109.5 . . ?
C00I C00N H00M 109.5 . . ?
C00I C00N H00N 109.5 . . ?
C00I C00N H00O 109.5 . . ?
H00M C00N H00N 109.5 . . ?
H00M C00N H00O 109.5 . . ?
H00N C00N H00O 109.5 . . ?
C00H C00O H00P 109.5 . . ?
C00H C00O H00Q 109.5 . . ?
C00H C00O H00R 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
H00P C00O H00R 109.5 . . ?
H00Q C00O H00R 109.5 . . ?
C00H C00P H00S 109.5 . . ?
C00H C00P H00T 109.5 . . ?
C00H C00P H00U 109.5 . . ?
H00S C00P H00T 109.5 . . ?
H00S C00P H00U 109.5 . . ?
H00T C00P H00U 109.5 . . ?
C00H C00Q H00V 109.5 . . ?
C00H C00Q H00W 109.5 . . ?
C00H C00Q H00X 109.5 . . ?
H00V C00Q H00W 109.5 . . ?
H00V C00Q H00X 109.5 . . ?
H00W C00Q H00X 109.5 . . ?
C00H C00R H00Y 109.5 . . ?
C00H C00R H 109.5 . . ?
C00H C00R HA 109.5 . . ?
H00Y C00R H 109.5 . . ?
H00Y C00R HA 109.5 . . ?
H C00R HA 109.5 . . ?
C00H C1 H1A 109.5 . . ?
C00H C1 H1B 109.5 . . ?
C00H C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00H C2 H2A 109.5 . . ?
C00H C2 H2B 109.5 . . ?
C00H C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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 C008 C00C C00D 179.4(2) . . . . ?
O001 C008 C00C C00I -0.8(4) . . . . ?
N002 C00B C00E C00F 178.3(2) . . . . ?
N002 C00B C00G C00K -179.4(2) . . . . ?
N003 C00F C00J C00K 177.9(2) . . . . ?
O004 N003 C00F C00E 5.7(4) . . . . ?
O004 N003 C00F C00J -173.1(3) . . . . ?
O005 N003 C00F C00E -174.9(2) . . . . ?
O005 N003 C00F C00J 6.3(4) . . . . ?
C006 C008 C00C C00D 0.8(4) . . . . ?
C006 C008 C00C C00I -179.3(2) . . . . ?
C008 C006 C009 N002 1.2(4) . . . . ?
C008 C006 C00A C007 -0.6(4) . . . . ?
C008 C00C C00D C007 -0.5(4) . . . . ?
C008 C00C C00I C00L -59.5(3) . . . . ?
C008 C00C C00I C00M 61.7(3) . . . . ?
C008 C00C C00I C00N -179.6(3) . . . . ?
C009 N002 C00B C00E 46.9(4) . . . . ?
C009 N002 C00B C00G -135.3(3) . . . . ?
C009 C006 C008 O001 1.3(4) . . . . ?
C009 C006 C008 C00C 179.9(2) . . . . ?
C009 C006 C00A C007 179.2(2) . . . . ?
C00A C006 C008 O001 -178.9(2) . . . . ?
C00A C006 C008 C00C -0.3(4) . . . . ?
C00A C006 C009 N002 -178.6(3) . . . . ?
C00A C007 C00D C00C -0.4(4) . . . . ?
C00A C007 C00H C00O 3.9(4) . . . . ?
C00A C007 C00H C00P 124.1(3) . . . . ?
C00A C007 C00H C00Q -116.2(3) . . . . ?
C00A C007 C00H C00R -56.9(10) . . . . ?
C00A C007 C00H C1 57.4(11) . . . . ?
C00A C007 C00H C2 -173.8(15) . . . . ?
C00B N002 C009 C006 -176.6(2) . . . . ?
C00B C00E C00F N003 -178.1(2) . . . . ?
C00B C00E C00F C00J 0.7(4) . . . . ?
C00B C00G C00K C00J 1.3(4) . . . . ?
C00D C007 C00A C006 0.9(4) . . . . ?
C00D C007 C00H C00O -176.4(3) . . . . ?
C00D C007 C00H C00P -56.2(4) . . . . ?
C00D C007 C00H C00Q 63.5(4) . . . . ?
C00D C007 C00H C00R 122.8(10) . . . . ?
C00D C007 C00H C1 -122.9(11) . . . . ?
C00D C007 C00H C2 5.9(15) . . . . ?
C00D C00C C00I C00L 120.4(3) . . . . ?
C00D C00C C00I C00M -118.5(3) . . . . ?
C00D C00C C00I C00N 0.3(4) . . . . ?
C00E C00B C00G C00K -1.6(4) . . . . ?
C00E C00F C00J C00K -0.9(4) . . . . ?
C00F C00J C00K C00G -0.1(4) . . . . ?
C00G C00B C00E C00F 0.6(4) . . . . ?
C00H C007 C00A C006 -179.4(2) . . . . ?
C00H C007 C00D C00C 179.9(2) . . . . ?
C00I C00C C00D C007 179.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_15point2degC
_database_code_depnum_ccdc_archive 'CCDC 2291944'
loop_
_audit_author_name
_audit_author_address
'Shodai Hasebe'
;Waseda University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_15point2degC        
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: This is because we input the calibrated true temperature manually after measurement. Note that the temperature difference between the default temperature (293K) and the true temperature is <40K.
;
# Added during the CSD deposition process: Thursday 31 August 2023 06:53 AM
# end Validation Reply Form

_audit_creation_date             2022-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0419(6)
_cell_length_b                   10.3191(11)
_cell_length_c                   16.7479(18)
_cell_angle_alpha                101.248(7)
_cell_angle_beta                 92.177(6)
_cell_angle_gamma                101.546(7)
_cell_volume                     1000.17(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7890
_cell_measurement_temperature    288.35
_cell_measurement_theta_max      68
_cell_measurement_theta_min      4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.6147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR(Rigaku,1995)
_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    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11123
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.233
_diffrn_reflns_theta_min         4.470
_diffrn_ambient_temperature      288.35
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2058
_reflns_number_total             3575
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0745
_refine_ls_restrained_S_all      1.088
_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)+(0.0722P)²+0.1851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1729
_refine_ls_wR_factor_ref         0.1950
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C00I \\sim C2 \\sim C00R \\sim C1: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C00Q \\sim C00I \\sim C00P \\sim C00O: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 C00I, C2, C00R, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00I, C00P, C00O, C00Q
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=
 Sof(C00R)=Sof(H00Y)=Sof(H)=Sof(HA)=1-FVAR(1)
 Sof(C00O)=Sof(H00P)=Sof(H00Q)=Sof(H00R)=Sof(C00P)=Sof(H00S)=Sof(H00T)=
 Sof(H00U)=Sof(C00Q)=Sof(H00V)=Sof(H00W)=Sof(H00X)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00B(H00B), C00F(H00F), C00G(H00G), C00J(H00J),
 C00K(H00K)
5.b Idealised Me refined as rotating group:
 C00L(H00C,H00D,H00E), C00M(H00H,H00I,H00L), C00N(H00M,H00N,H00O), C00O(H00P,
 H00Q,H00R), C00P(H00S,H00T,H00U), C00Q(H00V,H00W,H00X), C1(H1A,H1B,H1C),
 C2(H2A,H2B,H2C), C00R(H00Y,H,HA)
5.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 0.3512(4) 0.39759(18) 0.31623(12) 0.0745(6) Uani 1 1 d . . . . .
H001 H 0.2742 0.4416 0.3451 0.112 Uiso 1 1 calc R U . . .
N002 N 0.1890(4) 0.6058(2) 0.38112(14) 0.0660(6) Uani 1 1 d . . . . .
N003 N 0.1541(6) 0.9872(3) 0.60144(16) 0.0829(8) Uani 1 1 d . . . . .
O004 O 0.3561(5) 1.0294(3) 0.59793(16) 0.1148(9) Uani 1 1 d . . . . .
O005 O 0.0381(5) 1.0450(2) 0.64803(15) 0.1144(9) Uani 1 1 d . . . . .
C006 C 0.4431(5) 0.6092(3) 0.27434(15) 0.0587(7) Uani 1 1 d . . . . .
C007 C 0.4611(5) 0.4737(3) 0.26645(16) 0.0588(7) Uani 1 1 d . . . . .
C008 C 0.3061(5) 0.6699(3) 0.33342(16) 0.0640(7) Uani 1 1 d . . . . .
H008 H 0.3027 0.7606 0.3370 0.077 Uiso 1 1 calc R U . . .
C009 C 0.6912(5) 0.6361(3) 0.16601(16) 0.0592(7) Uani 1 1 d . . . . .
C00A C 0.1693(5) 0.7988(3) 0.48978(16) 0.0643(8) Uani 1 1 d . . . . .
H00A H 0.3179 0.8404 0.4845 0.077 Uiso 1 1 calc R U . . .
C00B C 0.5602(5) 0.6871(3) 0.22407(16) 0.0616(7) Uani 1 1 d . . . . .
H00B H 0.5490 0.7770 0.2301 0.074 Uiso 1 1 calc R U . . .
C00C C 0.0696(5) 0.6757(3) 0.44010(16) 0.0612(7) Uani 1 1 d . . . . .
C00D C 0.0432(5) 0.8583(3) 0.54731(16) 0.0638(8) Uani 1 1 d . . . . .
C00E C 0.5953(5) 0.4169(3) 0.20910(16) 0.0588(7) Uani 1 1 d . . . . .
C00F C 0.7045(5) 0.5003(3) 0.16077(15) 0.0613(7) Uani 1 1 d . . . . .
H00F H 0.7933 0.4638 0.1219 0.074 Uiso 1 1 calc R U . . .
C00G C -0.1522(5) 0.6158(3) 0.44991(17) 0.0698(8) Uani 1 1 d . . . . .
H00G H -0.2189 0.5321 0.4175 0.084 Uiso 1 1 calc R U . . .
C00H C 0.6206(5) 0.2695(3) 0.20004(17) 0.0659(8) Uani 1 1 d . . . . .
C00I C 0.8189(5) 0.7186(3) 0.10957(17) 0.0656(8) Uani 1 1 d . U . . .
C00J C -0.1772(6) 0.8024(3) 0.55684(18) 0.0715(8) Uani 1 1 d . . . . .
H00J H -0.2589 0.8460 0.5955 0.086 Uiso 1 1 calc R U . . .
C00K C -0.2738(5) 0.6792(3) 0.50718(19) 0.0766(9) Uani 1 1 d . . . . .
H00K H -0.4229 0.6387 0.5125 0.092 Uiso 1 1 calc R U . . .
C00L C 0.3888(5) 0.1726(3) 0.1780(2) 0.0873(10) Uani 1 1 d . . . . .
H00C H 0.2905 0.1918 0.2205 0.131 Uiso 1 1 calc R U . . .
H00D H 0.4073 0.0811 0.1724 0.131 Uiso 1 1 calc R U . . .
H00E H 0.3236 0.1843 0.1274 0.131 Uiso 1 1 calc R U . . .
C00M C 0.7277(5) 0.2490(3) 0.28001(19) 0.0875(10) Uani 1 1 d . . . . .
H00H H 0.8728 0.3096 0.2936 0.131 Uiso 1 1 calc R U . . .
H00I H 0.7465 0.1574 0.2733 0.131 Uiso 1 1 calc R U . . .
H00L H 0.6307 0.2671 0.3231 0.131 Uiso 1 1 calc R U . . .
C00N C 0.7751(6) 0.2323(3) 0.1328(2) 0.0946(11) Uani 1 1 d . . . . .
H00M H 0.7101 0.2410 0.0814 0.142 Uiso 1 1 calc R U . . .
H00N H 0.7909 0.1408 0.1296 0.142 Uiso 1 1 calc R U . . .
H00O H 0.9215 0.2920 0.1452 0.142 Uiso 1 1 calc R U . . .
C00O C 0.7713(9) 0.8596(4) 0.1208(3) 0.1043(19) Uani 0.811(5) 1 d . U P A 1
H00P H 0.6118 0.8534 0.1105 0.156 Uiso 0.811(5) 1 calc R U P A 1
H00Q H 0.8527 0.9069 0.0833 0.156 Uiso 0.811(5) 1 calc R U P A 1
H00R H 0.8193 0.9078 0.1757 0.156 Uiso 0.811(5) 1 calc R U P A 1
C00P C 0.7485(9) 0.6472(4) 0.0203(2) 0.0983(17) Uani 0.811(5) 1 d . U P A 1
H00S H 0.7788 0.5578 0.0114 0.148 Uiso 0.811(5) 1 calc R U P A 1
H00T H 0.8331 0.6976 -0.0151 0.148 Uiso 0.811(5) 1 calc R U P A 1
H00U H 0.5895 0.6413 0.0088 0.148 Uiso 0.811(5) 1 calc R U P A 1
C00Q C 1.0724(7) 0.7311(6) 0.1259(3) 0.1075(18) Uani 0.811(5) 1 d . U P A 1
H00V H 1.1192 0.7783 0.1812 0.161 Uiso 0.811(5) 1 calc R U P A 1
H00W H 1.1524 0.7803 0.0890 0.161 Uiso 0.811(5) 1 calc R U P A 1
H00X H 1.1057 0.6425 0.1180 0.161 Uiso 0.811(5) 1 calc R U P A 1
C1 C 0.967(4) 0.646(2) 0.0541(14) 0.103(6) Uani 0.189(5) 1 d . U P A 2
H1A H 1.0679 0.6115 0.0863 0.155 Uiso 0.189(5) 1 calc R U P A 2
H1B H 1.0540 0.7074 0.0252 0.155 Uiso 0.189(5) 1 calc R U P A 2
H1C H 0.8736 0.5720 0.0157 0.155 Uiso 0.189(5) 1 calc R U P A 2
C2 C 0.646(3) 0.773(2) 0.0614(12) 0.089(5) Uani 0.189(5) 1 d . U P A 2
H2A H 0.5381 0.6986 0.0291 0.134 Uiso 0.189(5) 1 calc R U P A 2
H2B H 0.7251 0.8268 0.0263 0.134 Uiso 0.189(5) 1 calc R U P A 2
H2C H 0.5692 0.8278 0.0990 0.134 Uiso 0.189(5) 1 calc R U P A 2
C00R C 0.988(3) 0.8501(18) 0.1658(11) 0.085(5) Uani 0.189(5) 1 d . U P A 2
H00Y H 0.9003 0.9052 0.1982 0.127 Uiso 0.189(5) 1 calc R U P A 2
H H 1.0746 0.9015 0.1313 0.127 Uiso 0.189(5) 1 calc R U P A 2
HA H 1.0885 0.8210 0.2010 0.127 Uiso 0.189(5) 1 calc R U P A 2


_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 H001 0.8200 . ?
O001 C007 1.357(3) . ?
N002 C008 1.280(3) . ?
N002 C00C 1.415(3) . ?
N003 O004 1.218(3) . ?
N003 O005 1.218(3) . ?
N003 C00D 1.472(4) . ?
C006 C007 1.406(3) . ?
C006 C008 1.444(3) . ?
C006 C00B 1.392(3) . ?
C007 C00E 1.398(3) . ?
C008 H008 0.9300 . ?
C009 C00B 1.369(3) . ?
C009 C00F 1.405(3) . ?
C009 C00I 1.523(3) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.383(4) . ?
C00A C00D 1.378(4) . ?
C00B H00B 0.9300 . ?
C00C C00G 1.389(4) . ?
C00D C00J 1.370(4) . ?
C00E C00F 1.385(3) . ?
C00E C00H 1.537(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00K 1.375(4) . ?
C00H C00L 1.534(4) . ?
C00H C00M 1.535(4) . ?
C00H C00N 1.530(4) . ?
C00I C00O 1.516(4) . ?
C00I C00P 1.535(5) . ?
C00I C00Q 1.521(5) . ?
C00I C1 1.513(18) . ?
C00I C2 1.549(18) . ?
C00I C00R 1.625(17) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.379(4) . ?
C00K H00K 0.9300 . ?
C00L H00C 0.9600 . ?
C00L H00D 0.9600 . ?
C00L H00E 0.9600 . ?
C00M H00H 0.9600 . ?
C00M H00I 0.9600 . ?
C00M H00L 0.9600 . ?
C00N H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?
C00O H00P 0.9600 . ?
C00O H00Q 0.9600 . ?
C00O H00R 0.9600 . ?
C00P H00S 0.9600 . ?
C00P H00T 0.9600 . ?
C00P H00U 0.9600 . ?
C00Q H00V 0.9600 . ?
C00Q H00W 0.9600 . ?
C00Q H00X 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C00R H00Y 0.9600 . ?
C00R H 0.9600 . ?
C00R HA 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
C007 O001 H001 109.5 . . ?
C008 N002 C00C 119.6(2) . . ?
O004 N003 C00D 118.6(3) . . ?
O005 N003 O004 123.7(3) . . ?
O005 N003 C00D 117.7(3) . . ?
C007 C006 C008 121.6(2) . . ?
C00B C006 C007 119.3(2) . . ?
C00B C006 C008 119.1(2) . . ?
O001 C007 C006 119.8(2) . . ?
O001 C007 C00E 119.4(2) . . ?
C00E C007 C006 120.8(2) . . ?
N002 C008 C006 123.6(3) . . ?
N002 C008 H008 118.2 . . ?
C006 C008 H008 118.2 . . ?
C00B C009 C00F 116.1(2) . . ?
C00B C009 C00I 123.5(2) . . ?
C00F C009 C00I 120.4(2) . . ?
C00C C00A H00A 120.8 . . ?
C00D C00A H00A 120.8 . . ?
C00D C00A C00C 118.4(3) . . ?
C006 C00B H00B 118.8 . . ?
C009 C00B C006 122.4(2) . . ?
C009 C00B H00B 118.8 . . ?
C00A C00C N002 122.0(3) . . ?
C00A C00C C00G 119.4(3) . . ?
C00G C00C N002 118.5(3) . . ?
C00A C00D N003 117.7(3) . . ?
C00J C00D N003 119.1(3) . . ?
C00J C00D C00A 123.2(3) . . ?
C007 C00E C00H 121.8(2) . . ?
C00F C00E C007 116.5(2) . . ?
C00F C00E C00H 121.7(2) . . ?
C009 C00F H00F 117.5 . . ?
C00E C00F C009 124.9(3) . . ?
C00E C00F H00F 117.5 . . ?
C00C C00G H00G 119.7 . . ?
C00K C00G C00C 120.5(3) . . ?
C00K C00G H00G 119.7 . . ?
C00L C00H C00E 110.4(2) . . ?
C00L C00H C00M 109.6(2) . . ?
C00M C00H C00E 110.0(2) . . ?
C00N C00H C00E 111.4(2) . . ?
C00N C00H C00L 107.9(3) . . ?
C00N C00H C00M 107.3(2) . . ?
C009 C00I C00P 109.6(3) . . ?
C009 C00I C2 108.6(6) . . ?
C009 C00I C00R 108.2(6) . . ?
C00O C00I C009 112.5(3) . . ?
C00O C00I C00P 107.8(3) . . ?
C00O C00I C00Q 108.5(3) . . ?
C00Q C00I C009 109.6(3) . . ?
C00Q C00I C00P 108.8(3) . . ?
C1 C00I C009 114.8(7) . . ?
C1 C00I C2 112.4(12) . . ?
C1 C00I C00R 106.1(12) . . ?
C2 C00I C00R 106.5(11) . . ?
C00D C00J H00J 121.1 . . ?
C00D C00J C00K 117.7(3) . . ?
C00K C00J H00J 121.1 . . ?
C00G C00K C00J 120.8(3) . . ?
C00G C00K H00K 119.6 . . ?
C00J C00K H00K 119.6 . . ?
C00H C00L H00C 109.5 . . ?
C00H C00L H00D 109.5 . . ?
C00H C00L H00E 109.5 . . ?
H00C C00L H00D 109.5 . . ?
H00C C00L H00E 109.5 . . ?
H00D C00L H00E 109.5 . . ?
C00H C00M H00H 109.5 . . ?
C00H C00M H00I 109.5 . . ?
C00H C00M H00L 109.5 . . ?
H00H C00M H00I 109.5 . . ?
H00H C00M H00L 109.5 . . ?
H00I C00M H00L 109.5 . . ?
C00H C00N H00M 109.5 . . ?
C00H C00N H00N 109.5 . . ?
C00H C00N H00O 109.5 . . ?
H00M C00N H00N 109.5 . . ?
H00M C00N H00O 109.5 . . ?
H00N C00N H00O 109.5 . . ?
C00I C00O H00P 109.5 . . ?
C00I C00O H00Q 109.5 . . ?
C00I C00O H00R 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
H00P C00O H00R 109.5 . . ?
H00Q C00O H00R 109.5 . . ?
C00I C00P H00S 109.5 . . ?
C00I C00P H00T 109.5 . . ?
C00I C00P H00U 109.5 . . ?
H00S C00P H00T 109.5 . . ?
H00S C00P H00U 109.5 . . ?
H00T C00P H00U 109.5 . . ?
C00I C00Q H00V 109.5 . . ?
C00I C00Q H00W 109.5 . . ?
C00I C00Q H00X 109.5 . . ?
H00V C00Q H00W 109.5 . . ?
H00V C00Q H00X 109.5 . . ?
H00W C00Q H00X 109.5 . . ?
C00I C1 H1A 109.5 . . ?
C00I C1 H1B 109.5 . . ?
C00I C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00I C2 H2A 109.5 . . ?
C00I C2 H2B 109.5 . . ?
C00I C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C00I C00R H00Y 109.5 . . ?
C00I C00R H 109.5 . . ?
C00I C00R HA 109.5 . . ?
H00Y C00R H 109.5 . . ?
H00Y C00R HA 109.5 . . ?
H C00R HA 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 C007 C00E C00F -179.4(2) . . . . ?
O001 C007 C00E C00H 0.6(4) . . . . ?
N002 C00C C00G C00K 179.2(2) . . . . ?
N003 C00D C00J C00K -177.7(2) . . . . ?
O004 N003 C00D C00A -6.2(4) . . . . ?
O004 N003 C00D C00J 172.9(3) . . . . ?
O005 N003 C00D C00A 174.5(3) . . . . ?
O005 N003 C00D C00J -6.4(4) . . . . ?
C006 C007 C00E C00F -0.9(4) . . . . ?
C006 C007 C00E C00H 179.1(2) . . . . ?
C007 C006 C008 N002 -1.4(4) . . . . ?
C007 C006 C00B C009 0.8(4) . . . . ?
C007 C00E C00F C009 0.6(4) . . . . ?
C007 C00E C00H C00L 59.7(3) . . . . ?
C007 C00E C00H C00M -61.4(4) . . . . ?
C007 C00E C00H C00N 179.7(3) . . . . ?
C008 N002 C00C C00A -46.9(4) . . . . ?
C008 N002 C00C C00G 135.4(3) . . . . ?
C008 C006 C007 O001 -1.2(4) . . . . ?
C008 C006 C007 C00E -179.8(2) . . . . ?
C008 C006 C00B C009 -179.2(2) . . . . ?
C00A C00C C00G C00K 1.4(4) . . . . ?
C00A C00D C00J C00K 1.4(4) . . . . ?
C00B C006 C007 O001 178.7(2) . . . . ?
C00B C006 C007 C00E 0.2(4) . . . . ?
C00B C006 C008 N002 178.6(3) . . . . ?
C00B C009 C00F C00E 0.3(4) . . . . ?
C00B C009 C00I C00O -4.1(4) . . . . ?
C00B C009 C00I C00P -124.0(3) . . . . ?
C00B C009 C00I C00Q 116.7(4) . . . . ?
C00B C009 C00I C1 175.7(12) . . . . ?
C00B C009 C00I C2 -57.6(10) . . . . ?
C00B C009 C00I C00R 57.5(9) . . . . ?
C00C N002 C008 C006 176.6(2) . . . . ?
C00C C00A C00D N003 178.1(2) . . . . ?
C00C C00A C00D C00J -1.0(4) . . . . ?
C00C C00G C00K C00J -1.0(4) . . . . ?
C00D C00A C00C N002 -178.1(2) . . . . ?
C00D C00A C00C C00G -0.4(4) . . . . ?
C00D C00J C00K C00G -0.3(4) . . . . ?
C00F C009 C00B C006 -1.1(4) . . . . ?
C00F C009 C00I C00O 176.3(3) . . . . ?
C00F C009 C00I C00P 56.3(4) . . . . ?
C00F C009 C00I C00Q -62.9(4) . . . . ?
C00F C009 C00I C1 -3.9(13) . . . . ?
C00F C009 C00I C2 122.7(10) . . . . ?
C00F C009 C00I C00R -122.1(8) . . . . ?
C00F C00E C00H C00L -120.3(3) . . . . ?
C00F C00E C00H C00M 118.6(3) . . . . ?
C00F C00E C00H C00N -0.3(4) . . . . ?
C00H C00E C00F C009 -179.4(2) . . . . ?
C00I C009 C00B C006 179.3(3) . . . . ?
C00I C009 C00F C00E 180.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_23point6degC
_database_code_depnum_ccdc_archive 'CCDC 2291945'
loop_
_audit_author_name
_audit_author_address
'Shodai Hasebe'
;Waseda University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_23point6degC        
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: This is because we input the calibrated true temperature manually after measurement. Note that the temperature difference between the default temperature (293K) and the true temperature is <40K.
;
# Added during the CSD deposition process: Thursday 31 August 2023 06:53 AM
# end Validation Reply Form

_audit_creation_date             2022-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0399(7)
_cell_length_b                   10.3202(11)
_cell_length_c                   16.7772(18)
_cell_angle_alpha                101.178(7)
_cell_angle_beta                 92.181(6)
_cell_angle_gamma                101.469(7)
_cell_volume                     1002.25(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7707
_cell_measurement_temperature    296.75
_cell_measurement_theta_max      68
_cell_measurement_theta_min      4
_shelx_estimated_absorpt_T_max   1
_shelx_estimated_absorpt_T_min   0.624
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.6204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR(Rigaku,1995)
_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    1.174
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11147
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.105
_diffrn_reflns_theta_min         4.467
_diffrn_ambient_temperature      296.75
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2031
_reflns_number_total             3581
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3581
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0797
_refine_ls_restrained_S_all      1.152
_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)+(0.0650P)²+0.2154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1820
_refine_ls_wR_factor_ref         0.2019
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C00I \\sim C00O \\sim C00P \\sim C00Q: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
C00I \\sim C1 \\sim C00R \\sim C2: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 C00I, C00P, C00O, C00Q
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00I, C1, C00R, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=
 Sof(C00R)=Sof(H00Y)=Sof(H)=Sof(HA)=1-FVAR(1)
 Sof(C00O)=Sof(H00P)=Sof(H00Q)=Sof(H00R)=Sof(C00P)=Sof(H00S)=Sof(H00T)=
 Sof(H00U)=Sof(C00Q)=Sof(H00V)=Sof(H00W)=Sof(H00X)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00G), C00J(H00J),
 C00K(H00K)
5.b Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00F), C00M(H00H,H00I,H00L), C00N(H00M,H00N,H00O), C00O(H00P,
 H00Q,H00R), C00P(H00S,H00T,H00U), C00Q(H00V,H00W,H00X), C1(H1A,H1B,H1C),
 C2(H2A,H2B,H2C), C00R(H00Y,H,HA)
5.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 0.3523(4) 0.3982(2) 0.31641(13) 0.0769(7) Uani 1 1 d . . . . .
H001 H 0.2759 0.4422 0.3456 0.115 Uiso 1 1 calc R U . . .
N002 N 0.1896(4) 0.6061(2) 0.38120(15) 0.0684(7) Uani 1 1 d . . . . .
N003 N 0.1544(6) 0.9867(3) 0.60122(18) 0.0857(9) Uani 1 1 d . . . . .
O004 O 0.3558(5) 1.0291(3) 0.59768(17) 0.1192(10) Uani 1 1 d . . . . .
O005 O 0.0385(5) 1.0447(3) 0.64778(17) 0.1182(10) Uani 1 1 d . . . . .
C006 C 0.4615(5) 0.4743(3) 0.26664(17) 0.0609(8) Uani 1 1 d . . . . .
C007 C 0.4433(5) 0.6096(3) 0.27441(16) 0.0605(8) Uani 1 1 d . . . . .
C008 C 0.6911(5) 0.6367(3) 0.16613(17) 0.0616(8) Uani 1 1 d . . . . .
C009 C 0.3062(5) 0.6704(3) 0.33352(17) 0.0665(8) Uani 1 1 d . . . . .
H009 H 0.3026 0.7610 0.3371 0.080 Uiso 1 1 calc R U . . .
C00A C 0.5959(5) 0.4175(3) 0.20939(17) 0.0612(8) Uani 1 1 d . . . . .
C00B C 0.0698(5) 0.6757(3) 0.44009(17) 0.0632(8) Uani 1 1 d . . . . .
C00C C 0.5597(5) 0.6876(3) 0.22409(17) 0.0640(8) Uani 1 1 d . . . . .
H00C H 0.5479 0.7774 0.2300 0.077 Uiso 1 1 calc R U . . .
C00D C 0.1699(5) 0.7985(3) 0.48959(18) 0.0663(8) Uani 1 1 d . . . . .
H00D H 0.3186 0.8399 0.4843 0.080 Uiso 1 1 calc R U . . .
C00E C 0.7044(5) 0.5012(3) 0.16097(17) 0.0636(8) Uani 1 1 d . . . . .
H00E H 0.7928 0.4646 0.1221 0.076 Uiso 1 1 calc R U . . .
C00F C 0.0434(6) 0.8580(3) 0.54702(18) 0.0665(8) Uani 1 1 d . . . . .
C00G C -0.1515(6) 0.6163(3) 0.45000(19) 0.0727(9) Uani 1 1 d . . . . .
H00G H -0.2183 0.5328 0.4176 0.087 Uiso 1 1 calc R U . . .
C00H C 0.6216(5) 0.2703(3) 0.20028(19) 0.0685(8) Uani 1 1 d . . . . .
C00I C 0.8177(6) 0.7192(3) 0.10974(18) 0.0683(8) Uani 1 1 d . U . . .
C00J C -0.1763(6) 0.8023(4) 0.55682(19) 0.0749(9) Uani 1 1 d . . . . .
H00J H -0.2577 0.8458 0.5956 0.090 Uiso 1 1 calc R U . . .
C00K C -0.2734(6) 0.6793(4) 0.5072(2) 0.0798(10) Uani 1 1 d . . . . .
H00K H -0.4226 0.6388 0.5124 0.096 Uiso 1 1 calc R U . . .
C00L C 0.3899(6) 0.1734(3) 0.1786(2) 0.0909(11) Uani 1 1 d . . . . .
H00A H 0.2919 0.1925 0.2211 0.136 Uiso 1 1 calc R U . . .
H00B H 0.4087 0.0820 0.1730 0.136 Uiso 1 1 calc R U . . .
H00F H 0.3242 0.1852 0.1282 0.136 Uiso 1 1 calc R U . . .
C00M C 0.7291(6) 0.2497(3) 0.2801(2) 0.0903(11) Uani 1 1 d . . . . .
H00H H 0.8745 0.3098 0.2934 0.135 Uiso 1 1 calc R U . . .
H00I H 0.7472 0.1580 0.2736 0.135 Uiso 1 1 calc R U . . .
H00L H 0.6326 0.2682 0.3232 0.135 Uiso 1 1 calc R U . . .
C00N C 0.7764(6) 0.2334(3) 0.1333(2) 0.0974(12) Uani 1 1 d . . . . .
H00M H 0.7104 0.2408 0.0818 0.146 Uiso 1 1 calc R U . . .
H00N H 0.7942 0.1423 0.1307 0.146 Uiso 1 1 calc R U . . .
H00O H 0.9219 0.2938 0.1453 0.146 Uiso 1 1 calc R U . . .
C00O C 0.7693(11) 0.8597(5) 0.1209(4) 0.110(2) Uani 0.793(6) 1 d . U P A 1
H00P H 0.6100 0.8534 0.1096 0.165 Uiso 0.793(6) 1 calc R U P A 1
H00Q H 0.8526 0.9077 0.0841 0.165 Uiso 0.793(6) 1 calc R U P A 1
H00R H 0.8146 0.9073 0.1760 0.165 Uiso 0.793(6) 1 calc R U P A 1
C00P C 0.7458(10) 0.6479(5) 0.0209(3) 0.1009(19) Uani 0.793(6) 1 d . U P A 1
H00S H 0.7749 0.5583 0.0120 0.151 Uiso 0.793(6) 1 calc R U P A 1
H00T H 0.8306 0.6979 -0.0147 0.151 Uiso 0.793(6) 1 calc R U P A 1
H00U H 0.5870 0.6430 0.0097 0.151 Uiso 0.793(6) 1 calc R U P A 1
C00Q C 1.0708(8) 0.7312(6) 0.1258(4) 0.114(2) Uani 0.793(6) 1 d . U P A 1
H00V H 1.1172 0.7762 0.1813 0.171 Uiso 0.793(6) 1 calc R U P A 1
H00W H 1.1508 0.7824 0.0898 0.171 Uiso 0.793(6) 1 calc R U P A 1
H00X H 1.1043 0.6427 0.1165 0.171 Uiso 0.793(6) 1 calc R U P A 1
C1 C 0.645(3) 0.776(2) 0.0617(12) 0.093(5) Uani 0.207(6) 1 d . U P A 2
H1A H 0.5369 0.7027 0.0288 0.139 Uiso 0.207(6) 1 calc R U P A 2
H1B H 0.7250 0.8308 0.0273 0.139 Uiso 0.207(6) 1 calc R U P A 2
H1C H 0.5678 0.8304 0.0995 0.139 Uiso 0.207(6) 1 calc R U P A 2
C2 C 0.988(3) 0.8513(18) 0.1659(10) 0.089(5) Uani 0.207(6) 1 d . U P A 2
H2A H 0.9000 0.9079 0.1971 0.133 Uiso 0.207(6) 1 calc R U P A 2
H2B H 1.0773 0.9012 0.1314 0.133 Uiso 0.207(6) 1 calc R U P A 2
H2C H 1.0857 0.8224 0.2021 0.133 Uiso 0.207(6) 1 calc R U P A 2
C00R C 0.964(4) 0.646(2) 0.0533(14) 0.108(6) Uani 0.207(6) 1 d . U P A 2
H00Y H 1.0781 0.6213 0.0850 0.162 Uiso 0.207(6) 1 calc R U P A 2
H H 1.0344 0.7043 0.0192 0.162 Uiso 0.207(6) 1 calc R U P A 2
HA H 0.8707 0.5662 0.0199 0.162 Uiso 0.207(6) 1 calc R U P A 2


_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 H001 0.8200 . ?
O001 C006 1.357(3) . ?
N002 C009 1.280(3) . ?
N002 C00B 1.415(3) . ?
N003 O004 1.216(4) . ?
N003 O005 1.218(3) . ?
N003 C00F 1.474(4) . ?
C006 C007 1.403(4) . ?
C006 C00A 1.398(4) . ?
C007 C009 1.446(4) . ?
C007 C00C 1.393(4) . ?
C008 C00C 1.370(4) . ?
C008 C00E 1.404(4) . ?
C008 C00I 1.521(4) . ?
C009 H009 0.9300 . ?
C00A C00E 1.386(3) . ?
C00A C00H 1.536(4) . ?
C00B C00D 1.382(4) . ?
C00B C00G 1.386(4) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00F 1.379(4) . ?
C00E H00E 0.9300 . ?
C00F C00J 1.367(4) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.374(4) . ?
C00H C00L 1.535(4) . ?
C00H C00M 1.536(4) . ?
C00H C00N 1.529(4) . ?
C00I C00O 1.513(5) . ?
C00I C00P 1.534(5) . ?
C00I C00Q 1.518(5) . ?
C00I C1 1.564(18) . ?
C00I C2 1.634(17) . ?
C00I C00R 1.515(18) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.380(4) . ?
C00K H00K 0.9300 . ?
C00L H00A 0.9600 . ?
C00L H00B 0.9600 . ?
C00L H00F 0.9600 . ?
C00M H00H 0.9600 . ?
C00M H00I 0.9600 . ?
C00M H00L 0.9600 . ?
C00N H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?
C00O H00P 0.9600 . ?
C00O H00Q 0.9600 . ?
C00O H00R 0.9600 . ?
C00P H00S 0.9600 . ?
C00P H00T 0.9600 . ?
C00P H00U 0.9600 . ?
C00Q H00V 0.9600 . ?
C00Q H00W 0.9600 . ?
C00Q H00X 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C00R H00Y 0.9600 . ?
C00R H 0.9600 . ?
C00R HA 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 H001 109.5 . . ?
C009 N002 C00B 119.5(3) . . ?
O004 N003 O005 123.5(3) . . ?
O004 N003 C00F 118.7(3) . . ?
O005 N003 C00F 117.8(3) . . ?
O001 C006 C007 119.9(3) . . ?
O001 C006 C00A 119.3(3) . . ?
C00A C006 C007 120.8(3) . . ?
C006 C007 C009 121.7(3) . . ?
C00C C007 C006 119.4(3) . . ?
C00C C007 C009 118.9(3) . . ?
C00C C008 C00E 116.0(3) . . ?
C00C C008 C00I 123.4(3) . . ?
C00E C008 C00I 120.6(3) . . ?
N002 C009 C007 123.4(3) . . ?
N002 C009 H009 118.3 . . ?
C007 C009 H009 118.3 . . ?
C006 C00A C00H 122.0(3) . . ?
C00E C00A C006 116.3(3) . . ?
C00E C00A C00H 121.7(3) . . ?
C00D C00B N002 121.8(3) . . ?
C00D C00B C00G 119.4(3) . . ?
C00G C00B N002 118.7(3) . . ?
C007 C00C H00C 118.8 . . ?
C008 C00C C007 122.3(3) . . ?
C008 C00C H00C 118.8 . . ?
C00B C00D H00D 120.9 . . ?
C00F C00D C00B 118.2(3) . . ?
C00F C00D H00D 120.9 . . ?
C008 C00E H00E 117.5 . . ?
C00A C00E C008 125.1(3) . . ?
C00A C00E H00E 117.5 . . ?
C00D C00F N003 117.7(3) . . ?
C00J C00F N003 119.0(3) . . ?
C00J C00F C00D 123.3(3) . . ?
C00B C00G H00G 119.6 . . ?
C00K C00G C00B 120.8(3) . . ?
C00K C00G H00G 119.6 . . ?
C00A C00H C00M 110.0(3) . . ?
C00L C00H C00A 110.4(3) . . ?
C00L C00H C00M 109.5(3) . . ?
C00N C00H C00A 111.5(2) . . ?
C00N C00H C00L 108.1(3) . . ?
C00N C00H C00M 107.2(3) . . ?
C008 C00I C00P 109.4(3) . . ?
C008 C00I C1 109.2(7) . . ?
C008 C00I C2 108.2(6) . . ?
C00O C00I C008 112.5(3) . . ?
C00O C00I C00P 107.7(4) . . ?
C00O C00I C00Q 108.8(4) . . ?
C00Q C00I C008 109.4(3) . . ?
C00Q C00I C00P 109.0(4) . . ?
C1 C00I C2 105.7(11) . . ?
C00R C00I C008 114.9(7) . . ?
C00R C00I C1 111.8(12) . . ?
C00R C00I C2 106.6(12) . . ?
C00F C00J H00J 121.1 . . ?
C00F C00J C00K 117.7(3) . . ?
C00K C00J H00J 121.1 . . ?
C00G C00K C00J 120.6(3) . . ?
C00G C00K H00K 119.7 . . ?
C00J C00K H00K 119.7 . . ?
C00H C00L H00A 109.5 . . ?
C00H C00L H00B 109.5 . . ?
C00H C00L H00F 109.5 . . ?
H00A C00L H00B 109.5 . . ?
H00A C00L H00F 109.5 . . ?
H00B C00L H00F 109.5 . . ?
C00H C00M H00H 109.5 . . ?
C00H C00M H00I 109.5 . . ?
C00H C00M H00L 109.5 . . ?
H00H C00M H00I 109.5 . . ?
H00H C00M H00L 109.5 . . ?
H00I C00M H00L 109.5 . . ?
C00H C00N H00M 109.5 . . ?
C00H C00N H00N 109.5 . . ?
C00H C00N H00O 109.5 . . ?
H00M C00N H00N 109.5 . . ?
H00M C00N H00O 109.5 . . ?
H00N C00N H00O 109.5 . . ?
C00I C00O H00P 109.5 . . ?
C00I C00O H00Q 109.5 . . ?
C00I C00O H00R 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
H00P C00O H00R 109.5 . . ?
H00Q C00O H00R 109.5 . . ?
C00I C00P H00S 109.5 . . ?
C00I C00P H00T 109.5 . . ?
C00I C00P H00U 109.5 . . ?
H00S C00P H00T 109.5 . . ?
H00S C00P H00U 109.5 . . ?
H00T C00P H00U 109.5 . . ?
C00I C00Q H00V 109.5 . . ?
C00I C00Q H00W 109.5 . . ?
C00I C00Q H00X 109.5 . . ?
H00V C00Q H00W 109.5 . . ?
H00V C00Q H00X 109.5 . . ?
H00W C00Q H00X 109.5 . . ?
C00I C1 H1A 109.5 . . ?
C00I C1 H1B 109.5 . . ?
C00I C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00I C2 H2A 109.5 . . ?
C00I C2 H2B 109.5 . . ?
C00I C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C00I C00R H00Y 109.5 . . ?
C00I C00R H 109.5 . . ?
C00I C00R HA 109.5 . . ?
H00Y C00R H 109.5 . . ?
H00Y C00R HA 109.5 . . ?
H C00R HA 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_32point0degC
_database_code_depnum_ccdc_archive 'CCDC 2291946'
loop_
_audit_author_name
_audit_author_address
'Shodai Hasebe'
;Waseda University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_32point0degC        
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: This is because we input the calibrated true temperature manually after measurement. Note that the temperature difference between the default temperature (293K) and the true temperature is <40K.
;
# Added during the CSD deposition process: Thursday 31 August 2023 06:53 AM
# end Validation Reply Form

_audit_creation_date             2022-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0394(8)
_cell_length_b                   10.3207(13)
_cell_length_c                   16.801(2)
_cell_angle_alpha                101.124(7)
_cell_angle_beta                 92.180(6)
_cell_angle_gamma                101.408(7)
_cell_volume                     1004.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7456
_cell_measurement_temperature    305.15
_cell_measurement_theta_max      68.055
_cell_measurement_theta_min      4.465
_shelx_estimated_absorpt_T_max   1
_shelx_estimated_absorpt_T_min   0.6342
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.6342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR(Rigaku,1995)
_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    1.172
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11160
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.054
_diffrn_reflns_theta_min         4.465
_diffrn_ambient_temperature      305.15
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1930
_reflns_number_total             3586
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0802
_refine_ls_restrained_S_all      1.124
_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)+(0.0765P)²+0.1629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2133
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C00I \\sim C1 \\sim C00R \\sim C2: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C00Q \\sim C00P \\sim C00I \\sim C00O: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 C1, C00I, C00R, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00I, C00P, C00O, C00Q
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=
 Sof(C00R)=Sof(H00Y)=Sof(H)=Sof(HA)=1-FVAR(1)
 Sof(C00O)=Sof(H00P)=Sof(H00Q)=Sof(H00R)=Sof(C00P)=Sof(H00S)=Sof(H00T)=
 Sof(H00U)=Sof(C00Q)=Sof(H00V)=Sof(H00W)=Sof(H00X)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00G), C00J(H00J),
 C00K(H00K)
5.b Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00F), C00M(H00H,H00I,H00L), C00N(H00M,H00N,H00O), C00O(H00P,
 H00Q,H00R), C00P(H00S,H00T,H00U), C00Q(H00V,H00W,H00X), C1(H1A,H1B,H1C),
 C2(H2A,H2B,H2C), C00R(H00Y,H,HA)
5.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 0.3529(4) 0.3987(2) 0.31656(13) 0.0802(7) Uani 1 1 d . . . . .
H001 H 0.2763 0.4427 0.3455 0.120 Uiso 1 1 calc R U . . .
N002 N 0.1900(4) 0.6064(2) 0.38131(15) 0.0714(7) Uani 1 1 d . . . . .
N3 N 0.1547(7) 0.9865(3) 0.60114(18) 0.0894(9) Uani 1 1 d . . . . .
O004 O 0.3559(6) 1.0287(3) 0.59759(17) 0.1240(11) Uani 1 1 d . . . . .
O5 O 0.0387(5) 1.0443(3) 0.64756(17) 0.1224(10) Uani 1 1 d . . . . .
C006 C 0.4622(5) 0.4747(3) 0.26664(17) 0.0635(8) Uani 1 1 d . . . . .
C007 C 0.4436(5) 0.6098(3) 0.27450(16) 0.0635(8) Uani 1 1 d . . . . .
C008 C 0.3065(5) 0.6707(3) 0.33368(18) 0.0694(8) Uani 1 1 d . . . . .
H008 H 0.3029 0.7613 0.3373 0.083 Uiso 1 1 calc R U . . .
C009 C 0.6902(5) 0.6371(3) 0.16622(17) 0.0645(8) Uani 1 1 d . . . . .
C00A C 0.0705(6) 0.6760(3) 0.44007(18) 0.0661(8) Uani 1 1 d . . . . .
C00B C 0.5958(5) 0.4179(3) 0.20952(17) 0.0634(8) Uani 1 1 d . . . . .
C00C C 0.5591(5) 0.6879(3) 0.22418(17) 0.0669(8) Uani 1 1 d . . . . .
H00C H 0.5469 0.7777 0.2301 0.080 Uiso 1 1 calc R U . . .
C00D C 0.7040(5) 0.5016(3) 0.16112(17) 0.0664(8) Uani 1 1 d . . . . .
H00D H 0.7926 0.4651 0.1223 0.080 Uiso 1 1 calc R U . . .
C00E C 0.1700(5) 0.7986(3) 0.48949(18) 0.0686(8) Uani 1 1 d . . . . .
H00E H 0.3184 0.8401 0.4841 0.082 Uiso 1 1 calc R U . . .
C00F C 0.0441(6) 0.8580(3) 0.54707(18) 0.0695(9) Uani 1 1 d . . . . .
C00G C -0.1501(6) 0.6167(3) 0.45008(19) 0.0760(9) Uani 1 1 d . . . . .
H00G H -0.2166 0.5332 0.4177 0.091 Uiso 1 1 calc R U . . .
C00H C 0.6219(6) 0.2708(3) 0.20042(19) 0.0716(9) Uani 1 1 d . . . . .
C00I C 0.8167(6) 0.7196(3) 0.10968(18) 0.0720(9) Uani 1 1 d . U . . .
C00J C -0.1755(6) 0.8020(4) 0.55671(19) 0.0780(10) Uani 1 1 d . . . . .
H00J H -0.2569 0.8452 0.5955 0.094 Uiso 1 1 calc R U . . .
C00K C -0.2726(6) 0.6791(4) 0.5071(2) 0.0829(10) Uani 1 1 d . . . . .
H00K H -0.4217 0.6385 0.5124 0.099 Uiso 1 1 calc R U . . .
C00L C 0.3904(6) 0.1740(3) 0.1790(2) 0.0947(11) Uani 1 1 d . . . . .
H00A H 0.2924 0.1933 0.2214 0.142 Uiso 1 1 calc R U . . .
H00B H 0.4093 0.0826 0.1736 0.142 Uiso 1 1 calc R U . . .
H00F H 0.3246 0.1855 0.1285 0.142 Uiso 1 1 calc R U . . .
C00M C 0.7299(6) 0.2506(3) 0.2804(2) 0.0945(11) Uani 1 1 d . . . . .
H00H H 0.8751 0.3109 0.2935 0.142 Uiso 1 1 calc R U . . .
H00I H 0.7485 0.1591 0.2741 0.142 Uiso 1 1 calc R U . . .
H00L H 0.6334 0.2694 0.3234 0.142 Uiso 1 1 calc R U . . .
C00N C 0.7771(6) 0.2342(3) 0.1336(2) 0.1007(12) Uani 1 1 d . . . . .
H00M H 0.7122 0.2431 0.0823 0.151 Uiso 1 1 calc R U . . .
H00N H 0.7932 0.1426 0.1303 0.151 Uiso 1 1 calc R U . . .
H00O H 0.9231 0.2937 0.1460 0.151 Uiso 1 1 calc R U . . .
C00O C 0.7679(11) 0.8600(5) 0.1209(4) 0.116(2) Uani 0.780(6) 1 d . U P A 1
H00P H 0.8136 0.9074 0.1759 0.174 Uiso 0.780(6) 1 calc R U P A 1
H00Q H 0.6085 0.8536 0.1099 0.174 Uiso 0.780(6) 1 calc R U P A 1
H00R H 0.8505 0.9080 0.0841 0.174 Uiso 0.780(6) 1 calc R U P A 1
C00P C 0.7456(11) 0.6483(5) 0.0211(3) 0.106(2) Uani 0.780(6) 1 d . U P A 1
H00S H 0.8287 0.6989 -0.0145 0.160 Uiso 0.780(6) 1 calc R U P A 1
H00T H 0.5863 0.6418 0.0100 0.160 Uiso 0.780(6) 1 calc R U P A 1
H00U H 0.7774 0.5593 0.0122 0.160 Uiso 0.780(6) 1 calc R U P A 1
C00Q C 1.0698(9) 0.7315(7) 0.1258(4) 0.120(2) Uani 0.780(6) 1 d . U P A 1
H00V H 1.1033 0.6429 0.1169 0.179 Uiso 0.780(6) 1 calc R U P A 1
H00W H 1.1162 0.7769 0.1812 0.179 Uiso 0.780(6) 1 calc R U P A 1
H00X H 1.1500 0.7822 0.0897 0.179 Uiso 0.780(6) 1 calc R U P A 1
C1 C 0.644(3) 0.774(2) 0.0613(12) 0.097(5) Uani 0.220(6) 1 d . U P A 2
H1A H 0.7233 0.8303 0.0276 0.146 Uiso 0.220(6) 1 calc R U P A 2
H1B H 0.5628 0.8266 0.0987 0.146 Uiso 0.220(6) 1 calc R U P A 2
H1C H 0.5390 0.7000 0.0278 0.146 Uiso 0.220(6) 1 calc R U P A 2
C2 C 0.988(3) 0.8507(18) 0.1656(10) 0.093(5) Uani 0.220(6) 1 d . U P A 2
H2A H 1.0877 0.8209 0.2009 0.139 Uiso 0.220(6) 1 calc R U P A 2
H2B H 0.9019 0.9069 0.1977 0.139 Uiso 0.220(6) 1 calc R U P A 2
H2C H 1.0764 0.9011 0.1310 0.139 Uiso 0.220(6) 1 calc R U P A 2
C00R C 0.963(4) 0.648(2) 0.0534(14) 0.111(6) Uani 0.220(6) 1 d . U P A 2
H00Y H 1.0840 0.6284 0.0849 0.166 Uiso 0.220(6) 1 calc R U P A 2
H H 1.0250 0.7039 0.0170 0.166 Uiso 0.220(6) 1 calc R U P A 2
HA H 0.8727 0.5645 0.0226 0.166 Uiso 0.220(6) 1 calc R U P A 2


_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 H001 0.8200 . ?
O001 C006 1.359(3) . ?
N002 C008 1.280(3) . ?
N002 C00A 1.413(4) . ?
N3 O004 1.215(4) . ?
N3 O5 1.217(3) . ?
N3 C00F 1.473(4) . ?
C006 C007 1.402(4) . ?
C006 C00B 1.394(4) . ?
C007 C008 1.448(4) . ?
C007 C00C 1.392(4) . ?
C008 H008 0.9300 . ?
C009 C00C 1.370(4) . ?
C009 C00D 1.404(4) . ?
C009 C00I 1.524(4) . ?
C00A C00E 1.381(4) . ?
C00A C00G 1.383(4) . ?
C00B C00D 1.387(4) . ?
C00B C00H 1.536(4) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00F 1.379(4) . ?
C00F C00J 1.367(4) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.373(4) . ?
C00H C00L 1.533(4) . ?
C00H C00M 1.539(4) . ?
C00H C00N 1.530(4) . ?
C00I C00O 1.513(5) . ?
C00I C00P 1.531(5) . ?
C00I C00Q 1.519(6) . ?
C00I C1 1.554(17) . ?
C00I C2 1.633(17) . ?
C00I C00R 1.510(17) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.380(4) . ?
C00K H00K 0.9300 . ?
C00L H00A 0.9600 . ?
C00L H00B 0.9600 . ?
C00L H00F 0.9600 . ?
C00M H00H 0.9600 . ?
C00M H00I 0.9600 . ?
C00M H00L 0.9600 . ?
C00N H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?
C00O H00P 0.9600 . ?
C00O H00Q 0.9600 . ?
C00O H00R 0.9600 . ?
C00P H00S 0.9600 . ?
C00P H00T 0.9600 . ?
C00P H00U 0.9600 . ?
C00Q H00V 0.9600 . ?
C00Q H00W 0.9600 . ?
C00Q H00X 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C00R H00Y 0.9600 . ?
C00R H 0.9600 . ?
C00R HA 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 H001 109.5 . . ?
C008 N002 C00A 119.5(3) . . ?
O004 N3 O5 123.6(4) . . ?
O004 N3 C00F 118.6(3) . . ?
O5 N3 C00F 117.8(4) . . ?
O001 C006 C007 119.7(3) . . ?
O001 C006 C00B 119.3(3) . . ?
C00B C006 C007 121.0(3) . . ?
C006 C007 C008 121.8(3) . . ?
C00C C007 C006 119.4(3) . . ?
C00C C007 C008 118.8(3) . . ?
N002 C008 C007 123.4(3) . . ?
N002 C008 H008 118.3 . . ?
C007 C008 H008 118.3 . . ?
C00C C009 C00D 116.1(3) . . ?
C00C C009 C00I 123.4(3) . . ?
C00D C009 C00I 120.5(3) . . ?
C00E C00A N002 122.0(3) . . ?
C00E C00A C00G 119.3(3) . . ?
C00G C00A N002 118.7(3) . . ?
C006 C00B C00H 122.0(3) . . ?
C00D C00B C006 116.3(3) . . ?
C00D C00B C00H 121.7(3) . . ?
C007 C00C H00C 118.9 . . ?
C009 C00C C007 122.2(3) . . ?
C009 C00C H00C 118.9 . . ?
C009 C00D H00D 117.5 . . ?
C00B C00D C009 125.0(3) . . ?
C00B C00D H00D 117.5 . . ?
C00A C00E H00E 120.8 . . ?
C00F C00E C00A 118.5(3) . . ?
C00F C00E H00E 120.8 . . ?
C00E C00F N3 117.9(3) . . ?
C00J C00F N3 119.1(3) . . ?
C00J C00F C00E 123.0(3) . . ?
C00A C00G H00G 119.5 . . ?
C00K C00G C00A 121.0(3) . . ?
C00K C00G H00G 119.5 . . ?
C00B C00H C00M 109.7(3) . . ?
C00L C00H C00B 110.4(3) . . ?
C00L C00H C00M 109.6(3) . . ?
C00N C00H C00B 111.4(2) . . ?
C00N C00H C00L 108.3(3) . . ?
C00N C00H C00M 107.3(3) . . ?
C009 C00I C00P 109.5(3) . . ?
C009 C00I C1 109.0(6) . . ?
C009 C00I C2 108.2(6) . . ?
C00O C00I C009 112.4(3) . . ?
C00O C00I C00P 107.9(4) . . ?
C00O C00I C00Q 108.8(4) . . ?
C00Q C00I C009 109.3(3) . . ?
C00Q C00I C00P 108.9(4) . . ?
C1 C00I C2 106.9(11) . . ?
C00R C00I C009 115.2(7) . . ?
C00R C00I C1 111.2(12) . . ?
C00R C00I C2 105.9(11) . . ?
C00F C00J H00J 121.0 . . ?
C00F C00J C00K 118.0(3) . . ?
C00K C00J H00J 121.0 . . ?
C00G C00K C00J 120.3(3) . . ?
C00G C00K H00K 119.9 . . ?
C00J C00K H00K 119.9 . . ?
C00H C00L H00A 109.5 . . ?
C00H C00L H00B 109.5 . . ?
C00H C00L H00F 109.5 . . ?
H00A C00L H00B 109.5 . . ?
H00A C00L H00F 109.5 . . ?
H00B C00L H00F 109.5 . . ?
C00H C00M H00H 109.5 . . ?
C00H C00M H00I 109.5 . . ?
C00H C00M H00L 109.5 . . ?
H00H C00M H00I 109.5 . . ?
H00H C00M H00L 109.5 . . ?
H00I C00M H00L 109.5 . . ?
C00H C00N H00M 109.5 . . ?
C00H C00N H00N 109.5 . . ?
C00H C00N H00O 109.5 . . ?
H00M C00N H00N 109.5 . . ?
H00M C00N H00O 109.5 . . ?
H00N C00N H00O 109.5 . . ?
C00I C00O H00P 109.5 . . ?
C00I C00O H00Q 109.5 . . ?
C00I C00O H00R 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
H00P C00O H00R 109.5 . . ?
H00Q C00O H00R 109.5 . . ?
C00I C00P H00S 109.5 . . ?
C00I C00P H00T 109.5 . . ?
C00I C00P H00U 109.5 . . ?
H00S C00P H00T 109.5 . . ?
H00S C00P H00U 109.5 . . ?
H00T C00P H00U 109.5 . . ?
C00I C00Q H00V 109.5 . . ?
C00I C00Q H00W 109.5 . . ?
C00I C00Q H00X 109.5 . . ?
H00V C00Q H00W 109.5 . . ?
H00V C00Q H00X 109.5 . . ?
H00W C00Q H00X 109.5 . . ?
C00I C1 H1A 109.5 . . ?
C00I C1 H1B 109.5 . . ?
C00I C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00I C2 H2A 109.5 . . ?
C00I C2 H2B 109.5 . . ?
C00I C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C00I C00R H00Y 109.5 . . ?
C00I C00R H 109.5 . . ?
C00I C00R HA 109.5 . . ?
H00Y C00R H 109.5 . . ?
H00Y C00R HA 109.5 . . ?
H C00R HA 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_40point4degC
_database_code_depnum_ccdc_archive 'CCDC 2291947'
loop_
_audit_author_name
_audit_author_address
'Shodai Hasebe'
;Waseda University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_40point4degC        
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: This is because we input the calibrated true temperature manually after measurement. Note that the temperature difference between the default temperature (293K) and the true temperature is <40K.
;
# Added during the CSD deposition process: Thursday 31 August 2023 06:53 AM
# end Validation Reply Form

_audit_creation_date             2022-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0405(8)
_cell_length_b                   10.3230(13)
_cell_length_c                   16.826(2)
_cell_angle_alpha                101.079(7)
_cell_angle_beta                 92.174(6)
_cell_angle_gamma                101.364(7)
_cell_volume                     1006.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7419
_cell_measurement_temperature    313.55
_cell_measurement_theta_max      68
_cell_measurement_theta_min      4
_shelx_estimated_absorpt_T_max   1
_shelx_estimated_absorpt_T_min   0.6656
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.6656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR(Rigaku,1995)
_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    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11191
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.167
_diffrn_reflns_theta_min         4.463
_diffrn_ambient_temperature      313.55
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1818
_reflns_number_total             3589
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.0823
_refine_ls_restrained_S_all      1.101
_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)+(0.0958P)²+0.0184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2249
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C2 \\sim C00I \\sim C1 \\sim C00R: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C00I \\sim C00O \\sim C00P \\sim C00Q: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 C2, C00I, C1, C00R
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00O, C00P, C00I, C00Q
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=
 Sof(C00R)=Sof(H00Y)=Sof(H)=Sof(HA)=1-FVAR(1)
 Sof(C00O)=Sof(H00P)=Sof(H00Q)=Sof(H00R)=Sof(C00P)=Sof(H00S)=Sof(H00T)=
 Sof(H00U)=Sof(C00Q)=Sof(H00V)=Sof(H00W)=Sof(H00X)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00D(H00D), C00E(H00E), C00H(H00H), C00J(H00J),
 C00K(H00K)
5.b Idealised Me refined as rotating group:
 C00L(H00A,H00C,H00F), C00M(H00G,H00I,H00L), C00N(H00M,H00N,H00O), C00O(H00P,
 H00Q,H00R), C00P(H00S,H00T,H00U), C00Q(H00V,H00W,H00X), C1(H1A,H1B,H1C),
 C2(H2A,H2B,H2C), C00R(H00Y,H,HA)
5.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 0.3537(4) 0.39921(19) 0.31666(12) 0.0854(7) Uani 1 1 d . . . . .
H001 H 0.2744 0.4425 0.3447 0.128 Uiso 1 1 calc R U . . .
N002 N 0.1902(4) 0.6067(2) 0.38146(15) 0.0766(7) Uani 1 1 d . . . . .
N3 N 0.1550(6) 0.9861(3) 0.60102(18) 0.0939(9) Uani 1 1 d . . . . .
O004 O 0.3559(5) 1.0282(3) 0.59730(16) 0.1306(11) Uani 1 1 d . . . . .
C005 C 0.4629(5) 0.4752(3) 0.26674(17) 0.0674(8) Uani 1 1 d . . . . .
O5 O 0.0390(5) 1.0437(3) 0.64731(16) 0.1293(10) Uani 1 1 d . . . . .
C007 C 0.4431(5) 0.6100(3) 0.27456(16) 0.0673(8) Uani 1 1 d . . . . .
C008 C 0.6891(5) 0.6373(3) 0.16629(17) 0.0688(8) Uani 1 1 d . . . . .
C009 C 0.3062(5) 0.6707(3) 0.33374(18) 0.0749(8) Uani 1 1 d . . . . .
H009 H 0.3024 0.7613 0.3373 0.090 Uiso 1 1 calc R U . . .
C00A C 0.5959(5) 0.4185(3) 0.20973(17) 0.0671(8) Uani 1 1 d . . . . .
C00B C 0.7039(5) 0.5020(3) 0.16119(16) 0.0704(8) Uani 1 1 d . . . . .
H00B H 0.7927 0.4657 0.1224 0.084 Uiso 1 1 calc R U . . .
C00C C 0.0709(6) 0.6760(3) 0.44017(17) 0.0697(8) Uani 1 1 d . . . . .
C00D C 0.1705(5) 0.7988(3) 0.48929(18) 0.0732(8) Uani 1 1 d . . . . .
H00D H 0.3186 0.8406 0.4836 0.088 Uiso 1 1 calc R U . . .
C00E C 0.5586(5) 0.6878(3) 0.22428(17) 0.0716(8) Uani 1 1 d . . . . .
H00E H 0.5467 0.7775 0.2303 0.086 Uiso 1 1 calc R U . . .
C00F C 0.0444(6) 0.8575(3) 0.54683(18) 0.0739(9) Uani 1 1 d . . . . .
C00G C 0.6228(5) 0.2716(3) 0.20077(18) 0.0753(9) Uani 1 1 d . . . . .
C00H C -0.1492(6) 0.6170(3) 0.45033(19) 0.0809(9) Uani 1 1 d . . . . .
H00H H -0.2154 0.5336 0.4180 0.097 Uiso 1 1 calc R U . . .
C00I C 0.8160(6) 0.7200(3) 0.11013(18) 0.0760(9) Uani 1 1 d . U . . .
C00J C -0.1753(6) 0.8018(4) 0.55674(19) 0.0829(9) Uani 1 1 d . . . . .
H00J H -0.2567 0.8450 0.5955 0.099 Uiso 1 1 calc R U . . .
C00K C -0.2721(6) 0.6789(4) 0.5070(2) 0.0875(10) Uani 1 1 d . . . . .
H00K H -0.4211 0.6382 0.5121 0.105 Uiso 1 1 calc R U . . .
C00L C 0.3912(6) 0.1747(3) 0.1793(2) 0.1009(11) Uani 1 1 d . . . . .
H00A H 0.2938 0.1932 0.2220 0.151 Uiso 1 1 calc R U . . .
H00C H 0.4105 0.0833 0.1733 0.151 Uiso 1 1 calc R U . . .
H00F H 0.3247 0.1871 0.1293 0.151 Uiso 1 1 calc R U . . .
C00M C 0.7306(6) 0.2513(3) 0.2805(2) 0.1001(11) Uani 1 1 d . . . . .
H00G H 0.8756 0.3116 0.2936 0.150 Uiso 1 1 calc R U . . .
H00I H 0.7494 0.1598 0.2742 0.150 Uiso 1 1 calc R U . . .
H00L H 0.6340 0.2699 0.3234 0.150 Uiso 1 1 calc R U . . .
C00N C 0.7775(6) 0.2347(3) 0.1337(2) 0.1067(12) Uani 1 1 d . . . . .
H00M H 0.7118 0.2430 0.0826 0.160 Uiso 1 1 calc R U . . .
H00N H 0.7945 0.1434 0.1308 0.160 Uiso 1 1 calc R U . . .
H00O H 0.9233 0.2945 0.1458 0.160 Uiso 1 1 calc R U . . .
C00O C 0.7434(11) 0.6491(5) 0.0215(3) 0.113(2) Uani 0.767(6) 1 d . U P A 1
H00P H 0.5846 0.6444 0.0105 0.169 Uiso 0.767(6) 1 calc R U P A 1
H00Q H 0.7723 0.5594 0.0126 0.169 Uiso 0.767(6) 1 calc R U P A 1
H00R H 0.8280 0.6989 -0.0141 0.169 Uiso 0.767(6) 1 calc R U P A 1
C00P C 0.7675(11) 0.8607(5) 0.1215(4) 0.126(2) Uani 0.767(6) 1 d . U P A 1
H00S H 0.8515 0.9091 0.0851 0.188 Uiso 0.767(6) 1 calc R U P A 1
H00T H 0.8118 0.9076 0.1765 0.188 Uiso 0.767(6) 1 calc R U P A 1
H00U H 0.6085 0.8546 0.1100 0.188 Uiso 0.767(6) 1 calc R U P A 1
C00Q C 1.0693(8) 0.7319(7) 0.1257(4) 0.128(2) Uani 0.767(6) 1 d . U P A 1
H00V H 1.1485 0.7815 0.0890 0.192 Uiso 0.767(6) 1 calc R U P A 1
H00W H 1.1026 0.6433 0.1174 0.192 Uiso 0.767(6) 1 calc R U P A 1
H00X H 1.1167 0.7783 0.1807 0.192 Uiso 0.767(6) 1 calc R U P A 1
C1 C 0.960(4) 0.6472(18) 0.0535(13) 0.120(6) Uani 0.233(6) 1 d . U P A 2
H1A H 0.8729 0.5599 0.0276 0.180 Uiso 0.233(6) 1 calc R U P A 2
H1B H 1.0905 0.6367 0.0838 0.180 Uiso 0.233(6) 1 calc R U P A 2
H1C H 1.0069 0.6986 0.0130 0.180 Uiso 0.233(6) 1 calc R U P A 2
C2 C 0.645(3) 0.777(2) 0.0632(12) 0.107(5) Uani 0.233(6) 1 d . U P A 2
H2A H 0.5681 0.8306 0.1011 0.160 Uiso 0.233(6) 1 calc R U P A 2
H2B H 0.5373 0.7035 0.0304 0.160 Uiso 0.233(6) 1 calc R U P A 2
H2C H 0.7249 0.8317 0.0290 0.160 Uiso 0.233(6) 1 calc R U P A 2
C00R C 0.989(3) 0.8503(16) 0.1660(9) 0.099(5) Uani 0.233(6) 1 d . U P A 2
H00Y H 1.0839 0.8976 0.1316 0.148 Uiso 0.233(6) 1 calc R U P A 2
H H 1.0825 0.8201 0.2031 0.148 Uiso 0.233(6) 1 calc R U P A 2
HA H 0.9040 0.9096 0.1959 0.148 Uiso 0.233(6) 1 calc R U P A 2


_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 H001 0.8200 . ?
O001 C005 1.359(3) . ?
N002 C009 1.279(3) . ?
N002 C00C 1.412(3) . ?
N3 O004 1.214(3) . ?
N3 O5 1.216(3) . ?
N3 C00F 1.476(4) . ?
C005 C007 1.401(4) . ?
C005 C00A 1.392(4) . ?
C007 C009 1.447(4) . ?
C007 C00E 1.390(3) . ?
C008 C00B 1.403(3) . ?
C008 C00E 1.367(3) . ?
C008 C00I 1.522(4) . ?
C009 H009 0.9300 . ?
C00A C00B 1.387(3) . ?
C00A C00G 1.537(3) . ?
C00B H00B 0.9300 . ?
C00C C00D 1.383(4) . ?
C00C C00H 1.380(4) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.377(4) . ?
C00E H00E 0.9300 . ?
C00F C00J 1.369(4) . ?
C00G C00L 1.536(4) . ?
C00G C00M 1.536(4) . ?
C00G C00N 1.532(4) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.369(4) . ?
C00I C00O 1.535(5) . ?
C00I C00P 1.515(5) . ?
C00I C00Q 1.519(5) . ?
C00I C1 1.507(16) . ?
C00I C2 1.543(16) . ?
C00I C00R 1.635(15) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.383(4) . ?
C00K H00K 0.9300 . ?
C00L H00A 0.9600 . ?
C00L H00C 0.9600 . ?
C00L H00F 0.9600 . ?
C00M H00G 0.9600 . ?
C00M H00I 0.9600 . ?
C00M H00L 0.9600 . ?
C00N H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?
C00O H00P 0.9600 . ?
C00O H00Q 0.9600 . ?
C00O H00R 0.9600 . ?
C00P H00S 0.9600 . ?
C00P H00T 0.9600 . ?
C00P H00U 0.9600 . ?
C00Q H00V 0.9600 . ?
C00Q H00W 0.9600 . ?
C00Q H00X 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C00R H00Y 0.9600 . ?
C00R H 0.9600 . ?
C00R HA 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
C005 O001 H001 109.5 . . ?
C009 N002 C00C 119.7(3) . . ?
O004 N3 O5 123.7(4) . . ?
O004 N3 C00F 118.5(3) . . ?
O5 N3 C00F 117.8(3) . . ?
O001 C005 C007 119.5(3) . . ?
O001 C005 C00A 119.4(3) . . ?
C00A C005 C007 121.1(3) . . ?
C005 C007 C009 121.9(3) . . ?
C00E C007 C005 119.1(3) . . ?
C00E C007 C009 119.0(3) . . ?
C00B C008 C00I 120.4(3) . . ?
C00E C008 C00B 116.1(3) . . ?
C00E C008 C00I 123.5(3) . . ?
N002 C009 C007 123.6(3) . . ?
N002 C009 H009 118.2 . . ?
C007 C009 H009 118.2 . . ?
C005 C00A C00G 122.1(3) . . ?
C00B C00A C005 116.4(3) . . ?
C00B C00A C00G 121.5(3) . . ?
C008 C00B H00B 117.6 . . ?
C00A C00B C008 124.8(3) . . ?
C00A C00B H00B 117.6 . . ?
C00D C00C N002 121.8(3) . . ?
C00H C00C N002 118.8(3) . . ?
C00H C00C C00D 119.3(3) . . ?
C00C C00D H00D 120.9 . . ?
C00F C00D C00C 118.1(3) . . ?
C00F C00D H00D 120.9 . . ?
C007 C00E H00E 118.8 . . ?
C008 C00E C007 122.5(3) . . ?
C008 C00E H00E 118.8 . . ?
C00D C00F N3 117.8(3) . . ?
C00J C00F N3 118.9(3) . . ?
C00J C00F C00D 123.4(3) . . ?
C00L C00G C00A 110.3(2) . . ?
C00L C00G C00M 109.6(2) . . ?
C00M C00G C00A 109.9(2) . . ?
C00N C00G C00A 111.5(2) . . ?
C00N C00G C00L 108.1(3) . . ?
C00N C00G C00M 107.4(3) . . ?
C00C C00H H00H 119.3 . . ?
C00K C00H C00C 121.3(3) . . ?
C00K C00H H00H 119.3 . . ?
C008 C00I C00O 109.3(3) . . ?
C008 C00I C2 109.0(6) . . ?
C008 C00I C00R 108.4(5) . . ?
C00P C00I C008 112.5(3) . . ?
C00P C00I C00O 107.7(4) . . ?
C00P C00I C00Q 108.7(4) . . ?
C00Q C00I C008 109.7(3) . . ?
C00Q C00I C00O 108.9(4) . . ?
C1 C00I C008 115.0(7) . . ?
C1 C00I C2 111.5(11) . . ?
C1 C00I C00R 106.1(11) . . ?
C2 C00I C00R 106.5(10) . . ?
C00F C00J H00J 121.2 . . ?
C00F C00J C00K 117.6(3) . . ?
C00K C00J H00J 121.2 . . ?
C00H C00K C00J 120.2(3) . . ?
C00H C00K H00K 119.9 . . ?
C00J C00K H00K 119.9 . . ?
C00G C00L H00A 109.5 . . ?
C00G C00L H00C 109.5 . . ?
C00G C00L H00F 109.5 . . ?
H00A C00L H00C 109.5 . . ?
H00A C00L H00F 109.5 . . ?
H00C C00L H00F 109.5 . . ?
C00G C00M H00G 109.5 . . ?
C00G C00M H00I 109.5 . . ?
C00G C00M H00L 109.5 . . ?
H00G C00M H00I 109.5 . . ?
H00G C00M H00L 109.5 . . ?
H00I C00M H00L 109.5 . . ?
C00G C00N H00M 109.5 . . ?
C00G C00N H00N 109.5 . . ?
C00G C00N H00O 109.5 . . ?
H00M C00N H00N 109.5 . . ?
H00M C00N H00O 109.5 . . ?
H00N C00N H00O 109.5 . . ?
C00I C00O H00P 109.5 . . ?
C00I C00O H00Q 109.5 . . ?
C00I C00O H00R 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
H00P C00O H00R 109.5 . . ?
H00Q C00O H00R 109.5 . . ?
C00I C00P H00S 109.5 . . ?
C00I C00P H00T 109.5 . . ?
C00I C00P H00U 109.5 . . ?
H00S C00P H00T 109.5 . . ?
H00S C00P H00U 109.5 . . ?
H00T C00P H00U 109.5 . . ?
C00I C00Q H00V 109.5 . . ?
C00I C00Q H00W 109.5 . . ?
C00I C00Q H00X 109.5 . . ?
H00V C00Q H00W 109.5 . . ?
H00V C00Q H00X 109.5 . . ?
H00W C00Q H00X 109.5 . . ?
C00I C1 H1A 109.5 . . ?
C00I C1 H1B 109.5 . . ?
C00I C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00I C2 H2A 109.5 . . ?
C00I C2 H2B 109.5 . . ?
C00I C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C00I C00R H00Y 109.5 . . ?
C00I C00R H 109.5 . . ?
C00I C00R HA 109.5 . . ?
H00Y C00R H 109.5 . . ?
H00Y C00R HA 109.5 . . ?
H C00R HA 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_48point8degC
_database_code_depnum_ccdc_archive 'CCDC 2291948'
loop_
_audit_author_name
_audit_author_address
'Shodai Hasebe'
;Waseda University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_48point8degC        
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: This is because we input the calibrated true temperature manually after measurement. Note that the temperature difference between the default temperature (293K) and the true temperature is <40K.
;
# Added during the CSD deposition process: Thursday 31 August 2023 06:53 AM
# end Validation Reply Form

_audit_creation_date             2022-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0445(9)
_cell_length_b                   10.3300(14)
_cell_length_c                   16.853(2)
_cell_angle_alpha                101.035(7)
_cell_angle_beta                 92.153(6)
_cell_angle_gamma                101.338(7)
_cell_volume                     1009.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7085
_cell_measurement_temperature    321.95
_cell_measurement_theta_max      68
_cell_measurement_theta_min      4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.6498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR(Rigaku,1995)
_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    1.166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11179
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.182
_diffrn_reflns_theta_min         4.458
_diffrn_ambient_temperature      321.95
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1754
_reflns_number_total             3600
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3600
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1424
_refine_ls_R_factor_gt           0.0861
_refine_ls_restrained_S_all      1.100
_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)+(0.1094P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2163
_refine_ls_wR_factor_ref         0.2458
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C00I \\sim C1 \\sim C2 \\sim C00R: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C00I \\sim C00O \\sim C00P \\sim C00Q: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 C00I, C1, C2, C00R
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00I, C00O, C00P, C00Q
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=
 Sof(C00R)=Sof(H00Z)=Sof(H)=Sof(HA)=1-FVAR(1)
 Sof(C00O)=Sof(H00Q)=Sof(H00R)=Sof(H00S)=Sof(C00P)=Sof(H00T)=Sof(H00U)=
 Sof(H00V)=Sof(C00Q)=Sof(H00W)=Sof(H00X)=Sof(H00Y)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00E(H00E), C00F(H00F), C00H(H00H), C00J(H00J),
 C00K(H00K)
5.b Idealised Me refined as rotating group:
 C00L(H00A,H00D,H00G), C00M(H00I,H00L,H00M), C00N(H00N,H00O,H00P), C00O(H00Q,
 H00R,H00S), C00P(H00T,H00U,H00V), C00Q(H00W,H00X,H00Y), C1(H1A,H1B,H1C),
 C2(H2A,H2B,H2C), C00R(H00Z,H,HA)
5.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 0.3541(4) 0.3995(2) 0.31677(13) 0.0897(7) Uani 1 1 d . . . . .
H001 H 0.2762 0.4431 0.3452 0.134 Uiso 1 1 calc R U . . .
N002 N 0.1907(4) 0.6072(2) 0.38150(16) 0.0801(8) Uani 1 1 d . . . . .
N3 N 0.1547(7) 0.9857(3) 0.60096(19) 0.0986(10) Uani 1 1 d . . . . .
O8 O 0.3559(6) 1.0277(3) 0.59727(17) 0.1360(12) Uani 1 1 d . . . . .
C005 C 0.4437(5) 0.6101(3) 0.27465(17) 0.0706(8) Uani 1 1 d . . . . .
C006 C 0.4628(5) 0.4754(3) 0.26682(18) 0.0710(8) Uani 1 1 d . . . . .
O007 O 0.0395(5) 1.0433(3) 0.64707(18) 0.1348(11) Uani 1 1 d . . . . .
C008 C 0.5963(5) 0.4185(3) 0.20962(18) 0.0704(8) Uani 1 1 d . . . . .
C009 C 0.6892(5) 0.6375(3) 0.16625(18) 0.0730(9) Uani 1 1 d . . . . .
C00A C 0.0712(6) 0.6764(3) 0.44016(19) 0.0735(9) Uani 1 1 d . . . . .
C00B C 0.3064(5) 0.6708(3) 0.33367(19) 0.0783(9) Uani 1 1 d . . . . .
H00B H 0.3022 0.7612 0.3370 0.094 Uiso 1 1 calc R U . . .
C00C C 0.1713(5) 0.7988(3) 0.48938(19) 0.0766(9) Uani 1 1 d . . . . .
H00C H 0.3195 0.8403 0.4839 0.092 Uiso 1 1 calc R U . . .
C00D C 0.0446(7) 0.8575(3) 0.54681(19) 0.0778(9) Uani 1 1 d . . . . .
C00E C 0.5587(5) 0.6881(3) 0.22442(19) 0.0753(9) Uani 1 1 d . . . . .
H00E H 0.5467 0.7778 0.2305 0.090 Uiso 1 1 calc R U . . .
C00F C 0.7036(5) 0.5026(3) 0.16124(17) 0.0744(9) Uani 1 1 d . . . . .
H00F H 0.7920 0.4664 0.1224 0.089 Uiso 1 1 calc R U . . .
C00G C 0.6227(6) 0.2720(3) 0.2009(2) 0.0795(9) Uani 1 1 d . . . . .
C00H C -0.1488(6) 0.6174(3) 0.4504(2) 0.0847(10) Uani 1 1 d . . . . .
H00H H -0.2148 0.5341 0.4181 0.102 Uiso 1 1 calc R U . . .
C00I C 0.8149(6) 0.7203(3) 0.11022(19) 0.0805(9) Uani 1 1 d . U . . .
C00J C -0.1749(7) 0.8015(4) 0.5566(2) 0.0869(10) Uani 1 1 d . . . . .
H00J H -0.2563 0.8445 0.5954 0.104 Uiso 1 1 calc R U . . .
C00K C -0.2714(6) 0.6790(4) 0.5069(2) 0.0916(10) Uani 1 1 d . . . . .
H00K H -0.4203 0.6383 0.5120 0.110 Uiso 1 1 calc R U . . .
C00L C 0.3915(6) 0.1752(3) 0.1797(2) 0.1061(12) Uani 1 1 d . . . . .
H00A H 0.2946 0.1934 0.2225 0.159 Uiso 1 1 calc R U . . .
H00D H 0.4110 0.0839 0.1734 0.159 Uiso 1 1 calc R U . . .
H00G H 0.3243 0.1879 0.1300 0.159 Uiso 1 1 calc R U . . .
C00M C 0.7309(6) 0.2517(3) 0.2804(2) 0.1052(12) Uani 1 1 d . . . . .
H00I H 0.8753 0.3123 0.2936 0.158 Uiso 1 1 calc R U . . .
H00L H 0.7508 0.1604 0.2740 0.158 Uiso 1 1 calc R U . . .
H00M H 0.6341 0.2696 0.3233 0.158 Uiso 1 1 calc R U . . .
C00N C 0.7781(6) 0.2352(3) 0.1339(2) 0.1118(13) Uani 1 1 d . . . . .
H00N H 0.7135 0.2445 0.0829 0.168 Uiso 1 1 calc R U . . .
H00O H 0.7937 0.1436 0.1306 0.168 Uiso 1 1 calc R U . . .
H00P H 0.9241 0.2943 0.1463 0.168 Uiso 1 1 calc R U . . .
C00O C 0.7670(12) 0.8609(6) 0.1218(4) 0.130(3) Uani 0.755(6) 1 d . U P A 1
H00Q H 0.8117 0.9075 0.1767 0.195 Uiso 0.755(6) 1 calc R U P A 1
H00R H 0.6080 0.8550 0.1105 0.195 Uiso 0.755(6) 1 calc R U P A 1
H00S H 0.8507 0.9093 0.0855 0.195 Uiso 0.755(6) 1 calc R U P A 1
C00P C 0.7427(12) 0.6493(6) 0.0218(3) 0.118(2) Uani 0.755(6) 1 d . U P A 1
H00T H 0.8268 0.6993 -0.0137 0.177 Uiso 0.755(6) 1 calc R U P A 1
H00U H 0.5839 0.6444 0.0108 0.177 Uiso 0.755(6) 1 calc R U P A 1
H00V H 0.7722 0.5599 0.0129 0.177 Uiso 0.755(6) 1 calc R U P A 1
C00Q C 1.0679(9) 0.7329(7) 0.1260(5) 0.133(3) Uani 0.755(6) 1 d . U P A 1
H00W H 1.1022 0.6446 0.1177 0.200 Uiso 0.755(6) 1 calc R U P A 1
H00X H 1.1147 0.7792 0.1808 0.200 Uiso 0.755(6) 1 calc R U P A 1
H00Y H 1.1469 0.7828 0.0893 0.200 Uiso 0.755(6) 1 calc R U P A 1
C1 C 0.645(3) 0.777(2) 0.0633(12) 0.110(5) Uani 0.245(6) 1 d . U P A 2
H1A H 0.5657 0.8295 0.1010 0.166 Uiso 0.245(6) 1 calc R U P A 2
H1B H 0.5382 0.7036 0.0300 0.166 Uiso 0.245(6) 1 calc R U P A 2
H1C H 0.7245 0.8326 0.0297 0.166 Uiso 0.245(6) 1 calc R U P A 2
C2 C 0.987(3) 0.8511(16) 0.1662(9) 0.102(5) Uani 0.245(6) 1 d . U P A 2
H2A H 1.0863 0.8209 0.2013 0.152 Uiso 0.245(6) 1 calc R U P A 2
H2B H 0.9010 0.9072 0.1984 0.152 Uiso 0.245(6) 1 calc R U P A 2
H2C H 1.0753 0.9017 0.1319 0.152 Uiso 0.245(6) 1 calc R U P A 2
C00R C 0.961(4) 0.6479(18) 0.0546(13) 0.125(6) Uani 0.245(6) 1 d . U P A 2
H00Z H 1.0128 0.7005 0.0152 0.187 Uiso 0.245(6) 1 calc R U P A 2
H H 0.8739 0.5616 0.0274 0.187 Uiso 0.245(6) 1 calc R U P A 2
HA H 1.0884 0.6354 0.0857 0.187 Uiso 0.245(6) 1 calc R U P A 2


_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 H001 0.8200 . ?
O001 C006 1.359(3) . ?
N002 C00A 1.413(4) . ?
N002 C00B 1.279(3) . ?
N3 O8 1.216(4) . ?
N3 O007 1.212(3) . ?
N3 C00D 1.474(4) . ?
C005 C006 1.400(4) . ?
C005 C00B 1.449(4) . ?
C005 C00E 1.390(4) . ?
C006 C008 1.398(4) . ?
C008 C00F 1.389(4) . ?
C008 C00G 1.533(4) . ?
C009 C00E 1.371(4) . ?
C009 C00F 1.400(4) . ?
C009 C00I 1.519(4) . ?
C00A C00C 1.384(4) . ?
C00A C00H 1.381(4) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00D 1.380(4) . ?
C00D C00J 1.369(4) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G C00L 1.535(4) . ?
C00G C00M 1.538(4) . ?
C00G C00N 1.535(4) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.367(4) . ?
C00I C00O 1.514(5) . ?
C00I C00P 1.535(6) . ?
C00I C00Q 1.518(6) . ?
C00I C1 1.541(16) . ?
C00I C2 1.639(16) . ?
C00I C00R 1.506(16) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.382(4) . ?
C00K H00K 0.9300 . ?
C00L H00A 0.9600 . ?
C00L H00D 0.9600 . ?
C00L H00G 0.9600 . ?
C00M H00I 0.9600 . ?
C00M H00L 0.9600 . ?
C00M H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?
C00N H00P 0.9600 . ?
C00O H00Q 0.9600 . ?
C00O H00R 0.9600 . ?
C00O H00S 0.9600 . ?
C00P H00T 0.9600 . ?
C00P H00U 0.9600 . ?
C00P H00V 0.9600 . ?
C00Q H00W 0.9600 . ?
C00Q H00X 0.9600 . ?
C00Q H00Y 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C00R H00Z 0.9600 . ?
C00R H 0.9600 . ?
C00R HA 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 H001 109.5 . . ?
C00B N002 C00A 119.9(3) . . ?
O8 N3 C00D 118.4(4) . . ?
O007 N3 O8 123.5(4) . . ?
O007 N3 C00D 118.1(4) . . ?
C006 C005 C00B 121.8(3) . . ?
C00E C005 C006 119.4(3) . . ?
C00E C005 C00B 118.9(3) . . ?
O001 C006 C005 119.6(3) . . ?
O001 C006 C008 119.4(3) . . ?
C008 C006 C005 121.0(3) . . ?
C006 C008 C00G 121.9(3) . . ?
C00F C008 C006 116.1(3) . . ?
C00F C008 C00G 122.0(3) . . ?
C00E C009 C00F 115.9(3) . . ?
C00E C009 C00I 123.4(3) . . ?
C00F C009 C00I 120.7(3) . . ?
C00C C00A N002 121.7(3) . . ?
C00H C00A N002 118.8(3) . . ?
C00H C00A C00C 119.4(3) . . ?
N002 C00B C005 123.8(3) . . ?
N002 C00B H00B 118.1 . . ?
C005 C00B H00B 118.1 . . ?
C00A C00C H00C 121.0 . . ?
C00D C00C C00A 118.0(3) . . ?
C00D C00C H00C 121.0 . . ?
C00C C00D N3 117.8(4) . . ?
C00J C00D N3 118.9(4) . . ?
C00J C00D C00C 123.3(3) . . ?
C005 C00E H00E 118.8 . . ?
C009 C00E C005 122.4(3) . . ?
C009 C00E H00E 118.8 . . ?
C008 C00F C009 125.2(3) . . ?
C008 C00F H00F 117.4 . . ?
C009 C00F H00F 117.4 . . ?
C008 C00G C00L 110.4(3) . . ?
C008 C00G C00M 109.9(3) . . ?
C008 C00G C00N 111.4(3) . . ?
C00L C00G C00M 109.6(3) . . ?
C00N C00G C00L 108.3(3) . . ?
C00N C00G C00M 107.2(3) . . ?
C00A C00H H00H 119.3 . . ?
C00K C00H C00A 121.3(3) . . ?
C00K C00H H00H 119.3 . . ?
C009 C00I C00P 109.3(3) . . ?
C009 C00I C1 109.2(6) . . ?
C009 C00I C2 108.2(5) . . ?
C00O C00I C009 112.6(3) . . ?
C00O C00I C00P 108.0(4) . . ?
C00O C00I C00Q 108.2(4) . . ?
C00Q C00I C009 109.6(3) . . ?
C00Q C00I C00P 109.1(4) . . ?
C1 C00I C2 106.3(10) . . ?
C00R C00I C009 114.7(7) . . ?
C00R C00I C1 112.1(12) . . ?
C00R C00I C2 105.9(11) . . ?
C00D C00J H00J 121.2 . . ?
C00D C00J C00K 117.7(3) . . ?
C00K C00J H00J 121.2 . . ?
C00H C00K C00J 120.3(3) . . ?
C00H C00K H00K 119.9 . . ?
C00J C00K H00K 119.9 . . ?
C00G C00L H00A 109.5 . . ?
C00G C00L H00D 109.5 . . ?
C00G C00L H00G 109.5 . . ?
H00A C00L H00D 109.5 . . ?
H00A C00L H00G 109.5 . . ?
H00D C00L H00G 109.5 . . ?
C00G C00M H00I 109.5 . . ?
C00G C00M H00L 109.5 . . ?
C00G C00M H00M 109.5 . . ?
H00I C00M H00L 109.5 . . ?
H00I C00M H00M 109.5 . . ?
H00L C00M H00M 109.5 . . ?
C00G C00N H00N 109.5 . . ?
C00G C00N H00O 109.5 . . ?
C00G C00N H00P 109.5 . . ?
H00N C00N H00O 109.5 . . ?
H00N C00N H00P 109.5 . . ?
H00O C00N H00P 109.5 . . ?
C00I C00O H00Q 109.5 . . ?
C00I C00O H00R 109.5 . . ?
C00I C00O H00S 109.5 . . ?
H00Q C00O H00R 109.5 . . ?
H00Q C00O H00S 109.5 . . ?
H00R C00O H00S 109.5 . . ?
C00I C00P H00T 109.5 . . ?
C00I C00P H00U 109.5 . . ?
C00I C00P H00V 109.5 . . ?
H00T C00P H00U 109.5 . . ?
H00T C00P H00V 109.5 . . ?
H00U C00P H00V 109.5 . . ?
C00I C00Q H00W 109.5 . . ?
C00I C00Q H00X 109.5 . . ?
C00I C00Q H00Y 109.5 . . ?
H00W C00Q H00X 109.5 . . ?
H00W C00Q H00Y 109.5 . . ?
H00X C00Q H00Y 109.5 . . ?
C00I C1 H1A 109.5 . . ?
C00I C1 H1B 109.5 . . ?
C00I C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00I C2 H2A 109.5 . . ?
C00I C2 H2B 109.5 . . ?
C00I C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C00I C00R H00Z 109.5 . . ?
C00I C00R H 109.5 . . ?
C00I C00R HA 109.5 . . ?
H00Z C00R H 109.5 . . ?
H00Z C00R HA 109.5 . . ?
H C00R HA 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 C006 C008 C00F -179.5(3) . . . . ?
O001 C006 C008 C00G 0.5(5) . . . . ?
N002 C00A C00C C00D -178.0(3) . . . . ?
N002 C00A C00H C00K 179.2(3) . . . . ?
N3 C00D C00J C00K -177.8(3) . . . . ?
O8 N3 C00D C00C -6.1(5) . . . . ?
O8 N3 C00D C00J 172.7(3) . . . . ?
C005 C006 C008 C00F -0.9(4) . . . . ?
C005 C006 C008 C00G 179.0(3) . . . . ?
C006 C005 C00B N002 -1.2(5) . . . . ?
C006 C005 C00E C009 0.8(5) . . . . ?
C006 C008 C00F C009 0.6(5) . . . . ?
C006 C008 C00G C00L 59.8(4) . . . . ?
C006 C008 C00G C00M -61.2(4) . . . . ?
C006 C008 C00G C00N -179.9(3) . . . . ?
O007 N3 C00D C00C 174.1(3) . . . . ?
O007 N3 C00D C00J -7.0(5) . . . . ?
C00A N002 C00B C005 176.6(3) . . . . ?
C00A C00C C00D N3 177.9(2) . . . . ?
C00A C00C C00D C00J -0.9(5) . . . . ?
C00A C00H C00K C00J -1.3(5) . . . . ?
C00B N002 C00A C00C -47.3(4) . . . . ?
C00B N002 C00A C00H 135.1(3) . . . . ?
C00B C005 C006 O001 -1.4(5) . . . . ?
C00B C005 C006 C008 -179.9(3) . . . . ?
C00B C005 C00E C009 -179.0(3) . . . . ?
C00C C00A C00H C00K 1.5(5) . . . . ?
C00C C00D C00J C00K 1.0(5) . . . . ?
C00D C00J C00K C00H 0.1(5) . . . . ?
C00E C005 C006 O001 178.8(3) . . . . ?
C00E C005 C006 C008 0.3(5) . . . . ?
C00E C005 C00B N002 178.6(3) . . . . ?
C00E C009 C00F C008 0.4(5) . . . . ?
C00E C009 C00I C00O -4.0(6) . . . . ?
C00E C009 C00I C00P -124.0(4) . . . . ?
C00E C009 C00I C00Q 116.5(5) . . . . ?
C00E C009 C00I C1 -57.1(10) . . . . ?
C00E C009 C00I C2 58.2(8) . . . . ?
C00E C009 C00I C00R 176.1(12) . . . . ?
C00F C008 C00G C00L -120.3(3) . . . . ?
C00F C008 C00G C00M 118.7(3) . . . . ?
C00F C008 C00G C00N 0.0(4) . . . . ?
C00F C009 C00E C005 -1.1(5) . . . . ?
C00F C009 C00I C00O 176.7(4) . . . . ?
C00F C009 C00I C00P 56.7(5) . . . . ?
C00F C009 C00I C00Q -62.8(5) . . . . ?
C00F C009 C00I C1 123.5(10) . . . . ?
C00F C009 C00I C2 -121.2(8) . . . . ?
C00F C009 C00I C00R -3.2(13) . . . . ?
C00G C008 C00F C009 -179.3(3) . . . . ?
C00H C00A C00C C00D -0.4(4) . . . . ?
C00I C009 C00E C005 179.5(3) . . . . ?
C00I C009 C00F C008 179.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_6point8degC
_database_code_depnum_ccdc_archive 'CCDC 2291943'
loop_
_audit_author_name
_audit_author_address
'Shodai Hasebe'
;Waseda University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_6point8degC         
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: This is because we input the calibrated true temperature manually after measurement. Note that the temperature difference between the default temperature (293K) and the true temperature is <40K.
;
# Added during the CSD deposition process: Thursday 31 August 2023 06:53 AM
# end Validation Reply Form

_audit_creation_date             2022-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0455(6)
_cell_length_b                   10.3195(10)
_cell_length_c                   16.7114(17)
_cell_angle_alpha                101.333(7)
_cell_angle_beta                 92.155(6)
_cell_angle_gamma                101.650(7)
_cell_volume                     997.93(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7964
_cell_measurement_temperature    279.95
_cell_measurement_theta_max      68
_cell_measurement_theta_min      4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.6222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR(Rigaku,1995)
_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    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11113
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         4.473
_diffrn_ambient_temperature      279.95
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2124
_reflns_number_total             3562
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3562
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0738
_refine_ls_restrained_S_all      1.108
_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)+(0.0755P)²+0.1630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1741
_refine_ls_wR_factor_ref         0.1973
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C00I \\sim C00R \\sim C2 \\sim C1: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C00I \\sim C00Q \\sim C00P \\sim C00O: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 C00I, C00R, C2, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00I, C00Q, C00P, C00O
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C00R)=Sof(H00Y)=Sof(H)=Sof(HA)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=
 Sof(H2A)=Sof(H2B)=Sof(H2C)=1-FVAR(1)
 Sof(C00O)=Sof(H00P)=Sof(H00Q)=Sof(H00R)=Sof(C00P)=Sof(H00S)=Sof(H00T)=
 Sof(H00U)=Sof(C00Q)=Sof(H00V)=Sof(H00W)=Sof(H00X)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00G(H00G), C00J(H00J),
 C00K(H00K)
5.b Idealised Me refined as rotating group:
 C00L(H00A,H00E,H00F), C00M(H00H,H00I,H00L), C00N(H00M,H00N,H00O), C00O(H00P,
 H00Q,H00R), C00P(H00S,H00T,H00U), C00Q(H00V,H00W,H00X), C00R(H00Y,H,HA),
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
5.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 0.3500(3) 0.39687(18) 0.31599(12) 0.0715(6) Uani 1 1 d . . . . .
H001 H 0.2682 0.4395 0.3433 0.107 Uiso 1 1 calc R U . . .
N002 N 0.1885(4) 0.6052(2) 0.38097(14) 0.0636(6) Uani 1 1 d . . . . .
N003 N 0.1539(6) 0.9877(3) 0.60167(16) 0.0799(8) Uani 1 1 d . . . . .
O004 O 0.3557(5) 1.0299(2) 0.59818(16) 0.1106(9) Uani 1 1 d . . . . .
O005 O 0.0379(5) 1.0456(2) 0.64841(15) 0.1095(9) Uani 1 1 d . . . . .
C006 C 0.4430(5) 0.6084(3) 0.27413(15) 0.0566(7) Uani 1 1 d . . . . .
C007 C 0.6918(5) 0.6355(3) 0.16584(16) 0.0567(7) Uani 1 1 d . . . . .
C008 C 0.4604(5) 0.4729(3) 0.26616(16) 0.0573(7) Uani 1 1 d . . . . .
C009 C 0.3059(5) 0.6695(3) 0.33319(16) 0.0615(7) Uani 1 1 d . . . . .
H009 H 0.3026 0.7602 0.3367 0.074 Uiso 1 1 calc R U . . .
C00A C 0.0688(5) 0.6754(3) 0.44004(16) 0.0586(7) Uani 1 1 d . . . . .
C00B C 0.1693(5) 0.7987(3) 0.48979(16) 0.0610(7) Uani 1 1 d . . . . .
H00B H 0.3181 0.8402 0.4846 0.073 Uiso 1 1 calc R U . . .
C00C C 0.5605(5) 0.6866(3) 0.22400(16) 0.0594(7) Uani 1 1 d . . . . .
H00C H 0.5496 0.7766 0.2302 0.071 Uiso 1 1 calc R U . . .
C00D C 0.7048(5) 0.4997(3) 0.16054(15) 0.0595(7) Uani 1 1 d . . . . .
H00D H 0.7940 0.4633 0.1217 0.071 Uiso 1 1 calc R U . . .
C00E C 0.5949(5) 0.4160(3) 0.20872(16) 0.0567(7) Uani 1 1 d . . . . .
C00F C 0.0430(5) 0.8584(3) 0.54731(16) 0.0611(7) Uani 1 1 d . . . . .
C00G C -0.1529(5) 0.6156(3) 0.44985(17) 0.0670(8) Uani 1 1 d . . . . .
H00G H -0.2196 0.5316 0.4175 0.080 Uiso 1 1 calc R U . . .
C00H C 0.6189(5) 0.2684(3) 0.19966(17) 0.0640(8) Uani 1 1 d . . . . .
C00I C 0.8205(5) 0.7180(3) 0.10929(17) 0.0626(7) Uani 1 1 d . U . . .
C00J C -0.1774(6) 0.8026(3) 0.55674(17) 0.0693(8) Uani 1 1 d . . . . .
H00J H -0.2589 0.8464 0.5955 0.083 Uiso 1 1 calc R U . . .
C00K C -0.2750(5) 0.6793(3) 0.50693(18) 0.0731(8) Uani 1 1 d . . . . .
H00K H -0.4245 0.6390 0.5120 0.088 Uiso 1 1 calc R U . . .
C00L C 0.3871(5) 0.1717(3) 0.1775(2) 0.0839(10) Uani 1 1 d . . . . .
H00A H 0.2892 0.1905 0.2203 0.126 Uiso 1 1 calc R U . . .
H00E H 0.4051 0.0800 0.1714 0.126 Uiso 1 1 calc R U . . .
H00F H 0.3216 0.1839 0.1270 0.126 Uiso 1 1 calc R U . . .
C00M C 0.7258(5) 0.2482(3) 0.27992(19) 0.0834(10) Uani 1 1 d . . . . .
H00H H 0.8712 0.3087 0.2934 0.125 Uiso 1 1 calc R U . . .
H00I H 0.7437 0.1565 0.2734 0.125 Uiso 1 1 calc R U . . .
H00L H 0.6292 0.2669 0.3231 0.125 Uiso 1 1 calc R U . . .
C00N C 0.7737(6) 0.2314(3) 0.1324(2) 0.0910(11) Uani 1 1 d . . . . .
H00M H 0.7086 0.2396 0.0809 0.137 Uiso 1 1 calc R U . . .
H00N H 0.7897 0.1399 0.1293 0.137 Uiso 1 1 calc R U . . .
H00O H 0.9198 0.2913 0.1449 0.137 Uiso 1 1 calc R U . . .
C00O C 0.7736(9) 0.8592(4) 0.1206(3) 0.0989(17) Uani 0.830(5) 1 d . U P A 1
H00P H 0.8190 0.9068 0.1760 0.148 Uiso 0.830(5) 1 calc R U P A 1
H00Q H 0.6145 0.8530 0.1092 0.148 Uiso 0.830(5) 1 calc R U P A 1
H00R H 0.8574 0.9070 0.0838 0.148 Uiso 0.830(5) 1 calc R U P A 1
C00P C 0.7514(8) 0.6464(4) 0.0199(2) 0.0924(15) Uani 0.830(5) 1 d . U P A 1
H00S H 0.8365 0.6969 -0.0154 0.139 Uiso 0.830(5) 1 calc R U P A 1
H00T H 0.5925 0.6404 0.0081 0.139 Uiso 0.830(5) 1 calc R U P A 1
H00U H 0.7817 0.5571 0.0111 0.139 Uiso 0.830(5) 1 calc R U P A 1
C00Q C 1.0737(7) 0.7307(5) 0.1263(3) 0.1006(17) Uani 0.830(5) 1 d . U P A 1
H00V H 1.1196 0.7780 0.1818 0.151 Uiso 0.830(5) 1 calc R U P A 1
H00W H 1.1546 0.7799 0.0895 0.151 Uiso 0.830(5) 1 calc R U P A 1
H00X H 1.1068 0.6421 0.1185 0.151 Uiso 0.830(5) 1 calc R U P A 1
C00R C 0.974(4) 0.645(2) 0.0548(15) 0.101(6) Uani 0.170(5) 1 d . U P A 2
H00Y H 1.0586 0.7065 0.0251 0.151 Uiso 0.170(5) 1 calc R U P A 2
H H 0.8826 0.5694 0.0169 0.151 Uiso 0.170(5) 1 calc R U P A 2
HA H 1.0760 0.6141 0.0881 0.151 Uiso 0.170(5) 1 calc R U P A 2
C1 C 0.648(3) 0.772(2) 0.0606(13) 0.085(6) Uani 0.170(5) 1 d . U P A 2
H1A H 0.5658 0.8236 0.0981 0.128 Uiso 0.170(5) 1 calc R U P A 2
H1B H 0.5433 0.6971 0.0265 0.128 Uiso 0.170(5) 1 calc R U P A 2
H1C H 0.7269 0.8284 0.0269 0.128 Uiso 0.170(5) 1 calc R U P A 2
C2 C 0.988(3) 0.8507(19) 0.1660(11) 0.079(5) Uani 0.170(5) 1 d . U P A 2
H2A H 1.0898 0.8225 0.2011 0.119 Uiso 0.170(5) 1 calc R U P A 2
H2B H 0.8993 0.9049 0.1987 0.119 Uiso 0.170(5) 1 calc R U P A 2
H2C H 1.0735 0.9030 0.1315 0.119 Uiso 0.170(5) 1 calc R U P A 2


_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 H001 0.8200 . ?
O001 C008 1.357(3) . ?
N002 C009 1.282(3) . ?
N002 C00A 1.417(3) . ?
N003 O004 1.217(3) . ?
N003 O005 1.219(3) . ?
N003 C00F 1.474(4) . ?
C006 C008 1.404(3) . ?
C006 C009 1.445(3) . ?
C006 C00C 1.392(3) . ?
C007 C00C 1.371(3) . ?
C007 C00D 1.404(3) . ?
C007 C00I 1.526(3) . ?
C008 C00E 1.399(3) . ?
C009 H009 0.9300 . ?
C00A C00B 1.384(4) . ?
C00A C00G 1.388(4) . ?
C00B H00B 0.9300 . ?
C00B C00F 1.378(4) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00E 1.385(3) . ?
C00E C00H 1.538(3) . ?
C00F C00J 1.369(4) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.374(4) . ?
C00H C00L 1.532(4) . ?
C00H C00M 1.536(4) . ?
C00H C00N 1.529(4) . ?
C00I C00O 1.517(4) . ?
C00I C00P 1.531(5) . ?
C00I C00Q 1.521(5) . ?
C00I C00R 1.52(2) . ?
C00I C1 1.554(19) . ?
C00I C2 1.630(19) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.379(4) . ?
C00K H00K 0.9300 . ?
C00L H00A 0.9600 . ?
C00L H00E 0.9600 . ?
C00L H00F 0.9600 . ?
C00M H00H 0.9600 . ?
C00M H00I 0.9600 . ?
C00M H00L 0.9600 . ?
C00N H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?
C00O H00P 0.9600 . ?
C00O H00Q 0.9600 . ?
C00O H00R 0.9600 . ?
C00P H00S 0.9600 . ?
C00P H00T 0.9600 . ?
C00P H00U 0.9600 . ?
C00Q H00V 0.9600 . ?
C00Q H00W 0.9600 . ?
C00Q H00X 0.9600 . ?
C00R H00Y 0.9600 . ?
C00R H 0.9600 . ?
C00R HA 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
C008 O001 H001 109.5 . . ?
C009 N002 C00A 119.4(2) . . ?
O004 N003 O005 123.7(3) . . ?
O004 N003 C00F 118.5(3) . . ?
O005 N003 C00F 117.8(3) . . ?
C008 C006 C009 121.8(2) . . ?
C00C C006 C008 119.5(2) . . ?
C00C C006 C009 118.7(2) . . ?
C00C C007 C00D 116.2(2) . . ?
C00C C007 C00I 123.5(2) . . ?
C00D C007 C00I 120.3(2) . . ?
O001 C008 C006 119.8(2) . . ?
O001 C008 C00E 119.4(2) . . ?
C00E C008 C006 120.8(2) . . ?
N002 C009 C006 123.4(3) . . ?
N002 C009 H009 118.3 . . ?
C006 C009 H009 118.3 . . ?
C00B C00A N002 121.8(3) . . ?
C00B C00A C00G 119.5(3) . . ?
C00G C00A N002 118.6(3) . . ?
C00A C00B H00B 120.9 . . ?
C00F C00B C00A 118.2(3) . . ?
C00F C00B H00B 120.9 . . ?
C006 C00C H00C 118.9 . . ?
C007 C00C C006 122.2(2) . . ?
C007 C00C H00C 118.9 . . ?
C007 C00D H00D 117.5 . . ?
C00E C00D C007 125.0(2) . . ?
C00E C00D H00D 117.5 . . ?
C008 C00E C00H 121.7(2) . . ?
C00D C00E C008 116.4(2) . . ?
C00D C00E C00H 121.9(2) . . ?
C00B C00F N003 117.7(3) . . ?
C00J C00F N003 119.0(3) . . ?
C00J C00F C00B 123.2(3) . . ?
C00A C00G H00G 119.7 . . ?
C00K C00G C00A 120.7(3) . . ?
C00K C00G H00G 119.7 . . ?
C00L C00H C00E 110.5(2) . . ?
C00L C00H C00M 109.8(2) . . ?
C00M C00H C00E 109.9(2) . . ?
C00N C00H C00E 111.2(2) . . ?
C00N C00H C00L 108.1(3) . . ?
C00N C00H C00M 107.3(2) . . ?
C007 C00I C00P 109.7(2) . . ?
C007 C00I C1 108.4(7) . . ?
C007 C00I C2 108.1(6) . . ?
C00O C00I C007 112.5(2) . . ?
C00O C00I C00P 108.0(3) . . ?
C00O C00I C00Q 108.4(3) . . ?
C00Q C00I C007 109.4(2) . . ?
C00Q C00I C00P 108.9(3) . . ?
C00R C00I C007 114.7(8) . . ?
C00R C00I C1 113.2(13) . . ?
C00R C00I C2 105.6(13) . . ?
C1 C00I C2 106.2(12) . . ?
C00F C00J H00J 121.0 . . ?
C00F C00J C00K 117.9(3) . . ?
C00K C00J H00J 121.0 . . ?
C00G C00K C00J 120.5(3) . . ?
C00G C00K H00K 119.7 . . ?
C00J C00K H00K 119.7 . . ?
C00H C00L H00A 109.5 . . ?
C00H C00L H00E 109.5 . . ?
C00H C00L H00F 109.5 . . ?
H00A C00L H00E 109.5 . . ?
H00A C00L H00F 109.5 . . ?
H00E C00L H00F 109.5 . . ?
C00H C00M H00H 109.5 . . ?
C00H C00M H00I 109.5 . . ?
C00H C00M H00L 109.5 . . ?
H00H C00M H00I 109.5 . . ?
H00H C00M H00L 109.5 . . ?
H00I C00M H00L 109.5 . . ?
C00H C00N H00M 109.5 . . ?
C00H C00N H00N 109.5 . . ?
C00H C00N H00O 109.5 . . ?
H00M C00N H00N 109.5 . . ?
H00M C00N H00O 109.5 . . ?
H00N C00N H00O 109.5 . . ?
C00I C00O H00P 109.5 . . ?
C00I C00O H00Q 109.5 . . ?
C00I C00O H00R 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
H00P C00O H00R 109.5 . . ?
H00Q C00O H00R 109.5 . . ?
C00I C00P H00S 109.5 . . ?
C00I C00P H00T 109.5 . . ?
C00I C00P H00U 109.5 . . ?
H00S C00P H00T 109.5 . . ?
H00S C00P H00U 109.5 . . ?
H00T C00P H00U 109.5 . . ?
C00I C00Q H00V 109.5 . . ?
C00I C00Q H00W 109.5 . . ?
C00I C00Q H00X 109.5 . . ?
H00V C00Q H00W 109.5 . . ?
H00V C00Q H00X 109.5 . . ?
H00W C00Q H00X 109.5 . . ?
C00I C00R H00Y 109.5 . . ?
C00I C00R H 109.5 . . ?
C00I C00R HA 109.5 . . ?
H00Y C00R H 109.5 . . ?
H00Y C00R HA 109.5 . . ?
H C00R HA 109.5 . . ?
C00I C1 H1A 109.5 . . ?
C00I C1 H1B 109.5 . . ?
C00I C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00I C2 H2A 109.5 . . ?
C00I C2 H2B 109.5 . . ?
C00I C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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 C008 C00E C00D -179.3(2) . . . . ?
O001 C008 C00E C00H 0.8(4) . . . . ?
N002 C00A C00B C00F -178.1(2) . . . . ?
N002 C00A C00G C00K 179.4(2) . . . . ?
N003 C00F C00J C00K -177.9(2) . . . . ?
O004 N003 C00F C00B -6.1(4) . . . . ?
O004 N003 C00F C00J 173.0(3) . . . . ?
O005 N003 C00F C00B 174.7(2) . . . . ?
O005 N003 C00F C00J -6.2(4) . . . . ?
C006 C008 C00E C00D -0.9(4) . . . . ?
C006 C008 C00E C00H 179.2(2) . . . . ?
C007 C00D C00E C008 0.5(4) . . . . ?
C007 C00D C00E C00H -179.6(2) . . . . ?
C008 C006 C009 N002 -1.3(4) . . . . ?
C008 C006 C00C C007 0.8(4) . . . . ?
C008 C00E C00H C00L 59.6(3) . . . . ?
C008 C00E C00H C00M -61.7(4) . . . . ?
C008 C00E C00H C00N 179.6(3) . . . . ?
C009 N002 C00A C00B -47.0(4) . . . . ?
C009 N002 C00A C00G 135.4(3) . . . . ?
C009 C006 C008 O001 -1.4(4) . . . . ?
C009 C006 C008 C00E -179.8(2) . . . . ?
C009 C006 C00C C007 -179.2(2) . . . . ?
C00A N002 C009 C006 176.6(2) . . . . ?
C00A C00B C00F N003 178.2(2) . . . . ?
C00A C00B C00F C00J -1.0(4) . . . . ?
C00A C00G C00K C00J -1.4(4) . . . . ?
C00B C00A C00G C00K 1.7(4) . . . . ?
C00B C00F C00J C00K 1.2(4) . . . . ?
C00C C006 C008 O001 178.6(2) . . . . ?
C00C C006 C008 C00E 0.2(4) . . . . ?
C00C C006 C009 N002 178.7(3) . . . . ?
C00C C007 C00D C00E 0.5(4) . . . . ?
C00C C007 C00I C00O -4.0(4) . . . . ?
C00C C007 C00I C00P -124.2(3) . . . . ?
C00C C007 C00I C00Q 116.5(4) . . . . ?
C00C C007 C00I C00R 174.5(13) . . . . ?
C00C C007 C00I C1 -57.9(11) . . . . ?
C00C C007 C00I C2 56.9(9) . . . . ?
C00D C007 C00C C006 -1.1(4) . . . . ?
C00D C007 C00I C00O 176.4(3) . . . . ?
C00D C007 C00I C00P 56.2(4) . . . . ?
C00D C007 C00I C00Q -63.1(4) . . . . ?
C00D C007 C00I C00R -5.1(13) . . . . ?
C00D C007 C00I C1 122.5(11) . . . . ?
C00D C007 C00I C2 -122.7(9) . . . . ?
C00D C00E C00H C00L -120.3(3) . . . . ?
C00D C00E C00H C00M 118.4(3) . . . . ?
C00D C00E C00H C00N -0.3(4) . . . . ?
C00F C00J C00K C00G 0.0(4) . . . . ?
C00G C00A C00B C00F -0.5(4) . . . . ?
C00I C007 C00C C006 179.3(3) . . . . ?
C00I C007 C00D C00E -179.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_57point2degC
_database_code_depnum_ccdc_archive 'CCDC 2291949'
loop_
_audit_author_name
_audit_author_address
'Shodai Hasebe'
;Waseda University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_57point2degC        
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: This is because we input the calibrated true temperature manually after measurement. Note that the temperature difference between the default temperature (293K) and the true temperature is <40K.
;
# Added during the CSD deposition process: Thursday 31 August 2023 06:53 AM
# end Validation Reply Form

_audit_creation_date             2022-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0467(10)
_cell_length_b                   10.3324(17)
_cell_length_c                   16.871(3)
_cell_angle_alpha                101.000(7)
_cell_angle_beta                 92.143(6)
_cell_angle_gamma                101.307(7)
_cell_volume                     1011.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6722
_cell_measurement_temperature    330.35
_cell_measurement_theta_max      68
_cell_measurement_theta_min      4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.6409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR(Rigaku,1995)
_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    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11190
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.170
_diffrn_reflns_theta_min         4.456
_diffrn_ambient_temperature      330.35
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1754
_reflns_number_total             3605
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.0865
_refine_ls_restrained_S_all      1.088
_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)+(0.1058P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2088
_refine_ls_wR_factor_ref         0.2395
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C2 \\sim C00I \\sim C00R \\sim C1: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C00Q \\sim C00I \\sim C00P \\sim C00O: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 C00I, C2, C00R, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00Q, C00I, C00P, C00O
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C00R)=Sof(H00Z)=Sof(H)=Sof(HA)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=
 Sof(H2A)=Sof(H2B)=Sof(H2C)=1-FVAR(1)
 Sof(C00O)=Sof(H00Q)=Sof(H00R)=Sof(H00S)=Sof(C00P)=Sof(H00T)=Sof(H00U)=
 Sof(H00V)=Sof(C00Q)=Sof(H00W)=Sof(H00X)=Sof(H00Y)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00J(H00J),
 C00K(H00K)
5.b Idealised Me refined as rotating group:
 C00L(H00B,H00D,H00H), C00M(H00I,H00L,H00M), C00N(H00N,H00O,H00P), C00O(H00Q,
 H00R,H00S), C00P(H00T,H00U,H00V), C00Q(H00W,H00X,H00Y), C00R(H00Z,H,HA),
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
5.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 0.6457(4) 0.60027(19) 0.68321(13) 0.0929(7) Uani 1 1 d . . . . .
H001 H 0.7321 0.5593 0.6576 0.139 Uiso 1 1 calc R U . . .
N002 N 0.8080(4) 0.3923(2) 0.61830(15) 0.0829(8) Uani 1 1 d . . . . .
N3 N 0.8437(7) 0.0141(3) 0.39905(19) 0.1011(10) Uani 1 1 d . . . . .
O8 O 0.6439(6) -0.0274(3) 0.40324(17) 0.1407(12) Uani 1 1 d . . . . .
C005 C 0.5560(5) 0.3890(3) 0.72520(16) 0.0725(8) Uani 1 1 d . . . . .
C006 C 0.5371(5) 0.5241(3) 0.73317(17) 0.0732(8) Uani 1 1 d . . . . .
O007 O 0.9602(5) -0.0431(3) 0.35327(17) 0.1377(11) Uani 1 1 d . . . . .
C008 C 0.3108(5) 0.3617(3) 0.83349(17) 0.0744(9) Uani 1 1 d . . . . .
C009 C 0.4037(5) 0.5809(3) 0.79018(17) 0.0727(8) Uani 1 1 d . . . . .
C00A C 0.8295(5) 0.2016(3) 0.51079(18) 0.0785(9) Uani 1 1 d . . . . .
H00A H 0.6816 0.1601 0.5165 0.094 Uiso 1 1 calc R U . . .
C00B C 0.9281(6) 0.3235(3) 0.55971(18) 0.0762(9) Uani 1 1 d . . . . .
C00C C 0.6925(5) 0.3284(3) 0.66606(18) 0.0807(9) Uani 1 1 d . . . . .
H00C H 0.6964 0.2379 0.6626 0.097 Uiso 1 1 calc R U . . .
C00D C 0.9543(7) 0.1424(3) 0.45324(19) 0.0801(9) Uani 1 1 d . . . . .
C00E C 0.2966(5) 0.4969(3) 0.83841(17) 0.0767(9) Uani 1 1 d . . . . .
H00E H 0.2082 0.5332 0.8772 0.092 Uiso 1 1 calc R U . . .
C00F C 0.4413(5) 0.3115(3) 0.77554(18) 0.0774(9) Uani 1 1 d . . . . .
H00F H 0.4537 0.2219 0.7696 0.093 Uiso 1 1 calc R U . . .
C00G C 1.1481(6) 0.3827(3) 0.5496(2) 0.0877(10) Uani 1 1 d . . . . .
H00G H 1.2141 0.4659 0.5818 0.105 Uiso 1 1 calc R U . . .
C00H C 0.3773(6) 0.7277(3) 0.79912(19) 0.0820(9) Uani 1 1 d . . . . .
C00I C 0.1850(6) 0.2793(3) 0.88942(19) 0.0823(9) Uani 1 1 d . U . . .
C00J C 1.2707(6) 0.3206(4) 0.4928(2) 0.0953(10) Uani 1 1 d . . . . .
H00J H 1.4197 0.3610 0.4877 0.114 Uiso 1 1 calc R U . . .
C00K C 1.1737(7) 0.1985(4) 0.4433(2) 0.0890(10) Uani 1 1 d . . . . .
H00K H 1.2548 0.1556 0.4045 0.107 Uiso 1 1 calc R U . . .
C00L C 0.2686(6) 0.7485(3) 0.7197(2) 0.1096(12) Uani 1 1 d . . . . .
H00B H 0.3669 0.7329 0.6771 0.164 Uiso 1 1 calc R U . . .
H00D H 0.2452 0.8391 0.7267 0.164 Uiso 1 1 calc R U . . .
H00H H 0.1259 0.6863 0.7059 0.164 Uiso 1 1 calc R U . . .
C00M C 0.6073(6) 0.8241(3) 0.8199(2) 0.1103(12) Uani 1 1 d . . . . .
H00I H 0.6754 0.8112 0.8693 0.165 Uiso 1 1 calc R U . . .
H00L H 0.5874 0.9154 0.8265 0.165 Uiso 1 1 calc R U . . .
H00M H 0.7036 0.8064 0.7769 0.165 Uiso 1 1 calc R U . . .
C00N C 0.2225(6) 0.7645(3) 0.8662(2) 0.1128(12) Uani 1 1 d . . . . .
H00N H 0.0765 0.7054 0.8539 0.169 Uiso 1 1 calc R U . . .
H00O H 0.2068 0.8560 0.8695 0.169 Uiso 1 1 calc R U . . .
H00P H 0.2875 0.7551 0.9170 0.169 Uiso 1 1 calc R U . . .
C00O C 0.2350(12) 0.1392(6) 0.8783(4) 0.134(3) Uani 0.748(6) 1 d . U P A 1
H00Q H 0.1891 0.0918 0.8236 0.201 Uiso 0.748(6) 1 calc R U P A 1
H00R H 0.1532 0.0911 0.9151 0.201 Uiso 0.748(6) 1 calc R U P A 1
H00S H 0.3943 0.1458 0.8890 0.201 Uiso 0.748(6) 1 calc R U P A 1
C00P C 0.2571(12) 0.3502(6) 0.9778(3) 0.124(2) Uani 0.748(6) 1 d . U P A 1
H00T H 0.4165 0.3569 0.9883 0.186 Uiso 0.748(6) 1 calc R U P A 1
H00U H 0.1755 0.2992 1.0133 0.186 Uiso 0.748(6) 1 calc R U P A 1
H00V H 0.2245 0.4389 0.9869 0.186 Uiso 0.748(6) 1 calc R U P A 1
C00Q C -0.0665(9) 0.2678(7) 0.8744(5) 0.139(3) Uani 0.748(6) 1 d . U P A 1
H00W H -0.0994 0.3563 0.8817 0.209 Uiso 0.748(6) 1 calc R U P A 1
H00X H -0.1450 0.2197 0.9118 0.209 Uiso 0.748(6) 1 calc R U P A 1
H00Y H -0.1149 0.2201 0.8200 0.209 Uiso 0.748(6) 1 calc R U P A 1
C00R C 0.012(3) 0.1477(16) 0.8333(9) 0.109(5) Uani 0.252(6) 1 d . U P A 2
H00Z H -0.0814 0.1775 0.7961 0.163 Uiso 0.252(6) 1 calc R U P A 2
H H -0.0817 0.1000 0.8675 0.163 Uiso 0.252(6) 1 calc R U P A 2
HA H 0.0986 0.0890 0.8035 0.163 Uiso 0.252(6) 1 calc R U P A 2
C1 C 0.352(3) 0.2197(19) 0.9355(11) 0.111(5) Uani 0.252(6) 1 d . U P A 2
H1A H 0.4221 0.1620 0.8976 0.167 Uiso 0.252(6) 1 calc R U P A 2
H1B H 0.2715 0.1685 0.9713 0.167 Uiso 0.252(6) 1 calc R U P A 2
H1C H 0.4655 0.2914 0.9665 0.167 Uiso 0.252(6) 1 calc R U P A 2
C2 C 0.036(4) 0.3503(17) 0.9442(13) 0.126(6) Uani 0.252(6) 1 d . U P A 2
H2A H 0.1240 0.4326 0.9759 0.189 Uiso 0.252(6) 1 calc R U P A 2
H2B H -0.0296 0.2932 0.9796 0.189 Uiso 0.252(6) 1 calc R U P A 2
H2C H -0.0829 0.3703 0.9121 0.189 Uiso 0.252(6) 1 calc R U P A 2


_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 H001 0.8200 . ?
O001 C006 1.361(3) . ?
N002 C00B 1.413(4) . ?
N002 C00C 1.280(3) . ?
N3 O8 1.210(3) . ?
N3 O007 1.213(3) . ?
N3 C00D 1.479(4) . ?
C005 C006 1.404(4) . ?
C005 C00C 1.447(4) . ?
C005 C00F 1.389(3) . ?
C006 C009 1.396(4) . ?
C008 C00E 1.404(3) . ?
C008 C00F 1.368(3) . ?
C008 C00I 1.516(4) . ?
C009 C00E 1.386(3) . ?
C009 C00H 1.536(4) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.377(4) . ?
C00A C00D 1.376(4) . ?
C00B C00G 1.382(4) . ?
C00C H00C 0.9300 . ?
C00D C00K 1.370(4) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00J 1.372(4) . ?
C00H C00L 1.540(4) . ?
C00H C00M 1.529(4) . ?
C00H C00N 1.534(4) . ?
C00I C00O 1.515(6) . ?
C00I C00P 1.536(6) . ?
C00I C00Q 1.510(6) . ?
C00I C00R 1.648(15) . ?
C00I C1 1.539(16) . ?
C00I C2 1.508(15) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.380(4) . ?
C00K H00K 0.9300 . ?
C00L H00B 0.9600 . ?
C00L H00D 0.9600 . ?
C00L H00H 0.9600 . ?
C00M H00I 0.9600 . ?
C00M H00L 0.9600 . ?
C00M H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?
C00N H00P 0.9600 . ?
C00O H00Q 0.9600 . ?
C00O H00R 0.9600 . ?
C00O H00S 0.9600 . ?
C00P H00T 0.9600 . ?
C00P H00U 0.9600 . ?
C00P H00V 0.9600 . ?
C00Q H00W 0.9600 . ?
C00Q H00X 0.9600 . ?
C00Q H00Y 0.9600 . ?
C00R H00Z 0.9600 . ?
C00R H 0.9600 . ?
C00R HA 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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 H001 109.5 . . ?
C00C N002 C00B 119.9(3) . . ?
O8 N3 O007 124.2(4) . . ?
O8 N3 C00D 118.2(4) . . ?
O007 N3 C00D 117.6(4) . . ?
C006 C005 C00C 121.7(3) . . ?
C00F C005 C006 119.2(3) . . ?
C00F C005 C00C 119.1(3) . . ?
O001 C006 C005 119.7(3) . . ?
O001 C006 C009 119.3(3) . . ?
C009 C006 C005 121.1(3) . . ?
C00E C008 C00I 120.6(3) . . ?
C00F C008 C00E 115.8(3) . . ?
C00F C008 C00I 123.6(3) . . ?
C006 C009 C00H 122.0(3) . . ?
C00E C009 C006 116.0(3) . . ?
C00E C009 C00H 121.9(3) . . ?
C00B C00A H00A 120.7 . . ?
C00D C00A H00A 120.7 . . ?
C00D C00A C00B 118.7(3) . . ?
C00A C00B N002 121.8(3) . . ?
C00A C00B C00G 119.2(3) . . ?
C00G C00B N002 118.9(3) . . ?
N002 C00C C005 123.7(3) . . ?
N002 C00C H00C 118.2 . . ?
C005 C00C H00C 118.2 . . ?
C00A C00D N3 118.1(3) . . ?
C00K C00D N3 119.0(4) . . ?
C00K C00D C00A 122.9(3) . . ?
C008 C00E H00E 117.3 . . ?
C009 C00E C008 125.3(3) . . ?
C009 C00E H00E 117.3 . . ?
C005 C00F H00F 118.7 . . ?
C008 C00F C005 122.6(3) . . ?
C008 C00F H00F 118.7 . . ?
C00B C00G H00G 119.5 . . ?
C00J C00G C00B 121.1(3) . . ?
C00J C00G H00G 119.5 . . ?
C009 C00H C00L 110.0(3) . . ?
C00M C00H C009 110.5(3) . . ?
C00M C00H C00L 109.4(2) . . ?
C00M C00H C00N 108.2(3) . . ?
C00N C00H C009 111.4(3) . . ?
C00N C00H C00L 107.2(3) . . ?
C008 C00I C00P 109.3(3) . . ?
C008 C00I C00R 108.2(5) . . ?
C008 C00I C1 109.8(6) . . ?
C00O C00I C008 112.3(3) . . ?
C00O C00I C00P 107.6(4) . . ?
C00Q C00I C008 109.7(3) . . ?
C00Q C00I C00O 109.1(4) . . ?
C00Q C00I C00P 108.7(4) . . ?
C1 C00I C00R 105.0(10) . . ?
C2 C00I C008 115.1(6) . . ?
C2 C00I C00R 105.0(11) . . ?
C2 C00I C1 113.0(11) . . ?
C00G C00J H00J 119.9 . . ?
C00G C00J C00K 120.2(3) . . ?
C00K C00J H00J 119.9 . . ?
C00D C00K C00J 117.9(3) . . ?
C00D C00K H00K 121.0 . . ?
C00J C00K H00K 121.0 . . ?
C00H C00L H00B 109.5 . . ?
C00H C00L H00D 109.5 . . ?
C00H C00L H00H 109.5 . . ?
H00B C00L H00D 109.5 . . ?
H00B C00L H00H 109.5 . . ?
H00D C00L H00H 109.5 . . ?
C00H C00M H00I 109.5 . . ?
C00H C00M H00L 109.5 . . ?
C00H C00M H00M 109.5 . . ?
H00I C00M H00L 109.5 . . ?
H00I C00M H00M 109.5 . . ?
H00L C00M H00M 109.5 . . ?
C00H C00N H00N 109.5 . . ?
C00H C00N H00O 109.5 . . ?
C00H C00N H00P 109.5 . . ?
H00N C00N H00O 109.5 . . ?
H00N C00N H00P 109.5 . . ?
H00O C00N H00P 109.5 . . ?
C00I C00O H00Q 109.5 . . ?
C00I C00O H00R 109.5 . . ?
C00I C00O H00S 109.5 . . ?
H00Q C00O H00R 109.5 . . ?
H00Q C00O H00S 109.5 . . ?
H00R C00O H00S 109.5 . . ?
C00I C00P H00T 109.5 . . ?
C00I C00P H00U 109.5 . . ?
C00I C00P H00V 109.5 . . ?
H00T C00P H00U 109.5 . . ?
H00T C00P H00V 109.5 . . ?
H00U C00P H00V 109.5 . . ?
C00I C00Q H00W 109.5 . . ?
C00I C00Q H00X 109.5 . . ?
C00I C00Q H00Y 109.5 . . ?
H00W C00Q H00X 109.5 . . ?
H00W C00Q H00Y 109.5 . . ?
H00X C00Q H00Y 109.5 . . ?
C00I C00R H00Z 109.5 . . ?
C00I C00R H 109.5 . . ?
C00I C00R HA 109.5 . . ?
H00Z C00R H 109.5 . . ?
H00Z C00R HA 109.5 . . ?
H C00R HA 109.5 . . ?
C00I C1 H1A 109.5 . . ?
C00I C1 H1B 109.5 . . ?
C00I C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00I C2 H2A 109.5 . . ?
C00I C2 H2B 109.5 . . ?
C00I C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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 C006 C009 C00E 179.4(3) . . . . ?
O001 C006 C009 C00H -0.7(4) . . . . ?
N002 C00B C00G C00J -179.2(3) . . . . ?
N3 C00D C00K C00J 177.8(3) . . . . ?
O8 N3 C00D C00A 6.0(5) . . . . ?
O8 N3 C00D C00K -172.9(3) . . . . ?
C005 C006 C009 C00E 1.1(4) . . . . ?
C005 C006 C009 C00H -179.0(3) . . . . ?
C006 C005 C00C N002 1.4(5) . . . . ?
C006 C005 C00F C008 -0.5(5) . . . . ?
C006 C009 C00E C008 -0.7(5) . . . . ?
C006 C009 C00H C00L 61.4(4) . . . . ?
C006 C009 C00H C00M -59.4(4) . . . . ?
C006 C009 C00H C00N -179.8(3) . . . . ?
O007 N3 C00D C00A -173.9(3) . . . . ?
O007 N3 C00D C00K 7.3(4) . . . . ?
C00A C00B C00G C00J -1.3(5) . . . . ?
C00A C00D C00K C00J -1.0(5) . . . . ?
C00B N002 C00C C005 -177.0(3) . . . . ?
C00B C00A C00D N3 -177.7(2) . . . . ?
C00B C00A C00D C00K 1.1(4) . . . . ?
C00B C00G C00J C00K 1.4(5) . . . . ?
C00C N002 C00B C00A 47.2(4) . . . . ?
C00C N002 C00B C00G -134.9(3) . . . . ?
C00C C005 C006 O001 1.3(4) . . . . ?
C00C C005 C006 C009 179.6(3) . . . . ?
C00C C005 C00F C008 179.3(3) . . . . ?
C00D C00A C00B N002 177.9(2) . . . . ?
C00D C00A C00B C00G 0.1(4) . . . . ?
C00E C008 C00F C005 0.9(4) . . . . ?
C00E C008 C00I C00O -176.1(4) . . . . ?
C00E C008 C00I C00P -56.7(5) . . . . ?
C00E C008 C00I C00Q 62.4(5) . . . . ?
C00E C008 C00I C00R 121.3(8) . . . . ?
C00E C008 C00I C1 -124.6(9) . . . . ?
C00E C008 C00I C2 4.2(12) . . . . ?
C00E C009 C00H C00L -118.7(3) . . . . ?
C00E C009 C00H C00M 120.5(3) . . . . ?
C00E C009 C00H C00N 0.1(4) . . . . ?
C00F C005 C006 O001 -178.9(2) . . . . ?
C00F C005 C006 C009 -0.6(4) . . . . ?
C00F C005 C00C N002 -178.4(3) . . . . ?
C00F C008 C00E C009 -0.3(5) . . . . ?
C00F C008 C00I C00O 4.5(6) . . . . ?
C00F C008 C00I C00P 123.9(4) . . . . ?
C00F C008 C00I C00Q -117.0(5) . . . . ?
C00F C008 C00I C00R -58.1(8) . . . . ?
C00F C008 C00I C1 56.0(9) . . . . ?
C00F C008 C00I C2 -175.2(11) . . . . ?
C00G C00J C00K C00D -0.3(5) . . . . ?
C00H C009 C00E C008 179.4(3) . . . . ?
C00I C008 C00E C009 -179.8(3) . . . . ?
C00I C008 C00F C005 -179.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
















