# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1997893'
loop_
_audit_author_name
_audit_author_address
'Shixuan Cao'
;Nankai University
China
;
_audit_update_record             
;
2020-04-20 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N3 O3'
_chemical_formula_weight         351.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.184(2)
_cell_length_b                   9.4457(19)
_cell_length_c                   17.793(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.40(3)
_cell_angle_gamma                90
_cell_volume                     1803.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4812
_cell_measurement_theta_min      1.8981
_cell_measurement_theta_max      27.9143

_exptl_crystal_description       monoclinic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8777
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17640
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.464
_diffrn_reflns_theta_max         27.914
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4299
_reflns_number_gt                3451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0797P)²+0.0147P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4299
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55814(8) 0.70846(9) -0.00128(6) 0.0309(2) Uani 1 1 d . . . . .
O2 O 0.64965(9) 0.61433(10) -0.11058(5) 0.0360(3) Uani 1 1 d . . . . .
O3 O 0.83877(10) 0.51540(10) -0.05832(6) 0.0350(3) Uani 1 1 d . . . . .
N1 N 0.80931(11) 0.94832(11) 0.06910(7) 0.0320(3) Uani 1 1 d . . . . .
N2 N 0.68869(11) 0.89026(12) 0.05294(7) 0.0320(3) Uani 1 1 d . . . . .
N3 N 0.76529(10) 0.68631(11) 0.00709(6) 0.0257(3) Uani 1 1 d . . . . .
C1 C 0.93235(15) 0.48520(15) 0.14702(9) 0.0356(3) Uani 1 1 d . . . . .
H1 H 0.960946 0.443980 0.106548 0.043 Uiso 1 1 calc R U . . .
C2 C 0.93119(16) 0.40587(17) 0.21213(10) 0.0460(4) Uani 1 1 d . . . . .
H2 H 0.958842 0.310344 0.216059 0.055 Uiso 1 1 calc R U . . .
C3 C 0.89032(15) 0.46422(19) 0.27115(9) 0.0459(4) Uani 1 1 d . . . . .
H3 H 0.889120 0.409175 0.315616 0.055 Uiso 1 1 calc R U . . .
C4 C 0.85117(16) 0.6028(2) 0.26546(9) 0.0491(4) Uani 1 1 d . . . . .
H4 H 0.823340 0.643632 0.306344 0.059 Uiso 1 1 calc R U . . .
C5 C 0.85201(15) 0.68343(17) 0.20044(8) 0.0395(4) Uani 1 1 d . . . . .
H5 H 0.825095 0.779209 0.197004 0.047 Uiso 1 1 calc R U . . .
C6 C 0.89206(12) 0.62434(13) 0.14056(7) 0.0267(3) Uani 1 1 d . . . . .
C7 C 0.88652(12) 0.70602(12) 0.06611(7) 0.0247(3) Uani 1 1 d . . . . .
H7 H 0.953585 0.669814 0.044041 0.030 Uiso 1 1 calc R U . . .
C8 C 0.90293(13) 0.86477(13) 0.07805(7) 0.0271(3) Uani 1 1 d . . . . .
C9 C 1.02938(13) 0.92759(14) 0.10254(7) 0.0279(3) Uani 1 1 d . . . . .
C10 C 1.13671(14) 0.84521(15) 0.11582(9) 0.0368(3) Uani 1 1 d . . . . .
H10 H 1.129957 0.746250 0.106015 0.044 Uiso 1 1 calc R U . . .
C11 C 1.25333(15) 0.90719(17) 0.14330(10) 0.0435(4) Uani 1 1 d . . . . .
H11 H 1.325842 0.850047 0.151890 0.052 Uiso 1 1 calc R U . . .
C12 C 1.26564(15) 1.04994(16) 0.15830(9) 0.0407(4) Uani 1 1 d . . . . .
H12 H 1.345955 1.091204 0.177600 0.049 Uiso 1 1 calc R U . . .
C13 C 1.15980(14) 1.13289(15) 0.14498(8) 0.0364(3) Uani 1 1 d . . . . .
H13 H 1.167415 1.231743 0.155036 0.044 Uiso 1 1 calc R U . . .
C14 C 1.04300(14) 1.07266(14) 0.11711(8) 0.0312(3) Uani 1 1 d . . . . .
H14 H 0.971009 1.130852 0.107747 0.037 Uiso 1 1 calc R U . . .
C15 C 0.66976(12) 0.76897(13) 0.01941(7) 0.0264(3) Uani 1 1 d . . . . .
C16 C 0.45290(13) 0.79904(15) -0.00343(9) 0.0368(3) Uani 1 1 d . . . . .
H16A H 0.450948 0.880359 -0.038856 0.044 Uiso 1 1 calc R U . . .
H16B H 0.458848 0.835809 0.049610 0.044 Uiso 1 1 calc R U . . .
C17 C 0.33801(14) 0.71105(17) -0.03271(11) 0.0453(4) Uani 1 1 d . . . . .
H17A H 0.332017 0.677608 -0.085788 0.068 Uiso 1 1 calc R U . . .
H17B H 0.264535 0.768273 -0.033599 0.068 Uiso 1 1 calc R U . . .
H17C H 0.342183 0.629609 0.002055 0.068 Uiso 1 1 calc R U . . .
C18 C 0.75668(13) 0.59596(13) -0.05566(7) 0.0269(3) Uani 1 1 d . . . . .
C19 C 0.61754(17) 0.51616(19) -0.17596(9) 0.0472(4) Uani 1 1 d . . . . .
H19A H 0.672702 0.432228 -0.164215 0.057 Uiso 1 1 calc R U . . .
H19B H 0.627930 0.562279 -0.223687 0.057 Uiso 1 1 calc R U . . .
C20 C 0.48673(17) 0.47314(18) -0.18845(11) 0.0509(4) Uani 1 1 d . . . . .
H20A H 0.480000 0.414015 -0.144563 0.076 Uiso 1 1 calc R U . . .
H20B H 0.458607 0.419217 -0.237329 0.076 Uiso 1 1 calc R U . . .
H20C H 0.434580 0.557581 -0.191749 0.076 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.3271(16) . ?
O1 C16 1.4469(16) . ?
O2 C18 1.3257(17) . ?
O2 C19 1.4512(17) . ?
O3 C18 1.2036(16) . ?
N1 C8 1.2847(17) . ?
N1 N2 1.4086(16) . ?
N2 C15 1.2814(17) . ?
N3 C18 1.3869(16) . ?
N3 C15 1.3897(16) . ?
N3 C7 1.4737(17) . ?
C1 C2 1.383(2) . ?
C1 C6 1.3836(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.373(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3845(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.5190(17) . ?
C7 C8 1.5183(17) . ?
C7 H7 1.0000 . ?
C8 C9 1.4813(19) . ?
C9 C10 1.3936(19) . ?
C9 C14 1.3949(19) . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C16 C17 1.495(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 C20 1.474(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C15 O1 C16 116.56(10) . . ?
C18 O2 C19 118.35(12) . . ?
C8 N1 N2 119.09(11) . . ?
C15 N2 N1 117.78(11) . . ?
C18 N3 C15 126.23(11) . . ?
C18 N3 C7 119.48(11) . . ?
C15 N3 C7 114.22(10) . . ?
C2 C1 C6 120.30(14) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.46(15) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.58(14) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.46(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.02(15) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 119.17(13) . . ?
C1 C6 C7 119.15(11) . . ?
C5 C6 C7 121.60(12) . . ?
N3 C7 C8 105.96(10) . . ?
N3 C7 C6 111.11(10) . . ?
C8 C7 C6 113.95(10) . . ?
N3 C7 H7 108.6 . . ?
C8 C7 H7 108.6 . . ?
C6 C7 H7 108.6 . . ?
N1 C8 C9 117.86(12) . . ?
N1 C8 C7 121.82(12) . . ?
C9 C8 C7 120.30(11) . . ?
C10 C9 C14 118.25(12) . . ?
C10 C9 C8 122.09(12) . . ?
C14 C9 C8 119.56(12) . . ?
C11 C10 C9 120.23(13) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 121.04(15) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.25(14) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 120.32(13) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 120.91(13) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
N2 C15 O1 122.22(12) . . ?
N2 C15 N3 122.85(12) . . ?
O1 C15 N3 114.78(11) . . ?
O1 C16 C17 107.05(12) . . ?
O1 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
O1 C16 H16B 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 O2 126.43(12) . . ?
O3 C18 N3 122.71(12) . . ?
O2 C18 N3 110.85(11) . . ?
O2 C19 C20 107.91(13) . . ?
O2 C19 H19A 110.1 . . ?
C20 C19 H19A 110.1 . . ?
O2 C19 H19B 110.1 . . ?
C20 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C15 -25.76(18) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
C2 C1 C6 C7 -176.10(13) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 C7 175.98(13) . . . . ?
C18 N3 C7 C8 132.30(11) . . . . ?
C15 N3 C7 C8 -44.83(13) . . . . ?
C18 N3 C7 C6 -103.44(13) . . . . ?
C15 N3 C7 C6 79.43(13) . . . . ?
C1 C6 C7 N3 88.34(15) . . . . ?
C5 C6 C7 N3 -88.42(15) . . . . ?
C1 C6 C7 C8 -152.06(13) . . . . ?
C5 C6 C7 C8 31.18(18) . . . . ?
N2 N1 C8 C9 -174.20(11) . . . . ?
N2 N1 C8 C7 4.35(18) . . . . ?
N3 C7 C8 N1 29.72(16) . . . . ?
C6 C7 C8 N1 -92.75(15) . . . . ?
N3 C7 C8 C9 -151.77(11) . . . . ?
C6 C7 C8 C9 85.77(14) . . . . ?
N1 C8 C9 C10 178.23(12) . . . . ?
C7 C8 C9 C10 -0.35(18) . . . . ?
N1 C8 C9 C14 1.82(18) . . . . ?
C7 C8 C9 C14 -176.76(11) . . . . ?
C14 C9 C10 C11 0.4(2) . . . . ?
C8 C9 C10 C11 -176.04(13) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C9 0.6(2) . . . . ?
C10 C9 C14 C13 -0.85(19) . . . . ?
C8 C9 C14 C13 175.70(12) . . . . ?
N1 N2 C15 O1 -176.99(11) . . . . ?
N1 N2 C15 N3 7.83(19) . . . . ?
C16 O1 C15 N2 15.70(18) . . . . ?
C16 O1 C15 N3 -168.76(11) . . . . ?
C18 N3 C15 N2 -147.13(13) . . . . ?
C7 N3 C15 N2 29.77(17) . . . . ?
C18 N3 C15 O1 37.36(17) . . . . ?
C7 N3 C15 O1 -145.74(11) . . . . ?
C15 O1 C16 C17 176.56(12) . . . . ?
C19 O2 C18 O3 9.4(2) . . . . ?
C19 O2 C18 N3 -172.13(12) . . . . ?
C15 N3 C18 O3 -171.30(12) . . . . ?
C7 N3 C18 O3 11.95(18) . . . . ?
C15 N3 C18 O2 10.20(17) . . . . ?
C7 N3 C18 O2 -166.55(10) . . . . ?
C18 O2 C19 C20 133.88(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C16 H16A N2 0.99 2.64 3.3330(19) 127.1 3_675 yes

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_R20190423D1
_database_code_depnum_ccdc_archive 'CCDC 1997894'
loop_
_audit_author_name
_audit_author_address
'Shixuan Cao'
;Nankai University
China
;
_audit_update_record             
;
2020-04-20 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 N3 O3'
_chemical_formula_weight         379.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.229(2)
_cell_length_b                   25.970(5)
_cell_length_c                   8.0314(16)
_cell_angle_alpha                90
_cell_angle_beta                 109.33(3)
_cell_angle_gamma                90
_cell_volume                     2013.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4368
_cell_measurement_theta_min      2.2512
_cell_measurement_theta_max      27.9223

_exptl_crystal_description       monoclinic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9033
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16735
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.110
_diffrn_reflns_theta_max         27.896
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4797
_reflns_number_gt                3788
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4797
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.10758(11) 0.17673(4) -0.08503(14) 0.0320(3) Uani 1 1 d . . . . .
O2 O -0.20924(10) 0.09809(4) -0.10627(13) 0.0257(3) Uani 1 1 d . . . . .
O3 O -0.13535(10) 0.04819(4) 0.20386(14) 0.0281(3) Uani 1 1 d . . . . .
N1 N -0.02599(12) 0.11720(4) 0.13160(16) 0.0235(3) Uani 1 1 d . . . . .
N2 N 0.09798(13) 0.04207(5) 0.25347(18) 0.0302(3) Uani 1 1 d . . . . .
N3 N 0.21365(12) 0.06404(5) 0.22072(18) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.10097(14) 0.14692(5) 0.21633(19) 0.0221(3) Uani 1 1 d . . . . .
H1 H 0.098412 0.178361 0.143456 0.027 Uiso 1 1 calc R U . . .
C2 C 0.11229(14) 0.16416(5) 0.40097(19) 0.0214(3) Uani 1 1 d . . . . .
C3 C 0.22844(15) 0.15351(6) 0.5455(2) 0.0289(4) Uani 1 1 d . . . . .
H3 H 0.302116 0.133899 0.530398 0.035 Uiso 1 1 calc R U . . .
C4 C 0.23790(17) 0.17131(6) 0.7125(2) 0.0337(4) Uani 1 1 d . . . . .
H4 H 0.318001 0.164036 0.810844 0.040 Uiso 1 1 calc R U . . .
C5 C 0.13080(16) 0.19954(6) 0.7349(2) 0.0310(4) Uani 1 1 d . . . . .
H5 H 0.136856 0.211640 0.848864 0.037 Uiso 1 1 calc R U . . .
C6 C 0.01479(16) 0.21021(6) 0.5917(2) 0.0306(4) Uani 1 1 d . . . . .
H6 H -0.058998 0.229651 0.607212 0.037 Uiso 1 1 calc R U . . .
C7 C 0.00564(15) 0.19270(6) 0.4259(2) 0.0274(3) Uani 1 1 d . . . . .
H7 H -0.074481 0.200271 0.327875 0.033 Uiso 1 1 calc R U . . .
C8 C 0.21984(14) 0.11336(6) 0.20808(19) 0.0238(3) Uani 1 1 d . . . . .
C9 C 0.34404(14) 0.13670(6) 0.18354(19) 0.0245(3) Uani 1 1 d . . . . .
C10 C 0.36221(15) 0.18987(6) 0.1885(2) 0.0292(4) Uani 1 1 d . . . . .
H10 H 0.294295 0.211541 0.209039 0.035 Uiso 1 1 calc R U . . .
C11 C 0.47825(17) 0.21154(7) 0.1638(2) 0.0380(4) Uani 1 1 d . . . . .
H11 H 0.489532 0.247877 0.167310 0.046 Uiso 1 1 calc R U . . .
C12 C 0.57771(16) 0.18016(7) 0.1341(2) 0.0395(4) Uani 1 1 d . . . . .
H12 H 0.656494 0.194991 0.115055 0.047 Uiso 1 1 calc R U . . .
C13 C 0.56241(16) 0.12732(7) 0.1320(2) 0.0361(4) Uani 1 1 d . . . . .
H13 H 0.631371 0.105821 0.113234 0.043 Uiso 1 1 calc R U . . .
C14 C 0.44678(15) 0.10556(6) 0.1573(2) 0.0302(4) Uani 1 1 d . . . . .
H14 H 0.437306 0.069168 0.156793 0.036 Uiso 1 1 calc R U . . .
C15 C -0.01657(15) 0.06702(6) 0.1958(2) 0.0248(3) Uani 1 1 d . . . . .
C16 C -0.13964(16) -0.00664(6) 0.2367(2) 0.0347(4) Uani 1 1 d . . . . .
H16A H -0.073978 -0.015461 0.354657 0.042 Uiso 1 1 calc R U . . .
H16B H -0.114388 -0.026555 0.146688 0.042 Uiso 1 1 calc R U . . .
C17 C -0.28500(17) -0.01858(7) 0.2271(3) 0.0450(5) Uani 1 1 d . . . . .
H17A H -0.306682 -0.000098 0.321068 0.067 Uiso 1 1 calc R U . . .
H17B H -0.294419 -0.055712 0.241690 0.067 Uiso 1 1 calc R U . . .
H17C H -0.349154 -0.007759 0.112148 0.067 Uiso 1 1 calc R U . . .
C18 C -0.11702(14) 0.13415(6) -0.03044(19) 0.0232(3) Uani 1 1 d . . . . .
C19 C -0.29470(15) 0.10205(6) -0.2973(2) 0.0262(3) Uani 1 1 d . . . . .
C20 C -0.19788(17) 0.09407(7) -0.4023(2) 0.0355(4) Uani 1 1 d . . . . .
H20A H -0.127337 0.121214 -0.373009 0.053 Uiso 1 1 calc R U . . .
H20B H -0.250798 0.095428 -0.528691 0.053 Uiso 1 1 calc R U . . .
H20C H -0.152767 0.060405 -0.373336 0.053 Uiso 1 1 calc R U . . .
C21 C -0.39362(16) 0.05724(6) -0.3184(2) 0.0367(4) Uani 1 1 d . . . . .
H21A H -0.340661 0.025292 -0.283081 0.055 Uiso 1 1 calc R U . . .
H21B H -0.453013 0.054646 -0.442101 0.055 Uiso 1 1 calc R U . . .
H21C H -0.451202 0.062768 -0.243828 0.055 Uiso 1 1 calc R U . . .
C22 C -0.37327(16) 0.15260(6) -0.3387(2) 0.0353(4) Uani 1 1 d . . . . .
H22A H -0.418777 0.159037 -0.250803 0.053 Uiso 1 1 calc R U . . .
H22B H -0.443300 0.150724 -0.456369 0.053 Uiso 1 1 calc R U . . .
H22C H -0.308494 0.180669 -0.335627 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C18 1.2050(17) . ?
O2 C18 1.3257(17) . ?
O2 C19 1.4969(18) . ?
O3 C15 1.3311(17) . ?
O3 C16 1.4512(18) . ?
N1 C15 1.3930(18) . ?
N1 C18 1.3971(19) . ?
N1 C1 1.4696(17) . ?
N2 C15 1.2837(18) . ?
N2 N3 1.4145(17) . ?
N3 C8 1.2881(19) . ?
C1 C8 1.5151(19) . ?
C1 C2 1.516(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.386(2) . ?
C2 C7 1.3869(19) . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.478(2) . ?
C9 C10 1.392(2) . ?
C9 C14 1.396(2) . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C16 C17 1.496(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 C20 1.513(2) . ?
C19 C21 1.514(2) . ?
C19 C22 1.517(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C18 O2 C19 120.50(11) . . ?
C15 O3 C16 116.89(11) . . ?
C15 N1 C18 125.63(12) . . ?
C15 N1 C1 112.18(11) . . ?
C18 N1 C1 118.69(12) . . ?
C15 N2 N3 116.67(12) . . ?
C8 N3 N2 118.81(12) . . ?
N1 C1 C8 106.06(11) . . ?
N1 C1 C2 112.19(12) . . ?
C8 C1 C2 114.21(12) . . ?
N1 C1 H1 108.1 . . ?
C8 C1 H1 108.1 . . ?
C2 C1 H1 108.1 . . ?
C3 C2 C7 118.87(14) . . ?
C3 C2 C1 121.78(13) . . ?
C7 C2 C1 119.32(13) . . ?
C2 C3 C4 120.50(14) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.87(15) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.93(15) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.20(15) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 120.63(14) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
N3 C8 C9 119.01(13) . . ?
N3 C8 C1 120.49(12) . . ?
C9 C8 C1 120.50(13) . . ?
C10 C9 C14 118.60(14) . . ?
C10 C9 C8 121.01(13) . . ?
C14 C9 C8 120.38(14) . . ?
C11 C10 C9 120.75(15) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.91(16) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.01(15) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.18(15) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.52(15) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
N2 C15 O3 122.39(13) . . ?
N2 C15 N1 123.29(13) . . ?
O3 C15 N1 114.16(12) . . ?
O3 C16 C17 106.46(13) . . ?
O3 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
O3 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 O2 127.71(14) . . ?
O1 C18 N1 121.27(13) . . ?
O2 C18 N1 111.02(12) . . ?
O2 C19 C20 107.11(12) . . ?
O2 C19 C21 101.76(12) . . ?
C20 C19 C21 111.64(14) . . ?
O2 C19 C22 111.79(12) . . ?
C20 C19 C22 113.17(14) . . ?
C21 C19 C22 110.76(13) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C15 N2 N3 C8 29.1(2) . . . . ?
C15 N1 C1 C8 48.93(16) . . . . ?
C18 N1 C1 C8 -111.18(14) . . . . ?
C15 N1 C1 C2 -76.40(15) . . . . ?
C18 N1 C1 C2 123.48(14) . . . . ?
N1 C1 C2 C3 126.20(14) . . . . ?
C8 C1 C2 C3 5.47(19) . . . . ?
N1 C1 C2 C7 -55.76(17) . . . . ?
C8 C1 C2 C7 -176.49(12) . . . . ?
C7 C2 C3 C4 -0.2(2) . . . . ?
C1 C2 C3 C4 177.83(14) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C3 C2 C7 C6 0.0(2) . . . . ?
C1 C2 C7 C6 -178.13(13) . . . . ?
N2 N3 C8 C9 176.71(12) . . . . ?
N2 N3 C8 C1 -3.9(2) . . . . ?
N1 C1 C8 N3 -34.19(18) . . . . ?
C2 C1 C8 N3 89.89(16) . . . . ?
N1 C1 C8 C9 145.17(13) . . . . ?
C2 C1 C8 C9 -90.75(16) . . . . ?
N3 C8 C9 C10 -172.92(14) . . . . ?
C1 C8 C9 C10 7.7(2) . . . . ?
N3 C8 C9 C14 6.2(2) . . . . ?
C1 C8 C9 C14 -173.20(13) . . . . ?
C14 C9 C10 C11 1.5(2) . . . . ?
C8 C9 C10 C11 -179.41(14) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C9 0.6(2) . . . . ?
C10 C9 C14 C13 -1.7(2) . . . . ?
C8 C9 C14 C13 179.17(14) . . . . ?
N3 N2 C15 O3 173.71(13) . . . . ?
N3 N2 C15 N1 -11.1(2) . . . . ?
C16 O3 C15 N2 -15.9(2) . . . . ?
C16 O3 C15 N1 168.47(13) . . . . ?
C18 N1 C15 N2 128.46(16) . . . . ?
C1 N1 C15 N2 -30.0(2) . . . . ?
C18 N1 C15 O3 -55.98(19) . . . . ?
C1 N1 C15 O3 145.56(12) . . . . ?
C15 O3 C16 C17 -176.15(14) . . . . ?
C19 O2 C18 O1 15.6(2) . . . . ?
C19 O2 C18 N1 -165.11(11) . . . . ?
C15 N1 C18 O1 -171.23(14) . . . . ?
C1 N1 C18 O1 -14.0(2) . . . . ?
C15 N1 C18 O2 9.4(2) . . . . ?
C1 N1 C18 O2 166.65(11) . . . . ?
C18 O2 C19 C20 69.08(16) . . . . ?
C18 O2 C19 C21 -173.65(12) . . . . ?
C18 O2 C19 C22 -55.41(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C22 H22C O1 0.98 2.35 2.875(2) 112.4 . yes
C21 H21A N3 0.98 2.62 3.601(2) 174.1 3 yes

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1997895'
loop_
_audit_author_name
_audit_author_address
'Shixuan Cao'
;Nankai University
China
;
_audit_update_record             
;
2020-04-20 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_audit_creation_date             2020-04-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_chemical_formula_moiety         'C21 H23 N3 O3'
_chemical_formula_sum            'C21 H23 N3 O3'
_chemical_formula_weight         365.435
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.5924(17)
_cell_length_b                   10.775(2)
_cell_length_c                   11.247(2)
_cell_angle_alpha                105.66(3)
_cell_angle_beta                 103.08(3)
_cell_angle_gamma                101.25(3)
_cell_volume                     939.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2743
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9544
_cell_measurement_theta_min      2.0404
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8130
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             388.181
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.9941
_diffrn_reflns_Laue_measured_fraction_max 0.9904
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11190
_diffrn_reflns_point_group_measured_fraction_full 0.9941
_diffrn_reflns_point_group_measured_fraction_max 0.9904
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         2.04
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.9941
_diffrn_measured_fraction_theta_max 0.9904
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3123
_reflns_number_total             4438
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.2540
_refine_diff_density_min         -0.3301
_refine_diff_density_rms         0.0769
_refine_ls_d_res_high            0.7605
_refine_ls_d_res_low             9.9813
_refine_ls_goodness_of_fit_ref   0.9896
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      0.9896
_refine_ls_shift/su_max          0.0217
_refine_ls_shift/su_mean         0.0011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1270
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C20(H20a,H20b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C18(H18a,H18b,H18c), C21(H21a,H21b,H21c)
;
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_refinement_flags_posn
O1 O 0.82834(13) 0.01509(11) -0.04457(11) 0.0305(3) Uani 1.000000 .
O2 O 0.59826(14) 0.05631(11) -0.14910(10) 0.0311(3) Uani 1.000000 .
O3 O 0.50395(12) 0.23963(10) -0.00247(10) 0.0235(3) Uani 1.000000 .
N1 N 0.76673(14) 0.21068(12) 0.03897(11) 0.0205(3) Uani 1.000000 .
N2 N 0.72399(15) 0.42591(12) 0.09695(12) 0.0231(3) Uani 1.000000 .
N3 N 0.89804(15) 0.48085(13) 0.13598(12) 0.0240(3) Uani 1.000000 .
C1 C 0.92459(17) 0.26051(14) 0.14524(13) 0.0202(3) Uani 1.000000 .
H1 H 1.00411(17) 0.21114(14) 0.11691(13) 0.0242(4) Uiso 1.000000 R
C2 C 0.90224(17) 0.23668(15) 0.26847(14) 0.0206(3) Uani 1.000000 .
C3 C 0.91438(19) 0.11593(16) 0.28691(16) 0.0277(4) Uani 1.000000 .
H3 H 0.93819(19) 0.05017(16) 0.22349(16) 0.0332(4) Uiso 1.000000 R
C4 C 0.8918(2) 0.09108(18) 0.39785(17) 0.0351(4) Uani 1.000000 .
H4 H 0.8993(2) 0.00821(18) 0.40974(17) 0.0421(5) Uiso 1.000000 R
C5 C 0.8584(2) 0.18709(19) 0.49081(16) 0.0363(4) Uani 1.000000 .
H5 H 0.8440(2) 0.17020(19) 0.56683(16) 0.0436(5) Uiso 1.000000 R
C6 C 0.8458(2) 0.30781(18) 0.47368(15) 0.0328(4) Uani 1.000000 .
H6 H 0.8221(2) 0.37330(18) 0.53745(15) 0.0394(5) Uiso 1.000000 R
C7 C 0.86797(19) 0.33258(16) 0.36255(15) 0.0259(3) Uani 1.000000 .
H7 H 0.85970(19) 0.41535(16) 0.35075(15) 0.0311(4) Uiso 1.000000 R
C8 C 0.99303(17) 0.40667(14) 0.16227(13) 0.0193(3) Uani 1.000000 .
C9 C 1.17399(17) 0.46955(15) 0.21597(14) 0.0209(3) Uani 1.000000 .
C10 C 1.24295(19) 0.59688(15) 0.21268(14) 0.0236(3) Uani 1.000000 .
H10 H 1.17364(19) 0.64146(15) 0.17193(14) 0.0283(4) Uiso 1.000000 R
C11 C 1.41127(19) 0.65855(15) 0.26828(14) 0.0254(3) Uani 1.000000 .
H11 H 1.45560(19) 0.74547(15) 0.26582(14) 0.0305(4) Uiso 1.000000 R
C12 C 1.51748(18) 0.59538(16) 0.32804(14) 0.0241(3) Uani 1.000000 .
C13 C 1.44840(18) 0.46917(16) 0.33131(14) 0.0250(3) Uani 1.000000 .
H13 H 1.51788(18) 0.42486(16) 0.37232(14) 0.0300(4) Uiso 1.000000 R
C14 C 1.27995(18) 0.40642(16) 0.27591(14) 0.0243(3) Uani 1.000000 .
H14 H 1.23600(18) 0.31958(16) 0.27869(14) 0.0291(4) Uiso 1.000000 R
C15 C 1.70143(19) 0.66022(17) 0.38241(16) 0.0309(4) Uani 1.000000 .
H15a H 1.7564(2) 0.6279(8) 0.3175(4) 0.0463(6) Uiso 1.000000 GR
H15b H 1.7226(2) 0.75769(18) 0.4055(10) 0.0463(6) Uiso 1.000000 GR
H15c H 1.7451(3) 0.6373(9) 0.4596(6) 0.0463(6) Uiso 1.000000 GR
C16 C 0.66637(17) 0.29817(15) 0.04503(14) 0.0205(3) Uani 1.000000 .
C17 C 0.39813(18) 0.32922(15) -0.01732(15) 0.0221(3) Uani 1.000000 .
H17a H 0.40386(18) 0.38939(15) 0.06835(15) 0.0265(4) Uiso 1.000000 R
H17b H 0.43481(18) 0.38477(15) -0.06831(15) 0.0265(4) Uiso 1.000000 R
C18 C 0.22388(19) 0.24189(16) -0.08627(17) 0.0297(4) Uani 1.000000 .
H18a H 0.2191(3) 0.1853(8) -0.1721(4) 0.0446(6) Uiso 1.000000 GR
H18b H 0.1907(5) 0.1851(8) -0.0363(5) 0.0446(6) Uiso 1.000000 GR
H18c H 0.1482(3) 0.29832(16) -0.0953(9) 0.0446(6) Uiso 1.000000 GR
C19 C 0.73578(18) 0.08498(15) -0.05294(14) 0.0219(3) Uani 1.000000 .
C20 C 0.5487(2) -0.07795(16) -0.24327(15) 0.0307(4) Uani 1.000000 .
H20a H 0.5883(2) -0.14006(16) -0.20077(15) 0.0368(5) Uiso 1.000000 R
H20b H 0.4260(2) -0.10968(16) -0.27644(15) 0.0368(5) Uiso 1.000000 R
C21 C 0.6188(2) -0.0789(2) -0.35316(18) 0.0453(5) Uani 1.000000 .
H21a H 0.5838(13) -0.0144(9) -0.3928(8) 0.0680(7) Uiso 1.000000 GR
H21b H 0.7404(2) -0.0541(12) -0.3213(3) 0.0680(7) Uiso 1.000000 GR
H21c H 0.5785(13) -0.1688(4) -0.4176(6) 0.0680(7) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.2028(17) . ?
O2 C19 1.3267(18) . ?
O2 C20 1.4576(19) . ?
O3 C16 1.3298(18) . ?
O3 C17 1.4653(17) . ?
N1 C1 1.4807(19) . ?
N1 C16 1.3950(17) . ?
N1 C19 1.3976(19) . ?
N2 N3 1.4131(17) . ?
N2 C16 1.2846(19) . ?
N3 C8 1.2904(18) . ?
C1 H1 1.0000 . ?
C1 C2 1.5223(19) . ?
C1 C8 1.513(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.394(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.478(2) . ?
C9 C10 1.398(2) . ?
C9 C14 1.399(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(2) . ?
C12 C13 1.388(2) . ?
C12 C15 1.504(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C15 H15a 0.9800 . ?
C15 H15b 0.9800 . ?
C15 H15c 0.9800 . ?
C17 H17a 0.9900 . ?
C17 H17b 0.9900 . ?
C17 C18 1.503(2) . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C20 H20a 0.9900 . ?
C20 H20b 0.9900 . ?
C20 C21 1.491(2) . ?
C21 H21a 0.9800 . ?
C21 H21b 0.9800 . ?
C21 H21c 0.9800 . ?

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
C20 O2 C19 115.69(12) . . ?
C17 O3 C16 115.80(11) . . ?
C16 N1 C1 114.08(11) . . ?
C19 N1 C1 117.68(12) . . ?
C19 N1 C16 128.23(12) . . ?
C16 N2 N3 117.91(12) . . ?
C8 N3 N2 118.94(12) . . ?
H1 C1 N1 108.11(7) . . ?
C2 C1 N1 112.28(12) . . ?
C2 C1 H1 108.11(8) . . ?
C8 C1 N1 106.61(11) . . ?
C8 C1 H1 108.11(8) . . ?
C8 C1 C2 113.43(12) . . ?
C3 C2 C1 119.27(14) . . ?
C7 C2 C1 121.44(13) . . ?
C7 C2 C3 119.29(14) . . ?
H3 C3 C2 119.86(9) . . ?
C4 C3 C2 120.28(16) . . ?
C4 C3 H3 119.86(10) . . ?
H4 C4 C3 120.01(10) . . ?
C5 C4 C3 119.97(16) . . ?
C5 C4 H4 120.01(10) . . ?
H5 C5 C4 119.81(10) . . ?
C6 C5 C4 120.38(16) . . ?
C6 C5 H5 119.81(10) . . ?
H6 C6 C5 120.17(10) . . ?
C7 C6 C5 119.67(16) . . ?
C7 C6 H6 120.17(10) . . ?
C6 C7 C2 120.42(15) . . ?
H7 C7 C2 119.79(9) . . ?
H7 C7 C6 119.79(10) . . ?
C1 C8 N3 122.21(13) . . ?
C9 C8 N3 118.20(13) . . ?
C9 C8 C1 119.54(12) . . ?
C10 C9 C8 120.51(13) . . ?
C14 C9 C8 121.29(13) . . ?
C14 C9 C10 118.15(13) . . ?
H10 C10 C9 119.70(8) . . ?
C11 C10 C9 120.60(14) . . ?
C11 C10 H10 119.70(9) . . ?
H11 C11 C10 119.35(9) . . ?
C12 C11 C10 121.30(14) . . ?
C12 C11 H11 119.35(9) . . ?
C13 C12 C11 117.88(14) . . ?
C15 C12 C11 120.94(14) . . ?
C15 C12 C13 121.14(14) . . ?
H13 C13 C12 119.35(9) . . ?
C14 C13 C12 121.31(14) . . ?
C14 C13 H13 119.35(9) . . ?
C13 C14 C9 120.75(14) . . ?
H14 C14 C9 119.62(9) . . ?
H14 C14 C13 119.62(9) . . ?
H15a C15 C12 109.5 . . ?
H15b C15 C12 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C12 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
N1 C16 O3 115.13(12) . . ?
N2 C16 O3 121.54(13) . . ?
N2 C16 N1 123.28(13) . . ?
H17a C17 O3 110.34(7) . . ?
H17b C17 O3 110.34(7) . . ?
H17b C17 H17a 108.6 . . ?
C18 C17 O3 106.92(11) . . ?
C18 C17 H17a 110.34(9) . . ?
C18 C17 H17b 110.34(8) . . ?
H18a C18 C17 109.5 . . ?
H18b C18 C17 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C17 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
O2 C19 O1 125.50(14) . . ?
N1 C19 O1 122.30(13) . . ?
N1 C19 O2 112.16(12) . . ?
H20a C20 O2 109.45(8) . . ?
H20b C20 O2 109.45(8) . . ?
H20b C20 H20a 108.0 . . ?
C21 C20 O2 110.94(14) . . ?
C21 C20 H20a 109.45(11) . . ?
C21 C20 H20b 109.45(10) . . ?
H21a C21 C20 109.5 . . ?
H21b C21 C20 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C20 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 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
O1 C19 O2 C20 7.28(19) . . . . ?
O1 C19 N1 C1 3.61(18) . . . . ?
O1 C19 N1 C16 -176.11(14) . . . . ?
O2 C19 N1 C1 -174.47(12) . . . . ?
O2 C19 N1 C16 5.80(17) . . . . ?
O3 C16 N1 C1 -148.90(12) . . . . ?
O3 C16 N1 C19 30.83(16) . . . . ?
O3 C16 N2 N3 -175.21(13) . . . . ?
N1 C1 C2 C3 87.93(13) . . . . ?
N1 C1 C2 C7 -91.32(13) . . . . ?
N1 C1 C8 N3 29.23(14) . . . . ?
N1 C1 C8 C9 -153.45(10) . . . . ?
N1 C16 N2 N3 7.63(16) . . . . ?
N2 N3 C8 C1 3.65(15) . . . . ?
N2 N3 C8 C9 -173.70(12) . . . . ?
N3 C8 C1 C2 -94.86(15) . . . . ?
N3 C8 C9 C10 -13.31(16) . . . . ?
N3 C8 C9 C14 164.07(13) . . . . ?
C1 C2 C3 C4 -178.98(13) . . . . ?
C1 C2 C7 C6 179.13(14) . . . . ?
C1 C8 C9 C10 169.26(13) . . . . ?
C1 C8 C9 C14 -13.35(15) . . . . ?
C2 C3 C4 C5 -0.50(18) . . . . ?
C2 C7 C6 C5 0.18(18) . . . . ?
C3 C4 C5 C6 0.56(19) . . . . ?
C4 C5 C6 C7 -0.40(19) . . . . ?
C8 C9 C10 C11 176.98(13) . . . . ?
C8 C9 C14 C13 -176.94(14) . . . . ?
C9 C10 C11 C12 0.64(17) . . . . ?
C9 C14 C13 C12 -0.67(17) . . . . ?
C10 C11 C12 C13 -0.77(17) . . . . ?
C10 C11 C12 C15 176.97(14) . . . . ?
C11 C12 C13 C14 0.78(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
