# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_xfp_100c_auto
_database_code_depnum_ccdc_archive 'CCDC 2179669'
loop_
_audit_author_name
_audit_author_address
'Fayang Xie'
;School of Pharmaceutical Sciences, Tsinghua University, Beijing, China
China
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2022-12-29 downloaded from the CCDC.
;
_audit_creation_date             2022-01-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H18 N2 O2'
_chemical_formula_sum            'C20 H18 N2 O2'
_chemical_formula_weight         318.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H17 N2 O2'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.7961(2)
_cell_length_b                   14.7189(3)
_cell_length_c                   12.7861(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1655.40(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10882
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.0460
_cell_measurement_theta_min      4.5750
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12126
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.061
_diffrn_reflns_theta_min         4.581
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  92.00   0.50    0.05    --  103.25 -77.00 150.00  122
  2  ω     31.00  75.00   0.50    0.05    --  103.25 -61.00 -30.00   88
  3  ω    -26.00  46.00   0.50    0.05    --   46.95 -37.00-120.00  144
  4  ω     31.00  56.00   0.50    0.05    --  103.25 -61.00-120.00   50
  5  ω     31.00  75.00   0.50    0.05    --  103.25 -61.00 -60.00   88
  6  ω     37.00  71.00   0.50    0.05    --  103.25 -61.00  30.00   68
  7  ω     33.00  74.00   0.50    0.05    --  103.25 -61.00  60.00   82
  8  ω     86.00 176.00   0.50    0.05    --  103.25  86.00   6.00  180
  9  ω     78.00 176.00   0.50    0.05    --  103.25 129.00  75.00  196
 10  ω     31.00 111.00   0.50    0.05    --  103.25-125.00  30.00  160
 11  ω   -102.00 -28.00   0.50    0.05    -- -101.00  77.00-120.00  148
 12  ω    -68.00 -28.00   0.50    0.05    -- -101.00  61.00 -60.00   80
 13  ω   -115.00 -28.00   0.50    0.05    -- -101.00 129.00  75.00  174
 14  ω   -102.00 -28.00   0.50    0.05    -- -101.00  77.00  90.00  148
 15  ω    -23.00  29.00   0.50    0.05    --  -46.95  19.00   0.00  104
 16  ω   -120.00 -34.00   0.50    0.05    --  -46.95 -35.00  54.00  172
 17  ω   -174.00 -88.00   0.50    0.05    -- -101.00 -35.00  54.00  172
 18  ω   -119.00 -74.00   0.50    0.05    --  -46.95-125.00 -90.00   90
 19  ω    -15.00  10.00   0.50    0.05    --   47.70 -35.00  54.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0545785000
_diffrn_orient_matrix_UB_12      -0.0815314000
_diffrn_orient_matrix_UB_13      -0.0655095000
_diffrn_orient_matrix_UB_21      0.0579680000
_diffrn_orient_matrix_UB_22      -0.0655087000
_diffrn_orient_matrix_UB_23      0.0850391000
_diffrn_orient_matrix_UB_31      -0.1560084000
_diffrn_orient_matrix_UB_32      0.0041832000
_diffrn_orient_matrix_UB_33      0.0546878000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3038
_reflns_number_total             3117
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 1180 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0628
_refine_ls_restrained_S_all      1.184
_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)+(0.0131P)²+3.3011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1452
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C4(H4a,H4b)
2.b Aromatic/amide H refined with riding coordinates:
 N9(H9), C23(H23), C24(H24), C14(H14), C21(H21), C6(H6), C11(H11), C12(H12),
 C20(H20), C7(H7), C22(H22)
2.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c)
;
_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
O18 O 1.0227(4) 0.5827(3) 0.1824(3) 0.0308(8) Uani 1 1 d . . . . .
O15 O 0.3218(4) 0.6859(3) 0.7055(3) 0.0323(9) Uani 1 1 d . . . . .
N5 N 0.7687(4) 0.5563(3) 0.1805(3) 0.0229(9) Uani 1 1 d . . . . .
N9 N 0.2966(5) 0.5841(3) 0.2936(3) 0.0259(9) Uani 1 1 d . . . . .
H9 H 0.220437 0.572092 0.251167 0.031 Uiso 1 1 calc R U . . .
C1 C 0.4303(5) 0.6230(3) 0.4369(4) 0.0216(10) Uani 1 1 d . . . . .
C2 C 0.5342(5) 0.5995(3) 0.3559(4) 0.0219(10) Uani 1 1 d . . . . .
C13 C 0.3204(6) 0.6632(3) 0.6016(4) 0.0248(11) Uani 1 1 d . . . . .
C23 C 1.0216(6) 0.6499(3) -0.1370(4) 0.0272(11) Uani 1 1 d . . . . .
H23 H 1.102210 0.635782 -0.183694 0.033 Uiso 1 1 calc R U . . .
C8 C 0.4493(5) 0.5763(3) 0.2687(4) 0.0237(10) Uani 1 1 d . . . . .
C10 C 0.2830(6) 0.6135(3) 0.3954(4) 0.0245(11) Uani 1 1 d . . . . .
C24 C 1.0141(5) 0.6086(3) -0.0392(4) 0.0254(11) Uani 1 1 d . . . . .
H24 H 1.091250 0.567039 -0.018910 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7043(5) 0.5942(3) 0.3665(4) 0.0235(10) Uani 1 1 d . . . . .
H3A H 0.730333 0.576787 0.439153 0.028 Uiso 1 1 calc R U . . .
H3B H 0.748575 0.654908 0.352988 0.028 Uiso 1 1 calc R U . . .
C14 C 0.4494(6) 0.6480(3) 0.5428(4) 0.0248(11) Uani 1 1 d . . . . .
H14 H 0.547810 0.654132 0.572566 0.030 Uiso 1 1 calc R U . . .
C21 C 0.7926(6) 0.7334(3) -0.0967(4) 0.0286(11) Uani 1 1 d . . . . .
H21 H 0.718006 0.776931 -0.115924 0.034 Uiso 1 1 calc R U . . .
C6 C 0.6321(5) 0.5442(3) 0.1246(4) 0.0255(11) Uani 1 1 d . . . . .
H6 H 0.640486 0.531542 0.051949 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1524(6) 0.6312(3) 0.4548(4) 0.0274(11) Uani 1 1 d . . . . .
H11 H 0.053621 0.626316 0.425369 0.033 Uiso 1 1 calc R U . . .
C12 C 0.1734(6) 0.6560(3) 0.5578(4) 0.0288(12) Uani 1 1 d . . . . .
H12 H 0.087251 0.668506 0.600180 0.035 Uiso 1 1 calc R U . . .
C20 C 0.7846(6) 0.6906(3) 0.0008(4) 0.0263(10) Uani 1 1 d . . . . .
H20 H 0.704132 0.704527 0.047697 0.032 Uiso 1 1 calc R U . . .
C17 C 0.8989(5) 0.5864(3) 0.1348(4) 0.0249(11) Uani 1 1 d . . . . .
C4 C 0.7743(6) 0.5257(3) 0.2913(4) 0.0247(11) Uani 1 1 d . . . . .
H4A H 0.881531 0.515095 0.311307 0.030 Uiso 1 1 calc R U . . .
H4B H 0.719431 0.467248 0.297701 0.030 Uiso 1 1 calc R U . . .
C19 C 0.8955(5) 0.6272(3) 0.0289(4) 0.0242(11) Uani 1 1 d . . . . .
C7 C 0.4929(6) 0.5487(3) 0.1641(4) 0.0285(12) Uani 1 1 d . . . . .
H7 H 0.412365 0.532010 0.118473 0.034 Uiso 1 1 calc R U . . .
C22 C 0.9100(6) 0.7122(3) -0.1658(4) 0.0293(12) Uani 1 1 d . . . . .
H22 H 0.913806 0.740220 -0.232654 0.035 Uiso 1 1 calc R U . . .
C16 C 0.4658(6) 0.6871(4) 0.7563(4) 0.0344(13) Uani 1 1 d . . . . .
H16A H 0.530493 0.733519 0.724062 0.052 Uiso 1 1 calc R U . . .
H16B H 0.514201 0.627479 0.749338 0.052 Uiso 1 1 calc R U . . .
H16C H 0.451767 0.701264 0.830616 0.052 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
O18 C17 1.248(6) . ?
O15 C13 1.370(6) . ?
O15 C16 1.423(6) . ?
N5 C6 1.409(6) . ?
N5 C17 1.360(6) . ?
N5 C4 1.487(6) . ?
N9 H9 0.8800 . ?
N9 C8 1.385(6) . ?
N9 C10 1.377(6) . ?
C1 C2 1.424(7) . ?
C1 C10 1.407(7) . ?
C1 C14 1.413(7) . ?
C2 C8 1.384(7) . ?
C2 C3 1.505(6) . ?
C13 C14 1.379(7) . ?
C13 C12 1.413(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(7) . ?
C23 C22 1.392(7) . ?
C8 C7 1.450(7) . ?
C10 C11 1.402(7) . ?
C24 H24 0.9500 . ?
C24 C19 1.386(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.523(6) . ?
C14 H14 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.399(7) . ?
C21 C22 1.394(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.326(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(8) . ?
C12 H12 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.397(7) . ?
C17 C19 1.481(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C7 H7 0.9500 . ?
C22 H22 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C13 O15 C16 117.0(4) . . ?
C6 N5 C4 118.2(4) . . ?
C17 N5 C6 122.8(4) . . ?
C17 N5 C4 118.7(4) . . ?
C8 N9 H9 125.4 . . ?
C10 N9 H9 125.4 . . ?
C10 N9 C8 109.1(4) . . ?
C10 C1 C2 106.9(4) . . ?
C10 C1 C14 119.8(4) . . ?
C14 C1 C2 133.2(5) . . ?
C1 C2 C3 125.8(5) . . ?
C8 C2 C1 107.5(4) . . ?
C8 C2 C3 126.6(4) . . ?
O15 C13 C14 124.1(5) . . ?
O15 C13 C12 114.3(5) . . ?
C14 C13 C12 121.6(5) . . ?
C24 C23 H23 120.3 . . ?
C24 C23 C22 119.4(5) . . ?
C22 C23 H23 120.3 . . ?
N9 C8 C7 119.4(4) . . ?
C2 C8 N9 108.5(4) . . ?
C2 C8 C7 132.0(4) . . ?
N9 C10 C1 108.0(4) . . ?
N9 C10 C11 129.9(5) . . ?
C11 C10 C1 122.1(5) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 C23 120.9(5) . . ?
C19 C24 H24 119.5 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C2 C3 C4 112.3(4) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C1 C14 H14 121.1 . . ?
C13 C14 C1 117.8(5) . . ?
C13 C14 H14 121.1 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C22 C21 C20 120.1(5) . . ?
N5 C6 H6 117.0 . . ?
C7 C6 N5 126.0(5) . . ?
C7 C6 H6 117.0 . . ?
C10 C11 H11 121.4 . . ?
C12 C11 C10 117.2(5) . . ?
C12 C11 H11 121.4 . . ?
C13 C12 H12 119.3 . . ?
C11 C12 C13 121.4(5) . . ?
C11 C12 H12 119.3 . . ?
C21 C20 H20 120.2 . . ?
C19 C20 C21 119.6(5) . . ?
C19 C20 H20 120.2 . . ?
O18 C17 N5 120.7(5) . . ?
O18 C17 C19 118.7(4) . . ?
N5 C17 C19 120.5(4) . . ?
N5 C4 C3 112.9(4) . . ?
N5 C4 H4A 109.0 . . ?
N5 C4 H4B 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C24 C19 C20 119.7(5) . . ?
C24 C19 C17 118.6(4) . . ?
C20 C19 C17 121.3(4) . . ?
C8 C7 H7 116.2 . . ?
C6 C7 C8 127.6(5) . . ?
C6 C7 H7 116.2 . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N9 H9 O18 0.88 1.96 2.798(5) 159.8 1_455 yes

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
O18 C17 C19 C24 40.1(6) . . . . ?
O18 C17 C19 C20 -133.3(5) . . . . ?
O15 C13 C14 C1 178.6(4) . . . . ?
O15 C13 C12 C11 -178.2(4) . . . . ?
N5 C6 C7 C8 7.2(9) . . . . ?
N5 C17 C19 C24 -142.0(5) . . . . ?
N5 C17 C19 C20 44.6(6) . . . . ?
N9 C8 C7 C6 174.8(5) . . . . ?
N9 C10 C11 C12 176.9(5) . . . . ?
C1 C2 C8 N9 -0.5(5) . . . . ?
C1 C2 C8 C7 178.7(5) . . . . ?
C1 C2 C3 C4 151.2(4) . . . . ?
C1 C10 C11 C12 -1.9(7) . . . . ?
C2 C1 C10 N9 0.8(5) . . . . ?
C2 C1 C10 C11 179.9(4) . . . . ?
C2 C1 C14 C13 -177.4(5) . . . . ?
C2 C8 C7 C6 -4.3(9) . . . . ?
C2 C3 C4 N5 70.7(5) . . . . ?
C23 C24 C19 C20 -2.2(7) . . . . ?
C23 C24 C19 C17 -175.7(4) . . . . ?
C8 N9 C10 C1 -1.2(5) . . . . ?
C8 N9 C10 C11 179.9(5) . . . . ?
C8 C2 C3 C4 -23.7(7) . . . . ?
C10 N9 C8 C2 1.0(5) . . . . ?
C10 N9 C8 C7 -178.2(4) . . . . ?
C10 C1 C2 C8 -0.2(5) . . . . ?
C10 C1 C2 C3 -176.0(4) . . . . ?
C10 C1 C14 C13 -0.7(6) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C24 C23 C22 C21 0.6(7) . . . . ?
C3 C2 C8 N9 175.2(4) . . . . ?
C3 C2 C8 C7 -5.6(9) . . . . ?
C14 C1 C2 C8 176.8(5) . . . . ?
C14 C1 C2 C3 1.1(8) . . . . ?
C14 C1 C10 N9 -176.7(4) . . . . ?
C14 C1 C10 C11 2.4(7) . . . . ?
C14 C13 C12 C11 1.7(7) . . . . ?
C21 C20 C19 C24 1.2(7) . . . . ?
C21 C20 C19 C17 174.6(4) . . . . ?
C6 N5 C17 O18 -168.6(4) . . . . ?
C6 N5 C17 C19 13.5(7) . . . . ?
C6 N5 C4 C3 -81.2(5) . . . . ?
C12 C13 C14 C1 -1.2(7) . . . . ?
C20 C21 C22 C23 -1.5(7) . . . . ?
C17 N5 C6 C7 -153.0(5) . . . . ?
C17 N5 C4 C3 105.0(5) . . . . ?
C4 N5 C6 C7 33.5(7) . . . . ?
C4 N5 C17 O18 4.9(7) . . . . ?
C4 N5 C17 C19 -173.0(4) . . . . ?
C22 C23 C24 C19 1.3(7) . . . . ?
C22 C21 C20 C19 0.6(7) . . . . ?
C16 O15 C13 C14 -4.7(7) . . . . ?
C16 O15 C13 C12 175.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.184
_oxdiff_exptl_absorpt_empirical_full_min 0.783
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ???????'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_750
_database_code_depnum_ccdc_archive 'CCDC 2179725'
loop_
_audit_author_name
_audit_author_address
'Fayang Xie'
;School of Pharmaceutical Sciences, Tsinghua University, Beijing, China
China
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2022-12-29 downloaded from the CCDC.
;
_audit_creation_date             2017-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H19 N O'
_chemical_formula_sum            'C12 H19 N O'
_chemical_formula_weight         193.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1N1O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.0479(5)
_cell_length_b                   10.5812(7)
_cell_length_c                   29.416(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2193.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2746
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5300
_cell_measurement_theta_min      4.0060
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9693
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.740
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.9937
_diffrn_measured_fraction_theta_max 0.8871
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  20.00   0.50    1.45    --   -0.10 -82.00 -60.00  106
  2  ω    -79.00 -40.00   0.50    1.45    --   -0.10 -19.00-150.00   78
  3  ω    -41.00   6.00   0.50    1.45    --   -0.10 -77.00   0.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0268339000
_diffrn_orient_matrix_UB_12      0.0067687000
_diffrn_orient_matrix_UB_13      -0.0231230000
_diffrn_orient_matrix_UB_21      0.0950567000
_diffrn_orient_matrix_UB_22      0.0114024000
_diffrn_orient_matrix_UB_23      0.0067583000
_diffrn_orient_matrix_UB_31      0.0191754000
_diffrn_orient_matrix_UB_32      -0.0657036000
_diffrn_orient_matrix_UB_33      -0.0011982000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1867
_reflns_number_total             2156
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0443P)²+1.1479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1253
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C 0.4934(2) 0.31313(17) 0.56337(6) 0.0403(4) Uani 1 1 d . . . . .
H1A H 0.3857 0.2611 0.5549 0.048 Uiso 1 1 calc R . . . .
H1B H 0.5520 0.2750 0.5899 0.048 Uiso 1 1 calc R . . . .
C2 C 0.6355(3) 0.31255(18) 0.52454(6) 0.0438(4) Uani 1 1 d . . . . .
H2A H 0.5685 0.3169 0.4958 0.053 Uiso 1 1 calc R . . . .
H2B H 0.7076 0.2345 0.5251 0.053 Uiso 1 1 calc R . . . .
C3 C 0.7701(3) 0.42460(17) 0.52863(6) 0.0397(4) Uani 1 1 d . . . . .
H3A H 0.8780 0.4098 0.5089 0.048 Uiso 1 1 calc R . . . .
H3B H 0.7053 0.4994 0.5176 0.048 Uiso 1 1 calc R . . . .
C4 C 0.8435(2) 0.45160(16) 0.57610(6) 0.0342(4) Uani 1 1 d . . . . .
C5 C 0.7186(2) 0.50935(15) 0.60905(5) 0.0306(4) Uani 1 1 d . . . . .
C6 C 0.8106(2) 0.57113(17) 0.65012(6) 0.0387(4) Uani 1 1 d . . . . .
H6A H 0.8322 0.5072 0.6732 0.046 Uiso 1 1 calc R . . . .
H6B H 0.9333 0.6046 0.6412 0.046 Uiso 1 1 calc R . . . .
C7 C 0.6935(3) 0.67717(17) 0.67065(6) 0.0410(4) Uani 1 1 d . . . . .
H7A H 0.7031 0.7511 0.6513 0.049 Uiso 1 1 calc R . . . .
H7B H 0.7460 0.6991 0.7001 0.049 Uiso 1 1 calc R . . . .
C8 C 0.4842(2) 0.64299(16) 0.67650(6) 0.0375(4) Uani 1 1 d . . . . .
C9 C 0.4060(2) 0.60960(19) 0.62947(6) 0.0428(4) Uani 1 1 d . . . . .
H9A H 0.2788 0.5759 0.6330 0.051 Uiso 1 1 calc R . . . .
H9B H 0.3966 0.6864 0.6116 0.051 Uiso 1 1 calc R . . . .
C10 C 0.5243(2) 0.51502(16) 0.60368(5) 0.0313(4) Uani 1 1 d . . . . .
C11 C 0.4615(3) 0.5311(2) 0.70884(7) 0.0557(5) Uani 1 1 d . . . . .
H11A H 0.3291 0.5135 0.7131 0.084 Uiso 1 1 calc GR . . . .
H11B H 0.5182 0.5513 0.7376 0.084 Uiso 1 1 calc GR . . . .
H11C H 0.5230 0.4582 0.6962 0.084 Uiso 1 1 calc GR . . . .
C12 C 0.3749(3) 0.7566(2) 0.69489(8) 0.0597(6) Uani 1 1 d . . . . .
H12A H 0.2432 0.7350 0.6979 0.090 Uiso 1 1 calc GR . . . .
H12B H 0.3877 0.8263 0.6742 0.090 Uiso 1 1 calc GR . . . .
H12C H 0.4250 0.7799 0.7241 0.090 Uiso 1 1 calc GR . . . .
N1 N 0.4252(2) 0.43799(15) 0.57554(5) 0.0387(4) Uani 1 1 d . . . . .
O1 O 1.01438(16) 0.43595(14) 0.58433(5) 0.0537(4) Uani 1 1 d . . . . .
H1 H 0.308(3) 0.4442(19) 0.5771(7) 0.045(6) Uiso 1 1 d . . . . .


_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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.519(2) . ?
C1 N1 1.451(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.523(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.516(2) . ?
C4 C5 1.445(2) . ?
C4 O1 1.2398(19) . ?
C5 C6 1.519(2) . ?
C5 C10 1.380(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.518(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.529(2) . ?
C8 C9 1.530(2) . ?
C8 C11 1.527(3) . ?
C8 C12 1.527(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.507(2) . ?
C10 N1 1.356(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1 0.83(2) . ?

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
H1A C1 H1B 107.6 . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
N1 C1 C2 114.05(15) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C1 C2 C3 110.38(14) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 C2 115.57(15) . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C5 C4 C3 119.34(14) . . ?
O1 C4 C3 119.07(16) . . ?
O1 C4 C5 121.15(16) . . ?
C4 C5 C6 117.10(14) . . ?
C10 C5 C4 123.10(14) . . ?
C10 C5 C6 119.73(14) . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.71(14) . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C6 C7 C8 113.25(14) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 C9 107.48(14) . . ?
C11 C8 C7 110.76(16) . . ?
C11 C8 C9 110.29(16) . . ?
C12 C8 C7 109.92(15) . . ?
C12 C8 C9 108.69(16) . . ?
C12 C8 C11 109.66(16) . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.14(14) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C5 C10 C9 121.35(15) . . ?
N1 C10 C5 123.71(15) . . ?
N1 C10 C9 114.93(14) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 H1 114.5(14) . . ?
C10 N1 C1 121.85(14) . . ?
C10 N1 H1 115.6(14) . . ?

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
C1 C2 C3 C4 43.0(2) . . . . ?
C2 C1 N1 C10 -83.1(2) . . . . ?
C2 C3 C4 C5 -74.6(2) . . . . ?
C2 C3 C4 O1 112.92(19) . . . . ?
C3 C4 C5 C6 -161.50(15) . . . . ?
C3 C4 C5 C10 15.7(2) . . . . ?
C4 C5 C6 C7 153.19(15) . . . . ?
C4 C5 C10 C9 -159.76(16) . . . . ?
C4 C5 C10 N1 20.3(3) . . . . ?
C5 C6 C7 C8 46.1(2) . . . . ?
C5 C10 N1 C1 26.4(3) . . . . ?
C6 C5 C10 C9 17.3(2) . . . . ?
C6 C5 C10 N1 -162.58(16) . . . . ?
C6 C7 C8 C9 -58.89(19) . . . . ?
C6 C7 C8 C11 61.6(2) . . . . ?
C6 C7 C8 C12 -177.01(16) . . . . ?
C7 C8 C9 C10 50.3(2) . . . . ?
C8 C9 C10 C5 -31.6(2) . . . . ?
C8 C9 C10 N1 148.30(16) . . . . ?
C9 C10 N1 C1 -153.53(16) . . . . ?
C10 C5 C6 C7 -24.1(2) . . . . ?
C11 C8 C9 C10 -70.6(2) . . . . ?
C12 C8 C9 C10 169.20(16) . . . . ?
N1 C1 C2 C3 39.1(2) . . . . ?
O1 C4 C5 C6 10.8(2) . . . . ?
O1 C4 C5 C10 -172.01(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.316
_oxdiff_exptl_absorpt_empirical_full_min 0.505
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ???????'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_749
_database_code_depnum_ccdc_archive 'CCDC 2179723'
loop_
_audit_author_name
_audit_author_address
'Fayang Xie'
;School of Pharmaceutical Sciences, Tsinghua University, Beijing, China
China
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2022-12-29 downloaded from the CCDC.
;
_audit_creation_date             2017-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H21 N O'
_chemical_formula_sum            'C17 H21 N O'
_chemical_formula_weight         255.35
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1N1O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, z+1/2'

_cell_length_a                   24.820(3)
_cell_length_b                   16.9474(15)
_cell_length_c                   6.8317(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2873.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2444
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0220
_cell_measurement_theta_min      4.2740
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6111
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.008
_diffrn_reflns_theta_min         3.610
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.9933
_diffrn_measured_fraction_theta_max 0.9022
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00  -1.00   0.50    6.51    --   -0.10 -38.00 120.00  112
  2  ω    -26.00   4.00   0.50    6.51    --   -0.10 -82.00 -90.00   60
  3  ω    -41.00   1.00   0.50    6.51    --   -0.10 -77.00  60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0033109000
_diffrn_orient_matrix_UB_12      -0.0415188000
_diffrn_orient_matrix_UB_13      -0.0033851000
_diffrn_orient_matrix_UB_21      -0.0269303000
_diffrn_orient_matrix_UB_22      -0.0040900000
_diffrn_orient_matrix_UB_23      -0.0334371000
_diffrn_orient_matrix_UB_31      0.0090387000
_diffrn_orient_matrix_UB_32      0.0028304000
_diffrn_orient_matrix_UB_33      -0.0982729000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.868
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                2292
_reflns_number_total             2647
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 844 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2647
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.3378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C 0.33745(8) 0.64783(11) 0.3613(3) 0.0485(5) Uani 1 1 d . . . . .
C2 C 0.30882(9) 0.58405(12) 0.4846(3) 0.0530(5) Uani 1 1 d . . . . .
H2A H 0.2993 0.5406 0.3989 0.064 Uiso 1 1 calc R . . . .
H2B H 0.3342 0.5640 0.5804 0.064 Uiso 1 1 calc R . . . .
C3 C 0.25858(9) 0.61069(12) 0.5911(3) 0.0479(5) Uani 1 1 d . . . . .
C4 C 0.20874(8) 0.61755(11) 0.4834(3) 0.0447(5) Uani 1 1 d . . . . .
C5 C 0.20936(9) 0.62041(12) 0.2816(3) 0.0518(5) Uani 1 1 d . . . . .
H5 H 0.1780 0.6055 0.2170 0.062 Uiso 1 1 calc R . . . .
C6 C 0.29377(9) 0.69157(12) 0.2479(3) 0.0546(5) Uani 1 1 d . . . . .
H6A H 0.2781 0.7311 0.3333 0.066 Uiso 1 1 calc R . . . .
H6B H 0.3106 0.7191 0.1395 0.066 Uiso 1 1 calc R . . . .
C7 C 0.37798(10) 0.60965(13) 0.2194(3) 0.0621(6) Uani 1 1 d . . . . .
H7A H 0.3597 0.5691 0.1444 0.075 Uiso 1 1 calc R . . . .
H7B H 0.3907 0.6494 0.1282 0.075 Uiso 1 1 calc R . . . .
C8 C 0.42577(11) 0.57348(18) 0.3224(5) 0.0809(8) Uani 1 1 d . . . . .
H8A H 0.4137 0.5313 0.4076 0.097 Uiso 1 1 calc R . . . .
H8B H 0.4503 0.5512 0.2266 0.097 Uiso 1 1 calc R . . . .
C9 C 0.45472(12) 0.6352(2) 0.4415(6) 0.0995(11) Uani 1 1 d . . . . .
H9A H 0.4691 0.6753 0.3547 0.119 Uiso 1 1 calc R . . . .
H9B H 0.4847 0.6110 0.5099 0.119 Uiso 1 1 calc R . . . .
C10 C 0.41706(11) 0.6740(2) 0.5903(5) 0.0885(9) Uani 1 1 d . . . . .
H10A H 0.4063 0.6353 0.6872 0.106 Uiso 1 1 calc R . . . .
H10B H 0.4361 0.7161 0.6573 0.106 Uiso 1 1 calc R . . . .
C11 C 0.36712(9) 0.70761(14) 0.4910(4) 0.0639(6) Uani 1 1 d . . . . .
H11A H 0.3777 0.7524 0.4114 0.077 Uiso 1 1 calc R . . . .
H11B H 0.3425 0.7266 0.5908 0.077 Uiso 1 1 calc R . . . .
C12 C 0.15561(9) 0.61542(11) 0.5827(3) 0.0498(5) Uani 1 1 d . . . . .
C13 C 0.14646(10) 0.56984(13) 0.7508(3) 0.0593(6) Uani 1 1 d . . . . .
H13 H 0.1750 0.5432 0.8089 0.071 Uiso 1 1 calc R . . . .
C14 C 0.09580(11) 0.56414(17) 0.8306(4) 0.0780(8) Uani 1 1 d . . . . .
H14 H 0.0905 0.5333 0.9416 0.094 Uiso 1 1 calc R . . . .
C15 C 0.05309(13) 0.6032(2) 0.7491(6) 0.0892(9) Uani 1 1 d . . . . .
H15 H 0.0188 0.5977 0.8021 0.107 Uiso 1 1 calc R . . . .
C16 C 0.06124(11) 0.65108(19) 0.5871(5) 0.0819(8) Uani 1 1 d . . . . .
H16 H 0.0326 0.6791 0.5333 0.098 Uiso 1 1 calc R . . . .
C17 C 0.11214(10) 0.65688(14) 0.5059(4) 0.0640(6) Uani 1 1 d . . . . .
H17 H 0.1174 0.6892 0.3976 0.077 Uiso 1 1 calc R . . . .
N1 N 0.25068(9) 0.64255(12) 0.1712(3) 0.0570(5) Uani 1 1 d . . . . .
O1 O 0.26111(7) 0.61937(11) 0.7707(2) 0.0678(5) Uani 1 1 d . . . . .
H1 H 0.2466(9) 0.6360(16) 0.049(5) 0.071(8) Uiso 1 1 d . . . . .


_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
C1 C2 1.543(3) . ?
C1 C6 1.525(3) . ?
C1 C7 1.540(3) . ?
C1 C11 1.534(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.513(3) . ?
C3 C4 1.444(3) . ?
C3 O1 1.237(2) . ?
C4 C5 1.380(3) . ?
C4 C12 1.483(3) . ?
C5 H5 0.9300 . ?
C5 N1 1.327(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N1 1.452(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.509(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.508(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.529(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.523(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.403(3) . ?
C12 C17 1.390(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(4) . ?
C17 H17 0.9300 . ?
N1 H1 0.85(3) . ?

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
C6 C1 C2 106.88(16) . . ?
C6 C1 C7 110.41(18) . . ?
C6 C1 C11 108.28(17) . . ?
C7 C1 C2 110.49(17) . . ?
C11 C1 C2 111.62(18) . . ?
C11 C1 C7 109.12(17) . . ?
C1 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 C1 115.65(17) . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C4 C3 C2 119.02(18) . . ?
O1 C3 C2 118.1(2) . . ?
O1 C3 C4 122.6(2) . . ?
C3 C4 C12 121.79(17) . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 C12 117.9(2) . . ?
C4 C5 H5 117.0 . . ?
N1 C5 C4 125.9(2) . . ?
N1 C5 H5 117.0 . . ?
C1 C6 H6A 108.4 . . ?
C1 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
N1 C6 C1 115.40(17) . . ?
N1 C6 H6A 108.4 . . ?
N1 C6 H6B 108.4 . . ?
C1 C7 H7A 109.0 . . ?
C1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C1 113.0(2) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 C7 110.1(2) . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C8 C9 C10 111.4(2) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.2(2) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C1 C11 H11A 108.8 . . ?
C1 C11 H11B 108.8 . . ?
C10 C11 C1 113.6(2) . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C4 122.1(2) . . ?
C17 C12 C4 120.3(2) . . ?
C17 C12 C13 117.5(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.4(2) . . ?
C16 C17 H17 119.3 . . ?
C5 N1 C6 121.7(2) . . ?
C5 N1 H1 115.5(17) . . ?
C6 N1 H1 121.2(17) . . ?

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
C1 C2 C3 C4 79.0(2) . . . . ?
C1 C2 C3 O1 -106.9(2) . . . . ?
C1 C6 N1 C5 82.4(3) . . . . ?
C1 C7 C8 C9 -58.3(3) . . . . ?
C2 C1 C6 N1 -39.5(2) . . . . ?
C2 C1 C7 C8 -68.7(3) . . . . ?
C2 C1 C11 C10 71.0(3) . . . . ?
C2 C3 C4 C5 -17.0(3) . . . . ?
C2 C3 C4 C12 158.17(18) . . . . ?
C3 C4 C5 N1 -23.1(3) . . . . ?
C3 C4 C12 C13 -33.1(3) . . . . ?
C3 C4 C12 C17 149.4(2) . . . . ?
C4 C5 N1 C6 -21.6(3) . . . . ?
C4 C12 C13 C14 -174.8(2) . . . . ?
C4 C12 C17 C16 175.0(2) . . . . ?
C5 C4 C12 C13 142.1(2) . . . . ?
C5 C4 C12 C17 -35.3(3) . . . . ?
C6 C1 C2 C3 -44.8(2) . . . . ?
C6 C1 C7 C8 173.3(2) . . . . ?
C6 C1 C11 C10 -171.7(2) . . . . ?
C7 C1 C2 C3 -164.9(2) . . . . ?
C7 C1 C6 N1 80.7(2) . . . . ?
C7 C1 C11 C10 -51.4(3) . . . . ?
C7 C8 C9 C10 57.4(4) . . . . ?
C8 C9 C10 C11 -54.7(4) . . . . ?
C9 C10 C11 C1 52.6(3) . . . . ?
C11 C1 C2 C3 73.5(2) . . . . ?
C11 C1 C6 N1 -159.87(19) . . . . ?
C11 C1 C7 C8 54.4(3) . . . . ?
C12 C4 C5 N1 161.6(2) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C12 C17 C16 -2.5(3) . . . . ?
C13 C14 C15 C16 -1.9(4) . . . . ?
C14 C15 C16 C17 2.0(4) . . . . ?
C15 C16 C17 C12 0.3(4) . . . . ?
C17 C12 C13 C14 2.7(3) . . . . ?
O1 C3 C4 C5 169.2(2) . . . . ?
O1 C3 C4 C12 -15.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.546
_oxdiff_exptl_absorpt_empirical_full_min 0.448
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ???????'
####################################################################### 
# 
# 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_20181217xiefayang-2
_database_code_depnum_ccdc_archive 'CCDC 2179728'
loop_
_audit_author_name
_audit_author_address
'Fayang Xie'
;School of Pharmaceutical Sciences, Tsinghua University, Beijing, China
China
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2022-12-29 downloaded from the CCDC.
;
_audit_creation_date             2018-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H21 N O'
_chemical_formula_sum            'C13 H21 N O'
_chemical_formula_weight         207.31
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1335(7)
_cell_length_b                   6.9499(4)
_cell_length_c                   19.3720(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.031(6)
_cell_angle_gamma                90
_cell_volume                     1220.44(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1144
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      70.7590
_cell_measurement_theta_min      5.1320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4057
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.536
_diffrn_reflns_theta_min         4.600
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  22.00   1.00    1.50    --  -40.81  57.00 -90.00   90
  2  ω    -90.00   0.00   1.00    1.50    --  -40.81 -19.00  60.00   90
  3  ω     32.00 127.00   1.00    5.50    --  100.91 -45.00  30.00   95
  4  ω     79.00 173.00   1.00    5.50    --  100.91  61.00-180.00   94
  5  ω    115.00 173.00   1.00    5.50    --  100.91 125.00  60.00   58
  6  ω     73.00 150.00   1.00    5.50    --  100.91  61.00 -90.00   77
  7  ω     79.00 130.00   1.00    5.50    --  100.91 -15.00-150.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0602957000
_diffrn_orient_matrix_UB_12      -0.1010785000
_diffrn_orient_matrix_UB_13      -0.0615140000
_diffrn_orient_matrix_UB_21      0.1418187000
_diffrn_orient_matrix_UB_22      0.1211830000
_diffrn_orient_matrix_UB_23      0.0126993000
_diffrn_orient_matrix_UB_31      0.0717709000
_diffrn_orient_matrix_UB_32      -0.1559537000
_diffrn_orient_matrix_UB_33      0.0495821000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1650
_reflns_number_total             2299
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0616
_refine_ls_restrained_S_all      1.059
_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)+(0.0910P)²+0.3177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1873
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0714(2) 0.7611(2) 0.16879(9) 0.0401(5) Uani 1 1 d . . . . .
H1 H 0.0760 0.6404 0.1787 0.048 Uiso 1 1 calc R . . . .
O2 O 0.0797(3) 1.3451(2) 0.17134(10) 0.0711(6) Uani 1 1 d . . . . .
C3 C 0.2219(3) 1.0527(3) 0.17682(11) 0.0447(5) Uani 1 1 d . . . . .
H3 H 0.2532 1.0305 0.2264 0.054 Uiso 1 1 calc R . . . .
C4 C -0.0531(3) 1.0576(3) 0.17479(13) 0.0501(6) Uani 1 1 d . . . . .
H4 H -0.1425 1.1215 0.1749 0.060 Uiso 1 1 calc R . . . .
C5 C 0.1968(2) 0.8539(3) 0.14283(11) 0.0386(5) Uani 1 1 d . . . . .
H5 H 0.2845 0.7753 0.1567 0.046 Uiso 1 1 calc R . . . .
C6 C -0.0507(3) 0.8596(3) 0.17749(11) 0.0415(5) Uani 1 1 d . . . . .
C7 C 0.3038(3) 0.9716(4) 0.03742(14) 0.0573(7) Uani 1 1 d . . . . .
H7A H 0.3935 0.8984 0.0499 0.069 Uiso 1 1 calc R . . . .
H7B H 0.2877 0.9818 -0.0129 0.069 Uiso 1 1 calc R . . . .
C8 C 0.0772(3) 1.1666(3) 0.17186(11) 0.0492(6) Uani 1 1 d . . . . .
C9 C 0.1745(3) 0.8665(3) 0.06288(11) 0.0437(5) Uani 1 1 d . . . . .
H9 H 0.0850 0.9417 0.0490 0.052 Uiso 1 1 calc R . . . .
C10 C -0.1825(3) 0.7420(4) 0.18814(14) 0.0544(6) Uani 1 1 d . . . . .
H10A H -0.2498 0.8192 0.2116 0.065 Uiso 1 1 calc R . . . .
H10B H -0.1519 0.6329 0.2177 0.065 Uiso 1 1 calc R . . . .
C11 C 0.1542(4) 0.6694(4) 0.02917(14) 0.0621(7) Uani 1 1 d . . . . .
H11A H 0.2425 0.5950 0.0404 0.093 Uiso 1 1 calc GR . . . .
H11B H 0.1344 0.6839 -0.0204 0.093 Uiso 1 1 calc GR . . . .
H11C H 0.0730 0.6047 0.0462 0.093 Uiso 1 1 calc GR . . . .
C12 C 0.3465(3) 1.1596(4) 0.14862(14) 0.0620(7) Uani 1 1 d . . . . .
H12A H 0.4389 1.0941 0.1631 0.074 Uiso 1 1 calc R . . . .
H12B H 0.3534 1.2886 0.1679 0.074 Uiso 1 1 calc R . . . .
C13 C 0.3220(4) 1.1716(4) 0.06892(14) 0.0674(8) Uani 1 1 d . . . . .
H13A H 0.2345 1.2474 0.0544 0.081 Uiso 1 1 calc R . . . .
H13B H 0.4056 1.2351 0.0523 0.081 Uiso 1 1 calc R . . . .
C14 C -0.2612(4) 0.6705(6) 0.12008(16) 0.0803(10) Uani 1 1 d . . . . .
H14A H -0.2965 0.7805 0.0920 0.096 Uiso 1 1 calc R . . . .
H14B H -0.1911 0.6022 0.0953 0.096 Uiso 1 1 calc R . . . .
C15 C -0.3890(4) 0.5404(5) 0.12745(19) 0.0834(10) Uani 1 1 d . . . . .
H15A H -0.4408 0.5136 0.0823 0.125 Uiso 1 1 calc GR . . . .
H15B H -0.4546 0.6020 0.1557 0.125 Uiso 1 1 calc GR . . . .
H15C H -0.3535 0.4222 0.1491 0.125 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.457(3) . ?
N1 C6 1.336(3) . ?
O2 C8 1.241(3) . ?
C3 C5 1.536(3) . ?
C3 C8 1.534(4) . ?
C3 C12 1.515(3) . ?
C4 C6 1.377(3) . ?
C4 C8 1.417(4) . ?
C5 C9 1.540(3) . ?
C6 C10 1.491(3) . ?
C7 C9 1.521(4) . ?
C7 C13 1.519(4) . ?
C9 C11 1.519(3) . ?
C10 C14 1.507(4) . ?
C12 C13 1.535(4) . ?
C14 C15 1.497(4) . ?

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
C6 N1 C5 121.31(17) . . ?
C8 C3 C5 110.78(18) . . ?
C12 C3 C5 111.5(2) . . ?
C12 C3 C8 113.8(2) . . ?
C6 C4 C8 121.7(2) . . ?
N1 C5 C3 109.45(18) . . ?
N1 C5 C9 111.09(17) . . ?
C3 C5 C9 111.99(17) . . ?
N1 C6 C4 121.1(2) . . ?
N1 C6 C10 115.90(19) . . ?
C4 C6 C10 122.9(2) . . ?
C13 C7 C9 111.1(2) . . ?
O2 C8 C3 120.0(2) . . ?
O2 C8 C4 123.4(3) . . ?
C4 C8 C3 116.32(19) . . ?
C7 C9 C5 109.95(19) . . ?
C11 C9 C5 112.05(19) . . ?
C11 C9 C7 110.6(2) . . ?
C6 C10 C14 111.5(2) . . ?
C3 C12 C13 111.5(2) . . ?
C7 C13 C12 110.5(2) . . ?
C15 C14 C10 114.2(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.363
_oxdiff_exptl_absorpt_empirical_full_min 0.821
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ???????'
####################################################################### 
# 
# 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_20181224xiefayang
_database_code_depnum_ccdc_archive 'CCDC 2179726'
loop_
_audit_author_name
_audit_author_address
'Fayang Xie'
;School of Pharmaceutical Sciences, Tsinghua University, Beijing, China
China
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2022-12-29 downloaded from the CCDC.
;
_audit_creation_date             2018-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H21 N O'
_chemical_formula_sum            'C13 H21 N O'
_chemical_formula_weight         207.31
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.3301(2)
_cell_length_b                   19.5449(6)
_cell_length_c                   12.1194(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.176(2)
_cell_angle_gamma                90
_cell_volume                     1259.20(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    273.00(10)
_cell_measurement_theta_max      69.8520
_cell_measurement_theta_min      4.2730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.527
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7898
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.388
_diffrn_reflns_theta_min         4.301
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      273.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  34.00   1.00    1.00    --  -40.81  19.00  60.00   98
  2  ω   -115.00 -21.00   1.00    1.00    --  -40.81 -38.00-120.00   94
  3  ω     63.00  97.00   1.00    1.00    --   40.81-125.00 150.00   34
  4  ω     23.00  66.00   1.00    1.00    --   40.81-125.00-150.00   43
  5  ω     28.00  55.00   1.00    1.00    --   40.81-125.00 150.00   27
  6  ω     82.00 117.00   1.00    3.00    --  100.91-125.00-120.00   35
  7  ω     73.00 141.00   1.00    3.00    --  100.91  61.00-120.00   68
  8  ω    109.00 174.00   1.00    3.00    --  100.91 125.00  30.00   65
  9  ω     34.00  96.00   1.00    3.00    --  100.91 -95.00 -30.00   62
 10  ω     31.00  61.00   1.00    3.00    --  100.91 -30.00  90.00   30
 11  ω    138.00 171.00   1.00    3.00    --  100.91  45.00  90.00   33
 12  ω    106.00 170.00   1.00    3.00    --  100.91 125.00 -30.00   64
 13  ω    140.00 168.00   1.00    3.00    --  100.91  45.00 120.00   28
 14  ω     75.00 161.00   1.00    3.00    --  100.91  61.00-180.00   86
 15  ω     75.00 125.00   1.00    3.00    --  100.91  45.00 120.00   50
 16  ω     94.00 146.00   1.00    3.00    --  100.91 125.00 120.00   52
 17  ω     77.00 102.00   1.00    3.00    --  100.91  45.00  90.00   25
 18  ω     35.00 133.00   1.00    3.00    --  100.91 -77.00  30.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0334530000
_diffrn_orient_matrix_UB_12      -0.0777573000
_diffrn_orient_matrix_UB_13      0.0138961000
_diffrn_orient_matrix_UB_21      0.2543033000
_diffrn_orient_matrix_UB_22      -0.0036383000
_diffrn_orient_matrix_UB_23      0.0688911000
_diffrn_orient_matrix_UB_31      -0.1348341000
_diffrn_orient_matrix_UB_32      0.0124526000
_diffrn_orient_matrix_UB_33      0.1063274000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1887
_reflns_number_total             2413
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0839
_refine_ls_restrained_S_all      1.163
_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)+(0.1240P)²+0.4353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2401
_refine_ls_wR_factor_ref         0.2552
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C002 \\sim C004 \\sim C005 \\sim C006 \\sim C007 \\sim C008 \\sim C009 \\sim
C00A \\sim C00B \\sim C00C \\sim C00D \\sim C00E \\sim C00F: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C002(H002), C004(H004), C005(H005)
3.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C00A(H00C,H00D), C00B(H00E,H00F), C00D(H00K,H00J), C00F(H00P,
 H00O)
3.c Aromatic/amide H refined with riding coordinates:
 N001(H001), C009(H009)
3.d Idealised Me refined as rotating group:
 C00C(H00G,H00H,H00I), C00E(H00L,H00M,H00N)
;
_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
N001 N 0.7623(4) 0.25913(11) 0.71167(17) 0.0703(6) Uani 1 1 d . . . . .
H001 H 0.6751 0.2615 0.7685 0.084 Uiso 1 1 calc R . . . .
C002 C 0.9351(4) 0.20302(13) 0.70107(18) 0.0604(6) Uani 1 1 d . U . . .
H002 H 1.1065 0.2206 0.7157 0.072 Uiso 1 1 calc R . . . .
O003 O 1.0376(6) 0.22498(16) 0.4156(2) 0.1256(11) Uani 1 1 d . . . . .
C004 C 0.9089(4) 0.17630(13) 0.58257(19) 0.0643(7) Uani 1 1 d . U . . .
H004 H 1.0442 0.1433 0.5734 0.077 Uiso 1 1 calc R . . . .
C005 C 0.6549(5) 0.13961(15) 0.5576(2) 0.0748(7) Uani 1 1 d . U . . .
H005 H 0.5209 0.1734 0.5642 0.090 Uiso 1 1 calc R . . . .
C006 C 0.9401(6) 0.23533(16) 0.5040(2) 0.0776(8) Uani 1 1 d . U . . .
C007 C 0.8922(5) 0.14824(16) 0.7859(2) 0.0770(8) Uani 1 1 d . U . . .
H00A H 1.0288 0.1154 0.7873 0.092 Uiso 1 1 calc R . . . .
H00B H 0.8931 0.1690 0.8586 0.092 Uiso 1 1 calc R . . . .
C008 C 0.7374(6) 0.30704(15) 0.6342(2) 0.0822(8) Uani 1 1 d . U . . .
C009 C 0.8383(6) 0.29852(16) 0.5348(2) 0.0845(9) Uani 1 1 d . U . . .
H009 H 0.8399 0.3353 0.4862 0.101 Uiso 1 1 calc R . . . .
C00A C 0.6457(6) 0.11150(17) 0.7607(3) 0.0870(9) Uani 1 1 d . U . . .
H00C H 0.5078 0.1427 0.7709 0.104 Uiso 1 1 calc R . . . .
H00D H 0.6331 0.0738 0.8121 0.104 Uiso 1 1 calc R . . . .
C00B C 0.6235(7) 0.08432(16) 0.6435(3) 0.0903(9) Uani 1 1 d . U . . .
H00E H 0.4600 0.0630 0.6292 0.108 Uiso 1 1 calc R . . . .
H00F H 0.7505 0.0494 0.6362 0.108 Uiso 1 1 calc R . . . .
C00C C 0.6277(9) 0.1106(2) 0.4402(3) 0.1231(14) Uani 1 1 d . U . . .
H00G H 0.6563 0.1463 0.3882 0.185 Uiso 1 1 calc GR . . . .
H00H H 0.4612 0.0926 0.4255 0.185 Uiso 1 1 calc GR . . . .
H00I H 0.7487 0.0748 0.4333 0.185 Uiso 1 1 calc GR . . . .
C00D C 0.5934(12) 0.3699(2) 0.6685(4) 0.1374(16) Uani 1 1 d . U . . .
H00K H 0.4995 0.3561 0.7304 0.165 Uiso 1 1 calc R . . . .
H00J H 0.7183 0.4026 0.6974 0.165 Uiso 1 1 calc R . . . .
C00E C 0.2981(9) 0.4633(2) 0.6417(4) 0.1349(16) Uani 1 1 d . U . . .
H00L H 0.3401 0.5031 0.6004 0.202 Uiso 1 1 calc GR . . . .
H00M H 0.3420 0.4709 0.7189 0.202 Uiso 1 1 calc GR . . . .
H00N H 0.1209 0.4547 0.6304 0.202 Uiso 1 1 calc GR . . . .
C00F C 0.4417(13) 0.4025(3) 0.6029(5) 0.183(2) Uani 1 1 d . U . . .
H00P H 0.3185 0.3699 0.5722 0.220 Uiso 1 1 calc R . . . .
H00O H 0.5359 0.4180 0.5420 0.220 Uiso 1 1 calc R . . . .


_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
N001 H001 0.8600 . ?
N001 C002 1.444(3) . ?
N001 C008 1.325(3) . ?
C002 H002 0.9800 . ?
C002 C004 1.525(3) . ?
C002 C007 1.513(3) . ?
O003 C006 1.241(3) . ?
C004 H004 0.9800 . ?
C004 C005 1.542(4) . ?
C004 C006 1.513(4) . ?
C005 H005 0.9800 . ?
C005 C00B 1.518(4) . ?
C005 C00C 1.528(4) . ?
C006 C009 1.411(4) . ?
C007 H00A 0.9700 . ?
C007 H00B 0.9700 . ?
C007 C00A 1.509(4) . ?
C008 C009 1.365(4) . ?
C008 C00D 1.522(5) . ?
C009 H009 0.9300 . ?
C00A H00C 0.9700 . ?
C00A H00D 0.9700 . ?
C00A C00B 1.514(5) . ?
C00B H00E 0.9700 . ?
C00B H00F 0.9700 . ?
C00C H00G 0.9600 . ?
C00C H00H 0.9600 . ?
C00C H00I 0.9600 . ?
C00D H00K 0.9700 . ?
C00D H00J 0.9700 . ?
C00D C00F 1.265(6) . ?
C00E H00L 0.9600 . ?
C00E H00M 0.9600 . ?
C00E H00N 0.9600 . ?
C00E C00F 1.507(6) . ?
C00F H00P 0.9700 . ?
C00F H00O 0.9700 . ?

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
C002 N001 H001 119.8 . . ?
C008 N001 H001 119.8 . . ?
C008 N001 C002 120.4(2) . . ?
N001 C002 H002 108.1 . . ?
N001 C002 C004 109.19(19) . . ?
N001 C002 C007 110.4(2) . . ?
C004 C002 H002 108.1 . . ?
C007 C002 H002 108.1 . . ?
C007 C002 C004 112.9(2) . . ?
C002 C004 H004 108.3 . . ?
C002 C004 C005 111.28(19) . . ?
C005 C004 H004 108.3 . . ?
C006 C004 C002 109.0(2) . . ?
C006 C004 H004 108.3 . . ?
C006 C004 C005 111.5(2) . . ?
C004 C005 H005 107.8 . . ?
C00B C005 C004 109.6(2) . . ?
C00B C005 H005 107.8 . . ?
C00B C005 C00C 111.5(3) . . ?
C00C C005 C004 112.2(3) . . ?
C00C C005 H005 107.8 . . ?
O003 C006 C004 119.4(3) . . ?
O003 C006 C009 124.4(3) . . ?
C009 C006 C004 116.0(2) . . ?
C002 C007 H00A 109.3 . . ?
C002 C007 H00B 109.3 . . ?
H00A C007 H00B 107.9 . . ?
C00A C007 C002 111.8(2) . . ?
C00A C007 H00A 109.3 . . ?
C00A C007 H00B 109.3 . . ?
N001 C008 C009 120.9(3) . . ?
N001 C008 C00D 113.8(3) . . ?
C009 C008 C00D 125.3(3) . . ?
C006 C009 H009 119.2 . . ?
C008 C009 C006 121.7(3) . . ?
C008 C009 H009 119.2 . . ?
C007 C00A H00C 109.4 . . ?
C007 C00A H00D 109.4 . . ?
C007 C00A C00B 111.4(2) . . ?
H00C C00A H00D 108.0 . . ?
C00B C00A H00C 109.4 . . ?
C00B C00A H00D 109.4 . . ?
C005 C00B H00E 109.0 . . ?
C005 C00B H00F 109.0 . . ?
C00A C00B C005 112.9(2) . . ?
C00A C00B H00E 109.0 . . ?
C00A C00B H00F 109.0 . . ?
H00E C00B H00F 107.8 . . ?
C005 C00C H00G 109.5 . . ?
C005 C00C H00H 109.5 . . ?
C005 C00C H00I 109.5 . . ?
H00G C00C H00H 109.5 . . ?
H00G C00C H00I 109.5 . . ?
H00H C00C H00I 109.5 . . ?
C008 C00D H00K 106.5 . . ?
C008 C00D H00J 106.5 . . ?
H00K C00D H00J 106.5 . . ?
C00F C00D C008 123.2(4) . . ?
C00F C00D H00K 106.5 . . ?
C00F C00D H00J 106.5 . . ?
H00L C00E H00M 109.5 . . ?
H00L C00E H00N 109.5 . . ?
H00M C00E H00N 109.5 . . ?
C00F C00E H00L 109.5 . . ?
C00F C00E H00M 109.5 . . ?
C00F C00E H00N 109.5 . . ?
C00D C00F C00E 121.1(5) . . ?
C00D C00F H00P 107.0 . . ?
C00D C00F H00O 107.0 . . ?
C00E C00F H00P 107.0 . . ?
C00E C00F H00O 107.0 . . ?
H00P C00F H00O 106.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.588
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ???????'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_4164xfy
_database_code_depnum_ccdc_archive 'CCDC 2182442'
loop_
_audit_author_name
_audit_author_address
'Fayang Xie'
;School of Pharmaceutical Sciences, Tsinghua University, Beijing, China
China
;
_audit_update_record             
;
2022-06-28 deposited with the CCDC.	2022-12-29 downloaded from the CCDC.
;
_audit_creation_date             2022-06-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C11 H10 N O'
_chemical_formula_weight         172.20
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.00810(10)
_cell_length_b                   15.7243(2)
_cell_length_c                   12.7801(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.522(2)
_cell_angle_gamma                90
_cell_volume                     989.50(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3154
_cell_measurement_temperature    99.98(16)
_cell_measurement_theta_max      66.2280
_cell_measurement_theta_min      6.6410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             364
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.928
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3834
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        66.873
_diffrn_reflns_theta_max         66.873
_diffrn_reflns_theta_min         4.504
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     52.00  77.00   0.50    0.50    --   -0.70  21.00-162.00   50
  2  ω     44.00  69.00   0.50    0.50    --   90.00  21.00-162.00   50
  3  ω    -68.00 -43.00   0.50    0.50    --    0.70   0.00-180.00   50
  4  ω     -1.00  74.00   0.50    0.50    --    0.70   0.00-180.00  150
  5  ω     74.00 104.00   0.50    0.50    --   90.00  37.00  60.00   60
  6  ω    144.00 171.00   0.50    0.50    --   90.00  46.00 -30.00   54
  7  ω      1.00  73.00   0.50    0.50    --   90.00   9.00   0.00  144
  8  ω    115.00 140.00   0.50    0.50    --   90.00   9.00   0.00   50
  9  ω    105.00 131.00   0.50    0.50    --   90.00  46.00 -30.00   52
 10  ω     15.00  41.00   0.50    0.50    --   90.00  37.00  60.00   52
 11  ω    140.00 165.00   0.50    0.50    --   90.00  37.00 -30.00   50
 12  ω    111.00 173.00   0.50    0.50    --   90.00   9.00-180.00  124
 13  ω     20.00  46.00   0.50    0.50    --   90.00  28.00 -30.00   52
 14  ω      3.00 179.00   0.50    0.50    --   90.00  46.00  30.00  352
 15  ω     91.00 123.00   0.50    0.50    --   90.00  21.00-162.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0271578000
_diffrn_orient_matrix_UB_12      0.0035314000
_diffrn_orient_matrix_UB_13      -0.1220063000
_diffrn_orient_matrix_UB_21      -0.1039345000
_diffrn_orient_matrix_UB_22      0.0921698000
_diffrn_orient_matrix_UB_23      0.0002647000
_diffrn_orient_matrix_UB_31      0.2937994000
_diffrn_orient_matrix_UB_32      0.0329051000
_diffrn_orient_matrix_UB_33      0.0124323000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1553
_reflns_number_total             1619
_reflns_odcompleteness_completeness 91.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.899
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0726
_refine_ls_restrained_S_all      2.899
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2917
_refine_ls_wR_factor_ref         0.3005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6)
;
_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
C1 C 0.2403(5) 0.29464(15) 0.51850(17) 0.0224(7) Uani 1 1 d . . . . .
N1 N 0.2754(4) 0.24328(12) 0.73063(13) 0.0223(7) Uani 1 1 d . . . . .
H1 H 0.2888 0.2276 0.7959 0.027 Uiso 1 1 calc R U . . .
O1 O 0.2203(4) 0.31858(10) 0.42295(11) 0.0274(7) Uani 1 1 d . . . . .
C2 C 0.0826(5) 0.33633(15) 0.58855(17) 0.0226(7) Uani 1 1 d . . . . .
C3 C -0.0990(5) 0.40408(15) 0.55097(18) 0.0268(7) Uani 1 1 d . . . . .
H3 H -0.1223 0.4215 0.4803 0.032 Uiso 1 1 calc R U . . .
C4 C -0.2406(6) 0.44371(19) 0.6212(2) 0.0427(9) Uani 1 1 d . . . . .
H4 H -0.3422 0.4922 0.5994 0.051 Uiso 1 1 calc R U . . .
C5 C -0.2332(5) 0.41219(15) 0.72362(18) 0.0271(7) Uani 1 1 d . . . . .
H5 H -0.3501 0.4343 0.7655 0.032 Uiso 1 1 calc R U . . .
C6 C -0.0522(5) 0.34776(15) 0.76381(16) 0.0244(7) Uani 1 1 d . . . . .
H6 H -0.0337 0.3304 0.8343 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1042(5) 0.30907(13) 0.69387(17) 0.0210(7) Uani 1 1 d . . . . .
C8 C 0.4248(5) 0.20183(15) 0.66778(17) 0.0219(7) Uani 1 1 d . . . . .
C9 C 0.4153(4) 0.22569(14) 0.56316(16) 0.0214(7) Uani 1 1 d . . . . .
C10 C 0.5722(5) 0.17966(15) 0.49259(18) 0.0251(7) Uani 1 1 d . . . . .
H10A H 0.6734 0.2208 0.4589 0.030 Uiso 1 1 calc R U . . .
H10B H 0.4455 0.1516 0.4368 0.030 Uiso 1 1 calc R U . . .
C11 C 0.7667(5) 0.11457(15) 0.54870(18) 0.0262(7) Uani 1 1 d . . . . .
H11A H 0.8094 0.0740 0.4970 0.031 Uiso 1 1 calc R U . . .
H11B H 0.9342 0.1426 0.5808 0.031 Uiso 1 1 calc R U . . .
C12 C 0.6545(7) 0.06795(18) 0.6330(2) 0.0411(9) Uani 1 1 d . . . . .
H12A H 0.7861 0.0264 0.6664 0.049 Uiso 1 1 calc R U . . .
H12B H 0.4911 0.0378 0.6009 0.049 Uiso 1 1 calc R U . . .
C13 C 0.5890(5) 0.12868(15) 0.71648(17) 0.0258(7) Uani 1 1 d . . . . .
H13A H 0.4897 0.0986 0.7635 0.031 Uiso 1 1 calc R U . . .
H13B H 0.7568 0.1495 0.7589 0.031 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
C1 O1 1.264(3) . ?
C1 C2 1.454(3) . ?
C1 C9 1.445(3) . ?
N1 H1 0.8600 . ?
N1 C7 1.371(3) . ?
N1 C8 1.360(3) . ?
C2 C3 1.426(3) . ?
C2 C7 1.398(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.427(3) . ?
C8 C9 1.381(3) . ?
C8 C13 1.483(3) . ?
C9 C10 1.488(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.502(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.495(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.511(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
O1 C1 C2 120.3(2) . . ?
O1 C1 C9 122.7(2) . . ?
C9 C1 C2 117.0(2) . . ?
C7 N1 H1 118.8 . . ?
C8 N1 H1 118.8 . . ?
C8 N1 C7 122.44(18) . . ?
C3 C2 C1 120.9(2) . . ?
C7 C2 C1 120.0(2) . . ?
C7 C2 C3 119.1(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C7 118.25(19) . . ?
C7 C6 H6 120.9 . . ?
N1 C7 C2 119.7(2) . . ?
N1 C7 C6 119.16(19) . . ?
C2 C7 C6 121.2(2) . . ?
N1 C8 C9 121.1(2) . . ?
N1 C8 C13 116.53(18) . . ?
C9 C8 C13 122.4(2) . . ?
C1 C9 C10 118.37(19) . . ?
C8 C9 C1 119.8(2) . . ?
C8 C9 C10 121.7(2) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C9 C10 C11 114.23(19) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C10 112.45(19) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 C13 110.9(2) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C8 C13 C12 111.66(19) . . ?
C8 C13 H13A 109.3 . . ?
C8 C13 H13B 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?

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
C1 C2 C3 C4 -178.3(2) . . . . ?
C1 C2 C7 N1 0.3(3) . . . . ?
C1 C2 C7 C6 -178.79(18) . . . . ?
C1 C9 C10 C11 174.71(18) . . . . ?
N1 C8 C9 C1 -1.3(4) . . . . ?
N1 C8 C9 C10 -178.46(18) . . . . ?
N1 C8 C13 C12 157.5(2) . . . . ?
O1 C1 C2 C3 0.7(4) . . . . ?
O1 C1 C2 C7 179.51(19) . . . . ?
O1 C1 C9 C8 -179.0(2) . . . . ?
O1 C1 C9 C10 -1.7(4) . . . . ?
C2 C1 C9 C8 0.6(3) . . . . ?
C2 C1 C9 C10 177.88(18) . . . . ?
C2 C3 C4 C5 -7.7(4) . . . . ?
C3 C2 C7 N1 179.17(19) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C3 C4 C5 C6 9.6(4) . . . . ?
C4 C5 C6 C7 -6.4(4) . . . . ?
C5 C6 C7 N1 -177.40(18) . . . . ?
C5 C6 C7 C2 1.7(3) . . . . ?
C7 N1 C8 C9 1.5(3) . . . . ?
C7 N1 C8 C13 -176.57(19) . . . . ?
C7 C2 C3 C4 2.8(4) . . . . ?
C8 N1 C7 C2 -1.0(3) . . . . ?
C8 N1 C7 C6 178.13(19) . . . . ?
C8 C9 C10 C11 -8.0(3) . . . . ?
C9 C1 C2 C3 -178.97(19) . . . . ?
C9 C1 C2 C7 -0.1(3) . . . . ?
C9 C8 C13 C12 -20.5(3) . . . . ?
C9 C10 C11 C12 37.9(3) . . . . ?
C10 C11 C12 C13 -59.7(3) . . . . ?
C11 C12 C13 C8 49.7(3) . . . . ?
C13 C8 C9 C1 176.67(19) . . . . ?
C13 C8 C9 C10 -0.5(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.965
_oxdiff_exptl_absorpt_empirical_full_min 0.424
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ???????'
