# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

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

data_lizhen_0218-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2170036'
loop_
_audit_author_name
_audit_author_address
'Zhen Li'
;lanzhou university
China
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_audit_creation_date             2022-02-18
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N O2'
_chemical_formula_sum            'C17 H21 N O2'
_chemical_formula_weight         271.35
_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                   9.8106(2)
_cell_length_b                   17.8042(2)
_cell_length_c                   9.8334(2)
_cell_angle_alpha                90
_cell_angle_beta                 119.489(3)
_cell_angle_gamma                90
_cell_volume                     1495.08(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11077
_cell_measurement_temperature    295.99(10)
_cell_measurement_theta_max      77.3510
_cell_measurement_theta_min      4.9830
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (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    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14667
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.485
_diffrn_reflns_theta_min         4.968
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     96.00 167.00   0.50    0.06    --  107.75  37.00   0.00  142
  2  ω    144.00 175.00   0.50    0.06    --  107.75  80.00  73.00   62
  3  ω    116.00 171.00   0.50    0.06    --  107.75  37.00 -30.00  110
  4  ω    116.00 173.00   0.50    0.06    --  107.75  19.00-150.00  114
  5  ω    -24.00  29.00   0.50    0.05    --   47.57 -80.00 -50.00  106
  6  ω    -25.00  23.00   0.50    0.05    --   47.57 -19.00 -30.00   96
  7  ω    -12.00  13.00   0.50    0.05    --   47.57 -19.00 -60.00   50
  8  ω    -25.00  39.00   0.50    0.05    --   47.57 -37.00-150.00  128
  9  ω    -25.00   0.00   0.50    0.05    --   47.57 -19.00-150.00   50
 10  ω     49.00 113.00   0.50    0.06    --  107.75 -80.00 -50.00  128
 11  ω     35.00  61.00   0.50    0.06    --  107.75 -57.00  90.00   52
 12  ω     35.00  60.00   0.50    0.06    --  107.75 -57.00 150.00   50
 13  ω     36.00  62.00   0.50    0.06    --  107.75 -57.00   0.00   52
 14  ω     36.00  62.00   0.50    0.06    --  107.75 -57.00-120.00   52
 15  ω    -69.00 -44.00   0.50    0.05    --  -47.57  80.00  73.00   50
 16  ω    -41.00  15.00   0.50    0.05    --  -47.57  80.00  73.00  112
 17  ω    -68.00 -27.00   0.50    0.06    -- -100.00  57.00  90.00   82
 18  ω    -61.00 -30.00   0.50    0.06    -- -100.00  57.00 120.00   62
 19  ω    -76.00 -51.00   0.50    0.06    -- -100.00  80.00  73.00   50
 20  ω    -69.00 -27.00   0.50    0.06    -- -100.00  57.00  60.00   84
 21  ω    -67.00 -42.00   0.50    0.06    -- -100.00  57.00 -60.00   50
 22  ω    -68.00 -32.00   0.50    0.06    -- -100.00  57.00 -90.00   72
 23  ω   -151.00 -87.00   0.50    0.06    -- -100.00 -80.00 -50.00  128
 24  ω   -154.00-128.00   0.50    0.06    -- -100.00 -80.00 -50.00   52
 25  ω     71.00 103.00   0.50    0.05    --   47.57-154.00  77.00   64
 26  ω    -26.00  23.00   0.50    0.05    --   47.57 -19.00-120.00   98
 27  ω     36.00  62.00   0.50    0.05    --   47.57  57.00-180.00   52
 28  ω     -6.00  29.00   0.50    0.05    --   47.57 -37.00 -90.00   70
 29  ω     88.00 120.00   0.50    0.05    --   47.57  57.00-180.00   64
 30  ω     12.00  39.00   0.50    0.05    --   47.57 -37.00  90.00   54
 31  ω    -57.00 -27.00   0.50    0.06    -- -100.00 125.00  60.00   60
 32  ω   -168.00-142.00   0.50    0.06    -- -100.00-125.00-180.00   52
 33  ω    -83.00 -57.00   0.50    0.06    -- -100.00  77.00 -90.00   52
 34  ω   -119.00 -87.00   0.50    0.06    -- -100.00-125.00-180.00   64
 35  ω   -107.00 -60.00   0.50    0.06    -- -100.00 125.00   0.00   94
 36  ω   -111.00 -85.00   0.50    0.06    -- -100.00 125.00  60.00   52
 37  ω   -172.00-109.00   0.50    0.06    -- -100.00 -37.00 150.00  126
 38  ω     58.00  96.00   0.50    0.06    --  107.75-120.00-124.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1784948000
_diffrn_orient_matrix_UB_12      -0.0116072000
_diffrn_orient_matrix_UB_13      0.0953445000
_diffrn_orient_matrix_UB_21      0.0250088000
_diffrn_orient_matrix_UB_22      0.0851672000
_diffrn_orient_matrix_UB_23      -0.0051055000
_diffrn_orient_matrix_UB_31      -0.0060236000
_diffrn_orient_matrix_UB_32      0.0101050000
_diffrn_orient_matrix_UB_33      0.1525723000
_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                2695
_reflns_number_total             2988
_reflns_odcompleteness_completeness 98.74
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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         0.213
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0110(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.039
_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)+(0.0527P)²+0.2189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1049
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C12(H12), C14(H14), C16(H16)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_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
O1 O 0.58397(10) 0.55175(4) 0.26027(10) 0.0480(2) Uani 1 1 d . . . . .
O2 O 0.44479(10) 0.63702(6) 0.07379(10) 0.0593(3) Uani 1 1 d . . . . .
N1 N 0.62927(11) 0.78343(5) 0.44844(11) 0.0449(2) Uani 1 1 d . . . . .
H1 H 0.562540 0.807685 0.464265 0.054 Uiso 1 1 calc R . . . .
C1 C 0.64243(12) 0.70605(6) 0.45003(12) 0.0404(3) Uani 1 1 d . . . . .
C2 C 0.73826(13) 0.81579(6) 0.41793(12) 0.0426(3) Uani 1 1 d . . . . .
C3 C 0.76117(12) 0.68782(6) 0.42018(12) 0.0419(3) Uani 1 1 d . . . . .
C4 C 0.82182(12) 0.75703(6) 0.39686(12) 0.0416(3) Uani 1 1 d . . . . .
C5 C 0.53851(14) 0.65931(7) 0.48776(13) 0.0447(3) Uani 1 1 d . . . . .
H5A H 0.538577 0.681643 0.577771 0.054 Uiso 1 1 calc R . . . .
H5B H 0.586026 0.610042 0.519389 0.054 Uiso 1 1 calc R . . . .
C6 C 0.46003(13) 0.59631(6) 0.17835(13) 0.0438(3) Uani 1 1 d . . . . .
C7 C 0.82592(14) 0.61181(7) 0.41714(14) 0.0489(3) Uani 1 1 d . . . . .
H7A H 0.831557 0.582047 0.502391 0.059 Uiso 1 1 calc R . . . .
H7B H 0.931832 0.617960 0.435305 0.059 Uiso 1 1 calc R . . . .
C8 C 0.36473(13) 0.64790(7) 0.35909(13) 0.0447(3) Uani 1 1 d . . . . .
C9 C 0.73129(14) 0.56886(7) 0.26569(14) 0.0463(3) Uani 1 1 d . . . . .
H9 H 0.712723 0.600383 0.176481 0.056 Uiso 1 1 calc R . . . .
C10 C 0.93853(14) 0.77483(7) 0.35979(14) 0.0512(3) Uani 1 1 d . . . . .
H10 H 0.994101 0.736939 0.343394 0.061 Uiso 1 1 calc R . . . .
C11 C 0.34606(14) 0.58775(7) 0.23677(14) 0.0482(3) Uani 1 1 d . . . . .
H11A H 0.359185 0.538354 0.283250 0.058 Uiso 1 1 calc R . . . .
H11B H 0.240588 0.590594 0.148719 0.058 Uiso 1 1 calc R . . . .
C12 C 0.77025(16) 0.89095(7) 0.40634(14) 0.0525(3) Uani 1 1 d . . . . .
H12 H 0.714561 0.929280 0.421295 0.063 Uiso 1 1 calc R . . . .
C13 C 0.28897(15) 0.72120(8) 0.27629(16) 0.0579(3) Uani 1 1 d . . . . .
H13A H 0.300397 0.758237 0.352163 0.087 Uiso 1 1 calc GR . . . .
H13B H 0.179732 0.712903 0.205165 0.087 Uiso 1 1 calc GR . . . .
H13C H 0.339064 0.738642 0.219398 0.087 Uiso 1 1 calc GR . . . .
C14 C 0.97014(15) 0.84900(8) 0.34785(16) 0.0577(3) Uani 1 1 d . . . . .
H14 H 1.047803 0.861034 0.323368 0.069 Uiso 1 1 calc R . . . .
C15 C 0.80418(18) 0.49510(8) 0.25938(18) 0.0648(4) Uani 1 1 d . . . . .
H15A H 0.826261 0.465604 0.349672 0.097 Uiso 1 1 calc GR . . . .
H15B H 0.899727 0.504580 0.257823 0.097 Uiso 1 1 calc GR . . . .
H15C H 0.732843 0.468249 0.166639 0.097 Uiso 1 1 calc GR . . . .
C16 C 0.88781(16) 0.90647(8) 0.37180(15) 0.0578(3) Uani 1 1 d . . . . .
H16 H 0.912484 0.956185 0.364398 0.069 Uiso 1 1 calc R . . . .
C17 C 0.27670(18) 0.61757(10) 0.44002(19) 0.0677(4) Uani 1 1 d . . . . .
H17A H 0.329065 0.573631 0.499395 0.102 Uiso 1 1 calc GR . . . .
H17B H 0.171532 0.604811 0.362761 0.102 Uiso 1 1 calc GR . . . .
H17C H 0.274336 0.655278 0.508622 0.102 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
O1 C6 1.3389(14) . ?
O1 C9 1.4522(14) . ?
O2 C6 1.2057(14) . ?
N1 C1 1.3830(15) . ?
N1 C2 1.3717(15) . ?
C1 C3 1.3730(15) . ?
C1 C5 1.4972(16) . ?
C2 C4 1.4060(16) . ?
C2 C12 1.3918(17) . ?
C3 C4 1.4350(16) . ?
C3 C7 1.5015(16) . ?
C4 C10 1.3983(16) . ?
C5 C8 1.5573(16) . ?
C6 C11 1.4952(16) . ?
C7 C9 1.5177(17) . ?
C8 C11 1.5526(16) . ?
C8 C13 1.5241(17) . ?
C8 C17 1.5322(17) . ?
C9 C15 1.5111(17) . ?
C10 C14 1.3746(18) . ?
C12 C16 1.3811(19) . ?
C14 C16 1.394(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
C6 O1 C9 119.37(9) . . ?
C2 N1 C1 110.03(9) . . ?
N1 C1 C5 119.02(10) . . ?
C3 C1 N1 108.50(10) . . ?
C3 C1 C5 132.41(10) . . ?
N1 C2 C4 107.06(10) . . ?
N1 C2 C12 130.79(11) . . ?
C12 C2 C4 122.15(11) . . ?
C1 C3 C4 107.06(10) . . ?
C1 C3 C7 128.98(11) . . ?
C4 C3 C7 123.92(10) . . ?
C2 C4 C3 107.32(10) . . ?
C10 C4 C2 118.77(11) . . ?
C10 C4 C3 133.90(11) . . ?
C1 C5 C8 118.55(9) . . ?
O1 C6 C11 109.74(10) . . ?
O2 C6 O1 124.33(11) . . ?
O2 C6 C11 125.93(11) . . ?
C3 C7 C9 114.41(9) . . ?
C11 C8 C5 112.58(9) . . ?
C13 C8 C5 111.92(10) . . ?
C13 C8 C11 109.65(10) . . ?
C13 C8 C17 109.14(11) . . ?
C17 C8 C5 107.19(10) . . ?
C17 C8 C11 106.12(10) . . ?
O1 C9 C7 104.99(9) . . ?
O1 C9 C15 107.38(10) . . ?
C15 C9 C7 113.89(11) . . ?
C14 C10 C4 119.22(12) . . ?
C6 C11 C8 113.70(9) . . ?
C16 C12 C2 117.49(12) . . ?
C10 C14 C16 121.12(12) . . ?
C12 C16 C14 121.23(12) . . ?

_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 3.567
_oxdiff_exptl_absorpt_empirical_full_min 0.385
