# Electronic Supplementary Material (ESI) for Green 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_xt0619
_database_code_depnum_ccdc_archive 'CCDC 2166562'
loop_
_audit_author_name
_audit_author_address
'Huawen Huang'
;Xiangtan University
China
;
_audit_update_record             
;
2022-04-14 deposited with the CCDC.	2022-07-13 downloaded from the CCDC.
;
_audit_creation_date             2021-06-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N O2'
_chemical_formula_sum            'C18 H19 N O2'
_chemical_formula_weight         281.34
_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 0.0033 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                   8.8424(9)
_cell_length_b                   12.5877(12)
_cell_length_c                   26.417(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2940.4(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2652
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      28.3280
_cell_measurement_theta_min      2.7840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7598
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.772
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_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    -28.00  20.00   1.00    2.00    --  -11.27  77.00 -30.00   48
  2  ω    -12.00  63.00   1.00    2.00    --   11.90  77.00-180.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0354707000
_diffrn_orient_matrix_UB_12      0.0197894000
_diffrn_orient_matrix_UB_13      -0.0221018000
_diffrn_orient_matrix_UB_21      0.0019503000
_diffrn_orient_matrix_UB_22      -0.0515767000
_diffrn_orient_matrix_UB_23      -0.0107764000
_diffrn_orient_matrix_UB_31      -0.0720569000
_diffrn_orient_matrix_UB_32      -0.0112077000
_diffrn_orient_matrix_UB_33      0.0106587000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2091
_reflns_number_total             2587
_reflns_odcompleteness_completeness 99.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.077
_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)+(0.0483P)²+0.8156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 C18(H18A,H18B,H18C)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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 0.85684(13) 0.37184(11) 0.68614(5) 0.0378(3) Uani 1 1 d . . . . .
H1 H 0.839029 0.379271 0.716399 0.057 Uiso 1 1 calc R U . . .
O2 O 0.30677(14) 0.38767(9) 0.70735(5) 0.0328(3) Uani 1 1 d . . . . .
N1 N 0.28867(15) 0.34068(10) 0.62400(5) 0.0254(3) Uani 1 1 d . . . . .
C1 C 0.64587(18) 0.44464(13) 0.63892(6) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.6231(2) 0.45635(15) 0.58737(7) 0.0334(4) Uani 1 1 d . . . . .
H2 H 0.652139 0.402256 0.565445 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5576(2) 0.54798(16) 0.56806(8) 0.0449(5) Uani 1 1 d . . . . .
H3 H 0.542985 0.555119 0.533357 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5143(2) 0.62799(16) 0.60019(9) 0.0465(6) Uani 1 1 d . . . . .
H4 H 0.470061 0.689267 0.587231 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5360(2) 0.61787(15) 0.65139(8) 0.0411(5) Uani 1 1 d . . . . .
H5 H 0.506919 0.672324 0.673101 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6012(2) 0.52652(13) 0.67064(7) 0.0326(4) Uani 1 1 d . . . . .
H6 H 0.615194 0.519947 0.705386 0.039 Uiso 1 1 calc R U . . .
C7 C 0.71997(18) 0.34605(13) 0.66004(6) 0.0263(4) Uani 1 1 d . . . . .
H7 H 0.747483 0.301027 0.631212 0.032 Uiso 1 1 calc R U . . .
C8 C 0.61693(18) 0.28017(14) 0.69445(6) 0.0260(4) Uani 1 1 d . . . . .
H8A H 0.596419 0.321542 0.724657 0.031 Uiso 1 1 calc R U . . .
H8B H 0.672498 0.217482 0.704942 0.031 Uiso 1 1 calc R U . . .
C9 C 0.46470(18) 0.24367(12) 0.67237(6) 0.0230(4) Uani 1 1 d . . . . .
C10 C 0.4008(2) 0.15407(13) 0.70576(7) 0.0320(4) Uani 1 1 d . . . . .
H10A H 0.303385 0.133050 0.693207 0.048 Uiso 1 1 calc R U . . .
H10B H 0.390878 0.178978 0.739951 0.048 Uiso 1 1 calc R U . . .
H10C H 0.468185 0.094316 0.704956 0.048 Uiso 1 1 calc R U . . .
C11 C 0.46795(17) 0.21050(12) 0.61756(6) 0.0213(4) Uani 1 1 d . . . . .
C12 C 0.34717(18) 0.33318(13) 0.67156(6) 0.0241(4) Uani 1 1 d . . . . .
C13 C 0.36081(17) 0.26923(13) 0.59104(6) 0.0233(4) Uani 1 1 d . . . . .
C14 C 0.3363(2) 0.25406(14) 0.54019(7) 0.0317(4) Uani 1 1 d . . . . .
H14 H 0.264399 0.293566 0.522698 0.038 Uiso 1 1 calc R U . . .
C15 C 0.4231(2) 0.17735(15) 0.51591(7) 0.0343(4) Uani 1 1 d . . . . .
H15 H 0.408536 0.165145 0.481529 0.041 Uiso 1 1 calc R U . . .
C16 C 0.5303(2) 0.11895(14) 0.54168(7) 0.0315(4) Uani 1 1 d . . . . .
H16 H 0.587201 0.068286 0.524553 0.038 Uiso 1 1 calc R U . . .
C17 C 0.55365(19) 0.13538(13) 0.59305(6) 0.0266(4) Uani 1 1 d . . . . .
H17 H 0.625966 0.096273 0.610548 0.032 Uiso 1 1 calc R U . . .
C18 C 0.1768(2) 0.41943(14) 0.60944(7) 0.0371(5) Uani 1 1 d . . . . .
H18A H 0.224984 0.474689 0.590257 0.056 Uiso 1 1 d R U . . .
H18B H 0.131364 0.449259 0.639267 0.056 Uiso 1 1 d R U . . .
H18C H 0.100334 0.386329 0.589037 0.056 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C7 1.4302(19) . ?
O2 C12 1.2216(19) . ?
N1 C12 1.362(2) . ?
N1 C13 1.405(2) . ?
N1 C18 1.452(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.386(2) . ?
C1 C7 1.510(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.531(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.537(2) . ?
C9 C10 1.539(2) . ?
C9 C11 1.507(2) . ?
C9 C12 1.533(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C13 1.391(2) . ?
C11 C17 1.374(2) . ?
C13 C14 1.374(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(2) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9601 . ?
C18 H18B 0.9611 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
C12 N1 C13 110.78(13) . . ?
C12 N1 C18 123.39(14) . . ?
C13 N1 C18 125.60(14) . . ?
C2 C1 C6 118.30(16) . . ?
C2 C1 C7 120.93(15) . . ?
C6 C1 C7 120.76(16) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.71(18) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.95(19) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.19(19) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.86(19) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.99(18) . . ?
C5 C6 H6 119.5 . . ?
O1 C7 C1 111.03(13) . . ?
O1 C7 H7 107.2 . . ?
O1 C7 C8 109.89(13) . . ?
C1 C7 H7 107.2 . . ?
C1 C7 C8 113.97(14) . . ?
C8 C7 H7 107.2 . . ?
C7 C8 H8A 108.0 . . ?
C7 C8 H8B 108.0 . . ?
C7 C8 C9 117.23(14) . . ?
H8A C8 H8B 107.2 . . ?
C9 C8 H8A 108.0 . . ?
C9 C8 H8B 108.0 . . ?
C8 C9 C10 108.84(13) . . ?
C11 C9 C8 115.51(13) . . ?
C11 C9 C10 110.76(13) . . ?
C11 C9 C12 101.72(12) . . ?
C12 C9 C8 112.29(13) . . ?
C12 C9 C10 107.31(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C9 108.89(13) . . ?
C17 C11 C9 130.84(15) . . ?
C17 C11 C13 120.26(15) . . ?
O2 C12 N1 124.33(15) . . ?
O2 C12 C9 126.89(15) . . ?
N1 C12 C9 108.74(14) . . ?
C11 C13 N1 109.71(14) . . ?
C14 C13 N1 128.55(15) . . ?
C14 C13 C11 121.74(15) . . ?
C13 C14 H14 121.3 . . ?
C13 C14 C15 117.42(16) . . ?
C15 C14 H14 121.3 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.45(17) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.36(16) . . ?
C17 C16 H16 119.8 . . ?
C11 C17 C16 118.76(16) . . ?
C11 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
N1 C18 H18A 109.4 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.4 . . ?
H18A C18 H18B 109.6 . . ?
H18A C18 H18C 109.3 . . ?
H18B C18 H18C 109.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C9 -179.18(13) . . . . ?
N1 C13 C14 C15 -179.79(16) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C7 C8 C9 55.5(2) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C2 C1 C7 O1 119.02(16) . . . . ?
C2 C1 C7 C8 -116.24(17) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C1 C7 O1 -59.9(2) . . . . ?
C6 C1 C7 C8 64.9(2) . . . . ?
C7 C1 C2 C3 -178.79(16) . . . . ?
C7 C1 C6 C5 178.71(16) . . . . ?
C7 C8 C9 C10 163.73(14) . . . . ?
C7 C8 C9 C11 38.4(2) . . . . ?
C7 C8 C9 C12 -77.61(18) . . . . ?
C8 C9 C11 C13 -124.96(15) . . . . ?
C8 C9 C11 C17 56.2(2) . . . . ?
C8 C9 C12 O2 -54.2(2) . . . . ?
C8 C9 C12 N1 128.04(14) . . . . ?
C9 C11 C13 N1 1.23(17) . . . . ?
C9 C11 C13 C14 -178.55(15) . . . . ?
C9 C11 C17 C16 178.27(15) . . . . ?
C10 C9 C11 C13 110.73(15) . . . . ?
C10 C9 C11 C17 -68.1(2) . . . . ?
C10 C9 C12 O2 65.4(2) . . . . ?
C10 C9 C12 N1 -112.40(15) . . . . ?
C11 C9 C12 O2 -178.26(16) . . . . ?
C11 C9 C12 N1 3.96(16) . . . . ?
C11 C13 C14 C15 -0.1(2) . . . . ?
C12 N1 C13 C11 1.48(18) . . . . ?
C12 N1 C13 C14 -178.75(16) . . . . ?
C12 C9 C11 C13 -3.07(16) . . . . ?
C12 C9 C11 C17 178.06(16) . . . . ?
C13 N1 C12 O2 178.64(15) . . . . ?
C13 N1 C12 C9 -3.51(17) . . . . ?
C13 C11 C17 C16 -0.5(2) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C11 0.1(2) . . . . ?
C17 C11 C13 N1 -179.76(14) . . . . ?
C17 C11 C13 C14 0.5(2) . . . . ?
C18 N1 C12 O2 3.9(3) . . . . ?
C18 N1 C12 C9 -178.28(14) . . . . ?
C18 N1 C13 C11 176.11(15) . . . . ?
C18 N1 C13 C14 -4.1(3) . . . . ?

_olex2_date_sample_data_collection 2021-06-19
_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 1.796
_oxdiff_exptl_absorpt_empirical_full_min 0.543
####################################################################### 
# 
# 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_3064
_database_code_depnum_ccdc_archive 'CCDC 2166563'
loop_
_audit_author_name
_audit_author_address
'Huawen Huang'
;Xiangtan University
China
;
_audit_update_record             
;
2022-04-14 deposited with the CCDC.	2022-07-13 downloaded from the CCDC.
;
_audit_creation_date             2021-06-30
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N O2'
_chemical_formula_sum            'C18 H19 N O2'
_chemical_formula_weight         281.34
_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 0.0033 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8246(6)
_cell_length_b                   9.2051(7)
_cell_length_c                   10.7849(12)
_cell_angle_alpha                94.614(8)
_cell_angle_beta                 101.272(8)
_cell_angle_gamma                99.213(7)
_cell_volume                     746.96(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2599
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      29.0250
_cell_measurement_theta_min      2.6780
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4822
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.938
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  59.00   1.00    1.20    --  -11.43  57.00  30.00   99
  2  ω    -79.00  11.00   1.00    1.20    --  -11.43 -57.00-120.00   90
  3  ω    -15.00  77.00   1.00    1.20    --   12.05  77.00 150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0109620000
_diffrn_orient_matrix_UB_12      -0.0252344000
_diffrn_orient_matrix_UB_13      -0.0613617000
_diffrn_orient_matrix_UB_21      0.0706826000
_diffrn_orient_matrix_UB_22      -0.0342571000
_diffrn_orient_matrix_UB_23      0.0281516000
_diffrn_orient_matrix_UB_31      -0.0609367000
_diffrn_orient_matrix_UB_32      -0.0660735000
_diffrn_orient_matrix_UB_33      -0.0004289000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2228
_reflns_number_total             2633
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.054
_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)+(0.0633P)²+0.0976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1209
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.64645(15) 0.11554(13) 0.43413(11) 0.0366(3) Uani 1 1 d . . . . .
O2 O 0.39681(14) 0.19836(13) 0.60842(10) 0.0306(3) Uani 1 1 d . . . . .
H2 H 0.375799 0.108902 0.586094 0.046 Uiso 1 1 calc R U . . .
N1 N 0.71910(16) 0.36628(15) 0.49065(12) 0.0276(3) Uani 1 1 d . . . . .
C1 C 0.81995(19) 0.46311(17) 0.59580(14) 0.0254(4) Uani 1 1 d . . . . .
C2 C 0.8620(2) 0.61573(19) 0.60885(17) 0.0346(4) Uani 1 1 d . . . . .
H2A H 0.820538 0.669690 0.543642 0.041 Uiso 1 1 calc R U . . .
C3 C 0.9685(2) 0.6856(2) 0.72316(18) 0.0420(5) Uani 1 1 d . . . . .
H3 H 1.000763 0.788226 0.734093 0.050 Uiso 1 1 calc R U . . .
C4 C 1.0275(2) 0.6061(2) 0.82080(17) 0.0433(5) Uani 1 1 d . . . . .
H4 H 1.097865 0.655468 0.896786 0.052 Uiso 1 1 calc R U . . .
C5 C 0.9822(2) 0.45224(19) 0.80621(16) 0.0349(4) Uani 1 1 d . . . . .
H5 H 1.021467 0.398555 0.872205 0.042 Uiso 1 1 calc R U . . .
C6 C 0.87897(18) 0.38063(17) 0.69341(14) 0.0252(4) Uani 1 1 d . . . . .
C7 C 0.80765(19) 0.21834(16) 0.65048(14) 0.0239(4) Uani 1 1 d . . . . .
C8 C 0.67620(19) 0.15316(17) 0.73069(14) 0.0248(4) Uani 1 1 d . . . . .
H8A H 0.634059 0.049142 0.699845 0.030 Uiso 1 1 calc R U . . .
H8B H 0.739846 0.158964 0.818181 0.030 Uiso 1 1 calc R U . . .
C9 C 0.51637(19) 0.22874(17) 0.72899(13) 0.0244(4) Uani 1 1 d . . . . .
H9 H 0.561166 0.335725 0.742167 0.029 Uiso 1 1 calc R U . . .
C10 C 0.42404(18) 0.19269(17) 0.83694(14) 0.0245(4) Uani 1 1 d . . . . .
C11 C 0.4090(2) 0.3047(2) 0.92419(17) 0.0398(4) Uani 1 1 d . . . . .
H11 H 0.456766 0.402052 0.916819 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3236(3) 0.2750(2) 1.02314(18) 0.0465(5) Uani 1 1 d . . . . .
H12 H 0.314974 0.351993 1.081686 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2517(2) 0.1316(2) 1.03432(16) 0.0392(5) Uani 1 1 d . . . . .
H13 H 0.194125 0.111046 1.100290 0.047 Uiso 1 1 calc R U . . .
C14 C 0.2655(2) 0.0193(2) 0.94796(15) 0.0345(4) Uani 1 1 d . . . . .
H14 H 0.216493 -0.077737 0.955360 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3513(2) 0.04827(18) 0.84971(14) 0.0296(4) Uani 1 1 d . . . . .
H15 H 0.360380 -0.029293 0.791933 0.035 Uiso 1 1 calc R U . . .
C16 C 0.9521(2) 0.1242(2) 0.65353(17) 0.0365(4) Uani 1 1 d . . . . .
H16A H 0.900187 0.025812 0.613720 0.055 Uiso 1 1 calc R U . . .
H16B H 1.008766 0.120112 0.740254 0.055 Uiso 1 1 calc R U . . .
H16C H 1.038234 0.167622 0.608553 0.055 Uiso 1 1 calc R U . . .
C17 C 0.6363(2) 0.4129(2) 0.37198(16) 0.0409(5) Uani 1 1 d . . . . .
H17A H 0.555560 0.476922 0.388081 0.061 Uiso 1 1 calc R U . . .
H17B H 0.572639 0.327505 0.314922 0.061 Uiso 1 1 calc R U . . .
H17C H 0.725635 0.465221 0.334243 0.061 Uiso 1 1 calc R U . . .
C18 C 0.71302(19) 0.22202(18) 0.51290(14) 0.0260(4) Uani 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
O1 C18 1.2180(19) . ?
O2 H2 0.8200 . ?
O2 C9 1.4235(18) . ?
N1 C1 1.402(2) . ?
N1 C17 1.448(2) . ?
N1 C18 1.363(2) . ?
C1 C2 1.380(2) . ?
C1 C6 1.396(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(2) . ?
C6 C7 1.509(2) . ?
C7 C8 1.5492(18) . ?
C7 C16 1.527(2) . ?
C7 C18 1.529(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.523(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.5171(19) . ?
C10 C11 1.374(2) . ?
C10 C15 1.389(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H2 109.5 . . ?
C1 N1 C17 124.46(14) . . ?
C18 N1 C1 111.39(12) . . ?
C18 N1 C17 124.13(15) . . ?
C2 C1 N1 128.87(14) . . ?
C2 C1 C6 122.02(16) . . ?
C6 C1 N1 109.11(13) . . ?
C1 C2 H2A 121.3 . . ?
C1 C2 C3 117.36(15) . . ?
C3 C2 H2A 121.3 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.46(16) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.30(17) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.29(16) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 109.01(13) . . ?
C5 C6 C1 119.57(15) . . ?
C5 C6 C7 131.41(14) . . ?
C6 C7 C8 111.39(12) . . ?
C6 C7 C16 113.48(12) . . ?
C6 C7 C18 101.74(12) . . ?
C16 C7 C8 109.02(12) . . ?
C16 C7 C18 109.90(13) . . ?
C18 C7 C8 111.16(12) . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C7 115.23(11) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
O2 C9 C8 111.61(12) . . ?
O2 C9 H9 106.8 . . ?
O2 C9 C10 111.93(11) . . ?
C8 C9 H9 106.8 . . ?
C10 C9 C8 112.43(11) . . ?
C10 C9 H9 106.8 . . ?
C11 C10 C9 119.92(14) . . ?
C11 C10 C15 118.42(13) . . ?
C15 C10 C9 121.66(14) . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.12(16) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.80(17) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.62(15) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.77(15) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.26(16) . . ?
C14 C15 H15 119.9 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 N1 124.86(14) . . ?
O1 C18 C7 126.62(14) . . ?
N1 C18 C7 108.49(13) . . ?

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
O2 C9 C10 C11 -113.09(16) . . . . ?
O2 C9 C10 C15 66.09(18) . . . . ?
N1 C1 C2 C3 -178.53(14) . . . . ?
N1 C1 C6 C5 179.47(13) . . . . ?
N1 C1 C6 C7 -1.61(16) . . . . ?
C1 N1 C18 O1 -173.89(13) . . . . ?
C1 N1 C18 C7 4.50(16) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C1 C6 C7 C8 -114.54(13) . . . . ?
C1 C6 C7 C16 121.97(14) . . . . ?
C1 C6 C7 C18 3.97(14) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C2 C1 C6 C7 178.84(13) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 C7 -179.19(15) . . . . ?
C5 C6 C7 C8 64.2(2) . . . . ?
C5 C6 C7 C16 -59.3(2) . . . . ?
C5 C6 C7 C18 -177.29(15) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C6 C7 C8 C9 58.25(17) . . . . ?
C6 C7 C18 O1 173.29(14) . . . . ?
C6 C7 C18 N1 -5.07(15) . . . . ?
C7 C8 C9 O2 70.35(16) . . . . ?
C7 C8 C9 C10 -162.91(13) . . . . ?
C8 C7 C18 O1 -68.03(19) . . . . ?
C8 C7 C18 N1 113.62(13) . . . . ?
C8 C9 C10 C11 120.35(16) . . . . ?
C8 C9 C10 C15 -60.47(18) . . . . ?
C9 C10 C11 C12 179.34(16) . . . . ?
C9 C10 C15 C14 -178.94(14) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C10 C15 C14 0.2(2) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C10 -0.4(2) . . . . ?
C15 C10 C11 C12 0.1(3) . . . . ?
C16 C7 C8 C9 -175.76(13) . . . . ?
C16 C7 C18 O1 52.75(19) . . . . ?
C16 C7 C18 N1 -125.60(13) . . . . ?
C17 N1 C1 C2 -0.6(2) . . . . ?
C17 N1 C1 C6 179.89(14) . . . . ?
C17 N1 C18 O1 4.4(2) . . . . ?
C17 N1 C18 C7 -177.26(13) . . . . ?
C18 N1 C1 C2 177.64(14) . . . . ?
C18 N1 C1 C6 -1.87(17) . . . . ?
C18 C7 C8 C9 -54.45(18) . . . . ?

_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 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.642
