# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_exp_847
_database_code_depnum_ccdc_archive 'CCDC 1917989'
loop_
_audit_author_name
_audit_author_address
'Wen-Biao Wu'
;East China Normal University
China
;
_audit_update_record             
;
2019-05-23 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_audit_creation_date             2019-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 O2'
_chemical_formula_sum            'C15 H16 O2'
_chemical_formula_weight         228.28
_chemical_absolute_configuration ?
_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'
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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   8.78830(10)
_cell_length_b                   12.6773(2)
_cell_length_c                   10.4803(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.0970(10)
_cell_angle_gamma                90
_cell_volume                     1152.94(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9578
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1910
_cell_measurement_theta_min      6.1580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10931
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.443
_diffrn_reflns_theta_min         6.180
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  10.00   1.00    1.00    --    0.00 -57.00-120.00   27
  2  ω     55.00  89.00   1.00    1.00    --    0.00  38.00-150.00   34
  3  ω    -82.00 -56.00   1.00    1.00    --    0.00 -82.00-150.00   26
  4  ω     27.00  88.00   1.00    1.00    --    0.00  77.00-120.00   61
  5  ω    -17.00  21.00   1.00    1.00    --    0.00  38.00-150.00   38
  6  ω    -23.00  14.00   1.00    1.00    --    0.00  77.00-120.00   37
  7  ω     24.00  50.00   1.00    1.00    --    0.00  38.00-150.00   26
  8  ω    -28.00  19.00   1.00    1.00    --    0.00 -82.00-150.00   47
  9  ω    -86.00 -34.00   1.00    1.00    --    0.00 -57.00-120.00   52
 10  ω    -23.00  10.00   1.00    1.00    --    0.00  57.00 150.00   33
 11  ω    -19.00  31.00   1.00    1.00    --    0.00  38.00   0.00   50
 12  ω     56.00  81.00   1.00    1.00    --    0.00  38.00   0.00   25
 13  ω    -16.00  26.00   1.00    1.00    --    0.00  38.00  60.00   42
 14  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 15  ω    123.00 170.00   1.00    1.00    --   95.80  61.00 120.00   47
 16  ω      6.00  65.00   1.00    1.00    --   95.80 -82.00 150.00   59
 17  ω     72.00  97.00   1.00    1.00    --   95.80  61.00 120.00   25
 18  ω    144.00 170.00   1.00    1.00    --   95.80  45.00  30.00   26
 19  ω    127.00 175.00   1.00    1.00    --   95.80  82.00 150.00   48
 20  ω     75.00 175.00   1.00    1.00    --   95.80  57.00  46.73  100
 21  ω     65.00  95.00   1.00    1.00    --   95.80  77.00 -90.00   30
 22  ω     78.00 107.00   1.00    1.00    --   95.80  45.00 120.00   29
 23  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 24  ω    138.00 185.00   1.00    1.00    --   95.80  77.00-120.00   47
 25  ω     63.00  95.00   1.00    1.00    --   95.80  82.00 -30.00   32
 26  ω    124.00 185.00   1.00    1.00    --   95.80  82.00 -30.00   61
 27  ω     45.00 123.00   1.00    1.00    --   95.80 -82.00 -90.00   78
 28  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 29  ω     66.00 104.00   1.00    1.00    --   95.80  77.00 120.00   38
 30  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 31  ω     76.00 131.00   1.00    1.00    --   95.80  45.00  30.00   55
 32  ω     66.00  92.00   1.00    1.00    --   95.80  77.00  60.00   26
 33  ω     74.00 100.00   1.00    1.00    --   95.80  61.00-180.00   26
 34  ω     76.00 112.00   1.00    1.00    --   95.80  45.00 -90.00   36
 35  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 36  ω     67.00  93.00   1.00    1.00    --   95.80  77.00  30.00   26
 37  ω     73.00 150.00   1.00    1.00    --   95.80  61.00 -90.00   77
 38  ω     63.00  97.00   1.00    1.00    --   95.80  82.00-180.00   34
 39  ω     75.00 110.00   1.00    1.00    --   95.80  45.00 -30.00   35
 40  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  90.00   25
 41  ω     30.00 114.00   1.00    1.00    --   95.80 -77.00-150.00   84
 42  ω     75.00 160.00   1.00    1.00    --   95.80  45.00-120.00   85
 43  ω    125.00 185.00   1.00    1.00    --   95.80  82.00  60.00   60
 44  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 45  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 46  ω     76.00 102.00   1.00    1.00    --   95.80  61.00  90.00   26
 47  ω    125.00 181.00   1.00    1.00    --   95.80  61.00  90.00   56
 48  ω     70.00 102.00   1.00    1.00    --   95.80 -82.00 150.00   32
 49  ω     10.00 122.00   1.00    1.00    --   95.80 -82.00   0.00  112
 50  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 51  ω     75.00 111.00   1.00    1.00    --   95.80  45.00-180.00   36
 52  ω     82.00 142.00   1.00    1.00    --   95.80  45.00-150.00   60
 53  ω    148.00 185.00   1.00    1.00    --   95.80  45.00-150.00   37
 54  ω     75.00 100.00   1.00    1.00    --   95.80  45.00  90.00   25
 55  ω     74.00 100.00   1.00    1.00    --   95.80  61.00  30.00   26
 56  ω     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 57  ω    123.00 149.00   1.00    1.00    --   95.80  73.00 -36.75   26
 58  ω    123.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   62
 59  ω     23.00  75.00   1.00    1.00    --   95.80 -82.00  60.00   52
 60  ω     95.00 120.00   1.00    1.00    --   95.80 -82.00  60.00   25
 61  ω     67.00 117.00   1.00    1.00    --   95.80  73.00 -36.75   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0486944000
_diffrn_orient_matrix_UB_12      -0.1168264000
_diffrn_orient_matrix_UB_13      0.0074676000
_diffrn_orient_matrix_UB_21      -0.1594243000
_diffrn_orient_matrix_UB_22      -0.0313668000
_diffrn_orient_matrix_UB_23      -0.0733697000
_diffrn_orient_matrix_UB_31      0.0609041000
_diffrn_orient_matrix_UB_32      0.0110309000
_diffrn_orient_matrix_UB_33      -0.1294466000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                2184
_reflns_number_total             2186
_reflns_odcompleteness_completeness 99.82
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.179
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1006 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(12)
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.045
_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)+(0.0546P)²+0.3822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0845
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C9(H9A,H9B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C3(H3), C2(H2), C4(H4)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 0.33103(16) 0.43254(10) 0.37148(13) 0.0220(3) Uani 1 1 d . . . . .
O2 O 0.56779(19) 0.94542(11) 0.58340(15) 0.0275(4) Uani 1 1 d . . . . .
C1 C 0.4423(2) 0.38240(15) 0.4565(2) 0.0194(4) Uani 1 1 d . . . . .
C13 C 0.3252(2) 0.54562(14) 0.3842(2) 0.0220(4) Uani 1 1 d . . . . .
H13A H 0.279357 0.563240 0.459755 0.026 Uiso 1 1 calc R . . . .
H13B H 0.260242 0.574827 0.309034 0.026 Uiso 1 1 calc R . . . .
C7 C 0.5875(2) 0.55302(14) 0.51798(19) 0.0185(4) Uani 1 1 d . . . . .
H7 H 0.695044 0.567062 0.509449 0.022 Uiso 1 1 calc R . . . .
C12 C 0.4849(2) 0.59508(14) 0.39687(19) 0.0199(4) Uani 1 1 d . . . . .
H12 H 0.530870 0.573677 0.321584 0.024 Uiso 1 1 calc R . . . .
C11 C 0.4746(2) 0.71337(15) 0.39658(19) 0.0204(4) Uani 1 1 d . . . . .
H11 H 0.432099 0.746237 0.319832 0.025 Uiso 1 1 calc R . . . .
C10 C 0.5222(2) 0.77478(14) 0.4989(2) 0.0191(4) Uani 1 1 d . . . . .
C5 C 0.6751(2) 0.37447(16) 0.6100(2) 0.0213(4) Uani 1 1 d . . . . .
H5 H 0.759452 0.407847 0.658118 0.026 Uiso 1 1 calc R . . . .
C3 C 0.5349(2) 0.21563(14) 0.5485(2) 0.0232(4) Uani 1 1 d . . . . .
H3 H 0.524002 0.142968 0.555253 0.028 Uiso 1 1 calc R . . . .
C14 C 0.5173(2) 0.89197(13) 0.4893(2) 0.0199(4) Uani 1 1 d . . . . .
C9 C 0.5871(3) 0.72955(14) 0.6292(2) 0.0212(4) Uani 1 1 d . . . . .
H9A H 0.543739 0.766969 0.695765 0.025 Uiso 1 1 calc R . . . .
H9B H 0.697837 0.739899 0.645090 0.025 Uiso 1 1 calc R . . . .
C6 C 0.5675(2) 0.43475(14) 0.5286(2) 0.0194(4) Uani 1 1 d . . . . .
C8 C 0.5517(2) 0.61203(15) 0.63743(19) 0.0200(4) Uani 1 1 d . . . . .
H8A H 0.443808 0.602788 0.644489 0.024 Uiso 1 1 calc R . . . .
H8B H 0.612810 0.582520 0.714329 0.024 Uiso 1 1 calc R . . . .
C2 C 0.4269(2) 0.27304(15) 0.4661(2) 0.0223(4) Uani 1 1 d . . . . .
H2 H 0.343925 0.238813 0.417143 0.027 Uiso 1 1 calc R . . . .
C4 C 0.6593(2) 0.26626(16) 0.6211(2) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.731730 0.227841 0.676713 0.028 Uiso 1 1 calc R . . . .
C15 C 0.4498(3) 0.94369(15) 0.3637(2) 0.0253(5) Uani 1 1 d . . . . .
H15A H 0.458271 1.018916 0.372654 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.343191 0.924468 0.341811 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.504814 0.920668 0.296570 0.038 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 C1 1.371(2) . ?
O1 C13 1.441(2) . ?
O2 C14 1.221(2) . ?
C1 C6 1.399(3) . ?
C1 C2 1.398(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.523(3) . ?
C7 H7 0.9800 . ?
C7 C12 1.532(3) . ?
C7 C6 1.516(2) . ?
C7 C8 1.533(3) . ?
C12 H12 0.9800 . ?
C12 C11 1.502(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.338(3) . ?
C10 C14 1.489(2) . ?
C10 C9 1.507(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(3) . ?
C5 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.385(3) . ?
C3 C4 1.386(3) . ?
C14 C15 1.506(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.527(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C1 O1 C13 115.67(15) . . ?
O1 C1 C6 123.38(16) . . ?
O1 C1 C2 116.04(17) . . ?
C2 C1 C6 120.57(18) . . ?
O1 C13 H13A 109.3 . . ?
O1 C13 H13B 109.3 . . ?
O1 C13 C12 111.83(16) . . ?
H13A C13 H13B 107.9 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C12 C7 H7 108.1 . . ?
C12 C7 C8 109.70(15) . . ?
C6 C7 H7 108.1 . . ?
C6 C7 C12 110.20(15) . . ?
C6 C7 C8 112.44(16) . . ?
C8 C7 H7 108.1 . . ?
C13 C12 C7 110.03(16) . . ?
C13 C12 H12 107.9 . . ?
C7 C12 H12 107.9 . . ?
C11 C12 C13 110.87(16) . . ?
C11 C12 C7 112.12(15) . . ?
C11 C12 H12 107.9 . . ?
C12 C11 H11 117.7 . . ?
C10 C11 C12 124.62(17) . . ?
C10 C11 H11 117.7 . . ?
C11 C10 C14 121.59(17) . . ?
C11 C10 C9 122.04(16) . . ?
C14 C10 C9 116.35(15) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.73(18) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.14(17) . . ?
C4 C3 H3 119.9 . . ?
O2 C14 C10 119.72(17) . . ?
O2 C14 C15 120.47(16) . . ?
C10 C14 C15 119.80(16) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C10 C9 C8 111.78(15) . . ?
H9A C9 H9B 107.9 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C1 C6 C7 121.32(16) . . ?
C5 C6 C1 117.95(16) . . ?
C5 C6 C7 120.73(17) . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 C7 111.11(16) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.07(19) . . ?
C3 C2 H2 120.0 . . ?
C5 C4 C3 119.54(18) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 2.248
_oxdiff_exptl_absorpt_empirical_full_min 0.445
####################################################################### 
# 
# 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_2044
_database_code_depnum_ccdc_archive 'CCDC 2089395'
loop_
_audit_author_name
_audit_author_address
'Wen-Biao Wu'
;East China Normal University
China
;
_audit_update_record             
;
2021-06-11 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_audit_creation_date             2021-06-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 Br N O'
_chemical_formula_sum            'C17 H18 Br N O'
_chemical_formula_weight         332.23
_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'
Br Br -0.6763 1.2805 '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                   19.7377(2)
_cell_length_b                   9.57380(10)
_cell_length_c                   7.61300(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.0900(10)
_cell_angle_gamma                90
_cell_volume                     1420.52(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10676
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      74.0590
_cell_measurement_theta_min      4.5170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            13942
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.623
_diffrn_reflns_theta_min         4.537
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  19.00   1.00    1.00    --    0.00 -38.00  90.00   37
  2  ω    -10.00  24.00   1.00    1.00    --    0.00 -77.00-180.00   34
  3  ω    -89.00 -32.00   1.00    1.00    --    0.00 -19.00 -30.00   57
  4  ω    -88.00 -40.00   1.00    1.00    --    0.00 -38.00  90.00   48
  5  ω    -10.00  24.00   1.00    1.00    --    0.00 -19.00 -30.00   34
  6  ω    -65.00 -40.00   1.00    1.00    --    0.00 -77.00-180.00   25
  7  ω      6.00 118.00   1.00    1.00    --   95.80 -61.00 -60.00  112
  8  ω    103.00 128.00   1.00    1.00    --   95.80 -82.00 150.00   25
  9  ω     69.00 127.00   1.00    1.00    --   95.80  15.00  60.00   58
 10  ω     77.00 126.00   1.00    1.00    --   95.80 -82.00-120.00   49
 11  ω      7.00 101.00   1.00    1.00    --   95.80 -15.00 120.00   94
 12  ω     11.00  72.00   1.00    1.00    --   95.80 -82.00-120.00   61
 13  ω     50.00  89.00   1.00    1.00    --   95.80 -82.00 150.00   39
 14  ω     26.00  60.00   1.00    1.00    --   95.80 -82.00 -60.00   34
 15  ω     80.00 156.00   1.00    1.00    --   95.80  30.00 150.00   76
 16  ω     11.00 124.00   1.00    1.00    --   95.80 -82.00  60.00  113
 17  ω      7.00 108.00   1.00    1.00    --   95.80 -61.00  60.00  101
 18  ω     73.00 119.00   1.00    1.00    --   95.80 -82.00 -60.00   46
 19  ω    110.00 183.00   1.00    1.00    --   95.80  30.00 120.00   73
 20  ω     55.00 127.00   1.00    1.00    --   95.80 -82.00-180.00   72
 21  ω     93.00 118.00   1.00    1.00    --   95.80  45.00  30.00   25
 22  ω    147.00 184.00   1.00    1.00    --   95.80  45.00  30.00   37
 23  ω     73.00  98.00   1.00    1.00    --   95.80 -82.00 -30.00   25
 24  ω    151.00 185.00   1.00    1.00    --   95.80  15.00  60.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0400562000
_diffrn_orient_matrix_UB_12      -0.1373319000
_diffrn_orient_matrix_UB_13      -0.0083648000
_diffrn_orient_matrix_UB_21      0.0679647000
_diffrn_orient_matrix_UB_22      0.0787265000
_diffrn_orient_matrix_UB_23      0.0572695000
_diffrn_orient_matrix_UB_31      -0.0050742000
_diffrn_orient_matrix_UB_32      -0.0287272000
_diffrn_orient_matrix_UB_33      0.1966081000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2770
_reflns_number_total             2860
_reflns_odcompleteness_completeness 99.82
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.00160(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.079
_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)+(0.0386P)²+0.9612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0740
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
2.d 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
Br1 Br 0.09238(2) -0.04297(2) -0.03363(3) 0.02370(10) Uani 1 1 d . . . . .
O1 O 0.44546(8) 0.71138(18) 0.4265(2) 0.0396(4) Uani 1 1 d . . . . .
N1 N 0.32698(10) 0.53415(19) 0.6341(2) 0.0304(4) Uani 1 1 d . . . . .
C1 C 0.18090(9) 0.34836(19) 0.0727(2) 0.0175(3) Uani 1 1 d . . . . .
C2 C 0.16867(9) 0.20443(19) 0.0663(2) 0.0189(3) Uani 1 1 d . . . . .
H2 H 0.201470 0.143149 0.123711 0.023 Uiso 1 1 calc R . . . .
C3 C 0.10768(10) 0.1536(2) -0.0256(2) 0.0193(4) Uani 1 1 d . . . . .
C4 C 0.05681(9) 0.2421(2) -0.1102(2) 0.0221(4) Uani 1 1 d . . . . .
H4 H 0.015583 0.206795 -0.169710 0.026 Uiso 1 1 calc R . . . .
C5 C 0.06945(9) 0.3837(2) -0.1031(2) 0.0222(4) Uani 1 1 d . . . . .
H5 H 0.035951 0.444276 -0.158882 0.027 Uiso 1 1 calc R . . . .
C6 C 0.13121(10) 0.43928(19) -0.0145(2) 0.0193(4) Uani 1 1 d . . . . .
C7 C 0.14262(10) 0.5957(2) -0.0160(3) 0.0232(4) Uani 1 1 d . . . . .
H7A H 0.115949 0.639621 0.065363 0.028 Uiso 1 1 calc R . . . .
H7B H 0.126250 0.631384 -0.134403 0.028 Uiso 1 1 calc R . . . .
C8 C 0.21802(10) 0.6354(2) 0.0373(2) 0.0227(4) Uani 1 1 d . . . . .
H8A H 0.243776 0.609338 -0.056182 0.027 Uiso 1 1 calc R . . . .
H8B H 0.222302 0.735463 0.055582 0.027 Uiso 1 1 calc R . . . .
C9 C 0.24607(10) 0.55828(18) 0.2090(3) 0.0192(4) Uani 1 1 d . . . . .
H9 H 0.213281 0.573227 0.291388 0.023 Uiso 1 1 calc R . . . .
C10 C 0.31614(9) 0.61444(18) 0.3018(2) 0.0185(4) Uani 1 1 d . . . . .
H10 H 0.314152 0.716711 0.299117 0.022 Uiso 1 1 calc R . . . .
C11 C 0.37716(9) 0.56837(19) 0.2114(2) 0.0189(4) Uani 1 1 d . . . . .
H11 H 0.369812 0.608989 0.091771 0.023 Uiso 1 1 calc R . . . .
C12 C 0.37776(9) 0.4093(2) 0.1882(3) 0.0215(4) Uani 1 1 d . . . . .
H12A H 0.414795 0.383195 0.124849 0.026 Uiso 1 1 calc R . . . .
H12B H 0.385935 0.364922 0.304192 0.026 Uiso 1 1 calc R . . . .
C13 C 0.30968(9) 0.35807(19) 0.0852(2) 0.0211(4) Uani 1 1 d . . . . .
H13A H 0.310963 0.257137 0.075214 0.025 Uiso 1 1 calc R . . . .
H13B H 0.303497 0.396711 -0.034015 0.025 Uiso 1 1 calc R . . . .
C14 C 0.24855(9) 0.40014(18) 0.1758(2) 0.0171(3) Uani 1 1 d . . . . .
H14 H 0.254734 0.354284 0.292353 0.021 Uiso 1 1 calc R . . . .
C15 C 0.44480(10) 0.6271(2) 0.3076(3) 0.0235(4) Uani 1 1 d . . . . .
C16 C 0.50965(10) 0.5784(2) 0.2494(3) 0.0292(4) Uani 1 1 d . . . . .
H16A H 0.547644 0.631063 0.310165 0.044 Uiso 1 1 calc GR . . . .
H16B H 0.506576 0.591668 0.123357 0.044 Uiso 1 1 calc GR . . . .
H16C H 0.516386 0.481048 0.277111 0.044 Uiso 1 1 calc GR . . . .
C17 C 0.32500(9) 0.56971(19) 0.4898(3) 0.0214(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
Br1 C3 1.9054(19) . ?
O1 C15 1.211(2) . ?
N1 C17 1.145(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.398(3) . ?
C1 C14 1.521(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(3) . ?
C3 C4 1.392(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(3) . ?
C6 C7 1.515(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.527(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.527(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.547(2) . ?
C9 C14 1.537(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.543(2) . ?
C10 C17 1.478(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.533(2) . ?
C11 C15 1.525(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.526(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.535(2) . ?
C14 H14 0.9800 . ?
C15 C16 1.494(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C2 C1 C14 118.13(15) . . ?
C6 C1 C2 119.53(16) . . ?
C6 C1 C14 122.33(16) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.76(17) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 Br1 119.02(14) . . ?
C2 C3 C4 121.81(17) . . ?
C4 C3 Br1 119.17(14) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.90(17) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.05(17) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 118.93(17) . . ?
C1 C6 C7 121.69(16) . . ?
C5 C6 C7 119.38(16) . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C6 C7 C8 112.55(15) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 C7 108.27(15) . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C8 C9 H9 106.9 . . ?
C8 C9 C10 113.57(15) . . ?
C8 C9 C14 110.60(15) . . ?
C10 C9 H9 106.9 . . ?
C14 C9 H9 106.9 . . ?
C14 C9 C10 111.60(14) . . ?
C9 C10 H10 107.9 . . ?
C11 C10 C9 113.70(15) . . ?
C11 C10 H10 107.9 . . ?
C17 C10 C9 107.57(15) . . ?
C17 C10 H10 107.9 . . ?
C17 C10 C11 111.58(15) . . ?
C10 C11 H11 106.8 . . ?
C12 C11 C10 110.86(15) . . ?
C12 C11 H11 106.8 . . ?
C15 C11 C10 111.49(15) . . ?
C15 C11 H11 106.8 . . ?
C15 C11 C12 113.55(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 C11 110.87(15) . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C12 C13 C14 112.07(15) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C1 C14 C9 110.96(14) . . ?
C1 C14 C13 111.76(14) . . ?
C1 C14 H14 107.2 . . ?
C9 C14 H14 107.2 . . ?
C13 C14 C9 112.34(15) . . ?
C13 C14 H14 107.2 . . ?
O1 C15 C11 120.65(17) . . ?
O1 C15 C16 121.43(18) . . ?
C16 C15 C11 117.92(17) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C10 175.2(2) . . ?

_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 5.594
_oxdiff_exptl_absorpt_empirical_full_min 0.331
####################################################################### 
# 
# 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_879
_database_code_depnum_ccdc_archive 'CCDC 1921832'
loop_
_audit_author_name
_audit_author_address
'Wen-Biao Wu'
;East China Normal University
China
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_audit_creation_date             2019-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 O'
_chemical_formula_sum            'C16 H18 O'
_chemical_formula_weight         226.30
_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'
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                   7.27630(10)
_cell_length_b                   13.18790(10)
_cell_length_c                   12.60950(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.1790(10)
_cell_angle_gamma                90
_cell_volume                     1206.78(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17005
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.0780
_cell_measurement_theta_min      4.8500
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.836
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25070
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.434
_diffrn_reflns_theta_min         4.859
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00  70.00   1.00    1.00    --    0.00  57.00  90.00   26
  2  ω    -17.00  62.00   1.00    1.00    --    0.00  38.00  60.00   79
  3  ω     64.00  89.00   1.00    1.00    --    0.00  57.00-180.00   25
  4  ω    -18.00  89.00   1.00    1.00    --    0.00  38.00 -90.00  107
  5  ω    -19.00  32.00   1.00    1.00    --    0.00  38.00 -30.00   51
  6  ω    -89.00 -37.00   1.00    1.00    --    0.00 -57.00 150.00   52
  7  ω     57.00  82.00   1.00    1.00    --    0.00  77.00  90.00   25
  8  ω      8.00  47.00   1.00    1.00    --    0.00  77.00  90.00   39
  9  ω     10.00  37.00   1.00    1.00    --    0.00  57.00  90.00   27
 10  ω    -29.00  23.00   1.00    1.00    --    0.00 -57.00 150.00   52
 11  ω    -23.00  24.00   1.00    1.00    --    0.00  57.00-180.00   47
 12  ω     29.00  57.00   1.00    1.00    --    0.00  57.00-180.00   28
 13  ω     41.00  83.00   1.00    1.00    --    0.00  38.00 -30.00   42
 14  ω     49.00 118.00   1.00    1.00    --   95.80 -82.00  60.00   69
 15  ω     71.00 181.00   1.00    1.00    --   95.80  61.00   0.00  110
 16  ω     71.00 164.00   1.00    1.00    --   95.80  61.00  30.00   93
 17  ω    116.00 184.00   1.00    1.00    --   95.80  45.00 120.00   68
 18  ω     75.00 112.00   1.00    1.00    --   95.80  45.00 120.00   37
 19  ω     63.00 185.00   1.00    1.00    --   95.80  82.00-150.00  122
 20  ω     68.00 148.00   1.00    1.00    --   95.80  68.00  63.11   80
 21  ω     75.00 103.00   1.00    1.00    --   95.80  45.00   0.00   28
 22  ω     71.00 156.00   1.00    1.00    --   95.80  61.00 -90.00   85
 23  ω    108.00 134.00   1.00    1.00    --   95.80  45.00   0.00   26
 24  ω     65.00  92.00   1.00    1.00    --   95.80  77.00 150.00   27
 25  ω     65.00 100.00   1.00    1.00    --   95.80  77.00 -90.00   35
 26  ω    143.00 174.00   1.00    1.00    --   95.80  45.00-150.00   31
 27  ω     60.00  86.00   1.00    1.00    --   95.80 -77.00-150.00   26
 28  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 29  ω     99.00 125.00   1.00    1.00    --   95.80  82.00  30.00   26
 30  ω     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 31  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 32  ω      7.00  46.00   1.00    1.00    --   95.80 -77.00-150.00   39
 33  ω     63.00  98.00   1.00    1.00    --   95.80  82.00 -60.00   35
 34  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 35  ω    118.00 177.00   1.00    1.00    --   95.80  82.00-180.00   59
 36  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 37  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 38  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 39  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 40  ω     97.00 122.00   1.00    1.00    --   95.80  82.00  60.00   25
 41  ω    122.00 147.00   1.00    1.00    --   95.80  77.00-120.00   25
 42  ω     64.00  91.00   1.00    1.00    --   95.80  82.00  90.00   27
 43  ω     75.00 160.00   1.00    1.00    --   95.80  45.00-180.00   85
 44  ω     11.00 107.00   1.00    1.00    --   95.80 -61.00 -90.00   96
 45  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 46  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 47  ω     57.00 123.00   1.00    1.00    --   95.80 -77.00  90.00   66
 48  ω     74.00 101.00   1.00    1.00    --   95.80  61.00-150.00   27
 49  ω     75.00 158.00   1.00    1.00    --   95.80  45.00 150.00   83
 50  ω      9.00 128.00   1.00    1.00    --   95.80 -82.00 -90.00  119
 51  ω      6.00 115.00   1.00    1.00    --   95.80 -82.00 150.00  109
 52  ω     75.00 100.00   1.00    1.00    --   95.80  45.00-150.00   25
 53  ω     65.00  97.00   1.00    1.00    --   95.80  77.00-120.00   32
 54  ω     64.00  90.00   1.00    1.00    --   95.80  82.00 150.00   26
 55  ω     67.00 179.00   1.00    1.00    --   95.80  72.00 -65.32  112
 56  ω    148.00 185.00   1.00    1.00    --   95.80  53.00 153.40   37
 57  ω     93.00 119.00   1.00    1.00    --   95.80 -82.00 -30.00   26
 58  ω     73.00  99.00   1.00    1.00    --   95.80  53.00 153.40   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0557865000
_diffrn_orient_matrix_UB_12      0.1124506000
_diffrn_orient_matrix_UB_13      -0.0045678000
_diffrn_orient_matrix_UB_21      0.1257746000
_diffrn_orient_matrix_UB_22      -0.0134281000
_diffrn_orient_matrix_UB_23      0.1026535000
_diffrn_orient_matrix_UB_31      0.1618132000
_diffrn_orient_matrix_UB_32      -0.0284542000
_diffrn_orient_matrix_UB_33      -0.0666460000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2371
_reflns_number_total             2436
_reflns_odcompleteness_completeness 99.91
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.421
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.038
_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)+(0.0514P)²+0.6685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1109
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10)
2.d 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
O1 O 0.88586(13) 0.73891(8) 0.56639(8) 0.0279(3) Uani 1 1 d . . . . .
C1 C 0.07980(17) 0.61687(9) 0.34552(10) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.04009(17) 0.51324(10) 0.34971(11) 0.0229(3) Uani 1 1 d . . . . .
H2 H 0.113342 0.471567 0.394769 0.027 Uiso 1 1 calc R . . . .
C3 C -0.10605(18) 0.47144(10) 0.28815(11) 0.0240(3) Uani 1 1 d . . . . .
H3 H -0.129453 0.402210 0.291077 0.029 Uiso 1 1 calc R . . . .
C4 C -0.21751(17) 0.53380(10) 0.22193(11) 0.0233(3) Uani 1 1 d . . . . .
H4 H -0.316372 0.506440 0.180574 0.028 Uiso 1 1 calc R . . . .
C5 C -0.18106(17) 0.63680(10) 0.21763(10) 0.0211(3) Uani 1 1 d . . . . .
H5 H -0.256584 0.678154 0.173474 0.025 Uiso 1 1 calc R . . . .
C6 C -0.03258(16) 0.67956(9) 0.27862(10) 0.0188(3) Uani 1 1 d . . . . .
C7 C 0.00061(18) 0.79257(9) 0.27400(10) 0.0218(3) Uani 1 1 d . . . . .
H7A H -0.083372 0.826797 0.318434 0.026 Uiso 1 1 calc R . . . .
H7B H -0.025854 0.815882 0.201536 0.026 Uiso 1 1 calc R . . . .
C8 C 0.19768(18) 0.82113(10) 0.31090(11) 0.0236(3) Uani 1 1 d . . . . .
H8A H 0.208417 0.894315 0.315952 0.028 Uiso 1 1 calc R . . . .
H8B H 0.280819 0.797584 0.259423 0.028 Uiso 1 1 calc R . . . .
C9 C 0.25145(17) 0.77342(9) 0.41954(10) 0.0206(3) Uani 1 1 d . . . . .
H9 H 0.159905 0.795237 0.468075 0.025 Uiso 1 1 calc R . . . .
C10 C 0.43612(18) 0.81084(10) 0.46462(10) 0.0222(3) Uani 1 1 d . . . . .
H10 H 0.447130 0.879689 0.479737 0.027 Uiso 1 1 calc R . . . .
C11 C 0.58619(17) 0.75306(9) 0.48479(10) 0.0192(3) Uani 1 1 d . . . . .
C12 C 0.58590(17) 0.64176(10) 0.45748(11) 0.0221(3) Uani 1 1 d . . . . .
H12A H 0.575024 0.602099 0.521506 0.027 Uiso 1 1 calc R . . . .
H12B H 0.701502 0.624064 0.428442 0.027 Uiso 1 1 calc R . . . .
C13 C 0.42607(17) 0.61632(10) 0.37649(10) 0.0213(3) Uani 1 1 d . . . . .
H13A H 0.417739 0.543404 0.367275 0.026 Uiso 1 1 calc R . . . .
H13B H 0.448132 0.646325 0.308338 0.026 Uiso 1 1 calc R . . . .
C14 C 0.24427(16) 0.65695(9) 0.41441(10) 0.0195(3) Uani 1 1 d . . . . .
H14 H 0.233480 0.631907 0.486863 0.023 Uiso 1 1 calc R . . . .
C15 C 0.75732(17) 0.79506(10) 0.53949(10) 0.0211(3) Uani 1 1 d . . . . .
C16 C 0.77006(19) 0.90705(10) 0.56432(11) 0.0274(3) Uani 1 1 d . . . . .
H16A H 0.683746 0.923962 0.615609 0.041 Uiso 1 1 calc GR . . . .
H16B H 0.741881 0.945290 0.500412 0.041 Uiso 1 1 calc GR . . . .
H16C H 0.892630 0.923053 0.592708 0.041 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 C15 1.2215(16) . ?
C1 C2 1.3986(17) . ?
C1 C6 1.4012(17) . ?
C1 C14 1.5214(16) . ?
C2 H2 0.9300 . ?
C2 C3 1.3845(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.3902(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.3858(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.3984(17) . ?
C6 C7 1.5116(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5223(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.5322(18) . ?
C9 H9 0.9800 . ?
C9 C10 1.5036(17) . ?
C9 C14 1.5381(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.3406(18) . ?
C11 C12 1.5077(17) . ?
C11 C15 1.4859(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5281(17) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.5355(17) . ?
C14 H14 0.9800 . ?
C15 C16 1.5112(18) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C2 C1 C6 119.09(11) . . ?
C2 C1 C14 118.29(11) . . ?
C6 C1 C14 122.62(11) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.35(12) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.46(12) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.89(12) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.08(12) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 121.14(11) . . ?
C5 C6 C1 119.12(11) . . ?
C5 C6 C7 119.71(11) . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C6 C7 C8 112.44(10) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C7 C8 C9 110.19(11) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C8 C9 H9 107.3 . . ?
C8 C9 C14 111.52(10) . . ?
C10 C9 C8 111.48(11) . . ?
C10 C9 H9 107.3 . . ?
C10 C9 C14 111.74(10) . . ?
C14 C9 H9 107.3 . . ?
C9 C10 H10 117.3 . . ?
C11 C10 C9 125.33(12) . . ?
C11 C10 H10 117.3 . . ?
C10 C11 C12 121.50(11) . . ?
C10 C11 C15 121.30(12) . . ?
C15 C11 C12 117.14(11) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 C13 110.77(10) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C12 C13 C14 110.26(10) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C1 C14 C9 113.20(10) . . ?
C1 C14 C13 111.14(10) . . ?
C1 C14 H14 107.6 . . ?
C9 C14 H14 107.6 . . ?
C13 C14 C9 109.52(10) . . ?
C13 C14 H14 107.6 . . ?
O1 C15 C11 120.11(12) . . ?
O1 C15 C16 120.06(12) . . ?
C11 C15 C16 119.81(11) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_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 2.707
_oxdiff_exptl_absorpt_empirical_full_min 0.396
####################################################################### 
# 
# 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_2169
_database_code_depnum_ccdc_archive 'CCDC 2101568'
loop_
_audit_author_name
_audit_author_address
'Wen-Biao Wu'
;East China Normal University
China
;
_audit_update_record             
;
2021-08-05 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_audit_creation_date             2021-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 N O2'
_chemical_formula_sum            'C18 H21 N O2'
_chemical_formula_weight         283.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2466(2)
_cell_length_b                   8.3731(2)
_cell_length_c                   12.6472(3)
_cell_angle_alpha                95.047(2)
_cell_angle_beta                 96.626(2)
_cell_angle_gamma                94.254(2)
_cell_volume                     756.54(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10273
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.0700
_cell_measurement_theta_min      3.5260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14785
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         3.535
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -33.00   1.00    1.00    --    0.00 -82.00-150.00   55
  2  ω    -35.00  -9.00   1.00    1.00    --    0.00 -38.00 120.00   26
  3  ω    -18.00  35.00   1.00    1.00    --    0.00  38.00  60.00   53
  4  ω    -19.00  30.00   1.00    1.00    --    0.00  38.00-150.00   49
  5  ω     64.00  89.00   1.00    1.00    --    0.00  38.00-150.00   25
  6  ω    -26.00  14.00   1.00    1.00    --    0.00 -82.00-150.00   40
  7  ω    -16.00  43.00   1.00    1.00    --    0.00  38.00 150.00   59
  8  ω    -74.00 -46.00   1.00    1.00    --    0.00 -38.00 120.00   28
  9  ω    -23.00  85.00   1.00    1.00    --    0.00  19.00 -60.00  108
 10  ω     44.00  69.00   1.00    1.00    --    0.00  38.00  60.00   25
 11  ω     75.00 117.00   1.00    1.00    --   95.80  45.00 -30.00   42
 12  ω     98.00 124.00   1.00    1.00    --   95.80  77.00 150.00   26
 13  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 14  ω    141.00 167.00   1.00    1.00    --   95.80  77.00  30.00   26
 15  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 16  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 150.00   26
 17  ω    151.00 178.00   1.00    1.00    --   95.80  59.00  74.53   27
 18  ω     65.00 136.00   1.00    1.00    --   95.80  82.00-120.00   71
 19  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 20  ω     72.00  98.00   1.00    1.00    --   95.80  61.00   0.00   26
 21  ω     65.00  91.00   1.00    1.00    --   95.80  82.00 150.00   26
 22  ω     76.00 101.00   1.00    1.00    --   95.80  45.00  30.00   25
 23  ω    123.00 185.00   1.00    1.00    --   95.80  45.00  30.00   62
 24  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 25  ω    141.00 175.00   1.00    1.00    --   95.80  77.00  60.00   34
 26  ω     75.00 135.00   1.00    1.00    --   95.80  45.00   0.00   60
 27  ω    151.00 179.00   1.00    1.00    --   95.80  45.00   0.00   28
 28  ω      6.00 128.00   1.00    1.00    --   95.80 -82.00 -30.00  122
 29  ω     71.00 182.00   1.00    1.00    --   95.80  61.00 120.00  111
 30  ω     76.00 132.00   1.00    1.00    --   95.80  61.00  30.00   56
 31  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 32  ω     73.00 125.00   1.00    1.00    --   95.80 -82.00  66.66   52
 33  ω     88.00 125.00   1.00    1.00    --   95.80 -82.00-120.00   37
 34  ω     28.00  85.00   1.00    1.00    --   95.80 -82.00-120.00   57
 35  ω     66.00  92.00   1.00    1.00    --   95.80  82.00 120.00   26
 36  ω     76.00 131.00   1.00    1.00    --   95.80  61.00-180.00   55
 37  ω     72.00 136.00   1.00    1.00    --   95.80  61.00  90.00   64
 38  ω    122.00 185.00   1.00    1.00    --   95.80  77.00 -30.00   63
 39  ω     64.00 158.00   1.00    1.00    --   95.80  82.00-180.00   94
 40  ω      8.00 120.00   1.00    1.00    --   95.80 -61.00  30.00  112
 41  ω     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 42  ω     63.00  96.00   1.00    1.00    --   95.80  82.00  30.00   33
 43  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 44  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 45  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 46  ω     36.00  62.00   1.00    1.00    --   95.80 -82.00  66.66   26
 47  ω     71.00 122.00   1.00    1.00    --   95.80  59.00  74.53   51
 48  ω     75.00 101.00   1.00    1.00    --   95.80  61.00 -60.00   26
 49  ω    154.00 185.00   1.00    1.00    --   95.80  61.00 -60.00   31
 50  ω     67.00  93.00   1.00    1.00    --   95.80  77.00 -90.00   26
 51  ω    141.00 168.00   1.00    1.00    --   95.80  77.00 -90.00   27
 52  ω     77.00 160.00   1.00    1.00    --   95.80  30.00 -90.00   83
 53  ω     71.00  98.00   1.00    1.00    --   95.80  61.00-120.00   27
 54  ω     73.00  99.00   1.00    1.00    --   95.80  61.00 150.00   26
 55  ω     62.00 116.00   1.00    1.00    --   95.80 -61.00 -60.00   54
 56  ω     65.00 112.00   1.00    1.00    --   95.80  77.00-150.00   47
 57  ω     60.00 125.00   1.00    1.00    --   95.80 -82.00-180.00   65
 58  ω     71.00 180.00   1.00    1.00    --   95.80  58.00 -70.70  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0325604000
_diffrn_orient_matrix_UB_12      0.0376282000
_diffrn_orient_matrix_UB_13      0.1224832000
_diffrn_orient_matrix_UB_21      0.1076318000
_diffrn_orient_matrix_UB_22      0.1613977000
_diffrn_orient_matrix_UB_23      -0.0129325000
_diffrn_orient_matrix_UB_31      -0.1830173000
_diffrn_orient_matrix_UB_32      0.0830698000
_diffrn_orient_matrix_UB_33      -0.0035614000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2546
_reflns_number_total             2694
_reflns_odcompleteness_completeness 99.56
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.275
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.033
_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)+(0.0498P)²+0.2534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1077
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_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 0.47674(14) 0.13145(12) 0.20687(7) 0.0411(3) Uani 1 1 d . . . . .
O2 O 0.27903(16) 0.46494(13) 1.01100(8) 0.0496(3) Uani 1 1 d . . . . .
N1 N 0.0931(2) 0.10117(16) 0.86314(10) 0.0531(4) Uani 1 1 d . . . . .
C1 C 0.50105(17) 0.22240(15) 0.49453(10) 0.0305(3) Uani 1 1 d . . . . .
C2 C 0.54670(18) 0.18890(15) 0.39162(10) 0.0334(3) Uani 1 1 d . . . . .
H2 H 0.671395 0.184816 0.381450 0.040 Uiso 1 1 calc R . . . .
C3 C 0.41150(19) 0.16144(15) 0.30385(10) 0.0329(3) Uani 1 1 d . . . . .
C4 C 0.22434(19) 0.16301(17) 0.31810(10) 0.0369(3) Uani 1 1 d . . . . .
H4 H 0.131774 0.143725 0.260028 0.044 Uiso 1 1 calc R . . . .
C5 C 0.17896(19) 0.19409(17) 0.42119(10) 0.0365(3) Uani 1 1 d . . . . .
H5 H 0.053805 0.193892 0.431196 0.044 Uiso 1 1 calc R . . . .
C6 C 0.31312(18) 0.22556(15) 0.51025(10) 0.0308(3) Uani 1 1 d . . . . .
C7 C 0.25260(17) 0.26747(15) 0.61986(10) 0.0300(3) Uani 1 1 d . . . . .
H7 H 0.147628 0.190705 0.628129 0.036 Uiso 1 1 calc R . . . .
C8 C 0.18367(19) 0.43600(16) 0.62669(10) 0.0352(3) Uani 1 1 d . . . . .
H8A H 0.281087 0.512118 0.609953 0.042 Uiso 1 1 calc R . . . .
H8B H 0.076630 0.437443 0.573224 0.042 Uiso 1 1 calc R . . . .
C9 C 0.1290(2) 0.49057(17) 0.73634(11) 0.0376(3) Uani 1 1 d . . . . .
H9A H 0.021487 0.422876 0.750041 0.045 Uiso 1 1 calc R . . . .
H9B H 0.094775 0.600456 0.737080 0.045 Uiso 1 1 calc R . . . .
C10 C 0.29104(18) 0.48080(15) 0.82447(10) 0.0322(3) Uani 1 1 d . . . . .
H10 H 0.395670 0.551547 0.808038 0.039 Uiso 1 1 calc R . . . .
C11 C 0.35506(18) 0.30944(15) 0.82050(10) 0.0325(3) Uani 1 1 d . . . . .
H11 H 0.464436 0.309346 0.873869 0.039 Uiso 1 1 calc R . . . .
C12 C 0.40968(18) 0.25073(15) 0.70982(10) 0.0315(3) Uani 1 1 d . . . . .
H12 H 0.427813 0.135942 0.710196 0.038 Uiso 1 1 calc R . . . .
C13 C 0.59237(18) 0.33602(17) 0.68748(11) 0.0380(3) Uani 1 1 d . . . . .
H13A H 0.687060 0.333781 0.748033 0.046 Uiso 1 1 calc R . . . .
H13B H 0.575040 0.447557 0.676978 0.046 Uiso 1 1 calc R . . . .
C14 C 0.65534(18) 0.25157(18) 0.58717(11) 0.0371(3) Uani 1 1 d . . . . .
H14A H 0.758486 0.316815 0.565929 0.044 Uiso 1 1 calc R . . . .
H14B H 0.699959 0.149238 0.603939 0.044 Uiso 1 1 calc R . . . .
C15 C 0.24819(19) 0.54211(16) 0.93506(11) 0.0368(3) Uani 1 1 d . . . . .
C16 C 0.1700(3) 0.70141(19) 0.94702(13) 0.0531(4) Uani 1 1 d . . . . .
H16A H 0.038667 0.688845 0.923208 0.080 Uiso 1 1 calc GR . . . .
H16B H 0.230678 0.774134 0.904733 0.080 Uiso 1 1 calc GR . . . .
H16C H 0.190444 0.743925 1.020818 0.080 Uiso 1 1 calc GR . . . .
C17 C 0.2076(2) 0.19396(16) 0.84699(10) 0.0373(3) Uani 1 1 d . . . . .
C18 C 0.3430(2) 0.1102(2) 0.11412(11) 0.0495(4) Uani 1 1 d . . . . .
H18A H 0.405198 0.090370 0.051801 0.074 Uiso 1 1 calc GR . . . .
H18B H 0.278169 0.205564 0.108678 0.074 Uiso 1 1 calc GR . . . .
H18C H 0.255463 0.020201 0.119255 0.074 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 C3 1.3742(15) . ?
O1 C18 1.4219(17) . ?
O2 C15 1.2128(17) . ?
N1 C17 1.1425(18) . ?
C1 C2 1.3896(18) . ?
C1 C6 1.4006(18) . ?
C1 C14 1.5130(17) . ?
C2 C3 1.3840(19) . ?
C3 C4 1.390(2) . ?
C4 C5 1.3884(19) . ?
C5 C6 1.3929(18) . ?
C6 C7 1.5214(17) . ?
C7 C8 1.5302(18) . ?
C7 C12 1.5370(17) . ?
C8 C9 1.5268(18) . ?
C9 C10 1.5351(18) . ?
C10 C11 1.5388(18) . ?
C10 C15 1.5211(18) . ?
C11 C12 1.5471(17) . ?
C11 C17 1.4749(19) . ?
C12 C13 1.5245(18) . ?
C13 C14 1.5302(19) . ?
C15 C16 1.490(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
C3 O1 C18 117.28(11) . . ?
C2 C1 C6 119.21(12) . . ?
C2 C1 C14 119.22(11) . . ?
C6 C1 C14 121.57(11) . . ?
C3 C2 C1 121.75(12) . . ?
O1 C3 C2 115.49(12) . . ?
O1 C3 C4 124.72(12) . . ?
C2 C3 C4 119.78(12) . . ?
C5 C4 C3 118.35(12) . . ?
C4 C5 C6 122.72(13) . . ?
C1 C6 C7 122.24(11) . . ?
C5 C6 C1 118.17(12) . . ?
C5 C6 C7 119.56(11) . . ?
C6 C7 C8 110.16(10) . . ?
C6 C7 C12 111.37(10) . . ?
C8 C7 C12 111.93(10) . . ?
C9 C8 C7 113.44(10) . . ?
C8 C9 C10 110.71(11) . . ?
C9 C10 C11 110.36(10) . . ?
C15 C10 C9 113.09(11) . . ?
C15 C10 C11 112.60(11) . . ?
C10 C11 C12 112.64(10) . . ?
C17 C11 C10 110.86(11) . . ?
C17 C11 C12 108.38(10) . . ?
C7 C12 C11 111.30(10) . . ?
C13 C12 C7 110.67(10) . . ?
C13 C12 C11 112.38(10) . . ?
C12 C13 C14 109.37(11) . . ?
C1 C14 C13 112.78(11) . . ?
O2 C15 C10 121.11(13) . . ?
O2 C15 C16 121.27(13) . . ?
C16 C15 C10 117.61(12) . . ?
N1 C17 C11 177.02(14) . . ?

_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 1.863
_oxdiff_exptl_absorpt_empirical_full_min 0.628
####################################################################### 
# 
# 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_947
_database_code_depnum_ccdc_archive 'CCDC 2076484'
loop_
_audit_author_name
_audit_author_address
'Wen-Biao Wu'
;East China Normal University
China
;
_audit_update_record             
;
2021-04-09 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_audit_creation_date             2019-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H32 O2'
_chemical_formula_sum            'C25 H32 O2'
_chemical_formula_weight         364.50
_chemical_absolute_configuration ad
_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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.1960(5)
_cell_length_b                   6.2725(2)
_cell_length_c                   13.2067(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.530(4)
_cell_angle_gamma                90
_cell_volume                     1001.59(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1720
_cell_measurement_theta_min      4.5940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21715
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.386
_diffrn_reflns_theta_min         4.642
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     94.00 125.00   1.00    1.00    --   95.80   4.00   5.00   31
  2  ω    156.00 182.00   1.00    1.00    --   95.80   4.00   5.00   26
  3  ω      7.00  32.00   1.00    1.00    --   95.80  -4.00-171.00   25
  4  ω     29.00  55.00   1.00    1.00    --   95.80   4.00   5.00   26
  5  ω     19.00  60.00   1.00    1.00    --    0.00  57.00  30.00   41
  6  ω    -23.00  15.00   1.00    1.00    --    0.00  57.00  30.00   38
  7  ω    -11.00  28.00   1.00    1.00    --    0.00   4.00   5.00   39
  8  ω    -77.00 -32.00   1.00    1.00    --    0.00  -4.00-171.00   45
  9  ω     21.00  70.00   1.00    1.00    --    0.00  38.00-120.00   49
 10  ω      5.00  84.00   1.00    1.00    --    0.00  57.00 120.00   79
 11  ω     35.00  75.00   1.00    1.00    --    0.00  57.00 150.00   40
 12  ω    -23.00  89.00   1.00    1.00    --    0.00  57.00-120.00  112
 13  ω      2.00  29.00   1.00    1.00    --    0.00  77.00 -90.00   27
 14  ω    -16.00  13.00   1.00    1.00    --    0.00  -4.00-171.00   29
 15  ω     37.00  87.00   1.00    1.00    --    0.00  77.00 -90.00   50
 16  ω     54.00  88.00   1.00    1.00    --    0.00  38.00  90.00   34
 17  ω    -83.00 -56.00   1.00    1.00    --    0.00   4.00   5.00   27
 18  ω    -19.00  41.00   1.00    1.00    --    0.00  38.00  90.00   60
 19  ω     66.00 104.00   1.00    1.00    --   95.80  82.00  30.00   38
 20  ω    145.00 171.00   1.00    1.00    --   95.80  73.00-155.52   26
 21  ω      7.00  38.00   1.00    1.00    --   95.80 -82.00  60.00   31
 22  ω     67.00  93.00   1.00    1.00    --   95.80  73.00-155.52   26
 23  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 24  ω     72.00 184.00   1.00    1.00    --   95.80  61.00 150.00  112
 25  ω    110.00 182.00   1.00    1.00    --   95.80  77.00  60.00   72
 26  ω    126.00 152.00   1.00    1.00    --   95.80  77.00-180.00   26
 27  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 28  ω      6.00 125.00   1.00    1.00    --   95.80 -77.00   0.00  119
 29  ω      6.00 126.00   1.00    1.00    --   95.80 -77.00-180.00  120
 30  ω     75.00 159.00   1.00    1.00    --   95.80  45.00 -90.00   84
 31  ω     71.00 102.00   1.00    1.00    --   95.80  61.00  90.00   31
 32  ω    147.00 178.00   1.00    1.00    --   95.80  61.00  90.00   31
 33  ω     65.00  93.00   1.00    1.00    --   95.80  77.00 120.00   28
 34  ω     71.00  97.00   1.00    1.00    --   95.80  61.00 -90.00   26
 35  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 36  ω    110.00 153.00   1.00    1.00    --   95.80  77.00   0.00   43
 37  ω     38.00  71.00   1.00    1.00    --   95.80 -82.00 -30.00   33
 38  ω     65.00 104.00   1.00    1.00    --   95.80  77.00   0.00   39
 39  ω     64.00  89.00   1.00    1.00    --   95.80  82.00 120.00   25
 40  ω    139.00 183.00   1.00    1.00    --   95.80  77.00-120.00   44
 41  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 42  ω     65.00 100.00   1.00    1.00    --   95.80  82.00  90.00   35
 43  ω      8.00 114.00   1.00    1.00    --   95.80 -82.00 150.00  106
 44  ω     76.00 114.00   1.00    1.00    --   95.80 -82.00 -30.00   38
 45  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 46  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 47  ω    154.00 181.00   1.00    1.00    --   95.80  82.00 -90.00   27
 48  ω     75.00 116.00   1.00    1.00    --   95.80  45.00   0.00   41
 49  ω     75.00 158.00   1.00    1.00    --   95.80  45.00  90.00   83
 50  ω     72.00 165.00   1.00    1.00    --   95.80  61.00-150.00   93
 51  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 52  ω     51.00 121.00   1.00    1.00    --   95.80 -82.00-120.00   70
 53  ω     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 54  ω    150.00 175.00   1.00    1.00    --   95.80  82.00   0.00   25
 55  ω     65.00  92.00   1.00    1.00    --   95.80  77.00-150.00   27
 56  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 57  ω     65.00  97.00   1.00    1.00    --   95.80  77.00 -60.00   32
 58  ω     76.00 103.00   1.00    1.00    --   95.80  45.00  60.00   27
 59  ω    119.00 153.00   1.00    1.00    --   95.80  45.00  60.00   34
 60  ω     78.00 109.00   1.00    1.00    --   95.80  61.00-180.00   31
 61  ω     74.00 184.00   1.00    1.00    --   95.80  61.00   0.00  110
 62  ω     65.00 101.00   1.00    1.00    --   95.80  82.00-150.00   36
 63  ω     64.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   25
 64  ω     74.00 146.00   1.00    1.00    --   95.80  50.00 -57.10   72
 65  ω     67.00  93.00   1.00    1.00    --   95.80  71.00 153.66   26
 66  ω     71.00  96.00   1.00    1.00    --   95.80  63.00 -12.30   25
 67  ω    146.00 171.00   1.00    1.00    --   95.80  82.00  30.00   25
 68  ω     49.00 110.00   1.00    1.00    --   95.80 -82.00  60.00   61
 69  ω    160.00 185.00   1.00    1.00    --   95.80  -4.00-171.00   25
 70  ω     83.00 118.00   1.00    1.00    --   95.80  -4.00-171.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0070652000
_diffrn_orient_matrix_UB_12      0.2451783000
_diffrn_orient_matrix_UB_13      0.0010518000
_diffrn_orient_matrix_UB_21      0.1249777000
_diffrn_orient_matrix_UB_22      0.0139515000
_diffrn_orient_matrix_UB_23      -0.0067954000
_diffrn_orient_matrix_UB_31      -0.0241168000
_diffrn_orient_matrix_UB_32      0.0010427000
_diffrn_orient_matrix_UB_33      -0.1174306000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                3786
_reflns_number_total             3981
_reflns_odcompleteness_completeness 99.34
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.374
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 
;
 Flack x determined using 1494 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3981
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0858
_refine_ls_restrained_S_all      1.083
_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)+(0.1657P)²+0.9415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2572
_refine_ls_wR_factor_ref         0.2587
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6), C10(H10), C19(H19), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C17(H17A,H17B), C18(H18A,
 H18B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C13(H13), C15(H15)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_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 0.0529(4) 0.6542(9) 0.7421(4) 0.0532(13) Uani 1 1 d . . . . .
O2 O 0.8025(3) 0.5303(8) -0.0177(3) 0.0445(11) Uani 1 1 d . . . . .
C1 C 0.1980(4) 0.3393(9) 0.4514(4) 0.0310(11) Uani 1 1 d . . . . .
H1 H 0.152085 0.223731 0.418910 0.037 Uiso 1 1 calc R . . . .
C2 C 0.1776(4) 0.3483(9) 0.5613(4) 0.0315(11) Uani 1 1 d . . . . .
H2 H 0.198363 0.231050 0.602471 0.038 Uiso 1 1 calc R . . . .
C3 C 0.1319(4) 0.5130(9) 0.6032(4) 0.0299(11) Uani 1 1 d . . . . .
C4 C 0.1061(5) 0.7172(9) 0.5453(4) 0.0371(13) Uani 1 1 d . . . . .
H4A H 0.119403 0.837026 0.591734 0.045 Uiso 1 1 calc R . . . .
H4B H 0.028567 0.718731 0.517089 0.045 Uiso 1 1 calc R . . . .
C5 C 0.1767(5) 0.7410(9) 0.4595(4) 0.0349(12) Uani 1 1 d . . . . .
H5A H 0.253563 0.758071 0.488108 0.042 Uiso 1 1 calc R . . . .
H5B H 0.154148 0.867571 0.419974 0.042 Uiso 1 1 calc R . . . .
C6 C 0.1648(4) 0.5456(9) 0.3897(4) 0.0312(11) Uani 1 1 d . . . . .
H6 H 0.087627 0.533498 0.358424 0.037 Uiso 1 1 calc R . . . .
C7 C 0.2408(4) 0.5387(9) 0.3047(4) 0.0306(11) Uani 1 1 d . . . . .
C8 C 0.2636(4) 0.7497(9) 0.2522(4) 0.0330(11) Uani 1 1 d . . . . .
H8A H 0.196040 0.798974 0.212112 0.040 Uiso 1 1 calc R . . . .
H8B H 0.286318 0.856492 0.303854 0.040 Uiso 1 1 calc R . . . .
C9 C 0.3538(4) 0.7256(10) 0.1826(4) 0.0352(12) Uani 1 1 d . . . . .
H9A H 0.372191 0.865537 0.158519 0.042 Uiso 1 1 calc R . . . .
H9B H 0.324767 0.641520 0.123433 0.042 Uiso 1 1 calc R . . . .
C10 C 0.4600(4) 0.6191(8) 0.2349(4) 0.0303(11) Uani 1 1 d . . . . .
H10 H 0.492189 0.719559 0.287383 0.036 Uiso 1 1 calc R . . . .
C11 C 0.5479(4) 0.5846(9) 0.1648(4) 0.0307(11) Uani 1 1 d . . . . .
C12 C 0.5592(4) 0.7223(10) 0.0833(4) 0.0348(12) Uani 1 1 d . . . . .
H12 H 0.508879 0.833339 0.069643 0.042 Uiso 1 1 calc R . . . .
C13 C 0.6415(5) 0.6994(10) 0.0232(4) 0.0392(13) Uani 1 1 d . . . . .
H13 H 0.646266 0.794567 -0.030059 0.047 Uiso 1 1 calc R . . . .
C14 C 0.7190(4) 0.5338(10) 0.0410(4) 0.0360(12) Uani 1 1 d . . . . .
C15 C 0.7073(4) 0.3913(10) 0.1195(4) 0.0347(12) Uani 1 1 d . . . . .
H15 H 0.756414 0.277726 0.131117 0.042 Uiso 1 1 calc R . . . .
C16 C 0.6229(4) 0.4152(9) 0.1815(4) 0.0314(11) Uani 1 1 d . . . . .
C17 C 0.6174(5) 0.2511(9) 0.2649(4) 0.0356(12) Uani 1 1 d . . . . .
H17A H 0.691636 0.222724 0.298218 0.043 Uiso 1 1 calc R . . . .
H17B H 0.587905 0.119024 0.234227 0.043 Uiso 1 1 calc R . . . .
C18 C 0.5453(4) 0.3234(9) 0.3451(4) 0.0322(11) Uani 1 1 d . . . . .
H18A H 0.530999 0.203606 0.387925 0.039 Uiso 1 1 calc R . . . .
H18B H 0.583798 0.432190 0.388250 0.039 Uiso 1 1 calc R . . . .
C19 C 0.4368(4) 0.4119(8) 0.2925(4) 0.0305(11) Uani 1 1 d . . . . .
H19 H 0.404393 0.306920 0.242307 0.037 Uiso 1 1 calc R . . . .
C20 C 0.3520(4) 0.4632(8) 0.3640(4) 0.0293(11) Uani 1 1 d . . . . .
H20 H 0.381622 0.582695 0.406953 0.035 Uiso 1 1 calc R . . . .
C21 C 0.3201(4) 0.2883(8) 0.4362(4) 0.0296(11) Uani 1 1 d . . . . .
H21A H 0.367918 0.292563 0.500876 0.036 Uiso 1 1 calc R . . . .
H21B H 0.325373 0.148354 0.405912 0.036 Uiso 1 1 calc R . . . .
C22 C 0.1005(4) 0.5044(10) 0.7091(4) 0.0361(12) Uani 1 1 d . . . . .
C23 C 0.1287(5) 0.3093(11) 0.7729(4) 0.0427(14) Uani 1 1 d . . . . .
H23A H 0.207468 0.290154 0.783165 0.064 Uiso 1 1 calc GR . . . .
H23B H 0.094340 0.186857 0.738541 0.064 Uiso 1 1 calc GR . . . .
H23C H 0.102357 0.326087 0.837816 0.064 Uiso 1 1 calc GR . . . .
C24 C 0.1913(5) 0.3769(11) 0.2249(4) 0.0385(13) Uani 1 1 d . . . . .
H24A H 0.188046 0.239443 0.256364 0.058 Uiso 1 1 calc GR . . . .
H24B H 0.236804 0.368648 0.170985 0.058 Uiso 1 1 calc GR . . . .
H24C H 0.118101 0.421026 0.197382 0.058 Uiso 1 1 calc GR . . . .
C25 C 0.8870(5) 0.3765(14) 0.0055(5) 0.0520(18) Uani 1 1 d . . . . .
H25A H 0.940948 0.392154 -0.040801 0.078 Uiso 1 1 calc GR . . . .
H25B H 0.855465 0.236181 -0.001367 0.078 Uiso 1 1 calc GR . . . .
H25C H 0.921811 0.396960 0.074263 0.078 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 C22 1.215(7) . ?
O2 C14 1.359(6) . ?
O2 C25 1.416(9) . ?
C1 H1 0.9800 . ?
C1 C2 1.506(7) . ?
C1 C6 1.554(7) . ?
C1 C21 1.561(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.329(7) . ?
C3 C4 1.504(7) . ?
C3 C22 1.498(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.517(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.529(8) . ?
C6 H6 0.9800 . ?
C6 C7 1.546(7) . ?
C7 C8 1.537(7) . ?
C7 C20 1.548(7) . ?
C7 C24 1.529(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.531(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.539(7) . ?
C10 H10 0.9800 . ?
C10 C11 1.521(7) . ?
C10 C19 1.551(7) . ?
C11 C12 1.401(8) . ?
C11 C16 1.401(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.367(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.403(9) . ?
C14 C15 1.390(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.405(7) . ?
C16 C17 1.515(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.531(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.517(7) . ?
C19 H19 0.9800 . ?
C19 C20 1.524(7) . ?
C20 H20 0.9800 . ?
C20 C21 1.537(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.500(8) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C14 O2 C25 117.8(5) . . ?
C2 C1 H1 107.0 . . ?
C2 C1 C6 114.2(4) . . ?
C2 C1 C21 114.4(4) . . ?
C6 C1 H1 107.0 . . ?
C6 C1 C21 106.9(4) . . ?
C21 C1 H1 107.0 . . ?
C1 C2 H2 117.9 . . ?
C3 C2 C1 124.2(5) . . ?
C3 C2 H2 117.9 . . ?
C2 C3 C4 121.4(5) . . ?
C2 C3 C22 122.2(5) . . ?
C4 C3 C22 116.3(5) . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C3 C4 C5 111.2(4) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 C6 110.7(5) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C1 C6 H6 109.0 . . ?
C5 C6 C1 110.7(4) . . ?
C5 C6 H6 109.0 . . ?
C5 C6 C7 116.2(4) . . ?
C7 C6 C1 102.5(4) . . ?
C7 C6 H6 109.0 . . ?
C6 C7 C20 102.1(4) . . ?
C8 C7 C6 117.7(4) . . ?
C8 C7 C20 107.0(4) . . ?
C24 C7 C6 107.4(4) . . ?
C24 C7 C8 109.8(4) . . ?
C24 C7 C20 112.7(4) . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 111.9(4) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C8 C9 C10 113.7(4) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C9 C10 H10 105.9 . . ?
C9 C10 C19 112.8(4) . . ?
C11 C10 C9 114.1(4) . . ?
C11 C10 H10 105.9 . . ?
C11 C10 C19 111.6(4) . . ?
C19 C10 H10 105.9 . . ?
C12 C11 C10 121.9(5) . . ?
C16 C11 C10 120.7(5) . . ?
C16 C11 C12 117.5(5) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 C11 122.3(5) . . ?
C13 C12 H12 118.8 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.7(5) . . ?
C14 C13 H13 119.7 . . ?
O2 C14 C13 117.0(5) . . ?
O2 C14 C15 124.9(5) . . ?
C15 C14 C13 118.0(5) . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.3(5) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 C15 120.2(5) . . ?
C11 C16 C17 122.6(5) . . ?
C15 C16 C17 117.2(5) . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C16 C17 C18 112.7(5) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 C17 109.7(4) . . ?
C19 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
C10 C19 H19 108.3 . . ?
C18 C19 C10 109.1(4) . . ?
C18 C19 H19 108.3 . . ?
C18 C19 C20 114.6(4) . . ?
C20 C19 C10 108.0(4) . . ?
C20 C19 H19 108.3 . . ?
C7 C20 H20 106.9 . . ?
C19 C20 C7 111.8(4) . . ?
C19 C20 H20 106.9 . . ?
C19 C20 C21 118.8(4) . . ?
C21 C20 C7 104.8(4) . . ?
C21 C20 H20 106.9 . . ?
C1 C21 H21A 110.8 . . ?
C1 C21 H21B 110.8 . . ?
C20 C21 C1 104.9(4) . . ?
C20 C21 H21A 110.8 . . ?
C20 C21 H21B 110.8 . . ?
H21A C21 H21B 108.9 . . ?
O1 C22 C3 120.0(5) . . ?
O1 C22 C23 120.9(5) . . ?
C23 C22 C3 119.1(5) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7 C24 H24A 109.5 . . ?
C7 C24 H24B 109.5 . . ?
C7 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_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 3.013
_oxdiff_exptl_absorpt_empirical_full_min 0.413
####################################################################### 
# 
# 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_1154
_database_code_depnum_ccdc_archive 'CCDC 2083519'
loop_
_audit_author_name
_audit_author_address
'Wen-Biao Wu'
;East China Normal University
China
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_audit_creation_date             2020-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O'
_chemical_formula_sum            'C20 H17 N O'
_chemical_formula_weight         287.35
_chemical_absolute_configuration unk
_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      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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.55952(19)
_cell_length_b                   7.19955(14)
_cell_length_c                   33.3740(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1576.11(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10042
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5650
_cell_measurement_theta_min      5.2840
_shelx_estimated_absorpt_T_max   0.869
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48811
_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_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    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            32998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         6.697
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  45.00   1.00    1.00    --    0.00  82.00 120.00   75
  2  ω    -88.00  -2.00   1.00    1.00    --    0.00 -57.00 120.00   86
  3  ω     -3.00  34.00   1.00    1.00    --    0.00  19.00  90.00   37
  4  ω     48.00  84.00   1.00    1.00    --    0.00  82.00 120.00   36
  5  ω    -48.00  23.00   1.00    1.00    --    0.00 -57.00   0.00   71
  6  ω     29.00  89.00   1.00    1.00    --    0.00  19.00-180.00   60
  7  ω    -19.00  20.00   1.00    1.00    --    0.00  19.00-180.00   39
  8  ω    -21.00  86.00   1.00    1.00    --    0.00  19.00 -60.00  107
  9  ω     -5.00  22.00   1.00    1.00    --    0.00  57.00 120.00   27
 10  ω     72.00 141.00   1.00    1.00    --   95.80  56.00-155.65   69
 11  ω     94.00 183.00   1.00    1.00    --   95.80  79.00-105.36   89
 12  ω     64.00  91.00   1.00    1.00    --   95.80  79.00-105.36   27
 13  ω     63.00 107.00   1.00    1.00    --   95.80  81.00  99.10   44
 14  ω    138.00 179.00   1.00    1.00    --   95.80  81.00  99.10   41
 15  ω    136.00 185.00   1.00    1.00    --   95.80  63.00 -54.19   49
 16  ω     74.00  99.00   1.00    1.00    --   95.80  54.00  -9.01   25
 17  ω    148.00 174.00   1.00    1.00    --   95.80  78.00 140.50   26
 18  ω    120.00 185.00   1.00    1.00    --   95.80  75.00-156.18   65
 19  ω     66.00  92.00   1.00    1.00    --   95.80  75.00-156.18   26
 20  ω     97.00 124.00   1.00    1.00    --   95.80  78.00 140.50   27
 21  ω     66.00  91.00   1.00    1.00    --   95.80  74.00 172.50   25
 22  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 23  ω     65.00  92.00   1.00    1.00    --   95.80  77.00 -30.00   27
 24  ω     76.00 102.00   1.00    1.00    --   95.80  45.00 -90.00   26
 25  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 26  ω      7.00 128.00   1.00    1.00    --   95.80 -82.00-150.00  121
 27  ω     99.00 182.00   1.00    1.00    --   95.80  82.00 -90.00   83
 28  ω     71.00 108.00   1.00    1.00    --   95.80  61.00   0.00   37
 29  ω     34.00  59.00   1.00    1.00    --   95.80 -82.00 120.00   25
 30  ω     71.00 103.00   1.00    1.00    --   95.80 -82.00 120.00   32
 31  ω     70.00 104.00   1.00    1.00    --   95.80  63.00 -54.19   34
 32  ω    145.00 171.00   1.00    1.00    --   95.80  77.00  55.21   26
 33  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 34  ω    117.00 142.00   1.00    1.00    --   95.80  82.00-150.00   25
 35  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  55.21   26
 36  ω     65.00  95.00   1.00    1.00    --   95.80  78.00 140.50   30
 37  ω    145.00 171.00   1.00    1.00    --   95.80  77.00  30.00   26
 38  ω     63.00  90.00   1.00    1.00    --   95.80  82.00-150.00   27
 39  ω    159.00 185.00   1.00    1.00    --   95.80  77.00 120.00   26
 40  ω     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 41  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 42  ω     59.00 127.00   1.00    1.00    --   95.80 -82.00 -60.00   68
 43  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 44  ω    111.00 184.00   1.00    1.00    --   95.80  82.00 150.00   73
 45  ω    113.00 139.00   1.00    1.00    --   95.80  56.00  24.21   26
 46  ω     75.00 100.00   1.00    1.00    --   95.80  61.00  60.00   25
 47  ω     94.00 138.00   1.00    1.00    --   95.80  77.00 120.00   44
 48  ω     64.00  89.00   1.00    1.00    --   95.80  82.00 120.00   25
 49  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 50  ω     72.00 105.00   1.00    1.00    --   95.80  56.00  24.21   33
 51  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 52  ω     75.00 156.00   1.00    1.00    --   95.80  45.00-180.00   81
 53  ω     66.00 115.00   1.00    1.00    --   95.80  77.00-150.00   49
 54  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 55  ω    158.00 185.00   1.00    1.00    --   95.80  56.00-155.65   27
 56  ω     76.00 171.00   1.00    1.00    --   95.80  45.00 120.00   95
 57  ω    124.00 150.00   1.00    1.00    --   95.80  54.00  -9.01   26
 58  ω    148.00 178.00   1.00    1.00    --   95.80  49.00  56.36   30
 59  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 60  ω     63.00 173.00   1.00    1.00    --   95.80  82.00  60.00  110
 61  ω     71.00 149.00   1.00    1.00    --   95.80  61.00 -30.00   78
 62  ω     14.00 113.00   1.00    1.00    --   95.80 -61.00-150.00   99
 63  ω     16.00 123.00   1.00    1.00    --   95.80 -82.00  60.00  107
 64  ω     74.00 142.00   1.00    1.00    --   95.80  49.00  56.36   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0018928000
_diffrn_orient_matrix_UB_12      0.0496753000
_diffrn_orient_matrix_UB_13      0.0448899000
_diffrn_orient_matrix_UB_21      -0.0104720000
_diffrn_orient_matrix_UB_22      0.2079197000
_diffrn_orient_matrix_UB_23      -0.0107231000
_diffrn_orient_matrix_UB_31      -0.2346435000
_diffrn_orient_matrix_UB_32      -0.0088519000
_diffrn_orient_matrix_UB_33      0.0008494000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2596
_reflns_number_total             2806
_reflns_odcompleteness_completeness 99.77
_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 1.171.39.28b (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.078
_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)+(0.0558P)²+0.2626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1052
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: C01(0.5) C02(0.5) N01(0.5) N02(0.5)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C12(H12a,H12b)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_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
C1 C -0.7470(5) -0.5160(4) -0.21941(7) 0.0456(6) Uani 1 1 d . . . . .
H1 H -0.618220 -0.513188 -0.231043 0.055 Uiso 1 1 calc R . . . .
C01 C -0.3755(9) 0.0458(7) -0.14494(16) 0.0420(12) Uani 0.5 1 d . . P . .
C02 C -0.4945(10) -0.2173(6) -0.10405(13) 0.0439(13) Uani 0.5 1 d . . P . .
C2 C -0.8786(5) -0.6609(4) -0.22777(7) 0.0524(7) Uani 1 1 d . . . . .
H2 H -0.838231 -0.754859 -0.245167 0.063 Uiso 1 1 calc R . . . .
C3 C -1.0700(5) -0.6671(4) -0.21042(8) 0.0528(7) Uani 1 1 d . . . . .
H3 H -1.157283 -0.765701 -0.215873 0.063 Uiso 1 1 calc R . . . .
C4 C -1.1311(5) -0.5264(4) -0.18498(7) 0.0476(6) Uani 1 1 d . . . . .
H4 H -1.260190 -0.530208 -0.173470 0.057 Uiso 1 1 calc R . . . .
C5 C -1.0017(4) -0.3800(4) -0.17652(7) 0.0428(6) Uani 1 1 d . . . . .
H5 H -1.044267 -0.285470 -0.159468 0.051 Uiso 1 1 calc R . . . .
C6 C -0.8075(4) -0.3736(3) -0.19348(7) 0.0403(6) Uani 1 1 d . . . . .
C7 C -0.6616(4) -0.2172(4) -0.18597(7) 0.0426(6) Uani 1 1 d . . . . .
C8 C -0.7128(4) -0.0719(3) -0.15448(7) 0.0412(6) Uani 1 1 d . . . . .
H8 H -0.851756 -0.028778 -0.159894 0.049 Uiso 1 1 calc R . . . .
C9 C -0.5732(4) 0.0979(4) -0.15648(8) 0.0445(6) Uani 1 1 d . . . . .
H9 H -0.571054 0.147391 -0.183830 0.053 Uiso 1 1 calc R . . . .
C10 C -0.6479(5) 0.2476(3) -0.12736(7) 0.0449(6) Uani 1 1 d . . . . .
H10A H -0.782223 0.289178 -0.135588 0.054 Uiso 1 1 calc R . . . .
H10B H -0.556592 0.353443 -0.128581 0.054 Uiso 1 1 calc R . . . .
C11 C -0.6585(4) 0.1770(3) -0.08402(7) 0.0431(6) Uani 1 1 d . . . . .
H11 H -0.519181 0.149061 -0.075301 0.052 Uiso 1 1 calc R . . . .
C12 C -0.7821(5) -0.0028(3) -0.08163(7) 0.0445(6) Uani 1 1 d . . . . .
H12A H -0.924280 0.025524 -0.086801 0.053 Uiso 1 1 calc R . . . .
H12B H -0.772595 -0.051874 -0.054628 0.053 Uiso 1 1 calc R . . . .
C13 C -0.7114(5) -0.1534(3) -0.11137(7) 0.0446(6) Uani 1 1 d . . . . .
C14 C -0.7447(4) 0.3224(3) -0.05585(7) 0.0412(6) Uani 1 1 d . . . . .
C15 C -0.9351(4) 0.4029(4) -0.06286(8) 0.0455(6) Uani 1 1 d . . . . .
H15 H -1.009631 0.367971 -0.085333 0.055 Uiso 1 1 calc R . . . .
C16 C -1.0144(5) 0.5341(3) -0.03677(8) 0.0485(7) Uani 1 1 d . . . . .
H16 H -1.141212 0.586724 -0.041931 0.058 Uiso 1 1 calc R . . . .
C17 C -0.9065(5) 0.5869(4) -0.00321(9) 0.0494(7) Uani 1 1 d . . . . .
H17 H -0.959430 0.675626 0.014177 0.059 Uiso 1 1 calc R . . . .
C18 C -0.7198(5) 0.5071(4) 0.00433(8) 0.0506(7) Uani 1 1 d . . . . .
H18 H -0.646958 0.541308 0.027077 0.061 Uiso 1 1 calc R . . . .
C19 C -0.6390(4) 0.3758(3) -0.02180(8) 0.0457(6) Uani 1 1 d . . . . .
H19 H -0.512477 0.323242 -0.016348 0.055 Uiso 1 1 calc R . . . .
N01 N -0.2096(8) 0.0126(8) -0.13427(17) 0.0652(14) Uani 0.5 1 d . . P . .
N02 N -0.3265(9) -0.2643(7) -0.09880(13) 0.0608(14) Uani 0.5 1 d . . P . .
O1 O -0.5032(3) -0.2053(3) -0.20497(6) 0.0553(5) 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
C1 C2 1.383(4) . ?
C1 C6 1.399(3) . ?
C01 C9 1.403(6) . ?
C01 N01 1.170(7) . ?
C02 C13 1.516(7) . ?
C02 N02 1.166(7) . ?
C2 C3 1.383(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.395(4) . ?
C6 C7 1.499(4) . ?
C7 C8 1.520(3) . ?
C7 O1 1.220(3) . ?
C8 C9 1.529(4) . ?
C8 C13 1.554(3) . ?
C9 C10 1.532(4) . ?
C10 C11 1.535(3) . ?
C11 C12 1.529(4) . ?
C11 C14 1.517(3) . ?
C12 C13 1.542(3) . ?
C14 C15 1.396(4) . ?
C14 C19 1.386(4) . ?
C15 C16 1.386(4) . ?
C16 C17 1.379(4) . ?
C17 C18 1.376(4) . ?
C18 C19 1.391(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
C2 C1 C6 120.0(3) . . ?
N01 C01 C9 175.9(5) . . ?
N02 C02 C13 179.0(5) . . ?
C1 C2 C3 120.4(3) . . ?
C4 C3 C2 119.8(3) . . ?
C3 C4 C5 120.4(3) . . ?
C4 C5 C6 120.2(2) . . ?
C1 C6 C7 118.2(2) . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 122.7(2) . . ?
C6 C7 C8 119.4(2) . . ?
O1 C7 C6 120.6(2) . . ?
O1 C7 C8 119.9(3) . . ?
C7 C8 C9 112.8(2) . . ?
C7 C8 C13 112.27(19) . . ?
C9 C8 C13 109.8(2) . . ?
C01 C9 C8 109.1(3) . . ?
C01 C9 C10 108.1(3) . . ?
C8 C9 C10 110.1(2) . . ?
C9 C10 C11 112.3(2) . . ?
C12 C11 C10 110.7(2) . . ?
C14 C11 C10 111.84(19) . . ?
C14 C11 C12 110.8(2) . . ?
C11 C12 C13 113.7(2) . . ?
C02 C13 C8 105.6(3) . . ?
C02 C13 C12 113.1(3) . . ?
C12 C13 C8 109.18(19) . . ?
C15 C14 C11 121.1(2) . . ?
C19 C14 C11 120.9(2) . . ?
C19 C14 C15 118.0(2) . . ?
C16 C15 C14 120.9(3) . . ?
C17 C16 C15 120.4(3) . . ?
C18 C17 C16 119.4(3) . . ?
C17 C18 C19 120.5(3) . . ?
C14 C19 C18 120.8(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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.554
