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

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

data_3a
_database_code_depnum_ccdc_archive 'CCDC 1996953'
loop_
_audit_author_name
_audit_author_address
'Ying-Chun Chen'
;Sichuan University
China
;
_audit_update_record             
;
2021-12-02 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_audit_creation_date             2019-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N O2'
_chemical_formula_sum            'C21 H15 N O2'
_chemical_formula_weight         313.34
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.6996(2)
_cell_length_b                   10.0320(3)
_cell_length_c                   18.0221(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1572.86(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4658
_cell_measurement_temperature    170(20)
_cell_measurement_theta_max      72.9070
_cell_measurement_theta_min      4.4190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6745
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.027
_diffrn_reflns_theta_max         67.027
_diffrn_reflns_theta_min         4.908
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170(20)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00  60.00   84
  2  ω    -35.00  65.00   1.00    1.00    --   36.04 -19.00   0.00  100
  3  ω      9.00 104.00   1.00    1.00    --   36.04  77.00  60.00   95
  4  ω     23.00  89.00   1.00    1.00    --   36.04-125.00 120.00   66
  5  ω     39.00 109.00   1.00    1.00    --  108.71 -94.00  30.00   70
  6  ω     39.00 109.00   1.00    1.00    --  108.71 -94.00 -60.00   70
  7  ω    100.00 178.00   1.00    1.00    --  108.71 111.00-180.00   78
  8  ω     39.00 109.00   1.00    1.00    --  108.71 -94.00 120.00   70
  9  ω    100.00 178.00   1.00    1.00    --  108.71 111.00   0.00   78
 10  ω     39.00 109.00   1.00    1.00    --  108.71 -94.00 -30.00   70
 11  ω     39.00 178.00   1.00    1.00    --  108.71   0.00 -90.00  139
 12  ω   -105.00 -30.00   1.00    1.00    --  -36.04 -38.00 -60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1688605000
_diffrn_orient_matrix_UB_12      -0.0424235000
_diffrn_orient_matrix_UB_13      0.0104276000
_diffrn_orient_matrix_UB_21      0.0307289000
_diffrn_orient_matrix_UB_22      0.0263626000
_diffrn_orient_matrix_UB_23      -0.0828689000
_diffrn_orient_matrix_UB_31      0.0436766000
_diffrn_orient_matrix_UB_32      0.1452450000
_diffrn_orient_matrix_UB_33      0.0180665000
_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         0.723
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2759
_reflns_number_total             2801
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 
;
 Flack x determined using 1127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2801
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.090
_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)+(0.1076P)²+0.0754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1355
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00B(H00B), C00D(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O)
;
_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
O001 O 0.95232(19) 0.60245(17) 0.28627(11) 0.0134(4) Uani 1 1 d . . . . .
O002 O 0.7372(2) 0.2197(2) 0.31568(13) 0.0253(5) Uani 1 1 d . . . . .
N003 N 0.4160(3) 0.5618(3) 0.33781(16) 0.0331(7) Uani 1 1 d . . . . .
C004 C 0.7966(3) 0.7203(2) 0.37102(14) 0.0112(5) Uani 1 1 d . . . . .
C005 C 0.8070(3) 0.6191(2) 0.31140(14) 0.0091(5) Uani 1 1 d . . . . .
C006 C 0.6886(3) 0.5509(2) 0.28229(14) 0.0104(5) Uani 1 1 d . . . . .
C007 C 0.7212(3) 0.5332(3) 0.14355(15) 0.0123(5) Uani 1 1 d . . . . .
C008 C 0.9911(3) 0.2991(3) 0.34472(16) 0.0171(6) Uani 1 1 d . . . . .
H008 H 1.0193 0.2426 0.3847 0.020 Uiso 1 1 calc R . . . .
C009 C 0.9979(3) 0.4718(3) 0.25628(15) 0.0125(5) Uani 1 1 d . . . . .
H009 H 1.0698 0.4828 0.2134 0.015 Uiso 1 1 calc R . . . .
C00A C 1.0756(3) 0.3992(3) 0.31923(16) 0.0166(6) Uani 1 1 d . . . . .
H00A H 1.1737 0.4225 0.3384 0.020 Uiso 1 1 calc R . . . .
C00B C 0.7157(3) 0.4580(2) 0.21737(15) 0.0116(5) Uani 1 1 d . . . . .
H00B H 0.6291 0.3925 0.2153 0.014 Uiso 1 1 calc R . . . .
C00C C 0.5382(3) 0.5600(3) 0.31415(15) 0.0159(6) Uani 1 1 d . . . . .
C00D C 0.8638(3) 0.3821(2) 0.23532(13) 0.0114(6) Uani 1 1 d . . . . .
H00D H 0.8937 0.3282 0.1910 0.014 Uiso 1 1 calc R . . . .
C00E C 0.6420(4) 0.7208(3) 0.06763(17) 0.0241(7) Uani 1 1 d . . . . .
H00E H 0.5826 0.7996 0.0620 0.029 Uiso 1 1 calc R . . . .
C00F C 0.7329(4) 0.6768(3) 0.00996(16) 0.0249(7) Uani 1 1 d . . . . .
H00F H 0.7394 0.7265 -0.0348 0.030 Uiso 1 1 calc R . . . .
C00G C 0.8473(3) 0.2884(2) 0.30204(15) 0.0140(6) Uani 1 1 d . . . . .
C00H C 0.8086(3) 0.4884(3) 0.08396(16) 0.0197(6) Uani 1 1 d . . . . .
H00H H 0.8652 0.4078 0.0885 0.024 Uiso 1 1 calc R . . . .
C00I C 0.6981(3) 0.8288(3) 0.36454(16) 0.0181(6) Uani 1 1 d . . . . .
H00I H 0.6369 0.8392 0.3213 0.022 Uiso 1 1 calc R . . . .
C00J C 0.8860(3) 0.7062(3) 0.43465(15) 0.0175(6) Uani 1 1 d . . . . .
H00J H 0.9555 0.6335 0.4388 0.021 Uiso 1 1 calc R . . . .
C00K C 0.6366(3) 0.6501(3) 0.13423(16) 0.0182(6) Uani 1 1 d . . . . .
H00K H 0.5745 0.6820 0.1738 0.022 Uiso 1 1 calc R . . . .
C00L C 0.8738(4) 0.7976(3) 0.49166(17) 0.0246(7) Uani 1 1 d . . . . .
H00L H 0.9332 0.7869 0.5355 0.029 Uiso 1 1 calc R . . . .
C00M C 0.6893(4) 0.9219(3) 0.42136(19) 0.0256(7) Uani 1 1 d . . . . .
H00M H 0.6243 0.9974 0.4164 0.031 Uiso 1 1 calc R . . . .
C00N C 0.7747(4) 0.9048(3) 0.48480(17) 0.0239(7) Uani 1 1 d . . . . .
H00N H 0.7657 0.9671 0.5243 0.029 Uiso 1 1 calc R . . . .
C00O C 0.8144(4) 0.5595(3) 0.01820(17) 0.0259(7) Uani 1 1 d . . . . .
H00O H 0.8752 0.5272 -0.0218 0.031 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C005 1.353(3) . ?
O001 C009 1.472(3) . ?
O002 C00G 1.205(3) . ?
N003 C00C 1.145(4) . ?
C004 C005 1.481(3) . ?
C004 C00I 1.390(4) . ?
C004 C00J 1.393(4) . ?
C005 C006 1.343(4) . ?
C006 C00B 1.515(3) . ?
C006 C00C 1.432(4) . ?
C007 C00B 1.530(4) . ?
C007 C00H 1.390(4) . ?
C007 C00K 1.394(4) . ?
C008 H008 0.9500 . ?
C008 C00A 1.326(4) . ?
C008 C00G 1.472(4) . ?
C009 H009 1.0000 . ?
C009 C00A 1.508(4) . ?
C009 C00D 1.521(3) . ?
C00A H00A 0.9500 . ?
C00B H00B 1.0000 . ?
C00B C00D 1.531(3) . ?
C00D H00D 1.0000 . ?
C00D C00G 1.533(4) . ?
C00E H00E 0.9500 . ?
C00E C00F 1.378(5) . ?
C00E C00K 1.395(4) . ?
C00F H00F 0.9500 . ?
C00F C00O 1.382(5) . ?
C00H H00H 0.9500 . ?
C00H C00O 1.384(4) . ?
C00I H00I 0.9500 . ?
C00I C00M 1.388(4) . ?
C00J H00J 0.9500 . ?
C00J C00L 1.381(4) . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00L C00N 1.384(4) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.374(5) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?

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
C005 O001 C009 118.98(19) . . ?
C00I C004 C005 120.9(2) . . ?
C00I C004 C00J 119.6(2) . . ?
C00J C004 C005 119.6(2) . . ?
O001 C005 C004 112.6(2) . . ?
C006 C005 O001 121.5(2) . . ?
C006 C005 C004 125.8(2) . . ?
C005 C006 C00B 119.7(2) . . ?
C005 C006 C00C 120.8(2) . . ?
C00C C006 C00B 119.4(2) . . ?
C00H C007 C00B 122.0(2) . . ?
C00H C007 C00K 117.8(3) . . ?
C00K C007 C00B 120.2(2) . . ?
C00A C008 H008 124.9 . . ?
C00A C008 C00G 110.2(2) . . ?
C00G C008 H008 124.9 . . ?
O001 C009 H009 110.7 . . ?
O001 C009 C00A 105.9(2) . . ?
O001 C009 C00D 114.3(2) . . ?
C00A C009 H009 110.7 . . ?
C00A C009 C00D 104.2(2) . . ?
C00D C009 H009 110.7 . . ?
C008 C00A C009 112.2(2) . . ?
C008 C00A H00A 123.9 . . ?
C009 C00A H00A 123.9 . . ?
C006 C00B C007 111.89(19) . . ?
C006 C00B H00B 108.4 . . ?
C006 C00B C00D 105.9(2) . . ?
C007 C00B H00B 108.4 . . ?
C007 C00B C00D 113.7(2) . . ?
C00D C00B H00B 108.4 . . ?
N003 C00C C006 176.7(3) . . ?
C009 C00D C00B 113.9(2) . . ?
C009 C00D H00D 108.6 . . ?
C009 C00D C00G 103.9(2) . . ?
C00B C00D H00D 108.6 . . ?
C00B C00D C00G 113.1(2) . . ?
C00G C00D H00D 108.6 . . ?
C00F C00E H00E 119.8 . . ?
C00F C00E C00K 120.3(3) . . ?
C00K C00E H00E 119.8 . . ?
C00E C00F H00F 120.5 . . ?
C00E C00F C00O 119.1(3) . . ?
C00O C00F H00F 120.5 . . ?
O002 C00G C008 127.6(2) . . ?
O002 C00G C00D 125.8(2) . . ?
C008 C00G C00D 106.6(2) . . ?
C007 C00H H00H 119.5 . . ?
C00O C00H C007 121.0(3) . . ?
C00O C00H H00H 119.5 . . ?
C004 C00I H00I 120.0 . . ?
C00M C00I C004 119.9(3) . . ?
C00M C00I H00I 120.0 . . ?
C004 C00J H00J 119.9 . . ?
C00L C00J C004 120.1(3) . . ?
C00L C00J H00J 119.9 . . ?
C007 C00K C00E 120.9(3) . . ?
C007 C00K H00K 119.5 . . ?
C00E C00K H00K 119.5 . . ?
C00J C00L H00L 120.1 . . ?
C00J C00L C00N 119.9(3) . . ?
C00N C00L H00L 120.1 . . ?
C00I C00M H00M 120.0 . . ?
C00N C00M C00I 120.0(3) . . ?
C00N C00M H00M 120.0 . . ?
C00L C00N H00N 119.7 . . ?
C00M C00N C00L 120.5(3) . . ?
C00M C00N H00N 119.7 . . ?
C00F C00O C00H 120.8(3) . . ?
C00F C00O H00O 119.6 . . ?
C00H C00O H00O 119.6 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-03-20
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.440
_oxdiff_exptl_absorpt_empirical_full_min 0.520
####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1996954'
loop_
_audit_author_name
_audit_author_address
'Ying-Chun Chen'
;Sichuan University
China
;
_audit_update_record             
;
2021-12-02 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_audit_creation_date             2020-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N O2'
_chemical_formula_sum            'C21 H15 N O2'
_chemical_formula_weight         313.34
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.63882(14)
_cell_length_b                   14.4059(4)
_cell_length_c                   17.5126(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1674.88(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4082
_cell_measurement_temperature    292.28(10)
_cell_measurement_theta_max      71.3920
_cell_measurement_theta_min      3.9190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.237
_diffrn_reflns_theta_min         3.973
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.28(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -16.00   1.00    1.00    --  -34.85 -57.00 -30.00   87
  2  ω    -34.00  53.00   1.00    1.00    --   34.85 -57.00  30.00   87
  3  ω    -34.00  53.00   1.00    1.00    --   34.85 -57.00   0.00   87
  4  ω     23.00  90.00   1.00    1.00    --   34.85-125.00-120.00   67
  5  ω    -36.00  57.00   1.00    1.00    --   34.85 -38.00  90.00   93
  6  ω      6.00 104.00   1.00    1.00    --   34.85  77.00 -60.00   98
  7  ω      1.00  75.00   1.00    1.00    --   34.85 -99.00 -30.00   74
  8  ω     37.00 110.00   1.00    1.00    --  106.90 -94.00 -90.00   73
  9  ω     87.00 175.00   1.00    1.00    --  106.90  61.00  90.00   88
 10  ω     37.00 110.00   1.00    1.00    --  106.90 -94.00   0.00   73
 11  ω     87.00 177.00   1.00    1.00    --  106.90  45.00 -90.00   90
 12  ω     37.00 110.00   1.00    1.00    --  106.90 -94.00-180.00   73
 13  ω    100.00 178.00   1.00    1.00    --  106.90 111.00  60.00   78
 14  ω     35.00 152.00   1.00    1.00    --  106.90 -15.00  90.00  117
 15  ω   -103.00 -36.00   1.00    1.00    --  -34.85 -57.00-180.00   67
 16  ω   -103.00 -16.00   1.00    1.00    --  -34.85 -57.00  90.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0228591000
_diffrn_orient_matrix_UB_12      0.1054359000
_diffrn_orient_matrix_UB_13      -0.0119822000
_diffrn_orient_matrix_UB_21      0.0513745000
_diffrn_orient_matrix_UB_22      -0.0165474000
_diffrn_orient_matrix_UB_23      -0.0847118000
_diffrn_orient_matrix_UB_31      -0.2250870000
_diffrn_orient_matrix_UB_32      0.0069605000
_diffrn_orient_matrix_UB_33      -0.0204959000
_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         0.708
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2938
_reflns_number_total             3195
_reflns_odcompleteness_completeness 99.89
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.061
_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)+(0.0835P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1291
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C008(H008), C00A(H00A)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O)
;
_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
O001 O 0.2790(3) 0.47589(13) 0.69782(10) 0.0539(5) Uani 1 1 d . . . . .
O002 O 0.8715(3) 0.6566(2) 0.72040(14) 0.0892(9) Uani 1 1 d . . . . .
N003 N 0.4233(4) 0.47721(19) 0.42981(13) 0.0619(6) Uani 1 1 d . . . . .
C004 C 0.4055(4) 0.50384(16) 0.57456(13) 0.0403(5) Uani 1 1 d . . . . .
C005 C 0.2714(3) 0.46252(16) 0.62124(13) 0.0411(5) Uani 1 1 d . . . . .
C006 C 0.4787(4) 0.67128(17) 0.60519(13) 0.0417(5) Uani 1 1 d . . . . .
C007 C 0.4711(4) 0.49344(19) 0.73304(13) 0.0493(6) Uani 1 1 d . . . . .
H007 H 0.5218 0.4351 0.7544 0.059 Uiso 1 1 calc R . . . .
C008 C 0.6352(4) 0.53593(19) 0.68318(13) 0.0462(6) Uani 1 1 d . . . . .
H008 H 0.7405 0.4894 0.6745 0.055 Uiso 1 1 calc R . . . .
C009 C 0.1018(4) 0.40168(16) 0.59961(14) 0.0433(5) Uani 1 1 d . . . . .
C00A C 0.5590(3) 0.57212(17) 0.60480(12) 0.0410(5) Uani 1 1 d . . . . .
H00A H 0.6741 0.5708 0.5698 0.049 Uiso 1 1 calc R . . . .
C00B C 0.4088(3) 0.48713(16) 0.49436(13) 0.0426(5) Uani 1 1 d . . . . .
C00C C 0.7206(4) 0.6135(2) 0.73305(15) 0.0553(7) Uani 1 1 d . . . . .
C00D C -0.0117(4) 0.41557(18) 0.53420(15) 0.0480(6) Uani 1 1 d . . . . .
H00D H 0.0180 0.4650 0.5019 0.058 Uiso 1 1 calc R . . . .
C00E C 0.2863(4) 0.69352(18) 0.63019(16) 0.0518(6) Uani 1 1 d . . . . .
H00E H 0.2016 0.6466 0.6475 0.062 Uiso 1 1 calc R . . . .
C00F C 0.4424(4) 0.5611(2) 0.79676(14) 0.0600(7) Uani 1 1 d . . . . .
H00F H 0.3372 0.5583 0.8317 0.072 Uiso 1 1 calc R . . . .
C00G C 0.2186(5) 0.7844(2) 0.62971(17) 0.0612(7) Uani 1 1 d . . . . .
H00G H 0.0893 0.7983 0.6466 0.073 Uiso 1 1 calc R . . . .
C00H C -0.1678(4) 0.3567(2) 0.51677(19) 0.0623(8) Uani 1 1 d . . . . .
H00H H -0.2441 0.3669 0.4730 0.075 Uiso 1 1 calc R . . . .
C00I C -0.2121(5) 0.2826(2) 0.5636(2) 0.0795(11) Uani 1 1 d . . . . .
H00I H -0.3162 0.2421 0.5510 0.095 Uiso 1 1 calc R . . . .
C00J C 0.5999(5) 0.7424(2) 0.57910(18) 0.0624(7) Uani 1 1 d . . . . .
H00J H 0.7289 0.7294 0.5614 0.075 Uiso 1 1 calc R . . . .
C00K C 0.0527(5) 0.32795(19) 0.64743(19) 0.0628(8) Uani 1 1 d . . . . .
H00K H 0.1251 0.3188 0.6923 0.075 Uiso 1 1 calc R . . . .
C00L C 0.5846(5) 0.6256(2) 0.79754(16) 0.0628(8) Uani 1 1 d . . . . .
H00L H 0.5961 0.6720 0.8341 0.075 Uiso 1 1 calc R . . . .
C00M C 0.5301(6) 0.8334(2) 0.5791(2) 0.0784(10) Uani 1 1 d . . . . .
H00M H 0.6134 0.8807 0.5615 0.094 Uiso 1 1 calc R . . . .
C00N C 0.3428(6) 0.8539(2) 0.60422(19) 0.0693(9) Uani 1 1 d . . . . .
H00N H 0.2982 0.9151 0.6042 0.083 Uiso 1 1 calc R . . . .
C00O C -0.1014(6) 0.2688(2) 0.6291(2) 0.0822(11) Uani 1 1 d . . . . .
H00O H -0.1314 0.2191 0.6610 0.099 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C005 1.356(3) . ?
O001 C007 1.439(3) . ?
O002 C00C 1.200(3) . ?
N003 C00B 1.144(3) . ?
C004 C005 1.347(3) . ?
C004 C00A 1.512(3) . ?
C004 C00B 1.425(3) . ?
C005 C009 1.477(3) . ?
C006 C00A 1.525(3) . ?
C006 C00E 1.388(4) . ?
C006 C00J 1.380(3) . ?
C007 H007 0.9800 . ?
C007 C008 1.525(3) . ?
C007 C00F 1.494(4) . ?
C008 H008 0.9800 . ?
C008 C00A 1.553(3) . ?
C008 C00C 1.527(4) . ?
C009 C00D 1.385(3) . ?
C009 C00K 1.391(4) . ?
C00A H00A 0.9800 . ?
C00C C00L 1.456(4) . ?
C00D H00D 0.9300 . ?
C00D C00H 1.374(4) . ?
C00E H00E 0.9300 . ?
C00E C00G 1.385(4) . ?
C00F H00F 0.9300 . ?
C00F C00L 1.324(4) . ?
C00G H00G 0.9300 . ?
C00G C00N 1.371(4) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.378(5) . ?
C00I H00I 0.9300 . ?
C00I C00O 1.376(5) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.389(5) . ?
C00K H00K 0.9300 . ?
C00K C00O 1.370(4) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.352(5) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?

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
C005 O001 C007 118.81(19) . . ?
C005 C004 C00A 121.3(2) . . ?
C005 C004 C00B 122.2(2) . . ?
C00B C004 C00A 116.4(2) . . ?
O001 C005 C009 111.5(2) . . ?
C004 C005 O001 120.9(2) . . ?
C004 C005 C009 127.6(2) . . ?
C00E C006 C00A 122.7(2) . . ?
C00J C006 C00A 119.4(2) . . ?
C00J C006 C00E 118.0(3) . . ?
O001 C007 H007 108.5 . . ?
O001 C007 C008 117.29(19) . . ?
O001 C007 C00F 108.8(2) . . ?
C008 C007 H007 108.5 . . ?
C00F C007 H007 108.5 . . ?
C00F C007 C008 104.9(2) . . ?
C007 C008 H008 108.9 . . ?
C007 C008 C00A 114.1(2) . . ?
C007 C008 C00C 103.37(19) . . ?
C00A C008 H008 108.9 . . ?
C00C C008 H008 108.9 . . ?
C00C C008 C00A 112.4(2) . . ?
C00D C009 C005 122.8(2) . . ?
C00D C009 C00K 118.7(2) . . ?
C00K C009 C005 118.5(2) . . ?
C004 C00A C006 112.03(19) . . ?
C004 C00A C008 108.1(2) . . ?
C004 C00A H00A 107.1 . . ?
C006 C00A C008 115.12(19) . . ?
C006 C00A H00A 107.1 . . ?
C008 C00A H00A 107.1 . . ?
N003 C00B C004 175.3(3) . . ?
O002 C00C C008 125.7(3) . . ?
O002 C00C C00L 126.8(3) . . ?
C00L C00C C008 107.5(2) . . ?
C009 C00D H00D 119.8 . . ?
C00H C00D C009 120.3(3) . . ?
C00H C00D H00D 119.8 . . ?
C006 C00E H00E 119.5 . . ?
C00G C00E C006 121.0(3) . . ?
C00G C00E H00E 119.5 . . ?
C007 C00F H00F 124.0 . . ?
C00L C00F C007 112.0(2) . . ?
C00L C00F H00F 124.0 . . ?
C00E C00G H00G 120.1 . . ?
C00N C00G C00E 119.8(3) . . ?
C00N C00G H00G 120.1 . . ?
C00D C00H H00H 119.8 . . ?
C00D C00H C00I 120.5(3) . . ?
C00I C00H H00H 119.8 . . ?
C00H C00I H00I 120.2 . . ?
C00O C00I C00H 119.6(3) . . ?
C00O C00I H00I 120.2 . . ?
C006 C00J H00J 119.8 . . ?
C006 C00J C00M 120.4(3) . . ?
C00M C00J H00J 119.8 . . ?
C009 C00K H00K 119.7 . . ?
C00O C00K C009 120.6(3) . . ?
C00O C00K H00K 119.7 . . ?
C00C C00L H00L 124.8 . . ?
C00F C00L C00C 110.5(2) . . ?
C00F C00L H00L 124.8 . . ?
C00J C00M H00M 119.6 . . ?
C00N C00M C00J 120.8(3) . . ?
C00N C00M H00M 119.6 . . ?
C00G C00N H00N 120.0 . . ?
C00M C00N C00G 119.9(3) . . ?
C00M C00N H00N 120.0 . . ?
C00I C00O H00O 119.9 . . ?
C00K C00O C00I 120.3(3) . . ?
C00K C00O H00O 119.9 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-01-15
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.850
_oxdiff_exptl_absorpt_empirical_full_min 0.631
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2125794'
loop_
_audit_author_name
_audit_author_address
'Ying-Chun Chen'
;Sichuan University
China
;
_audit_update_record             
;
2021-12-02 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_audit_creation_date             2020-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N O2'
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.7662(2)
_cell_length_b                   12.8859(3)
_cell_length_c                   16.6700(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1668.23(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3303
_cell_measurement_temperature    295.2(2)
_cell_measurement_theta_max      71.1780
_cell_measurement_theta_min      5.7360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9019
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.610
_diffrn_reflns_theta_min         4.337
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.2(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  33.00   1.00    2.06    --  -34.98  57.00 -30.00   86
  2  ω    -90.00  -2.00   1.00    2.06    --  -34.98 125.00   0.00   88
  3  ω     23.00  90.00   1.00    2.06    --   34.98-125.00-180.00   67
  4  ω    -33.00  53.00   1.00    2.06    --   34.98 -57.00-120.00   86
  5  ω      6.00 104.00   1.00    2.06    --   34.98  77.00  30.00   98
  6  ω     16.00 103.00   1.00    2.06    --   34.98  57.00 150.00   87
  7  ω     39.00 127.00   1.00    8.26    --  106.90 -61.00  60.00   88
  8  ω     37.00 110.00   1.00    8.26    --  106.90 -94.00 120.00   73
  9  ω     35.00 133.00   1.00    8.26    --  106.90 -30.00   0.00   98
 10  ω     37.00 110.00   1.00    8.26    --  106.90 -94.00-150.00   73
 11  ω    100.00 178.00   1.00    8.26    --  106.90 111.00 -60.00   78
 12  ω     37.00 127.00   1.00    8.26    --  106.90 -45.00 150.00   90
 13  ω     35.00 133.00   1.00    8.26    --  106.90 -30.00 -90.00   98
 14  ω    -37.00  71.00   1.00    2.06    --   34.98 -19.00  90.00  108
 15  ω     16.00 103.00   1.00    2.06    --   34.98  57.00 -90.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1914822000
_diffrn_orient_matrix_UB_12      -0.0134674000
_diffrn_orient_matrix_UB_13      0.0218299000
_diffrn_orient_matrix_UB_21      0.0484371000
_diffrn_orient_matrix_UB_22      -0.0069679000
_diffrn_orient_matrix_UB_23      0.0894351000
_diffrn_orient_matrix_UB_31      -0.0188596000
_diffrn_orient_matrix_UB_32      0.1186049000
_diffrn_orient_matrix_UB_33      0.0077079000
_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         0.726
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2873
_reflns_number_total             3165
_reflns_odcompleteness_completeness 99.94
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1076 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.041
_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)+(0.0833P)²+0.1880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1452
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005), C00A(H00A), C00B(H00B), C00D(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00H,H00I), C00O(H00P,H00Q)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00J), C00J(H00K),
 C00K(H00L), C00L(H00M), C00M(H00N), C00N(H00O)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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
O001 O 0.3087(3) 0.31675(17) 0.18036(13) 0.0517(5) Uani 1 1 d . . . . .
O002 O 0.5650(4) 0.4958(2) 0.2334(2) 0.0869(10) Uani 1 1 d . . . . .
H002 H 0.6522 0.5313 0.2293 0.130 Uiso 1 1 calc GR . . . .
C003 C 0.1860(4) 0.3902(2) 0.18598(17) 0.0430(6) Uani 1 1 d . . . . .
C004 C 0.0308(4) 0.5247(2) 0.2562(2) 0.0499(7) Uani 1 1 d . . . . .
C005 C 0.2753(4) 0.4407(2) 0.32711(17) 0.0425(6) Uani 1 1 d . . . . .
H005 H 0.3251 0.5092 0.3377 0.051 Uiso 1 1 calc R . . . .
C006 C 0.1661(4) 0.4499(2) 0.25206(17) 0.0420(6) Uani 1 1 d . . . . .
C007 C 0.0793(4) 0.3947(2) 0.11285(18) 0.0464(7) Uani 1 1 d . . . . .
N008 N -0.0739(5) 0.5859(2) 0.2639(2) 0.0726(9) Uani 1 1 d . . . . .
C009 C 0.1624(4) 0.4126(2) 0.39855(18) 0.0462(7) Uani 1 1 d . . . . .
C00A C 0.4254(4) 0.3650(2) 0.31297(18) 0.0435(6) Uani 1 1 d . . . . .
H00A H 0.4481 0.3310 0.3645 0.052 Uiso 1 1 calc R . . . .
C00B C 0.3887(4) 0.2788(2) 0.2526(2) 0.0483(7) Uani 1 1 d . . . . .
H00B H 0.3189 0.2239 0.2771 0.058 Uiso 1 1 calc R . . . .
C00C C 0.0230(5) 0.4881(3) 0.0801(2) 0.0579(8) Uani 1 1 d . . . . .
H00C H 0.0530 0.5506 0.1042 0.069 Uiso 1 1 calc R . . . .
C00D C 0.5967(4) 0.4124(2) 0.2852(2) 0.0507(7) Uani 1 1 d . . . . .
H00D H 0.6650 0.4351 0.3314 0.061 Uiso 1 1 calc R . . . .
C00E C 0.0330(5) 0.3030(3) 0.0750(2) 0.0576(8) Uani 1 1 d . . . . .
H00E H 0.0696 0.2399 0.0961 0.069 Uiso 1 1 calc R . . . .
C00F C 0.1438(5) 0.4824(3) 0.4612(2) 0.0613(9) Uani 1 1 d . . . . .
H00F H 0.2004 0.5460 0.4591 0.074 Uiso 1 1 calc R . . . .
C00G C 0.0728(5) 0.3199(3) 0.4028(2) 0.0604(8) Uani 1 1 d . . . . .
H00G H 0.0817 0.2724 0.3610 0.073 Uiso 1 1 calc R . . . .
C00H C 0.5664(5) 0.2379(3) 0.2300(3) 0.0621(9) Uani 1 1 d . . . . .
H00H H 0.5980 0.1799 0.2640 0.074 Uiso 1 1 calc R . . . .
H00I H 0.5677 0.2150 0.1745 0.074 Uiso 1 1 calc R . . . .
C00I C -0.0661(6) 0.3040(3) 0.0070(2) 0.0726(11) Uani 1 1 d . . . . .
H00J H -0.0958 0.2419 -0.0178 0.087 Uiso 1 1 calc R . . . .
C00J C -0.0428(6) 0.3656(4) 0.5301(3) 0.0757(11) Uani 1 1 d . . . . .
H00K H -0.1095 0.3494 0.5747 0.091 Uiso 1 1 calc R . . . .
C00K C -0.0781(5) 0.4878(3) 0.0113(2) 0.0674(10) Uani 1 1 d . . . . .
H00L H -0.1162 0.5503 -0.0102 0.081 Uiso 1 1 calc R . . . .
C00L C -0.1218(6) 0.3970(4) -0.0247(3) 0.0769(11) Uani 1 1 d . . . . .
H00M H -0.1893 0.3976 -0.0708 0.092 Uiso 1 1 calc R . . . .
C00M C 0.0430(6) 0.4589(4) 0.5265(2) 0.0771(12) Uani 1 1 d . . . . .
H00N H 0.0327 0.5062 0.5684 0.092 Uiso 1 1 calc R . . . .
C00N C -0.0300(6) 0.2970(3) 0.4683(3) 0.0743(11) Uani 1 1 d . . . . .
H00O H -0.0903 0.2346 0.4701 0.089 Uiso 1 1 calc R . . . .
C00O C 0.6864(6) 0.3254(3) 0.2417(4) 0.0995(19) Uani 1 1 d . . . . .
H00P H 0.7271 0.3498 0.1900 0.119 Uiso 1 1 calc R . . . .
H00Q H 0.7852 0.3024 0.2725 0.119 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C003 1.346(4) . ?
O001 C00B 1.441(4) . ?
O002 H002 0.8200 . ?
O002 C00D 1.402(4) . ?
C003 C006 1.352(4) . ?
C003 C007 1.475(4) . ?
C004 C006 1.428(4) . ?
C004 N008 1.140(4) . ?
C005 H005 0.9800 . ?
C005 C006 1.516(4) . ?
C005 C009 1.522(4) . ?
C005 C00A 1.537(4) . ?
C007 C00C 1.392(5) . ?
C007 C00E 1.387(4) . ?
C009 C00F 1.386(5) . ?
C009 C00G 1.385(5) . ?
C00A H00A 0.9800 . ?
C00A C00B 1.526(4) . ?
C00A C00D 1.535(4) . ?
C00B H00B 0.9800 . ?
C00B C00H 1.524(4) . ?
C00C H00C 0.9300 . ?
C00C C00K 1.390(5) . ?
C00D H00D 0.9800 . ?
C00D C00O 1.506(5) . ?
C00E H00E 0.9300 . ?
C00E C00I 1.370(5) . ?
C00F H00F 0.9300 . ?
C00F C00M 1.375(6) . ?
C00G H00G 0.9300 . ?
C00G C00N 1.385(5) . ?
C00H H00H 0.9700 . ?
C00H H00I 0.9700 . ?
C00H C00O 1.476(6) . ?
C00I H00J 0.9300 . ?
C00I C00L 1.380(6) . ?
C00J H00K 0.9300 . ?
C00J C00M 1.376(7) . ?
C00J C00N 1.361(6) . ?
C00K H00L 0.9300 . ?
C00K C00L 1.357(6) . ?
C00L H00M 0.9300 . ?
C00M H00N 0.9300 . ?
C00N H00O 0.9300 . ?
C00O H00P 0.9700 . ?
C00O H00Q 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C003 O001 C00B 119.1(2) . . ?
C00D O002 H002 109.5 . . ?
O001 C003 C006 122.5(3) . . ?
O001 C003 C007 111.6(2) . . ?
C006 C003 C007 125.9(3) . . ?
N008 C004 C006 176.0(4) . . ?
C006 C005 H005 107.4 . . ?
C006 C005 C009 110.0(2) . . ?
C006 C005 C00A 110.3(2) . . ?
C009 C005 H005 107.4 . . ?
C009 C005 C00A 114.0(2) . . ?
C00A C005 H005 107.4 . . ?
C003 C006 C004 120.5(3) . . ?
C003 C006 C005 124.3(3) . . ?
C004 C006 C005 115.1(3) . . ?
C00C C007 C003 122.3(3) . . ?
C00E C007 C003 119.2(3) . . ?
C00E C007 C00C 118.5(3) . . ?
C00F C009 C005 119.7(3) . . ?
C00G C009 C005 122.3(3) . . ?
C00G C009 C00F 118.0(3) . . ?
C005 C00A H00A 106.6 . . ?
C00B C00A C005 114.9(2) . . ?
C00B C00A H00A 106.6 . . ?
C00B C00A C00D 104.6(2) . . ?
C00D C00A C005 116.9(2) . . ?
C00D C00A H00A 106.6 . . ?
O001 C00B C00A 112.6(2) . . ?
O001 C00B H00B 110.8 . . ?
O001 C00B C00H 107.5(3) . . ?
C00A C00B H00B 110.8 . . ?
C00H C00B C00A 104.3(3) . . ?
C00H C00B H00B 110.8 . . ?
C007 C00C H00C 120.1 . . ?
C00K C00C C007 119.9(3) . . ?
C00K C00C H00C 120.1 . . ?
O002 C00D C00A 109.8(3) . . ?
O002 C00D H00D 110.5 . . ?
O002 C00D C00O 110.8(4) . . ?
C00A C00D H00D 110.6 . . ?
C00O C00D C00A 104.5(3) . . ?
C00O C00D H00D 110.5 . . ?
C007 C00E H00E 119.6 . . ?
C00I C00E C007 120.9(4) . . ?
C00I C00E H00E 119.6 . . ?
C009 C00F H00F 119.6 . . ?
C00M C00F C009 120.8(4) . . ?
C00M C00F H00F 119.6 . . ?
C009 C00G H00G 119.5 . . ?
C009 C00G C00N 120.9(4) . . ?
C00N C00G H00G 119.5 . . ?
C00B C00H H00H 110.5 . . ?
C00B C00H H00I 110.5 . . ?
H00H C00H H00I 108.7 . . ?
C00O C00H C00B 105.9(3) . . ?
C00O C00H H00H 110.5 . . ?
C00O C00H H00I 110.5 . . ?
C00E C00I H00J 120.0 . . ?
C00E C00I C00L 120.1(4) . . ?
C00L C00I H00J 120.0 . . ?
C00M C00J H00K 120.0 . . ?
C00N C00J H00K 120.0 . . ?
C00N C00J C00M 119.9(4) . . ?
C00C C00K H00L 119.7 . . ?
C00L C00K C00C 120.6(4) . . ?
C00L C00K H00L 119.7 . . ?
C00I C00L H00M 120.0 . . ?
C00K C00L C00I 120.0(4) . . ?
C00K C00L H00M 120.0 . . ?
C00F C00M C00J 120.2(4) . . ?
C00F C00M H00N 119.9 . . ?
C00J C00M H00N 119.9 . . ?
C00G C00N H00O 120.0 . . ?
C00J C00N C00G 120.0(4) . . ?
C00J C00N H00O 120.0 . . ?
C00D C00O H00P 109.7 . . ?
C00D C00O H00Q 109.7 . . ?
C00H C00O C00D 109.9(3) . . ?
C00H C00O H00P 109.7 . . ?
C00H C00O H00Q 109.7 . . ?
H00P C00O H00Q 108.2 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-09-22
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.573
_oxdiff_exptl_absorpt_empirical_full_min 0.669
