# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_wtl-zlx-p1
_database_code_depnum_ccdc_archive 'CCDC 2004465'
loop_
_audit_author_name
_audit_author_address
zlx
;zlx
China
;
_audit_update_record             
;
2020-05-18 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_audit_creation_date             2019-06-03
_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 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36
_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                   9.61101(18)
_cell_length_b                   10.7261(2)
_cell_length_c                   15.5952(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1607.68(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3753
_cell_measurement_temperature    296.63(16)
_cell_measurement_theta_max      71.4930
_cell_measurement_theta_min      4.9450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64614
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8852
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.704
_diffrn_reflns_theta_min         5.004
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.63(16)
_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    -53.00  31.00   1.00    1.00    --  -36.29  57.00 -60.00   84
  2  ω   -106.00  33.00   1.00    1.00    --  -36.29   0.00 -60.00  139
  3  ω      1.00  75.00   1.00    1.00    --   36.29 -99.00-120.00   74
  4  ω     88.00 173.00   1.00    1.61    --  106.21  61.00   0.00   85
  5  ω     79.00 174.00   1.00    1.61    --  106.21  77.00  90.00   95
  6  ω     37.00 109.00   1.00    1.61    --  106.21 -94.00   0.00   72
  7  ω     89.00 175.00   1.00    1.61    --  106.21  45.00 120.00   86
  8  ω     39.00 124.00   1.00    1.61    --  106.21 -61.00 150.00   85
  9  ω     68.00 177.00   1.00    1.61    --  106.21  15.00-120.00  109
 10  ω     37.00 109.00   1.00    1.61    --  106.21 -94.00-120.00   72
 11  ω     57.00 150.00   1.00    1.61    --  106.21 178.00  30.00   93
 12  ω   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00-150.00   94
 13  ω    -31.00  22.00   1.00    1.00    --   36.29 -57.00  60.00   53
;
_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      -0.0829550000
_diffrn_orient_matrix_UB_12      -0.1227356000
_diffrn_orient_matrix_UB_13      0.0044948000
_diffrn_orient_matrix_UB_21      -0.0018229000
_diffrn_orient_matrix_UB_22      -0.0066307000
_diffrn_orient_matrix_UB_23      -0.0986731000
_diffrn_orient_matrix_UB_31      0.1371814000
_diffrn_orient_matrix_UB_32      -0.0742450000
_diffrn_orient_matrix_UB_33      0.0014005000
_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         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                2935
_reflns_number_total             3096
_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         0.333
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.162
_refine_ls_abs_structure_details 
;
 Flack x determined using 1167 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0726
_refine_ls_restrained_S_all      1.115
_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)+(0.1206P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1640
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C005(H005), C00A(H00A), C00B(H00B), C00D(H00D), 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 -0.1707(2) -0.6481(2) -0.32731(13) 0.0464(5) Uani 1 1 d . . . . .
O002 O -0.0242(2) -0.5569(2) -0.45917(17) 0.0546(6) Uani 1 1 d . . . . .
N003 N -0.3160(3) -0.7274(2) -0.47375(14) 0.0410(5) Uani 1 1 d . . . . .
H003 H -0.3416 -0.7405 -0.5258 0.049 Uiso 1 1 calc R . . . .
C004 C -0.1389(3) -0.5121(3) -0.45073(18) 0.0400(6) Uani 1 1 d . . . . .
C005 C -0.5434(3) -0.7641(3) -0.35465(19) 0.0446(6) Uani 1 1 d . . . . .
H005 H -0.5077 -0.8302 -0.3863 0.053 Uiso 1 1 calc R . . . .
C006 C -0.4840(3) -0.6475(2) -0.36191(16) 0.0353(6) Uani 1 1 d . . . . .
C007 C -0.1869(3) -0.4075(2) -0.50606(18) 0.0389(6) Uani 1 1 d . . . . .
C008 C -0.2387(3) -0.5622(3) -0.38269(16) 0.0385(6) Uani 1 1 d . . . . .
H008 H -0.2709 -0.4916 -0.3480 0.046 Uiso 1 1 calc R . . . .
C009 C -0.3672(3) -0.6219(3) -0.42597(16) 0.0363(6) Uani 1 1 d . . . . .
H009 H -0.4029 -0.5615 -0.4677 0.044 Uiso 1 1 calc R . . . .
C00A C -0.2922(4) -0.3259(3) -0.4817(2) 0.0500(7) Uani 1 1 d . . . . .
H00A H -0.3373 -0.3368 -0.4294 0.060 Uiso 1 1 calc R . . . .
C00B C -0.6484(3) -0.5701(4) -0.2576(2) 0.0544(8) Uani 1 1 d . . . . .
H00B H -0.6833 -0.5045 -0.2251 0.065 Uiso 1 1 calc R . . . .
C00C C -0.2236(3) -0.8074(3) -0.43251(18) 0.0407(6) Uani 1 1 d . . . . .
C00D C -0.1226(4) -0.3904(3) -0.58538(19) 0.0498(7) Uani 1 1 d . . . . .
H00D H -0.0524 -0.4444 -0.6028 0.060 Uiso 1 1 calc R . . . .
C00E C -0.5377(3) -0.5505(3) -0.3125(2) 0.0462(7) Uani 1 1 d . . . . .
H00E H -0.4984 -0.4715 -0.3165 0.055 Uiso 1 1 calc R . . . .
C00F C -0.1995(3) -0.9278(3) -0.4615(2) 0.0511(7) Uani 1 1 d . . . . .
H00F H -0.2483 -0.9577 -0.5087 0.061 Uiso 1 1 calc R . . . .
C00G C -0.1493(3) -0.7648(3) -0.36108(19) 0.0430(6) Uani 1 1 d . . . . .
C00H C -0.2662(4) -0.2128(3) -0.6133(2) 0.0608(9) Uani 1 1 d . . . . .
H00H H -0.2929 -0.1478 -0.6491 0.073 Uiso 1 1 calc R . . . .
C00I C -0.1032(4) -1.0041(3) -0.4209(3) 0.0625(10) Uani 1 1 d . . . . .
H00I H -0.0878 -1.0844 -0.4414 0.075 Uiso 1 1 calc R . . . .
C00J C -0.3301(4) -0.2280(3) -0.5353(3) 0.0605(9) Uani 1 1 d . . . . .
H00J H -0.3991 -0.1726 -0.5182 0.073 Uiso 1 1 calc R . . . .
C00K C -0.0532(3) -0.8419(4) -0.3205(2) 0.0577(9) Uani 1 1 d . . . . .
H00K H -0.0041 -0.8130 -0.2732 0.069 Uiso 1 1 calc R . . . .
C00L C -0.7072(4) -0.6871(4) -0.2511(2) 0.0573(8) Uani 1 1 d . . . . .
H00L H -0.7810 -0.7008 -0.2136 0.069 Uiso 1 1 calc R . . . .
C00M C -0.1633(4) -0.2929(4) -0.6384(2) 0.0609(9) Uani 1 1 d . . . . .
H00M H -0.1204 -0.2821 -0.6914 0.073 Uiso 1 1 calc R . . . .
C00N C -0.6561(3) -0.7838(3) -0.3005(2) 0.0560(8) Uani 1 1 d . . . . .
H00N H -0.6971 -0.8622 -0.2975 0.067 Uiso 1 1 calc R . . . .
C00O C -0.0306(4) -0.9620(4) -0.3507(3) 0.0686(11) Uani 1 1 d . . . . .
H00O H 0.0334 -1.0136 -0.3236 0.082 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 C008 1.422(3) . ?
O001 C00G 1.374(4) . ?
O002 C004 1.210(4) . ?
N003 H003 0.8600 . ?
N003 C009 1.442(4) . ?
N003 C00C 1.392(4) . ?
C004 C007 1.488(4) . ?
C004 C008 1.528(4) . ?
C005 H005 0.9300 . ?
C005 C006 1.379(4) . ?
C005 C00N 1.389(4) . ?
C006 C009 1.528(3) . ?
C006 C00E 1.394(4) . ?
C007 C00A 1.391(4) . ?
C007 C00D 1.395(4) . ?
C008 H008 0.9800 . ?
C008 C009 1.546(4) . ?
C009 H009 0.9800 . ?
C00A H00A 0.9300 . ?
C00A C00J 1.391(5) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.382(4) . ?
C00B C00L 1.380(5) . ?
C00C C00F 1.389(4) . ?
C00C C00G 1.400(4) . ?
C00D H00D 0.9300 . ?
C00D C00M 1.390(5) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00I 1.388(5) . ?
C00G C00K 1.392(4) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.372(6) . ?
C00H C00M 1.367(6) . ?
C00I H00I 0.9300 . ?
C00I C00O 1.375(6) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00O 1.388(6) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.382(5) . ?
C00M H00M 0.9300 . ?
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
C00G O001 C008 115.2(2) . . ?
C009 N003 H003 121.2 . . ?
C00C N003 H003 121.2 . . ?
C00C N003 C009 117.5(2) . . ?
O002 C004 C007 121.3(3) . . ?
O002 C004 C008 120.5(3) . . ?
C007 C004 C008 118.2(2) . . ?
C006 C005 H005 119.7 . . ?
C006 C005 C00N 120.7(3) . . ?
C00N C005 H005 119.7 . . ?
C005 C006 C009 121.4(3) . . ?
C005 C006 C00E 118.6(3) . . ?
C00E C006 C009 119.9(2) . . ?
C00A C007 C004 122.8(3) . . ?
C00A C007 C00D 118.8(3) . . ?
C00D C007 C004 118.4(3) . . ?
O001 C008 C004 111.1(2) . . ?
O001 C008 H008 108.0 . . ?
O001 C008 C009 111.3(2) . . ?
C004 C008 H008 108.0 . . ?
C004 C008 C009 110.1(2) . . ?
C009 C008 H008 108.0 . . ?
N003 C009 C006 116.6(2) . . ?
N003 C009 C008 106.2(2) . . ?
N003 C009 H009 107.2 . . ?
C006 C009 C008 112.1(2) . . ?
C006 C009 H009 107.2 . . ?
C008 C009 H009 107.2 . . ?
C007 C00A H00A 120.0 . . ?
C00J C00A C007 120.1(3) . . ?
C00J C00A H00A 120.0 . . ?
C00E C00B H00B 120.0 . . ?
C00L C00B H00B 120.0 . . ?
C00L C00B C00E 120.0(3) . . ?
N003 C00C C00G 119.5(3) . . ?
C00F C00C N003 122.0(3) . . ?
C00F C00C C00G 118.5(3) . . ?
C007 C00D H00D 119.9 . . ?
C00M C00D C007 120.2(3) . . ?
C00M C00D H00D 119.9 . . ?
C006 C00E H00E 119.5 . . ?
C00B C00E C006 120.9(3) . . ?
C00B C00E H00E 119.5 . . ?
C00C C00F H00F 119.6 . . ?
C00I C00F C00C 120.8(4) . . ?
C00I C00F H00F 119.6 . . ?
O001 C00G C00C 121.7(3) . . ?
O001 C00G C00K 117.8(3) . . ?
C00K C00G C00C 120.4(3) . . ?
C00J C00H H00H 119.9 . . ?
C00M C00H H00H 119.9 . . ?
C00M C00H C00J 120.2(3) . . ?
C00F C00I H00I 119.7 . . ?
C00O C00I C00F 120.5(4) . . ?
C00O C00I H00I 119.7 . . ?
C00A C00J H00J 119.8 . . ?
C00H C00J C00A 120.4(3) . . ?
C00H C00J H00J 119.8 . . ?
C00G C00K H00K 120.0 . . ?
C00O C00K C00G 120.1(4) . . ?
C00O C00K H00K 120.0 . . ?
C00B C00L H00L 120.2 . . ?
C00B C00L C00N 119.7(3) . . ?
C00N C00L H00L 120.2 . . ?
C00D C00M H00M 119.8 . . ?
C00H C00M C00D 120.4(3) . . ?
C00H C00M H00M 119.8 . . ?
C005 C00N H00N 119.9 . . ?
C00L C00N C005 120.1(3) . . ?
C00L C00N H00N 119.9 . . ?
C00I C00O C00K 119.7(3) . . ?
C00I C00O H00O 120.1 . . ?
C00K C00O H00O 120.1 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-06-03
_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 1.606
_oxdiff_exptl_absorpt_empirical_full_min 0.776
####################################################################### 
# 
# 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_wtl-zlx-2
_database_code_depnum_ccdc_archive 'CCDC 2004466'
loop_
_audit_author_name
_audit_author_address
zlx
;zlx
China
;
_audit_update_record             
;
2020-05-18 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_audit_creation_date             2019-09-11
_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         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39
_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                   8.4921(2)
_cell_length_b                   13.5753(4)
_cell_length_c                   15.0981(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1740.54(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3849
_cell_measurement_temperature    295.88(16)
_cell_measurement_theta_max      71.5490
_cell_measurement_theta_min      4.3440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63155
_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    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7797
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.397
_diffrn_reflns_theta_min         4.380
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.88(16)
_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 0.993
_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 -19.00   1.00    1.00    --  -36.04 -57.00 -60.00   84
  2  ω    -89.00  -2.00   1.00    1.00    --  -36.04 125.00-180.00   87
  3  ω   -105.00  33.00   1.00    1.00    --  -36.04   0.00-180.00  138
  4  ω    100.00 176.00   1.00    1.00    --  106.21 111.00   0.00   76
  5  ω     38.00 124.00   1.00    1.00    --  106.21 -45.00   0.00   86
  6  ω     37.00 109.00   1.00    1.00    --  106.21 -94.00 -60.00   72
  7  ω     38.00 124.00   1.00    1.00    --  106.21 -45.00 -90.00   86
  8  ω     88.00 173.00   1.00    1.00    --  106.21  61.00 -30.00   85
  9  ω     85.00 176.00   1.00    1.00    --  106.21  30.00-120.00   91
 10  ω     39.00 133.00   1.00    1.00    --  106.21 -77.00  60.00   94
 11  ω   -103.00 -52.00   1.00    1.00    --  -36.04 -57.00 120.00   51
;
_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      -0.1690366000
_diffrn_orient_matrix_UB_12      0.0152348000
_diffrn_orient_matrix_UB_13      -0.0345410000
_diffrn_orient_matrix_UB_21      -0.0656309000
_diffrn_orient_matrix_UB_22      -0.0271465000
_diffrn_orient_matrix_UB_23      0.0919853000
_diffrn_orient_matrix_UB_31      0.0070353000
_diffrn_orient_matrix_UB_32      0.1090494000
_diffrn_orient_matrix_UB_33      0.0276597000
_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         0.718
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3132
_reflns_number_total             3330
_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         0.391
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details 
;
 Flack x determined using 1216 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   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.116
_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)+(0.1149P)²+0.0107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1667
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00D,H00E), C00N(H00F,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), C005(H005), C006(H006), C009(H009), C00A(H00A), C00C(H00C),
 C00G(H00G), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
;
_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 0.5622(3) 0.18822(17) 0.31179(15) 0.0490(6) Uani 1 1 d . . . . .
O002 O 0.4197(3) 0.37666(18) 0.22682(18) 0.0564(7) Uani 1 1 d . . . . .
N003 N 0.8077(3) 0.29886(19) 0.38238(16) 0.0420(6) Uani 1 1 d . . . . .
H003 H 0.9039 0.3170 0.3893 0.050 Uiso 1 1 calc R . . . .
C004 C 0.7951(3) 0.4251(2) 0.26741(17) 0.0331(6) Uani 1 1 d . . . . .
C005 C 0.5628(4) 0.0850(2) 0.4363(2) 0.0388(6) Uani 1 1 d . . . . .
H005 H 0.4864 0.0465 0.4089 0.047 Uiso 1 1 calc R . . . .
C006 C 0.7219(3) 0.5112(2) 0.2422(2) 0.0388(6) Uani 1 1 d . . . . .
H006 H 0.6167 0.5212 0.2567 0.047 Uiso 1 1 calc R . . . .
C007 C 0.6249(3) 0.16557(19) 0.39289(18) 0.0319(6) Uani 1 1 d . . . . .
C008 C 0.7431(3) 0.2222(2) 0.43174(18) 0.0334(6) Uani 1 1 d . . . . .
C009 C 0.7939(4) 0.1973(2) 0.5159(2) 0.0418(7) Uani 1 1 d . . . . .
H009 H 0.8726 0.2344 0.5428 0.050 Uiso 1 1 calc R . . . .
C00A C 0.7292(4) 0.1179(2) 0.5608(2) 0.0474(8) Uani 1 1 d . . . . .
H00A H 0.7632 0.1029 0.6178 0.057 Uiso 1 1 calc R . . . .
C00B C 0.7039(3) 0.3472(2) 0.31801(17) 0.0341(6) Uani 1 1 d . . . . .
H00B H 0.6178 0.3794 0.3501 0.041 Uiso 1 1 calc R . . . .
C00C C 0.6149(4) 0.0615(2) 0.5211(2) 0.0464(8) Uani 1 1 d . . . . .
H00C H 0.5724 0.0078 0.5508 0.056 Uiso 1 1 calc R . . . .
C00D C 0.5178(4) 0.1529(2) 0.10904(19) 0.0414(7) Uani 1 1 d . . . . .
C00E C 0.4274(4) 0.2324(2) 0.13858(18) 0.0373(6) Uani 1 1 d . . . . .
C00F C 0.4858(3) 0.3009(2) 0.20760(18) 0.0345(6) Uani 1 1 d . . . . .
C00G C 0.8035(4) 0.5835(2) 0.1953(2) 0.0489(8) Uani 1 1 d . . . . .
H00G H 0.7525 0.6411 0.1781 0.059 Uiso 1 1 calc R . . . .
C00H C 0.7505(4) 0.2212(2) 0.1944(2) 0.0424(7) Uani 1 1 d . . . . .
H00D H 0.8431 0.1997 0.2266 0.051 Uiso 1 1 calc R . . . .
H00E H 0.7831 0.2710 0.1521 0.051 Uiso 1 1 calc R . . . .
C00I C 0.6338(3) 0.26557(19) 0.25848(17) 0.0321(6) Uani 1 1 d . . . . .
C00J C 0.9557(3) 0.4128(2) 0.2473(2) 0.0428(7) Uani 1 1 d . . . . .
H00J H 1.0083 0.3563 0.2658 0.051 Uiso 1 1 calc R . . . .
C00K C 0.9599(4) 0.5693(3) 0.1744(2) 0.0504(8) Uani 1 1 d . . . . .
H00K H 1.0143 0.6173 0.1429 0.060 Uiso 1 1 calc R . . . .
C00L C 1.0358(4) 0.4845(3) 0.2000(2) 0.0516(8) Uani 1 1 d . . . . .
H00L H 1.1412 0.4752 0.1856 0.062 Uiso 1 1 calc R . . . .
C00M C 0.2745(4) 0.2464(3) 0.1056(2) 0.0524(8) Uani 1 1 d . . . . .
H00M H 0.2143 0.2993 0.1252 0.063 Uiso 1 1 calc R . . . .
C00N C 0.6795(4) 0.1336(3) 0.1447(3) 0.0517(8) Uani 1 1 d . . . . .
H00F H 0.7484 0.1163 0.0958 0.062 Uiso 1 1 calc R . . . .
H00H H 0.6749 0.0775 0.1844 0.062 Uiso 1 1 calc R . . . .
C00O C 0.4524(5) 0.0909(3) 0.0449(2) 0.0574(9) Uani 1 1 d . . . . .
H00O H 0.5120 0.0385 0.0237 0.069 Uiso 1 1 calc R . . . .
C00P C 0.2136(5) 0.1813(3) 0.0439(3) 0.0667(11) Uani 1 1 d . . . . .
H00P H 0.1111 0.1893 0.0235 0.080 Uiso 1 1 calc R . . . .
C00Q C 0.3045(6) 0.1046(3) 0.0127(3) 0.0691(12) Uani 1 1 d . . . . .
H00Q H 0.2648 0.0623 -0.0304 0.083 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 C007 1.370(3) . ?
O001 C00I 1.456(3) . ?
O002 C00F 1.208(4) . ?
N003 H003 0.8600 . ?
N003 C008 1.392(4) . ?
N003 C00B 1.467(4) . ?
C004 C006 1.378(4) . ?
C004 C00B 1.517(4) . ?
C004 C00J 1.407(4) . ?
C005 H005 0.9300 . ?
C005 C007 1.380(4) . ?
C005 C00C 1.391(4) . ?
C006 H006 0.9300 . ?
C006 C00G 1.395(5) . ?
C007 C008 1.394(4) . ?
C008 C009 1.384(4) . ?
C009 H009 0.9300 . ?
C009 C00A 1.386(5) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.374(5) . ?
C00B H00B 0.9800 . ?
C00B C00I 1.546(4) . ?
C00C H00C 0.9300 . ?
C00D C00E 1.397(4) . ?
C00D C00N 1.498(5) . ?
C00D C00O 1.398(4) . ?
C00E C00F 1.482(4) . ?
C00E C00M 1.403(4) . ?
C00F C00I 1.549(4) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.379(5) . ?
C00H H00D 0.9700 . ?
C00H H00E 0.9700 . ?
C00H C00I 1.510(4) . ?
C00H C00N 1.531(5) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.385(5) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.375(5) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00P 1.384(5) . ?
C00N H00F 0.9700 . ?
C00N H00H 0.9700 . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.359(6) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.380(7) . ?
C00Q H00Q 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
C007 O001 C00I 119.6(2) . . ?
C008 N003 H003 121.5 . . ?
C008 N003 C00B 116.9(2) . . ?
C00B N003 H003 121.5 . . ?
C006 C004 C00B 120.0(2) . . ?
C006 C004 C00J 118.6(3) . . ?
C00J C004 C00B 121.4(3) . . ?
C007 C005 H005 120.1 . . ?
C007 C005 C00C 119.8(3) . . ?
C00C C005 H005 120.1 . . ?
C004 C006 H006 119.6 . . ?
C004 C006 C00G 120.9(3) . . ?
C00G C006 H006 119.6 . . ?
O001 C007 C005 117.0(2) . . ?
O001 C007 C008 122.2(3) . . ?
C005 C007 C008 120.9(3) . . ?
N003 C008 C007 118.1(2) . . ?
C009 C008 N003 123.4(3) . . ?
C009 C008 C007 118.5(3) . . ?
C008 C009 H009 119.5 . . ?
C008 C009 C00A 121.0(3) . . ?
C00A C009 H009 119.5 . . ?
C009 C00A H00A 120.0 . . ?
C00C C00A C009 120.0(3) . . ?
C00C C00A H00A 120.0 . . ?
N003 C00B C004 109.8(2) . . ?
N003 C00B H00B 108.6 . . ?
N003 C00B C00I 107.2(2) . . ?
C004 C00B H00B 108.6 . . ?
C004 C00B C00I 113.8(2) . . ?
C00I C00B H00B 108.6 . . ?
C005 C00C H00C 120.0 . . ?
C00A C00C C005 119.9(3) . . ?
C00A C00C H00C 120.0 . . ?
C00E C00D C00N 121.6(3) . . ?
C00E C00D C00O 117.9(3) . . ?
C00O C00D C00N 120.5(3) . . ?
C00D C00E C00F 121.7(3) . . ?
C00D C00E C00M 120.0(3) . . ?
C00M C00E C00F 118.3(3) . . ?
O002 C00F C00E 123.2(3) . . ?
O002 C00F C00I 121.5(3) . . ?
C00E C00F C00I 115.2(2) . . ?
C006 C00G H00G 120.1 . . ?
C00K C00G C006 119.7(3) . . ?
C00K C00G H00G 120.1 . . ?
H00D C00H H00E 108.0 . . ?
C00I C00H H00D 109.3 . . ?
C00I C00H H00E 109.3 . . ?
C00I C00H C00N 111.4(3) . . ?
C00N C00H H00D 109.3 . . ?
C00N C00H H00E 109.3 . . ?
O001 C00I C00B 110.9(2) . . ?
O001 C00I C00F 99.1(2) . . ?
O001 C00I C00H 109.9(2) . . ?
C00B C00I C00F 112.3(2) . . ?
C00H C00I C00B 113.9(2) . . ?
C00H C00I C00F 109.8(2) . . ?
C004 C00J H00J 119.9 . . ?
C00L C00J C004 120.3(3) . . ?
C00L C00J H00J 119.9 . . ?
C00G C00K H00K 119.8 . . ?
C00L C00K C00G 120.3(3) . . ?
C00L C00K H00K 119.8 . . ?
C00J C00L H00L 119.9 . . ?
C00K C00L C00J 120.2(3) . . ?
C00K C00L H00L 119.9 . . ?
C00E C00M H00M 120.1 . . ?
C00P C00M C00E 119.8(4) . . ?
C00P C00M H00M 120.1 . . ?
C00D C00N C00H 113.7(3) . . ?
C00D C00N H00F 108.8 . . ?
C00D C00N H00H 108.8 . . ?
C00H C00N H00F 108.8 . . ?
C00H C00N H00H 108.8 . . ?
H00F C00N H00H 107.7 . . ?
C00D C00O H00O 118.9 . . ?
C00Q C00O C00D 122.2(4) . . ?
C00Q C00O H00O 118.9 . . ?
C00M C00P H00P 119.9 . . ?
C00M C00P C00Q 120.2(4) . . ?
C00Q C00P H00P 119.9 . . ?
C00O C00Q C00P 119.8(4) . . ?
C00O C00Q H00Q 120.1 . . ?
C00P C00Q H00Q 120.1 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-09-11
_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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.602
