# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_lxf-190411-150k
_database_code_depnum_ccdc_archive 'CCDC 1897162'
loop_
_audit_author_name
_audit_author_address
'Xuefeng Li'
;Southwest Minzu University
China
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;
_audit_creation_date             2019-04-11
_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         'C21 H18 O3'
_chemical_formula_sum            'C21 H18 O3'
_chemical_formula_weight         318.35
_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      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                   8.5720(3)
_cell_length_b                   9.4216(2)
_cell_length_c                   20.1701(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1628.99(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.6440
_cell_measurement_theta_min      4.3610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71920
_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    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6074
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        64.207
_diffrn_reflns_theta_max         64.207
_diffrn_reflns_theta_min         4.384
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(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 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   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00 -90.00   84
  2  ω    -94.00  -6.00   1.00    1.00    --  -36.29 132.00-167.00   88
  3  ω     20.00 104.00   1.00    1.00    --   36.29  57.00-180.00   84
  4  ω      1.00  75.00   1.00    1.00    --   36.29 -99.00 120.00   74
  5  ω     39.00 115.00   1.00    1.87    --  108.71-111.00   0.00   76
  6  ω     40.00 126.00   1.00    1.87    --  108.71 -45.00 150.00   86
  7  ω     91.00 177.00   1.00    1.87    --  108.71  45.00 -90.00   86
  8  ω     39.00 109.00   1.00    1.87    --  108.71 -94.00 150.00   70
  9  ω     39.00 115.00   1.00    1.87    --  108.71-111.00 -30.00   76
 10  ω     39.00 109.00   1.00    1.87    --  108.71 -94.00-120.00   70
 11  ω     91.00 166.00   1.00    1.87    --  108.71  45.00 150.00   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      0.1667673000
_diffrn_orient_matrix_UB_12      0.0082976000
_diffrn_orient_matrix_UB_13      -0.0283121000
_diffrn_orient_matrix_UB_21      -0.0670831000
_diffrn_orient_matrix_UB_22      0.0270278000
_diffrn_orient_matrix_UB_23      -0.0697416000
_diffrn_orient_matrix_UB_31      0.0027360000
_diffrn_orient_matrix_UB_32      0.1609917000
_diffrn_orient_matrix_UB_33      0.0129924000
_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         0.706
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2544
_reflns_number_total             2684
_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 1.171.38.46 (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         0.224
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1001 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.056
_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)+(0.0955P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1327
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005), C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00C,H00E), C00G(H00G,H00H), C00J(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00F), C00H(H00I), C00K(H00L),
 C00L(H00M), C00M(H00N), C00N(H00O), C00O(H00P)
;
_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 0.3704(3) 0.7645(2) 0.57765(11) 0.0299(5) Uani 1 1 d . . . . .
O002 O 0.5080(3) 0.8280(2) 0.46292(12) 0.0342(5) Uani 1 1 d . . . . .
O003 O 0.7234(3) 0.4421(2) 0.66266(12) 0.0376(6) Uani 1 1 d . . . . .
C004 C 0.4648(3) 0.7289(3) 0.62824(14) 0.0249(6) Uani 1 1 d . . . . .
C005 C 0.3802(3) 0.6531(3) 0.52837(14) 0.0233(6) Uani 1 1 d . . . . .
H005 H 0.2761 0.6135 0.5206 0.028 Uiso 1 1 calc R . . . .
C006 C 0.5394(3) 0.6046(3) 0.62079(14) 0.0228(6) Uani 1 1 d . . . . .
C007 C 0.4074(4) 0.3930(3) 0.56763(13) 0.0242(6) Uani 1 1 d . . . . .
C008 C 0.4431(3) 0.7143(3) 0.46408(15) 0.0239(6) Uani 1 1 d . . . . .
C009 C 0.4897(3) 0.5344(3) 0.55673(14) 0.0224(6) Uani 1 1 d . . . . .
H009 H 0.5801 0.5215 0.5276 0.027 Uiso 1 1 calc R . . . .
C00A C 0.3354(4) 0.5012(3) 0.40217(16) 0.0294(7) Uani 1 1 d . . . . .
H00A H 0.2813 0.4729 0.4399 0.035 Uiso 1 1 calc R . . . .
C00B C 0.5087(4) 0.6645(3) 0.34707(16) 0.0327(7) Uani 1 1 d . . . . .
H00B H 0.5698 0.7461 0.3478 0.039 Uiso 1 1 calc R . . . .
C00C C 0.4266(3) 0.6243(3) 0.40351(14) 0.0258(6) Uani 1 1 d . . . . .
C00D C 0.2632(4) 0.3882(3) 0.59860(15) 0.0308(7) Uani 1 1 d . . . . .
H00D H 0.2156 0.4721 0.6121 0.037 Uiso 1 1 calc R . . . .
C00E C 0.5365(4) 0.7396(3) 0.74558(16) 0.0363(7) Uani 1 1 d . . . . .
H00C H 0.5642 0.8047 0.7809 0.044 Uiso 1 1 calc R . . . .
H00E H 0.4548 0.6777 0.7620 0.044 Uiso 1 1 calc R . . . .
C00F C 0.4779(4) 0.2676(3) 0.54856(15) 0.0310(7) Uani 1 1 d . . . . .
H00F H 0.5755 0.2696 0.5284 0.037 Uiso 1 1 calc R . . . .
C00G C 0.4738(4) 0.8247(3) 0.68650(16) 0.0318(7) Uani 1 1 d . . . . .
H00G H 0.3712 0.8620 0.6967 0.038 Uiso 1 1 calc R . . . .
H00H H 0.5427 0.9037 0.6770 0.038 Uiso 1 1 calc R . . . .
C00H C 0.5000(4) 0.5839(4) 0.28995(16) 0.0421(8) Uani 1 1 d . . . . .
H00I H 0.5557 0.6106 0.2524 0.051 Uiso 1 1 calc R . . . .
C00I C 0.6516(3) 0.5532(3) 0.66869(15) 0.0259(6) Uani 1 1 d . . . . .
C00J C 0.6774(4) 0.6513(3) 0.72770(15) 0.0325(7) Uani 1 1 d . . . . .
H00J H 0.7067 0.5944 0.7658 0.039 Uiso 1 1 calc R . . . .
H00K H 0.7638 0.7143 0.7178 0.039 Uiso 1 1 calc R . . . .
C00K C 0.2611(5) 0.1349(3) 0.59006(17) 0.0438(9) Uani 1 1 d . . . . .
H00L H 0.2121 0.0485 0.5978 0.053 Uiso 1 1 calc R . . . .
C00L C 0.1897(4) 0.2602(4) 0.60964(17) 0.0424(9) Uani 1 1 d . . . . .
H00M H 0.0926 0.2578 0.6301 0.051 Uiso 1 1 calc R . . . .
C00M C 0.3256(4) 0.4207(3) 0.34433(18) 0.0390(8) Uani 1 1 d . . . . .
H00N H 0.2641 0.3395 0.3431 0.047 Uiso 1 1 calc R . . . .
C00N C 0.4078(5) 0.4627(4) 0.28895(17) 0.0455(10) Uani 1 1 d . . . . .
H00O H 0.4014 0.4091 0.2503 0.055 Uiso 1 1 calc R . . . .
C00O C 0.4035(5) 0.1382(3) 0.55933(17) 0.0407(8) Uani 1 1 d . . . . .
H00P H 0.4505 0.0541 0.5457 0.049 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 C004 1.345(4) . ?
O001 C005 1.448(3) . ?
O002 C008 1.207(3) . ?
O003 C00I 1.220(4) . ?
C004 C006 1.342(4) . ?
C004 C00G 1.484(4) . ?
C005 H005 0.9800 . ?
C005 C008 1.518(4) . ?
C005 C009 1.568(4) . ?
C006 C009 1.513(4) . ?
C006 C00I 1.447(4) . ?
C007 C009 1.524(4) . ?
C007 C00D 1.385(4) . ?
C007 C00F 1.381(4) . ?
C008 C00C 1.494(4) . ?
C009 H009 0.9800 . ?
C00A H00A 0.9300 . ?
C00A C00C 1.399(4) . ?
C00A C00M 1.394(5) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.391(4) . ?
C00B C00H 1.382(5) . ?
C00D H00D 0.9300 . ?
C00D C00L 1.379(4) . ?
C00E H00C 0.9700 . ?
C00E H00E 0.9700 . ?
C00E C00G 1.533(5) . ?
C00E C00J 1.511(5) . ?
C00F H00F 0.9300 . ?
C00F C00O 1.393(4) . ?
C00G H00G 0.9700 . ?
C00G H00H 0.9700 . ?
C00H H00I 0.9300 . ?
C00H C00N 1.388(6) . ?
C00I C00J 1.523(4) . ?
C00J H00J 0.9700 . ?
C00J H00K 0.9700 . ?
C00K H00L 0.9300 . ?
C00K C00L 1.386(6) . ?
C00K C00O 1.370(6) . ?
C00L H00M 0.9300 . ?
C00M H00N 0.9300 . ?
C00M C00N 1.379(5) . ?
C00N H00O 0.9300 . ?
C00O H00P 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
C004 O001 C005 107.8(2) . . ?
O001 C004 C00G 118.7(2) . . ?
C006 C004 O001 114.8(3) . . ?
C006 C004 C00G 126.4(3) . . ?
O001 C005 H005 109.4 . . ?
O001 C005 C008 109.3(2) . . ?
O001 C005 C009 107.5(2) . . ?
C008 C005 H005 109.4 . . ?
C008 C005 C009 111.7(2) . . ?
C009 C005 H005 109.4 . . ?
C004 C006 C009 110.0(2) . . ?
C004 C006 C00I 122.3(3) . . ?
C00I C006 C009 127.7(2) . . ?
C00D C007 C009 120.4(3) . . ?
C00F C007 C009 120.3(3) . . ?
C00F C007 C00D 119.2(3) . . ?
O002 C008 C005 121.2(3) . . ?
O002 C008 C00C 122.1(3) . . ?
C00C C008 C005 116.7(2) . . ?
C005 C009 H009 110.1 . . ?
C006 C009 C005 99.7(2) . . ?
C006 C009 C007 112.9(2) . . ?
C006 C009 H009 110.1 . . ?
C007 C009 C005 113.5(2) . . ?
C007 C009 H009 110.1 . . ?
C00C C00A H00A 120.0 . . ?
C00M C00A H00A 120.0 . . ?
C00M C00A C00C 120.1(3) . . ?
C00C C00B H00B 119.8 . . ?
C00H C00B H00B 119.8 . . ?
C00H C00B C00C 120.4(3) . . ?
C00A C00C C008 122.6(3) . . ?
C00B C00C C008 117.8(3) . . ?
C00B C00C C00A 119.5(3) . . ?
C007 C00D H00D 119.7 . . ?
C00L C00D C007 120.6(3) . . ?
C00L C00D H00D 119.7 . . ?
H00C C00E H00E 107.8 . . ?
C00G C00E H00C 109.1 . . ?
C00G C00E H00E 109.1 . . ?
C00J C00E H00C 109.1 . . ?
C00J C00E H00E 109.1 . . ?
C00J C00E C00G 112.5(3) . . ?
C007 C00F H00F 119.8 . . ?
C007 C00F C00O 120.3(3) . . ?
C00O C00F H00F 119.8 . . ?
C004 C00G C00E 108.4(2) . . ?
C004 C00G H00G 110.0 . . ?
C004 C00G H00H 110.0 . . ?
C00E C00G H00G 110.0 . . ?
C00E C00G H00H 110.0 . . ?
H00G C00G H00H 108.4 . . ?
C00B C00H H00I 120.2 . . ?
C00B C00H C00N 119.6(3) . . ?
C00N C00H H00I 120.2 . . ?
O003 C00I C006 123.8(3) . . ?
O003 C00I C00J 121.7(3) . . ?
C006 C00I C00J 114.5(2) . . ?
C00E C00J C00I 113.9(3) . . ?
C00E C00J H00J 108.8 . . ?
C00E C00J H00K 108.8 . . ?
C00I C00J H00J 108.8 . . ?
C00I C00J H00K 108.8 . . ?
H00J C00J H00K 107.7 . . ?
C00L C00K H00L 119.9 . . ?
C00O C00K H00L 119.9 . . ?
C00O C00K C00L 120.2(3) . . ?
C00D C00L C00K 119.8(3) . . ?
C00D C00L H00M 120.1 . . ?
C00K C00L H00M 120.1 . . ?
C00A C00M H00N 120.3 . . ?
C00N C00M C00A 119.4(3) . . ?
C00N C00M H00N 120.3 . . ?
C00H C00N H00O 119.5 . . ?
C00M C00N C00H 121.0(3) . . ?
C00M C00N H00O 119.5 . . ?
C00F C00O H00P 120.1 . . ?
C00K C00O C00F 119.9(3) . . ?
C00K C00O H00P 120.1 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-04-11
_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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.799
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_compound_source        EtOH
####################################################################### 
# 
# 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_mo_d1_0ma
_database_code_depnum_ccdc_archive 'CCDC 1897164'
loop_
_audit_author_name
_audit_author_address
'Xuefeng Li'
;Southwest Minzu University
China
;
_audit_update_record             
;
2019-04-11 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 N O3'
_chemical_formula_weight         303.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   8.6309(5)
_cell_length_b                   20.4650(11)
_cell_length_c                   8.3752(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.814(2)
_cell_angle_gamma                90
_cell_volume                     1474.10(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6011
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.17

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20225
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.636
_diffrn_reflns_theta_max         28.697
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3807
_reflns_number_gt                2439
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0686P)²+0.5805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3807
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1642
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.10607(19) 0.60102(7) 0.87433(19) 0.0371(4) Uani 1 1 d . . . . .
N1 N 0.1832(2) 0.65202(8) 0.8732(2) 0.0278(4) Uani 1 1 d . . . . .
O2 O 0.15734(18) 0.70027(7) 0.95381(18) 0.0341(4) Uani 1 1 d . . . . .
O3 O 0.41389(19) 0.54598(7) 0.7525(2) 0.0371(4) Uani 1 1 d . . . . .
C1 C 0.6517(3) 0.91464(10) 0.5625(3) 0.0315(5) Uani 1 1 d . . . . .
H1 H 0.680407 0.958204 0.539165 0.038 Uiso 1 1 calc R U . . .
C2 C 0.5178(3) 0.90285(9) 0.6429(3) 0.0298(5) Uani 1 1 d . . . . .
H6 H 0.456694 0.938555 0.673793 0.036 Uiso 1 1 calc R U . . .
C3 C 0.4749(2) 0.84024(9) 0.6769(2) 0.0250(4) Uani 1 1 d . . . . .
H7 H 0.383642 0.833076 0.730459 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5645(2) 0.78594(9) 0.6334(2) 0.0224(4) Uani 1 1 d . . . . .
C5 C 0.5250(2) 0.71920(9) 0.6660(2) 0.0228(4) Uani 1 1 d . . . . .
C6 C 0.3931(2) 0.70668(9) 0.7600(2) 0.0229(4) Uani 1 1 d . . . . .
H8 H 0.362684 0.742091 0.823671 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3096(2) 0.65200(9) 0.7682(2) 0.0238(4) Uani 1 1 d . . . . .
C8 C 0.3263(2) 0.58625(9) 0.6877(2) 0.0251(4) Uani 1 1 d . . . . .
C9 C 0.2365(2) 0.57394(9) 0.5330(2) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.2366(3) 0.51076(10) 0.4695(3) 0.0310(5) Uani 1 1 d . . . . .
H9 H 0.294891 0.477143 0.524886 0.037 Uiso 1 1 calc R U . . .
C11 C 0.1515(3) 0.49730(10) 0.3260(3) 0.0351(5) Uani 1 1 d . . . . .
H10 H 0.150601 0.454291 0.283240 0.042 Uiso 1 1 calc R U . . .
C12 C 0.0676(3) 0.54638(11) 0.2445(3) 0.0342(5) Uani 1 1 d . . . . .
H2 H 0.008920 0.536809 0.146168 0.041 Uiso 1 1 calc R U . . .
C13 C 0.7405(3) 0.86374(10) 0.5179(2) 0.0293(5) Uani 1 1 d . . . . .
H3 H 0.830922 0.872176 0.463917 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6992(2) 0.79828(9) 0.5512(2) 0.0242(4) Uani 1 1 d . . . . .
C15 C 0.7894(2) 0.74528(10) 0.5025(2) 0.0291(5) Uani 1 1 d . . . . .
H4 H 0.879339 0.753575 0.447565 0.035 Uiso 1 1 calc R U . . .
C16 C 0.7487(3) 0.68227(10) 0.5336(3) 0.0308(5) Uani 1 1 d . . . . .
H5 H 0.809544 0.647156 0.498882 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6180(2) 0.66926(10) 0.6164(2) 0.0276(4) Uani 1 1 d . . . . .
H13 H 0.592397 0.625255 0.638958 0.033 Uiso 1 1 calc R U . . .
C19 C 0.0686(3) 0.60950(10) 0.3053(3) 0.0313(5) Uani 1 1 d . . . . .
H12 H 0.012316 0.643160 0.247895 0.038 Uiso 1 1 calc R U . . .
C20 C 0.1519(2) 0.62326(9) 0.4501(2) 0.0255(4) Uani 1 1 d . . . . .
H11 H 0.151504 0.666235 0.492966 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.239(2) . ?
N1 O2 1.227(2) . ?
N1 C7 1.457(2) . ?
O3 C8 1.215(2) . ?
C1 C13 1.364(3) . ?
C1 C2 1.406(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(3) . ?
C2 H6 0.9500 . ?
C3 C4 1.419(3) . ?
C3 H7 0.9500 . ?
C4 C14 1.423(3) . ?
C4 C5 1.440(3) . ?
C5 C17 1.385(3) . ?
C5 C6 1.459(3) . ?
C6 C7 1.336(3) . ?
C6 H8 0.9500 . ?
C7 C8 1.518(3) . ?
C8 C9 1.474(3) . ?
C9 C20 1.396(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.383(3) . ?
C10 H9 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H10 0.9500 . ?
C12 C19 1.388(3) . ?
C12 H2 0.9500 . ?
C13 C14 1.420(3) . ?
C13 H3 0.9500 . ?
C14 C15 1.415(3) . ?
C15 C16 1.367(3) . ?
C15 H4 0.9500 . ?
C16 C17 1.399(3) . ?
C16 H5 0.9500 . ?
C17 H13 0.9500 . ?
C19 C20 1.386(3) . ?
C19 H12 0.9500 . ?
C20 H11 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
O2 N1 O1 123.43(17) . . ?
O2 N1 C7 120.82(16) . . ?
O1 N1 C7 115.75(16) . . ?
C13 C1 C2 120.22(18) . . ?
C13 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.49(19) . . ?
C3 C2 H6 119.8 . . ?
C1 C2 H6 119.8 . . ?
C2 C3 C4 121.07(19) . . ?
C2 C3 H7 119.5 . . ?
C4 C3 H7 119.5 . . ?
C3 C4 C14 118.07(17) . . ?
C3 C4 C5 123.45(17) . . ?
C14 C4 C5 118.47(17) . . ?
C17 C5 C4 119.37(17) . . ?
C17 C5 C6 122.02(17) . . ?
C4 C5 C6 118.49(16) . . ?
C7 C6 C5 128.58(17) . . ?
C7 C6 H8 115.7 . . ?
C5 C6 H8 115.7 . . ?
C6 C7 N1 117.74(17) . . ?
C6 C7 C8 130.36(18) . . ?
N1 C7 C8 111.87(15) . . ?
O3 C8 C9 122.56(18) . . ?
O3 C8 C7 118.78(18) . . ?
C9 C8 C7 118.66(17) . . ?
C20 C9 C10 119.75(19) . . ?
C20 C9 C8 121.87(17) . . ?
C10 C9 C8 118.38(18) . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H9 120.1 . . ?
C9 C10 H9 120.1 . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H10 119.9 . . ?
C12 C11 H10 119.9 . . ?
C11 C12 C19 120.5(2) . . ?
C11 C12 H2 119.8 . . ?
C19 C12 H2 119.8 . . ?
C1 C13 C14 120.72(19) . . ?
C1 C13 H3 119.6 . . ?
C14 C13 H3 119.6 . . ?
C15 C14 C13 120.89(18) . . ?
C15 C14 C4 119.69(17) . . ?
C13 C14 C4 119.42(18) . . ?
C16 C15 C14 120.76(18) . . ?
C16 C15 H4 119.6 . . ?
C14 C15 H4 119.6 . . ?
C15 C16 C17 120.34(19) . . ?
C15 C16 H5 119.8 . . ?
C17 C16 H5 119.8 . . ?
C5 C17 C16 121.36(18) . . ?
C5 C17 H13 119.3 . . ?
C16 C17 H13 119.3 . . ?
C20 C19 C12 119.8(2) . . ?
C20 C19 H12 120.1 . . ?
C12 C19 H12 120.1 . . ?
C19 C20 C9 119.99(18) . . ?
C19 C20 H11 120.0 . . ?
C9 C20 H11 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C14 -0.9(3) . . . . ?
C2 C3 C4 C5 -179.97(19) . . . . ?
C3 C4 C5 C17 178.78(19) . . . . ?
C14 C4 C5 C17 -0.3(3) . . . . ?
C3 C4 C5 C6 -5.1(3) . . . . ?
C14 C4 C5 C6 175.83(17) . . . . ?
C17 C5 C6 C7 -24.3(3) . . . . ?
C4 C5 C6 C7 159.7(2) . . . . ?
C5 C6 C7 N1 179.54(18) . . . . ?
C5 C6 C7 C8 1.5(4) . . . . ?
O2 N1 C7 C6 -1.7(3) . . . . ?
O1 N1 C7 C6 178.19(18) . . . . ?
O2 N1 C7 C8 176.70(17) . . . . ?
O1 N1 C7 C8 -3.4(2) . . . . ?
C6 C7 C8 O3 86.7(3) . . . . ?
N1 C7 C8 O3 -91.4(2) . . . . ?
C6 C7 C8 C9 -92.8(3) . . . . ?
N1 C7 C8 C9 89.1(2) . . . . ?
O3 C8 C9 C20 -171.7(2) . . . . ?
C7 C8 C9 C20 7.8(3) . . . . ?
O3 C8 C9 C10 8.7(3) . . . . ?
C7 C8 C9 C10 -171.84(18) . . . . ?
C20 C9 C10 C11 -0.7(3) . . . . ?
C8 C9 C10 C11 178.94(19) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C19 0.3(3) . . . . ?
C2 C1 C13 C14 0.2(3) . . . . ?
C1 C13 C14 C15 178.8(2) . . . . ?
C1 C13 C14 C4 -0.6(3) . . . . ?
C3 C4 C14 C15 -178.48(18) . . . . ?
C5 C4 C14 C15 0.6(3) . . . . ?
C3 C4 C14 C13 0.9(3) . . . . ?
C5 C4 C14 C13 -179.96(18) . . . . ?
C13 C14 C15 C16 -179.5(2) . . . . ?
C4 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C4 C5 C17 C16 -0.7(3) . . . . ?
C6 C5 C17 C16 -176.6(2) . . . . ?
C15 C16 C17 C5 1.3(3) . . . . ?
C11 C12 C19 C20 -1.1(3) . . . . ?
C12 C19 C20 C9 1.0(3) . . . . ?
C10 C9 C20 C19 -0.1(3) . . . . ?
C8 C9 C20 C19 -179.75(18) . . . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.067


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc/petroleum ether'
