# 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_yxh
_database_code_depnum_ccdc_archive 'CCDC 1919097'
loop_
_audit_author_name
_audit_author_address
'Xinhe Yang'
;Henan Normal University
China
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O5'
_chemical_formula_sum            'C20 H17 N O5'
_chemical_formula_weight         351.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   9.08830(10)
_cell_length_b                   9.08830(10)
_cell_length_c                   41.3484(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3415.26(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15073
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2190
_cell_measurement_theta_min      2.1070
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            22632
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.747
_diffrn_reflns_theta_min         4.277
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 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   -115.00 -17.00   1.00    1.00    --  -41.11 -38.00 -90.00   98
  2  ω   -114.00 -60.00   1.00    1.00    --  -41.11-146.00 107.00   54
  3  ω    -66.00  33.00   1.00    1.00    --  -41.11  38.00   0.00   99
  4  ω     23.00  97.00   1.00    1.00    --   41.11-125.00 -90.00   74
  5  ω     25.00 109.00   1.00    1.00    --  106.95 -95.00-180.00   84
  6  ω     31.00 135.00   1.00    1.00    --  106.95 -30.00 150.00  104
  7  ω     79.00 178.00   1.00    1.00    --  106.95  30.00 120.00   99
  8  ω     31.00 140.00   1.00    1.00    --  106.95 -77.00-150.00  109
  9  ω     94.00 178.00   1.00    1.00    --  106.95 125.00-180.00   84
 10  ω     25.00 160.00   1.00    1.00    --  106.95 -15.00  30.00  135
 11  ω   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00 150.00  108
 12  ω   -115.00 -17.00   1.00    1.00    --  -41.11 -38.00-180.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1251312000
_diffrn_orient_matrix_UB_12      -0.0114687000
_diffrn_orient_matrix_UB_13      0.0250225000
_diffrn_orient_matrix_UB_21      -0.1144815000
_diffrn_orient_matrix_UB_22      0.0064270000
_diffrn_orient_matrix_UB_23      -0.0274755000
_diffrn_orient_matrix_UB_31      0.0041881000
_diffrn_orient_matrix_UB_32      -0.1688306000
_diffrn_orient_matrix_UB_33      -0.0027832000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3364
_reflns_number_total             3424
_reflns_odcompleteness_completeness 99.95
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.796
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 
;
 Flack x determined using 1258 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       0.0030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0768
_refine_ls_restrained_S_all      1.087
_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)+(0.1246P)²+4.3748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2148
_refine_ls_wR_factor_ref         0.2155
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O5, C12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O5 \\sim C12: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C2(H2), C17(H17), C18(H18), C14(H14), C11(H11),
 C15(H15)
4.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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
O1 O 0.3683(3) 0.7838(3) 0.42920(6) 0.0270(7) Uani 1 1 d . . . . .
O2 O 0.1553(4) 0.9746(4) 0.43020(8) 0.0368(8) Uani 1 1 d . . . . .
O3 O 0.2237(5) 1.0583(4) 0.47660(8) 0.0487(10) Uani 1 1 d . . . . .
N1 N 0.2273(4) 0.9685(4) 0.45496(8) 0.0272(8) Uani 1 1 d . . . . .
O5 O 0.6817(6) 0.8766(7) 0.52664(11) 0.0758(16) Uani 1 1 d . U . . .
C6 C 0.3075(5) 0.6461(5) 0.42497(9) 0.0262(9) Uani 1 1 d . . . . .
C5 C 0.3209(5) 0.5652(5) 0.39681(9) 0.0271(9) Uani 1 1 d . . . . .
H5 H 0.372168 0.601199 0.379018 0.032 Uiso 1 1 calc R . . . .
C1 C 0.2336(5) 0.5943(5) 0.45190(9) 0.0287(9) Uani 1 1 d . . . . .
C7 C 0.3269(5) 0.8340(5) 0.46034(9) 0.0267(9) Uani 1 1 d . . . . .
C4 C 0.2539(5) 0.4272(5) 0.39631(10) 0.0296(9) Uani 1 1 d . . . . .
H4 H 0.259393 0.369923 0.377706 0.036 Uiso 1 1 calc R . . . .
C3 C 0.1792(5) 0.3738(5) 0.42316(10) 0.0319(10) Uani 1 1 d . . . . .
H3 H 0.135225 0.281467 0.422282 0.038 Uiso 1 1 calc R . . . .
C2 C 0.1694(6) 0.4571(5) 0.45150(10) 0.0318(9) Uani 1 1 d . . . . .
H2 H 0.120865 0.420792 0.469611 0.038 Uiso 1 1 calc R . . . .
C17 C 0.1114(6) 0.8017(5) 0.57986(10) 0.0327(10) Uani 1 1 d . . . . .
H17 H 0.070220 0.888965 0.587327 0.039 Uiso 1 1 calc R . . . .
O4 O 0.5963(5) 0.6736(8) 0.54877(10) 0.090(2) Uani 1 1 d . . . . .
C18 C 0.1930(6) 0.8024(5) 0.55134(10) 0.0361(11) Uani 1 1 d . . . . .
H18 H 0.205350 0.889618 0.539896 0.043 Uiso 1 1 calc R . . . .
C14 C 0.2385(6) 0.5449(5) 0.55764(10) 0.0378(11) Uani 1 1 d . . . . .
H14 H 0.282273 0.458136 0.550566 0.045 Uiso 1 1 calc R . . . .
C8 C 0.2432(5) 0.7100(5) 0.47822(9) 0.0293(10) Uani 1 1 d . . . . .
H8 H 0.145073 0.742817 0.484869 0.035 Uiso 1 1 calc R . . . .
C11 C 0.4551(5) 0.8723(5) 0.48094(10) 0.0325(10) Uani 1 1 d . . . . .
H11 H 0.520364 0.948894 0.476900 0.039 Uiso 1 1 calc R . . . .
C10 C 0.4628(6) 0.7813(6) 0.50595(10) 0.0393(12) Uani 1 1 d . . . . .
C13 C 0.2559(6) 0.6728(5) 0.53995(9) 0.0346(11) Uani 1 1 d . . . . .
C9 C 0.3393(7) 0.6704(5) 0.50806(10) 0.0384(12) Uani 1 1 d . . . . .
H9 H 0.380377 0.571734 0.504876 0.046 Uiso 1 1 calc R . . . .
C16 C 0.0904(5) 0.6727(6) 0.59737(11) 0.0374(11) Uani 1 1 d . . . . .
C15 C 0.1563(6) 0.5453(6) 0.58583(12) 0.0415(12) Uani 1 1 d . . . . .
H15 H 0.145021 0.458088 0.597325 0.050 Uiso 1 1 calc R . . . .
C19 C -0.0067(9) 0.6698(9) 0.62716(17) 0.074(2) Uani 1 1 d . . . . .
H19A H 0.017389 0.751642 0.640858 0.111 Uiso 1 1 calc GR . . . .
H19B H 0.008986 0.579625 0.638733 0.111 Uiso 1 1 calc GR . . . .
H19C H -0.108047 0.676423 0.620759 0.111 Uiso 1 1 calc GR . . . .
C12 C 0.5839(9) 0.7703(10) 0.52905(15) 0.0734(17) Uani 1 1 d . U . . .
C20 C 0.7983(10) 0.8533(12) 0.5492(3) 0.112(4) Uani 1 1 d . . . . .
H20A H 0.887975 0.833838 0.537724 0.168 Uiso 1 1 calc GR . . . .
H20B H 0.774942 0.770747 0.562782 0.168 Uiso 1 1 calc GR . . . .
H20C H 0.810382 0.939550 0.562356 0.168 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.379(5) . ?
O1 C7 1.417(4) . ?
O2 N1 1.217(5) . ?
O3 N1 1.211(5) . ?
N1 C7 1.537(5) . ?
O5 C12 1.316(11) . ?
O5 C20 1.429(10) . ?
C6 C5 1.383(5) . ?
C6 C1 1.383(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.395(6) . ?
C1 C2 1.377(7) . ?
C1 C8 1.516(5) . ?
C7 C8 1.548(6) . ?
C7 C11 1.484(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.389(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.398(6) . ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.393(6) . ?
C17 C16 1.391(7) . ?
O4 C12 1.205(10) . ?
C18 H18 0.9300 . ?
C18 C13 1.391(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.383(6) . ?
C14 C15 1.385(7) . ?
C8 H8 0.9800 . ?
C8 C9 1.554(6) . ?
C11 H11 0.9300 . ?
C11 C10 1.326(7) . ?
C10 C9 1.511(9) . ?
C10 C12 1.461(7) . ?
C13 C9 1.521(6) . ?
C9 H9 0.9800 . ?
C16 C15 1.388(8) . ?
C16 C19 1.515(7) . ?
C15 H15 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C7 107.5(3) . . ?
O2 N1 C7 118.3(3) . . ?
O3 N1 O2 125.2(4) . . ?
O3 N1 C7 116.4(3) . . ?
C12 O5 C20 110.0(7) . . ?
O1 C6 C5 123.6(4) . . ?
O1 C6 C1 113.6(3) . . ?
C5 C6 C1 122.7(4) . . ?
C6 C5 H5 121.6 . . ?
C6 C5 C4 116.9(4) . . ?
C4 C5 H5 121.6 . . ?
C6 C1 C8 108.3(4) . . ?
C2 C1 C6 120.3(4) . . ?
C2 C1 C8 131.4(4) . . ?
O1 C7 N1 106.3(3) . . ?
O1 C7 C8 109.3(3) . . ?
O1 C7 C11 112.9(4) . . ?
N1 C7 C8 111.0(4) . . ?
C11 C7 N1 111.0(3) . . ?
C11 C7 C8 106.4(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4 119.5 . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.8(4) . . ?
C2 C3 H3 119.6 . . ?
C1 C2 C3 118.3(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.2(4) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 C17 120.1(4) . . ?
C13 C18 H18 120.0 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(5) . . ?
C15 C14 H14 119.9 . . ?
C1 C8 C7 101.0(3) . . ?
C1 C8 H8 111.1 . . ?
C1 C8 C9 116.2(3) . . ?
C7 C8 H8 111.1 . . ?
C7 C8 C9 105.8(4) . . ?
C9 C8 H8 111.1 . . ?
C7 C11 H11 125.0 . . ?
C10 C11 C7 110.1(5) . . ?
C10 C11 H11 125.0 . . ?
C11 C10 C9 114.9(4) . . ?
C11 C10 C12 126.3(7) . . ?
C12 C10 C9 118.5(6) . . ?
C18 C13 C9 120.7(4) . . ?
C14 C13 C18 119.1(4) . . ?
C14 C13 C9 120.2(4) . . ?
C8 C9 H9 108.6 . . ?
C10 C9 C8 102.5(4) . . ?
C10 C9 C13 114.2(4) . . ?
C10 C9 H9 108.6 . . ?
C13 C9 C8 113.9(4) . . ?
C13 C9 H9 108.6 . . ?
C17 C16 C19 121.2(5) . . ?
C15 C16 C17 117.7(4) . . ?
C15 C16 C19 121.1(5) . . ?
C14 C15 C16 121.6(5) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C12 C10 114.2(7) . . ?
O4 C12 O5 121.6(6) . . ?
O4 C12 C10 124.3(9) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.711
####################################################################### 
# 
# 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_yxh-2-20181211
_database_code_depnum_ccdc_archive 'CCDC 1919105'
loop_
_audit_author_name
_audit_author_address
'Xinhe Yang'
;Henan Normal University
China
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O5'
_chemical_formula_sum            'C16 H17 N O5'
_chemical_formula_weight         303.30
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   6.23380(10)
_cell_length_b                   11.66010(10)
_cell_length_c                   21.6605(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1574.43(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9143
_cell_measurement_temperature    286(4)
_cell_measurement_theta_max      70.8120
_cell_measurement_theta_min      5.5550
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.751
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54590
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15520
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.249
_diffrn_reflns_theta_min         4.082
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      286(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -16.00   1.00    1.24    --  -35.37 -38.00 120.00   89
  2  ω     23.00  89.00   1.00    1.24    --   35.37-125.00 -30.00   66
  3  ω      1.00  74.00   1.00    1.24    --   35.37 -99.00   0.00   73
  4  ω      9.00 103.00   1.00    1.24    --   35.37  77.00  60.00   94
  5  ω     85.00 176.00   1.00    4.96    --  106.50  30.00  60.00   91
  6  ω     37.00 109.00   1.00    4.96    --  106.50 -95.00 150.00   72
  7  ω     37.00 109.00   1.00    4.96    --  106.50 -95.00  30.00   72
  8  ω    100.00 176.00   1.00    4.96    --  106.50 111.00-150.00   76
  9  ω     57.00 151.00   1.00    4.96    --  106.50 178.00 120.00   94
 10  ω    -58.00  35.00   1.00    1.24    --  -35.37  29.00 101.00   93
 11  ω      9.00 103.00   1.00    1.24    --   35.37  77.00   0.00   94
 12  ω    -32.00  52.00   1.00    1.24    --   35.37 -57.00 150.00   84
 13  ω     19.00 103.00   1.00    1.24    --   35.37  57.00 -60.00   84
 14  ω     89.00 175.00   1.00    4.96    --  106.50  45.00 120.00   86
 15  ω     40.00 125.00   1.00    4.96    --  106.50 -61.00-180.00   85
 16  ω     85.00 176.00   1.00    4.96    --  106.50  30.00 -30.00   91
 17  ω     68.00 178.00   1.00    4.96    --  106.50  15.00-120.00  110
 18  ω    -54.00  34.00   1.00    1.24    --  -35.37  38.00 -60.00   88
 19  ω     23.00  89.00   1.00    1.24    --   35.37-125.00 150.00   66
 20  ω      9.00 103.00   1.00    1.24    --   35.37  77.00 150.00   94
 21  ω     19.00 103.00   1.00    1.24    --   35.37  57.00-120.00   84
 22  ω     88.00 173.00   1.00    4.96    --  106.50  61.00   0.00   85
 23  ω     89.00 175.00   1.00    4.96    --  106.50  45.00 150.00   86
 24  ω     88.00 173.00   1.00    4.96    --  106.50  61.00 -90.00   85
 25  ω     84.00 177.00   1.00    4.96    --  106.50  29.00 101.00   93
 26  ω      9.00  82.00   1.00    1.24    --   35.37  77.00 -30.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, 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      -0.0853290000
_diffrn_orient_matrix_UB_12      -0.1226040000
_diffrn_orient_matrix_UB_13      0.0100724000
_diffrn_orient_matrix_UB_21      -0.0326700000
_diffrn_orient_matrix_UB_22      -0.0133964000
_diffrn_orient_matrix_UB_23      -0.0701307000
_diffrn_orient_matrix_UB_31      0.2295886000
_diffrn_orient_matrix_UB_32      -0.0474182000
_diffrn_orient_matrix_UB_33      -0.0062433000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                2821
_reflns_number_total             3000
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 1069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_coef       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.070
_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)+(0.0433P)²+0.1903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0892
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00B,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I)
2.d Idealised Me refined as rotating group:
 C00K(H00E,H00J,H00K), C00L(H00L,H00M,H00N), C00M(H00O,H00P,H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.8986(2) 0.44316(12) 0.50709(7) 0.0475(4) Uani 1 1 d . . . . .
O002 O 0.3009(3) 0.46227(17) 0.69928(8) 0.0647(5) Uani 1 1 d . . . . .
O003 O 0.6407(3) 0.41200(18) 0.72051(7) 0.0677(5) Uani 1 1 d . . . . .
N004 N 0.9197(3) 0.63938(15) 0.53175(9) 0.0489(4) Uani 1 1 d . . . . .
O005 O 0.9213(4) 0.70715(15) 0.57357(9) 0.0738(6) Uani 1 1 d . . . . .
O006 O 1.0069(4) 0.65472(18) 0.48303(10) 0.0909(8) Uani 1 1 d . . . . .
C007 C 0.5689(3) 0.49070(17) 0.62450(9) 0.0410(4) Uani 1 1 d . . . . .
C008 C 0.4865(3) 0.45439(18) 0.68586(9) 0.0429(5) Uani 1 1 d . . . . .
C009 C 0.5526(3) 0.44941(17) 0.46985(9) 0.0411(4) Uani 1 1 d . . . . .
C00A C 0.5590(3) 0.54323(16) 0.51747(8) 0.0385(4) Uani 1 1 d . . . . .
H00A H 0.537167 0.618880 0.498787 0.046 Uiso 1 1 calc R . . . .
C00B C 0.7500(3) 0.39653(17) 0.46682(9) 0.0425(5) Uani 1 1 d . . . . .
C00C C 0.7921(3) 0.52849(16) 0.54141(9) 0.0396(4) Uani 1 1 d . . . . .
C00D C 0.7728(4) 0.49819(17) 0.60821(9) 0.0428(5) Uani 1 1 d . . . . .
H00D H 0.888231 0.486258 0.634650 0.051 Uiso 1 1 calc R . . . .
C00E C 0.4147(3) 0.52593(19) 0.57444(9) 0.0433(5) Uani 1 1 d . . . . .
H00B H 0.341376 0.596477 0.585273 0.052 Uiso 1 1 calc R . . . .
H00C H 0.308954 0.466499 0.567032 0.052 Uiso 1 1 calc R . . . .
C00F C 0.7931(5) 0.30597(19) 0.42782(12) 0.0576(6) Uani 1 1 d . . . . .
H00F H 0.926491 0.270320 0.427226 0.069 Uiso 1 1 calc R . . . .
C00G C 0.3897(4) 0.4124(2) 0.43192(10) 0.0567(6) Uani 1 1 d . . . . .
H00G H 0.255371 0.447061 0.433257 0.068 Uiso 1 1 calc R . . . .
C00H C 0.4299(5) 0.3224(3) 0.39157(12) 0.0690(8) Uani 1 1 d . . . . .
H00H H 0.321544 0.296615 0.365515 0.083 Uiso 1 1 calc R . . . .
C00I C 0.6286(5) 0.2709(2) 0.38980(13) 0.0686(8) Uani 1 1 d . . . . .
H00I H 0.652294 0.211089 0.362259 0.082 Uiso 1 1 calc R . . . .
C00J C 0.6041(5) 0.3697(3) 0.78406(11) 0.0699(7) Uani 1 1 d . . . . .
C00K C 0.4555(8) 0.2691(3) 0.78150(18) 0.1054(13) Uani 1 1 d . . . . .
H00E H 0.316023 0.294196 0.768460 0.158 Uiso 1 1 calc GR . . . .
H00J H 0.445319 0.234911 0.821705 0.158 Uiso 1 1 calc GR . . . .
H00K H 0.509866 0.213709 0.752692 0.158 Uiso 1 1 calc GR . . . .
C00L C 0.5111(10) 0.4638(3) 0.82280(13) 0.1297(19) Uani 1 1 d . . . . .
H00L H 0.599700 0.530847 0.819577 0.195 Uiso 1 1 calc GR . . . .
H00M H 0.504925 0.439426 0.865098 0.195 Uiso 1 1 calc GR . . . .
H00N H 0.369030 0.481374 0.808542 0.195 Uiso 1 1 calc GR . . . .
C00M C 0.8241(8) 0.3358(6) 0.8040(2) 0.178(3) Uani 1 1 d . . . . .
H00O H 0.876284 0.275648 0.777690 0.267 Uiso 1 1 calc GR . . . .
H00P H 0.819786 0.309092 0.845878 0.267 Uiso 1 1 calc GR . . . .
H00Q H 0.918027 0.400851 0.801169 0.267 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00B 1.384(3) . ?
O001 C00C 1.408(2) . ?
O002 C008 1.197(3) . ?
O003 C008 1.316(3) . ?
O003 C00J 1.480(3) . ?
N004 O005 1.202(2) . ?
N004 O006 1.201(3) . ?
N004 C00C 1.532(2) . ?
C007 C008 1.486(3) . ?
C007 C00D 1.322(3) . ?
C007 C00E 1.506(3) . ?
C009 C00A 1.504(3) . ?
C009 C00B 1.378(3) . ?
C009 C00G 1.376(3) . ?
C00A H00A 0.9800 . ?
C00A C00C 1.552(3) . ?
C00A C00E 1.540(3) . ?
C00B C00F 1.379(3) . ?
C00C C00D 1.494(3) . ?
C00D H00D 0.9300 . ?
C00E H00B 0.9700 . ?
C00E H00C 0.9700 . ?
C00F H00F 0.9300 . ?
C00F C00I 1.377(4) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.389(3) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.377(5) . ?
C00I H00I 0.9300 . ?
C00J C00K 1.495(5) . ?
C00J C00L 1.498(5) . ?
C00J C00M 1.491(5) . ?
C00K H00E 0.9600 . ?
C00K H00J 0.9600 . ?
C00K H00K 0.9600 . ?
C00L H00L 0.9600 . ?
C00L H00M 0.9600 . ?
C00L H00N 0.9600 . ?
C00M H00O 0.9600 . ?
C00M H00P 0.9600 . ?
C00M H00Q 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00B O001 C00C 107.15(15) . . ?
C008 O003 C00J 122.9(2) . . ?
O005 N004 C00C 117.15(18) . . ?
O006 N004 O005 124.1(2) . . ?
O006 N004 C00C 118.74(18) . . ?
C008 C007 C00E 120.09(18) . . ?
C00D C007 C008 126.11(19) . . ?
C00D C007 C00E 113.78(18) . . ?
O002 C008 O003 126.6(2) . . ?
O002 C008 C007 122.0(2) . . ?
O003 C008 C007 111.39(18) . . ?
C00B C009 C00A 109.55(18) . . ?
C00G C009 C00A 131.1(2) . . ?
C00G C009 C00B 119.4(2) . . ?
C009 C00A H00A 111.6 . . ?
C009 C00A C00C 99.98(15) . . ?
C009 C00A C00E 116.02(16) . . ?
C00C C00A H00A 111.6 . . ?
C00E C00A H00A 111.6 . . ?
C00E C00A C00C 105.34(15) . . ?
C009 C00B O001 113.07(17) . . ?
C009 C00B C00F 123.1(2) . . ?
C00F C00B O001 123.8(2) . . ?
O001 C00C N004 106.23(15) . . ?
O001 C00C C00A 110.07(16) . . ?
O001 C00C C00D 112.46(16) . . ?
N004 C00C C00A 110.29(15) . . ?
C00D C00C N004 111.93(17) . . ?
C00D C00C C00A 105.92(16) . . ?
C007 C00D C00C 110.57(18) . . ?
C007 C00D H00D 124.7 . . ?
C00C C00D H00D 124.7 . . ?
C007 C00E C00A 103.89(16) . . ?
C007 C00E H00B 111.0 . . ?
C007 C00E H00C 111.0 . . ?
C00A C00E H00B 111.0 . . ?
C00A C00E H00C 111.0 . . ?
H00B C00E H00C 109.0 . . ?
C00B C00F H00F 121.7 . . ?
C00I C00F C00B 116.6(2) . . ?
C00I C00F H00F 121.7 . . ?
C009 C00G H00G 120.7 . . ?
C009 C00G C00H 118.7(3) . . ?
C00H C00G H00G 120.7 . . ?
C00G C00H H00H 119.7 . . ?
C00I C00H C00G 120.6(3) . . ?
C00I C00H H00H 119.7 . . ?
C00F C00I H00I 119.2 . . ?
C00H C00I C00F 121.6(2) . . ?
C00H C00I H00I 119.2 . . ?
O003 C00J C00K 108.8(2) . . ?
O003 C00J C00L 109.6(2) . . ?
O003 C00J C00M 102.4(3) . . ?
C00K C00J C00L 110.8(3) . . ?
C00M C00J C00K 111.9(4) . . ?
C00M C00J C00L 112.8(4) . . ?
C00J C00K H00E 109.5 . . ?
C00J C00K H00J 109.5 . . ?
C00J C00K H00K 109.5 . . ?
H00E C00K H00J 109.5 . . ?
H00E C00K H00K 109.5 . . ?
H00J C00K H00K 109.5 . . ?
C00J C00L H00L 109.5 . . ?
C00J C00L H00M 109.5 . . ?
C00J C00L H00N 109.5 . . ?
H00L C00L H00M 109.5 . . ?
H00L C00L H00N 109.5 . . ?
H00M C00L H00N 109.5 . . ?
C00J C00M H00O 109.5 . . ?
C00J C00M H00P 109.5 . . ?
C00J C00M H00Q 109.5 . . ?
H00O C00M H00P 109.5 . . ?
H00O C00M H00Q 109.5 . . ?
H00P C00M H00Q 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.551
