# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_SAY1535-1
_database_code_depnum_ccdc_archive 'CCDC 1940271'
loop_
_audit_author_name
_audit_author_address
'Masafumi Hirano'
;Tokyo University of Agriculture and Technology
Japan
;
_audit_update_record             
;
2019-07-13 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H19 N O5'
_chemical_formula_moiety         'C21 H19 N O5'
_chemical_formula_weight         365.38
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.192(4)
_cell_length_b                   13.350(7)
_cell_length_c                   19.898(11)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.983(7)
_cell_angle_gamma                90.0000
_cell_volume                     1907.9(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3065
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.28
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            paleYellow
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.074
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768.00
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.993

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            15044
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         3.052
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4340
_reflns_number_gt                1896
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1447
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1810
_refine_ls_wR_factor_gt          0.1377
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4340
_refine_ls_number_parameters     244
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0891P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.7751(3) -0.13688(16) 0.54331(10) 0.1068(7) Uani 1 1 d . . . . .
O2 O -0.8328(3) -0.21258(13) 0.63967(10) 0.0900(6) Uani 1 1 d . . . . .
O3 O 0.1059(3) 0.05395(13) 0.92936(9) 0.0941(6) Uani 1 1 d . . . . .
O4 O 0.8506(3) 0.37857(16) 0.70400(12) 0.1080(7) Uani 1 1 d . . . . .
O5 O 0.8833(3) 0.37423(17) 0.59736(12) 0.1183(8) Uani 1 1 d . . . . .
N1 N 0.7951(3) 0.35654(16) 0.64701(14) 0.0809(6) Uani 1 1 d . . . . .
C1 C -0.7304(4) -0.15566(18) 0.60092(14) 0.0689(7) Uani 1 1 d . . . . .
C2 C -0.5628(4) -0.12028(17) 0.63809(12) 0.0659(6) Uani 1 1 d . . . . .
H2 H -0.536983 -0.143019 0.681758 0.079 Uiso 1 1 calc R U . . .
C3 C -0.4464(4) -0.05658(16) 0.61118(12) 0.0704(7) Uani 1 1 d . . . . .
H3 H -0.471627 -0.037863 0.566616 0.084 Uiso 1 1 calc R U . . .
C4 C -0.2846(4) -0.01429(17) 0.64554(12) 0.0712(7) Uani 1 1 d . . . . .
H4 H -0.260832 -0.030691 0.690593 0.085 Uiso 1 1 calc R U . . .
C5 C -0.1652(4) 0.04762(17) 0.61648(12) 0.0740(7) Uani 1 1 d . . . . .
H5 H -0.190749 0.061428 0.571132 0.089 Uiso 1 1 calc R U . . .
C6 C -0.0011(4) 0.09546(17) 0.64750(12) 0.0676(7) Uani 1 1 d . . . . .
C7 C 0.1136(4) 0.14360(17) 0.60623(13) 0.0723(7) Uani 1 1 d . . . . .
H7 H 0.075760 0.140331 0.560868 0.087 Uiso 1 1 calc R U . . .
C8 C -1.0004(5) -0.2534(2) 0.60892(19) 0.1167(11) Uani 1 1 d . . . . .
H8A H -1.062579 -0.292825 0.641268 0.140 Uiso 1 1 calc R U . . .
H8B H -1.080562 -0.199797 0.593290 0.140 Uiso 1 1 calc R U . . .
H8C H -0.970599 -0.294833 0.571563 0.140 Uiso 1 1 calc R U . . .
C9 C 0.0324(3) 0.08479(15) 0.72176(12) 0.0615(6) Uani 1 1 d . . . . .
C10 C -0.0937(4) 0.12129(17) 0.76623(13) 0.0726(7) Uani 1 1 d . . . . .
H10 H -0.200577 0.153904 0.749475 0.087 Uiso 1 1 calc R U . . .
C11 C -0.0637(4) 0.11014(18) 0.83418(13) 0.0784(8) Uani 1 1 d . . . . .
H11 H -0.149662 0.135633 0.863038 0.094 Uiso 1 1 calc R U . . .
C12 C 0.0928(4) 0.06149(16) 0.86038(12) 0.0673(7) Uani 1 1 d . . . . .
C13 C 0.2199(3) 0.02459(16) 0.81779(12) 0.0647(6) Uani 1 1 d . . . . .
H13 H 0.325882 -0.008635 0.834756 0.078 Uiso 1 1 calc R U . . .
C14 C 0.1883(4) 0.03746(15) 0.74931(12) 0.0666(7) Uani 1 1 d . . . . .
H14 H 0.275914 0.013163 0.720644 0.080 Uiso 1 1 calc R U . . .
C15 C 0.2489(4) -0.0064(2) 0.95836(14) 0.0950(9) Uani 1 1 d . . . . .
H15A H 0.243145 -0.005443 1.006454 0.114 Uiso 1 1 calc R U . . .
H15B H 0.233820 -0.073837 0.942323 0.114 Uiso 1 1 calc R U . . .
H15C H 0.367323 0.019046 0.946115 0.114 Uiso 1 1 calc R U . . .
C16 C 0.2852(4) 0.19951(16) 0.62003(12) 0.0657(6) Uani 1 1 d . . . . .
C17 C 0.3397(4) 0.24311(17) 0.68171(12) 0.0706(7) Uani 1 1 d . . . . .
H17 H 0.262894 0.236930 0.717666 0.085 Uiso 1 1 calc R U . . .
C18 C 0.5037(4) 0.29479(16) 0.69046(12) 0.0687(7) Uani 1 1 d . . . . .
H18 H 0.537914 0.323209 0.731947 0.082 Uiso 1 1 calc R U . . .
C19 C 0.6168(4) 0.30421(16) 0.63752(13) 0.0663(6) Uani 1 1 d . . . . .
C20 C 0.5678(4) 0.26452(19) 0.57522(13) 0.0787(8) Uani 1 1 d . . . . .
H20 H 0.644424 0.272528 0.539385 0.094 Uiso 1 1 calc R U . . .
C21 C 0.4034(4) 0.21293(18) 0.56729(13) 0.0791(8) Uani 1 1 d . . . . .
H21 H 0.369359 0.185956 0.525342 0.095 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.201(3) . ?
O2 C1 1.332(3) . ?
O2 C8 1.431(3) . ?
O3 C12 1.375(3) . ?
O3 C15 1.406(3) . ?
O4 N1 1.219(3) . ?
O5 N1 1.225(3) . ?
N1 C19 1.464(3) . ?
C1 C2 1.460(4) . ?
C2 C3 1.326(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.435(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.344(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.451(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.356(3) . ?
C6 C9 1.491(3) . ?
C7 C16 1.456(3) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.376(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.366(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.396(3) . ?
C16 C21 1.396(3) . ?
C17 C18 1.370(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(3) . ?
C20 C21 1.370(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
C1 O2 C8 116.6(2) . . ?
C12 O3 C15 117.5(2) . . ?
O4 N1 O5 123.1(3) . . ?
O4 N1 C19 118.5(2) . . ?
O5 N1 C19 118.4(3) . . ?
O1 C1 O2 122.9(3) . . ?
O1 C1 C2 126.1(3) . . ?
O2 C1 C2 111.0(2) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 125.0(2) . . ?
C2 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?
C5 C4 C3 123.9(2) . . ?
C5 C4 H4 118.1 . . ?
C3 C4 H4 118.1 . . ?
C4 C5 C6 127.7(2) . . ?
C4 C5 H5 116.2 . . ?
C6 C5 H5 116.2 . . ?
C7 C6 C5 117.2(2) . . ?
C7 C6 C9 125.0(2) . . ?
C5 C6 C9 117.7(2) . . ?
C6 C7 C16 131.7(2) . . ?
C6 C7 H7 114.2 . . ?
C16 C7 H7 114.2 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 116.9(2) . . ?
C14 C9 C6 121.7(2) . . ?
C10 C9 C6 121.4(2) . . ?
C11 C10 C9 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 O3 125.3(2) . . ?
C13 C12 C11 119.6(2) . . ?
O3 C12 C11 115.1(2) . . ?
C12 C13 C14 119.0(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C9 C14 C13 122.6(2) . . ?
C9 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.0(2) . . ?
C17 C16 C7 125.2(2) . . ?
C21 C16 C7 117.9(2) . . ?
C18 C17 C16 121.5(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 119.4(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C20 121.5(2) . . ?
C18 C19 N1 119.7(2) . . ?
C20 C19 N1 118.8(2) . . ?
C21 C20 C19 118.4(2) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C20 C21 C16 122.2(2) . . ?
C20 C21 H21 118.9 . . ?
C16 C21 H21 118.9 . . ?

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
C8 O2 C1 O1 1.3(4) . . . . ?
C8 O2 C1 C2 -179.2(2) . . . . ?
O1 C1 C2 C3 4.4(4) . . . . ?
O2 C1 C2 C3 -175.1(2) . . . . ?
C1 C2 C3 C4 176.5(2) . . . . ?
C2 C3 C4 C5 177.7(2) . . . . ?
C3 C4 C5 C6 178.5(2) . . . . ?
C4 C5 C6 C7 170.8(2) . . . . ?
C4 C5 C6 C9 -6.9(4) . . . . ?
C5 C6 C7 C16 179.1(2) . . . . ?
C9 C6 C7 C16 -3.3(4) . . . . ?
C7 C6 C9 C14 -59.8(3) . . . . ?
C5 C6 C9 C14 117.8(3) . . . . ?
C7 C6 C9 C10 120.9(3) . . . . ?
C5 C6 C9 C10 -61.5(3) . . . . ?
C14 C9 C10 C11 -0.2(4) . . . . ?
C6 C9 C10 C11 179.1(2) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C15 O3 C12 C13 -7.9(4) . . . . ?
C15 O3 C12 C11 171.6(2) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C10 C11 C12 O3 -179.2(2) . . . . ?
O3 C12 C13 C14 179.8(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C10 C9 C14 C13 0.9(3) . . . . ?
C6 C9 C14 C13 -178.4(2) . . . . ?
C12 C13 C14 C9 -1.0(4) . . . . ?
C6 C7 C16 C17 -22.0(4) . . . . ?
C6 C7 C16 C21 159.6(3) . . . . ?
C21 C16 C17 C18 -1.4(4) . . . . ?
C7 C16 C17 C18 -179.9(2) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C17 C18 C19 N1 -178.0(2) . . . . ?
O4 N1 C19 C18 9.9(3) . . . . ?
O5 N1 C19 C18 -171.6(2) . . . . ?
O4 N1 C19 C20 -169.4(2) . . . . ?
O5 N1 C19 C20 9.1(4) . . . . ?
C18 C19 C20 C21 -1.3(4) . . . . ?
N1 C19 C20 C21 178.0(2) . . . . ?
C19 C20 C21 C16 0.0(4) . . . . ?
C17 C16 C21 C20 1.4(4) . . . . ?
C7 C16 C21 C20 179.9(2) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'methyl (2E,4E,6Z)-6-(4-methoxyphenyl)-7-(4-nitrophenyl)hepta-2,4,6-trienoate'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
_chemical_properties_physical    Heat-sensitive
