# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_aa519
_database_code_depnum_ccdc_archive 'CCDC 2046872'
loop_
_audit_author_name
_audit_author_address
'Leslaw Sieron'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2020-11-27 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;

#===============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
methyl (R,E)-5-phenyl-6-(pyridin-2-yl)hex-2-enoate
;
_chemical_formula_moiety         'C18 H19 N O2'
_chemical_formula_structural     ?
_chemical_formula_sum            'C18 H19 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         281.34

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'

#===============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   5.7216(1)
_cell_length_b                   15.4964(1)
_cell_length_c                   17.3718(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1540.26(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    36526
_cell_measurement_theta_min      3.826
_cell_measurement_theta_max      78.978

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.076
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

#===============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_detector_area_resol_mean 5.8140

# number of measured reflections (redundant set)
_diffrn_reflns_number            41794
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0083
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000

# number of unique reflections
_reflns_number_total             2719
# number of observed reflections (> n sig(I))
_reflns_number_gt                2694
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#===============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0224P)²+0.2924P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'shelxl-2018/3 (sheldrick 2018)'
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1105 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2719
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0541
_refine_ls_wR_factor_gt          0.0540
_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
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.024

#===============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.74836(18) 0.32941(7) 0.17802(6) 1.000 0.0274(3) d . . .
O2 O Uani 0.49872(19) 0.32829(7) 0.07833(6) 1.000 0.0318(3) d . . .
N1 N Uani 0.1981(2) 0.36657(9) 0.57035(7) 1.000 0.0295(4) d . . .
C1 C Uani -0.0065(3) 0.37436(9) 0.53335(8) 1.000 0.0213(4) d . . .
C2 C Uani -0.1898(3) 0.42263(9) 0.56325(8) 1.000 0.0262(4) d . . .
C3 C Uani -0.1616(3) 0.46450(9) 0.63335(8) 1.000 0.0281(4) d . . .
C4 C Uani 0.0480(3) 0.45614(10) 0.67199(8) 1.000 0.0281(4) d . . .
C5 C Uani 0.2196(3) 0.40651(11) 0.63845(8) 1.000 0.0316(5) d . . .
C6 C Uani -0.0274(3) 0.32661(9) 0.45801(8) 1.000 0.0245(4) d . . .
C7 C Uani 0.1638(3) 0.35088(9) 0.39946(8) 1.000 0.0217(4) d . . .
C8 C Uani 0.1476(3) 0.44553(9) 0.37686(7) 1.000 0.0199(4) d . . .
C9 C Uani 0.3213(3) 0.50366(9) 0.39774(8) 1.000 0.0236(4) d . . .
C10 C Uani 0.3035(3) 0.59088(10) 0.37934(9) 1.000 0.0280(4) d . . .
C11 C Uani 0.1101(3) 0.62124(9) 0.34009(8) 1.000 0.0261(4) d . . .
C12 C Uani -0.0649(3) 0.56412(9) 0.31894(8) 1.000 0.0252(4) d . . .
C13 C Uani -0.0459(3) 0.47707(9) 0.33668(8) 1.000 0.0239(4) d . . .
C14 C Uani 0.1522(3) 0.28963(9) 0.32948(8) 1.000 0.0240(4) d . . .
C15 C Uani 0.3535(3) 0.30065(9) 0.27593(8) 1.000 0.0232(4) d . . .
C16 C Uani 0.3385(3) 0.31668(9) 0.20106(8) 1.000 0.0234(4) d . . .
C17 C Uani 0.5507(3) 0.32536(9) 0.15370(8) 1.000 0.0223(4) d . . .
C18 C Uani 0.6958(3) 0.33562(12) 0.02648(9) 1.000 0.0392(6) d . . .
H2 H Uiso -0.33328 0.42698 0.53599 1.000 0.0310 c RU . .
H3 H Uiso -0.28454 0.49833 0.65435 1.000 0.0340 c RU . .
H4 H Uiso 0.07294 0.48372 0.72013 1.000 0.0340 c RU . .
H5 H Uiso 0.36310 0.40014 0.66539 1.000 0.0380 c RU . .
H6A H Uiso -0.18234 0.33898 0.43516 1.000 0.0290 c RU . .
H6B H Uiso -0.01915 0.26382 0.46817 1.000 0.0290 c RU . .
H7 H Uiso 0.31853 0.34193 0.42499 1.000 0.0260 c RU . .
H9 H Uiso 0.45447 0.48356 0.42505 1.000 0.0280 c RU . .
H10 H Uiso 0.42459 0.62959 0.39379 1.000 0.0340 c RU . .
H11 H Uiso 0.09725 0.68077 0.32771 1.000 0.0310 c RU . .
H12 H Uiso -0.19851 0.58465 0.29215 1.000 0.0300 c RU . .
H13 H Uiso -0.16605 0.43843 0.32130 1.000 0.0290 c RU . .
H14A H Uiso 0.14891 0.22923 0.34802 1.000 0.0290 c RU . .
H14B H Uiso 0.00514 0.30040 0.30103 1.000 0.0290 c RU . .
H15 H Uiso 0.50584 0.29577 0.29725 1.000 0.0280 c RU . .
H16 H Uiso 0.18913 0.32262 0.17775 1.000 0.0280 c RU . .
H18A H Uiso 0.64034 0.35247 -0.02473 1.000 0.0590 c RU . .
H18B H Uiso 0.77625 0.27991 0.02315 1.000 0.0590 c RU . .
H18C H Uiso 0.80431 0.37944 0.04592 1.000 0.0590 c RU . .


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C17 1.209(2)
O2 C17 1.3434(18)
O2 C18 1.448(2)
N1 C1 1.341(2)
N1 C5 1.3408(19)
C1 C2 1.389(2)
C1 C6 1.508(2)
C2 C3 1.389(2)
C3 C4 1.380(2)
C4 C5 1.377(2)
C6 C7 1.540(2)
C7 C8 1.521(2)
C7 C14 1.544(2)
C8 C9 1.390(2)
C8 C13 1.397(2)
C9 C10 1.393(2)
C10 C11 1.382(2)
C11 C12 1.386(2)
C12 C13 1.388(2)
C14 C15 1.490(2)
C15 C16 1.327(2)
C16 C17 1.473(2)
C2 H2 0.9500
C3 H3 0.9500
C4 H4 0.9500
C5 H5 0.9500
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7 1.0000
C9 H9 0.9500
C10 H10 0.9500
C11 H11 0.9500
C12 H12 0.9500
C13 H13 0.9500
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15 0.9500
C16 H16 0.9500
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C17 O2 C18 115.89(12)
C1 N1 C5 117.48(13)
N1 C1 C2 121.90(13)
N1 C1 C6 116.17(14)
C2 C1 C6 121.93(14)
C1 C2 C3 119.45(15)
C2 C3 C4 118.90(15)
C3 C4 C5 117.79(13)
N1 C5 C4 124.47(15)
C1 C6 C7 113.38(13)
C6 C7 C8 111.26(12)
C6 C7 C14 109.84(12)
C8 C7 C14 112.77(11)
C7 C8 C9 120.94(14)
C7 C8 C13 120.97(14)
C9 C8 C13 118.06(13)
C8 C9 C10 121.13(15)
C9 C10 C11 120.14(15)
C10 C11 C12 119.45(13)
C11 C12 C13 120.35(15)
C8 C13 C12 120.86(14)
C7 C14 C15 112.82(13)
C14 C15 C16 125.68(15)
C15 C16 C17 120.75(15)
O1 C17 O2 123.09(14)
O1 C17 C16 125.50(13)
O2 C17 C16 111.41(14)
C1 C2 H2 120.00
C3 C2 H2 120.00
C2 C3 H3 121.00
C4 C3 H3 121.00
C3 C4 H4 121.00
C5 C4 H4 121.00
N1 C5 H5 118.00
C4 C5 H5 118.00
C1 C6 H6A 109.00
C1 C6 H6B 109.00
C7 C6 H6A 109.00
C7 C6 H6B 109.00
H6A C6 H6B 108.00
C6 C7 H7 108.00
C8 C7 H7 108.00
C14 C7 H7 108.00
C8 C9 H9 119.00
C10 C9 H9 119.00
C9 C10 H10 120.00
C11 C10 H10 120.00
C10 C11 H11 120.00
C12 C11 H11 120.00
C11 C12 H12 120.00
C13 C12 H12 120.00
C8 C13 H13 120.00
C12 C13 H13 120.00
C7 C14 H14A 109.00
C7 C14 H14B 109.00
C15 C14 H14A 109.00
C15 C14 H14B 109.00
H14A C14 H14B 108.00
C14 C15 H15 117.00
C16 C15 H15 117.00
C15 C16 H16 120.00
C17 C16 H16 120.00
O2 C18 H18A 109.00
O2 C18 H18B 109.00
O2 C18 H18C 109.00
H18A C18 H18B 109.00
H18A C18 H18C 109.00
H18B C18 H18C 109.00

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
C18 O2 C17 O1 0.8(2)
C18 O2 C17 C16 -179.19(12)
C5 N1 C1 C2 0.8(2)
C5 N1 C1 C6 -178.32(13)
C1 N1 C5 C4 -1.4(2)
N1 C1 C2 C3 0.2(2)
C6 C1 C2 C3 179.28(13)
N1 C1 C6 C7 -56.34(17)
C2 C1 C6 C7 124.55(15)
C1 C2 C3 C4 -0.7(2)
C2 C3 C4 C5 0.2(2)
C3 C4 C5 N1 0.9(2)
C1 C6 C7 C8 -63.02(16)
C1 C6 C7 C14 171.41(12)
C6 C7 C8 C9 112.62(16)
C6 C7 C8 C13 -65.29(17)
C14 C7 C8 C9 -123.45(15)
C14 C7 C8 C13 58.64(19)
C6 C7 C14 C15 -171.44(12)
C8 C7 C14 C15 63.85(18)
C7 C8 C9 C10 -177.89(14)
C13 C8 C9 C10 0.1(2)
C7 C8 C13 C12 177.28(13)
C9 C8 C13 C12 -0.7(2)
C8 C9 C10 C11 0.4(2)
C9 C10 C11 C12 -0.3(2)
C10 C11 C12 C13 -0.3(2)
C11 C12 C13 C8 0.8(2)
C7 C14 C15 C16 -125.37(16)
C14 C15 C16 C17 -179.32(13)
C15 C16 C17 O1 -9.4(2)
C15 C16 C17 O2 170.58(13)

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C11 H11 O1 0.95 2.47 3.3408(18) 153 4_655
C16 H16 O1 0.95 2.52 3.406(2) 154 1_455

