# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_021223_a512_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2hnqgc
_database_code_depnum_ccdc_archive 'CCDC 2313823'
loop_
_audit_author_name
_audit_author_address
'Dinesh Kumar Gopalakrishnan'
;Indian Institute of Technology, Delhi
India
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-12-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        'Naphthylidene butenolide'
_chemical_formula_moiety         'C21 H14 O2'
_chemical_formula_sum            'C21 H14 O2'
_chemical_formula_weight         298.32
_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 0.0033 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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.1483(7)
_cell_length_b                   18.7780(15)
_cell_length_c                   9.9744(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.770(3)
_cell_angle_gamma                90
_cell_volume                     1508.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6652
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1464 before and 0.0716 after correction.
The Ratio of minimum to maximum transmission is 0.9232.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_preparation       'As mentioned in paper'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            47156
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.169
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1793
_reflns_number_total             2951
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.050
_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)+(0.0520P)²+0.1853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1262
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C009(H009), C00C(H00C), C00D(H00D), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N)
;
_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 0.02464(17) 0.66419(8) 0.45467(14) 0.0598(4) Uani 1 1 d . . . . .
O002 O -0.21950(19) 0.72143(9) 0.40707(17) 0.0815(5) Uani 1 1 d . . . . .
C003 C 0.2301(2) 0.68049(10) 0.1467(2) 0.0493(5) Uani 1 1 d . . . . .
C004 C 0.1217(2) 0.68309(10) 0.2520(2) 0.0493(5) Uani 1 1 d . . . . .
C005 C 0.1587(2) 0.65116(11) 0.3862(2) 0.0512(5) Uani 1 1 d . . . . .
C006 C 0.1636(3) 0.66287(10) 0.0145(2) 0.0567(6) Uani 1 1 d . . . . .
H006 H 0.050754 0.653132 -0.007287 0.068 Uiso 1 1 calc R U . . .
C007 C 0.4711(3) 0.56252(10) 0.6455(2) 0.0521(5) Uani 1 1 d . . . . .
C008 C 0.3984(2) 0.69611(11) 0.1761(2) 0.0564(6) Uani 1 1 d . . . . .
H008 H 0.445015 0.708066 0.264181 0.068 Uiso 1 1 calc R U . . .
C009 C 0.2881(2) 0.61194(11) 0.4412(2) 0.0538(5) Uani 1 1 d . . . . .
H009 H 0.376584 0.609892 0.392340 0.065 Uiso 1 1 calc R U . . .
C00A C 0.3091(3) 0.57171(10) 0.5683(2) 0.0520(5) Uani 1 1 d . . . . .
C00B C 0.4892(3) 0.51596(11) 0.7588(2) 0.0584(6) Uani 1 1 d . . . . .
C00C C -0.0306(2) 0.71180(11) 0.2411(2) 0.0574(6) Uani 1 1 d . . . . .
H00C H -0.086783 0.734076 0.164324 0.069 Uiso 1 1 calc R U . . .
C00D C 0.6126(3) 0.59995(11) 0.6166(2) 0.0613(6) Uani 1 1 d . . . . .
H00D H 0.602731 0.630851 0.542923 0.074 Uiso 1 1 calc R U . . .
C00E C -0.0934(3) 0.70249(12) 0.3684(2) 0.0619(6) Uani 1 1 d . . . . .
C00F C 0.1774(3) 0.53697(12) 0.6089(2) 0.0637(6) Uani 1 1 d . . . . .
H00F H 0.071514 0.544496 0.561277 0.076 Uiso 1 1 calc R U . . .
C00G C 0.2649(3) 0.65973(11) -0.0853(2) 0.0660(6) Uani 1 1 d . . . . .
H00G H 0.219976 0.647266 -0.173488 0.079 Uiso 1 1 calc R U . . .
C00H C 0.4963(3) 0.69394(12) 0.0752(2) 0.0646(6) Uani 1 1 d . . . . .
H00H H 0.608340 0.705558 0.095378 0.078 Uiso 1 1 calc R U . . .
C00I C 0.4310(3) 0.67495(11) -0.0542(3) 0.0664(7) Uani 1 1 d . . . . .
H00I H 0.498971 0.672338 -0.120941 0.080 Uiso 1 1 calc R U . . .
C00J C 0.7622(3) 0.59113(14) 0.6953(3) 0.0766(7) Uani 1 1 d . . . . .
H00J H 0.854060 0.615982 0.675153 0.092 Uiso 1 1 calc R U . . .
C00K C 0.1970(3) 0.49059(12) 0.7197(3) 0.0743(7) Uani 1 1 d . . . . .
H00K H 0.105173 0.467287 0.743904 0.089 Uiso 1 1 calc R U . . .
C00L C 0.3489(3) 0.47956(12) 0.7915(2) 0.0708(7) Uani 1 1 d . . . . .
H00L H 0.361438 0.447556 0.863461 0.085 Uiso 1 1 calc R U . . .
C00M C 0.6474(3) 0.50801(13) 0.8378(2) 0.0734(7) Uani 1 1 d . . . . .
H00M H 0.660987 0.477224 0.911685 0.088 Uiso 1 1 calc R U . . .
C00N C 0.7794(3) 0.54488(15) 0.8068(3) 0.0825(8) Uani 1 1 d . . . . .
H00N H 0.882706 0.539441 0.860084 0.099 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
O001 C005 1.395(2) . ?
O001 C00E 1.389(3) . ?
O002 C00E 1.204(2) . ?
C003 C004 1.473(3) . ?
C003 C006 1.387(3) . ?
C003 C008 1.389(3) . ?
C004 C005 1.455(3) . ?
C004 C00C 1.342(3) . ?
C005 C009 1.334(3) . ?
C006 H006 0.9300 . ?
C006 C00G 1.388(3) . ?
C007 C00A 1.433(3) . ?
C007 C00B 1.419(3) . ?
C007 C00D 1.417(3) . ?
C008 H008 0.9300 . ?
C008 C00H 1.377(3) . ?
C009 H009 0.9300 . ?
C009 C00A 1.464(3) . ?
C00A C00F 1.369(3) . ?
C00B C00L 1.412(3) . ?
C00B C00M 1.412(3) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.450(3) . ?
C00D H00D 0.9300 . ?
C00D C00J 1.356(3) . ?
C00F H00F 0.9300 . ?
C00F C00K 1.396(3) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.372(3) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.366(3) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00N 1.401(3) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.348(3) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.354(3) . ?
C00N H00N 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
C00E O001 C005 107.91(16) . . ?
C006 C003 C004 119.70(18) . . ?
C006 C003 C008 118.77(19) . . ?
C008 C003 C004 121.53(18) . . ?
C005 C004 C003 125.40(17) . . ?
C00C C004 C003 127.13(18) . . ?
C00C C004 C005 107.41(18) . . ?
O001 C005 C004 108.07(17) . . ?
C009 C005 O001 121.63(19) . . ?
C009 C005 C004 130.20(19) . . ?
C003 C006 H006 119.9 . . ?
C00G C006 C003 120.2(2) . . ?
C00G C006 H006 119.9 . . ?
C00B C007 C00A 118.52(19) . . ?
C00D C007 C00A 122.83(19) . . ?
C00D C007 C00B 118.6(2) . . ?
C003 C008 H008 119.9 . . ?
C00H C008 C003 120.2(2) . . ?
C00H C008 H008 119.9 . . ?
C005 C009 H009 115.8 . . ?
C005 C009 C00A 128.45(19) . . ?
C00A C009 H009 115.8 . . ?
C007 C00A C009 120.25(18) . . ?
C00F C00A C007 118.9(2) . . ?
C00F C00A C009 120.6(2) . . ?
C00L C00B C007 119.5(2) . . ?
C00M C00B C007 119.0(2) . . ?
C00M C00B C00L 121.5(2) . . ?
C004 C00C H00C 125.5 . . ?
C004 C00C C00E 109.05(19) . . ?
C00E C00C H00C 125.5 . . ?
C007 C00D H00D 119.7 . . ?
C00J C00D C007 120.6(2) . . ?
C00J C00D H00D 119.7 . . ?
O001 C00E C00C 107.49(18) . . ?
O002 C00E O001 119.9(2) . . ?
O002 C00E C00C 132.6(2) . . ?
C00A C00F H00F 119.0 . . ?
C00A C00F C00K 122.1(2) . . ?
C00K C00F H00F 119.0 . . ?
C006 C00G H00G 119.9 . . ?
C00I C00G C006 120.2(2) . . ?
C00I C00G H00G 119.9 . . ?
C008 C00H H00H 119.6 . . ?
C00I C00H C008 120.8(2) . . ?
C00I C00H H00H 119.6 . . ?
C00G C00I H00I 120.1 . . ?
C00H C00I C00G 119.8(2) . . ?
C00H C00I H00I 120.1 . . ?
C00D C00J H00J 119.7 . . ?
C00D C00J C00N 120.5(2) . . ?
C00N C00J H00J 119.7 . . ?
C00F C00K H00K 120.0 . . ?
C00L C00K C00F 120.1(2) . . ?
C00L C00K H00K 120.0 . . ?
C00B C00L H00L 119.6 . . ?
C00K C00L C00B 120.9(2) . . ?
C00K C00L H00L 119.6 . . ?
C00B C00M H00M 119.7 . . ?
C00N C00M C00B 120.5(2) . . ?
C00N C00M H00M 119.7 . . ?
C00J C00N H00N 119.6 . . ?
C00M C00N C00J 120.7(2) . . ?
C00M C00N H00N 119.6 . . ?

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
O001 C005 C009 C00A 6.1(3) . . . . ?
C003 C004 C005 O001 -179.02(17) . . . . ?
C003 C004 C005 C009 -2.8(3) . . . . ?
C003 C004 C00C C00E 179.76(19) . . . . ?
C003 C006 C00G C00I -0.9(3) . . . . ?
C003 C008 C00H C00I -1.5(3) . . . . ?
C004 C003 C006 C00G -179.50(18) . . . . ?
C004 C003 C008 C00H -179.33(19) . . . . ?
C004 C005 C009 C00A -169.7(2) . . . . ?
C004 C00C C00E O001 -2.5(2) . . . . ?
C004 C00C C00E O002 177.0(2) . . . . ?
C005 O001 C00E O002 -178.3(2) . . . . ?
C005 O001 C00E C00C 1.3(2) . . . . ?
C005 C004 C00C C00E 2.6(2) . . . . ?
C005 C009 C00A C007 -149.0(2) . . . . ?
C005 C009 C00A C00F 37.0(3) . . . . ?
C006 C003 C004 C005 133.2(2) . . . . ?
C006 C003 C004 C00C -43.4(3) . . . . ?
C006 C003 C008 C00H -0.1(3) . . . . ?
C006 C00G C00I C00H -0.7(3) . . . . ?
C007 C00A C00F C00K -2.7(3) . . . . ?
C007 C00B C00L C00K -2.6(3) . . . . ?
C007 C00B C00M C00N 0.7(3) . . . . ?
C007 C00D C00J C00N -0.1(3) . . . . ?
C008 C003 C004 C005 -47.5(3) . . . . ?
C008 C003 C004 C00C 135.8(2) . . . . ?
C008 C003 C006 C00G 1.2(3) . . . . ?
C008 C00H C00I C00G 1.8(3) . . . . ?
C009 C00A C00F C00K 171.4(2) . . . . ?
C00A C007 C00B C00L 0.7(3) . . . . ?
C00A C007 C00B C00M -178.26(18) . . . . ?
C00A C007 C00D C00J 177.8(2) . . . . ?
C00A C00F C00K C00L 0.9(4) . . . . ?
C00B C007 C00A C009 -172.25(17) . . . . ?
C00B C007 C00A C00F 1.9(3) . . . . ?
C00B C007 C00D C00J 0.3(3) . . . . ?
C00B C00M C00N C00J -0.5(4) . . . . ?
C00C C004 C005 O001 -1.8(2) . . . . ?
C00C C004 C005 C009 174.4(2) . . . . ?
C00D C007 C00A C009 10.2(3) . . . . ?
C00D C007 C00A C00F -175.7(2) . . . . ?
C00D C007 C00B C00L 178.36(18) . . . . ?
C00D C007 C00B C00M -0.6(3) . . . . ?
C00D C00J C00N C00M 0.2(4) . . . . ?
C00E O001 C005 C004 0.2(2) . . . . ?
C00E O001 C005 C009 -176.38(19) . . . . ?
C00F C00K C00L C00B 1.8(4) . . . . ?
C00L C00B C00M C00N -178.2(2) . . . . ?
C00M C00B C00L C00K 176.3(2) . . . . ?

_olex2_submission_original_sample_id 'Naphthylidene butenolide'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_121223_6mem_1_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2hnqkg
_database_code_depnum_ccdc_archive 'CCDC 2313826'
loop_
_audit_author_name
_audit_author_address
'Dinesh Kumar Gopalakrishnan'
;Indian Institute of Technology, Delhi
India
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-12-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        Dienoate
_chemical_formula_moiety         'C21 H18 O4'
_chemical_formula_sum            'C21 H18 O4'
_chemical_formula_weight         334.35
_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 0.0033 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4870(10)
_cell_length_b                   10.1115(12)
_cell_length_c                   10.5324(11)
_cell_angle_alpha                91.975(4)
_cell_angle_beta                 93.296(4)
_cell_angle_gamma                108.179(4)
_cell_volume                     856.01(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.73
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6962
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0782 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.9327.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull whiteish white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_preparation       'As mentioned in the paper'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42554
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.304
_diffrn_reflns_theta_min         2.123
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4272
_reflns_number_total             6039
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         6039
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.003
_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)+(0.0858P)²+0.1571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1675
_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 Secondary CH2 refined with riding coordinates:
 C00E(H00B,H00C), C00O(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00P(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 0.43639(12) 0.84780(10) 0.03551(9) 0.0477(2) Uani 1 1 d . . . . .
O002 O 0.16715(12) 0.75059(12) 0.03913(10) 0.0552(3) Uani 1 1 d . . . . .
O003 O 0.55061(13) 0.76517(10) 0.60988(9) 0.0552(3) Uani 1 1 d . . . . .
O004 O 0.51755(17) 0.82408(11) 0.41111(10) 0.0720(4) Uani 1 1 d . . . . .
C005 C 0.33917(13) 0.66165(11) 0.17770(10) 0.0347(2) Uani 1 1 d . . . . .
C006 C 0.49382(13) 0.62703(11) 0.16529(10) 0.0349(2) Uani 1 1 d . . . . .
C007 C 0.62655(14) 0.73111(13) 0.12105(11) 0.0407(2) Uani 1 1 d . . . . .
C008 C 0.23149(14) 0.62393(12) 0.26739(11) 0.0376(2) Uani 1 1 d . . . . .
H008 H 0.136132 0.650459 0.257956 0.045 Uiso 1 1 calc R U . . .
C009 C 0.30366(15) 0.75452(12) 0.08009(11) 0.0395(2) Uani 1 1 d . . . . .
C00A C 0.36103(16) 0.59796(13) 0.47795(11) 0.0424(3) Uani 1 1 d . . . . .
H00A H 0.364190 0.539980 0.544045 0.051 Uiso 1 1 calc R U . . .
C00B C 0.24722(14) 0.54417(12) 0.38069(10) 0.0364(2) Uani 1 1 d . . . . .
C00C C 0.11961(14) 0.40528(12) 0.38487(11) 0.0383(2) Uani 1 1 d . . . . .
C00D C 0.50940(15) 0.49668(13) 0.18704(11) 0.0410(2) Uani 1 1 d . . . . .
H00D H 0.421144 0.426802 0.216092 0.049 Uiso 1 1 calc R U . . .
C00E C 0.59806(16) 0.86783(13) 0.10209(13) 0.0484(3) Uani 1 1 d . . . . .
H00B H 0.603712 0.916206 0.184201 0.058 Uiso 1 1 calc R U . . .
H00C H 0.684714 0.925165 0.053146 0.058 Uiso 1 1 calc R U . . .
C00F C 0.48173(17) 0.73969(13) 0.49085(12) 0.0450(3) Uani 1 1 d . . . . .
C00G C 0.77343(16) 0.70446(16) 0.09856(13) 0.0515(3) Uani 1 1 d . . . . .
H00G H 0.861895 0.773712 0.068998 0.062 Uiso 1 1 calc R U . . .
C00H C 0.65775(18) 0.47142(16) 0.16509(13) 0.0493(3) Uani 1 1 d . . . . .
H00H H 0.669207 0.384793 0.180677 0.059 Uiso 1 1 calc R U . . .
C00I C 0.02587(18) 0.34031(14) 0.27456(13) 0.0504(3) Uani 1 1 d . . . . .
H00I H 0.045325 0.383734 0.197990 0.060 Uiso 1 1 calc R U . . .
C00J C 0.78790(17) 0.57425(18) 0.12030(14) 0.0545(3) Uani 1 1 d . . . . .
H00J H 0.886089 0.556079 0.104583 0.065 Uiso 1 1 calc R U . . .
C00K C 0.08760(19) 0.33688(15) 0.49834(13) 0.0528(3) Uani 1 1 d . . . . .
H00K H 0.147974 0.378222 0.573756 0.063 Uiso 1 1 calc R U . . .
C00L C -0.0960(2) 0.21210(16) 0.27639(17) 0.0630(4) Uani 1 1 d . . . . .
H00L H -0.157903 0.170555 0.201587 0.076 Uiso 1 1 calc R U . . .
C00M C -0.0330(2) 0.20845(16) 0.49915(15) 0.0634(4) Uani 1 1 d . . . . .
H00M H -0.051838 0.163529 0.575030 0.076 Uiso 1 1 calc R U . . .
C00N C -0.1257(2) 0.14597(17) 0.38906(17) 0.0630(4) Uani 1 1 d . . . . .
H00N H -0.207646 0.059973 0.390683 0.076 Uiso 1 1 calc R U . . .
C00O C 0.6726(2) 0.90138(16) 0.63806(15) 0.0609(4) Uani 1 1 d . . . . .
H00E H 0.626826 0.973883 0.612279 0.073 Uiso 1 1 calc R U . . .
H00F H 0.770889 0.909545 0.592368 0.073 Uiso 1 1 calc R U . . .
C00P C 0.7158(3) 0.9159(2) 0.77694(18) 0.0769(5) Uani 1 1 d . . . . .
H00O H 0.797923 1.004841 0.798342 0.115 Uiso 1 1 calc R U . . .
H00P H 0.759506 0.842999 0.801537 0.115 Uiso 1 1 calc R U . . .
H00Q H 0.618053 0.909453 0.821127 0.115 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
O001 C009 1.3444(14) . ?
O001 C00E 1.4566(16) . ?
O002 C009 1.2010(15) . ?
O003 C00F 1.3339(16) . ?
O003 C00O 1.4503(17) . ?
O004 C00F 1.2011(15) . ?
C005 C006 1.4716(15) . ?
C005 C008 1.3340(15) . ?
C005 C009 1.4957(15) . ?
C006 C007 1.3958(15) . ?
C006 C00D 1.3904(16) . ?
C007 C00E 1.4938(19) . ?
C007 C00G 1.3863(18) . ?
C008 H008 0.9300 . ?
C008 C00B 1.4858(15) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.3410(17) . ?
C00A C00F 1.4752(17) . ?
C00B C00C 1.4859(16) . ?
C00C C00I 1.3890(18) . ?
C00C C00K 1.3991(17) . ?
C00D H00D 0.9300 . ?
C00D C00H 1.3906(18) . ?
C00E H00B 0.9700 . ?
C00E H00C 0.9700 . ?
C00G H00G 0.9300 . ?
C00G C00J 1.385(2) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.379(2) . ?
C00I H00I 0.9300 . ?
C00I C00L 1.3851(19) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00M 1.3808(19) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.379(2) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.377(2) . ?
C00N H00N 0.9300 . ?
C00O H00E 0.9700 . ?
C00O H00F 0.9700 . ?
C00O C00P 1.478(2) . ?
C00P H00O 0.9600 . ?
C00P H00P 0.9600 . ?
C00P 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
C009 O001 C00E 117.51(9) . . ?
C00F O003 C00O 116.09(11) . . ?
C006 C005 C009 115.29(9) . . ?
C008 C005 C006 127.74(10) . . ?
C008 C005 C009 116.93(10) . . ?
C007 C006 C005 116.17(10) . . ?
C00D C006 C005 123.85(10) . . ?
C00D C006 C007 119.85(11) . . ?
C006 C007 C00E 115.73(11) . . ?
C00G C007 C006 120.06(12) . . ?
C00G C007 C00E 124.21(11) . . ?
C005 C008 H008 116.4 . . ?
C005 C008 C00B 127.12(10) . . ?
C00B C008 H008 116.4 . . ?
O001 C009 C005 116.42(10) . . ?
O002 C009 O001 118.69(10) . . ?
O002 C009 C005 124.89(11) . . ?
C00B C00A H00A 116.7 . . ?
C00B C00A C00F 126.67(10) . . ?
C00F C00A H00A 116.7 . . ?
C00A C00B C008 122.31(10) . . ?
C00A C00B C00C 121.73(10) . . ?
C00C C00B C008 115.76(10) . . ?
C00I C00C C00B 120.16(10) . . ?
C00I C00C C00K 117.90(11) . . ?
C00K C00C C00B 121.93(11) . . ?
C006 C00D H00D 120.2 . . ?
C006 C00D C00H 119.60(12) . . ?
C00H C00D H00D 120.2 . . ?
O001 C00E C007 110.86(10) . . ?
O001 C00E H00B 109.5 . . ?
O001 C00E H00C 109.5 . . ?
C007 C00E H00B 109.5 . . ?
C007 C00E H00C 109.5 . . ?
H00B C00E H00C 108.1 . . ?
O003 C00F C00A 109.38(10) . . ?
O004 C00F O003 122.40(12) . . ?
O004 C00F C00A 128.22(12) . . ?
C007 C00G H00G 120.1 . . ?
C00J C00G C007 119.74(13) . . ?
C00J C00G H00G 120.1 . . ?
C00D C00H H00H 119.9 . . ?
C00J C00H C00D 120.28(13) . . ?
C00J C00H H00H 119.9 . . ?
C00C C00I H00I 119.4 . . ?
C00L C00I C00C 121.28(12) . . ?
C00L C00I H00I 119.4 . . ?
C00G C00J H00J 119.8 . . ?
C00H C00J C00G 120.46(12) . . ?
C00H C00J H00J 119.8 . . ?
C00C C00K H00K 119.8 . . ?
C00M C00K C00C 120.47(13) . . ?
C00M C00K H00K 119.8 . . ?
C00I C00L H00L 120.0 . . ?
C00I C00L C00N 120.06(14) . . ?
C00N C00L H00L 120.0 . . ?
C00K C00M H00M 119.6 . . ?
C00N C00M C00K 120.87(13) . . ?
C00N C00M H00M 119.6 . . ?
C00L C00N H00N 120.3 . . ?
C00M C00N C00L 119.41(13) . . ?
C00M C00N H00N 120.3 . . ?
O003 C00O H00E 110.2 . . ?
O003 C00O H00F 110.2 . . ?
O003 C00O C00P 107.57(13) . . ?
H00E C00O H00F 108.5 . . ?
C00P C00O H00E 110.2 . . ?
C00P C00O H00F 110.2 . . ?
C00O C00P H00O 109.5 . . ?
C00O C00P H00P 109.5 . . ?
C00O C00P H00Q 109.5 . . ?
H00O C00P H00P 109.5 . . ?
H00O C00P H00Q 109.5 . . ?
H00P C00P H00Q 109.5 . . ?

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
C005 C006 C007 C00E 4.70(15) . . . . ?
C005 C006 C007 C00G -175.80(11) . . . . ?
C005 C006 C00D C00H 175.96(11) . . . . ?
C005 C008 C00B C00A 68.97(18) . . . . ?
C005 C008 C00B C00C -116.05(13) . . . . ?
C006 C005 C008 C00B 3.7(2) . . . . ?
C006 C005 C009 O001 -31.56(15) . . . . ?
C006 C005 C009 O002 147.89(13) . . . . ?
C006 C007 C00E O001 -45.78(14) . . . . ?
C006 C007 C00G C00J -0.07(19) . . . . ?
C006 C00D C00H C00J -0.92(19) . . . . ?
C007 C006 C00D C00H 0.34(17) . . . . ?
C007 C00G C00J C00H -0.5(2) . . . . ?
C008 C005 C006 C007 -143.36(12) . . . . ?
C008 C005 C006 C00D 40.87(18) . . . . ?
C008 C005 C009 O001 146.28(11) . . . . ?
C008 C005 C009 O002 -34.27(18) . . . . ?
C008 C00B C00C C00I 18.03(17) . . . . ?
C008 C00B C00C C00K -160.90(12) . . . . ?
C009 O001 C00E C007 49.72(15) . . . . ?
C009 C005 C006 C007 34.21(14) . . . . ?
C009 C005 C006 C00D -141.56(11) . . . . ?
C009 C005 C008 C00B -173.81(11) . . . . ?
C00A C00B C00C C00I -166.96(13) . . . . ?
C00A C00B C00C C00K 14.10(19) . . . . ?
C00B C00A C00F O003 167.44(13) . . . . ?
C00B C00A C00F O004 -12.2(3) . . . . ?
C00B C00C C00I C00L -178.74(14) . . . . ?
C00B C00C C00K C00M 179.37(14) . . . . ?
C00C C00I C00L C00N -0.4(3) . . . . ?
C00C C00K C00M C00N -0.9(3) . . . . ?
C00D C006 C007 C00E -179.34(11) . . . . ?
C00D C006 C007 C00G 0.15(17) . . . . ?
C00D C00H C00J C00G 1.0(2) . . . . ?
C00E O001 C009 O002 169.27(12) . . . . ?
C00E O001 C009 C005 -11.24(16) . . . . ?
C00E C007 C00G C00J 179.38(12) . . . . ?
C00F O003 C00O C00P 172.28(15) . . . . ?
C00F C00A C00B C008 1.6(2) . . . . ?
C00F C00A C00B C00C -173.03(12) . . . . ?
C00G C007 C00E O001 134.75(13) . . . . ?
C00I C00C C00K C00M 0.4(2) . . . . ?
C00I C00L C00N C00M -0.1(3) . . . . ?
C00K C00C C00I C00L 0.2(2) . . . . ?
C00K C00M C00N C00L 0.8(3) . . . . ?
C00O O003 C00F O004 -0.2(2) . . . . ?
C00O O003 C00F C00A -179.85(13) . . . . ?

_olex2_submission_original_sample_id Dienoate
_olex2_submission_special_instructions 'No special instructions were received'
