# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_larnaud5_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2114432'
loop_
_audit_author_name
_audit_author_address
'Jean-Francois Lohier'
;LCMT ENSICAEN
France
;
_audit_update_record             
;
2021-10-07 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
(Z)-4-fluoro-2-isobutyl-5-phtalimidopent-3-en-1-oic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 F N O4'
_chemical_formula_sum            'C17 H18 F N O4'
_chemical_formula_weight         319.32

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   31.87(3)
_cell_length_b                   5.876(8)
_cell_length_c                   8.328(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1560(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8287
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.50

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   0.6028
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Sadabs 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13152
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.760
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             3316
_reflns_number_gt                3079
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_max     0.871
_reflns_Friedel_fraction_full    0.911

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+0.2269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1223 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3316
_refine_ls_number_parameters     214
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.39703(4) 0.4120(2) 0.52810(17) 0.0317(3) Uani 1 1 d . . . . .
O2 O 0.30210(4) 0.8757(3) 0.6447(2) 0.0332(4) Uani 1 1 d . . . . .
O4 O 0.38594(5) 1.0825(3) 0.1876(2) 0.0339(4) Uani 1 1 d . . . . .
O1 O 0.35071(4) 0.2504(2) 0.9102(2) 0.0313(4) Uani 1 1 d . . . . .
O3 O 0.36941(5) 0.7417(3) 0.0889(2) 0.0370(4) Uani 1 1 d . . . . .
N1 N 0.33632(4) 0.5722(3) 0.7627(2) 0.0218(4) Uani 1 1 d . . . . .
C8 C 0.30083(5) 0.6960(3) 0.7142(2) 0.0225(4) Uani 1 1 d . . . . .
C6 C 0.26414(6) 0.5607(3) 0.7684(3) 0.0217(4) Uani 1 1 d . . . . .
C5 C 0.22175(6) 0.5994(3) 0.7466(3) 0.0257(4) Uani 1 1 d . . . . .
H5 H 0.211806 0.729774 0.690883 0.031 Uiso 1 1 calc R U . . .
C1 C 0.27894(6) 0.3705(3) 0.8497(2) 0.0214(4) Uani 1 1 d . . . . .
C10 C 0.39379(6) 0.6361(3) 0.5725(3) 0.0224(4) Uani 1 1 d . . . . .
C14 C 0.46352(5) 0.8666(3) 0.2763(3) 0.0207(4) Uani 1 1 d . . . . .
H14A H 0.471879 0.840895 0.163216 0.025 Uiso 1 1 calc R U . . .
H14B H 0.461308 1.033044 0.292582 0.025 Uiso 1 1 calc R U . . .
C9 C 0.37889(5) 0.6601(4) 0.7410(2) 0.0242(4) Uani 1 1 d . . . . .
H9A H 0.398216 0.577042 0.813296 0.029 Uiso 1 1 calc R U . . .
H9B H 0.379521 0.822855 0.771664 0.029 Uiso 1 1 calc R U . . .
C7 C 0.32566(6) 0.3798(3) 0.8495(2) 0.0223(4) Uani 1 1 d . . . . .
C2 C 0.25181(7) 0.2117(3) 0.9138(3) 0.0272(4) Uani 1 1 d . . . . .
H2 H 0.261838 0.082484 0.970611 0.033 Uiso 1 1 calc R U . . .
C11 C 0.40375(5) 0.7984(3) 0.4710(2) 0.0198(4) Uani 1 1 d . . . . .
H11 H 0.400670 0.951268 0.506128 0.024 Uiso 1 1 calc R U . . .
C15 C 0.49823(5) 0.7754(3) 0.3852(3) 0.0218(4) Uani 1 1 d . . . . .
H15 H 0.491159 0.815741 0.498698 0.026 Uiso 1 1 calc R U . . .
C12 C 0.41973(5) 0.7600(3) 0.3027(2) 0.0196(4) Uani 1 1 d . . . . .
H12 H 0.422015 0.592208 0.284565 0.024 Uiso 1 1 calc R U . . .
C17 C 0.50310(7) 0.5179(4) 0.3743(3) 0.0311(5) Uani 1 1 d . . . . .
H17A H 0.477497 0.444332 0.413620 0.047 Uiso 1 1 calc R U . . .
H17B H 0.527016 0.469610 0.439877 0.047 Uiso 1 1 calc R U . . .
H17C H 0.507914 0.474205 0.262196 0.047 Uiso 1 1 calc R U . . .
C4 C 0.19442(6) 0.4392(4) 0.8098(3) 0.0288(5) Uani 1 1 d . . . . .
H4 H 0.165051 0.459740 0.796797 0.035 Uiso 1 1 calc R U . . .
C13 C 0.38891(6) 0.8557(4) 0.1815(2) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.20907(6) 0.2493(4) 0.8915(3) 0.0299(5) Uani 1 1 d . . . . .
H3 H 0.189500 0.142686 0.933234 0.036 Uiso 1 1 calc R U . . .
C16 C 0.53975(6) 0.8908(4) 0.3415(3) 0.0301(5) Uani 1 1 d . . . . .
H16A H 0.547467 0.850580 0.231179 0.045 Uiso 1 1 calc R U . . .
H16B H 0.561761 0.839339 0.415217 0.045 Uiso 1 1 calc R U . . .
H16C H 0.536602 1.056211 0.350114 0.045 Uiso 1 1 calc R U . . .
H1 H 0.3686(13) 1.127(7) 0.105(7) 0.098(13) Uiso 1 1 d . . . . .


_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
F1 C10 1.372(3) . ?
O2 C8 1.205(3) . ?
O4 C13 1.337(3) . ?
O1 C7 1.213(2) . ?
O3 C13 1.196(3) . ?
N1 C7 1.384(3) . ?
N1 C8 1.404(3) . ?
N1 C9 1.463(3) . ?
C8 C6 1.484(3) . ?
C6 C5 1.382(3) . ?
C6 C1 1.389(3) . ?
C5 C4 1.387(3) . ?
C1 C2 1.380(3) . ?
C1 C7 1.490(3) . ?
C10 C11 1.313(3) . ?
C10 C9 1.488(3) . ?
C14 C15 1.528(3) . ?
C14 C12 1.546(3) . ?
C2 C3 1.393(3) . ?
C11 C12 1.508(3) . ?
C15 C17 1.524(3) . ?
C15 C16 1.531(3) . ?
C12 C13 1.517(3) . ?
C4 C3 1.388(3) . ?

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
C7 N1 C8 112.05(16) . . ?
C7 N1 C9 125.47(15) . . ?
C8 N1 C9 121.93(17) . . ?
O2 C8 N1 124.41(17) . . ?
O2 C8 C6 129.93(17) . . ?
N1 C8 C6 105.66(18) . . ?
C5 C6 C1 121.92(17) . . ?
C5 C6 C8 129.94(19) . . ?
C1 C6 C8 108.14(17) . . ?
C6 C5 C4 116.90(19) . . ?
C2 C1 C6 121.31(18) . . ?
C2 C1 C7 130.66(18) . . ?
C6 C1 C7 108.03(16) . . ?
C11 C10 F1 120.3(2) . . ?
C11 C10 C9 128.0(2) . . ?
F1 C10 C9 111.67(17) . . ?
C15 C14 C12 115.29(17) . . ?
N1 C9 C10 112.27(16) . . ?
O1 C7 N1 124.61(18) . . ?
O1 C7 C1 129.39(18) . . ?
N1 C7 C1 106.00(15) . . ?
C1 C2 C3 117.01(19) . . ?
C10 C11 C12 124.8(2) . . ?
C17 C15 C14 112.72(17) . . ?
C17 C15 C16 109.72(16) . . ?
C14 C15 C16 109.24(18) . . ?
C11 C12 C13 110.15(16) . . ?
C11 C12 C14 112.12(16) . . ?
C13 C12 C14 109.86(17) . . ?
C5 C4 C3 121.38(19) . . ?
O3 C13 O4 123.11(19) . . ?
O3 C13 C12 123.9(2) . . ?
O4 C13 C12 112.95(17) . . ?
C4 C3 C2 121.48(19) . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.032

