# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_jmcm220131
_audit_block_doi                 10.5517/ccdc.csd.cc2f5dz0
_database_code_depnum_ccdc_archive 'CCDC 2239532'
loop_
_audit_author_name
_audit_author_address
'Corine Bailly'
;Service de Radiocristallographie Federation de Chimie Le Bel Universite de Strasbourg
France
;
_audit_update_record             
;
2023-02-02 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-(4-nitrobenzyl)-4-(perfluorophenyl)isochromane
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 F5 N O3'
_chemical_formula_sum            'C22 H14 F5 N O3'
_chemical_formula_weight         435.34

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   41.4191(17)
_cell_length_b                   6.5104(3)
_cell_length_c                   14.0699(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.700(3)
_cell_angle_gamma                90
_cell_volume                     3750.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      66.37

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.186
_shelx_estimated_absorpt_T_min   0.815
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6091
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Cu-ImuS DIAMOND microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72332
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.158
_diffrn_reflns_theta_max         66.527
_diffrn_reflns_theta_full        66.527
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6631
_reflns_number_gt                4677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1247P)²+6.2158P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6631
_refine_ls_number_parameters     560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0826
_refine_ls_wR_factor_ref         0.2430
_refine_ls_wR_factor_gt          0.2203
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.76725(9) 0.2971(7) 0.6010(3) 0.0411(9) Uani 1 1 d . . . . .
C2 C 0.73773(9) 0.2018(7) 0.5711(2) 0.0402(9) Uani 1 1 d . . . . .
H2 H 0.7370 0.0597 0.5554 0.048 Uiso 1 1 calc R U . . .
C3 C 0.70920(10) 0.3153(7) 0.5640(3) 0.0451(10) Uani 1 1 d . . . . .
H3 H 0.6890 0.2527 0.5391 0.054 Uiso 1 1 calc R U . . .
C4 C 0.70981(11) 0.5211(7) 0.5930(3) 0.0510(11) Uani 1 1 d . . . . .
C5 C 0.74006(11) 0.6128(7) 0.6215(3) 0.0508(11) Uani 1 1 d . . . . .
H5 H 0.7409 0.7534 0.6397 0.061 Uiso 1 1 calc R U . . .
C6 C 0.76924(11) 0.5041(7) 0.6240(3) 0.0471(10) Uani 1 1 d . . . . .
H6 H 0.7898 0.5699 0.6409 0.056 Uiso 1 1 calc R U . . .
C7 C 0.67781(12) 0.6339(9) 0.5971(3) 0.0605(12) Uani 1 1 d . . . . .
H7A H 0.6626 0.5392 0.6231 0.073 Uiso 1 1 calc R U . . .
H7B H 0.6822 0.7503 0.6425 0.073 Uiso 1 1 calc R U . . .
C8 C 0.66150(11) 0.7143(9) 0.5032(3) 0.0614(13) Uani 1 1 d . . . . .
H8 H 0.6773 0.8078 0.4776 0.074 Uiso 1 1 calc R U . . .
C9 C 0.63127(10) 0.8358(8) 0.5102(3) 0.0507(11) Uani 1 1 d . . . . .
C10 C 0.63237(11) 0.9983(8) 0.5776(3) 0.0550(12) Uani 1 1 d . . . . .
H10 H 0.6521 1.0239 0.6200 0.066 Uiso 1 1 calc R U . . .
C11 C 0.60595(11) 1.1180(8) 0.5831(3) 0.0534(11) Uani 1 1 d . . . . .
H11 H 0.6071 1.2240 0.6299 0.064 Uiso 1 1 calc R U . . .
C12 C 0.57759(12) 1.0860(8) 0.5209(3) 0.0592(12) Uani 1 1 d . . . . .
H12 H 0.5597 1.1769 0.5213 0.071 Uiso 1 1 calc R U . . .
C13 C 0.57488(12) 0.9243(9) 0.4583(3) 0.0642(14) Uani 1 1 d . . . . .
H13 H 0.5545 0.8958 0.4197 0.077 Uiso 1 1 calc R U . . .
C14 C 0.60200(11) 0.8006(8) 0.4507(3) 0.0533(11) Uani 1 1 d . . . . .
C15 C 0.59983(12) 0.6184(9) 0.3817(3) 0.0639(13) Uani 1 1 d . . . . .
H15 H 0.5929 0.4959 0.4165 0.077 Uiso 1 1 calc R U . . .
C16 C 0.63332(12) 0.5741(11) 0.3571(3) 0.0764(18) Uani 1 1 d . . . . .
H16A H 0.6323 0.4507 0.3156 0.092 Uiso 1 1 calc R U . . .
H16B H 0.6405 0.6912 0.3206 0.092 Uiso 1 1 calc R U . . .
C17 C 0.57472(11) 0.6488(8) 0.2912(3) 0.0550(12) Uani 1 1 d . . . . .
C18 C 0.57411(11) 0.8114(8) 0.2289(4) 0.0597(12) Uani 1 1 d . . . . .
C19 C 0.55050(12) 0.8348(8) 0.1495(4) 0.0619(13) Uani 1 1 d . . . . .
C20 C 0.52626(11) 0.6928(9) 0.1318(3) 0.0572(12) Uani 1 1 d . . . . .
C21 C 0.52612(11) 0.5299(8) 0.1911(3) 0.0561(12) Uani 1 1 d . . . . .
C22 C 0.54996(13) 0.5089(8) 0.2688(3) 0.0588(12) Uani 1 1 d . . . . .
C23 C 0.73089(9) 0.3272(7) 0.8241(3) 0.0414(9) Uani 1 1 d . . . . .
C24 C 0.72910(10) 0.5320(7) 0.8501(3) 0.0437(10) Uani 1 1 d . . . . .
H24 H 0.7087 0.6010 0.8439 0.052 Uiso 1 1 calc R U . . .
C25 C 0.75773(9) 0.6327(7) 0.8852(3) 0.0421(9) Uani 1 1 d . . . . .
H25 H 0.7569 0.7724 0.9043 0.050 Uiso 1 1 calc R U . . .
C26 C 0.78782(9) 0.5332(7) 0.8932(3) 0.0420(9) Uani 1 1 d . . . . .
C27 C 0.78858(10) 0.3297(7) 0.8642(3) 0.0413(9) Uani 1 1 d . . . . .
H27 H 0.8090 0.2612 0.8675 0.050 Uiso 1 1 calc R U . . .
C28 C 0.76010(9) 0.2251(7) 0.8306(3) 0.0426(9) Uani 1 1 d . . . . .
H28 H 0.7607 0.0849 0.8123 0.051 Uiso 1 1 calc R U . . .
C29 C 0.81931(10) 0.6460(7) 0.9308(3) 0.0456(10) Uani 1 1 d . . . . .
H29A H 0.8339 0.5527 0.9730 0.055 Uiso 1 1 calc R U . . .
H29B H 0.8142 0.7646 0.9700 0.055 Uiso 1 1 calc R U . . .
C30 C 0.83722(9) 0.7231(7) 0.8502(3) 0.0430(9) Uani 1 1 d . . . . .
H30 H 0.8222 0.8153 0.8073 0.052 Uiso 1 1 calc R U . . .
C31 C 0.86780(9) 0.8438(7) 0.8889(3) 0.0391(9) Uani 1 1 d . . . . .
C32 C 0.86598(10) 1.0085(7) 0.9511(3) 0.0433(9) Uani 1 1 d . . . . .
H32 H 0.8456 1.0400 0.9710 0.052 Uiso 1 1 calc R U . . .
C33 C 0.89287(10) 1.1268(7) 0.9845(3) 0.0454(10) Uani 1 1 d . . . . .
H33 H 0.8911 1.2379 1.0272 0.054 Uiso 1 1 calc R U . . .
C34 C 0.92268(10) 1.0825(7) 0.9553(3) 0.0461(10) Uani 1 1 d . . . . .
H34 H 0.9413 1.1648 0.9767 0.055 Uiso 1 1 calc R U . . .
C35 C 0.92504(10) 0.9179(7) 0.8948(3) 0.0443(10) Uani 1 1 d . . . . .
H35 H 0.9456 0.8851 0.8769 0.053 Uiso 1 1 calc R U . . .
C36 C 0.89788(9) 0.7989(7) 0.8595(3) 0.0394(9) Uani 1 1 d . . . . .
C37 C 0.89998(9) 0.6191(7) 0.7920(3) 0.0429(9) Uani 1 1 d . . . . .
H37 H 0.9059 0.4945 0.8324 0.051 Uiso 1 1 calc R U . . .
C38 C 0.86651(10) 0.5809(9) 0.7332(3) 0.0572(13) Uani 1 1 d . . . . .
H38A H 0.8598 0.7012 0.6918 0.069 Uiso 1 1 calc R U . . .
H38B H 0.8674 0.4594 0.6913 0.069 Uiso 1 1 calc R U . . .
C39 C 0.92592(9) 0.6467(7) 0.7270(3) 0.0412(9) Uani 1 1 d . . . . .
C40 C 0.95047(9) 0.5041(7) 0.7254(3) 0.0411(9) Uani 1 1 d . . . . .
C41 C 0.97436(9) 0.5237(7) 0.6679(3) 0.0427(9) Uani 1 1 d . . . . .
C42 C 0.97451(9) 0.6906(7) 0.6097(3) 0.0429(10) Uani 1 1 d . . . . .
C43 C 0.95052(11) 0.8360(7) 0.6085(3) 0.0479(10) Uani 1 1 d . . . . .
C44 C 0.92665(9) 0.8121(7) 0.6668(3) 0.0437(9) Uani 1 1 d . . . . .
N1 N 0.79704(8) 0.1759(6) 0.6117(2) 0.0463(9) Uani 1 1 d . . . . .
N2 N 0.70050(9) 0.2162(7) 0.7878(2) 0.0509(9) Uani 1 1 d . . . . .
O1 O 0.79490(7) -0.0089(6) 0.6307(2) 0.0540(8) Uani 1 1 d . . . . .
O2 O 0.82263(7) 0.2602(6) 0.6014(2) 0.0618(9) Uani 1 1 d . . . . .
O3 O 0.65616(9) 0.5413(7) 0.4396(2) 0.0777(12) Uani 1 1 d . . . . .
O4 O 0.67503(7) 0.3106(6) 0.7773(2) 0.0626(9) Uani 1 1 d . . . . .
O5 O 0.70266(8) 0.0314(6) 0.7691(2) 0.0602(9) Uani 1 1 d . . . . .
O6 O 0.84358(7) 0.5469(5) 0.7969(2) 0.0519(8) Uani 1 1 d . . . . .
F1 F 0.59753(8) 0.9578(6) 0.2479(2) 0.0853(10) Uani 1 1 d . . . . .
F2 F 0.55119(9) 0.9990(6) 0.0917(3) 0.0949(12) Uani 1 1 d . . . . .
F3 F 0.50307(7) 0.7131(6) 0.0545(2) 0.0802(10) Uani 1 1 d . . . . .
F4 F 0.50229(8) 0.3858(6) 0.1711(2) 0.0871(11) Uani 1 1 d . . . . .
F5 F 0.54792(8) 0.3402(5) 0.3244(2) 0.0825(10) Uani 1 1 d . . . . .
F6 F 0.95182(6) 0.3344(4) 0.78123(18) 0.0576(7) Uani 1 1 d . . . . .
F7 F 0.99749(6) 0.3775(5) 0.66863(19) 0.0610(7) Uani 1 1 d . . . . .
F8 F 0.99724(6) 0.7115(5) 0.55191(17) 0.0566(7) Uani 1 1 d . . . . .
F9 F 0.94997(7) 1.0006(5) 0.5503(2) 0.0671(8) Uani 1 1 d . . . . .
F10 F 0.90368(6) 0.9598(4) 0.66362(19) 0.0598(7) Uani 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
C1 C2 1.379(5) . ?
C1 C6 1.385(6) . ?
C1 N1 1.453(5) . ?
C2 C3 1.385(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(6) . ?
C4 C7 1.524(6) . ?
C5 C6 1.396(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.484(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O3 1.435(6) . ?
C8 C9 1.497(6) . ?
C8 H8 1.0000 . ?
C9 C14 1.384(6) . ?
C9 C10 1.417(7) . ?
C10 C11 1.355(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.370(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.367(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.527(7) . ?
C15 C16 1.508(7) . ?
C15 C17 1.530(6) . ?
C15 H15 1.0000 . ?
C16 O3 1.399(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.372(7) . ?
C17 C18 1.373(7) . ?
C18 F1 1.357(6) . ?
C18 C19 1.377(7) . ?
C19 F2 1.346(6) . ?
C19 C20 1.360(7) . ?
C20 F3 1.344(5) . ?
C20 C21 1.351(7) . ?
C21 F4 1.360(6) . ?
C21 C22 1.364(7) . ?
C22 F5 1.359(6) . ?
C23 C28 1.372(6) . ?
C23 C24 1.387(6) . ?
C23 N2 1.474(5) . ?
C24 C25 1.380(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(6) . ?
C26 C29 1.520(5) . ?
C27 C28 1.382(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.531(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 O6 1.416(5) . ?
C30 C31 1.520(5) . ?
C30 H30 1.0000 . ?
C31 C32 1.393(6) . ?
C31 C36 1.402(5) . ?
C32 C33 1.377(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.389(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.381(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.394(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.518(6) . ?
C37 C38 1.523(6) . ?
C37 C39 1.523(5) . ?
C37 H37 1.0000 . ?
C38 O6 1.419(5) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C44 1.373(6) . ?
C39 C40 1.379(6) . ?
C40 F6 1.352(5) . ?
C40 C41 1.376(5) . ?
C41 F7 1.349(5) . ?
C41 C42 1.361(6) . ?
C42 F8 1.340(4) . ?
C42 C43 1.371(6) . ?
C43 F9 1.347(5) . ?
C43 C44 1.385(6) . ?
C44 F10 1.349(5) . ?
N1 O2 1.222(4) . ?
N1 O1 1.239(5) . ?
N2 O4 1.211(5) . ?
N2 O5 1.238(5) . ?

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
C2 C1 C6 121.9(4) . . ?
C2 C1 N1 119.1(4) . . ?
C6 C1 N1 119.0(4) . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.1(4) . . ?
C5 C4 C7 122.2(4) . . ?
C3 C4 C7 119.7(4) . . ?
C4 C5 C6 121.9(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 117.8(4) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C8 C7 C4 114.7(4) . . ?
C8 C7 H7A 108.6 . . ?
C4 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C4 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
O3 C8 C7 106.5(4) . . ?
O3 C8 C9 113.9(4) . . ?
C7 C8 C9 113.6(4) . . ?
O3 C8 H8 107.5 . . ?
C7 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C14 C9 C10 117.7(4) . . ?
C14 C9 C8 122.5(4) . . ?
C10 C9 C8 119.7(4) . . ?
C11 C10 C9 121.5(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 119.8(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.5(5) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.3(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 119.9(4) . . ?
C9 C14 C15 118.4(4) . . ?
C13 C14 C15 121.7(4) . . ?
C16 C15 C14 109.1(4) . . ?
C16 C15 C17 111.5(4) . . ?
C14 C15 C17 113.3(4) . . ?
C16 C15 H15 107.6 . . ?
C14 C15 H15 107.6 . . ?
C17 C15 H15 107.6 . . ?
O3 C16 C15 111.6(4) . . ?
O3 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
O3 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C22 C17 C18 115.1(4) . . ?
C22 C17 C15 119.8(5) . . ?
C18 C17 C15 125.1(5) . . ?
F1 C18 C17 118.2(4) . . ?
F1 C18 C19 118.7(5) . . ?
C17 C18 C19 123.1(5) . . ?
F2 C19 C20 120.8(4) . . ?
F2 C19 C18 120.0(5) . . ?
C20 C19 C18 119.2(5) . . ?
F3 C20 C21 120.5(5) . . ?
F3 C20 C19 119.9(5) . . ?
C21 C20 C19 119.5(4) . . ?
C20 C21 F4 119.0(4) . . ?
C20 C21 C22 120.2(5) . . ?
F4 C21 C22 120.8(5) . . ?
F5 C22 C21 116.2(5) . . ?
F5 C22 C17 120.9(4) . . ?
C21 C22 C17 122.9(5) . . ?
C28 C23 C24 122.0(4) . . ?
C28 C23 N2 118.9(4) . . ?
C24 C23 N2 119.1(4) . . ?
C25 C24 C23 118.3(4) . . ?
C25 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
C24 C25 C26 121.2(4) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C27 C26 C25 118.7(4) . . ?
C27 C26 C29 120.5(4) . . ?
C25 C26 C29 120.9(4) . . ?
C28 C27 C26 121.0(4) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C23 C28 C27 118.9(4) . . ?
C23 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C26 C29 C30 112.8(3) . . ?
C26 C29 H29A 109.0 . . ?
C30 C29 H29A 109.0 . . ?
C26 C29 H29B 109.0 . . ?
C30 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
O6 C30 C31 113.4(3) . . ?
O6 C30 C29 106.0(4) . . ?
C31 C30 C29 112.0(3) . . ?
O6 C30 H30 108.4 . . ?
C31 C30 H30 108.4 . . ?
C29 C30 H30 108.4 . . ?
C32 C31 C36 118.7(4) . . ?
C32 C31 C30 120.1(3) . . ?
C36 C31 C30 121.0(4) . . ?
C33 C32 C31 121.8(4) . . ?
C33 C32 H32 119.1 . . ?
C31 C32 H32 119.1 . . ?
C32 C33 C34 119.4(4) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C35 C34 C33 119.5(4) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 121.5(4) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C35 C36 C31 118.9(4) . . ?
C35 C36 C37 122.2(3) . . ?
C31 C36 C37 118.9(3) . . ?
C36 C37 C38 109.4(3) . . ?
C36 C37 C39 113.4(3) . . ?
C38 C37 C39 111.1(3) . . ?
C36 C37 H37 107.6 . . ?
C38 C37 H37 107.6 . . ?
C39 C37 H37 107.6 . . ?
O6 C38 C37 108.9(3) . . ?
O6 C38 H38A 109.9 . . ?
C37 C38 H38A 109.9 . . ?
O6 C38 H38B 109.9 . . ?
C37 C38 H38B 109.9 . . ?
H38A C38 H38B 108.3 . . ?
C44 C39 C40 115.7(3) . . ?
C44 C39 C37 123.1(4) . . ?
C40 C39 C37 121.2(4) . . ?
F6 C40 C41 116.6(4) . . ?
F6 C40 C39 120.5(3) . . ?
C41 C40 C39 123.0(4) . . ?
F7 C41 C42 120.0(3) . . ?
F7 C41 C40 120.2(4) . . ?
C42 C41 C40 119.8(4) . . ?
F8 C42 C41 120.9(4) . . ?
F8 C42 C43 119.8(4) . . ?
C41 C42 C43 119.3(3) . . ?
F9 C43 C42 120.1(4) . . ?
F9 C43 C44 120.1(4) . . ?
C42 C43 C44 119.8(4) . . ?
F10 C44 C39 119.9(3) . . ?
F10 C44 C43 117.6(4) . . ?
C39 C44 C43 122.5(4) . . ?
O2 N1 O1 123.6(4) . . ?
O2 N1 C1 118.8(4) . . ?
O1 N1 C1 117.5(3) . . ?
O4 N2 O5 123.9(4) . . ?
O4 N2 C23 118.4(4) . . ?
O5 N2 C23 117.7(4) . . ?
C16 O3 C8 114.8(4) . . ?
C30 O6 C38 113.8(3) . . ?

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
C6 C1 C2 C3 -0.3(5) . . . . ?
N1 C1 C2 C3 177.8(3) . . . . ?
C1 C2 C3 C4 -4.4(6) . . . . ?
C2 C3 C4 C5 5.3(6) . . . . ?
C2 C3 C4 C7 -171.9(4) . . . . ?
C3 C4 C5 C6 -1.7(6) . . . . ?
C7 C4 C5 C6 175.4(4) . . . . ?
C2 C1 C6 C5 3.7(5) . . . . ?
N1 C1 C6 C5 -174.3(3) . . . . ?
C4 C5 C6 C1 -2.7(6) . . . . ?
C5 C4 C7 C8 101.3(5) . . . . ?
C3 C4 C7 C8 -81.6(6) . . . . ?
C4 C7 C8 O3 57.5(6) . . . . ?
C4 C7 C8 C9 -176.3(5) . . . . ?
O3 C8 C9 C14 -8.5(7) . . . . ?
C7 C8 C9 C14 -130.7(5) . . . . ?
O3 C8 C9 C10 173.7(4) . . . . ?
C7 C8 C9 C10 51.5(7) . . . . ?
C14 C9 C10 C11 -1.0(7) . . . . ?
C8 C9 C10 C11 176.9(5) . . . . ?
C9 C10 C11 C12 -1.6(8) . . . . ?
C10 C11 C12 C13 5.0(8) . . . . ?
C11 C12 C13 C14 -5.9(8) . . . . ?
C10 C9 C14 C13 0.2(7) . . . . ?
C8 C9 C14 C13 -177.6(5) . . . . ?
C10 C9 C14 C15 -176.5(4) . . . . ?
C8 C9 C14 C15 5.7(7) . . . . ?
C12 C13 C14 C9 3.2(8) . . . . ?
C12 C13 C14 C15 179.8(5) . . . . ?
C9 C14 C15 C16 -27.6(6) . . . . ?
C13 C14 C15 C16 155.7(5) . . . . ?
C9 C14 C15 C17 -152.5(5) . . . . ?
C13 C14 C15 C17 30.8(7) . . . . ?
C14 C15 C16 O3 55.5(7) . . . . ?
C17 C15 C16 O3 -178.6(5) . . . . ?
C16 C15 C17 C22 113.3(6) . . . . ?
C14 C15 C17 C22 -123.1(5) . . . . ?
C16 C15 C17 C18 -68.3(7) . . . . ?
C14 C15 C17 C18 55.3(7) . . . . ?
C22 C17 C18 F1 178.7(4) . . . . ?
C15 C17 C18 F1 0.2(8) . . . . ?
C22 C17 C18 C19 0.2(8) . . . . ?
C15 C17 C18 C19 -178.3(5) . . . . ?
F1 C18 C19 F2 0.9(8) . . . . ?
C17 C18 C19 F2 179.5(5) . . . . ?
F1 C18 C19 C20 -177.7(5) . . . . ?
C17 C18 C19 C20 0.9(8) . . . . ?
F2 C19 C20 F3 1.5(8) . . . . ?
C18 C19 C20 F3 -179.8(5) . . . . ?
F2 C19 C20 C21 -179.8(5) . . . . ?
C18 C19 C20 C21 -1.2(8) . . . . ?
F3 C20 C21 F4 0.5(7) . . . . ?
C19 C20 C21 F4 -178.1(5) . . . . ?
F3 C20 C21 C22 179.2(4) . . . . ?
C19 C20 C21 C22 0.6(8) . . . . ?
C20 C21 C22 F5 -179.9(4) . . . . ?
F4 C21 C22 F5 -1.2(7) . . . . ?
C20 C21 C22 C17 0.5(8) . . . . ?
F4 C21 C22 C17 179.2(5) . . . . ?
C18 C17 C22 F5 179.6(4) . . . . ?
C15 C17 C22 F5 -1.9(7) . . . . ?
C18 C17 C22 C21 -0.8(7) . . . . ?
C15 C17 C22 C21 177.8(5) . . . . ?
C28 C23 C24 C25 -1.3(6) . . . . ?
N2 C23 C24 C25 179.1(3) . . . . ?
C23 C24 C25 C26 1.0(6) . . . . ?
C24 C25 C26 C27 0.5(6) . . . . ?
C24 C25 C26 C29 179.2(3) . . . . ?
C25 C26 C27 C28 -1.8(5) . . . . ?
C29 C26 C27 C28 179.5(3) . . . . ?
C24 C23 C28 C27 0.1(6) . . . . ?
N2 C23 C28 C27 179.6(3) . . . . ?
C26 C27 C28 C23 1.5(5) . . . . ?
C27 C26 C29 C30 80.1(5) . . . . ?
C25 C26 C29 C30 -98.5(4) . . . . ?
C26 C29 C30 O6 -58.4(5) . . . . ?
C26 C29 C30 C31 177.4(4) . . . . ?
O6 C30 C31 C32 -173.2(4) . . . . ?
C29 C30 C31 C32 -53.3(5) . . . . ?
O6 C30 C31 C36 9.9(5) . . . . ?
C29 C30 C31 C36 129.9(4) . . . . ?
C36 C31 C32 C33 -0.3(6) . . . . ?
C30 C31 C32 C33 -177.2(4) . . . . ?
C31 C32 C33 C34 0.4(6) . . . . ?
C32 C33 C34 C35 -1.4(6) . . . . ?
C33 C34 C35 C36 2.3(6) . . . . ?
C34 C35 C36 C31 -2.2(6) . . . . ?
C34 C35 C36 C37 179.2(4) . . . . ?
C32 C31 C36 C35 1.2(6) . . . . ?
C30 C31 C36 C35 178.1(4) . . . . ?
C32 C31 C36 C37 179.8(4) . . . . ?
C30 C31 C36 C37 -3.3(6) . . . . ?
C35 C36 C37 C38 -155.4(4) . . . . ?
C31 C36 C37 C38 26.0(5) . . . . ?
C35 C36 C37 C39 -30.8(5) . . . . ?
C31 C36 C37 C39 150.6(4) . . . . ?
C36 C37 C38 O6 -56.7(5) . . . . ?
C39 C37 C38 O6 177.4(4) . . . . ?
C36 C37 C39 C44 -56.3(5) . . . . ?
C38 C37 C39 C44 67.4(5) . . . . ?
C36 C37 C39 C40 123.6(4) . . . . ?
C38 C37 C39 C40 -112.7(5) . . . . ?
C44 C39 C40 F6 -179.3(4) . . . . ?
C37 C39 C40 F6 0.7(6) . . . . ?
C44 C39 C40 C41 0.0(6) . . . . ?
C37 C39 C40 C41 -179.9(4) . . . . ?
F6 C40 C41 F7 0.3(6) . . . . ?
C39 C40 C41 F7 -179.1(4) . . . . ?
F6 C40 C41 C42 179.9(3) . . . . ?
C39 C40 C41 C42 0.5(6) . . . . ?
F7 C41 C42 F8 0.7(6) . . . . ?
C40 C41 C42 F8 -179.0(4) . . . . ?
F7 C41 C42 C43 178.9(4) . . . . ?
C40 C41 C42 C43 -0.7(6) . . . . ?
F8 C42 C43 F9 -0.7(6) . . . . ?
C41 C42 C43 F9 -179.0(4) . . . . ?
F8 C42 C43 C44 178.7(4) . . . . ?
C41 C42 C43 C44 0.4(6) . . . . ?
C40 C39 C44 F10 -179.8(4) . . . . ?
C37 C39 C44 F10 0.2(6) . . . . ?
C40 C39 C44 C43 -0.4(6) . . . . ?
C37 C39 C44 C43 179.6(4) . . . . ?
F9 C43 C44 F10 -1.0(6) . . . . ?
C42 C43 C44 F10 179.6(4) . . . . ?
F9 C43 C44 C39 179.6(4) . . . . ?
C42 C43 C44 C39 0.2(7) . . . . ?
C2 C1 N1 O2 152.1(4) . . . . ?
C6 C1 N1 O2 -29.8(5) . . . . ?
C2 C1 N1 O1 -27.8(5) . . . . ?
C6 C1 N1 O1 150.3(4) . . . . ?
C28 C23 N2 O4 -176.0(4) . . . . ?
C24 C23 N2 O4 3.6(5) . . . . ?
C28 C23 N2 O5 3.6(5) . . . . ?
C24 C23 N2 O5 -176.9(4) . . . . ?
C15 C16 O3 C8 -62.7(7) . . . . ?
C7 C8 O3 C16 163.1(5) . . . . ?
C9 C8 O3 C16 37.0(7) . . . . ?
C31 C30 O6 C38 -42.9(5) . . . . ?
C29 C30 O6 C38 -166.2(3) . . . . ?
C37 C38 O6 C30 68.1(5) . . . . ?

_refine_diff_density_max         0.817
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.085


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hx'
####################################################################### 
# 
# 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_jmcm220204
_audit_block_doi                 10.5517/ccdc.csd.cc2f5f24
_database_code_depnum_ccdc_archive 'CCDC 2239535'
loop_
_audit_author_name
_audit_author_address
'Corine Bailly'
;Service de Radiocristallographie Federation de Chimie Le Bel Universite de Strasbourg
France
;
_audit_update_record             
;
2023-02-02 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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'

_cell_length_a                   7.9798(4)
_cell_length_b                   10.8805(5)
_cell_length_c                   8.4210(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.053(2)
_cell_angle_gamma                90
_cell_volume                     651.15(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      32.01

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7128
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21584
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.866
_diffrn_reflns_theta_max         32.024
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4510
_reflns_number_gt                4384
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.991

_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0519P)²+0.0460P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2080 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.18(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4510
_refine_ls_number_parameters     181
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C1 C 0.04525(16) 0.88049(11) 0.28327(16) 0.0171(2) Uani 1 1 d . . . . .
C2 C 0.07027(17) 0.78860(12) 0.40551(17) 0.0196(2) Uani 1 1 d . . . . .
H2 H -0.0342 0.7441 0.4011 0.024 Uiso 1 1 calc R U . . .
C3 C 0.25215(18) 0.76289(12) 0.53514(17) 0.0191(2) Uani 1 1 d . . . . .
H3 H 0.2720 0.7002 0.6204 0.023 Uiso 1 1 calc R U . . .
C4 C 0.40574(16) 0.82793(11) 0.54169(15) 0.0159(2) Uani 1 1 d . . . . .
C5 C 0.37443(17) 0.92175(12) 0.41728(18) 0.0202(2) Uani 1 1 d . . . . .
H5 H 0.4781 0.9676 0.4224 0.024 Uiso 1 1 calc R U . . .
C6 C 0.19376(17) 0.94874(12) 0.28644(18) 0.0204(2) Uani 1 1 d . . . . .
H6 H 0.1726 1.0120 0.2017 0.024 Uiso 1 1 calc R U . . .
C7 C 0.60371(16) 0.79515(11) 0.67613(16) 0.0171(2) Uani 1 1 d . . . . .
H7A H 0.5999 0.7451 0.7726 0.021 Uiso 1 1 calc R U . . .
H7B H 0.6750 0.8712 0.7300 0.021 Uiso 1 1 calc R U . . .
C8 C 0.70376(15) 0.72300(10) 0.58783(15) 0.0149(2) Uani 1 1 d . . . . .
H8 H 0.7077 0.7751 0.4918 0.018 Uiso 1 1 calc R U . . .
C9 C 0.90433(15) 0.68525(11) 0.71608(15) 0.0149(2) Uani 1 1 d . . . . .
C10 C 1.02618(17) 0.76593(12) 0.84778(16) 0.0187(2) Uani 1 1 d . . . . .
H10 H 0.9834 0.8457 0.8575 0.022 Uiso 1 1 calc R U . . .
C11 C 1.20942(18) 0.73067(14) 0.96467(18) 0.0228(3) Uani 1 1 d . . . . .
H11 H 1.2904 0.7860 1.0538 0.027 Uiso 1 1 calc R U . . .
C12 C 1.27349(19) 0.61416(14) 0.95045(18) 0.0236(3) Uani 1 1 d . . . . .
H12 H 1.3976 0.5893 1.0309 0.028 Uiso 1 1 calc R U . . .
C13 C 1.15512(18) 0.53434(12) 0.81816(17) 0.0211(2) Uani 1 1 d . . . . .
H13 H 1.2000 0.4555 0.8074 0.025 Uiso 1 1 calc R U . . .
C14 C 0.97010(17) 0.56857(11) 0.70007(15) 0.0165(2) Uani 1 1 d . . . . .
C15 C 0.84384(19) 0.47913(12) 0.55939(17) 0.0201(2) Uani 1 1 d . . . . .
H15A H 0.8051 0.4128 0.6163 0.024 Uiso 1 1 calc R U . . .
H15B H 0.9140 0.4412 0.5006 0.024 Uiso 1 1 calc R U . . .
C16 C 0.67044(18) 0.54362(12) 0.42078(17) 0.0200(2) Uani 1 1 d . . . . .
H16A H 0.7055 0.5956 0.3440 0.024 Uiso 1 1 calc R U . . .
H16B H 0.5777 0.4819 0.3443 0.024 Uiso 1 1 calc R U . . .
O1 O -0.16640(15) 0.98834(10) 0.03568(15) 0.0272(2) Uani 1 1 d . . . . .
O2 O -0.27654(14) 0.84470(12) 0.14047(17) 0.0336(3) Uani 1 1 d . . . . .
O3 O 0.58875(12) 0.61810(8) 0.50684(13) 0.01875(18) Uani 1 1 d . . . . .
N1 N -0.14569(15) 0.90607(11) 0.14384(16) 0.0216(2) Uani 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
C1 C2 1.3828(18) . ?
C1 C6 1.3885(18) . ?
C1 N1 1.4664(15) . ?
C2 C3 1.3911(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3944(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.4015(17) . ?
C4 C7 1.5092(16) . ?
C5 C6 1.3906(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5318(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O3 1.4285(14) . ?
C8 C9 1.5246(15) . ?
C8 H8 1.0000 . ?
C9 C10 1.4018(17) . ?
C9 C14 1.4035(16) . ?
C10 C11 1.3946(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.4043(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.5099(18) . ?
C15 C16 1.5167(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O3 1.4271(15) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
O1 N1 1.2334(17) . ?
O2 N1 1.2288(16) . ?

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
C2 C1 C6 122.64(11) . . ?
C2 C1 N1 118.62(11) . . ?
C6 C1 N1 118.74(11) . . ?
C1 C2 C3 118.39(11) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 120.90(12) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.04(11) . . ?
C3 C4 C7 120.74(11) . . ?
C5 C4 C7 120.18(11) . . ?
C6 C5 C4 120.94(11) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 118.07(12) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C4 C7 C8 110.84(9) . . ?
C4 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
O3 C8 C9 111.25(9) . . ?
O3 C8 C7 106.13(9) . . ?
C9 C8 C7 113.90(9) . . ?
O3 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C10 C9 C14 119.16(11) . . ?
C10 C9 C8 121.25(10) . . ?
C14 C9 C8 119.58(10) . . ?
C11 C10 C9 120.90(12) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.86(13) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 119.72(12) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.96(12) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 119.38(11) . . ?
C9 C14 C15 120.87(11) . . ?
C13 C14 C15 119.75(11) . . ?
C14 C15 C16 110.81(10) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O3 C16 C15 109.84(10) . . ?
O3 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
O3 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C16 O3 C8 110.70(9) . . ?
O2 N1 O1 123.39(12) . . ?
O2 N1 C1 118.54(12) . . ?
O1 N1 C1 118.07(11) . . ?

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
C6 C1 C2 C3 -0.84(19) . . . . ?
N1 C1 C2 C3 178.62(11) . . . . ?
C1 C2 C3 C4 -0.12(19) . . . . ?
C2 C3 C4 C5 1.14(19) . . . . ?
C2 C3 C4 C7 -176.63(12) . . . . ?
C3 C4 C5 C6 -1.25(19) . . . . ?
C7 C4 C5 C6 176.53(12) . . . . ?
C2 C1 C6 C5 0.73(19) . . . . ?
N1 C1 C6 C5 -178.73(12) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C3 C4 C7 C8 103.06(13) . . . . ?
C5 C4 C7 C8 -74.68(14) . . . . ?
C4 C7 C8 O3 -56.60(12) . . . . ?
C4 C7 C8 C9 -179.34(10) . . . . ?
O3 C8 C9 C10 -161.10(11) . . . . ?
C7 C8 C9 C10 -41.21(15) . . . . ?
O3 C8 C9 C14 20.27(15) . . . . ?
C7 C8 C9 C14 140.16(11) . . . . ?
C14 C9 C10 C11 -1.41(19) . . . . ?
C8 C9 C10 C11 179.96(12) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C13 0.9(2) . . . . ?
C11 C12 C13 C14 -1.1(2) . . . . ?
C10 C9 C14 C13 1.15(17) . . . . ?
C8 C9 C14 C13 179.81(11) . . . . ?
C10 C9 C14 C15 -179.66(11) . . . . ?
C8 C9 C14 C15 -1.00(17) . . . . ?
C12 C13 C14 C9 0.10(18) . . . . ?
C12 C13 C14 C15 -179.09(12) . . . . ?
C9 C14 C15 C16 14.43(16) . . . . ?
C13 C14 C15 C16 -166.39(11) . . . . ?
C14 C15 C16 O3 -47.93(14) . . . . ?
C15 C16 O3 C8 71.38(13) . . . . ?
C9 C8 O3 C16 -55.31(13) . . . . ?
C7 C8 O3 C16 -179.71(9) . . . . ?
C2 C1 N1 O2 -0.15(18) . . . . ?
C6 C1 N1 O2 179.33(13) . . . . ?
C2 C1 N1 O1 179.90(12) . . . . ?
C6 C1 N1 O1 -0.62(17) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_jmcm220530
_audit_block_doi                 10.5517/ccdc.csd.cc2f5f02
_database_code_depnum_ccdc_archive 'CCDC 2239533'
loop_
_audit_author_name
_audit_author_address
'Corine Bailly'
;Service de Radiocristallographie Federation de Chimie Le Bel Universite de Strasbourg
France
;
_audit_update_record             
;
2023-02-02 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-(4-nitrobenzyl)-3a,4,5,6-tetrahydro-1H,3H-benzo[de]isochromene
_chemical_name_common            ?
_chemical_melting_point          415-417
_chemical_formula_moiety         'C19 H19 N O3'
_chemical_formula_sum            'C19 H19 N O3'
_chemical_formula_weight         309.35

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.9718(3)
_cell_length_b                   9.2217(3)
_cell_length_c                   11.1636(4)
_cell_angle_alpha                100.8750(10)
_cell_angle_beta                 90.0200(10)
_cell_angle_gamma                110.5260(10)
_cell_volume                     752.80(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.04

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7130
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39094
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.862
_diffrn_reflns_theta_max         28.044
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3652
_reflns_number_gt                3349
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0540P)²+0.2532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3652
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
C1 C 0.51369(14) 0.41073(12) 0.13417(9) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.32919(14) 0.33790(12) 0.13741(10) 0.0218(2) Uani 1 1 d . . . . .
H2 H 0.2745 0.2260 0.1226 0.026 Uiso 1 1 calc R U . . .
C3 C 0.22741(14) 0.43323(12) 0.16288(10) 0.0217(2) Uani 1 1 d . . . . .
H3 H 0.1010 0.3856 0.1647 0.026 Uiso 1 1 calc R U . . .
C4 C 0.30681(14) 0.59836(12) 0.18603(9) 0.0200(2) Uani 1 1 d . . . . .
C5 C 0.49286(14) 0.66701(12) 0.18313(10) 0.0224(2) Uani 1 1 d . . . . .
H5 H 0.5486 0.7789 0.1995 0.027 Uiso 1 1 calc R U . . .
C6 C 0.59737(14) 0.57346(12) 0.15659(9) 0.0212(2) Uani 1 1 d . . . . .
H6 H 0.7238 0.6203 0.1539 0.025 Uiso 1 1 calc R U . . .
C7 C 0.18496(14) 0.69318(12) 0.21164(11) 0.0242(2) Uani 1 1 d . . . . .
H7A H 0.1230 0.6684 0.2861 0.029 Uiso 1 1 calc R U . . .
H7B H 0.0918 0.6568 0.1429 0.029 Uiso 1 1 calc R U . . .
C8 C 0.27431(14) 0.87249(12) 0.22961(9) 0.0209(2) Uani 1 1 d . . . . .
H8 H 0.3451 0.8983 0.1576 0.025 Uiso 1 1 calc R U . . .
C9 C 0.13562(13) 0.95311(11) 0.24011(9) 0.0198(2) Uani 1 1 d . . . . .
C10 C 0.00604(14) 0.91373(12) 0.14352(10) 0.0228(2) Uani 1 1 d . . . . .
H10 H 0.0035 0.8358 0.0737 0.027 Uiso 1 1 calc R U . . .
C11 C -0.11950(14) 0.98804(13) 0.14902(10) 0.0244(2) Uani 1 1 d . . . . .
H11 H -0.2086 0.9599 0.0837 0.029 Uiso 1 1 calc R U . . .
C12 C -0.11370(14) 1.10346(13) 0.25043(10) 0.0240(2) Uani 1 1 d . . . . .
H12 H -0.2008 1.1526 0.2545 0.029 Uiso 1 1 calc R U . . .
C13 C 0.01765(14) 1.14847(12) 0.34647(10) 0.0219(2) Uani 1 1 d . . . . .
C14 C 0.02987(16) 1.28715(14) 0.44861(11) 0.0289(2) Uani 1 1 d . . . . .
H14A H -0.0876 1.2647 0.4849 0.035 Uiso 1 1 calc R U . . .
H14B H 0.0529 1.3822 0.4129 0.035 Uiso 1 1 calc R U . . .
C15 C 0.17583(16) 1.32413(14) 0.55072(11) 0.0290(2) Uani 1 1 d . . . . .
H15A H 0.2078 1.4351 0.5947 0.035 Uiso 1 1 calc R U . . .
H15B H 0.1294 1.2545 0.6100 0.035 Uiso 1 1 calc R U . . .
C16 C 0.34301(15) 1.29932(12) 0.49834(10) 0.0249(2) Uani 1 1 d . . . . .
H16A H 0.3867 1.3647 0.4360 0.030 Uiso 1 1 calc R U . . .
H16B H 0.4396 1.3316 0.5643 0.030 Uiso 1 1 calc R U . . .
C17 C 0.29499(14) 1.12511(12) 0.44054(9) 0.0207(2) Uani 1 1 d . . . . .
H17 H 0.2537 1.0622 0.5057 0.025 Uiso 1 1 calc R U . . .
C18 C 0.14280(13) 1.07181(11) 0.34189(9) 0.0194(2) Uani 1 1 d . . . . .
C19 C 0.45189(14) 1.08763(12) 0.38452(10) 0.0233(2) Uani 1 1 d . . . . .
H19A H 0.4940 1.1469 0.3184 0.028 Uiso 1 1 calc R U . . .
H19B H 0.5525 1.1197 0.4475 0.028 Uiso 1 1 calc R U . . .
O1 O 0.78730(11) 0.37772(10) 0.10449(9) 0.0361(2) Uani 1 1 d . . . . .
O2 O 0.54714(12) 0.16766(9) 0.07596(8) 0.0316(2) Uani 1 1 d . . . . .
O3 O 0.39563(11) 0.92152(9) 0.33615(7) 0.02579(18) Uani 1 1 d . . . . .
N1 N 0.62353(12) 0.31211(11) 0.10329(8) 0.02339(19) Uani 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
C1 C6 1.3841(14) . ?
C1 C2 1.3900(15) . ?
C1 N1 1.4673(13) . ?
C2 C3 1.3849(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.4007(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3968(14) . ?
C4 C7 1.5136(14) . ?
C5 C6 1.3906(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5266(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O3 1.4297(12) . ?
C8 C9 1.5272(14) . ?
C8 H8 1.0000 . ?
C9 C10 1.3965(14) . ?
C9 C18 1.4068(14) . ?
C10 C11 1.3929(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.3883(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.3945(15) . ?
C12 H12 0.9500 . ?
C13 C18 1.4067(14) . ?
C13 C14 1.5190(15) . ?
C14 C15 1.5308(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5279(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5235(14) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C19 1.5156(14) . ?
C17 C18 1.5176(14) . ?
C17 H17 1.0000 . ?
C19 O3 1.4301(12) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
O1 N1 1.2303(12) . ?
O2 N1 1.2313(12) . ?

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 C1 C2 122.27(9) . . ?
C6 C1 N1 118.67(9) . . ?
C2 C1 N1 119.04(9) . . ?
C3 C2 C1 118.07(9) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 121.45(9) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.72(9) . . ?
C5 C4 C7 123.42(9) . . ?
C3 C4 C7 117.85(9) . . ?
C6 C5 C4 120.75(9) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 118.72(9) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C4 C7 C8 116.58(9) . . ?
C4 C7 H7A 108.1 . . ?
C8 C7 H7A 108.1 . . ?
C4 C7 H7B 108.1 . . ?
C8 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
O3 C8 C7 106.31(8) . . ?
O3 C8 C9 112.82(8) . . ?
C7 C8 C9 111.54(8) . . ?
O3 C8 H8 108.7 . . ?
C7 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
C10 C9 C18 119.82(9) . . ?
C10 C9 C8 118.97(9) . . ?
C18 C9 C8 121.11(9) . . ?
C11 C10 C9 120.35(10) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.65(10) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 121.18(10) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C18 119.21(9) . . ?
C12 C13 C14 118.89(9) . . ?
C18 C13 C14 121.75(10) . . ?
C13 C14 C15 114.57(9) . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 110.70(9) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 108.79(9) . . ?
C17 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C19 C17 C18 108.24(8) . . ?
C19 C17 C16 113.12(9) . . ?
C18 C17 C16 110.81(8) . . ?
C19 C17 H17 108.2 . . ?
C18 C17 H17 108.2 . . ?
C16 C17 H17 108.2 . . ?
C13 C18 C9 119.75(9) . . ?
C13 C18 C17 120.60(9) . . ?
C9 C18 C17 119.46(9) . . ?
O3 C19 C17 109.06(8) . . ?
O3 C19 H19A 109.9 . . ?
C17 C19 H19A 109.9 . . ?
O3 C19 H19B 109.9 . . ?
C17 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
C8 O3 C19 112.67(8) . . ?
O1 N1 O2 123.12(9) . . ?
O1 N1 C1 118.47(9) . . ?
O2 N1 C1 118.40(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
C6 C1 C2 C3 0.67(15) . . . . ?
N1 C1 C2 C3 -177.95(9) . . . . ?
C1 C2 C3 C4 -0.61(16) . . . . ?
C2 C3 C4 C5 -0.02(16) . . . . ?
C2 C3 C4 C7 179.33(9) . . . . ?
C3 C4 C5 C6 0.63(16) . . . . ?
C7 C4 C5 C6 -178.67(10) . . . . ?
C2 C1 C6 C5 -0.07(15) . . . . ?
N1 C1 C6 C5 178.55(9) . . . . ?
C4 C5 C6 C1 -0.59(16) . . . . ?
C5 C4 C7 C8 2.54(15) . . . . ?
C3 C4 C7 C8 -176.77(9) . . . . ?
C4 C7 C8 O3 -63.16(11) . . . . ?
C4 C7 C8 C9 173.48(9) . . . . ?
O3 C8 C9 C10 -178.65(9) . . . . ?
C7 C8 C9 C10 -59.07(12) . . . . ?
O3 C8 C9 C18 4.91(13) . . . . ?
C7 C8 C9 C18 124.49(10) . . . . ?
C18 C9 C10 C11 -1.91(15) . . . . ?
C8 C9 C10 C11 -178.40(9) . . . . ?
C9 C10 C11 C12 0.94(16) . . . . ?
C10 C11 C12 C13 1.03(16) . . . . ?
C11 C12 C13 C18 -2.00(15) . . . . ?
C11 C12 C13 C14 173.57(10) . . . . ?
C12 C13 C14 C15 178.70(10) . . . . ?
C18 C13 C14 C15 -5.85(15) . . . . ?
C13 C14 C15 C16 37.30(13) . . . . ?
C14 C15 C16 C17 -63.99(12) . . . . ?
C15 C16 C17 C19 179.51(9) . . . . ?
C15 C16 C17 C18 57.75(11) . . . . ?
C12 C13 C18 C9 1.00(15) . . . . ?
C14 C13 C18 C9 -174.43(9) . . . . ?
C12 C13 C18 C17 175.90(9) . . . . ?
C14 C13 C18 C17 0.46(15) . . . . ?
C10 C9 C18 C13 0.93(15) . . . . ?
C8 C9 C18 C13 177.33(9) . . . . ?
C10 C9 C18 C17 -174.02(9) . . . . ?
C8 C9 C18 C17 2.38(14) . . . . ?
C19 C17 C18 C13 -151.31(9) . . . . ?
C16 C17 C18 C13 -26.74(13) . . . . ?
C19 C17 C18 C9 23.59(12) . . . . ?
C16 C17 C18 C9 148.17(9) . . . . ?
C18 C17 C19 O3 -58.57(11) . . . . ?
C16 C17 C19 O3 178.24(8) . . . . ?
C7 C8 O3 C19 -163.64(8) . . . . ?
C9 C8 O3 C19 -41.08(11) . . . . ?
C17 C19 O3 C8 70.47(11) . . . . ?
C6 C1 N1 O1 3.61(14) . . . . ?
C2 C1 N1 O1 -177.72(10) . . . . ?
C6 C1 N1 O2 -175.53(9) . . . . ?
C2 C1 N1 O2 3.14(14) . . . . ?

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hx'
####################################################################### 
# 
# 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_jmcm220531
_audit_block_doi                 10.5517/ccdc.csd.cc2f5f13
_database_code_depnum_ccdc_archive 'CCDC 2239534'
loop_
_audit_author_name
_audit_author_address
'Corine Bailly'
;Service de Radiocristallographie Federation de Chimie Le Bel Universite de Strasbourg
France
;
_audit_update_record             
;
2023-02-02 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-(3,5-bis(trifluoromethyl)benzyl)-6,7-dimethoxyisochromane
_chemical_name_common            ?
_chemical_melting_point          416-418
_chemical_formula_moiety         'C20 H18 F6 O3'
_chemical_formula_sum            'C20 H18 F6 O3'
_chemical_formula_weight         420.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6103(7)
_cell_length_b                   7.9713(5)
_cell_length_c                   27.483(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.244(3)
_cell_angle_gamma                90
_cell_volume                     1885.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9819
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.97

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7261
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            78056
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.464
_diffrn_reflns_theta_max         28.011
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4574
_reflns_number_gt                3963
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0543P)²+1.3549P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4574
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_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
C1 C 0.45807(15) 0.32482(18) 0.40013(5) 0.0190(3) Uani 1 1 d . . . . .
C2 C 0.39820(16) 0.48426(19) 0.39082(5) 0.0209(3) Uani 1 1 d . . . . .
H2 H 0.4176 0.5379 0.3607 0.025 Uiso 1 1 calc R U . . .
C3 C 0.31010(16) 0.56498(18) 0.42559(5) 0.0210(3) Uani 1 1 d . . . . .
C4 C 0.28006(16) 0.48943(18) 0.47002(5) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.2211 0.5457 0.4938 0.024 Uiso 1 1 calc R U . . .
C5 C 0.33847(16) 0.32981(18) 0.47865(5) 0.0185(3) Uani 1 1 d . . . . .
C6 C 0.42747(16) 0.24769(18) 0.44433(5) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.4674 0.1389 0.4511 0.023 Uiso 1 1 calc R U . . .
C7 C 0.2401(2) 0.7329(2) 0.41411(6) 0.0293(3) Uani 1 1 d . . . . .
C8 C 0.29858(18) 0.24001(19) 0.52468(5) 0.0236(3) Uani 1 1 d . . . . .
C9 C 0.56122(16) 0.24213(19) 0.36329(5) 0.0215(3) Uani 1 1 d . . . . .
H9A H 0.5227 0.2690 0.3300 0.026 Uiso 1 1 calc R U . . .
H9B H 0.5575 0.1188 0.3675 0.026 Uiso 1 1 calc R U . . .
C10 C 0.72873(15) 0.30314(18) 0.36977(5) 0.0171(3) Uani 1 1 d . . . . .
H10 H 0.7305 0.4280 0.3663 0.021 Uiso 1 1 calc R U . . .
C11 C 0.83790(15) 0.22698(17) 0.33294(5) 0.0165(3) Uani 1 1 d . . . . .
C12 C 0.80150(16) 0.23929(17) 0.28293(5) 0.0183(3) Uani 1 1 d . . . . .
H12 H 0.7092 0.2953 0.2725 0.022 Uiso 1 1 calc R U . . .
C13 C 0.89880(16) 0.17061(17) 0.24854(5) 0.0185(3) Uani 1 1 d . . . . .
C14 C 1.03659(16) 0.08975(17) 0.26419(5) 0.0188(3) Uani 1 1 d . . . . .
C15 C 1.07364(15) 0.08028(17) 0.31323(5) 0.0186(3) Uani 1 1 d . . . . .
H15 H 1.1672 0.0266 0.3236 0.022 Uiso 1 1 calc R U . . .
C16 C 0.97502(15) 0.14888(17) 0.34803(5) 0.0165(3) Uani 1 1 d . . . . .
C17 C 1.02037(16) 0.1433(2) 0.40137(5) 0.0221(3) Uani 1 1 d . . . . .
H17A H 1.1338 0.1606 0.4054 0.027 Uiso 1 1 calc R U . . .
H17B H 0.9944 0.0321 0.4150 0.027 Uiso 1 1 calc R U . . .
C18 C 0.93446(17) 0.2787(2) 0.42822(5) 0.0248(3) Uani 1 1 d . . . . .
H18A H 0.9565 0.2692 0.4636 0.030 Uiso 1 1 calc R U . . .
H18B H 0.9696 0.3906 0.4173 0.030 Uiso 1 1 calc R U . . .
C19 C 0.7352(2) 0.2596(2) 0.18245(6) 0.0336(4) Uani 1 1 d . . . . .
H19A H 0.6439 0.2017 0.1950 0.050 Uiso 1 1 calc R U . . .
H19B H 0.7308 0.2585 0.1468 0.050 Uiso 1 1 calc R U . . .
H19C H 0.7364 0.3758 0.1941 0.050 Uiso 1 1 calc R U . . .
C20 C 1.2769(2) -0.0342(3) 0.24190(6) 0.0367(4) Uani 1 1 d . . . . .
H20A H 1.3367 0.0545 0.2584 0.055 Uiso 1 1 calc R U . . .
H20B H 1.3319 -0.0712 0.2130 0.055 Uiso 1 1 calc R U . . .
H20C H 1.2645 -0.1293 0.2641 0.055 Uiso 1 1 calc R U . . .
O1 O 0.77175(12) 0.26092(14) 0.41867(3) 0.0228(2) Uani 1 1 d . . . . .
O2 O 0.87334(13) 0.17570(14) 0.19931(4) 0.0255(2) Uani 1 1 d . . . . .
O3 O 1.12767(13) 0.02891(14) 0.22776(4) 0.0261(2) Uani 1 1 d . . . . .
F1 F 0.32714(13) 0.82558(13) 0.38479(4) 0.0390(3) Uani 1 1 d . . . . .
F2 F 0.10211(13) 0.71778(16) 0.39119(6) 0.0555(4) Uani 1 1 d . . . . .
F3 F 0.21908(17) 0.82596(14) 0.45377(4) 0.0533(4) Uani 1 1 d . . . . .
F4 F 0.18697(15) 0.12790(18) 0.51748(4) 0.0529(4) Uani 1 1 d . . . . .
F5 F 0.2507(2) 0.34327(16) 0.55909(4) 0.0650(5) Uani 1 1 d . . . . .
F6 F 0.41807(14) 0.15598(16) 0.54412(4) 0.0469(3) Uani 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
C1 C6 1.3917(19) . ?
C1 C2 1.393(2) . ?
C1 C9 1.5122(18) . ?
C2 C3 1.3909(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3907(19) . ?
C3 C7 1.498(2) . ?
C4 C5 1.3867(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3916(18) . ?
C5 C8 1.5001(19) . ?
C6 H6 0.9500 . ?
C7 F3 1.334(2) . ?
C7 F1 1.3352(19) . ?
C7 F2 1.338(2) . ?
C8 F4 1.324(2) . ?
C8 F5 1.3261(18) . ?
C8 F6 1.3299(18) . ?
C9 C10 1.5289(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O1 1.4265(16) . ?
C10 C11 1.5225(17) . ?
C10 H10 1.0000 . ?
C11 C16 1.3901(18) . ?
C11 C12 1.4064(18) . ?
C12 C13 1.3890(18) . ?
C12 H12 0.9500 . ?
C13 O2 1.3666(16) . ?
C13 C14 1.4093(19) . ?
C14 O3 1.3737(16) . ?
C14 C15 1.3803(19) . ?
C15 C16 1.4035(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.5095(18) . ?
C17 C18 1.510(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O1 1.4269(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O2 1.4325(19) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O3 1.426(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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 C1 C2 119.14(12) . . ?
C6 C1 C9 121.12(13) . . ?
C2 C1 C9 119.67(13) . . ?
C3 C2 C1 120.07(13) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 121.17(13) . . ?
C4 C3 C7 119.36(13) . . ?
C2 C3 C7 119.41(13) . . ?
C5 C4 C3 118.28(13) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 121.24(13) . . ?
C4 C5 C8 119.55(12) . . ?
C6 C5 C8 119.13(13) . . ?
C5 C6 C1 120.09(13) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
F3 C7 F1 105.86(15) . . ?
F3 C7 F2 107.42(14) . . ?
F1 C7 F2 105.66(13) . . ?
F3 C7 C3 112.68(13) . . ?
F1 C7 C3 113.16(13) . . ?
F2 C7 C3 111.57(14) . . ?
F4 C8 F5 106.85(15) . . ?
F4 C8 F6 105.83(13) . . ?
F5 C8 F6 106.02(13) . . ?
F4 C8 C5 112.01(12) . . ?
F5 C8 C5 112.69(13) . . ?
F6 C8 C5 112.94(13) . . ?
C1 C9 C10 110.47(11) . . ?
C1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O1 C10 C11 112.39(11) . . ?
O1 C10 C9 105.05(11) . . ?
C11 C10 C9 112.97(11) . . ?
O1 C10 H10 108.8 . . ?
C11 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
C16 C11 C12 119.51(12) . . ?
C16 C11 C10 120.85(12) . . ?
C12 C11 C10 119.62(12) . . ?
C13 C12 C11 120.84(12) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
O2 C13 C12 125.16(12) . . ?
O2 C13 C14 115.58(12) . . ?
C12 C13 C14 119.26(12) . . ?
O3 C14 C15 124.68(12) . . ?
O3 C14 C13 115.40(12) . . ?
C15 C14 C13 119.89(12) . . ?
C14 C15 C16 120.91(12) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 119.58(12) . . ?
C11 C16 C17 120.21(12) . . ?
C15 C16 C17 120.18(12) . . ?
C16 C17 C18 109.53(12) . . ?
C16 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O1 C18 C17 109.16(12) . . ?
O1 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
O1 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 O1 C18 112.56(11) . . ?
C13 O2 C19 116.63(11) . . ?
C14 O3 C20 116.81(12) . . ?

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
C6 C1 C2 C3 0.5(2) . . . . ?
C9 C1 C2 C3 -176.56(13) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C2 C3 C7 -177.08(14) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C7 C3 C4 C5 176.24(14) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C3 C4 C5 C8 -175.64(13) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C8 C5 C6 C1 176.18(13) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C9 C1 C6 C5 176.83(13) . . . . ?
C4 C3 C7 F3 30.0(2) . . . . ?
C2 C3 C7 F3 -152.84(15) . . . . ?
C4 C3 C7 F1 150.03(15) . . . . ?
C2 C3 C7 F1 -32.8(2) . . . . ?
C4 C3 C7 F2 -90.98(18) . . . . ?
C2 C3 C7 F2 86.21(18) . . . . ?
C4 C5 C8 F4 100.69(17) . . . . ?
C6 C5 C8 F4 -76.23(18) . . . . ?
C4 C5 C8 F5 -19.8(2) . . . . ?
C6 C5 C8 F5 163.25(15) . . . . ?
C4 C5 C8 F6 -139.94(14) . . . . ?
C6 C5 C8 F6 43.14(19) . . . . ?
C6 C1 C9 C10 -93.87(16) . . . . ?
C2 C1 C9 C10 83.12(16) . . . . ?
C1 C9 C10 O1 58.38(15) . . . . ?
C1 C9 C10 C11 -178.78(11) . . . . ?
O1 C10 C11 C16 -9.21(18) . . . . ?
C9 C10 C11 C16 -127.87(14) . . . . ?
O1 C10 C11 C12 172.34(12) . . . . ?
C9 C10 C11 C12 53.68(17) . . . . ?
C16 C11 C12 C13 1.7(2) . . . . ?
C10 C11 C12 C13 -179.84(13) . . . . ?
C11 C12 C13 O2 179.83(13) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
O2 C13 C14 O3 0.81(18) . . . . ?
C12 C13 C14 O3 -178.55(13) . . . . ?
O2 C13 C14 C15 179.09(13) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
O3 C14 C15 C16 178.71(13) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C12 C11 C16 C15 -1.3(2) . . . . ?
C10 C11 C16 C15 -179.79(12) . . . . ?
C12 C11 C16 C17 176.50(13) . . . . ?
C10 C11 C16 C17 -2.0(2) . . . . ?
C14 C15 C16 C11 0.2(2) . . . . ?
C14 C15 C16 C17 -177.63(13) . . . . ?
C11 C16 C17 C18 -20.21(18) . . . . ?
C15 C16 C17 C18 157.62(13) . . . . ?
C16 C17 C18 O1 54.44(16) . . . . ?
C11 C10 O1 C18 45.17(16) . . . . ?
C9 C10 O1 C18 168.39(12) . . . . ?
C17 C18 O1 C10 -70.05(15) . . . . ?
C12 C13 O2 C19 0.3(2) . . . . ?
C14 C13 O2 C19 -179.05(14) . . . . ?
C15 C14 O3 C20 -6.0(2) . . . . ?
C13 C14 O3 C20 172.19(14) . . . . ?

_refine_diff_density_max         0.541
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hx'
