#------------------------------------------------------------------------------
#$Date: 2023-04-13 15:19:33 +0300 (Thu, 13 Apr 2023) $
#$Revision: 282621 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/84/1568416.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1568416
loop_
_publ_author_name
'Muller, Cyprien'
'Horký, Filip'
'Vayer, Marie'
'Golushko, Andrei'
'Lebœuf, David'
'Moran, Joseph'
_publ_section_title
;
 Synthesis of functionalised isochromans: epoxides as aldehyde surrogates
 in hexafluoroisopropanol
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              2983
_journal_page_last               2989
_journal_paper_doi               10.1039/D2SC06692K
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C20 H18 F6 O3'
_chemical_formula_sum            'C20 H18 F6 O3'
_chemical_formula_weight         420.34
_chemical_melting_point          417.0(10)
_chemical_name_systematic
1-(3,5-bis(trifluoromethyl)benzyl)-6,7-dimethoxyisochromane
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2f5f13
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-02-02 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.244(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6103(7)
_cell_length_b                   7.9713(5)
_cell_length_c                   27.483(2)
_cell_measurement_reflns_used    9819
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.46
_cell_volume                     1885.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            78056
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.011
_diffrn_reflns_theta_min         2.464
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Hx'
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0543P)²+1.3549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3963
_reflns_number_total             4574
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc06692k2.cif
_cod_data_source_block           jmcm220531
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '416-418' was changed to
'417.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1568413--1568416.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1568416
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.995
#END Tags that were not found in dictionaries
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'
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 . . . . .
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'
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_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_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) . . . . ?
