#------------------------------------------------------------------------------
#$Date: 2023-04-13 15:19:33 +0300 (Thu, 13 Apr 2023) $
#$Revision: 282621 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/84/1568415.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_1568415
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         'C19 H19 N O3'
_chemical_formula_sum            'C19 H19 N O3'
_chemical_formula_weight         309.35
_chemical_melting_point          416.0(10)
_chemical_name_systematic
1-(4-nitrobenzyl)-3a,4,5,6-tetrahydro-1H,3H-benzo[de]isochromene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2f5f02
_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                100.8750(10)
_cell_angle_beta                 90.0200(10)
_cell_angle_gamma                110.5260(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9718(3)
_cell_length_b                   9.2217(3)
_cell_length_c                   11.1636(4)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.41
_cell_volume                     752.80(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0240
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            39094
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.044
_diffrn_reflns_theta_min         1.862
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Hx'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0540P)²+0.2532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3349
_reflns_number_total             3652
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc06692k2.cif
_cod_data_source_block           jmcm220530
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '415-417' was changed to
'416.0(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_database_code               1568415
#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   0.989
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 . . . . .
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'
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_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_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) . . . . ?
