#------------------------------------------------------------------------------
#$Date: 2024-03-04 21:47:46 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290081 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/26/7132675.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_7132675
loop_
_publ_author_name
'Yu, Jiulong'
'Wu, Jinyu'
'Zhu, Yu'
'Xiong, Dong'
'Yang, Lin'
'Li, Jun'
'Zheng, Jianfeng'
_publ_section_title
;
 Chiral phosphoric acid-catalyzed enantioselective [5+1] cycloaddition
 reaction of C,N-cyclic azomethine imines with isocyanides.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2637
_journal_page_last               2640
_journal_paper_doi               10.1039/d3cc05890e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C19 H16 F2 O2'
_chemical_formula_weight         314.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc29hwk8
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.534(2)
_cell_length_b                   12.716(3)
_cell_length_c                   15.945(4)
_cell_measurement_reflns_used    6113
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      66.32
_cell_measurement_theta_min      2.77
_cell_volume                     1527.6(7)
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1260)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 VENTURE DUO PHOTON III'
_diffrn_radiation_monochromator  'Helios MX Multilayer Optic'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10659
_diffrn_reflns_theta_full        66.74
_diffrn_reflns_theta_max         66.74
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_type              'Incoatec Ius 3.0'
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.215
_refine_ls_abs_structure_details
;

Flack x determined using 913 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2445
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0318
_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)+(0.0347P)²+0.6455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.826
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                2276
_reflns_number_total             2445
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc05890e2.cif
_cod_data_source_block           20210910a
_cod_depositor_comments
'Adding full bibliography for 7132675--7132678.cif.'
_cod_database_code               7132675
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.6454(3) 0.13962(15) 0.39603(15) 0.0431(6) Uani d . . . 1 . .
F F2 0.8857(3) 0.17976(15) 0.46044(15) 0.0406(6) Uani d . . . 1 . .
O O1 0.7432(3) 0.33224(16) 0.36040(15) 0.0277(5) Uani d . . . 1 . .
O O2 0.5471(4) 0.56591(18) 0.50993(18) 0.0401(6) Uani d . . . 1 . .
C C1 0.6243(4) 0.1644(2) 0.5437(2) 0.0236(7) Uani d . . . 1 . .
C C2 0.4518(4) 0.1218(2) 0.5454(2) 0.0256(7) Uani d . . . 1 . .
C C3 0.3812(4) 0.0918(2) 0.6225(2) 0.0265(7) Uani d . . . 1 . .
H H3 0.266681 0.060614 0.623964 0.032000 Uiso calc U . R 1 . .
C C4 0.4718(5) 0.1059(2) 0.6972(2) 0.0259(7) Uani d . . . 1 . .
C C5 0.6381(5) 0.1517(2) 0.6940(2) 0.0275(8) Uani d . . . 1 . .
H H5 0.700011 0.163749 0.744977 0.033000 Uiso calc U . R 1 . .
C C6 0.7186(4) 0.1807(2) 0.6187(2) 0.0261(7) Uani d . . . 1 . .
C C7 0.7067(4) 0.1985(2) 0.4613(2) 0.0281(7) Uani d . . . 1 . .
C C8 0.6797(4) 0.3130(2) 0.4391(2) 0.0243(7) Uani d . . . 1 . .
C C9 0.6100(4) 0.3863(2) 0.4891(2) 0.0264(7) Uani d . . . 1 . .
H H9 0.562073 0.366147 0.541796 0.032000 Uiso calc U . R 1 . .
C C10 0.6058(4) 0.4964(2) 0.4645(2) 0.0281(7) Uani d . . . 1 . .
C C11 0.6792(4) 0.5169(2) 0.3805(2) 0.0259(7) Uani d . . . 1 . .
C C12 0.6863(5) 0.6188(3) 0.3466(3) 0.0322(8) Uani d . . . 1 . .
H H12 0.645660 0.676869 0.378774 0.039000 Uiso calc U . R 1 . .
C C13 0.7518(5) 0.6348(3) 0.2671(2) 0.0356(9) Uani d . . . 1 . .
H H13 0.757292 0.703985 0.244773 0.043000 Uiso calc U . R 1 . .
C C14 0.8097(5) 0.5506(3) 0.2194(3) 0.0354(8) Uani d . . . 1 . .
H H14 0.853847 0.562701 0.164441 0.042000 Uiso calc U . R 1 . .
C C15 0.8045(5) 0.4494(3) 0.2503(2) 0.0305(8) Uani d . . . 1 . .
H H15 0.843402 0.391595 0.217289 0.037000 Uiso calc U . R 1 . .
C C16 0.7401(5) 0.4344(2) 0.3317(2) 0.0263(7) Uani d . . . 1 . .
C C17 0.3332(5) 0.1085(3) 0.4697(3) 0.0395(9) Uani d . . . 1 . .
H H17A 0.210966 0.096032 0.488203 0.059000 Uiso calc U . R 1 . .
H H17B 0.374220 0.048469 0.436391 0.059000 Uiso calc U . R 1 . .
H H17C 0.337520 0.172426 0.435420 0.059000 Uiso calc U . R 1 . .
C C18 0.3915(6) 0.0737(3) 0.7799(2) 0.0395(9) Uani d . . . 1 . .
H H18A 0.435155 0.120333 0.824298 0.059000 Uiso calc U . R 1 . .
H H18B 0.425269 0.001047 0.792640 0.059000 Uiso calc U . R 1 . .
H H18C 0.261917 0.078918 0.776524 0.059000 Uiso calc U . R 1 . .
C C19 0.9021(4) 0.2288(3) 0.6244(3) 0.0381(9) Uani d . . . 1 . .
H H19A 0.925562 0.250180 0.682407 0.057000 Uiso calc U . R 1 . .
H H19B 0.908746 0.290438 0.587649 0.057000 Uiso calc U . R 1 . .
H H19C 0.990767 0.176873 0.606868 0.057000 Uiso calc U . R 1 . .
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'
F F 0.0727 0.0534 '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'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/ajoc.202200031 2022
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O1 C16 . . 118.0(3) ?
C6 C1 C2 . . 120.5(3) ?
C6 C1 C7 . . 119.2(3) ?
C2 C1 C7 . . 120.3(3) ?
C3 C2 C1 . . 118.3(3) ?
C3 C2 C17 . . 116.7(3) ?
C1 C2 C17 . . 125.0(3) ?
C4 C3 C2 . . 122.4(3) ?
C4 C3 H3 . . 118.800000 ?
C2 C3 H3 . . 118.800000 ?
C5 C4 C3 . . 118.0(3) ?
C5 C4 C18 . . 120.7(3) ?
C3 C4 C18 . . 121.3(3) ?
C4 C5 C6 . . 122.5(3) ?
C4 C5 H5 . . 118.700000 ?
C6 C5 H5 . . 118.700000 ?
C5 C6 C1 . . 118.2(3) ?
C5 C6 C19 . . 116.9(3) ?
C1 C6 C19 . . 124.9(3) ?
F1 C7 F2 . . 103.3(3) ?
F1 C7 C8 . . 107.7(3) ?
F2 C7 C8 . . 107.3(3) ?
F1 C7 C1 . . 111.4(3) ?
F2 C7 C1 . . 111.2(3) ?
C8 C7 C1 . . 115.0(3) ?
C9 C8 O1 . . 124.1(3) ?
C9 C8 C7 . . 125.9(3) ?
O1 C8 C7 . . 109.9(3) ?
C8 C9 C10 . . 121.4(3) ?
C8 C9 H9 . . 119.300000 ?
C10 C9 H9 . . 119.300000 ?
O2 C10 C9 . . 122.9(3) ?
O2 C10 C11 . . 123.1(3) ?
C9 C10 C11 . . 114.0(3) ?
C16 C11 C12 . . 118.0(3) ?
C16 C11 C10 . . 120.1(3) ?
C12 C11 C10 . . 121.8(3) ?
C13 C12 C11 . . 120.3(3) ?
C13 C12 H12 . . 119.900000 ?
C11 C12 H12 . . 119.900000 ?
C12 C13 C14 . . 120.3(3) ?
C12 C13 H13 . . 119.800000 ?
C14 C13 H13 . . 119.800000 ?
C15 C14 C13 . . 121.2(4) ?
C15 C14 H14 . . 119.400000 ?
C13 C14 H14 . . 119.400000 ?
C14 C15 C16 . . 117.9(3) ?
C14 C15 H15 . . 121.000000 ?
C16 C15 H15 . . 121.000000 ?
O1 C16 C11 . . 122.2(3) ?
O1 C16 C15 . . 115.5(3) ?
C11 C16 C15 . . 122.3(3) ?
C2 C17 H17A . . 109.500000 ?
C2 C17 H17B . . 109.500000 ?
H17A C17 H17B . . 109.500000 ?
C2 C17 H17C . . 109.500000 ?
H17A C17 H17C . . 109.500000 ?
H17B C17 H17C . . 109.500000 ?
C4 C18 H18A . . 109.500000 ?
C4 C18 H18B . . 109.500000 ?
H18A C18 H18B . . 109.500000 ?
C4 C18 H18C . . 109.500000 ?
H18A C18 H18C . . 109.500000 ?
H18B C18 H18C . . 109.500000 ?
C6 C19 H19A . . 109.500000 ?
C6 C19 H19B . . 109.500000 ?
H19A C19 H19B . . 109.500000 ?
C6 C19 H19C . . 109.500000 ?
H19A C19 H19C . . 109.500000 ?
H19B C19 H19C . . 109.500000 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C7 . 1.363(4) ?
F2 C7 . 1.369(4) ?
O1 C8 . 1.366(4) ?
O1 C16 . 1.378(4) ?
O2 C10 . 1.225(4) ?
C1 C6 . 1.406(5) ?
C1 C2 . 1.408(4) ?
C1 C7 . 1.517(5) ?
C2 C3 . 1.394(5) ?
C2 C17 . 1.510(5) ?
C3 C4 . 1.383(5) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.383(5) ?
C4 C18 . 1.508(5) ?
C5 C6 . 1.394(5) ?
C5 H5 . 0.950000 ?
C6 C19 . 1.514(4) ?
C7 C8 . 1.512(4) ?
C8 C9 . 1.334(5) ?
C9 C10 . 1.455(5) ?
C9 H9 . 0.950000 ?
C10 C11 . 1.473(5) ?
C11 C16 . 1.384(5) ?
C11 C12 . 1.404(5) ?
C12 C13 . 1.376(6) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.384(6) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.378(5) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.398(5) ?
C15 H15 . 0.950000 ?
C17 H17A . 0.980000 ?
C17 H17B . 0.980000 ?
C17 H17C . 0.980000 ?
C18 H18A . 0.980000 ?
C18 H18B . 0.980000 ?
C18 H18C . 0.980000 ?
C19 H19A . 0.980000 ?
C19 H19B . 0.980000 ?
C19 H19C . 0.980000 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -3.0(4) ?
C7 C1 C2 C3 . . . . -179.8(3) ?
C6 C1 C2 C17 . . . . 175.1(3) ?
C7 C1 C2 C17 . . . . -1.7(5) ?
C1 C2 C3 C4 . . . . 2.3(4) ?
C17 C2 C3 C4 . . . . -176.0(3) ?
C2 C3 C4 C5 . . . . 0.1(4) ?
C2 C3 C4 C18 . . . . 179.4(3) ?
C3 C4 C5 C6 . . . . -1.9(5) ?
C18 C4 C5 C6 . . . . 178.8(3) ?
C4 C5 C6 C1 . . . . 1.2(4) ?
C4 C5 C6 C19 . . . . -179.2(3) ?
C2 C1 C6 C5 . . . . 1.3(4) ?
C7 C1 C6 C5 . . . . 178.1(3) ?
C2 C1 C6 C19 . . . . -178.2(3) ?
C7 C1 C6 C19 . . . . -1.4(4) ?
C6 C1 C7 F1 . . . . 153.0(3) ?
C2 C1 C7 F1 . . . . -30.3(4) ?
C6 C1 C7 F2 . . . . 38.2(4) ?
C2 C1 C7 F2 . . . . -145.0(3) ?
C6 C1 C7 C8 . . . . -84.1(4) ?
C2 C1 C7 C8 . . . . 92.7(3) ?
C16 O1 C8 C9 . . . . 2.1(5) ?
C16 O1 C8 C7 . . . . -175.9(3) ?
F1 C7 C8 C9 . . . . 133.1(3) ?
F2 C7 C8 C9 . . . . -116.2(4) ?
C1 C7 C8 C9 . . . . 8.2(5) ?
F1 C7 C8 O1 . . . . -48.9(4) ?
F2 C7 C8 O1 . . . . 61.8(3) ?
C1 C7 C8 O1 . . . . -173.8(3) ?
O1 C8 C9 C10 . . . . -3.8(5) ?
C7 C8 C9 C10 . . . . 173.9(3) ?
C8 C9 C10 O2 . . . . -178.0(3) ?
C8 C9 C10 C11 . . . . 1.8(5) ?
O2 C10 C11 C16 . . . . -178.7(3) ?
C9 C10 C11 C16 . . . . 1.6(4) ?
O2 C10 C11 C12 . . . . -0.1(5) ?
C9 C10 C11 C12 . . . . -179.8(3) ?
C16 C11 C12 C13 . . . . 0.2(5) ?
C10 C11 C12 C13 . . . . -178.5(3) ?
C11 C12 C13 C14 . . . . 0.6(6) ?
C12 C13 C14 C15 . . . . -0.4(6) ?
C13 C14 C15 C16 . . . . -0.5(5) ?
C8 O1 C16 C11 . . . . 1.5(5) ?
C8 O1 C16 C15 . . . . -179.2(3) ?
C12 C11 C16 O1 . . . . 178.1(3) ?
C10 C11 C16 O1 . . . . -3.2(5) ?
C12 C11 C16 C15 . . . . -1.2(5) ?
C10 C11 C16 C15 . . . . 177.5(3) ?
C14 C15 C16 O1 . . . . -178.0(3) ?
C14 C15 C16 C11 . . . . 1.4(5) ?
