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#$Date: 2024-01-06 09:14:26 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288720 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/01/1570174.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_1570174
loop_
_publ_author_name
'Zhang, Ying'
'Yang, Jimin'
'Ruan, Yu-Long'
'Liao, Ling'
'Ma, Chuang'
'Xue, Xiao-Song'
'Yu, Jin-Sheng'
_publ_section_title
;
 Nickel-catalysed asymmetric hydromonofluoromethylation of 1,3-enynes for
 enantioselective construction of monofluoromethyl-tethered chiral
 allenes.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              12676
_journal_page_last               12683
_journal_paper_doi               10.1039/d3sc04474b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C13 H15 F O2'
_chemical_formula_weight         222.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.606(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7657(2)
_cell_length_b                   8.4827(4)
_cell_length_c                   12.1582(5)
_cell_measurement_temperature    571(2)
_cell_volume                     586.30(4)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10142
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         3.687
_exptl_absorpt_coefficient_mu    0.779
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1977
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0419
_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)+(0.0527P)²+0.0372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.892
_reflns_number_gt                1796
_reflns_number_total             1977
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04474b2.cif
_cod_data_source_block           exp_2845
_cod_depositor_comments
'Adding full bibliography for 1570174--1570176.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1570174
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_min   0.783
_shelx_estimated_absorpt_t_max   0.847
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
F1 F -0.5714(3) -0.6181(2) -0.88376(13) 0.0520(5) Uani 1 1 d . . . . .
O1 O -0.7721(4) -0.3285(3) -0.94486(19) 0.0579(6) Uani 1 1 d . . . . .
H1 H -0.807685 -0.247063 -0.979953 0.087 Uiso 1 1 calc R U . . .
O2 O -0.1270(4) -0.5485(3) -0.94490(18) 0.0588(6) Uani 1 1 d . . . . .
H2 H 0.006183 -0.488173 -0.954872 0.071 Uiso 1 1 d R U . . .
C1 C -1.0226(6) -0.6583(5) -0.3874(3) 0.0586(9) Uani 1 1 d . . . . .
H1A H -1.127287 -0.731261 -0.425050 0.070 Uiso 1 1 calc R U . . .
C2 C -1.0592(6) -0.5990(5) -0.2853(3) 0.0680(10) Uani 1 1 d . . . . .
H2A H -1.189926 -0.631131 -0.255496 0.082 Uiso 1 1 calc R U . . .
C3 C -0.9044(7) -0.4938(5) -0.2284(3) 0.0699(10) Uani 1 1 d . . . . .
H3 H -0.928952 -0.455126 -0.159701 0.084 Uiso 1 1 calc R U . . .
C4 C -0.7129(7) -0.4452(5) -0.2728(3) 0.0658(9) Uani 1 1 d . . . . .
H4 H -0.606746 -0.374407 -0.233595 0.079 Uiso 1 1 calc R U . . .
C5 C -0.6770(6) -0.5006(4) -0.3747(3) 0.0561(8) Uani 1 1 d . . . . .
H5 H -0.548467 -0.464853 -0.404732 0.067 Uiso 1 1 calc R U . . .
C6 C -0.8300(5) -0.6091(4) -0.4334(2) 0.0488(7) Uani 1 1 d . . . . .
C7 C -0.7876(7) -0.6744(5) -0.5410(3) 0.0606(9) Uani 1 1 d . . . . .
H7 H -0.878835 -0.759447 -0.570822 0.073 Uiso 1 1 calc R U . . .
C8 C -0.6299(6) -0.6199(5) -0.5968(2) 0.0609(8) Uani 1 1 d . . . . .
C9 C -0.4708(6) -0.5622(5) -0.6483(3) 0.0620(9) Uani 1 1 d . . . . .
H9 H -0.318996 -0.602112 -0.630153 0.074 Uiso 1 1 calc R U . . .
C10 C -0.5126(5) -0.4356(4) -0.7352(2) 0.0508(7) Uani 1 1 d . . . . .
H10A H -0.422904 -0.343182 -0.706937 0.061 Uiso 1 1 calc R U . . .
H10B H -0.677770 -0.407019 -0.746271 0.061 Uiso 1 1 calc R U . . .
C11 C -0.4484(5) -0.4783(3) -0.8475(2) 0.0422(6) Uani 1 1 d . . . . .
C12 C -0.5261(5) -0.3544(4) -0.9350(3) 0.0529(7) Uani 1 1 d . . . . .
H12A H -0.442393 -0.256772 -0.914497 0.063 Uiso 1 1 calc R U . . .
H12B H -0.489092 -0.388709 -1.006226 0.063 Uiso 1 1 calc R U . . .
C13 C -0.1879(5) -0.5136(4) -0.8390(3) 0.0533(8) Uani 1 1 d . . . . .
H13A H -0.097634 -0.423266 -0.807112 0.064 Uiso 1 1 calc R U . . .
H13B H -0.147086 -0.602580 -0.789472 0.064 Uiso 1 1 calc R U . . .
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_
_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
C12 O1 H1 109.5 . . ?
C13 O2 H2 109.4 . . ?
C2 C1 C6 120.2(3) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.3(3) . . ?
C5 C6 C7 121.3(3) . . ?
C1 C6 C7 120.4(3) . . ?
C8 C7 C6 124.0(4) . . ?
C8 C7 H7 118.0 . . ?
C6 C7 H7 118.0 . . ?
C9 C8 C7 177.5(4) . . ?
C8 C9 C10 124.8(3) . . ?
C8 C9 H9 117.6 . . ?
C10 C9 H9 117.6 . . ?
C9 C10 C11 115.4(3) . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
F1 C11 C12 106.8(2) . . ?
F1 C11 C10 107.2(2) . . ?
C12 C11 C10 112.3(3) . . ?
F1 C11 C13 107.2(2) . . ?
C12 C11 C13 111.0(2) . . ?
C10 C11 C13 111.9(2) . . ?
O1 C12 C11 110.0(2) . . ?
O1 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
O1 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O2 C13 C11 111.8(2) . . ?
O2 C13 H13A 109.3 . . ?
C11 C13 H13A 109.3 . . ?
O2 C13 H13B 109.3 . . ?
C11 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
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
F1 C11 1.413(3) . ?
O1 C12 1.421(4) . ?
O1 H1 0.8200 . ?
O2 C13 1.421(4) . ?
O2 H2 0.9473 . ?
C1 C2 1.387(5) . ?
C1 C6 1.389(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.366(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.370(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.478(4) . ?
C7 C8 1.306(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.291(5) . ?
C9 C10 1.497(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.517(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.510(4) . ?
C11 C13 1.518(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
