#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:19:14 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179017 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/15/4121573.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_4121573
loop_
_publ_author_name
'Liang, Yufan'
'Fu, Gregory C.'
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi
 Cross-Couplings of Racemic α,α-Dihaloketones.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5520
_journal_page_last               5524
_journal_paper_doi               10.1021/ja501815p
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H22 Cl F O, C0.58 H1.16 Cl1.16'
_chemical_formula_sum            'C27.58 H23.16 Cl2.16 F O'
_chemical_formula_weight         466.24
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-08-20
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.076(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4485(6)
_cell_length_b                   5.9142(3)
_cell_length_c                   17.0352(8)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.48
_cell_measurement_theta_min      2.16
_cell_volume                     1153.23(10)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            62094
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.564
_diffrn_reflns_theta_min         1.779
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       needle
_exptl_crystal_F_000             484.8
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 3069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.005(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         11432
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0499
_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)+(0.0717P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                8151
_reflns_number_total             11432
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja501815p_si_005.cif
_cod_data_source_block           crystal_005
_cod_depositor_comments
'Adding full bibliography for 4121570--4121574.cif.'
_cod_database_code               4121573
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C28-Cl2 \\sim C28-Cl3A \\sim C28-Cl3B \\sim C28-Cl3C
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Cl3A \\sim Cl3B \\sim Cl3C \\sim Cl2 \\sim C28: within 3.2A with sigma of 0.01 and sigma for terminal atoms of 0.005
4. Others
 1*[Sof(Cl3A)]+1*[Sof(Cl3B)]+1*[Sof(Cl3C)]-1*[Sof(Cl2)+Sof(C28)+Sof(H28A)+
 Sof(H28B)]=0 with esd of 0.0001
 Sof(Cl2)=Sof(C28)=Sof(H28A)=Sof(H28B)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C28(H28A,H28B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27)
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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.
;
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
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
Cl1 Cl -0.31493(6) -0.81130(11) -0.38253(3) 0.03278(15) Uani 1 1 d . . . . .
F1 F -0.31729(10) -0.90033(18) -0.78646(6) 0.0137(2) Uani 1 1 d . . . . .
O1 O -0.33902(12) -0.3198(2) -0.72344(7) 0.0161(2) Uani 1 1 d . . . . .
H1 H -0.3514 -0.2623 -0.7679 0.024 Uiso 1 1 calc R U . . .
C1 C -0.28719(16) -0.6682(3) -0.78564(10) 0.0113(3) Uani 1 1 d . . . . .
C2 C -0.37037(16) -0.5518(3) -0.72529(10) 0.0120(3) Uani 1 1 d . . . . .
C3 C -0.30902(16) -0.5802(3) -0.86860(10) 0.0121(3) Uani 1 1 d . . . . .
C4 C -0.26518(17) -0.3711(3) -0.89297(11) 0.0157(3) Uani 1 1 d . . . . .
H4 H -0.2218 -0.2799 -0.8569 0.019 Uiso 1 1 calc R U . . .
C5 C -0.28463(17) -0.2956(4) -0.96980(10) 0.0184(3) Uani 1 1 d . . . . .
H5 H -0.2556 -0.1525 -0.9856 0.022 Uiso 1 1 calc R U . . .
C6 C -0.34638(18) -0.4295(4) -1.02318(11) 0.0209(4) Uani 1 1 d . . . . .
H6 H -0.3580 -0.3801 -1.0758 0.025 Uiso 1 1 calc R U . . .
C7 C -0.39096(18) -0.6353(4) -0.99926(11) 0.0200(4) Uani 1 1 d . . . . .
H7 H -0.4342 -0.7261 -1.0355 0.024 Uiso 1 1 calc R U . . .
C8 C -0.37296(16) -0.7103(3) -0.92240(11) 0.0153(3) Uani 1 1 d . . . . .
H8 H -0.4045 -0.8513 -0.9066 0.018 Uiso 1 1 calc R U . . .
C9 C -0.15793(16) -0.6523(3) -0.76068(10) 0.0143(3) Uani 1 1 d . . . . .
H9A H -0.1306 -0.4954 -0.7689 0.017 Uiso 1 1 calc R U . . .
H9B H -0.1504 -0.6860 -0.7039 0.017 Uiso 1 1 calc R U . . .
C10 C -0.08038(15) -0.8115(4) -0.80519(10) 0.0149(3) Uani 1 1 d . . . . .
C11 C -0.04908(17) -0.7697(4) -0.88299(11) 0.0203(4) Uani 1 1 d . . . . .
H11 H -0.0765 -0.6370 -0.9088 0.024 Uiso 1 1 calc R U . . .
C12 C 0.02155(19) -0.9199(5) -0.92265(13) 0.0270(5) Uani 1 1 d . . . . .
H12 H 0.0418 -0.8893 -0.9754 0.032 Uiso 1 1 calc R U . . .
C13 C 0.06293(18) -1.1144(4) -0.88624(14) 0.0252(5) Uani 1 1 d . . . . .
H13 H 0.1103 -1.2177 -0.9141 0.030 Uiso 1 1 calc R U . . .
C14 C 0.03469(18) -1.1570(4) -0.80903(14) 0.0239(4) Uani 1 1 d . . . . .
H14 H 0.0642 -1.2882 -0.7833 0.029 Uiso 1 1 calc R U . . .
C15 C -0.03712(18) -1.0072(4) -0.76881(13) 0.0206(4) Uani 1 1 d . . . . .
H15 H -0.0568 -1.0386 -0.7160 0.025 Uiso 1 1 calc R U . . .
C16 C -0.35313(16) -0.6300(3) -0.63983(10) 0.0128(3) Uani 1 1 d . . . . .
C17 C -0.38434(19) -0.4760(3) -0.58130(11) 0.0179(4) Uani 1 1 d . . . . .
H17 H -0.4133 -0.3313 -0.5961 0.022 Uiso 1 1 calc R U . . .
C18 C -0.3740(2) -0.5302(4) -0.50224(12) 0.0218(4) Uani 1 1 d . . . . .
H18 H -0.3958 -0.4242 -0.4633 0.026 Uiso 1 1 calc R U . . .
C19 C -0.33126(19) -0.7411(4) -0.48100(11) 0.0197(4) Uani 1 1 d . . . . .
C20 C -0.30217(19) -0.8995(4) -0.53731(11) 0.0193(4) Uani 1 1 d . . . . .
H20 H -0.2745 -1.0447 -0.5221 0.023 Uiso 1 1 calc R U . . .
C21 C -0.31400(18) -0.8431(3) -0.61681(10) 0.0168(4) Uani 1 1 d . . . . .
H21 H -0.2951 -0.9518 -0.6556 0.020 Uiso 1 1 calc R U . . .
C22 C -0.49825(16) -0.5871(3) -0.75066(10) 0.0127(3) Uani 1 1 d . . . . .
C23 C -0.55924(18) -0.4212(3) -0.79247(11) 0.0172(3) Uani 1 1 d . . . . .
H23 H -0.5205 -0.2853 -0.8064 0.021 Uiso 1 1 calc R U . . .
C24 C -0.67615(19) -0.4514(4) -0.81413(12) 0.0208(4) Uani 1 1 d . . . . .
H24 H -0.7162 -0.3364 -0.8428 0.025 Uiso 1 1 calc R U . . .
C25 C -0.73431(18) -0.6478(4) -0.79423(12) 0.0207(4) Uani 1 1 d . . . . .
H25 H -0.8143 -0.6676 -0.8084 0.025 Uiso 1 1 calc R U . . .
C26 C -0.67386(17) -0.8158(4) -0.75311(11) 0.0199(4) Uani 1 1 d . . . . .
H26 H -0.7127 -0.9519 -0.7396 0.024 Uiso 1 1 calc R U . . .
C27 C -0.55746(17) -0.7861(3) -0.73170(10) 0.0165(3) Uani 1 1 d . . . . .
H27 H -0.5174 -0.9025 -0.7038 0.020 Uiso 1 1 calc R U . . .
Cl2 Cl 0.0762(3) -1.8036(7) -0.57673(18) 0.1355(13) Uani 0.581(3) 1 d D U P A 1
Cl3A Cl -0.0738(8) -1.365(2) -0.5696(6) 0.156(2) Uani 0.235(3) 1 d D U P A 1
C28 C 0.0381(9) -1.5326(17) -0.5956(7) 0.141(2) Uani 0.581(3) 1 d D U P A 1
H28A H 0.1081 -1.4455 -0.5790 0.169 Uiso 0.581(3) 1 calc R U P A 1
H28B H 0.0363 -1.5250 -0.6537 0.169 Uiso 0.581(3) 1 calc R U P A 1
Cl3B Cl 0.0144(19) -1.292(4) -0.5390(13) 0.158(3) Uani 0.106(3) 1 d D U P B 2
Cl3C Cl -0.0295(9) -1.504(2) -0.5084(6) 0.169(3) Uani 0.240(3) 1 d D U P C 3
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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
F1 C1 C2 106.29(13)
F1 C1 C3 106.66(14)
F1 C1 C9 107.18(14)
C3 C1 C2 111.50(14)
C3 C1 C9 112.15(14)
C9 C1 C2 112.61(14)
O1 C2 C1 106.35(14)
O1 C2 C16 104.00(14)
O1 C2 C22 112.20(15)
C16 C2 C1 114.78(14)
C22 C2 C1 110.06(14)
C22 C2 C16 109.34(14)
C4 C3 C1 121.57(16)
C8 C3 C1 119.78(16)
C8 C3 C4 118.64(16)
C5 C4 C3 120.55(18)
C6 C5 C4 120.1(2)
C7 C6 C5 119.63(18)
C6 C7 C8 120.50(19)
C3 C8 C7 120.55(19)
C10 C9 C1 113.33(15)
C11 C10 C9 121.90(18)
C15 C10 C9 120.05(16)
C15 C10 C11 118.05(18)
C12 C11 C10 120.6(2)
C11 C12 C13 120.8(2)
C14 C13 C12 119.5(2)
C13 C14 C15 120.1(2)
C14 C15 C10 120.9(2)
C17 C16 C2 116.65(16)
C21 C16 C2 125.05(16)
C21 C16 C17 118.23(17)
C18 C17 C16 121.49(19)
C19 C18 C17 119.00(19)
C18 C19 Cl1 119.94(16)
C18 C19 C20 121.06(18)
C20 C19 Cl1 119.00(17)
C19 C20 C21 119.28(19)
C16 C21 C20 120.90(17)
C23 C22 C2 121.02(17)
C23 C22 C27 118.07(18)
C27 C22 C2 120.91(16)
C22 C23 C24 121.01(19)
C25 C24 C23 120.45(19)
C24 C25 C26 119.03(19)
C27 C26 C25 120.6(2)
C26 C27 C22 120.89(19)
Cl3A C28 Cl2 134.6(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C19 1.7347(19)
F1 C1 1.416(2)
O1 C2 1.419(2)
C1 C2 1.573(2)
C1 C3 1.522(2)
C1 C9 1.535(2)
C2 C16 1.537(2)
C2 C22 1.533(3)
C3 C4 1.400(3)
C3 C8 1.394(3)
C4 C5 1.397(3)
C5 C6 1.389(3)
C6 C7 1.384(3)
C7 C8 1.394(3)
C9 C10 1.508(3)
C10 C11 1.402(3)
C10 C15 1.399(3)
C11 C12 1.386(3)
C12 C13 1.386(4)
C13 C14 1.383(3)
C14 C15 1.397(3)
C16 C17 1.402(3)
C16 C21 1.392(3)
C17 C18 1.387(3)
C18 C19 1.386(3)
C19 C20 1.386(3)
C20 C21 1.399(3)
C22 C23 1.393(3)
C22 C27 1.399(3)
C23 C24 1.393(3)
C24 C25 1.384(3)
C25 C26 1.392(3)
C26 C27 1.386(3)
Cl2 C28 1.691(10)
Cl3A C28 1.687(11)
