#------------------------------------------------------------------------------
#$Date: 2019-11-04 14:13:09 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222980 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/44/4034462.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_4034462
loop_
_publ_author_name
'Khatri, Hari R.'
'Han, Changho'
'Luong, Erica'
'Pan, Xiaoliang'
'Adam, Amna T.'
'Alshammari, Maali D.'
'Shao, Yihan'
'Colby, David A.'
_publ_section_title
;
 Controlling the Cleavage of Carbon-Carbon Bonds To Generate
 α,α-Difluorobenzyl Carbanions for the Construction of
 Difluoromethylbenzenes.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11665
_journal_page_last               11675
_journal_paper_doi               10.1021/acs.joc.9b01595
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C9 H6 F5 N O4'
_chemical_formula_weight         287.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.9833(6)
_cell_length_b                   6.3684(3)
_cell_length_c                   19.2501(5)
_cell_measurement_reflns_used    16307
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1
_cell_volume                     2082.02(13)
_computing_cell_refinement       'HKL3000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'Nonius Collect (Nonius, 1998)'
_computing_data_reduction        'HKL3000 (Otwinowski & Minor, 1997)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev946 (Hübschle et al., 2011)
;
_computing_structure_solution
;
 Direct methods (SIR2004, Burla et al., 2005)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16307
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.845
_diffrn_reflns_theta_min         2.116
_diffrn_source                   'fine focus X-ray tube'
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_correction_T_min  0.8570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0350
_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)+(0.0536P)²+0.6866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2047
_reflns_number_total             2476
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01595_si_002.cif
_cod_data_source_block           ch87
_cod_database_code               4034462
_shelx_shelxl_version_number     2018/3
_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   0.891
_shelx_estimated_absorpt_t_max   0.943
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
F1 F 0.02998(5) 0.26478(16) 0.17871(5) 0.0393(3) Uani 1 1 d . .
F2 F 0.03085(6) 0.55962(17) 0.12128(5) 0.0430(3) Uani 1 1 d . .
F3 F 0.06993(6) 0.04170(14) 0.07111(5) 0.0408(3) Uani 1 1 d . .
F4 F 0.17014(5) 0.14131(14) 0.01191(4) 0.0332(2) Uani 1 1 d . .
F5 F 0.06322(5) 0.32079(15) 0.00831(4) 0.0352(2) Uani 1 1 d . .
O1 O 0.18855(6) 0.21618(16) 0.15319(5) 0.0236(2) Uani 1 1 d . .
H1O H 0.2247(13) 0.160(3) 0.1295(10) 0.047(6) Uiso 1 1 d . .
O2 O 0.18674(6) 0.50837(16) 0.08514(5) 0.0254(2) Uani 1 1 d . .
H2O H 0.1745(13) 0.541(4) 0.0496(12) 0.050(6) Uiso 1 1 d . .
N1 N 0.16770(7) 0.8721(2) 0.40392(6) 0.0265(3) Uani 1 1 d . .
O3 O 0.19552(7) 1.04803(19) 0.39812(6) 0.0405(3) Uani 1 1 d . .
O4 O 0.15235(8) 0.79026(18) 0.46015(5) 0.0368(3) Uani 1 1 d . .
C1 C 0.10569(7) 0.5407(2) 0.22344(6) 0.0211(3) Uani 1 1 d . .
C2 C 0.13230(8) 0.7461(2) 0.21824(7) 0.0241(3) Uani 1 1 d . .
H2 H 0.134405 0.813153 0.174190 0.029 Uiso 1 1 calc R U
C3 C 0.15584(8) 0.8537(2) 0.27746(7) 0.0248(3) Uani 1 1 d . .
H3 H 0.175568 0.993000 0.274571 0.030 Uiso 1 1 calc R U
C4 C 0.14975(8) 0.7524(2) 0.34070(6) 0.0219(3) Uani 1 1 d . .
C5 C 0.12463(8) 0.5471(2) 0.34723(7) 0.0243(3) Uani 1 1 d . .
H5 H 0.122257 0.481127 0.391440 0.029 Uiso 1 1 calc R U
C6 C 0.10300(8) 0.4400(2) 0.28767(7) 0.0238(3) Uani 1 1 d . .
H6 H 0.086314 0.297934 0.290565 0.029 Uiso 1 1 calc R U
C7 C 0.07679(8) 0.4281(2) 0.15945(7) 0.0243(3) Uani 1 1 d . .
C8 C 0.14236(8) 0.3416(2) 0.11148(6) 0.0196(3) Uani 1 1 d . .
C9 C 0.10964(8) 0.2096(2) 0.05006(7) 0.0249(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'
N N 0.0061 0.0033 '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
C8 O1 H1O 110.2(13)
C8 O2 H2O 113.3(17)
O3 N1 O4 123.47(12)
O3 N1 C4 118.76(12)
O4 N1 C4 117.75(12)
C2 C1 C6 120.56(12)
C2 C1 C7 119.71(12)
C6 C1 C7 119.69(12)
C1 C2 C3 119.96(12)
C1 C2 H2 120.0
C3 C2 H2 120.0
C4 C3 C2 118.13(13)
C4 C3 H3 120.9
C2 C3 H3 120.9
C5 C4 C3 123.04(12)
C5 C4 N1 118.72(12)
C3 C4 N1 118.19(12)
C4 C5 C6 118.24(12)
C4 C5 H5 120.9
C6 C5 H5 120.9
C5 C6 C1 119.99(12)
C5 C6 H6 120.0
C1 C6 H6 120.0
F2 C7 F1 106.42(11)
F2 C7 C1 109.57(11)
F1 C7 C1 109.35(11)
F2 C7 C8 108.03(11)
F1 C7 C8 108.13(11)
C1 C7 C8 114.99(11)
O1 C8 O2 110.18(11)
O1 C8 C7 105.56(10)
O2 C8 C7 109.53(11)
O1 C8 C9 109.48(11)
O2 C8 C9 109.15(10)
C7 C8 C9 112.90(11)
F3 C9 F5 108.18(11)
F3 C9 F4 107.23(12)
F5 C9 F4 107.28(11)
F3 C9 C8 112.66(11)
F5 C9 C8 112.58(11)
F4 C9 C8 108.63(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C7 1.3605(17)
F2 C7 1.3603(16)
F3 C9 1.3277(16)
F4 C9 1.3359(16)
F5 C9 1.3299(16)
O1 C8 1.3778(15)
O1 H1O 0.85(2)
O2 C8 1.3974(16)
O2 H2O 0.75(2)
N1 O3 1.2210(17)
N1 O4 1.2294(16)
N1 C4 1.4680(16)
C1 C2 1.3876(19)
C1 C6 1.3935(18)
C1 C7 1.5078(18)
C2 C3 1.3888(19)
C2 H2 0.9500
C3 C4 1.3816(18)
C3 H3 0.9500
C4 C5 1.381(2)
C5 C6 1.3835(18)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.5478(18)
C8 C9 1.5535(18)
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
C6 C1 C2 C3 -0.6(2)
C7 C1 C2 C3 177.26(12)
C1 C2 C3 C4 -1.8(2)
C2 C3 C4 C5 2.8(2)
C2 C3 C4 N1 -174.49(12)
O3 N1 C4 C5 174.55(13)
O4 N1 C4 C5 -6.78(18)
O3 N1 C4 C3 -7.99(19)
O4 N1 C4 C3 170.67(13)
C3 C4 C5 C6 -1.4(2)
N1 C4 C5 C6 175.88(12)
C4 C5 C6 C1 -1.0(2)
C2 C1 C6 C5 2.0(2)
C7 C1 C6 C5 -175.82(12)
C2 C1 C7 F2 -42.96(16)
C6 C1 C7 F2 134.90(13)
C2 C1 C7 F1 -159.25(12)
C6 C1 C7 F1 18.62(17)
C2 C1 C7 C8 78.91(16)
C6 C1 C7 C8 -103.22(14)
F2 C7 C8 O1 177.86(10)
F1 C7 C8 O1 -67.34(13)
C1 C7 C8 O1 55.16(14)
F2 C7 C8 O2 59.26(14)
F1 C7 C8 O2 174.06(10)
C1 C7 C8 O2 -63.44(14)
F2 C7 C8 C9 -62.58(14)
F1 C7 C8 C9 52.22(14)
C1 C7 C8 C9 174.72(11)
O1 C8 C9 F3 56.19(15)
O2 C8 C9 F3 176.86(11)
C7 C8 C9 F3 -61.09(15)
O1 C8 C9 F5 178.86(11)
O2 C8 C9 F5 -60.47(14)
C7 C8 C9 F5 61.59(14)
O1 C8 C9 F4 -62.47(14)
O2 C8 C9 F4 58.20(14)
C7 C8 C9 F4 -179.74(11)
