#------------------------------------------------------------------------------
#$Date: 2021-11-06 19:56:37 +0100 (Sat 06 de Nov de 2021) $
#$Revision: 270392 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/90/7129002.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_7129002
loop_
_publ_author_name
'Lauzon, Samuel'
'Ollevier, Thierry'
_publ_section_title
;
 2,2'-Bipyridine-α,α'-trifluoromethyl-diol ligand: synthesis and
 application in the asymmetric Et₂Zn alkylation of aldehydes.
;
_journal_issue                   84
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11025
_journal_page_last               11028
_journal_paper_doi               10.1039/d1cc04556c
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H10 F6 N2 O2'
_chemical_formula_sum            'C14 H10 F6 N2 O2'
_chemical_formula_weight         352.24
_space_group_crystal_system      tetragonal
_space_group_IT_number           94
_space_group_name_Hall           'P 4n 2n'
_space_group_name_H-M_alt        'P 42 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-07-23 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5873(2)
_cell_length_b                   14.5873(2)
_cell_length_c                   6.7844(2)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    120
_cell_measurement_theta_max      60.569
_cell_measurement_theta_min      3.729
_cell_volume                     1443.65(5)
_computing_cell_refinement
;
SAINT (2013) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon III CMOS Detector'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21453
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.538
_diffrn_reflns_theta_min         3.728
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.199914
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0984 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.8576.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       fragment
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'crystallized from Hexane/EtOAc 90:10 at 77 C'
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0299
_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)+(0.0406P)²+0.4212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0794
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1627
_reflns_number_total             1641
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04556c2.cif
_cod_data_source_block           olev78
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7129001--7129003.cif.
;
_cod_original_cell_volume        1443.65(6)
_cod_database_code               7129002
_shelx_shelxl_version_number     2016/6
_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_max   0.926
_shelx_estimated_absorpt_t_min   0.837
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
;
_shelx_res_file
;
TITL olev78_a.res in P4(2)2(1)2
    olev78.res
    created by SHELXL-2016/6 at 17:10:46 on 07-Aug-2020
REM Old TITL olev78 in P4(3)2(1)2
REM SHELXT solution in P4(2)2(1)2
REM R1 0.209, Rweak 0.039, Alpha 0.001, Orientation as input
REM Flack x = 0.287 ( 0.021 ) from Parsons' quotients
REM Formula found by SHELXT: C7 N2 F3
CELL 1.34139 14.5873 14.5873 6.7844 90 90 90
ZERR 4 0.0002 0.0002 0.0002 0 0 0
LATT -1
SYMM -X,-Y,+Z
SYMM 0.5-Y,0.5+X,0.5+Z
SYMM 0.5+Y,0.5-X,0.5+Z
SYMM 0.5-X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,0.5-Z
SYMM +Y,+X,-Z
SYMM -Y,-X,-Z
SFAC C H F N O
DISP C 0.0137 0.0057 57.1
DISP F 0.0583 0.04 317.7
DISP H -0 0 0.6
DISP N 0.0241 0.0134 109.9
DISP O 0.0389 0.0241 193.4
UNIT 56 40 24 8 8

L.S. 25
PLAN  5
SIZE 0.085 0.109 0.201
TEMP 0
CONF
HTAB O1 N1
BOND $H
list 4
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\olev78.hkl">
REM </olex2.extras>

WGHT    0.040600    0.421200
EXTI    0.008316
FVAR       1.47892
F1    3    0.786699    0.586572    0.550564    11.00000    0.07174    0.11075 =
         0.03645   -0.02976    0.01688   -0.05975
F2    3    0.908873    0.611134    0.385251    11.00000    0.02991    0.04176 =
         0.04549    0.00258   -0.00848   -0.01588
F3    3    0.870068    0.473246    0.457446    11.00000    0.07466    0.05205 =
         0.09614    0.03812   -0.05771   -0.02753
O1    5    0.757132    0.635879    0.154220    11.00000    0.02479    0.02536 =
         0.06916    0.01398   -0.00556   -0.00471
N1    4    0.620850    0.526193    0.233714    11.00000    0.02016    0.01899 =
         0.01979   -0.00120   -0.00073   -0.00187
C1    1    0.701596    0.483382    0.232721    11.00000    0.02143    0.02163 =
         0.01933   -0.00254    0.00006   -0.00135
C2    1    0.711298    0.388667    0.245422    11.00000    0.02246    0.02264 =
         0.02605   -0.00263    0.00014    0.00278
AFIX  43
H2    2    0.768916    0.361378    0.245040    11.00000   -1.20000
AFIX   0
C3    1    0.632151    0.336314    0.258672    11.00000    0.02779    0.01696 =
         0.02479   -0.00067   -0.00109   -0.00054
AFIX  43
H3    2    0.635859    0.272830    0.268428    11.00000   -1.20000
AFIX   0
C4    1    0.547646    0.379373    0.257247    11.00000    0.02391    0.01910 =
         0.02037   -0.00039   -0.00049   -0.00399
AFIX  43
H4    2    0.493889    0.345235    0.263834    11.00000   -1.20000
AFIX   0
C5    1    0.544337    0.474878    0.245764    11.00000    0.02075    0.01890 =
         0.01591   -0.00076   -0.00033   -0.00160
C6    1    0.783535    0.547635    0.211714    11.00000    0.02021    0.02230 =
         0.02757    0.00041    0.00074   -0.00210
AFIX  13
H6    2    0.824243    0.522688    0.110090    11.00000   -1.20000
AFIX   0
C7    1    0.837097    0.554299    0.402463    11.00000    0.03688    0.03846 =
         0.03527    0.00497   -0.00727   -0.01657
H1    2    0.700989    0.636489    0.172178    11.00000    0.05446
HKLF 4




REM  olev78_a.res in P4(2)2(1)2
REM R1 =  0.0299 for    1627 Fo > 4sig(Fo)  and  0.0301 for all    1641 data
REM    114 parameters refined using      0 restraints

END

WGHT      0.0406      0.4224

REM Highest difference peak  0.219,  deepest hole -0.198,  1-sigma level  0.036
Q1    1   0.8302  0.5014  0.5036  11.00000  0.05    0.22
Q2    1   0.7448  0.5099  0.2226  11.00000  0.05    0.22
Q3    1   0.7130  0.4378  0.2828  11.00000  0.05    0.18
Q4    1   0.7012  0.4335  0.2319  11.00000  0.05    0.17
Q5    1   0.5000  0.5000  0.2607  10.50000  0.05    0.16
;
_shelx_res_checksum              23540
_olex2_exptl_crystal_mounting_method 'mouned on a cryoloop'
_olex2_submission_original_sample_id SL-IV-173a
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y, x, -z'
'-y, -x, -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 0.78670(12) 0.58657(15) 0.5506(2) 0.0730(6) Uani 1 1 d . . . . .
F2 F 0.90887(8) 0.61113(9) 0.3853(2) 0.0391(3) Uani 1 1 d . . . . .
F3 F 0.87007(12) 0.47325(11) 0.4574(3) 0.0743(7) Uani 1 1 d . . . . .
O1 O 0.75713(10) 0.63588(10) 0.1542(3) 0.0398(4) Uani 1 1 d . . . . .
N1 N 0.62085(9) 0.52619(9) 0.2337(2) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.70160(11) 0.48338(11) 0.2327(2) 0.0208(3) Uani 1 1 d . . . . .
C2 C 0.71130(11) 0.38867(11) 0.2454(3) 0.0237(4) Uani 1 1 d . . . . .
H2 H 0.768916 0.361378 0.245040 0.028 Uiso 1 1 calc R U . . .
C3 C 0.63215(11) 0.33631(11) 0.2587(3) 0.0232(3) Uani 1 1 d . . . . .
H3 H 0.635859 0.272830 0.268428 0.028 Uiso 1 1 calc R U . . .
C4 C 0.54765(11) 0.37937(11) 0.2572(2) 0.0211(3) Uani 1 1 d . . . . .
H4 H 0.493889 0.345235 0.263834 0.025 Uiso 1 1 calc R U . . .
C5 C 0.54434(10) 0.47488(10) 0.2458(2) 0.0185(3) Uani 1 1 d . . . . .
C6 C 0.78354(11) 0.54764(12) 0.2117(3) 0.0234(4) Uani 1 1 d . . . . .
H6 H 0.824243 0.522688 0.110090 0.028 Uiso 1 1 calc R U . . .
C7 C 0.83710(15) 0.55430(15) 0.4025(3) 0.0369(5) Uani 1 1 d . . . . .
H1 H 0.701(2) 0.636(2) 0.172(5) 0.054(9) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0717(11) 0.1108(15) 0.0364(7) -0.0298(9) 0.0169(7) -0.0597(10)
F2 0.0299(6) 0.0418(7) 0.0455(7) 0.0026(5) -0.0085(5) -0.0159(5)
F3 0.0747(11) 0.0521(9) 0.0961(14) 0.0381(9) -0.0577(11) -0.0275(8)
O1 0.0248(7) 0.0254(7) 0.0692(11) 0.0140(7) -0.0056(7) -0.0047(5)
N1 0.0202(6) 0.0190(6) 0.0198(6) -0.0012(5) -0.0007(5) -0.0019(5)
C1 0.0214(7) 0.0216(8) 0.0193(7) -0.0025(6) 0.0001(6) -0.0014(6)
C2 0.0225(7) 0.0226(8) 0.0261(8) -0.0026(7) 0.0001(7) 0.0028(6)
C3 0.0278(8) 0.0170(7) 0.0248(7) -0.0007(7) -0.0011(7) -0.0005(6)
C4 0.0239(7) 0.0191(7) 0.0204(7) -0.0004(6) -0.0005(6) -0.0040(5)
C5 0.0207(7) 0.0189(7) 0.0159(6) -0.0008(5) -0.0003(6) -0.0016(6)
C6 0.0202(7) 0.0223(8) 0.0276(8) 0.0004(6) 0.0007(6) -0.0021(6)
C7 0.0369(10) 0.0385(11) 0.0353(10) 0.0050(8) -0.0073(8) -0.0166(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0057 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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 O1 H1 104(2) . . ?
C1 N1 C5 118.18(13) . . ?
N1 C1 C2 123.69(15) . . ?
N1 C1 C6 113.88(13) . . ?
C2 C1 C6 122.42(15) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.77(15) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.42(14) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 118.96(14) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.97(14) . . ?
N1 C5 C5 116.56(16) . 2_665 ?
C4 C5 C5 121.46(17) . 2_665 ?
O1 C6 C1 112.06(14) . . ?
O1 C6 H6 108.2 . . ?
O1 C6 C7 108.73(15) . . ?
C1 C6 H6 108.2 . . ?
C7 C6 C1 111.33(15) . . ?
C7 C6 H6 108.2 . . ?
F1 C7 F2 106.16(17) . . ?
F1 C7 C6 112.50(18) . . ?
F2 C7 C6 111.60(16) . . ?
F3 C7 F1 107.6(2) . . ?
F3 C7 F2 106.97(17) . . ?
F3 C7 C6 111.66(18) . . ?
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 C7 1.331(3) . ?
F2 C7 1.341(2) . ?
F3 C7 1.330(3) . ?
O1 C6 1.399(2) . ?
O1 H1 0.83(3) . ?
N1 C1 1.333(2) . ?
N1 C5 1.3464(19) . ?
C1 C2 1.392(2) . ?
C1 C6 1.526(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.396(2) . ?
C5 C5 1.487(3) 2_665 ?
C6 H6 0.9800 . ?
C6 C7 1.515(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.83(3) 2.03(3) 2.6083(19) 126(3) .
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
O1 C6 C7 F1 63.5(2) . . . . ?
O1 C6 C7 F2 -55.7(2) . . . . ?
O1 C6 C7 F3 -175.34(17) . . . . ?
N1 C1 C2 C3 0.4(3) . . . . ?
N1 C1 C6 O1 -13.3(2) . . . . ?
N1 C1 C6 C7 108.77(18) . . . . ?
C1 N1 C5 C4 0.1(2) . . . . ?
C1 N1 C5 C5 -179.80(11) . . . 2_665 ?
C1 C2 C3 C4 0.5(2) . . . . ?
C1 C6 C7 F1 -60.4(2) . . . . ?
C1 C6 C7 F2 -179.61(16) . . . . ?
C1 C6 C7 F3 60.7(2) . . . . ?
C2 C1 C6 O1 165.49(16) . . . . ?
C2 C1 C6 C7 -72.5(2) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C3 C4 C5 N1 0.8(2) . . . . ?
C3 C4 C5 C5 -179.35(11) . . . 2_665 ?
C5 N1 C1 C2 -0.7(3) . . . . ?
C5 N1 C1 C6 178.06(14) . . . . ?
C6 C1 C2 C3 -178.23(16) . . . . ?
