#------------------------------------------------------------------------------
#$Date: 2021-11-06 19:56:37 +0100 (Sat 06 de Nov de 2021) $
#$Revision: 270392 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/90/7129001.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_7129001
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         'C7 H5 Br F3 N O'
_chemical_formula_sum            'C7 H5 Br F3 N O'
_chemical_formula_weight         256.03
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-16
_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                   7.2520(6)
_cell_length_b                   8.5655(8)
_cell_length_c                   13.9821(12)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.963
_cell_measurement_theta_min      3.160
_cell_volume                     868.53(13)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22485
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.958
_diffrn_reflns_theta_min         6.059
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.8
_exptl_absorpt_coefficient_mu    6.634
_exptl_absorpt_correction_T_max  0.5220
_exptl_absorpt_correction_T_min  0.2563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1433 before and 0.0441 after correction.
The Ratio of minimum to maximum transmission is 0.4910.
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    1.958
_exptl_crystal_description       Block
_exptl_crystal_F_000             496
_exptl_crystal_recrystallization_method 'crystallized fromHexane (70 C)'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 659 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0172
_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)+(0.0241P)²+0.3583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0449
_refine_ls_wR_factor_ref         0.0449
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                1620
_reflns_number_total             1620
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04556c2.cif
_cod_data_source_block           olev75
_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_database_code               7129001
_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_max   0.503
_shelx_estimated_absorpt_t_min   0.218
_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 olev75_a.res in P2(1)2(1)2(1)
    olev75.res
    created by SHELXL-2018/3 at 13:32:18 on 16-Jun-2020
REM Old TITL olev75 in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.082, Rweak 0.035, Alpha 0.004, Orientation as input
REM Flack x = 0.006 ( 0.007 ) from Parsons' quotients
REM Formula found by SHELXT: C7 N O F3 Br
CELL 1.54178 7.252 8.5655 13.9821 90 90 90
ZERR 4 0.0006 0.0008 0.0012 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br F N O
UNIT 28 20 4 12 4 4
EQIV $1 1-X,0.5+Y,1.5-Z
EQIV $2 1-X,-0.5+Y,1.5-Z

L.S. 30 0 0
PLAN  5
SIZE 0.12 0.14 0.33
TEMP -173
HTAB C6 O1_$2
HTAB O1 N1_$1
CONF
BOND $H
list 4
MORE -1
HTAB
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\olev75.hkl">
REM </olex2.extras>

WGHT    0.024100    0.358300
FVAR       1.07872
BR1   3    0.282401    0.289425    0.567665    11.00000    0.03393    0.01913 =
         0.03143   -0.00666   -0.00278   -0.00431
F3    4    0.250317    0.943391    0.844492    11.00000    0.03127    0.03568 =
         0.02398   -0.01278    0.00625   -0.00196
F2    4    0.118692    0.747694    0.775338    11.00000    0.03188    0.03580 =
         0.03486   -0.01072    0.01418   -0.01345
F1    4    0.129701    0.970996    0.705043    11.00000    0.03092    0.03682 =
         0.03725   -0.00615   -0.00523    0.01390
O1    6    0.515281    0.961795    0.699561    11.00000    0.02952    0.02107 =
         0.01723   -0.00063    0.00149   -0.00752
N1    5    0.352924    0.586943    0.630278    11.00000    0.01619    0.01832 =
         0.01783   -0.00083   -0.00076    0.00192
C1    1    0.329166    0.505977    0.550643    11.00000    0.01538    0.01773 =
         0.02357   -0.00371   -0.00192    0.00234
C2    1    0.336495    0.567454    0.459126    11.00000    0.01829    0.02892 =
         0.01866   -0.00640   -0.00320    0.00370
AFIX  43
H2    2    0.322112    0.503614    0.404069    11.00000   -1.20000
AFIX   0
C5    1    0.381192    0.741342    0.621802    11.00000    0.01281    0.01724 =
         0.01778   -0.00011    0.00009    0.00283
C6    1    0.410466    0.827101    0.715510    11.00000    0.02011    0.01446 =
         0.01742    0.00061   -0.00027   -0.00016
AFIX  13
H6    2    0.478283    0.757336    0.760802    11.00000   -1.20000
AFIX   0
C7    1    0.225695    0.872174    0.759754    11.00000    0.02482    0.02166 =
         0.02228   -0.00470    0.00341   -0.00090
C3    1    0.365921    0.727064    0.451974    11.00000    0.02323    0.03133 =
         0.01635    0.00360   -0.00072    0.00410
AFIX  43
H3    2    0.371504    0.775300    0.390860    11.00000   -1.20000
AFIX   0
C4    1    0.387137    0.816004    0.533846    11.00000    0.01939    0.02032 =
         0.02116    0.00172    0.00045    0.00294
AFIX  43
H4    2    0.405349    0.925648    0.529899    11.00000   -1.20000
AFIX   0
H1    2    0.560736    0.996645    0.750549    11.00000    0.04681
HKLF 4




REM  olev75_a.res in P2(1)2(1)2(1)
REM wR2 = 0.044885, GooF = S = 1.17260, Restrained GooF = 1.17260 for all data
REM R1 = 0.017178 for 1620 Fo > 4sig(Fo) and 0.017178 for all 1620 data
REM 122 parameters refined using 0 restraints

END

WGHT      0.0241      0.3583

REM Instructions for potential hydrogen bonds
HTAB C6 Br1_$1
HTAB C6 O1_$2
HTAB O1 N1_$1

REM Highest difference peak  0.428,  deepest hole -0.380,  1-sigma level  0.060
Q1    1   0.2840  0.2138  0.5262  11.00000  0.05    0.43
Q2    1   0.2703  0.3612  0.5228  11.00000  0.05    0.33
Q3    1   0.2690  0.3587  0.6109  11.00000  0.05    0.29
Q4    1   0.2857  0.2046  0.6176  11.00000  0.05    0.22
Q5    1   0.3836  0.7824  0.6683  11.00000  0.05    0.20
;
_shelx_res_checksum              6264
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id SL-IV-159a
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
Br1 Br 0.28240(4) 0.28943(3) 0.56767(2) 0.02816(11) Uani 1 1 d . . . . .
F3 F 0.2503(2) 0.9434(2) 0.84449(11) 0.0303(4) Uani 1 1 d . . . . .
F2 F 0.1187(3) 0.7477(2) 0.77534(13) 0.0342(4) Uani 1 1 d . . . . .
F1 F 0.1297(3) 0.9710(2) 0.70504(14) 0.0350(4) Uani 1 1 d . . . . .
O1 O 0.5153(3) 0.9618(2) 0.69956(14) 0.0226(4) Uani 1 1 d . . . . .
N1 N 0.3529(3) 0.5869(3) 0.63028(15) 0.0174(4) Uani 1 1 d . . . . .
C1 C 0.3292(3) 0.5060(3) 0.55064(19) 0.0189(5) Uani 1 1 d . . . . .
C2 C 0.3365(4) 0.5675(3) 0.45913(19) 0.0220(6) Uani 1 1 d . . . . .
H2 H 0.322112 0.503614 0.404069 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3812(3) 0.7413(3) 0.62180(18) 0.0159(5) Uani 1 1 d . . . . .
C6 C 0.4105(3) 0.8271(3) 0.71551(19) 0.0173(5) Uani 1 1 d . . . . .
H6 H 0.478283 0.757336 0.760802 0.021 Uiso 1 1 calc R U . . .
C7 C 0.2257(4) 0.8722(3) 0.75975(19) 0.0229(5) Uani 1 1 d . . . . .
C3 C 0.3659(4) 0.7271(4) 0.45197(18) 0.0236(6) Uani 1 1 d . . . . .
H3 H 0.371504 0.775300 0.390860 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3871(4) 0.8160(3) 0.53385(19) 0.0203(5) Uani 1 1 d . . . . .
H4 H 0.405349 0.925648 0.529899 0.024 Uiso 1 1 calc R U . . .
H1 H 0.561(6) 0.997(6) 0.751(4) 0.047(13) 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
Br1 0.03393(17) 0.01913(15) 0.03143(16) -0.00666(11) -0.00278(12) -0.00431(12)
F3 0.0313(9) 0.0357(9) 0.0240(8) -0.0128(7) 0.0063(7) -0.0020(7)
F2 0.0319(9) 0.0358(11) 0.0349(9) -0.0107(7) 0.0142(8) -0.0135(8)
F1 0.0309(8) 0.0368(10) 0.0373(10) -0.0061(8) -0.0052(8) 0.0139(8)
O1 0.0295(10) 0.0211(9) 0.0172(10) -0.0006(8) 0.0015(8) -0.0075(8)
N1 0.0162(10) 0.0183(11) 0.0178(10) -0.0008(8) -0.0008(9) 0.0019(9)
C1 0.0154(11) 0.0177(12) 0.0236(13) -0.0037(10) -0.0019(9) 0.0023(9)
C2 0.0183(13) 0.0289(14) 0.0187(12) -0.0064(11) -0.0032(9) 0.0037(10)
C5 0.0128(11) 0.0172(12) 0.0178(12) -0.0001(9) 0.0001(9) 0.0028(9)
C6 0.0201(12) 0.0145(12) 0.0174(12) 0.0006(10) -0.0003(10) -0.0002(9)
C7 0.0248(13) 0.0217(12) 0.0223(12) -0.0047(10) 0.0034(11) -0.0009(12)
C3 0.0232(12) 0.0313(14) 0.0163(12) 0.0036(11) -0.0007(10) 0.0041(12)
C4 0.0194(12) 0.0203(14) 0.0212(12) 0.0017(10) 0.0004(9) 0.0029(10)
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'
Br Br -0.6763 1.2805 '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'
N N 0.0311 0.0180 '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
C6 O1 H1 112(3) . . ?
C1 N1 C5 117.5(2) . . ?
N1 C1 Br1 115.43(19) . . ?
N1 C1 C2 125.0(2) . . ?
C2 C1 Br1 119.58(19) . . ?
C1 C2 H2 121.7 . . ?
C1 C2 C3 116.6(2) . . ?
C3 C2 H2 121.7 . . ?
N1 C5 C6 114.9(2) . . ?
N1 C5 C4 122.5(2) . . ?
C4 C5 C6 122.6(2) . . ?
O1 C6 C5 109.7(2) . . ?
O1 C6 H6 109.1 . . ?
O1 C6 C7 109.5(2) . . ?
C5 C6 H6 109.1 . . ?
C5 C6 C7 110.5(2) . . ?
C7 C6 H6 109.1 . . ?
F3 C7 C6 110.8(2) . . ?
F2 C7 F3 107.2(2) . . ?
F2 C7 C6 112.0(2) . . ?
F1 C7 F3 106.6(2) . . ?
F1 C7 F2 107.2(2) . . ?
F1 C7 C6 112.7(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 H4 120.8 . . ?
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
Br1 C1 1.901(3) . ?
F3 C7 1.345(3) . ?
F2 C7 1.337(3) . ?
F1 C7 1.337(4) . ?
O1 C6 1.399(3) . ?
O1 H1 0.84(5) . ?
N1 C1 1.323(3) . ?
N1 C5 1.344(3) . ?
C1 C2 1.385(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C5 C6 1.517(3) . ?
C5 C4 1.387(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.526(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(4) . ?
C4 H4 0.9500 . ?
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
_geom_hbond_publ_flag
C6 H6 O1 1.00 2.59 3.390(3) 136.7 3_646 yes
O1 H1 N1 0.84(5) 1.94(5) 2.779(3) 175(4) 3_656 yes
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
Br1 C1 C2 C3 178.2(2) . . . . ?
O1 C6 C7 F3 -61.2(3) . . . . ?
O1 C6 C7 F2 179.1(2) . . . . ?
O1 C6 C7 F1 58.2(3) . . . . ?
N1 C1 C2 C3 -1.9(4) . . . . ?
N1 C5 C6 O1 153.8(2) . . . . ?
N1 C5 C6 C7 -85.4(3) . . . . ?
N1 C5 C4 C3 -1.0(4) . . . . ?
C1 N1 C5 C6 -179.1(2) . . . . ?
C1 N1 C5 C4 -0.4(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C5 N1 C1 Br1 -178.17(18) . . . . ?
C5 N1 C1 C2 2.0(4) . . . . ?
C5 C6 C7 F3 177.8(2) . . . . ?
C5 C6 C7 F2 58.2(3) . . . . ?
C5 C6 C7 F1 -62.8(3) . . . . ?
C6 C5 C4 C3 177.5(2) . . . . ?
C4 C5 C6 O1 -24.8(3) . . . . ?
C4 C5 C6 C7 96.0(3) . . . . ?
