#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:30:03 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272644 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/89/7708974.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_7708974
loop_
_publ_author_name
'Piyasaengthong, Akkharadet'
'Williams, Luke J.'
'Yufit, Dmitry S.'
'Walton, James W.'
_publ_section_title
;
 Novel ruthenium complexes bearing bipyridine-based and N-heterocyclic
 carbene-supported pyridine (NCN) ligands: the influence of ligands on
 catalytic transfer hydrogenation of ketones.
;
_journal_issue                   1
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              340
_journal_page_last               351
_journal_paper_doi               10.1039/d1dt03240b
_journal_volume                  51
_journal_year                    2021
_chemical_formula_moiety         'C12 H10 Br2 N2'
_chemical_formula_sum            'C12 H10 Br2 N2'
_chemical_formula_weight         342.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-27 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1004(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0100(4)
_cell_length_b                   4.4177(2)
_cell_length_c                   10.9527(4)
_cell_measurement_reflns_used    8334
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.41
_cell_measurement_theta_min      3.40
_cell_volume                     579.63(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8661
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.499
_diffrn_reflns_theta_min         3.401
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.964
_exptl_absorpt_correction_T_max  0.6553
_exptl_absorpt_correction_T_min  0.3242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;    
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0656 before and 0.0368 after correction. 
The Ratio of minimum to maximum transmission is 0.4947. 
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.135
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0201
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0210P)²+0.6050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0520
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1455
_reflns_number_total             1609
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL 19srv299 in P21/c #14
REM reset to P21/c #14
CELL 0.71073 12.01 4.4177 10.9527 90 94.1004 90
ZERR 2 0.0004 0.0002 0.0004 0 0.0014 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Br N
UNIT 24 20 4 4
EQIV $1 -X,1-Y,1-Z

L.S. 9
PLAN  5
SIZE 0.09 0.18 0.19
TEMP -153.15
CONF N1 C1 C1_$1 N1_$1
CONF N1 C1 C1_$1 C2_$1
CONF N1_$1 C1_$1 C1 C2
CONF C2 C1 C1_$1 C2_$1
CONF N1 C5 C6 Br1
CONF C4 C5 C6 Br1
BOND $h
fmap 2
acta 
OMIT -2 59
WGHT 0.021 0.605
FVAR 0.25951
REM <olex2.extras>
REM <HklSrc "%.\\19srv299.hkl">
REM </olex2.extras>

Br1   3     0.41648  0.57005  0.64622  11.00000  0.01485  0.02251  0.01632 =
 -0.00142 -0.00339 -0.00083 
N1    4     0.14163  0.63658  0.51616  11.00000  0.01191  0.01320  0.01277 =
 0.00089 -0.00226 -0.00022 
C1    1     0.05257  0.48085  0.46867  11.00000  0.01200  0.01174  0.01055 =
 0.00232 -0.00254  0.00067 
C2    1     0.05672  0.29420  0.36662  11.00000  0.01417  0.01589  0.01256 =
 -0.00173 -0.00194  0.00028 
AFIX 43
H2    2    -0.00752  0.18505  0.33610  11.00000 -1.20000 
AFIX 0
C3    1     0.15635  0.27020  0.31015  11.00000  0.01796  0.01863  0.01167 =
 -0.00183 -0.00070  0.00324 
AFIX 43
H3    2     0.16161  0.14383  0.24062  11.00000 -1.20000 
AFIX 0
C4    1     0.24809  0.43471  0.35746  11.00000  0.01454  0.01833  0.01382 =
 0.00273  0.00159  0.00168 
AFIX 43
H4    2     0.31702  0.42541  0.32014  11.00000 -1.20000 
AFIX 0
C5    1     0.23718  0.61315  0.46037  11.00000  0.01331  0.01400  0.01305 =
 0.00357 -0.00169  0.00002 
C6    1     0.33268  0.79594  0.51468  11.00000  0.01474  0.01742  0.01992 =
 0.00281 -0.00212 -0.00125 
AFIX 23
H6a   2     0.30427  0.98696  0.54807  11.00000 -1.20000 
H6b   2     0.38309  0.84804  0.45017  11.00000 -1.20000 
AFIX 0
HKLF 4

END
;
_cod_data_source_file            d1dt03240b2.cif
_cod_data_source_block           L0_19srv299
_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 7708973--7708976.cif.
;
_cod_database_code               7708974
_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_max   0.573
_shelx_estimated_absorpt_t_min   0.351
_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.41648(2) 0.57006(5) 0.64622(2) 0.01811(7) Uani 1 1 d . . . . .
N1 N 0.14163(13) 0.6366(4) 0.51616(14) 0.0128(3) Uani 1 1 d . . . . .
C1 C 0.05256(15) 0.4809(4) 0.46867(16) 0.0116(3) Uani 1 1 d . . . . .
C2 C 0.05672(15) 0.2942(4) 0.36662(16) 0.0143(3) Uani 1 1 d . . . . .
H2 H -0.007517 0.185045 0.336103 0.017 Uiso 1 1 calc R . . . .
C3 C 0.15635(16) 0.2702(5) 0.31016(17) 0.0162(4) Uani 1 1 d . . . . .
H3 H 0.161604 0.143835 0.240620 0.019 Uiso 1 1 calc R . . . .
C4 C 0.24809(16) 0.4347(4) 0.35746(17) 0.0155(3) Uani 1 1 d . . . . .
H4 H 0.317018 0.425406 0.320135 0.019 Uiso 1 1 calc R . . . .
C5 C 0.23718(15) 0.6131(4) 0.46037(16) 0.0136(3) Uani 1 1 d . . . . .
C6 C 0.33268(16) 0.7959(5) 0.51468(18) 0.0175(4) Uani 1 1 d . . . . .
H6A H 0.304269 0.986966 0.548070 0.021 Uiso 1 1 calc R . . . .
H6B H 0.383091 0.848042 0.450168 0.021 Uiso 1 1 calc R . . . .
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 0.01485(10) 0.02251(11) 0.01632(10) -0.00142(7) -0.00339(6) -0.00083(8)
N1 0.0119(7) 0.0132(7) 0.0128(7) 0.0009(5) -0.0023(5) -0.0002(6)
C1 0.0120(8) 0.0117(8) 0.0106(7) 0.0023(6) -0.0025(6) 0.0007(6)
C2 0.0142(8) 0.0159(9) 0.0126(8) -0.0017(7) -0.0019(6) 0.0003(7)
C3 0.0180(9) 0.0186(9) 0.0117(8) -0.0018(7) -0.0007(7) 0.0032(7)
C4 0.0145(8) 0.0183(9) 0.0138(8) 0.0027(7) 0.0016(6) 0.0017(7)
C5 0.0133(8) 0.0140(8) 0.0130(8) 0.0036(6) -0.0017(6) 0.0000(7)
C6 0.0147(8) 0.0174(9) 0.0199(9) 0.0028(7) -0.0021(7) -0.0012(7)
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'
Br Br -0.2901 2.4595 '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'
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
C5 N1 C1 117.82(16) . . ?
N1 C1 C1 116.2(2) . 3_566 ?
N1 C1 C2 122.70(17) . . ?
C2 C1 C1 121.2(2) . 3_566 ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.92(17) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.65(17) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.76(17) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 123.13(17) . . ?
N1 C5 C6 115.78(16) . . ?
C4 C5 C6 121.09(17) . . ?
Br1 C6 H6A 109.5 . . ?
Br1 C6 H6B 109.5 . . ?
C5 C6 Br1 110.84(13) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
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 C6 1.9690(19) . ?
N1 C1 1.345(2) . ?
N1 C5 1.342(2) . ?
C1 C1 1.489(4) 3_566 ?
C1 C2 1.393(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 C6 1.491(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
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
N1 C1 C1 N1 180.000(0) . . 3_566 3_566 ?
N1 C1 C1 C2 -0.2(3) . . 3_566 3_566 ?
N1 C1 C1 C2 0.2(3) 3_566 3_566 . . ?
N1 C5 C6 Br1 87.29(17) . . . . ?
C2 C1 C1 C2 180.000(0) . . 3_566 3_566 ?
C4 C5 C6 Br1 -93.54(19) . . . . ?
