#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:58:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180325 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/39/7153981.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_7153981
loop_
_publ_author_name
'Sadler, Scott A.'
'Tajuddin, Hazmi'
'Mkhalid, Ibraheem A. I.'
'Batsanov, Andrei S.'
'Albesa-Jove, David'
'Cheung, Man Sing'
'Maxwell, Aoife C.'
'Shukla, Lena'
'Roberts, Bryan'
'Blakemore, David C.'
'Lin, Zhenyang'
'Marder, Todd B.'
'Steel, Patrick G.'
_publ_section_title
;
 Iridium-catalyzed C-H borylation of pyridines.
;
_journal_issue                   37
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7318
_journal_page_last               7327
_journal_paper_doi               10.1039/c4ob01565g
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C10 H10 N2 S'
_chemical_formula_sum            'C10 H10 N2 S'
_chemical_formula_weight         190.26
_chemical_melting_point          324
_chemical_name_systematic
;
 2,3-dimethy-5-thiophen-2-yl-pyrazine
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-02-24
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.168(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1352(19)
_cell_length_b                   12.292(3)
_cell_length_c                   11.175(3)
_cell_measurement_reflns_used    868
_cell_measurement_temperature    250
_cell_measurement_theta_max      29.258
_cell_measurement_theta_min      3.303
_cell_volume                     977.5(4)
_computing_cell_refinement       'SMART V5.625 (Bruker, 2001)'
_computing_data_collection       'SMART version 4.05 (Siemens, 1995)'
_computing_data_reduction        'SAINT V6.45 (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      250
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7011
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.467
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0372
_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)+(0.0516P)²+0.2351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1411
_reflns_number_total             1720
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ob01565g2.cif
_cod_data_source_block           S14
_cod_depositor_comments
'Adding full bibliography for 7153976--7153981.cif.'
_cod_database_code               7153981
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2014-1
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Uiso(H9A)=Uiso(H9B)=Uiso(H9C)=FVAR(1)
 Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=FVAR(2)
3.a Rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
#END Tags that were not found in dictionaries
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
S1 S 0.51909(8) 0.22601(5) 0.30142(5) 0.0641(2) Uani 1 1 d .
N1 N -0.0495(3) 0.34521(17) 0.02237(15) 0.0694(5) Uani 1 1 d .
N2 N 0.1438(2) 0.33077(13) 0.24693(13) 0.0505(4) Uani 1 1 d .
C1 C 0.6803(3) 0.1371(2) 0.2521(2) 0.0736(7) Uani 1 1 d .
H1 H 0.7899 0.1154 0.2976 0.088 Uiso 1 1 calc R
C2 C 0.6312(3) 0.1019(2) 0.1402(2) 0.0766(7) Uani 1 1 d .
H2 H 0.7031 0.0523 0.0988 0.092 Uiso 1 1 calc R
C3 C 0.4610(3) 0.14715(19) 0.09139(19) 0.0620(5) Uani 1 1 d .
H3 H 0.4077 0.1310 0.0140 0.074 Uiso 1 1 calc R
C4 C 0.3811(3) 0.21716(15) 0.16840(16) 0.0487(5) Uani 1 1 d .
C5 C 0.2076(3) 0.28003(15) 0.15090(16) 0.0475(4) Uani 1 1 d .
C6 C -0.0152(3) 0.38772(17) 0.23085(18) 0.0548(5) Uani 1 1 d .
C7 C -0.1141(3) 0.39453(17) 0.1178(2) 0.0613(5) Uani 1 1 d .
C8 C 0.1100(3) 0.28852(18) 0.03933(18) 0.0619(6) Uani 1 1 d .
H8 H 0.1577 0.2532 -0.0266 0.074 Uiso 1 1 calc R
C9 C -0.2947(3) 0.4571(2) 0.0974(3) 0.0872(8) Uani 1 1 d .
H9A H -0.2727 0.5329 0.1179 0.132(7) Uiso 1 1 d GR
H9B H -0.3877 0.4272 0.1473 0.132(7) Uiso 1 1 d GR
H9C H -0.3401 0.4515 0.0137 0.132(7) Uiso 1 1 d GR
C10 C -0.0842(3) 0.4433(2) 0.3393(2) 0.0764(7) Uani 1 1 d .
H10A H -0.0913 0.5211 0.3251 0.118(6) Uiso 1 1 d GR
H10B H 0.0020 0.4288 0.4086 0.118(6) Uiso 1 1 d GR
H10C H -0.2079 0.4158 0.3539 0.118(6) Uiso 1 1 d GR
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
S1 0.0650(4) 0.0787(4) 0.0477(3) -0.0061(3) -0.0012(2) -0.0017(3)
N1 0.0707(12) 0.0841(14) 0.0522(11) 0.0060(10) -0.0040(8) 0.0047(10)
N2 0.0556(9) 0.0516(9) 0.0446(9) -0.0045(7) 0.0056(7) -0.0076(8)
C1 0.0594(13) 0.0927(17) 0.0685(15) 0.0006(13) 0.0019(11) 0.0071(12)
C2 0.0696(15) 0.0913(18) 0.0703(15) -0.0090(13) 0.0148(12) 0.0133(13)
C3 0.0663(13) 0.0720(14) 0.0481(11) -0.0066(10) 0.0076(9) -0.0004(11)
C4 0.0552(11) 0.0523(11) 0.0389(10) 0.0023(8) 0.0061(8) -0.0085(9)
C5 0.0551(11) 0.0473(10) 0.0406(10) 0.0006(8) 0.0065(8) -0.0098(8)
C6 0.0553(11) 0.0496(11) 0.0598(12) -0.0042(9) 0.0067(9) -0.0080(9)
C7 0.0600(12) 0.0570(13) 0.0664(13) 0.0054(10) 0.0024(10) -0.0018(10)
C8 0.0676(14) 0.0740(14) 0.0439(11) -0.0005(10) 0.0034(9) 0.0018(11)
C9 0.0724(16) 0.0890(18) 0.099(2) 0.0116(15) -0.0012(14) 0.0163(14)
C10 0.0680(15) 0.0822(17) 0.0801(16) -0.0249(13) 0.0122(12) 0.0008(12)
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'
S S 0.1246 0.1234 '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
C1 S1 C4 92.12(10)
C8 N1 C7 117.57(19)
C6 N2 C5 117.94(17)
S1 C1 H1 124.1
C2 C1 S1 111.73(19)
C2 C1 H1 124.1
C1 C2 H2 123.5
C1 C2 C3 113.0(2)
C3 C2 H2 123.5
C2 C3 H3 123.5
C4 C3 C2 113.0(2)
C4 C3 H3 123.5
C3 C4 S1 110.09(16)
C3 C4 C5 129.46(18)
C5 C4 S1 120.45(14)
N2 C5 C4 118.05(17)
N2 C5 C8 120.25(19)
C8 C5 C4 121.70(18)
N2 C6 C7 121.28(18)
N2 C6 C10 117.04(19)
C7 C6 C10 121.7(2)
N1 C7 C6 120.70(19)
N1 C7 C9 116.9(2)
C6 C7 C9 122.4(2)
N1 C8 C5 122.2(2)
N1 C8 H8 118.9
C5 C8 H8 118.9
C7 C9 H9A 109.5
C7 C9 H9B 109.5
C7 C9 H9C 109.4
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C6 C10 H10A 109.4
C6 C10 H10B 109.5
C6 C10 H10C 109.4
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.707(2)
S1 C4 1.7256(19)
N1 C7 1.337(3)
N1 C8 1.336(3)
N2 C5 1.349(2)
N2 C6 1.334(3)
C1 H1 0.9400
C1 C2 1.346(3)
C2 H2 0.9400
C2 C3 1.409(3)
C3 H3 0.9400
C3 C4 1.370(3)
C4 C5 1.461(3)
C5 C8 1.387(3)
C6 C7 1.404(3)
C6 C10 1.504(3)
C7 C9 1.503(3)
C8 H8 0.9400
C9 H9A 0.9700
C9 H9B 0.9701
C9 H9C 0.9698
C10 H10A 0.9700
C10 H10B 0.9699
C10 H10C 0.9699
