#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:19:14 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179017 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/15/4121575.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_4121575
loop_
_publ_author_name
'Foo, Klement'
'Sella, Eran'
'Thomé, Isabelle'
'Eastgate, Martin D.'
'Baran, Phil S.'
_publ_section_title
;
 A mild, ferrocene-catalyzed C-h imidation of (hetero)arenes.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5279
_journal_page_last               5282
_journal_paper_doi               10.1021/ja501879c
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C8 H6 Br N O2 S'
_chemical_formula_sum            'C8 H6 Br N O2 S'
_chemical_formula_weight         260.11
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   10.1024(4)
_cell_length_b                   20.0404(10)
_cell_length_c                   13.0272(5)
_cell_measurement_reflns_used    4715
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.55
_cell_volume                     2637.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus rotating andoe'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17288
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    4.874
_exptl_absorpt_correction_T_max  0.6414
_exptl_absorpt_correction_T_min  0.4741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.965
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         3.039
_refine_diff_density_min         -1.563
_refine_diff_density_rms         0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     224
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0740
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0899P)²+35.6892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2136
_reflns_number_gt                2210
_reflns_number_total             2773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja501879c_si_002.cif
_cod_data_source_block           baran365
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4121575--4121576.cif.
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4121575
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 1.03092(8) 0.58088(4) 0.40067(6) 0.0365(3) Uani 1 1 d U
S1 S 0.78065(17) 0.57780(9) 0.53376(14) 0.0249(4) Uani 1 1 d U
O1 O 0.3471(5) 0.5944(3) 0.4219(4) 0.0314(12) Uani 1 1 d U
N1 N 0.5082(5) 0.5822(3) 0.5435(5) 0.0218(12) Uani 1 1 d U
C1 C 0.8464(8) 0.5813(4) 0.4123(6) 0.0286(15) Uani 1 1 d U
O2 O 0.6194(5) 0.5720(3) 0.6980(4) 0.0320(13) Uani 1 1 d U
C2 C 0.7563(7) 0.5833(4) 0.3361(6) 0.0281(15) Uani 1 1 d U
H2A H 0.7769 0.5842 0.2649 0.034 Uiso 1 1 calc R
C3 C 0.6260(7) 0.5841(4) 0.3773(6) 0.0270(15) Uani 1 1 d U
H3A H 0.5490 0.5861 0.3356 0.032 Uiso 1 1 calc R
C4 C 0.6210(6) 0.5819(4) 0.4813(6) 0.0217(14) Uani 1 1 d U
C5 C 0.3795(6) 0.5901(4) 0.5104(6) 0.0233(14) Uani 1 1 d U
C6 C 0.2900(7) 0.5891(4) 0.6035(5) 0.0272(15) Uani 1 1 d U
H6A H 0.2307 0.5497 0.6014 0.033 Uiso 1 1 calc R
H6B H 0.2351 0.6299 0.6060 0.033 Uiso 1 1 calc R
C7 C 0.3819(6) 0.5855(4) 0.6972(5) 0.0227(14) Uani 1 1 d U
H7A H 0.3749 0.6266 0.7391 0.027 Uiso 1 1 calc R
H7B H 0.3600 0.5465 0.7406 0.027 Uiso 1 1 calc R
C8 C 0.5167(7) 0.5788(4) 0.6525(6) 0.0262(15) Uani 1 1 d U
Br1' Br 1.01924(10) 0.7500 0.59963(9) 0.0309(3) Uani 1 2 d SU
S1' S 0.7699(2) 0.7500 0.46590(18) 0.0223(5) Uani 1 2 d SU
O1' O 0.3355(7) 0.7500 0.5776(5) 0.0276(16) Uani 1 2 d SU
N1' N 0.4992(7) 0.7500 0.4529(7) 0.0183(16) Uani 1 2 d SU
C1' C 0.8352(9) 0.7500 0.5863(7) 0.0204(18) Uani 1 2 d SU
O2' O 0.6127(7) 0.7500 0.3007(5) 0.0290(17) Uani 1 2 d SU
C2' C 0.7440(10) 0.7500 0.6633(8) 0.0241(19) Uani 1 2 d SU
H2'A H 0.7652 0.7500 0.7343 0.029 Uiso 1 2 calc SR
C3' C 0.6158(10) 0.7500 0.6245(8) 0.024(2) Uani 1 2 d SU
H3'A H 0.5386 0.7500 0.6662 0.029 Uiso 1 2 calc SR
C4' C 0.6132(8) 0.7500 0.5172(7) 0.0195(18) Uani 1 2 d SU
C5' C 0.3711(8) 0.7500 0.4884(8) 0.0184(18) Uani 1 2 d SU
C6' C 0.2777(10) 0.7500 0.3948(7) 0.0227(19) Uani 1 2 d SU
H6'A H 0.2209 0.7098 0.3943 0.027 Uiso 0.50 1 calc PR
H6'B H 0.2209 0.7902 0.3943 0.027 Uiso 0.50 1 calc PR
C7' C 0.3736(9) 0.7500 0.3026(8) 0.027(2) Uani 1 2 d SU
H7'A H 0.3596 0.7099 0.2597 0.033 Uiso 0.50 1 calc PR
H7'B H 0.3596 0.7901 0.2597 0.033 Uiso 0.50 1 calc PR
C8' C 0.5066(8) 0.7500 0.3460(8) 0.0198(19) Uani 1 2 d SU
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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C4 89.7(4)
C5 N1 C4 126.0(6)
C5 N1 C8 111.9(6)
C4 N1 C8 121.9(6)
C2 C1 S1 114.7(6)
C2 C1 Br1 127.9(6)
S1 C1 Br1 117.4(4)
C1 C2 C3 110.3(7)
C1 C2 H2A 124.8
C3 C2 H2A 124.8
C4 C3 C2 114.3(7)
C4 C3 H3A 122.8
C2 C3 H3A 122.8
C3 C4 N1 127.5(6)
C3 C4 S1 110.9(5)
N1 C4 S1 121.6(5)
O1 C5 N1 124.4(6)
O1 C5 C6 127.4(6)
N1 C5 C6 108.2(6)
C5 C6 C7 106.0(6)
C5 C6 H6A 110.5
C7 C6 H6A 110.5
C5 C6 H6B 110.5
C7 C6 H6B 110.5
H6A C6 H6B 108.7
C8 C7 C6 104.3(6)
C8 C7 H7A 110.9
C6 C7 H7A 110.9
C8 C7 H7B 110.9
C6 C7 H7B 110.9
H7A C7 H7B 108.9
O2 C8 N1 123.3(7)
O2 C8 C7 127.4(7)
N1 C8 C7 109.3(6)
C1' S1' C4' 89.9(5)
C5' N1' C8' 112.7(8)
C5' N1' C4' 124.3(9)
C8' N1' C4' 123.0(7)
C2' C1' S1' 114.6(7)
C2' C1' Br1' 127.2(7)
S1' C1' Br1' 118.1(6)
C1' C2' C3' 111.3(9)
C1' C2' H2'A 124.4
C3' C2' H2'A 124.4
C2' C3' C4' 112.4(9)
C2' C3' H3'A 123.8
C4' C3' H3'A 123.8
C3' C4' N1' 127.1(9)
C3' C4' S1' 111.8(7)
N1' C4' S1' 121.1(7)
O1' C5' N1' 126.8(9)
O1' C5' C6' 125.1(8)
N1' C5' C6' 108.0(8)
C7' C6' C5' 103.4(8)
C7' C6' H6'A 111.1
C5' C6' H6'A 111.1
C7' C6' H6'B 111.1
C5' C6' H6'B 111.1
H6'A C6' H6'B 109.0
C8' C7' C6' 106.1(8)
C8' C7' H7'A 110.5
C6' C7' H7'A 110.5
C8' C7' H7'B 110.5
C6' C7' H7'B 110.5
H7'A C7' H7'B 108.7
O2' C8' N1' 121.9(8)
O2' C8' C7' 128.4(10)
N1' C8' C7' 109.7(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.870(8)
S1 C1 1.718(8)
S1 C4 1.754(6)
O1 C5 1.202(9)
N1 C5 1.379(8)
N1 C4 1.398(9)
N1 C8 1.425(11)
C1 C2 1.348(11)
O2 C8 1.202(9)
C2 C3 1.422(10)
C2 H2A 0.9500
C3 C4 1.356(10)
C3 H3A 0.9500
C5 C6 1.512(10)
C6 C7 1.535(10)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.487(9)
C7 H7A 0.9900
C7 H7B 0.9900
Br1' C1' 1.868(10)
S1' C1' 1.701(9)
S1' C4' 1.719(9)
O1' C5' 1.215(12)
N1' C5' 1.375(11)
N1' C8' 1.395(13)
N1' C4' 1.423(11)
C1' C2' 1.362(14)
O2' C8' 1.223(12)
C2' C3' 1.390(14)
C2' H2'A 0.9500
C3' C4' 1.398(13)
C3' H3'A 0.9500
C5' C6' 1.542(13)
C6' C7' 1.542(13)
C6' H6'A 0.9900
C6' H6'B 0.9900
C7' C8' 1.458(12)
C7' H7'A 0.9900
C7' H7'B 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
C4 S1 C1 C2 -1.8(7)
C4 S1 C1 Br1 178.8(5)
S1 C1 C2 C3 1.8(9)
Br1 C1 C2 C3 -178.9(6)
C1 C2 C3 C4 -0.7(10)
C2 C3 C4 N1 179.7(7)
C2 C3 C4 S1 -0.6(9)
C5 N1 C4 C3 -5.3(12)
C8 N1 C4 C3 179.1(8)
C5 N1 C4 S1 175.1(6)
C8 N1 C4 S1 -0.5(9)
C1 S1 C4 C3 1.3(6)
C1 S1 C4 N1 -179.0(6)
C4 N1 C5 O1 3.8(12)
C8 N1 C5 O1 179.8(8)
C4 N1 C5 C6 -178.6(6)
C8 N1 C5 C6 -2.6(8)
O1 C5 C6 C7 -177.9(8)
N1 C5 C6 C7 4.6(8)
C5 C6 C7 C8 -4.7(8)
C5 N1 C8 O2 180.0(7)
C4 N1 C8 O2 -3.9(11)
C5 N1 C8 C7 -0.6(8)
C4 N1 C8 C7 175.6(6)
C6 C7 C8 O2 -177.2(8)
C6 C7 C8 N1 3.4(8)
C4' S1' C1' C2' 0.000(2)
C4' S1' C1' Br1' 180.0
S1' C1' C2' C3' 0.000(2)
Br1' C1' C2' C3' 180.000(2)
C1' C2' C3' C4' 0.000(2)
C2' C3' C4' N1' 180.000(2)
C2' C3' C4' S1' 0.000(2)
C5' N1' C4' C3' 0.000(2)
C8' N1' C4' C3' 180.000(2)
C5' N1' C4' S1' 180.0
C8' N1' C4' S1' 0.000(1)
C1' S1' C4' C3' 0.000(2)
C1' S1' C4' N1' 180.000(1)
C8' N1' C5' O1' 180.000(1)
C4' N1' C5' O1' 0.000(2)
C8' N1' C5' C6' 0.000(1)
C4' N1' C5' C6' 180.000(1)
O1' C5' C6' C7' 180.000(2)
N1' C5' C6' C7' 0.000(1)
C5' C6' C7' C8' 0.000(1)
C5' N1' C8' O2' 180.000(1)
C4' N1' C8' O2' 0.000(2)
C5' N1' C8' C7' 0.000(1)
C4' N1' C8' C7' 180.000(1)
C6' C7' C8' O2' 180.000(1)
C6' C7' C8' N1' 0.000(1)
