#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:22:52 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179018 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/16/4121624.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_4121624
loop_
_publ_author_name
'Gui, Jinghan'
'Zhou, Qianghui'
'Pan, Chung-Mao'
'Yabe, Yuki'
'Burns, Aaron C.'
'Collins, Michael R.'
'Ornelas, Martha A.'
'Ishihara, Yoshihiro'
'Baran, Phil S.'
_publ_section_title
;
 C-H Methylation of Heteroarenes Inspired by Radical SAM Methyl
 Transferase.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4853
_journal_page_last               4856
_journal_paper_doi               10.1021/ja5007838
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C11 H11 N3 O2 S, 0.5(C2 H4 Cl2), H2 O'
_chemical_formula_sum            'C12 H15 Cl N3 O3 S'
_chemical_formula_weight         316.78
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-01-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.711(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.464(4)
_cell_length_b                   5.2123(6)
_cell_length_c                   16.8968(17)
_cell_measurement_reflns_used    4411
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.953
_cell_measurement_theta_min      2.462
_cell_volume                     2885.9(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41812
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.782
_diffrn_reflns_theta_min         1.243
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.0921
_exptl_absorpt_correction_T_min  0.0670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1100 before and 0.0567 after correction.
The Ratio of minimum to maximum transmission is 0.7275.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       Blade
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.008
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0518
_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)+(0.0396P)²+11.5946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2011
_reflns_number_total             2768
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5007838_si_004.cif
_cod_data_source_block           PFLJ315
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/automatic-downloads/current/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 
;
_cod_database_code               4121624
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-4
_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   0.997
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All H(H,H) groups
2. Restrained distances
 O1S-H1S
 0.9 with sigma of 0.02
 H1SE-O1S
 0.9 with sigma of 0.02
 H1S-H1SE
 1.4 with sigma of 0.02
 N3-H3B = N3-H3A
 0.9 with sigma of 0.02
 O1S-H1SF
 0.9 with sigma of 0.02
 H1SF-H1S
 1.4 with sigma of 0.02
3. Others
 Sof(C1SB)=Sof(H1SC)=Sof(H1SD)=1-FVAR(1)
 Sof(C1S)=Sof(H1SA)=Sof(H1SB)=FVAR(1)
 Fixed Sof: H1SE(0.5) H1SF(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C1S(H1SA,H1SB), C1SB(H1SC,H1SD)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.38281(2) 0.64312(16) 0.89526(5) 0.0266(2) Uani 1 1 d . . . .
O1 O 0.41126(7) 0.7616(5) 0.96028(14) 0.0351(6) Uani 1 1 d . . . .
O2 O 0.37658(8) 0.3717(4) 0.89934(16) 0.0382(6) Uani 1 1 d . . . .
N1 N 0.29585(8) 0.6777(5) 1.11005(15) 0.0259(6) Uani 1 1 d . . . .
N2 N 0.28330(8) 0.5125(5) 1.04904(15) 0.0225(6) Uani 1 1 d . . . .
N3 N 0.28041(8) 0.3736(5) 0.92038(16) 0.0232(6) Uani 1 1 d D . . .
H3A H 0.2836(11) 0.400(7) 0.8711(13) 0.035(10) Uiso 1 1 d D . . .
H3B H 0.2622(8) 0.261(5) 0.9302(19) 0.028(9) Uiso 1 1 d D . . .
C1 C 0.31873(10) 0.8764(7) 1.10051(19) 0.0282(7) Uani 1 1 d . . . .
H1 H 0.3266 0.9927 1.1442 0.034 Uiso 1 1 calc R . . .
C2 C 0.33177(10) 0.9220(6) 1.02836(19) 0.0254(7) Uani 1 1 d . . . .
H2 H 0.3486 1.0652 1.0234 0.031 Uiso 1 1 calc R . . .
C3 C 0.31996(9) 0.7581(6) 0.96540(17) 0.0199(7) Uani 1 1 d . . . .
C4 C 0.29456(9) 0.5493(6) 0.97786(17) 0.0195(7) Uani 1 1 d . . . .
C5 C 0.33457(9) 0.7973(6) 0.88767(18) 0.0224(7) Uani 1 1 d . . . .
H5A H 0.3373 0.9830 0.8776 0.027 Uiso 1 1 calc R . . .
H5B H 0.3146 0.7239 0.8420 0.027 Uiso 1 1 calc R . . .
C6 C 0.39701(10) 0.7177(6) 0.8029(2) 0.0266(7) Uani 1 1 d . . . .
C7 C 0.38404(11) 0.5619(7) 0.7360(2) 0.0360(9) Uani 1 1 d . . . .
H7 H 0.3672 0.4171 0.7392 0.043 Uiso 1 1 calc R . . .
C8 C 0.39600(12) 0.6208(8) 0.6644(2) 0.0413(9) Uani 1 1 d . . . .
H8 H 0.3871 0.5163 0.6182 0.050 Uiso 1 1 calc R . . .
C9 C 0.42062(11) 0.8289(8) 0.6596(2) 0.0399(9) Uani 1 1 d . . . .
H9 H 0.4288 0.8672 0.6103 0.048 Uiso 1 1 calc R . . .
C10 C 0.43348(11) 0.9838(8) 0.7273(2) 0.0414(9) Uani 1 1 d . . . .
H10 H 0.4505 1.1277 0.7241 0.050 Uiso 1 1 calc R . . .
C11 C 0.42155(11) 0.9284(7) 0.7990(2) 0.0348(9) Uani 1 1 d . . . .
H11 H 0.4301 1.0340 0.8452 0.042 Uiso 1 1 calc R . . .
Cl1S Cl 0.49925(3) 0.3928(3) 0.87756(7) 0.0632(4) Uani 1 1 d . . . .
C1S C 0.5071(2) 0.575(2) 0.9680(10) 0.036(4) Uani 0.51(3) 1 d . P A 1
H1SA H 0.5364 0.6164 0.9855 0.043 Uiso 0.51(3) 1 calc R P A 1
H1SB H 0.4917 0.7381 0.9584 0.043 Uiso 0.51(3) 1 calc R P A 1
C1SB C 0.4940(3) 0.371(2) 0.9813(14) 0.055(6) Uani 0.49(3) 1 d . P A 2
H1SC H 0.4654 0.3302 0.9844 0.066 Uiso 0.49(3) 1 calc R P A 2
H1SD H 0.5120 0.2352 1.0099 0.066 Uiso 0.49(3) 1 calc R P A 2
O1S O 0.26623(8) 0.5672(5) 1.24551(14) 0.0353(6) Uani 1 1 d D . . .
H1S H 0.2785(12) 0.582(8) 1.2033(18) 0.062(14) Uiso 1 1 d D . . .
H1SE H 0.267(3) 0.734(6) 1.262(4) 0.093 Uiso 0.5 1 d DR P B 1
H1SF H 0.255(3) 0.408(9) 1.238(5) 0.093 Uiso 0.5 1 d DR P C 2
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'
Cl Cl 0.1484 0.1585 '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'
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
O1 S1 C5 108.08(15) .
O1 S1 C6 109.00(15) .
O2 S1 O1 117.84(16) .
O2 S1 C5 108.04(15) .
O2 S1 C6 109.12(16) .
C6 S1 C5 103.85(15) .
C1 N1 N2 120.6(3) .
N1 N2 C4 119.6(3) .
H3A N3 H3B 120(3) .
C4 N3 H3A 119(3) .
C4 N3 H3B 118(2) .
N1 C1 H1 118.9 .
N1 C1 C2 122.2(3) .
C2 C1 H1 118.9 .
C1 C2 H2 120.5 .
C3 C2 C1 118.9(3) .
C3 C2 H2 120.5 .
C2 C3 C4 116.9(3) .
C2 C3 C5 120.2(3) .
C4 C3 C5 122.9(3) .
N2 C4 N3 115.2(3) .
N2 C4 C3 121.7(3) .
N3 C4 C3 123.1(3) .
S1 C5 H5A 109.9 .
S1 C5 H5B 109.9 .
C3 C5 S1 109.0(2) .
C3 C5 H5A 109.9 .
C3 C5 H5B 109.9 .
H5A C5 H5B 108.3 .
C7 C6 S1 119.7(3) .
C11 C6 S1 119.1(3) .
C11 C6 C7 121.2(3) .
C6 C7 H7 120.5 .
C8 C7 C6 119.0(3) .
C8 C7 H7 120.5 .
C7 C8 H8 119.6 .
C9 C8 C7 120.7(4) .
C9 C8 H8 119.6 .
C8 C9 H9 120.1 .
C8 C9 C10 119.7(3) .
C10 C9 H9 120.1 .
C9 C10 H10 119.9 .
C11 C10 C9 120.2(4) .
C11 C10 H10 119.9 .
C6 C11 C10 119.2(3) .
C6 C11 H11 120.4 .
C10 C11 H11 120.4 .
Cl1S C1S H1SA 109.8 .
Cl1S C1S H1SB 109.8 .
C1S C1S Cl1S 109.4(12) 5_667
C1S C1S H1SA 109.8 5_667
C1S C1S H1SB 109.8 5_667
H1SA C1S H1SB 108.2 .
Cl1S C1SB H1SC 110.5 .
Cl1S C1SB H1SD 110.5 .
C1SB C1SB Cl1S 106.3(15) 5_667
C1SB C1SB H1SC 110.5 5_667
C1SB C1SB H1SD 110.5 5_667
H1SC C1SB H1SD 108.7 .
H1S O1S H1SE 100(3) .
H1S O1S H1SF 102(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.439(3) .
S1 O2 1.434(3) .
S1 C5 1.784(3) .
S1 C6 1.765(3) .
N1 N2 1.344(4) .
N1 C1 1.317(4) .
N2 C4 1.345(4) .
N3 H3A 0.872(18) .
N3 H3B 0.887(18) .
N3 C4 1.349(4) .
C1 H1 0.9500 .
C1 C2 1.396(5) .
C2 H2 0.9500 .
C2 C3 1.359(4) .
C3 C4 1.423(4) .
C3 C5 1.505(4) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.388(5) .
C6 C11 1.381(5) .
C7 H7 0.9500 .
C7 C8 1.382(5) .
C8 H8 0.9500 .
C8 C9 1.375(6) .
C9 H9 0.9500 .
C9 C10 1.395(5) .
C10 H10 0.9500 .
C10 C11 1.381(5) .
C11 H11 0.9500 .
Cl1S C1S 1.773(18) .
Cl1S C1SB 1.80(2) .
C1S C1S 1.49(3) 5_667
C1S H1SA 0.9900 .
C1S H1SB 0.9900 .
C1SB C1SB 1.50(3) 5_667
C1SB H1SC 0.9900 .
C1SB H1SD 0.9900 .
O1S H1S 0.895(19) .
O1S H1SE 0.91(2) .
O1S H1SF 0.90(2) .
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
N3 H3A O1S 0.872(18) 2.09(2) 2.912(3) 157(3) 6_565
N3 H3B N2 0.887(18) 2.164(19) 3.051(4) 178(3) 7_557
O1S H1S N1 0.895(19) 1.86(2) 2.734(3) 166(4) .
O1S H1SE N3 0.91(2) 2.68(8) 2.912(3) 96(5) 6_566
O1S H1SE O1S 0.91(2) 2.06(6) 2.839(2) 143(9) 4_557
O1S H1SF O1S 0.90(2) 1.96(2) 2.839(2) 164(7) 4_547
