#------------------------------------------------------------------------------
#$Date: 2016-03-05 12:47:04 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177919 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/48/7154857.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_7154857
loop_
_publ_author_name
'Murray, Paul M.'
'Bellany, Fiona'
'Benhamou, Laure'
'Bučar, Dejan-Krešimir'
'Tabor, Alethea B.'
'Sheppard, Tom D.'
_publ_section_title
;
 The application of design of experiments (DoE) reaction optimisation and
 solvent selection in the development of new synthetic chemistry.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2373
_journal_page_last               2384
_journal_paper_doi               10.1039/c5ob01892g
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H11 N5 S'
_chemical_formula_sum            'C9 H11 N5 S'
_chemical_formula_weight         221.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-09-10T10:50:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-09-10 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.0057(3)
_cell_length_b                   4.06460(10)
_cell_length_c                   12.0663(2)
_cell_measurement_reflns_used    8618
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      73.4440
_cell_measurement_theta_min      4.1770
_cell_volume                     1030.22(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.03
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_laue_measured_fraction_full 1
_diffrn_reflns_laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13406
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.99
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.611
_diffrn_reflns_theta_min         4.209
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.582
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics, implemented in 
SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2040
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0387P)²+0.1641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0684
_reflns_Friedel_coverage         0.899
_reflns_friedel_fraction_full    1
_reflns_friedel_fraction_max     0.989
_reflns_number_gt                1980
_reflns_number_total             2040
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ob01892g3.cif
_cod_data_source_block           13b
_cod_depositor_comments
'Adding full bibliography for 7154857--7154858.cif.'
_cod_database_code               7154857
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, 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
S1 S 0.50793(2) 0.15728(16) 0.53023(6) 0.04479(19) Uani 1 1 d . .
N3 N 0.71012(9) 0.7618(5) 0.45329(14) 0.0290(4) Uani 1 1 d . .
C5 C 0.65802(11) 0.5920(6) 0.41027(17) 0.0291(5) Uani 1 1 d . .
N2 N 0.61653(9) 0.4703(5) 0.48309(15) 0.0314(4) Uani 1 1 d . .
C9 C 0.79565(10) 1.0508(6) 0.44665(19) 0.0320(5) Uani 1 1 d . .
N4 N 0.75481(9) 0.8973(5) 0.38070(15) 0.0316(4) Uani 1 1 d . .
C2 C 0.56588(11) 0.3195(6) 0.4404(2) 0.0353(5) Uani 1 1 d . .
N1 N 0.55206(10) 0.2769(6) 0.33323(18) 0.0435(5) Uani 1 1 d . .
H1N H 0.7069(18) 0.766(8) 0.708(3) 0.065 Uiso 1 1 d . U
H2N H 0.6571(19) 0.590(9) 0.641(3) 0.065 Uiso 1 1 d . U
C4 C 0.64999(11) 0.5572(7) 0.29599(18) 0.0377(5) Uani 1 1 d . .
H4 H 0.6795 0.6372 0.2453 0.045 Uiso 1 1 calc R U
C3 C 0.59556(13) 0.3973(8) 0.2635(2) 0.0437(6) Uani 1 1 d . .
H3 H 0.5885 0.371 0.1879 0.052 Uiso 1 1 calc R U
C10 C 0.85302(12) 1.2184(7) 0.3996(2) 0.0418(6) Uani 1 1 d . .
H10A H 0.889 1.0739 0.4043 0.063 Uiso 1 1 calc R U
H10B H 0.8615 1.4156 0.4408 0.063 Uiso 1 1 calc R U
H10C H 0.8453 1.2734 0.3234 0.063 Uiso 1 1 calc R U
N5 N 0.68861(10) 0.7426(7) 0.64959(16) 0.0400(5) Uani 1 1 d . .
C7 C 0.72461(10) 0.8363(6) 0.56230(16) 0.0306(5) Uani 1 1 d . .
C8 C 0.77946(10) 1.0224(6) 0.55910(18) 0.0335(5) Uani 1 1 d . .
H8 H 0.8013 1.111 0.6192 0.04 Uiso 1 1 calc R U
C1 C 0.54321(12) 0.2298(8) 0.6631(2) 0.0446(6) Uani 1 1 d . .
H1A H 0.585 0.1345 0.665 0.067 Uiso 1 1 calc R U
H1B H 0.5173 0.1313 0.7197 0.067 Uiso 1 1 calc R U
H1C H 0.5462 0.4624 0.6759 0.067 Uiso 1 1 calc R U
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 0.0308(3) 0.0477(4) 0.0559(4) 0.0008(3) -0.0030(3) -0.0074(2)
N3 0.0278(9) 0.0369(11) 0.0223(8) -0.0010(8) -0.0004(7) 0.0002(8)
C5 0.0276(10) 0.0324(12) 0.0273(10) -0.0034(8) -0.0040(8) 0.0054(9)
N2 0.0270(9) 0.0349(11) 0.0323(9) -0.0026(8) -0.0042(7) 0.0018(8)
C9 0.0306(10) 0.0342(13) 0.0311(10) 0.0023(9) -0.0012(9) 0.0037(9)
N4 0.0292(9) 0.0395(11) 0.0260(8) 0.0012(8) 0.0019(7) 0.0017(8)
C2 0.0297(10) 0.0346(14) 0.0417(12) -0.0045(10) -0.0042(9) 0.0038(9)
N1 0.0355(11) 0.0525(14) 0.0424(11) -0.0110(10) -0.0109(9) 0.0008(10)
C4 0.0365(12) 0.0498(16) 0.0269(10) -0.0030(11) -0.0036(9) 0.0042(11)
C3 0.0404(13) 0.0592(16) 0.0316(12) -0.0109(11) -0.0103(10) 0.0055(12)
C10 0.0366(12) 0.0482(16) 0.0406(13) 0.0065(11) 0.0030(10) -0.0040(11)
N5 0.0365(11) 0.0615(14) 0.0220(9) -0.0016(9) -0.0002(8) -0.0076(11)
C7 0.0290(10) 0.0382(13) 0.0245(10) -0.0036(9) -0.0030(8) 0.0022(9)
C8 0.0330(10) 0.0394(13) 0.0280(10) -0.0024(10) -0.0039(8) -0.0016(9)
C1 0.0340(12) 0.0550(16) 0.0447(14) 0.0076(13) 0.0051(10) -0.0032(12)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C2 S1 C1 101.77(12)
C7 N3 C5 129.42(19)
C7 N3 N4 111.21(17)
C5 N3 N4 119.29(17)
N2 C5 N3 116.85(18)
N2 C5 C4 122.3(2)
N3 C5 C4 120.8(2)
C2 N2 C5 116.0(2)
N4 C9 C8 112.6(2)
N4 C9 C10 120.5(2)
C8 C9 C10 126.8(2)
C9 N4 N3 104.12(17)
N2 C2 N1 127.4(2)
N2 C2 S1 119.13(19)
N1 C2 S1 113.43(19)
C3 N1 C2 114.4(2)
C3 C4 C5 115.5(2)
C3 C4 H4 122.2
C5 C4 H4 122.2
N1 C3 C4 124.3(2)
N1 C3 H3 117.9
C4 C3 H3 117.9
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C7 N5 H1N 112(3)
C7 N5 H2N 121(2)
H1N N5 H2N 121(3)
N5 C7 C8 130.1(2)
N5 C7 N3 123.8(2)
C8 C7 N3 106.10(18)
C7 C8 C9 105.95(19)
C7 C8 H8 127
C9 C8 H8 127
S1 C1 H1A 109.5
S1 C1 H1B 109.5
H1A C1 H1B 109.5
S1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.759(3)
S1 C1 1.791(3)
N3 C7 1.384(3)
N3 C5 1.394(3)
N3 N4 1.397(3)
C5 N2 1.333(3)
C5 C4 1.396(3)
N2 C2 1.332(3)
C9 N4 1.326(3)
C9 C8 1.404(3)
C9 C10 1.496(3)
C2 N1 1.336(3)
N1 C3 1.335(4)
C4 C3 1.373(4)
C4 H4 0.93
C3 H3 0.93
C10 H10A 0.96
C10 H10B 0.96
C10 H10C 0.96
N5 C7 1.351(3)
N5 H1N 0.81(4)
N5 H2N 0.91(4)
C7 C8 1.379(3)
C8 H8 0.93
C1 H1A 0.96
C1 H1B 0.96
C1 H1C 0.96
