#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:13:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180417 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/86/7208602.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_7208602
loop_
_publ_author_name
'Štrukil, Vjekoslav'
'Igrc, Marina D.'
'Fábián, László'
'Eckert-Maksić, Mirjana'
'Childs, Scott L.'
'Reid, David G.'
'Duer, Melinda J.'
'Halasz, Ivan'
'Mottillo, Cristina'
'Friščić, Tomislav'
_publ_section_title
;
 A model for a solvent-free synthetic organic research laboratory:
 click-mechanosynthesis and structural characterization of thioureas
 without bulk solvents
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              2462
_journal_paper_doi               10.1039/c2gc35799b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C11 H13 N3 O3 S'
_chemical_formula_sum            'C11 H13 N3 O3 S'
_chemical_formula_weight         267.30
_chemical_name_common            N-(4-nitrophenyl)-N'-(morpholino)thiourea
_chemical_name_systematic
;
N-(4-nitrophenyl)-N'-(morpholino)thiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 90.788(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2252(2)
_cell_length_b                   10.5172(3)
_cell_length_c                   11.1949(2)
_cell_measurement_reflns_used    5406
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      1.00
_cell_volume                     1203.79(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11967
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         32.00
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                2986
_reflns_number_total             4139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2gc35799b.txt
_cod_data_source_block           4j-form1
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7208602
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.08124(3) 0.18288(3) 0.02280(2) 0.02646(9) Uani 1 1 d .
O3 O -0.19432(7) 0.01785(8) 0.35947(6) 0.02758(18) Uani 1 1 d .
N1 N -0.13737(8) 0.32202(8) 0.03140(7) 0.02131(19) Uani 1 1 d .
H1 H -0.1980 0.3570 0.0757 0.026 Uiso 1 1 calc R
N2 N -0.14387(9) 0.48606(10) -0.44652(7) 0.0269(2) Uani 1 1 d .
O1 O -0.11795(8) 0.40917(9) -0.52547(6) 0.0331(2) Uani 1 1 d .
O2 O -0.17488(9) 0.59696(9) -0.46653(7) 0.0383(2) Uani 1 1 d .
N3 N -0.09474(8) 0.19933(9) 0.19623(8) 0.0247(2) Uani 1 1 d .
C1 C -0.05671(10) 0.23526(10) 0.08586(8) 0.0206(2) Uani 1 1 d .
C2 C -0.13255(9) 0.36066(10) -0.08904(8) 0.0198(2) Uani 1 1 d .
C3 C -0.14783(10) 0.48931(11) -0.11457(8) 0.0234(2) Uani 1 1 d .
H3 H -0.1567 0.5486 -0.0511 0.028 Uiso 1 1 calc R
C4 C -0.15018(10) 0.53182(11) -0.23213(9) 0.0240(2) Uani 1 1 d .
H4 H -0.1605 0.6196 -0.2501 0.029 Uiso 1 1 calc R
C5 C -0.13710(10) 0.44272(11) -0.32248(8) 0.0219(2) Uani 1 1 d .
C6 C -0.12165(10) 0.31461(11) -0.29938(9) 0.0233(2) Uani 1 1 d .
H6 H -0.1124 0.2559 -0.3632 0.028 Uiso 1 1 calc R
C7 C -0.11974(10) 0.27267(11) -0.18183(9) 0.0222(2) Uani 1 1 d .
H7 H -0.1098 0.1847 -0.1645 0.027 Uiso 1 1 calc R
C8 C -0.22741(10) 0.21298(11) 0.24383(9) 0.0251(2) Uani 1 1 d .
H8A H -0.2855 0.2524 0.1828 0.030 Uiso 1 1 calc R
H8B H -0.2252 0.2689 0.3150 0.030 Uiso 1 1 calc R
C9 C -0.27939(10) 0.08392(11) 0.27742(9) 0.0259(2) Uani 1 1 d .
H9A H -0.3663 0.0942 0.3141 0.031 Uiso 1 1 calc R
H9B H -0.2908 0.0321 0.2042 0.031 Uiso 1 1 calc R
C10 C -0.06757(11) 0.00283(12) 0.30836(10) 0.0310(3) Uani 1 1 d .
H10A H -0.0751 -0.0488 0.2347 0.037 Uiso 1 1 calc R
H10B H -0.0096 -0.0429 0.3654 0.037 Uiso 1 1 calc R
C11 C -0.00853(11) 0.13015(12) 0.27913(9) 0.0293(3) Uani 1 1 d .
H11A H 0.0039 0.1802 0.3533 0.035 Uiso 1 1 calc R
H11B H 0.0781 0.1178 0.2425 0.035 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 O3 C9 109.96(8)
C1 N1 C2 126.15(9)
C1 N1 H1 116.9
C2 N1 H1 116.9
O2 N2 O1 123.44(9)
O2 N2 C5 118.54(9)
O1 N2 C5 118.02(10)
C1 N3 C11 122.61(9)
C1 N3 C8 125.52(9)
C11 N3 C8 111.65(8)
N3 C1 N1 114.45(9)
N3 C1 S1 123.06(8)
N1 C1 S1 122.44(7)
C3 C2 C7 120.16(9)
C3 C2 N1 118.13(9)
C7 C2 N1 121.63(10)
C4 C3 C2 120.51(10)
C4 C3 H3 119.7
C2 C3 H3 119.7
C5 C4 C3 118.22(10)
C5 C4 H4 120.9
C3 C4 H4 120.9
C6 C5 C4 122.33(9)
C6 C5 N2 119.07(9)
C4 C5 N2 118.57(10)
C5 C6 C7 119.20(10)
C5 C6 H6 120.4
C7 C6 H6 120.4
C6 C7 C2 119.58(10)
C6 C7 H7 120.2
C2 C7 H7 120.2
N3 C8 C9 109.42(9)
N3 C8 H8A 109.8
C9 C8 H8A 109.8
N3 C8 H8B 109.8
C9 C8 H8B 109.8
H8A C8 H8B 108.2
O3 C9 C8 112.51(9)
O3 C9 H9A 109.1
C8 C9 H9A 109.1
O3 C9 H9B 109.1
C8 C9 H9B 109.1
H9A C9 H9B 107.8
O3 C10 C11 110.86(10)
O3 C10 H10A 109.5
C11 C10 H10A 109.5
O3 C10 H10B 109.5
C11 C10 H10B 109.5
H10A C10 H10B 108.1
N3 C11 C10 109.86(9)
N3 C11 H11A 109.7
C10 C11 H11A 109.7
N3 C11 H11B 109.7
C10 C11 H11B 109.7
H11A C11 H11B 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6790(11)
O3 C10 1.4326(13)
O3 C9 1.4357(12)
N1 C1 1.3677(13)
N1 C2 1.4097(12)
N1 H1 0.8800
N2 O2 1.2285(13)
N2 O1 1.2296(13)
N2 C5 1.4623(12)
N3 C1 1.3542(13)
N3 C11 1.4646(13)
N3 C8 1.4713(13)
C2 C3 1.3913(15)
C2 C7 1.3986(14)
C3 C4 1.3899(13)
C3 H3 0.9500
C4 C5 1.3866(15)
C4 H4 0.9500
C5 C6 1.3807(15)
C6 C7 1.3878(14)
C6 H6 0.9500
C7 H7 0.9500
C8 C9 1.5073(16)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.5067(17)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9900
C11 H11B 0.9900
