#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/47/2204781.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2204781
loop_
_publ_author_name
'Yamin, Bohari M.'
'Hassan, Ibrahim N.'
_publ_section_title
;
 1-(2-Morpholinoethyl)-3-(3-phenylacryloyl)thiourea
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2513
_journal_page_last               o2514
_journal_paper_doi               10.1107/S1600536804030831
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H21 N3 O2 S'
_chemical_formula_moiety         'C16 H21 N3 O2 S'
_chemical_formula_sum            'C16 H21 N3 O2 S'
_chemical_formula_weight         319.42
_chemical_melting_point          .4505E-305
_chemical_name_systematic
;
1-(2-Morpholinoethyl)-3-(3-phenylacryloyl)thiourea
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.711(4)
_cell_angle_beta                 93.971(4)
_cell_angle_gamma                104.444(4)
_cell_formula_units_Z            2
_cell_length_a                   6.1452(14)
_cell_length_b                   9.731(2)
_cell_length_c                   14.690(3)
_cell_measurement_reflns_used    775
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.4
_cell_volume                     835.6(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8635
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         1.4
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.15
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3267
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.15
_refine_ls_R_factor_all          0.065
_refine_ls_R_factor_gt           0.053
_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)+(0.0564P)²+0.1504P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.125
_refine_ls_wR_factor_ref         0.131
_reflns_number_gt                2748
_reflns_number_total             3267
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rn6031.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2204781
_cod_database_fobs_code          2204781
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S1 1.35549(10) 1.27527(6) 0.61140(4) 0.0698(2) Uani d . 1 S
O1 0.8294(3) 0.98484(15) 0.74904(12) 0.0746(5) Uani d . 1 O
O2 1.0481(3) 0.52357(16) 0.76382(12) 0.0729(4) Uani d . 1 O
N1 1.0153(3) 1.19653(17) 0.70893(12) 0.0567(4) Uani d . 1 N
H1A 1.0213 1.2868 0.7161 0.068 Uiso calc R 1 H
N2 1.1533(3) 1.01339(18) 0.63855(12) 0.0611(5) Uani d . 1 N
H2A 1.0518 0.9585 0.6639 0.073 Uiso calc R 1 H
N3 1.1277(3) 0.72743(16) 0.64278(11) 0.0529(4) Uani d . 1 N
C1 0.3781(4) 1.3261(3) 0.90010(16) 0.0727(6) Uani d . 1 C
H1 0.4452 1.3748 0.8552 0.087 Uiso calc R 1 H
C2 0.2427(5) 1.3862(3) 0.95621(19) 0.0870(8) Uani d . 1 C
H2 0.2179 1.4742 0.9481 0.104 Uiso calc R 1 H
C3 0.1453(4) 1.3182(3) 1.02322(18) 0.0830(7) Uani d . 1 C
H3 0.0564 1.3603 1.0614 0.100 Uiso calc R 1 H
C4 0.1780(5) 1.1890(3) 1.0342(2) 0.0911(8) Uani d . 1 C
H4 0.1132 1.1426 1.0804 0.109 Uiso calc R 1 H
C5 0.3078(4) 1.1263(3) 0.97658(19) 0.0830(7) Uani d . 1 C
H5 0.3237 1.0355 0.9828 0.100 Uiso calc R 1 H
C6 0.4148(3) 1.1952(2) 0.90991(14) 0.0581(5) Uani d . 1 C
C7 0.5619(4) 1.1298(2) 0.85385(14) 0.0600(5) Uani d . 1 C
H7 0.5414 1.0312 0.8508 0.072 Uiso calc R 1 H
C8 0.7194(4) 1.1943(2) 0.80725(14) 0.0592(5) Uani d . 1 C
H8 0.7455 1.2928 0.8081 0.071 Uiso calc R 1 H
C9 0.8556(3) 1.1142(2) 0.75376(14) 0.0562(5) Uani d . 1 C
C10 1.1680(3) 1.1521(2) 0.65354(13) 0.0530(5) Uani d . 1 C
C11 1.2957(4) 0.9461(2) 0.58235(16) 0.0660(6) Uani d . 1 C
H11A 1.4441 0.9635 0.6161 0.079 Uiso calc R 1 H
H11B 1.3137 0.9862 0.5259 0.079 Uiso calc R 1 H
C12 1.1847(4) 0.7870(2) 0.55938(15) 0.0671(6) Uani d . 1 C
H12A 1.0481 0.7699 0.5173 0.081 Uiso calc R 1 H
H12B 1.2860 0.7383 0.5283 0.081 Uiso calc R 1 H
C13 1.3131(4) 0.6869(2) 0.68884(18) 0.0690(6) Uani d . 1 C
H13A 1.4458 0.7684 0.7014 0.083 Uiso calc R 1 H
H13B 1.3500 0.6091 0.6487 0.083 Uiso calc R 1 H
C14 1.2488(4) 0.6393(3) 0.77800(19) 0.0784(7) Uani d . 1 C
H14A 1.3717 0.6089 0.8067 0.094 Uiso calc R 1 H
H14B 1.2256 0.7201 0.8200 0.094 Uiso calc R 1 H
C15 0.8693(4) 0.5653(3) 0.71794(17) 0.0700(6) Uani d . 1 C
H15A 0.8382 0.6463 0.7570 0.084 Uiso calc R 1 H
H15B 0.7334 0.4861 0.7078 0.084 Uiso calc R 1 H
C16 0.9283(4) 0.6063(2) 0.62717(16) 0.0677(6) Uani d . 1 C
H16A 0.9574 0.5253 0.5874 0.081 Uiso calc R 1 H
H16B 0.8030 0.6324 0.5967 0.081 Uiso calc R 1 H
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
_geom_angle_publ_flag
C15 O2 C14 109.53(16) ?
C9 N1 C10 128.18(17) yes
C9 N1 H1A 115.9 ?
C10 N1 H1A 115.9 ?
C10 N2 C11 124.72(17) yes
C10 N2 H2A 117.6 ?
C11 N2 H2A 117.6 ?
C16 N3 C13 109.11(17) ?
C16 N3 C12 113.62(17) ?
C13 N3 C12 113.36(17) ?
C6 C1 C2 120.7(2) ?
C6 C1 H1 119.6 ?
C2 C1 H1 119.6 ?
C3 C2 C1 120.7(2) ?
C3 C2 H2 119.6 ?
C1 C2 H2 119.6 ?
C4 C3 C2 119.7(2) ?
C4 C3 H3 120.1 ?
C2 C3 H3 120.1 ?
C3 C4 C5 119.9(2) ?
C3 C4 H4 120.1 ?
C5 C4 H4 120.1 ?
C4 C5 C6 121.6(2) ?
C4 C5 H5 119.2 ?
C6 C5 H5 119.2 ?
C1 C6 C5 117.3(2) ?
C1 C6 C7 122.47(19) ?
C5 C6 C7 120.3(2) ?
C8 C7 C6 127.4(2) ?
C8 C7 H7 116.3 ?
C6 C7 H7 116.3 ?
C7 C8 C9 121.38(19) ?
C7 C8 H8 119.3 ?
C9 C8 H8 119.3 ?
O1 C9 N1 122.43(19) ?
O1 C9 C8 122.82(18) ?
N1 C9 C8 114.75(18) ?
N2 C10 N1 116.43(17) yes
N2 C10 S1 124.57(15) ?
N1 C10 S1 119.00(15) ?
N2 C11 C12 108.07(17) ?
N2 C11 H11A 110.1 ?
C12 C11 H11A 110.1 ?
N2 C11 H11B 110.1 ?
C12 C11 H11B 110.1 ?
H11A C11 H11B 108.4 ?
N3 C12 C11 111.27(17) ?
N3 C12 H12A 109.4 ?
C11 C12 H12A 109.4 ?
N3 C12 H12B 109.4 ?
C11 C12 H12B 109.4 ?
H12A C12 H12B 108.0 ?
N3 C13 C14 110.20(18) ?
N3 C13 H13A 109.6 ?
C14 C13 H13A 109.6 ?
N3 C13 H13B 109.6 ?
C14 C13 H13B 109.6 ?
H13A C13 H13B 108.1 ?
O2 C14 C13 111.9(2) ?
O2 C14 H14A 109.2 ?
C13 C14 H14A 109.2 ?
O2 C14 H14B 109.2 ?
C13 C14 H14B 109.2 ?
H14A C14 H14B 107.9 ?
O2 C15 C16 111.33(18) ?
O2 C15 H15A 109.4 ?
C16 C15 H15A 109.4 ?
O2 C15 H15B 109.4 ?
C16 C15 H15B 109.4 ?
H15A C15 H15B 108.0 ?
N3 C16 C15 109.23(18) ?
N3 C16 H16A 109.8 ?
C15 C16 H16A 109.8 ?
N3 C16 H16B 109.8 ?
C15 C16 H16B 109.8 ?
H16A C16 H16B 108.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C10 1.6675(19) yes
O1 C9 1.219(2) yes
O2 C15 1.425(3) yes
O2 C14 1.426(3) yes
N1 C9 1.377(2) yes
N1 C10 1.389(3) yes
N1 H1A 0.8600 ?
N2 C10 1.314(3) yes
N2 C11 1.449(3) yes
N2 H2A 0.8600 ?
N3 C16 1.450(3) yes
N3 C13 1.453(3) yes
N3 C12 1.460(3) yes
C1 C6 1.375(3) ?
C1 C2 1.380(3) ?
C1 H1 0.9300 ?
C2 C3 1.359(3) ?
C2 H2 0.9300 ?
C3 C4 1.352(4) ?
C3 H3 0.9300 ?
C4 C5 1.380(3) ?
C4 H4 0.9300 ?
C5 C6 1.382(3) ?
C5 H5 0.9300 ?
C6 C7 1.459(3) ?
C7 C8 1.311(3) yes
C7 H7 0.9300 ?
C8 C9 1.468(3) ?
C8 H8 0.9300 ?
C11 C12 1.503(3) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 C14 1.500(3) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 C16 1.492(3) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2A O1 1_555 0.86 1.95 2.642(3) 136 yes
N2 H2A N3 1_555 0.86 2.39 2.758(2) 107 yes
C7 H7 O1 1_555 0.93 2.48 2.813(3) 101 yes
N1 H1A O2 1_565 0.86 2.27 3.114(2) 169 yes
C15 H15B S1 1_445 0.97 2.81 3.731(3) 159 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654773
