#------------------------------------------------------------------------------
#$Date: 2015-11-15 04:22:59 +0200 (Sun, 15 Nov 2015) $
#$Revision: 170323 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/13/2241311.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_2241311
loop_
_publ_author_name
'Anitha, B. R.'
'Gunaseelan, A. Thomas'
'Vinduvahini, M.'
'Kavitha, H. D.'
'Devarajegowda, H. C.'
_publ_section_title
;
 Crystal structure of (7-fluoro-2-oxo-2H-chromen-4-yl)methyl
 morpholine-4-carbodithioate
;
_journal_coeditor_code           HB7537
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o928
_journal_page_last               o929
_journal_paper_doi               10.1107/S2056989015021179
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C15 H14 F N O3 S2'
_chemical_formula_moiety         'C15 H14 F N O3 S2'
_chemical_formula_sum            'C15 H14 F N O3 S2'
_chemical_formula_weight         339.39
_chemical_melting_point          413
_chemical_name_systematic
;
(7-Fluoro-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodithioate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                74.779(2)
_cell_angle_beta                 87.653(2)
_cell_angle_gamma                74.241(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0285(3)
_cell_length_b                   7.8845(3)
_cell_length_c                   14.8151(6)
_cell_measurement_reflns_used    2683
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.991
_cell_measurement_theta_min      1.425
_cell_volume                     762.01(5)
_computing_cell_refinement
;
SAINT (Bruker, 2001)
;
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_data_reduction
;
SAINT (Bruker, 2001)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'ω and φ scans'
_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  0.1708
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10293
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         1.425
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       Plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.869
_refine_diff_density_min         -1.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.2574
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0425P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1263
_reflns_number_gt                1352
_reflns_number_total             2683
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7537sup1.cif
_cod_data_source_block           I
_cod_database_code               2241311
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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_occupancy
F F1 0.9653(3) 0.2708(3) 0.50738(15) 0.0859(8) Uani d 1
S S2 0.29218(11) 0.78840(9) 0.14758(6) 0.0461(3) Uani d 1
S S3 -0.06235(10) 0.70598(9) 0.07735(7) 0.0518(3) Uani d 1
O O4 0.4232(3) 0.1520(2) 0.38952(16) 0.0527(7) Uani d 1
O O5 0.1885(3) 0.0795(2) 0.32697(18) 0.0719(9) Uani d 1
O O6 0.4365(3) 0.7772(3) -0.19559(19) 0.0646(8) Uani d 1
N N7 0.2427(3) 0.7703(3) -0.0227(2) 0.0398(8) Uani d 1
C C8 0.2533(5) 0.2013(4) 0.3352(3) 0.0501(11) Uani d 1
C C9 0.1673(4) 0.3931(3) 0.2956(2) 0.0439(10) Uani d 1
H H9 0.0452 0.4306 0.2640 0.053 Uiso calc 1
C C10 0.2554(4) 0.5204(3) 0.3023(2) 0.0388(9) Uani d 1
C C11 0.4419(4) 0.4640(3) 0.3540(2) 0.0391(9) Uani d 1
C C12 0.5198(4) 0.2788(3) 0.3958(2) 0.0428(9) Uani d 1
C C13 0.5487(5) 0.5827(4) 0.3661(2) 0.0506(10) Uani d 1
H H13 0.4997 0.7074 0.3394 0.061 Uiso calc 1
C C14 0.7248(5) 0.5187(4) 0.4167(3) 0.0581(11) Uani d 1
H H14 0.7959 0.5983 0.4237 0.070 Uiso calc 1
C C15 0.7935(5) 0.3342(5) 0.4566(3) 0.0576(11) Uani d 1
C C16 0.6958(4) 0.2118(4) 0.4476(2) 0.0540(11) Uani d 1
H H16 0.7458 0.0876 0.4754 0.065 Uiso calc 1
C C17 0.1662(4) 0.7184(3) 0.2536(2) 0.0455(10) Uani d 1
H H17A 0.1744 0.7928 0.2953 0.055 Uiso calc 1
H H17B 0.0276 0.7377 0.2387 0.055 Uiso calc 1
C C18 0.1546(4) 0.7529(3) 0.0590(2) 0.0358(9) Uani d 1
C C19 0.1388(5) 0.7751(4) -0.1081(3) 0.0513(11) Uani d 1
H H19A 0.0697 0.9005 -0.1387 0.062 Uiso calc 1
H H19B 0.0410 0.7068 -0.0910 0.062 Uiso calc 1
C C20 0.2771(5) 0.6969(4) -0.1743(3) 0.0647(12) Uani d 1
H H20A 0.3295 0.5666 -0.1473 0.078 Uiso calc 1
H H20B 0.2047 0.7139 -0.2318 0.078 Uiso calc 1
C C21 0.5445(4) 0.7488(4) -0.1116(3) 0.0568(11) Uani d 1
H H21A 0.6569 0.7993 -0.1262 0.068 Uiso calc 1
H H21B 0.5948 0.6187 -0.0837 0.068 Uiso calc 1
C C22 0.4230(4) 0.8337(4) -0.0435(3) 0.0468(10) Uani d 1
H H22A 0.3857 0.9654 -0.0683 0.056 Uiso calc 1
H H22B 0.5005 0.8042 0.0140 0.056 Uiso calc 1
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'
F F 0.0171 0.0103 '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
C18 S2 C17 104.01(14)
C8 O4 C12 121.2(2)
C20 O6 C21 108.9(3)
C18 N7 C19 121.1(2)
C18 N7 C22 124.6(3)
C19 N7 C22 112.4(3)
O5 C8 O4 116.7(3)
O5 C8 C9 126.3(3)
O4 C8 C9 117.0(3)
C10 C9 C8 122.8(3)
C10 C9 H9 118.6
C8 C9 H9 118.6
C9 C10 C11 119.0(3)
C9 C10 C17 120.7(3)
C11 C10 C17 120.3(2)
C12 C11 C13 117.5(3)
C12 C11 C10 117.9(2)
C13 C11 C10 124.6(3)
O4 C12 C16 116.1(2)
O4 C12 C11 121.7(3)
C16 C12 C11 122.1(3)
C14 C13 C11 121.2(3)
C14 C13 H13 119.4
C11 C13 H13 119.4
C15 C14 C13 118.5(3)
C15 C14 H14 120.7
C13 C14 H14 120.7
F1 C15 C16 118.2(3)
F1 C15 C14 118.8(3)
C16 C15 C14 123.0(3)
C15 C16 C12 117.6(3)
C15 C16 H16 121.2
C12 C16 H16 121.2
C10 C17 S2 111.30(19)
C10 C17 H17A 109.4
S2 C17 H17A 109.4
C10 C17 H17B 109.4
S2 C17 H17B 109.4
H17A C17 H17B 108.0
N7 C18 S3 124.0(3)
N7 C18 S2 113.0(2)
S3 C18 S2 123.0(2)
N7 C19 C20 111.8(3)
N7 C19 H19A 109.2
C20 C19 H19A 109.2
N7 C19 H19B 109.2
C20 C19 H19B 109.2
H19A C19 H19B 107.9
O6 C20 C19 112.9(3)
O6 C20 H20A 109.0
C19 C20 H20A 109.0
O6 C20 H20B 109.0
C19 C20 H20B 109.0
H20A C20 H20B 107.8
O6 C21 C22 112.4(3)
O6 C21 H21A 109.1
C22 C21 H21A 109.1
O6 C21 H21B 109.1
C22 C21 H21B 109.1
H21A C21 H21B 107.9
C21 C22 N7 111.6(2)
C21 C22 H22A 109.3
N7 C22 H22A 109.3
C21 C22 H22B 109.3
N7 C22 H22B 109.3
H22A C22 H22B 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C15 1.350(3)
S2 C18 1.783(3)
S2 C17 1.804(3)
S3 C18 1.660(3)
O4 C8 1.374(3)
O4 C12 1.375(3)
O5 C8 1.203(3)
O6 C20 1.417(3)
O6 C21 1.419(4)
N7 C18 1.329(4)
N7 C19 1.473(4)
N7 C22 1.478(3)
C8 C9 1.437(4)
C9 C10 1.340(3)
C9 H9 0.9300
C10 C11 1.446(4)
C10 C17 1.504(3)
C11 C12 1.390(3)
C11 C13 1.398(4)
C12 C16 1.382(4)
C13 C14 1.373(4)
C13 H13 0.9300
C14 C15 1.374(4)
C14 H14 0.9300
C15 C16 1.362(4)
C16 H16 0.9300
C17 H17A 0.9700
C17 H17B 0.9700
C19 C20 1.484(4)
C19 H19A 0.9700
C19 H19B 0.9700
C20 H20A 0.9700
C20 H20B 0.9700
C21 C22 1.472(4)
C21 H21A 0.9700
C21 H21B 0.9700
C22 H22A 0.9700
C22 H22B 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
C14 H14 F1 2_766 0.93 2.56 3.451(3) 161 yes
C17 H17A O5 1_565 0.97 2.45 3.346(3) 153 yes
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
C12 O4 C8 O5 173.5(3)
C12 O4 C8 C9 -8.1(5)
O5 C8 C9 C10 -175.2(3)
O4 C8 C9 C10 6.6(5)
C8 C9 C10 C11 -2.1(5)
C8 C9 C10 C17 175.5(3)
C9 C10 C11 C12 -0.9(5)
C17 C10 C11 C12 -178.5(3)
C9 C10 C11 C13 179.9(3)
C17 C10 C11 C13 2.3(6)
C8 O4 C12 C16 -176.0(3)
C8 O4 C12 C11 5.4(5)
C13 C11 C12 O4 178.5(3)
C10 C11 C12 O4 -0.7(5)
C13 C11 C12 C16 0.1(5)
C10 C11 C12 C16 -179.2(3)
C12 C11 C13 C14 0.5(5)
C10 C11 C13 C14 179.7(3)
C11 C13 C14 C15 -0.9(6)
C13 C14 C15 F1 -179.1(3)
C13 C14 C15 C16 0.6(6)
F1 C15 C16 C12 179.7(3)
C14 C15 C16 C12 0.0(6)
O4 C12 C16 C15 -178.9(3)
C11 C12 C16 C15 -0.3(5)
C9 C10 C17 S2 -101.8(3)
C11 C10 C17 S2 75.8(4)
C18 S2 C17 C10 92.2(2)
C19 N7 C18 S3 9.0(3)
C22 N7 C18 S3 172.21(18)
C19 N7 C18 S2 -170.17(18)
C22 N7 C18 S2 -7.0(3)
C17 S2 C18 N7 -170.21(18)
C17 S2 C18 S3 10.60(18)
C18 N7 C19 C20 -149.2(3)
C22 N7 C19 C20 45.7(3)
C21 O6 C20 C19 59.9(4)
N7 C19 C20 O6 -53.0(4)
C20 O6 C21 C22 -61.1(3)
O6 C21 C22 N7 55.4(4)
C18 N7 C22 C21 148.5(3)
C19 N7 C22 C21 -47.0(3)

_cod_database_fobs_code 2241311
