#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:00:19 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/96/7239654.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_7239654
loop_
_publ_author_name
'Arenaza-Corona, Antonino'
'Villamil-Ramos, Raúl'
'Guerrero-Álvarez, Jorge'
'Höpfl, Herbert'
'Barba, Victor'
_publ_section_title
;
 Bis-Dithiocarbamates derived from 1,10-diaza-18-crown-6 as ligand tectons
 for 1D, 2D and 3D supramolecular structure arrangements
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1063
_journal_page_last               1077
_journal_paper_doi               10.1039/C9CE01755K
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C6 H16 N, C7 H12 N O2 S2'
_chemical_formula_sum            'C13 H28 N2 O2 S2'
_chemical_formula_weight         308.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-01 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                107.997(3)
_cell_angle_beta                 97.814(4)
_cell_angle_gamma                112.553(3)
_cell_formula_units_Z            2
_cell_length_a                   9.218(2)
_cell_length_b                   9.960(2)
_cell_length_c                   11.516(2)
_cell_measurement_reflns_used    911
_cell_measurement_temperature    295.15(2)
_cell_measurement_theta_max      20.75
_cell_measurement_theta_min      2.41
_cell_volume                     888.8(3)
_computing_cell_refinement       'SAINT v6.02A (Bruker, 2001)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v6.02A (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1986 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7623
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        23.498
_diffrn_reflns_theta_max         23.498
_diffrn_reflns_theta_min         1.943
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0561
_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)+(0.0638P)²+0.6642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2238
_reflns_number_total             2628
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01755k2.cif
_cod_data_source_block           48vbarbm
_cod_depositor_comments
;Adding full bibliography for 7239651--7239656.cif.

 Adding full bibliography for 7239651--7239656.cif.
;
_cod_database_code               7239654
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -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
H2 H 0.184(4) 0.859(4) 0.497(4) 0.075(11) Uiso 1 1 d .
S1 S 0.93061(12) 0.57964(10) 0.25364(8) 0.0562(3) Uani 1 1 d .
S2 S 1.20031(12) 0.90573(11) 0.33001(8) 0.0633(3) Uani 1 1 d .
O1 O 0.7101(2) 0.7120(3) -0.0604(2) 0.0544(6) Uani 1 1 d .
O2 O 1.3080(3) 0.9944(2) -0.0075(2) 0.0470(6) Uani 1 1 d .
N1 N 0.9989(3) 0.7277(3) 0.0970(2) 0.0385(6) Uani 1 1 d .
N2 N 0.1814(4) 0.8469(4) 0.5832(3) 0.0702(9) Uani 1 1 d .
C1 C 1.0387(4) 0.7349(4) 0.2167(3) 0.0430(7) Uani 1 1 d .
C2 C 0.8675(4) 0.5863(3) -0.0072(3) 0.0416(7) Uani 1 1 d .
H2A H 0.8582 0.4937 0.0088 0.050 Uiso 1 1 calc R
H2B H 0.8967 0.5773 -0.0861 0.050 Uiso 1 1 calc R
C3 C 0.7050(4) 0.5883(4) -0.0231(3) 0.0486(8) Uani 1 1 d .
H3A H 0.6208 0.4878 -0.0872 0.058 Uiso 1 1 calc R
H3B H 0.6773 0.6030 0.0568 0.058 Uiso 1 1 calc R
C4 C 0.5628(4) 0.7262(4) -0.0698(4) 0.0519(9) Uani 1 1 d .
H4A H 0.5360 0.7396 0.0103 0.062 Uiso 1 1 calc R
H4B H 0.4735 0.6312 -0.1361 0.062 Uiso 1 1 calc R
C5 C 1.4150(4) 1.1346(4) 0.1008(3) 0.0475(8) Uani 1 1 d .
H5A H 1.5204 1.1353 0.1250 0.057 Uiso 1 1 calc R
H5B H 1.3691 1.1389 0.1720 0.057 Uiso 1 1 calc R
C6 C 1.2319(4) 0.8616(4) 0.0237(3) 0.0453(8) Uani 1 1 d .
H6A H 1.3086 0.8661 0.0930 0.054 Uiso 1 1 calc R
H6B H 1.2003 0.7648 -0.0496 0.054 Uiso 1 1 calc R
C7 C 1.0819(4) 0.8614(3) 0.0627(3) 0.0412(7) Uani 1 1 d .
H7A H 1.1143 0.9593 0.1350 0.049 Uiso 1 1 calc R
H7B H 1.0059 0.8570 -0.0071 0.049 Uiso 1 1 calc R
C8 C 0.3192(7) 0.9913(6) 0.6773(4) 0.1023(16) Uani 1 1 d .
H8A H 0.4205 0.9977 0.6585 0.123 Uiso 1 1 calc R
H8B H 0.3256 0.9890 0.7614 0.123 Uiso 1 1 calc R
C9 C 0.2994(9) 1.1393(6) 0.6765(5) 0.133(3) Uani 1 1 d .
H9A H 0.2994 1.1448 0.5948 0.200 Uiso 1 1 calc GR
H9B H 0.3888 1.2330 0.7416 0.200 Uiso 1 1 calc GR
H9C H 0.1976 1.1315 0.6928 0.200 Uiso 1 1 calc GR
C10 C 0.2162(6) 0.7034(5) 0.5758(5) 0.0900(14) Uani 1 1 d .
H10A H 0.2404 0.7044 0.6608 0.108 Uiso 1 1 calc R
H10B H 0.1177 0.6063 0.5232 0.108 Uiso 1 1 calc R
C11 C 0.3503(7) 0.7028(7) 0.5243(6) 0.1166(19) Uani 1 1 d .
H11A H 0.3281 0.7030 0.4405 0.175 Uiso 1 1 calc GR
H11B H 0.3623 0.6098 0.5196 0.175 Uiso 1 1 calc GR
H11C H 0.4499 0.7953 0.5787 0.175 Uiso 1 1 calc GR
C12 C 0.0106(6) 0.8080(6) 0.5913(4) 0.0844(13) Uani 1 1 d .
H12A H -0.0133 0.8935 0.5874 0.101 Uiso 1 1 calc R
H12B H -0.0648 0.7133 0.5171 0.101 Uiso 1 1 calc R
C13 C -0.0210(7) 0.7824(6) 0.7066(5) 0.1027(16) Uani 1 1 d .
H13A H -0.0116 0.6895 0.7061 0.154 Uiso 1 1 calc GR
H13B H -0.1296 0.7686 0.7078 0.154 Uiso 1 1 calc GR
H13C H 0.0577 0.8725 0.7810 0.154 Uiso 1 1 calc GR
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_site_symmetry_3
C4 O1 C3 113.0(2) .
C5 O2 C6 113.1(2) .
C1 N1 C2 122.3(2) .
C1 N1 C7 122.4(2) .
C7 N1 C2 115.3(2) .
C8 N2 C10 108.9(4) .
C8 N2 C12 120.2(4) .
C12 N2 C10 109.2(3) .
S1 C1 S2 121.52(18) .
N1 C1 S1 120.5(2) .
N1 C1 S2 117.9(2) .
N1 C2 C3 113.1(2) .
O1 C3 C2 110.1(2) .
O1 C4 C5 108.6(2) 2_775
O2 C5 C4 109.2(3) 2_775
O2 C6 C7 109.8(2) .
N1 C7 C6 112.3(2) .
N2 C8 C9 110.7(4) .
C11 C10 N2 113.9(4) .
C13 C12 N2 115.2(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.704(3) .
S2 C1 1.724(3) .
O1 C3 1.412(4) .
O1 C4 1.411(4) .
O2 C5 1.418(4) .
O2 C6 1.422(3) .
N1 C1 1.350(4) .
N1 C2 1.463(4) .
N1 C7 1.463(4) .
N2 C8 1.455(6) .
N2 C10 1.561(5) .
N2 C12 1.494(5) .
C2 C3 1.493(4) .
C4 C5 1.483(4) 2_775
C5 C4 1.483(4) 2_775
C6 C7 1.510(4) .
C8 C9 1.556(7) .
C10 C11 1.443(7) .
C12 C13 1.473(6) .
