#------------------------------------------------------------------------------
#$Date: 2022-02-04 22:04:33 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/41/7244101.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_7244101
loop_
_publ_author_name
'Delledonne, Andrea'
'Orlandini, Martina'
'Mazzeo, Paolo P.'
'Sissa, Cristina'
'Bacchi, Alessia'
'Terenziani, Francesca'
'Pelagatti, Paolo'
_publ_section_title
;
 Bis-isonicotinoyl linkers containing polyaromatic scaffolds: synthesis,
 structure and spectroscopic properties.
;
_journal_issue                   2
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              1191
_journal_page_last               1201
_journal_paper_doi               10.1039/d1cp04438a
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C2 H6 O S, C11 H8 N2 O'
_chemical_formula_sum            'C13 H14 N2 O2 S'
_chemical_formula_weight         262.32
_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   geom
_audit_creation_date             2021-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-22 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                96.092(2)
_cell_angle_beta                 103.963(2)
_cell_angle_gamma                111.340(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6003(5)
_cell_length_b                   9.7756(7)
_cell_length_c                   9.7883(7)
_cell_measurement_reflns_used    2640
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.467
_cell_measurement_theta_min      2.195
_cell_volume                     642.06(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture, Photon II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6838
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.467
_diffrn_reflns_theta_min         2.195
_exptl_absorpt_coefficient_mu    0.247
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       prism
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0447
_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)+(0.0368P)²+0.2336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1981
_reflns_number_total             2640
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cp04438a2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7244101--7244105.cif.'
_cod_database_code               7244101
_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) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C007(H007), C00A(H00A), C00B(H00B), C00C(H00C), C00E(H00E),
 C00G(H00G), C00H(H00H)
2.b Idealised Me refined as rotating group:
 C00F(H00D,H00F,H00I), C00I(H00J,H00K,H00L)
;
_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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.32134(8) 0.52833(6) 0.67175(6) 0.04403(19) Uani 1 1 d . . . . .
O002 O 0.2650(2) 0.45525(18) 0.51533(16) 0.0537(4) Uani 1 1 d . . . . .
N003 N 0.2746(3) 0.16625(19) 0.41383(17) 0.0395(4) Uani 1 1 d . . . . .
H003 H 0.3245 0.2611 0.4503 0.047 Uiso 1 1 calc R . . . .
O004 O 0.2420(3) -0.06004(18) 0.47083(17) 0.0700(6) Uani 1 1 d . . . . .
N005 N 0.6030(3) 0.2962(2) 0.9509(2) 0.0542(5) Uani 1 1 d . . . . .
C006 C 0.0309(3) -0.0521(2) 0.0326(2) 0.0341(4) Uani 1 1 d . . . . .
C007 C 0.1175(3) 0.2264(2) 0.1992(2) 0.0396(5) Uani 1 1 d . . . . .
H007 H 0.1482 0.3199 0.2549 0.047 Uiso 1 1 calc R . . . .
C008 C 0.1755(3) 0.1209(2) 0.2641(2) 0.0353(5) Uani 1 1 d . . . . .
C009 C 0.4067(3) 0.1566(2) 0.6603(2) 0.0378(5) Uani 1 1 d . . . . .
C00A C 0.0172(3) 0.1928(2) 0.0561(2) 0.0406(5) Uani 1 1 d . . . . .
H00A H -0.0204 0.2637 0.0158 0.049 Uiso 1 1 calc R . . . .
C00B C 0.5606(3) 0.2975(2) 0.7002(2) 0.0437(5) Uani 1 1 d . . . . .
H00B H 0.6011 0.3488 0.6310 0.052 Uiso 1 1 calc R . . . .
C00C C 0.1347(3) -0.0159(2) 0.1813(2) 0.0384(5) Uani 1 1 d . . . . .
H00C H 0.1755 -0.0847 0.2231 0.046 Uiso 1 1 calc R . . . .
C00D C 0.2990(3) 0.0757(2) 0.5059(2) 0.0421(5) Uani 1 1 d . . . . .
C00E C 0.3544(3) 0.0867(3) 0.7688(2) 0.0463(5) Uani 1 1 d . . . . .
H00E H 0.2533 -0.0089 0.7466 0.056 Uiso 1 1 calc R . . . .
C00F C 0.2570(4) 0.6852(3) 0.6747(3) 0.0569(6) Uani 1 1 d . . . . .
H00D H 0.3409 0.7590 0.6351 0.085 Uiso 1 1 calc GR . . . .
H00F H 0.2739 0.7281 0.7723 0.085 Uiso 1 1 calc GR . . . .
H00I H 0.1212 0.6535 0.6183 0.085 Uiso 1 1 calc GR . . . .
C00G C 0.6527(4) 0.3603(3) 0.8454(2) 0.0523(6) Uani 1 1 d . . . . .
H00G H 0.7574 0.4544 0.8710 0.063 Uiso 1 1 calc R . . . .
C00H C 0.4541(4) 0.1609(3) 0.9102(2) 0.0535(6) Uani 1 1 d . . . . .
H00H H 0.4150 0.1133 0.9818 0.064 Uiso 1 1 calc R . . . .
C00I C 0.1362(5) 0.4127(3) 0.7396(3) 0.0766(9) Uani 1 1 d . . . . .
H00J H 0.0079 0.3999 0.6810 0.115 Uiso 1 1 calc GR . . . .
H00K H 0.1577 0.4593 0.8370 0.115 Uiso 1 1 calc GR . . . .
H00L H 0.1428 0.3163 0.7375 0.115 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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O002 S001 C00F 106.24(10) . . ?
O002 S001 C00I 105.92(12) . . ?
C00F S001 C00I 98.38(14) . . ?
C008 N003 H003 116.6 . . ?
C00D N003 H003 116.6 . . ?
C00D N003 C008 126.75(18) . . ?
C00G N005 C00H 115.8(2) . . ?
C006 C006 C00A 117.6(2) 2 2 ?
C00C C006 C006 120.5(2) . 2 ?
C00C C006 C00A 121.87(19) . 2 ?
C008 C007 H007 119.6 . . ?
C00A C007 H007 119.6 . . ?
C00A C007 C008 120.84(19) . . ?
C007 C008 N003 116.04(17) . . ?
C00C C008 N003 124.31(19) . . ?
C00C C008 C007 119.65(18) . . ?
C00B C009 C00D 123.10(19) . . ?
C00B C009 C00E 117.73(19) . . ?
C00E C009 C00D 119.15(19) . . ?
C006 C00A H00A 119.4 2 . ?
C007 C00A C006 121.29(19) . 2 ?
C007 C00A H00A 119.4 . . ?
C009 C00B H00B 120.8 . . ?
C00G C00B C009 118.4(2) . . ?
C00G C00B H00B 120.8 . . ?
C006 C00C H00C 120.0 . . ?
C008 C00C C006 120.08(19) . . ?
C008 C00C H00C 120.0 . . ?
N003 C00D C009 114.48(18) . . ?
O004 C00D N003 124.7(2) . . ?
O004 C00D C009 120.81(19) . . ?
C009 C00E H00E 120.5 . . ?
C00H C00E C009 119.0(2) . . ?
C00H C00E H00E 120.5 . . ?
S001 C00F H00D 109.5 . . ?
S001 C00F H00F 109.5 . . ?
S001 C00F H00I 109.5 . . ?
H00D C00F H00F 109.5 . . ?
H00D C00F H00I 109.5 . . ?
H00F C00F H00I 109.5 . . ?
N005 C00G C00B 124.8(2) . . ?
N005 C00G H00G 117.6 . . ?
C00B C00G H00G 117.6 . . ?
N005 C00H C00E 124.2(2) . . ?
N005 C00H H00H 117.9 . . ?
C00E C00H H00H 117.9 . . ?
S001 C00I H00J 109.5 . . ?
S001 C00I H00K 109.5 . . ?
S001 C00I H00L 109.5 . . ?
H00J C00I H00K 109.5 . . ?
H00J C00I H00L 109.5 . . ?
H00K C00I H00L 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O002 1.5056(15) . ?
S001 C00F 1.771(2) . ?
S001 C00I 1.775(3) . ?
N003 H003 0.8600 . ?
N003 C008 1.413(2) . ?
N003 C00D 1.356(3) . ?
O004 C00D 1.216(3) . ?
N005 C00G 1.325(3) . ?
N005 C00H 1.331(3) . ?
C006 C006 1.416(4) 2 ?
C006 C00A 1.416(3) 2 ?
C006 C00C 1.414(3) . ?
C007 H007 0.9300 . ?
C007 C008 1.412(3) . ?
C007 C00A 1.363(3) . ?
C008 C00C 1.374(3) . ?
C009 C00B 1.382(3) . ?
C009 C00D 1.502(3) . ?
C009 C00E 1.383(3) . ?
C00A C006 1.416(3) 2 ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00B C00G 1.382(3) . ?
C00C H00C 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00H 1.377(3) . ?
C00F H00D 0.9600 . ?
C00F H00F 0.9600 . ?
C00F H00I 0.9600 . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I H00J 0.9600 . ?
C00I H00K 0.9600 . ?
C00I H00L 0.9600 . ?
