#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:08:20 +0300 (Sun, 06 Sep 2020) $
#$Revision: 255945 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/70/7127001.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_7127001
loop_
_publ_author_name
'Bhunia, Supriya'
'Dolai, Anirban'
'Samanta, Subhas'
_publ_section_title
;
 Robust bi-directional photoswitching of thiomethyl substituted
 arylazopyrazoles under visible light.
;
_journal_issue                   70
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10247
_journal_page_last               10250
_journal_paper_doi               10.1039/d0cc04098c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C13 H16 N4 S'
_chemical_formula_sum            'C13 H16 N4 S'
_chemical_formula_weight         260.36
_chemical_properties_physical    Photo-sensitive
_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             2020-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-10 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                80.680(3)
_cell_angle_beta                 89.072(3)
_cell_angle_gamma                84.658(16)
_cell_formula_units_Z            2
_cell_length_a                   6.9549(12)
_cell_length_b                   8.8714(13)
_cell_length_c                   11.149(2)
_cell_measurement_reflns_used    10604
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.611
_cell_measurement_theta_min      1.851
_cell_volume                     675.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker-AXS SMART APEXII diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10604
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.611
_diffrn_reflns_theta_min         1.851
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol-Diethyl ether'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.975
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0726
_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)+(0.1672P)²+0.0736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2084
_refine_ls_wR_factor_ref         0.2251
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2561
_reflns_number_total             3091
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc04098c2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 7127000--7127001.cif.'
_cod_database_code               7127001
_shelx_shelxl_version_number     2018/3
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C4(H4)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C12(H12A,H12B,
 H12C)
;
_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
S1 S 0.26172(10) -0.01427(6) 0.70888(5) 0.0626(3) Uani 1 1 d . . . . .
N1 N 0.2294(2) 0.30442(18) 0.63037(14) 0.0414(4) Uani 1 1 d . . . . .
N2 N 0.2421(2) 0.44230(18) 0.58476(14) 0.0402(4) Uani 1 1 d . . . . .
N3 N 0.2679(2) 0.6020(2) 0.27779(16) 0.0515(5) Uani 1 1 d . . . . .
N4 N 0.2569(3) 0.4551(2) 0.25971(17) 0.0561(5) Uani 1 1 d . . . . .
C7 C 0.2489(2) 0.4704(2) 0.45926(16) 0.0400(4) Uani 1 1 d . . . . .
C1 C 0.2255(3) 0.2747(2) 0.75936(17) 0.0395(4) Uani 1 1 d . . . . .
C8 C 0.2629(3) 0.6180(2) 0.39480(18) 0.0456(5) Uani 1 1 d . . . . .
C10 C 0.2451(3) 0.3734(2) 0.36981(18) 0.0470(5) Uani 1 1 d . . . . .
C2 C 0.2404(3) 0.1187(2) 0.81031(17) 0.0426(4) Uani 1 1 d . . . . .
C6 C 0.2065(3) 0.3863(3) 0.8336(2) 0.0519(5) Uani 1 1 d . . . . .
H6 H 0.193704 0.489518 0.799282 0.062 Uiso 1 1 calc R . . . .
C3 C 0.2408(4) 0.0793(3) 0.9364(2) 0.0572(6) Uani 1 1 d . . . . .
H3 H 0.252554 -0.023488 0.971894 0.069 Uiso 1 1 calc R . . . .
C11 C 0.2303(4) 0.2047(3) 0.3836(2) 0.0628(6) Uani 1 1 d . . . . .
H11A H 0.236274 0.173605 0.304934 0.094 Uiso 1 1 calc GR . . . .
H11B H 0.109977 0.180623 0.421989 0.094 Uiso 1 1 calc GR . . . .
H11C H 0.335285 0.151245 0.432705 0.094 Uiso 1 1 calc GR . . . .
C5 C 0.2064(4) 0.3445(3) 0.9590(2) 0.0644(6) Uani 1 1 d . . . . .
H5 H 0.194628 0.419444 1.008802 0.077 Uiso 1 1 calc R . . . .
C13 C 0.2702(4) 0.7659(3) 0.4392(3) 0.0617(6) Uani 1 1 d . . . . .
H13A H 0.377481 0.816723 0.402412 0.093 Uiso 1 1 calc GR . . . .
H13B H 0.285382 0.747272 0.525972 0.093 Uiso 1 1 calc GR . . . .
H13C H 0.152455 0.829501 0.418179 0.093 Uiso 1 1 calc GR . . . .
C4 C 0.2239(4) 0.1923(3) 1.0092(2) 0.0664(7) Uani 1 1 d . . . . .
H4 H 0.224380 0.164626 1.093273 0.080 Uiso 1 1 calc R . . . .
C14 C 0.2776(4) 0.7216(3) 0.1720(2) 0.0657(7) Uani 1 1 d . . . . .
H14A H 0.149519 0.765921 0.149393 0.099 Uiso 1 1 calc GR . . . .
H14B H 0.336647 0.677843 0.105506 0.099 Uiso 1 1 calc GR . . . .
H14C H 0.353059 0.799684 0.191297 0.099 Uiso 1 1 calc GR . . . .
C12 C 0.2887(5) -0.1958(3) 0.8077(3) 0.0834(9) Uani 1 1 d . . . . .
H12A H 0.398610 -0.199385 0.859395 0.125 Uiso 1 1 calc GR . . . .
H12B H 0.307319 -0.276799 0.759843 0.125 Uiso 1 1 calc GR . . . .
H12C H 0.174722 -0.208406 0.856590 0.125 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'
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
C2 S1 C12 103.27(12) . . ?
N2 N1 C1 114.96(16) . . ?
N1 N2 C7 114.77(16) . . ?
N4 N3 C14 118.6(2) . . ?
C8 N3 N4 113.48(17) . . ?
C8 N3 C14 127.9(2) . . ?
C10 N4 N3 105.48(18) . . ?
N2 C7 C8 121.70(17) . . ?
N2 C7 C10 132.66(17) . . ?
C8 C7 C10 105.64(17) . . ?
C2 C1 N1 114.82(17) . . ?
C6 C1 N1 124.87(18) . . ?
C6 C1 C2 120.31(18) . . ?
N3 C8 C7 105.40(17) . . ?
N3 C8 C13 124.39(19) . . ?
C7 C8 C13 130.21(19) . . ?
N4 C10 C7 110.00(19) . . ?
N4 C10 C11 119.7(2) . . ?
C7 C10 C11 130.27(19) . . ?
C1 C2 S1 117.00(15) . . ?
C3 C2 S1 124.41(17) . . ?
C3 C2 C1 118.6(2) . . ?
C1 C6 H6 119.9 . . ?
C1 C6 C5 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
S1 C2 1.757(2) . ?
S1 C12 1.794(3) . ?
N1 N2 1.257(2) . ?
N1 C1 1.420(2) . ?
N2 C7 1.382(2) . ?
N3 N4 1.360(3) . ?
N3 C8 1.334(3) . ?
N3 C14 1.458(3) . ?
N4 C10 1.326(3) . ?
C7 C8 1.399(3) . ?
C7 C10 1.420(3) . ?
C1 C2 1.403(3) . ?
C1 C6 1.386(3) . ?
C8 C13 1.481(3) . ?
C10 C11 1.493(3) . ?
C2 C3 1.393(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.387(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.370(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C4 H4 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C2 C3 C4 179.78(18) . . . . ?
N1 N2 C7 C8 179.95(15) . . . . ?
N1 N2 C7 C10 -0.3(3) . . . . ?
N1 C1 C2 S1 0.1(2) . . . . ?
N1 C1 C2 C3 179.02(17) . . . . ?
N1 C1 C6 C5 -179.3(2) . . . . ?
N2 N1 C1 C2 -170.93(16) . . . . ?
N2 N1 C1 C6 9.8(3) . . . . ?
N2 C7 C8 N3 179.41(16) . . . . ?
N2 C7 C8 C13 -1.0(3) . . . . ?
N2 C7 C10 N4 -179.49(18) . . . . ?
N2 C7 C10 C11 0.6(4) . . . . ?
N3 N4 C10 C7 -0.1(2) . . . . ?
N3 N4 C10 C11 179.8(2) . . . . ?
N4 N3 C8 C7 0.4(2) . . . . ?
N4 N3 C8 C13 -179.25(19) . . . . ?
C1 N1 N2 C7 179.01(14) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C6 C5 C4 -0.5(4) . . . . ?
C8 N3 N4 C10 -0.2(2) . . . . ?
C8 C7 C10 N4 0.3(2) . . . . ?
C8 C7 C10 C11 -179.6(2) . . . . ?
C10 C7 C8 N3 -0.4(2) . . . . ?
C10 C7 C8 C13 179.2(2) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C6 C1 C2 S1 179.40(15) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
C6 C5 C4 C3 -0.3(4) . . . . ?
C14 N3 N4 C10 -178.47(17) . . . . ?
C14 N3 C8 C7 178.47(18) . . . . ?
C14 N3 C8 C13 -1.2(3) . . . . ?
C12 S1 C2 C1 177.26(17) . . . . ?
C12 S1 C2 C3 -1.6(2) . . . . ?
