# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TS_AS-MW_C30H40O2N2S2_Cu_100K_X1
_database_code_depnum_ccdc_archive 'CCDC 2257067'
loop_
_audit_author_name
_audit_author_address
'Thomas Schmedake'
;University of North Carolina at Charlotte
United States of America
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_audit_creation_date             2023-04-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
loop_
_audit_author_email
ashibu@uncc.edu
Tom.Schmedake@uncc.edu
Michael.Walter@uncc.edu
_chemical_name_systematic        
2,5-Bis(4-heptyloxyphenyl)thiazolo[5,4-d]thiazole
_chemical_formula_moiety         'C30 H38 N2 O2 S2'
_chemical_formula_sum            'C30 H38 N2 O2 S2'
_chemical_formula_weight         522.781
_chemical_oxdiff_formula         'C30 H40 O2 N2 S2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   31.0223(11)
_cell_length_b                   7.1900(3)
_cell_length_c                   6.0107(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.400(3)
_cell_angle_gamma                90
_cell_volume                     1340.29(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      66.3780
_cell_measurement_theta_min      4.2690
_exptl_absorpt_coefficient_mu    2.032
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       irregular
_exptl_crystal_F_000             562.870
_exptl_crystal_preparation       'described in paper'
_exptl_crystal_recrystallization_method 
'Diffusion of hexane into chloroform solution'
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.035
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.9929
_diffrn_reflns_Laue_measured_fraction_max 0.9929
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            12196
_diffrn_reflns_point_group_measured_fraction_full 0.9929
_diffrn_reflns_point_group_measured_fraction_max 0.9929
_diffrn_reflns_theta_full        66.9182
_diffrn_reflns_theta_max         66.92
_diffrn_reflns_theta_min         4.28
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4419
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9929
_diffrn_measured_fraction_theta_max 0.9929
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -18.00   1.00    1.52    --  -41.49 125.00 -90.00   80
  2  ω     17.00 116.00   1.00    1.52    --   41.49  38.00 120.00   99
  3  ω    -31.00  70.00   1.00    1.52    --   41.49 -57.00 -30.00  101
  4  ω     67.00 166.00   1.00    6.08    --   92.50  45.00  90.00   99
  5  ω     60.00 169.00   1.00    6.08    --   92.50  77.00 -30.00  109
  6  ω     60.00 169.00   1.00    6.08    --   92.50  77.00  30.00  109
  7  ω     13.00 127.00   1.00    6.08    --   92.50 -83.00 132.15  114
  8  ω      9.00 129.00   1.00    6.08    --   92.50 -88.00-164.34  120
  9  ω     20.00 122.00   1.00    6.08    --   92.50 -61.00  60.00  102
 10  ω      9.00 129.00   1.00    6.08    --   92.50 -89.00 -81.05  120
 11  ω     11.00 128.00   1.00    6.08    --   92.50 -86.00  44.77  117
 12  ω     10.00  85.00   1.00    6.08    --   92.50 -95.00-120.00   75
 13  ω     11.00  84.00   1.00    6.08    --   92.50 -97.00 -81.00   73
 14  ω     70.00 149.00   1.00    6.08    --   92.50  30.00 -30.00   79
 15  ω     71.00  97.00   1.00    6.08    --   92.50 -80.00 -36.29   26
 16  ω     34.00  79.00   1.00    6.08    --   92.50 -95.00   0.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0232171000
_diffrn_orient_matrix_UB_12      0.1782583000
_diffrn_orient_matrix_UB_13      -0.0801708000
_diffrn_orient_matrix_UB_21      -0.0110626000
_diffrn_orient_matrix_UB_22      -0.0944766000
_diffrn_orient_matrix_UB_23      -0.2241778000
_diffrn_orient_matrix_UB_31      -0.0424776000
_diffrn_orient_matrix_UB_32      -0.0725577000
_diffrn_orient_matrix_UB_33      0.0949372000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_special_details          'olex2.solve using Charge Flipping'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              36
_reflns_limit_h_min              -36
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                1783
_reflns_number_total             2371
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.8156
_refine_diff_density_min         -0.4350
_refine_diff_density_rms         0.1273
_refine_ls_d_res_high            0.8380
_refine_ls_d_res_low             10.3377
_refine_ls_goodness_of_fit_ref   1.1031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0744
_refine_ls_restrained_S_all      1.1031
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0935P)²+2.7180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2012
_refine_ls_wR_factor_ref         0.2214
_refine_special_details          'olex2.refine using Gauss-Newton'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1B) = Uanis(N1A)
3. Others
 Fixed Sof: S1B(0.5) N1B(0.5) S1A(0.5) N1A(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C10(H10a,H10b), C11(H11a,H11b), C13(H13a,H13b), C14(H14a,
 H14b), C9(H9a,H9b)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C7(H7), C4(H4)
4.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_disorder_group
C3 C 0.61173(12) 0.9996(5) 0.3190(6) 0.0266(8) Uani 1.000000 . .
C5 C 0.66486(12) 0.9161(5) 0.0471(6) 0.0287(9) Uani 1.000000 . .
H5 H 0.67175(12) 0.8558(5) -0.0880(6) 0.0344(10) Uiso 1.000000 R .
C12 C 0.86215(12) 1.0384(6) -0.3709(7) 0.0320(9) Uani 1.000000 . .
H12a H 0.85996(12) 1.1750(6) -0.3883(7) 0.0384(11) Uiso 1.000000 R .
H12b H 0.87934(12) 1.0135(6) -0.2332(7) 0.0384(11) Uiso 1.000000 R .
C10 C 0.79580(13) 1.0348(6) -0.1353(6) 0.0306(9) Uani 1.000000 . .
H10a H 0.81464(13) 1.0070(6) -0.0042(6) 0.0368(11) Uiso 1.000000 R .
H10b H 0.79341(13) 1.1717(6) -0.1479(6) 0.0368(11) Uiso 1.000000 R .
C11 C 0.81709(12) 0.9599(5) -0.3431(6) 0.0292(9) Uani 1.000000 . .
H11a H 0.79902(12) 0.9920(5) -0.4756(6) 0.0350(11) Uiso 1.000000 R .
H11b H 0.81878(12) 0.8226(5) -0.3337(6) 0.0350(11) Uiso 1.000000 R .
C6 C 0.69708(12) 1.0051(5) 0.1734(6) 0.0247(8) Uani 1.000000 . .
C13 C 0.88620(12) 0.9599(6) -0.5680(6) 0.0312(9) Uani 1.000000 . .
H13a H 0.88844(12) 0.8232(6) -0.5514(6) 0.0375(11) Uiso 1.000000 R .
H13b H 0.86928(12) 0.9857(6) -0.7063(6) 0.0375(11) Uiso 1.000000 R .
C2 C 0.56712(12) 0.9974(5) 0.3915(6) 0.0245(8) Uani 1.000000 . .
C14 C 0.93107(13) 1.0401(6) -0.5902(7) 0.0374(10) Uani 1.000000 . .
H14a H 0.92874(13) 1.1762(6) -0.6121(7) 0.0448(12) Uiso 1.000000 R .
H14b H 0.94764(13) 1.0183(6) -0.4498(7) 0.0448(12) Uiso 1.000000 R .
C1 C 0.50615(15) 1.0367(5) 0.5986(7) 0.0342(10) Uani 1.000000 . .
C8 C 0.64436(13) 1.0865(5) 0.4460(6) 0.0271(8) Uani 1.000000 . .
H8 H 0.63754(13) 1.1445(5) 0.5828(6) 0.0325(10) Uiso 1.000000 R .
C9 C 0.75172(12) 0.9555(6) -0.0967(6) 0.0291(9) Uani 1.000000 . .
H9a H 0.73102(12) 0.9982(6) -0.2138(6) 0.0350(11) Uiso 1.000000 R .
H9b H 0.75266(12) 0.8179(6) -0.0987(6) 0.0350(11) Uiso 1.000000 R .
C7 C 0.68600(12) 1.0890(5) 0.3752(6) 0.0274(8) Uani 1.000000 . .
H7 H 0.70771(12) 1.1484(5) 0.4639(6) 0.0329(10) Uiso 1.000000 R .
O1 O 0.73905(8) 1.0215(4) 0.1180(4) 0.0294(7) Uani 1.000000 . .
C15 C 0.95586(14) 0.9569(7) -0.7827(8) 0.0445(12) Uani 1.000000 . .
H15a H 0.9594(10) 0.8229(11) -0.759(3) 0.0667(17) Uiso 1.000000 GR .
H15b H 0.9398(6) 0.979(4) -0.9227(10) 0.0667(17) Uiso 1.000000 GR .
H15c H 0.9843(5) 1.016(3) -0.790(4) 0.0667(17) Uiso 1.000000 GR .
C4 C 0.62301(12) 0.9159(5) 0.1190(6) 0.0278(8) Uani 1.000000 . .
H4 H 0.60124(12) 0.8572(5) 0.0300(6) 0.0334(10) Uiso 1.000000 R .
S1B S 0.55543(8) 1.0864(4) 0.6617(4) 0.0259(6) Uani 0.500000 . 1
N1B N 0.4639(3) 1.0581(14) 0.7169(18) 0.038(2) Uani 0.500000 . 1
S1A S 0.47461(9) 1.0805(4) 0.7947(4) 0.0292(6) Uani 0.500000 . 2
N1A N 0.4464(3) 0.9508(14) 0.4206(18) 0.038(2) Uani 0.500000 . 2


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
C3 C2 1.461(5) . ?
C3 C8 1.400(5) . ?
C3 C4 1.396(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(5) . ?
C5 C4 1.378(5) . ?
C12 H12a 0.9900 . ?
C12 H12b 0.9900 . ?
C12 C11 1.521(6) . ?
C12 C13 1.523(5) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C10 C11 1.525(5) . ?
C10 C9 1.505(5) . ?
C11 H11a 0.9900 . ?
C11 H11b 0.9900 . ?
C6 C7 1.405(5) . ?
C6 O1 1.357(5) . ?
C13 H13a 0.9900 . ?
C13 H13b 0.9900 . ?
C13 C14 1.516(6) . ?
C2 S1B 1.791(4) . ?
C2 N1B 1.217(10) 3_676 ?
C2 S1A 1.781(4) 3_676 ?
C2 N1A 1.270(12) 3_676 ?
C14 H14a 0.9900 . ?
C14 H14b 0.9900 . ?
C14 C15 1.527(6) . ?
C1 C1 1.344(8) 3_676 ?
C1 S1B 1.606(5) . ?
C1 N1B 1.514(12) . ?
C1 S1A 1.582(5) . ?
C1 N1A 1.481(12) 3_676 ?
C8 H8 0.9500 . ?
C8 C7 1.370(6) . ?
C9 H9a 0.9900 . ?
C9 H9b 0.9900 . ?
C9 O1 1.438(4) . ?
C7 H7 0.9500 . ?
C15 H15a 0.9800 . ?
C15 H15b 0.9800 . ?
C15 H15c 0.9800 . ?
C4 H4 0.9500 . ?

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
C8 C3 C2 121.3(3) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 C8 117.9(4) . . ?
C6 C5 H5 120.1(2) . . ?
C4 C5 H5 120.1(2) . . ?
C4 C5 C6 119.8(4) . . ?
H12b C12 H12a 107.6 . . ?
C11 C12 H12a 108.6(2) . . ?
C11 C12 H12b 108.6(2) . . ?
C13 C12 H12a 108.6(2) . . ?
C13 C12 H12b 108.6(2) . . ?
C13 C12 C11 114.7(3) . . ?
H10b C10 H10a 107.7 . . ?
C11 C10 H10a 108.8(2) . . ?
C11 C10 H10b 108.8(2) . . ?
C9 C10 H10a 108.8(2) . . ?
C9 C10 H10b 108.8(2) . . ?
C9 C10 C11 114.0(3) . . ?
C10 C11 C12 112.1(3) . . ?
H11a C11 C12 109.2(2) . . ?
H11a C11 C10 109.2(2) . . ?
H11b C11 C12 109.2(2) . . ?
H11b C11 C10 109.2(2) . . ?
H11b C11 H11a 107.9 . . ?
C7 C6 C5 118.6(3) . . ?
O1 C6 C5 125.8(3) . . ?
O1 C6 C7 115.5(3) . . ?
H13a C13 C12 108.9(2) . . ?
H13b C13 C12 108.9(2) . . ?
H13b C13 H13a 107.7 . . ?
C14 C13 C12 113.3(3) . . ?
C14 C13 H13a 108.9(2) . . ?
C14 C13 H13b 108.9(2) . . ?
S1B C2 C3 118.8(3) . . ?
N1B C2 C3 125.9(6) 3_676 . ?
N1B C2 S1B 115.3(6) 3_676 . ?
S1A C2 C3 119.7(3) 3_676 . ?
S1A C2 S1B 121.5(2) 3_676 . ?
S1A C2 N1B 6.6(6) 3_676 3_676 ?
N1A C2 C3 126.8(5) 3_676 . ?
N1A C2 S1B 8.3(5) 3_676 . ?
N1A C2 N1B 107.3(7) 3_676 3_676 ?
N1A C2 S1A 113.6(5) 3_676 3_676 ?
H14a C14 C13 108.9(2) . . ?
H14b C14 C13 108.9(2) . . ?
H14b C14 H14a 107.7 . . ?
C15 C14 C13 113.5(4) . . ?
C15 C14 H14a 108.9(3) . . ?
C15 C14 H14b 108.9(2) . . ?
N1B C1 S1B 134.1(5) . . ?
S1A C1 S1B 112.5(3) . . ?
S1A C1 N1B 21.8(3) . . ?
N1A C1 S1B 20.5(4) 3_676 . ?
N1A C1 N1B 154.6(6) 3_676 . ?
N1A C1 S1A 132.8(5) 3_676 . ?
H8 C8 C3 119.6(2) . . ?
C7 C8 C3 120.7(3) . . ?
C7 C8 H8 119.6(2) . . ?
H9a C9 C10 110.4(2) . . ?
H9b C9 C10 110.4(2) . . ?
H9b C9 H9a 108.6 . . ?
O1 C9 C10 106.4(3) . . ?
O1 C9 H9a 110.44(18) . . ?
O1 C9 H9b 110.44(19) . . ?
C8 C7 C6 121.0(3) . . ?
H7 C7 C6 119.5(2) . . ?
H7 C7 C8 119.5(2) . . ?
C9 O1 C6 118.5(3) . . ?
H15a C15 C14 109.5 . . ?
H15b C15 C14 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C14 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
C5 C4 C3 121.8(4) . . ?
H4 C4 C3 119.1(2) . . ?
H4 C4 C5 119.1(2) . . ?
C1 S1B C2 85.3(2) . . ?
C1 N1B C2 113.4(8) . 3_676 ?
C1 S1A C2 85.6(2) . 3_676 ?
C1 N1A C2 113.7(7) 3_676 3_676 ?

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
C3 C2 N1B C1 -178.2(7) . . 3_676 3_676 ?
C3 C2 N1A C1 177.7(7) . . 3_676 . ?
C3 C8 C7 C6 0.2(4) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C5 C6 O1 C9 5.3(4) . . . . ?
C12 C11 C10 C9 -177.9(3) . . . . ?
C12 C13 C14 C15 178.0(4) . . . . ?
C10 C9 O1 C6 165.7(3) . . . . ?
C2 S1B C1 C1 -1.0(4) . . . 3_676 ?
C2 S1B C1 N1B -178.9(6) . . . . ?
C2 S1B C1 S1A 177.94(19) . . . . ?
C2 S1B C1 N1A 5.2(13) . . . 3_676 ?
C2 N1B C1 C1 -1.4(8) . 3_676 3_676 . ?
C2 N1B C1 S1B 179.6(4) 3_676 . . . ?
C2 N1B C1 S1A -172.6(17) 3_676 . . . ?
C2 N1B C1 N1A 177.0(10) . 3_676 3_676 . ?
C2 S1A C1 C1 2.5(4) . 3_676 3_676 . ?
C2 S1A C1 S1B 178.60(18) 3_676 . . . ?
C2 S1A C1 N1B 4.6(12) 3_676 . . . ?
C2 S1A C1 N1A 177.9(6) . 3_676 3_676 . ?
C2 N1A C1 C1 2.6(9) . 3_676 . 3_676 ?
C2 N1A C1 S1B -172.1(18) . 3_676 . . ?
C2 N1A C1 N1B -178.9(9) . 3_676 . . ?
C2 N1A C1 S1A 178.8(4) . 3_676 . . ?


_olex2_exptl_crystal_mounting_method 'Mounted on cryoloop with mineral oil'
_olex2_submission_original_sample_id HeptoxyphenylTTZ
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.779
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SJ_MW_C24H26O2N2S2_x1_Cu2
_database_code_depnum_ccdc_archive 'CCDC 2257068'
loop_
_audit_author_name
_audit_author_address
'Thomas Schmedake'
;University of North Carolina at Charlotte
United States of America
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_audit_creation_date             2023-04-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
loop_
_audit_author_email
ashibu@uncc.edu
Tom.Schmedake@uncc.edu
Michael.Walter@uncc.edu
_chemical_name_systematic        
2,5-Bis(4-butoxyphenyl)thiazolo[5,4-d]thiazole
_chemical_formula_moiety         'C24 H26 N2 O2 S2'
_chemical_formula_sum            'C24 H26 N2 O2 S2'
_chemical_formula_weight         438.618
_chemical_oxdiff_formula         'C24 H26 O2 N2 S2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   5.4441(5)
_cell_length_b                   7.4759(7)
_cell_length_c                   14.1023(13)
_cell_angle_alpha                84.330(8)
_cell_angle_beta                 82.922(8)
_cell_angle_gamma                70.044(8)
_cell_volume                     534.39(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2053
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      66.6740
_cell_measurement_theta_min      6.3050
_exptl_absorpt_coefficient_mu    2.446
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       plate
_exptl_crystal_F_000             233.320
_exptl_crystal_preparation       'described in paper'
_exptl_crystal_recrystallization_method 
'Diffusion of hexanes into chloroform solution'
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.511
_exptl_crystal_size_min          0.036
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.9900
_diffrn_reflns_Laue_measured_fraction_max 0.9900
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4008
_diffrn_reflns_point_group_measured_fraction_full 0.9900
_diffrn_reflns_point_group_measured_fraction_max 0.9900
_diffrn_reflns_theta_full        66.8005
_diffrn_reflns_theta_max         66.80
_diffrn_reflns_theta_min         6.31
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4419
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9900
_diffrn_measured_fraction_theta_max 0.9900
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  68.00   1.00    1.00    --   41.49 -57.00 -30.00   97
  2  ω     64.00  89.00   1.00    1.00    --   92.50-125.00   0.00   25
  3  ω     75.00 102.00   1.00    1.00    --   92.50 -91.00  31.92   27
  4  ω     80.00 122.00   1.00    1.00    --   92.50 -61.00  60.00   42
  5  ω     77.00 104.00   1.00    1.00    --   92.50 -90.00 -11.65   27
  6  ω     79.00 116.00   1.00    1.00    --   92.50 -93.00 -83.34   37
  7  ω     59.00  85.00   1.00    1.00    --   92.50 -30.00   0.00   26
  8  ω     41.00  80.00   1.00    1.00    --   92.50  15.00 -90.00   39
  9  ω     94.00 173.00   1.00    1.00    --   92.50  15.00 -90.00   79
 10  ω    136.00 162.00   1.00    1.00    --   92.50  30.00 -30.00   26
 11  ω     84.00 164.00   1.00    1.00    --   92.50  61.00 120.00   80
 12  ω    125.00 157.00   1.00    1.00    --   92.50 125.00 120.00   32
 13  ω     75.00 101.00   1.00    1.00    --   92.50  30.00 -30.00   26
 14  ω     60.00 112.00   1.00    1.00    --   92.50  77.00 -60.00   52
 15  ω    141.00 166.00   1.00    1.00    --   92.50 125.00-180.00   25
 16  ω     35.00  60.00   1.00    1.00    --   92.50 -45.00   0.00   25
 17  ω     41.00  67.00   1.00    1.00    --   92.50 -90.00 -11.65   26
 18  ω     16.00  42.00   1.00    1.00    --   92.50 -30.00   0.00   26
 19  ω      9.00  52.00   1.00    1.00    --   92.50 -91.00  31.92   43
 20  ω      9.00 108.00   1.00    1.00    --   92.50 -92.00  96.57   99
 21  ω     84.00 129.00   1.00    1.00    --   92.50 -88.00 158.48   45
 22  ω     18.00 106.00   1.00    1.00    --   41.49  57.00 120.00   88
 23  ω     19.00  44.00   1.00    1.00    --   92.50 -88.00 158.48   25
 24  ω     25.00  77.00   1.00    1.00    --   92.50-125.00-120.00   52
 25  ω     31.00  97.00   1.00    1.00    --   92.50 -45.00-180.00   66
 26  ω    -63.00 -37.00   1.00    1.00    --  -41.49 152.00 148.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2210550000
_diffrn_orient_matrix_UB_12      -0.1271613000
_diffrn_orient_matrix_UB_13      -0.0674847000
_diffrn_orient_matrix_UB_21      0.1541957000
_diffrn_orient_matrix_UB_22      -0.0958834000
_diffrn_orient_matrix_UB_23      0.0864413000
_diffrn_orient_matrix_UB_31      -0.1372196000
_diffrn_orient_matrix_UB_32      -0.1512564000
_diffrn_orient_matrix_UB_33      0.0116795000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_special_details          'olex2.solve using Charge Flipping'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1655
_reflns_number_total             1873
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.4012
_refine_diff_density_min         -0.2812
_refine_diff_density_rms         0.0647
_refine_ls_d_res_high            0.8387
_refine_ls_d_res_low             7.0140
_refine_ls_goodness_of_fit_ref   1.0742
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1873
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.0742
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+0.1865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1008
_refine_special_details          'olex2.refine using Gauss-Newton'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C4(H4)
2.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c)
;
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_refinement_flags_posn
S1 S 0.17237(9) 0.64595(6) 0.93095(3) 0.02056(18) Uani 1.000000 .
O1 O 0.3695(2) 0.82376(18) 0.45882(9) 0.0200(3) Uani 1.000000 .
N1 N 0.6742(3) 0.4882(2) 0.88312(11) 0.0184(4) Uani 1.000000 .
C5 C 0.1784(4) 0.8092(2) 0.61514(13) 0.0183(4) Uani 1.000000 .
H5 H 0.0153(4) 0.8857(2) 0.59269(13) 0.0220(5) Uiso 1.000000 R
C7 C 0.6429(4) 0.6416(3) 0.58389(13) 0.0178(4) Uani 1.000000 .
H7 H 0.7967(4) 0.6035(3) 0.54046(13) 0.0213(5) Uiso 1.000000 R
C8 C 0.6539(4) 0.5844(2) 0.68036(13) 0.0175(4) Uani 1.000000 .
H8 H 0.8167(4) 0.5063(2) 0.70250(13) 0.0210(5) Uiso 1.000000 R
C2 C 0.4513(4) 0.5831(2) 0.84744(13) 0.0165(4) Uani 1.000000 .
C9 C 0.5925(4) 0.7725(3) 0.38792(13) 0.0182(4) Uani 1.000000 .
H9a H 0.7320(4) 0.8177(3) 0.40444(13) 0.0219(5) Uiso 1.000000 R
H9b H 0.6650(4) 0.6324(3) 0.38396(13) 0.0219(5) Uiso 1.000000 R
C3 C 0.4307(4) 0.6392(2) 0.74555(13) 0.0163(4) Uani 1.000000 .
C6 C 0.4040(4) 0.7556(2) 0.55138(13) 0.0170(4) Uani 1.000000 .
C10 C 0.4935(4) 0.8677(3) 0.29389(13) 0.0190(4) Uani 1.000000 .
H10a H 0.3509(4) 0.8232(3) 0.27985(13) 0.0228(5) Uiso 1.000000 R
H10b H 0.4186(4) 1.0072(3) 0.30001(13) 0.0228(5) Uiso 1.000000 R
C4 C 0.1919(4) 0.7512(3) 0.71107(13) 0.0182(4) Uani 1.000000 .
H4 H 0.0373(4) 0.7878(3) 0.75414(13) 0.0218(5) Uiso 1.000000 R
C1 C 0.3733(4) 0.5368(3) 1.02024(13) 0.0173(4) Uani 1.000000 .
C11 C 0.7069(4) 0.8268(3) 0.21057(13) 0.0212(4) Uani 1.000000 .
H11a H 0.8437(4) 0.8796(3) 0.22205(13) 0.0255(5) Uiso 1.000000 R
H11b H 0.7902(4) 0.6872(3) 0.20672(13) 0.0255(5) Uiso 1.000000 R
C12 C 0.5969(5) 0.9135(3) 0.11593(14) 0.0272(5) Uani 1.000000 .
H12a H 0.7400(6) 0.8876(18) 0.0642(2) 0.0408(7) Uiso 1.000000 GR
H12b H 0.467(2) 0.8570(16) 0.1029(5) 0.0408(7) Uiso 1.000000 GR
H12c H 0.513(3) 1.0515(4) 0.1198(4) 0.0408(7) Uiso 1.000000 GR


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 1.7595(18) . ?
S1 C1 1.7249(19) . ?
O1 C9 1.442(2) . ?
O1 C6 1.365(2) . ?
N1 C2 1.312(2) . ?
N1 C1 1.362(2) 2_667 ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C5 C4 1.382(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(3) . ?
C7 C6 1.393(3) . ?
C8 H8 0.9500 . ?
C8 C3 1.396(3) . ?
C2 C3 1.463(3) . ?
C9 H9a 0.9900 . ?
C9 H9b 0.9900 . ?
C9 C10 1.511(2) . ?
C3 C4 1.400(3) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C10 C11 1.522(3) . ?
C4 H4 0.9500 . ?
C1 C1 1.372(4) 2_667 ?
C11 H11a 0.9900 . ?
C11 H11b 0.9900 . ?
C11 C12 1.523(3) . ?
C12 H12a 0.9800 . ?
C12 H12b 0.9800 . ?
C12 H12c 0.9800 . ?

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
C1 S1 C2 88.55(8) . . ?
C6 O1 C9 118.68(14) . . ?
C1 N1 C2 108.70(16) 2_667 . ?
C6 C5 H5 120.01(10) . . ?
C4 C5 H5 120.01(11) . . ?
C4 C5 C6 119.98(17) . . ?
C8 C7 H7 120.34(11) . . ?
C6 C7 H7 120.34(11) . . ?
C6 C7 C8 119.33(17) . . ?
H8 C8 C7 119.33(11) . . ?
C3 C8 C7 121.33(17) . . ?
C3 C8 H8 119.33(10) . . ?
N1 C2 S1 115.62(13) . . ?
C3 C2 S1 120.98(14) . . ?
C3 C2 N1 123.38(16) . . ?
H9a C9 O1 110.47(9) . . ?
H9b C9 O1 110.47(9) . . ?
H9b C9 H9a 108.7 . . ?
C10 C9 O1 106.32(14) . . ?
C10 C9 H9a 110.47(10) . . ?
C10 C9 H9b 110.47(10) . . ?
C2 C3 C8 119.95(16) . . ?
C4 C3 C8 118.37(16) . . ?
C4 C3 C2 121.67(17) . . ?
C5 C6 O1 115.13(16) . . ?
C7 C6 O1 124.73(16) . . ?
C7 C6 C5 120.14(16) . . ?
H10a C10 C9 108.98(10) . . ?
H10b C10 C9 108.98(10) . . ?
H10b C10 H10a 107.8 . . ?
C11 C10 C9 113.00(15) . . ?
C11 C10 H10a 108.98(10) . . ?
C11 C10 H10b 108.98(10) . . ?
C3 C4 C5 120.84(17) . . ?
H4 C4 C5 119.58(11) . . ?
H4 C4 C3 119.58(11) . . ?
N1 C1 S1 132.88(15) 2_667 . ?
C1 C1 S1 108.84(18) 2_667 . ?
C1 C1 N1 118.3(2) 2_667 2_667 ?
H11a C11 C10 109.29(10) . . ?
H11b C11 C10 109.29(10) . . ?
H11b C11 H11a 108.0 . . ?
C12 C11 C10 111.64(16) . . ?
C12 C11 H11a 109.29(11) . . ?
C12 C11 H11b 109.29(10) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?

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 N1 C1 -0.07(15) . . . 2_667 ?
S1 C2 C3 C8 -178.70(14) . . . . ?
S1 C2 C3 C4 2.76(17) . . . . ?
S1 C1 N1 C2 179.57(18) . . 2_667 2_667 ?
S1 C1 C1 S1 -180.00(13) . . 2_667 2_667 ?
S1 C1 C1 N1 0.61(13) . . 2_667 . ?
O1 C9 C10 C11 -179.78(14) . . . . ?
O1 C6 C5 C4 -178.74(15) . . . . ?
O1 C6 C7 C8 178.68(18) . . . . ?
N1 C2 C3 C8 2.8(2) . . . . ?
N1 C2 C3 C4 -175.72(17) . . . . ?
N1 C1 C1 N1 180.0(2) . 2_667 . 2_667 ?
C5 C6 C7 C8 -0.8(2) . . . . ?
C5 C4 C3 C8 -1.2(2) . . . . ?
C5 C4 C3 C2 177.33(16) . . . . ?
C7 C8 C3 C2 -177.38(17) . . . . ?
C7 C8 C3 C4 1.2(2) . . . . ?
C9 C10 C11 C12 176.12(16) . . . . ?


_olex2_exptl_crystal_mounting_method 'Mounted on cryoloop with mineral oil'
_olex2_submission_original_sample_id ButoxyphenylTTZ
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.804
_oxdiff_exptl_absorpt_empirical_full_min 0.582
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AS_PropoxyTTz_auto
_database_code_depnum_ccdc_archive 'CCDC 2257069'
loop_
_audit_author_name
_audit_author_address
'Thomas Schmedake'
;University of North Carolina at Charlotte
United States of America
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_audit_creation_date             2023-04-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
loop_
_audit_author_email
ashibu@uncc.edu
Tom.Schmedake@uncc.edu
_chemical_name_systematic        
2,5-Bis(4-propoxyphenyl)thiazolo[5,4-d]thiazole
_chemical_formula_moiety         'C22 H22 N2 O2 S2'
_chemical_formula_sum            'C22 H22 N2 O2 S2'
_chemical_formula_weight         410.564
_chemical_oxdiff_formula         'C22 H22 N2 S2 O2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   16.2976(4)
_cell_length_b                   7.46099(19)
_cell_length_c                   7.9920(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.418(2)
_cell_angle_gamma                90
_cell_volume                     965.71(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5251
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      66.7110
_cell_measurement_theta_min      5.4460
_exptl_absorpt_coefficient_mu    2.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       irregular
_exptl_crystal_F_000             434.564
_exptl_crystal_preparation       'described in paper'
_exptl_crystal_recrystallization_method 
'Diffusion of hexane into chloroform solution'
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.364
_exptl_crystal_size_min          0.197
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.9982
_diffrn_reflns_Laue_measured_fraction_max 0.9982
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8742
_diffrn_reflns_point_group_measured_fraction_full 0.9982
_diffrn_reflns_point_group_measured_fraction_max 0.9982
_diffrn_reflns_theta_full        66.6705
_diffrn_reflns_theta_max         66.67
_diffrn_reflns_theta_min         5.46
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4419
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00 115.00   1.00    1.00    --   41.49  57.00  30.00  102
  2  ω    -33.00  66.00   1.00    1.00    --   41.49 -38.00-120.00   99
  3  ω     80.00 169.00   1.00    1.00    --   92.50  77.00 150.00   89
  4  ω     19.00  87.00   1.00    1.00    --   92.50-125.00 120.00   68
  5  ω     80.00 169.00   1.00    1.00    --   92.50  77.00 -90.00   89
  6  ω     11.00 128.00   1.00    1.00    --   92.50 -86.00 -55.68  117
  7  ω     10.00  81.00   1.00    1.00    --   92.50 -95.00-120.00   71
  8  ω     80.00 169.00   1.00    1.00    --   92.50  77.00 120.00   89
  9  ω     16.00 125.00   1.00    1.00    --   92.50 -77.00  30.00  109
 10  ω     19.00  87.00   1.00    1.00    --   92.50-125.00  60.00   68
 11  ω     10.00  81.00   1.00    1.00    --   92.50 -95.00   0.00   71
 12  ω     11.00 145.00   1.00    1.00    --   92.50 -15.00 -30.00  134
 13  ω     10.00 116.00   1.00    1.00    --   41.49  73.00-115.60  106
 14  ω     62.00 115.00   1.00    1.00    --   41.49 149.00 -88.00   53
 15  ω     13.00 115.00   1.00    1.00    --   41.49  57.00 150.00  102
 16  ω     63.00  90.00   1.00    1.00    --   92.50  61.00 -30.00   27
 17  ω     64.00 169.00   1.00    1.00    --   92.50  30.00  60.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  AS_PropoxyTTz_auto
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0361367000
_diffrn_orient_matrix_UB_12      0.0179533000
_diffrn_orient_matrix_UB_13      -0.1857875000
_diffrn_orient_matrix_UB_21      -0.0875616000
_diffrn_orient_matrix_UB_22      0.0123290000
_diffrn_orient_matrix_UB_23      0.0544895000
_diffrn_orient_matrix_UB_31      0.0083955000
_diffrn_orient_matrix_UB_32      0.2052985000
_diffrn_orient_matrix_UB_33      0.0129775000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_special_details          'olex2.solve using Charge Flipping'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1506
_reflns_number_total             1698
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2172
_refine_diff_density_min         -0.2834
_refine_diff_density_rms         0.0565
_refine_ls_d_res_high            0.8396
_refine_ls_d_res_low             8.0977
_refine_ls_goodness_of_fit_ref   1.0745
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.0745
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+0.2922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0780
_refine_special_details          'olex2.refine using Gauss-Newton'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1B) = Uanis(S1A)
3. Others
 Sof(S1B)=Sof(N1B)=1-FVAR(1)
 Sof(S1A)=Sof(N1A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C5(H5)
4.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c)
;
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_refinement_flags_posn
_atom_site_disorder_group
S1A S 0.50319(4) 0.10367(7) 0.73880(6) 0.01586(19) Uani 0.803(3) . 1
O1 O 0.16439(6) -0.00852(14) 1.12858(12) 0.0204(3) Uani 1.000000 . .
N1A N 0.3961(2) -0.0633(5) 0.5261(4) 0.0186(7) Uani 0.803(3) . 1
C3 C 0.34285(8) 0.00348(19) 0.79439(17) 0.0163(3) Uani 1.000000 . .
C2 C 0.40550(8) 0.00525(18) 0.67637(16) 0.0157(3) Uani 1.000000 . .
C4 C 0.26667(9) -0.08169(19) 0.75447(17) 0.0177(3) Uani 1.000000 . .
H4 H 0.25478(9) -0.13909(19) 0.64843(17) 0.0212(4) Uiso 1.000000 R .
C7 C 0.30116(9) 0.08294(19) 1.06689(17) 0.0184(3) Uani 1.000000 . .
H7 H 0.31349(9) 0.13792(19) 1.17396(17) 0.0221(4) Uiso 1.000000 R .
C6 C 0.22533(9) -0.00049(19) 1.02477(17) 0.0168(3) Uani 1.000000 . .
C8 C 0.35851(9) 0.08520(19) 0.95158(17) 0.0181(3) Uani 1.000000 . .
H8 H 0.40987(9) 0.14396(19) 0.98029(17) 0.0217(4) Uiso 1.000000 R .
C5 C 0.20863(9) -0.08309(19) 0.86776(18) 0.0185(3) Uani 1.000000 . .
H5 H 0.15700(9) -0.14061(19) 0.83877(18) 0.0222(4) Uiso 1.000000 R .
C9 C 0.18192(9) 0.0745(2) 1.29183(17) 0.0214(3) Uani 1.000000 . .
H9a H 0.22766(9) 0.0107(2) 1.35881(17) 0.0257(4) Uiso 1.000000 R .
H9b H 0.19862(9) 0.2009(2) 1.27887(17) 0.0257(4) Uiso 1.000000 R .
C1 C 0.53044(9) 0.0435(2) 0.54910(18) 0.0203(3) Uani 1.000000 . .
C10 C 0.10467(9) 0.0658(2) 1.38008(19) 0.0246(4) Uani 1.000000 . .
H10a H 0.08601(9) -0.0604(2) 1.38292(19) 0.0295(4) Uiso 1.000000 R .
H10b H 0.11792(9) 0.1066(2) 1.49786(19) 0.0295(4) Uiso 1.000000 R .
C11 C 0.03478(10) 0.1799(2) 1.2950(2) 0.0296(4) Uani 1.000000 . .
H11a H 0.0195(5) 0.1364(10) 1.1800(5) 0.0443(6) Uiso 1.000000 GR .
H11b H -0.0131(3) 0.1718(13) 1.3588(8) 0.0443(6) Uiso 1.000000 GR .
H11c H 0.0529(3) 0.3049(3) 1.2914(13) 0.0443(6) Uiso 1.000000 GR .
S1B S 0.3837(3) -0.1087(6) 0.4789(6) 0.0222(9) Uani 0.197(3) . 2
N1B N 0.4744(6) 0.0751(11) 0.7040(10) 0.01586(19) Uani 0.197(3) . 2


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
S1A C2 1.7735(14) . ?
S1A C1 1.6875(15) . ?
O1 C6 1.3649(17) . ?
O1 C9 1.4437(17) . ?
N1A C2 1.299(3) . ?
N1A C1 1.406(4) 3_656 ?
C3 C2 1.4655(19) . ?
C3 C4 1.399(2) . ?
C3 C8 1.3941(19) . ?
C2 S1B 1.793(4) . ?
C2 N1B 1.235(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.391(2) . ?
C7 C8 1.384(2) . ?
C6 C5 1.397(2) . ?
C8 H8 0.9500 . ?
C5 H5 0.9500 . ?
C9 H9a 0.9900 . ?
C9 H9b 0.9900 . ?
C9 C10 1.512(2) . ?
C1 C1 1.359(3) 3_656 ?
C1 S1B 1.521(5) 3_656 ?
C1 N1B 1.636(7) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C10 C11 1.520(2) . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?

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
C1 S1A C2 87.44(7) . . ?
C9 O1 C6 116.53(11) . . ?
C1 N1A C2 109.6(2) 3_656 . ?
C4 C3 C2 121.44(12) . . ?
C8 C3 C2 120.36(13) . . ?
C8 C3 C4 118.19(13) . . ?
N1A C2 S1A 115.65(18) . . ?
C3 C2 S1A 119.40(10) . . ?
C3 C2 N1A 124.94(19) . . ?
S1B C2 S1A 121.80(16) . . ?
S1B C2 N1A 7.1(3) . . ?
S1B C2 C3 118.61(17) . . ?
N1B C2 S1A 6.0(4) . . ?
N1B C2 N1A 110.0(4) . . ?
N1B C2 C3 125.0(4) . . ?
N1B C2 S1B 116.3(4) . . ?
H4 C4 C3 119.69(8) . . ?
C5 C4 C3 120.62(13) . . ?
C5 C4 H4 119.69(8) . . ?
C6 C7 H7 120.26(8) . . ?
C8 C7 H7 120.26(8) . . ?
C8 C7 C6 119.48(13) . . ?
C7 C6 O1 124.04(13) . . ?
C5 C6 O1 116.40(12) . . ?
C5 C6 C7 119.56(13) . . ?
C7 C8 C3 121.69(13) . . ?
H8 C8 C3 119.15(8) . . ?
H8 C8 C7 119.15(8) . . ?
C6 C5 C4 120.44(13) . . ?
H5 C5 C4 119.78(8) . . ?
H5 C5 C6 119.78(8) . . ?
H9a C9 O1 110.06(7) . . ?
H9b C9 O1 110.06(7) . . ?
H9b C9 H9a 108.4 . . ?
C10 C9 O1 108.19(12) . . ?
C10 C9 H9a 110.06(8) . . ?
C10 C9 H9b 110.06(9) . . ?
N1A C1 S1A 132.69(15) 3_656 . ?
C1 C1 S1A 113.41(16) 3_656 . ?
C1 C1 N1A 113.9(2) 3_656 3_656 ?
S1B C1 S1A 112.70(18) 3_656 . ?
S1B C1 N1A 20.36(15) 3_656 3_656 ?
N1B C1 S1A 19.3(3) . . ?
N1B C1 N1A 152.0(3) . 3_656 ?
N1B C1 S1B 131.8(3) . 3_656 ?
H10a C10 C9 109.01(9) . . ?
H10b C10 C9 109.01(8) . . ?
H10b C10 H10a 107.8 . . ?
C11 C10 C9 112.87(12) . . ?
C11 C10 H10a 109.01(9) . . ?
C11 C10 H10b 109.01(8) . . ?
H11a C11 C10 109.5 . . ?
H11b C11 C10 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C10 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C1 S1B C2 83.3(2) 3_656 . ?
C1 N1B C2 112.2(6) . . ?

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
S1A C2 N1A C1 1.18(12) . . . 3_656 ?
S1A C2 C3 C4 -176.26(11) . . . . ?
S1A C2 C3 C8 2.76(13) . . . . ?
S1A C2 N1B C1 155(3) . . . . ?
S1A C1 N1A C2 -179.8(3) . . 3_656 3_656 ?
S1A C1 C1 S1A 180.00(11) . . 3_656 3_656 ?
S1A C1 C1 N1A 0.88(19) . . 3_656 . ?
S1A C1 C1 S1B -4.5(3) . . 3_656 . ?
S1A C1 C1 N1B -178.2(3) . . 3_656 3_656 ?
S1A C1 S1B C2 178.8(3) . . 3_656 3_656 ?
S1A C1 N1B C2 -172.0(5) . . . . ?
O1 C6 C7 C8 -179.31(14) . . . . ?
O1 C6 C5 C4 180.00(12) . . . . ?
O1 C9 C10 C11 -66.59(13) . . . . ?
N1A C2 C3 C4 2.6(3) . . . . ?
N1A C2 C3 C8 -178.3(2) . . . . ?
N1A C2 N1B C1 -4.2(2) . . . . ?
N1A C1 C1 N1A -180.0(3) . 3_656 . 3_656 ?
N1A C1 C1 S1B -174.65(17) . 3_656 . 3_656 ?
N1A C1 C1 N1B -0.9(3) . 3_656 . . ?
N1A C1 S1B C2 -8.5(11) . 3_656 . . ?
N1A C1 N1B C2 -178.6(9) 3_656 . . . ?
C3 C2 N1B C1 177.1(4) . . . . ?
C3 C4 C5 C6 -0.47(17) . . . . ?
C3 C8 C7 C6 -0.97(17) . . . . ?
C2 S1B C1 C1 5.6(3) . . 3_656 . ?
C2 S1B C1 N1B 177.3(4) . . 3_656 3_656 ?
C2 N1B C1 C1 3.1(5) . . . 3_656 ?
C2 N1B C1 S1B 177.1(4) . . . 3_656 ?
C4 C5 C6 C7 -0.26(16) . . . . ?


_olex2_exptl_crystal_mounting_method 'Mounted on cryoloop with mineral oil'
_olex2_submission_original_sample_id PropoxyphenylTTZ
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.891
_oxdiff_exptl_absorpt_empirical_full_min 0.618
