Synthesis and electronic properties of A3B-thienyl porphyrins: experimental and computational investigations
Kumar, Poomani Ram; Britto, Neethinathan Johnee; Kathiravan, Arunkumar; Neels, Antonia; Jaccob, Madhavan; Mothi, Ebrahim M.; New Journal of Chemistry 43 (2019) 1569–; doi:10.1039/C8NJ04289F

data_7058041
_publ_section_title
;
 Synthesis and electronic properties of A3B-thienyl porphyrins:
 experimental and computational investigations
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1569
_journal_paper_doi               10.1039/C8NJ04289F
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C38 H24 N4 O S2.8, 0.2(S)'
_chemical_formula_sum            'C38 H24 N4 O S3'
_chemical_formula_weight         648.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-04 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.419(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6311(3)
_cell_length_b                   11.1557(5)
_cell_length_c                   21.0852(9)
_cell_measurement_reflns_used    17157
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.48
_cell_measurement_theta_min      1.83
_cell_volume                     1556.99(12)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_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    'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14651
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.230
_diffrn_reflns_theta_max         25.230
_diffrn_reflns_theta_min         1.935
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     163
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0835
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0729P)^2^+1.6599P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1883
_refine_ls_wR_factor_ref         0.2002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2187
_reflns_number_total             2775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj04289f2.cif
_cod_data_source_block           comp-6
_cod_depositor_comments
'Adding full bibliography for 7058040--7058041.cif.'
_cod_database_code               7058041
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.921
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
2. Shared sites
{S1, C1A}
{C16, S1A}
3. Restrained distances
 C11-S2 = C11-S2A = C14-S2 = C14A-S2A
 1.7 with sigma of 0.02
 C11-C12 = C12-C13 = C13-C14 = C11-C12A = C12A-C13A = C13A-C14A
 1.4 with sigma of 0.02
 C11-C19 = C19-C20 = C20-C21 = C21-C22 = C22-C23
 1.38 with sigma of 0.02
 H7-H1B
 -2 with sigma of 0.01
 C22A-C21A \\sim C20A-C21A
 with sigma of 0.001
 C22A-O1A \\sim O1A-C20A
 with sigma of 0.0001
 C5-C15 \\sim C11A-C5
 with sigma of 0.001
 O1-C21 \\sim O1A-C21A
 with sigma of 0.001
 C23A-C5 \\sim C5-C19A
 with sigma of 0.001
4. Restrained planarity
 C11, C19, C20, C21, C22, C23, O1
 with sigma of 0.02
 S2, C11, C12, C13, C14
 with sigma of 0.02
 S2A, C11, C12A, C13A, C14A
 with sigma of 0.02
 C5, C11A, C23A, C22A, C21A, C20A, C19A, O1A
 with sigma of 0.0001
5. Uiso/Uaniso restraints and constraints
C13A \\sim C14A \\sim S2A: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002
C11 \\sim C12 \\sim C13: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002
: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(S1) = Uanis(C1A)
Uanis(C16) = Uanis(S1A)
6. Rigid body (RIGU) restrains
 C11, O1, C19, C20, C21, C22, C23, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11, S2A, C14A, C12A, C13A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11, S2, C12, C13, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11, C12, C13, C14, S2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O1A, C11A, C20A, C21A, C22A, C23A, C19A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
7. Others
 Fixed Sof: C15(0.9) C16(0.8) H16(0.8) C17(0.9) H17(0.9) C18(0.9) H18(0.9)
 S1(0.8) S2(0.3) C12(0.3) H12(0.3) C13(0.3) H13(0.3) C14(0.3) H14(0.3) S2A(0.3)
 C14A(0.3) H14A(0.3) C12A(0.3) H12A(0.3) C13A(0.3) H13A(0.3) O1(0.4) H1B(0.4)
 C19(0.4) H19(0.4) C20(0.4) H20(0.4) C21(0.4) C22(0.4) H22(0.4) C23(0.4)
 H23(0.4) O1A(0.1) H1AA(0.1) C11A(0.1) C19A(0.1) H19A(0.1) C20A(0.1) H20A(0.1)
 C21A(0.1) C22A(0.1) H22A(0.1) C23A(0.1) H23A(0.1) C1A(0.1) H1A(0.1) S1A(0.1)
 Fixed Uiso: O1A(0.05) C11A(0.05) C19A(0.05) C20A(0.05) C21A(0.05) C22A(0.05)
 C23A(0.05)
8.a Riding coordinates:
 C1A(H1A)
8.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18), N1(H1),
 C12(H12), C13(H13), C14(H14), C14A(H14A), C12A(H12A), C13A(H13A), C19(H19),
 C20(H20), C22(H22), C23(H23), C19A(H19A), C20A(H20A), C22A(H22A), C23A(H23A)
8.c Fitted hexagon refined as free rotating group:
 C11A(C19A,C20A,C21A,C22A,C23A)
8.d Idealised tetrahedral OH refined as rotating group:
 O1(H1B), O1A(H1AA)
;
_shelx_res_checksum              41069
_shelx_hkl_checksum              58750
_olex2_submission_special_instructions 'No special instructions were received'