Nonlinear optical properties of diaromatic stilbene, butadiene and thiophene derivatives
Kukkonen, Esa; Lahtinen, Elmeri; Myllyperkiö, Pasi; Haukka, Matti; Konu, Jari; New Journal of Chemistry 45 (2021) 6640–6650; doi:10.1039/D1NJ00456E

data_7060479
_publ_section_title
;
 Nonlinear optical properties of diaromatic stilbene, butadiene and
 thiophene derivatives
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6640
_journal_page_last               6650
_journal_paper_doi               10.1039/D1NJ00456E
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C13 H11 N O2 S'
_chemical_formula_sum            'C13 H11 N O2 S'
_chemical_formula_weight         245.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.743(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.2659(2)
_cell_length_b                   7.50740(10)
_cell_length_c                   27.4441(4)
_cell_measurement_reflns_used    4974
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.5610
_cell_measurement_theta_min      4.1500
_cell_volume                     2318.50(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -119.00  -3.00   1.00   10.00    --  -41.78 -19.00   0.00  116
  2  \w    -66.00  25.00   1.00   10.00    --  -41.78  37.00-180.00   91
  3  \w      5.00  31.00   1.00   10.00    --   41.78 -99.00 -90.00   26
  4  \w     38.00 136.00   1.00   40.00    --  112.00 -30.00 150.00   98
  5  \w     39.00 116.00   1.00   40.00    --  112.00-111.00  90.00   77
  6  \w    108.00 162.00   1.00   40.00    --  112.00 111.00-150.00   54
  7  \w     87.00 175.00   1.00   40.00    --  112.00  45.00 -30.00   88
  8  \w     32.00 109.00   1.00   40.00    --  112.00 -94.00 120.00   77
  9  \w     41.00 124.00   1.00   40.00    --  112.00 -77.00 150.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0228830000
_diffrn_orient_matrix_UB_12      -0.0726041000
_diffrn_orient_matrix_UB_13      0.0521205000
_diffrn_orient_matrix_UB_21      -0.1275872000
_diffrn_orient_matrix_UB_22      -0.0740366000
_diffrn_orient_matrix_UB_23      -0.0007968000
_diffrn_orient_matrix_UB_31      0.0439977000
_diffrn_orient_matrix_UB_32      -0.1770865000
_diffrn_orient_matrix_UB_33      -0.0210162000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            9641
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.833
_diffrn_reflns_theta_min         3.224
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.390
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.5040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4115
_reflns_number_total             4756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj00456e2.cif
_cod_data_source_block           compound_3b
_cod_depositor_comments
'Adding full bibliography for 7060468--7060480.cif.'
_cod_database_code               7060479
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.870
_shelx_estimated_absorpt_t_min   0.646
_reflns_odcompleteness_completeness 98.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              27514
_ins_header
;
TITL ek1834_m in P2(1)/n 
REM P2(1)/n (#14 in standard setting)
CELL 1.54184  11.265928   7.507423  27.444062  90.0000  92.7428  90.0000
ZERR   10.00   0.000210   0.000130   0.000445   0.0000   0.0016   0.0000
LATT  1
SYMM -x+1/2, y+1/2,-z+1/2 
SFAC C H N O
UNIT 110.00 100.00 10.00 10.00
TREF
HKLF 4
END
;
_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 1.247
_oxdiff_exptl_absorpt_empirical_full_min 0.772