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_7060480
_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         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-24
_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                109.5280(10)
_cell_angle_beta                 103.3890(10)
_cell_angle_gamma                90.9490(10)
_cell_formula_units_Z            6
_cell_length_a                   11.6720(2)
_cell_length_b                   11.8172(2)
_cell_length_c                   14.7910(2)
_cell_measurement_reflns_used    44313
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.5430
_cell_measurement_theta_min      3.2260
_cell_volume                     1860.67(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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     -1.00  25.00   1.00    1.00    --   38.00  95.00-153.25   26
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.78 -37.00 -30.00   99
  3  \w    -66.00  33.00   1.00    1.00    --  -41.78  37.00 150.00   99
  4  \w    -34.00  74.00   1.00    1.00    --   41.78 -77.00-180.00  108
  5  \w     14.00 114.00   1.00    1.00    --   41.78  57.00 150.00  100
  6  \w     17.00 116.00   1.00    1.00    --   41.78  37.00  30.00   99
  7  \w     23.00  98.00   1.00    1.00    --   41.78-125.00  60.00   75
  8  \w     11.00  38.00   1.00    1.00    --   46.00  84.00  23.63   27
  9  \w     17.00  45.00   1.00    1.00    --   50.00  80.00 -29.30   28
 10  \w     16.00  45.00   1.00    1.00    --   50.00  82.00  98.61   29
 11  \w     16.00  45.00   1.00    1.00    --   50.00  82.00-134.05   29
 12  \w     17.00  45.00   1.00    1.00    --   50.00  80.00 -96.44   28
 13  \w     30.00 137.00   1.00    1.00    --   62.00  75.00  56.98  107
 14  \w     29.00 138.00   1.00    1.00    --   62.00  77.00 166.54  109
 15  \w     34.00 142.00   1.00    1.00    --   66.00  76.00 -21.20  108
 16  \w     34.00 142.00   1.00    1.00    --   66.00  76.00-122.58  108
 17  \w     34.00 141.00   1.00    1.00    --   66.00  75.00 -89.04  107
 18  \w     33.00 142.00   1.00    1.00    --   66.00  77.00 109.95  109
 19  \w     38.00 145.00   1.00    1.00    --   70.00  74.00 131.66  107
 20  \w     37.00 146.00   1.00    1.00    --   70.00  77.00 -59.68  109
 21  \w     41.00 150.00   1.00    1.00    --   74.00  77.00-125.49  109
 22  \w     42.00 150.00   1.00    1.00    --   74.00  76.00-164.20  108
 23  \w     47.00 151.00   1.00    3.00    --   78.00  69.00  80.42  104
 24  \w     53.00 154.00   1.00    3.00    --   82.00  62.00 119.13  101
 25  \w     52.00 155.00   1.00    3.00    --   82.00  65.00 -23.54  103
 26  \w     50.00 157.00   1.00    3.00    --   82.00  74.00   0.50  107
 27  \w     52.00 155.00   1.00    3.00    --   82.00  68.00-163.33  103
 28  \w     55.00 159.00   1.00    3.00    --   86.00  69.00 158.37  104
 29  \w     53.00 162.00   1.00    3.00    --   86.00  77.00  14.40  109
 30  \w     55.00 160.00   1.00    3.00    --   86.00  72.00-140.26  105
 31  \w     76.00 178.00   1.00    3.00    --  106.00  68.00  67.11  102
 32  \w     83.00 178.00   1.00    3.00    --  112.00  61.00   0.00   95
 33  \w     79.00 178.00   1.00    3.00    --  112.00  77.00  60.00   99
 34  \w     83.00 178.00   1.00    3.00    --  112.00  61.00 -90.00   95
 35  \w     29.00 109.00   1.00    3.00    --  112.00 -94.00  90.00   80
 36  \w     79.00 178.00   1.00    3.00    --  112.00  77.00 150.00   99
 37  \w     36.00 116.00   1.00    3.00    --  112.00-111.00-150.00   80
 38  \w     79.00 178.00   1.00    3.00    --  112.00  77.00   0.00   99
 39  \w     79.00 178.00   1.00    3.00    --  112.00  77.00 -90.00   99
 40  \w     36.00 116.00   1.00    3.00    --  112.00-111.00  60.00   80
 41  \w     79.00 178.00   1.00    3.00    --  112.00  77.00 120.00   99
 42  \w     29.00 109.00   1.00    3.00    --  112.00 -94.00 -90.00   80
 43  \w     79.00 178.00   1.00    3.00    --  112.00  77.00-150.00   99
 44  \w     79.00 178.00   1.00    3.00    --  112.00  77.00  90.00   99
 45  \w     36.00 116.00   1.00    3.00    --  112.00-111.00  30.00   80
 46  \w     40.00 141.00   1.00    3.00    --  112.00 -61.00 120.00  101
 47  \w     79.00 178.00   1.00    3.00    --  112.00  77.00 -60.00   99
 48  \w     79.00 178.00   1.00    3.00    --  112.00  77.00-120.00   99
 49  \w     83.00 178.00   1.00    3.00    --  112.00  61.00-120.00   95
 50  \w     83.00 178.00   1.00    3.00    --  112.00  61.00  90.00   95
 51  \w     79.00 178.00   1.00    3.00    --  112.00  77.00-180.00   99
 52  \w     79.00 178.00   1.00    3.00    --  112.00  77.00  30.00   99
 53  \w     29.00 109.00   1.00    3.00    --  112.00 -94.00 120.00   80
 54  \w     29.00 109.00   1.00    3.00    --  112.00 -94.00 -30.00   80
 55  \w     79.00 178.00   1.00    3.00    --  112.00  77.00 -30.00   99
 56  \w     83.00 178.00   1.00    3.00    --  112.00  61.00 150.00   95
 57  \w   -114.00 -14.00   1.00    1.00    --  -41.78 -57.00-180.00  100
 58  \w      6.00  33.00   1.00    1.00    --   42.00  88.00  71.80   27
 59  \w     16.00 119.00   1.00    1.00    --   46.00  67.00 -14.87  103
 60  \w     11.00  38.00   1.00    1.00    --   46.00  84.00 177.90   27
 61  \w     26.00 133.00   1.00    1.00    --   58.00  75.00  18.53  107
 62  \w     34.00 132.00   1.00    1.00    --   66.00  76.00  82.90   98
 63  \w     38.00 146.00   1.00    1.00    --   70.00  76.00-171.19  108
 64  \w     38.00 145.00   1.00    1.00    --   70.00  75.00   3.28  107
 65  \w     44.00 147.00   1.00    1.00    --   74.00  66.00  57.91  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1186014000
_diffrn_orient_matrix_UB_12      -0.0556060000
_diffrn_orient_matrix_UB_13      0.0117282000
_diffrn_orient_matrix_UB_21      0.0122192000
_diffrn_orient_matrix_UB_22      0.0100232000
_diffrn_orient_matrix_UB_23      -0.0986176000
_diffrn_orient_matrix_UB_31      0.0662386000
_diffrn_orient_matrix_UB_32      0.1270589000
_diffrn_orient_matrix_UB_33      0.0563507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            72195
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.984
_diffrn_reflns_theta_min         3.276
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         7769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0573P)^2^+0.5361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7134
_reflns_number_total             7769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj00456e2.cif
_cod_data_source_block           compound_1c
_cod_depositor_comments
'Adding full bibliography for 7060468--7060480.cif.'
_cod_database_code               7060480
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H13 N1 O3'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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), C13(H13),
 C14(H14), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
  C26(H26), C28(H28), C29(H29), C32(H32), C33(H33), C35(H35), C36(H36),
 C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              42596
_ins_header
;
TITL jk1903_a in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184  11.672032  11.817150  14.790987 109.5282 103.3892  90.9488
ZERR    5.00   0.000164   0.000186   0.000208   0.0014   0.0012   0.0012
LATT  1
SFAC C H N O
UNIT 75.00 65.00 5.00 15.00
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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.803