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_7060475
_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         'C16 H12 F N O2'
_chemical_formula_sum            'C16 H12 F N O2'
_chemical_formula_weight         269.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-12 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.703(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1272(2)
_cell_length_b                   12.8757(4)
_cell_length_c                   7.3763(3)
_cell_measurement_reflns_used    2735
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.1180
_cell_measurement_theta_min      3.4030
_cell_volume                     654.74(4)
_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    'ShelXD (Sheldrick, 2008)'
_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 0.994
_diffrn_measured_fraction_theta_max 0.916
_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   -113.00 -18.00   1.00    2.00    --  -41.65 -57.00 150.00   95
  2  \w    -74.00  34.00   1.00    2.00    --  -41.65  77.00-120.00  108
  3  \w   -105.00 -21.00   1.00    2.00    --  -41.65 -57.00   0.00   84
  4  \w     -7.00  70.00   1.00    2.00    --   41.65 -57.00   0.00   77
  5  \w     36.00 116.00   1.00    8.00    --  112.00-111.00   0.00   80
  6  \w     31.00 154.00   1.00    8.00    --  112.00 -15.00 120.00  123
  7  \w     37.00 137.00   1.00    8.00    --  112.00 -30.00  30.00  100
  8  \w     33.00  73.00   1.00    8.00    --  112.00 -94.00-120.00   40
  9  \w     65.00 122.00   1.00    8.00    --  112.00-126.00 123.00   57
 10  \w    106.00 131.00   1.00    8.00    --  112.00 111.00 -90.00   25
 11  \w    152.00 178.00   1.00    8.00    --  112.00 111.00 -90.00   26
 12  \w     72.00 123.00   1.00    8.00    --  112.00 178.00  30.00   51
 13  \w    108.00 178.00   1.00    8.00    --  112.00  30.00 120.00   70
 14  \w     36.00 102.00   1.00    8.00    --  112.00 -94.00 -90.00   66
 15  \w     30.00 108.00   1.00    8.00    --  112.00 -94.00 120.00   78
 16  \w     46.00 136.00   1.00    8.00    --  112.00 -45.00 -60.00   90
 17  \w     40.00 104.00   1.00    8.00    --  112.00-111.00-150.00   64
;
_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      0.0596964000
_diffrn_orient_matrix_UB_12      -0.1131870000
_diffrn_orient_matrix_UB_13      -0.0212480000
_diffrn_orient_matrix_UB_21      0.1921401000
_diffrn_orient_matrix_UB_22      0.0382345000
_diffrn_orient_matrix_UB_23      -0.0199978000
_diffrn_orient_matrix_UB_31      0.0784816000
_diffrn_orient_matrix_UB_32      -0.0074046000
_diffrn_orient_matrix_UB_33      0.2214361000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4854
_diffrn_reflns_point_group_measured_fraction_full 0.702
_diffrn_reflns_point_group_measured_fraction_max 0.632
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         85.299
_diffrn_reflns_theta_min         3.433
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.746
_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    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details
;
 Flack x determined using 462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     484
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0334
_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/[\s^2^(Fo^2^)+(0.0648P)^2^+0.0266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.373
_reflns_Friedel_fraction_full    0.406
_reflns_Friedel_fraction_max     0.346
_reflns_number_gt                1777
_reflns_number_total             1881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj00456e2.cif
_cod_data_source_block           compound_2a
_cod_depositor_comments
'Adding full bibliography for 7060468--7060480.cif.'
_cod_database_code               7060475
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H12 F1 N1 O2'
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1C-N1C \\sim O2C-N1C
 with sigma of 0.001
 O1C-C1C \\sim C1C-O2C
 with sigma of 0.001
 C5C-C1C \\sim C5B-C1B
 with sigma of 0.04
 N1C-O1C \\sim N1B-O1B
 with sigma of 0.02
 N1C-O2C \\sim N1B-O2B
 with sigma of 0.02
 N1C-C1C \\sim N1B-C1B
 with sigma of 0.02
 F1C-C14C \\sim F1B-C14B
 with sigma of 0.02
 C15C-C13C \\sim C15B-C13B
 with sigma of 0.04
 O2C-C1C \\sim O2B-C1B
 with sigma of 0.04
 C11C-C16C \\sim C11B-C16B
 with sigma of 0.02
 C11C-C12C \\sim C11B-C12B
 with sigma of 0.02
 C11C-C10C \\sim C11B-C10B
 with sigma of 0.02
 C6C-C2C \\sim C6B-C2B
 with sigma of 0.04
 C16C-C15C \\sim C16B-C15B
 with sigma of 0.02
 C15C-C14C \\sim C15B-C14B
 with sigma of 0.02
 C14C-C13C \\sim C14B-C13B
 with sigma of 0.02
 C16C-C10C \\sim C16B-C10B
 with sigma of 0.04
 C14C-C12C \\sim C14B-C12B
 with sigma of 0.04
 C13C-C12C \\sim C13B-C12B
 with sigma of 0.02
 C8C-C4C \\sim C8B-C4B
 with sigma of 0.04
 C9C-C8C \\sim C9B-C8B
 with sigma of 0.02
 C9C-C10C \\sim C9B-C10B
 with sigma of 0.02
 C7C-C3C \\sim C7B-C3B
 with sigma of 0.04
 C4C-C2C \\sim C4B-C2B
 with sigma of 0.04
 C8C-C7C \\sim C8B-C7B
 with sigma of 0.02
 C7C-C4C \\sim C7B-C4B
 with sigma of 0.02
 C4C-C5C \\sim C4B-C5B
 with sigma of 0.02
 C4C-C3C \\sim C4B-C3B
 with sigma of 0.02
 C5C-C6C \\sim C5B-C6B
 with sigma of 0.02
 C6C-C1C \\sim C6B-C1B
 with sigma of 0.02
 C12C-C10C \\sim C12B-C10B
 with sigma of 0.04
 C1C-C2C \\sim C1B-C2B
 with sigma of 0.02
 C9C-C7C \\sim C9B-C7B
 with sigma of 0.04
 C2C-C3C \\sim C2B-C3B
 with sigma of 0.02
 C8C-C10C \\sim C8B-C10B
 with sigma of 0.04
 N1C-C6C \\sim N1B-C6B
 with sigma of 0.04
 N1C-C2C \\sim N1B-C2B
 with sigma of 0.04
 C7C-C5C \\sim C7B-C5B
 with sigma of 0.04
 F1C-C15C \\sim F1B-C15B
 with sigma of 0.04
 F1C-C13C \\sim F1B-C13B
 with sigma of 0.04
 O1C-O2C \\sim O1B-O2B
 with sigma of 0.04
 C4C-C6C \\sim C4B-C6B
 with sigma of 0.04
 O1C-C1C \\sim O1B-C1B
 with sigma of 0.04
 C11C-C15C \\sim C11B-C15B
 with sigma of 0.04
 C11C-C13C \\sim C11B-C13B
 with sigma of 0.04
 C11C-C9C \\sim C11B-C9B
 with sigma of 0.04
 C5C-C3C \\sim C5B-C3B
 with sigma of 0.04
 C1C-C3C \\sim C1B-C3B
 with sigma of 0.04
 C16C-C14C \\sim C16B-C14B
 with sigma of 0.04
 C16C-C12C \\sim C16B-C12B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: F1A(0.4) O1A(0.4) O2A(0.4) N1A(0.4) C1A(0.4) C2A(0.4) H2A(0.4)
 C3A(0.4) H3A(0.4) C4A(0.4) C5A(0.4) H5A(0.4) C6A(0.4) H6A(0.4) C7A(0.4)
 H7A(0.4) C8A(0.4) H8A(0.4) C9A(0.4) H9A(0.4) C10A(0.4) H10A(0.4) C11A(0.4)
 C12A(0.4) H12A(0.4) C13A(0.4) H13A(0.4) C14A(0.4) C15A(0.4) H15A(0.4)
 C16A(0.4) H16A(0.4) F1B(0.4) O1B(0.4) O2B(0.4) N1B(0.4) C1B(0.4) C2B(0.4)
 H2B(0.4) C3B(0.4) H3B(0.4) C4B(0.4) C5B(0.4) H5B(0.4) C6B(0.4) H6B(0.4)
 C7B(0.4) H7B(0.4) C8B(0.4) H8B(0.4) C9B(0.4) H9B(0.4) C10B(0.4) H10B(0.4)
 C11B(0.4) C12B(0.4) H12B(0.4) C13B(0.4) H13B(0.4) C14B(0.4) C15B(0.4)
 H15B(0.4) C16B(0.4) H16B(0.4) F1C(0.2) O1C(0.2) O2C(0.2) N1C(0.2) C4C(0.2)
 C5C(0.2) H5C(0.2) C6C(0.2) H6C(0.2) C1C(0.2) C2C(0.2) H2C(0.2) C3C(0.2)
 H3C(0.2) C7C(0.2) H7C(0.2) C8C(0.2) H8C(0.2) C9C(0.2) H9C(0.2) C10C(0.2)
 H10C(0.2) C11C(0.2) C16C(0.2) H16C(0.2) C15C(0.2) H15C(0.2) C14C(0.2)
 C13C(0.2) H13C(0.2) C12C(0.2) H12C(0.2)
5.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A),
 C10A(H10A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A), C2B(H2B), C3B(H3B),
  C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B), C12B(H12B),
 C13B(H13B), C15B(H15B), C16B(H16B), C5C(H5C), C6C(H6C), C2C(H2C), C3C(H3C),
 C7C(H7C), C8C(H8C), C9C(H9C), C10C(H10C), C16C(H16C), C15C(H15C), C13C(H13C),
 C12C(H12C)
5.b Fitted hexagon refined as free rotating group:
 C4C(C5C,C6C,C1C,C2C,C3C), C11C(C16C,C15C,C14C,C13C,C12C)
;
_shelx_res_checksum              77849
_ins_header
;
TITL ek1926_a_Pc_small in Pc 
REM Pc (#7 in standard setting)
CELL 1.54184   7.376128  12.878279   7.126359  90.0000 104.7024  90.0000
ZERR    2.00   0.000357   0.000410   0.000224   0.0000   0.0040   0.0000
LATT -1
SYMM  x,-y, z+1/2 
SFAC C H N O F
UNIT 32.00 24.00 2.00 4.00 2.00
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 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.660