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_7060470
_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 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-04
_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                 96.417(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9378(4)
_cell_length_b                   7.3721(7)
_cell_length_c                   15.3569(12)
_cell_measurement_reflns_used    1219
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      74.6780
_cell_measurement_theta_min      2.8290
_cell_volume                     668.02(9)
_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      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_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    -95.00 -51.00   1.00   10.00    --  -41.65 125.00-180.00   44
  2  \w    -67.00  24.00   1.00   10.00    --  -41.65  57.00 120.00   91
  3  \w    -66.00  33.00   1.00   10.00    --  -41.65  37.00 -90.00   99
  4  \w   -113.00 -20.00   1.00   10.00    --  -41.65 -57.00 -30.00   93
  5  \w    106.00 163.00   1.00   80.00    --  112.00 111.00 -30.00   57
  6  \w     45.00 116.00   1.00   80.00    --  112.00-111.00  60.00   71
  7  \w     39.00 129.00   1.00   80.00    --  112.00 -77.00-120.00   90
  8  \w     45.00 109.00   1.00   80.00    --  112.00 -94.00-180.00   64
  9  \w    101.00 168.00   1.00   80.00    --  112.00  77.00  60.00   67
 10  \w     49.00 125.00   1.00   80.00    --  112.00 -45.00   0.00   76
 11  \w     82.00 108.00   1.00   80.00    --  112.00  77.00 120.00   26
 12  \w    132.00 176.00   1.00   80.00    --  112.00  77.00 120.00   44
 13  \w     86.00 173.00   1.00   80.00    --  112.00  45.00  30.00   87
 14  \w    102.00 172.00   1.00   80.00    --  112.00  61.00 -60.00   70
;
_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      -0.1336932000
_diffrn_orient_matrix_UB_12      -0.1766289000
_diffrn_orient_matrix_UB_13      0.0100555000
_diffrn_orient_matrix_UB_21      0.2205563000
_diffrn_orient_matrix_UB_22      -0.0961701000
_diffrn_orient_matrix_UB_23      0.0367385000
_diffrn_orient_matrix_UB_31      -0.0409957000
_diffrn_orient_matrix_UB_32      0.0566809000
_diffrn_orient_matrix_UB_33      0.0934656000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3947
_diffrn_reflns_point_group_measured_fraction_full 0.813
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.761
_diffrn_reflns_theta_min         2.896
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.922
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 410 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0855
_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^)+(0.1281P)^2^+0.3516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2365
_refine_ls_wR_factor_ref         0.2602
_reflns_Friedel_coverage         0.483
_reflns_Friedel_fraction_full    0.595
_reflns_Friedel_fraction_max     0.553
_reflns_number_gt                1671
_reflns_number_total             2194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj00456e2.cif
_cod_data_source_block           compound_1e
_cod_depositor_comments
'Adding full bibliography for 7060468--7060480.cif.'
_cod_database_code               7060470
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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. Restrained distances
 C8B-C7B
 1.3 with sigma of 0.02
 C9-C8B
 1.4 with sigma of 0.02
 C7B-C4
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C8B) = Uanis(C7B)
Uanis(C13B) = Uanis(C14B) = Uanis(C10B) = Uanis(C11B)
Uanis(C13A) = Uanis(C14A) = Uanis(C10A) = Uanis(C11A)
Uanis(O2B) = Uanis(O1B)
Uanis(C3B) = Uanis(C2B) = Uanis(C6B) = Uanis(C5B)
Uanis(C16B) = Uanis(C15B)
Uanis(C5A) = Uanis(C6A) = Uanis(C2A) = Uanis(C3A)
4. Others
 Fixed Sof: O1A(0.6) O2A(0.6) C2A(0.6) H2A(0.6) C3A(0.6) H3A(0.6) C5A(0.6)
 H5A(0.6) C6A(0.6) H6A(0.6) C7A(0.75) H7A(0.75) C8A(0.75) H8A(0.75) C10A(0.6)
 H10A(0.6) C11A(0.6) H11A(0.6) C13A(0.6) H13A(0.6) C14A(0.6) H14A(0.6)
 C15A(0.6) H15A(0.6) H15B(0.6) H15C(0.6) C16A(0.6) H16A(0.6) H16B(0.6)
 H16C(0.6) O1B(0.4) O2B(0.4) C3B(0.4) H3B(0.4) C2B(0.4) H2B(0.4) C6B(0.4)
 H6B(0.4) C5B(0.4) H5B(0.4) C7B(0.25) H7B(0.25) C8B(0.25) H8B(0.25) C11B(0.4)
 H11B(0.4) C10B(0.4) H10B(0.4) C14B(0.4) H14B(0.4) C13B(0.4) H13B(0.4)
 C15B(0.4) H15D(0.4) H15E(0.4) H15F(0.4) C16B(0.4) H16D(0.4) H16E(0.4) H16F(0.4)
5.a Me refined with riding coordinates:
 C15A(H15A,H15B,H15C), C16A(H16A,H16B,H16C), C15B(H15D,H15E,H15F), C16B(H16D,
 H16E,H16F)
5.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C10A(H10A),
 C11A(H11A), C13A(H13A), C14A(H14A), C3B(H3B), C2B(H2B), C6B(H6B), C5B(H5B),
 C7B(H7B), C8B(H8B), C11B(H11B), C10B(H10B), C14B(H14B), C13B(H13B)
;
_shelx_res_checksum              53230
_ins_header
;
TITL ek1918_a_P21 in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 1.54184   5.937789   7.372117  15.356879  90.0000  96.4174  90.0000
ZERR    3.00   0.000429   0.000681   0.001194   0.0000   0.0066   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H N O
UNIT 33.00 30.00 3.00 3.00
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 1.308
_oxdiff_exptl_absorpt_empirical_full_min 0.758