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_7060472
_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 H14 Cl N O4'
_chemical_formula_sum            'C16 H14 Cl N O4'
_chemical_formula_weight         319.73
_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             2021-02-25
_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                 93.821(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.2178(2)
_cell_length_b                   16.5839(6)
_cell_length_c                   10.2700(4)
_cell_measurement_reflns_used    1711
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.4350
_cell_measurement_theta_min      4.2640
_cell_volume                     716.76(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      120.01(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   -107.00 -25.00   1.00    1.00    --  -41.65 -37.00 150.00   82
  2  \w    -60.00  24.00   1.00    1.00    --  -41.65  37.00 -30.00   84
  3  \w     45.00  83.00   1.00    1.00    --   41.65-125.00 120.00   38
  4  \w    101.00 174.00   1.00    2.00    --  112.00 111.00  90.00   73
  5  \w     42.00  91.00   1.00    2.00    --  112.00 -94.00  30.00   49
  6  \w     37.00 128.00   1.00    2.00    --  112.00 -30.00-180.00   91
  7  \w     77.00 104.00   1.00    2.00    --  112.00 -94.00  60.00   27
  8  \w     32.00  71.00   1.00    2.00    --  112.00 -94.00  60.00   39
  9  \w     63.00 141.00   1.00    2.00    --  112.00 -61.00  30.00   78
 10  \w     40.00 133.00   1.00    2.00    --  112.00 -61.00 150.00   93
;
_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      -0.0620266000
_diffrn_orient_matrix_UB_12      0.0435017000
_diffrn_orient_matrix_UB_13      0.1285330000
_diffrn_orient_matrix_UB_21      -0.0832803000
_diffrn_orient_matrix_UB_22      0.0777831000
_diffrn_orient_matrix_UB_23      -0.0767051000
_diffrn_orient_matrix_UB_31      -0.3509222000
_diffrn_orient_matrix_UB_32      -0.0261243000
_diffrn_orient_matrix_UB_33      -0.0148044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2847
_diffrn_reflns_point_group_measured_fraction_full 0.719
_diffrn_reflns_point_group_measured_fraction_max 0.683
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.873
_diffrn_reflns_theta_min         4.315
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.863
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0685P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.354
_reflns_Friedel_fraction_full    0.420
_reflns_Friedel_fraction_max     0.370
_reflns_number_gt                1977
_reflns_number_total             2072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj00456e2.cif
_cod_data_source_block           compound_1a_noncentro
_cod_depositor_comments
'Adding full bibliography for 7060468--7060480.cif.'
_cod_database_code               7060472
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H14 Cl N O'
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.439
_reflns_odcompleteness_completeness 99.02
_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)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              74104
_ins_header
;
TITL ek1833_a2 in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 1.54184   4.217774  16.583920  10.269984  90.0000  93.8207  90.0000
ZERR    2.00   0.000160   0.000558   0.000413   0.0000   0.0037   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H N O Cl
UNIT 32.00 28.00 2.00 2.00 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 1.520
_oxdiff_exptl_absorpt_empirical_full_min 0.753