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_7060469
_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         'C14 H9 Br N2 O5'
_chemical_formula_sum            'C14 H9 Br N2 O5'
_chemical_formula_weight         365.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 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                90
_cell_angle_beta                 93.319(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.82360(10)
_cell_length_b                   26.8722(5)
_cell_length_c                   13.2409(2)
_cell_measurement_reflns_used    3851
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      75.9940
_cell_measurement_theta_min      4.6650
_cell_volume                     1358.20(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 0.998
_diffrn_measured_fraction_theta_max 0.985
_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    -61.00  27.00   1.00    1.50    --  -41.65  37.00-150.00   88
  2  \w   -121.00  -1.00   1.00    1.50    --  -41.65 -19.00  30.00  120
  3  \w     25.00  67.00   1.00    1.50    --   41.65-125.00 -60.00   42
  4  \w      1.00  83.00   1.00    1.50    --   41.65 -99.00   0.00   82
  5  \w     68.00  98.00   1.00    1.50    --   41.65-125.00 -60.00   30
  6  \w     77.00 116.00   1.00    7.00    --  112.00-111.00 -30.00   39
  7  \w     68.00 151.00   1.00    7.00    --  112.00 178.00-180.00   83
  8  \w     57.00 151.00   1.00    7.00    --  112.00 178.00-150.00   94
  9  \w     37.00 116.00   1.00    7.00    --  112.00-111.00-180.00   79
 10  \w    150.00 178.00   1.00    7.00    --  112.00  45.00 -30.00   28
 11  \w     41.00 140.00   1.00    7.00    --  112.00 -30.00 150.00   99
 12  \w    133.00 177.00   1.00    7.00    --  112.00  15.00-150.00   44
 13  \w     86.00 132.00   1.00    7.00    --  112.00  45.00 -30.00   46
 14  \w     61.00 115.00   1.00    7.00    --  112.00  15.00-150.00   54
 15  \w     36.00 140.00   1.00    7.00    --  112.00 -77.00-180.00  104
 16  \w     42.00 129.00   1.00    7.00    --  112.00 -61.00 -60.00   87
 17  \w     39.00 140.00   1.00    7.00    --  112.00 -30.00 -60.00  101
;
_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      0.0361770000
_diffrn_orient_matrix_UB_12      0.0556393000
_diffrn_orient_matrix_UB_13      -0.0254254000
_diffrn_orient_matrix_UB_21      -0.0745792000
_diffrn_orient_matrix_UB_22      0.0135918000
_diffrn_orient_matrix_UB_23      0.1097502000
_diffrn_orient_matrix_UB_31      0.3948638000
_diffrn_orient_matrix_UB_32      -0.0025351000
_diffrn_orient_matrix_UB_33      0.0299700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5023
_diffrn_reflns_point_group_measured_fraction_full 0.728
_diffrn_reflns_point_group_measured_fraction_max 0.707
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.739
_diffrn_reflns_theta_min         3.289
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.397
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.356
_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    1.786
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.612
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2021
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0600P)^2^+0.8315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.427
_reflns_Friedel_fraction_full    0.455
_reflns_Friedel_fraction_max     0.426
_reflns_number_gt                1997
_reflns_number_total             2021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj00456e2.cif
_cod_data_source_block           compound_1b
_cod_depositor_comments
'Adding full bibliography for 7060468--7060480.cif.'
_cod_database_code               7060469
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H19 N2 O5 Br1'
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.174
_reflns_odcompleteness_completeness 99.65
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5A), C6(H6), C7(H7), C8(H8), C10(H10), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_res_checksum              23746
_ins_header
;
TITL ek1917_a_Cc in Cc 
REM Cc (#9 in standard setting)
CELL 1.54184   3.823607  26.872166  13.240861  90.0000  93.3186  90.0000
ZERR    4.00   0.000066   0.000512   0.000247   0.0000   0.0017   0.0000
LATT -7
SYMM  x,-y, z+1/2 
SFAC C H N O Br
UNIT 56.00 76.00 8.00 20.00 4.00
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 2.333
_oxdiff_exptl_absorpt_empirical_full_min 0.483