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_7060478
_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         'C32 H28 Cl2 N2 O8'
_chemical_formula_sum            'C32 H28 Cl2 N2 O8'
_chemical_formula_weight         639.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.264(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6720(3)
_cell_length_b                   10.3954(2)
_cell_length_c                   18.9716(3)
_cell_measurement_reflns_used    3254
_cell_measurement_temperature    121(1)
_cell_measurement_theta_max      75.4050
_cell_measurement_theta_min      4.6490
_cell_volume                     2888.88(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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      121(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.956
_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   -115.00 -17.00   1.00   15.00    --  -41.65 -37.00  90.00   98
  2  \w   -114.00 -15.00   1.00   15.00    --  -41.65 -57.00-150.00   99
  3  \w    100.00 178.00   1.00   75.00    --  112.00  30.00 150.00   78
  4  \w     42.00 115.00   1.00   75.00    --  112.00-111.00-120.00   73
  5  \w     36.00 140.00   1.00   75.00    --  112.00 -30.00 -30.00  104
  6  \w     42.00 141.00   1.00   75.00    --  112.00 -61.00  60.00   99
;
_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      0.0925206000
_diffrn_orient_matrix_UB_12      -0.0202670000
_diffrn_orient_matrix_UB_13      -0.0329874000
_diffrn_orient_matrix_UB_21      -0.0485496000
_diffrn_orient_matrix_UB_22      -0.0019641000
_diffrn_orient_matrix_UB_23      -0.0741477000
_diffrn_orient_matrix_UB_31      0.0120484000
_diffrn_orient_matrix_UB_32      0.1467631000
_diffrn_orient_matrix_UB_33      -0.0055121000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4692
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.760
_diffrn_reflns_theta_min         4.669
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.514
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.979
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0556P)^2^+2.3576P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2707
_reflns_number_total             2910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj00456e2.cif
_cod_data_source_block           compound_4_Ccell
_cod_depositor_comments
'Adding full bibliography for 7060468--7060480.cif.'
_cod_database_code               7060478
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H14 N1 O4 Cl1'
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.770
_reflns_odcompleteness_completeness 99.10
_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
 O1-N1 \\sim O1A-N1A
 with sigma of 0.02
 N1-C1 \\sim N1A-C1
 with sigma of 0.02
 N1-O2 \\sim N1A-O2A
 with sigma of 0.02
 C1-O2 \\sim C1-O2A
 with sigma of 0.04
 O1-O2 \\sim O1A-O2A
 with sigma of 0.04
 O1-C1 \\sim O1A-C1
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O2A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 O1, N1, C1, O2, O1A, N1A, O2A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: O1(0.566) O2(0.566) N1(0.566) O1A(0.434) O2A(0.434) N1A(0.434)
6.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14)
6.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c)
;
_shelx_res_checksum              46248
_ins_header
;
TITL ek1923_a in C2/c 
REM C2/c (#15 in standard setting)
CELL 1.54184  14.671952  10.395449  18.971650  90.0000  93.2637  90.0000
ZERR    7.00   0.000261   0.000174   0.000334   0.0000   0.0016   0.0000
LATT  7
SYMM -x, y,-z+1/2 
SFAC C H N O Cl
UNIT 112.00 98.00 7.00 28.00 7.00
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 1.414
_oxdiff_exptl_absorpt_empirical_full_min 0.848