Syntheses and quadratic nonlinear optical properties of 2,7-fluorenylene- and 1,4-phenylene-functionalized o-carboranes.
Jiang, Peng; Wang, Zhaojin; Moxey, Graeme J.; Morshedi, Mahbod; Barlow, Adam; Wang, Genmiao; Quintana, Cristóbal; Zhang, Chi; Cifuentes, Marie P.; Humphrey, Mark G.; Dalton transactions (Cambridge, England : 2003) 48 (2019) 12549–12559; doi:10.1039/c9dt02645b

data_7700668
_publ_section_title
;
 Syntheses and quadratic nonlinear optical properties of 2,7-fluorenylene-
 and 1,4-phenylene-functionalized o-carboranes.
;
_journal_issue                   33
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12549
_journal_page_last               12559
_journal_paper_doi               10.1039/c9dt02645b
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C38 H43 N Si'
_chemical_formula_sum            'C38 H43 N Si'
_chemical_formula_weight         541.82
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2019-06-22 deposited with the CCDC.    2019-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                67.144(5)
_cell_angle_beta                 77.412(4)
_cell_angle_gamma                80.202(4)
_cell_formula_units_Z            2
_cell_length_a                   9.6878(5)
_cell_length_b                   13.3183(6)
_cell_length_c                   14.0198(8)
_cell_measurement_reflns_used    6358
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.1560
_cell_measurement_theta_min      3.4450
_cell_volume                     1619.44(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega    6.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -99.0000  150.0000 67

  2 omega  -30.00   55.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -38.0000 -150.0000 85

  3 omega   56.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   57.0000   90.0000 41

  4 omega   20.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   57.0000    0.0000 54

  5 omega  -19.00   61.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -77.0000   30.0000 80

  6 omega   37.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254 -125.0000  -90.0000 52

  7 omega   11.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   19.0000 -150.0000 96

  8 omega   43.00   89.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 46

  9 omega   75.00  109.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 34

 10 omega   59.00  130.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 71

 11 omega   60.00  108.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 48

 12 omega   38.00   84.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 46

 13 omega   47.00   96.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000    0.0000 49

 14 omega   42.00   97.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 55

 15 omega  101.00  131.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 30

 16 omega   43.00   97.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 54

 17 omega   94.00  133.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 39

 18 omega   38.00   89.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 51

 19 omega   39.00   78.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 39

 20 omega   81.00  114.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 33

 21 omega   39.00   90.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 51

 22 omega  146.00  174.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 28

 23 omega   83.00  108.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 25

 24 omega   42.00   70.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 28

 25 omega   62.00  118.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 56

 26 omega   99.00  172.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 73

 27 omega   40.00   89.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 49

 28 omega   95.00  177.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -30.0000 82

 29 omega   48.00   89.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -30.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0613980000
_diffrn_orient_matrix_UB_12      0.0141141000
_diffrn_orient_matrix_UB_13      0.0860951000
_diffrn_orient_matrix_UB_21      0.1245386000
_diffrn_orient_matrix_UB_22      0.0554753000
_diffrn_orient_matrix_UB_23      -0.0826613000
_diffrn_orient_matrix_UB_31      -0.0866689000
_diffrn_orient_matrix_UB_32      0.1123592000
_diffrn_orient_matrix_UB_33      -0.0195904000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12065
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.269
_diffrn_reflns_theta_min         3.470
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.099
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         6316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0374P)^2^+0.6273P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5468
_reflns_number_total             6316
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt02645b2.cif
_cod_data_source_block           GM498
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct Methods' was changed to
'direct'.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7700666--7700674.cif.
;
_cod_original_cell_volume        1619.43(15)
_cod_database_code               7700668
_chemical_oxdiff_formula         'C38 H43 N1 Si1'
_reflns_odcompleteness_completeness 98.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C7(H7A,H7B), C11(H11A,H11B), C8(H8A,H8B), C13(H13A,H13B),
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C35(H35), C28(H28), C32(H32), C4(H4), C29(H29), C18(H18), C19(H19),
 C34(H34), C22(H22), C23(H23), C33(H33), C31(H31), C25(H25), C27(H27), C26(H26)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C14(H14A,H14B,
 H14C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              86229
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'