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_7700672
_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         'C28 H29 B10 N'
_chemical_formula_sum            'C28 H29 B10 N'
_chemical_formula_weight         487.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 97.4343(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1826(2)
_cell_length_b                   7.76362(13)
_cell_length_c                   31.4490(6)
_cell_measurement_reflns_used    15591
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.2030
_cell_measurement_theta_min      2.8160
_cell_volume                     2707.37(8)
_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 0.998
_diffrn_measurement_details
;
  1 omega   50.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   57.0000  -60.0000 50

  2 omega   49.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   57.0000 -150.0000 26

  3 omega   56.00   92.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 36

  4 omega   66.00   92.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 26

  5 omega   92.00  121.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 29

  6 omega   77.00  103.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -83.0000   21.1189 26

  7 omega   96.00  136.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -81.0000   55.6040 40

  8 omega   97.00  128.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 31

  9 omega   93.00  119.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -118.0000   89.4086 26

 10 omega   88.00  114.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 26

 11 omega   74.00  100.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 26

 12 omega   65.00   91.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   60.0000 26

 13 omega   59.00   89.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 30

 14 omega   42.00   89.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 47

 15 omega   53.00  101.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 48

 16 omega   89.00  115.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 26

 17 omega   91.00  116.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 25

 18 omega   98.00  125.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -180.0000 27

 19 omega  117.00  145.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -180.0000 28

 20 omega  147.00  178.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 31

 21 omega  147.00  172.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 25

 22 omega  103.00  128.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 25

 23 omega   93.00  119.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 26

 24 omega   92.00  142.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 50

 25 omega  129.00  172.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 43

 26 omega  113.00  172.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 59

 27 omega  143.00  169.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 26

 28 omega  120.00  174.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 54

 29 omega  118.00  144.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 26

 30 omega   91.00  117.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 26

 31 omega   91.00  117.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 26

 32 omega   91.00  166.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 75

 33 omega   92.00  137.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 45

 34 omega   92.00  160.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 68

 35 omega   75.00  115.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 40

 36 omega   50.00  107.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 57

 37 omega   47.00   73.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -180.0000 26

 38 omega   62.00  104.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 42

 39 omega   38.00   75.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 37

 40 omega   40.00   66.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 26

 41 omega   40.00   65.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 25

 42 omega   40.00   66.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 26

 43 omega   45.00   72.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 27

 44 omega   38.00   63.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 25

 45 omega   42.00   94.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 52

 46 omega   53.00   78.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 25

 47 omega   54.00   80.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -118.0000   89.4086 26

 48 omega   46.00  106.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 60

 49 omega   46.00  105.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 59

 50 omega   47.00   98.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 51

 51 omega   43.00  107.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 64

 52 omega   44.00   69.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -81.0000   55.6040 25

 53 omega   40.00   67.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 27

 54 omega   59.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   57.0000  150.0000 43

 55 omega   58.00   88.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 30

 56 omega  -32.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -38.0000   60.0000 87

 57 omega   33.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -77.0000   60.0000 25

 58 omega   43.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -99.0000   60.0000 32

 59 omega   31.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -99.0000  -30.0000 36

 60 omega   41.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254 -125.0000 -150.0000 46

 61 omega  -25.00   52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -77.0000 -120.0000 77

 62 omega  -31.00   51.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -57.0000    0.0000 82
;
_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      0.1036752000
_diffrn_orient_matrix_UB_12      -0.0588924000
_diffrn_orient_matrix_UB_13      0.0339540000
_diffrn_orient_matrix_UB_21      0.0355526000
_diffrn_orient_matrix_UB_22      -0.1384083000
_diffrn_orient_matrix_UB_23      -0.0311237000
_diffrn_orient_matrix_UB_31      0.0853133000
_diffrn_orient_matrix_UB_32      0.1294547000
_diffrn_orient_matrix_UB_33      -0.0178842000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            29135
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.987
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93338
_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    1.196
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.223
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         29135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.223
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.1205
_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^)+17.5265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3268
_refine_ls_wR_factor_ref         0.3276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                27555
_reflns_number_total             29135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt02645b2.cif
_cod_data_source_block           GM483
_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        2707.38(9)
_cod_database_code               7700672
_chemical_oxdiff_formula         'C28 H29 B10 N1'
_reflns_odcompleteness_completeness 96.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.628(5) 0.372(5)
2. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5A), C7(H7A), C8(H8A), C12(H12), C13(H13), C15(H15), C16(H16),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
3.b Boron cage BH refined with riding coordinates:
 B1(H1), B2(H2), B3(H3), B4(H4), B5(H5), B6(H6), B7(H7), B8(H8), B9(H9),
 B10(H10), C1(H1A)
;
_shelx_res_checksum              53103
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'