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_7700671
_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         'C32 H37 B10 N'
_chemical_formula_sum            'C32 H37 B10 N'
_chemical_formula_weight         543.72
_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
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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                97.508(4)
_cell_angle_beta                 91.388(4)
_cell_angle_gamma                90.186(4)
_cell_formula_units_Z            4
_cell_length_a                   10.8530(5)
_cell_length_b                   14.4693(7)
_cell_length_c                   20.0555(9)
_cell_measurement_reflns_used    6247
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      71.9310
_cell_measurement_theta_min      3.5380
_cell_volume                     3121.4(3)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
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_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      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_details
;
  1 omega   31.00   95.00   1.0000    3.9650
omega____ theta____ kappa____ phi______ frames
    -       36.0254   77.0000 -120.0000 64

  2 omega  -35.00   55.00   1.0000    3.9650
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -19.0000  -30.0000 90

  3 omega   33.00   88.00   1.0000    3.9650
omega____ theta____ kappa____ phi______ frames
    -       36.0254 -125.0000   60.0000 55

  4 omega    1.00   75.00   1.0000    3.9650
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -99.0000 -150.0000 74

  5 omega   19.00  104.00   1.0000    3.9650
omega____ theta____ kappa____ phi______ frames
    -       36.0254   77.0000  -60.0000 85

  6 omega  -31.00   53.00   1.0000    3.9650
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -57.0000   90.0000 84

  7 omega   38.00   90.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 52

  8 omega   38.00   90.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 52

  9 omega   68.00  150.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000    0.0000 82

 10 omega   83.00  173.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 90

 11 omega   65.00  116.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 51

 12 omega   39.00   66.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 27

 13 omega   73.00  109.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 36

 14 omega   41.00   93.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 52

 15 omega   50.00  126.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   90.0000 76

 16 omega   44.00   98.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 54

 17 omega   38.00  116.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 78

 18 omega   37.00  122.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 85

 19 omega  108.00  172.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   52.0000   93.0000 64

 20 omega   41.00  125.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 84
;
_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      -0.0861281000
_diffrn_orient_matrix_UB_12      0.0628284000
_diffrn_orient_matrix_UB_13      0.0458161000
_diffrn_orient_matrix_UB_21      0.1060286000
_diffrn_orient_matrix_UB_22      0.0706050000
_diffrn_orient_matrix_UB_23      0.0179085000
_diffrn_orient_matrix_UB_31      -0.0387517000
_diffrn_orient_matrix_UB_32      0.0510001000
_diffrn_orient_matrix_UB_33      -0.0598907000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20096
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.126
_diffrn_reflns_theta_min         3.081
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94937
_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            colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     778
_refine_ls_number_reflns         11985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.1395
_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^)+(0.1306P)^2^+25.0250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3810
_refine_ls_wR_factor_ref         0.3894
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9936
_reflns_number_total             11985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt02645b2.cif
_cod_data_source_block           GM465
_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        3121.5(3)
_cod_database_code               7700671
_chemical_oxdiff_formula         'C32 H37 B10 N1'
_reflns_odcompleteness_completeness 99.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9779(10) 0.0221(10)
2. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C3A(H3AB,H3AC), C4A(H4AB,H4AC),
 C5A(H5AB,H5AC)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8A), C9(H9A), C11(H11), C12(H12), C16(H16), C17(H17), C19(H19), C20(H20),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32), C8A(H8AB), C9A(H9AB), C11A(H11A), C12A(H12A), C16A(H16A),
 C17A(H17A), C19A(H19A), C20A(H20A), C22A(H22A), C23A(H23A), C24A(H24A),
 C25A(H25A), C26A(H26A), C28A(H28A), C29A(H29A), C30A(H30A), C31A(H31A),
 C32A(H32A)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C6A(H6AB,H6AC,H6AD)
3.d 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), B1A(H1A), B2A(H2A), B3A(H3AA), B4A(H4AA), B5A(H5AA), B6A(H6AA),
 B7A(H7A), B8A(H8AA), B9A(H9AA), B10A(H10A)
;
_shelx_res_checksum              41730
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'