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_7700673
_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 H23 N'
_chemical_formula_sum            'C32 H23 N'
_chemical_formula_weight         421.51
_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                84.313(5)
_cell_angle_beta                 82.206(5)
_cell_angle_gamma                64.163(6)
_cell_formula_units_Z            4
_cell_length_a                   10.1137(7)
_cell_length_b                   10.5179(6)
_cell_length_c                   24.2285(15)
_cell_measurement_reflns_used    2676
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.0660
_cell_measurement_theta_min      3.6770
_cell_volume                     2295.9(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
;
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 0.991
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
  1 omega    9.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   77.0000   60.0000 81

  2 omega   37.00   75.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -99.0000  -90.0000 38

  3 omega   32.00  103.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   38.0000  -60.0000 71

  4 omega   19.00  103.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   57.0000 -150.0000 84

  5 omega   22.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   57.0000  150.0000 76

  6 omega   33.00   96.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   57.0000    0.0000 63

  7 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

  8 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

  9 omega   48.00  107.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 59

 10 omega   38.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 52

 11 omega   63.00  116.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 53

 12 omega   61.00  108.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 47

 13 omega   38.00   86.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 48

 14 omega   92.00  162.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 70

 15 omega   56.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 34

 16 omega   40.00  119.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 79

 17 omega  141.00  177.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   30.0000 36

 18 omega   40.00   94.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 54

 19 omega   39.00  136.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   30.0000 97
;
_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      0.0824550000
_diffrn_orient_matrix_UB_12      0.0504958000
_diffrn_orient_matrix_UB_13      0.0351953000
_diffrn_orient_matrix_UB_21      0.1262657000
_diffrn_orient_matrix_UB_22      -0.0325203000
_diffrn_orient_matrix_UB_23      -0.0475496000
_diffrn_orient_matrix_UB_31      -0.0787998000
_diffrn_orient_matrix_UB_32      0.1514253000
_diffrn_orient_matrix_UB_33      -0.0250475000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13041
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.283
_diffrn_reflns_theta_min         3.686
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97308
_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    1.219
_exptl_crystal_description       rectangle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_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     595
_refine_ls_number_reflns         8737
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0266P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1425
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5607
_reflns_number_total             8737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt02645b2.cif
_cod_data_source_block           GM481
_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_database_code               7700673
_chemical_oxdiff_formula         'C32 H23 N1'
_reflns_odcompleteness_completeness 99.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C21A, C22A, C23A, C24A, C25A, C26A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), 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), C3A(H3A),
 C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), 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)
;
_shelx_res_checksum              95233
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'