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_7700667
_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         'C12 H23 B10 I'
_chemical_formula_sum            'C12 H23 B10 I'
_chemical_formula_weight         402.30
_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                 91.4799(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.66445(9)
_cell_length_b                   24.0864(3)
_cell_length_c                   9.93244(11)
_cell_measurement_reflns_used    7049
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.2780
_cell_measurement_theta_min      4.8210
_cell_volume                     1833.01(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   54.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   57.0000   90.0000 35

  2 omega   66.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 26

  3 omega  104.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -60.0000 35

  4 omega  134.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 41

  5 omega  143.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 25

  6 omega  137.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 41

  7 omega  149.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 28

  8 omega  113.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 26

  9 omega  101.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 44

 10 omega  104.00  140.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 36

 11 omega  118.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 26

 12 omega   49.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -60.0000 39

 13 omega   54.00   80.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 26

 14 omega   52.00   78.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 26

 15 omega   46.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -47.0000  -98.2485 44

 16 omega   55.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -180.0000 44

 17 omega   47.00   77.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 30

 18 omega   39.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 47

 19 omega   28.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254 -125.0000 -180.0000 53

 20 omega   42.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 46

 21 omega   60.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 25

 22 omega   53.00   78.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 25

 23 omega   43.00   80.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 37

 24 omega   66.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 38

 25 omega   41.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254 -125.0000  -60.0000 48

 26 omega   24.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254 -125.0000   60.0000 63

 27 omega   39.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 37

 28 omega   38.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 27

 29 omega    1.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -99.0000 -120.0000 42

 30 omega  -28.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -57.0000  -90.0000 71
;
_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      0.0753398000
_diffrn_orient_matrix_UB_12      -0.0467309000
_diffrn_orient_matrix_UB_13      0.0900473000
_diffrn_orient_matrix_UB_21      -0.1511014000
_diffrn_orient_matrix_UB_22      0.0077478000
_diffrn_orient_matrix_UB_23      0.0975441000
_diffrn_orient_matrix_UB_31      -0.1091538000
_diffrn_orient_matrix_UB_32      -0.0429755000
_diffrn_orient_matrix_UB_33      -0.0803425000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10125
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.401
_diffrn_reflns_theta_min         3.670
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63038
_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    1.458
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.058
_refine_diff_density_max         1.015
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+1.4464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0580
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3539
_reflns_number_total             3629
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt02645b2.cif
_cod_data_source_block           GM469
_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               7700667
_chemical_oxdiff_formula         'C20 H20 B10 I1'
_reflns_odcompleteness_completeness 96.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. 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
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8A), C9(H9A), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
2.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)
;
_shelx_res_checksum              42860
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'