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_7700670
_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         'C27 H43 B10 I'
_chemical_formula_sum            'C27 H43 B10 I'
_chemical_formula_weight         602.61
_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                 99.7934(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.37394(8)
_cell_length_b                   15.47174(10)
_cell_length_c                   16.34898(12)
_cell_measurement_reflns_used    15398
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.1550
_cell_measurement_theta_min      2.7490
_cell_volume                     3084.34(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 0.996
_diffrn_measurement_details
;
  1 omega   51.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -15.00   55.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1504  -38.0000    0.0000 70

  3 omega   47.00   73.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1504 -125.0000   90.0000 26

  4 omega   25.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1504   38.0000  -60.0000 80

  5 omega  -31.00   42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1504  -57.0000 -180.0000 73

  6 omega   21.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1504   57.0000  150.0000 74

  7 omega   39.00   84.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1504   57.0000    0.0000 45

  8 omega   28.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1504 -125.0000  -30.0000 57

  9 omega  150.00  178.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 28

 10 omega   91.00  171.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 80

 11 omega   73.00  121.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 48

 12 omega  103.00  143.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 40

 13 omega   38.00  115.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 77

 14 omega   46.00   72.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 26

 15 omega   51.00   77.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -125.0000  104.9450 26

 16 omega   60.00   98.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 38

 17 omega   37.00  143.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -30.0000 106

 18 omega   38.00   90.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 52

 19 omega   38.00   89.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 51

 20 omega   91.00  116.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 25

 21 omega   41.00  125.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 84

 22 omega   41.00   78.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 37

 23 omega   81.00  107.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 26

 24 omega   40.00   94.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 54

 25 omega   97.00  171.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 74

 26 omega  153.00  178.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 25

 27 omega   82.00  121.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -125.0000  104.9450 39

 28 omega   73.00  115.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 42

 29 omega   93.00  119.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -118.0000 -162.9269 26

 30 omega   42.00  126.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 84

 31 omega   40.00   87.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -118.0000 -162.9269 47
;
_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      0.0727737000
_diffrn_orient_matrix_UB_12      0.0658007000
_diffrn_orient_matrix_UB_13      -0.0359346000
_diffrn_orient_matrix_UB_21      -0.0504430000
_diffrn_orient_matrix_UB_22      -0.0284544000
_diffrn_orient_matrix_UB_23      -0.0885900000
_diffrn_orient_matrix_UB_31      -0.0900865000
_diffrn_orient_matrix_UB_32      0.0691278000
_diffrn_orient_matrix_UB_33      -0.0022416000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23841
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.179
_diffrn_reflns_theta_min         3.625
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75381
_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    1.298
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0527P)^2^+4.6143P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5830
_reflns_number_total             6056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt02645b2.cif
_cod_data_source_block           GM467
_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               7700670
_chemical_oxdiff_formula         'C27 H43 B10 I1'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8A), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C)
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              45747
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'