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_7700666
_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         'C20 H27 B10 N O2'
_chemical_formula_sum            'C20 H27 B10 N O2'
_chemical_formula_weight         421.52
_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                 106.060(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.7572(10)
_cell_length_b                   7.1356(4)
_cell_length_c                   16.9222(9)
_cell_measurement_reflns_used    1984
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      71.9320
_cell_measurement_theta_min      4.6690
_cell_volume                     2292.6(2)
_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      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
  1 omega  -28.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5254  -38.0000  -60.0000 81

  2 omega  -18.00   50.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5254  -57.0000   90.0000 68

  3 omega   25.00   72.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5254 -122.0000  -84.0000 47

  4 omega  -25.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5254  -57.0000   30.0000 71

  5 omega   41.00   97.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 56

  6 omega   39.00  110.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  -90.0000 71

  7 omega   40.00   91.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 51

  8 omega   39.00   91.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 52

  9 omega   93.00  160.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 67

 10 omega   44.00   71.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  120.0000 27

 11 omega   44.00   98.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 54

 12 omega   44.00  123.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 79
;
_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      0.0582462000
_diffrn_orient_matrix_UB_12      0.0218673000
_diffrn_orient_matrix_UB_13      0.0816364000
_diffrn_orient_matrix_UB_21      -0.0558168000
_diffrn_orient_matrix_UB_22      0.0557409000
_diffrn_orient_matrix_UB_23      0.0437857000
_diffrn_orient_matrix_UB_31      -0.0088163000
_diffrn_orient_matrix_UB_32      -0.2072342000
_diffrn_orient_matrix_UB_33      0.0202249000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7232
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.328
_diffrn_reflns_theta_min         4.658
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80315
_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    1.221
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0643
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0814P)^2^+0.2575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1802
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3184
_reflns_number_total             4393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt02645b2.cif
_cod_data_source_block           GM446
_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               7700666
_chemical_oxdiff_formula         'C20 H27 B10 N1 O2'
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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(HE,HF), C4(H4A,HG), C5(HH,HI)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9A), C11(HM), C12(H12), C16(HN), C17(HO), C19(HP), C20(HQ)
2.c Idealised Me refined as rotating group:
 C6(HJ,HK,HL)
2.d Boron cage BH refined with riding coordinates:
 B1(H), B2(HA), B3(HB), B4(H4), B5(H5), B6(H6), B7(HC), B8(HD), B9(H9), B10(H10)
;
_shelx_res_checksum              52365
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'