#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/78/1517883.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1517883
loop_
_publ_author_name
'Zhang, Zuolun'
'Edkins, Robert M.'
'Nitsch, Jörn'
'Fucke, Katharina'
'Steffen, Andreas'
'Longobardi, Lauren E.'
'Stephan, Douglas W.'
'Lambert, Christoph'
'Marder, Todd B.'
_publ_section_title
;
 Optical and electronic properties of air-stable organoboron compounds
 with strongly electron-accepting bis(fluoromesityl)boryl groups
;
_journal_issue                   1
_journal_name_full               'Chem. Sci.'
_journal_page_first              308
_journal_paper_doi               10.1039/C4SC02410A
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C36 H36 B N'
_chemical_formula_sum            'C36 H36 B N'
_chemical_formula_weight         493.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-07-24
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.720(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8391(3)
_cell_length_b                   34.0268(11)
_cell_length_c                   9.5807(3)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.39
_cell_volume                     2831.26(16)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            31666
_diffrn_reflns_theta_full        25.9925
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.24
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9381
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.9381.
The λ/2 correction factor is 0.0000.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1577
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056.3818
_exptl_crystal_preparation       'soaked in perfluoro polyether oil'
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.2459
_refine_diff_density_min         -0.3475
_refine_diff_density_rms         0.0847
_refine_ls_d_res_high            0.8109
_refine_ls_d_res_low             9.0727
_refine_ls_goodness_of_fit_ref   1.0575
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    60
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0575
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0683P)²+1.1350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -10
_reflns_limit_k_max              41
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              -6
_reflns_number_gt                4703
_reflns_number_total             5556
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4sc02410a2.cif
_cod_data_source_block           13S090
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 1517881--1517885.cif.
;
_cod_database_code               1517883
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C35(H35), C23(H23), C21(H21), C20(H20), C32(H32), C28(H28), C34(H34),
 C36(H36), C24(H24), C26(H26), C30(H30), C12(H12), C27(H27), C29(H29), C3(H3),
 C33(H33), C5(H5), C14(H14)
2.b Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C16(H16a,H16b,H16c), C18(H18a,H18b,H18c), C9(H9a,H9b,H9c),
 C8(H8a,H8b,H8c), C17(H17a,H17b,H17c)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
N1 N 0.61232(13) 0.28907(3) -0.15128(13) 0.0187(3) Uani 1.000000 .
C1 C 1.07893(16) 0.41980(4) 0.22344(16) 0.0189(3) Uani 1.000000 .
C2 C 1.21785(16) 0.41694(4) 0.32326(16) 0.0188(3) Uani 1.000000 .
C3 C 1.35713(16) 0.42821(4) 0.28634(16) 0.0206(3) Uani 1.000000 .
H3 H 1.44969(16) 0.42559(4) 0.35423(16) 0.0248(4) Uiso 1.000000 R
C4 C 1.36348(16) 0.44319(4) 0.15233(17) 0.0209(3) Uani 1.000000 .
C5 C 1.22586(17) 0.44731(4) 0.05605(16) 0.0225(3) Uani 1.000000 .
H5 H 1.22791(17) 0.45819(4) -0.03489(16) 0.0270(4) Uiso 1.000000 R
C6 C 1.08533(17) 0.43599(4) 0.08861(16) 0.0214(3) Uani 1.000000 .
C7 C 1.22092(17) 0.40058(5) 0.47045(16) 0.0242(3) Uani 1.000000 .
H7a H 1.1538(10) 0.4164(2) 0.5190(5) 0.0363(5) Uiso 1.000000 GR
H7b H 1.1844(12) 0.37333(11) 0.46315(16) 0.0363(5) Uiso 1.000000 GR
H7c H 1.3265(3) 0.4014(3) 0.5246(4) 0.0363(5) Uiso 1.000000 GR
C8 C 1.51359(17) 0.45552(5) 0.11333(18) 0.0268(3) Uani 1.000000 .
H8a H 1.5271(7) 0.48394(7) 0.1270(12) 0.0402(5) Uiso 1.000000 GR
H8b H 1.5986(2) 0.4417(3) 0.1739(8) 0.0402(5) Uiso 1.000000 GR
H8c H 1.5129(5) 0.4490(3) 0.0136(4) 0.0402(5) Uiso 1.000000 GR
C9 C 0.94302(18) 0.44284(5) -0.02384(17) 0.0282(4) Uani 1.000000 .
H9a H 0.9380(7) 0.4230(2) -0.0988(7) 0.0423(5) Uiso 1.000000 GR
H9b H 0.8511(2) 0.4408(3) 0.0193(3) 0.0423(5) Uiso 1.000000 GR
H9c H 0.9478(7) 0.46910(14) -0.0648(9) 0.0423(5) Uiso 1.000000 GR
C10 C 0.85020(16) 0.41601(4) 0.38812(16) 0.0195(3) Uani 1.000000 .
C11 C 0.82240(16) 0.45637(4) 0.41066(16) 0.0224(3) Uani 1.000000 .
C12 C 0.74206(17) 0.46759(5) 0.51632(17) 0.0262(3) Uani 1.000000 .
H12 H 0.72118(17) 0.49468(5) 0.52742(17) 0.0314(4) Uiso 1.000000 R
C13 C 0.69161(17) 0.44058(5) 0.60570(17) 0.0268(4) Uani 1.000000 .
C14 C 0.72597(17) 0.40122(5) 0.58890(16) 0.0258(3) Uani 1.000000 .
H14 H 0.69651(17) 0.38236(5) 0.65192(16) 0.0310(4) Uiso 1.000000 R
C15 C 0.80244(16) 0.38860(4) 0.48222(16) 0.0217(3) Uani 1.000000 .
C16 C 0.87546(19) 0.48826(4) 0.32101(19) 0.0284(4) Uani 1.000000 .
H16a H 0.98821(19) 0.4895(2) 0.3405(10) 0.0427(5) Uiso 1.000000 GR
H16b H 0.8390(12) 0.48238(19) 0.22023(19) 0.0427(5) Uiso 1.000000 GR
H16c H 0.8336(11) 0.51361(7) 0.3441(9) 0.0427(5) Uiso 1.000000 GR
C17 C 0.6020(2) 0.45352(6) 0.7168(2) 0.0376(4) Uani 1.000000 .
H17a H 0.6583(8) 0.4745(3) 0.7747(10) 0.0564(7) Uiso 1.000000 GR
H17b H 0.5009(6) 0.4634(4) 0.6703(2) 0.0564(7) Uiso 1.000000 GR
H17c H 0.5883(14) 0.43116(11) 0.7777(9) 0.0564(7) Uiso 1.000000 GR
C18 C 0.83504(18) 0.34507(5) 0.47531(18) 0.0270(3) Uani 1.000000 .
H18a H 0.7504(7) 0.33228(7) 0.4106(10) 0.0405(5) Uiso 1.000000 GR
H18b H 0.9314(7) 0.34113(5) 0.4405(12) 0.0405(5) Uiso 1.000000 GR
H18c H 0.8444(13) 0.33359(8) 0.5704(3) 0.0405(5) Uiso 1.000000 GR
C19 C 0.84055(16) 0.37087(4) 0.15270(16) 0.0192(3) Uani 1.000000 .
C20 C 0.68353(16) 0.36219(4) 0.14066(15) 0.0189(3) Uani 1.000000 .
H20 H 0.62746(16) 0.37470(4) 0.20367(15) 0.0227(4) Uiso 1.000000 R
C21 C 0.60696(16) 0.33623(4) 0.04106(15) 0.0183(3) Uani 1.000000 .
H21 H 0.49982(16) 0.33181(4) 0.03507(15) 0.0219(4) Uiso 1.000000 R
C22 C 0.68652(16) 0.31640(4) -0.05110(15) 0.0177(3) Uani 1.000000 .
C23 C 0.84402(16) 0.32388(4) -0.03972(16) 0.0214(3) Uani 1.000000 .
H23 H 0.90090(16) 0.31044(4) -0.09991(16) 0.0257(4) Uiso 1.000000 R
C24 C 0.91724(16) 0.35061(4) 0.05813(16) 0.0214(3) Uani 1.000000 .
H24 H 1.02371(16) 0.35556(4) 0.06197(16) 0.0257(4) Uiso 1.000000 R
C25 C 0.69474(15) 0.25516(4) -0.18501(15) 0.0165(3) Uani 1.000000 .
C26 C 0.78325(16) 0.23299(4) -0.07784(15) 0.0206(3) Uani 1.000000 .
H26 H 0.79652(16) 0.24143(4) 0.01818(15) 0.0247(4) Uiso 1.000000 R
C27 C 0.85206(17) 0.19850(4) -0.11172(16) 0.0221(3) Uani 1.000000 .
H27 H 0.91307(17) 0.18344(4) -0.03870(16) 0.0265(4) Uiso 1.000000 R
C28 C 0.83223(17) 0.18591(4) -0.25169(16) 0.0217(3) Uani 1.000000 .
H28 H 0.87633(17) 0.16180(4) -0.27420(16) 0.0261(4) Uiso 1.000000 R
C29 C 0.74759(17) 0.20872(4) -0.35866(16) 0.0209(3) Uani 1.000000 .
H29 H 0.73636(17) 0.20053(4) -0.45484(16) 0.0251(4) Uiso 1.000000 R
C30 C 0.67939(16) 0.24334(4) -0.32604(15) 0.0186(3) Uani 1.000000 .
H30 H 0.62233(16) 0.25896(4) -0.39968(15) 0.0223(4) Uiso 1.000000 R
C31 C 0.44839(16) 0.28743(4) -0.18737(14) 0.0169(3) Uani 1.000000 .
C32 C 0.36283(17) 0.32128(4) -0.22923(15) 0.0197(3) Uani 1.000000 .
H32 H 0.41390(17) 0.34569(4) -0.23376(15) 0.0237(4) Uiso 1.000000 R
C33 C 0.20355(17) 0.31944(5) -0.26426(15) 0.0220(3) Uani 1.000000 .
H33 H 0.14588(17) 0.34274(5) -0.29013(15) 0.0264(4) Uiso 1.000000 R
C34 C 0.12763(16) 0.28368(5) -0.26176(15) 0.0214(3) Uani 1.000000 .
H34 H 0.01867(16) 0.28237(5) -0.28791(15) 0.0257(4) Uiso 1.000000 R
C35 C 0.21241(16) 0.25004(4) -0.22080(15) 0.0207(3) Uani 1.000000 .
H35 H 0.16112(16) 0.22558(4) -0.21861(15) 0.0249(4) Uiso 1.000000 R
C36 C 0.37169(16) 0.25173(4) -0.18289(15) 0.0187(3) Uani 1.000000 .
H36 H 0.42864(16) 0.22852(4) -0.15382(15) 0.0225(4) Uiso 1.000000 R
B1 B 0.92416(18) 0.40245(5) 0.25768(18) 0.0191(3) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C22 N1 C25 119.58(11)
C22 N1 C31 120.95(11)
C25 N1 C31 116.74(11)
C6 C1 C2 117.87(13)
B1 C1 C2 120.74(13)
B1 C1 C6 121.22(13)
C3 C2 C1 120.40(14)
C3 C2 C7 118.28(13)
C7 C2 C1 121.29(13)
C2 C3 C4 121.52(13)
C5 C4 C3 117.93(13)
C8 C4 C3 121.35(13)
C8 C4 C5 120.71(14)
C6 C5 C4 122.09(14)
C5 C6 C1 120.12(13)
C9 C6 C1 122.71(13)
C9 C6 C5 117.15(14)
C11 C10 C15 117.41(14)
B1 C10 C11 120.72(13)
B1 C10 C15 121.79(13)
C12 C11 C10 120.12(15)
C16 C11 C10 121.84(14)
C16 C11 C12 118.04(14)
C11 C12 C13 122.24(14)
C14 C13 C12 117.74(14)
C17 C13 C12 121.01(15)
C17 C13 C14 121.25(16)
C13 C14 C15 121.88(15)
C14 C15 C10 120.47(14)
C18 C15 C10 122.39(14)
C18 C15 C14 117.12(14)
C24 C19 C20 115.55(13)
B1 C19 C20 122.72(13)
B1 C19 C24 121.64(13)
C21 C20 C19 122.79(13)
C20 C21 C22 120.31(13)
C21 C22 N1 121.56(12)
C21 C22 C23 118.18(13)
C23 C22 N1 120.25(12)
C24 C23 C22 120.50(13)
C19 C24 C23 122.63(13)
C26 C25 N1 120.64(13)
C30 C25 N1 119.32(13)
C30 C25 C26 119.96(13)
C27 C26 C25 119.77(13)
C26 C27 C28 120.34(14)
C29 C28 C27 119.64(14)
C30 C29 C28 120.42(14)
C29 C30 C25 119.79(13)
C32 C31 N1 120.61(12)
C36 C31 N1 120.25(12)
C36 C31 C32 119.14(13)
C33 C32 C31 120.26(13)
C34 C33 C32 120.42(13)
C33 C34 C35 119.37(13)
C36 C35 C34 120.61(13)
C35 C36 C31 120.19(13)
C10 B1 C1 123.78(13)
C10 B1 C19 119.59(13)
C19 B1 C1 116.62(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C22 1.4080(18)
N1 C25 1.4331(18)
N1 C31 1.4268(17)
C1 C2 1.412(2)
C1 C6 1.415(2)
C1 B1 1.579(2)
C2 C3 1.396(2)
C2 C7 1.512(2)
C4 C3 1.392(2)
C4 C5 1.390(2)
C4 C8 1.504(2)
C6 C5 1.390(2)
C6 C9 1.514(2)
C10 C11 1.419(2)
C10 C15 1.415(2)
C10 B1 1.583(2)
C12 C11 1.394(2)
C13 C12 1.385(2)
C13 C14 1.389(2)
C13 C17 1.506(2)
C15 C14 1.394(2)
C15 C18 1.513(2)
C16 C11 1.512(2)
C19 C20 1.403(2)
C19 C24 1.409(2)
C19 B1 1.561(2)
C21 C20 1.382(2)
C22 C21 1.400(2)
C22 C23 1.3994(19)
C23 C24 1.378(2)
C25 C26 1.392(2)
C25 C30 1.392(2)
C26 C27 1.388(2)
C28 C27 1.388(2)
C28 C29 1.388(2)
C30 C29 1.385(2)
C31 C32 1.395(2)
C31 C36 1.396(2)
C32 C33 1.387(2)
C34 C33 1.392(2)
C35 C34 1.384(2)
C35 C36 1.388(2)
