#------------------------------------------------------------------------------
#$Date: 2017-12-08 01:46:12 +0200 (Fri, 08 Dec 2017) $
#$Revision: 204039 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/68/4126809.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_4126809
loop_
_publ_author_name
'Liu, Kanglei'
'Lalancette, Roger A.'
'Jäkle, Frieder'
_publ_section_title
;
 B-N Lewis Pair Functionalization of Anthracene: Structural Dynamics,
 Optoelectronic Properties, and O2 Sensitization.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b11062
_journal_year                    2017
_chemical_formula_moiety         'C26 H20 N2'
_chemical_formula_sum            'C26 H20 N2'
_chemical_formula_weight         360.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 117.944(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.246(4)
_cell_length_b                   9.4695(18)
_cell_length_c                   11.785(2)
_cell_measurement_reflns_used    6096
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      4.94
_cell_volume                     1897.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7896
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.715
_diffrn_reflns_theta_min         5.203
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.218
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0371
_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/[σ²(Fo²)+(0.0540P)²+1.2259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1498
_reflns_number_total             1658
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b11062_si_002.cif
_cod_data_source_block           151109RAL_KL_61_100K_0m_a
_cod_database_code               4126809
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_exptl_absorpt_special_details
'crystal mounted on a Cryoloop using Paratone-N'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.64429(6) 0.51726(11) 0.61587(10) 0.0206(3) Uani 1 1 d . .
C1 C 0.69510(7) 0.62470(12) 0.66957(12) 0.0181(3) Uani 1 1 d . .
C2 C 0.71766(8) 0.67352(13) 0.79273(12) 0.0211(3) Uani 1 1 d . .
H2 H 0.7554 0.7469 0.8289 0.025 Uiso 1 1 calc R U
C3 C 0.68369(8) 0.61234(13) 0.86204(13) 0.0232(3) Uani 1 1 d . .
H3 H 0.6972 0.6444 0.9462 0.028 Uiso 1 1 calc R U
C4 C 0.63007(8) 0.50448(14) 0.80694(13) 0.0230(3) Uani 1 1 d . .
H4 H 0.6053 0.4629 0.8520 0.028 Uiso 1 1 calc R U
C5 C 0.61263(7) 0.45729(13) 0.68487(13) 0.0219(3) Uani 1 1 d . .
C6 C 0.55653(9) 0.33753(15) 0.62158(14) 0.0321(4) Uani 1 1 d . .
H6A H 0.5049 0.3754 0.5611 0.048 Uiso 1 1 calc R U
H6B H 0.5516 0.2811 0.6871 0.048 Uiso 1 1 calc R U
H6C H 0.5765 0.2780 0.5752 0.048 Uiso 1 1 calc R U
C7 C 0.72477(7) 0.69148(12) 0.58512(12) 0.0182(3) Uani 1 1 d . .
C8 C 0.68408(7) 0.80674(12) 0.50718(12) 0.0183(3) Uani 1 1 d . .
C9 C 0.79053(7) 0.63457(13) 0.57998(12) 0.0183(3) Uani 1 1 d . .
C10 C 0.83285(7) 0.51739(13) 0.65797(12) 0.0213(3) Uani 1 1 d . .
H10 H 0.8172 0.4787 0.7168 0.026 Uiso 1 1 calc R U
C11 C 0.89506(8) 0.46007(14) 0.64979(13) 0.0241(3) Uani 1 1 d . .
H11 H 0.9218 0.3811 0.7017 0.029 Uiso 1 1 calc R U
C12 C 0.92029(8) 0.51762(13) 0.56405(13) 0.0239(3) Uani 1 1 d . .
H12 H 0.9639 0.4771 0.5590 0.029 Uiso 1 1 calc R U
C13 C 0.88243(7) 0.63047(13) 0.48911(12) 0.0206(3) Uani 1 1 d . .
H13 H 0.9006 0.6684 0.4331 0.025 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C5 117.95(11) . .
N1 C1 C2 123.15(11) . .
N1 C1 C7 115.17(11) . .
C2 C1 C7 121.66(11) . .
C1 C2 C3 118.31(12) . .
C1 C2 H2 120.8 . .
C3 C2 H2 120.8 . .
C4 C3 C2 119.10(12) . .
C4 C3 H3 120.4 . .
C2 C3 H3 120.4 . .
C3 C4 C5 119.36(12) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
N1 C5 C4 122.06(12) . .
N1 C5 C6 116.20(12) . .
C4 C5 C6 121.74(12) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C9 C7 C8 120.53(11) . .
C9 C7 C1 119.90(11) . .
C8 C7 C1 119.50(11) . .
C7 C8 C13 122.38(11) . 7_666
C7 C8 C9 119.65(11) . 7_666
C13 C8 C9 117.97(11) 7_666 7_666
C7 C9 C10 121.67(11) . .
C7 C9 C8 119.81(11) . 7_666
C10 C9 C8 118.51(11) . 7_666
C11 C10 C9 121.39(12) . .
C11 C10 H10 119.3 . .
C9 C10 H10 119.3 . .
C10 C11 C12 120.27(12) . .
C10 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
C13 C12 C11 120.41(12) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C12 C13 C8 121.43(12) . 7_666
C12 C13 H13 119.3 . .
C8 C13 H13 119.3 7_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3460(16) .
N1 C5 1.3489(16) .
C1 C2 1.3851(18) .
C1 C7 1.4997(17) .
C2 C3 1.3895(18) .
C2 H2 0.9500 .
C3 C4 1.3791(19) .
C3 H3 0.9500 .
C4 C5 1.389(2) .
C4 H4 0.9500 .
C5 C6 1.5011(18) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C9 1.4027(17) .
C7 C8 1.4050(18) .
C8 C13 1.4305(17) 7_666
C8 C9 1.4399(17) 7_666
C9 C10 1.4275(18) .
C9 C8 1.4399(17) 7_666
C10 C11 1.3585(18) .
C10 H10 0.9500 .
C11 C12 1.4189(19) .
C11 H11 0.9500 .
C12 C13 1.3601(18) .
C12 H12 0.9500 .
C13 C8 1.4305(17) 7_666
C13 H13 0.9500 .
