#------------------------------------------------------------------------------
#$Date: 2016-03-25 22:33:55 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180015 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/09/7030922.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_7030922
loop_
_publ_author_name
'Seven, Omer'
'Popp, Sebastian'
'Bolte, Michael'
'Lerner, Hans-Wolfram'
'Wagner, Matthias'
_publ_section_title
;
 Synthesis and characterisation of the complete series of B-N analogues of
 triptycene.
;
_journal_issue                   22
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8241
_journal_page_last               8253
_journal_paper_doi               10.1039/c4dt00442f
_journal_volume                  43
_journal_year                    2014
_chemical_formula_moiety         'C15 H14 B2 Br N6, Br C H2 Cl2'
_chemical_formula_sum            'C16 H16 B2 Br2 Cl2 N6'
_chemical_formula_weight         544.69
_chemical_name_systematic        ?
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0607(5)
_cell_length_b                   9.6544(6)
_cell_length_c                   18.1880(8)
_cell_measurement_reflns_used    40520
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      3.36
_cell_volume                     2117.79(18)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1048
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37320
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_min         3.378
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    4.095
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0353
_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/[σ²(Fo²)+(0.0352P)²+2.0261P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0794
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2070
_reflns_number_total             2170
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4dt00442f2.cif
_cod_data_source_block           wa1655
_cod_database_code               7030922
#BEGIN Tags that were not found in dictionaries:
_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. 
;
_shelx_estimated_absorpt_t_min   0.495
_shelx_estimated_absorpt_t_max   0.821
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
_atom_site_refinement_flags_occupancy
Br1 Br 0.99831(3) 0.7500 0.46015(2) 0.02714(13) Uani 1 2 d S T P
Br2 Br 1.22518(3) 0.7500 0.35129(2) 0.02520(13) Uani 1 2 d S T P
B1 B 0.5731(3) 0.7500 0.6582(2) 0.0195(8) Uani 1 2 d S T P
B2 B 0.3964(4) 0.7500 0.7472(3) 0.0244(9) Uani 1 2 d S T P
H2 H 0.319(4) 0.7500 0.788(3) 0.029 Uiso 1 2 d S U P
N1 N 0.4579(3) 0.7500 0.61923(18) 0.0216(6) Uani 1 2 d S T P
N2 N 0.3675(3) 0.7500 0.66461(19) 0.0239(7) Uani 1 2 d S T P
C3 C 0.2770(3) 0.7500 0.6227(3) 0.0303(9) Uani 1 2 d S T P
H3 H 0.2028 0.7500 0.6402 0.036 Uiso 1 2 calc R U P
C4 C 0.3082(4) 0.7500 0.5497(3) 0.0338(10) Uani 1 2 d S T P
H4 H 0.2609 0.7500 0.5080 0.041 Uiso 1 2 calc R U P
C5 C 0.4229(3) 0.7500 0.5501(2) 0.0272(9) Uani 1 2 d S T P
H5 H 0.4690 0.7500 0.5078 0.033 Uiso 1 2 calc R U P
N11 N 0.56735(18) 0.6239(2) 0.71297(12) 0.0202(5) Uani 1 1 d . . .
N12 N 0.47516(18) 0.6247(2) 0.75736(13) 0.0235(5) Uani 1 1 d . . .
C13 C 0.4860(2) 0.5234(3) 0.80701(16) 0.0271(6) Uani 1 1 d . . .
H13 H 0.4337 0.5009 0.8442 0.033 Uiso 1 1 calc R U .
C14 C 0.5856(3) 0.4570(3) 0.79519(17) 0.0298(6) Uani 1 1 d . . .
H14 H 0.6149 0.3811 0.8222 0.036 Uiso 1 1 calc R U .
C15 C 0.6343(2) 0.5232(3) 0.73623(16) 0.0249(6) Uani 1 1 d . . .
H15 H 0.7043 0.5006 0.7155 0.030 Uiso 1 1 calc R U .
C21 C 0.6735(3) 0.7500 0.6022(2) 0.0199(7) Uani 1 2 d S T P
C22 C 0.7204(2) 0.6263(3) 0.57684(15) 0.0226(6) Uani 1 1 d . . .
H22 H 0.6867 0.5407 0.5898 0.027 Uiso 1 1 calc R U .
C23 C 0.8150(2) 0.6253(3) 0.53317(15) 0.0235(6) Uani 1 1 d . . .
H23 H 0.8461 0.5403 0.5168 0.028 Uiso 1 1 calc R U .
C24 C 0.8629(3) 0.7500 0.5140(2) 0.0217(8) Uani 1 2 d S T P
C1L C 0.4390(4) 0.2500 0.6660(3) 0.0343(10) Uani 1 2 d S T P
H1L1 H 0.5209 0.2500 0.6696 0.041 Uiso 1 2 calc R U P
H1L2 H 0.4082 0.2500 0.7164 0.041 Uiso 1 2 calc R U P
Cl1 Cl 0.39452(9) 0.39951(9) 0.61892(6) 0.0550(3) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
N1 B1 N11 104.4(2) . 7_575
N1 B1 N11 104.4(2) . .
N11 B1 N11 101.3(3) 7_575 .
N1 B1 C21 112.9(3) . .
N11 B1 C21 116.2(2) 7_575 .
N11 B1 C21 116.2(2) . .
N2 B2 N12 104.8(2) . 7_575
N2 B2 N12 104.8(2) . .
N12 B2 N12 102.7(3) 7_575 .
N2 B2 H2 115(2) . .
N12 B2 H2 114.0(12) 7_575 .
N12 B2 H2 114.0(12) . .
C5 N1 N2 108.6(3) . .
C5 N1 B1 135.6(3) . .
N2 N1 B1 115.8(3) . .
C3 N2 N1 107.9(3) . .
C3 N2 B2 138.1(4) . .
N1 N2 B2 114.1(3) . .
N2 C3 C4 109.2(4) . .
N2 C3 H3 125.4 . .
C4 C3 H3 125.4 . .
C3 C4 C5 105.5(4) . .
C3 C4 H4 127.2 . .
C5 C4 H4 127.2 . .
N1 C5 C4 108.9(4) . .
N1 C5 H5 125.6 . .
C4 C5 H5 125.6 . .
C15 N11 N12 107.9(2) . .
C15 N11 B1 137.6(2) . .
N12 N11 B1 113.8(2) . .
C13 N12 N11 108.3(2) . .
C13 N12 B2 135.4(3) . .
N11 N12 B2 115.5(2) . .
N12 C13 C14 108.6(3) . .
N12 C13 H13 125.7 . .
C14 C13 H13 125.7 . .
C13 C14 C15 106.1(3) . .
C13 C14 H14 127.0 . .
C15 C14 H14 127.0 . .
N11 C15 C14 109.1(2) . .
N11 C15 H15 125.5 . .
C14 C15 H15 125.5 . .
C22 C21 C22 117.1(3) 7_575 .
C22 C21 B1 121.45(17) 7_575 .
C22 C21 B1 121.45(17) . .
C23 C22 C21 121.8(3) . .
C23 C22 H22 119.1 . .
C21 C22 H22 119.1 . .
C24 C23 C22 118.8(3) . .
C24 C23 H23 120.6 . .
C22 C23 H23 120.6 . .
C23 C24 C23 121.5(3) . 7_575
C23 C24 Br1 119.25(17) . .
C23 C24 Br1 119.25(17) 7_575 .
Cl1 C1L Cl1 110.1(2) 7_565 .
Cl1 C1L H1L1 109.6 7_565 .
Cl1 C1L H1L1 109.6 . .
Cl1 C1L H1L2 109.6 7_565 .
Cl1 C1L H1L2 109.6 . .
H1L1 C1L H1L2 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C24 1.905(4) .
B1 N1 1.561(5) .
B1 N11 1.574(3) 7_575
B1 N11 1.574(3) .
B1 C21 1.582(5) .
B2 N2 1.541(6) .
B2 N12 1.549(3) 7_575
B2 N12 1.549(3) .
B2 H2 1.19(5) .
N1 C5 1.325(5) .
N1 N2 1.368(5) .
N2 C3 1.331(5) .
C3 C4 1.379(7) .
C3 H3 0.9500 .
C4 C5 1.383(6) .
C4 H4 0.9500 .
C5 H5 0.9500 .
N11 C15 1.333(3) .
N11 N12 1.374(3) .
N12 C13 1.337(4) .
C13 C14 1.379(4) .
C13 H13 0.9500 .
C14 C15 1.379(4) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C21 C22 1.401(3) 7_575
C21 C22 1.401(3) .
C22 C23 1.390(4) .
C22 H22 0.9500 .
C23 C24 1.380(3) .
C23 H23 0.9500 .
C24 C23 1.380(3) 7_575
C1L Cl1 1.761(3) 7_565
C1L Cl1 1.761(3) .
C1L H1L1 0.9900 .
C1L H1L2 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 Br2 0.95 2.88 3.745(5) 151.7 1_455
C13 H13 Br2 0.95 3.09 3.755(3) 128.3 2_665
C14 H14 Br1 0.95 3.12 3.744(3) 124.4 2_665
C15 H15 Br2 0.95 2.84 3.516(3) 129.2 5_766
C1L H1L1 Br2 0.99 3.09 4.063(5) 169.1 5_766
C1L H1L2 Br2 0.99 2.93 3.909(5) 168.8 2_665
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N11 B1 N1 C5 127.03(18) 7_575 .
N11 B1 N1 C5 -127.03(18) . .
C21 B1 N1 C5 0.000(2) . .
N11 B1 N1 N2 -52.97(18) 7_575 .
N11 B1 N1 N2 52.97(18) . .
C21 B1 N1 N2 180.000(1) . .
C5 N1 N2 C3 0.000(1) . .
B1 N1 N2 C3 180.000(1) . .
C5 N1 N2 B2 180.000(1) . .
B1 N1 N2 B2 0.000(1) . .
N12 B2 N2 C3 -126.15(19) 7_575 .
N12 B2 N2 C3 126.15(19) . .
N12 B2 N2 N1 53.85(19) 7_575 .
N12 B2 N2 N1 -53.85(19) . .
N1 N2 C3 C4 0.000(1) . .
B2 N2 C3 C4 180.000(1) . .
N2 C3 C4 C5 0.000(1) . .
N2 N1 C5 C4 0.000(1) . .
B1 N1 C5 C4 180.000(1) . .
C3 C4 C5 N1 0.000(1) . .
N1 B1 N11 C15 140.0(3) . .
N11 B1 N11 C15 -111.8(3) 7_575 .
C21 B1 N11 C15 15.1(5) . .
N1 B1 N11 N12 -51.4(3) . .
N11 B1 N11 N12 56.8(3) 7_575 .
C21 B1 N11 N12 -176.3(2) . .
C15 N11 N12 C13 -0.6(3) . .
B1 N11 N12 C13 -172.6(2) . .
C15 N11 N12 B2 170.3(2) . .
B1 N11 N12 B2 -1.6(3) . .
N2 B2 N12 C13 -137.1(3) . .
N12 B2 N12 C13 113.6(3) 7_575 .
N2 B2 N12 N11 55.1(3) . .
N12 B2 N12 N11 -54.2(4) 7_575 .
N11 N12 C13 C14 0.3(3) . .
B2 N12 C13 C14 -168.0(3) . .
N12 C13 C14 C15 0.1(3) . .
N12 N11 C15 C14 0.7(3) . .
B1 N11 C15 C14 169.7(3) . .
C13 C14 C15 N11 -0.5(3) . .
N1 B1 C21 C22 90.5(3) . 7_575
N11 B1 C21 C22 -29.9(5) 7_575 7_575
N11 B1 C21 C22 -149.0(3) . 7_575
N1 B1 C21 C22 -90.5(3) . .
N11 B1 C21 C22 149.0(3) 7_575 .
N11 B1 C21 C22 29.9(5) . .
C22 C21 C22 C23 5.1(5) 7_575 .
B1 C21 C22 C23 -173.8(3) . .
C21 C22 C23 C24 -0.6(4) . .
C22 C23 C24 C23 -4.3(6) . 7_575
C22 C23 C24 Br1 175.6(2) . .
