#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/07/2200738.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2200738
loop_
_publ_author_name
'Wolfgang Kliegel'
'Lutz Preu'
'Ulf Riebe'
'Brian O. Patrick'
'Steven J. Rettig'
'James Trotter'
_publ_section_title
;
 A BONBON 6-membered ring heterocycle
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o943
_journal_page_last               o944
_journal_paper_doi               10.1107/S1600536801014866
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C26 H28 B2 N2 O2'
_chemical_formula_moiety         'C26 H28 B2 N2 O2'
_chemical_formula_sum            'C26 H28 B2 N2 O2'
_chemical_formula_weight         422.14
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 95.444(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9184(3)
_cell_length_b                   8.8703(3)
_cell_length_c                   18.7337(9)
_cell_measurement_reflns_used    6804
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      3.17
_cell_volume                     1144.47(8)
_computing_cell_refinement       d*TREK
_computing_data_collection
'd*TREK (Molecular Structure Corporation, 1996-1998)'
_computing_data_reduction        d*TREK
_computing_publication_material  TEXSAN
_computing_structure_refinement
'TEXSAN (Molecular Structure Corporation, 1992-1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 11.76
_diffrn_measurement_device_type  'Rigaku/ADSC CCD'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .7107
_diffrn_reflns_av_R_equivalents  .028
_diffrn_reflns_av_sigmaI/netI    .070
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9941
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         3.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .076
_exptl_absorpt_correction_T_max  .98
_exptl_absorpt_correction_T_min  .96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'd*TREK (Molecular Structure Corporation, 1996-1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .25
_refine_diff_density_max         .32
_refine_diff_density_min         -.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.91
_refine_ls_goodness_of_fit_ref   1.91
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .059
_refine_ls_R_factor_gt           .037
_refine_ls_shift/su_max          .005
_refine_ls_shift/su_mean         .002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[σ²(Fo²)]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .118
_refine_ls_wR_factor_ref         .058
_reflns_number_gt                2059
_reflns_number_total             2514
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            om6050.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2200738
loop_
_symmetry_equiv_pos_as_xyz
'  +x,  +y,  +z'
1/2-x,1/2+y,1/2-z
'  -x,  -y,  -z'
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
O1 .30565(8) .52581(7) .01485(4) .0189(2) Uani d ? . 1.000
N1 .39880(10) .62161(9) -.03335(5) .0177(2) Uani d ? . 1.000
C1 .27420(10) .75650(10) -.04507(7) .0288(3) Uani d ? . 1.000
C2 .31750(10) .30040(10) -.07083(5) .0203(2) Uani d ? . 1.000
C3 .1584(2) .36280(10) -.11227(6) .0317(3) Uani d ? . 1.000
C4 .1030(2) .3134(2) -.18177(7) .0442(4) Uani d ? . 1.000
C5 .2011(2) .1980(2) -.21108(6) .0462(4) Uani d ? . 1.000
C6 .3545(2) .1297(2) -.17050(7) .0436(4) Uani d ? . 1.000
C7 .4121(2) .18150(10) -.10167(6) .0315(3) Uani d ? . 1.000
C8 .27590(10) .27590(10) .07272(5) .0189(2) Uani d ? . 1.000
C9 .26140(10) .34550(10) .13907(6) .0257(3) Uani d ? . 1.000
C10 .1824(2) .27060(10) .19474(6) .0319(3) Uani d ? . 1.000
C11 .11670(10) .12380(10) .18547(6) .0309(3) Uani d ? . 1.000
C12 .13030(10) .05200(10) .12055(6) .0282(3) Uani d ? . 1.000
C13 .20890(10) .12770(10) .06504(6) .0228(3) Uani d ? . 1.000
B1 .36770(10) .36560(10) .00934(6) .0174(3) Uani d ? . 1.000
H1 .391(2) .5710(10) -.0767(7) .024(3) Uiso d ? . 1.000
H2 .3439 .8343 -.0695 .035 Uiso c ? . 1.000
H3 .1549 .7294 -.0747 .035 Uiso c ? . 1.000
H4 .2413 .7952 .0013 .035 Uiso c ? . 1.000
H5 .0841 .4435 -.0918 .038 Uiso c ? . 1.000
H6 -.0069 .3613 -.2099 .053 Uiso c ? . 1.000
H7 .1631 .1641 -.2602 .055 Uiso c ? . 1.000
H8 .4227 .0449 -.1903 .052 Uiso c ? . 1.000
H9 .5223 .1329 -.0740 .038 Uiso c ? . 1.000
H10 .3078 .4492 .1465 .031 Uiso c ? . 1.000
H11 .1733 .3218 .2406 .038 Uiso c ? . 1.000
H12 .0609 .0711 .2246 .037 Uiso c ? . 1.000
H13 .0846 -.0520 .1137 .034 Uiso c ? . 1.000
H14 .2174 .0756 .0193 .027 Uiso c ? . 1.000
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .002 .002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H .000 .000
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
B .000 .001
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N .004 .003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O .008 .006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 O1 B1 . . 111.78(6) yes
O1 N1 C1 . . 106.39(7) yes
O1 N1 B1 . 3_665 110.95(7) yes
O1 N1 H1 . . 105.8(8) no
C1 N1 B1 . 3_665 122.01(7) yes
C1 N1 H1 . . 106.3(8) no
B1 N1 H1 3_665 . 104.3(7) no
N1 C1 H2 . . 109.4 no
N1 C1 H3 . . 109.4 no
N1 C1 H4 . . 109.4 no
H2 C1 H3 . . 109.6 no
H2 C1 H4 . . 109.5 no
H3 C1 H4 . . 109.5 no
C3 C2 C7 . . 116.40(10) yes
C3 C2 B1 . . 117.52(9) yes
C7 C2 B1 . . 126.01(9) yes
C2 C3 C4 . . 121.80(10) yes
C2 C3 H5 . . 119.1 no
C4 C3 H5 . . 119.2 no
C3 C4 C5 . . 120.40(10) yes
C3 C4 H6 . . 119.8 no
C5 C4 H6 . . 119.8 no
C4 C5 C6 . . 119.30(10) yes
C4 C5 H7 . . 120.4 no
C6 C5 H7 . . 120.4 no
C5 C6 C7 . . 120.10(10) yes
C5 C6 H8 . . 119.8 no
C7 C6 H8 . . 120.0 no
C2 C7 C6 . . 122.00(10) yes
C2 C7 H9 . . 119.1 no
C6 C7 H9 . . 119.0 no
C9 C8 C13 . . 117.08(9) yes
C9 C8 B1 . . 120.25(9) yes
C13 C8 B1 . . 122.68(9) yes
C8 C9 C10 . . 121.40(10) yes
C8 C9 H10 . . 119.3 no
C10 C9 H10 . . 119.2 no
C9 C10 C11 . . 120.20(10) yes
C9 C10 H11 . . 119.9 no
C11 C10 H11 . . 119.9 no
C10 C11 C12 . . 119.60(10) yes
C10 C11 H12 . . 120.3 no
C12 C11 H12 . . 120.1 no
C11 C12 C13 . . 119.90(10) yes
C11 C12 H13 . . 120.1 no
C13 C12 H13 . . 119.9 no
C8 C13 C12 . . 121.80(10) yes
C8 C13 H14 . . 119.1 no
C12 C13 H14 . . 119.1 no
O1 B1 N1 . 3_665 101.40(7) yes
O1 B1 C2 . . 111.58(8) yes
O1 B1 C8 . . 106.50(7) yes
N1 B1 C2 3_665 . 113.50(8) yes
N1 B1 C8 3_665 . 106.21(7) yes
C2 B1 C8 . . 116.34(8) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 . . 1.4360(10) yes
O1 B1 . . 1.4910(10) yes
N1 C1 . . 1.4790(10) yes
N1 B1 . 3_665 1.6400(10) yes
N1 H1 . . .930(10) no
C1 H2 . . .98 no
C1 H3 . . .98 no
C1 H4 . . .98 no
C2 C3 . . 1.4000(10) yes
C2 C7 . . 1.395(2) yes
C2 B1 . . 1.6160(10) yes
C3 C4 . . 1.393(2) yes
C3 H5 . . .98 no
C4 C5 . . 1.372(2) yes
C4 H6 . . .98 no
C5 C6 . . 1.385(2) yes
C5 H7 . . .98 no
C6 C7 . . 1.391(2) yes
C6 H8 . . .98 no
C7 H9 . . .98 no
C8 C9 . . 1.400(2) yes
C8 C13 . . 1.3970(10) yes
C8 B1 . . 1.6090(10) yes
C9 C10 . . 1.391(2) yes
C9 H10 . . .98 no
C10 C11 . . 1.384(2) yes
C10 H11 . . .98 no
C11 C12 . . 1.384(2) yes
C11 H12 . . .98 no
C12 C13 . . 1.3910(10) yes
C12 H13 . . .98 no
C13 H14 . . .98 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
C1 C12 3.4590(10) 3_565 no
C1 C13 3.4830(10) 3_565 no
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N1 B1 C2 . 3_665 3_665 -58.70(10) no
O1 N1 B1 C8 . 3_665 3_665 172.27(7) no
O1 N1 B1 O1 . 3_665 3_665 61.14(9) no
O1 B1 N1 C1 . 3_665 3_665 172.29(8) no
O1 B1 C2 C3 . . . -28.50(10) no
O1 B1 C2 C7 . . . 155.16(9) no
O1 B1 C8 C9 . . . -36.00(10) no
O1 B1 C8 C13 . . . 144.35(8) no
N1 O1 B1 C2 . . . -59.41(9) no
N1 O1 B1 C8 . . . 172.64(7) no
N1 O1 B1 N1 . . 3_665 61.73(9) no
N1 B1 C2 C3 3_665 3_665 3_665 142.28(9) no
N1 B1 C2 C7 3_665 3_665 3_665 -41.30(10) no
N1 B1 C8 C9 3_665 3_665 3_665 -71.50(10) no
N1 B1 C8 C13 3_665 3_665 3_665 108.14(9) no
C1 N1 O1 B1 . . . 157.63(8) no
C1 N1 B1 C2 . 3_665 3_665 67.90(10) no
C1 N1 B1 C8 . 3_665 3_665 -61.20(10) no
C2 C3 C4 C5 . . . 1.7(2) no
C2 C7 C6 C5 . . . 1.0(2) no
C2 B1 C8 C9 . . . -161.06(9) no
C2 B1 C8 C13 . . . 19.30(10) no
C3 C2 C7 C6 . . . 1.5(2) no
C3 C2 B1 C8 . . . 94.00(10) no
C3 C4 C5 C6 . . . .8(2) no
C4 C3 C2 C7 . . . -2.8(2) no
C4 C3 C2 B1 . . . -179.50(10) no
C4 C5 C6 C7 . . . -2.1(2) no
C6 C7 C2 B1 . . . 177.90(10) no
C7 C2 B1 C8 . . . -82.40(10) no
C8 C9 C10 C11 . . . .3(2) no
C8 C13 C12 C11 . . . .10(10) no
C9 C8 C13 C12 . . . .20(10) no
C9 C10 C11 C12 . . . .1(2) no
C10 C9 C8 C13 . . . -.40(10) no
C10 C9 C8 B1 . . . 179.90(8) no
C10 C11 C12 C13 . . . -.3(2) no
C12 C13 C8 B1 . . . 179.90(8) no
B1 O1 N1 B1 . . 3_665 -67.60(9) no
