#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/35/2013578.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_2013578
loop_
_publ_author_name
'Sopková-de Oliveira Santos, Jana'
'Bouillon, Alexandre'
'Lancelot, Jean-Charles'
'Rault, Sylvain'
_publ_section_title
;
 2-Bromo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, a new
 unexpected bifunctional building block for combinatorial chemistry
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o596
_journal_page_last               o597
_journal_paper_doi               10.1107/S0108270103016767
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C11 H15 B Br N O2'
_chemical_formula_moiety         'C11 H15 B Br N O2'
_chemical_formula_sum            'C11 H15 B Br N O2'
_chemical_formula_weight         283.96
_chemical_melting_point          401
_chemical_name_systematic
;
2-bromo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4917(8)
_cell_length_b                   12.3270(10)
_cell_length_c                   15.8440(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      18
_cell_volume                     1267.9(2)
_computing_cell_refinement       'CAD-4-PC Software'
_computing_data_collection       'CAD-4-PC Software (Enraf-Nonius, 1996)'
_computing_data_reduction        'JANA98 (Petříček & Dušek, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.087
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4581
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        3.8
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.226
_exptl_absorpt_correction_T_max  0.660
_exptl_absorpt_correction_T_min  0.140
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'GAUSSIAN98 (Frisch et al., 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.79
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.154
_refine_ls_R_factor_gt           0.062
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0878P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.133
_refine_ls_wR_factor_ref         0.166
_reflns_number_gt                1857
_reflns_number_total             3689
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1698.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'YES' changed to 'yes' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_geom_bond_publ_flag'
value 'YES' changed to 'yes' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'YES' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (3
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2013578
_cod_database_fobs_code          2013578
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1 0.06477(12) 0.48664(6) 0.41940(4) 0.0776(3) Uani d . 1 . . Br
C2 0.2434(10) 0.4161(4) 0.4982(3) 0.0500(13) Uani d . 1 . . C
C3 0.4517(11) 0.4148(4) 0.4825(4) 0.0600(15) Uani d . 1 . . C
H3 0.5054 0.4464 0.4339 0.072 Uiso calc R 1 . . H
C4 0.5767(11) 0.3662(5) 0.5397(4) 0.0606(14) Uani d . 1 . . C
H4 0.7183 0.3632 0.5312 0.073 Uiso calc R 1 . . H
C5 0.4876(8) 0.3209(4) 0.6117(3) 0.0489(13) Uani d . 1 . . C
H5 0.5699 0.2881 0.6524 0.059 Uiso calc R 1 . . H
C6 0.2777(9) 0.3249(4) 0.6222(3) 0.0450(12) Uani d . 1 . . C
N1 0.1530(7) 0.3742(3) 0.5656(3) 0.0451(10) Uani d . 1 . . N
B 0.1730(10) 0.2706(5) 0.7015(4) 0.0432(14) Uani d . 1 . . B
O1 0.2950(5) 0.2368(3) 0.7680(3) 0.0574(10) Uani d . 1 . . O
O2 -0.0263(5) 0.2496(3) 0.7116(2) 0.0532(10) Uani d . 1 . . O
C7 0.1640(9) 0.1704(5) 0.8213(3) 0.0525(14) Uani d . 1 . . C
C71 0.2287(12) 0.1855(7) 0.9124(4) 0.080(2) Uani d . 1 . . C
H71A 0.3698 0.1638 0.9189 0.09(2) Uiso calc R 1 . . H
H71B 0.1428 0.1419 0.9482 0.11(3) Uiso calc R 1 . . H
H71C 0.2144 0.2604 0.9277 0.09(3) Uiso calc R 1 . . H
C72 0.2005(12) 0.0533(5) 0.7955(5) 0.076(2) Uani d . 1 . . C
H72A 0.1649 0.0442 0.7371 0.14(4) Uiso calc R 1 . . H
H72B 0.1166 0.0064 0.8295 0.11(3) Uiso calc R 1 . . H
H72C 0.3431 0.0354 0.8035 0.08(2) Uiso calc R 1 . . H
C8 -0.0525(10) 0.2112(5) 0.7996(3) 0.0524(13) Uani d . 1 . . C
C81 -0.2187(10) 0.1240(8) 0.7989(5) 0.081(2) Uani d . 1 . . C
H81A -0.3487 0.1561 0.7844 0.09(2) Uiso calc R 1 . . H
H81B -0.2281 0.0915 0.8539 0.067(19) Uiso calc R 1 . . H
H81C -0.1841 0.0694 0.7581 0.16(5) Uiso calc R 1 . . H
C82 -0.1194(16) 0.3095(7) 0.8494(5) 0.101(3) Uani d . 1 . . C
H82A -0.0124 0.3632 0.8481 0.15(4) Uiso calc R 1 . . H
H82B -0.1457 0.2887 0.9068 0.075(19) Uiso calc R 1 . . H
H82C -0.2427 0.3389 0.8250 0.13(4) Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.1015(5) 0.0815(5) 0.0498(3) 0.0145(4) 0.0040(4) 0.0246(3)
C2 0.067(4) 0.047(3) 0.036(3) 0.008(2) 0.004(3) 0.006(2)
C3 0.079(4) 0.051(3) 0.050(3) -0.003(3) 0.016(3) 0.008(2)
C4 0.058(3) 0.061(3) 0.062(4) -0.004(3) 0.013(3) -0.001(3)
C5 0.055(3) 0.050(3) 0.042(3) -0.003(2) 0.002(2) 0.007(2)
C6 0.060(3) 0.034(3) 0.042(3) -0.005(2) 0.005(3) -0.002(2)
N1 0.063(3) 0.036(2) 0.036(2) 0.0008(18) 0.0012(19) 0.0059(18)
B 0.057(4) 0.037(3) 0.035(3) 0.004(3) 0.001(3) 0.003(2)
O1 0.055(2) 0.066(2) 0.051(2) -0.008(2) -0.0047(19) 0.020(2)
O2 0.051(2) 0.071(2) 0.0377(19) 0.0027(19) -0.0007(16) 0.0186(18)
C7 0.063(3) 0.056(3) 0.039(3) -0.010(3) 0.000(3) 0.015(3)
C71 0.086(5) 0.112(6) 0.043(3) -0.021(4) -0.012(4) 0.027(4)
C72 0.074(4) 0.062(4) 0.093(6) 0.006(3) 0.007(4) 0.015(4)
C8 0.057(3) 0.060(3) 0.040(3) 0.012(3) 0.008(3) 0.010(2)
C81 0.055(4) 0.114(6) 0.075(5) -0.016(4) -0.005(3) 0.045(5)
C82 0.146(8) 0.100(6) 0.056(4) 0.047(7) 0.031(5) 0.022(4)
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N1 C2 C3 125.3(5) ?
N1 C2 Br1 115.8(4) ?
C3 C2 Br1 118.9(4) ?
C4 C3 C2 118.2(5) ?
C4 C3 H3 120.9 ?
C2 C3 H3 120.9 ?
C3 C4 C5 118.4(6) ?
C3 C4 H4 120.8 ?
C5 C4 H4 120.8 ?
C6 C5 C4 119.7(6) ?
C6 C5 H5 120.2 ?
C4 C5 H5 120.2 ?
N1 C6 C5 122.0(5) ?
N1 C6 B 117.4(5) ?
C5 C6 B 120.5(5) ?
C2 N1 C6 116.4(5) ?
O2 B O1 114.1(5) yes
O2 B C6 126.7(5) yes
O1 B C6 119.2(5) yes
B O1 C7 106.1(4) ?
B O2 C8 106.7(4) ?
O1 C7 C71 108.8(5) ?
O1 C7 C72 106.7(5) ?
C71 C7 C72 109.3(6) ?
O1 C7 C8 102.8(4) ?
C71 C7 C8 115.3(5) ?
C72 C7 C8 113.3(5) ?
C7 C71 H71A 109.5 ?
C7 C71 H71B 109.5 ?
H71A C71 H71B 109.5 ?
C7 C71 H71C 109.5 ?
H71A C71 H71C 109.5 ?
H71B C71 H71C 109.5 ?
C7 C72 H72A 109.5 ?
C7 C72 H72B 109.5 ?
H72A C72 H72B 109.5 ?
C7 C72 H72C 109.5 ?
H72A C72 H72C 109.5 ?
H72B C72 H72C 109.5 ?
O2 C8 C82 105.6(5) ?
O2 C8 C81 107.5(5) ?
C82 C8 C81 111.5(7) ?
O2 C8 C7 102.2(4) ?
C82 C8 C7 114.2(6) ?
C81 C8 C7 114.8(5) ?
C8 C81 H81A 109.5 ?
C8 C81 H81B 109.5 ?
H81A C81 H81B 109.5 ?
C8 C81 H81C 109.5 ?
H81A C81 H81C 109.5 ?
H81B C81 H81C 109.5 ?
C8 C82 H82A 109.5 ?
C8 C82 H82B 109.5 ?
H82A C82 H82B 109.5 ?
C8 C82 H82C 109.5 ?
H82A C82 H82C 109.5 ?
H82B C82 H82C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.913(6) ?
C2 N1 . 1.324(7) ?
C2 C3 . 1.375(9) ?
C3 C4 . 1.356(9) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.396(8) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.373(8) ?
C5 H5 . 0.9300 ?
C6 N1 . 1.351(7) ?
C6 B . 1.578(8) yes
B O2 . 1.328(7) yes
B O1 . 1.383(7) yes
O1 C7 . 1.451(6) yes
O2 C8 . 1.483(6) yes
C7 C71 . 1.514(8) ?
C7 C72 . 1.518(9) ?
C7 C8 . 1.532(9) yes
C71 H71A . 0.9600 ?
C71 H71B . 0.9600 ?
C71 H71C . 0.9600 ?
C72 H72A . 0.9600 ?
C72 H72B . 0.9600 ?
C72 H72C . 0.9600 ?
C8 C82 . 1.510(9) ?
C8 C81 . 1.523(10) ?
C81 H81A . 0.9600 ?
C81 H81B . 0.9600 ?
C81 H81C . 0.9600 ?
C82 H82A . 0.9600 ?
C82 H82B . 0.9600 ?
C82 H82C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16498376
