#------------------------------------------------------------------------------
#$Date: 2022-05-04 11:36:19 +0300 (Wed, 04 May 2022) $
#$Revision: 274880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105137.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_8105137
loop_
_publ_author_name
'Zhang, Ji-Run'
'Deng, Hao'
'Liu, Tong'
_publ_section_title
;
 The crystal structure of
 3-bromo-6-methoxy-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine,
 C13H19BBrNO3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              451
_journal_page_last               452
_journal_paper_doi               10.1515/ncrs-2019-0756
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C13 H19 B Br N O3'
_chemical_formula_sum            'C13 H19 B Br N O3'
_chemical_formula_weight         328.01
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                106.938(2)
_cell_angle_beta                 105.657(2)
_cell_angle_gamma                106.628(2)
_cell_formula_units_Z            2
_cell_length_a                   6.5459(3)
_cell_length_b                   11.2565(5)
_cell_length_c                   11.8529(5)
_cell_measurement_reflns_used    5055
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.424
_cell_measurement_theta_min      3.300
_cell_volume                     738.71(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9092
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         3.300
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.785
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1029 before and 0.0426 after correction. The Ratio of minimum to maximum transmission is 0.6532. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0286
_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)+(0.0245P)²+0.2508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0641
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2931
_reflns_number_total             3356
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0756_suppl.cif
_cod_data_source_block           0902jt60_0m
_cod_database_code               8105137
_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_max   0.808
_shelx_estimated_absorpt_t_min   0.664
_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:
 C4(H4)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C7(H7A,H7B,H7C), C1(H1A,H1B,H1C),
 C13(H13A,H13B,H13C), C11(H11A,H11B,H11C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.6832(4) 0.2552(2) 0.46623(19) 0.0235(4) Uani 1 1 d . . . . .
Br1 Br 0.48104(4) 0.29330(2) 0.01250(2) 0.03610(8) Uani 1 1 d . . . . .
C1 C 0.7962(4) 0.1217(2) -0.02188(18) 0.0359(5) Uani 1 1 d . . . . .
H1A H 0.888080 0.206264 -0.023754 0.054 Uiso 1 1 calc GR . . . .
H1B H 0.648763 0.076348 -0.095781 0.054 Uiso 1 1 calc GR . . . .
H1C H 0.880997 0.062582 -0.024993 0.054 Uiso 1 1 calc GR . . . .
C2 C 0.7514(3) 0.15211(19) 0.09884(17) 0.0259(4) Uani 1 1 d . . . . .
C3 C 0.6202(3) 0.22479(19) 0.12749(17) 0.0261(4) Uani 1 1 d . . . . .
C4 C 0.5935(3) 0.25312(19) 0.24355(17) 0.0262(4) Uani 1 1 d . . . . .
H4 H 0.503053 0.302869 0.262392 0.031 Uiso 1 1 calc R . . . .
C5 C 0.6984(3) 0.20908(18) 0.33224(16) 0.0237(4) Uani 1 1 d . . . . .
C6 C 0.8221(3) 0.13227(18) 0.29263(16) 0.0236(4) Uani 1 1 d . . . . .
C7 C 1.0333(4) -0.0014(2) 0.33081(19) 0.0318(4) Uani 1 1 d . . . . .
H7A H 0.929361 -0.074235 0.247196 0.048 Uiso 1 1 calc GR . . . .
H7B H 1.078136 -0.040533 0.392499 0.048 Uiso 1 1 calc GR . . . .
H7C H 1.171592 0.053372 0.323600 0.048 Uiso 1 1 calc GR . . . .
C9 C 0.7191(3) 0.28905(19) 0.67033(16) 0.0245(4) Uani 1 1 d . . . . .
C10 C 0.6096(3) 0.38222(19) 0.62608(16) 0.0253(4) Uani 1 1 d . . . . .
C11 C 0.7802(4) 0.5269(2) 0.6734(2) 0.0354(5) Uani 1 1 d . . . . .
H11A H 0.918540 0.526928 0.656276 0.053 Uiso 1 1 calc GR . . . .
H11B H 0.823345 0.572655 0.765534 0.053 Uiso 1 1 calc GR . . . .
H11C H 0.708844 0.574643 0.628886 0.053 Uiso 1 1 calc GR . . . .
C12 C 0.3928(4) 0.3792(2) 0.65081(19) 0.0345(5) Uani 1 1 d . . . . .
H12A H 0.335480 0.439467 0.619151 0.052 Uiso 1 1 calc GR . . . .
H12B H 0.428760 0.409383 0.742832 0.052 Uiso 1 1 calc GR . . . .
H12C H 0.274290 0.286730 0.606405 0.052 Uiso 1 1 calc GR . . . .
C13 C 0.9224(4) 0.3610(2) 0.79788(18) 0.0348(5) Uani 1 1 d . . . . .
H13A H 0.985013 0.296413 0.816562 0.052 Uiso 1 1 calc GR . . . .
H13B H 0.871152 0.399121 0.865187 0.052 Uiso 1 1 calc GR . . . .
H13C H 1.042345 0.433840 0.794377 0.052 Uiso 1 1 calc GR . . . .
C14 C 0.5439(4) 0.1645(2) 0.66675(18) 0.0321(4) Uani 1 1 d . . . . .
H14A H 0.414104 0.119498 0.583598 0.048 Uiso 1 1 calc GR . . . .
H14B H 0.487182 0.191329 0.734652 0.048 Uiso 1 1 calc GR . . . .
H14C H 0.617113 0.102204 0.679675 0.048 Uiso 1 1 calc GR . . . .
N1 N 0.8487(3) 0.10511(16) 0.18210(14) 0.0262(3) Uani 1 1 d . . . . .
O1 O 0.8042(2) 0.24100(13) 0.57073(11) 0.0259(3) Uani 1 1 d . . . . .
O2 O 0.5450(2) 0.32268(13) 0.48730(11) 0.0271(3) Uani 1 1 d . . . . .
O3 O 0.9169(2) 0.08245(13) 0.37358(12) 0.0276(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'
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'
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
B1 O1 C9 106.91(14) . .
B1 O2 C10 106.81(13) . .
C6 O3 C7 116.85(14) . .
C6 N1 C2 119.23(16) . .
C4 C3 Br1 118.37(14) . .
C2 C3 Br1 121.26(13) . .
C2 C3 C4 120.34(16) . .
C3 C4 H4 119.8 . .
C5 C4 C3 120.37(17) . .
C5 C4 H4 119.8 . .
O3 C6 C5 116.72(15) . .
N1 C6 O3 118.41(16) . .
N1 C6 C5 124.87(16) . .
N1 C2 C3 120.08(16) . .
N1 C2 C1 116.17(16) . .
C3 C2 C1 123.75(17) . .
C4 C5 C6 115.04(16) . .
C4 C5 B1 118.40(16) . .
C6 C5 B1 126.44(16) . .
O1 C9 C10 102.54(13) . .
O1 C9 C14 106.51(14) . .
O1 C9 C13 108.12(15) . .
C14 C9 C10 113.41(15) . .
C13 C9 C10 114.70(16) . .
C13 C9 C14 110.76(16) . .
O2 C10 C9 101.95(13) . .
O2 C10 C12 108.08(15) . .
O2 C10 C11 106.30(15) . .
C12 C10 C9 115.17(16) . .
C12 C10 C11 110.61(16) . .
C11 C10 C9 113.82(16) . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C9 C14 H14A 109.5 . .
C9 C14 H14B 109.5 . .
C9 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O3 C7 H7A 109.5 . .
O3 C7 H7B 109.5 . .
O3 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C9 C13 H13A 109.5 . .
C9 C13 H13B 109.5 . .
C9 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
O1 B1 O2 114.06(16) . .
O1 B1 C5 126.56(17) . .
O2 B1 C5 119.30(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.9042(17) .
O1 C9 1.467(2) .
O1 B1 1.359(2) .
O2 C10 1.468(2) .
O2 B1 1.365(2) .
O3 C6 1.346(2) .
O3 C7 1.439(2) .
N1 C6 1.327(2) .
N1 C2 1.348(2) .
C3 C4 1.389(2) .
C3 C2 1.386(3) .
C4 H4 0.9500 .
C4 C5 1.390(2) .
C6 C5 1.411(2) .
C2 C1 1.500(2) .
C5 B1 1.561(3) .
C9 C10 1.561(3) .
C9 C14 1.517(3) .
C9 C13 1.515(3) .
C10 C12 1.517(3) .
C10 C11 1.518(3) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
