#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/20/7122097.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_7122097
loop_
_publ_author_name
'Morgan, Lewis C. F.'
'Kim, Yejin'
'Blandy, Jack N.'
'Murray, Claire A.'
'Christensen, Kirsten E.'
'Thompson, Amber L.'
_publ_section_title
;
 Unexpected behaviour in derivatives of Barluenga's reagent,
 Hal(Coll)₂X (Coll = 2,4,6-trimethyl pyridine, collidine; Hal =
 I, Br; X = PF₆, ClO₄ & BF₄).
;
_journal_issue                   70
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9849
_journal_page_last               9852
_journal_paper_doi               10.1039/c8cc05430d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C16 H22 Br N2, B F4'
_chemical_formula_sum            'C16 H22 B Br F4 N2'
_chemical_formula_weight         409.07
_chemical_melting_point          ?
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-06-05
_audit_creation_method           CRYSTALS_ver_14.61_build_6720
_audit_update_record
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.7977(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.0149(3)
_cell_length_b                   8.50144(7)
_cell_length_c                   15.54176(17)
_cell_measurement_reflns_used    22418
_cell_measurement_temperature    300
_cell_measurement_theta_max      76
_cell_measurement_theta_min      5
_cell_volume                     3765.79(7)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            41023
_diffrn_reflns_theta_full        74.863
_diffrn_reflns_theta_max         76.390
_diffrn_reflns_theta_min         3.101
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.321
_exptl_absorpt_correction_T_max  0.38
_exptl_absorpt_correction_T_min  0.27
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1664.000
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.32
_refine_ls_extinction_coef       95(8)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3920
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.0003091
_refine_ls_shift/su_mean         0.0000245
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 1.50P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1023
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1023
_reflns_limit_h_max              35
_reflns_limit_h_min              -36
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3575
_reflns_number_total             3935
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   5.44
_oxford_diffrn_Wilson_scale      0.19
_oxford_refine_ls_r_factor_ref   0.0367
_oxford_refine_ls_scale          2.64(3)
_oxford_reflns_number_all        3920
_oxford_structure_analysis_title 099KEC14-300K
_cod_data_source_file            c8cc05430d2.cif
_cod_data_source_block           BrColl2BF4-300K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7122093--7122107.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7122097
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
x+1/2,-y+1/2,z+1/2
-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.7500 0.2500 0.5000 0.0686 1.0000 Uani S . . . .
N11 N 0.74710(6) 0.0212(2) 0.44437(11) 0.0670 1.0000 Uani . . . . .
C12 C 0.78667(8) -0.0638(3) 0.44893(14) 0.0700 1.0000 Uani . . . . .
C13 C 0.78509(9) -0.2059(3) 0.40556(17) 0.0772 1.0000 Uani . . . . .
C14 C 0.74408(10) -0.2615(3) 0.35668(17) 0.0793 1.0000 Uani . . . . .
C15 C 0.70434(9) -0.1723(3) 0.35489(16) 0.0818 1.0000 Uani . . . . .
C16 C 0.70562(8) -0.0323(3) 0.39984(15) 0.0746 1.0000 Uani . . . . .
C17 C 0.83157(9) 0.0005(3) 0.5012(2) 0.0928 1.0000 Uani . . . . .
C18 C 0.74226(13) -0.4139(4) 0.3058(2) 0.1125 1.0000 Uani . . . . .
C19 C 0.66233(10) 0.0654(4) 0.3987(2) 0.1055 1.0000 Uani . . . . .
Br2 Br 0.5000 0.5000 0.5000 0.0806 1.0000 Uani S . . . .
N21 N 0.53353(8) 0.4764(2) 0.39050(16) 0.0813 1.0000 Uani . . . . .
C22 C 0.54780(9) 0.6064(3) 0.3519(2) 0.0869 1.0000 Uani . . . . .
C23 C 0.57181(10) 0.5912(4) 0.2848(2) 0.0954 1.0000 Uani . . . . .
C24 C 0.58180(10) 0.4444(4) 0.2542(2) 0.0963 1.0000 Uani . . . . .
C25 C 0.56576(11) 0.3147(4) 0.2938(2) 0.0981 1.0000 Uani . . . . .
C26 C 0.54159(10) 0.3316(3) 0.3613(2) 0.0891 1.0000 Uani . . . . .
C27 C 0.53639(16) 0.7647(3) 0.3844(3) 0.1163 1.0000 Uani . . . . .
C28 C 0.60905(14) 0.4266(6) 0.1824(3) 0.1270 1.0000 Uani . . . . .
C29 C 0.52371(17) 0.1923(3) 0.4025(3) 0.1250 1.0000 Uani . . . . .
B1 B 0.61102(14) 0.0502(5) 0.6339(2) 0.1025 1.0000 Uani D U . . .
F11 F 0.6176(4) 0.1877(6) 0.6081(6) 0.2221 0.580(7) Uani D U P 1 1
F12 F 0.5823(2) 0.0507(7) 0.6917(4) 0.1641 0.580(7) Uani D U P 1 1
F13 F 0.5929(3) -0.0451(8) 0.5691(3) 0.1958 0.580(7) Uani D U P 1 1
F14 F 0.64851(18) -0.0262(10) 0.6756(5) 0.2056 0.580(7) Uani D U P 1 1
F111 F 0.5778(3) 0.1490(13) 0.5983(7) 0.2588 0.420(7) Uani D U P 1 2
F112 F 0.6096(6) 0.0116(14) 0.7103(4) 0.2909 0.420(7) Uani D U P 1 2
F113 F 0.6163(4) -0.0595(10) 0.5798(6) 0.1952 0.420(7) Uani D U P 1 2
F114 F 0.6506(3) 0.1435(12) 0.6403(7) 0.2075 0.420(7) Uani D U P 1 2
H131 H 0.8120 -0.2612 0.4075 0.0927 1.0000 Uiso R . . . .
H151 H 0.6755 -0.2073 0.3228 0.0983 1.0000 Uiso R . . . .
H171 H 0.8550 -0.0738 0.5031 0.1391 1.0000 Uiso R . . . .
H172 H 0.8398 0.0942 0.4751 0.1382 1.0000 Uiso R . . . .
H173 H 0.8270 0.0246 0.5593 0.1377 1.0000 Uiso R . . . .
H181 H 0.7164 -0.4741 0.3147 0.1694 1.0000 Uiso R . . . .
H182 H 0.7394 -0.3933 0.2456 0.1693 1.0000 Uiso R . . . .
H183 H 0.7698 -0.4755 0.3249 0.1691 1.0000 Uiso R . . . .
H191 H 0.6600 0.0873 0.4567 0.1576 1.0000 Uiso R . . . .
H192 H 0.6644 0.1646 0.3728 0.1576 1.0000 Uiso R . . . .
H193 H 0.6337 0.0151 0.3716 0.1570 1.0000 Uiso R . . . .
H231 H 0.5803 0.6827 0.2584 0.1128 1.0000 Uiso R . . . .
H251 H 0.5709 0.2148 0.2734 0.1171 1.0000 Uiso R . . . .
H271 H 0.5474 0.8447 0.3530 0.1736 1.0000 Uiso R . . . .
H272 H 0.5499 0.7828 0.4448 0.1731 1.0000 Uiso R . . . .
H273 H 0.5034 0.7781 0.3779 0.1730 1.0000 Uiso R . . . .
H281 H 0.5916 0.3667 0.1355 0.1902 1.0000 Uiso R . . . .
H282 H 0.6375 0.3747 0.2058 0.1893 1.0000 Uiso R . . . .
H283 H 0.6163 0.5263 0.1632 0.1898 1.0000 Uiso R . . . .
H291 H 0.4911 0.2053 0.4023 0.1879 1.0000 Uiso R . . . .
H292 H 0.5414 0.1824 0.4600 0.1875 1.0000 Uiso R . . . .
H293 H 0.5282 0.1028 0.3689 0.1875 1.0000 Uiso R . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N11 4_656 Br1 N11 179.99 yes
Br1 . N11 C12 120.10(16) yes
Br1 . N11 C16 118.75(15) yes
C12 . N11 C16 121.0(2) yes
N11 . C12 C13 119.6(2) yes
N11 . C12 C17 118.5(2) yes
C13 . C12 C17 121.9(2) yes
C12 . C13 C14 121.3(2) yes
C12 . C13 H131 119.2 no
C14 . C13 H131 119.5 no
C13 . C14 C15 117.3(2) yes
C13 . C14 C18 121.8(3) yes
C15 . C14 C18 120.9(3) yes
C14 . C15 C16 121.6(3) yes
C14 . C15 H151 119.7 no
C16 . C15 H151 118.7 no
C15 . C16 N11 119.2(2) yes
C15 . C16 C19 121.9(2) yes
N11 . C16 C19 118.8(2) yes
C12 . C17 H171 109.0 no
C12 . C17 H172 109.7 no
H171 . C17 H172 110.2 no
C12 . C17 H173 109.2 no
H171 . C17 H173 110.3 no
H172 . C17 H173 108.4 no
C14 . C18 H181 109.9 no
C14 . C18 H182 110.4 no
H181 . C18 H182 108.9 no
C14 . C18 H183 111.2 no
H181 . C18 H183 107.5 no
H182 . C18 H183 108.9 no
C16 . C19 H191 108.0 no
C16 . C19 H192 112.3 no
H191 . C19 H192 104.9 no
C16 . C19 H193 114.4 no
H191 . C19 H193 107.4 no
H192 . C19 H193 109.3 no
N21 2_666 Br2 N21 179.99 yes
Br2 . N21 C22 120.06(18) yes
Br2 . N21 C26 119.4(2) yes
C22 . N21 C26 120.5(3) yes
N21 . C22 C23 120.1(2) yes
N21 . C22 C27 118.5(3) yes
C23 . C22 C27 121.3(3) yes
C22 . C23 C24 121.2(3) yes
C22 . C23 H231 118.2 no
C24 . C23 H231 120.6 no
C23 . C24 C25 117.0(3) yes
C23 . C24 C28 121.6(4) yes
C25 . C24 C28 121.4(3) yes
C24 . C25 C26 121.2(3) yes
C24 . C25 H251 119.1 no
C26 . C25 H251 119.6 no
C25 . C26 N21 119.8(3) yes
C25 . C26 C29 121.0(3) yes
N21 . C26 C29 119.1(3) yes
C22 . C27 H271 111.2 no
C22 . C27 H272 113.5 no
H271 . C27 H272 106.3 no
C22 . C27 H273 110.7 no
H271 . C27 H273 107.2 no
H272 . C27 H273 107.7 no
C24 . C28 H281 110.2 no
C24 . C28 H282 107.8 no
H281 . C28 H282 110.2 no
C24 . C28 H283 109.1 no
H281 . C28 H283 111.1 no
H282 . C28 H283 108.3 no
C26 . C29 H291 109.5 no
C26 . C29 H292 107.8 no
H291 . C29 H292 112.1 no
C26 . C29 H293 107.8 no
H291 . C29 H293 109.4 no
H292 . C29 H293 110.1 no
F11 . B1 F12 111.3(5) yes
F11 . B1 F13 112.8(5) yes
F12 . B1 F13 107.7(5) yes
F11 . B1 F14 116.7(6) yes
F12 . B1 F14 103.4(5) yes
F13 . B1 F14 104.2(5) yes
F111 . B1 F112 114.8(7) yes
F111 . B1 F113 110.8(6) yes
F112 . B1 F113 117.7(7) yes
F111 . B1 F114 101.3(6) yes
F112 . B1 F114 105.0(6) yes
F113 . B1 F114 105.3(6) yes
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 N11 4_656 2.1239(18) yes
Br1 N11 . 2.1239(18) yes
N11 C12 . 1.347(3) yes
N11 C16 . 1.350(3) yes
C12 C13 . 1.380(3) yes
C12 C17 . 1.503(4) yes
C13 C14 . 1.371(4) yes
C13 H131 . 0.908 no
C14 C15 . 1.376(4) yes
C14 C18 . 1.513(4) yes
C15 C16 . 1.377(4) yes
C15 H151 . 0.938 no
C16 C19 . 1.503(4) yes
C17 H171 . 0.925 no
C17 H172 . 0.945 no
C17 H173 . 0.959 no
C18 H181 . 0.940 no
C18 H182 . 0.941 no
C18 H183 . 0.955 no
C19 H191 . 0.935 no
C19 H192 . 0.941 no
C19 H193 . 0.959 no
Br2 N21 2_666 2.122(3) yes
Br2 N21 . 2.122(3) yes
N21 C22 . 1.358(4) yes
N21 C26 . 1.348(3) yes
C22 C23 . 1.364(4) yes
C22 C27 . 1.496(4) yes
C23 C24 . 1.385(4) yes
C23 H231 . 0.934 no
C24 C25 . 1.385(5) yes
C24 C28 . 1.491(5) yes
C25 C26 . 1.374(5) yes
C25 H251 . 0.929 no
C26 C29 . 1.486(5) yes
C27 H271 . 0.928 no
C27 H272 . 0.960 no
C27 H273 . 0.949 no
C28 H281 . 0.952 no
C28 H282 . 0.946 no
C28 H283 . 0.935 no
C29 H291 . 0.952 no
C29 H292 . 0.947 no
C29 H293 . 0.946 no
B1 F11 . 1.262(5) yes
B1 F12 . 1.335(5) yes
B1 F13 . 1.323(5) yes
B1 F14 . 1.327(5) yes
B1 F111 . 1.319(6) yes
B1 F112 . 1.239(6) yes
B1 F113 . 1.284(6) yes
B1 F114 . 1.385(6) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188983
