#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/21/7122106.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_7122106
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, Cl O4'
_chemical_formula_sum            'C16 H22 Br Cl N2 O4'
_chemical_formula_weight         421.72
_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                 99.565(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.8059(14)
_cell_length_b                   8.5296(3)
_cell_length_c                   15.8383(7)
_cell_measurement_reflns_used    7301
_cell_measurement_temperature    300
_cell_measurement_theta_max      75
_cell_measurement_theta_min      5
_cell_volume                     3837.4(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.987
_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     1.54180
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20990
_diffrn_reflns_theta_full        75.249
_diffrn_reflns_theta_max         76.785
_diffrn_reflns_theta_min         3.111
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.389
_exptl_absorpt_correction_T_max  0.70
_exptl_absorpt_correction_T_min  0.40
_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    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.54
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3981
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.0003745
_refine_ls_shift/su_mean         0.0000223
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.08P)² + 3.16P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1369
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1367
_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                3385
_reflns_number_total             3997
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   5.62
_oxford_diffrn_Wilson_scale      0.34
_oxford_refine_ls_r_factor_ref   0.0516
_oxford_refine_ls_scale          1.826(16)
_oxford_reflns_number_all        3982
_oxford_structure_analysis_title 067YK14-300K
_cod_data_source_file            c8cc05430d2.cif
_cod_data_source_block           BrColl2ClO4-II-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               7122106
_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 0.0704 1.0000 Uani S . . . .
N11 N 0.74665(10) 0.0241(3) 0.44328(17) 0.0693 1.0000 Uani . . . . .
C12 C 0.78563(12) -0.0654(4) 0.4481(2) 0.0717 1.0000 Uani . . . . .
C13 C 0.78357(14) -0.2066(5) 0.4053(2) 0.0794 1.0000 Uani . . . . .
C14 C 0.74273(15) -0.2574(4) 0.3570(2) 0.0816 1.0000 Uani . . . . .
C15 C 0.70309(15) -0.1655(5) 0.3547(2) 0.0844 1.0000 Uani . . . . .
C16 C 0.70495(13) -0.0250(5) 0.3982(2) 0.0784 1.0000 Uani . . . . .
C17 C 0.83030(14) -0.0063(5) 0.5000(3) 0.0928 1.0000 Uani . . . . .
C18 C 0.7406(2) -0.4089(6) 0.3067(4) 0.1217 1.0000 Uani . . . . .
C19 C 0.66232(15) 0.0771(7) 0.3960(3) 0.1093 1.0000 Uani . . . . .
Br2 Br 0.5000 0.5000 0.5000 0.0731 1.0000 Uani S . . . .
N21 N 0.53308(10) 0.4737(3) 0.3911(2) 0.0732 1.0000 Uani . . . . .
C22 C 0.54837(13) 0.6011(4) 0.3536(3) 0.0792 1.0000 Uani . . . . .
C23 C 0.57214(14) 0.5846(5) 0.2865(3) 0.0871 1.0000 Uani . . . . .
C24 C 0.58105(13) 0.4375(5) 0.2554(3) 0.0855 1.0000 Uani . . . . .
C25 C 0.56426(14) 0.3103(4) 0.2942(3) 0.0848 1.0000 Uani . . . . .
C26 C 0.54011(13) 0.3283(4) 0.3613(2) 0.0775 1.0000 Uani . . . . .
C27 C 0.5389(2) 0.7607(4) 0.3870(4) 0.1133 1.0000 Uani . . . . .
C28 C 0.60817(19) 0.4190(7) 0.1831(3) 0.1139 1.0000 Uani . . . . .
C29 C 0.5211(2) 0.1903(4) 0.4021(3) 0.1104 1.0000 Uani . . . . .
Cl1 Cl 0.61146(4) 0.06374(14) 0.62998(7) 0.0965 1.0000 Uani D U . . .
O11 O 0.6079(6) 0.2087(8) 0.5972(8) 0.2196 0.560(11) Uani D U P 1 1
O12 O 0.5841(4) 0.0540(11) 0.6943(6) 0.1578 0.560(11) Uani D U P 1 1
O13 O 0.5945(5) -0.0462(10) 0.5672(5) 0.1721 0.560(11) Uani D U P 1 1
O14 O 0.6557(3) 0.020(2) 0.6652(8) 0.2832 0.560(11) Uani D U P 1 1
O111 O 0.5747(4) 0.1613(17) 0.5975(10) 0.2141 0.440(11) Uani D U P 1 2
O112 O 0.6082(7) 0.0138(17) 0.7091(5) 0.2438 0.440(11) Uani D U P 1 2
O113 O 0.6162(5) -0.0534(14) 0.5743(8) 0.1763 0.440(11) Uani D U P 1 2
O114 O 0.6518(4) 0.1607(13) 0.6379(8) 0.1681 0.440(11) Uani D U P 1 2
H131 H 0.8102 -0.2663 0.4093 0.0950 1.0000 Uiso R . . . .
H151 H 0.6743 -0.1981 0.3222 0.1010 1.0000 Uiso R . . . .
H171 H 0.8550 -0.0797 0.4972 0.1388 1.0000 Uiso R . . . .
H172 H 0.8381 0.0918 0.4758 0.1392 1.0000 Uiso R . . . .
H173 H 0.8274 0.0098 0.5588 0.1384 1.0000 Uiso R . . . .
H181 H 0.7102 -0.4555 0.3058 0.1831 1.0000 Uiso R . . . .
H182 H 0.7449 -0.3829 0.2496 0.1828 1.0000 Uiso R . . . .
H183 H 0.7654 -0.4808 0.3321 0.1828 1.0000 Uiso R . . . .
H191 H 0.6611 0.1090 0.4536 0.1639 1.0000 Uiso R . . . .
H192 H 0.6653 0.1692 0.3630 0.1639 1.0000 Uiso R . . . .
H193 H 0.6348 0.0208 0.3725 0.1639 1.0000 Uiso R . . . .
H231 H 0.5819 0.6744 0.2626 0.1046 1.0000 Uiso R . . . .
H251 H 0.5690 0.2091 0.2746 0.1014 1.0000 Uiso R . . . .
H271 H 0.5529 0.8404 0.3567 0.1698 1.0000 Uiso R . . . .
H272 H 0.5527 0.7686 0.4464 0.1695 1.0000 Uiso R . . . .
H273 H 0.5059 0.7774 0.3797 0.1695 1.0000 Uiso R . . . .
H281 H 0.5897 0.3579 0.1398 0.1710 1.0000 Uiso R . . . .
H282 H 0.6362 0.3646 0.2057 0.1704 1.0000 Uiso R . . . .
H283 H 0.6149 0.5225 0.1632 0.1708 1.0000 Uiso R . . . .
H291 H 0.4878 0.2012 0.4043 0.1659 1.0000 Uiso R . . . .
H292 H 0.5390 0.1790 0.4581 0.1659 1.0000 Uiso R . . . .
H293 H 0.5262 0.0985 0.3703 0.1653 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'
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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 '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'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'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 120.7(2) yes
Br1 . N11 C16 118.5(2) yes
C12 . N11 C16 120.7(3) yes
N11 . C12 C13 119.9(3) yes
N11 . C12 C17 118.2(3) yes
C13 . C12 C17 121.8(3) yes
C12 . C13 C14 121.1(3) yes
C12 . C13 H131 119.2 no
C14 . C13 H131 119.8 no
C13 . C14 C15 117.9(4) yes
C13 . C14 C18 121.5(4) yes
C15 . C14 C18 120.7(4) yes
C14 . C15 C16 121.1(4) yes
C14 . C15 H151 119.8 no
C16 . C15 H151 119.1 no
C15 . C16 N11 119.3(3) yes
C15 . C16 C19 121.9(4) yes
N11 . C16 C19 118.8(4) yes
C12 . C17 H171 109.5 no
C12 . C17 H172 108.1 no
H171 . C17 H172 109.1 no
C12 . C17 H173 112.2 no
H171 . C17 H173 108.9 no
H172 . C17 H173 109.0 no
C14 . C18 H181 108.5 no
C14 . C18 H182 107.4 no
H181 . C18 H182 110.0 no
C14 . C18 H183 110.9 no
H181 . C18 H183 110.4 no
H182 . C18 H183 109.6 no
C16 . C19 H191 107.5 no
C16 . C19 H192 110.1 no
H191 . C19 H192 107.9 no
C16 . C19 H193 110.1 no
H191 . C19 H193 110.9 no
H192 . C19 H193 110.3 no
N21 2_666 Br2 N21 179.99 yes
Br2 . N21 C22 119.9(2) yes
Br2 . N21 C26 119.6(3) yes
C22 . N21 C26 120.5(3) yes
N21 . C22 C23 120.2(3) yes
N21 . C22 C27 118.9(4) yes
C23 . C22 C27 120.8(4) yes
C22 . C23 C24 121.1(4) yes
C22 . C23 H231 117.5 no
C24 . C23 H231 121.4 no
C23 . C24 C25 117.1(4) yes
C23 . C24 C28 121.2(4) yes
C25 . C24 C28 121.7(4) yes
C24 . C25 C26 121.3(3) yes
C24 . C25 H251 120.0 no
C26 . C25 H251 118.7 no
C25 . C26 N21 119.7(4) yes
C25 . C26 C29 121.2(3) yes
N21 . C26 C29 119.1(4) yes
C22 . C27 H271 110.5 no
C22 . C27 H272 109.8 no
H271 . C27 H272 107.4 no
C22 . C27 H273 109.3 no
H271 . C27 H273 109.2 no
H272 . C27 H273 110.7 no
C24 . C28 H281 108.0 no
C24 . C28 H282 106.4 no
H281 . C28 H282 110.1 no
C24 . C28 H283 108.1 no
H281 . C28 H283 112.6 no
H282 . C28 H283 111.5 no
C26 . C29 H291 112.1 no
C26 . C29 H292 107.6 no
H291 . C29 H292 111.2 no
C26 . C29 H293 108.6 no
H291 . C29 H293 109.6 no
H292 . C29 H293 107.5 no
O11 . Cl1 O12 108.8(5) yes
O11 . Cl1 O13 110.5(6) yes
O12 . Cl1 O13 107.9(6) yes
O11 . Cl1 O14 115.0(7) yes
O12 . Cl1 O14 106.9(6) yes
O13 . Cl1 O14 107.6(6) yes
O111 . Cl1 O112 111.8(7) yes
O111 . Cl1 O113 110.9(6) yes
O112 . Cl1 O113 113.9(7) yes
O111 . Cl1 O114 104.4(6) yes
O112 . Cl1 O114 106.7(6) yes
O113 . Cl1 O114 108.6(7) 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 2.121(3) yes
Br1 N11 . 2.121(3) yes
N11 C12 . 1.350(4) yes
N11 C16 . 1.358(5) yes
C12 C13 . 1.378(5) yes
C12 C17 . 1.494(6) yes
C13 C14 . 1.363(6) yes
C13 H131 . 0.913 no
C14 C15 . 1.380(5) yes
C14 C18 . 1.514(6) yes
C15 C16 . 1.379(5) yes
C15 H151 . 0.943 no
C16 C19 . 1.501(5) yes
C17 H171 . 0.954 no
C17 H172 . 0.963 no
C17 H173 . 0.958 no
C18 H181 . 0.961 no
C18 H182 . 0.958 no
C18 H183 . 0.976 no
C19 H191 . 0.958 no
C19 H192 . 0.955 no
C19 H193 . 0.949 no
Br2 N21 2_666 2.117(3) yes
Br2 N21 . 2.117(3) yes
N21 C22 . 1.347(5) yes
N21 C26 . 1.354(4) yes
C22 C23 . 1.363(6) yes
C22 C27 . 1.502(5) yes
C23 C24 . 1.387(6) yes
C23 H231 . 0.919 no
C24 C25 . 1.373(6) yes
C24 C28 . 1.498(6) yes
C25 C26 . 1.373(6) yes
C25 H251 . 0.934 no
C26 C29 . 1.490(6) yes
C27 H271 . 0.959 no
C27 H272 . 0.961 no
C27 H273 . 0.948 no
C28 H281 . 0.949 no
C28 H282 . 0.949 no
C28 H283 . 0.968 no
C29 H291 . 0.970 no
C29 H292 . 0.954 no
C29 H293 . 0.956 no
Cl1 O11 . 1.338(6) yes
Cl1 O12 . 1.391(6) yes
Cl1 O13 . 1.395(6) yes
Cl1 O14 . 1.356(6) yes
Cl1 O111 . 1.377(7) yes
Cl1 O112 . 1.342(7) yes
Cl1 O113 . 1.355(6) yes
Cl1 O114 . 1.415(6) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C13 H131 O113 4_646 177 0.91 2.60 3.511(6) yes
C18 H183 O14 4_646 139 0.98 2.29 3.094(6) yes
C19 H193 O112 6_554 123 0.95 2.59 3.202(6) yes
C23 H231 O12 6_564 163 0.92 2.56 3.452(6) yes
C25 H251 O112 6_554 159 0.93 2.52 3.409(6) yes
C27 H273 O111 2_666 164 0.95 2.46 3.387(6) yes
C28 H283 O11 6_564 164 0.97 2.51 3.454(6) yes
C29 H292 O111 . 174 0.95 2.28 3.230(6) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188985
