#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/20/7122095.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_7122095
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 I N2, Cl O4'
_chemical_formula_sum            'C16 H22 Cl I N2 O4'
_chemical_formula_weight         468.72
_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                 100.803(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.1018(8)
_cell_length_b                   8.5668(2)
_cell_length_c                   15.9883(5)
_cell_measurement_reflns_used    4166
_cell_measurement_temperature    300
_cell_measurement_theta_max      75
_cell_measurement_theta_min      5
_cell_volume                     3915.39(19)
_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    'Refined from known structure'
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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  0.033
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11165
_diffrn_reflns_theta_full        73.879
_diffrn_reflns_theta_max         76.164
_diffrn_reflns_theta_min         5.391
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    14.293
_exptl_absorpt_correction_T_max  0.737
_exptl_absorpt_correction_T_min  0.139
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
; 
 Gaussian Integration (Busing and Levy, 1957) 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1872.000
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.59
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4027
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.0002712
_refine_ls_shift/su_mean         0.0000244
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 2.07P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1018
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1016
_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                3283
_reflns_number_total             4035
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0441
_oxford_refine_ls_scale          1.847(11)
_oxford_reflns_number_all        4028
_oxford_structure_analysis_title 099lcm18
_cod_data_source_file            c8cc05430d2.cif
_cod_data_source_block           IColl2ClO4-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               7122095
_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
I1 I 0.7500 0.2500 0.5000 0.0769 1.0000 Uani S . . . .
N11 N 0.74648(12) 0.0058(4) 0.4408(2) 0.0718 1.0000 Uani . . . . .
C12 C 0.78544(15) -0.0812(6) 0.4458(3) 0.0746 1.0000 Uani . . . . .
C13 C 0.78405(17) -0.2199(6) 0.4025(3) 0.0819 1.0000 Uani . . . . .
C14 C 0.74319(19) -0.2717(6) 0.3523(3) 0.0846 1.0000 Uani . . . . .
C15 C 0.70377(18) -0.1819(7) 0.3509(3) 0.0880 1.0000 Uani . . . . .
C16 C 0.70528(17) -0.0449(6) 0.3950(3) 0.0831 1.0000 Uani . . . . .
C17 C 0.83059(17) -0.0222(7) 0.4978(4) 0.0957 1.0000 Uani . . . . .
C18 C 0.7407(3) -0.4201(8) 0.2999(4) 0.1225 1.0000 Uani . . . . .
C19 C 0.6617(2) 0.0519(9) 0.3934(5) 0.1200 1.0000 Uani . . . . .
I2 I 0.5000 0.5000 0.5000 0.0791 1.0000 Uani S . . . .
N21 N 0.53480(12) 0.4698(4) 0.3838(3) 0.0773 1.0000 Uani . . . . .
C22 C 0.54983(16) 0.5960(5) 0.3466(4) 0.0843 1.0000 Uani . . . . .
C23 C 0.57431(17) 0.5774(6) 0.2818(4) 0.0912 1.0000 Uani . . . . .
C24 C 0.58413(16) 0.4314(7) 0.2531(3) 0.0901 1.0000 Uani . . . . .
C25 C 0.56681(18) 0.3061(6) 0.2915(4) 0.0902 1.0000 Uani . . . . .
C26 C 0.54230(16) 0.3242(5) 0.3559(3) 0.0812 1.0000 Uani . . . . .
C27 C 0.5398(3) 0.7551(6) 0.3763(5) 0.1119 1.0000 Uani . . . . .
C28 C 0.6120(2) 0.4108(10) 0.1846(4) 0.1213 1.0000 Uani . . . . .
C29 C 0.5230(3) 0.1871(6) 0.3955(4) 0.1145 1.0000 Uani . . . . .
Cl1 Cl 0.61012(5) 0.06625(17) 0.62601(9) 0.0971 1.0000 Uani D U . . .
O11 O 0.6058(6) 0.2106(8) 0.5885(7) 0.1967 0.625(9) Uani D U P 1 1
O12 O 0.5827(4) 0.0631(12) 0.6891(7) 0.1646 0.625(9) Uani D U P 1 1
O13 O 0.5931(5) -0.0449(11) 0.5647(6) 0.1770 0.625(9) Uani D U P 1 1
O14 O 0.6545(3) 0.031(2) 0.6621(9) 0.2547 0.625(9) Uani D U P 1 1
O111 O 0.5687(5) 0.141(2) 0.6057(13) 0.2254 0.375(9) Uani D U P 1 2
O112 O 0.6168(8) 0.001(2) 0.7051(6) 0.2373 0.375(9) Uani D U P 1 2
O113 O 0.6144(6) -0.0460(19) 0.5660(10) 0.1622 0.375(9) Uani D U P 1 2
O114 O 0.6465(5) 0.1732(19) 0.6270(12) 0.1726 0.375(9) Uani D U P 1 2
H131 H 0.8109 -0.2787 0.4078 0.0981 1.0000 Uiso R . . . .
H151 H 0.6752 -0.2168 0.3196 0.1060 1.0000 Uiso R . . . .
H171 H 0.8538 -0.1013 0.4990 0.1437 1.0000 Uiso R . . . .
H172 H 0.8400 0.0709 0.4721 0.1437 1.0000 Uiso R . . . .
H173 H 0.8262 -0.0002 0.5545 0.1435 1.0000 Uiso R . . . .
H181 H 0.7166 -0.4864 0.3127 0.1840 1.0000 Uiso R . . . .
H182 H 0.7333 -0.3935 0.2406 0.1840 1.0000 Uiso R . . . .
H183 H 0.7701 -0.4738 0.3117 0.1840 1.0000 Uiso R . . . .
H191 H 0.6581 0.0732 0.4500 0.1801 1.0000 Uiso R . . . .
H192 H 0.6640 0.1493 0.3654 0.1797 1.0000 Uiso R . . . .
H193 H 0.6348 -0.0040 0.3650 0.1798 1.0000 Uiso R . . . .
H231 H 0.5836 0.6651 0.2562 0.1089 1.0000 Uiso R . . . .
H251 H 0.5716 0.2053 0.2729 0.1078 1.0000 Uiso R . . . .
H271 H 0.5531 0.8303 0.3450 0.1679 1.0000 Uiso R . . . .
H272 H 0.5530 0.7653 0.4356 0.1677 1.0000 Uiso R . . . .
H273 H 0.5066 0.7701 0.3675 0.1677 1.0000 Uiso R . . . .
H281 H 0.5972 0.3340 0.1456 0.1820 1.0000 Uiso R . . . .
H282 H 0.6428 0.3775 0.2097 0.1819 1.0000 Uiso R . . . .
H283 H 0.6137 0.5093 0.1564 0.1821 1.0000 Uiso R . . . .
H291 H 0.4898 0.1969 0.3906 0.1718 1.0000 Uiso R . . . .
H292 H 0.5380 0.1798 0.4541 0.1718 1.0000 Uiso R . . . .
H293 H 0.5295 0.0961 0.3660 0.1718 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
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 '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'
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'
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'
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 -4 0.0600
0 1 5 0.0800
-1 1 0 0.1000
1 -1 1 0.0600
1 0 0 0.0010
-1 0 0 0.0400
0 0 -1 0.0800
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 I1 N11 179.99 yes
I1 . N11 C12 120.6(3) yes
I1 . N11 C16 118.9(3) yes
C12 . N11 C16 120.4(4) yes
N11 . C12 C13 120.3(4) yes
N11 . C12 C17 119.0(4) yes
C13 . C12 C17 120.7(4) yes
C12 . C13 C14 120.9(4) yes
C12 . C13 H131 118.9 no
C14 . C13 H131 120.2 no
C13 . C14 C15 117.1(5) yes
C13 . C14 C18 122.6(5) yes
C15 . C14 C18 120.4(5) yes
C14 . C15 C16 121.7(5) yes
C14 . C15 H151 119.0 no
C16 . C15 H151 119.3 no
C15 . C16 N11 119.6(4) yes
C15 . C16 C19 121.1(5) yes
N11 . C16 C19 119.3(5) yes
C12 . C17 H171 108.3 no
C12 . C17 H172 109.4 no
H171 . C17 H172 109.9 no
C12 . C17 H173 109.3 no
H171 . C17 H173 109.9 no
H172 . C17 H173 109.9 no
C14 . C18 H181 109.9 no
C14 . C18 H182 109.1 no
H181 . C18 H182 108.4 no
C14 . C18 H183 110.2 no
H181 . C18 H183 109.7 no
H182 . C18 H183 109.5 no
C16 . C19 H191 109.4 no
C16 . C19 H192 110.8 no
H191 . C19 H192 108.0 no
C16 . C19 H193 110.0 no
H191 . C19 H193 108.8 no
H192 . C19 H193 109.8 no
N21 2_666 I2 N21 179.99 yes
I2 . N21 C22 119.8(3) yes
I2 . N21 C26 119.6(3) yes
C22 . N21 C26 120.5(4) yes
N21 . C22 C23 119.9(4) yes
N21 . C22 C27 119.7(5) yes
C23 . C22 C27 120.5(5) yes
C22 . C23 C24 121.7(5) yes
C22 . C23 H231 118.6 no
C24 . C23 H231 119.7 no
C23 . C24 C25 116.2(5) yes
C23 . C24 C28 121.8(6) yes
C25 . C24 C28 122.0(5) yes
C24 . C25 C26 122.3(5) yes
C24 . C25 H251 119.4 no
C26 . C25 H251 118.3 no
C25 . C26 N21 119.4(5) yes
C25 . C26 C29 121.4(4) yes
N21 . C26 C29 119.2(5) yes
C22 . C27 H271 109.4 no
C22 . C27 H272 109.4 no
H271 . C27 H272 109.4 no
C22 . C27 H273 109.2 no
H271 . C27 H273 109.5 no
H272 . C27 H273 109.9 no
C24 . C28 H281 108.8 no
C24 . C28 H282 108.9 no
H281 . C28 H282 110.0 no
C24 . C28 H283 108.9 no
H281 . C28 H283 110.7 no
H282 . C28 H283 109.4 no
C26 . C29 H291 110.5 no
C26 . C29 H292 109.0 no
H291 . C29 H292 110.7 no
C26 . C29 H293 108.1 no
H291 . C29 H293 108.9 no
H292 . C29 H293 109.6 no
O11 . Cl1 O12 108.4(5) yes
O11 . Cl1 O13 108.6(6) yes
O12 . Cl1 O13 108.6(6) yes
O11 . Cl1 O14 113.0(6) yes
O12 . Cl1 O14 108.6(6) yes
O13 . Cl1 O14 109.6(6) yes
O111 . Cl1 O112 112.7(8) yes
O111 . Cl1 O113 110.9(7) yes
O112 . Cl1 O113 110.1(7) yes
O111 . Cl1 O114 109.2(8) yes
O112 . Cl1 O114 106.3(7) yes
O113 . Cl1 O114 107.4(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
I1 N11 4_656 2.291(4) yes
I1 N11 . 2.291(4) yes
N11 C12 . 1.347(5) yes
N11 C16 . 1.354(6) yes
C12 C13 . 1.372(7) yes
C12 C17 . 1.504(7) yes
C13 C14 . 1.378(7) yes
C13 H131 . 0.920 no
C14 C15 . 1.378(7) yes
C14 C18 . 1.517(7) yes
C15 C16 . 1.366(7) yes
C15 H151 . 0.935 no
C16 C19 . 1.511(7) yes
C17 H171 . 0.955 no
C17 H172 . 0.960 no
C17 H173 . 0.959 no
C18 H181 . 0.955 no
C18 H182 . 0.959 no
C18 H183 . 0.959 no
C19 H191 . 0.949 no
C19 H192 . 0.956 no
C19 H193 . 0.956 no
I2 N21 2_666 2.291(4) yes
I2 N21 . 2.291(4) yes
N21 C22 . 1.346(6) yes
N21 C26 . 1.356(5) yes
C22 C23 . 1.373(8) yes
C22 C27 . 1.490(6) yes
C23 C24 . 1.381(7) yes
C23 H231 . 0.920 no
C24 C25 . 1.378(8) yes
C24 C28 . 1.489(8) yes
C25 C26 . 1.367(8) yes
C25 H251 . 0.933 no
C26 C29 . 1.493(8) yes
C27 H271 . 0.942 no
C27 H272 . 0.958 no
C27 H273 . 0.957 no
C28 H281 . 0.953 no
C28 H282 . 0.955 no
C28 H283 . 0.962 no
C29 H291 . 0.957 no
C29 H292 . 0.959 no
C29 H293 . 0.948 no
Cl1 O11 . 1.369(6) yes
Cl1 O12 . 1.399(6) yes
Cl1 O13 . 1.390(6) yes
Cl1 O14 . 1.345(6) yes
Cl1 O111 . 1.350(7) yes
Cl1 O112 . 1.362(7) yes
Cl1 O113 . 1.380(7) yes
Cl1 O114 . 1.397(7) 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
C18 H183 O14 4_646 164 0.96 2.21 3.144(8) yes
C23 H231 O12 6_564 161 0.92 2.56 3.446(8) yes
C25 H251 O112 6_554 153 0.93 2.56 3.422(8) yes
C27 H273 O111 2_666 159 0.96 2.43 3.344(8) yes
C29 H292 O111 . 173 0.96 2.44 3.398(8) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188982
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
-26 6 8 x
8 0 2 x
6 0 2 x
4 0 2 x
-4 0 2 x
-1 1 4 x
3 1 2 x
