#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/21/7122107.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_7122107
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             2018-06-04
_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                 102.602(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.0825(6)
_cell_length_b                   8.5757(2)
_cell_length_c                   15.4139(3)
_cell_measurement_reflns_used    6392
_cell_measurement_temperature    100
_cell_measurement_theta_max      75
_cell_measurement_theta_min      5
_cell_volume                     3751.66(14)
_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      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_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    0.0447
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12365
_diffrn_reflns_theta_full        74.051
_diffrn_reflns_theta_max         76.341
_diffrn_reflns_theta_min         5.389
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    14.917
_exptl_absorpt_correction_T_max  0.748
_exptl_absorpt_correction_T_min  0.136
_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    1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1871.992
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.041
_refine_diff_density_max         1.21
_refine_diff_density_min         -0.67
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.0002682
_refine_ls_shift/su_mean         0.0000228
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 7.68P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1036
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1035
_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                3455
_reflns_number_total             3878
_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   0.0395
_oxford_refine_ls_scale          1.611(10)
_oxford_reflns_number_all        3870
_oxford_structure_analysis_title 100lcm18
_cod_data_source_file            c8cc05430d2.cif
_cod_data_source_block           IColl2ClO4-II-100K
_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               7122107
_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
I1 I 0.7500 0.2500 0.5000 0.0367 1.0000 Uani S
N11 N 0.74490(12) 0.0040(3) 0.4430(2) 0.0383 1.0000 Uani .
C12 C 0.78439(13) -0.0821(4) 0.4463(2) 0.0372 1.0000 Uani .
C13 C 0.78199(13) -0.2215(5) 0.4010(3) 0.0395 1.0000 Uani .
C14 C 0.73925(14) -0.2758(5) 0.3503(3) 0.0414 1.0000 Uani .
C15 C 0.69932(14) -0.1869(5) 0.3509(3) 0.0425 1.0000 Uani .
C16 C 0.70256(14) -0.0490(5) 0.3983(3) 0.0427 1.0000 Uani .
C17 C 0.83064(14) -0.0210(5) 0.4990(3) 0.0457 1.0000 Uani .
C18 C 0.73570(17) -0.4223(6) 0.2959(3) 0.0543 1.0000 Uani .
C19 C 0.65898(16) 0.0457(7) 0.3998(4) 0.0610 1.0000 Uani .
I2 I 0.5000 0.5000 0.5000 0.0367 1.0000 Uani S
N21 N 0.53526(11) 0.4679(4) 0.3828(2) 0.0391 1.0000 Uani .
C22 C 0.54934(12) 0.5931(4) 0.3423(3) 0.0395 1.0000 Uani .
C23 C 0.57378(13) 0.5751(4) 0.2754(3) 0.0413 1.0000 Uani .
C24 C 0.58448(12) 0.4261(5) 0.2486(3) 0.0440 1.0000 Uani .
C25 C 0.56795(14) 0.3002(5) 0.2891(3) 0.0465 1.0000 Uani .
C26 C 0.54346(14) 0.3212(4) 0.3557(3) 0.0439 1.0000 Uani .
C27 C 0.53766(17) 0.7531(4) 0.3702(3) 0.0492 1.0000 Uani .
C28 C 0.61263(15) 0.4045(5) 0.1792(3) 0.0528 1.0000 Uani .
C29 C 0.5255(2) 0.1849(5) 0.3988(4) 0.0630 1.0000 Uani .
Cl1 Cl 0.61060(4) 0.04983(12) 0.63223(7) 0.0492 1.0000 Uani .
O11 O 0.6197(3) 0.1980(6) 0.6039(4) 0.1299 1.0000 Uani .
O12 O 0.57960(16) 0.0623(4) 0.6918(4) 0.0847 1.0000 Uani .
O13 O 0.5926(2) -0.0515(5) 0.5598(3) 0.0939 1.0000 Uani .
O14 O 0.65184(16) -0.0230(6) 0.6826(4) 0.1134 1.0000 Uani .
H131 H 0.8096 -0.2790 0.4042 0.0468 1.0000 Uiso R
H151 H 0.6698 -0.2205 0.3179 0.0505 1.0000 Uiso R
H171 H 0.8551 -0.0972 0.4996 0.0685 1.0000 Uiso R
H172 H 0.8391 0.0738 0.4737 0.0686 1.0000 Uiso R
H173 H 0.8285 -0.0009 0.5583 0.0686 1.0000 Uiso R
H181 H 0.7086 -0.4822 0.2993 0.0811 1.0000 Uiso R
H182 H 0.7333 -0.3939 0.2358 0.0813 1.0000 Uiso R
H183 H 0.7631 -0.4851 0.3134 0.0812 1.0000 Uiso R
H191 H 0.6565 0.0668 0.4602 0.0908 1.0000 Uiso R
H192 H 0.6601 0.1438 0.3691 0.0904 1.0000 Uiso R
H193 H 0.6319 -0.0110 0.3695 0.0910 1.0000 Uiso R
H231 H 0.5829 0.6623 0.2474 0.0503 1.0000 Uiso R
H251 H 0.5732 0.1995 0.2710 0.0559 1.0000 Uiso R
H271 H 0.5465 0.8273 0.3306 0.0738 1.0000 Uiso R
H272 H 0.5551 0.7735 0.4307 0.0735 1.0000 Uiso R
H273 H 0.5047 0.7615 0.3671 0.0738 1.0000 Uiso R
H281 H 0.5972 0.3299 0.1357 0.0789 1.0000 Uiso R
H282 H 0.6439 0.3688 0.2070 0.0787 1.0000 Uiso R
H283 H 0.6149 0.5026 0.1509 0.0791 1.0000 Uiso R
H291 H 0.4923 0.1944 0.3972 0.0948 1.0000 Uiso R
H292 H 0.5424 0.1777 0.4607 0.0950 1.0000 Uiso R
H293 H 0.5309 0.0922 0.3679 0.0949 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 0.0800
1 -1 -1 0.0800
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 120.4(3) yes
I1 . N11 C16 118.9(3) yes
C12 . N11 C16 120.4(3) yes
N11 . C12 C13 120.2(3) yes
N11 . C12 C17 118.7(3) yes
C13 . C12 C17 121.0(3) 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(4) yes
C13 . C14 C18 122.4(4) yes
C15 . C14 C18 120.4(4) yes
C14 . C15 C16 120.8(4) yes
C14 . C15 H151 119.5 no
C16 . C15 H151 119.7 no
C15 . C16 N11 120.4(4) yes
C15 . C16 C19 120.5(4) yes
N11 . C16 C19 119.1(4) yes
C12 . C17 H171 109.9 no
C12 . C17 H172 110.8 no
H171 . C17 H172 108.9 no
C12 . C17 H173 110.2 no
H171 . C17 H173 108.6 no
H172 . C17 H173 108.5 no
C14 . C18 H181 112.3 no
C14 . C18 H182 108.2 no
H181 . C18 H182 107.9 no
C14 . C18 H183 111.4 no
H181 . C18 H183 109.3 no
H182 . C18 H183 107.6 no
C16 . C19 H191 110.8 no
C16 . C19 H192 110.0 no
H191 . C19 H192 109.0 no
C16 . C19 H193 108.8 no
H191 . C19 H193 109.8 no
H192 . C19 H193 108.3 no
N21 2_666 I2 N21 179.99 yes
I2 . N21 C22 120.3(2) yes
I2 . N21 C26 119.6(3) yes
C22 . N21 C26 120.1(4) yes
N21 . C22 C23 120.9(3) yes
N21 . C22 C27 119.0(4) yes
C23 . C22 C27 120.1(4) yes
C22 . C23 C24 120.4(4) yes
C22 . C23 H231 120.1 no
C24 . C23 H231 119.5 no
C23 . C24 C25 117.2(4) yes
C23 . C24 C28 121.2(4) yes
C25 . C24 C28 121.7(4) yes
C24 . C25 C26 121.3(4) yes
C24 . C25 H251 119.5 no
C26 . C25 H251 119.2 no
C25 . C26 N21 120.1(4) yes
C25 . C26 C29 121.0(4) yes
N21 . C26 C29 119.0(4) yes
C22 . C27 H271 108.4 no
C22 . C27 H272 109.6 no
H271 . C27 H272 109.7 no
C22 . C27 H273 110.1 no
H271 . C27 H273 109.1 no
H272 . C27 H273 109.9 no
C24 . C28 H281 109.5 no
C24 . C28 H282 109.4 no
H281 . C28 H282 110.5 no
C24 . C28 H283 108.6 no
H281 . C28 H283 109.6 no
H282 . C28 H283 109.2 no
C26 . C29 H291 111.6 no
C26 . C29 H292 109.6 no
H291 . C29 H292 108.4 no
C26 . C29 H293 108.6 no
H291 . C29 H293 109.2 no
H292 . C29 H293 109.4 no
O11 . Cl1 O12 109.0(3) yes
O11 . Cl1 O13 112.1(3) yes
O12 . Cl1 O13 112.1(3) yes
O11 . Cl1 O14 112.2(4) yes
O12 . Cl1 O14 104.9(4) yes
O13 . Cl1 O14 106.4(3) 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 2.278(3) yes
I1 N11 . 2.278(3) yes
N11 C12 . 1.357(5) yes
N11 C16 . 1.352(5) yes
C12 C13 . 1.379(5) yes
C12 C17 . 1.505(5) yes
C13 C14 . 1.396(6) yes
C13 H131 . 0.934 no
C14 C15 . 1.391(6) yes
C14 C18 . 1.501(6) yes
C15 C16 . 1.383(6) yes
C15 H151 . 0.941 no
C16 C19 . 1.509(5) yes
C17 H171 . 0.964 no
C17 H172 . 0.957 no
C17 H173 . 0.945 no
C18 H181 . 0.951 no
C18 H182 . 0.946 no
C18 H183 . 0.951 no
C19 H191 . 0.966 no
C19 H192 . 0.968 no
C19 H193 . 0.956 no
I2 N21 2_666 2.280(3) yes
I2 N21 . 2.280(3) yes
N21 C22 . 1.350(5) yes
N21 C26 . 1.362(5) yes
C22 C23 . 1.382(6) yes
C22 C27 . 1.499(5) yes
C23 C24 . 1.400(5) yes
C23 H231 . 0.930 no
C24 C25 . 1.385(6) yes
C24 C28 . 1.493(6) yes
C25 C26 . 1.383(6) yes
C25 H251 . 0.930 no
C26 C29 . 1.494(6) yes
C27 H271 . 0.955 no
C27 H272 . 0.975 no
C27 H273 . 0.953 no
C28 H281 . 0.964 no
C28 H282 . 0.968 no
C28 H283 . 0.957 no
C29 H291 . 0.965 no
C29 H292 . 0.975 no
C29 H293 . 0.957 no
Cl1 O11 . 1.388(5) yes
Cl1 O12 . 1.424(4) yes
Cl1 O13 . 1.421(4) yes
Cl1 O14 . 1.423(5) 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 O14 4_646 142 0.93 2.57 3.353(6) yes
C18 H183 O14 4_646 140 0.95 2.46 3.249(6) yes
C23 H231 O12 6_564 157 0.93 2.51 3.384(6) yes
C25 H251 O12 6_554 169 0.93 2.58 3.500(6) yes
C27 H272 O13 1_565 154 0.98 2.54 3.444(6) 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
-3 1 1 x
8 0 2 x
6 0 2 x
4 0 2 x
-1 1 4 x
-4 0 2 x
1 1 1 x
-23 7 8 x
