#------------------------------------------------------------------------------
#$Date: 2024-01-06 08:16:45 +0100 (sáb 06 de ene de 2024) $
#$Revision: 288727 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/01/1570142.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_1570142
loop_
_publ_author_name
'Millet, C. R. P.'
'Noone, E.'
'Schellbach, A. V.'
'Pahl, J.'
'Łosiewicz, J'
'Nichol, G. S.'
'Ingleson, M. J.'
_publ_section_title
;
 Borylation directed borylation of N-alkyl anilines using iodine
 activated pyrazaboles.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              12041
_journal_page_last               12048
_journal_paper_doi               10.1039/d3sc04269c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C6 H8 B2 I2 N4'
_chemical_formula_sum            'C6 H8 B2 I2 N4'
_chemical_formula_weight         411.58
_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
_audit_creation_date             2023-08-09
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-09 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                102.544(7)
_cell_angle_beta                 91.351(5)
_cell_angle_gamma                112.430(7)
_cell_formula_units_Z            2
_cell_length_a                   7.6116(5)
_cell_length_b                   7.7121(7)
_cell_length_c                   10.8808(7)
_cell_measurement_reflns_used    3217
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      28.4880
_cell_measurement_theta_min      3.8800
_cell_volume                     572.28(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  -6.00   1.00   30.00    --  -15.73  99.00 -49.00   57
  2  ω    -15.00  64.00   1.00   30.00    --   16.98 -99.00-156.00   79
  3  ω    -42.00  24.00   1.00   30.00    --  -15.73 -77.00-180.00   66
  4  ω    -15.00  64.00   1.00   30.00    --   16.98 -99.00 -90.00   79
  5  ω    -67.00  54.00   1.00   30.00    --   16.98 -38.00 -60.00  121
  6  ω    -15.00  64.00   1.00   30.00    --   16.98 -99.00 -30.00   79
  7  ω    -42.00  56.00   1.00   30.00    --   16.98 -77.00  60.00   98
  8  ω    -42.00  24.00   1.00   30.00    --  -15.73 -77.00  30.00   66
  9  ω    -42.00   2.00   1.00   30.00    --  -15.73 -77.00 120.00   44
 10  ω   -100.00  21.00   1.00   30.00    --  -15.73 -57.00 -30.00  121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4678
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.878
_diffrn_reflns_theta_min         3.222
_exptl_absorpt_coefficient_mu    5.461
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.389
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.029
_refine_diff_density_max         1.196
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         4678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0294
_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)+(0.0422P)²+0.5421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0744
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4005
_reflns_number_total             4678
_reflns_threshold_expression     'I > 2σ(I)'
_twin_special_details
;
Component 2 rotated by 179.9668° 
 around [0.00 1.00 0.00] (reciprocal) or [0.36 0.92 0.15] (direct)
;
_cod_data_source_file            d3sc04269c2.cif
_cod_data_source_block           mi19017_mo_2comp_refinalized_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 1570141--1570144.cif.'
_cod_database_code               1570142
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5396(9)
 0.4604(9)
2. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
3.a Ternary CH refined with riding coordinates:
 B2(H2A), B1(H1A)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C2(H2), C5(H5), C1(H1), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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
I2 I -0.00888(4) 0.19260(5) 0.76043(3) 0.01738(10) Uani 1 1 d . . . . .
I1 I 0.22622(5) 0.80321(4) 0.86762(3) 0.01916(10) Uani 1 1 d . . . . .
N4 N 0.4428(6) 0.4072(6) 0.7715(4) 0.0125(8) Uani 1 1 d . . . . .
N3 N 0.5183(6) 0.6044(6) 0.8028(4) 0.0138(9) Uani 1 1 d . . . . .
N1 N 0.3326(6) 0.6030(6) 0.6124(4) 0.0142(9) Uani 1 1 d . . . . .
N2 N 0.2636(6) 0.4066(6) 0.5793(4) 0.0151(9) Uani 1 1 d . . . . .
C6 C 0.5495(7) 0.3482(8) 0.8392(5) 0.0162(12) Uani 1 1 d . . . . .
H6 H 0.527280 0.217320 0.835918 0.019 Uiso 1 1 calc R U . . .
C4 C 0.6722(7) 0.6663(7) 0.8893(5) 0.0150(11) Uani 1 1 d . . . . .
H4 H 0.751458 0.797823 0.927003 0.018 Uiso 1 1 calc R U . . .
C2 C 0.2010(7) 0.5068(9) 0.4126(5) 0.0208(10) Uani 1 1 d . . . . .
H2 H 0.157396 0.507650 0.330266 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6967(7) 0.5083(9) 0.9145(4) 0.0166(10) Uani 1 1 d . . . . .
H5 H 0.793928 0.509505 0.971486 0.020 Uiso 1 1 calc R U . . .
C1 C 0.2943(8) 0.6642(8) 0.5118(5) 0.0190(12) Uani 1 1 d . . . . .
H1 H 0.326719 0.795370 0.509996 0.023 Uiso 1 1 calc R U . . .
B2 B 0.2724(8) 0.2848(8) 0.6700(6) 0.0150(11) Uani 1 1 d . . . . .
H2A H 0.290336 0.167267 0.622615 0.018 Uiso 1 1 calc R U . . .
C3 C 0.1834(7) 0.3462(8) 0.4569(5) 0.0166(11) Uani 1 1 d . . . . .
H3 H 0.124791 0.215441 0.409428 0.020 Uiso 1 1 calc R U . . .
B1 B 0.4362(8) 0.7232(8) 0.7438(6) 0.0161(11) Uani 1 1 d . . . . .
H1A H 0.542786 0.844053 0.735299 0.019 Uiso 1 1 calc R U . . .
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'
I I -0.4742 1.8119 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 -1 -5 0.0633
-10 0 5 0.0667
-1 10 0 0.0338
1 -10 0 0.0239
8 -7 8 0.0105
-7 1 12 0.0782
-8 7 -9 0.0141
7 -1 -12 0.0800
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
_geom_angle_publ_flag
N3 N4 B2 123.1(4) . . ?
C6 N4 N3 108.2(4) . . ?
C6 N4 B2 128.7(4) . . ?
N4 N3 B1 123.2(4) . . ?
C4 N3 N4 108.0(4) . . ?
C4 N3 B1 128.8(4) . . ?
N2 N1 B1 122.7(4) . . ?
C1 N1 N2 108.5(4) . . ?
C1 N1 B1 128.8(5) . . ?
N1 N2 B2 123.8(4) . . ?
C3 N2 N1 107.8(4) . . ?
C3 N2 B2 128.4(4) . . ?
N4 C6 H6 125.4 . . ?
N4 C6 C5 109.2(5) . . ?
C5 C6 H6 125.4 . . ?
N3 C4 H4 125.3 . . ?
N3 C4 C5 109.3(5) . . ?
C5 C4 H4 125.3 . . ?
C1 C2 H2 127.0 . . ?
C1 C2 C3 105.9(4) . . ?
C3 C2 H2 127.0 . . ?
C6 C5 H5 127.3 . . ?
C4 C5 C6 105.3(4) . . ?
C4 C5 H5 127.3 . . ?
N1 C1 C2 109.1(5) . . ?
N1 C1 H1 125.5 . . ?
C2 C1 H1 125.5 . . ?
I2 B2 H2A 109.6 . . ?
N4 B2 I2 110.7(3) . . ?
N4 B2 H2A 109.6 . . ?
N2 B2 I2 109.1(3) . . ?
N2 B2 N4 108.1(4) . . ?
N2 B2 H2A 109.6 . . ?
N2 C3 C2 108.7(5) . . ?
N2 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
I1 B1 H1A 109.4 . . ?
N3 B1 I1 110.5(4) . . ?
N3 B1 N1 108.5(4) . . ?
N3 B1 H1A 109.4 . . ?
N1 B1 I1 109.8(3) . . ?
N1 B1 H1A 109.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 B2 2.302(6) . ?
I1 B1 2.290(6) . ?
N4 N3 1.363(5) . ?
N4 C6 1.345(6) . ?
N4 B2 1.529(7) . ?
N3 C4 1.346(6) . ?
N3 B1 1.522(7) . ?
N1 N2 1.359(5) . ?
N1 C1 1.349(7) . ?
N1 B1 1.530(7) . ?
N2 B2 1.519(7) . ?
N2 C3 1.356(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.383(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(7) . ?
C2 H2 0.9500 . ?
C2 C1 1.371(8) . ?
C2 C3 1.386(8) . ?
C5 H5 0.9500 . ?
C1 H1 0.9500 . ?
B2 H2A 1.0000 . ?
C3 H3 0.9500 . ?
B1 H1A 1.0000 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 N3 C4 C5 -0.1(6) . . . . ?
N4 N3 B1 I1 94.1(5) . . . . ?
N4 N3 B1 N1 -26.2(6) . . . . ?
N4 C6 C5 C4 0.4(5) . . . . ?
N3 N4 C6 C5 -0.5(6) . . . . ?
N3 N4 B2 I2 -95.6(5) . . . . ?
N3 N4 B2 N2 23.8(6) . . . . ?
N3 C4 C5 C6 -0.2(5) . . . . ?
N1 N2 B2 I2 93.7(5) . . . . ?
N1 N2 B2 N4 -26.8(6) . . . . ?
N1 N2 C3 C2 -0.4(5) . . . . ?
N2 N1 C1 C2 -0.4(6) . . . . ?
N2 N1 B1 I1 -97.4(4) . . . . ?
N2 N1 B1 N3 23.4(6) . . . . ?
C6 N4 N3 C4 0.4(6) . . . . ?
C6 N4 N3 B1 179.4(4) . . . . ?
C6 N4 B2 I2 88.2(5) . . . . ?
C6 N4 B2 N2 -152.3(5) . . . . ?
C4 N3 B1 I1 -87.1(5) . . . . ?
C4 N3 B1 N1 152.6(5) . . . . ?
C1 N1 N2 B2 -177.3(4) . . . . ?
C1 N1 N2 C3 0.5(6) . . . . ?
C1 N1 B1 I1 83.1(6) . . . . ?
C1 N1 B1 N3 -156.0(5) . . . . ?
C1 C2 C3 N2 0.1(5) . . . . ?
B2 N4 N3 C4 -176.5(4) . . . . ?
B2 N4 N3 B1 2.5(7) . . . . ?
B2 N4 C6 C5 176.1(4) . . . . ?
B2 N2 C3 C2 177.2(4) . . . . ?
C3 N2 B2 I2 -83.6(5) . . . . ?
C3 N2 B2 N4 156.0(4) . . . . ?
C3 C2 C1 N1 0.1(5) . . . . ?
B1 N3 C4 C5 -179.0(5) . . . . ?
B1 N1 N2 B2 3.2(7) . . . . ?
B1 N1 N2 C3 -179.1(4) . . . . ?
B1 N1 C1 C2 179.1(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5396(9)
2 0.4604(9)
