#------------------------------------------------------------------------------
#$Date: 2024-09-06 04:47:29 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294616 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/33/7063397.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_7063397
loop_
_publ_author_name
'Deng, Yaqi'
'Yin, Jiabin'
'Hu, Zongjing'
'Xue, Jian'
'Ji, Jian'
'Zhu, Tong'
'Liu, Shunying'
_publ_section_title
;
 Iodide ion-enabled highly regioselective α-C(sp3)--H triazolization of
 ethers with N-sulfonyl-1,2,3-triazoles
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15002
_journal_page_last               15007
_journal_paper_doi               10.1039/D4NJ02699C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C12 H12 Br N3 O2'
_chemical_formula_sum            'C12 H12 Br N3 O2'
_chemical_formula_weight         310.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-04 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.2030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8086(2)
_cell_length_b                   9.1808(2)
_cell_length_c                   9.3863(2)
_cell_measurement_reflns_used    12196
_cell_measurement_temperature    297.52(10)
_cell_measurement_theta_max      74.1340
_cell_measurement_theta_min      3.0060
_cell_volume                     1266.04(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.52(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  32.00   1.00    1.00    --    0.00 -82.00  60.00   84
  2  ω    -84.00 -57.00   1.00    1.00    --    0.00 -82.00  60.00   27
  3  ω    -44.00  24.00   1.00    1.00    --    0.00 -19.00  90.00   68
  4  ω    -88.00  19.00   1.00    1.00    --    0.00 -37.00 -30.00  107
  5  ω    -19.00  78.00   1.00    1.00    --    0.00  37.00-120.00   97
  6  ω    -85.00 -49.00   1.00    1.00    --    0.00 -19.00  90.00   36
  7  ω      9.00  76.00   1.00    1.00    --    0.00  19.00  30.00   67
  8  ω    -24.00   3.00   1.00    1.00    --    0.00  19.00  30.00   27
  9  ω    -30.00  35.00   1.00    1.00    --    0.00  82.00  90.00   65
 10  ω     41.00  66.00   1.00    1.00    --    0.00  82.00  90.00   25
 11  ω     68.00  94.00   1.00    1.00    --   95.80  74.00  51.97   26
 12  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 150.00   26
 13  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 14  ω     71.00  97.00   1.00    1.00    --   95.80  61.00  30.00   26
 15  ω      6.00 128.00   1.00    1.00    --   95.80 -82.00  90.00  122
 16  ω     68.00  94.00   1.00    1.00    --   95.80  68.00 -72.90   26
 17  ω     69.00 105.00   1.00    1.00    --   95.80  65.00-112.90   36
 18  ω    126.00 179.00   1.00    1.00    --   95.80  75.00 -13.97   53
 19  ω     93.00 127.00   1.00    1.00    --   95.80 -82.00-150.00   34
 20  ω     54.00  82.00   1.00    1.00    --   95.80 -82.00-150.00   28
 21  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 22  ω     63.00  94.00   1.00    1.00    --   95.80  82.00  60.00   31
 23  ω     63.00  97.00   1.00    1.00    --   95.80  82.00-180.00   34
 24  ω     65.00  96.00   1.00    1.00    --   95.80  77.00   0.00   31
 25  ω      6.00  71.00   1.00    1.00    --   95.80 -82.00  30.00   65
 26  ω     75.00 104.00   1.00    1.00    --   95.80 -82.00  30.00   29
 27  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 28  ω     63.00  95.00   1.00    1.00    --   95.80  82.00-120.00   32
 29  ω     71.00 109.00   1.00    1.00    --   95.80  61.00  60.00   38
 30  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 31  ω     66.00  91.00   1.00    1.00    --   95.80  75.00 -13.97   25
 32  ω     69.00  95.00   1.00    1.00    --   95.80  67.00 -29.19   26
 33  ω     20.00  48.00   1.00    1.00    --   95.80 -82.00-150.00   28
 34  ω     64.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   25
 35  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 36  ω     65.00  95.00   1.00    1.00    --   95.80  77.00-150.00   30
 37  ω     75.00 108.00   1.00    1.00    --   95.80  45.00-180.00   33
 38  ω    116.00 142.00   1.00    1.00    --   95.80  45.00-180.00   26
 39  ω     75.00 185.00   1.00    1.00    --   95.80  45.00 -60.00  110
 40  ω     66.00  92.00   1.00    1.00    --   95.80  77.00-180.00   26
 41  ω     64.00  90.00   1.00    1.00    --   95.80  82.00 120.00   26
 42  ω    110.00 184.00   1.00    1.00    --   95.80  82.00 120.00   74
 43  ω     37.00 127.00   1.00    1.00    --   95.80 -82.00-180.00   90
 44  ω     76.00 133.00   1.00    1.00    --   95.80  30.00 -90.00   57
 45  ω    136.00 175.00   1.00    1.00    --   95.80  30.00 -90.00   39
 46  ω     75.00 113.00   1.00    1.00    --   95.80  45.00-150.00   38
 47  ω     77.00 180.00   1.00    1.00    --   95.80  45.00  60.00  103
 48  ω     75.00 166.00   1.00    1.00    --   95.80  45.00 120.00   91
 49  ω     68.00  94.00   1.00    1.00    --   95.80  74.00  85.91   26
 50  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 51  ω     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 52  ω    141.00 169.00   1.00    1.00    --   95.80  45.00 150.00   28
 53  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 54  ω     75.00 108.00   1.00    1.00    --   95.80  45.00 150.00   33
 55  ω     95.00 120.00   1.00    1.00    --   95.80 -61.00  30.00   25
 56  ω     72.00  98.00   1.00    1.00    --   95.80  61.00 120.00   26
 57  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 58  ω     65.00  91.00   1.00    1.00    --   95.80  82.00  30.00   26
 59  ω    117.00 185.00   1.00    1.00    --   95.80  82.00  30.00   68
 60  ω     10.00 128.00   1.00    1.00    --   95.80 -82.00 -30.00  118
 61  ω     51.00  76.00   1.00    1.00    --   95.80 -61.00  30.00   25
 62  ω      9.00  44.00   1.00    1.00    --   95.80 -61.00  30.00   35
 63  ω     75.00 173.00   1.00    1.00    --   95.80  45.00 -30.00   98
 64  ω    143.00 176.00   1.00    1.00    --   95.80  74.00  51.97   33
 65  ω    142.00 167.00   1.00    1.00    --   95.80  65.00-112.90   25
 66  ω    114.00 146.00   1.00    1.00    --   95.80  38.00-118.64   32
 67  ω     79.00 104.00   1.00    1.00    --   95.80  38.00-118.64   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0630499000
_diffrn_orient_matrix_UB_12      0.0139327000
_diffrn_orient_matrix_UB_13      0.1428102000
_diffrn_orient_matrix_UB_21      0.0836219000
_diffrn_orient_matrix_UB_22      -0.0187361000
_diffrn_orient_matrix_UB_23      -0.0806084000
_diffrn_orient_matrix_UB_31      0.0041353000
_diffrn_orient_matrix_UB_32      0.1663470000
_diffrn_orient_matrix_UB_33      -0.0211199000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26271
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         3.008
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0511P)²+0.7540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2012
_reflns_number_total             2253
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj02699c2.cif
_cod_data_source_block           exp_2860
_cod_depositor_comments          'Adding full bibliography for 7063397.cif.'
_cod_database_code               7063397
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_max   0.443
_shelx_estimated_absorpt_t_min   0.284
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C5(H5), C4(H4), C8(H8)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.633
_oxdiff_exptl_absorpt_empirical_full_min 0.539
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_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
Br1 Br 0.81756(2) 0.20065(5) 0.47414(5) 0.0863(2) Uani 1 1 d . . . . .
O1 O 0.16111(14) 0.3974(2) 0.2809(3) 0.0757(6) Uani 1 1 d . . . . .
O2 O 0.02993(16) 0.2838(3) 0.4399(3) 0.0863(8) Uani 1 1 d . . . . .
N1 N 0.34867(16) 0.2656(3) 0.4179(3) 0.0614(6) Uani 1 1 d . . . . .
N2 N 0.26502(16) 0.2245(3) 0.3682(3) 0.0614(6) Uani 1 1 d . . . . .
N3 N 0.25887(17) 0.1090(3) 0.2832(3) 0.0745(7) Uani 1 1 d . . . . .
C6 C 0.50073(18) 0.1727(3) 0.3919(3) 0.0512(6) Uani 1 1 d . . . . .
C7 C 0.40188(19) 0.1681(3) 0.3623(3) 0.0540(6) Uani 1 1 d . . . . .
C3 C 0.6891(2) 0.1866(3) 0.4436(3) 0.0593(7) Uani 1 1 d . . . . .
C2 C 0.6483(2) 0.0738(3) 0.3630(3) 0.0605(7) Uani 1 1 d . . . . .
H2 H 0.683512 0.002587 0.325920 0.073 Uiso 1 1 calc R . . . .
C1 C 0.55463(19) 0.0677(3) 0.3380(3) 0.0576(6) Uani 1 1 d . . . . .
H1 H 0.526950 -0.008555 0.283731 0.069 Uiso 1 1 calc R . . . .
C9 C 0.1855(2) 0.3046(3) 0.3988(3) 0.0651(8) Uani 1 1 d . . . . .
H9 H 0.201191 0.363271 0.485556 0.078 Uiso 1 1 calc R . . . .
C5 C 0.5438(2) 0.2833(3) 0.4764(3) 0.0628(7) Uani 1 1 d . . . . .
H5 H 0.508905 0.352801 0.516536 0.075 Uiso 1 1 calc R . . . .
C4 C 0.6376(2) 0.2913(3) 0.5016(3) 0.0651(8) Uani 1 1 d . . . . .
H4 H 0.665737 0.366369 0.556992 0.078 Uiso 1 1 calc R . . . .
C8 C 0.3453(2) 0.0714(4) 0.2798(3) 0.0715(8) Uani 1 1 d . . . . .
H8 H 0.364812 -0.007624 0.229717 0.086 Uiso 1 1 calc R . . . .
C11 C 0.0040(2) 0.3733(4) 0.3194(4) 0.0752(9) Uani 1 1 d . . . . .
H11A H -0.050247 0.427769 0.333608 0.090 Uiso 1 1 calc R . . . .
H11B H -0.009937 0.313224 0.234415 0.090 Uiso 1 1 calc R . . . .
C12 C 0.0787(2) 0.4754(4) 0.2985(5) 0.0862(10) Uani 1 1 d . . . . .
H12A H 0.060865 0.534799 0.214131 0.103 Uiso 1 1 calc R . . . .
H12B H 0.089653 0.539689 0.380828 0.103 Uiso 1 1 calc R . . . .
C10 C 0.1095(2) 0.2040(4) 0.4205(5) 0.0829(11) Uani 1 1 d . . . . .
H10A H 0.096984 0.140489 0.337810 0.099 Uiso 1 1 calc R . . . .
H10B H 0.127097 0.143618 0.504269 0.099 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C9 O1 C12 110.4(2) . . ?
C11 O2 C10 110.2(3) . . ?
N2 N1 C7 104.0(2) . . ?
N1 N2 C9 122.3(2) . . ?
N3 N2 N1 115.6(2) . . ?
N3 N2 C9 122.1(2) . . ?
N2 N3 C8 103.2(3) . . ?
C1 C6 C7 121.4(3) . . ?
C1 C6 C5 118.1(3) . . ?
C5 C6 C7 120.5(2) . . ?
N1 C7 C6 122.1(3) . . ?
N1 C7 C8 107.5(3) . . ?
C8 C7 C6 130.3(3) . . ?
C2 C3 Br1 119.8(2) . . ?
C2 C3 C4 121.0(3) . . ?
C4 C3 Br1 119.2(2) . . ?
C3 C2 H2 120.5 . . ?
C3 C2 C1 119.1(3) . . ?
C1 C2 H2 120.5 . . ?
C6 C1 H1 119.2 . . ?
C2 C1 C6 121.5(3) . . ?
C2 C1 H1 119.2 . . ?
O1 C9 N2 106.7(2) . . ?
O1 C9 H9 109.3 . . ?
O1 C9 C10 111.1(3) . . ?
N2 C9 H9 109.3 . . ?
N2 C9 C10 111.1(3) . . ?
C10 C9 H9 109.3 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N3 C8 C7 109.6(3) . . ?
N3 C8 H8 125.2 . . ?
C7 C8 H8 125.2 . . ?
O2 C11 H11A 109.7 . . ?
O2 C11 H11B 109.7 . . ?
O2 C11 C12 110.0(3) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
O1 C12 C11 110.9(3) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
O2 C10 C9 110.6(3) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
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
Br1 C3 1.893(3) . ?
O1 C9 1.407(4) . ?
O1 C12 1.442(4) . ?
O2 C11 1.412(4) . ?
O2 C10 1.418(4) . ?
N1 N2 1.323(3) . ?
N1 C7 1.341(4) . ?
N2 N3 1.323(4) . ?
N2 C9 1.447(4) . ?
N3 C8 1.330(4) . ?
C6 C7 1.456(4) . ?
C6 C1 1.387(4) . ?
C6 C5 1.393(4) . ?
C7 C8 1.388(4) . ?
C3 C2 1.377(4) . ?
C3 C4 1.380(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.379(4) . ?
C1 H1 0.9300 . ?
C9 H9 0.9800 . ?
C9 C10 1.490(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(4) . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.481(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
