#------------------------------------------------------------------------------
#$Date: 2023-12-05 17:03:40 +0200 (Tue, 05 Dec 2023) $
#$Revision: 288040 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/66/7126633.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_7126633
loop_
_publ_author_name
'Liu, Yongchun'
'Ding, Na'
'Tan, Xiaoju'
'Li, Xiaoxiao'
'Zhao, Zhigang'
_publ_section_title
;
 Iron(ii)-chloride-catalyzed regioselective azidation of allenamides with
 TMSN₃.
;
_journal_issue                   54
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7507
_journal_page_last               7510
_journal_paper_doi               10.1039/c9cc10056c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C16 H15 Cl F N4 O2'
_chemical_formula_sum            'C16 H15 Cl F N4 O2'
_chemical_formula_weight         349.77
_chemical_name_systematic
;
 (E)-N-(3-azidoprop-1-en-1-yl)-N-(4-fluorophenyl)-4-methylbenzenesulfonamide
;
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-12-10 deposited with the CCDC.	2020-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                75.573(7)
_cell_angle_beta                 74.716(6)
_cell_angle_gamma                70.172(6)
_cell_formula_units_Z            2
_cell_length_a                   8.6867(5)
_cell_length_b                   8.7858(7)
_cell_length_c                   12.2020(10)
_cell_measurement_reflns_used    2776
_cell_measurement_temperature    295.0(4)
_cell_measurement_theta_max      72.2740
_cell_measurement_theta_min      5.4290
_cell_volume                     831.86(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      295.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  75.00   1.00    1.00    --   36.04 -99.00-180.00   74
  2  ω      7.00 107.00   1.00    1.00    --   36.04  19.00 -60.00  100
  3  ω     19.00 103.00   1.00    1.00    --   36.04  57.00 120.00   84
  4  ω     23.00  89.00   1.00    1.00    --   36.04-125.00 -30.00   66
  5  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00  30.00   70
  6  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00 120.00   53
  7  ω     91.00 176.00   1.00    1.00    --  108.00  45.00-120.00   85
  8  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00  90.00   53
  9  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00-150.00   53
 10  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00   0.00   53
 11  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00-120.00   53
 12  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00 -90.00   53
 13  ω     40.00  98.00   1.00    1.00    --  108.00 -45.00  60.00   58
 14  ω     40.00  98.00   1.00    1.00    --  108.00 -45.00  90.00   58
 15  ω     38.00 116.00   1.00    1.00    --  108.00-111.00 -90.00   78
 16  ω    -33.00  55.00   1.00    1.00    --   36.04 -38.00 -30.00   88
 17  ω    -33.00  55.00   1.00    1.00    --   36.04 -38.00-150.00   88
 18  ω     17.00 105.00   1.00    1.00    --   36.04  38.00  30.00   88
 19  ω     28.00  53.00   1.00    1.00    --   36.67 -57.00  60.00   25
 20  ω    -17.00  24.00   1.00    1.00    --   36.67 -19.00  90.00   41
 21  ω     44.00  82.00   1.00    1.00    --   36.67-125.00  90.00   38
 22  ω    -10.00  16.00   1.00    1.00    --   36.67 -57.00  60.00   26
 23  ω     37.00  64.00   1.00    1.00    --   36.67 -99.00 -60.00   27
 24  ω     41.00  66.00   1.00    1.00    --   36.67 -19.00  90.00   25
 25  ω    103.00 142.00   1.00    1.00    --  108.00 111.00-180.00   39
 26  ω     76.00 106.00   1.00    1.00    --  108.00 -94.00  90.00   30
 27  ω     44.00 104.00   1.00    1.00    --  108.00 -94.00 -60.00   60
 28  ω     51.00  86.00   1.00    1.00    --  108.00 -45.00 -60.00   35
 29  ω    103.00 146.00   1.00    1.00    --  108.00 178.00 -60.00   43
 30  ω     46.00  72.00   1.00    1.00    --  108.00 -94.00  90.00   26
 31  ω     56.00  82.00   1.00    1.00    --  108.00 -45.00-180.00   26
 32  ω    109.00 173.00   1.00    1.00    --  108.00  15.00-180.00   64
 33  ω     73.00  99.00   1.00    1.00    --  108.00  15.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0016526000
_diffrn_orient_matrix_UB_12      0.1520514000
_diffrn_orient_matrix_UB_13      -0.0960141000
_diffrn_orient_matrix_UB_21      0.0524458000
_diffrn_orient_matrix_UB_22      -0.1100302000
_diffrn_orient_matrix_UB_23      -0.0919565000
_diffrn_orient_matrix_UB_31      -0.1849794000
_diffrn_orient_matrix_UB_32      0.0250738000
_diffrn_orient_matrix_UB_33      0.0019522000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6881
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.547
_diffrn_reflns_theta_min         5.437
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.281
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0671
_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)+(0.1510P)²+0.1643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1995
_refine_ls_wR_factor_ref         0.2093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2835
_reflns_number_total             3217
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc10056c2.cif
_cod_data_source_block           lxx-lyc-1-2
_cod_depositor_comments          'Adding full bibliography for 7126633.cif.'
_cod_original_cell_volume        831.85(11)
_cod_database_code               7126633
_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.
;
_reflns_odcompleteness_completeness 99.87
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00O(H00K,H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00G)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-04-17
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.868
_oxdiff_exptl_absorpt_empirical_full_min 0.674
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
Cl01 Cl 0.85989(7) 0.81023(7) 0.55766(5) 0.0513(3) Uani 1 1 d . . . . .
O002 O 0.9458(2) 0.7268(3) 0.46206(16) 0.0597(5) Uani 1 1 d . . . . .
O003 O 0.8071(2) 0.9842(2) 0.54145(18) 0.0604(5) Uani 1 1 d . . . . .
F004 F 0.2241(3) 1.0809(3) 0.94506(19) 0.0957(7) Uani 1 1 d . . . . .
N005 N 0.6871(3) 0.7522(3) 0.61101(18) 0.0498(5) Uani 1 1 d . . . . .
C006 C 0.5657(3) 0.8364(3) 0.6987(2) 0.0469(5) Uani 1 1 d . . . . .
C007 C 0.9779(3) 0.7318(3) 0.6672(2) 0.0458(5) Uani 1 1 d . . . . .
C008 C 0.6917(3) 0.5925(3) 0.6050(2) 0.0544(6) Uani 1 1 d . . . . .
H008 H 0.7871 0.5306 0.5620 0.065 Uiso 1 1 calc R . . . .
C009 C 0.4264(3) 0.9582(4) 0.6703(2) 0.0551(6) Uani 1 1 d . . . . .
H009 H 0.4107 0.9852 0.5945 0.066 Uiso 1 1 calc R . . . .
N00A N 0.7375(6) 0.2351(4) 0.7940(3) 0.0918(11) Uani 1 1 d . . . . .
C00B C 1.1429(4) 0.6035(4) 0.8506(2) 0.0585(7) Uani 1 1 d . . . . .
C00C C 1.0532(4) 0.5647(3) 0.6916(2) 0.0547(6) Uani 1 1 d . . . . .
H00C H 1.0492 0.4949 0.6469 0.066 Uiso 1 1 calc R . . . .
C00D C 0.5866(4) 0.7927(4) 0.8128(2) 0.0578(7) Uani 1 1 d . . . . .
H00D H 0.6786 0.7076 0.8330 0.069 Uiso 1 1 calc R . . . .
C00E C 0.9857(4) 0.8356(3) 0.7326(3) 0.0612(7) Uani 1 1 d . . . . .
H00E H 0.9371 0.9483 0.7147 0.073 Uiso 1 1 calc R . . . .
C00F C 1.1347(4) 0.5025(4) 0.7838(3) 0.0626(7) Uani 1 1 d . . . . .
H00F H 1.1851 0.3900 0.8010 0.075 Uiso 1 1 calc R . . . .
N00G N 0.6131(6) 0.2400(4) 0.7633(4) 0.1043(12) Uani 1 1 d . . . . .
C00H C 1.0656(4) 0.7711(4) 0.8241(3) 0.0655(7) Uani 1 1 d . . . . .
H00H H 1.0682 0.8409 0.8694 0.079 Uiso 1 1 calc R . . . .
C00I C 0.4716(4) 0.8751(4) 0.8956(3) 0.0637(7) Uani 1 1 d . . . . .
H00I H 0.4850 0.8473 0.9719 0.076 Uiso 1 1 calc R . . . .
C00J C 0.3099(4) 1.0410(4) 0.7529(3) 0.0632(7) Uani 1 1 d . . . . .
H00J H 0.2154 1.1233 0.7340 0.076 Uiso 1 1 calc R . . . .
C00K C 0.3368(4) 0.9990(4) 0.8636(3) 0.0623(7) Uani 1 1 d . . . . .
C00L C 0.5713(4) 0.5239(4) 0.6554(3) 0.0707(8) Uani 1 1 d . . . . .
H00L H 0.4723 0.5850 0.6957 0.085 Uiso 1 1 calc R . . . .
N00M N 0.8481(7) 0.2242(6) 0.8290(4) 0.1202(15) Uani 1 1 d . . . . .
C00N C 1.2306(5) 0.5315(6) 0.9522(3) 0.0866(11) Uani 1 1 d . . . . .
H00A H 1.1491 0.5344 1.0228 0.130 Uiso 1 1 calc GR . . . .
H00B H 1.3024 0.5947 0.9506 0.130 Uiso 1 1 calc GR . . . .
H00G H 1.2958 0.4198 0.9474 0.130 Uiso 1 1 calc GR . . . .
C00O C 0.5897(5) 0.3521(5) 0.6495(4) 0.0881(12) Uani 1 1 d . . . . .
H00K H 0.6852 0.3143 0.5899 0.106 Uiso 1 1 calc R . . . .
H00M H 0.4911 0.3478 0.6286 0.106 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
O002 Cl01 N005 105.62(11) . . ?
O002 Cl01 C007 108.86(11) . . ?
O003 Cl01 O002 120.74(12) . . ?
O003 Cl01 N005 105.88(11) . . ?
O003 Cl01 C007 109.23(12) . . ?
N005 Cl01 C007 105.40(11) . . ?
C006 N005 Cl01 116.95(17) . . ?
C008 N005 Cl01 118.84(17) . . ?
C008 N005 C006 119.6(2) . . ?
C009 C006 N005 119.9(2) . . ?
C009 C006 C00D 119.6(2) . . ?
C00D C006 N005 120.4(2) . . ?
C00C C007 Cl01 119.28(19) . . ?
C00C C007 C00E 120.6(2) . . ?
C00E C007 Cl01 120.0(2) . . ?
N005 C008 H008 117.4 . . ?
C00L C008 N005 125.2(3) . . ?
C00L C008 H008 117.4 . . ?
C006 C009 H009 119.7 . . ?
C006 C009 C00J 120.7(3) . . ?
C00J C009 H009 119.7 . . ?
N00M N00A N00G 175.3(5) . . ?
C00F C00B C00H 118.3(3) . . ?
C00F C00B C00N 120.2(3) . . ?
C00H C00B C00N 121.4(3) . . ?
C007 C00C H00C 120.6 . . ?
C007 C00C C00F 118.9(2) . . ?
C00F C00C H00C 120.6 . . ?
C006 C00D H00D 120.0 . . ?
C00I C00D C006 120.1(3) . . ?
C00I C00D H00D 120.0 . . ?
C007 C00E H00E 120.3 . . ?
C00H C00E C007 119.5(3) . . ?
C00H C00E H00E 120.3 . . ?
C00B C00F C00C 121.5(3) . . ?
C00B C00F H00F 119.3 . . ?
C00C C00F H00F 119.3 . . ?
N00A N00G C00O 113.4(3) . . ?
C00B C00H H00H 119.4 . . ?
C00E C00H C00B 121.2(3) . . ?
C00E C00H H00H 119.4 . . ?
C00D C00I H00I 120.6 . . ?
C00K C00I C00D 118.7(3) . . ?
C00K C00I H00I 120.6 . . ?
C009 C00J H00J 120.8 . . ?
C00K C00J C009 118.3(3) . . ?
C00K C00J H00J 120.8 . . ?
F004 C00K C00I 118.7(3) . . ?
F004 C00K C00J 118.8(3) . . ?
C00I C00K C00J 122.5(3) . . ?
C008 C00L H00L 119.2 . . ?
C008 C00L C00O 121.7(3) . . ?
C00O C00L H00L 119.2 . . ?
C00B C00N H00A 109.5 . . ?
C00B C00N H00B 109.5 . . ?
C00B C00N H00G 109.5 . . ?
H00A C00N H00B 109.5 . . ?
H00A C00N H00G 109.5 . . ?
H00B C00N H00G 109.5 . . ?
N00G C00O H00K 109.4 . . ?
N00G C00O H00M 109.4 . . ?
C00L C00O N00G 111.3(3) . . ?
C00L C00O H00K 109.4 . . ?
C00L C00O H00M 109.4 . . ?
H00K C00O H00M 108.0 . . ?
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
Cl01 O002 1.432(2) . ?
Cl01 O003 1.4169(19) . ?
Cl01 N005 1.666(2) . ?
Cl01 C007 1.760(2) . ?
F004 C00K 1.352(3) . ?
N005 C006 1.440(3) . ?
N005 C008 1.410(3) . ?
C006 C009 1.374(4) . ?
C006 C00D 1.392(4) . ?
C007 C00C 1.381(3) . ?
C007 C00E 1.381(4) . ?
C008 H008 0.9300 . ?
C008 C00L 1.318(4) . ?
C009 H009 0.9300 . ?
C009 C00J 1.377(4) . ?
N00A N00G 1.217(6) . ?
N00A N00M 1.118(6) . ?
C00B C00F 1.375(4) . ?
C00B C00H 1.389(4) . ?
C00B C00N 1.515(4) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.385(4) . ?
C00D H00D 0.9300 . ?
C00D C00I 1.373(4) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.370(4) . ?
C00F H00F 0.9300 . ?
N00G C00O 1.507(6) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00K 1.369(5) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.369(4) . ?
C00L H00L 0.9300 . ?
C00L C00O 1.482(5) . ?
C00N H00A 0.9600 . ?
C00N H00B 0.9600 . ?
C00N H00G 0.9600 . ?
C00O H00K 0.9700 . ?
C00O H00M 0.9700 . ?
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2023-12-05T16:15:01+02:00
;
 Added the '_chemical_name_systematic' data item and marked the entry as having
 errors.
;
loop_
_cod_entry_issue_id
_cod_entry_issue_author
_cod_entry_issue_date
_cod_entry_issue_severity
_cod_entry_issue_origin
_cod_entry_issue_description
1 'Vaitkus, Antanas' 2023-12-05T16:15:01+02:00 error original
;
 Crystal structure model contains an atom site with an incorrectly assigned atom
 type. Atom site 'Cl1' should be occupied by a sulphur atom instead of a
 chlorine atom. 
;
