#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/80/7128096.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_7128096
loop_
_publ_author_name
'Liu, Jin-Biao'
'Ren, Miaofeng'
'Lai, Xiaojing'
'Qiu, Guanyinsheng'
_publ_section_title
;
 Iron-catalyzed stereoselective haloamidation of amide-tethered alkynes.
;
_journal_issue                   35
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4259
_journal_page_last               4262
_journal_paper_doi               10.1039/d1cc00870f
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C15 H10 Cl N O'
_chemical_formula_sum            'C15 H10 Cl N O'
_chemical_formula_weight         255.69
_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             2020-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-29 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.895(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2298(4)
_cell_length_b                   20.4052(11)
_cell_length_c                   11.8040(10)
_cell_measurement_reflns_used    1152
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.7710
_cell_measurement_theta_min      4.4490
_cell_volume                     1227.90(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00   4.00   1.00    5.00    --  -15.89  57.00 150.00   30
  2  ω    -49.00  60.00   1.00    5.00    --   16.05   0.00-120.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0770184000
_diffrn_orient_matrix_UB_12      0.0006835000
_diffrn_orient_matrix_UB_13      0.0576504000
_diffrn_orient_matrix_UB_21      -0.0125644000
_diffrn_orient_matrix_UB_22      0.0345900000
_diffrn_orient_matrix_UB_23      0.0009956000
_diffrn_orient_matrix_UB_31      -0.1150000000
_diffrn_orient_matrix_UB_32      -0.0032799000
_diffrn_orient_matrix_UB_33      0.0219670000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.899
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3130
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.480
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.038
_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     163
_refine_ls_number_reflns         1943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0377
_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)+(0.0358P)²+0.4896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1577
_reflns_number_total             1943
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc00870f2.cif
_cod_data_source_block           20180425-1
_cod_depositor_comments          'Adding full bibliography for 7128096.cif.'
_cod_database_code               7128096
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N Cl'
_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   0.965
_shelx_estimated_absorpt_t_min   0.943
_reflns_odcompleteness_completeness 87.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C11(H11), C7(H7), C15(H15), C5(H5), C6(H6), C12(H12),
 C13(H13), C14(H14)
;
_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 1.065
_oxdiff_exptl_absorpt_empirical_full_min 0.892
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
Cl1 Cl 0.98623(11) 0.31066(3) 0.59065(5) 0.0564(2) Uani 1 1 d . . . . .
O1 O 0.7192(3) 0.53797(7) 0.40057(15) 0.0532(4) Uani 1 1 d . . . . .
N1 N 0.7680(3) 0.42960(8) 0.45536(15) 0.0406(4) Uani 1 1 d . . . . .
H1 H 0.9102 0.4334 0.5081 0.049 Uiso 1 1 calc R . . . .
C2 C 0.6395(4) 0.36969(9) 0.42469(18) 0.0362(5) Uani 1 1 d . . . . .
C8 C 0.4057(4) 0.45330(10) 0.31603(19) 0.0399(5) Uani 1 1 d . . . . .
C1 C 0.6443(4) 0.48090(9) 0.39305(19) 0.0401(5) Uani 1 1 d . . . . .
C10 C 0.6040(4) 0.24726(9) 0.43362(19) 0.0368(5) Uani 1 1 d . . . . .
C3 C 0.4041(4) 0.38575(9) 0.33403(19) 0.0378(5) Uani 1 1 d . . . . .
C9 C 0.7177(4) 0.31194(9) 0.47289(18) 0.0379(5) Uani 1 1 d . . . . .
C4 C 0.1970(4) 0.34824(11) 0.27375(19) 0.0446(5) Uani 1 1 d . . . . .
H4 H 0.1920 0.3032 0.2855 0.054 Uiso 1 1 calc R . . . .
C11 C 0.6411(4) 0.22090(10) 0.3304(2) 0.0468(6) Uani 1 1 d . . . . .
H11 H 0.7402 0.2438 0.2872 0.056 Uiso 1 1 calc R . . . .
C7 C 0.2064(4) 0.48455(11) 0.2384(2) 0.0507(6) Uani 1 1 d . . . . .
H7 H 0.2098 0.5296 0.2271 0.061 Uiso 1 1 calc R . . . .
C15 C 0.4594(4) 0.21181(11) 0.4971(2) 0.0512(6) Uani 1 1 d . . . . .
H15 H 0.4350 0.2281 0.5676 0.061 Uiso 1 1 calc R . . . .
C5 C -0.0018(4) 0.37953(11) 0.1958(2) 0.0518(6) Uani 1 1 d . . . . .
H5 H -0.1414 0.3549 0.1543 0.062 Uiso 1 1 calc R . . . .
C6 C 0.0014(4) 0.44659(11) 0.1778(2) 0.0539(6) Uani 1 1 d . . . . .
H6 H -0.1351 0.4663 0.1247 0.065 Uiso 1 1 calc R . . . .
C12 C 0.5331(5) 0.16109(11) 0.2903(2) 0.0512(6) Uani 1 1 d . . . . .
H12 H 0.5603 0.1439 0.2209 0.061 Uiso 1 1 calc R . . . .
C13 C 0.3868(5) 0.12743(11) 0.3528(2) 0.0584(7) Uani 1 1 d . . . . .
H13 H 0.3111 0.0876 0.3254 0.070 Uiso 1 1 calc R . . . .
C14 C 0.3511(5) 0.15232(12) 0.4562(2) 0.0630(7) Uani 1 1 d . . . . .
H14 H 0.2530 0.1289 0.4991 0.076 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
C2 N1 H1 123.6 . . ?
C1 N1 H1 123.6 . . ?
C1 N1 C2 112.90(16) . . ?
N1 C2 C3 105.51(16) . . ?
C9 C2 N1 125.21(18) . . ?
C9 C2 C3 129.24(18) . . ?
C3 C8 C1 108.35(18) . . ?
C7 C8 C1 129.76(19) . . ?
C7 C8 C3 121.9(2) . . ?
O1 C1 N1 126.0(2) . . ?
O1 C1 C8 128.1(2) . . ?
N1 C1 C8 105.89(16) . . ?
C11 C10 C9 119.81(19) . . ?
C15 C10 C9 121.83(19) . . ?
C15 C10 C11 118.4(2) . . ?
C8 C3 C2 107.31(17) . . ?
C4 C3 C2 132.77(19) . . ?
C4 C3 C8 119.86(19) . . ?
C2 C9 Cl1 118.03(15) . . ?
C2 C9 C10 126.28(19) . . ?
C10 C9 Cl1 115.65(15) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 H4 120.9 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.4 . . ?
C8 C7 H7 121.1 . . ?
C8 C7 C6 117.8(2) . . ?
C6 C7 H7 121.1 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(2) . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C15 C14 H14 119.7 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
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
Cl1 C9 1.742(2) . ?
O1 C1 1.226(2) . ?
N1 H1 0.8600 . ?
N1 C2 1.403(2) . ?
N1 C1 1.357(3) . ?
C2 C3 1.476(3) . ?
C2 C9 1.332(3) . ?
C8 C1 1.481(3) . ?
C8 C3 1.395(3) . ?
C8 C7 1.381(3) . ?
C10 C9 1.479(3) . ?
C10 C11 1.385(3) . ?
C10 C15 1.382(3) . ?
C3 C4 1.386(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.380(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.361(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(4) . ?
C14 H14 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 138984447
