#------------------------------------------------------------------------------
#$Date: 2021-07-04 04:36:25 +0300 (Sun, 04 Jul 2021) $
#$Revision: 266962 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/88/4518810.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_4518810
loop_
_publ_author_name
'Das, Siuli'
'Mondal, Rakesh'
'Chakraborty, Gargi'
'Guin, Amit Kumar'
'Das, Abhishek'
'Paul, Nanda D.'
_publ_section_title
;
 Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of
 N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              7498
_journal_page_last               7512
_journal_paper_doi               10.1021/acscatal.1c00275
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C19 H13 Cl5 N4 Zn'
_chemical_formula_weight         539.97
_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_method           SHELXL-2014/7
_cell_angle_alpha                79.705(8)
_cell_angle_beta                 87.577(8)
_cell_angle_gamma                80.445(8)
_cell_formula_units_Z            2
_cell_length_a                   9.167(3)
_cell_length_b                   9.525(3)
_cell_length_c                   11.969(4)
_cell_measurement_reflns_used    32227
_cell_measurement_temperature    129(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.2
_cell_volume                     1013.9(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      129(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1106
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32227
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.360
_diffrn_reflns_theta_min         2.202
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.885
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6607
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.794
_refine_diff_density_min         -1.209
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.0077(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0312
_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)+(0.0416P)²+0.3360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0873
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4401
_reflns_number_total             5039
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c00275_si_002.cif
_cod_data_source_block           SDN24_0m_a
_cod_depositor_comments          'Adding full bibliography for 4518810.cif.'
_cod_original_cell_volume        1013.9(5)
_cod_database_code               4518810
_shelx_shelxl_version_number     2014/7
_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.
;
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
Zn01 Zn 0.74240(2) 0.31020(2) 0.30799(2) 0.01489(8) Uani 1 1 d . . . . .
Cl2 Cl 0.90938(5) 0.35989(5) 0.17265(4) 0.01958(11) Uani 1 1 d . . . . .
Cl3 Cl 0.69718(5) 0.08495(5) 0.35304(4) 0.02206(11) Uani 1 1 d . . . . .
Cl1 Cl 0.28881(6) 0.13491(6) -0.15161(4) 0.02460(12) Uani 1 1 d . . . . .
Cl4 Cl 0.12275(6) 0.86652(6) 0.10281(5) 0.02634(12) Uani 1 1 d . . . . .
Cl5 Cl 0.19770(9) 1.04082(7) 0.26061(8) 0.0594(2) Uani 1 1 d . . . . .
N1 N 0.84957(17) 0.32498(16) 0.46391(13) 0.0144(3) Uani 1 1 d . . . . .
N4 N 0.52370(16) 0.41304(16) 0.18605(13) 0.0145(3) Uani 1 1 d . . . . .
N2 N 0.62553(16) 0.49591(16) 0.35369(13) 0.0130(3) Uani 1 1 d . . . . .
N3 N 0.44919(17) 0.52636(16) 0.20893(13) 0.0149(3) Uani 1 1 d . . . . .
C12 C 0.79773(19) 0.44840(19) 0.50231(15) 0.0130(3) Uani 1 1 d . . . . .
C10 C 0.51107(19) 0.57753(19) 0.29810(15) 0.0137(3) Uani 1 1 d . . . . .
C18 C 0.5534(2) 0.2460(2) 0.05897(16) 0.0171(4) Uani 1 1 d . . . . .
H18 H 0.6528 0.2177 0.0838 0.021 Uiso 1 1 calc R U . . .
C13 C 0.4612(2) 0.35273(19) 0.10306(15) 0.0152(3) Uani 1 1 d . . . . .
C11 C 0.67756(19) 0.54280(19) 0.44152(15) 0.0132(3) Uani 1 1 d . . . . .
C7 C 0.61755(19) 0.67334(19) 0.47557(16) 0.0150(3) Uani 1 1 d . . . . .
C8 C 0.4973(2) 0.7585(2) 0.41302(16) 0.0174(4) Uani 1 1 d . . . . .
H8 H 0.4542 0.8493 0.4317 0.021 Uiso 1 1 calc R U . . .
C3 C 0.9661(2) 0.3879(2) 0.65677(16) 0.0178(4) Uani 1 1 d . . . . .
H3 H 1.0070 0.4081 0.7226 0.021 Uiso 1 1 calc R U . . .
C2 C 1.0177(2) 0.2620(2) 0.61784(16) 0.0189(4) Uani 1 1 d . . . . .
H2 H 1.0945 0.1938 0.6568 0.023 Uiso 1 1 calc R U . . .
C9 C 0.4435(2) 0.7088(2) 0.32493(16) 0.0169(4) Uani 1 1 d . . . . .
H9 H 0.3612 0.7635 0.2829 0.020 Uiso 1 1 calc R U . . .
C4 C 0.8519(2) 0.4870(2) 0.59819(15) 0.0150(3) Uani 1 1 d . . . . .
C15 C 0.2608(2) 0.3270(2) -0.00923(17) 0.0190(4) Uani 1 1 d . . . . .
H15 H 0.1606 0.3528 -0.0322 0.023 Uiso 1 1 calc R U . . .
C6 C 0.6786(2) 0.7115(2) 0.57155(16) 0.0174(4) Uani 1 1 d . . . . .
H6 H 0.6402 0.8010 0.5945 0.021 Uiso 1 1 calc R U . . .
C16 C 0.3543(2) 0.2213(2) -0.05313(16) 0.0175(4) Uani 1 1 d . . . . .
C17 C 0.5008(2) 0.1801(2) -0.02157(16) 0.0180(4) Uani 1 1 d . . . . .
H17 H 0.5636 0.1082 -0.0544 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7902(2) 0.6220(2) 0.63013(16) 0.0178(4) Uani 1 1 d . . . . .
H5 H 0.8285 0.6496 0.6940 0.021 Uiso 1 1 calc R U . . .
C1 C 0.9571(2) 0.2342(2) 0.52064(16) 0.0169(4) Uani 1 1 d . . . . .
H1 H 0.9945 0.1467 0.4943 0.020 Uiso 1 1 calc R U . . .
C14 C 0.3151(2) 0.3951(2) 0.06883(17) 0.0185(4) Uani 1 1 d . . . . .
H14 H 0.2532 0.4702 0.0989 0.022 Uiso 1 1 calc R U . . .
C19 C 0.0716(2) 1.0264(2) 0.1594(2) 0.0279(5) Uani 1 1 d . . . . .
H19 H 0.0666 1.1109 0.0973 0.033 Uiso 1 1 calc R U . . .
H20 H -0.0280 1.0272 0.1950 0.033 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'
N N 0.0061 0.0033 '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'
Zn Zn 0.2839 1.4301 '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
N2 Zn01 N1 76.85(6) . . ?
N2 Zn01 Cl3 128.86(5) . . ?
N1 Zn01 Cl3 99.20(4) . . ?
N2 Zn01 Cl2 111.52(5) . . ?
N1 Zn01 Cl2 103.94(5) . . ?
Cl3 Zn01 Cl2 118.70(2) . . ?
N2 Zn01 N4 67.36(6) . . ?
N1 Zn01 N4 143.60(6) . . ?
Cl3 Zn01 N4 98.09(4) . . ?
Cl2 Zn01 N4 95.32(4) . . ?
C1 N1 C12 118.05(16) . . ?
C1 N1 Zn01 129.44(13) . . ?
C12 N1 Zn01 112.48(11) . . ?
N3 N4 C13 114.65(15) . . ?
N3 N4 Zn01 115.65(12) . . ?
C13 N4 Zn01 129.23(12) . . ?
C10 N2 C11 117.98(16) . . ?
C10 N2 Zn01 124.92(12) . . ?
C11 N2 Zn01 116.88(12) . . ?
N4 N3 C10 112.64(15) . . ?
N1 C12 C4 123.89(16) . . ?
N1 C12 C11 116.96(16) . . ?
C4 C12 C11 119.13(17) . . ?
N2 C10 C9 123.40(16) . . ?
N2 C10 N3 118.92(16) . . ?
C9 C10 N3 117.63(16) . . ?
C13 C18 C17 119.67(17) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C13 C14 121.23(17) . . ?
C18 C13 N4 115.90(16) . . ?
C14 C13 N4 122.86(17) . . ?
N2 C11 C7 123.18(16) . . ?
N2 C11 C12 116.19(16) . . ?
C7 C11 C12 120.61(16) . . ?
C11 C7 C8 117.18(17) . . ?
C11 C7 C6 118.78(16) . . ?
C8 C7 C6 124.03(17) . . ?
C9 C8 C7 119.22(17) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C2 C3 C4 119.24(17) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C2 C1 119.69(17) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C8 C9 C10 119.02(17) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C12 C4 C3 116.63(17) . . ?
C12 C4 C5 119.11(17) . . ?
C3 C4 C5 124.26(17) . . ?
C16 C15 C14 118.81(17) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C5 C6 C7 120.84(18) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C15 C16 C17 122.46(18) . . ?
C15 C16 Cl1 119.62(14) . . ?
C17 C16 Cl1 117.92(15) . . ?
C18 C17 C16 118.44(18) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C6 C5 C4 121.47(17) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N1 C1 C2 122.49(18) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C15 C14 C13 119.34(18) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
Cl5 C19 Cl4 111.43(11) . . ?
Cl5 C19 H19 109.3 . . ?
Cl4 C19 H19 109.3 . . ?
Cl5 C19 H20 109.3 . . ?
Cl4 C19 H20 109.3 . . ?
H19 C19 H20 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
Zn01 N2 2.0599(16) . ?
Zn01 N1 2.1824(16) . ?
Zn01 Cl3 2.2201(8) . ?
Zn01 Cl2 2.2243(7) . ?
Zn01 N4 2.4887(16) . ?
Cl1 C16 1.732(2) . ?
Cl4 C19 1.762(2) . ?
Cl5 C19 1.747(2) . ?
N1 C1 1.320(2) . ?
N1 C12 1.345(2) . ?
N4 N3 1.246(2) . ?
N4 C13 1.416(2) . ?
N2 C10 1.323(2) . ?
N2 C11 1.346(2) . ?
N3 C10 1.424(2) . ?
C12 C4 1.399(3) . ?
C12 C11 1.434(2) . ?
C10 C9 1.385(3) . ?
C18 C13 1.377(3) . ?
C18 C17 1.383(3) . ?
C18 H18 0.9500 . ?
C13 C14 1.390(3) . ?
C11 C7 1.396(3) . ?
C7 C8 1.410(3) . ?
C7 C6 1.427(3) . ?
C8 C9 1.371(3) . ?
C8 H8 0.9500 . ?
C3 C2 1.368(3) . ?
C3 C4 1.406(3) . ?
C3 H3 0.9500 . ?
C2 C1 1.395(3) . ?
C2 H2 0.9500 . ?
C9 H9 0.9500 . ?
C4 C5 1.427(3) . ?
C15 C16 1.374(3) . ?
C15 C14 1.380(3) . ?
C15 H15 0.9500 . ?
C6 C5 1.350(3) . ?
C6 H6 0.9500 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9500 . ?
C5 H5 0.9500 . ?
C1 H1 0.9500 . ?
C14 H14 0.9500 . ?
C19 H19 0.9900 . ?
C19 H20 0.9900 . ?
