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#$Date: 2024-09-06 04:56:46 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160070.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_7160070
loop_
_publ_author_name
'Jana, Debashis'
'Roy, Sima'
'Naskar, Srijita'
'Halder, Supriyo'
'Kanrar, Gopal'
'Pramanik, Kausikisankar'
_publ_section_title
;
 Potent pincer-zinc catalyzed homogeneous α-alkylation and
 Friedländer quinoline synthesis reaction of secondary
 alcohols/ketones with primary alcohols.
;
_journal_issue                   31
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6393
_journal_page_last               6408
_journal_paper_doi               10.1039/d4ob00988f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C16 H12 Cl N'
_chemical_formula_sum            'C16 H12 Cl N'
_chemical_formula_weight         253.72
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-19
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-04-17 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6371(5)
_cell_length_b                   12.4931(8)
_cell_length_c                   13.4370(8)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.23
_cell_volume                     1282.04(14)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Brucker D8 Quest SC-XRD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28901
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.719
_diffrn_reflns_theta_min         2.226
_diffrn_source_current           0.99
_diffrn_source_power             0.0495
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.5621
_exptl_absorpt_correction_T_min  0.4849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1608 before and 0.0692 after correction.
The Ratio of minimum to maximum transmission is 0.8627.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.33(14)
_refine_ls_extinction_method     nonef
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2433
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0496
_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)+(0.0286P)²+0.3257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2164
_reflns_number_total             2433
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00988f2.cif
_cod_data_source_block           10aj
_cod_depositor_comments
'Adding full bibliography for 7160068--7160071.cif.'
_cod_database_code               7160070
_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: 0.67(14)
 0.33(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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 0.9724(2) 0.66319(14) 0.89350(12) 0.1131(6) Uani 1 1 d . . . . .
N1 N 0.7964(4) 0.5920(2) 0.4724(3) 0.0585(8) Uani 1 1 d . . . . .
C1 C 0.7388(4) 0.6718(3) 0.4174(3) 0.0517(9) Uani 1 1 d . . . . .
C2 C 0.7157(5) 0.7764(3) 0.4560(3) 0.0574(10) Uani 1 1 d . . . . .
H2 H 0.676346 0.831141 0.414750 0.069 Uiso 1 1 calc R U . . .
C3 C 0.7509(5) 0.7966(3) 0.5525(3) 0.0587(10) Uani 1 1 d . . . . .
H3 H 0.734667 0.865007 0.578209 0.070 Uiso 1 1 calc R U . . .
C4 C 0.8123(5) 0.7137(3) 0.6140(3) 0.0539(9) Uani 1 1 d . . . . .
C5 C 0.8542(5) 0.7278(4) 0.7154(3) 0.0661(11) Uani 1 1 d . . . . .
H5 H 0.838126 0.793985 0.745681 0.079 Uiso 1 1 calc R U . . .
C6 C 0.9177(6) 0.6448(4) 0.7681(3) 0.0723(12) Uani 1 1 d . . . . .
C7 C 0.9420(6) 0.5434(4) 0.7266(4) 0.0769(13) Uani 1 1 d . . . . .
H7 H 0.986335 0.487723 0.765010 0.092 Uiso 1 1 calc R U . . .
C8 C 0.8999(5) 0.5270(3) 0.6294(3) 0.0694(11) Uani 1 1 d . . . . .
H8 H 0.914540 0.459409 0.601570 0.083 Uiso 1 1 calc R U . . .
C9 C 0.8342(5) 0.6116(3) 0.5699(3) 0.0545(9) Uani 1 1 d . . . . .
C10 C 0.7005(5) 0.6500(3) 0.3107(3) 0.0556(10) Uani 1 1 d . . . . .
C11 C 0.7664(5) 0.7197(3) 0.2391(3) 0.0680(11) Uani 1 1 d . . . . .
H11 H 0.831434 0.778797 0.259183 0.082 Uiso 1 1 calc R U . . .
C12 C 0.7374(7) 0.7030(4) 0.1397(3) 0.0824(14) Uani 1 1 d . . . . .
H12 H 0.785228 0.749495 0.092925 0.099 Uiso 1 1 calc R U . . .
C13 C 0.6382(7) 0.6180(4) 0.1092(4) 0.0814(13) Uani 1 1 d . . . . .
H13 H 0.616924 0.606860 0.041883 0.098 Uiso 1 1 calc R U . . .
C14 C 0.5701(6) 0.5492(4) 0.1793(4) 0.0756(13) Uani 1 1 d . . . . .
H14 H 0.501924 0.491850 0.158008 0.091 Uiso 1 1 calc R U . . .
C15 C 0.5997(5) 0.5623(3) 0.2807(3) 0.0610(10) Uani 1 1 d . . . . .
C16 C 0.5171(7) 0.4871(4) 0.3545(4) 0.0807(14) Uani 1 1 d . . . . .
H16A H 0.606147 0.443396 0.384284 0.121 Uiso 1 1 calc R U . . .
H16B H 0.433725 0.442291 0.320985 0.121 Uiso 1 1 calc R U . . .
H16C H 0.458678 0.527719 0.405256 0.121 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'
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
C1 N1 C9 118.3(3) . . ?
N1 C1 C2 122.3(3) . . ?
N1 C1 C10 117.8(3) . . ?
C2 C1 C10 119.8(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 123.5(4) . . ?
C3 C4 C9 117.2(3) . . ?
C5 C4 C9 119.3(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 Cl1 119.4(4) . . ?
C5 C6 C7 122.5(4) . . ?
C7 C6 Cl1 118.1(4) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.2(4) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(4) . . ?
C9 C8 H8 119.6 . . ?
N1 C9 C4 122.6(3) . . ?
N1 C9 C8 118.8(3) . . ?
C4 C9 C8 118.6(4) . . ?
C11 C10 C1 118.7(3) . . ?
C11 C10 C15 119.3(4) . . ?
C15 C10 C1 122.0(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(4) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(5) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.4(5) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 118.9 . . ?
C13 C14 C15 122.3(4) . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C16 122.0(4) . . ?
C14 C15 C10 117.7(4) . . ?
C14 C15 C16 120.2(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 C6 1.751(5) . ?
N1 C1 1.317(5) . ?
N1 C9 1.365(5) . ?
C1 C2 1.417(5) . ?
C1 C10 1.488(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.348(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.406(5) . ?
C4 C5 1.411(6) . ?
C4 C9 1.416(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.346(6) . ?
C6 C7 1.396(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.361(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.417(5) . ?
C10 C11 1.392(5) . ?
C10 C15 1.398(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.367(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(6) . ?
C15 C16 1.505(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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
Cl1 C6 C7 C8 179.8(3) . . . . ?
N1 C1 C2 C3 -0.9(5) . . . . ?
N1 C1 C10 C11 -131.8(4) . . . . ?
N1 C1 C10 C15 48.7(5) . . . . ?
C1 N1 C9 C4 0.6(5) . . . . ?
C1 N1 C9 C8 -178.6(3) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
C1 C10 C11 C12 179.2(4) . . . . ?
C1 C10 C15 C14 179.5(3) . . . . ?
C1 C10 C15 C16 2.6(6) . . . . ?
C2 C1 C10 C11 47.1(5) . . . . ?
C2 C1 C10 C15 -132.4(4) . . . . ?
C2 C3 C4 C5 179.3(4) . . . . ?
C2 C3 C4 C9 0.1(5) . . . . ?
C3 C4 C5 C6 -177.8(4) . . . . ?
C3 C4 C9 N1 -0.7(5) . . . . ?
C3 C4 C9 C8 178.5(3) . . . . ?
C4 C5 C6 Cl1 179.1(3) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
C5 C4 C9 N1 180.0(3) . . . . ?
C5 C4 C9 C8 -0.8(5) . . . . ?
C5 C6 C7 C8 -0.1(7) . . . . ?
C6 C7 C8 C9 0.8(6) . . . . ?
C7 C8 C9 N1 179.0(4) . . . . ?
C7 C8 C9 C4 -0.3(5) . . . . ?
C9 N1 C1 C2 0.3(5) . . . . ?
C9 N1 C1 C10 179.1(3) . . . . ?
C9 C4 C5 C6 1.4(5) . . . . ?
C10 C1 C2 C3 -179.7(3) . . . . ?
C10 C11 C12 C13 1.7(7) . . . . ?
C11 C10 C15 C14 0.0(5) . . . . ?
C11 C10 C15 C16 -176.9(4) . . . . ?
C11 C12 C13 C14 -0.8(8) . . . . ?
C12 C13 C14 C15 -0.5(7) . . . . ?
C13 C14 C15 C10 0.9(6) . . . . ?
C13 C14 C15 C16 177.8(4) . . . . ?
C15 C10 C11 C12 -1.3(6) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.67(14)
2 0.33(14)
