#------------------------------------------------------------------------------
#$Date: 2022-07-23 06:13:03 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276885 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/52/7245211.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_7245211
loop_
_publ_author_name
'Mehreen, Saba'
'Zia, Mehwash'
'Khan, Ajmal'
'Hussain, Javid'
'Ullah, Saeed'
'Anwar, Muhammad U.'
'Al-Harrasi, Ahmed'
'Naseer, Muhammad Moazzam'
_publ_section_title
;
 Phenoxy pendant isatins as potent α-glucosidase inhibitors: reciprocal
 carbonyl⋯carbonyl interactions, antiparallel π⋯π stacking
 driven solid state self-assembly and biological evaluation
;
_journal_issue                   32
_journal_name_full               'RSC Advances'
_journal_page_first              20919
_journal_page_last               20928
_journal_paper_doi               10.1039/D2RA03307K
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C16 H11 Cl F N O3'
_chemical_formula_sum            'C16 H11 Cl F N O3'
_chemical_formula_weight         319.71
_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-2018/3
_audit_update_record
;
2022-05-26 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                92.36(5)
_cell_angle_beta                 106.63(4)
_cell_angle_gamma                116.57(4)
_cell_formula_units_Z            2
_cell_length_a                   8.324(10)
_cell_length_b                   8.326(10)
_cell_length_c                   12.233(16)
_cell_measurement_reflns_used    4619
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.47
_cell_measurement_theta_min      2.85
_cell_volume                     712.3(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16520
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.556
_diffrn_reflns_theta_min         2.845
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0457
_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)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1822
_reflns_number_total             2928
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra03307k2.cif
_cod_data_source_block           SM_8_0m_a_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        712.2(15)
_cod_database_code               7245211
_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.
;
_shelx_estimated_absorpt_t_min   0.845
_shelx_estimated_absorpt_t_max   0.986
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
Cl1 Cl 0.28927(10) 0.62311(10) 0.73392(6) 0.0585(2) Uani 1 1 d . . . . .
F1 F -0.2403(3) -0.0057(2) -0.14843(16) 0.0929(6) Uani 1 1 d . . . . .
O2 O 0.3178(2) 0.5986(2) 0.17792(12) 0.0420(4) Uani 1 1 d . . . . .
O3 O 0.9399(2) 0.8471(2) 0.37826(13) 0.0480(4) Uani 1 1 d . . . . .
O4 O 0.9415(2) 0.7351(2) 0.60351(14) 0.0495(5) Uani 1 1 d . . . . .
N1 N 0.6489(2) 0.8197(2) 0.37383(14) 0.0342(4) Uani 1 1 d . . . . .
C1 C -0.0962(4) 0.1439(4) -0.0680(2) 0.0551(7) Uani 1 1 d . . . . .
C2 C -0.1132(4) 0.1739(4) 0.0379(2) 0.0553(7) Uani 1 1 d . . . . .
H2 H -0.219356 0.092096 0.054787 0.066 Uiso 1 1 calc R U . . .
C3 C 0.0298(3) 0.3275(3) 0.1192(2) 0.0447(6) Uani 1 1 d . . . . .
H3 H 0.021104 0.350464 0.191705 0.054 Uiso 1 1 calc R U . . .
C4 C 0.1865(3) 0.4474(3) 0.09231(17) 0.0338(5) Uani 1 1 d . . . . .
C5 C 0.2017(4) 0.4122(3) -0.01471(18) 0.0442(6) Uani 1 1 d . . . . .
H5 H 0.308623 0.491642 -0.031892 0.053 Uiso 1 1 calc R U . . .
C6 C 0.0572(4) 0.2584(4) -0.0959(2) 0.0547(7) Uani 1 1 d . . . . .
H6 H 0.064780 0.233693 -0.168542 0.066 Uiso 1 1 calc R U . . .
C7 C 0.4893(3) 0.7216(3) 0.16106(18) 0.0416(6) Uani 1 1 d . . . . .
H7A H 0.460934 0.766316 0.089828 0.050 Uiso 1 1 calc R U . . .
H7B H 0.563190 0.660672 0.155534 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5995(3) 0.8780(3) 0.26427(17) 0.0427(6) Uani 1 1 d . . . . .
H8A H 0.715835 0.967059 0.253776 0.051 Uiso 1 1 calc R U . . .
H8B H 0.523755 0.937704 0.267846 0.051 Uiso 1 1 calc R U . . .
C9 C 0.8155(3) 0.8131(3) 0.42051(18) 0.0355(5) Uani 1 1 d . . . . .
C10 C 0.8160(3) 0.7569(3) 0.53977(18) 0.0334(5) Uani 1 1 d . . . . .
C11 C 0.6380(3) 0.7364(3) 0.55087(16) 0.0293(5) Uani 1 1 d . . . . .
C12 C 0.5411(3) 0.7732(3) 0.45008(17) 0.0309(5) Uani 1 1 d . . . . .
C13 C 0.3665(3) 0.7638(3) 0.43531(19) 0.0396(6) Uani 1 1 d . . . . .
H13 H 0.301266 0.787932 0.368219 0.048 Uiso 1 1 calc R U . . .
C14 C 0.2913(3) 0.7171(3) 0.5241(2) 0.0410(6) Uani 1 1 d . . . . .
H14 H 0.173711 0.709959 0.516277 0.049 Uiso 1 1 calc R U . . .
C15 C 0.3884(3) 0.6808(3) 0.62422(19) 0.0359(5) Uani 1 1 d . . . . .
C16 C 0.5630(3) 0.6889(3) 0.63945(17) 0.0330(5) Uani 1 1 d . . . . .
H16 H 0.627457 0.663588 0.706260 0.040 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'
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'
F F 0.0171 0.0103 '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
C4 O2 C7 118.66(18) . . ?
C9 N1 C12 110.60(19) . . ?
C9 N1 C8 123.16(19) . . ?
C12 N1 C8 126.14(19) . . ?
C6 C1 F1 119.1(3) . . ?
C6 C1 C2 122.6(2) . . ?
F1 C1 C2 118.3(3) . . ?
C1 C2 C3 118.8(3) . . ?
C2 C3 C4 119.7(2) . . ?
O2 C4 C3 115.0(2) . . ?
O2 C4 C5 124.6(2) . . ?
C3 C4 C5 120.4(2) . . ?
C6 C5 C4 119.6(2) . . ?
C1 C6 C5 118.9(2) . . ?
O2 C7 C8 107.11(19) . . ?
N1 C8 C7 112.9(2) . . ?
O3 C9 N1 127.2(2) . . ?
O3 C9 C10 126.7(2) . . ?
N1 C9 C10 106.17(19) . . ?
O4 C10 C11 131.1(2) . . ?
O4 C10 C9 123.7(2) . . ?
C11 C10 C9 105.17(18) . . ?
C16 C11 C12 121.6(2) . . ?
C16 C11 C10 130.8(2) . . ?
C12 C11 C10 107.57(19) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 N1 128.7(2) . . ?
C11 C12 N1 110.5(2) . . ?
C12 C13 C14 117.7(2) . . ?
C15 C14 C13 121.2(2) . . ?
C16 C15 C14 121.5(2) . . ?
C16 C15 Cl1 118.74(18) . . ?
C14 C15 Cl1 119.80(19) . . ?
C15 C16 C11 117.2(2) . . ?
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 C15 1.745(3) . ?
F1 C1 1.359(3) . ?
O2 C4 1.372(3) . ?
O2 C7 1.417(3) . ?
O3 C9 1.214(3) . ?
O4 C10 1.203(3) . ?
N1 C9 1.368(3) . ?
N1 C12 1.422(3) . ?
N1 C8 1.455(3) . ?
C1 C6 1.358(4) . ?
C1 C2 1.368(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.383(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.381(4) . ?
C7 C8 1.505(3) . ?
C9 C10 1.550(4) . ?
C10 C11 1.461(3) . ?
C11 C16 1.386(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.378(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.389(4) . ?
C15 C16 1.381(3) . ?
