#------------------------------------------------------------------------------
#$Date: 2022-02-22 04:11:06 +0200 (Tue, 22 Feb 2022) $
#$Revision: 273078 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/44/7244467.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_7244467
loop_
_publ_author_name
'Al-Majid, Abdullah Mohammed'
'Alammari, Abdullah Saleh'
'Alshahrani, Saeed'
'Haukka, Matti'
'Islam, Mohammad Shahidul'
'Barakat, Assem'
_publ_section_title
;
 Cu(ii)-thiophene-2,5-bis(amino-alcohol) mediated asymmetric Aldol
 reaction and Domino Knoevenagel Michael cyclization: a new highly
 efficient Lewis acid catalyst
;
_journal_issue                   10
_journal_name_full               'RSC Advances'
_journal_page_first              6149
_journal_page_last               6165
_journal_paper_doi               10.1039/D2RA00674J
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C11 H10 N2 O5, 0.167(H2 O)'
_chemical_formula_sum            'C11 H10.33 N2 O5.17'
_chemical_formula_weight         253.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-19 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.317(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.0082(4)
_cell_length_b                   9.9146(2)
_cell_length_c                   11.4233(2)
_cell_measurement_reflns_used    9087
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      76.5290
_cell_measurement_theta_min      4.4570
_cell_volume                     2242.25(8)
_computing_cell_refinement
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_data_collection
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_molecular_graphics
'CrystaMaker X (CrystalMaker Software ltd., 2021)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15099
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.759
_diffrn_reflns_theta_min         4.467
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.039
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       plate
_exptl_crystal_F_000             1053
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0398
_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)+(0.0588P)²+2.3065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2165
_reflns_number_total             2362
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra00674j2.cif
_cod_data_source_block           aa5no2
_cod_original_cell_volume        2242.24(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7244467
_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   0.796
_shelx_estimated_absorpt_t_max   0.960
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'
'-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
N1 N 0.70939(6) 0.55524(11) 0.63796(9) 0.0186(2) Uani 1 1 d . . . . .
H1 H 0.7202(10) 0.5647(19) 0.7149(18) 0.029(5) Uiso 1 1 d . . . . .
N2 N 0.60629(7) 0.91100(12) 0.28115(11) 0.0274(3) Uani 1 1 d . . . . .
O1 O 0.57143(5) 0.42782(10) 0.57080(9) 0.0254(2) Uani 1 1 d . . . . .
O2 O 0.73752(5) 0.42969(10) 0.38583(8) 0.0174(2) Uani 1 1 d . . . . .
H2 H 0.7512(11) 0.348(2) 0.3962(19) 0.043(6) Uiso 1 1 d . . . . .
O3 O 0.73118(5) 0.32910(10) 0.62997(8) 0.0231(2) Uani 1 1 d . . . . .
O4 O 0.59375(10) 0.86485(13) 0.18158(11) 0.0587(5) Uani 1 1 d . . . . .
O5 O 0.60115(7) 1.03132(11) 0.30244(11) 0.0398(3) Uani 1 1 d . . . . .
C1 C 0.50756(8) 0.27110(17) 0.44177(16) 0.0337(4) Uani 1 1 d . . . . .
H1A H 0.477118 0.271302 0.501710 0.050 Uiso 1 1 calc R U . . .
H1B H 0.522853 0.178778 0.430263 0.050 Uiso 1 1 calc R U . . .
H1C H 0.483574 0.305743 0.366936 0.050 Uiso 1 1 calc R U . . .
C2 C 0.56745(7) 0.35907(13) 0.48220(12) 0.0214(3) Uani 1 1 d . . . . .
C3 C 0.62441(7) 0.35670(13) 0.40840(12) 0.0199(3) Uani 1 1 d . . . . .
H3A H 0.605859 0.379638 0.325717 0.024 Uiso 1 1 calc R U . . .
H3B H 0.642564 0.263804 0.408532 0.024 Uiso 1 1 calc R U . . .
C4 C 0.68250(6) 0.45312(13) 0.45044(10) 0.0162(3) Uani 1 1 d . . . . .
C5 C 0.70981(6) 0.43460(13) 0.58332(11) 0.0176(3) Uani 1 1 d . . . . .
C6 C 0.68193(6) 0.65579(13) 0.55982(11) 0.0170(3) Uani 1 1 d . . . . .
C7 C 0.67245(7) 0.79031(14) 0.58489(11) 0.0197(3) Uani 1 1 d . . . . .
H7 H 0.683471 0.824670 0.662927 0.024 Uiso 1 1 calc R U . . .
C8 C 0.64613(7) 0.87327(13) 0.49129(12) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.638735 0.966331 0.504512 0.024 Uiso 1 1 calc R U . . .
C9 C 0.63076(7) 0.81948(13) 0.37862(11) 0.0197(3) Uani 1 1 d . . . . .
C10 C 0.63895(7) 0.68273(13) 0.35288(11) 0.0181(3) Uani 1 1 d . . . . .
H10 H 0.627160 0.647946 0.275139 0.022 Uiso 1 1 calc R U . . .
C11 C 0.66490(6) 0.60169(13) 0.44598(11) 0.0165(3) Uani 1 1 d . . . . .
O6 O 0.500000 0.5020(5) 0.250000 0.0268(9) Uani 0.3333 2 d S T P . .
H6 H 0.515(3) 0.553(6) 0.196(5) 0.033(15) Uiso 0.3333 1 d . . P . .
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'
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
C5 N1 C6 111.42(10) . . ?
C5 N1 H1 122.7(12) . . ?
C6 N1 H1 125.4(12) . . ?
O4 N2 O5 122.65(13) . . ?
O4 N2 C9 118.57(12) . . ?
O5 N2 C9 118.74(12) . . ?
C4 O2 H2 109.6(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 122.45(13) . . ?
O1 C2 C3 120.65(12) . . ?
C1 C2 C3 116.88(12) . . ?
C2 C3 C4 114.54(11) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
O2 C4 C11 109.47(10) . . ?
O2 C4 C3 110.09(10) . . ?
C11 C4 C3 115.83(11) . . ?
O2 C4 C5 107.32(10) . . ?
C11 C4 C5 101.30(10) . . ?
C3 C4 C5 112.25(10) . . ?
O3 C5 N1 125.57(12) . . ?
O3 C5 C4 125.48(12) . . ?
N1 C5 C4 108.87(11) . . ?
C7 C6 N1 127.52(12) . . ?
C7 C6 C11 122.60(12) . . ?
N1 C6 C11 109.88(11) . . ?
C6 C7 C8 117.33(12) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
C9 C8 C7 119.66(12) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 123.36(12) . . ?
C8 C9 N2 118.19(12) . . ?
C10 C9 N2 118.42(12) . . ?
C11 C10 C9 116.48(12) . . ?
C11 C10 H10 121.8 . . ?
C9 C10 H10 121.8 . . ?
C10 C11 C6 120.54(12) . . ?
C10 C11 C4 130.95(11) . . ?
C6 C11 C4 108.47(11) . . ?
H6 O6 H6 111(8) . 2_655 ?
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
N1 C5 1.3497(17) . yes
N1 C6 1.3967(17) . yes
N1 H1 0.88(2) . ?
N2 O4 1.2180(17) . yes
N2 O5 1.2247(17) . yes
N2 C9 1.4647(17) . yes
O1 C2 1.2132(18) . yes
O2 C4 1.4304(15) . yes
O2 H2 0.86(2) . ?
O3 C5 1.2227(17) . yes
C1 C2 1.500(2) . yes
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5126(18) . ?
C3 C4 1.5277(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.5136(17) . ?
C4 C5 1.5480(17) . ?
C6 C7 1.3829(18) . ?
C6 C11 1.4024(17) . ?
C7 C8 1.3907(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3860(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.4020(19) . ?
C10 C11 1.3735(18) . ?
C10 H10 0.9500 . ?
O6 H6 0.88(6) . ?
O6 H6 0.88(6) 2_655 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.88(2) 1.93(2) 2.8098(14) 174.0(18) 6_566 yes
O2 H2 O3 0.86(2) 1.82(2) 2.6534(14) 162(2) 7_656 yes
C1 H1C O6 0.98 2.41 3.157(4) 132.7 . yes
C3 H3A O6 0.99 2.49 3.200(3) 128.8 . yes
C10 H10 O1 0.95 2.55 3.4856(16) 168.3 6_565 yes
O6 H6 O1 0.88(6) 1.95(6) 2.7503(16) 150(6) 6_565 yes
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
O1 C2 C3 C4 -3.95(18) . . . . ?
C1 C2 C3 C4 177.26(12) . . . . ?
C2 C3 C4 O2 171.84(10) . . . . ?
C2 C3 C4 C11 -63.32(14) . . . . ?
C2 C3 C4 C5 52.35(14) . . . . ?
C6 N1 C5 O3 179.67(12) . . . . ?
C6 N1 C5 C4 2.77(14) . . . . ?
O2 C4 C5 O3 -64.59(16) . . . . ?
C11 C4 C5 O3 -179.32(13) . . . . ?
C3 C4 C5 O3 56.50(17) . . . . ?
O2 C4 C5 N1 112.32(11) . . . . ?
C11 C4 C5 N1 -2.41(13) . . . . ?
C3 C4 C5 N1 -126.59(12) . . . . ?
C5 N1 C6 C7 178.85(12) . . . . ?
C5 N1 C6 C11 -1.96(15) . . . . ?
N1 C6 C7 C8 177.82(12) . . . . ?
C11 C6 C7 C8 -1.28(19) . . . . ?
C6 C7 C8 C9 -0.09(19) . . . . ?
C7 C8 C9 C10 1.4(2) . . . . ?
C7 C8 C9 N2 -177.03(12) . . . . ?
O4 N2 C9 C8 178.79(16) . . . . ?
O5 N2 C9 C8 0.9(2) . . . . ?
O4 N2 C9 C10 0.3(2) . . . . ?
O5 N2 C9 C10 -177.62(14) . . . . ?
C8 C9 C10 C11 -1.3(2) . . . . ?
N2 C9 C10 C11 177.13(12) . . . . ?
C9 C10 C11 C6 -0.07(19) . . . . ?
C9 C10 C11 C4 -177.70(12) . . . . ?
C7 C6 C11 C10 1.4(2) . . . . ?
N1 C6 C11 C10 -177.86(11) . . . . ?
C7 C6 C11 C4 179.49(11) . . . . ?
N1 C6 C11 C4 0.25(14) . . . . ?
O2 C4 C11 C10 65.97(17) . . . . ?
C3 C4 C11 C10 -59.19(18) . . . . ?
C5 C4 C11 C10 179.09(13) . . . . ?
O2 C4 C11 C6 -111.87(11) . . . . ?
C3 C4 C11 C6 122.97(12) . . . . ?
C5 C4 C11 C6 1.25(13) . . . . ?
