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#$Date: 2022-05-07 01:31:54 +0300 (Sat, 07 May 2022) $
#$Revision: 275152 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/48/7244898.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_7244898
loop_
_publ_author_name
'Dolai, Gobinda'
'Giri, Rajat Subhra'
'Mandal, Bhubaneswar'
_publ_section_title
;
 Versatility in self-assembly and morphology of non-coded anthranilic acid
 and phenylglycine based dipeptide stereoisomers
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00158F
_journal_year                    2022
_chemical_formula_moiety         'C21 H24 N2 O5'
_chemical_formula_sum            'C21 H24 N2 O5'
_chemical_formula_weight         384.42
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           Triclinic'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-10-30 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                109.580(2)
_cell_angle_beta                 98.665(2)
_cell_angle_gamma                117.163(2)
_cell_formula_units_Z            2
_cell_length_a                   10.5740(6)
_cell_length_b                   10.9521(7)
_cell_length_c                   11.4570(8)
_cell_measurement_reflns_used    2799
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.98
_cell_measurement_theta_min      2.32
_cell_volume                     1036.68(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15191
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       niddle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.1128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1981
_reflns_number_gt                2224
_reflns_number_total             3648
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ce00158f2.cif
_cod_data_source_block           l_ph_y_ome_bkp_0m_a
_cod_original_cell_volume        1036.68(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7244898
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.5812(2) 0.5342(2) 0.3748(2) 0.0606(6) Uani 1 1 d . . .
O1 O 0.1131(2) 0.3452(2) 0.3824(2) 0.0634(6) Uani 1 1 d . . .
O5 O 0.6134(3) 0.7380(2) -0.0795(2) 0.0652(6) Uani 1 1 d . . .
O4 O 0.5292(3) 0.7657(2) 0.0869(2) 0.0651(6) Uani 1 1 d . . .
O2 O 0.1294(2) 0.4683(3) 0.2558(2) 0.0715(7) Uani 1 1 d . . .
N2 N 0.5926(2) 0.6624(2) 0.2527(2) 0.0470(6) Uani 1 1 d . . .
H2 H 0.5601 0.7159 0.2357 0.056 Uiso 1 1 calc R . .
N1 N 0.3352(3) 0.5416(3) 0.4196(2) 0.0544(7) Uani 1 1 d . . .
H1 H 0.3662 0.5278 0.4851 0.065 Uiso 1 1 calc R . .
C13 C 0.5455(3) 0.6109(3) 0.3394(3) 0.0439(7) Uani 1 1 d . . .
C19 C 0.6891(3) 0.6672(3) 0.0747(3) 0.0441(7) Uani 1 1 d . . .
C14 C 0.6874(3) 0.6403(3) 0.1866(3) 0.0440(7) Uani 1 1 d . . .
C20 C 0.6020(3) 0.7273(3) 0.0306(3) 0.0470(7) Uani 1 1 d . . .
C5 C 0.1868(3) 0.4524(3) 0.3440(3) 0.0475(7) Uani 1 1 d . . .
C6 C 0.4453(3) 0.6604(3) 0.3949(3) 0.0452(7) Uani 1 1 d . . .
H6 H 0.3894 0.6722 0.3276 0.054 Uiso 1 1 calc R . .
C7 C 0.5401(3) 0.8144(3) 0.5194(3) 0.0470(7) Uani 1 1 d . . .
C18 C 0.7798(3) 0.6399(3) 0.0064(3) 0.0569(8) Uani 1 1 d . . .
H18 H 0.7808 0.6561 -0.0682 0.068 Uiso 1 1 calc R . .
C15 C 0.7806(3) 0.5935(3) 0.2287(3) 0.0565(8) Uani 1 1 d . . .
H15 H 0.7832 0.5789 0.3042 0.068 Uiso 1 1 calc R . .
C8 C 0.4682(4) 0.8817(4) 0.5765(3) 0.0660(9) Uani 1 1 d . . .
H8 H 0.3632 0.8318 0.5373 0.079 Uiso 1 1 calc R . .
C16 C 0.8682(4) 0.5692(4) 0.1587(4) 0.0666(9) Uani 1 1 d . . .
H16 H 0.9300 0.5382 0.1877 0.080 Uiso 1 1 calc R . .
C17 C 0.8669(4) 0.5898(4) 0.0466(3) 0.0673(9) Uani 1 1 d . . .
H17 H 0.9247 0.5698 -0.0013 0.081 Uiso 1 1 calc R . .
C9 C 0.5471(6) 1.0205(5) 0.6896(4) 0.0817(11) Uani 1 1 d . . .
H9 H 0.4956 1.0629 0.7271 0.098 Uiso 1 1 calc R . .
C1 C -0.0438(4) 0.2209(4) 0.3079(4) 0.0790(11) Uani 1 1 d . . .
C12 C 0.6939(4) 0.8917(4) 0.5784(4) 0.0899(13) Uani 1 1 d . . .
H12 H 0.7459 0.8491 0.5424 0.108 Uiso 1 1 calc R . .
C21 C 0.5353(5) 0.7998(4) -0.1294(3) 0.0838(12) Uani 1 1 d . . .
H21A H 0.4326 0.7493 -0.1312 0.126 Uiso 1 1 calc R . .
H21B H 0.5336 0.7824 -0.2177 0.126 Uiso 1 1 calc R . .
H21C H 0.5878 0.9087 -0.0724 0.126 Uiso 1 1 calc R . .
C10 C 0.6985(6) 1.0945(4) 0.7455(4) 0.0962(13) Uani 1 1 d . . .
H10 H 0.7525 1.1888 0.8220 0.115 Uiso 1 1 calc R . .
C3 C -0.0782(4) 0.1255(5) 0.3817(5) 0.0983(13) Uani 1 1 d . . .
H3A H -0.0187 0.0803 0.3758 0.147 Uiso 1 1 calc R . .
H3B H -0.1847 0.0451 0.3428 0.147 Uiso 1 1 calc R . .
H3C H -0.0533 0.1903 0.4733 0.147 Uiso 1 1 calc R . .
C11 C 0.7737(5) 1.0320(5) 0.6904(5) 0.1184(18) Uani 1 1 d . . .
H11 H 0.8792 1.0843 0.7287 0.142 Uiso 1 1 calc R . .
C4 C -0.1459(5) 0.2768(8) 0.3007(8) 0.194(4) Uani 1 1 d . . .
H4A H -0.1255 0.3482 0.3885 0.291 Uiso 1 1 calc R . .
H4B H -0.2499 0.1910 0.2634 0.291 Uiso 1 1 calc R . .
H4C H -0.1289 0.3279 0.2457 0.291 Uiso 1 1 calc R . .
C2 C -0.0526(8) 0.1270(6) 0.1718(6) 0.194(3) Uani 1 1 d . . .
H2A H -0.0176 0.1916 0.1292 0.291 Uiso 1 1 calc R . .
H2B H -0.1562 0.0428 0.1190 0.291 Uiso 1 1 calc R . .
H2C H 0.0105 0.0872 0.1809 0.291 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'
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
C5 O1 C1 121.9(2) . . ?
C20 O5 C21 117.0(2) . . ?
C13 N2 C14 128.6(2) . . ?
C13 N2 H2 115.7 . . ?
C14 N2 H2 115.7 . . ?
C5 N1 C6 122.2(2) . . ?
C5 N1 H1 118.9 . . ?
C6 N1 H1 118.9 . . ?
O3 C13 N2 124.3(3) . . ?
O3 C13 C6 121.3(2) . . ?
N2 C13 C6 114.4(2) . . ?
C18 C19 C14 118.6(2) . . ?
C18 C19 C20 119.5(3) . . ?
C14 C19 C20 122.0(2) . . ?
C15 C14 N2 122.1(3) . . ?
C15 C14 C19 119.2(2) . . ?
N2 C14 C19 118.8(2) . . ?
O4 C20 O5 122.0(3) . . ?
O4 C20 C19 125.4(3) . . ?
O5 C20 C19 112.6(2) . . ?
O2 C5 N1 124.6(3) . . ?
O2 C5 O1 125.7(3) . . ?
N1 C5 O1 109.7(2) . . ?
N1 C6 C7 111.3(2) . . ?
N1 C6 C13 109.9(2) . . ?
C7 C6 C13 111.3(2) . . ?
N1 C6 H6 108.1 . . ?
C7 C6 H6 108.1 . . ?
C13 C6 H6 108.1 . . ?
C12 C7 C8 117.4(3) . . ?
C12 C7 C6 123.8(3) . . ?
C8 C7 C6 118.8(3) . . ?
C17 C18 C19 121.5(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C9 C8 C7 121.8(3) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C15 C16 C17 121.4(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
O1 C1 C4 112.2(4) . . ?
O1 C1 C3 104.4(3) . . ?
C4 C1 C3 111.1(4) . . ?
O1 C1 C2 107.1(4) . . ?
C4 C1 C2 112.3(5) . . ?
C3 C1 C2 109.3(4) . . ?
C7 C12 C11 121.0(3) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C10 C11 C12 120.0(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
O3 C13 1.218(3) . ?
O1 C5 1.340(3) . ?
O1 C1 1.438(4) . ?
O5 C20 1.322(3) . ?
O5 C21 1.448(4) . ?
O4 C20 1.204(3) . ?
O2 C5 1.203(3) . ?
N2 C13 1.350(3) . ?
N2 C14 1.402(3) . ?
N2 H2 0.8600 . ?
N1 C5 1.339(3) . ?
N1 C6 1.446(3) . ?
N1 H1 0.8600 . ?
C13 C6 1.522(4) . ?
C19 C18 1.397(4) . ?
C19 C14 1.410(4) . ?
C19 C20 1.474(4) . ?
C14 C15 1.396(4) . ?
C6 C7 1.516(4) . ?
C6 H6 0.9800 . ?
C7 C12 1.358(4) . ?
C7 C8 1.373(4) . ?
C18 C17 1.366(4) . ?
C18 H18 0.9300 . ?
C15 C16 1.371(4) . ?
C15 H15 0.9300 . ?
C8 C9 1.372(5) . ?
C8 H8 0.9300 . ?
C16 C17 1.375(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C9 C10 1.337(6) . ?
C9 H9 0.9300 . ?
C1 C4 1.469(6) . ?
C1 C3 1.509(5) . ?
C1 C2 1.514(6) . ?
C12 C11 1.374(5) . ?
C12 H12 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C10 C11 1.364(6) . ?
C10 H10 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C11 H11 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
