#------------------------------------------------------------------------------
#$Date: 2022-05-07 01:31:54 +0300 (Sat, 07 May 2022) $
#$Revision: 275152 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/49/7244900.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_7244900
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                109.577(2)
_cell_angle_beta                 98.666(2)
_cell_angle_gamma                117.160(2)
_cell_formula_units_Z            2
_cell_length_a                   10.5787(6)
_cell_length_b                   10.9535(6)
_cell_length_c                   11.4597(7)
_cell_measurement_reflns_used    5093
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      2.23
_cell_volume                     1037.58(11)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0507
_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            30304
_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    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       niddle
_exptl_crystal_F_000             408.0
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0541
_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+0.4187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1860
_reflns_number_gt                2472
_reflns_number_total             3654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ce00158f2.cif
_cod_data_source_block           adgdphgoant_0m_a
_cod_original_cell_volume        1037.58(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7244900
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 0.4191(2) 0.4662(2) 0.62548(19) 0.0611(5) Uani 1 1 d . . .
O5 O 0.3867(2) 0.2620(2) 1.07954(19) 0.0658(6) Uani 1 1 d . . .
O1 O 0.88723(19) 0.6550(2) 0.6175(2) 0.0644(6) Uani 1 1 d . . .
O4 O 0.4709(3) 0.2344(2) 0.9132(2) 0.0666(6) Uani 1 1 d . . .
O2 O 0.8705(2) 0.5315(2) 0.7439(2) 0.0724(6) Uani 1 1 d . . .
N2 N 0.4074(2) 0.3376(2) 0.7474(2) 0.0472(5) Uani 1 1 d . . .
H2 H 0.4396 0.2838 0.7643 0.057 Uiso 1 1 calc R . .
N1 N 0.6652(2) 0.4590(2) 0.5806(2) 0.0565(6) Uani 1 1 d . . .
H1 H 0.6342 0.4729 0.5153 0.068 Uiso 1 1 calc R . .
C14 C 0.3125(3) 0.3601(3) 0.8135(2) 0.0447(6) Uani 1 1 d . . .
C20 C 0.3977(3) 0.2725(3) 0.9692(2) 0.0474(6) Uani 1 1 d . . .
C13 C 0.4549(3) 0.3894(3) 0.6606(2) 0.0449(6) Uani 1 1 d . . .
C19 C 0.3105(3) 0.3328(3) 0.9257(2) 0.0446(6) Uani 1 1 d . . .
C5 C 0.8129(3) 0.5475(3) 0.6557(3) 0.0489(6) Uani 1 1 d . . .
C6 C 0.5548(3) 0.3399(3) 0.6054(3) 0.0463(6) Uani 1 1 d . . .
H6 H 0.6106 0.3281 0.6728 0.056 Uiso 1 1 calc R . .
C7 C 0.4602(3) 0.1858(3) 0.4807(3) 0.0490(6) Uani 1 1 d . . .
C15 C 0.2195(3) 0.4066(3) 0.7720(3) 0.0576(7) Uani 1 1 d . . .
H15 H 0.2168 0.4210 0.6964 0.069 Uiso 1 1 calc R . .
C18 C 0.2209(3) 0.3604(3) 0.9937(3) 0.0576(7) Uani 1 1 d . . .
H18 H 0.2201 0.3443 1.0684 0.069 Uiso 1 1 calc R . .
C8 C 0.5321(4) 0.1182(4) 0.4239(3) 0.0675(8) Uani 1 1 d . . .
H8 H 0.6370 0.1673 0.4629 0.081 Uiso 1 1 calc R . .
C16 C 0.1316(3) 0.4314(4) 0.8418(3) 0.0694(8) Uani 1 1 d . . .
H16 H 0.0701 0.4626 0.8129 0.083 Uiso 1 1 calc R . .
C17 C 0.1336(3) 0.4106(4) 0.9537(3) 0.0692(8) Uani 1 1 d . . .
H17 H 0.0760 0.4305 1.0018 0.083 Uiso 1 1 calc R . .
C9 C 0.4515(5) -0.0211(4) 0.3102(4) 0.0840(11) Uani 1 1 d . . .
H9 H 0.5027 -0.0634 0.2720 0.101 Uiso 1 1 calc R . .
C1 C 1.0440(3) 0.7787(4) 0.6917(4) 0.0807(10) Uani 1 1 d . . .
C21 C 0.4647(4) 0.2003(4) 1.1291(3) 0.0838(11) Uani 1 1 d . . .
H21A H 0.4162 0.0929 1.0689 0.126 Uiso 1 1 calc R . .
H21B H 0.4606 0.2114 1.2149 0.126 Uiso 1 1 calc R . .
H21C H 0.5691 0.2556 1.1365 0.126 Uiso 1 1 calc R . .
C12 C 0.3063(4) 0.1083(4) 0.4221(4) 0.0895(11) Uani 1 1 d . . .
H12 H 0.2544 0.1509 0.4583 0.107 Uiso 1 1 calc R . .
C10 C 0.2999(6) -0.0959(4) 0.2543(4) 0.0971(12) Uani 1 1 d . . .
H10 H 0.2455 -0.1906 0.1782 0.117 Uiso 1 1 calc R . .
C4 C 1.0777(4) 0.8739(4) 0.6181(5) 0.1017(13) Uani 1 1 d . . .
H4A H 1.0556 0.8098 0.5270 0.153 Uiso 1 1 calc R . .
H4B H 1.1834 0.9564 0.6584 0.153 Uiso 1 1 calc R . .
H4C H 1.0157 0.9163 0.6218 0.153 Uiso 1 1 calc R . .
C11 C 0.2261(5) -0.0323(5) 0.3098(5) 0.1188(16) Uani 1 1 d . . .
H11 H 0.1208 -0.0841 0.2716 0.143 Uiso 1 1 calc R . .
C3 C 1.1453(5) 0.7220(8) 0.6976(8) 0.200(4) Uani 1 1 d . . .
H3A H 1.1299 0.6725 0.7539 0.299 Uiso 1 1 calc R . .
H3B H 1.2494 0.8072 0.7330 0.299 Uiso 1 1 calc R . .
H3C H 1.1229 0.6491 0.6099 0.299 Uiso 1 1 calc R . .
C2 C 1.0523(8) 0.8734(6) 0.8284(6) 0.200(4) Uani 1 1 d . . .
H2A H 0.9701 0.8893 0.8186 0.300 Uiso 1 1 calc R . .
H2B H 1.1478 0.9715 0.8724 0.300 Uiso 1 1 calc R . .
H2C H 1.0442 0.8189 0.8802 0.300 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
C20 O5 C21 117.0(2) . . ?
C5 O1 C1 122.0(2) . . ?
C13 N2 C14 128.5(2) . . ?
C13 N2 H2 115.8 . . ?
C14 N2 H2 115.8 . . ?
C5 N1 C6 122.2(2) . . ?
C5 N1 H1 118.9 . . ?
C6 N1 H1 118.9 . . ?
C15 C14 N2 122.5(2) . . ?
C15 C14 C19 118.9(2) . . ?
N2 C14 C19 118.6(2) . . ?
O4 C20 O5 121.8(2) . . ?
O4 C20 C19 125.7(2) . . ?
O5 C20 C19 112.4(2) . . ?
O3 C13 N2 124.1(2) . . ?
O3 C13 C6 121.6(2) . . ?
N2 C13 C6 114.3(2) . . ?
C18 C19 C14 118.5(2) . . ?
C18 C19 C20 119.7(2) . . ?
C14 C19 C20 121.7(2) . . ?
O2 C5 N1 124.6(2) . . ?
O2 C5 O1 125.5(2) . . ?
N1 C5 O1 110.0(2) . . ?
N1 C6 C7 111.2(2) . . ?
N1 C6 C13 109.81(19) . . ?
C7 C6 C13 111.46(19) . . ?
N1 C6 H6 108.1 . . ?
C7 C6 H6 108.1 . . ?
C13 C6 H6 108.1 . . ?
C12 C7 C8 117.5(3) . . ?
C12 C7 C6 123.6(2) . . ?
C8 C7 C6 118.9(2) . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C18 C19 121.7(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 119.5(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
O1 C1 C3 112.1(4) . . ?
O1 C1 C4 104.1(3) . . ?
C3 C1 C4 111.2(3) . . ?
O1 C1 C2 106.8(3) . . ?
C3 C1 C2 113.1(5) . . ?
C4 C1 C2 109.0(4) . . ?
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 . . ?
C7 C12 C11 121.0(3) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C9 C10 C11 119.4(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
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 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
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 . . ?
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) . ?
O5 C20 1.325(3) . ?
O5 C21 1.444(3) . ?
O1 C5 1.342(3) . ?
O1 C1 1.436(3) . ?
O4 C20 1.205(3) . ?
O2 C5 1.206(3) . ?
N2 C13 1.354(3) . ?
N2 C14 1.405(3) . ?
N2 H2 0.8600 . ?
N1 C5 1.332(3) . ?
N1 C6 1.451(3) . ?
N1 H1 0.8600 . ?
C14 C15 1.390(3) . ?
C14 C19 1.415(3) . ?
C20 C19 1.474(3) . ?
C13 C6 1.518(4) . ?
C19 C18 1.388(4) . ?
C6 C7 1.518(4) . ?
C6 H6 0.9800 . ?
C7 C12 1.360(4) . ?
C7 C8 1.376(4) . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C18 C17 1.367(4) . ?
C18 H18 0.9300 . ?
C8 C9 1.377(5) . ?
C8 H8 0.9300 . ?
C16 C17 1.374(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C9 C10 1.339(5) . ?
C9 H9 0.9300 . ?
C1 C3 1.468(6) . ?
C1 C4 1.505(4) . ?
C1 C2 1.524(7) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C12 C11 1.378(5) . ?
C12 H12 0.9300 . ?
C10 C11 1.359(5) . ?
C10 H10 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C11 H11 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
