#------------------------------------------------------------------------------
#$Date: 2022-05-07 01:31:54 +0300 (Sat, 07 May 2022) $
#$Revision: 275152 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/48/7244897.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_7244897
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           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   'P 1 21 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                90.00
_cell_angle_beta                 105.531(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9889(9)
_cell_length_b                   10.8567(12)
_cell_length_c                   9.9953(10)
_cell_measurement_reflns_used    4790
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.31
_cell_measurement_theta_min      2.56
_cell_volume                     1044.38(18)
_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-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  0.0884
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24291
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.222
_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         0.151
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(15)
_refine_ls_extinction_coef       0.039(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0468
_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+0.1716P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                2708
_reflns_number_total             3657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ce00158f2.cif
_cod_data_source_block           antphg_gd_bhm_0ma_a
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7244897
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
O1 O 0.1728(2) 0.7174(2) 0.5522(2) 0.0638(6) Uani 1 1 d . . .
O3 O 0.3788(2) 0.4280(2) 0.7681(2) 0.0653(6) Uani 1 1 d . . .
O2 O 0.2268(2) 0.6884(2) 0.3481(2) 0.0660(6) Uani 1 1 d . . .
N1 N 0.2836(2) 0.5497(2) 0.5260(2) 0.0535(6) Uani 1 1 d . . .
H1 H 0.2884 0.5424 0.6128 0.064 Uiso 1 1 calc R . .
N2 N 0.5685(2) 0.3180(2) 0.7761(2) 0.0527(6) Uani 1 1 d . . .
H2 H 0.6169 0.2766 0.7325 0.063 Uiso 1 1 calc R . .
O5 O 0.6384(3) 0.4817(3) 1.0957(3) 0.0922(9) Uani 1 1 d . . .
O4 O 0.6826(3) 0.5397(3) 0.8982(3) 0.0921(9) Uani 1 1 d . . .
C5 C 0.2277(3) 0.6560(3) 0.4646(3) 0.0525(7) Uani 1 1 d . . .
C12 C 0.4497(3) 0.3712(3) 0.7056(3) 0.0508(7) Uani 1 1 d . . .
C6 C 0.3347(3) 0.4501(3) 0.4652(3) 0.0538(7) Uani 1 1 d . . .
C13 C 0.6161(3) 0.3301(3) 0.9268(3) 0.0508(7) Uani 1 1 d . . .
H13 H 0.5420 0.3016 0.9667 0.061 Uiso 1 1 calc R . .
C20 C 0.6474(3) 0.4630(3) 0.9671(4) 0.0626(9) Uani 1 1 d . . .
C1 C 0.0981(4) 0.8343(3) 0.5126(3) 0.0672(9) Uani 1 1 d . . .
C11 C 0.4105(3) 0.3578(3) 0.5519(3) 0.0533(7) Uani 1 1 d . . .
C14 C 0.7437(3) 0.2506(3) 0.9836(3) 0.0504(7) Uani 1 1 d . . .
C10 C 0.4478(3) 0.2518(4) 0.4916(4) 0.0716(10) Uani 1 1 d . . .
H10 H 0.4938 0.1885 0.5482 0.086 Uiso 1 1 calc R . .
C15 C 0.8712(3) 0.2872(3) 0.9705(4) 0.0679(9) Uani 1 1 d . . .
H15 H 0.8796 0.3609 0.9259 0.082 Uiso 1 1 calc R . .
C7 C 0.3086(4) 0.4372(4) 0.3223(3) 0.0736(10) Uani 1 1 d . . .
H7 H 0.2622 0.4992 0.2636 0.088 Uiso 1 1 calc R . .
C19 C 0.7343(4) 0.1441(4) 1.0507(4) 0.0724(10) Uani 1 1 d . . .
H19 H 0.6485 0.1193 1.0609 0.087 Uiso 1 1 calc R . .
C9 C 0.4175(4) 0.2395(5) 0.3495(4) 0.0936(14) Uani 1 1 d . . .
H9 H 0.4419 0.1682 0.3101 0.112 Uiso 1 1 calc R . .
C8 C 0.3514(4) 0.3329(5) 0.2674(4) 0.0902(13) Uani 1 1 d . . .
H8 H 0.3346 0.3262 0.1715 0.108 Uiso 1 1 calc R . .
C17 C 0.9761(5) 0.1095(5) 1.0921(4) 0.0907(13) Uani 1 1 d . . .
H17 H 1.0551 0.0630 1.1309 0.109 Uiso 1 1 calc R . .
C2 C 0.0567(5) 0.8674(4) 0.6426(4) 0.0881(12) Uani 1 1 d . . .
H2A H -0.0052 0.8057 0.6605 0.132 Uiso 1 1 calc R . .
H2B H 0.0108 0.9459 0.6304 0.132 Uiso 1 1 calc R . .
H2C H 0.1381 0.8716 0.7197 0.132 Uiso 1 1 calc R . .
C16 C 0.9860(4) 0.2154(4) 1.0230(4) 0.0823(12) Uani 1 1 d . . .
H16 H 1.0716 0.2393 1.0112 0.099 Uiso 1 1 calc R . .
C18 C 0.8496(5) 0.0716(5) 1.1043(5) 0.0979(14) Uani 1 1 d . . .
H18 H 0.8412 -0.0023 1.1483 0.118 Uiso 1 1 calc R . .
C4 C -0.0272(5) 0.8099(5) 0.3919(4) 0.1086(17) Uani 1 1 d . . .
H4A H 0.0029 0.7897 0.3110 0.163 Uiso 1 1 calc R . .
H4B H -0.0847 0.8821 0.3737 0.163 Uiso 1 1 calc R . .
H4C H -0.0793 0.7423 0.4142 0.163 Uiso 1 1 calc R . .
C3 C 0.1957(6) 0.9284(5) 0.4807(6) 0.1140(17) Uani 1 1 d . . .
H3A H 0.2796 0.9305 0.5551 0.171 Uiso 1 1 calc R . .
H3B H 0.1524 1.0080 0.4710 0.171 Uiso 1 1 calc R . .
H3C H 0.2174 0.9067 0.3958 0.171 Uiso 1 1 calc R . .
C21 C 0.6818(8) 0.6010(4) 1.1536(6) 0.145(3) Uani 1 1 d . . .
H21A H 0.7814 0.6046 1.1821 0.217 Uiso 1 1 calc R . .
H21B H 0.6461 0.6149 1.2324 0.217 Uiso 1 1 calc R . .
H21C H 0.6468 0.6632 1.0848 0.217 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 121.6(2) . . ?
C5 N1 C6 127.9(2) . . ?
C5 N1 H1 116.0 . . ?
C6 N1 H1 116.0 . . ?
C12 N2 C13 120.2(2) . . ?
C12 N2 H2 119.9 . . ?
C13 N2 H2 119.9 . . ?
C20 O5 C21 115.8(4) . . ?
O2 C5 O1 126.0(3) . . ?
O2 C5 N1 125.2(3) . . ?
O1 C5 N1 108.8(3) . . ?
O3 C12 N2 120.0(3) . . ?
O3 C12 C11 123.1(3) . . ?
N2 C12 C11 116.9(3) . . ?
C7 C6 N1 122.3(3) . . ?
C7 C6 C11 119.0(3) . . ?
N1 C6 C11 118.7(3) . . ?
N2 C13 C20 110.4(2) . . ?
N2 C13 C14 110.1(2) . . ?
C20 C13 C14 110.6(3) . . ?
N2 C13 H13 108.6 . . ?
C20 C13 H13 108.6 . . ?
C14 C13 H13 108.6 . . ?
O4 C20 O5 124.0(3) . . ?
O4 C20 C13 125.9(3) . . ?
O5 C20 C13 110.0(3) . . ?
O1 C1 C3 109.4(3) . . ?
O1 C1 C2 102.1(3) . . ?
C3 C1 C2 111.3(4) . . ?
O1 C1 C4 108.4(3) . . ?
C3 C1 C4 113.3(4) . . ?
C2 C1 C4 111.7(3) . . ?
C10 C11 C6 118.9(3) . . ?
C10 C11 C12 120.1(3) . . ?
C6 C11 C12 121.1(3) . . ?
C19 C14 C15 119.0(3) . . ?
C19 C14 C13 120.6(3) . . ?
C15 C14 C13 120.4(3) . . ?
C9 C10 C11 121.0(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C14 C19 C18 121.2(4) . . ?
C14 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C8 C9 C10 119.2(4) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C16 C17 C18 119.7(4) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
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 . . ?
C17 C16 C15 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C17 C18 C19 119.3(4) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 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 . . ?
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 . . ?
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 . . ?
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
O1 C5 1.330(4) . ?
O1 C1 1.472(4) . ?
O3 C12 1.228(3) . ?
O2 C5 1.215(4) . ?
N1 C5 1.356(4) . ?
N1 C6 1.401(4) . ?
N1 H1 0.8600 . ?
N2 C12 1.338(3) . ?
N2 C13 1.459(4) . ?
N2 H2 0.8600 . ?
O5 C20 1.328(4) . ?
O5 C21 1.437(6) . ?
O4 C20 1.192(4) . ?
C12 C11 1.487(4) . ?
C6 C7 1.389(4) . ?
C6 C11 1.407(4) . ?
C13 C20 1.508(5) . ?
C13 C14 1.518(4) . ?
C13 H13 0.9800 . ?
C1 C3 1.504(6) . ?
C1 C2 1.509(5) . ?
C1 C4 1.511(6) . ?
C11 C10 1.395(5) . ?
C14 C19 1.352(5) . ?
C14 C15 1.374(4) . ?
C10 C9 1.377(5) . ?
C10 H10 0.9300 . ?
C15 C16 1.370(5) . ?
C15 H15 0.9300 . ?
C7 C8 1.375(6) . ?
C7 H7 0.9300 . ?
C19 C18 1.379(5) . ?
C19 H19 0.9300 . ?
C9 C8 1.359(6) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C17 C16 1.358(6) . ?
C17 C18 1.365(6) . ?
C17 H17 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C16 H16 0.9300 . ?
C18 H18 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
