#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/49/4514980.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_4514980
loop_
_publ_author_name
'Sasmal, Supriya'
'Roy Chowdhury, Srayoshi'
'Podder, Debasish'
'Haldar, Debasish'
_publ_section_title
;
 Urea-Appended Amino Acid To Vitalize Yeast Growth, Enhance Fermentation,
 and Promote Ethanol Production.
;
_journal_issue                   8
_journal_name_full               'ACS omega'
_journal_page_first              13172
_journal_page_last               13179
_journal_paper_doi               10.1021/acsomega.9b01260
_journal_volume                  4
_journal_year                    2019
_chemical_absolute_configuration s
_chemical_formula_moiety         'C7 H17 N5 O4'
_chemical_formula_sum            'C7 H17 N5 O4'
_chemical_formula_weight         235.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.066(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5481(2)
_cell_length_b                   8.9419(3)
_cell_length_c                   7.9881(2)
_cell_measurement_reflns_used    3684
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      25.0070
_cell_measurement_theta_min      2.5260
_cell_volume                     537.79(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -122.00 -55.00   1.00    2.00    --  -25.76 178.00-180.00   67
  2  ω    -20.00  83.00   1.00    2.00    --   27.17 -99.00 150.00  103
  3  ω    -59.00 115.00   1.00    2.00    --   27.17  19.00 -60.00  174
  4  ω    -20.00  30.00   1.00    2.00    --  -25.76 -99.00 -60.00   50
  5  ω    -61.00 113.00   1.00    2.00    --   27.17 -19.00 150.00  174
  6  ω    -11.00 104.00   1.00    2.00    --   27.17  57.00  90.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0098270000
_diffrn_orient_matrix_UB_12      0.0788777000
_diffrn_orient_matrix_UB_13      0.0005846000
_diffrn_orient_matrix_UB_21      -0.0722929000
_diffrn_orient_matrix_UB_22      0.0064708000
_diffrn_orient_matrix_UB_23      0.0516663000
_diffrn_orient_matrix_UB_31      0.0596049000
_diffrn_orient_matrix_UB_32      -0.0051123000
_diffrn_orient_matrix_UB_33      0.0725043000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4729
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.556
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.25898
_exptl_crystal_size_mid          0.2359
_exptl_crystal_size_min          0.1158
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(6)
_refine_ls_extinction_coef       0.055(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1819
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0250
_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)+(0.0272P)²+0.1007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0590
_refine_ls_wR_factor_ref         0.0595
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_full    0.912
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                1769
_reflns_number_total             1819
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao9b01260_si_001.cif
_cod_data_source_block           uarg
_cod_database_code               4514980
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O'
_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_max   0.986
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 93.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Fixed occupancy and ADP/Uiso:
 H4A, H4B
2.b Free rotating group:
 O4(H4E,H4F)
2.c Ternary CH refined with riding coordinates:
 C2(H2A)
2.d Secondary CH2 refined with riding coordinates:
 C4(H4C,H4D), C5(H5C,H5D), C6(H6A,H6B)
2.e Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3)
2.f X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N5(H5A,H5B)
;
_olex2_date_sample_data_collection 2018-04-12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.830
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.2077(2) 0.06492(18) 1.17128(19) 0.0160(4) Uani 1 1 d .
O2 O -0.12249(19) 0.01808(18) 0.88637(18) 0.0144(4) Uani 1 1 d .
O3 O 0.01840(19) 0.05433(18) 0.65341(18) 0.0144(4) Uani 1 1 d .
N1 N 0.0898(3) -0.1246(2) 1.3134(2) 0.0157(4) Uani 1 1 d .
H1A H 0.094319 -0.072657 1.404265 0.019 Uiso 1 1 calc R
H1B H 0.048502 -0.214202 1.312866 0.019 Uiso 1 1 calc R
N2 N 0.1408(2) -0.1544(2) 1.0361(2) 0.0126(4) Uani 1 1 d .
H2 H 0.122652 -0.248387 1.050104 0.015 Uiso 1 1 calc R
N3 N 0.3525(2) -0.4251(2) 0.4980(2) 0.0121(4) Uani 1 1 d .
H3 H 0.250375 -0.433607 0.443962 0.015 Uiso 1 1 calc R
N4 N 0.6486(2) -0.3567(2) 0.4884(3) 0.0150(4) Uani 1 1 d .
H4A H 0.666(3) -0.378(3) 0.598(3) 0.018 Uiso 1 1 d .
H4B H 0.742(3) -0.360(3) 0.425(3) 0.018 Uiso 1 1 d .
N5 N 0.4618(2) -0.3596(2) 0.2484(2) 0.0154(4) Uani 1 1 d .
H5A H 0.358748 -0.374999 0.198287 0.018 Uiso 1 1 calc R
H5B H 0.548396 -0.330710 0.191956 0.018 Uiso 1 1 calc R
C1 C 0.1474(3) -0.0654(3) 1.1719(3) 0.0127(5) Uani 1 1 d .
C2 C 0.1627(3) -0.1008(2) 0.8667(3) 0.0117(5) Uani 1 1 d .
H2A H 0.271601 -0.040934 0.868912 0.014 Uiso 1 1 calc R
C3 C 0.0064(3) -0.0021(3) 0.7980(3) 0.0115(5) Uani 1 1 d .
C4 C 0.1846(3) -0.2353(3) 0.7509(3) 0.0132(5) Uani 1 1 d .
H4C H 0.084234 -0.301870 0.759626 0.016 Uiso 1 1 calc R
H4D H 0.181774 -0.200005 0.635939 0.016 Uiso 1 1 calc R
C5 C 0.3545(3) -0.3233(3) 0.7891(3) 0.0133(5) Uani 1 1 d .
H5C H 0.361207 -0.354853 0.905530 0.016 Uiso 1 1 calc R
H5D H 0.455663 -0.259195 0.773423 0.016 Uiso 1 1 calc R
C6 C 0.3643(3) -0.4608(3) 0.6766(3) 0.0125(5) Uani 1 1 d .
H6A H 0.475315 -0.512585 0.704847 0.015 Uiso 1 1 calc R
H6B H 0.268245 -0.528352 0.699139 0.015 Uiso 1 1 calc R
C7 C 0.4870(3) -0.3806(2) 0.4128(3) 0.0118(5) Uani 1 1 d .
O4 O 0.2678(2) -0.72813(19) 0.9342(2) 0.0192(4) Uani 1 1 d .
H4E H 0.250955 -0.793120 1.009123 0.029 Uiso 1 1 d G
H4F H 0.233366 -0.646393 0.975381 0.029 Uiso 1 1 d G
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
C1 N2 C2 123.7(2)
C7 N3 C6 125.01(18)
O1 C1 N1 120.5(2)
O1 C1 N2 122.8(2)
N2 C1 N1 116.6(2)
N2 C2 C3 112.62(17)
N2 C2 C4 109.07(18)
C4 C2 C3 110.26(17)
O2 C3 O3 124.2(2)
O2 C3 C2 119.08(19)
O3 C3 C2 116.68(18)
C5 C4 C2 114.31(19)
C4 C5 C6 112.02(17)
N3 C6 C5 113.38(18)
N3 C7 N4 121.5(2)
N3 C7 N5 119.35(19)
N5 C7 N4 119.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.251(3)
O2 C3 1.255(3)
O3 C3 1.269(3)
N1 C1 1.348(3)
N2 C1 1.343(3)
N2 C2 1.456(3)
N3 C6 1.458(3)
N3 C7 1.323(3)
N4 C7 1.339(3)
N5 C7 1.326(3)
C2 C3 1.543(3)
C2 C4 1.533(3)
C4 C5 1.517(3)
C5 C6 1.528(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168345512
