#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:11:46 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229033 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/06/7230614.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_7230614
loop_
_publ_author_name
'Kumar, Vineet'
'Goswami, Pramod Kumar'
'Thaimattam, Ram'
'Ramanan, Arunachalam'
_publ_section_title
;
 Multicomponent solids of uracil derivatives -- orotic and isoorotic acids
;
_journal_issue                   25
_journal_name_full               CrystEngComm
_journal_page_first              3490
_journal_paper_doi               10.1039/C8CE00486B
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C5 H3 N2 O4, C5 H7 N2'
_chemical_formula_sum            'C10 H10 N4 O4'
_chemical_formula_weight         250.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-10-08
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_audit_update_record
;
2018-03-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.377(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.194(2)
_cell_length_b                   5.1402(10)
_cell_length_c                   17.488(3)
_cell_measurement_reflns_used    571
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.16
_cell_measurement_theta_min      2.67
_cell_volume                     1081.5(3)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.1112
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12101
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         1.693
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.795097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0451 before and 0.0290 after correction.
The Ratio of minimum to maximum transmission is 0.7951.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1667
_refine_ls_R_factor_gt           0.0806
_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)+(0.0496P)²+0.7910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1825
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1369
_reflns_number_total             2674
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00486b2.cif
_cod_data_source_block           vj220am
_cod_depositor_comments
'Adding full bibliography for 7230605--7230614.cif.'
_cod_original_cell_volume        1081.5(4)
_cod_database_code               7230614
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), N7(H7), C19(H19), N4(H4), C13(H13), C18(H18), C17(H17), C12(H12)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_shelx_shelxl_version_number     2017/1
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N5 N 0.8837(2) 0.2500(5) 0.46377(15) 0.0348(7) Uani 1 1 d .
H5 H 0.896568 0.377880 0.495698 0.042 Uiso 1 1 calc R
O3 O 1.05422(18) 0.3097(4) 0.43166(14) 0.0461(7) Uani 1 1 d .
O1 O 0.9021(2) -0.4442(5) 0.27536(16) 0.0547(7) Uani 1 1 d .
O2 O 0.7256(2) -0.4570(5) 0.29604(16) 0.0582(8) Uani 1 1 d .
C6 C 0.9661(3) 0.1902(6) 0.42242(18) 0.0347(8) Uani 1 1 d .
C2 C 0.8427(3) -0.1458(6) 0.36305(19) 0.0374(8) Uani 1 1 d .
N7 N 0.9410(2) -0.0134(5) 0.37071(17) 0.0464(8) Uani 1 1 d .
H7 H 0.989177 -0.058257 0.342327 0.056 Uiso 1 1 calc R
O4 O 0.7139(2) 0.1979(5) 0.49953(15) 0.0564(7) Uani 1 1 d .
C1 C 0.8225(3) -0.3706(6) 0.30556(19) 0.0393(9) Uani 1 1 d .
C19 C 0.7663(3) -0.0805(6) 0.40560(18) 0.0331(8) Uani 1 1 d .
H19 H 0.700155 -0.174129 0.399623 0.040 Uiso 1 1 calc R
C4 C 0.7816(3) 0.1276(6) 0.4601(2) 0.0380(8) Uani 1 1 d .
N1 N 0.8329(2) 0.0973(5) 0.18132(17) 0.0454(8) Uani 1 1 d .
H1A H 0.851644 0.224276 0.212765 0.054 Uiso 1 1 calc R
H1B H 0.883076 0.012135 0.162489 0.054 Uiso 1 1 calc R
N4 N 0.6505(2) 0.1681(5) 0.19189(16) 0.0411(7) Uani 1 1 d .
H4 H 0.672216 0.292713 0.223548 0.049 Uiso 1 1 calc R
C15 C 0.7271(3) 0.0330(6) 0.16193(18) 0.0349(8) Uani 1 1 d .
C13 C 0.5403(3) 0.1176(7) 0.1747(2) 0.0551(10) Uani 1 1 d .
H13 H 0.490332 0.218123 0.196739 0.066 Uiso 1 1 calc R
C18 C 0.6891(3) -0.1732(7) 0.1113(2) 0.0466(9) Uani 1 1 d .
H18 H 0.739741 -0.274174 0.089983 0.056 Uiso 1 1 calc R
C17 C 0.5795(3) -0.2243(8) 0.0938(2) 0.0557(11) Uani 1 1 d .
H17 H 0.555015 -0.359343 0.059869 0.067 Uiso 1 1 calc R
C12 C 0.5024(3) -0.0773(8) 0.1258(2) 0.0609(12) Uani 1 1 d .
H12 H 0.426747 -0.112636 0.113776 0.073 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
C6 N5 H5 116.4
C6 N5 C4 127.2(3)
C4 N5 H5 116.4
N5 C6 N7 114.4(3)
O3 C6 N5 121.5(3)
O3 C6 N7 124.1(3)
N7 C2 C1 119.2(3)
C19 C2 N7 120.3(3)
C19 C2 C1 120.5(3)
C6 N7 H7 118.7
C2 N7 C6 122.5(3)
C2 N7 H7 118.7
O1 C1 O2 128.8(3)
O1 C1 C2 117.3(3)
O2 C1 C2 113.9(3)
C2 C19 H19 118.8
C2 C19 C4 122.5(3)
C4 C19 H19 118.8
N5 C4 C19 113.1(3)
O4 C4 N5 121.8(3)
O4 C4 C19 125.2(3)
H1A N1 H1B 120.0
C15 N1 H1A 120.0
C15 N1 H1B 120.0
C15 N4 H4 118.5
C15 N4 C13 123.0(3)
C13 N4 H4 118.5
N1 C15 N4 119.0(3)
N1 C15 C18 123.8(3)
N4 C15 C18 117.2(3)
N4 C13 H13 119.7
C12 C13 N4 120.6(4)
C12 C13 H13 119.7
C15 C18 H18 119.9
C17 C18 C15 120.1(4)
C17 C18 H18 119.9
C18 C17 H17 119.6
C18 C17 C12 120.8(3)
C12 C17 H17 119.6
C13 C12 C17 118.2(4)
C13 C12 H12 120.9
C17 C12 H12 120.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N5 H5 0.8600
N5 C6 1.365(4)
N5 C4 1.387(4)
O3 C6 1.225(4)
O1 C1 1.238(4)
O2 C1 1.248(4)
C6 N7 1.384(4)
C2 N7 1.366(4)
C2 C1 1.525(4)
C2 C19 1.327(4)
N7 H7 0.8600
O4 C4 1.215(4)
C19 H19 0.9300
C19 C4 1.424(4)
N1 H1A 0.8600
N1 H1B 0.8600
N1 C15 1.322(4)
N4 H4 0.8600
N4 C15 1.337(4)
N4 C13 1.353(4)
C15 C18 1.410(5)
C13 H13 0.9300
C13 C12 1.349(5)
C18 H18 0.9300
C18 C17 1.347(5)
C17 H17 0.9300
C17 C12 1.392(5)
C12 H12 0.9300
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
N5 C6 N7 C2 -1.2(4)
O3 C6 N7 C2 178.6(3)
C6 N5 C4 O4 -179.7(3)
C6 N5 C4 C19 -0.4(4)
C2 C19 C4 N5 -0.4(5)
C2 C19 C4 O4 178.8(3)
N7 C2 C1 O1 8.9(5)
N7 C2 C1 O2 -171.6(3)
N7 C2 C19 C4 0.4(5)
C1 C2 N7 C6 -179.0(3)
C1 C2 C19 C4 179.9(3)
C19 C2 N7 C6 0.4(5)
C19 C2 C1 O1 -170.6(3)
C19 C2 C1 O2 8.9(5)
C4 N5 C6 O3 -178.6(3)
C4 N5 C6 N7 1.2(4)
N1 C15 C18 C17 -179.2(3)
N4 C15 C18 C17 1.2(5)
N4 C13 C12 C17 0.0(6)
C15 N4 C13 C12 0.5(6)
C15 C18 C17 C12 -0.7(6)
C13 N4 C15 N1 179.3(3)
C13 N4 C15 C18 -1.1(5)
C18 C17 C12 C13 0.1(6)
