#------------------------------------------------------------------------------
#$Date: 2019-11-22 19:37:28 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231350 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/65/4516513.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_4516513
loop_
_publ_author_name
'Krawczuk, Anna'
'Gryl, Marlena'
'Pitak, Mateusz B.'
'Stadnicka, Katarzyna'
_publ_section_title
;
 Electron Density Distribution of Urea in Co-crystals with Rigid and
 Flexible Dicarboxylic Acids
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5578
_journal_paper_doi               10.1021/acs.cgd.5b01253
_journal_volume                  15
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_iupac          'C5 H10 N2 O6'
_chemical_formula_moiety         'C4 H6 O5, C H4 N2 O'
_chemical_formula_sum            'C5 H10 N2 O6'
_chemical_formula_weight         194.15
_chemical_melting_point          403
_chemical_name_common            '(S)-(-)-malic acid urea addition compound'
_chemical_name_systematic
' '(S)-(-)-hydroxysuccinic acid urea addition compound''
_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'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             '27-Feb-02 T14:19:14-00:00'
_audit_creation_method           'XD routine XDCIF'
_cell_angle_alpha                90.00
_cell_angle_beta                 94.697(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6411(2)
_cell_length_b                   6.9162(2)
_cell_length_c                   9.0495(2)
_cell_measurement_reflns_used    4705
_cell_measurement_temperature    80(2)
_cell_measurement_theta_max      53.867
_cell_measurement_theta_min      0.998
_cell_measurement_wavelength     0.71073
_cell_volume                     414.26(2)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction
'HKL DENZO and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
Volkov et al, (2006), PLATON (Spek, 2003); 
ORTEP-3 for Windows (Farrugia, 1997); 
MERCURY (Version 3.3; Macrae et al., 2006)
;
_computing_publication_material  'Volkov et al, (2006)'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      80(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'ω scans at χ=55°'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13223
_diffrn_reflns_theta_full        53.37
_diffrn_reflns_theta_max         53.37
_diffrn_reflns_theta_min         3.67
_diffrn_source                   'Nonius KappaCCD'
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        HKL DENZO and Scalepack (Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.164
_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   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.904
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         9206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.021
_refine_ls_R_factor_gt           0.019
_refine_ls_shift/su_max          0.00004
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.025
_reflns_number_gt                9160
_reflns_number_total             9393
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg5b01253_si_003.cif
_cod_data_source_block           malurea
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4516513
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
O(11) 6.21(3) 0 0.001(11) -0.025(15) -0.070(8) 0.021(8) 0.001(8) -0.028(9)
0.063(10) -0.037(9) 0.022(7) -0.003(8) -0.023(11) -0.054(11) 0.013(8) 0.001(12)
-0.023(7) 0 0 0 0 0 0 0 0 0 0.9790(15) 1.02(2) 1.02(2) 1.02(2) 1.02(2) 1.02(2)
O(41) 6.18(3) 0 0.006(9) -0.013(16) -0.089(9) 0.020(8) 0.002(8) -0.014(9)
-0.083(8) 0.010(9) 0.003(9) -0.002(7) -0.031(9) -0.019(8) 0.028(10) 0.011(7)
0.007(12) 0 0 0 0 0 0 0 0 0 0.9790(15) 1.02(2) 1.02(2) 1.02(2) 1.02(2) 1.02(2)
O(51) 6.17(3) 0 -0.088(9) -0.002(16) -0.083(8) -0.051(8) -0.014(8) -0.014(9)
-0.052(8) -0.007(10) 0.022(7) 0.032(6) -0.022(12) 0.054(7) -0.010(12) -0.049(7)
0.008(12) 0 0 0 0 0 0 0 0 0 0.9790(15) 1.02(2) 1.02(2) 1.02(2) 1.02(2) 1.02(2)
O(12) 6.14(3) 0 0.037(16) -0.075(8) -0.076(11) -0.013(10) 0.000(9) 0.040(7)
0.008(8) 0.015(9) 0.081(11) 0.023(8) -0.038(8) 0.019(9) 0.030(9) -0.016(11)
0.027(8) 0 0 0 0 0 0 0 0 0 0.9790(15) 1.02(2) 1.02(2) 1.02(2) 1.02(2) 1.02(2)
O(42) 6.19(3) 0 -0.039(10) -0.059(13) -0.037(12) 0.030(10) 0.011(9) 0.063(8)
0.001(9) -0.015(9) 0.079(10) -0.001(9) -0.048(8) 0.037(9) 0.005(7) -0.020(8)
-0.006(10) 0 0 0 0 0 0 0 0 0 0.9790(15) 1.02(2) 1.02(2) 1.02(2) 1.02(2) 1.02(2)
O(3) 6.17(3) 0 -0.035(10) -0.103(15) -0.037(9) -0.020(8) -0.003(8) 0.046(8)
0.070(8) 0.007(8) 0.081(9) 0.017(7) 0.002(9) 0.045(9) 0.033(9) -0.030(10)
-0.057(8) 0 0 0 0 0 0 0 0 0 0.9790(15) 1.02(2) 1.02(2) 1.02(2) 1.02(2) 1.02(2)
N(51) 4.99(6) 0 0.006(15) -0.017(19) 0.00(2) 0.023(14) 0.009(11) -0.013(12)
0.013(12) -0.043(12) 0.140(19) -0.077(15) 0.061(18) 0.094(14) 0.036(14)
-0.008(14) -0.020(13) 0 0 0 0 0 0 0 0 0 0.989(4) 0.91(3) 0.91(3) 0.91(3)
0.91(3) 0.91(3)
N(52) 4.90(6) 0 -0.017(15) 0.01(3) 0.053(17) 0.031(13) 0.008(10) 0.016(13)
0.075(13) 0.043(11) 0.204(19) 0.015(11) -0.006(18) 0.116(15) 0.001(16)
-0.047(12) -0.017(17) 0 0 0 0 0 0 0 0 0 0.989(4) 0.91(3) 0.91(3) 0.91(3)
0.91(3) 0.91(3)
C(1) 4.07(4) 0 -0.13(3) -0.075(15) 0.076(15) 0.227(13) -0.016(14) 0.031(11)
-0.214(14) -0.001(13) 0.308(18) -0.05(2) 0.004(13) 0.251(18) 0.022(18)
-0.003(16) -0.010(16) 0 0 0 0 0 0 0 0 0 0.980(4) 0.961(14) 0.961(14) 0.961(14)
0.961(14) 0.961(14)
C(2) 3.84(6) 0 -0.057(16) -0.04(2) 0.03(2) 0.006(15) 0.011(12) 0.063(11)
-0.017(13) 0.033(12) 0.25(2) -0.049(16) 0.046(19) 0.001(14) -0.029(16)
0.007(15) -0.183(17) 0 0 0 0 0 0 0 0 0 0.980(4) 0.961(14) 0.961(14) 0.961(14)
0.961(14) 0.961(14)
C(3) 3.91(6) 0 0.019(15) -0.04(3) 0.020(17) 0.080(14) 0.002(12) 0.024(13)
0.074(12) 0.056(13) 0.240(18) 0.019(14) -0.03(2) -0.015(14) -0.035(18)
-0.050(16) -0.159(18) 0 0 0 0 0 0 0 0 0 0.980(4) 0.961(14) 0.961(14) 0.961(14)
0.961(14) 0.961(14)
C(4) 3.91(5) 0 0.059(15) -0.10(3) 0.064(16) 0.244(15) 0.017(10) -0.012(14)
-0.214(13) -0.016(14) 0.34(2) -0.019(14) -0.035(19) 0.266(18) 0.011(18)
-0.042(14) -0.007(19) 0 0 0 0 0 0 0 0 0 0.980(4) 0.961(14) 0.961(14) 0.961(14)
0.961(14) 0.961(14)
C(5) 3.93(6) 0 0.079(14) 0.00(3) 0.029(16) 0.194(13) -0.004(11) -0.043(16)
-0.198(13) 0.016(15) 0.37(2) -0.002(12) -0.03(2) 0.251(18) 0.02(2) 0.035(13)
0.07(2) 0 0 0 0 0 0 0 0 0 0.980(4) 0.961(14) 0.961(14) 0.961(14) 0.961(14)
0.961(14)
H(2A) 1.10(3) 0 0 0 0.13(2) 0.06(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.13 1.26 1.26 1.26 1.26 1.26
H(2B) 1.13(3) 0 0 0 0.167(19) 0.13(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.13 1.26 1.26 1.26 1.26 1.26
H(3) 1.02(3) 0 0 0 0.141(17) 0.09(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.13 1.26 1.26 1.26 1.26 1.26
H(521) 0.87(3) 0 0 0 0.192(19) 0.07(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.13 1.26 1.26 1.26 1.26 1.26
H(522) 0.95(3) 0 0 0 0.26(2) 0.16(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.13 1.26 1.26 1.26 1.26 1.26
H(511) 0.86(3) 0 0 0 0.231(17) 0.13(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.13 1.26 1.26 1.26 1.26 1.26
H(512) 0.84(3) 0 0 0 0.24(2) 0.05(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.13 1.26 1.26 1.26 1.26 1.26
H(3O) 0.90(3) 0 0 0 0.189(16) 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.13 1.26 1.26 1.26 1.26 1.26
H(42) 0.87(3) 0 0 0 0.100(18) 0.18(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.13 1.26 1.26 1.26 1.26 1.26
H(12) 0.87(3) 0 0 0 0.175(16) 0.14(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.13 1.26 1.26 1.26 1.26 1.26
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
O(11) O 0.52957(4) 0.36037(7) 0.09972(3) 0.014 Uani 1 2
O(41) O 0.23170(4) 0.38070(6) 0.39121(3) 0.013 Uani 1 2
O(51) O 0.84286(5) 0.38500(6) 0.58979(3) 0.014 Uani 1 2
O(12) O 0.45913(5) 0.33329(7) -0.14567(3) 0.015 Uani 1 2
O(42) O 0.14994(5) 0.15465(6) 0.21848(3) 0.014 Uani 1 2
O(3) O 0.19287(4) 0.66686(6) 0.17982(3) 0.012 Uani 1 2
N(51) N 0.71506(5) 0.21194(5) 0.39188(3) 0.015 Uani 1 2
N(52) N 0.72218(5) 0.54598(5) 0.38268(3) 0.015 Uani 1 2
C(1) C 0.41034(3) 0.37131(5) -0.00984(2) 0.01 Uani 1 2
C(2) C 0.19109(4) 0.42579(5) -0.00888(2) 0.011 Uani 1 2
C(3) C 0.12161(3) 0.48005(5) 0.14165(3) 0.01 Uani 1 2
C(4) C 0.17837(3) 0.33340(5) 0.26424(2) 0.01 Uani 1 2
C(5) C 0.75995(3) 0.381321 0.45905(2) 0.011 Uani 1 2
H(2A) H 0.099571 0.304452 -0.05287 0.027 Uani 1 2
H(2B) H 0.161307 0.547728 -0.084167 0.026 Uani 1 2
H(3) H -0.044191 0.487916 0.129109 0.027 Uani 1 2
H(521) H 0.642027 0.551506 0.282334 0.025 Uani 1 2
H(522) H 0.747376 0.672759 0.437602 0.026 Uani 1 2
H(511) H 0.630007 0.213163 0.293443 0.026 Uani 1 2
H(512) H 0.733463 0.093078 0.457384 0.027 Uani 1 2
H(3O) H 0.168781 0.704521 0.28127 0.023 Uani 1 2
H(42) H 0.161074 0.063696 0.301781 0.026 Uani 1 2
H(12) H 0.595069 0.278499 -0.146924 0.027 Uani 1 2
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(1) O(12) H(12) 112.56 1_555 1_555 1_555 yes
C(3) O(3) H(3O) 113.33 1_555 1_555 1_555 yes
O(11) C(1) O(12) 123.43(3) 1_555 1_555 1_555 yes
O(11) C(1) C(2) 125.10(2) 1_555 1_555 1_555 yes
O(12) C(1) C(2) 111.46(2) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 115.573(18) 1_555 1_555 1_555 yes
O(3) C(3) C(2) 108.99(2) 1_555 1_555 1_555 yes
O(3) C(3) C(4) 111.89(2) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 114.317(19) 1_555 1_555 1_555 yes
O(41) C(4) O(42) 124.97(3) 1_555 1_555 1_555 yes
O(41) C(4) C(3) 122.80(2) 1_555 1_555 1_555 yes
O(42) C(4) C(3) 112.09(2) 1_555 1_555 1_555 yes
O(51) C(5) N(51) 120.35(3) 1_555 1_555 1_555 yes
O(51) C(5) N(52) 120.83(3) 1_555 1_555 1_555 yes
N(51) C(5) N(52) 118.77(2) 1_555 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(11) C(1) 1.2194(3) 1_555 1_555 yes
O(41) C(4) 1.2191(3) 1_555 1_555 yes
O(51) C(5) 1.2638(3) 1_555 1_555 yes
O(12) C(1) 1.3230(3) 1_555 1_555 yes
O(12) H(12) 0.9800 1_555 1_555 yes
O(42) C(4) 1.3125(4) 1_555 1_555 yes
O(3) C(3) 1.4092(4) 1_555 1_555 yes
O(3) H(3O) 0.9800 1_555 1_555 yes
N(51) C(5) 1.3421(3) 1_555 1_555 yes
N(52) C(5) 1.3451(3) 1_555 1_555 yes
C(1) C(2) 1.5048(3) 1_555 1_555 yes
C(2) C(3) 1.5206(3) 1_555 1_555 yes
C(3) C(4) 1.5275(3) 1_555 1_555 yes
