#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:15:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180496 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/65/7216545.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_7216545
loop_
_publ_author_name
'Gryl, M.'
'Seidler, T.'
'Stadnicka, K.'
'Matulková, I.'
'Němec, I.'
'Tesařová, N.'
'Němec, P.'
_publ_section_title
;
 The crystal structure and optical properties of a pharmaceutical
 co-crystal -- the case of the melamine--barbital addition compound
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              5765
_journal_paper_doi               10.1039/c4ce00178h
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C8 H12 N2 O3, C3 H6 N6'
_chemical_formula_sum            'C11 H18 N8 O3'
_chemical_formula_weight         310.33
_chemical_name_common            'melamine barbital addition compound'
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_symmetry_space_group_name_Hall  'P 2ac -2'
_symmetry_space_group_name_H-M   'P m n 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5289(3)
_cell_length_b                   9.1191(3)
_cell_length_c                   8.6670(2)
_cell_measurement_reflns_used    8667
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      45.3807
_cell_measurement_theta_min      3.0857
_cell_volume                     753.12(4)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_molecular_graphics    'Ortep3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR-97 (ALTOMARE et al., 1999)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32340
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.498
_diffrn_reflns_theta_min         3.092
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 0 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.000
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         6553
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      0.898
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0453
_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)+(0.0462P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3971
_reflns_number_total             6553
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce00178h2.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 7216545.cif.'
_cod_database_code               7216545
#BEGIN Tags that were not found in dictionaries:
_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_min   0.977
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y, z'
'x+1/2, -y, 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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O2A O 0.5000 0.14287(14) 0.64262(13) 0.0160(2) Uani 1 2 d S T P
N3B N 0.12557(9) 0.12688(10) 0.71045(10) 0.01222(15) Uani 1 1 d . . .
N4B N 0.0000 0.22349(17) 0.91277(15) 0.0158(2) Uani 1 2 d DS T P
N1B N 0.0000 0.02349(15) 0.49635(16) 0.0131(2) Uani 1 2 d S T P
C4B C 0.0000 0.15799(16) 0.77447(16) 0.0110(2) Uani 1 2 d S T P
H4B H -0.0840(12) 0.2679(16) 0.9497(18) 0.013 Uiso 1 1 d D U .
C5A C 0.5000 0.43922(17) 1.00219(19) 0.0140(3) Uani 1 2 d S T P
C2A C 0.5000 0.22795(17) 0.75191(17) 0.0122(2) Uani 1 2 d S T P
N1A N 0.37722(10) 0.27840(11) 0.81509(11) 0.01347(16) Uani 1 1 d D . .
H1A H 0.2885(13) 0.2321(16) 0.7811(18) 0.016 Uiso 1 1 d D U .
C4A C 0.36693(12) 0.37011(12) 0.94041(12) 0.01475(19) Uani 1 1 d . . .
N2B N 0.24074(10) 0.02946(12) 0.50216(12) 0.01872(19) Uani 1 1 d D . .
H2B2 H 0.3285(13) 0.0581(17) 0.5493(17) 0.022 Uiso 1 1 d D U .
H2B1 H 0.2365(18) -0.0207(18) 0.4065(13) 0.022 Uiso 1 1 d D U .
O4A O 0.25227(9) 0.39843(11) 0.99502(12) 0.02398(19) Uani 1 1 d . . .
C2B C 0.11863(11) 0.06051(12) 0.57057(11) 0.01202(17) Uani 1 1 d . . .
C8A C 0.5000 0.4354(2) 1.18084(19) 0.0186(3) Uani 1 2 d DS T P
H81 H 0.5849(14) 0.4863(18) 1.2198(19) 0.022 Uiso 1 1 d D U .
C7A C 0.5000 0.60307(18) 0.9496(2) 0.0178(3) Uani 1 2 d DS T P
H71 H 0.5884(13) 0.6418(16) 0.9955(18) 0.021 Uiso 1 1 d D U .
C10A C 0.5000 0.6287(2) 0.7759(2) 0.0266(4) Uani 1 2 d DS T P
H11 H 0.5845(15) 0.5877(19) 0.728(2) 0.032 Uiso 1 1 d D U .
H12 H 0.5000 0.7366(15) 0.758(3) 0.032 Uiso 1 2 d DS U P
C9A C 0.5000 0.2816(3) 1.2499(3) 0.0360(5) Uani 1 2 d DS T P
H91 H 0.5840(17) 0.225(2) 1.219(2) 0.043 Uiso 1 1 d D U .
H92 H 0.5000 0.288(3) 1.3634(15) 0.043 Uiso 1 2 d DS U P
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
C4B N3B C2B 114.72(9) . .
C4B N4B H4B 119.4(10) . .
C2B N1B C2B 114.54(13) 3 .
N4B C4B N3B 117.51(6) . 3
N4B C4B N3B 117.51(6) . .
N3B C4B N3B 124.97(13) 3 .
C4A C5A C4A 113.78(13) . 3_655
C4A C5A C8A 110.14(9) . .
C4A C5A C8A 110.14(9) 3_655 .
C4A C5A C7A 107.15(9) . .
C4A C5A C7A 107.15(9) 3_655 .
C8A C5A C7A 108.25(13) . .
O2A C2A N1A 121.43(7) . .
O2A C2A N1A 121.43(7) . 3_655
N1A C2A N1A 117.13(13) . 3_655
C2A N1A C4A 125.49(10) . .
C2A N1A H1A 117.8(9) . .
C4A N1A H1A 115.7(9) . .
O4A C4A N1A 120.00(10) . .
O4A C4A C5A 121.70(11) . .
N1A C4A C5A 118.24(10) . .
C2B N2B H2B2 120.5(9) . .
C2B N2B H2B1 116.9(10) . .
H2B2 N2B H2B1 122.5(15) . .
N2B C2B N1B 117.83(10) . .
N2B C2B N3B 116.66(10) . .
N1B C2B N3B 125.51(10) . .
C9A C8A C5A 114.41(15) . .
C9A C8A H81 107.3(10) . .
C5A C8A H81 109.3(10) . .
C10A C7A C5A 115.78(14) . .
C10A C7A H71 109.9(9) . .
C5A C7A H71 102.8(9) . .
C7A C10A H11 111.0(11) . .
C7A C10A H12 107.8(17) . .
H11 C10A H12 108.1(14) . .
C8A C9A H91 111.7(13) . .
C8A C9A H92 109.6(16) . .
H91 C9A H92 107.7(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2A C2A 1.2244(19) .
N3B C4B 1.3491(11) .
N3B C2B 1.3566(13) .
N4B C4B 1.339(2) .
N4B H4B 0.952(10) .
N1B C2B 1.3437(13) 3
N1B C2B 1.3438(13) .
C4B N3B 1.3491(11) 3
C5A C4A 1.5138(14) .
C5A C4A 1.5138(14) 3_655
C5A C8A 1.549(2) .
C5A C7A 1.562(2) .
C2A N1A 1.3713(12) .
C2A N1A 1.3713(12) 3_655
N1A C4A 1.3743(14) .
N1A H1A 0.990(11) .
C4A O4A 1.2184(14) .
N2B C2B 1.3363(14) .
N2B H2B2 0.967(11) .
N2B H2B1 0.948(11) .
C8A C9A 1.525(3) .
C8A H81 0.992(11) .
C7A C10A 1.524(3) .
C7A H71 0.996(11) .
C10A H11 0.979(11) .
C10A H12 0.997(12) .
C9A H91 0.988(12) .
C9A H92 0.985(13) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4B H4B O4A 0.952(10) 2.036(11) 2.9718(12) 167.3(14) 3
N2B H2B2 O2A 0.967(11) 1.981(11) 2.9419(12) 172.7(14) .
N1A H1A N3B 0.990(11) 1.925(11) 2.9124(12) 174.9(13) .
N2B H2B1 N3B 0.948(11) 2.357(13) 3.1698(14) 143.6(14) 2_554
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2B N3B C4B N4B 179.93(13) . .
C2B N3B C4B N3B 0.6(2) . 3
O2A C2A N1A C4A 177.85(13) . .
N1A C2A N1A C4A -3.0(2) 3_655 .
C2A N1A C4A O4A -173.86(13) . .
C2A N1A C4A C5A 8.99(18) . .
C4A C5A C4A O4A 169.24(9) 3_655 .
C8A C5A C4A O4A 45.03(17) . .
C7A C5A C4A O4A -72.51(16) . .
C4A C5A C4A N1A -13.67(19) 3_655 .
C8A C5A C4A N1A -137.88(12) . .
C7A C5A C4A N1A 104.58(12) . .
C2B N1B C2B N2B -178.80(8) 3 .
C2B N1B C2B N3B 1.4(2) 3 .
C4B N3B C2B N2B 179.17(11) . .
C4B N3B C2B N1B -1.05(16) . .
C4A C5A C8A C9A 63.15(9) . .
C4A C5A C8A C9A -63.15(9) 3_655 .
C7A C5A C8A C9A 180.000(1) . .
C4A C5A C7A C10A -61.24(9) . .
C4A C5A C7A C10A 61.24(9) 3_655 .
C8A C5A C7A C10A 180.000(1) . .
