#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/02/7200287.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_7200287
loop_
_publ_author_name
'Karki, Shyam'
'Friščić, Tomislav'
'Jones, William'
_publ_section_title
;
 Control and interconversion of cocrystal stoichiometry in grinding:
 stepwise mechanism for the formation of a hydrogen-bonded cocrystal
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              470
_journal_paper_doi               10.1039/b812531g
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration
;
1473 Friedel pairs were averaged for the refinement.
;
_chemical_formula_moiety         '2(C6 H6 N2 O), C3 H4 O4'
_chemical_formula_sum            'C15 H16 N4 O6'
_chemical_formula_weight         348.32
_chemical_name_common            'nicotinamide:malonic acid 2/1'
_chemical_name_systematic
;
nicotinamide:malonic acid 2/1
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   32.9054(6)
_cell_length_b                   4.0078(1)
_cell_length_c                   12.3689(2)
_cell_measurement_reflns_used    11834
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.00
_cell_volume                     1631.19(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8534
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         3.72
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         1983
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0487P)²+0.2847P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                1780
_reflns_number_total             1983
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812531g.txt
_cod_data_source_block           (na)2.(mal)
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7200287
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07251(5) 0.1344(5) 0.41728(13) 0.0423(4) Uani 1 1 d . . .
O2 O 0.32014(5) -0.0976(4) -0.10065(13) 0.0406(4) Uani 1 1 d . . .
O3 O 0.31892(5) 0.2583(5) 0.42063(14) 0.0358(4) Uani 1 1 d . . .
H3A H 0.2996(9) 0.120(7) 0.477(2) 0.043 Uiso 1 1 d . . .
O4 O 0.35649(6) 0.3646(5) 0.56534(14) 0.0480(5) Uani 1 1 d . . .
O5 O 0.39507(6) 0.2974(5) 0.23603(14) 0.0465(4) Uani 1 1 d . . .
O6 O 0.43553(5) 0.2770(4) 0.37990(13) 0.0348(4) Uani 1 1 d . . .
H6A H 0.4519(9) 0.134(7) 0.332(2) 0.042 Uiso 1 1 d . . .
N1 N -0.01705(6) -0.4073(5) 0.26547(15) 0.0338(4) Uani 1 1 d . . .
N2 N 0.11471(6) 0.0964(6) 0.27426(17) 0.0437(5) Uani 1 1 d . . .
H2A H 0.1350 0.1893 0.3096 0.052 Uiso 1 1 calc R . .
H2B H 0.1180 0.0332 0.2067 0.052 Uiso 1 1 calc R . .
N3 N 0.22956(6) 0.4424(5) 0.04466(14) 0.0318(4) Uani 1 1 d . . .
N4 N 0.36360(6) -0.0186(6) 0.03800(16) 0.0455(5) Uani 1 1 d . . .
H4A H 0.3838 -0.1169 0.0040 0.055 Uiso 1 1 calc R . .
H4B H 0.3673 0.0618 0.1035 0.055 Uiso 1 1 calc R . .
C1 C 0.04583(7) -0.1052(5) 0.25842(17) 0.0289(4) Uani 1 1 d . . .
C2 C 0.04215(7) -0.0832(6) 0.14630(18) 0.0339(5) Uani 1 1 d . . .
H2 H 0.0629 0.0211 0.1048 0.041 Uiso 1 1 calc R . .
C3 C 0.00824(7) -0.2141(6) 0.0960(2) 0.0370(5) Uani 1 1 d . . .
H3 H 0.0049 -0.1939 0.0200 0.044 Uiso 1 1 calc R . .
C4 C -0.02076(7) -0.3746(6) 0.15781(19) 0.0348(5) Uani 1 1 d . . .
H4 H -0.0440 -0.4648 0.1231 0.042 Uiso 1 1 calc R . .
C5 C 0.01518(7) -0.2713(5) 0.31405(18) 0.0294(5) Uani 1 1 d . . .
H5 H 0.0173 -0.2890 0.3904 0.035 Uiso 1 1 calc R . .
C6 C 0.07921(7) 0.0517(6) 0.32279(18) 0.0321(5) Uani 1 1 d . . .
C7 C 0.29401(6) 0.1704(5) 0.05483(16) 0.0273(4) Uani 1 1 d . . .
C8 C 0.29212(7) 0.1802(6) 0.16672(18) 0.0351(5) Uani 1 1 d . . .
H8 H 0.3140 0.0967 0.2091 0.042 Uiso 1 1 calc R . .
C9 C 0.25781(7) 0.3139(6) 0.21610(19) 0.0363(5) Uani 1 1 d . . .
H9 H 0.2556 0.3159 0.2927 0.044 Uiso 1 1 calc R . .
C10 C 0.22724(7) 0.4430(6) 0.15315(19) 0.0342(5) Uani 1 1 d . . .
H10 H 0.2039 0.5348 0.1871 0.041 Uiso 1 1 calc R . .
C11 C 0.26194(7) 0.3070(6) -0.00276(18) 0.0299(5) Uani 1 1 d . . .
H11 H 0.2631 0.3038 -0.0795 0.036 Uiso 1 1 calc R . .
C12 C 0.32768(7) 0.0082(6) -0.00941(17) 0.0312(5) Uani 1 1 d . . .
C13 C 0.34946(6) 0.3984(5) 0.46960(18) 0.0285(4) Uani 1 1 d . . .
C14 C 0.37621(8) 0.6026(5) 0.3957(2) 0.0343(5) Uani 1 1 d . . .
H14A H 0.3934 0.7541 0.4394 0.041 Uiso 1 1 calc R . .
H14B H 0.3590 0.7409 0.3476 0.041 Uiso 1 1 calc R . .
C15 C 0.40311(6) 0.3783(5) 0.32776(17) 0.0292(4) Uani 1 1 d . . .
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
C13 O3 H3A 111.6(15) . . ?
C15 O6 H6A 109.1(17) . . ?
C5 N1 C4 118.6(2) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C11 N3 C10 119.1(2) . . ?
C12 N4 H4A 120.0 . . ?
C12 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C5 C1 C2 117.3(2) . . ?
C5 C1 C6 118.07(19) . . ?
C2 C1 C6 124.5(2) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
N1 C4 C3 122.1(2) . . ?
N1 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
N1 C5 C1 123.3(2) . . ?
N1 C5 H5 118.4 . . ?
C1 C5 H5 118.4 . . ?
O1 C6 N2 123.3(2) . . ?
O1 C6 C1 119.1(2) . . ?
N2 C6 C1 117.6(2) . . ?
C11 C7 C8 117.9(2) . . ?
C11 C7 C12 117.27(19) . . ?
C8 C7 C12 124.8(2) . . ?
C7 C8 C9 119.1(2) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N3 C10 C9 121.6(2) . . ?
N3 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
N3 C11 C7 122.9(2) . . ?
N3 C11 H11 118.5 . . ?
C7 C11 H11 118.5 . . ?
O2 C12 N4 123.9(2) . . ?
O2 C12 C7 118.9(2) . . ?
N4 C12 C7 117.19(19) . . ?
O4 C13 O3 123.6(2) . . ?
O4 C13 C14 122.7(2) . . ?
O3 C13 C14 113.7(2) . . ?
C13 C14 C15 110.78(16) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O5 C15 O6 123.8(2) . . ?
O5 C15 C14 123.4(2) . . ?
O6 C15 C14 112.74(19) . . ?
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 C6 1.235(3) . ?
O2 C12 1.231(3) . ?
O3 C13 1.301(3) . ?
O3 H3A 1.10(3) . ?
O4 C13 1.214(3) . ?
O5 C15 1.209(3) . ?
O6 C15 1.311(3) . ?
O6 H6A 0.99(3) . ?
N1 C5 1.335(3) . ?
N1 C4 1.344(3) . ?
N2 C6 1.326(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C11 1.332(3) . ?
N3 C10 1.344(3) . ?
N4 C12 1.324(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C1 C5 1.391(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.495(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C11 1.386(3) . ?
C7 C8 1.386(3) . ?
C7 C12 1.510(3) . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.510(3) . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 2.2(3) . . . . ?
C6 C1 C2 C3 -174.6(2) . . . . ?
C1 C2 C3 C4 -2.2(4) . . . . ?
C5 N1 C4 C3 1.9(3) . . . . ?
C2 C3 C4 N1 0.1(4) . . . . ?
C4 N1 C5 C1 -1.9(3) . . . . ?
C2 C1 C5 N1 -0.2(3) . . . . ?
C6 C1 C5 N1 176.8(2) . . . . ?
C5 C1 C6 O1 -25.2(3) . . . . ?
C2 C1 C6 O1 151.6(2) . . . . ?
C5 C1 C6 N2 155.2(2) . . . . ?
C2 C1 C6 N2 -28.0(3) . . . . ?
C11 C7 C8 C9 2.4(4) . . . . ?
C12 C7 C8 C9 -174.9(2) . . . . ?
C7 C8 C9 C10 -2.1(4) . . . . ?
C11 N3 C10 C9 1.4(4) . . . . ?
C8 C9 C10 N3 0.2(4) . . . . ?
C10 N3 C11 C7 -1.2(3) . . . . ?
C8 C7 C11 N3 -0.7(3) . . . . ?
C12 C7 C11 N3 176.7(2) . . . . ?
C11 C7 C12 O2 -24.3(3) . . . . ?
C8 C7 C12 O2 153.0(2) . . . . ?
C11 C7 C12 N4 157.5(2) . . . . ?
C8 C7 C12 N4 -25.3(4) . . . . ?
O4 C13 C14 C15 102.6(3) . . . . ?
O3 C13 C14 C15 -76.1(3) . . . . ?
C13 C14 C15 O5 97.4(3) . . . . ?
C13 C14 C15 O6 -81.4(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653538
