#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/05/7200584.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_7200584
loop_
_publ_author_name
'Orola, Liana'
'Veidis, Mikelis V.'
_publ_section_title
;
 Nicotinamide fumaric acid supramolecular cocrystals: diversity of
 stoichiometry
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              415
_journal_paper_doi               10.1039/b818667g
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C10 H10 N2 O5'
_chemical_formula_sum            'C10 H10 N2 O5'
_chemical_formula_weight         238.20
_chemical_name_common            'nicotinamide fumaric acid 1:1'
_chemical_name_systematic        'nicotinamide fumaric acid 1:1'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           CRYSTALS_ver_12.82
_cell_angle_alpha                90
_cell_angle_beta                 93.41(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.550(1)
_cell_length_b                   13.792(1)
_cell_length_c                   14.360(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1097.2(3)
_computing_cell_refinement       'CAD4 Express, (Straver, 1992)'
_computing_data_collection       'CAD4 Express, (Straver, 1992)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2247
_diffrn_reflns_theta_full        56.383
_diffrn_reflns_theta_max         67.931
_diffrn_reflns_theta_min         4.449
_diffrn_standards_decay_%        3.00
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.010
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.15
_refine_ls_extinction_coef       67.9(17)
_refine_ls_extinction_method
'Larson 1970 Crystallographic Computing eq 22'
_refine_ls_goodness_of_fit_ref   1.0483
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1634
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.000500
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
91.8 123. 53.1
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0582
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0579
_reflns_limit_h_max              5
_reflns_limit_h_min              -6
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                1634
_reflns_number_total             1931
_reflns_threshold_expression     I>3.00u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          2.60(2)
_cod_data_source_file            b818667g.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               7200584
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
H2 H -0.5466 0.9795 0.6037 0.0594 1.0000 Uiso . . . . . .
H7 H 0.4615 1.0800 0.8789 0.0556 1.0000 Uiso . . . . . .
H8 H 0.2079 1.1915 0.7999 0.0593 1.0000 Uiso . . . . . .
H9 H -0.1296 1.1354 0.7099 0.0522 1.0000 Uiso . . . . . .
H17 H 1.4361 0.7026 1.1359 0.0800 1.0000 Uiso . . . . . .
H13 H 0.7943 0.6437 0.9606 0.0530 1.0000 Uiso . . . . . .
H14 H 1.0045 0.8174 1.0133 0.0498 1.0000 Uiso . . . . . .
H10 H 0.5009 0.8902 0.8932 0.0764 1.0000 Uiso . . . . . .
N1 N -0.4225(3) 1.00610(10) 0.63409(10) 0.0506 1.0000 Uani . . . . . .
O2 O -0.3150(2) 0.85973(7) 0.69005(9) 0.0496 1.0000 Uani . . . . . .
C3 C -0.2788(3) 0.94805(11) 0.68502(10) 0.0370 1.0000 Uani . . . . . .
C4 C -0.0681(3) 0.99211(10) 0.73919(10) 0.0351 1.0000 Uani . . . . . .
C5 C 0.0913(3) 0.93145(11) 0.78856(11) 0.0399 1.0000 Uani . . . . . .
N6 N 0.2834(2) 0.96426(9) 0.83971(9) 0.0434 1.0000 Uani . . . . . .
C7 C 0.3227(3) 1.05956(12) 0.84267(12) 0.0465 1.0000 Uani . . . . . .
C8 C 0.1742(3) 1.12509(11) 0.79597(13) 0.0497 1.0000 Uani . . . . . .
C9 C -0.0255(3) 1.09084(11) 0.74334(12) 0.0444 1.0000 Uani . . . . . .
O17 O 1.3306(2) 0.73961(8) 1.10821(9) 0.0554 1.0000 Uani . . . . . .
O11 O 0.4328(2) 0.72704(8) 0.87189(9) 0.0532 1.0000 Uani . . . . . .
C12 C 0.5996(3) 0.76769(11) 0.91452(11) 0.0398 1.0000 Uani . . . . . .
C13 C 0.7997(3) 0.71157(12) 0.96203(12) 0.0437 1.0000 Uani . . . . . .
C14 C 0.9865(3) 0.75074(11) 1.00742(11) 0.0413 1.0000 Uani . . . . . .
C15 C 1.1737(3) 0.68893(12) 1.05573(11) 0.0411 1.0000 Uani . . . . . .
O16 O 1.1796(2) 0.60219(9) 1.04808(9) 0.0574 1.0000 Uani . . . . . .
O10 O 0.6197(2) 0.86101(8) 0.92398(9) 0.0517 1.0000 Uani . . . . . .
H5 H 0.0679 0.8621 0.7864 0.0493 1.0000 Uiso . . . . . .
H1 H -0.3914 1.0774 0.6306 0.0586 1.0000 Uiso . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H2 . N1 . C3 . 117.0 no
H2 . N1 . H1 . 121.4 no
C3 . N1 . H1 . 121.6 no
N1 . C3 . O2 . 122.31(14) yes
N1 . C3 . C4 . 118.04(13) yes
O2 . C3 . C4 . 119.64(13) yes
C3 . C4 . C5 . 118.56(13) yes
C3 . C4 . C9 . 123.32(14) yes
C5 . C4 . C9 . 118.12(14) yes
C4 . C5 . N6 . 122.83(14) yes
C4 . C5 . H5 . 120.2 no
N6 . C5 . H5 . 117.0 no
C5 . N6 . C7 . 118.36(13) yes
H7 . C7 . N6 . 116.0 no
H7 . C7 . C8 . 121.2 no
N6 . C7 . C8 . 122.83(14) yes
H8 . C8 . C7 . 120.2 no
H8 . C8 . C9 . 121.1 no
C7 . C8 . C9 . 118.66(14) yes
H9 . C9 . C8 . 119.7 no
H9 . C9 . C4 . 121.1 no
C8 . C9 . C4 . 119.21(14) yes
H17 . O17 . C15 . 111.1 no
O11 . C12 . C13 . 121.13(15) yes
O11 . C12 . O10 . 124.57(15) yes
C13 . C12 . O10 . 114.29(13) yes
C12 . C13 . H13 . 119.2 no
C12 . C13 . C14 . 124.21(15) yes
H13 . C13 . C14 . 116.6 no
H14 . C14 . C13 . 122.1 no
H14 . C14 . C15 . 117.3 no
C13 . C14 . C15 . 120.53(14) yes
C14 . C15 . O17 . 112.53(13) yes
C14 . C15 . O16 . 123.44(14) yes
O17 . C15 . O16 . 124.03(15) yes
H10 . O10 . C12 . 110.4 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
H2 . N1 . 0.874 no
H7 . C7 . 0.947 no
H8 . C8 . 0.936 no
H9 . C9 . 0.954 no
H17 . O17 . 0.857 no
H13 . C13 . 0.937 no
H14 . C14 . 0.928 no
H10 . O10 . 0.870 no
N1 . C3 . 1.3200(19) yes
N1 . H1 . 1.000 no
O2 . C3 . 1.2374(18) yes
C3 . C4 . 1.495(2) yes
C4 . C5 . 1.382(2) yes
C4 . C9 . 1.383(2) yes
C5 . N6 . 1.3369(19) yes
C5 . H5 . 0.966 no
N6 . C7 . 1.333(2) yes
C7 . C8 . 1.371(2) yes
C8 . C9 . 1.387(2) yes
O17 . C15 . 1.3177(19) yes
O11 . C12 . 1.2163(18) yes
C12 . C13 . 1.486(2) yes
C12 . O10 . 1.2983(19) yes
C13 . C14 . 1.308(2) yes
C14 . C15 . 1.484(2) yes
C15 . O16 . 1.2020(19) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N1 . H2 . O16 4_364 169.9 0.874 2.018 2.882(2) yes
O17 . H17 . O2 4_765 171.4 0.857 1.767 2.618(2) yes
O10 . H10 . N6 . 171.2 0.870 1.726 2.590(2) yes
N1 . H1 . O11 3_556 163.5 1.000 2.077 3.049(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25940819
