# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Mikelis Veidis'
_publ_contact_author_email       VEIDIS@LU.LV

_publ_section_title              
;
Nicotinamide fumaric acid cocrystals: diversity of stoichiometry
;
_publ_contact_author_address     
;
Department of Chemistry,
University of Latvia,
Kr. Valdemara 48,
Riga, LV-1013,
Latvia.
;
_publ_contact_author_fax         '+371 737 8736'

_publ_contact_author_phone       '+371 737 8718'

# Check this file using the IUCr facility at:
# http://checkcif.iucr.org/

# The content below is held in the file 'script/refcif.dat'. This is a text
# file which you may edit to reflect local conditions.
# Items which need looking at are represented by a '?'.
# Items for which there are choices are prefixed with 'choose from'.

_publ_contact_letter             
;
Please consider this CIF submission for
publication as a Short Format Paper in Acta
Crystallographica E. The figures have been
sent by mail.
;
_publ_requested_category         CO # choose from: FI FM FO CI CM CO AD
_publ_requested_coeditor_name    ?
loop_
_publ_author_name
'Mikelis Veidis'
'Liana Orola'

#======END

data_2
_database_code_depnum_ccdc_archive 'CCDC 686162'

_audit_creation_method           CRYSTALS_ver_12.82
_chemical_name_systematic        'nicotinamide fumaric acid 2:1'
_chemical_melting_point          ?

_cell_length_a                   5.592(3)
_cell_length_b                   12.044(1)
_cell_length_c                   13.131(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.00(5)
_cell_angle_gamma                90
_cell_volume                     879.5(6)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

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'

_cell_formula_units_Z            2

# Given Formula = C16 H16 N4 O6
# Dc = 1.36 Fooo = 376.00 Mu = 9.02 M = 180.16
# Found Formula = C16 H16 N4 O6
# Dc = 1.36 FOOO = 376.00 Mu = 9.02 M = 180.16

_chemical_formula_sum            'C16 H16 N4 O6'
_chemical_formula_moiety         'C16 H16 N4 O6'
_chemical_compound_source        ?
_chemical_formula_weight         360.33

_cell_measurement_reflns_used    25
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    295

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.902

# Sheldrick geometric approximatio 0.82 0.94
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω/2θ

_computing_data_collection       'CAD4 Express, (Straver, 1992)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_cell_refinement       'CAD4 Express, (Straver, 1992)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'

_diffrn_standards_interval_time  60
_diffrn_standards_interval_count ?
_diffrn_standards_number         2
_diffrn_standards_decay_%        2

_diffrn_ambient_temperature      295
_diffrn_reflns_number            1604
_reflns_number_total             1386
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections with Friedels Law is 1604
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1600

_diffrn_reflns_theta_min         4.995
_diffrn_reflns_theta_max         67.924
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        67.924
_diffrn_measured_fraction_theta_full 0.999

_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.22
_refine_diff_density_max         0.30

_refine_ls_number_reflns         1386
_refine_ls_number_restraints     0
_refine_ls_number_parameters     119

#_refine_ls_R_factor_ref 0.0527
_refine_ls_wR_factor_ref         0.0673
_refine_ls_goodness_of_fit_ref   1.1029

#_reflns_number_all 1587
_refine_ls_R_factor_all          0.0580
_refine_ls_wR_factor_all         0.0786

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                1386
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_gt          0.0673

_refine_ls_shift/su_max          0.000324

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_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:
2.99 1.83 2.14
;

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
O11 O 0.2701(2) 0.05773(10) 0.64942(8) 0.0599 1.0000 Uani . . . . . .
O10 O 0.0734(2) 0.13499(10) 0.51146(8) 0.0610 1.0000 Uani . . . . . .
O2 O -0.7515(2) 0.41112(11) 0.48895(9) 0.0680 1.0000 Uani . . . . . .
N6 N -0.1955(2) 0.23210(11) 0.63037(10) 0.0546 1.0000 Uani . . . . . .
N1 N -0.8444(3) 0.49175(13) 0.63406(11) 0.0636 1.0000 Uani . . . . . .
C4 C -0.5293(3) 0.35315(11) 0.64177(11) 0.0460 1.0000 Uani . . . . . .
C9 C -0.5167(3) 0.33311(13) 0.74646(11) 0.0537 1.0000 Uani . . . . . .
C3 C -0.7178(3) 0.42192(12) 0.58239(11) 0.0517 1.0000 Uani . . . . . .
C13 C 0.4022(3) 0.02650(13) 0.48485(11) 0.0518 1.0000 Uani . . . . . .
C7 C -0.1867(3) 0.21269(13) 0.73081(13) 0.0568 1.0000 Uani . . . . . .
C12 C 0.2426(3) 0.07389(12) 0.55789(11) 0.0473 1.0000 Uani . . . . . .
C5 C -0.3625(3) 0.30083(13) 0.58767(11) 0.0521 1.0000 Uani . . . . . .
C8 C -0.3439(3) 0.26141(14) 0.79134(12) 0.0593 1.0000 Uani . . . . . .
H13 H 0.3584 0.0357 0.4120 0.0645 1.0000 Uiso R . . . . .
H7 H -0.0665 0.1621 0.7602 0.0675 1.0000 Uiso R . . . . .
H5 H -0.3722 0.3156 0.5151 0.0629 1.0000 Uiso R . . . . .
H8 H -0.3317 0.2477 0.8642 0.0710 1.0000 Uiso R . . . . .
H1 H -0.8063 0.5008 0.7017 0.0748 1.0000 Uiso R . . . . .
H9 H -0.6232 0.3692 0.7875 0.0654 1.0000 Uiso R . . . . .
H2 H -0.9671 0.5279 0.5991 0.0764 1.0000 Uiso R . . . . .
H10 H 0.0003 0.1648 0.5610 0.0935 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O11 0.0689(7) 0.0694(8) 0.0423(6) 0.0061(5) 0.0101(5) 0.0144(5)
O10 0.0706(8) 0.0712(7) 0.0436(6) 0.0081(5) 0.0170(5) 0.0241(6)
O2 0.0827(9) 0.0772(8) 0.0403(7) -0.0114(5) -0.0106(5) 0.0294(6)
N6 0.0594(8) 0.0583(8) 0.0464(8) -0.0009(5) 0.0064(5) 0.0155(6)
N1 0.0722(9) 0.0716(9) 0.0444(7) -0.0115(6) -0.0063(6) 0.0296(7)
C4 0.0520(8) 0.0468(7) 0.0384(7) -0.0048(6) 0.0006(6) 0.0071(6)
C9 0.0688(10) 0.0543(8) 0.0384(7) -0.0041(6) 0.0075(6) 0.0125(7)
C3 0.0605(9) 0.0540(8) 0.0388(8) -0.0062(6) -0.0034(6) 0.0105(7)
C13 0.0593(9) 0.0574(9) 0.0400(8) 0.0031(6) 0.0110(6) 0.0071(6)
C7 0.066(1) 0.0553(9) 0.0478(8) -0.0005(6) 0.0003(7) 0.0146(7)
C12 0.0536(8) 0.0490(8) 0.0407(8) 0.0017(5) 0.0121(6) 0.0010(6)
C5 0.0629(9) 0.0557(8) 0.0382(7) 0.0005(6) 0.0076(6) 0.0108(7)
C8 0.0813(11) 0.0592(9) 0.0369(8) 0.0011(6) 0.0043(7) 0.0158(7)

_refine_ls_extinction_coef       240(30)
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'
_oxford_refine_ls_scale          4.33(2)
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
O11 . C12 . 1.2114(18) yes
O10 . C12 . 1.2993(18) yes
O10 . H10 . 0.880 no
O2 . C3 . 1.2286(19) yes
N6 . C7 . 1.335(2) yes
N6 . C5 . 1.327(2) yes
N1 . C3 . 1.330(2) yes
N1 . H1 . 0.899 no
N1 . H2 . 0.898 no
C4 . C9 . 1.390(2) yes
C4 . C3 . 1.495(2) yes
C4 . C5 . 1.382(2) yes
C9 . C8 . 1.381(2) yes
C9 . H9 . 0.949 no
C13 . C13 2_656 1.293(3) yes
C13 . C12 . 1.490(2) yes
C13 . H13 . 0.969 no
C7 . C8 . 1.377(3) yes
C7 . H7 . 0.957 no
C5 . H5 . 0.965 no
C8 . H8 . 0.966 no
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
C12 . O10 . H10 . 104.8 no
C7 . N6 . C5 . 118.56(13) yes
C3 . N1 . H1 . 119.8 no
C3 . N1 . H2 . 117.7 no
H1 . N1 . H2 . 122.4 no
C9 . C4 . C3 . 124.90(14) yes
C9 . C4 . C5 . 117.51(14) yes
C3 . C4 . C5 . 117.50(14) yes
C4 . C9 . C8 . 119.44(14) yes
C4 . C9 . H9 . 120.8 no
C8 . C9 . H9 . 119.8 no
C4 . C3 . N1 . 117.92(14) yes
C4 . C3 . O2 . 119.23(14) yes
N1 . C3 . O2 . 122.84(14) yes
C13 2_656 C13 . C12 . 122.37(18) yes
C13 2_656 C13 . H13 . 118.6 no
C12 . C13 . H13 . 119.0 no
N6 . C7 . C8 . 122.39(15) yes
N6 . C7 . H7 . 117.5 no
C8 . C7 . H7 . 120.1 no
C13 . C12 . O10 . 111.76(13) yes
C13 . C12 . O11 . 123.67(14) yes
O10 . C12 . O11 . 124.57(14) yes
C4 . C5 . N6 . 123.37(14) yes
C4 . C5 . H5 . 116.9 no
N6 . C5 . H5 . 119.8 no
C9 . C8 . C7 . 118.73(15) yes
C9 . C8 . H8 . 120.2 no
C7 . C8 . H8 . 121.0 no
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 . H1 . O11 3_456 165.4 0.899 2.061 2.940(2) yes
N1 . H2 . O2 2_366 172.2 0.898 1.993 2.885(3) yes
O10 . H10 . N6 . 164.7 0.880 1.701 2.561(2) yes
_chemical_name_common            'nicotinamide fumaric acid 2:1'

# Attachment 'nic-fa.cif'

# Supplementary Material (ESI) for Chemical Communications

data_1
_database_code_depnum_ccdc_archive 'CCDC 689435'

_audit_creation_method           CRYSTALS_ver_12.82
_chemical_name_systematic        'nicotinamide fumaric acid 1:1'
_chemical_melting_point          ?

_cell_length_a                   5.550(1)
_cell_length_b                   13.792(1)
_cell_length_c                   14.360(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.41(1)
_cell_angle_gamma                90
_cell_volume                     1097.2(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
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_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'

_cell_formula_units_Z            4

# Given Formula = C10 H10 N2 O5
# Dc = 1.44 Fooo = 496.00 Mu = 10.10 M = 238.20
# Found Formula = C10 H10 N2 O5
# Dc = 1.44 FOOO = 496.00 Mu = 10.10 M = 238.20

_chemical_formula_sum            'C10 H10 N2 O5'
_chemical_formula_moiety         'C10 H10 N2 O5'
_chemical_compound_source        ?
_chemical_formula_weight         238.20

_cell_measurement_reflns_used    25
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    293

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    1.010

# Sheldrick geometric approximatio 0.82 0.82
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω/2θ

_computing_data_collection       'CAD4 Express, (Straver, 1992)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_cell_refinement       'CAD4 Express, (Straver, 1992)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'

_diffrn_standards_interval_time  60
_diffrn_standards_interval_count ?
_diffrn_standards_number         2
_diffrn_standards_decay_%        3.00

_diffrn_ambient_temperature      293
_diffrn_reflns_number            2247
_reflns_number_total             1931
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections with Friedels Law is 1931
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1996

_diffrn_reflns_theta_min         4.449
_diffrn_reflns_theta_max         67.931
_diffrn_measured_fraction_theta_max 0.965

_diffrn_reflns_theta_full        56.383
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -6
_reflns_limit_h_max              5
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.15
_refine_diff_density_max         0.16

_refine_ls_number_reflns         1634
_refine_ls_number_restraints     0
_refine_ls_number_parameters     155

#_refine_ls_R_factor_ref 0.0329
_refine_ls_wR_factor_ref         0.0579
_refine_ls_goodness_of_fit_ref   1.0483

#_reflns_number_all 1923
_refine_ls_R_factor_all          0.0394
_refine_ls_wR_factor_all         0.0582

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                1634
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_gt          0.0579

_refine_ls_shift/su_max          0.000500

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_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
;

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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0442(9) 0.0345(7) 0.0695(9) 0.0081(6) -0.0262(7) -0.0067(6)
O2 0.0460(7) 0.0286(5) 0.0710(8) 0.0002(5) -0.0237(6) -0.0037(5)
C3 0.0338(8) 0.0304(7) 0.0457(8) 0.0001(6) -0.0070(6) -0.0002(6)
C4 0.0318(9) 0.0302(7) 0.0423(8) -0.0010(6) -0.0065(6) -0.0009(6)
C5 0.0380(9) 0.0289(7) 0.0511(9) -0.0004(6) -0.0105(7) -0.0001(6)
N6 0.0395(8) 0.0358(7) 0.0527(8) -0.0006(6) -0.0157(6) 0.0011(6)
C7 0.0410(10) 0.0390(9) 0.0574(10) -0.0078(7) -0.0158(8) -0.0032(7)
C8 0.0500(10) 0.0283(8) 0.0685(11) -0.0047(8) -0.0164(8) -0.0027(7)
C9 0.0419(10) 0.0314(8) 0.0577(10) 0.0004(7) -0.0154(7) 0.0032(7)
O17 0.0469(8) 0.0399(6) 0.0755(8) -0.0015(6) -0.0299(6) 0.0036(5)
O11 0.0417(7) 0.0421(7) 0.0725(8) -0.0015(6) -0.0241(6) -0.0051(5)
C12 0.0354(9) 0.0371(8) 0.0455(8) 0.0009(6) -0.0084(7) -0.0029(7)
C13 0.0391(9) 0.0358(8) 0.0547(9) 0.0021(7) -0.0095(7) 0.0027(7)
C14 0.0367(9) 0.0362(8) 0.0498(9) 0.0018(7) -0.0083(7) 0.0030(7)
C15 0.0329(9) 0.0384(9) 0.0507(9) 0.0008(7) -0.0078(7) 0.0012(6)
O16 0.0484(8) 0.0382(7) 0.0819(9) -0.0018(6) -0.0264(6) 0.0053(5)
O10 0.0463(7) 0.0353(6) 0.0695(8) 0.0027(5) -0.0285(6) 0.0003(5)

_refine_ls_extinction_coef       67.9(17)
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'
_oxford_refine_ls_scale          2.60(2)
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_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_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
_chemical_name_common            'nicotinamide fumaric acid 1:1'

