#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:58:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180458 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/27/7212760.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_7212760
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Rajbanshi, Arbin'
'Li, Z. Jane'
'Desper, John'
_publ_section_title
;
 Mapping out the synthetic landscape for re-crystallization,
 co-crystallization and salt formation
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              4231
_journal_paper_doi               10.1039/c0ce00052c
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety
;
(C8 H9 N2 O Br)2 (C4 H4 O4)
;
_chemical_formula_sum            'C20 H22 Br2 N4 O6'
_chemical_formula_weight         574.24
_chemical_name_systematic
;
AR-1c-aa13 [N-(5-bromo-2-pyridyl)propionamide]2, fumaric acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 90.961(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.8333(3)
_cell_length_b                   9.5923(5)
_cell_length_c                   23.7901(12)
_cell_measurement_reflns_used    7507
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.14
_cell_measurement_theta_min      2.29
_cell_volume                     1102.81(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            19971
_diffrn_reflns_theta_full        31.28
_diffrn_reflns_theta_max         31.28
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    3.721
_exptl_absorpt_correction_T_max  0.7551
_exptl_absorpt_correction_T_min  0.5232
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0296
_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)+(0.0300P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0669
_reflns_number_gt                2806
_reflns_number_total             3473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00052c.txt
_cod_data_source_block           ar0713m(D13)
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7212760
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Br1 Br 0.77917(4) -0.140736(19) 0.417648(7) 0.02370(7) Uani 1 1 d .
N11 N 0.3156(3) 0.21417(15) 0.40596(6) 0.0156(3) Uani 1 1 d .
C12 C 0.4189(4) 0.09027(18) 0.42056(7) 0.0176(3) Uani 1 1 d .
H12 H 0.3449 0.0433 0.4521 0.021 Uiso 1 1 calc R
C13 C 0.6284(4) 0.02848(17) 0.39155(7) 0.0173(3) Uani 1 1 d .
C14 C 0.7298(4) 0.09358(19) 0.34437(7) 0.0194(3) Uani 1 1 d .
H14 H 0.8695 0.0504 0.3228 0.023 Uiso 1 1 calc R
C15 C 0.6262(4) 0.22124(18) 0.32915(7) 0.0184(3) Uani 1 1 d .
H15 H 0.6936 0.2683 0.2970 0.022 Uiso 1 1 calc R
C16 C 0.4202(3) 0.28084(17) 0.36164(7) 0.0152(3) Uani 1 1 d .
N16 N 0.3058(3) 0.41018(16) 0.35190(6) 0.0165(3) Uani 1 1 d .
H16 H 0.186(4) 0.426(2) 0.3715(8) 0.020 Uiso 1 1 d .
C17 C 0.3981(4) 0.51260(18) 0.31657(7) 0.0174(3) Uani 1 1 d .
O17 O 0.5890(3) 0.49682(13) 0.28463(5) 0.0227(3) Uani 1 1 d .
C18 C 0.2365(4) 0.64551(18) 0.32132(8) 0.0229(4) Uani 1 1 d .
H18A H 0.2321 0.6739 0.3613 0.028 Uiso 1 1 calc R
H18B H 0.0435 0.6285 0.3085 0.028 Uiso 1 1 calc R
C19 C 0.3565(4) 0.76276(19) 0.28721(8) 0.0242(4) Uani 1 1 d .
H19A H 0.2507 0.8483 0.2937 0.036 Uiso 1 1 calc R
H19B H 0.3466 0.7386 0.2472 0.036 Uiso 1 1 calc R
H19C H 0.5501 0.7776 0.2986 0.036 Uiso 1 1 calc R
C21 C -0.2014(3) 0.40907(18) 0.46368(7) 0.0148(3) Uani 1 1 d .
O21 O -0.0948(3) 0.28584(13) 0.47280(5) 0.0182(3) Uani 1 1 d .
H21 H 0.015(5) 0.276(2) 0.4525(9) 0.022 Uiso 1 1 d .
O22 O -0.1247(3) 0.48995(13) 0.42785(5) 0.0195(3) Uani 1 1 d .
C22 C -0.4294(3) 0.44166(17) 0.50215(7) 0.0151(3) Uani 1 1 d .
H22 H -0.4749 0.3767 0.5307 0.018 Uiso 1 1 calc R
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'
Br Br -0.2901 2.4595 '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
C12 N11 C16 119.08(14) .
N11 C12 C13 122.09(15) .
N11 C12 H12 119.0 .
C13 C12 H12 119.0 .
C12 C13 C14 119.29(16) .
C12 C13 Br1 119.52(13) .
C14 C13 Br1 121.17(13) .
C15 C14 C13 119.06(15) .
C15 C14 H14 120.5 .
C13 C14 H14 120.5 .
C14 C15 C16 118.80(15) .
C14 C15 H15 120.6 .
C16 C15 H15 120.6 .
N11 C16 N16 114.01(14) .
N11 C16 C15 121.57(15) .
N16 C16 C15 124.43(15) .
C17 N16 C16 127.92(15) .
C17 N16 H16 119.3(16) .
C16 N16 H16 112.5(16) .
O17 C17 N16 123.51(16) .
O17 C17 C18 123.71(16) .
N16 C17 C18 112.78(14) .
C17 C18 C19 112.80(15) .
C17 C18 H18A 109.0 .
C19 C18 H18A 109.0 .
C17 C18 H18B 109.0 .
C19 C18 H18B 109.0 .
H18A C18 H18B 107.8 .
C18 C19 H19A 109.5 .
C18 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C18 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
O22 C21 O21 124.76(15) .
O22 C21 C22 122.61(15) .
O21 C21 C22 112.63(14) .
C21 O21 H21 107.2(17) .
C22 C22 C21 121.60(19) 3_466
C22 C22 H22 119.2 3_466
C21 C22 H22 119.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C13 1.8805(17) .
N11 C12 1.333(2) .
N11 C16 1.339(2) .
C12 C13 1.370(2) .
C12 H12 0.9500 .
C13 C14 1.382(2) .
C14 C15 1.369(2) .
C14 H14 0.9500 .
C15 C16 1.393(2) .
C15 H15 0.9500 .
C16 N16 1.376(2) .
N16 C17 1.372(2) .
N16 H16 0.76(2) .
C17 O17 1.215(2) .
C17 C18 1.500(2) .
C18 C19 1.509(2) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C21 O22 1.215(2) .
C21 O21 1.306(2) .
C21 C22 1.477(2) .
O21 H21 0.73(2) .
C22 C22 1.314(3) 3_466
C22 H22 0.9500 .
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
N16 H16 O22 0.76(2) 2.12(2) 2.8818(18) 174(2)
O21 H21 N11 0.73(2) 1.93(2) 2.6537(18) 168(2)
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_4
C16 N11 C12 C13 -0.3(2) .
N11 C12 C13 C14 -2.5(3) .
N11 C12 C13 Br1 175.91(13) .
C12 C13 C14 C15 2.7(3) .
Br1 C13 C14 C15 -175.62(13) .
C13 C14 C15 C16 -0.4(3) .
C12 N11 C16 N16 -177.43(15) .
C12 N11 C16 C15 2.7(2) .
C14 C15 C16 N11 -2.3(3) .
C14 C15 C16 N16 177.79(16) .
N11 C16 N16 C17 167.95(16) .
C15 C16 N16 C17 -12.2(3) .
C16 N16 C17 O17 6.4(3) .
C16 N16 C17 C18 -174.11(16) .
O17 C17 C18 C19 -6.6(3) .
N16 C17 C18 C19 173.84(15) .
O22 C21 C22 C22 3.2(3) 3_466
O21 C21 C22 C22 -176.94(19) 3_466
