#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:58:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180458 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/27/7212762.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_7212762
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 (C10 H18 O4)
;
_chemical_formula_sum            'C26 H36 Br2 N4 O6'
_chemical_formula_weight         660.41
_chemical_name_systematic
;
AR-BI-C4 N-(5-bromo-2-pyridyl)propionamide, HOOC-(CH2)8-COOH
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.293(2)
_cell_angle_beta                 81.204(2)
_cell_angle_gamma                88.593(2)
_cell_formula_units_Z            1
_cell_length_a                   5.1849(4)
_cell_length_b                   11.4665(8)
_cell_length_c                   12.4870(9)
_cell_measurement_reflns_used    6258
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.55
_cell_measurement_theta_min      3.60
_cell_volume                     694.66(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12522
_diffrn_reflns_theta_full        31.51
_diffrn_reflns_theta_max         31.51
_diffrn_reflns_theta_min         1.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.965
_exptl_absorpt_correction_T_max  0.7559
_exptl_absorpt_correction_T_min  0.3834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0313
_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)+(0.0400P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0758
_reflns_number_gt                3756
_reflns_number_total             4500
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00052c.txt
_cod_data_source_block           ar0921m(D15)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               7212762
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.77714(4) -0.454445(15) 0.213776(15) 0.02944(7) Uani 1 1 d .
N11 N 0.7338(3) -0.10891(12) 0.24309(11) 0.0194(3) Uani 1 1 d .
C12 C 0.9518(3) -0.05162(14) 0.17696(13) 0.0189(3) Uani 1 1 d .
N12 N 0.9752(3) 0.07005(12) 0.17075(12) 0.0206(3) Uani 1 1 d .
H12 H 0.855(4) 0.0941(19) 0.2089(18) 0.025 Uiso 1 1 d .
C13 C 1.1355(3) -0.11091(15) 0.11985(14) 0.0220(3) Uani 1 1 d .
H13 H 1.2898 -0.0686 0.0742 0.026 Uiso 1 1 calc R
C14 C 1.0873(3) -0.23214(15) 0.13148(14) 0.0234(3) Uani 1 1 d .
H14 H 1.2091 -0.2755 0.0944 0.028 Uiso 1 1 calc R
C15 C 0.8594(3) -0.29007(14) 0.19789(13) 0.0211(3) Uani 1 1 d .
C16 C 0.6886(3) -0.22603(14) 0.25227(14) 0.0213(3) Uani 1 1 d .
H16 H 0.5328 -0.2666 0.2980 0.026 Uiso 1 1 calc R
C21 C 1.1759(3) 0.15299(14) 0.11543(13) 0.0204(3) Uani 1 1 d .
O21 O 1.3740(2) 0.12933(11) 0.06230(11) 0.0298(3) Uani 1 1 d .
C22 C 1.1224(3) 0.27895(14) 0.12643(15) 0.0228(3) Uani 1 1 d .
H22A H 1.0406 0.2695 0.2059 0.027 Uiso 1 1 calc R
H22B H 0.9968 0.3203 0.0749 0.027 Uiso 1 1 calc R
C23 C 1.3670(3) 0.35937(15) 0.09733(16) 0.0280(4) Uani 1 1 d .
H23A H 1.3217 0.4397 0.1060 0.042 Uiso 1 1 calc R
H23B H 1.4466 0.3708 0.0181 0.042 Uiso 1 1 calc R
H23C H 1.4909 0.3197 0.1490 0.042 Uiso 1 1 calc R
C31 C 0.4066(3) 0.09111(13) 0.37417(13) 0.0185(3) Uani 1 1 d .
O31 O 0.3534(2) -0.02055(11) 0.37418(11) 0.0253(3) Uani 1 1 d .
H31 H 0.463(5) -0.040(2) 0.335(2) 0.030 Uiso 1 1 d .
O32 O 0.6072(2) 0.14713(11) 0.32375(11) 0.0260(3) Uani 1 1 d .
C32 C 0.1958(3) 0.14306(14) 0.44073(13) 0.0191(3) Uani 1 1 d .
H32A H 0.1672 0.0891 0.5215 0.023 Uiso 1 1 calc R
H32B H 0.0311 0.1437 0.4096 0.023 Uiso 1 1 calc R
C33 C 0.2624(3) 0.27277(14) 0.43627(14) 0.0212(3) Uani 1 1 d .
H33A H 0.4112 0.2698 0.4781 0.025 Uiso 1 1 calc R
H33B H 0.3188 0.3231 0.3555 0.025 Uiso 1 1 calc R
C34 C 0.0376(3) 0.33511(14) 0.48697(14) 0.0202(3) Uani 1 1 d .
H34A H -0.0164 0.2866 0.5684 0.024 Uiso 1 1 calc R
H34B H -0.1130 0.3372 0.4463 0.024 Uiso 1 1 calc R
C35 C 0.1117(3) 0.46564(14) 0.47809(15) 0.0222(3) Uani 1 1 d .
H35A H 0.2566 0.4625 0.5221 0.027 Uiso 1 1 calc R
H35B H 0.1761 0.5121 0.3970 0.027 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
C16 N11 C12 118.54(13) .
N11 C12 N12 113.74(13) .
N11 C12 C13 122.39(14) .
N12 C12 C13 123.87(14) .
C21 N12 C12 128.97(13) .
C21 N12 H12 116.2(15) .
C12 N12 H12 114.7(15) .
C14 C13 C12 118.27(14) .
C14 C13 H13 120.9 .
C12 C13 H13 120.9 .
C13 C14 C15 119.10(14) .
C13 C14 H14 120.5 .
C15 C14 H14 120.5 .
C16 C15 C14 119.33(14) .
C16 C15 Br1 119.48(12) .
C14 C15 Br1 121.19(12) .
N11 C16 C15 122.35(15) .
N11 C16 H16 118.8 .
C15 C16 H16 118.8 .
O21 C21 N12 124.20(15) .
O21 C21 C22 123.20(14) .
N12 C21 C22 112.59(13) .
C21 C22 C23 112.74(14) .
C21 C22 H22A 109.0 .
C23 C22 H22A 109.0 .
C21 C22 H22B 109.0 .
C23 C22 H22B 109.0 .
H22A C22 H22B 107.8 .
C22 C23 H23A 109.5 .
C22 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
C22 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
O32 C31 O31 122.75(14) .
O32 C31 C32 123.11(14) .
O31 C31 C32 114.13(13) .
C31 O31 H31 109.5(17) .
C31 C32 C33 112.39(12) .
C31 C32 H32A 109.1 .
C33 C32 H32A 109.1 .
C31 C32 H32B 109.1 .
C33 C32 H32B 109.1 .
H32A C32 H32B 107.9 .
C34 C33 C32 113.66(12) .
C34 C33 H33A 108.8 .
C32 C33 H33A 108.8 .
C34 C33 H33B 108.8 .
C32 C33 H33B 108.8 .
H33A C33 H33B 107.7 .
C33 C34 C35 111.72(13) .
C33 C34 H34A 109.3 .
C35 C34 H34A 109.3 .
C33 C34 H34B 109.3 .
C35 C34 H34B 109.3 .
H34A C34 H34B 107.9 .
C35 C35 C34 113.68(16) 2_566
C35 C35 H35A 108.8 2_566
C34 C35 H35A 108.8 .
C35 C35 H35B 108.8 2_566
C34 C35 H35B 108.8 .
H35A C35 H35B 107.7 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C15 1.8834(15) .
N11 C16 1.334(2) .
N11 C12 1.3392(19) .
C12 N12 1.3796(19) .
C12 C13 1.396(2) .
N12 C21 1.3683(19) .
N12 H12 0.82(2) .
C13 C14 1.376(2) .
C13 H13 0.9500 .
C14 C15 1.383(2) .
C14 H14 0.9500 .
C15 C16 1.374(2) .
C16 H16 0.9500 .
C21 O21 1.2092(19) .
C21 C22 1.509(2) .
C22 C23 1.514(2) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C31 O32 1.2096(19) .
C31 O31 1.3163(18) .
C31 C32 1.499(2) .
O31 H31 0.77(2) .
C32 C33 1.517(2) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.514(2) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C35 1.519(2) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C35 C35 1.516(3) 2_566
C35 H35A 0.9900 .
C35 H35B 0.9900 .
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
O31 H31 N11 0.77(2) 1.99(2) 2.7522(17) 174(2)
N12 H12 O32 0.82(2) 2.01(2) 2.8209(17) 169(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 N12 178.11(14) .
C16 N11 C12 C13 -1.6(2) .
N11 C12 N12 C21 177.01(16) .
C13 C12 N12 C21 -3.3(3) .
N11 C12 C13 C14 0.8(2) .
N12 C12 C13 C14 -178.92(16) .
C12 C13 C14 C15 0.6(3) .
C13 C14 C15 C16 -1.1(3) .
C13 C14 C15 Br1 178.20(13) .
C12 N11 C16 C15 1.1(2) .
C14 C15 C16 N11 0.3(3) .
Br1 C15 C16 N11 -179.04(12) .
C12 N12 C21 O21 -1.0(3) .
C12 N12 C21 C22 178.22(15) .
O21 C21 C22 C23 -17.8(2) .
N12 C21 C22 C23 162.97(15) .
O32 C31 C32 C33 0.5(2) .
O31 C31 C32 C33 -178.71(14) .
C31 C32 C33 C34 171.12(14) .
C32 C33 C34 C35 -178.69(14) .
C33 C34 C35 C35 176.85(18) 2_566
