#------------------------------------------------------------------------------
#$Date: 2016-02-04 08:05:34 +0200 (Thu, 04 Feb 2016) $
#$Revision: 175768 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/37/4513715.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_4513715
loop_
_publ_author_name
'Martins, Inês C. B.'
'Sardo, Mariana'
'Santos, Sérgio M.'
'Fernandes, Auguste'
'Antunes, Alexandra'
'André, Vânia'
'Mafra, Luís'
'Duarte, M. Teresa'
_publ_section_title
;
 Packing Interactions and Physicochemical Properties of Novel
 Multicomponent Crystal Forms of the Anti-Inflammatory Azelaic Acid
 Studied by X-ray and Solid-State NMR
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              154
_journal_paper_doi               10.1021/acs.cgd.5b01057
_journal_volume                  16
_journal_year                    2016
_chemical_formula_moiety         C9H15O4,0.5(C6H14N2)
_chemical_formula_sum            'C12 H22 N O4'
_chemical_formula_weight         244.31
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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            8
_cell_length_a                   10.3635(18)
_cell_length_b                   7.6322(18)
_cell_length_c                   33.649(6)
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      1.2
_cell_volume                     2661.5(9)
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_collection       'BRUKER SMART (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 3.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.1082
_diffrn_reflns_av_sigmaI/netI    0.1110
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            9577
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plates
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.238
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.2392
_refine_ls_R_factor_gt           0.0946
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1648P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2214
_refine_ls_wR_factor_ref         0.2874
_reflns_number_gt                985
_reflns_number_total             2629
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg5b01057_si_002.cif
_cod_data_source_block           AA:DABCO
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4513714--4513718.cif.
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4513715
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -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
C1 C 0.2703(6) 0.2500 0.55784(18) 0.0388(19) Uani 1 2 d S
C2 C 0.3203(6) 0.2500 0.59970(16) 0.0396(18) Uani 1 2 d S
H2A H 0.3751 0.1478 0.6028 0.047 Uiso 0.50 1 calc PR
H2B H 0.3751 0.3522 0.6028 0.047 Uiso 0.50 1 calc PR
C3 C 0.2254(6) 0.2500 0.63320(17) 0.045(2) Uani 1 2 d S
H3A H 0.1707 0.1474 0.6309 0.054 Uiso 0.50 1 calc PR
H3B H 0.1707 0.3526 0.6309 0.054 Uiso 0.50 1 calc PR
C4 C 0.2875(6) 0.2500 0.67368(17) 0.047(2) Uani 1 2 d S
H4A H 0.3427 0.1477 0.6755 0.056 Uiso 0.50 1 calc PR
H4B H 0.3427 0.3523 0.6755 0.056 Uiso 0.50 1 calc PR
C5 C 0.2015(7) 0.2500 0.70859(18) 0.065(3) Uani 1 2 d S
H5A H 0.1463 0.1475 0.7072 0.078 Uiso 0.50 1 calc PR
H5B H 0.1463 0.3525 0.7072 0.078 Uiso 0.50 1 calc PR
C6 C 0.2697(7) 0.2500 0.74817(18) 0.055(2) Uani 1 2 d S
H6A H 0.3252 0.1477 0.7491 0.066 Uiso 0.50 1 calc PR
H6B H 0.3252 0.3523 0.7491 0.066 Uiso 0.50 1 calc PR
C7 C 0.1893(7) 0.2500 0.78417(19) 0.072(3) Uani 1 2 d S
H7A H 0.1340 0.1476 0.7834 0.086 Uiso 0.50 1 calc PR
H7B H 0.1340 0.3524 0.7834 0.086 Uiso 0.50 1 calc PR
C8 C 0.2600(7) 0.2500 0.82277(19) 0.063(2) Uani 1 2 d S
H8A H 0.3156 0.1478 0.8231 0.075 Uiso 0.50 1 calc PR
H8B H 0.3156 0.3522 0.8231 0.075 Uiso 0.50 1 calc PR
C9 C 0.1859(7) 0.2500 0.85938(19) 0.058(2) Uani 1 2 d S
C10 C 0.1598(6) 0.2500 0.98879(18) 0.0389(17) Uani 1 2 d S
C11 C 0.0838(5) 0.2500 1.02651(17) 0.043(2) Uani 1 2 d S
H11A H 0.0284 0.1476 1.0265 0.051 Uiso 0.50 1 calc PR
H11B H 0.0284 0.3524 1.0265 0.051 Uiso 0.50 1 calc PR
C12 C 0.1603(5) 0.2500 1.06508(16) 0.0393(18) Uani 1 2 d S
H12A H 0.2152 0.1471 1.0660 0.047 Uiso 0.50 1 calc PR
H12B H 0.2152 0.3529 1.0660 0.047 Uiso 0.50 1 calc PR
C13 C 0.0716(6) 0.2500 1.10030(16) 0.0393(18) Uani 1 2 d S
H13A H 0.0164 0.1476 1.0985 0.047 Uiso 0.50 1 calc PR
H13B H 0.0164 0.3524 1.0985 0.047 Uiso 0.50 1 calc PR
C14 C 0.1367(6) 0.2500 1.14140(16) 0.0433(19) Uani 1 2 d S
H14A H 0.1914 0.1474 1.1435 0.052 Uiso 0.50 1 calc PR
H14B H 0.1914 0.3526 1.1435 0.052 Uiso 0.50 1 calc PR
C15 C 0.0437(7) 0.2500 1.17491(17) 0.063(2) Uani 1 2 d S
H15A H -0.0111 0.1475 1.1725 0.075 Uiso 0.50 1 calc PR
H15B H -0.0111 0.3525 1.1725 0.075 Uiso 0.50 1 calc PR
C16 C 0.1045(7) 0.2500 1.21589(18) 0.055(2) Uani 1 2 d S
H16A H 0.1590 0.1473 1.2185 0.066 Uiso 0.50 1 calc PR
H16B H 0.1590 0.3527 1.2185 0.066 Uiso 0.50 1 calc PR
C17 C 0.0077(9) 0.2500 1.2486(2) 0.102(4) Uani 1 2 d S
H17A H -0.0468 0.3523 1.2454 0.122 Uiso 0.50 1 calc PR
H17B H -0.0468 0.1477 1.2454 0.122 Uiso 0.50 1 calc PR
C18 C 0.0578(9) 0.2500 1.2897(2) 0.087(4) Uani 1 2 d S
C19 C 0.2165(5) 0.2500 1.39713(18) 0.047(2) Uani 1 2 d S
H19A H 0.2536 0.3529 1.3847 0.056 Uiso 0.50 1 calc PR
H19B H 0.2536 0.1471 1.3847 0.056 Uiso 0.50 1 calc PR
C20 C 0.2485(6) 0.2500 1.4410(2) 0.068(3) Uani 1 2 d S
H20A H 0.2988 0.1469 1.4477 0.081 Uiso 0.50 1 calc PR
H20B H 0.2988 0.3531 1.4477 0.081 Uiso 0.50 1 calc PR
C21 C 0.0197(5) 0.0954(8) 1.40933(15) 0.0661(18) Uani 1 1 d .
H21A H 0.0549 -0.0096 1.3972 0.079 Uiso 1 1 calc R
H21B H -0.0726 0.0969 1.4046 0.079 Uiso 1 1 calc R
C22 C 0.0457(5) 0.0929(9) 1.45341(15) 0.0661(19) Uani 1 1 d .
H22A H -0.0351 0.0944 1.4679 0.079 Uiso 1 1 calc R
H22B H 0.0922 -0.0129 1.4605 0.079 Uiso 1 1 calc R
N1 N 0.0787(5) 0.2500 1.39137(14) 0.0478(18) Uani 1 2 d S
H1 H 0.0616 0.2500 1.3648 0.057 Uiso 1 2 calc SR
N2 N 0.1240(5) 0.2500 1.46389(16) 0.063(2) Uani 1 2 d S
H2 H 0.131(8) 0.2500 1.489(3) 0.12(4) Uiso 1 2 d S
O1 O 0.3543(4) 0.2500 0.52969(12) 0.0610(18) Uani 1 2 d S
H1O H 0.440(7) 0.2500 0.536(2) 0.07(3) Uiso 1 2 d S
O2 O 0.1555(4) 0.2500 0.54949(12) 0.0590(16) Uani 1 2 d S
O3 O 0.2333(6) 0.2500 0.89174(17) 0.136(4) Uani 1 2 d S
O4 O 0.0984(7) 0.3733(12) 0.8613(2) 0.082(3) Uani 0.50 1 d P
O5 O 0.0922(5) 0.2500 0.95668(13) 0.0655(18) Uani 1 2 d SD
H5O H 0.115(9) 0.2500 0.9306(10) 0.16(5) Uiso 1 2 d SD
O6 O 0.2790(4) 0.2500 0.98845(13) 0.0616(17) Uani 1 2 d S
O7 O 0.1729(9) 0.2500 1.2964(2) 0.170(4) Uani 1 2 d S
O8 O -0.0098(7) 0.2500 1.31668(18) 0.206(6) Uani 1 2 d S
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
O2 C1 O1 119.3(6) . .
O2 C1 C2 123.5(6) . .
O1 C1 C2 117.2(5) . .
C3 C2 C1 118.7(5) . .
C2 C3 C4 113.6(5) . .
C5 C4 C3 117.5(6) . .
C4 C5 C6 114.8(6) . .
C7 C6 C5 117.5(6) . .
C6 C7 C8 116.1(6) . .
C9 C8 C7 118.6(6) . .
O3 C9 O4 103.9(5) . 7_565
O3 C9 O4 103.9(5) . .
O4 C9 O4 92.0(9) 7_565 .
O3 C9 C8 123.8(7) . .
O4 C9 C8 114.1(5) 7_565 .
O4 C9 C8 114.1(5) . .
O6 C10 O5 122.4(6) . .
O6 C10 C11 122.3(6) . .
O5 C10 C11 115.3(6) . .
C10 C11 C12 116.8(5) . .
C13 C12 C11 110.8(5) . .
C12 C13 C14 116.2(5) . .
C15 C14 C13 113.5(5) . .
C14 C15 C16 114.9(6) . .
C17 C16 C15 113.1(6) . .
C18 C17 C16 117.1(8) . .
O8 C18 O7 116.9(8) . .
O8 C18 C17 121.8(9) . .
O7 C18 C17 121.4(8) . .
N1 C19 C20 110.4(5) . .
N2 C20 C19 108.1(5) . .
N1 C21 C22 110.0(5) . .
N2 C22 C21 108.7(5) . .
C19 N1 C21 111.1(3) . 7_565
C19 N1 C21 111.1(3) . .
C21 N1 C21 107.9(6) 7_565 .
C22 N2 C22 107.2(5) . 7_565
C22 N2 C20 110.3(4) . .
C22 N2 C20 110.3(4) 7_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.223(7) .
C1 O1 1.286(7) .
C1 C2 1.501(8) .
C2 C3 1.496(8) .
C3 C4 1.506(8) .
C4 C5 1.475(9) .
C5 C6 1.508(9) .
C6 C7 1.470(9) .
C7 C8 1.491(9) .
C8 C9 1.452(9) .
C9 O3 1.195(8) .
C9 O4 1.309(8) 7_565
C9 O4 1.309(8) .
C10 O6 1.235(7) .
C10 O5 1.288(7) .
C10 C11 1.493(8) .
C11 C12 1.521(8) .
C12 C13 1.500(8) .
C13 C14 1.539(8) .
C14 C15 1.483(8) .
C15 C16 1.516(8) .
C16 C17 1.490(10) .
C17 C18 1.475(10) .
C18 O8 1.148(9) .
C18 O7 1.214(10) .
C19 N1 1.440(7) .
C19 C20 1.514(9) .
C20 N2 1.503(8) .
C21 N1 1.460(6) .
C21 C22 1.508(7) .
C22 N2 1.490(7) .
N1 C21 1.460(6) 7_565
N2 C22 1.490(7) 7_565
