#------------------------------------------------------------------------------
#$Date: 2022-09-20 00:26:17 +0200 (Tue 20 de Sep de 2022) $
#$Revision: 277984 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/55/7245507.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_7245507
loop_
_publ_author_name
'Li, Zihan'
'Fang, Xincao'
'Yang, Pengpeng'
'Li, Shushu'
'Wen, Qingshi'
'Zhuang, Wei'
'Wu, Jianglan'
'Zhu, Chenjie'
'Ying, Hanjie'
_publ_section_title
;
 Discovering Crystal Forms of the Bio-based Nylon 5O Monomer
 1,5-pentanediamine-O-phthalate: Insight into the Crystal Structures,
 Transformations and Stability
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00628F
_journal_year                    2022
_chemical_formula_sum            'C13 H24 N2 O6'
_chemical_formula_weight         304.34
_chemical_name_common            '1,5-Diaminopentane acidephtalique;'
_chemical_name_systematic
'1,5-Pentanediamine acidephtalique;1,5-Pentanediamine 1,2-phthalicacid'
_chemical_properties_physical    Moisture-sensitive,Hygroscopic,Heat-sensitive
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2020-05-28 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.762(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0825(7)
_cell_length_b                   12.6540(11)
_cell_length_c                   17.5329(15)
_cell_measurement_reflns_used    1315
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.666
_cell_measurement_theta_min      2.335
_cell_volume                     1563.4(2)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0832
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            2761
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0513
_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)+(0.0352P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                1594
_reflns_number_total             2761
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ce00628f2.cif
_cod_data_source_block           190719e
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7245507
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4962(4) 1.05724(19) 0.79093(11) 0.0355(7) Uani 1 1 d . . .
H1A H 0.4034 1.0223 0.8106 0.053 Uiso 1 1 calc R . .
H1B H 0.4857 1.1259 0.8005 0.053 Uiso 1 1 calc R . .
H1C H 0.6079 1.0339 0.8121 0.053 Uiso 1 1 calc R . .
N2 N 0.5789(4) 0.6997(2) 0.45343(13) 0.0449(8) Uani 1 1 d . . .
H2A H 0.6959 0.6828 0.4730 0.067 Uiso 1 1 calc R . .
H2B H 0.5741 0.7017 0.4025 0.067 Uiso 1 1 calc R . .
H2C H 0.4975 0.6516 0.4674 0.067 Uiso 1 1 calc R . .
O1 O 0.4729(4) 0.26475(17) 0.82913(11) 0.0543(7) Uani 1 1 d . . .
O2 O 0.5078(4) 0.30889(17) 0.70976(10) 0.0552(7) Uani 1 1 d . . .
O3 O 0.3254(3) 0.49626(17) 0.62995(10) 0.0415(6) Uani 1 1 d . . .
O4 O 0.6372(3) 0.52314(19) 0.63137(11) 0.0486(6) Uani 1 1 d . . .
O5 O 0.2613(3) 0.58148(17) 0.49051(10) 0.0516(7) Uani 1 1 d . . .
H5C H 0.2867 0.5493 0.5328 0.062 Uiso 1 1 d R . .
H5D H 0.2977 0.5434 0.4548 0.062 Uiso 1 1 d R . .
O6 O 0.5442(3) 0.20393(18) 0.98227(11) 0.0661(8) Uani 1 1 d . . .
H6C H 0.5261 0.2234 0.9357 0.079 Uiso 1 1 d R . .
H6D H 0.4514 0.1653 0.9920 0.079 Uiso 1 1 d R . .
C1 C 0.4934(4) 0.3317(2) 0.77739(16) 0.0328(8) Uani 1 1 d . . .
C2 C 0.4873(5) 0.5122(2) 0.66336(15) 0.0320(7) Uani 1 1 d . . .
C3 C 0.5028(4) 0.4462(2) 0.80190(14) 0.0269(7) Uani 1 1 d . . .
C4 C 0.5029(4) 0.5288(2) 0.74904(14) 0.0258(7) Uani 1 1 d . . .
C5 C 0.5130(5) 0.6318(3) 0.77413(15) 0.0406(9) Uani 1 1 d . . .
H5 H 0.5128 0.6862 0.7384 0.049 Uiso 1 1 calc R . .
C6 C 0.5233(5) 0.6563(3) 0.85129(16) 0.0451(9) Uani 1 1 d . . .
H6 H 0.5291 0.7264 0.8674 0.054 Uiso 1 1 calc R . .
C7 C 0.5249(5) 0.5757(3) 0.90360(16) 0.0411(8) Uani 1 1 d . . .
H7 H 0.5332 0.5910 0.9557 0.049 Uiso 1 1 calc R . .
C8 C 0.5143(4) 0.4720(3) 0.87917(15) 0.0356(8) Uani 1 1 d . . .
H8 H 0.5148 0.4182 0.9153 0.043 Uiso 1 1 calc R . .
C9 C 0.4821(4) 1.0398(2) 0.70668(14) 0.0327(7) Uani 1 1 d . . .
H9A H 0.5831 1.0785 0.6857 0.039 Uiso 1 1 calc R . .
H9B H 0.3623 1.0682 0.6839 0.039 Uiso 1 1 calc R . .
C10 C 0.4948(4) 0.9246(2) 0.68462(14) 0.0336(8) Uani 1 1 d . . .
H10A H 0.3899 0.8858 0.7027 0.040 Uiso 1 1 calc R . .
H10B H 0.6122 0.8947 0.7086 0.040 Uiso 1 1 calc R . .
C11 C 0.4886(4) 0.9142(2) 0.59779(15) 0.0365(8) Uani 1 1 d . . .
H11A H 0.3650 0.9377 0.5751 0.044 Uiso 1 1 calc R . .
H11B H 0.5827 0.9614 0.5799 0.044 Uiso 1 1 calc R . .
C12 C 0.5238(5) 0.8044(2) 0.56896(15) 0.0396(8) Uani 1 1 d . . .
H12A H 0.4242 0.7574 0.5825 0.047 Uiso 1 1 calc R . .
H12B H 0.6439 0.7783 0.5932 0.047 Uiso 1 1 calc R . .
C13 C 0.5279(5) 0.8048(2) 0.48243(15) 0.0418(9) Uani 1 1 d . . .
H13A H 0.4042 0.8253 0.4582 0.050 Uiso 1 1 calc R . .
H13B H 0.6195 0.8567 0.4687 0.050 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'
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
_geom_angle_publ_flag
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C13 N2 H2A 109.5 . . ?
C13 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C13 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
H5C O5 H5D 108.6 . . ?
H6C O6 H6D 108.3 . . ?
O2 C1 O1 124.1(3) . . ?
O2 C1 C3 119.4(3) . . ?
O1 C1 C3 116.4(2) . . ?
O3 C2 O4 125.8(2) . . ?
O3 C2 C4 117.4(3) . . ?
O4 C2 C4 116.6(3) . . ?
C8 C3 C4 117.9(3) . . ?
C8 C3 C1 120.0(3) . . ?
C4 C3 C1 122.1(2) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 C2 116.5(3) . . ?
C3 C4 C2 123.5(3) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 118.9(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 121.5(3) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
N1 C9 C10 113.4(2) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 110.0(2) . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C10 115.1(3) . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 C13 110.6(3) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N2 C13 C12 111.6(2) . . ?
N2 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.487(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C13 1.482(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
O1 C1 1.260(3) . ?
O2 C1 1.234(3) . ?
O3 C2 1.251(4) . ?
O4 C2 1.257(4) . ?
O5 H5C 0.8499 . ?
O5 H5D 0.8501 . ?
O6 H6C 0.8500 . ?
O6 H6D 0.8500 . ?
C1 C3 1.511(4) . ?
C2 C4 1.510(3) . ?
C3 C8 1.388(3) . ?
C3 C4 1.397(4) . ?
C4 C5 1.376(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.513(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.524(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.509(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.520(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C3 C8 -170.7(3) . . . . ?
O1 C1 C3 C8 8.5(4) . . . . ?
O2 C1 C3 C4 8.4(5) . . . . ?
O1 C1 C3 C4 -172.4(3) . . . . ?
C8 C3 C4 C5 -0.4(4) . . . . ?
C1 C3 C4 C5 -179.6(3) . . . . ?
C8 C3 C4 C2 -178.8(3) . . . . ?
C1 C3 C4 C2 2.1(5) . . . . ?
O3 C2 C4 C5 -98.1(3) . . . . ?
O4 C2 C4 C5 77.0(4) . . . . ?
O3 C2 C4 C3 80.3(4) . . . . ?
O4 C2 C4 C3 -104.7(4) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C2 C4 C5 C6 178.5(3) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C3 0.4(5) . . . . ?
C4 C3 C8 C7 0.2(5) . . . . ?
C1 C3 C8 C7 179.4(3) . . . . ?
N1 C9 C10 C11 -177.3(2) . . . . ?
C9 C10 C11 C12 173.0(3) . . . . ?
C10 C11 C12 C13 -176.0(3) . . . . ?
C11 C12 C13 N2 175.0(3) . . . . ?
