#------------------------------------------------------------------------------
#$Date: 2022-09-20 00:26:17 +0200 (Tue 20 de Sep de 2022) $
#$Revision: 277984 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/55/7245511.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_7245511
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            'C21 H26 N2 O8'
_chemical_formula_weight         434.44
_chemical_name_systematic
'1,5-pentanediamine-o-Phthalic acid salt; 1,5-pentanediamine-1,2-Phthalic acid salt'
_chemical_properties_physical    Moisture-sensitive,Heat-sensitive
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-08-30 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.730(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2457(12)
_cell_length_b                   18.4249(14)
_cell_length_c                   8.4299(6)
_cell_measurement_reflns_used    1809
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.554
_cell_measurement_theta_min      2.707
_cell_volume                     2214.7(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5226
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0592
_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)+(0.0548P)²+1.3625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                1179
_reflns_number_total             1940
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ce00628f2.cif
_cod_data_source_block           210827c
_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      C2/c
_cod_database_code               7245511
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.23935(15) 0.43672(11) 1.0964(3) 0.0439(6) Uani 1 1 d . . .
H1A H 0.2158 0.4077 1.1558 0.066 Uiso 1 1 calc R . .
H1B H 0.2820 0.4660 1.1668 0.066 Uiso 1 1 calc R . .
H1C H 0.2661 0.4100 1.0382 0.066 Uiso 1 1 calc R . .
O1 O 0.15316(17) 0.04697(10) 0.2012(3) 0.0748(7) Uani 1 1 d . . .
O2 O 0.17699(18) 0.14918(11) 0.0884(3) 0.0800(8) Uani 1 1 d . . .
O3 O 0.17060(16) 0.27877(10) 0.1188(3) 0.0679(7) Uani 1 1 d . . .
H3 H 0.1679 0.2348 0.1030 0.102 Uiso 1 1 calc R . .
O4 O 0.15121(16) 0.35766(10) 0.2965(3) 0.0672(7) Uani 1 1 d . . .
C1 C 0.1546(2) 0.11448(15) 0.2008(4) 0.0482(7) Uani 1 1 d . . .
C2 C 0.15165(18) 0.29341(14) 0.2538(3) 0.0428(7) Uani 1 1 d . . .
C3 C 0.12768(17) 0.15621(13) 0.3348(3) 0.0382(6) Uani 1 1 d . . .
C4 C 0.12885(17) 0.23335(14) 0.3600(3) 0.0394(7) Uani 1 1 d . . .
C5 C 0.1065(2) 0.26014(17) 0.4970(4) 0.0589(8) Uani 1 1 d . . .
H5 H 0.1082 0.3100 0.5155 0.071 Uiso 1 1 calc R . .
C6 C 0.0817(2) 0.2145(2) 0.6060(4) 0.0729(10) Uani 1 1 d . . .
H6 H 0.0676 0.2338 0.6960 0.087 Uiso 1 1 calc R . .
C7 C 0.0784(2) 0.1401(2) 0.5796(4) 0.0698(10) Uani 1 1 d . . .
H7 H 0.0610 0.1092 0.6506 0.084 Uiso 1 1 calc R . .
C8 C 0.10119(19) 0.11231(16) 0.4460(4) 0.0548(8) Uani 1 1 d . . .
H8 H 0.0988 0.0623 0.4296 0.066 Uiso 1 1 calc R . .
C9 C 0.16265(19) 0.48101(14) 0.9767(3) 0.0445(7) Uani 1 1 d . . .
H9A H 0.1878 0.5096 0.9061 0.053 Uiso 1 1 calc R . .
H9B H 0.1389 0.5144 1.0411 0.053 Uiso 1 1 calc R . .
C10 C 0.0821(2) 0.43473(14) 0.8637(3) 0.0488(7) Uani 1 1 d . . .
H10A H 0.0600 0.4034 0.9343 0.059 Uiso 1 1 calc R . .
H10B H 0.1048 0.4040 0.7931 0.059 Uiso 1 1 calc R . .
C11 C 0.0000 0.4803(2) 0.7500 0.0471(10) Uani 1 2 d S . .
H11A H -0.0222 0.5113 0.8209 0.056 Uiso 0.50 1 calc PR . .
H11B H 0.0222 0.5113 0.6791 0.056 Uiso 0.50 1 calc PR . .
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 . . ?
C2 O3 H3 109.5 . . ?
O1 C1 O2 120.6(3) . . ?
O1 C1 C3 119.2(3) . . ?
O2 C1 C3 120.2(2) . . ?
O4 C2 O3 118.7(2) . . ?
O4 C2 C4 119.5(2) . . ?
O3 C2 C4 121.8(2) . . ?
C8 C3 C4 117.6(2) . . ?
C8 C3 C1 114.7(2) . . ?
C4 C3 C1 127.7(2) . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 C2 113.4(2) . . ?
C3 C4 C2 128.2(2) . . ?
C6 C5 C4 122.1(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 119.3(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 C3 122.9(3) . . ?
C7 C8 H8 118.5 . . ?
C3 C8 H8 118.5 . . ?
N1 C9 C10 112.6(2) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 112.6(2) . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C10 113.4(3) 2_556 . ?
C10 C11 H11A 108.9 2_556 . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 2_556 . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
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 1.489(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O1 C1 1.244(3) . ?
O2 C1 1.285(3) . ?
O3 C2 1.298(3) . ?
O3 H3 0.8200 . ?
O4 C2 1.238(3) . ?
C1 C3 1.538(4) . ?
C2 C4 1.538(4) . ?
C3 C8 1.402(4) . ?
C3 C4 1.436(4) . ?
C4 C5 1.405(4) . ?
C5 C6 1.392(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.522(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.529(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C10 1.529(3) 2_556 ?
C11 H11A 0.9700 . ?
C11 H11B 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
O1 C1 C3 C8 -1.4(4) . . . . ?
O2 C1 C3 C8 177.6(3) . . . . ?
O1 C1 C3 C4 177.1(3) . . . . ?
O2 C1 C3 C4 -4.0(4) . . . . ?
C8 C3 C4 C5 2.0(4) . . . . ?
C1 C3 C4 C5 -176.4(2) . . . . ?
C8 C3 C4 C2 -177.7(2) . . . . ?
C1 C3 C4 C2 3.9(4) . . . . ?
O4 C2 C4 C5 1.8(4) . . . . ?
O3 C2 C4 C5 -177.5(3) . . . . ?
O4 C2 C4 C3 -178.4(3) . . . . ?
O3 C2 C4 C3 2.2(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C2 C4 C5 C6 178.6(3) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
C5 C6 C7 C8 1.0(5) . . . . ?
C6 C7 C8 C3 -0.1(5) . . . . ?
C4 C3 C8 C7 -1.4(4) . . . . ?
C1 C3 C8 C7 177.2(3) . . . . ?
N1 C9 C10 C11 175.68(18) . . . . ?
C9 C10 C11 C10 -179.6(3) . . . 2_556 ?
