#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/56/7215672.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_7215672
loop_
_publ_author_name
'Vilela, Sérgio M. F.'
'Ananias, Duarte'
'Silva, Patrícia'
'Nolasco, Mariela'
'Carlos, Luís D.'
'de Zea Bermudez, Verónica'
'Rocha, João'
'Tomé, João P. C.'
'Almeida Paz, Filipe A.'
_publ_section_title
;
 Coordination polymers based on a glycine-derivative ligand
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              8119
_journal_paper_doi               10.1039/C4CE00465E
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C9 H12 Cl N5 O4'
_chemical_formula_sum            'C9 H12 Cl N5 O4'
_chemical_formula_weight         289.69
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '25 February 2014'
_audit_creation_method           'SHELXL-97, manual editing plus enCIFer'
_cell_angle_alpha                90.00
_cell_angle_beta                 113.281(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2191(5)
_cell_length_b                   24.9432(19)
_cell_length_c                   7.4918(5)
_cell_measurement_reflns_used    3201
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.80
_cell_measurement_theta_min      3.07
_cell_volume                     1239.19(16)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT+ (Bruker, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ 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  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13354
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.9433
_exptl_absorpt_correction_T_min  0.9195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS (Sheldrick, 1997)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0476
_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)+(0.0633P)²+0.3332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                1910
_reflns_number_total             2810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00465e2.cif
_cod_data_source_block           L'
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7215670--7215672.cif.
;
_cod_original_cell_volume        1239.19(15)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7215672
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
Cl1 Cl 0.56983(9) 1.08580(3) 0.58075(9) 0.02657(19) Uani 1 1 d .
N1 N 0.8303(3) 1.00951(8) 0.6378(3) 0.0179(4) Uani 1 1 d .
N2 N 0.6347(3) 1.00873(8) 0.8302(3) 0.0174(4) Uani 1 1 d .
N3 N 0.8844(3) 0.94075(8) 0.8765(3) 0.0171(4) Uani 1 1 d .
N4 N 1.0668(3) 0.94266(8) 0.6873(3) 0.0185(4) Uani 1 1 d D
H4 H 1.090(4) 0.9597(10) 0.585(3) 0.028 Uiso 1 1 d D
N5 N 0.6941(3) 0.94203(8) 1.0591(3) 0.0188(4) Uani 1 1 d D
H5 H 0.595(3) 0.9589(10) 1.091(3) 0.028 Uiso 1 1 d D
O1 O 1.0857(3) 0.81155(8) 0.8842(3) 0.0341(5) Uani 1 1 d .
O2 O 0.8920(3) 0.84445(7) 0.5907(2) 0.0261(4) Uani 1 1 d .
O3 O 0.5978(3) 0.84086(7) 0.8841(3) 0.0265(4) Uani 1 1 d .
O4 O 0.8264(3) 0.80199(7) 1.1503(2) 0.0266(4) Uani 1 1 d .
C1 C 0.6925(3) 1.02789(10) 0.6970(3) 0.0175(5) Uani 1 1 d .
C2 C 0.7393(3) 0.96392(10) 0.9182(3) 0.0163(5) Uani 1 1 d .
C3 C 0.9238(3) 0.96465(9) 0.7357(3) 0.0160(5) Uani 1 1 d .
C4 C 1.1744(3) 0.89567(10) 0.7870(4) 0.0207(5) Uani 1 1 d .
H4A H 1.2416 0.9040 0.9273 0.025 Uiso 1 1 calc R
H4B H 1.2811 0.8875 0.7394 0.025 Uiso 1 1 calc R
C5 C 1.0461(4) 0.84632(10) 0.7631(3) 0.0221(6) Uani 1 1 d .
C6 C 0.7638(4) 0.79789(12) 0.5551(4) 0.0334(7) Uani 1 1 d .
H6A H 0.8464 0.7654 0.5798 0.050 Uiso 1 1 calc R
H6B H 0.6663 0.7981 0.4197 0.050 Uiso 1 1 calc R
H6C H 0.6915 0.7986 0.6417 0.050 Uiso 1 1 calc R
C7 C 0.7951(4) 0.89466(10) 1.1635(3) 0.0207(5) Uani 1 1 d .
H7A H 0.7702 0.8914 1.2839 0.025 Uiso 1 1 calc R
H7B H 0.9422 0.8987 1.2016 0.025 Uiso 1 1 calc R
C8 C 0.7251(3) 0.84378(10) 1.0450(3) 0.0198(5) Uani 1 1 d .
C9 C 0.7765(4) 0.75033(11) 1.0549(4) 0.0308(6) Uani 1 1 d .
H9A H 0.6298 0.7455 0.9998 0.046 Uiso 1 1 calc R
H9B H 0.8398 0.7219 1.1496 0.046 Uiso 1 1 calc R
H9C H 0.8261 0.7487 0.9507 0.046 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C3 112.55(19)
C1 N2 C2 112.53(19)
C2 N3 C3 115.0(2)
C3 N4 C4 120.51(19)
C3 N4 H4 115.7(17)
C4 N4 H4 123.7(17)
C2 N5 C7 122.15(19)
C2 N5 H5 117.8(16)
C7 N5 H5 120.1(16)
C5 O2 C6 115.9(2)
C8 O4 C9 115.5(2)
N2 C1 N1 129.5(2)
N2 C1 Cl1 115.52(17)
N1 C1 Cl1 115.01(17)
N3 C2 N5 117.8(2)
N3 C2 N2 125.2(2)
N5 C2 N2 116.99(19)
N3 C3 N4 117.3(2)
N3 C3 N1 125.2(2)
N4 C3 N1 117.5(2)
N4 C4 C5 114.99(19)
N4 C4 H4A 108.5
C5 C4 H4A 108.5
N4 C4 H4B 108.5
C5 C4 H4B 108.5
H4A C4 H4B 107.5
O1 C5 O2 124.3(2)
O1 C5 C4 123.1(2)
O2 C5 C4 112.5(2)
O2 C6 H6A 109.5
O2 C6 H6B 109.5
H6A C6 H6B 109.5
O2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N5 C7 C8 112.8(2)
N5 C7 H7A 109.0
C8 C7 H7A 109.0
N5 C7 H7B 109.0
C8 C7 H7B 109.0
H7A C7 H7B 107.8
O3 C8 O4 124.8(2)
O3 C8 C7 126.0(2)
O4 C8 C7 109.2(2)
O4 C9 H9A 109.5
O4 C9 H9B 109.5
H9A C9 H9B 109.5
O4 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.737(2)
N1 C1 1.321(3)
N1 C3 1.362(3)
N2 C1 1.315(3)
N2 C2 1.364(3)
N3 C2 1.336(3)
N3 C3 1.337(3)
N4 C3 1.339(3)
N4 C4 1.441(3)
N4 H4 0.944(10)
N5 C2 1.339(3)
N5 C7 1.445(3)
N5 H5 0.941(10)
O1 C5 1.205(3)
O2 C5 1.331(3)
O2 C6 1.443(3)
O3 C8 1.195(3)
O4 C8 1.337(3)
O4 C9 1.448(3)
C4 C5 1.508(4)
C4 H4A 0.9900
C4 H4B 0.9900
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.517(4)
C7 H7A 0.9900
C7 H7B 0.9900
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
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
_geom_hbond_site_symmetry_A
N4 H4 N1 0.944(10) 2.117(11) 3.055(3) 173(2) 3_776
N5 H5 N2 0.941(10) 2.124(10) 3.063(3) 176(2) 3_677
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
C2 N2 C1 N1 1.3(4)
C2 N2 C1 Cl1 -178.84(16)
C3 N1 C1 N2 -1.1(4)
C3 N1 C1 Cl1 179.02(16)
C3 N3 C2 N5 -179.5(2)
C3 N3 C2 N2 -0.4(3)
C7 N5 C2 N3 -0.6(3)
C7 N5 C2 N2 -179.8(2)
C1 N2 C2 N3 -0.4(3)
C1 N2 C2 N5 178.7(2)
C2 N3 C3 N4 -179.4(2)
C2 N3 C3 N1 0.6(3)
C4 N4 C3 N3 -1.0(3)
C4 N4 C3 N1 178.9(2)
C1 N1 C3 N3 0.0(3)
C1 N1 C3 N4 -179.9(2)
C3 N4 C4 C5 63.3(3)
C6 O2 C5 O1 2.2(3)
C6 O2 C5 C4 178.95(19)
N4 C4 C5 O1 -151.0(2)
N4 C4 C5 O2 32.2(3)
C2 N5 C7 C8 -75.3(3)
C9 O4 C8 O3 1.4(3)
C9 O4 C8 C7 -179.52(18)
N5 C7 C8 O3 -1.6(3)
N5 C7 C8 O4 179.38(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 125485352
