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#$Date: 2021-08-07 03:30:23 +0300 (Sat, 07 Aug 2021) $
#$Revision: 267977 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564332.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_1564332
loop_
_publ_author_name
'Ravi, Arthi'
'Shijad, Amina'
'Sureshan, Kana M.'
_publ_section_title
;
 Single-crystal-to-single-crystal synthesis of a pseudostarch via
 topochemical azide-alkyne cycloaddition polymerization
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03727G
_journal_year                    2021
_chemical_formula_moiety         'C9 H13 N3 O5'
_chemical_formula_sum            'C9 H13 N3 O5'
_chemical_formula_weight         243.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-10-16 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.159(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.792(2)
_cell_length_b                   17.062(5)
_cell_length_c                   9.698(3)
_cell_measurement_reflns_used    1701
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.62
_cell_measurement_theta_min      2.41
_cell_volume                     1061.6(6)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2013/5 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14418
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.523
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      1.521
_exptl_crystal_density_method    NONE
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0636P)²+0.4424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1238
_reflns_number_total             1868
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc03727g2.cif
_cod_data_source_block           POLYMER2
_cod_original_cell_volume        1061.5(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1564332
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.7644(4) 0.73138(16) 0.1667(3) 0.0249(7) Uani 1 1 d . . . . .
H4 H 0.7750 0.7343 0.2698 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7977(4) 0.64583(16) 0.1286(3) 0.0256(7) Uani 1 1 d . . . . .
H3 H 0.7927 0.6431 0.0266 0.031 Uiso 1 1 calc R U . . .
C2 C 0.6266(4) 0.59268(16) 0.1495(3) 0.0240(7) Uani 1 1 d . . . . .
H2 H 0.6512 0.5384 0.1263 0.029 Uiso 1 1 calc R U . . .
C1 C 0.4099(4) 0.61967(16) 0.0483(3) 0.0250(7) Uani 1 1 d . . . . .
H1 H 0.4106 0.6173 -0.0525 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3657(4) 0.70514(16) 0.0802(3) 0.0251(7) Uani 1 1 d . . . . .
H6 H 0.3547 0.7083 0.1783 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5449(4) 0.75981(15) 0.0715(3) 0.0246(7) Uani 1 1 d . . . . .
H5 H 0.5415 0.7610 -0.0303 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3547(5) 0.89301(17) 0.0400(3) 0.0313(7) Uani 1 1 d . . . . .
H9 H 0.2512 0.8850 -0.0495 0.038 Uiso 1 1 calc R U . . .
C7 C 0.7376(5) 0.53558(17) 0.3949(3) 0.0325(8) Uani 1 1 d . . . . .
H7B H 0.7715 0.5529 0.4953 0.039 Uiso 1 1 calc R U . . .
H7A H 0.8673 0.5261 0.3762 0.039 Uiso 1 1 calc R U . . .
C8 C 0.6133(4) 0.45915(17) 0.3744(3) 0.0287(7) Uani 1 1 d . . . . .
N1 N 0.5064(4) 0.84169(13) 0.1137(2) 0.0250(6) Uani 1 1 d . . . . .
N2 N 0.6311(4) 0.87322(15) 0.2407(3) 0.0346(7) Uani 1 1 d . . . . .
N3 N 0.4420(4) 0.44552(15) 0.2523(3) 0.0341(7) Uani 1 1 d . . . . .
O4 O 0.9241(3) 0.78099(13) 0.1425(2) 0.0387(6) Uani 1 1 d . . . . .
H4A H 1.0039 0.7961 0.2212 0.058 Uiso 1 1 calc R U . . .
O3 O 1.0005(3) 0.62021(13) 0.2218(2) 0.0348(6) Uani 1 1 d . . . . .
H3A H 1.0731 0.6092 0.1716 0.052 Uiso 1 1 calc R U . . .
O2 O 0.6228(3) 0.59680(11) 0.2984(2) 0.0287(5) Uani 1 1 d . . . . .
O1 O 0.2436(3) 0.56958(12) 0.0587(2) 0.0324(5) Uani 1 1 d . . . . .
H1A H 0.2926 0.5345 0.1177 0.049 Uiso 1 1 calc R U . . .
O6 O 0.1706(3) 0.72921(12) -0.0257(2) 0.0339(6) Uani 1 1 d . . . . .
H6A H 0.0938 0.7468 0.0168 0.051 Uiso 1 1 calc R U . . .
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
O4 C4 C3 109.7(2) . . ?
O4 C4 C5 110.1(2) . . ?
C3 C4 C5 110.0(2) . . ?
O4 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
C5 C4 H4 109.0 . . ?
O3 C3 C2 110.2(2) . . ?
O3 C3 C4 108.8(2) . . ?
C2 C3 C4 110.5(2) . . ?
O3 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
O2 C2 C3 111.3(2) . . ?
O2 C2 C1 107.0(2) . . ?
C3 C2 C1 110.1(2) . . ?
O2 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
O1 C1 C6 109.7(2) . . ?
O1 C1 C2 112.4(2) . . ?
C6 C1 C2 111.2(2) . . ?
O1 C1 H1 107.8 . . ?
C6 C1 H1 107.8 . . ?
C2 C1 H1 107.8 . . ?
O6 C6 C1 108.6(2) . . ?
O6 C6 C5 110.0(2) . . ?
C1 C6 C5 110.4(2) . . ?
O6 C6 H6 109.3 . . ?
C1 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
N1 C5 C4 110.3(2) . . ?
N1 C5 C6 109.4(2) . . ?
C4 C5 C6 113.3(2) . . ?
N1 C5 H5 107.9 . . ?
C4 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
N1 C9 C8 105.5(2) . 2_655 ?
N1 C9 H9 127.2 . . ?
C8 C9 H9 127.2 2_655 . ?
O2 C7 C8 112.0(2) . . ?
O2 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
O2 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
H7B C7 H7A 107.9 . . ?
C9 C8 N3 107.5(2) 2_645 . ?
C9 C8 C7 130.5(3) 2_645 . ?
N3 C8 C7 121.9(2) . . ?
N2 N1 C9 111.2(2) . . ?
N2 N1 C5 120.3(2) . . ?
C9 N1 C5 128.6(2) . . ?
N3 N2 N1 106.3(2) 2_655 . ?
N2 N3 C8 109.5(2) 2_645 . ?
C4 O4 H4A 109.5 . . ?
C3 O3 H3A 109.5 . . ?
C7 O2 C2 115.2(2) . . ?
C1 O1 H1A 109.5 . . ?
C6 O6 H6A 109.5 . . ?
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
C4 O4 1.454(3) . ?
C4 C3 1.540(4) . ?
C4 C5 1.551(4) . ?
C4 H4 0.9800 . ?
C3 O3 1.445(3) . ?
C3 C2 1.539(4) . ?
C3 H3 0.9800 . ?
C2 O2 1.454(3) . ?
C2 C1 1.548(4) . ?
C2 H2 0.9800 . ?
C1 O1 1.446(3) . ?
C1 C6 1.541(4) . ?
C1 H1 0.9800 . ?
C6 O6 1.444(3) . ?
C6 C5 1.558(4) . ?
C6 H6 0.9800 . ?
C5 N1 1.503(3) . ?
C5 H5 0.9800 . ?
C9 N1 1.363(4) . ?
C9 C8 1.376(4) 2_655 ?
C9 H9 0.9300 . ?
C7 O2 1.448(3) . ?
C7 C8 1.530(4) . ?
C7 H7B 0.9700 . ?
C7 H7A 0.9700 . ?
C8 C9 1.375(4) 2_645 ?
C8 N3 1.381(4) . ?
N1 N2 1.355(3) . ?
N2 N3 1.340(3) 2_655 ?
N3 N2 1.340(3) 2_645 ?
O4 H4A 0.8200 . ?
O3 H3A 0.8200 . ?
O1 H1A 0.8200 . ?
O6 H6A 0.8200 . ?
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
C3 H3 N2 0.98 2.64 3.570(4) 158.4 4_575
C1 H1 N3 0.98 2.68 3.560(4) 149.7 3_665
C9 H9 O3 0.93 2.31 3.238(4) 173.4 4_475
C7 H7A O3 0.97 2.56 3.172(4) 121.5 .
O4 H4A O6 0.82 2.38 3.107(3) 148.0 4_676
O3 H3A O1 0.82 1.96 2.772(3) 173.0 1_655
O1 H1A N3 0.82 2.04 2.857(3) 172.9 .
O6 H6A O4 0.82 2.02 2.834(3) 172.7 1_455
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
O4 C4 C3 O3 60.5(3) . . . . ?
C5 C4 C3 O3 -178.3(2) . . . . ?
O4 C4 C3 C2 -178.5(2) . . . . ?
C5 C4 C3 C2 -57.2(3) . . . . ?
O3 C3 C2 O2 62.2(3) . . . . ?
C4 C3 C2 O2 -58.0(3) . . . . ?
O3 C3 C2 C1 -179.3(2) . . . . ?
C4 C3 C2 C1 60.4(3) . . . . ?
O2 C2 C1 O1 -61.5(3) . . . . ?
C3 C2 C1 O1 177.5(2) . . . . ?
O2 C2 C1 C6 61.9(3) . . . . ?
C3 C2 C1 C6 -59.1(3) . . . . ?
O1 C1 C6 O6 -60.1(3) . . . . ?
C2 C1 C6 O6 174.9(2) . . . . ?
O1 C1 C6 C5 179.3(2) . . . . ?
C2 C1 C6 C5 54.2(3) . . . . ?
O4 C4 C5 N1 -62.2(3) . . . . ?
C3 C4 C5 N1 176.8(2) . . . . ?
O4 C4 C5 C6 174.7(2) . . . . ?
C3 C4 C5 C6 53.7(3) . . . . ?
O6 C6 C5 N1 64.2(3) . . . . ?
C1 C6 C5 N1 -175.9(2) . . . . ?
O6 C6 C5 C4 -172.2(2) . . . . ?
C1 C6 C5 C4 -52.3(3) . . . . ?
O2 C7 C8 C9 -166.0(3) . . . 2_645 ?
O2 C7 C8 N3 16.7(4) . . . . ?
C8 C9 N1 N2 -0.2(3) 2_655 . . . ?
C8 C9 N1 C5 179.4(2) 2_655 . . . ?
C4 C5 N1 N2 -14.7(3) . . . . ?
C6 C5 N1 N2 110.6(3) . . . . ?
C4 C5 N1 C9 165.6(3) . . . . ?
C6 C5 N1 C9 -69.0(3) . . . . ?
C9 N1 N2 N3 -0.1(3) . . . 2_655 ?
C5 N1 N2 N3 -179.8(2) . . . 2_655 ?
C9 C8 N3 N2 -0.5(3) 2_645 . . 2_645 ?
C7 C8 N3 N2 177.3(3) . . . 2_645 ?
C8 C7 O2 C2 -80.4(3) . . . . ?
C3 C2 O2 C7 -95.9(3) . . . . ?
C1 C2 O2 C7 143.8(2) . . . . ?
