#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/75/7157520.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_7157520
loop_
_publ_author_name
'Surendra Reddy, G.'
'Suresh Kumar, A.'
'Ramachary, Dhevalapally B.'
_publ_section_title
;
 Organocatalytic enone-azide [3 + 2]-cycloaddition: synthesis of
 functionally rich C/N-double vinyl 1,2,3-triazoles.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4470
_journal_page_last               4478
_journal_paper_doi               10.1039/d0ob00848f
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C19 H20 N4 O5'
_chemical_formula_weight         384.40
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/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
;
2020-03-25 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.240(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.271(3)
_cell_length_b                   8.4386(16)
_cell_length_c                   12.3780(19)
_cell_measurement_reflns_used    9807
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      2.66
_cell_volume                     1905.4(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            47139
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0718
_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)+(0.1019P)²+1.8533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1965
_refine_ls_wR_factor_ref         0.2081
_reflns_number_gt                2699
_reflns_number_total             3345
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob00848f4.cif
_cod_data_source_block           gsr125
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'None' was changed
to 'none' 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.

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 

 Adding full bibliography for 7157520--7157522.cif.

 Adding full bibliography for 7157520--7157522.cif.

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1905.5(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C4.75 H5 N O1.25'
_cod_original_formula_units_Z    16
_cod_original_formula_weight     96.10
_cod_database_code               7157520
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36385(12) 0.6370(3) 0.36140(17) 0.0424(6) Uani 1 1 d . . .
N3 N 0.42870(13) 0.7432(3) 0.49281(17) 0.0453(6) Uani 1 1 d . . .
O3 O 0.17414(12) 0.5117(3) 0.31002(17) 0.0704(7) Uani 1 1 d . . .
N2 N 0.36115(14) 0.7162(3) 0.45774(18) 0.0511(6) Uani 1 1 d . . .
O4 O 0.71237(13) 0.6647(4) 0.4105(2) 0.0829(8) Uani 1 1 d . . .
C11 C 0.47491(14) 0.6804(3) 0.42154(19) 0.0360(6) Uani 1 1 d . . .
C12 C 0.43403(14) 0.6118(3) 0.33790(19) 0.0360(6) Uani 1 1 d . . .
C15 C 0.58839(14) 0.6062(3) 0.3504(2) 0.0405(6) Uani 1 1 d . . .
O5 O 0.68998(13) 0.5572(4) 0.2506(2) 0.0904(10) Uani 1 1 d . . .
C10 C 0.55448(15) 0.6911(3) 0.4254(2) 0.0384(6) Uani 1 1 d . . .
C13 C 0.46663(15) 0.5359(3) 0.2443(2) 0.0414(6) Uani 1 1 d . . .
H13A H 0.4654 0.6087 0.1836 0.050 Uiso 1 1 calc R . .
H13B H 0.4388 0.4422 0.2228 0.050 Uiso 1 1 calc R . .
C14 C 0.54566(15) 0.4905(3) 0.2762(2) 0.0439(7) Uani 1 1 d . . .
H14A H 0.5717 0.4782 0.2106 0.053 Uiso 1 1 calc R . .
H14B H 0.5454 0.3881 0.3117 0.053 Uiso 1 1 calc R . .
C19 C 0.58921(18) 0.8005(4) 0.5090(2) 0.0565(8) Uani 1 1 d . . .
H19A H 0.5993 0.7434 0.5753 0.085 Uiso 1 1 calc R . .
H19B H 0.5564 0.8866 0.5216 0.085 Uiso 1 1 calc R . .
H19C H 0.6342 0.8415 0.4838 0.085 Uiso 1 1 calc R . .
C8 C 0.29714(16) 0.5959(4) 0.3022(2) 0.0495(7) Uani 1 1 d . . .
C16 C 0.66908(17) 0.6136(4) 0.3434(2) 0.0531(8) Uani 1 1 d . . .
C4 C 0.11780(16) 0.4402(4) 0.3581(2) 0.0562(8) Uani 1 1 d . . .
N4 N -0.06307(18) 0.2107(5) 0.4821(3) 0.0877(11) Uani 1 1 d . . .
C7 C 0.23976(17) 0.5396(5) 0.3743(3) 0.0611(9) Uani 1 1 d . . .
H7A H 0.2557 0.4428 0.4106 0.073 Uiso 1 1 calc R . .
H7B H 0.2313 0.6190 0.4289 0.073 Uiso 1 1 calc R . .
O1 O -0.12015(18) 0.2056(6) 0.4263(3) 0.1372(17) Uani 1 1 d . . .
C5 C 0.12094(17) 0.3876(5) 0.4642(3) 0.0642(9) Uani 1 1 d . . .
H5 H 0.1632 0.4026 0.5085 0.077 Uiso 1 1 calc R . .
O2 O -0.05696(19) 0.1565(6) 0.5720(3) 0.1384(18) Uani 1 1 d . . .
C3 C 0.05423(18) 0.4188(5) 0.2929(3) 0.0658(10) Uani 1 1 d . . .
H3 H 0.0519 0.4552 0.2219 0.079 Uiso 1 1 calc R . .
C9 C 0.29111(19) 0.6063(5) 0.1959(3) 0.0714(11) Uani 1 1 d . . .
H9A H 0.3307 0.6409 0.1581 0.086 Uiso 1 1 calc R . .
H9B H 0.2473 0.5791 0.1587 0.086 Uiso 1 1 calc R . .
C1 C -0.00067(17) 0.2908(5) 0.4383(3) 0.0625(9) Uani 1 1 d . . .
C6 C 0.06145(18) 0.3133(5) 0.5035(3) 0.0684(10) Uani 1 1 d . . .
H6 H 0.0632 0.2779 0.5747 0.082 Uiso 1 1 calc R . .
C2 C -0.00517(18) 0.3440(5) 0.3329(3) 0.0698(10) Uani 1 1 d . . .
H2 H -0.0479 0.3295 0.2894 0.084 Uiso 1 1 calc R . .
C17 C 0.7699(3) 0.5573(7) 0.2347(4) 0.1060(15) Uiso 1 1 d . . .
H17A H 0.7909 0.6592 0.2554 0.127 Uiso 1 1 calc R . .
H17B H 0.7940 0.4761 0.2793 0.127 Uiso 1 1 calc R . .
C18 C 0.7803(3) 0.5273(7) 0.1247(4) 0.1163(17) Uiso 1 1 d . . .
H18A H 0.7551 0.4316 0.1030 0.174 Uiso 1 1 calc R . .
H18B H 0.8317 0.5157 0.1144 0.174 Uiso 1 1 calc R . .
H18C H 0.7611 0.6142 0.0818 0.174 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
C12 N1 N2 110.3(2) . . ?
C12 N1 C8 130.2(2) . . ?
N2 N1 C8 119.5(2) . . ?
N2 N3 C11 109.0(2) . . ?
C4 O3 C7 117.7(2) . . ?
N3 N2 N1 107.1(2) . . ?
N3 C11 C12 108.8(2) . . ?
N3 C11 C10 127.5(2) . . ?
C12 C11 C10 123.5(2) . . ?
N1 C12 C11 104.8(2) . . ?
N1 C12 C13 131.9(2) . . ?
C11 C12 C13 123.3(2) . . ?
C10 C15 C16 121.0(3) . . ?
C10 C15 C14 121.0(2) . . ?
C16 C15 C14 117.9(2) . . ?
C16 O5 C17 116.8(3) . . ?
C15 C10 C11 116.1(2) . . ?
C15 C10 C19 127.4(3) . . ?
C11 C10 C19 116.4(2) . . ?
C12 C13 C14 108.9(2) . . ?
C12 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 C15 116.1(2) . . ?
C13 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C8 N1 121.1(3) . . ?
C9 C8 C7 126.6(3) . . ?
N1 C8 C7 112.2(2) . . ?
O4 C16 O5 121.5(3) . . ?
O4 C16 C15 126.5(3) . . ?
O5 C16 C15 111.9(3) . . ?
O3 C4 C5 124.5(3) . . ?
O3 C4 C3 115.7(3) . . ?
C5 C4 C3 119.9(3) . . ?
O2 N4 O1 122.9(3) . . ?
O2 N4 C1 119.2(3) . . ?
O1 N4 C1 117.9(3) . . ?
O3 C7 C8 108.5(2) . . ?
O3 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
O3 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C6 C1 C2 121.1(3) . . ?
C6 C1 N4 119.0(3) . . ?
C2 C1 N4 119.9(3) . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C18 C17 O5 108.4(4) . . ?
C18 C17 H17A 110.0 . . ?
O5 C17 H17A 110.0 . . ?
C18 C17 H17B 110.0 . . ?
O5 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
N1 C12 1.348(3) . ?
N1 N2 1.370(3) . ?
N1 C8 1.429(4) . ?
N3 N2 1.305(3) . ?
N3 C11 1.362(3) . ?
O3 C4 1.359(4) . ?
O3 C7 1.421(4) . ?
O4 C16 1.195(4) . ?
C11 C12 1.370(4) . ?
C11 C10 1.455(4) . ?
C12 C13 1.478(3) . ?
C15 C10 1.351(4) . ?
C15 C16 1.483(4) . ?
C15 C14 1.525(4) . ?
O5 C16 1.319(4) . ?
O5 C17 1.485(5) . ?
C10 C19 1.500(4) . ?
C13 C14 1.524(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C8 C9 1.316(4) . ?
C8 C7 1.493(4) . ?
C4 C5 1.384(4) . ?
C4 C3 1.388(4) . ?
N4 O2 1.202(4) . ?
N4 O1 1.219(4) . ?
N4 C1 1.456(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 C6 1.368(5) . ?
C5 H5 0.9300 . ?
C3 C2 1.371(5) . ?
C3 H3 0.9300 . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C1 C6 1.368(4) . ?
C1 C2 1.378(5) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C17 C18 1.408(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353420
