#------------------------------------------------------------------------------
#$Date: 2025-02-01 09:07:15 +0200 (Sat, 01 Feb 2025) $
#$Revision: 297561 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157521.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_7157521
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            'C17 H19 N3 O3'
_chemical_formula_weight         313.35
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -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                97.850(4)
_cell_angle_beta                 94.308(3)
_cell_angle_gamma                110.859(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2978(6)
_cell_length_b                   8.2873(8)
_cell_length_c                   14.1639(13)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.67
_cell_volume                     785.86(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28797
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.137(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0401
_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)+(0.0567P)²+0.2246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                2411
_reflns_number_total             2764
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob00848f4.cif
_cod_data_source_block           dbr151a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' 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_formula_sum            'C5.67 H6.33 N O'
_cod_original_formula_weight         104.45
_cod_original_formula_units_Z            6
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7157521
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O3 O 0.43129(17) 0.81420(17) 0.21843(8) 0.0555(3) Uani 1 1 d . . .
O1 O 0.72582(18) 0.62012(17) 0.93818(8) 0.0617(4) Uani 1 1 d . . .
N1 N 0.27382(18) 0.71639(16) 0.63306(9) 0.0412(3) Uani 1 1 d . . .
O2 O 0.10625(19) 0.7413(2) 0.18767(9) 0.0773(5) Uani 1 1 d . . .
N2 N 0.0906(2) 0.71926(19) 0.64573(10) 0.0513(4) Uani 1 1 d . . .
N3 N 0.01088(19) 0.73593(18) 0.56358(10) 0.0498(4) Uani 1 1 d . . .
C6 C 0.1167(2) 0.76624(19) 0.39857(11) 0.0402(4) Uani 1 1 d . . .
C2 C 0.3070(2) 0.73003(18) 0.54168(10) 0.0387(4) Uani 1 1 d . . .
C1 C 0.1402(2) 0.74259(19) 0.49807(11) 0.0398(4) Uani 1 1 d . . .
C12 C 0.3058(2) 0.5946(2) 0.77740(11) 0.0463(4) Uani 1 1 d . . .
H12 H 0.1688 0.5410 0.7710 0.056 Uiso 1 1 calc R . .
C5 C 0.2506(2) 0.7374(2) 0.34445(11) 0.0418(4) Uani 1 1 d . . .
C13 C 0.4215(2) 0.5740(2) 0.85255(11) 0.0499(4) Uani 1 1 d . . .
H13 H 0.3621 0.5075 0.8975 0.060 Uiso 1 1 calc R . .
C11 C 0.3950(2) 0.69620(19) 0.71109(10) 0.0407(4) Uani 1 1 d . . .
C8 C 0.2493(2) 0.7620(2) 0.24292(11) 0.0473(4) Uani 1 1 d . . .
C16 C 0.5982(2) 0.7754(2) 0.72088(11) 0.0474(4) Uani 1 1 d . . .
H16 H 0.6573 0.8450 0.6771 0.057 Uiso 1 1 calc R . .
C14 C 0.6256(2) 0.6514(2) 0.86174(11) 0.0463(4) Uani 1 1 d . . .
C3 C 0.4790(2) 0.7351(2) 0.49041(11) 0.0483(4) Uani 1 1 d . . .
H3A H 0.5435 0.6627 0.5154 0.058 Uiso 1 1 calc R . .
H3B H 0.5745 0.8544 0.4990 0.058 Uiso 1 1 calc R . .
C15 C 0.7148(2) 0.7522(2) 0.79532(11) 0.0499(4) Uani 1 1 d . . .
H15 H 0.8519 0.8037 0.8009 0.060 Uiso 1 1 calc R . .
C4 C 0.3996(2) 0.6657(3) 0.38451(11) 0.0534(4) Uani 1 1 d . . .
H4A H 0.3376 0.5389 0.3753 0.064 Uiso 1 1 calc R . .
H4B H 0.5101 0.6939 0.3476 0.064 Uiso 1 1 calc R . .
C7 C -0.0452(3) 0.8275(2) 0.36799(13) 0.0568(5) Uani 1 1 d . . .
H7A H -0.0292 0.8607 0.3059 0.085 Uiso 1 1 calc R . .
H7B H -0.0388 0.9266 0.4139 0.085 Uiso 1 1 calc R . .
H7C H -0.1712 0.7344 0.3647 0.085 Uiso 1 1 calc R . .
C9 C 0.4514(3) 0.8454(3) 0.12119(13) 0.0644(5) Uani 1 1 d . . .
H9A H 0.3854 0.9234 0.1060 0.077 Uiso 1 1 calc R . .
H9B H 0.3925 0.7358 0.0760 0.077 Uiso 1 1 calc R . .
C10 C 0.6667(3) 0.9266(3) 0.11505(15) 0.0757(6) Uani 1 1 d . . .
H10A H 0.7241 1.0330 0.1614 0.114 Uiso 1 1 calc R . .
H10B H 0.6854 0.9526 0.0517 0.114 Uiso 1 1 calc R . .
H10C H 0.7297 0.8467 0.1281 0.114 Uiso 1 1 calc R . .
C17 C 0.9350(3) 0.6991(3) 0.95262(15) 0.0720(6) Uani 1 1 d . . .
H17A H 0.9866 0.6587 0.8977 0.108 Uiso 1 1 calc R . .
H17B H 0.9859 0.6679 1.0090 0.108 Uiso 1 1 calc R . .
H17C H 0.9743 0.8243 0.9610 0.108 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
C8 O3 C9 117.06(13) . . ?
C14 O1 C17 118.17(14) . . ?
C2 N1 N2 110.05(12) . . ?
C2 N1 C11 130.02(12) . . ?
N2 N1 C11 119.90(12) . . ?
N3 N2 N1 107.34(12) . . ?
N2 N3 C1 108.67(12) . . ?
C5 C6 C1 115.64(13) . . ?
C5 C6 C7 126.90(14) . . ?
C1 C6 C7 117.39(13) . . ?
N1 C2 C1 105.04(13) . . ?
N1 C2 C3 132.29(13) . . ?
C1 C2 C3 122.67(13) . . ?
N3 C1 C2 108.88(13) . . ?
N3 C1 C6 127.82(14) . . ?
C2 C1 C6 123.25(13) . . ?
C13 C12 C11 119.58(15) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C6 C5 C8 121.74(14) . . ?
C6 C5 C4 120.54(13) . . ?
C8 C5 C4 117.58(13) . . ?
C12 C13 C14 120.53(14) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C16 C11 C12 119.97(15) . . ?
C16 C11 N1 120.80(13) . . ?
C12 C11 N1 119.23(14) . . ?
O2 C8 O3 122.44(15) . . ?
O2 C8 C5 126.20(15) . . ?
O3 C8 C5 111.35(13) . . ?
C11 C16 C15 120.51(14) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
O1 C14 C13 115.58(14) . . ?
O1 C14 C15 124.52(15) . . ?
C13 C14 C15 119.91(15) . . ?
C2 C3 C4 107.08(13) . . ?
C2 C3 H3A 110.3 . . ?
C4 C3 H3A 110.3 . . ?
C2 C3 H3B 110.3 . . ?
C4 C3 H3B 110.3 . . ?
H3A C3 H3B 108.6 . . ?
C16 C15 C14 119.48(15) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C3 C4 C5 114.75(14) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C9 C10 107.28(16) . . ?
O3 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
O3 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O3 C8 1.3313(19) . ?
O3 C9 1.444(2) . ?
O1 C14 1.3663(19) . ?
O1 C17 1.416(2) . ?
N1 C2 1.3468(18) . ?
N1 N2 1.3705(17) . ?
N1 C11 1.4285(19) . ?
O2 C8 1.2018(19) . ?
N2 N3 1.3079(19) . ?
N3 C1 1.3649(19) . ?
C6 C5 1.352(2) . ?
C6 C1 1.455(2) . ?
C6 C7 1.501(2) . ?
C2 C1 1.367(2) . ?
C2 C3 1.488(2) . ?
C12 C13 1.376(2) . ?
C12 C11 1.390(2) . ?
C12 H12 0.9300 . ?
C5 C8 1.480(2) . ?
C5 C4 1.522(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9300 . ?
C11 C16 1.378(2) . ?
C16 C15 1.382(2) . ?
C16 H16 0.9300 . ?
C14 C15 1.388(2) . ?
C3 C4 1.521(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C15 H15 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 C10 1.488(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
