#------------------------------------------------------------------------------
#$Date: 2021-09-06 11:10:09 +0200 (Mon 06 de Sep de 2021) $
#$Revision: 268535 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/86/7128653.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_7128653
loop_
_publ_author_name
'Chakraborti, Gargi'
'Mandal, Tirtha'
'Roy, Charles Patriot'
'Dash, Jyotirmayee'
_publ_section_title
;
 A [3+2] cycloaddition-1,2-acyl migration-hydrolysis cascade for
 regioselective synthesis of 1,2,3-triazoles in water.
;
_journal_issue                   64
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7970
_journal_page_last               7973
_journal_paper_doi               10.1039/d1cc02801d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C12 H13 N3 O2'
_chemical_formula_sum            'C12 H13 N3 O2'
_chemical_formula_weight         231.25
_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_date             2021-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-20 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.682(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.539(2)
_cell_length_b                   11.834(2)
_cell_length_c                   10.092(2)
_cell_measurement_reflns_used    2336
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.82
_cell_measurement_theta_min      2.81
_cell_volume                     1143.7(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      119.69
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker 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  0.0809
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8965
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.736
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1089 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.7541.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0382P)²+0.8368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1430
_reflns_number_total             2000
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02801d2.cif
_cod_data_source_block           test1_a
_cod_depositor_comments
'Adding full bibliography for 7128653--7128654.cif.'
_cod_original_cell_volume        1143.6(4)
_cod_database_code               7128653
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00E(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D)
2.c Idealised Me refined as rotating group:
 C00G(H00G,H00H,H00I), C00H(H00J,H00K,H00L)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O001 O 0.74797(18) 0.40123(14) 1.10838(17) 0.0261(5) Uani 1 1 d . . . . .
O002 O 0.65287(19) 0.57171(13) 1.02373(18) 0.0298(5) Uani 1 1 d . . . . .
N003 N 0.5024(2) 0.47663(16) 0.7595(2) 0.0230(5) Uani 1 1 d . . . . .
N1 N 0.5886(2) 0.41741(15) 0.8754(2) 0.0222(5) Uani 1 1 d . . . . .
N005 N 0.5947(2) 0.30548(16) 0.8522(2) 0.0258(5) Uani 1 1 d . . . . .
C006 C 0.4500(3) 0.40096(19) 0.6548(3) 0.0215(6) Uani 1 1 d . . . . .
C007 C 0.6654(3) 0.4724(2) 1.0099(3) 0.0231(6) Uani 1 1 d . . . . .
C008 C 0.3109(3) 0.5452(2) 0.4764(3) 0.0252(6) Uani 1 1 d . . . . .
H008 H 0.347088 0.600610 0.551018 0.030 Uiso 1 1 calc R . . . .
C009 C 0.3505(3) 0.43257(19) 0.5066(3) 0.0223(6) Uani 1 1 d . . . . .
C00A C 0.2967(3) 0.3529(2) 0.3958(3) 0.0240(6) Uani 1 1 d . . . . .
H00A H 0.324815 0.276187 0.416187 0.029 Uiso 1 1 calc R . . . .
C00B C 0.2188(3) 0.5761(2) 0.3375(3) 0.0271(6) Uani 1 1 d . . . . .
H00B H 0.192006 0.652988 0.316856 0.033 Uiso 1 1 calc R . . . .
C00C C 0.5078(3) 0.2940(2) 0.7145(3) 0.0273(6) Uani 1 1 d . . . . .
H00C H 0.486607 0.224642 0.662464 0.033 Uiso 1 1 calc R . . . .
C00D C 0.1651(3) 0.4962(2) 0.2282(3) 0.0284(6) Uani 1 1 d . . . . .
H00D H 0.102000 0.518736 0.132971 0.034 Uiso 1 1 calc R . . . .
C00E C 0.8308(3) 0.4539(2) 1.2495(3) 0.0264(6) Uani 1 1 d . . . . .
H00E H 0.769031 0.494923 1.284843 0.032 Uiso 1 1 calc R . . . .
H00F H 0.897782 0.508518 1.240154 0.032 Uiso 1 1 calc R . . . .
C00F C 0.2030(3) 0.3827(2) 0.2565(3) 0.0260(6) Uani 1 1 d . . . . .
C00G C 0.9074(3) 0.3620(2) 1.3539(3) 0.0302(7) Uani 1 1 d . . . . .
H00G H 0.840036 0.308986 1.362990 0.045 Uiso 1 1 calc GR . . . .
H00H H 0.964459 0.394976 1.449489 0.045 Uiso 1 1 calc GR . . . .
H00I H 0.967773 0.321864 1.317566 0.045 Uiso 1 1 calc GR . . . .
C00H C 0.1430(3) 0.2955(2) 0.1385(3) 0.0373(7) Uani 1 1 d . . . . .
H00J H 0.178102 0.220636 0.178465 0.056 Uiso 1 1 calc GR . . . .
H00K H 0.170831 0.312724 0.059369 0.056 Uiso 1 1 calc GR . . . .
H00L H 0.040915 0.296311 0.100588 0.056 Uiso 1 1 calc GR . . . .
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
C007 O001 C00E 113.57(18) . . ?
C006 N003 N1 104.42(18) . . ?
N003 N1 N005 115.15(19) . . ?
N003 N1 C007 120.28(18) . . ?
N005 N1 C007 124.56(19) . . ?
C00C N005 N1 102.81(19) . . ?
N003 C006 C009 121.6(2) . . ?
N003 C006 C00C 107.6(2) . . ?
C00C C006 C009 130.8(2) . . ?
O001 C007 N1 111.3(2) . . ?
O002 C007 O001 127.6(2) . . ?
O002 C007 N1 121.1(2) . . ?
C009 C008 H008 120.2 . . ?
C00B C008 H008 120.2 . . ?
C00B C008 C009 119.7(2) . . ?
C008 C009 C006 119.2(2) . . ?
C00A C009 C006 121.5(2) . . ?
C00A C009 C008 119.3(2) . . ?
C009 C00A H00A 119.3 . . ?
C00F C00A C009 121.5(2) . . ?
C00F C00A H00A 119.3 . . ?
C008 C00B H00B 119.7 . . ?
C008 C00B C00D 120.7(2) . . ?
C00D C00B H00B 119.7 . . ?
N005 C00C C006 110.0(2) . . ?
N005 C00C H00C 125.0 . . ?
C006 C00C H00C 125.0 . . ?
C00B C00D H00D 119.8 . . ?
C00B C00D C00F 120.5(2) . . ?
C00F C00D H00D 119.8 . . ?
O001 C00E H00E 110.2 . . ?
O001 C00E H00F 110.2 . . ?
O001 C00E C00G 107.62(19) . . ?
H00E C00E H00F 108.5 . . ?
C00G C00E H00E 110.2 . . ?
C00G C00E H00F 110.2 . . ?
C00A C00F C00D 118.4(2) . . ?
C00A C00F C00H 121.1(2) . . ?
C00D C00F C00H 120.6(2) . . ?
C00E C00G H00G 109.5 . . ?
C00E C00G H00H 109.5 . . ?
C00E C00G H00I 109.5 . . ?
H00G C00G H00H 109.5 . . ?
H00G C00G H00I 109.5 . . ?
H00H C00G H00I 109.5 . . ?
C00F C00H H00J 109.5 . . ?
C00F C00H H00K 109.5 . . ?
C00F C00H H00L 109.5 . . ?
H00J C00H H00K 109.5 . . ?
H00J C00H H00L 109.5 . . ?
H00K C00H H00L 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
O001 C007 1.316(3) . ?
O001 C00E 1.463(3) . ?
O002 C007 1.197(3) . ?
N003 N1 1.341(3) . ?
N003 C006 1.318(3) . ?
N1 N005 1.351(3) . ?
N1 C007 1.415(3) . ?
N005 C00C 1.313(3) . ?
C006 C009 1.472(3) . ?
C006 C00C 1.424(3) . ?
C008 H008 0.9500 . ?
C008 C009 1.392(3) . ?
C008 C00B 1.379(3) . ?
C009 C00A 1.390(3) . ?
C00A H00A 0.9500 . ?
C00A C00F 1.385(3) . ?
C00B H00B 0.9500 . ?
C00B C00D 1.382(3) . ?
C00C H00C 0.9500 . ?
C00D H00D 0.9500 . ?
C00D C00F 1.397(4) . ?
C00E H00E 0.9900 . ?
C00E H00F 0.9900 . ?
C00E C00G 1.495(3) . ?
C00F C00H 1.501(3) . ?
C00G H00G 0.9800 . ?
C00G H00H 0.9800 . ?
C00G H00I 0.9800 . ?
C00H H00J 0.9800 . ?
C00H H00K 0.9800 . ?
C00H H00L 0.9800 . ?
