#------------------------------------------------------------------------------
#$Date: 2022-02-04 22:02:41 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272774 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158443.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_7158443
loop_
_publ_author_name
'Rai, Vishakha'
'P, Kavyashree'
'Harmalkar, Sarvesh S.'
'Dhuri, Sundar N.'
'Maddani, Mahagundappa R.'
_publ_section_title
;
 1,6-Addition of 1,2,3-NH triazoles to para-quinone methides:
 Facile access to highly selective N¹ and N²
 substituted triazoles.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              345
_journal_page_last               351
_journal_paper_doi               10.1039/d1ob01717a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_sum            'C29 H32 N3 O'
_chemical_formula_weight         438.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-08-16 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.578(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0143(14)
_cell_length_b                   15.747(2)
_cell_length_c                   15.541(2)
_cell_measurement_reflns_used    5549
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.48
_cell_measurement_theta_min      2.91
_cell_volume                     2608.7(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34744
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.327
_diffrn_reflns_theta_min         2.587
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_description       block
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6880
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0089(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         6494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0598
_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)+(0.0767P)²+0.5234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3196
_reflns_number_total             6494
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01717a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7158442--7158443.cif.'
_cod_original_cell_volume        2608.6(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158443
_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.
;
loop_
_space_group_symop_operation_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_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
N1 N 0.53736(15) 0.40892(10) 0.39111(10) 0.0491(4) Uani 1 1 d . . . . .
C1 C 0.1439(2) 0.25059(16) 0.38802(16) 0.0653(6) Uani 1 1 d . . . . .
O1 O 0.02842(15) 0.21119(13) 0.36329(15) 0.1058(7) Uani 1 1 d . . . . .
N2 N 0.52033(17) 0.37006(11) 0.31312(12) 0.0615(5) Uani 1 1 d . . . . .
C2 C 0.2481(2) 0.19876(14) 0.42169(15) 0.0599(6) Uani 1 1 d . . . . .
C3 C 0.36427(19) 0.23871(13) 0.44650(14) 0.0559(5) Uani 1 1 d . . . . .
H3 H 0.435273 0.206012 0.469716 0.067 Uiso 1 1 calc R U . . .
N3 N 0.60160(16) 0.48154(10) 0.39817(11) 0.0535(4) Uani 1 1 d . . . . .
C4 C 0.37790(18) 0.32509(13) 0.43790(13) 0.0495(5) Uani 1 1 d . . . . .
C7 C 0.2354(2) 0.10233(16) 0.4317(2) 0.0822(8) Uani 1 1 d . . . . .
C6 C 0.15278(19) 0.33882(15) 0.37899(15) 0.0628(6) Uani 1 1 d . . . . .
C5 C 0.27199(19) 0.37370(14) 0.40448(14) 0.0577(5) Uani 1 1 d . . . . .
H5 H 0.281089 0.432009 0.398896 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3632(3) 0.06082(17) 0.4704(3) 0.1278(14) Uani 1 1 d . . . . .
H8A H 0.351995 0.001190 0.478664 0.192 Uiso 1 1 calc R U . . .
H8B H 0.402177 0.086510 0.526564 0.192 Uiso 1 1 calc R U . . .
H8C H 0.415637 0.068739 0.430139 0.192 Uiso 1 1 calc R U . . .
C9 C 0.1512(4) 0.0820(2) 0.4942(3) 0.1348(14) Uani 1 1 d . . . . .
H9A H 0.070263 0.107555 0.471573 0.202 Uiso 1 1 calc R U . . .
H9B H 0.188753 0.104181 0.552365 0.202 Uiso 1 1 calc R U . . .
H9C H 0.141808 0.021594 0.497774 0.202 Uiso 1 1 calc R U . . .
C10 C 0.1816(3) 0.06215(19) 0.3399(2) 0.1250(13) Uani 1 1 d . . . . .
H10A H 0.099402 0.084730 0.314439 0.188 Uiso 1 1 calc R U . . .
H10B H 0.176196 0.001708 0.346145 0.188 Uiso 1 1 calc R U . . .
H10C H 0.235462 0.074903 0.301741 0.188 Uiso 1 1 calc R U . . .
C11 C 0.0373(2) 0.39680(19) 0.3448(2) 0.0875(8) Uani 1 1 d . . . . .
C12 C 0.0754(3) 0.4902(2) 0.3465(3) 0.1292(14) Uani 1 1 d . . . . .
H12A H 0.129022 0.498645 0.307198 0.194 Uiso 1 1 calc R U . . .
H12B H 0.119395 0.505794 0.405879 0.194 Uiso 1 1 calc R U . . .
H12C H 0.001712 0.524736 0.327514 0.194 Uiso 1 1 calc R U . . .
C13 C -0.0301(3) 0.3744(3) 0.2488(3) 0.1426(15) Uani 1 1 d . . . . .
H13A H -0.100338 0.411696 0.228366 0.214 Uiso 1 1 calc R U . . .
H13B H -0.059076 0.316703 0.246206 0.214 Uiso 1 1 calc R U . . .
H13C H 0.026954 0.380622 0.211565 0.214 Uiso 1 1 calc R U . . .
C14 C -0.0514(3) 0.3890(3) 0.4065(3) 0.1364(14) Uani 1 1 d . . . . .
H14A H -0.119250 0.428628 0.388204 0.205 Uiso 1 1 calc R U . . .
H14B H -0.006052 0.401258 0.466518 0.205 Uiso 1 1 calc R U . . .
H14C H -0.084260 0.332335 0.403364 0.205 Uiso 1 1 calc R U . . .
C15 C 0.50344(18) 0.37059(13) 0.46816(13) 0.0510(5) Uani 1 1 d . . . . .
H15 H 0.490352 0.417772 0.505951 0.061 Uiso 1 1 calc R U . . .
C16 C 0.61014(19) 0.31848(13) 0.52329(13) 0.0534(5) Uani 1 1 d . . . . .
C17 C 0.6934(3) 0.2762(2) 0.48774(18) 0.0904(9) Uani 1 1 d . . . . .
H17 H 0.686610 0.280289 0.427012 0.108 Uiso 1 1 calc R U . . .
C18 C 0.7884(3) 0.2270(2) 0.5400(2) 0.1168(12) Uani 1 1 d . . . . .
H18 H 0.843916 0.197940 0.514337 0.140 Uiso 1 1 calc R U . . .
C19 C 0.7998(3) 0.2217(2) 0.6293(2) 0.1070(11) Uani 1 1 d . . . . .
H19 H 0.863568 0.189369 0.664988 0.128 Uiso 1 1 calc R U . . .
C20 C 0.7183(4) 0.2635(3) 0.6653(2) 0.1181(12) Uani 1 1 d . . . . .
H20 H 0.725974 0.259806 0.726151 0.142 Uiso 1 1 calc R U . . .
C21 C 0.6234(3) 0.3120(2) 0.61310(17) 0.0983(10) Uani 1 1 d . . . . .
H21 H 0.567949 0.340562 0.639182 0.118 Uiso 1 1 calc R U . . .
C22 C 0.5759(2) 0.42195(14) 0.26713(15) 0.0623(6) Uani 1 1 d . . . . .
H22 H 0.580182 0.412994 0.208813 0.075 Uiso 1 1 calc R U . . .
C23 C 0.62622(18) 0.49101(13) 0.31865(13) 0.0508(5) Uani 1 1 d . . . . .
C24 C 0.6990(2) 0.56272(13) 0.29797(15) 0.0573(5) Uani 1 1 d . . . . .
C25 C 0.7244(3) 0.56797(17) 0.21534(17) 0.0777(7) Uani 1 1 d . . . . .
H25 H 0.689776 0.528200 0.171837 0.093 Uiso 1 1 calc R U . . .
C26 C 0.7998(3) 0.6309(2) 0.1967(2) 0.1003(10) Uani 1 1 d . . . . .
H26 H 0.816850 0.633053 0.141049 0.120 Uiso 1 1 calc R U . . .
C27 C 0.8501(3) 0.6903(2) 0.2593(3) 0.1067(11) Uani 1 1 d . . . . .
H27 H 0.901963 0.732602 0.246641 0.128 Uiso 1 1 calc R U . . .
C28 C 0.8240(3) 0.68768(19) 0.3406(2) 0.1071(11) Uani 1 1 d . . . . .
H28 H 0.856428 0.728990 0.382902 0.129 Uiso 1 1 calc R U . . .
C29 C 0.7492(3) 0.62349(16) 0.36004(19) 0.0822(8) Uani 1 1 d . . . . .
H29 H 0.732842 0.621517 0.415864 0.099 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
N2 N1 N3 114.84(16) . . ?
N2 N1 C15 123.18(16) . . ?
N3 N1 C15 121.52(15) . . ?
O1 C1 C2 117.0(2) . . ?
O1 C1 C6 120.0(2) . . ?
C2 C1 C6 123.0(2) . . ?
N1 N2 C22 103.21(17) . . ?
C3 C2 C1 116.8(2) . . ?
C3 C2 C7 121.3(2) . . ?
C1 C2 C7 121.9(2) . . ?
C4 C3 C2 122.32(19) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
N1 N3 C23 104.24(16) . . ?
C3 C4 C5 118.72(19) . . ?
C3 C4 C15 123.16(18) . . ?
C5 C4 C15 118.04(18) . . ?
C8 C7 C9 107.8(3) . . ?
C8 C7 C2 111.3(2) . . ?
C9 C7 C2 110.8(2) . . ?
C8 C7 C10 106.9(3) . . ?
C9 C7 C10 110.4(3) . . ?
C2 C7 C10 109.7(2) . . ?
C5 C6 C1 116.67(19) . . ?
C5 C6 C11 120.1(2) . . ?
C1 C6 C11 123.2(2) . . ?
C4 C5 C6 122.5(2) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C13 107.6(3) . . ?
C12 C11 C14 106.3(3) . . ?
C13 C11 C14 111.2(3) . . ?
C12 C11 C6 111.3(2) . . ?
C13 C11 C6 110.7(3) . . ?
C14 C11 C6 109.6(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 111.35(16) . . ?
N1 C15 C4 109.80(15) . . ?
C16 C15 C4 115.84(17) . . ?
N1 C15 H15 106.4 . . ?
C16 C15 H15 106.4 . . ?
C4 C15 H15 106.4 . . ?
C17 C16 C21 117.9(2) . . ?
C17 C16 C15 123.0(2) . . ?
C21 C16 C15 119.1(2) . . ?
C16 C17 C18 121.5(3) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.8(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 120.7(3) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
N2 C22 C23 110.09(19) . . ?
N2 C22 H22 125.0 . . ?
C23 C22 H22 125.0 . . ?
N3 C23 C22 107.61(18) . . ?
N3 C23 C24 122.48(18) . . ?
C22 C23 C24 129.9(2) . . ?
C29 C24 C25 118.1(2) . . ?
C29 C24 C23 121.9(2) . . ?
C25 C24 C23 119.9(2) . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 119.8(3) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C29 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C24 C29 C28 120.8(3) . . ?
C24 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
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 N2 1.328(2) . ?
N1 N3 1.335(2) . ?
N1 C15 1.471(2) . ?
C1 O1 1.380(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.402(3) . ?
N2 C22 1.332(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.536(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
N3 C23 1.338(2) . ?
C4 C5 1.383(3) . ?
C4 C15 1.523(3) . ?
C7 C8 1.531(4) . ?
C7 C9 1.536(4) . ?
C7 C10 1.537(4) . ?
C6 C5 1.386(3) . ?
C6 C11 1.547(3) . ?
C5 H5 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.527(4) . ?
C11 C13 1.532(4) . ?
C11 C14 1.536(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.511(3) . ?
C15 H15 0.9800 . ?
C16 C17 1.358(3) . ?
C16 C21 1.370(3) . ?
C17 C18 1.388(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.344(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.467(3) . ?
C24 C29 1.372(3) . ?
C24 C25 1.384(3) . ?
C25 C26 1.370(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.363(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.365(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.384(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
