#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024515.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_4024515
loop_
_publ_author_name
'Chinmay Chowdhury'
'Sanjukta Mukherjee'
'Bimolendu Das'
'Basudeb Achari'
_publ_section_title
;
Expedient and Rapid Synthesis of 1,2,3-Triazolo[5,1-c]morpholines through
Palladium-Copper Catalysis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3612
_journal_page_last               3615
_journal_paper_doi               10.1021/jo900428j
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C24 H21 N3 O2'
_chemical_formula_weight         383.44
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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
_cell_angle_alpha                89.115(8)
_cell_angle_beta                 81.221(7)
_cell_angle_gamma                72.546(7)
_cell_formula_units_Z            2
_cell_length_a                   6.8927(7)
_cell_length_b                   9.7044(11)
_cell_length_c                   15.8321(18)
_cell_measurement_reflns_used    4227
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      2.21
_cell_volume                     997.89(19)
_computing_cell_refinement       'Apex 2, Bruker Kappa'
_computing_data_collection       'Apex 2, Bruker Kappa'
_computing_data_reduction        'Apex 2, Bruker Kappa'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa Apex 2'
_diffrn_measurement_method       'Difference Vectors'
_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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15479
_diffrn_reflns_theta_full        25.44
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_min         1.30
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Cube
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         3674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0685P)²+0.0216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                2635
_reflns_number_total             3674
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900428j_si_001.cif
_cod_data_source_block           snj_1_160_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024515
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
O1 O 0.33293(15) 0.98731(11) 0.78150(6) 0.0510(3) Uani 1 1 d . . .
O2 O 0.55921(17) 0.43018(12) 1.18281(7) 0.0622(3) Uani 1 1 d . . .
N3 N 0.74556(19) 0.79549(14) 0.97458(8) 0.0508(3) Uani 1 1 d . . .
N1 N 0.65039(18) 0.92617(13) 0.87044(7) 0.0450(3) Uani 1 1 d . . .
N2 N 0.80956(18) 0.87020(14) 0.91298(8) 0.0515(3) Uani 1 1 d . . .
C19 C 0.5550(2) 0.61393(16) 1.07733(9) 0.0452(4) Uani 1 1 d . . .
C2 C 0.4843(2) 0.88638(15) 0.90415(9) 0.0425(4) Uani 1 1 d . . .
C1 C 0.5465(2) 0.80178(15) 0.97100(9) 0.0422(4) Uani 1 1 d . . .
C20 C 0.4592(2) 0.53647(16) 1.13335(9) 0.0475(4) Uani 1 1 d . . .
C3 C 0.2924(2) 0.9413(2) 0.86613(10) 0.0495(4) Uani 1 1 d . . .
C23 C 0.2286(2) 0.75017(18) 1.04099(10) 0.0516(4) Uani 1 1 d . . .
C18 C 0.4403(2) 0.72256(15) 1.03054(9) 0.0423(4) Uani 1 1 d . . .
C5 C 0.6730(2) 1.00060(17) 0.79093(10) 0.0467(4) Uani 1 1 d . . .
C21 C 0.2487(3) 0.56416(19) 1.14273(11) 0.0574(4) Uani 1 1 d . . .
C6 C 0.7960(2) 0.89617(17) 0.71893(9) 0.0491(4) Uani 1 1 d . . .
C4 C 0.4527(2) 1.08413(17) 0.77665(10) 0.0481(4) Uani 1 1 d . . .
C22 C 0.1356(3) 0.67096(19) 1.09657(11) 0.0584(5) Uani 1 1 d . . .
C12 C 0.4468(2) 1.15672(17) 0.69252(10) 0.0519(4) Uani 1 1 d . . .
C7 C 0.7664(3) 0.76346(19) 0.70925(11) 0.0581(4) Uani 1 1 d . . .
C11 C 0.9406(3) 0.9333(2) 0.66132(13) 0.0717(5) Uani 1 1 d . . .
C24 C 0.7708(3) 0.4115(3) 1.18437(16) 0.0694(5) Uani 1 1 d . . .
C17 C 0.5149(4) 1.2761(2) 0.68026(13) 0.0743(6) Uani 1 1 d . . .
C8 C 0.8832(3) 0.6688(2) 0.64342(13) 0.0732(5) Uani 1 1 d . . .
C13 C 0.3763(3) 1.1071(2) 0.62589(12) 0.0750(6) Uani 1 1 d . . .
C16 C 0.5081(4) 1.3457(3) 0.60385(15) 0.0908(7) Uani 1 1 d . . .
C9 C 1.0259(3) 0.7078(3) 0.58668(14) 0.0846(7) Uani 1 1 d . . .
C14 C 0.3715(4) 1.1776(3) 0.54971(15) 0.0906(7) Uani 1 1 d . . .
C10 C 1.0544(4) 0.8390(3) 0.59506(15) 0.0913(7) Uani 1 1 d . . .
C15 C 0.4349(4) 1.2975(3) 0.53934(15) 0.0897(7) Uani 1 1 d . . .
H23 H 0.147(2) 0.8262(17) 1.0098(10) 0.057(4) Uiso 1 1 d . . .
H5 H 0.740(2) 1.0717(16) 0.7999(9) 0.048(4) Uiso 1 1 d . . .
H4 H 0.394(2) 1.1563(16) 0.8264(10) 0.054(4) Uiso 1 1 d . . .
H3B H 0.195(3) 1.0232(18) 0.9024(10) 0.060(5) Uiso 1 1 d . . .
H3A H 0.229(3) 0.8650(18) 0.8629(10) 0.061(5) Uiso 1 1 d . . .
H19 H 0.702(2) 0.5937(15) 1.0675(9) 0.049(4) Uiso 1 1 d . . .
H22 H -0.010(3) 0.6879(18) 1.1025(10) 0.068(5) Uiso 1 1 d . . .
H24C H 0.806(3) 0.335(2) 1.2257(12) 0.085(6) Uiso 1 1 d . . .
H21 H 0.185(3) 0.5149(17) 1.1822(11) 0.064(5) Uiso 1 1 d . . .
H24B H 0.786(3) 0.507(2) 1.2046(11) 0.080(6) Uiso 1 1 d . . .
H13 H 0.331(3) 1.019(2) 0.6373(13) 0.092(6) Uiso 1 1 d . . .
H24A H 0.854(3) 0.380(2) 1.1284(14) 0.086(7) Uiso 1 1 d . . .
H9 H 1.107(3) 0.642(2) 0.5414(13) 0.094(7) Uiso 1 1 d . . .
H7 H 0.665(3) 0.7348(18) 0.7465(11) 0.068(5) Uiso 1 1 d . . .
H8 H 0.860(3) 0.574(2) 0.6407(12) 0.087(6) Uiso 1 1 d . . .
H17 H 0.572(3) 1.305(2) 0.7240(13) 0.087(6) Uiso 1 1 d . . .
H15 H 0.430(3) 1.350(2) 0.4836(14) 0.103(7) Uiso 1 1 d . . .
H11 H 0.950(3) 1.031(2) 0.6675(12) 0.087(6) Uiso 1 1 d . . .
H16 H 0.563(4) 1.431(3) 0.6017(14) 0.114(8) Uiso 1 1 d . . .
H10 H 1.155(4) 0.866(2) 0.5528(14) 0.111(8) Uiso 1 1 d . . .
H14 H 0.324(4) 1.135(3) 0.5035(18) 0.141(10) Uiso 1 1 d . . .
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
C4 O1 C3 111.87(12) . . ?
C20 O2 C24 117.57(14) . . ?
N2 N3 C1 109.55(12) . . ?
N2 N1 C2 111.49(12) . . ?
N2 N1 C5 121.94(12) . . ?
C2 N1 C5 125.93(12) . . ?
N3 N2 N1 106.59(12) . . ?
C20 C19 C18 120.38(15) . . ?
C20 C19 H19 121.9(9) . . ?
C18 C19 H19 117.7(9) . . ?
N1 C2 C1 104.41(12) . . ?
N1 C2 C3 118.75(13) . . ?
C1 C2 C3 136.81(13) . . ?
N3 C1 C2 107.95(13) . . ?
N3 C1 C18 120.80(13) . . ?
C2 C1 C18 131.23(13) . . ?
O2 C20 C19 124.23(14) . . ?
O2 C20 C21 115.58(14) . . ?
C19 C20 C21 120.19(15) . . ?
O1 C3 C2 111.47(12) . . ?
O1 C3 H3B 109.8(9) . . ?
C2 C3 H3B 109.1(10) . . ?
O1 C3 H3A 107.0(9) . . ?
C2 C3 H3A 110.1(10) . . ?
H3B C3 H3A 109.4(13) . . ?
C22 C23 C18 119.98(15) . . ?
C22 C23 H23 120.3(10) . . ?
C18 C23 H23 119.7(10) . . ?
C23 C18 C19 118.91(14) . . ?
C23 C18 C1 121.99(14) . . ?
C19 C18 C1 119.09(14) . . ?
N1 C5 C6 111.11(12) . . ?
N1 C5 C4 105.83(11) . . ?
C6 C5 C4 114.39(13) . . ?
N1 C5 H5 107.8(8) . . ?
C6 C5 H5 110.8(9) . . ?
C4 C5 H5 106.6(9) . . ?
C22 C21 C20 119.49(16) . . ?
C22 C21 H21 120.9(11) . . ?
C20 C21 H21 119.5(11) . . ?
C11 C6 C7 118.85(17) . . ?
C11 C6 C5 119.70(16) . . ?
C7 C6 C5 121.45(14) . . ?
O1 C4 C12 109.39(13) . . ?
O1 C4 C5 109.13(12) . . ?
C12 C4 C5 112.82(12) . . ?
O1 C4 H4 107.9(8) . . ?
C12 C4 H4 111.8(8) . . ?
C5 C4 H4 105.7(9) . . ?
C23 C22 C21 121.05(16) . . ?
C23 C22 H22 120.0(10) . . ?
C21 C22 H22 119.0(10) . . ?
C17 C12 C13 118.27(17) . . ?
C17 C12 C4 119.68(16) . . ?
C13 C12 C4 122.05(16) . . ?
C6 C7 C8 120.35(19) . . ?
C6 C7 H7 121.6(10) . . ?
C8 C7 H7 118.0(10) . . ?
C6 C11 C10 120.4(2) . . ?
C6 C11 H11 116.7(11) . . ?
C10 C11 H11 122.8(12) . . ?
O2 C24 H24C 102.9(12) . . ?
O2 C24 H24B 108.6(11) . . ?
H24C C24 H24B 112.1(15) . . ?
O2 C24 H24A 111.8(12) . . ?
H24C C24 H24A 110.3(16) . . ?
H24B C24 H24A 110.9(16) . . ?
C12 C17 C16 120.6(2) . . ?
C12 C17 H17 118.1(12) . . ?
C16 C17 H17 121.2(12) . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 122.9(11) . . ?
C7 C8 H8 117.2(11) . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 115.5(12) . . ?
C14 C13 H13 124.2(12) . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 125.5(13) . . ?
C17 C16 H16 113.9(14) . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 120.0(13) . . ?
C8 C9 H9 119.8(13) . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 122.4(16) . . ?
C13 C14 H14 116.9(16) . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.1(13) . . ?
C11 C10 H10 120.6(13) . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.0(13) . . ?
C14 C15 H15 120.5(13) . . ?
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
O1 C4 1.4194(18) . ?
O1 C3 1.4195(18) . ?
O2 C20 1.3657(17) . ?
O2 C24 1.419(2) . ?
N3 N2 1.3076(17) . ?
N3 C1 1.3649(19) . ?
N1 N2 1.3450(16) . ?
N1 C2 1.3481(18) . ?
N1 C5 1.4526(19) . ?
C19 C20 1.373(2) . ?
C19 C18 1.393(2) . ?
C19 H19 0.963(16) . ?
C2 C1 1.371(2) . ?
C2 C3 1.485(2) . ?
C1 C18 1.456(2) . ?
C20 C21 1.379(2) . ?
C3 H3B 0.993(17) . ?
C3 H3A 0.973(17) . ?
C23 C22 1.371(2) . ?
C23 C18 1.386(2) . ?
C23 H23 0.963(16) . ?
C5 C6 1.507(2) . ?
C5 C4 1.541(2) . ?
C5 H5 0.959(16) . ?
C21 C22 1.372(2) . ?
C21 H21 0.917(17) . ?
C6 C11 1.373(2) . ?
C6 C7 1.377(2) . ?
C4 C12 1.497(2) . ?
C4 H4 1.012(15) . ?
C22 H22 0.956(18) . ?
C12 C17 1.376(3) . ?
C12 C13 1.376(3) . ?
C7 C8 1.381(3) . ?
C7 H7 0.951(17) . ?
C11 C10 1.379(3) . ?
C11 H11 0.98(2) . ?
C24 H24C 0.98(2) . ?
C24 H24B 1.02(2) . ?
C24 H24A 0.98(2) . ?
C17 C16 1.377(3) . ?
C17 H17 0.93(2) . ?
C8 C9 1.364(3) . ?
C8 H8 0.98(2) . ?
C13 C14 1.377(3) . ?
C13 H13 1.00(2) . ?
C16 C15 1.353(3) . ?
C16 H16 1.01(2) . ?
C9 C10 1.356(3) . ?
C9 H9 0.96(2) . ?
C14 C15 1.360(3) . ?
C14 H14 0.98(3) . ?
C10 H10 0.98(2) . ?
C15 H15 1.01(2) . ?
