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#$Date: 2022-12-05 11:53:03 +0200 (Mon, 05 Dec 2022) $
#$Revision: 279690 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106314.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_8106314
loop_
_publ_author_name
'Wang, Zhe'
'Hong, Wei'
'Wang, Hao'
_publ_section_title
;
 Crystal structure of methyl
 2-((4-((2-nitrophenoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl) benzoate,
 C18H16N4O5
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              831
_journal_page_last               832
_journal_paper_doi               10.1515/ncrs-2018-0041
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C18 H16 N4 O5'
_chemical_formula_sum            'C18 H16 N4 O5'
_chemical_formula_weight         368.35
_chemical_name_systematic
; 
Crystal structure of methyl 2-((4-((2-nitrophenoxy)methyl)-1H-1,2,3-triazol-1-yl)
methyl)benzoate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                102.046(3)
_cell_angle_beta                 97.453(3)
_cell_angle_gamma                99.280(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4076(6)
_cell_length_b                   8.6630(5)
_cell_length_c                   12.0763(8)
_cell_measurement_reflns_used    8932
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.083
_cell_measurement_theta_min      2.193
_cell_volume                     836.70(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    SHELXS-2018
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Bruker?Smart?Apex?CCD?area?detector
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            13503
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.451
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0396
_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)+(0.0478P)²+0.2664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2345
_reflns_number_total             2945
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0041_suppl.cif
_cod_data_source_block           40-1-NEW
_cod_database_code               8106314
_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.
;
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_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_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
C1 C -0.3210(2) 0.8863(2) 1.04268(17) 0.0349(5) Uani 1 1 d . . . . .
H1A H -0.431627 0.856403 0.997580 0.052 Uiso 1 1 calc R U . . .
H1B H -0.278612 1.000848 1.050113 0.052 Uiso 1 1 calc R U . . .
H1C H -0.324308 0.865645 1.119186 0.052 Uiso 1 1 calc R U . . .
C2 C -0.0615(2) 0.8167(2) 1.03980(15) 0.0240(4) Uani 1 1 d . . . . .
C3 C 0.0425(2) 0.71685(19) 0.97706(14) 0.0219(4) Uani 1 1 d . . . . .
C4 C 0.1719(2) 0.6819(2) 1.04606(15) 0.0264(4) Uani 1 1 d . . . . .
H4 H 0.187706 0.721566 1.126997 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2774(2) 0.5908(2) 0.99898(16) 0.0292(4) Uani 1 1 d . . . . .
H5 H 0.364446 0.567103 1.047063 0.035 Uiso 1 1 calc R U . . .
C6 C 0.2552(2) 0.5342(2) 0.88113(16) 0.0296(4) Uani 1 1 d . . . . .
H6 H 0.327278 0.471368 0.847905 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1277(2) 0.5691(2) 0.81122(15) 0.0258(4) Uani 1 1 d . . . . .
H7 H 0.113860 0.529653 0.730344 0.031 Uiso 1 1 calc R U . . .
C8 C 0.0199(2) 0.66052(19) 0.85714(14) 0.0202(4) Uani 1 1 d . . . . .
C9 C -0.1165(2) 0.6972(2) 0.77758(14) 0.0231(4) Uani 1 1 d . . . . .
H9A H -0.216805 0.615541 0.769888 0.028 Uiso 1 1 calc R U . . .
H9B H -0.139697 0.803522 0.812238 0.028 Uiso 1 1 calc R U . . .
C10 C 0.0344(2) 0.8044(2) 0.63306(14) 0.0205(4) Uani 1 1 d . . . . .
H10 H 0.110293 0.893324 0.681834 0.025 Uiso 1 1 calc R U . . .
C11 C 0.01394(19) 0.75617(18) 0.51664(14) 0.0175(4) Uani 1 1 d . . . . .
C12 C 0.1035(2) 0.82741(19) 0.43488(14) 0.0207(4) Uani 1 1 d . . . . .
H12A H 0.168895 0.752944 0.397466 0.025 Uiso 1 1 calc R U . . .
H12B H 0.026447 0.852292 0.374834 0.025 Uiso 1 1 calc R U . . .
C13 C 0.31234(19) 1.06010(19) 0.45574(14) 0.0185(4) Uani 1 1 d . . . . .
C14 C 0.3213(2) 1.0217(2) 0.33959(15) 0.0242(4) Uani 1 1 d . . . . .
H14 H 0.249872 0.929780 0.290471 0.029 Uiso 1 1 calc R U . . .
C15 C 0.4333(2) 1.1157(2) 0.29442(16) 0.0304(4) Uani 1 1 d . . . . .
H15 H 0.438301 1.086836 0.214794 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5378(2) 1.2509(2) 0.36352(17) 0.0313(5) Uani 1 1 d . . . . .
H16 H 0.613219 1.315591 0.331656 0.038 Uiso 1 1 calc R U . . .
C17 C 0.5313(2) 1.2906(2) 0.47893(16) 0.0278(4) Uani 1 1 d . . . . .
H17 H 0.603260 1.382802 0.527272 0.033 Uiso 1 1 calc R U . . .
C18 C 0.42052(19) 1.19703(19) 0.52509(14) 0.0201(4) Uani 1 1 d . . . . .
O1 O -0.01300(17) 0.90989(17) 1.13160(12) 0.0415(4) Uani 1 1 d . . . . .
O2 O -0.21560(14) 0.79185(14) 0.98537(10) 0.0283(3) Uani 1 1 d . . . . .
O3 O 0.20752(13) 0.97190(13) 0.50510(9) 0.0219(3) Uani 1 1 d . . . . .
O4 O 0.30660(17) 1.19395(16) 0.69004(11) 0.0371(3) Uani 1 1 d . . . . .
O5 O 0.54414(18) 1.33980(18) 0.70737(12) 0.0491(4) Uani 1 1 d . . . . .
N1 N -0.07676(16) 0.69827(16) 0.66396(11) 0.0194(3) Uani 1 1 d . . . . .
N2 N -0.16297(16) 0.58914(16) 0.57133(12) 0.0211(3) Uani 1 1 d . . . . .
N3 N -0.10834(16) 0.62464(16) 0.48047(12) 0.0210(3) Uani 1 1 d . . . . .
N4 N 0.42263(18) 1.24631(17) 0.64845(13) 0.0261(4) Uani 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
O2 C1 H1A 109.5 . .
O2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
O2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O1 C2 O2 122.57(16) . .
O1 C2 C3 123.65(17) . .
O2 C2 C3 113.77(14) . .
C4 C3 C8 119.69(16) . .
C4 C3 C2 115.35(16) . .
C8 C3 C2 124.95(16) . .
C5 C4 C3 121.24(17) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C4 C5 C6 119.35(17) . .
C4 C5 H5 120.3 . .
C6 C5 H5 120.3 . .
C5 C6 C7 120.10(17) . .
C5 C6 H6 120.0 . .
C7 C6 H6 120.0 . .
C6 C7 C8 121.39(17) . .
C6 C7 H7 119.3 . .
C8 C7 H7 119.3 . .
C7 C8 C3 118.23(16) . .
C7 C8 C9 119.63(15) . .
C3 C8 C9 122.14(15) . .
N1 C9 C8 112.76(14) . .
N1 C9 H9A 109.0 . .
C8 C9 H9A 109.0 . .
N1 C9 H9B 109.0 . .
C8 C9 H9B 109.0 . .
H9A C9 H9B 107.8 . .
N1 C10 C11 104.80(14) . .
N1 C10 H10 127.6 . .
C11 C10 H10 127.6 . .
N3 C11 C10 108.83(14) . .
N3 C11 C12 122.02(14) . .
C10 C11 C12 129.15(14) . .
O3 C12 C11 104.42(13) . .
O3 C12 H12A 110.9 . .
C11 C12 H12A 110.9 . .
O3 C12 H12B 110.9 . .
C11 C12 H12B 110.9 . .
H12A C12 H12B 108.9 . .
O3 C13 C14 123.51(14) . .
O3 C13 C18 118.86(14) . .
C14 C13 C18 117.62(15) . .
C15 C14 C13 120.76(16) . .
C15 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
C16 C15 C14 120.96(17) . .
C16 C15 H15 119.5 . .
C14 C15 H15 119.5 . .
C17 C16 C15 119.16(16) . .
C17 C16 H16 120.4 . .
C15 C16 H16 120.4 . .
C16 C17 C18 120.37(17) . .
C16 C17 H17 119.8 . .
C18 C17 H17 119.8 . .
C17 C18 C13 121.13(16) . .
C17 C18 N4 116.97(15) . .
C13 C18 N4 121.90(14) . .
C2 O2 C1 115.80(14) . .
C13 O3 C12 118.56(12) . .
N2 N1 C10 110.68(13) . .
N2 N1 C9 120.38(13) . .
C10 N1 C9 128.81(14) . .
N3 N2 N1 107.40(13) . .
N2 N3 C11 108.29(13) . .
O4 N4 O5 122.18(15) . .
O4 N4 C18 119.98(14) . .
O5 N4 C18 117.84(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.446(2) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 O1 1.204(2) .
C2 O2 1.337(2) .
C2 C3 1.493(3) .
C3 C4 1.395(2) .
C3 C8 1.405(2) .
C4 C5 1.379(3) .
C4 H4 0.9500 .
C5 C6 1.382(3) .
C5 H5 0.9500 .
C6 C7 1.389(3) .
C6 H6 0.9500 .
C7 C8 1.391(2) .
C7 H7 0.9500 .
C8 C9 1.516(2) .
C9 N1 1.455(2) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 N1 1.347(2) .
C10 C11 1.360(2) .
C10 H10 0.9500 .
C11 N3 1.358(2) .
C11 C12 1.490(2) .
C12 O3 1.4361(19) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 O3 1.3510(19) .
C13 C14 1.387(2) .
C13 C18 1.406(2) .
C14 C15 1.385(2) .
C14 H14 0.9500 .
C15 C16 1.382(3) .
C15 H15 0.9500 .
C16 C17 1.375(3) .
C16 H16 0.9500 .
C17 C18 1.384(2) .
C17 H17 0.9500 .
C18 N4 1.458(2) .
O4 N4 1.2204(19) .
O5 N4 1.2288(18) .
N1 N2 1.3408(19) .
N2 N3 1.3174(19) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C2 C3 C4 26.7(3) . . . .
O2 C2 C3 C4 -152.41(15) . . . .
O1 C2 C3 C8 -152.28(18) . . . .
O2 C2 C3 C8 28.6(2) . . . .
C8 C3 C4 C5 -0.9(2) . . . .
C2 C3 C4 C5 -179.96(15) . . . .
C3 C4 C5 C6 0.5(3) . . . .
C4 C5 C6 C7 0.0(3) . . . .
C5 C6 C7 C8 -0.1(3) . . . .
C6 C7 C8 C3 -0.3(2) . . . .
C6 C7 C8 C9 179.35(15) . . . .
C4 C3 C8 C7 0.8(2) . . . .
C2 C3 C8 C7 179.71(16) . . . .
C4 C3 C8 C9 -178.84(15) . . . .
C2 C3 C8 C9 0.1(2) . . . .
C7 C8 C9 N1 -27.1(2) . . . .
C3 C8 C9 N1 152.50(15) . . . .
N1 C10 C11 N3 0.50(18) . . . .
N1 C10 C11 C12 -179.72(16) . . . .
N3 C11 C12 O3 173.76(14) . . . .
C10 C11 C12 O3 -6.0(2) . . . .
O3 C13 C14 C15 -179.01(16) . . . .
C18 C13 C14 C15 0.0(2) . . . .
C13 C14 C15 C16 -0.6(3) . . . .
C14 C15 C16 C17 0.9(3) . . . .
C15 C16 C17 C18 -0.5(3) . . . .
C16 C17 C18 C13 -0.1(3) . . . .
C16 C17 C18 N4 179.34(15) . . . .
O3 C13 C18 C17 179.40(15) . . . .
C14 C13 C18 C17 0.4(2) . . . .
O3 C13 C18 N4 0.0(2) . . . .
C14 C13 C18 N4 -179.04(15) . . . .
O1 C2 O2 C1 1.1(2) . . . .
C3 C2 O2 C1 -179.82(14) . . . .
C14 C13 O3 C12 2.3(2) . . . .
C18 C13 O3 C12 -176.70(14) . . . .
C11 C12 O3 C13 176.39(13) . . . .
C11 C10 N1 N2 -0.18(18) . . . .
C11 C10 N1 C9 -175.87(15) . . . .
C8 C9 N1 N2 115.58(16) . . . .
C8 C9 N1 C10 -69.1(2) . . . .
C10 N1 N2 N3 -0.21(18) . . . .
C9 N1 N2 N3 175.90(14) . . . .
N1 N2 N3 C11 0.52(17) . . . .
C10 C11 N3 N2 -0.64(18) . . . .
C12 C11 N3 N2 179.55(14) . . . .
C17 C18 N4 O4 163.02(16) . . . .
C13 C18 N4 O4 -17.5(2) . . . .
C17 C18 N4 O5 -17.5(2) . . . .
C13 C18 N4 O5 161.95(16) . . . .
