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#$Date: 2022-12-08 11:39:14 +0200 (Thu, 08 Dec 2022) $
#$Revision: 279805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106371.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_8106371
loop_
_publ_author_name
'Sun, Yutong'
'Hong, Wei'
'Wang, Hao'
_publ_section_title
;
 Crystal structure of methyl
 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate,
 C24H21N3O5
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              985
_journal_page_last               986
_journal_paper_doi               10.1515/ncrs-2018-0040
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C24 H21 N3 O5'
_chemical_formula_sum            'C24 H21 N3 O5'
_chemical_formula_weight         431.44
_chemical_name_systematic
; 
Crystal structure of methyl 2-((1-2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.4167(7)
_cell_length_b                   14.0370(10)
_cell_length_c                   34.664(3)
_cell_measurement_reflns_used    5623
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.842
_cell_measurement_theta_min      2.084
_cell_volume                     4095.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXL'
_computing_publication_material  'Bruker SHELXL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            21579
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.350
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0457
_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)+(0.0439P)²+0.8145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2554
_reflns_number_total             3601
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0040_suppl.cif
_cod_data_source_block           19-4
_cod_database_code               8106371
_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   0.969
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
O4 O 0.33380(16) 0.51874(9) 0.34033(4) 0.0309(4) Uani 1 1 d . . . . .
O1 O 0.51320(18) 0.93696(10) 0.33939(4) 0.0365(4) Uani 1 1 d . . . . .
O5 O 0.49816(18) 0.50273(10) 0.28999(4) 0.0367(4) Uani 1 1 d . . . . .
O2 O 0.36574(18) 0.81591(10) 0.36067(4) 0.0371(4) Uani 1 1 d . . . . .
O3 O 0.55205(17) 0.50811(10) 0.39811(4) 0.0344(4) Uani 1 1 d . . . . .
N1 N 0.35294(19) 0.74176(11) 0.44629(4) 0.0247(4) Uani 1 1 d . . . . .
N3 N 0.4973(2) 0.65466(12) 0.48293(5) 0.0344(4) Uani 1 1 d . . . . .
N2 N 0.4092(2) 0.73249(12) 0.48247(5) 0.0360(5) Uani 1 1 d . . . . .
C11 C 0.4945(2) 0.61497(14) 0.44724(5) 0.0239(5) Uani 1 1 d . . . . .
C10 C 0.4024(2) 0.66959(13) 0.42383(5) 0.0232(5) Uani 1 1 d . . . . .
H10 H 0.378229 0.659055 0.397405 0.028 Uiso 1 1 calc R U . . .
C23 C 0.4576(2) 0.47959(14) 0.32212(5) 0.0250(5) Uani 1 1 d . . . . .
C13 C 0.5886(2) 0.42117(14) 0.38275(5) 0.0256(5) Uani 1 1 d . . . . .
C3 C 0.4191(2) 0.94782(14) 0.40299(5) 0.0238(5) Uani 1 1 d . . . . .
C8 C 0.3304(2) 0.91565(14) 0.43486(5) 0.0238(5) Uani 1 1 d . . . . .
C2 C 0.4279(2) 0.89182(15) 0.36639(5) 0.0274(5) Uani 1 1 d . . . . .
C17 C 0.5800(2) 0.31595(14) 0.32715(5) 0.0267(5) Uani 1 1 d . . . . .
C18 C 0.5396(2) 0.40414(14) 0.34538(5) 0.0249(5) Uani 1 1 d . . . . .
C7 C 0.3197(2) 0.97368(14) 0.46721(6) 0.0288(5) Uani 1 1 d . . . . .
H7 H 0.259411 0.952612 0.488751 0.035 Uiso 1 1 calc R U . . .
C16 C 0.6760(2) 0.24937(15) 0.34740(6) 0.0298(5) Uani 1 1 d . . . . .
C6 C 0.3947(2) 1.06165(15) 0.46888(6) 0.0300(5) Uani 1 1 d . . . . .
H6 H 0.384625 1.100397 0.491217 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6789(2) 0.35339(14) 0.40330(6) 0.0305(5) Uani 1 1 d . . . . .
H14 H 0.709305 0.365288 0.429247 0.037 Uiso 1 1 calc R U . . .
C9 C 0.2446(2) 0.82078(14) 0.43689(6) 0.0275(5) Uani 1 1 d . . . . .
H9A H 0.160331 0.824392 0.456752 0.033 Uiso 1 1 calc R U . . .
H9B H 0.193055 0.807876 0.411758 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5779(2) 0.52400(14) 0.43830(5) 0.0260(5) Uani 1 1 d . . . . .
H12A H 0.692841 0.529466 0.443924 0.031 Uiso 1 1 calc R U . . .
H12B H 0.533329 0.471037 0.453753 0.031 Uiso 1 1 calc R U . . .
C4 C 0.4949(2) 1.03615(15) 0.40526(6) 0.0291(5) Uani 1 1 d . . . . .
H4 H 0.555444 1.058107 0.383906 0.035 Uiso 1 1 calc R U . . .
C15 C 0.7220(2) 0.27074(15) 0.38558(6) 0.0332(5) Uani 1 1 d . . . . .
H15 H 0.785107 0.226093 0.399358 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4838(2) 1.09244(15) 0.43798(6) 0.0310(5) Uani 1 1 d . . . . .
H5 H 0.537421 1.151950 0.439097 0.037 Uiso 1 1 calc R U . . .
C19 C 0.5269(3) 0.29033(15) 0.28966(6) 0.0346(5) Uani 1 1 d . . . . .
H19 H 0.458115 0.331994 0.275984 0.042 Uiso 1 1 calc R U . . .
C24 C 0.2563(3) 0.59621(15) 0.32001(6) 0.0358(5) Uani 1 1 d . . . . .
H24A H 0.219097 0.573600 0.294833 0.054 Uiso 1 1 calc R U . . .
H24B H 0.331934 0.648504 0.316298 0.054 Uiso 1 1 calc R U . . .
H24C H 0.165584 0.618868 0.335163 0.054 Uiso 1 1 calc R U . . .
C22 C 0.7244(3) 0.16428(15) 0.32876(7) 0.0403(6) Uani 1 1 d . . . . .
H22 H 0.792157 0.121058 0.341961 0.048 Uiso 1 1 calc R U . . .
C20 C 0.5734(3) 0.20661(16) 0.27298(6) 0.0422(6) Uani 1 1 d . . . . .
H20 H 0.536076 0.190834 0.247919 0.051 Uiso 1 1 calc R U . . .
C21 C 0.6757(3) 0.14346(16) 0.29239(7) 0.0435(6) Uani 1 1 d . . . . .
H21 H 0.710424 0.086634 0.280124 0.052 Uiso 1 1 calc R U . . .
C1 C 0.5165(3) 0.89175(16) 0.30203(6) 0.0453(6) Uani 1 1 d . . . . .
H1A H 0.581389 0.929776 0.284321 0.068 Uiso 1 1 calc R U . . .
H1B H 0.408001 0.886928 0.291932 0.068 Uiso 1 1 calc R U . . .
H1C H 0.562201 0.827825 0.304453 0.068 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
C23 O4 C24 115.43(15) . .
C2 O1 C1 115.44(17) . .
C13 O3 C12 119.05(15) . .
C10 N1 N2 110.96(16) . .
C10 N1 C9 129.16(16) . .
N2 N1 C9 119.78(16) . .
N2 N3 C11 108.61(16) . .
N3 N2 N1 106.77(15) . .
N3 C11 C10 108.80(17) . .
N3 C11 C12 122.25(17) . .
C10 C11 C12 128.91(17) . .
N1 C10 C11 104.84(16) . .
N1 C10 H10 127.6 . .
C11 C10 H10 127.6 . .
O5 C23 O4 123.00(18) . .
O5 C23 C18 123.73(18) . .
O4 C23 C18 113.27(16) . .
O3 C13 C18 116.95(17) . .
O3 C13 C14 121.78(18) . .
C18 C13 C14 121.20(18) . .
C4 C3 C8 118.86(18) . .
C4 C3 C2 119.49(17) . .
C8 C3 C2 121.59(18) . .
C7 C8 C3 118.68(18) . .
C7 C8 C9 116.52(18) . .
C3 C8 C9 124.79(17) . .
O2 C2 O1 122.48(18) . .
O2 C2 C3 125.72(18) . .
O1 C2 C3 111.79(18) . .
C19 C17 C16 117.66(19) . .
C19 C17 C18 123.26(18) . .
C16 C17 C18 119.07(18) . .
C13 C18 C17 119.57(18) . .
C13 C18 C23 121.32(17) . .
C17 C18 C23 118.88(17) . .
C6 C7 C8 121.73(19) . .
C6 C7 H7 119.1 . .
C8 C7 H7 119.1 . .
C15 C16 C22 121.8(2) . .
C15 C16 C17 118.66(19) . .
C22 C16 C17 119.5(2) . .
C5 C6 C7 119.63(19) . .
C5 C6 H6 120.2 . .
C7 C6 H6 120.2 . .
C15 C14 C13 119.37(19) . .
C15 C14 H14 120.3 . .
C13 C14 H14 120.3 . .
N1 C9 C8 112.15(16) . .
N1 C9 H9A 109.2 . .
C8 C9 H9A 109.2 . .
N1 C9 H9B 109.2 . .
C8 C9 H9B 109.2 . .
H9A C9 H9B 107.9 . .
O3 C12 C11 105.38(15) . .
O3 C12 H12A 110.7 . .
C11 C12 H12A 110.7 . .
O3 C12 H12B 110.7 . .
C11 C12 H12B 110.7 . .
H12A C12 H12B 108.8 . .
C5 C4 C3 121.46(19) . .
C5 C4 H4 119.3 . .
C3 C4 H4 119.3 . .
C14 C15 C16 122.05(19) . .
C14 C15 H15 119.0 . .
C16 C15 H15 119.0 . .
C6 C5 C4 119.6(2) . .
C6 C5 H5 120.2 . .
C4 C5 H5 120.2 . .
C20 C19 C17 121.0(2) . .
C20 C19 H19 119.5 . .
C17 C19 H19 119.5 . .
O4 C24 H24A 109.5 . .
O4 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
O4 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C21 C22 C16 121.2(2) . .
C21 C22 H22 119.4 . .
C16 C22 H22 119.4 . .
C19 C20 C21 121.0(2) . .
C19 C20 H20 119.5 . .
C21 C20 H20 119.5 . .
C22 C21 C20 119.6(2) . .
C22 C21 H21 120.2 . .
C20 C21 H21 120.2 . .
O1 C1 H1A 109.5 . .
O1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
O1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 C23 1.337(2) .
O4 C24 1.451(2) .
O1 C2 1.339(2) .
O1 C1 1.442(2) .
O5 C23 1.209(2) .
O2 C2 1.204(2) .
O3 C13 1.366(2) .
O3 C12 1.428(2) .
N1 C10 1.344(2) .
N1 N2 1.347(2) .
N1 C9 1.472(2) .
N3 N2 1.320(2) .
N3 C11 1.357(2) .
C11 C10 1.359(3) .
C11 C12 1.490(3) .
C10 H10 0.9500 .
C23 C18 1.499(3) .
C13 C18 1.380(3) .
C13 C14 1.411(3) .
C3 C4 1.397(3) .
C3 C8 1.408(3) .
C3 C2 1.494(3) .
C8 C7 1.389(3) .
C8 C9 1.516(3) .
C17 C19 1.420(3) .
C17 C16 1.421(3) .
C17 C18 1.431(3) .
C7 C6 1.388(3) .
C7 H7 0.9500 .
C16 C15 1.411(3) .
C16 C22 1.418(3) .
C6 C5 1.377(3) .
C6 H6 0.9500 .
C14 C15 1.362(3) .
C14 H14 0.9500 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C4 C5 1.385(3) .
C4 H4 0.9500 .
C15 H15 0.9500 .
C5 H5 0.9500 .
C19 C20 1.367(3) .
C19 H19 0.9500 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C22 C21 1.358(3) .
C22 H22 0.9500 .
C20 C21 1.407(3) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
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
C11 N3 N2 N1 -0.6(2) . . . .
C10 N1 N2 N3 1.0(2) . . . .
C9 N1 N2 N3 177.70(16) . . . .
N2 N3 C11 C10 0.1(2) . . . .
N2 N3 C11 C12 -177.85(17) . . . .
N2 N1 C10 C11 -0.9(2) . . . .
C9 N1 C10 C11 -177.24(17) . . . .
N3 C11 C10 N1 0.5(2) . . . .
C12 C11 C10 N1 178.26(18) . . . .
C24 O4 C23 O5 -4.0(3) . . . .
C24 O4 C23 C18 176.38(16) . . . .
C12 O3 C13 C18 170.42(17) . . . .
C12 O3 C13 C14 -12.6(3) . . . .
C4 C3 C8 C7 0.9(3) . . . .
C2 C3 C8 C7 -176.34(17) . . . .
C4 C3 C8 C9 -178.73(17) . . . .
C2 C3 C8 C9 4.0(3) . . . .
C1 O1 C2 O2 4.2(3) . . . .
C1 O1 C2 C3 -174.89(17) . . . .
C4 C3 C2 O2 -178.7(2) . . . .
C8 C3 C2 O2 -1.5(3) . . . .
C4 C3 C2 O1 0.3(3) . . . .
C8 C3 C2 O1 177.58(17) . . . .
O3 C13 C18 C17 177.42(17) . . . .
C14 C13 C18 C17 0.4(3) . . . .
O3 C13 C18 C23 3.1(3) . . . .
C14 C13 C18 C23 -173.90(18) . . . .
C19 C17 C18 C13 176.27(19) . . . .
C16 C17 C18 C13 -2.8(3) . . . .
C19 C17 C18 C23 -9.3(3) . . . .
C16 C17 C18 C23 171.71(17) . . . .
O5 C23 C18 C13 128.8(2) . . . .
O4 C23 C18 C13 -51.6(2) . . . .
O5 C23 C18 C17 -45.6(3) . . . .
O4 C23 C18 C17 133.99(18) . . . .
C3 C8 C7 C6 -0.4(3) . . . .
C9 C8 C7 C6 179.27(17) . . . .
C19 C17 C16 C15 -176.17(18) . . . .
C18 C17 C16 C15 2.9(3) . . . .
C19 C17 C16 C22 4.6(3) . . . .
C18 C17 C16 C22 -176.33(18) . . . .
C8 C7 C6 C5 -0.7(3) . . . .
O3 C13 C14 C15 -175.09(18) . . . .
C18 C13 C14 C15 1.7(3) . . . .
C10 N1 C9 C8 -110.3(2) . . . .
N2 N1 C9 C8 73.6(2) . . . .
C7 C8 C9 N1 -99.38(19) . . . .
C3 C8 C9 N1 80.3(2) . . . .
C13 O3 C12 C11 -167.78(16) . . . .
N3 C11 C12 O3 -177.94(17) . . . .
C10 C11 C12 O3 4.6(3) . . . .
C8 C3 C4 C5 -0.3(3) . . . .
C2 C3 C4 C5 177.00(18) . . . .
C13 C14 C15 C16 -1.6(3) . . . .
C22 C16 C15 C14 178.46(19) . . . .
C17 C16 C15 C14 -0.8(3) . . . .
C7 C6 C5 C4 1.3(3) . . . .
C3 C4 C5 C6 -0.8(3) . . . .
C16 C17 C19 C20 -3.2(3) . . . .
C18 C17 C19 C20 177.71(19) . . . .
C15 C16 C22 C21 178.2(2) . . . .
C17 C16 C22 C21 -2.6(3) . . . .
C17 C19 C20 C21 -0.2(3) . . . .
C16 C22 C21 C20 -1.0(3) . . . .
C19 C20 C21 C22 2.4(3) . . . .
