#------------------------------------------------------------------------------
#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/27/8102789.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_8102789
loop_
_publ_author_name
'Ye-Chen Wang'
'Zhi-Yu Shao'
'Yun-Xia Deng'
'Xiao-Xia Yang'
_publ_section_title
;
 Crystal structure of methyl
 2-(1-(2-cyanophenoxy)-2-methoxy-2-oxoethyl)-4,5-dimethoxybenzoate,
 C20H19NO7
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              439
_journal_volume                  225
_journal_year                    2010
_chemical_formula_sum            'C20 H19 N O7'
_chemical_formula_weight         385.36
_chemical_name_systematic
; 
methyl 2-(1-(2-cyanophenoxy)-
2-methoxy-2-oxoethyl)-4,5-dimethoxybenzoate
;
_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                72.845(2)
_cell_angle_beta                 82.103(3)
_cell_angle_gamma                84.848(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7674(12)
_cell_length_b                   10.0605(14)
_cell_length_c                   11.1943(15)
_cell_measurement_reflns_used    1857
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.234
_cell_measurement_theta_min      4.836
_cell_volume                     933.2(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5149
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5532
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.237
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.035(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0868P)²+0.0038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1542
_reflns_number_gt                2602
_reflns_number_total             3609
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3096.cff
_cod_data_source_block           cd201246
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102789
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 0.71492(16) 0.74374(15) -0.01427(14) 0.0608(4) Uani 1 1 d . . .
O2 O 0.81775(15) 0.48999(15) 0.07660(15) 0.0604(4) Uani 1 1 d . . .
O3 O 0.39995(15) 0.21057(13) 0.32692(14) 0.0533(4) Uani 1 1 d . . .
O4 O 0.1293(2) 0.30605(17) 0.48818(17) 0.0752(5) Uani 1 1 d . . .
O5 O 0.32748(15) 0.43908(15) 0.46434(13) 0.0529(4) Uani 1 1 d . . .
O6 O 0.09609(16) 0.55208(15) 0.25709(15) 0.0603(4) Uani 1 1 d . . .
O7 O 0.15491(16) 0.76033(15) 0.12783(15) 0.0608(4) Uani 1 1 d . . .
N1 N 0.7266(3) 0.0138(3) 0.2974(3) 0.1034(9) Uani 1 1 d . . .
C1 C 0.3555(2) 0.58808(19) 0.16491(17) 0.0424(5) Uani 1 1 d . . .
C2 C 0.4567(2) 0.6871(2) 0.08872(19) 0.0471(5) Uani 1 1 d . . .
H2 H 0.4194 0.7785 0.0563 0.057 Uiso 1 1 calc R . .
C3 C 0.6091(2) 0.6529(2) 0.06073(18) 0.0463(5) Uani 1 1 d . . .
C4 C 0.6661(2) 0.5156(2) 0.10981(18) 0.0454(5) Uani 1 1 d . . .
C5 C 0.5672(2) 0.4182(2) 0.18685(18) 0.0441(5) Uani 1 1 d . . .
H5 H 0.6057 0.3275 0.2203 0.053 Uiso 1 1 calc R . .
C6 C 0.4121(2) 0.45152(19) 0.21597(17) 0.0402(4) Uani 1 1 d . . .
C7 C 0.3083(2) 0.33917(18) 0.29939(19) 0.0431(5) Uani 1 1 d . . .
H7 H 0.2236 0.3308 0.2538 0.052 Uiso 1 1 calc R . .
C8 C 0.2421(2) 0.36022(19) 0.42672(19) 0.0468(5) Uani 1 1 d . . .
C9 C 0.2762(3) 0.4569(3) 0.5879(2) 0.0711(7) Uani 1 1 d . . .
H9A H 0.1715 0.4944 0.5901 0.107 Uiso 1 1 calc R . .
H9B H 0.3410 0.5197 0.6046 0.107 Uiso 1 1 calc R . .
H9C H 0.2820 0.3683 0.6506 0.107 Uiso 1 1 calc R . .
C10 C 0.1909(2) 0.6286(2) 0.18939(19) 0.0450(5) Uani 1 1 d . . .
C11 C -0.0054(3) 0.8046(3) 0.1490(3) 0.0741(7) Uani 1 1 d . . .
H11A H -0.0677 0.7533 0.1158 0.111 Uiso 1 1 calc R . .
H11B H -0.0192 0.9023 0.1076 0.111 Uiso 1 1 calc R . .
H11C H -0.0358 0.7874 0.2377 0.111 Uiso 1 1 calc R . .
C12 C 0.6736(3) 0.8877(2) -0.0366(2) 0.0694(7) Uani 1 1 d . . .
H12A H 0.5874 0.9115 -0.0847 0.104 Uiso 1 1 calc R . .
H12B H 0.7594 0.9410 -0.0825 0.104 Uiso 1 1 calc R . .
H12C H 0.6459 0.9082 0.0424 0.104 Uiso 1 1 calc R . .
C13 C 0.8845(2) 0.3562(2) 0.1336(2) 0.0672(7) Uani 1 1 d . . .
H13A H 0.8749 0.3401 0.2231 0.101 Uiso 1 1 calc R . .
H13B H 0.9916 0.3516 0.1016 0.101 Uiso 1 1 calc R . .
H13C H 0.8322 0.2864 0.1146 0.101 Uiso 1 1 calc R . .
C14 C 0.3324(2) 0.08657(19) 0.34844(18) 0.0460(5) Uani 1 1 d . . .
C15 C 0.1765(2) 0.0679(2) 0.3642(2) 0.0534(5) Uani 1 1 d . . .
H15 H 0.1064 0.1437 0.3602 0.064 Uiso 1 1 calc R . .
C16 C 0.1245(3) -0.0631(2) 0.3860(2) 0.0614(6) Uani 1 1 d . . .
H16 H 0.0191 -0.0747 0.3954 0.074 Uiso 1 1 calc R . .
C17 C 0.2252(3) -0.1765(2) 0.3940(3) 0.0719(7) Uani 1 1 d . . .
H17 H 0.1883 -0.2649 0.4113 0.086 Uiso 1 1 calc R . .
C18 C 0.3806(3) -0.1593(2) 0.3766(2) 0.0719(7) Uani 1 1 d . . .
H18 H 0.4495 -0.2360 0.3806 0.086 Uiso 1 1 calc R . .
C19 C 0.4364(3) -0.0270(2) 0.3528(2) 0.0547(5) Uani 1 1 d . . .
C20 C 0.5979(3) -0.0048(2) 0.3249(2) 0.0688(7) 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
_geom_angle_publ_flag
C3 O1 C12 116.62(17) . . ?
C4 O2 C13 117.92(16) . . ?
C14 O3 C7 120.11(14) . . ?
C8 O5 C9 115.55(16) . . ?
C10 O7 C11 115.02(17) . . ?
C6 C1 C2 119.29(17) . . ?
C6 C1 C10 120.94(17) . . ?
C2 C1 C10 119.76(17) . . ?
C3 C2 C1 121.57(18) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 O1 124.94(18) . . ?
C2 C3 C4 119.45(17) . . ?
O1 C3 C4 115.61(17) . . ?
O2 C4 C5 125.08(18) . . ?
O2 C4 C3 115.77(17) . . ?
C5 C4 C3 119.15(18) . . ?
C4 C5 C6 122.02(18) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 118.51(17) . . ?
C5 C6 C7 119.60(16) . . ?
C1 C6 C7 121.87(16) . . ?
O3 C7 C6 107.33(14) . . ?
O3 C7 C8 106.13(15) . . ?
C6 C7 C8 115.27(15) . . ?
O3 C7 H7 109.3 . . ?
C6 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
O4 C8 O5 123.8(2) . . ?
O4 C8 C7 123.56(18) . . ?
O5 C8 C7 112.60(16) . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O6 C10 O7 122.28(18) . . ?
O6 C10 C1 124.61(18) . . ?
O7 C10 C1 113.11(17) . . ?
O7 C11 H11A 109.5 . . ?
O7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 C15 126.07(17) . . ?
O3 C14 C19 114.26(18) . . ?
C15 C14 C19 119.67(18) . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.6(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 119.3(2) . . ?
C14 C19 C20 119.3(2) . . ?
C18 C19 C20 121.3(2) . . ?
N1 C20 C19 177.1(3) . . ?
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 C3 1.373(2) . ?
O1 C12 1.418(3) . ?
O2 C4 1.353(2) . ?
O2 C13 1.420(3) . ?
O3 C14 1.372(2) . ?
O3 C7 1.435(2) . ?
O4 C8 1.199(2) . ?
O5 C8 1.326(2) . ?
O5 C9 1.452(3) . ?
O6 C10 1.206(2) . ?
O7 C10 1.333(2) . ?
O7 C11 1.445(3) . ?
N1 C20 1.145(3) . ?
C1 C6 1.397(3) . ?
C1 C2 1.399(3) . ?
C1 C10 1.475(3) . ?
C2 C3 1.367(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.518(3) . ?
C7 C8 1.530(3) . ?
C7 H7 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
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 C15 1.377(3) . ?
C14 C19 1.390(3) . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.397(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.430(4) . ?
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
_geom_torsion_publ_flag
C6 C1 C2 C3 1.4(3) . . . . ?
C10 C1 C2 C3 -178.04(17) . . . . ?
C1 C2 C3 O1 179.27(17) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C12 O1 C3 C2 17.2(3) . . . . ?
C12 O1 C3 C4 -163.16(19) . . . . ?
C13 O2 C4 C5 -5.9(3) . . . . ?
C13 O2 C4 C3 173.94(18) . . . . ?
C2 C3 C4 O2 179.34(17) . . . . ?
O1 C3 C4 O2 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
O1 C3 C4 C5 179.53(17) . . . . ?
O2 C4 C5 C6 -179.27(17) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 178.89(17) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
C10 C1 C6 C5 178.14(17) . . . . ?
C2 C1 C6 C7 179.98(17) . . . . ?
C10 C1 C6 C7 -0.5(3) . . . . ?
C14 O3 C7 C6 -150.34(16) . . . . ?
C14 O3 C7 C8 85.9(2) . . . . ?
C5 C6 C7 O3 -3.1(2) . . . . ?
C1 C6 C7 O3 175.55(16) . . . . ?
C5 C6 C7 C8 114.86(19) . . . . ?
C1 C6 C7 C8 -66.5(2) . . . . ?
C9 O5 C8 O4 0.2(3) . . . . ?
C9 O5 C8 C7 -176.63(17) . . . . ?
O3 C7 C8 O4 -82.3(2) . . . . ?
C6 C7 C8 O4 159.1(2) . . . . ?
O3 C7 C8 O5 94.51(17) . . . . ?
C6 C7 C8 O5 -24.1(2) . . . . ?
C11 O7 C10 O6 0.4(3) . . . . ?
C11 O7 C10 C1 179.99(18) . . . . ?
C6 C1 C10 O6 3.2(3) . . . . ?
C2 C1 C10 O6 -177.31(19) . . . . ?
C6 C1 C10 O7 -176.36(16) . . . . ?
C2 C1 C10 O7 3.1(3) . . . . ?
C7 O3 C14 C15 -9.8(3) . . . . ?
C7 O3 C14 C19 169.65(17) . . . . ?
O3 C14 C15 C16 -179.6(2) . . . . ?
C19 C14 C15 C16 0.9(3) . . . . ?
C14 C15 C16 C17 0.9(4) . . . . ?
C15 C16 C17 C18 -1.9(4) . . . . ?
C16 C17 C18 C19 1.1(4) . . . . ?
O3 C14 C19 C18 178.8(2) . . . . ?
C15 C14 C19 C18 -1.7(3) . . . . ?
O3 C14 C19 C20 -5.2(3) . . . . ?
C15 C14 C19 C20 174.3(2) . . . . ?
C17 C18 C19 C14 0.7(4) . . . . ?
C17 C18 C19 C20 -175.3(2) . . . . ?
C14 C19 C20 N1 -87(5) . . . . ?
C18 C19 C20 N1 89(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139207305
