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#$Date: 2023-09-18 10:07:43 +0300 (Mon, 18 Sep 2023) $
#$Revision: 286370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107497.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_8107497
loop_
_publ_author_name
'Xiong, Xin-Ting'
'Xiao, Pan-Lei'
'Ou-Yang, Xiao-Hui'
'Nie, Xu-Liang'
'Song, Xiu-Ying'
_publ_section_title
;
 Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl
 2-chloro-4-fluorobenzoate, C16H12ClFO5
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              571
_journal_page_last               573
_journal_paper_doi               10.1515/ncrs-2023-0092
_journal_volume                  238
_journal_year                    2023
_chemical_formula_sum            'C16 H12 Cl F O5'
_chemical_formula_weight         338.71
_chemical_name_systematic
'2-methoxy-4-(methoxycarbonyl)phenyl 2-chloro-4-fluorobenzoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.174(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7536(6)
_cell_length_b                   7.8281(3)
_cell_length_c                   14.0501(7)
_cell_measurement_reflns_used    2822
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.97
_cell_measurement_theta_min      2.21
_cell_volume                     1513.13(12)
_computing_cell_refinement       'APEX2, SAINT and SADABS [1]'
_computing_data_collection       'APEX2, SAINT and SADABS [1]'
_computing_data_reduction        'APEX2, SAINT and SADABS [1]'
_computing_molecular_graphics    'Diamond 4.0 [4]'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019) [3]'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019) [3]'
_computing_structure_solution    'XT, VERSION 2018/2 [2]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6080
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         3.434
_exptl_absorpt_coefficient_mu    0.286
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0056(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0367
_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)+(0.0339P)²+0.4884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2363
_reflns_number_total             2822
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0092_suppl_001.cif
_cod_data_source_block           YXG-CF-Cl_auto
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107497
_shelx_shelxl_version_number     2014/7
_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   0.942
_shelx_estimated_absorpt_t_max   0.964
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.76644(15) 0.9570(3) 0.08987(18) 0.0672(7) Uani 1 1 d . . . . .
H1A H 0.8002 0.8606 0.0764 0.101 Uiso 1 1 calc R U . . .
H1B H 0.8091 1.0186 0.1478 0.101 Uiso 1 1 calc R U . . .
H1C H 0.7455 1.0308 0.0313 0.101 Uiso 1 1 calc R U . . .
C2 C 0.60911(13) 0.8369(2) 0.03095(15) 0.0414(4) Uani 1 1 d . . . . .
C3 C 0.53025(12) 0.7670(2) 0.06189(13) 0.0364(4) Uani 1 1 d . . . . .
C4 C 0.53905(13) 0.7536(3) 0.16331(13) 0.0415(4) Uani 1 1 d . . . . .
H4 H 0.5937 0.7970 0.2146 0.050 Uiso 1 1 calc R U . . .
C5 C 0.46630(13) 0.6756(3) 0.18803(14) 0.0429(5) Uani 1 1 d . . . . .
H5 H 0.4724 0.6645 0.2560 0.052 Uiso 1 1 calc R U . . .
C6 C 0.38527(12) 0.6146(2) 0.11191(13) 0.0369(4) Uani 1 1 d . . . . .
C7 C 0.37411(12) 0.6290(2) 0.00935(14) 0.0401(4) Uani 1 1 d . . . . .
C8 C 0.44730(13) 0.7049(2) -0.01518(14) 0.0408(4) Uani 1 1 d . . . . .
H8 H 0.4413 0.7148 -0.0832 0.049 Uiso 1 1 calc R U . . .
C9 C 0.27435(16) 0.5799(4) -0.16443(16) 0.0722(7) Uani 1 1 d . . . . .
H9A H 0.2748 0.6991 -0.1803 0.108 Uiso 1 1 calc R U . . .
H9B H 0.2124 0.5316 -0.2042 0.108 Uiso 1 1 calc R U . . .
H9C H 0.3247 0.5222 -0.1801 0.108 Uiso 1 1 calc R U . . .
C10 C 0.22594(12) 0.5868(2) 0.11369(13) 0.0366(4) Uani 1 1 d . . . . .
C11 C 0.15806(12) 0.4512(2) 0.12021(12) 0.0322(4) Uani 1 1 d . . . . .
C12 C 0.18156(12) 0.2795(2) 0.11238(13) 0.0368(4) Uani 1 1 d . . . . .
H12 H 0.2412 0.2533 0.1075 0.044 Uiso 1 1 calc R U . . .
C13 C 0.11903(13) 0.1485(2) 0.11167(13) 0.0403(4) Uani 1 1 d . . . . .
H13 H 0.1352 0.0352 0.1057 0.048 Uiso 1 1 calc R U . . .
C14 C 0.03212(13) 0.1910(2) 0.12010(14) 0.0411(4) Uani 1 1 d . . . . .
C15 C 0.00527(13) 0.3559(2) 0.12967(14) 0.0398(4) Uani 1 1 d . . . . .
H15 H -0.0540 0.3796 0.1360 0.048 Uiso 1 1 calc R U . . .
C16 C 0.06870(12) 0.4859(2) 0.12965(12) 0.0334(4) Uani 1 1 d . . . . .
Cl1 Cl 0.03207(3) 0.69181(6) 0.14373(4) 0.04743(17) Uani 1 1 d . . . . .
F1 F -0.03085(9) 0.06512(15) 0.11894(10) 0.0646(4) Uani 1 1 d . . . . .
O1 O 0.68287(9) 0.8983(2) 0.11094(10) 0.0555(4) Uani 1 1 d . . . . .
O2 O 0.60874(10) 0.8366(2) -0.05449(11) 0.0566(4) Uani 1 1 d . . . . .
O3 O 0.29090(9) 0.5605(2) -0.05882(10) 0.0591(4) Uani 1 1 d . . . . .
O4 O 0.31685(8) 0.52082(16) 0.13770(10) 0.0448(3) Uani 1 1 d . . . . .
O5 O 0.20704(10) 0.73283(17) 0.08994(12) 0.0577(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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C15 C16 C11 121.21(16) . .
C15 C16 Cl1 116.45(13) . .
C11 C16 Cl1 122.33(13) . .
C16 C11 C12 117.52(16) . .
C16 C11 C10 123.15(15) . .
C12 C11 C10 119.27(15) . .
C13 C12 C11 122.03(17) . .
C13 C12 H12 119.0 . .
C11 C12 H12 119.0 . .
O5 C10 O4 122.79(17) . .
O5 C10 C11 127.33(17) . .
O4 C10 C11 109.87(15) . .
C7 C8 C3 120.10(17) . .
C7 C8 H8 120.0 . .
C3 C8 H8 120.0 . .
O3 C7 C8 125.47(17) . .
O3 C7 C6 115.72(16) . .
C8 C7 C6 118.78(16) . .
C14 C13 C12 117.64(17) . .
C14 C13 H13 121.2 . .
C12 C13 H13 121.2 . .
O2 C2 O1 123.32(17) . .
O2 C2 C3 124.86(17) . .
O1 C2 C3 111.80(16) . .
C14 C15 C16 118.27(16) . .
C14 C15 H15 120.9 . .
C16 C15 H15 120.9 . .
C5 C6 C7 121.51(16) . .
C5 C6 O4 119.26(16) . .
C7 C6 O4 118.92(15) . .
C6 C5 C4 119.67(17) . .
C6 C5 H5 120.2 . .
C4 C5 H5 120.2 . .
C4 C3 C8 120.08(17) . .
C4 C3 C2 122.39(16) . .
C8 C3 C2 117.44(16) . .
F1 C14 C13 118.90(16) . .
F1 C14 C15 117.79(16) . .
C13 C14 C15 123.32(17) . .
C5 C4 C3 119.85(16) . .
C5 C4 H4 120.1 . .
C3 C4 H4 120.1 . .
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 . .
O3 C9 H9A 109.5 . .
O3 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
O3 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C10 O4 C6 118.42(14) . .
C7 O3 C9 117.52(16) . .
C2 O1 C1 115.94(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C16 1.7339(18) .
C16 C15 1.383(2) .
C16 C11 1.399(2) .
C11 C12 1.402(2) .
C11 C10 1.485(2) .
C12 C13 1.377(2) .
C12 H12 0.9300 .
C10 O5 1.196(2) .
C10 O4 1.361(2) .
C8 C7 1.381(3) .
C8 C3 1.396(2) .
C8 H8 0.9300 .
C7 O3 1.365(2) .
C7 C6 1.395(2) .
C13 C14 1.371(3) .
C13 H13 0.9300 .
C2 O2 1.198(2) .
C2 O1 1.340(2) .
C2 C3 1.486(2) .
C15 C14 1.371(3) .
C15 H15 0.9300 .
C6 C5 1.370(2) .
C6 O4 1.398(2) .
C5 C4 1.384(2) .
C5 H5 0.9300 .
C3 C4 1.387(2) .
C14 F1 1.350(2) .
C4 H4 0.9300 .
C1 O1 1.443(2) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C9 O3 1.422(2) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13 O5 0.93 2.64 3.557(2) 171.2 1_545
C13 H13 O5 0.93 2.64 3.557(2) 171.2 1_545
