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#$Date: 2022-11-18 11:41:08 +0200 (Fri, 18 Nov 2022) $
#$Revision: 279392 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106158.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_8106158
loop_
_publ_author_name
'Yuan, Lin'
'Zhang, Min'
'Yuan, Xian-You'
'Liu, Fang'
_publ_section_title
;
 Crystal structure of diethyl
 2-(2-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19Cl1O6
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              377
_journal_page_last               378
_journal_paper_doi               10.1515/ncrs-2017-0260
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C16 H19 Cl O6'
_chemical_formula_sum            'C16 H19 Cl O6'
_chemical_formula_weight         342.76
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                101.910(11)
_cell_angle_beta                 100.040(11)
_cell_angle_gamma                110.345(10)
_cell_formula_units_Z            2
_cell_length_a                   7.827(8)
_cell_length_b                   9.253(9)
_cell_length_c                   12.978(13)
_cell_measurement_reflns_used    5663
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.45
_cell_volume                     830.7(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7724
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.66
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9131
_exptl_absorpt_correction_T_min  0.8930
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0334
_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)+(0.0463P)²+0.2182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                2612
_reflns_number_total             2914
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0260_suppl.cif
_cod_data_source_block           1504111_0m
_cod_database_code               8106158
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B), C13(H13A,H13B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.49710(8) 0.31396(7) 0.51100(4) 0.08036(19) Uani 1 d . . .
O2 O 0.61496(13) 0.32404(10) 0.76595(7) 0.0376(2) Uani 1 d . . .
O1 O 0.57604(14) 0.06040(11) 0.75375(8) 0.0435(2) Uani 1 d . . .
O6 O 0.36133(13) 0.21607(12) 1.05394(8) 0.0434(2) Uani 1 d . . .
O4 O 0.73344(13) 0.41942(11) 1.03399(8) 0.0437(2) Uani 1 d . . .
O3 O 0.73910(15) 0.17444(13) 1.00941(9) 0.0522(3) Uani 1 d . . .
C9 C 0.48353(19) 0.32145(16) 0.82934(11) 0.0382(3) Uani 1 d . . .
H9A H 0.3584 0.2886 0.7815 0.046 Uiso 1 calc . . R
H9B H 0.5194 0.4285 0.8775 0.046 Uiso 1 calc . . R
C7 C 0.5636(2) 0.16858(15) 0.69424(10) 0.0380(3) Uani 1 d . . .
H7 H 0.4342 0.1300 0.6482 0.046 Uiso 1 calc . . R
C11 C 0.66560(18) 0.26133(16) 0.98590(10) 0.0356(3) Uani 1 d . . .
C1 C 0.6979(2) 0.18326(16) 0.62409(11) 0.0411(3) Uani 1 d . . .
C8 C 0.4453(2) 0.04047(16) 0.81845(11) 0.0434(3) Uani 1 d . . .
H8A H 0.4582 -0.0329 0.8600 0.052 Uiso 1 calc . . R
H8B H 0.3174 -0.0063 0.7712 0.052 Uiso 1 calc . . R
C12 C 0.31255(19) 0.17965(17) 0.94631(11) 0.0417(3) Uani 1 d . . .
C6 C 0.6794(2) 0.25043(19) 0.53899(12) 0.0522(4) Uani 1 d . . .
O5 O 0.15421(15) 0.13210(18) 0.89003(10) 0.0713(4) Uani 1 d . . .
C2 C 0.8475(2) 0.13631(19) 0.64430(13) 0.0530(4) Uani 1 d . . .
H2 H 0.8625 0.0900 0.7006 0.064 Uiso 1 calc . . R
C13 C 0.9059(2) 0.48609(19) 1.12364(13) 0.0540(4) Uani 1 d . . .
H13A H 0.9607 0.6024 1.1397 0.065 Uiso 1 calc . . R
H13B H 0.9970 0.4459 1.1014 0.065 Uiso 1 calc . . R
C5 C 0.8056(3) 0.2708(2) 0.47540(15) 0.0735(6) Uani 1 d . . .
H5 H 0.7907 0.3156 0.4183 0.088 Uiso 1 calc . . R
C15 C 0.2060(2) 0.1813(2) 1.10553(14) 0.0623(5) Uani 1 d . . .
H15A H 0.1412 0.0659 1.0914 0.075 Uiso 1 calc . . R
H15B H 0.1156 0.2221 1.0759 0.075 Uiso 1 calc . . R
C16 C 0.2854(3) 0.2600(2) 1.22466(14) 0.0632(5) Uani 1 d . . .
H16A H 0.3437 0.3745 1.2381 0.095 Uiso 1 calc . . GR
H16B H 0.3782 0.2220 1.2528 0.095 Uiso 1 calc . . GR
H16C H 0.1858 0.2344 1.2604 0.095 Uiso 1 calc . . GR
C3 C 0.9744(3) 0.1579(2) 0.58139(17) 0.0726(6) Uani 1 d . . .
H3 H 1.0751 0.1271 0.5961 0.087 Uiso 1 calc . . R
C14 C 0.8679(3) 0.4424(2) 1.22419(13) 0.0655(5) Uani 1 d . . .
H14A H 0.8254 0.3279 1.2106 0.098 Uiso 1 calc . . GR
H14B H 0.7719 0.4760 1.2438 0.098 Uiso 1 calc . . GR
H14C H 0.9818 0.4951 1.2830 0.098 Uiso 1 calc . . GR
C4 C 0.9529(3) 0.2242(3) 0.49760(18) 0.0819(6) Uani 1 d . . .
H4 H 1.0387 0.2377 0.4554 0.098 Uiso 1 calc . . R
C10 C 0.48016(18) 0.20315(15) 0.89746(10) 0.0357(3) Uani 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'
Cl Cl 0.1484 0.1585 '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
C7 O2 C9 110.48(10) . .
C7 O1 C8 110.88(11) . .
C12 O6 C15 116.04(13) . .
C11 O4 C13 116.18(11) . .
O2 C9 H9A 109.7 . .
O2 C9 H9B 109.7 . .
O2 C9 C10 109.80(11) . .
H9A C9 H9B 108.2 . .
C10 C9 H9A 109.7 . .
C10 C9 H9B 109.7 . .
O2 C7 H7 109.7 . .
O2 C7 C1 107.47(11) . .
O1 C7 O2 110.52(13) . .
O1 C7 H7 109.7 . .
O1 C7 C1 109.82(12) . .
C1 C7 H7 109.7 . .
O4 C11 C10 111.81(11) . .
O3 C11 O4 124.49(14) . .
O3 C11 C10 123.70(13) . .
C6 C1 C7 120.27(14) . .
C6 C1 C2 118.13(15) . .
C2 C1 C7 121.55(14) . .
O1 C8 H8A 109.5 . .
O1 C8 H8B 109.5 . .
O1 C8 C10 110.85(11) . .
H8A C8 H8B 108.1 . .
C10 C8 H8A 109.5 . .
C10 C8 H8B 109.5 . .
O6 C12 C10 113.14(12) . .
O5 C12 O6 125.15(14) . .
O5 C12 C10 121.70(15) . .
C1 C6 Cl1 120.23(12) . .
C5 C6 Cl1 118.28(15) . .
C5 C6 C1 121.49(18) . .
C1 C2 H2 119.8 . .
C3 C2 C1 120.39(18) . .
C3 C2 H2 119.8 . .
O4 C13 H13A 109.3 . .
O4 C13 H13B 109.3 . .
O4 C13 C14 111.67(14) . .
H13A C13 H13B 107.9 . .
C14 C13 H13A 109.3 . .
C14 C13 H13B 109.3 . .
C6 C5 H5 120.4 . .
C4 C5 C6 119.2(2) . .
C4 C5 H5 120.4 . .
O6 C15 H15A 110.0 . .
O6 C15 H15B 110.0 . .
O6 C15 C16 108.33(15) . .
H15A C15 H15B 108.4 . .
C16 C15 H15A 110.0 . .
C16 C15 H15B 110.0 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C2 C3 H3 119.8 . .
C4 C3 C2 120.4(2) . .
C4 C3 H3 119.8 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C5 C4 H4 119.8 . .
C3 C4 C5 120.43(18) . .
C3 C4 H4 119.8 . .
C9 C10 C8 107.47(13) . .
C11 C10 C9 112.16(11) . .
C11 C10 C8 109.56(12) . .
C12 C10 C9 107.89(11) . .
C12 C10 C11 111.56(13) . .
C12 C10 C8 108.03(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C6 1.733(2) .
O2 C9 1.4218(19) .
O2 C7 1.418(2) .
O1 C7 1.4030(19) .
O1 C8 1.420(2) .
O6 C12 1.319(2) .
O6 C15 1.460(2) .
O4 C11 1.334(2) .
O4 C13 1.461(2) .
O3 C11 1.1967(19) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.539(2) .
C7 H7 0.9800 .
C7 C1 1.496(2) .
C11 C10 1.528(2) .
C1 C6 1.385(2) .
C1 C2 1.386(2) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 C10 1.540(2) .
C12 O5 1.198(2) .
C12 C10 1.523(2) .
C6 C5 1.382(3) .
C2 H2 0.9300 .
C2 C3 1.380(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C14 1.492(3) .
C5 H5 0.9300 .
C5 C4 1.371(3) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 C16 1.481(3) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C3 H3 0.9300 .
C3 C4 1.368(3) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C4 H4 0.9300 .
