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#$Date: 2023-01-13 10:29:08 +0200 (Fri, 13 Jan 2023) $
#$Revision: 280325 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106459.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_8106459
loop_
_publ_author_name
'Qi, Bo-Shu'
'Sun, Xiao-Nan'
'Yang, Huan-Huan'
'Fu, Ying'
'Ye, Fei'
_publ_section_title
;
 Crystal structure of 2-dichloromethyl-2-p-nitrophenyl-1,3-dioxolane,
 C10H9Cl2NO4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              137
_journal_page_last               138
_journal_paper_doi               10.1515/ncrs-2016-0192
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety
;
 'C10 H9 Cl2 N2 O4'  
;
_chemical_formula_sum            'C10 H9 Cl2 N2 O4'
_chemical_formula_weight         292.095
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.151(2)
_cell_length_b                   7.0923(14)
_cell_length_c                   29.243(6)
_cell_measurement_reflns_used    14097
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.33
_cell_volume                     2312.7(8)
_computing_cell_refinement       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_collection       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            20774
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  0.9506
_exptl_absorpt_correction_T_min  0.8886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
ABSCOR (Higashi, 1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.056
_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     154
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0459
_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)+(0.0739P)²+0.2750P] where P=(Fo²+2Fc²)/3' 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1348
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1765
_reflns_number_total             2641
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0192_suppl.cif
_cod_data_source_block           1
_cod_database_code               8106459
_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.
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C1 C 0.97875(19) 0.9758(3) 0.38665(7) 0.0432(5) Uani 1 1 d . . .
C2 C 1.0763(2) 1.0560(3) 0.40896(7) 0.0487(5) Uani 1 1 d . . .
H2 H 1.1532 1.0366 0.3976 0.058 Uiso 1 1 calc R . .
C3 C 1.0604(2) 1.1636(3) 0.44748(7) 0.0498(5) Uani 1 1 d . . .
H3 H 1.1258 1.2175 0.4623 0.060 Uiso 1 1 calc R . .
C4 C 0.9462(2) 1.1905(3) 0.46385(7) 0.0454(5) Uani 1 1 d . . .
C5 C 0.8466(2) 1.1170(3) 0.44197(8) 0.0519(6) Uani 1 1 d . . .
H5 H 0.7698 1.1396 0.4531 0.062 Uiso 1 1 calc R . .
C6 C 0.8642(2) 1.0092(4) 0.40324(8) 0.0499(5) Uani 1 1 d . . .
H6 H 0.7983 0.9583 0.3881 0.060 Uiso 1 1 calc R . .
C7 C 0.9980(2) 0.8459(4) 0.34583(8) 0.0494(6) Uani 1 1 d . . .
C8 C 1.0891(3) 0.5609(4) 0.35709(12) 0.0732(8) Uani 1 1 d . . .
H8A H 1.1091 0.5294 0.3885 0.088 Uiso 1 1 calc R . .
H8B H 1.1373 0.4835 0.3368 0.088 Uiso 1 1 calc R . .
C9 C 0.9622(3) 0.5297(4) 0.34866(13) 0.0836(10) Uani 1 1 d . . .
H9A H 0.9513 0.4576 0.3208 0.100 Uiso 1 1 calc R . .
H9B H 0.9268 0.4600 0.3738 0.100 Uiso 1 1 calc R . .
C10 C 0.9963(2) 0.9450(4) 0.29915(8) 0.0574(6) Uani 1 1 d . . .
H10 H 1.0068 0.8482 0.2756 0.069 Uiso 1 1 calc R . .
Cl1 Cl 1.11593(7) 1.10883(11) 0.29357(2) 0.0677(2) Uani 1 1 d . . .
Cl2 Cl 0.85863(7) 1.05993(13) 0.28860(3) 0.0794(3) Uani 1 1 d . . .
N1 N 0.93076(19) 1.2955(3) 0.50668(6) 0.0530(5) Uani 1 1 d . . .
O1 O 1.11029(15) 0.7530(2) 0.34872(6) 0.0585(5) Uani 1 1 d . . .
O2 O 0.90781(16) 0.7057(2) 0.34454(7) 0.0655(5) Uani 1 1 d . . .
O3 O 0.82968(18) 1.3431(3) 0.51767(7) 0.0826(6) Uani 1 1 d . . .
O4 O 1.01977(17) 1.3326(3) 0.52943(6) 0.0620(5) 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'
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
C6 C1 C2 119.1(2) . .
C6 C1 C7 120.5(2) . .
C2 C1 C7 120.3(2) . .
C3 C2 C1 120.8(2) . .
C3 C2 H2 119.6 . .
C1 C2 H2 119.6 . .
C2 C3 C4 118.9(2) . .
C2 C3 H3 120.6 . .
C4 C3 H3 120.6 . .
C3 C4 C5 122.0(2) . .
C3 C4 N1 118.4(2) . .
C5 C4 N1 119.5(2) . .
C6 C5 C4 118.4(2) . .
C6 C5 H5 120.8 . .
C4 C5 H5 120.8 . .
C5 C6 C1 120.8(2) . .
C5 C6 H6 119.6 . .
C1 C6 H6 119.6 . .
O2 C7 O1 107.63(19) . .
O2 C7 C1 110.21(19) . .
O1 C7 C1 111.07(18) . .
O2 C7 C10 106.78(19) . .
O1 C7 C10 106.07(19) . .
C1 C7 C10 114.7(2) . .
O1 C8 C9 106.4(2) . .
O1 C8 H8A 110.5 . .
C9 C8 H8A 110.5 . .
O1 C8 H8B 110.5 . .
C9 C8 H8B 110.5 . .
H8A C8 H8B 108.6 . .
O2 C9 C8 107.6(2) . .
O2 C9 H9A 110.2 . .
C8 C9 H9A 110.2 . .
O2 C9 H9B 110.2 . .
C8 C9 H9B 110.2 . .
H9A C9 H9B 108.5 . .
C7 C10 Cl2 112.18(17) . .
C7 C10 Cl1 111.81(17) . .
Cl2 C10 Cl1 109.56(15) . .
C7 C10 H10 107.7 . .
Cl2 C10 H10 107.7 . .
Cl1 C10 H10 107.7 . .
O3 N1 O4 123.2(2) . .
O3 N1 C4 118.3(2) . .
O4 N1 C4 118.6(2) . .
C8 O1 C7 108.2(2) . .
C9 O2 C7 108.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.387(3) .
C1 C2 1.390(3) .
C1 C7 1.523(3) .
C2 C3 1.372(3) .
C2 H2 0.9300 .
C3 C4 1.374(3) .
C3 H3 0.9300 .
C4 C5 1.383(3) .
C4 N1 1.467(3) .
C5 C6 1.380(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 O2 1.415(3) .
C7 O1 1.417(3) .
C7 C10 1.536(3) .
C8 O1 1.404(3) .
C8 C9 1.453(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 O2 1.393(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 Cl2 1.765(3) .
C10 Cl1 1.777(3) .
C10 H10 0.9800 .
N1 O3 1.220(3) .
N1 O4 1.223(3) .
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
C3 H3 O3 0.93 2.39 3.172(3) 142.0 4_576
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
C6 C1 C2 C3 1.4(3) . . . .
C7 C1 C2 C3 -175.9(2) . . . .
C1 C2 C3 C4 0.2(3) . . . .
C2 C3 C4 C5 -1.9(3) . . . .
C2 C3 C4 N1 176.1(2) . . . .
C3 C4 C5 C6 1.8(4) . . . .
N1 C4 C5 C6 -176.2(2) . . . .
C4 C5 C6 C1 -0.1(4) . . . .
C2 C1 C6 C5 -1.4(4) . . . .
C7 C1 C6 C5 175.8(2) . . . .
C6 C1 C7 O2 -29.9(3) . . . .
C2 C1 C7 O2 147.4(2) . . . .
C6 C1 C7 O1 -149.1(2) . . . .
C2 C1 C7 O1 28.2(3) . . . .
C6 C1 C7 C10 90.7(3) . . . .
C2 C1 C7 C10 -92.1(3) . . . .
O1 C8 C9 O2 -11.4(4) . . . .
O2 C7 C10 Cl2 62.6(2) . . . .
O1 C7 C10 Cl2 177.21(16) . . . .
C1 C7 C10 Cl2 -59.8(2) . . . .
O2 C7 C10 Cl1 -173.83(16) . . . .
O1 C7 C10 Cl1 -59.2(2) . . . .
C1 C7 C10 Cl1 63.8(2) . . . .
C3 C4 N1 O3 169.4(2) . . . .
C5 C4 N1 O3 -12.5(3) . . . .
C3 C4 N1 O4 -9.9(3) . . . .
C5 C4 N1 O4 168.2(2) . . . .
C9 C8 O1 C7 13.1(3) . . . .
O2 C7 O1 C8 -10.0(3) . . . .
C1 C7 O1 C8 110.7(2) . . . .
C10 C7 O1 C8 -124.0(2) . . . .
C8 C9 O2 C7 5.4(3) . . . .
O1 C7 O2 C9 2.7(3) . . . .
C1 C7 O2 C9 -118.6(2) . . . .
C10 C7 O2 C9 116.2(2) . . . .
