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#$Date: 2023-03-15 11:46:19 +0200 (Wed, 15 Mar 2023) $
#$Revision: 281885 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106934.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_8106934
loop_
_publ_author_name
'Su, Hongliang'
'Guo, Xiaoxiong'
'Zhou, Lunan'
'Du, Zhenting'
_publ_section_title
;
 Crystal structure of 1-(2-chlorophenyl)-2-(2-nitrophenyl)ethan-1-ol,
 C14H12ClNO3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              545
_journal_page_last               546
_journal_paper_doi               10.1515/ncrs-2015-0180
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C14 H12 Cl N O3'
_chemical_formula_sum            'C14 H12 Cl N O3'
_chemical_formula_weight         277.70
_chemical_melting_point          364
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 115.2310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2044(6)
_cell_length_b                   24.975(2)
_cell_length_c                   7.8562(8)
_cell_measurement_reflns_used    1623
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.566
_cell_measurement_theta_min      2.231
_cell_volume                     1278.7(2)
_computing_cell_refinement       'Bruker SMART (Bruker, 2005)'
_computing_data_collection       'Bruker SMART (Bruker, 2005)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2005)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6343
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_correction_T_min  0.8889
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0538
_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)+(0.0416P)²+1.1138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                1397
_reflns_number_total             2262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0180_suppl.cif
_cod_data_source_block           120324d
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8106934
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.3141(2) 0.53099(4) 0.07040(17) 0.0812(4) Uani 1 1 d . . .
N1 N 0.9623(5) 0.72283(15) 0.4125(5) 0.0607(9) Uani 1 1 d . . .
O1 O 0.5279(4) 0.69146(8) 0.2987(3) 0.0540(7) Uani 1 1 d . . .
H1 H 0.4987 0.7098 0.2043 0.081 Uiso 1 1 calc R . .
O2 O 0.9986(5) 0.69949(14) 0.5573(4) 0.0946(11) Uani 1 1 d . . .
O3 O 0.9469(5) 0.77175(13) 0.3968(5) 0.0877(10) Uani 1 1 d . . .
C1 C 0.5205(5) 0.63661(12) 0.2504(5) 0.0414(8) Uani 1 1 d . . .
H1A H 0.4446 0.6327 0.1138 0.050 Uiso 1 1 calc R . .
C2 C 0.7394(5) 0.61594(13) 0.3118(5) 0.0495(9) Uani 1 1 d . . .
H2A H 0.8175 0.6224 0.4454 0.059 Uiso 1 1 calc R . .
H2B H 0.7357 0.5776 0.2912 0.059 Uiso 1 1 calc R . .
C3 C 0.8453(5) 0.64267(12) 0.2053(4) 0.0378(7) Uani 1 1 d . . .
C4 C 0.9398(5) 0.69219(12) 0.2445(4) 0.0391(7) Uani 1 1 d . . .
C5 C 1.0212(5) 0.71602(13) 0.1337(5) 0.0484(9) Uani 1 1 d . . .
H5 H 1.0833 0.7495 0.1655 0.058 Uiso 1 1 calc R . .
C6 C 1.0099(6) 0.69016(16) -0.0232(5) 0.0556(10) Uani 1 1 d . . .
H6 H 1.0650 0.7057 -0.0991 0.067 Uiso 1 1 calc R . .
C7 C 0.9180(6) 0.64164(16) -0.0676(5) 0.0580(10) Uani 1 1 d . . .
H7 H 0.9113 0.6238 -0.1739 0.070 Uiso 1 1 calc R . .
C8 C 0.8344(5) 0.61844(13) 0.0422(5) 0.0512(9) Uani 1 1 d . . .
H8 H 0.7685 0.5856 0.0063 0.061 Uiso 1 1 calc R . .
C9 C 0.4142(5) 0.60509(12) 0.3464(5) 0.0415(8) Uani 1 1 d . . .
C10 C 0.3236(5) 0.55586(13) 0.2804(5) 0.0484(9) Uani 1 1 d . . .
C11 C 0.2347(6) 0.52593(14) 0.3733(6) 0.0617(10) Uani 1 1 d . . .
H11 H 0.1723 0.4934 0.3240 0.074 Uiso 1 1 calc R . .
C12 C 0.2391(6) 0.54463(16) 0.5387(6) 0.0634(11) Uani 1 1 d . . .
H12 H 0.1826 0.5243 0.6039 0.076 Uiso 1 1 calc R . .
C13 C 0.3260(6) 0.59295(17) 0.6082(5) 0.0624(11) Uani 1 1 d . . .
H13 H 0.3259 0.6059 0.7192 0.075 Uiso 1 1 calc R . .
C14 C 0.4144(5) 0.62285(14) 0.5137(5) 0.0512(9) Uani 1 1 d . . .
H14 H 0.4753 0.6555 0.5636 0.061 Uiso 1 1 calc R . .
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
O2 N1 O3 123.4(3) . .
O2 N1 C4 119.4(3) . .
O3 N1 C4 117.1(3) . .
C1 O1 H1 109.5 . .
O1 C1 C9 109.9(2) . .
O1 C1 C2 109.0(3) . .
C9 C1 C2 110.0(2) . .
O1 C1 H1A 109.3 . .
C9 C1 H1A 109.3 . .
C2 C1 H1A 109.3 . .
C3 C2 C1 111.9(3) . .
C3 C2 H2A 109.2 . .
C1 C2 H2A 109.2 . .
C3 C2 H2B 109.2 . .
C1 C2 H2B 109.2 . .
H2A C2 H2B 107.9 . .
C4 C3 C8 115.1(3) . .
C4 C3 C2 126.2(3) . .
C8 C3 C2 118.5(3) . .
C5 C4 C3 123.3(3) . .
C5 C4 N1 115.4(3) . .
C3 C4 N1 121.3(3) . .
C6 C5 C4 119.4(3) . .
C6 C5 H5 120.3 . .
C4 C5 H5 120.3 . .
C7 C6 C5 119.4(3) . .
C7 C6 H6 120.3 . .
C5 C6 H6 120.3 . .
C6 C7 C8 120.9(3) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C7 C8 C3 121.9(3) . .
C7 C8 H8 119.0 . .
C3 C8 H8 119.0 . .
C10 C9 C14 116.7(3) . .
C10 C9 C1 122.4(3) . .
C14 C9 C1 120.8(3) . .
C11 C10 C9 122.3(3) . .
C11 C10 Cl1 118.0(3) . .
C9 C10 Cl1 119.6(3) . .
C12 C11 C10 119.3(4) . .
C12 C11 H11 120.3 . .
C10 C11 H11 120.3 . .
C13 C12 C11 120.2(3) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C12 C13 C14 120.1(4) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
C13 C14 C9 121.4(3) . .
C13 C14 H14 119.3 . .
C9 C14 H14 119.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C10 1.737(4) .
N1 O2 1.203(4) .
N1 O3 1.228(4) .
N1 C4 1.474(4) .
O1 C1 1.416(4) .
O1 H1 0.8200 .
C1 C9 1.506(4) .
C1 C2 1.529(4) .
C1 H1A 0.9800 .
C2 C3 1.507(4) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.382(4) .
C3 C8 1.388(4) .
C4 C5 1.375(4) .
C5 C6 1.363(5) .
C5 H5 0.9300 .
C6 C7 1.354(5) .
C6 H6 0.9300 .
C7 C8 1.373(5) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C9 C10 1.385(4) .
C9 C14 1.387(4) .
C10 C11 1.378(5) .
C11 C12 1.369(5) .
C11 H11 0.9300 .
C12 C13 1.362(5) .
C12 H12 0.9300 .
C13 C14 1.385(5) .
C13 H13 0.9300 .
C14 H14 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O1 . H1 . O2B 4_464 149 0.82 2.54 3.274(4) yes
O1 . H1 . O3B 4_464 156 0.82 2.33 3.096(4) yes
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
O1 C1 C2 C3 -64.9(4) . . . .
C9 C1 C2 C3 174.5(3) . . . .
C1 C2 C3 C4 81.7(4) . . . .
C1 C2 C3 C8 -92.3(4) . . . .
C8 C3 C4 C5 -1.1(5) . . . .
C2 C3 C4 C5 -175.2(3) . . . .
C8 C3 C4 N1 179.8(3) . . . .
C2 C3 C4 N1 5.7(5) . . . .
O2 N1 C4 C5 -141.7(3) . . . .
O3 N1 C4 C5 36.7(4) . . . .
O2 N1 C4 C3 37.4(5) . . . .
O3 N1 C4 C3 -144.1(3) . . . .
C3 C4 C5 C6 -0.1(5) . . . .
N1 C4 C5 C6 179.0(3) . . . .
C4 C5 C6 C7 0.3(5) . . . .
C5 C6 C7 C8 0.6(6) . . . .
C6 C7 C8 C3 -1.9(6) . . . .
C4 C3 C8 C7 2.0(5) . . . .
C2 C3 C8 C7 176.7(3) . . . .
O1 C1 C9 C10 157.7(3) . . . .
C2 C1 C9 C10 -82.3(4) . . . .
O1 C1 C9 C14 -26.5(4) . . . .
C2 C1 C9 C14 93.5(4) . . . .
C14 C9 C10 C11 1.0(5) . . . .
C1 C9 C10 C11 176.9(3) . . . .
C14 C9 C10 Cl1 179.3(2) . . . .
C1 C9 C10 Cl1 -4.8(4) . . . .
C9 C10 C11 C12 -1.4(6) . . . .
Cl1 C10 C11 C12 -179.8(3) . . . .
C10 C11 C12 C13 1.7(6) . . . .
C11 C12 C13 C14 -1.5(6) . . . .
C12 C13 C14 C9 1.0(6) . . . .
C10 C9 C14 C13 -0.8(5) . . . .
C1 C9 C14 C13 -176.8(3) . . . .
