#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/33/2003375.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2003375
loop_
_publ_author_name
'Clegg, W.'
'Pogue, H. J.'
'Lowe, M. P.'
'Butterfield, I. M.'
'Jackson, R. F. W.'
_publ_section_title
;
 p-Nitrobenzyl Trichloroacetimidate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              741
_journal_page_last               743
_journal_paper_doi               10.1107/S0108270194010838
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C9 H7 Cl3 N2 O3'
_chemical_formula_weight         297.52
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0278(3)
_cell_length_b                   10.8550(5)
_cell_length_c                   15.6339(7)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12.17
_cell_measurement_theta_min      11.57
_cell_volume                     1192.66(9)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1988)'
_computing_data_reduction        'local programs'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  'SHELXL-93 and local programs'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1994)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measurement_device       'Stoe Siemens diffractometer'
_diffrn_measurement_method
'ω/θ scans with on-line profile fitting (Clegg,'
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3906
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_refine_diff_density_max         .170
_refine_diff_density_min         -.191
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_coef       0.0170(16)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1994)'
_refine_ls_goodness_of_fit_all   1.041
_refine_ls_goodness_of_fit_obs   1.031
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_restrained_S_obs      1.031
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_obs          0.0228
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
; calc w = 1/[\s^2^(F~o~^2^) + (0.0320P)^2^ + 0.2219P]
  where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.0623
_refine_ls_wR_factor_obs         0.0597
_reflns_number_observed          1992
_reflns_number_total             2098
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            mu1141.cif
_cod_data_source_block           rfwj10
_cod_original_sg_symbol_H-M      'P 212121'
_cod_database_code               2003375
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_type_symbol
Cl1 1 0.99911(9) 0.31196(5) 0.57317(4) 0.0624(2) Uani d Cl
Cl2 1 1.22786(7) 0.48565(5) 0.47767(4) 0.0581(2) Uani d Cl
Cl3 1 0.96329(10) 0.32843(6) 0.39029(4) 0.0684(2) Uani d Cl
N1 1 0.7031(3) 0.5310(2) 0.45281(13) 0.0556(5) Uani d N
H1 1 0.6964(35) 0.4821(23) 0.4069(16) 0.062(7) Uiso d H
N2 1 0.0801(3) 0.5283(2) 0.76184(11) 0.0533(4) Uani d N
O1 1 0.8898(2) 0.57606(13) 0.56784(9) 0.0480(3) Uani d O
O2 1 0.0589(3) 0.4194(2) 0.77976(12) 0.0759(5) Uani d O
O3 1 -0.0354(3) 0.6082(2) 0.77958(12) 0.0718(5) Uani d O
C1 1 1.0016(3) 0.4134(2) 0.48483(12) 0.0438(4) Uani d C
C2 1 0.8467(3) 0.5116(2) 0.49717(11) 0.0410(4) Uani d C
C3 1 0.7617(3) 0.6749(2) 0.5893(2) 0.0516(5) Uani d C
H3A 1 0.7269(32) 0.7149(22) 0.5428(15) 0.053(6) Uiso d H
H3B 1 0.8422(37) 0.7282(24) 0.6277(16) 0.061(7) Uiso d H
C4 1 0.5844(3) 0.6314(2) 0.63425(12) 0.0416(4) Uani d C
C5 1 0.4401(3) 0.7166(2) 0.64829(14) 0.0476(5) Uani d C
H5 1 0.4578(36) 0.7851(26) 0.6268(17) 0.060(7) Uiso d H
C6 1 0.2749(3) 0.6847(2) 0.69002(13) 0.0478(5) Uani d C
H6 1 0.1889(38) 0.7404(23) 0.6991(16) 0.060(7) Uiso d H
C7 1 0.2555(3) 0.5647(2) 0.71759(11) 0.0429(4) Uani d C
C8 1 0.3950(3) 0.4779(2) 0.70470(13) 0.0497(5) Uani d C
H8 1 0.3715(37) 0.3999(24) 0.7255(15) 0.057(6) Uiso d H
C9 1 0.5609(3) 0.5125(2) 0.66406(14) 0.0503(5) Uani d C
H9 1 0.6596(40) 0.4598(26) 0.6544(16) 0.067(8) Uiso d H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' .0033 .0016
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' .0000 .0000
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' .0061 .0033
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' .0106 .0060
Cl Cl 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' .1484 .158
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 H1 113.0(16) yes
O3 N2 O2 123.6(2) yes
O3 N2 C7 118.3(2) yes
O2 N2 C7 118.0(2) yes
C2 O1 C3 116.0(2) yes
C2 C1 Cl3 111.11(13) yes
C2 C1 Cl1 109.10(13) yes
Cl3 C1 Cl1 109.16(10) yes
C2 C1 Cl2 109.63(12) yes
Cl3 C1 Cl2 108.35(10) yes
Cl1 C1 Cl2 109.47(11) yes
N1 C2 O1 123.7(2) yes
N1 C2 C1 128.6(2) yes
O1 C2 C1 107.77(15) yes
O1 C3 C4 113.1(2) yes
O1 C3 H3A 110.5(15) no
C4 C3 H3A 108.0(16) no
O1 C3 H3B 102.5(15) no
C4 C3 H3B 111.5(15) no
H3A C3 H3B 111.(2) no
C9 C4 C5 118.8(2) yes
C9 C4 C3 123.3(2) yes
C5 C4 C3 117.9(2) yes
C6 C5 C4 121.5(2) yes
C6 C5 H5 123.1(18) no
C4 C5 H5 115.2(18) no
C5 C6 C7 118.0(2) yes
C5 C6 H6 119.3(17) no
C7 C6 H6 122.6(17) no
C8 C7 C6 122.1(2) yes
C8 C7 N2 118.9(2) yes
C6 C7 N2 119.0(2) yes
C7 C8 C9 118.9(2) yes
C7 C8 H8 116.7(16) no
C9 C8 H8 124.3(16) no
C8 C9 C4 120.7(2) yes
C8 C9 H9 123.3(17) no
C4 C9 H9 116.0(17) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.766(2) yes
Cl2 C1 1.777(2) yes
Cl3 C1 1.763(2) yes
N1 C2 1.242(3) yes
N1 H1 0.89(3) yes
N2 O3 1.220(3) yes
N2 O2 1.225(3) yes
N2 C7 1.468(3) yes
O1 C2 1.343(2) yes
O1 C3 1.440(2) yes
C1 C2 1.536(3) yes
C3 C4 1.506(3) yes
C3 H3A 0.88(2) no
C3 H3B 1.01(3) no
C4 C9 1.382(3) yes
C4 C5 1.390(3) yes
C5 C6 1.377(3) yes
C5 H5 0.82(3) no
C6 C7 1.378(3) yes
C6 H6 0.87(3) no
C7 C8 1.375(3) yes
C8 C9 1.379(3) yes
C8 H8 0.92(3) no
C9 H9 0.91(3) no
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_publ_flag
N1 C2 C1 Cl3 3.8(3) yes
O2 N2 C7 C6 174.3(2) yes
O3 N2 C7 C6 -6.5(3) yes
O2 N2 C7 C8 -5.5(3) yes
O3 N2 C7 C8 173.7(2) yes
Cl3 C1 C2 N1 3.8(3) yes
C1 C2 N1 H1 -3.1(17) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11851302
