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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/81/4508129.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_4508129
loop_
_publ_author_name
'Rybarczyk-Pirek, Agnieszka J.'
'Chęcińska, Lilianna'
'Małecka, Magdalena'
'Wojtulewski, Sławomir'
_publ_section_title
;
 Intermolecular Interactions of Trichloromethyl Group in the Crystal
 State, the Case of 2-Trichloromethyl-3H-4-quinazoline Polymorphs and
 1-Methyl-2-trichloroacetylpyrrole--Hirshfeld Surface Analysis of Chlorine
 Halogen Bonding
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3913
_journal_paper_doi               10.1021/cg400584w
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C9 H5 Cl3 N2 O'
_chemical_formula_weight         263.50
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.9421(12)
_cell_length_b                   17.846(4)
_cell_length_c                   19.075(4)
_cell_measurement_reflns_used    3971
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.8786
_cell_measurement_theta_min      3.1200
_cell_volume                     2022.8(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4052
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1780
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.875
_exptl_absorpt_correction_T_max  0.9176
_exptl_absorpt_correction_T_min  0.8444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0294
_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)+(0.0366P)²+1.2112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                1566
_reflns_number_total             1780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400584w_si_002.cif
_cod_data_source_block           1-orth
_cod_original_sg_symbol_H-M      'P bca'
_cod_database_code               4508129
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
H3 H 0.920(5) 0.9374(14) 0.4549(13) 0.030(7) Uiso 1 1 d .
Cl3 Cl 1.10761(9) 0.82423(3) 0.38372(3) 0.01683(16) Uani 1 1 d .
Cl2 Cl 0.70638(9) 0.76974(3) 0.45407(3) 0.01759(16) Uani 1 1 d .
Cl1 Cl 0.72821(9) 0.77304(3) 0.30326(3) 0.01704(16) Uani 1 1 d .
C21 C 0.8100(3) 0.82048(12) 0.38024(10) 0.0115(5) Uani 1 1 d .
O4 O 0.8060(3) 1.06307(8) 0.48288(7) 0.0193(4) Uani 1 1 d .
C2 C 0.7086(3) 0.89931(12) 0.38298(10) 0.0114(5) Uani 1 1 d .
C4 C 0.7198(4) 1.02002(12) 0.44012(10) 0.0139(5) Uani 1 1 d .
N3 N 0.8035(3) 0.94831(10) 0.43052(9) 0.0123(4) Uani 1 1 d .
C5 C 0.4217(4) 1.10861(13) 0.40114(11) 0.0174(5) Uani 1 1 d .
H5 H 0.4799 1.1450 0.4310 0.021 Uiso 1 1 calc R
C10 C 0.5247(3) 1.03847(12) 0.39674(10) 0.0121(5) Uani 1 1 d .
N1 N 0.5373(3) 0.91308(10) 0.34444(8) 0.0116(4) Uani 1 1 d .
C9 C 0.4381(3) 0.98351(12) 0.35125(10) 0.0111(4) Uani 1 1 d .
C6 C 0.2338(4) 1.12405(14) 0.36125(12) 0.0190(5) Uani 1 1 d .
H6 H 0.1653 1.1708 0.3642 0.023 Uiso 1 1 calc R
C8 C 0.2469(4) 1.00001(13) 0.31102(10) 0.0143(5) Uani 1 1 d .
H8 H 0.1880 0.9641 0.2808 0.017 Uiso 1 1 calc R
C7 C 0.1461(4) 1.06934(13) 0.31627(11) 0.0182(5) Uani 1 1 d .
H7 H 0.0188 1.0799 0.2897 0.022 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl3 0.0123(3) 0.0146(3) 0.0235(3) -0.0027(2) -0.0004(2) -0.0002(2)
Cl2 0.0248(3) 0.0138(3) 0.0142(3) 0.0043(2) 0.0058(2) 0.0011(2)
Cl1 0.0219(3) 0.0158(3) 0.0134(3) -0.0054(2) -0.0034(2) 0.0013(2)
C21 0.0121(11) 0.0124(12) 0.0100(10) 0.0002(8) 0.0000(8) -0.0029(9)
O4 0.0265(9) 0.0124(9) 0.0190(8) -0.0047(7) -0.0091(7) 0.0009(7)
C2 0.0147(11) 0.0116(12) 0.0079(9) 0.0001(8) 0.0026(8) -0.0031(9)
C4 0.0176(11) 0.0132(13) 0.0108(10) -0.0001(9) 0.0017(8) -0.0016(9)
N3 0.0155(9) 0.0089(10) 0.0124(9) -0.0003(7) -0.0039(7) 0.0008(8)
C5 0.0200(11) 0.0140(13) 0.0181(11) -0.0048(9) 0.0002(9) -0.0021(9)
C10 0.0141(11) 0.0115(12) 0.0106(9) 0.0011(8) 0.0009(8) -0.0011(9)
N1 0.0139(9) 0.0100(10) 0.0108(8) 0.0002(7) 0.0007(7) -0.0013(7)
C9 0.0155(10) 0.0086(12) 0.0091(9) 0.0009(8) 0.0033(8) -0.0018(9)
C6 0.0206(12) 0.0122(12) 0.0240(11) -0.0002(10) -0.0011(10) 0.0035(10)
C8 0.0178(11) 0.0123(12) 0.0127(10) -0.0002(9) -0.0012(8) -0.0024(9)
C7 0.0163(11) 0.0208(14) 0.0175(11) 0.0029(10) -0.0025(9) 0.0014(10)
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
C2 C21 Cl1 111.16(14)
C2 C21 Cl3 110.92(15)
Cl1 C21 Cl3 108.94(11)
C2 C21 Cl2 107.66(13)
Cl1 C21 Cl2 108.57(12)
Cl3 C21 Cl2 109.54(11)
N1 C2 N3 125.5(2)
N1 C2 C21 118.04(18)
N3 C2 C21 116.33(17)
O4 C4 N3 120.96(19)
O4 C4 C10 124.3(2)
N3 C4 C10 114.70(18)
C2 N3 C4 121.71(18)
C6 C5 C10 120.1(2)
C5 C10 C9 120.12(19)
C5 C10 C4 121.04(19)
C9 C10 C4 118.82(19)
C2 N1 C9 117.13(18)
N1 C9 C8 118.74(18)
N1 C9 C10 122.09(18)
C8 C9 C10 119.2(2)
C5 C6 C7 120.0(2)
C7 C8 C9 120.1(2)
C8 C7 C6 120.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl3 C21 1.771(2)
Cl2 C21 1.784(2)
Cl1 C21 1.763(2)
C21 C2 1.531(3)
O4 C4 1.232(2)
C2 N1 1.280(3)
C2 N3 1.380(3)
C4 N3 1.385(3)
C4 C10 1.462(3)
C5 C6 1.379(3)
C5 C10 1.396(3)
C10 C9 1.407(3)
N1 C9 1.394(3)
C9 C8 1.402(3)
C6 C7 1.400(3)
C8 C7 1.378(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 135403370
