#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/77/4507778.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_4507778
loop_
_publ_author_name
'Daszkiewicz, Marek'
_publ_section_title
;
 Elementary Graph-Set Descriptors in Crystal Structure Comparison of
 2-Methyl-4-Nitroanilinium Hexachloridostannate(IV), Bromide and Two
 Noncentrosymmertic Chlorides. X-Ray, Vibrational and Theoretical Studies
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2277
_journal_paper_doi               10.1021/cg301733r
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C7 H9 N2 O2, Cl'
_chemical_formula_sum            'C7 H9 Cl N2 O2'
_chemical_formula_weight         188.61
_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'
_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            4
_cell_length_a                   5.5223(4)
_cell_length_b                   7.7292(6)
_cell_length_c                   20.8328(16)
_cell_measurement_reflns_used    1835
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.81
_cell_volume                     889.21(12)
_computing_cell_refinement       'CrysAlis 1.171.32.6'
_computing_data_collection       'CrysAlis 1.171.32.6'
_computing_data_reduction        'CrysAlis 1.171.32.6'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2, 33.133pixel/mm'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'KUMA KM-4 with area CCD detector'
_diffrn_measurement_method       ω-scan
_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  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12732
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         2.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.391
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrysAlis 1.171.32.6'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 853 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.0283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0919
_reflns_number_gt                1835
_reflns_number_total             2118
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301733r_si_003.cif
_cod_data_source_block           m802
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4507778
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'
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
Cl Cl 0.50080(8) 0.14059(6) 0.07450(2) 0.04213(15) Uani 1 1 d .
C1 C 0.0301(3) 0.5056(2) 0.10999(8) 0.0326(4) Uani 1 1 d .
N1 N -0.0032(3) 0.34173(17) 0.07599(7) 0.0361(3) Uani 1 1 d .
H1A H 0.1177 0.2702 0.0857 0.054 Uiso 1 1 calc R
H1B H -0.0042 0.3610 0.0339 0.054 Uiso 1 1 calc R
H1C H -0.1432 0.2942 0.0877 0.054 Uiso 1 1 calc R
C2 C -0.1177(3) 0.6451(2) 0.09520(8) 0.0335(4) Uani 1 1 d .
C7 C -0.3186(4) 0.6342(3) 0.04623(10) 0.0456(5) Uani 1 1 d .
H7A H -0.4143 0.7378 0.0479 0.068 Uiso 1 1 calc R
H7B H -0.4192 0.5360 0.0555 0.068 Uiso 1 1 calc R
H7C H -0.2501 0.6219 0.0041 0.068 Uiso 1 1 calc R
C3 C -0.0744(3) 0.7989(3) 0.12746(8) 0.0386(4) Uani 1 1 d .
H3 H -0.1692 0.8957 0.1190 0.046 Uiso 1 1 calc R
C4 C 0.1092(4) 0.8080(2) 0.17193(9) 0.0383(4) Uani 1 1 d .
N2 N 0.1525(3) 0.9737(2) 0.20479(8) 0.0484(4) Uani 1 1 d .
O1 O 0.0396(3) 1.10054(17) 0.18744(7) 0.0598(4) Uani 1 1 d .
O2 O 0.2966(3) 0.9752(3) 0.24884(9) 0.0808(6) Uani 1 1 d .
C5 C 0.2542(3) 0.6690(3) 0.18683(9) 0.0424(4) Uani 1 1 d .
H5 H 0.3769 0.6787 0.2172 0.051 Uiso 1 1 calc R
C6 C 0.2125(3) 0.5149(3) 0.15542(9) 0.0399(4) Uani 1 1 d .
H6 H 0.3061 0.4180 0.1647 0.048 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
Cl 0.0345(2) 0.0399(2) 0.0519(3) -0.00089(18) -0.0012(2) 0.0041(2)
C1 0.0318(9) 0.0315(8) 0.0345(8) -0.0001(7) 0.0032(7) 0.0004(7)
N1 0.0326(7) 0.0317(7) 0.0440(7) -0.0015(6) -0.0032(8) 0.0027(7)
C2 0.0311(8) 0.0324(8) 0.0371(8) 0.0025(8) 0.0005(7) 0.0014(7)
C7 0.0395(10) 0.0451(10) 0.0523(11) -0.0018(10) -0.0097(9) 0.0078(9)
C3 0.0398(10) 0.0334(9) 0.0426(10) 0.0042(8) -0.0002(8) 0.0064(7)
C4 0.0452(10) 0.0321(8) 0.0376(9) -0.0032(7) 0.0015(8) -0.0018(7)
N2 0.0571(10) 0.0401(9) 0.0480(9) -0.0073(8) 0.0014(8) -0.0053(8)
O1 0.0857(12) 0.0338(7) 0.0600(8) -0.0053(6) 0.0042(9) 0.0048(7)
O2 0.0869(12) 0.0686(11) 0.0869(12) -0.0273(10) -0.0377(11) -0.0018(11)
C5 0.0405(10) 0.0448(11) 0.0420(10) -0.0016(9) -0.0091(8) 0.0019(8)
C6 0.0388(10) 0.0377(10) 0.0434(9) 0.0009(8) -0.0077(8) 0.0065(8)
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
C6 C1 C2 122.66(16)
C6 C1 N1 117.87(15)
C2 C1 N1 119.46(15)
C1 N1 H1A 109.5
C1 N1 H1B 109.5
H1A N1 H1B 109.5
C1 N1 H1C 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
C3 C2 C1 117.22(16)
C3 C2 C7 120.16(16)
C1 C2 C7 122.62(16)
C2 C7 H7A 109.5
C2 C7 H7B 109.5
H7A C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C4 C3 C2 119.86(16)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 122.77(17)
C3 C4 N2 118.56(17)
C5 C4 N2 118.68(17)
O2 N2 O1 123.50(18)
O2 N2 C4 117.82(18)
O1 N2 C4 118.66(17)
C4 C5 C6 118.07(16)
C4 C5 H5 121.0
C6 C5 H5 121.0
C5 C6 C1 119.42(17)
C5 C6 H6 120.3
C1 C6 H6 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.384(2)
C1 C2 1.387(2)
C1 N1 1.463(2)
N1 H1A 0.8900
N1 H1B 0.8900
N1 H1C 0.8900
C2 C3 1.386(3)
C2 C7 1.510(3)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C3 C4 1.375(3)
C3 H3 0.9300
C4 C5 1.376(3)
C4 N2 1.471(2)
N2 O2 1.215(2)
N2 O1 1.217(2)
C5 C6 1.379(3)
C5 H5 0.9300
C6 H6 0.9300
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
N1 H1A Cl 0.89 2.35 3.1880(15) 156.4 .
N1 H1A O1 0.89 2.53 2.987(2) 112.6 1_545
N1 H1B Cl 0.89 2.26 3.1382(15) 170.0 4_455
N1 H1C Cl 0.89 2.31 3.1498(15) 156.6 1_455
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
C6 C1 C2 C3 0.8(3)
N1 C1 C2 C3 -178.19(15)
C6 C1 C2 C7 -179.23(18)
N1 C1 C2 C7 1.7(3)
C1 C2 C3 C4 0.0(3)
C7 C2 C3 C4 -179.90(17)
C2 C3 C4 C5 -0.5(3)
C2 C3 C4 N2 179.27(16)
C3 C4 N2 O2 172.03(18)
C5 C4 N2 O2 -8.1(3)
C3 C4 N2 O1 -6.5(3)
C5 C4 N2 O1 173.28(17)
C3 C4 C5 C6 0.2(3)
N2 C4 C5 C6 -179.64(17)
C4 C5 C6 C1 0.7(3)
C2 C1 C6 C5 -1.2(3)
N1 C1 C6 C5 177.83(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146524
