#------------------------------------------------------------------------------
#$Date: 2024-02-05 14:06:27 +0200 (Mon, 05 Feb 2024) $
#$Revision: 289688 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/29/2022986.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_2022986
loop_
_publ_author_name
'Uppu, Rao M.'
'Babu, Sainath'
'Fronczek, Frank R.'
_publ_section_title
;
 Temperature-dependent solid-state phase transition with twinning in the
 crystal structure of 4-meth-oxy-anilinium chloride.
;
_journal_coeditor_code           HB8089
_journal_issue                   'Pt 1'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              58
_journal_page_last               61
_journal_paper_doi               10.1107/S2056989023010812
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C7 H10 N O+, Cl-'
_chemical_formula_moiety         'C7 H10 N O, Cl'
_chemical_formula_sum            'C7 H10 Cl N O'
_chemical_formula_weight         159.61
_chemical_name_systematic
;
4-Methoxyanilinium chloride
;
_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
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.8689(4)
_cell_length_b                   8.4361(3)
_cell_length_c                   21.7319(9)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    250.0(5)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.75
_cell_volume                     1625.96(12)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/1 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015)
;
_diffrn_ambient_temperature      250.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            73425
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.580
_diffrn_reflns_theta_min         1.874
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       'lath fragment'
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.215
_refine_ls_extinction_coef       0.0070(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2017/1 (Sheldrick 2015)
;
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0348P)²+0.6343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                2019
_reflns_number_total             2717
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8089sup1.cif
_cod_data_source_block           I_250K
_cod_depositor_comments
'Adding full bibliography for 2022986--2022987.cif.'
_cod_database_code               2022986
_cod_database_fobs_code          2022986
_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.
;
_shelx_estimated_absorpt_t_min   0.875
_shelx_estimated_absorpt_t_max   0.942
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.74847(4) 0.51434(4) 0.52125(2) 0.03992(12) Uani d 1 . .
O O1 0.65326(14) 0.80202(15) 0.20491(5) 0.0514(3) Uani d 1 . .
N N1 0.52441(19) 0.75043(18) 0.45535(6) 0.0547(4) Uani d 1 . .
H H1N 0.584233 0.818422 0.475901 0.082 Uiso calc 0.5 . .
H H2N 0.427238 0.776832 0.461481 0.082 Uiso calc 0.5 . .
H H3N 0.540574 0.651270 0.469129 0.082 Uiso calc 0.5 . .
H H4N 0.450464 0.679260 0.461773 0.082 Uiso calc 0.5 . .
H H5N 0.607459 0.720851 0.476193 0.082 Uiso calc 0.5 . .
H H6N 0.494123 0.846412 0.468545 0.082 Uiso calc 0.5 . .
C C1 0.55894(17) 0.75820(17) 0.38936(7) 0.0388(3) Uani d 1 . .
C C2 0.48090(17) 0.66401(19) 0.34891(7) 0.0427(3) Uani d 1 . .
H H2 0.408003 0.592462 0.363560 0.051 Uiso calc 1 . .
C C3 0.51002(17) 0.67476(19) 0.28628(7) 0.0406(3) Uani d 1 . .
H H3 0.456473 0.610978 0.258349 0.049 Uiso calc 1 . .
C C4 0.61767(17) 0.77925(17) 0.26521(6) 0.0371(3) Uani d 1 . .
C C5 0.6976(2) 0.8710(2) 0.30673(8) 0.0481(4) Uani d 1 . .
H H5 0.772702 0.940379 0.292416 0.058 Uiso calc 1 . .
C C6 0.6681(2) 0.8615(2) 0.36875(7) 0.0484(4) Uani d 1 . .
H H6 0.721776 0.924909 0.396768 0.058 Uiso calc 1 . .
C C7 0.5863(2) 0.6992(3) 0.16061(8) 0.0638(5) Uani d 1 . .
H H7A 0.611485 0.590164 0.170382 0.096 Uiso calc 1 . .
H H7B 0.624205 0.725123 0.119973 0.096 Uiso calc 1 . .
H H7C 0.477664 0.712315 0.161343 0.096 Uiso calc 1 . .
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C7 . . 117.88(14) ?
C1 N1 H1N . . 109.5 ?
C1 N1 H2N . . 109.5 ?
H1N N1 H2N . . 109.5 ?
C1 N1 H3N . . 109.5 ?
H1N N1 H3N . . 109.5 ?
H2N N1 H3N . . 109.5 ?
C1 N1 H4N . . 109.5 ?
C1 N1 H5N . . 109.5 ?
H4N N1 H5N . . 109.5 ?
C1 N1 H6N . . 109.5 ?
H4N N1 H6N . . 109.5 ?
H5N N1 H6N . . 109.5 ?
C2 C1 C6 . . 120.83(14) ?
C2 C1 N1 . . 119.65(14) ?
C6 C1 N1 . . 119.51(15) ?
C1 C2 C3 . . 119.76(14) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C4 C3 C2 . . 119.77(14) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
O1 C4 C3 . . 124.81(14) ?
O1 C4 C5 . . 115.46(14) ?
C3 C4 C5 . . 119.73(13) ?
C6 C5 C4 . . 120.60(15) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 119.28(15) ?
C5 C6 H6 . . 120.4 ?
C1 C6 H6 . . 120.4 ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.3615(17) ?
O1 C7 . 1.425(2) ?
N1 C1 . 1.4679(19) ?
N1 H1N . 0.9000 ?
N1 H2N . 0.9000 ?
N1 H3N . 0.9000 ?
N1 H4N . 0.9000 ?
N1 H5N . 0.9000 ?
N1 H6N . 0.9000 ?
C1 C2 . 1.372(2) ?
C1 C6 . 1.377(2) ?
C2 C3 . 1.388(2) ?
C2 H2 . 0.9400 ?
C3 C4 . 1.378(2) ?
C3 H3 . 0.9400 ?
C4 C5 . 1.384(2) ?
C5 C6 . 1.375(2) ?
C5 H5 . 0.9400 ?
C6 H6 . 0.9400 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C7 H7C . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N Cl1 8_765 0.90 2.43 3.3265(18) 174 yes
N1 H2N Cl1 4_466 0.90 2.40 3.1915(15) 147 yes
N1 H3N CL1 1_555 0.90 2.45 3.1570(16) 135 yes
N1 H4N Cl1 5_666 0.90 2.43 3.3323(18) 180 yes
N1 H5N Cl1 . 0.90 2.36 3.1570(15) 148 yes
N1 H6N Cl1 4_466 0.90 2.49 3.1915(17) 136 yes
C6 H6 Cl1 8_765 0.94 2.82 3.6323(16) 145 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.2(2) ?
N1 C1 C2 C3 . . . . 177.97(14) ?
C1 C2 C3 C4 . . . . 0.4(2) ?
C7 O1 C4 C3 . . . . -7.0(2) ?
C7 O1 C4 C5 . . . . 173.48(15) ?
C2 C3 C4 O1 . . . . -178.58(14) ?
C2 C3 C4 C5 . . . . 1.0(2) ?
O1 C4 C5 C6 . . . . 178.05(15) ?
C3 C4 C5 C6 . . . . -1.5(2) ?
C4 C5 C6 C1 . . . . 0.7(3) ?
C2 C1 C6 C5 . . . . 0.7(2) ?
N1 C1 C6 C5 . . . . -178.52(15) ?
