#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:52:38 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/95/2009535.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_2009535
loop_
_publ_author_name
'Garcia, J.G.'
'Fronczek, F.R.'
'Gandour, R.D.'
_publ_section_title
;
 2-Hydroxy-4,4-dimethyl-2-(2-methylphenyl)morpholinium bromide,
 C~13~H~20~NO~2~^+^.Br^{-^}
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              430
_journal_page_last               432
_journal_paper_doi               10.1107/S0108270193006559
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C13 H20 Br N O2'
_chemical_formula_weight         302.22
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source           'IntTabIV Tables 2.2B, 2.3.1'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6930(5)
_cell_length_b                   12.3768(9)
_cell_length_c                   12.4624(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1340.85(16)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4871
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_time  167
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.0
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.87
_refine_diff_density_min         -0.42
_refine_ls_goodness_of_fit_obs   1.549
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2144
_refine_ls_R_factor_obs          0.037
_refine_ls_shift/esd_max         0.02
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4F~o~^2^/[\s^2^(I) + 0.02F~o~^2^)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.037
_reflns_number_observed          2144
_reflns_number_total             3081
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            hh1076.cif
_cod_data_source_block           hh1076_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '4F~o~^2^/[\s^2^(I) +
0.02F~o~^2^)^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 4F~o~^2^/[\s^2^(I) + 0.02F~o~^2^)^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1340.8(3)
_cod_original_formula_sum        'C13 H20 Br1 N1 O2'
_cod_database_code               2009535
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
Br1 .96390(5) .44790(4) .05344(4)
O1 .7721(3) -.0072(2) .2090(3)
O2 .9126(3) .1318(3) .2827(3)
N .9207(3) .1134(3) .0403(3)
C1 .7968(4) .1606(4) .1130(4)
C2 .7831(4) .1061(3) .2201(4)
C3 .8978(5) -.0526(4) .1493(4)
C4 .9021(5) -.0074(4) .0394(4)
C5 1.0793(5) .1454(4) .0772(4)
C6 .8981(6) .1561(4) -.0706(4)
C7 .6307(5) .1419(4) .2727(4)
C8 .5004(5) .0752(4) .2572(4)
C9 .3621(6) .1013(5) .3043(4)
C10 .3478(6) .1926(4) .3635(5)
C11 .4698(6) .2601(4) .3749(4)
C12 .6168(5) .2375(4) .3299(4)
C13 .7412(6) .3190(4) .3434(5)
H20H .937(5) .081(3) .331(3)
H1a .719(4) .142(3) .072(3)
H1b .822(4) .236(3) .125(3)
H3a .882(5) -.129(4) .148(3)
H3b .997(5) -.044(4) .200(3)
H4a .980(4) -.032(3) .000(3)
H4b .798(5) -.021(3) .003(3)
H5a 1.091(4) .120(3) .156(3)
H5b 1.132(5) .115(3) .024(3)
H5c 1.079(5) .229(3) .084(3)
H6a .805(6) .124(5) -.105(4)
H6b .910(4) .239(3) -.069(3)
H6c .972(4) .127(3) -.122(3)
H8 .507(4) .014(3) .211(3)
H9 .301(8) .049(6) .280(5)
H10 .243(8) .218(5) .410(5)
H11 .459(4) .324(2) .410(2)
H13a .811(6) .273(4) .394(4)
H13b .699(5) .380(4) .390(3)
H13c .767(5) .339(4) .265(3)
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 O1 C3 112.8(3) yes
C1 N C4 108.1(3) yes
C1 N C5 111.4(3) yes
C1 N C6 108.8(3) yes
C4 N C5 111.2(3) yes
C4 N C6 109.3(4) yes
C5 N C6 108.1(3) yes
N C1 C2 114.4(3) yes
O1 C2 O2 109.5(3) yes
O1 C2 C1 111.4(4) yes
O1 C2 C7 105.5(3) yes
O2 C2 C1 109.2(3) yes
O2 C2 C7 112.8(3) yes
C1 C2 C7 108.5(3) yes
O1 C3 C4 110.5(4) yes
N C4 C3 111.8(4) yes
C2 C7 C8 117.5(4) yes
C2 C7 C12 122.5(4) yes
C8 C7 C12 119.9(4) yes
C7 C8 C9 120.2(4) yes
C8 C9 C10 120.6(5) yes
C9 C10 C11 119.9(5) yes
C10 C11 C12 122.7(5) yes
C7 C12 C11 116.6(4) yes
C7 C12 C13 125.0(4) yes
C11 C12 C13 118.4(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.412(5) yes
O1 C3 1.437(5) yes
O2 C2 1.406(5) yes
N C1 1.524(5) yes
N C4 1.504(6) yes
N C5 1.507(5) yes
N C6 1.492(6) yes
C1 C2 1.501(6) yes
C2 C7 1.543(6) yes
C3 C4 1.480(7) yes
C7 C8 1.415(6) yes
C7 C12 1.387(7) yes
C8 C9 1.377(6) yes
C9 C10 1.355(8) yes
C10 C11 1.357(7) yes
C11 C12 1.423(7) yes
C12 C13 1.488(7) 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_publ_flag
C2 O1 C3 C4 -60.7(5) yes
C4 N C1 C2 48.3(4) yes
N C1 C2 O1 -50.3(4) yes
N C1 C2 O2 70.7(4) yes
O2 C2 C7 C12 37.6(6) yes
H2OH O2 C2 O1 -30.(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139057072
