#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/29/4502926.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_4502926
loop_
_publ_author_name
'Kołodziejczak, Jerzy'
'Adamczyk-Woźniak, Agnieszka'
'Hachuła, Barbara'
'Barys, Maciej'
'Flakus, Henryk T.'
'Sporzyński, Andrzej'
'Koll, Aleksander'
_publ_section_title
;
 Intermolecular Interactions in the Solid State of Ionic Secondary Mannich
 Bases
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              589
_journal_paper_doi               10.1021/cg201179x
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C10 H14 Br N O'
_chemical_formula_weight         244.12
_chemical_name_systematic
; 
4-bromo-2-[(aminopropyl)methyl]-phenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 102.973(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9354(2)
_cell_length_b                   5.62810(10)
_cell_length_c                   16.6297(3)
_cell_measurement_temperature    100(2)
_cell_volume                     997.36(3)
_computing_cell_refinement       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KM4-CCD
_diffrn_measurement_method       /w
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11696
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    4.081
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_correction_T_min  0.458
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction,2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0187
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0260P)²+0.3034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0423
_refine_ls_wR_factor_ref         0.0458
_reflns_number_gt                1953
_reflns_number_total             2304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201179x_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4502926
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Br1 Br 0.369732(15) 0.10947(3) 0.828792(10) 0.01665(6) Uani 1 1 d
O1 O 0.02305(11) 0.71669(19) 0.57605(7) 0.0140(2) Uani 1 1 d
N8 N -0.10289(13) 0.1346(2) 0.56001(8) 0.0112(3) Uani 1 1 d
C1 C 0.05365(15) 0.3733(3) 0.66255(9) 0.0116(3) Uani 1 1 d
C2 C 0.09673(15) 0.5877(3) 0.63291(9) 0.0121(3) Uani 1 1 d
C6 C 0.13427(16) 0.2339(3) 0.72106(10) 0.0126(3) Uani 1 1 d
C7 C -0.08114(15) 0.3001(3) 0.63277(10) 0.0124(3) Uani 1 1 d
C5 C 0.25758(15) 0.3038(3) 0.75140(9) 0.0134(3) Uani 1 1 d
C3 C 0.22236(16) 0.6540(3) 0.66790(10) 0.0147(3) Uani 1 1 d
C4 C 0.30164(16) 0.5156(3) 0.72574(10) 0.0143(3) Uani 1 1 d
C11 C -0.25921(16) -0.1424(3) 0.47521(10) 0.0145(3) Uani 1 1 d
C12 C -0.23901(15) 0.0752(3) 0.53091(10) 0.0142(3) Uani 1 1 d
C13 C -0.39847(18) -0.1828(4) 0.43831(12) 0.0217(4) Uani 1 1 d
H72 H -0.1312(18) 0.438(3) 0.6161(11) 0.011(5) Uiso 1 1 d
H6 H 0.1033(18) 0.088(3) 0.7389(12) 0.015(5) Uiso 1 1 d
H71 H -0.1114(16) 0.217(3) 0.6739(11) 0.008(4) Uiso 1 1 d
H4 H 0.3848(19) 0.565(3) 0.7471(12) 0.016(5) Uiso 1 1 d
H122 H -0.2824(18) 0.220(3) 0.5021(11) 0.017(5) Uiso 1 1 d
H112 H -0.2136(17) -0.126(3) 0.4308(11) 0.012(4) Uiso 1 1 d
H121 H -0.2724(18) 0.047(3) 0.5778(12) 0.013(5) Uiso 1 1 d
H133 H -0.436(2) -0.045(4) 0.4058(13) 0.026(6) Uiso 1 1 d
H3 H 0.2520(17) 0.796(4) 0.6515(11) 0.014(5) Uiso 1 1 d
H111 H -0.2231(18) -0.279(3) 0.5064(11) 0.015(5) Uiso 1 1 d
H81 H -0.061(2) 0.006(4) 0.5742(13) 0.028(6) Uiso 1 1 d
H131 H -0.407(2) -0.318(4) 0.4045(14) 0.033(6) Uiso 1 1 d
H132 H -0.447(2) -0.215(4) 0.4818(13) 0.028(6) Uiso 1 1 d
H82 H -0.0820(18) 0.196(4) 0.5175(13) 0.018(5) Uiso 1 1 d
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'
Br Br -0.2901 2.4595 '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
C12 N8 C7 111.41(12)
C12 N8 H81 109.1(15)
C7 N8 H81 108.8(15)
C12 N8 H82 104.6(13)
C7 N8 H82 112.9(13)
H81 N8 H82 109.9(19)
C6 C1 C2 120.72(15)
C6 C1 C7 119.61(14)
C2 C1 C7 119.64(14)
O1 C2 C3 122.09(14)
O1 C2 C1 121.36(15)
C3 C2 C1 116.55(14)
C5 C6 C1 120.27(14)
C5 C6 H6 120.8(12)
C1 C6 H6 118.9(12)
N8 C7 C1 113.67(13)
N8 C7 H72 107.1(11)
C1 C7 H72 109.2(11)
N8 C7 H71 104.9(11)
C1 C7 H71 111.9(10)
H72 C7 H71 109.9(15)
C6 C5 C4 120.52(15)
C6 C5 Br1 120.52(12)
C4 C5 Br1 118.96(12)
C4 C3 C2 122.46(15)
C4 C3 H3 118.9(12)
C2 C3 H3 118.6(11)
C3 C4 C5 119.41(16)
C3 C4 H4 120.0(12)
C5 C4 H4 120.6(11)
C12 C11 C13 111.13(14)
C12 C11 H112 110.5(10)
C13 C11 H112 109.9(11)
C12 C11 H111 109.1(11)
C13 C11 H111 110.5(11)
H112 C11 H111 105.4(15)
N8 C12 C11 112.01(13)
N8 C12 H122 107.5(11)
C11 C12 H122 111.9(11)
N8 C12 H121 108.2(11)
C11 C12 H121 109.7(11)
H122 C12 H121 107.5(15)
C11 C13 H133 111.1(13)
C11 C13 H131 108.8(14)
H133 C13 H131 109.7(18)
C11 C13 H132 112.1(12)
H133 C13 H132 108.5(17)
H131 C13 H132 106.6(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.9099(16)
O1 C2 1.3146(19)
N8 C12 1.496(2)
N8 C7 1.503(2)
N8 H81 0.86(2)
N8 H82 0.86(2)
C1 C6 1.398(2)
C1 C2 1.423(2)
C1 C7 1.503(2)
C2 C3 1.416(2)
C6 C5 1.386(2)
C6 H6 0.960(19)
C7 H72 0.954(19)
C7 H71 0.948(18)
C5 C4 1.389(2)
C3 C4 1.382(2)
C3 H3 0.92(2)
C4 H4 0.94(2)
C11 C12 1.521(2)
C11 C13 1.526(2)
C11 H112 0.985(19)
C11 H111 0.959(19)
C12 H122 1.01(2)
C12 H121 0.95(2)
C13 H133 0.98(2)
C13 H131 0.94(2)
C13 H132 1.00(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145092
