#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/45/7154562.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_7154562
loop_
_publ_author_name
'Ozeryanskii, Valery A.'
'Gorbacheva, Anastasia Yu'
'Pozharskii, Alexander F.'
'Vlasenko, Marina P.'
'Tereznikov, Alexander Yu'
'Chernov'yants, Margarita S.'
_publ_section_title
;
 The first proton sponge-based amino acids: synthesis, acid-base
 properties and some reactivity.
;
_journal_issue                   31
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8524
_journal_page_last               8532
_journal_paper_doi               10.1039/c5ob01065a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C15 H19 N2 O2, Br'
_chemical_formula_sum            'C15 H19 Br N2 O2'
_chemical_formula_weight         339.23
_chemical_name_common
'N-Methyl-N-(8-dimethylaminonaphth-1-yl)aminoacetic acid hydrobromide'
_chemical_name_systematic
; 
 ? 
;
_chemical_temperature_decomposition 510.1(10)
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-05-13 deposited with the CCDC.
2015-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.653(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4871(8)
_cell_length_b                   12.1721(12)
_cell_length_c                   16.4565(17)
_cell_measurement_reflns_used    219
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     1494.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_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  0.0629
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10993
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    2.753
_exptl_absorpt_correction_T_max  0.683
_exptl_absorpt_correction_T_min  0.446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            grey
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.756
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0448
_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)+(0.0626P)²+0.5020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2827
_reflns_number_total             3567
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c5ob01065a2.cif
_cod_data_source_block           p21c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been given
as '236-238 deg.C (decomp.)'. '_chemical_melting_point' value
'236-238 deg.C (decomp.)' was changed to '510.1(10)' - it was
converted from degrees Celsius(C) to Kelvins(K), the average value
was taken and precision was estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154562--7154563.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7154562
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
_atom_site_refinement_flags
N1 N 0.3608(4) 1.1948(2) 0.47021(15) 0.0142(5) Uani 1 1 d .
Br1 Br -0.28519(4) 1.05210(3) 0.679131(18) 0.02191(13) Uani 1 1 d .
N2 N 0.1657(4) 1.2760(2) 0.34594(15) 0.0182(6) Uani 1 1 d .
H2N H 0.240(6) 1.224(4) 0.389(3) 0.033(11) Uiso 1 1 d .
O1 O 0.0104(3) 1.1773(2) 0.51349(15) 0.0278(6) Uani 1 1 d .
O2 O 0.0904(4) 1.0466(2) 0.60516(15) 0.0275(6) Uani 1 1 d .
H2O H -0.029(8) 1.057(4) 0.620(3) 0.051(15) Uiso 1 1 d .
C1 C 0.3530(4) 1.3006(2) 0.51077(17) 0.0141(6) Uani 1 1 d .
C2 C 0.4333(4) 1.3148(3) 0.58824(18) 0.0161(6) Uani 1 1 d .
H2A H 0.4940 1.2550 0.6154 0.019 Uiso 1 1 calc R
C3 C 0.4265(4) 1.4169(3) 0.62754(18) 0.0168(6) Uani 1 1 d .
H3A H 0.4807 1.4255 0.6814 0.020 Uiso 1 1 calc R
C4 C 0.3425(4) 1.5036(3) 0.58875(18) 0.0166(6) Uani 1 1 d .
H4A H 0.3381 1.5722 0.6160 0.020 Uiso 1 1 calc R
C5 C 0.2612(4) 1.4930(2) 0.50802(18) 0.0140(6) Uani 1 1 d .
C6 C 0.1755(4) 1.5841(3) 0.4678(2) 0.0178(6) Uani 1 1 d .
H6A H 0.1752 1.6532 0.4947 0.021 Uiso 1 1 calc R
C7 C 0.0934(4) 1.5738(3) 0.3910(2) 0.0192(7) Uani 1 1 d .
H7A H 0.0372 1.6358 0.3648 0.023 Uiso 1 1 calc R
C8 C 0.0917(4) 1.4732(3) 0.35093(19) 0.0189(6) Uani 1 1 d .
H8A H 0.0351 1.4668 0.2973 0.023 Uiso 1 1 calc R
C9 C 0.1712(4) 1.3833(2) 0.38842(17) 0.0146(6) Uani 1 1 d .
C10 C 0.2638(4) 1.3891(2) 0.46822(17) 0.0125(6) Uani 1 1 d .
C11 C 0.5412(4) 1.1742(3) 0.4423(2) 0.0203(7) Uani 1 1 d .
H11A H 0.5761 1.2362 0.4091 0.030 Uiso 1 1 calc R
H11B H 0.5386 1.1068 0.4096 0.030 Uiso 1 1 calc R
H11C H 0.6281 1.1659 0.4898 0.030 Uiso 1 1 calc R
C12 C 0.3072(4) 1.1020(3) 0.51967(18) 0.0180(6) Uani 1 1 d .
H12A H 0.3914 1.0959 0.5690 0.022 Uiso 1 1 calc R
H12B H 0.3148 1.0333 0.4880 0.022 Uiso 1 1 calc R
C13 C 0.1204(5) 1.1148(3) 0.54481(19) 0.0200(7) Uani 1 1 d .
C14 C 0.2671(5) 1.2766(3) 0.2722(2) 0.0289(8) Uani 1 1 d .
H14A H 0.2882 1.2009 0.2552 0.043 Uiso 1 1 calc R
H14B H 0.3822 1.3138 0.2845 0.043 Uiso 1 1 calc R
H14C H 0.1978 1.3157 0.2281 0.043 Uiso 1 1 calc R
C15 C -0.0221(5) 1.2349(3) 0.3261(2) 0.0243(7) Uani 1 1 d .
H15A H -0.0864 1.2348 0.3757 0.037 Uiso 1 1 calc R
H15B H -0.0182 1.1600 0.3044 0.037 Uiso 1 1 calc R
H15C H -0.0843 1.2830 0.2853 0.037 Uiso 1 1 calc R
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
C1 N1 C12 113.8(2)
C1 N1 C11 111.3(2)
C12 N1 C11 109.8(2)
C9 N2 C14 112.7(3)
C9 N2 C15 112.7(2)
C14 N2 C15 110.8(3)
C9 N2 H2N 103(2)
C14 N2 H2N 106(2)
C15 N2 H2N 112(2)
C13 O2 H2O 109(3)
C2 C1 C10 120.9(3)
C2 C1 N1 120.4(3)
C10 C1 N1 118.7(2)
C1 C2 C3 120.6(3)
C1 C2 H2A 119.7
C3 C2 H2A 119.7
C4 C3 C2 120.2(3)
C4 C3 H3A 119.9
C2 C3 H3A 119.9
C3 C4 C5 121.0(3)
C3 C4 H4A 119.5
C5 C4 H4A 119.5
C6 C5 C4 120.6(3)
C6 C5 C10 120.1(3)
C4 C5 C10 119.3(3)
C7 C6 C5 120.9(3)
C7 C6 H6A 119.6
C5 C6 H6A 119.6
C6 C7 C8 120.4(3)
C6 C7 H7A 119.8
C8 C7 H7A 119.8
C9 C8 C7 120.2(3)
C9 C8 H8A 119.9
C7 C8 H8A 119.9
C8 C9 C10 122.2(3)
C8 C9 N2 119.8(3)
C10 C9 N2 117.9(3)
C1 C10 C5 118.0(3)
C1 C10 C9 125.8(3)
C5 C10 C9 116.1(3)
N1 C11 H11A 109.5
N1 C11 H11B 109.5
H11A C11 H11B 109.5
N1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N1 C12 C13 112.1(3)
N1 C12 H12A 109.2
C13 C12 H12A 109.2
N1 C12 H12B 109.2
C13 C12 H12B 109.2
H12A C12 H12B 107.9
O1 C13 O2 124.3(3)
O1 C13 C12 124.6(3)
O2 C13 C12 111.1(3)
N2 C14 H14A 109.5
N2 C14 H14B 109.5
H14A C14 H14B 109.5
N2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N2 C15 H15A 109.5
N2 C15 H15B 109.5
H15A C15 H15B 109.5
N2 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.454(4)
N1 C12 1.467(4)
N1 C11 1.483(4)
N2 C9 1.480(4)
N2 C14 1.483(4)
N2 C15 1.503(4)
N2 H2N 1.08(4)
O1 C13 1.205(4)
O2 C13 1.328(4)
O2 H2O 0.95(6)
C1 C2 1.376(4)
C1 C10 1.422(4)
C2 C3 1.404(4)
C2 H2A 0.9500
C3 C4 1.360(5)
C3 H3A 0.9500
C4 C5 1.422(4)
C4 H4A 0.9500
C5 C6 1.417(4)
C5 C10 1.425(4)
C6 C7 1.366(4)
C6 H6A 0.9500
C7 C8 1.391(4)
C7 H7A 0.9500
C8 C9 1.368(4)
C8 H8A 0.9500
C9 C10 1.436(4)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.498(5)
C12 H12A 0.9900
C12 H12B 0.9900
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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
N2 H2N N1 1_555 1.08(4) 1.59(4) 2.610(4) 156(2)
O2 H2O Br1 1_555 0.95(6) 2.22(5) 3.154(4) 165(3)
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
C12 N1 C1 C2 50.4(4)
C11 N1 C1 C2 -74.4(3)
C12 N1 C1 C10 -130.8(3)
C11 N1 C1 C10 104.5(3)
C10 C1 C2 C3 1.0(5)
N1 C1 C2 C3 179.8(3)
C1 C2 C3 C4 -1.1(5)
C2 C3 C4 C5 -0.3(5)
C3 C4 C5 C6 -179.4(3)
C3 C4 C5 C10 1.7(5)
C4 C5 C6 C7 -178.4(3)
C10 C5 C6 C7 0.5(5)
C5 C6 C7 C8 0.4(5)
C6 C7 C8 C9 0.5(5)
C7 C8 C9 C10 -2.1(5)
C7 C8 C9 N2 178.8(3)
C14 N2 C9 C8 65.5(4)
C15 N2 C9 C8 -60.9(4)
C14 N2 C9 C10 -113.6(3)
C15 N2 C9 C10 120.0(3)
C2 C1 C10 C5 0.4(4)
N1 C1 C10 C5 -178.5(3)
C2 C1 C10 C9 -178.1(3)
N1 C1 C10 C9 3.0(5)
C6 C5 C10 C1 179.4(3)
C4 C5 C10 C1 -1.7(4)
C6 C5 C10 C9 -2.0(4)
C4 C5 C10 C9 176.9(3)
C8 C9 C10 C1 -178.6(3)
N2 C9 C10 C1 0.4(4)
C8 C9 C10 C5 2.8(4)
N2 C9 C10 C5 -178.1(3)
C1 N1 C12 C13 58.4(3)
C11 N1 C12 C13 -176.1(3)
N1 C12 C13 O1 17.1(4)
N1 C12 C13 O2 -164.2(2)
