#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/34/4513400.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_4513400
loop_
_publ_author_name
'George, Fanny'
'Norberg, Bernadette'
'Wouters, Johan'
'Leyssens, Tom'
_publ_section_title
;
 Structural Investigation of Substituent Effect on Hydrogen Bonding in
 (S)-Phenylglycine Amide Benzaldimines
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4005
_journal_paper_doi               10.1021/acs.cgd.5b00621
_journal_volume                  15
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C15 H13 Br N2 O'
_chemical_formula_sum            'C15 H13 Br N2 O'
_chemical_formula_weight         317.18
_chemical_name_systematic
;
 ?
;
_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                   7.0276(4)
_cell_length_b                   7.7445(5)
_cell_length_c                   25.6078(13)
_cell_measurement_reflns_used    2402
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2130
_cell_measurement_theta_min      3.3002
_cell_volume                     1393.71(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir2004
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3712
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω 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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5304
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    2.942
_exptl_absorpt_correction_T_max  0.7574
_exptl_absorpt_correction_T_min  0.3209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.018(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0898
_reflns_number_gt                2039
_reflns_number_total             2463
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00621_si_001.cif
_cod_data_source_block           m-Br
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 4513392--4513414.cif.
;
_cod_original_sg_symbol_H-M      'P21 21 21'
_cod_database_code               4513400
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.3479(4) 0.8385(3) 0.63147(11) 0.0357(6) Uani 1 1 d .
C2 C 0.4913(4) 0.8664(4) 0.59509(12) 0.0407(7) Uani 1 1 d .
H2 H 0.6139 0.8260 0.6013 0.049 Uiso 1 1 calc R
C3 C 0.4496(5) 0.9546(4) 0.54973(12) 0.0466(8) Uani 1 1 d .
C4 C 0.2720(5) 1.0173(5) 0.54021(12) 0.0574(9) Uani 1 1 d .
H4 H 0.2474 1.0786 0.5097 0.069 Uiso 1 1 calc R
C5 C 0.1286(5) 0.9895(5) 0.57613(13) 0.0597(9) Uani 1 1 d .
H5 H 0.0071 1.0320 0.5697 0.072 Uiso 1 1 calc R
C6 C 0.1648(5) 0.8986(4) 0.62177(13) 0.0486(8) Uani 1 1 d .
H6 H 0.0676 0.8782 0.6456 0.058 Uiso 1 1 calc R
C7 C 0.3906(4) 0.7405(3) 0.67935(12) 0.0335(7) Uani 1 1 d .
H7 H 0.5020 0.6757 0.6807 0.040 Uiso 1 1 calc R
C8 C 0.3319(4) 0.6221(3) 0.76118(11) 0.0326(6) Uani 1 1 d .
H8 H 0.4472 0.5588 0.7513 0.039 Uiso 1 1 calc R
C9 C 0.1708(4) 0.4926(3) 0.76942(11) 0.0345(6) Uani 1 1 d .
C10 C 0.3711(4) 0.7210(3) 0.81121(11) 0.0352(7) Uani 1 1 d .
C11 C 0.5588(4) 0.7513(4) 0.82635(14) 0.0433(8) Uani 1 1 d .
H11 H 0.6581 0.7097 0.8059 0.052 Uiso 1 1 calc R
C12 C 0.5988(5) 0.8422(5) 0.87129(14) 0.0549(9) Uani 1 1 d .
H12 H 0.7246 0.8615 0.8809 0.066 Uiso 1 1 calc R
C13 C 0.4552(6) 0.9039(5) 0.90164(14) 0.0601(10) Uani 1 1 d .
H13 H 0.4827 0.9647 0.9320 0.072 Uiso 1 1 calc R
C14 C 0.2695(6) 0.8761(5) 0.88727(14) 0.0623(10) Uani 1 1 d .
H14 H 0.1711 0.9189 0.9078 0.075 Uiso 1 1 calc R
C15 C 0.2283(5) 0.7844(5) 0.84218(13) 0.0518(9) Uani 1 1 d .
H15 H 0.1021 0.7657 0.8328 0.062 Uiso 1 1 calc R
N1 N 0.2823(3) 0.7406(3) 0.71872(9) 0.0318(5) Uani 1 1 d .
N2 N 0.0003(3) 0.5341(3) 0.75130(10) 0.0421(6) Uani 1 1 d .
H2A H -0.1035 0.4689 0.7541 0.051 Uiso 1 1 d .
H2B H -0.0257 0.6416 0.7371 0.051 Uiso 1 1 d .
O1 O 0.2029(3) 0.3564(3) 0.79274(9) 0.0457(5) Uani 1 1 d .
Br1 Br 0.64402(6) 0.98946(6) 0.499450(13) 0.0803(2) Uani 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
C2 C1 C6 120.0(3)
C2 C1 C7 119.4(3)
C6 C1 C7 120.6(3)
C3 C2 C1 119.2(3)
C3 C2 H2 120.4
C1 C2 H2 120.4
C4 C3 C2 121.5(3)
C4 C3 Br1 119.2(2)
C2 C3 Br1 119.3(2)
C3 C4 C5 119.6(3)
C3 C4 H4 120.2
C5 C4 H4 120.2
C4 C5 C6 120.4(3)
C4 C5 H5 119.8
C6 C5 H5 119.8
C5 C6 C1 119.3(3)
C5 C6 H6 120.3
C1 C6 H6 120.3
N1 C7 C1 122.8(2)
N1 C7 H7 118.6
C1 C7 H7 118.6
N1 C8 C10 110.71(19)
N1 C8 C9 109.7(2)
C10 C8 C9 110.4(2)
N1 C8 H8 108.6
C10 C8 H8 108.6
C9 C8 H8 108.6
O1 C9 N2 122.9(2)
O1 C9 C8 119.5(2)
N2 C9 C8 117.6(2)
C15 C10 C11 118.1(3)
C15 C10 C8 122.5(3)
C11 C10 C8 119.4(3)
C12 C11 C10 120.7(3)
C12 C11 H11 119.6
C10 C11 H11 119.6
C13 C12 C11 120.3(3)
C13 C12 H12 119.8
C11 C12 H12 119.8
C14 C13 C12 119.8(3)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.1(4)
C13 C14 H14 119.9
C15 C14 H14 119.9
C10 C15 C14 120.9(3)
C10 C15 H15 119.6
C14 C15 H15 119.6
C7 N1 C8 116.7(2)
C9 N2 H2A 125.2
C9 N2 H2B 122.2
H2A N2 H2B 112.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.389(4)
C1 C6 1.391(4)
C1 C7 1.473(4)
C2 C3 1.379(4)
C2 H2 0.9300
C3 C4 1.361(5)
C3 Br1 1.897(3)
C4 C5 1.381(5)
C4 H4 0.9300
C5 C6 1.388(4)
C5 H5 0.9300
C6 H6 0.9300
C7 N1 1.263(3)
C7 H7 0.9300
C8 N1 1.465(3)
C8 C10 1.518(4)
C8 C9 1.527(4)
C8 H8 0.9800
C9 O1 1.233(3)
C9 N2 1.324(3)
C10 C15 1.370(4)
C10 C11 1.395(4)
C11 C12 1.378(5)
C11 H11 0.9300
C12 C13 1.361(5)
C12 H12 0.9300
C13 C14 1.373(6)
C13 H13 0.9300
C14 C15 1.386(5)
C14 H14 0.9300
C15 H15 0.9300
N2 H2A 0.8899
N2 H2B 0.9270
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 0.3(4)
C7 C1 C2 C3 178.4(2)
C1 C2 C3 C4 1.1(5)
C1 C2 C3 Br1 -178.9(2)
C2 C3 C4 C5 -1.3(5)
Br1 C3 C4 C5 178.7(3)
C3 C4 C5 C6 0.2(5)
C4 C5 C6 C1 1.2(5)
C2 C1 C6 C5 -1.4(5)
C7 C1 C6 C5 -179.5(3)
C2 C1 C7 N1 164.7(3)
C6 C1 C7 N1 -17.2(4)
N1 C8 C9 O1 160.6(2)
C10 C8 C9 O1 -77.1(3)
N1 C8 C9 N2 -20.1(3)
C10 C8 C9 N2 102.2(3)
N1 C8 C10 C15 78.4(3)
C9 C8 C10 C15 -43.3(4)
N1 C8 C10 C11 -100.8(3)
C9 C8 C10 C11 137.5(3)
C15 C10 C11 C12 0.1(4)
C8 C10 C11 C12 179.3(3)
C10 C11 C12 C13 0.0(5)
C11 C12 C13 C14 -0.3(5)
C12 C13 C14 C15 0.5(6)
C11 C10 C15 C14 0.0(5)
C8 C10 C15 C14 -179.2(3)
C13 C14 C15 C10 -0.3(6)
C1 C7 N1 C8 173.3(2)
C10 C8 N1 C7 119.1(3)
C9 C8 N1 C7 -118.8(2)
