#------------------------------------------------------------------------------
#$Date: 2023-12-08 19:12:05 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288193 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/50/7115009.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_7115009
loop_
_publ_author_name
'Zhuang, Wei'
'Hazell, Rita G.'
'Jørgensen, Karl Anker'
_publ_contact_author             'Prof Karl Anker Jorgensen'
_publ_section_title
;
 Catalytic enantioselective addition of aromatic amines to enones:
 synthesis of optically active β-amino acid derivatives
;
_journal_issue                   14
_journal_name_full               'Chemical Communications'
_journal_page_first              1240
_journal_paper_doi               10.1039/b103334b
_journal_year                    2001
_chemical_formula_sum            'C19 H23 N2 O'
_chemical_formula_weight         296.42
_chemical_name_systematic
;                                   
(S)-(Methyl-phenyl-amino)-N-((S)-1-phenyl-ethyl)-butyramide
;
_space_group_IT_number           170
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   10.329(1)
_cell_length_b                   10.329(1)
_cell_length_c                   28.108(4)
_cell_measurement_reflns_used    3882
_cell_measurement_temperature    120
_cell_measurement_theta_max      22.3
_cell_measurement_theta_min      2.4
_cell_volume                     2597.0(5)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics
;                                   
ORTEP-III (Burnett & Johnson,  1996), KRYSTAL                     
;
_computing_publication_material  KRYSTAL
_computing_structure_refinement  'modified ORFLS(1962), KRYSTAL'
_computing_structure_solution
;                                   
SIR97 (Altomare et al., 1997 ), KRYSTAL                            
;
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_max 100
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       'ω rotation scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.155
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            29407
_diffrn_reflns_reduction_process 29407
_diffrn_reflns_theta_max         25.2
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.34(6)
_refine_diff_density_min         -0.43(6)
_refine_ls_extinction_coef       282(41)
_refine_ls_extinction_method
;                                   
Type 1 Lorentzian isotropic (Becker and Coppens, 1974)           
;
_refine_ls_goodness_of_fit_ref   1.38
_refine_ls_hydrogen_treatment    calculated
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1824
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          0.0011
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;                                   
w== 1/{[σcs(F²)+1.03F²]^1/2^- |F|}² 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.052
_reflns_number_gt                1824
_reflns_number_total             5067
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            b103334b.txt
_cod_data_source_block           wei8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

data name '_exptl_aabsorpt_process_details' was replaced with
'_exptl_absorpt_process_details' as specified in the replacement file
'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        2597(1)
_cod_original_sg_symbol_H-M      'P 6(5)'
_cod_original_formula_sum        C19H23N2O
_cod_database_code               7115009
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-y,+x-y,2/3+z
-x+y,-x,1/3+z
-x,-y,1/2+z
+y,-x+y,1/6+z
+x-y,+x,5/6+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
O1 0.1946(3) 0.0741(3) 0.2498 0.034(2) Uij
N1 0.5049(4) 0.2792(4) 0.1680(1) 0.031(3) Uij
N6 0.1126(3) 0.0413(3) 0.1730(1) 0.024(2) Uij
C1 0.5050(5) 0.3307(5) 0.1197(2) 0.045(4) Uij
C2 0.4564(4) 0.3451(4) 0.2056(2) 0.028(3) Uij
C3 0.5525(5) 0.5154(5) 0.2084(2) 0.044(4) Uij
C4 0.2886(4) 0.2920(4) 0.2002(2) 0.028(3) Uij
C5 0.1941(4) 0.1274(4) 0.2099(2) 0.024(3) Uij
C7 0.0207(4) -0.1230(4) 0.1770(2) 0.031(3) Uij
C8 -0.1010(5) -0.1762(5) 0.1384(2) 0.047(4) Uij
C9 0.1100(4) -0.2025(4) 0.1731(2) 0.029(3) Uij
C10 0.0412(5) -0.3546(5) 0.1840(2) 0.046(4) Uij
C11 0.1200(7) -0.4307(5) 0.1806(2) 0.058(5) Uij
C12 0.2655(6) -0.3590(6) 0.1660(2) 0.057(5) Uij
C13 0.3367(6) -0.2084(6) 0.1552(2) 0.061(5) Uij
C14 0.2582(5) -0.1306(5) 0.1582(2) 0.043(4) Uij
C15 0.6083(4) 0.2316(4) 0.1783(2) 0.026(3) Uij
C16 0.6213(9) 0.1908(9) 0.2223(2) 0.105(9) Uij
C17 0.7207(9) 0.1392(10) 0.2328(2) 0.111(10) Uij
C18 0.8064(5) 0.1272(5) 0.1990(2) 0.046(4) Uij
C19 0.7929(7) 0.1671(8) 0.1559(2) 0.088(8) Uij
C20 0.6951(7) 0.2184(8) 0.1445(2) 0.084(7) Uij
H6n 0.118 0.084 0.133 0.029 Uiso
H1a 0.603 0.407 0.110 0.054 Uiso
H1b 0.438 0.369 0.116 0.054 Uiso
H1c 0.475 0.250 0.100 0.054 Uiso
H2 0.468 0.307 0.235 0.034 Uiso
H3a 0.522 0.559 0.233 0.052 Uiso
H3b 0.547 0.557 0.179 0.052 Uiso
H3c 0.653 0.542 0.214 0.052 Uiso
H4a 0.270 0.313 0.169 0.034 Uiso
H4b 0.262 0.345 0.222 0.034 Uiso
H7 -0.026 -0.145 0.207 0.035 Uiso
H8a -0.160 -0.281 0.141 0.054 Uiso
H8b -0.057 -0.149 0.108 0.054 Uiso
H8c -0.161 -0.131 0.143 0.054 Uiso
H10 -0.060 -0.407 0.194 0.057 Uiso
H11 0.071 -0.534 0.189 0.070 Uiso
H12 0.319 -0.412 0.164 0.068 Uiso
H13 0.439 -0.156 0.146 0.069 Uiso
H14 0.307 -0.027 0.150 0.051 Uiso
H16 0.563 0.198 0.247 0.127 Uiso
H17 0.728 0.113 0.265 0.133 Uiso
H18 0.873 0.091 0.207 0.056 Uiso
H19 0.852 0.160 0.131 0.101 Uiso
H20 0.688 0.243 0.112 0.105 Uiso
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C15 117.1(3)
C2 N1 C15 120.3(3)
C1 N1 C2 116.0(3)
C5 N6 C7 121.8(3)
N1 C2 C3 113.1(3)
N1 C2 C4 110.2(3)
C3 C2 C4 112.4(3)
C2 C4 C5 111.3(3)
O1 C5 N6 122.5(3)
O1 C5 C4 121.1(4)
N6 C5 C4 116.4(4)
N6 C7 C9 113.6(3)
N6 C7 C8 107.3(3)
C8 C7 C9 111.4(3)
C10 C9 C14 118.2(4)
C7 C9 C14 122.6(4)
C7 C9 C10 119.2(4)
C9 C10 C11 120.6(5)
C10 C11 C12 120.7(5)
C11 C12 C13 120.0(5)
C12 C13 C14 119.8(5)
C9 C14 C13 120.7(4)
C16 C15 C20 116.1(4)
N1 C15 C16 121.0(4)
N1 C15 C20 122.8(4)
C15 C16 C17 121.6(5)
C16 C17 C18 121.6(5)
C17 C18 C19 116.5(4)
C18 C19 C20 123.0(5)
C15 C20 C19 121.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.251(4)
N1 C15 1.411(5)
N1 C1 1.458(5)
N1 C2 1.474(5)
N6 C5 1.351(5)
N6 C7 1.478(5)
C2 C3 1.530(6)
C2 C4 1.542(5)
C4 C5 1.503(5)
C7 C9 1.515(6)
C7 C8 1.539(5)
C9 C14 1.390(6)
C9 C10 1.396(6)
C10 C11 1.390(7)
C11 C12 1.365(7)
C12 C13 1.381(7)
C13 C14 1.401(6)
C15 C16 1.333(7)
C15 C20 1.360(6)
C16 C17 1.404(7)
C17 C18 1.345(7)
C18 C19 1.310(6)
C19 C20 1.393(7)
