#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/56/1505654.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_1505654
loop_
_publ_author_name
'Okamoto, Iwao'
'Yamasaki, Ryu'
'Sawamura, Mika'
'Kato, Takako'
'Nagayama, Naomi'
'Takeya, Tetsuya'
'Tamura, Osamu'
'Masu, Hyuma'
'Azumaya, Isao'
'Yamaguchi, Kentaro'
'Kagechika, Hiroyuki'
'Tanatani, Aya'
_publ_section_title
;
 Redox-induced conformational alteration of n,n-diarylamides.
;
_journal_issue                   26
_journal_name_full               'Organic letters'
_journal_page_first              5545
_journal_page_last               5547
_journal_paper_doi               10.1021/ol702504x
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.31
_chemical_name_systematic
; 
 ? 
;
_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                 109.123(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9486(17)
_cell_length_b                   13.132(3)
_cell_length_c                   12.841(3)
_cell_measurement_reflns_used    1842
_cell_measurement_temperature    298
_cell_measurement_theta_max      22.5105
_cell_measurement_theta_min      2.2855
_cell_volume                     1425.7(5)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'BrukerSmart1000 CCD'
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8358
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0417
_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)+(0.0525P)²+0.1854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                2003
_reflns_number_total             3247
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702504x1.cif
_cod_data_source_block           compound1(4131iaz)
_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      P2(1)/c
_cod_database_code               1505654
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
O1 O 0.82330(13) 1.18488(8) 0.42491(9) 0.0570(3) Uani 1 1 d .
N1 N 0.76806(14) 1.02954(8) 0.34657(10) 0.0414(3) Uani 1 1 d .
O2 O 0.51436(13) 0.97642(7) 0.16704(9) 0.0557(3) Uani 1 1 d .
C3 C 0.69301(17) 0.93153(10) 0.34137(12) 0.0420(3) Uani 1 1 d .
O3 O 0.72134(15) 0.69830(8) 0.50655(10) 0.0720(4) Uani 1 1 d .
C4 C 0.56679(17) 0.90504(10) 0.24840(12) 0.0429(3) Uani 1 1 d .
C1 C 0.74366(17) 1.10729(10) 0.40981(12) 0.0429(3) Uani 1 1 d .
C8 C 0.74879(17) 0.86397(11) 0.42851(12) 0.0466(4) Uani 1 1 d .
H8 H 0.8336 0.8822 0.4901 0.056 Uiso 1 1 calc R
C5 C 0.50065(19) 0.80880(11) 0.24444(14) 0.0509(4) Uani 1 1 d .
H5 H 0.4176 0.7892 0.1824 0.061 Uiso 1 1 calc R
C11 C 0.87826(17) 1.04165(11) 0.28693(12) 0.0428(3) Uani 1 1 d .
C7 C 0.67849(18) 0.76924(11) 0.42413(13) 0.0487(4) Uani 1 1 d .
C6 C 0.55654(19) 0.74212(11) 0.33118(14) 0.0528(4) Uani 1 1 d .
H6 H 0.5112 0.6779 0.3269 0.063 Uiso 1 1 calc R
C2 C 0.6133(2) 1.09443(13) 0.45786(15) 0.0628(5) Uani 1 1 d .
H2A H 0.5985 1.1570 0.4919 0.094 Uiso 1 1 calc R
H2B H 0.6407 1.0412 0.5121 0.094 Uiso 1 1 calc R
H2C H 0.5172 1.0768 0.4004 0.094 Uiso 1 1 calc R
C12 C 1.0049(2) 0.97646(12) 0.30652(15) 0.0580(4) Uani 1 1 d .
H12 H 1.0211 0.9252 0.3591 0.070 Uiso 1 1 calc R
C16 C 0.85658(19) 1.11835(12) 0.20940(13) 0.0542(4) Uani 1 1 d .
H16 H 0.7717 1.1629 0.1969 0.065 Uiso 1 1 calc R
C9 C 0.3915(2) 0.94564(13) 0.06940(13) 0.0598(4) Uani 1 1 d .
H9A H 0.4290 0.8913 0.0345 0.090 Uiso 1 1 calc R
H9B H 0.3609 1.0023 0.0197 0.090 Uiso 1 1 calc R
H9C H 0.3019 0.9226 0.0884 0.090 Uiso 1 1 calc R
C10 C 0.8315(2) 0.72804(17) 0.60934(17) 0.0831(6) Uani 1 1 d .
H10A H 0.9317 0.7424 0.6003 0.125 Uiso 1 1 calc R
H10B H 0.8439 0.6739 0.6617 0.125 Uiso 1 1 calc R
H10C H 0.7935 0.7879 0.6355 0.125 Uiso 1 1 calc R
C15 C 0.9595(2) 1.12918(15) 0.15084(15) 0.0671(5) Uani 1 1 d .
H15 H 0.9436 1.1805 0.0985 0.080 Uiso 1 1 calc R
C13 C 1.1088(2) 0.98803(15) 0.24669(19) 0.0773(6) Uani 1 1 d .
H13 H 1.1941 0.9439 0.2590 0.093 Uiso 1 1 calc R
C14 C 1.0857(3) 1.06431(16) 0.16958(18) 0.0788(6) Uani 1 1 d .
H14 H 1.1557 1.0719 0.1302 0.095 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C11 120.24(11)
C1 N1 C3 122.11(12)
C11 N1 C3 117.56(11)
C4 O2 C9 116.70(12)
C8 C3 C4 120.56(13)
C8 C3 N1 119.63(12)
C4 C3 N1 119.81(12)
C7 O3 C10 117.75(13)
O2 C4 C5 124.08(13)
O2 C4 C3 117.56(12)
C5 C4 C3 118.35(13)
O1 C1 N1 121.28(13)
O1 C1 C2 121.42(14)
N1 C1 C2 117.29(13)
C3 C8 C7 120.18(14)
C3 C8 H8 119.9
C7 C8 H8 119.9
C6 C5 C4 120.79(14)
C6 C5 H5 119.6
C4 C5 H5 119.6
C12 C11 C16 119.80(15)
C12 C11 N1 120.00(14)
C16 C11 N1 120.20(13)
O3 C7 C6 115.92(13)
O3 C7 C8 124.85(14)
C6 C7 C8 119.23(14)
C7 C6 C5 120.85(14)
C7 C6 H6 119.6
C5 C6 H6 119.6
C1 C2 H2A 109.5
C1 C2 H2B 109.5
H2A C2 H2B 109.5
C1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C11 C12 C13 119.29(17)
C11 C12 H12 120.4
C13 C12 H12 120.4
C15 C16 C11 120.51(16)
C15 C16 H16 119.7
C11 C16 H16 119.7
O2 C9 H9A 109.5
O2 C9 H9B 109.5
H9A C9 H9B 109.5
O2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O3 C10 H10A 109.5
O3 C10 H10B 109.5
H10A C10 H10B 109.5
O3 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C14 C15 C16 120.05(18)
C14 C15 H15 120.0
C16 C15 H15 120.0
C14 C13 C12 120.39(18)
C14 C13 H13 119.8
C12 C13 H13 119.8
C15 C14 C13 119.96(18)
C15 C14 H14 120.0
C13 C14 H14 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2220(16)
N1 C1 1.3660(18)
N1 C11 1.4418(18)
N1 C3 1.4431(17)
O2 C4 1.3671(17)
O2 C9 1.4288(19)
C3 C8 1.3866(19)
C3 C4 1.3923(19)
O3 C7 1.3672(18)
O3 C10 1.419(2)
C4 C5 1.389(2)
C1 C2 1.497(2)
C8 C7 1.387(2)
C8 H8 0.9300
C5 C6 1.376(2)
C5 H5 0.9300
C11 C12 1.376(2)
C11 C16 1.384(2)
C7 C6 1.374(2)
C6 H6 0.9300
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C12 C13 1.394(3)
C12 H12 0.9300
C16 C15 1.374(2)
C16 H16 0.9300
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C15 C14 1.371(3)
C15 H15 0.9300
C13 C14 1.376(3)
C13 H13 0.9300
C14 H14 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651661
