#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/59/1515955.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_1515955
loop_
_publ_author_name
'Ayitou, Anoklase Jean-Luc'
'Ugrinov, Angel'
'Sivaguru, J.'
_publ_section_title
;
 6pi-Photocyclization of O-tert-butylacrylanilides. N-substitution
 dictates the regiochemistry of cyclization.
;
_journal_issue                   6
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              751
_journal_page_last               754
_journal_paper_doi               10.1039/b903861b
_journal_volume                  8
_journal_year                    2009
_chemical_formula_sum            'C15 H21 N O'
_chemical_formula_weight         231.33
_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                 108.04(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.120(16)
_cell_length_b                   10.165(15)
_cell_length_c                   12.745(18)
_cell_measurement_reflns_used    895
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.80
_cell_measurement_theta_min      3.54
_cell_volume                     1370(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6779
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.692683
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.047(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1325P)²+0.2400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1872
_refine_ls_wR_factor_ref         0.2029
_reflns_number_gt                1905
_reflns_number_total             2388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b903861b.txt
_cod_data_source_block           Structure_4c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1515955
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
C1 C 1.0919(3) 0.0875(3) 0.1570(3) 0.0781(8) Uani 1 1 d .
H1A H 1.1166 0.0496 0.2296 0.117 Uiso 0.50 1 calc PR
H1B H 1.1496 0.1568 0.1544 0.117 Uiso 0.50 1 calc PR
H1C H 1.0935 0.0210 0.1040 0.117 Uiso 0.50 1 calc PR
H1D H 1.1232 0.1020 0.0958 0.117 Uiso 0.50 1 calc PR
H1E H 1.0902 -0.0052 0.1709 0.117 Uiso 0.50 1 calc PR
H1F H 1.1462 0.1306 0.2213 0.117 Uiso 0.50 1 calc PR
C2 C 0.8993(3) 0.2000(3) 0.0375(2) 0.0682(7) Uani 1 1 d .
H2A H 0.9361 0.2097 -0.0184 0.082 Uiso 1 1 calc R
H2B H 0.8180 0.2315 0.0276 0.082 Uiso 1 1 calc R
C3 C 0.96255(19) 0.1416(2) 0.13101(16) 0.0441(5) Uani 1 1 d .
C4 C 0.90835(16) 0.13878(18) 0.22354(14) 0.0371(5) Uani 1 1 d .
C5 C 0.7887(2) -0.0600(2) 0.13960(19) 0.0557(6) Uani 1 1 d .
H5A H 0.7177 -0.1095 0.1457 0.084 Uiso 0.50 1 calc PR
H5B H 0.8622 -0.1154 0.1577 0.084 Uiso 0.50 1 calc PR
H5C H 0.7710 -0.0283 0.0654 0.084 Uiso 0.50 1 calc PR
H5D H 0.8496 -0.0593 0.1002 0.084 Uiso 0.50 1 calc PR
H5E H 0.7051 -0.0534 0.0882 0.084 Uiso 0.50 1 calc PR
H5F H 0.7962 -0.1405 0.1805 0.084 Uiso 0.50 1 calc PR
C6 C 0.77044(16) 0.03528(17) 0.31188(14) 0.0350(5) Uani 1 1 d .
C7 C 0.65991(16) 0.09210(17) 0.32239(14) 0.0358(5) Uani 1 1 d .
C8 C 0.63140(19) 0.0589(2) 0.41792(16) 0.0446(5) Uani 1 1 d .
H8 H 0.5590 0.0941 0.4288 0.054 Uiso 1 1 calc R
C9 C 0.7062(2) -0.0241(2) 0.49732(17) 0.0529(6) Uani 1 1 d .
H9 H 0.6829 -0.0440 0.5596 0.063 Uiso 1 1 calc R
C10 C 0.8136(2) -0.0772(2) 0.48555(17) 0.0529(6) Uani 1 1 d .
H10 H 0.8644 -0.1323 0.5395 0.063 Uiso 1 1 calc R
C11 C 0.84537(19) -0.0477(2) 0.39269(17) 0.0459(6) Uani 1 1 d .
H11 H 0.9183 -0.0838 0.3835 0.055 Uiso 1 1 calc R
C12 C 0.57480(18) 0.18848(19) 0.23877(17) 0.0430(5) Uani 1 1 d .
C13 C 0.6472(2) 0.3166(2) 0.2386(2) 0.0669(7) Uani 1 1 d .
H13A H 0.7230 0.2979 0.2204 0.100 Uiso 1 1 calc R
H13B H 0.6690 0.3563 0.3104 0.100 Uiso 1 1 calc R
H13C H 0.5951 0.3759 0.1849 0.100 Uiso 1 1 calc R
C14 C 0.5310(3) 0.1313(3) 0.1222(2) 0.0742(8) Uani 1 1 d .
H14A H 0.6035 0.1072 0.1006 0.111 Uiso 1 1 calc R
H14B H 0.4823 0.1959 0.0719 0.111 Uiso 1 1 calc R
H14C H 0.4799 0.0548 0.1209 0.111 Uiso 1 1 calc R
C15 C 0.4556(2) 0.2242(3) 0.2676(3) 0.0727(8) Uani 1 1 d .
H15A H 0.4053 0.2843 0.2135 0.109 Uiso 1 1 calc R
H15B H 0.4787 0.2650 0.3391 0.109 Uiso 1 1 calc R
H15C H 0.4075 0.1460 0.2685 0.109 Uiso 1 1 calc R
N1 N 0.81224(14) 0.05327(15) 0.21690(12) 0.0380(5) Uani 1 1 d .
O1 O 0.94893(14) 0.21355(15) 0.30153(11) 0.0527(5) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 C1 H1A 109.5
C3 C1 H1B 109.5
H1A C1 H1B 109.5
C3 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C1 H1D 109.5
H1A C1 H1D 141.1
H1B C1 H1D 56.3
H1C C1 H1D 56.3
C3 C1 H1E 109.5
H1A C1 H1E 56.3
H1B C1 H1E 141.1
H1C C1 H1E 56.3
H1D C1 H1E 109.5
C3 C1 H1F 109.5
H1A C1 H1F 56.3
H1B C1 H1F 56.3
H1C C1 H1F 141.1
H1D C1 H1F 109.5
H1E C1 H1F 109.5
C3 C2 H2A 120.0
C3 C2 H2B 120.0
H2A C2 H2B 120.0
C2 C3 C1 125.3(2)
C2 C3 C4 119.5(2)
C1 C3 C4 114.93(19)
O1 C4 N1 122.25(17)
O1 C4 C3 119.80(18)
N1 C4 C3 117.94(16)
N1 C5 H5A 109.5
N1 C5 H5B 109.5
H5A C5 H5B 109.5
N1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N1 C5 H5D 109.5
H5A C5 H5D 141.1
H5B C5 H5D 56.3
H5C C5 H5D 56.3
N1 C5 H5E 109.5
H5A C5 H5E 56.3
H5B C5 H5E 141.1
H5C C5 H5E 56.3
H5D C5 H5E 109.5
N1 C5 H5F 109.5
H5A C5 H5F 56.3
H5B C5 H5F 56.3
H5C C5 H5F 141.1
H5D C5 H5F 109.5
H5E C5 H5F 109.5
C11 C6 C7 121.40(18)
C11 C6 N1 115.16(18)
C7 C6 N1 123.39(17)
C8 C7 C6 115.34(17)
C8 C7 C12 120.17(18)
C6 C7 C12 124.46(17)
C9 C8 C7 122.7(2)
C9 C8 H8 118.6
C7 C8 H8 118.6
C10 C9 C8 120.8(2)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 C11 118.6(2)
C9 C10 H10 120.7
C11 C10 H10 120.7
C10 C11 C6 121.1(2)
C10 C11 H11 119.4
C6 C11 H11 119.4
C15 C12 C14 106.6(2)
C15 C12 C13 107.1(2)
C14 C12 C13 109.3(2)
C15 C12 C7 112.26(19)
C14 C12 C7 111.94(19)
C13 C12 C7 109.37(19)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C4 N1 C6 118.83(15)
C4 N1 C5 120.70(16)
C6 N1 C5 115.07(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C3 1.478(4)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C1 H1D 0.9600
C1 H1E 0.9600
C1 H1F 0.9600
C2 C3 1.323(3)
C2 H2A 0.9300
C2 H2B 0.9300
C3 C4 1.482(3)
C4 O1 1.221(2)
C4 N1 1.360(3)
C5 N1 1.485(3)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C5 H5D 0.9600
C5 H5E 0.9600
C5 H5F 0.9600
C6 C11 1.391(3)
C6 C7 1.401(3)
C6 N1 1.436(3)
C7 C8 1.391(3)
C7 C12 1.538(3)
C8 C9 1.381(3)
C8 H8 0.9300
C9 C10 1.361(4)
C9 H9 0.9300
C10 C11 1.369(3)
C10 H10 0.9300
C11 H11 0.9300
C12 C15 1.526(3)
C12 C14 1.528(4)
C12 C13 1.531(4)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
