#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:17:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178378 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/00/4020017.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_4020017
loop_
_publ_author_name
'Francesca Aulenta'
'Michael G.B. Drew'
'Alison Foster'
'Wayne Hayes'
'Steven Rannard'
'David W. Thornthwaite'
'David R. Worrall'
'Tristan G.A. Youngs'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              63
_journal_page_last               78
_journal_paper_doi               10.1021/jo048799a
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C12 H14 N2 O2'
_chemical_formula_weight         218.25
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 98.771(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.600(15)
_cell_length_b                   6.370(9)
_cell_length_c                   14.560(17)
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_cell_volume                     1155(3)
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Marresearch Image Plate'
_diffrn_measurement_method
'95 frames at 2^o intervals, counting time 2 min.'
_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  0.0736
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6891
_diffrn_reflns_theta_max         25.82
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_ls_extinction_coef       0.012(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.1562
_refine_ls_R_factor_gt           0.1129
_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)+(0.1139P)²+1.7028P] where P=(Fo²+2Fc²)/3'
_refine_ls_wR_factor_gt          0.2632
_refine_ls_wR_factor_ref         0.2979
_reflns_number_gt                1505
_reflns_number_total             2119
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4020017
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C6 C 0.8052(3) 0.4348(7) 0.6636(3) 0.0371(11) Uani 1 d . . .
C1 C 0.8001(3) 0.5282(7) 0.7503(3) 0.0401(12) Uani 1 d . . .
H1A H 0.7566 0.4692 0.7897 0.048 Uiso 1 calc R . .
C2 C 0.8591(3) 0.7073(7) 0.7779(3) 0.0375(11) Uani 1 d . . .
N2 N 0.8579(4) 0.7962(7) 0.8653(3) 0.0568(13) Uani 1 d . . .
H2A1 H 0.8200 0.7399 0.9031 0.068 Uiso 1 calc R . .
H2A2 H 0.8949 0.9072 0.8813 0.068 Uiso 1 calc R . .
C3 C 0.9241(3) 0.7959(7) 0.7184(3) 0.0362(11) Uani 1 d . . .
H3 H 0.9632 0.9168 0.7362 0.043 Uiso 1 calc R . .
C4 C 0.9309(3) 0.7040(7) 0.6321(3) 0.0363(11) Uani 1 d . . .
C5 C 0.8714(4) 0.5250(7) 0.6050(3) 0.0398(11) Uani 1 d . . .
H5 H 0.8754 0.4644 0.5475 0.048 Uiso 1 calc R . .
C61 C 0.7420(4) 0.2448(7) 0.6370(3) 0.0438(12) Uani 1 d . . .
H61 H 0.6995 0.1964 0.6794 0.053 Uiso 1 calc R . .
C62 C 0.7387(4) 0.1342(8) 0.5592(4) 0.0498(13) Uani 1 d . . .
H62 H 0.7816 0.1805 0.5166 0.060 Uiso 1 calc R . .
C63 C 0.6742(4) -0.0527(8) 0.5344(4) 0.0505(13) Uani 1 d . . .
O63 O 0.6748(3) -0.1504(7) 0.4636(3) 0.0772(14) Uani 1 d . . .
C65 C 0.5458(4) -0.2904(9) 0.5763(4) 0.0650(17) Uani 1 d . . .
H651 H 0.5905 -0.4111 0.5684 0.078 Uiso 1 calc R . .
H652 H 0.4962 -0.2694 0.5192 0.078 Uiso 1 calc R . .
C67 C 0.4227(15) -0.432(3) 0.6549(12) 0.271(10) Uani 1 d . . .
H67A H 0.4000 -0.5144 0.6029 0.325 Uiso 1 calc R . .
H67B H 0.3892 -0.4443 0.7073 0.325 Uiso 1 calc R . .
C66 C 0.4868(9) -0.3241(16) 0.6544(8) 0.134(4) Uani 1 d . . .
H66 H 0.5071 -0.2446 0.7078 0.160 Uiso 1 calc R . .
N4 N 1.0022(4) 0.7853(7) 0.5757(3) 0.0560(13) Uani 1 d . . .
H41 H 1.0091 0.7242 0.5242 0.067 Uiso 1 calc R . .
H42 H 1.0390 0.8962 0.5926 0.067 Uiso 1 calc R . .
O64 O 0.6121(3) -0.1043(5) 0.5980(3) 0.0565(10) Uani 1 d . . .
