#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:07:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180466 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/35/7213528.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213528
loop_
_publ_author_name
'Bernhardt, Paul V.'
'Koch, Rainer'
'Moloney, Daniel W. J.'
'Shtaiwi, Majed'
'Wentrup, Curt'
_publ_section_title
;
 Twisting and planarization in push--pull ethylenesElectronic
 supplementary information (ESI) available: tables of X-ray
 crystallographic bond lengths and angles of compounds 8--19 (including
 selected torsional angles and hydrogen bonds), X-ray crystal structures
 of compounds 10, 11, 13, 16, and 18 (Figs. S1--S5) and packing diagrams
 for 17·H2O and 19·H2O (Figs. S6--S7). See
 http://www.rsc.org/suppdata/p2/b1/b109624a/
;
_journal_issue                   3
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              515
_journal_paper_doi               10.1039/b109624a
_journal_year                    2002
_chemical_formula_sum            'C14 H15 N O5'
_chemical_formula_weight         277.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2001-10-16T10:36:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                96.940(6)
_cell_angle_beta                 99.553(8)
_cell_angle_gamma                105.438(7)
_cell_formula_units_Z            2
_cell_length_a                   6.2148(6)
_cell_length_b                   9.5460(6)
_cell_length_c                   12.0590(10)
_cell_measurement_temperature    297(2)
_cell_volume                     669.72(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2543
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9691
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0804P)²+0.0976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1542
_reflns_number_gt                1361
_reflns_number_total             2317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b109624asup1.cif
_cod_data_source_block           989dm3
_cod_database_code               7213528
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C2 C 0.1572(5) 0.4323(3) 0.6699(2) 0.0437(7) Uani 1 1 d .
C4 C 0.0408(5) 0.3094(3) 0.8217(3) 0.0422(7) Uani 1 1 d .
C5 C -0.1814(4) 0.2498(3) 0.7473(2) 0.0383(7) Uani 1 1 d .
C6 C -0.1981(5) 0.2376(3) 0.6260(2) 0.0422(7) Uani 1 1 d .
C7 C -0.3716(5) 0.1754(3) 0.7893(2) 0.0411(7) Uani 1 1 d .
C10 C -0.3189(6) 0.3523(4) 0.9607(3) 0.0662(10) Uani 1 1 d .
H10A H -0.3472 0.3508 1.0365 0.099 Uiso 1 1 calc R
H10B H -0.4018 0.4108 0.9229 0.099 Uiso 1 1 calc R
H10C H -0.1586 0.3942 0.9648 0.099 Uiso 1 1 calc R
C11 C -0.7601(5) -0.0051(3) 0.7462(2) 0.0382(6) Uani 1 1 d .
C12 C -0.9408(5) -0.0505(3) 0.6544(3) 0.0472(7) Uani 1 1 d .
H12 H -0.9178 -0.0321 0.5826 0.057 Uiso 1 1 calc R
C13 C -1.1571(5) -0.1235(3) 0.6678(3) 0.0569(9) Uani 1 1 d .
H13 H -1.2795 -0.1528 0.6057 0.068 Uiso 1 1 calc R
C14 C -1.1887(6) -0.1521(3) 0.7732(3) 0.0605(9) Uani 1 1 d .
H14 H -1.3339 -0.1999 0.7829 0.073 Uiso 1 1 calc R
C15 C -1.0090(6) -0.1111(3) 0.8645(3) 0.0619(9) Uani 1 1 d .
H15 H -1.0318 -0.1328 0.9355 0.074 Uiso 1 1 calc R
C16 C -0.7930(5) -0.0373(3) 0.8512(3) 0.0533(8) Uani 1 1 d .
H16 H -0.6705 -0.0096 0.9133 0.064 Uiso 1 1 calc R
C21 C 0.0746(6) 0.5653(3) 0.6932(3) 0.0582(9) Uani 1 1 d .
H21A H 0.0374 0.5999 0.623 0.087 Uiso 1 1 calc R
H21B H 0.1923 0.6419 0.7458 0.087 Uiso 1 1 calc R
H21C H -0.0586 0.5389 0.7256 0.087 Uiso 1 1 calc R
C22 C 0.3650(6) 0.4617(4) 0.6182(3) 0.0663(10) Uani 1 1 d .
H22A H 0.3338 0.4987 0.5486 0.099 Uiso 1 1 calc R
H22B H 0.4044 0.3718 0.6022 0.099 Uiso 1 1 calc R
H22C H 0.4898 0.5335 0.6707 0.099 Uiso 1 1 calc R
N1 N -0.5439(4) 0.0698(2) 0.7232(2) 0.0430(6) Uani 1 1 d .
O1 O -0.0152(3) 0.3170(2) 0.58888(16) 0.0481(5) Uani 1 1 d .
O2 O -0.3936(4) 0.2017(2) 0.89663(17) 0.0554(6) Uani 1 1 d .
O3 O 0.2150(3) 0.3777(2) 0.77249(17) 0.0479(5) Uani 1 1 d .
O4 O 0.0929(3) 0.2998(2) 0.92111(18) 0.0552(6) Uani 1 1 d .
O6 O -0.3584(3) 0.1606(2) 0.55122(16) 0.0534(6) Uani 1 1 d .
H1 H -0.535(6) 0.058(3) 0.646(3) 0.065(10) Uiso 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 0 '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 0.006 '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
O3 C2 O1 109.4(2)
O3 C2 C22 106.6(2)
O1 C2 C22 105.5(2)
O3 C2 C21 111.1(2)
O1 C2 C21 110.4(2)
C22 C2 C21 113.7(3)
O4 C4 O3 116.3(3)
O4 C4 C5 127.4(3)
O3 C4 C5 116.2(2)
C7 C5 C6 119.1(2)
C7 C5 C4 120.7(3)
C6 C5 C4 118.8(2)
O6 C6 O1 115.7(3)
O6 C6 C5 126.9(3)
O1 C6 C5 117.4(2)
N1 C7 O2 113.9(3)
N1 C7 C5 121.9(3)
O2 C7 C5 124.2(2)
C12 C11 C16 119.6(3)
C12 C11 N1 116.1(3)
C16 C11 N1 124.2(3)
C11 C12 C13 120.6(3)
C14 C13 C12 119.3(3)
C13 C14 C15 120.6(3)
C14 C15 C16 120.0(3)
C11 C16 C15 119.8(3)
C7 N1 C11 129.7(3)
C6 O1 C2 118.3(2)
C7 O2 C10 120.7(2)
C4 O3 C2 118.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 O3 1.428(3)
C2 O1 1.442(3)
C2 C22 1.500(4)
C2 C21 1.504(4)
C4 O4 1.209(3)
C4 O3 1.372(3)
C4 C5 1.443(4)
C5 C7 1.413(4)
C5 C6 1.437(4)
C6 O6 1.224(3)
C6 O1 1.363(3)
C7 N1 1.321(3)
C7 O2 1.325(3)
C10 O2 1.462(4)
C11 C12 1.374(4)
C11 C16 1.374(4)
C11 N1 1.433(3)
C12 C13 1.385(4)
C13 C14 1.366(4)
C14 C15 1.367(5)
C15 C16 1.386(4)
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
O4 C4 C5 C7 2.9(5)
O3 C4 C5 C7 179.1(2)
O4 C4 C5 C6 -163.4(3)
O3 C4 C5 C6 12.8(4)
C7 C5 C6 O6 -4.9(4)
C4 C5 C6 O6 161.6(3)
C7 C5 C6 O1 176.7(2)
C4 C5 C6 O1 -16.8(4)
C6 C5 C7 N1 15.6(4)
C4 C5 C7 N1 -150.7(3)
C6 C5 C7 O2 -165.6(3)
C4 C5 C7 O2 28.1(4)
C16 C11 C12 C13 2.4(4)
N1 C11 C12 C13 -179.8(3)
C11 C12 C13 C14 -1.0(5)
C12 C13 C14 C15 -0.9(5)
C13 C14 C15 C16 1.3(5)
C12 C11 C16 C15 -2.0(4)
N1 C11 C16 C15 -179.5(3)
C14 C15 C16 C11 0.2(5)
O2 C7 N1 C11 9.3(4)
C5 C7 N1 C11 -171.8(3)
C12 C11 N1 C7 148.1(3)
C16 C11 N1 C7 -34.3(4)
O6 C6 O1 C2 167.1(2)
C5 C6 O1 C2 -14.3(4)
O3 C2 O1 C6 46.7(3)
C22 C2 O1 C6 161.0(2)
C21 C2 O1 C6 -75.9(3)
N1 C7 O2 C10 -142.1(3)
C5 C7 O2 C10 39.1(4)
O4 C4 O3 C2 -160.9(3)
C5 C4 O3 C2 22.4(3)
O1 C2 O3 C4 -51.1(3)
C22 C2 O3 C4 -164.6(2)
C21 C2 O3 C4 71.0(3)
