data_2016sot0035_s1_100k
_audit_creation_date              2016-05-18
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
loop_
  _publ_author_name
  _publ_author_email
  _publ_author_address
 'Light, M.E.' light@soton.ac.uk
;
University Road Highfield
Southampton
;
 'Hofman, G.' gh2c14@soton.ac.uk
;
University Road Highfield
Southampton
;
 'Linclau, B.' bruno.linclau@soton.ac.uk
;
University Road Highfield
Southampton
;

_publ_contact_author_address
;
University Road Highfield
Southampton
;
_publ_contact_author_email        light@soton.ac.uk
_publ_contact_author_name         'Light, M.E.'
_publ_contact_author_phone        02380599429
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C14 H15 N O4'
_chemical_formula_sum             'C14 H15 N O4'
_chemical_formula_weight          261.27
_chemical_melting_point           ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system       'orthorhombic'
_space_group_IT_number            61
_space_group_name_H-M_alt         'P b c a'
_space_group_name_Hall            '-P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'

_cell_length_a                    7.4200(2)
_cell_length_b                    13.6927(3)
_cell_length_c                    24.5834(5)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2497.67(10)
_cell_formula_units_Z             8
_cell_measurement_reflns_used     26524
_cell_measurement_temperature     100(2)
_cell_measurement_theta_max       71.836
_cell_measurement_theta_min       3.596
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     0.851
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_correction_T_min   0.6695
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan 
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             'clear colourless'
_exptl_crystal_colour_lustre      clear
_exptl_crystal_colour_modifier    .
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.390
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        slab
_exptl_crystal_F_000              1104
_exptl_crystal_recrystallization_method
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max           0.47
_exptl_crystal_size_mid           0.45
_exptl_crystal_size_min           0.14
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0317
_diffrn_reflns_av_unetI/netI      0.0159
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_l_max        28
_diffrn_reflns_limit_l_min        -30
_diffrn_reflns_number             26524
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full         67.687
_diffrn_reflns_theta_max          71.836
_diffrn_reflns_theta_min          3.596
_diffrn_ambient_temperature       100(2)
_diffrn_detector                  'Image plate'
_diffrn_detector_area_resol_mean  10
_diffrn_detector_type             'Rigaku Curved Fujifilm'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device        'three-circle quarter χ goniometer'
_diffrn_measurement_device_type   'Rigaku R-AXIS Spider'
_diffrn_measurement_device_type2  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method        'profile data from oscillation ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation     0.5
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            CuK\a
_diffrn_radiation_wavelength      1.54187
_diffrn_source                    'sealed x-ray tube'
_diffrn_source_current            55.0
_diffrn_source_power              2.475
_diffrn_source_target             Cu
_diffrn_source_voltage            45.0
_diffrn_special_details           ?
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 2375
_reflns_number_total              2432
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement
;
Rigaku (2004). RAPID-AUTO Ver. 3.1.1 Rigaku Corporation, Tokyo, Japan 
;
_computing_data_collection
;
Rigaku (2004). RAPID-AUTO Ver. 3.1.1 Rigaku Corporation, Tokyo, Japan 
;
_computing_data_reduction
;
Rigaku (2004). RAPID-AUTO Ver. 3.1.1 Rigaku Corporation, Tokyo, Japan 
;
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution     'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max          0.212
_refine_diff_density_min          -0.207
_refine_diff_density_rms          0.046
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.095
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      173
_refine_ls_number_reflns          2432
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0382
_refine_ls_R_factor_gt            0.0373
_refine_ls_restrained_S_all       1.095
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0402P)²+1.2440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0914
_refine_ls_wR_factor_ref          0.0920
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    ?
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_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O 0.89638(14) 0.58920(7) 0.62201(4) 0.0300(2) Uani 1 1 d . . . . .
 O2 O 0.58564(14) 0.31000(7) 0.69137(4) 0.0308(2) Uani 1 1 d . . . . .
 O3 O 0.48973(13) 0.52178(7) 0.65265(4) 0.0293(2) Uani 1 1 d . . . . .
 O4 O 0.49428(11) 0.46040(6) 0.56717(3) 0.0214(2) Uani 1 1 d . . . . .
 N1 N 0.84536(15) 0.45050(8) 0.66767(4) 0.0224(2) Uani 1 1 d . . . . .
 C1 C 1.0575(2) 0.56852(11) 0.70587(6) 0.0315(3) Uani 1 1 d . . . . .
 H1A H 1.1754 0.5388 0.6989 0.047 Uiso 1 1 calc GR . . . .
 H1B H 1.0125 0.5469 0.7414 0.047 Uiso 1 1 calc GR . . . .
 H1C H 1.0694 0.6398 0.7058 0.047 Uiso 1 1 calc GR . . . .
 C2 C 0.92732(18) 0.53804(10) 0.66213(5) 0.0242(3) Uani 1 1 d . . . . .
 C3 C 0.8891(2) 0.37536(10) 0.70840(5) 0.0281(3) Uani 1 1 d . . . . .
 H3A H 0.8561 0.3973 0.7455 0.034 Uiso 1 1 calc R . . . .
 H3B H 1.0190 0.3591 0.7077 0.034 Uiso 1 1 calc R . . . .
 C4 C 0.7771(2) 0.28973(11) 0.69127(6) 0.0297(3) Uani 1 1 d . . . . .
 H4 H 0.8209 0.2219 0.6985 0.036 Uiso 1 1 calc R . . . .
 C5 C 0.68397(18) 0.31160(10) 0.64053(5) 0.0250(3) Uani 1 1 d . . . . .
 H5 H 0.6646 0.2595 0.6126 0.030 Uiso 1 1 calc R . . . .
 C6 C 0.73216(18) 0.41486(9) 0.62353(5) 0.0212(3) Uani 1 1 d . . . . .
 H6 H 0.8012 0.4141 0.5886 0.025 Uiso 1 1 calc R . . . .
 C7 C 0.56066(18) 0.47471(9) 0.61736(5) 0.0208(3) Uani 1 1 d . . . . .
 C8 C 0.30696(17) 0.48842(9) 0.55706(5) 0.0221(3) Uani 1 1 d . . . . .
 H8A H 0.2974 0.5231 0.5219 0.027 Uiso 1 1 calc R . . . .
 H8B H 0.2641 0.5326 0.5862 0.027 Uiso 1 1 calc R . . . .
 C9 C 0.19423(17) 0.39723(9) 0.55591(5) 0.0201(3) Uani 1 1 d . . . . .
 C10 C 0.19679(17) 0.33237(9) 0.59984(5) 0.0218(3) Uani 1 1 d . . . . .
 H10 H 0.2671 0.3472 0.6311 0.026 Uiso 1 1 calc R . . . .
 C11 C 0.09781(17) 0.24671(10) 0.59827(6) 0.0246(3) Uani 1 1 d . . . . .
 H11 H 0.1016 0.2028 0.6282 0.029 Uiso 1 1 calc R . . . .
 C12 C -0.00711(18) 0.22495(10) 0.55297(6) 0.0270(3) Uani 1 1 d . . . . .
 H12 H -0.0759 0.1665 0.5520 0.032 Uiso 1 1 calc R . . . .
 C13 C -0.01104(18) 0.28878(10) 0.50928(6) 0.0264(3) Uani 1 1 d . . . . .
 H13 H -0.0831 0.2741 0.4784 0.032 Uiso 1 1 calc R . . . .
 C14 C 0.09018(17) 0.37429(10) 0.51047(5) 0.0226(3) Uani 1 1 d . . . . .
 H14 H 0.0884 0.4173 0.4801 0.027 Uiso 1 1 calc R . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 C2 1.2313(16) . ?
 O2 C4 1.4472(17) . ?
 O2 C5 1.4473(15) . ?
 O3 C7 1.2022(16) . ?
 O4 C7 1.3427(15) . ?
 O4 C8 1.4631(15) . ?
 N1 C2 1.3511(18) . ?
 N1 C3 1.4719(16) . ?
 N1 C6 1.4565(16) . ?
 C1 H1A 0.9800 . ?
 C1 H1B 0.9800 . ?
 C1 H1C 0.9800 . ?
 C1 C2 1.5046(19) . ?
 C3 H3A 0.9900 . ?
 C3 H3B 0.9900 . ?
 C3 C4 1.498(2) . ?
 C4 H4 1.0000 . ?
 C4 C5 1.4570(19) . ?
 C5 H5 1.0000 . ?
 C5 C6 1.5170(18) . ?
 C6 H6 1.0000 . ?
 C6 C7 1.5212(18) . ?
 C8 H8A 0.9900 . ?
 C8 H8B 0.9900 . ?
 C8 C9 1.5031(17) . ?
 C9 C10 1.3984(17) . ?
 C9 C14 1.3938(18) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.3844(19) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.3910(19) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.385(2) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.391(2) . ?
 C14 H14 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C4 O2 C5 60.45(8) . . ?
 C7 O4 C8 117.80(10) . . ?
 C2 N1 C3 126.14(11) . . ?
 C2 N1 C6 118.79(10) . . ?
 C6 N1 C3 113.56(11) . . ?
 H1A C1 H1B 109.5 . . ?
 H1A C1 H1C 109.5 . . ?
 H1B C1 H1C 109.5 . . ?
 C2 C1 H1A 109.5 . . ?
 C2 C1 H1B 109.5 . . ?
 C2 C1 H1C 109.5 . . ?
 O1 C2 N1 120.11(12) . . ?
 O1 C2 C1 122.31(13) . . ?
 N1 C2 C1 117.57(12) . . ?
 N1 C3 H3A 111.1 . . ?
 N1 C3 H3B 111.1 . . ?
 N1 C3 C4 103.51(11) . . ?
 H3A C3 H3B 109.0 . . ?
 C4 C3 H3A 111.1 . . ?
 C4 C3 H3B 111.1 . . ?
 O2 C4 C3 113.21(12) . . ?
 O2 C4 H4 119.8 . . ?
 O2 C4 C5 59.78(9) . . ?
 C3 C4 H4 119.8 . . ?
 C5 C4 C3 110.06(11) . . ?
 C5 C4 H4 119.8 . . ?
 O2 C5 C4 59.77(9) . . ?
 O2 C5 H5 120.6 . . ?
 O2 C5 C6 111.77(10) . . ?
 C4 C5 H5 120.6 . . ?
 C4 C5 C6 108.40(12) . . ?
 C6 C5 H5 120.6 . . ?
 N1 C6 C5 104.06(10) . . ?
 N1 C6 H6 110.4 . . ?
 N1 C6 C7 112.10(10) . . ?
 C5 C6 H6 110.4 . . ?
 C5 C6 C7 109.41(11) . . ?
 C7 C6 H6 110.4 . . ?
 O3 C7 O4 125.50(12) . . ?
 O3 C7 C6 125.67(11) . . ?
 O4 C7 C6 108.66(10) . . ?
 O4 C8 H8A 110.0 . . ?
 O4 C8 H8B 110.0 . . ?
 O4 C8 C9 108.31(10) . . ?
 H8A C8 H8B 108.4 . . ?
 C9 C8 H8A 110.0 . . ?
 C9 C8 H8B 110.0 . . ?
 C10 C9 C8 120.36(11) . . ?
 C14 C9 C8 120.70(11) . . ?
 C14 C9 C10 118.91(12) . . ?
 C9 C10 H10 119.7 . . ?
 C11 C10 C9 120.62(12) . . ?
 C11 C10 H10 119.7 . . ?
 C10 C11 H11 120.0 . . ?
 C10 C11 C12 120.05(12) . . ?
 C12 C11 H11 120.0 . . ?
 C11 C12 H12 120.1 . . ?
 C13 C12 C11 119.83(12) . . ?
 C13 C12 H12 120.1 . . ?
 C12 C13 H13 119.9 . . ?
 C12 C13 C14 120.22(12) . . ?
 C14 C13 H13 119.9 . . ?
 C9 C14 H14 119.8 . . ?
 C13 C14 C9 120.37(12) . . ?
 C13 C14 H14 119.8 . . ?

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
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 O2 C4 C5 C6 104.98(11) . . . . ?
 O2 C5 C6 N1 60.93(13) . . . . ?
 O2 C5 C6 C7 -59.03(14) . . . . ?
 O4 C8 C9 C10 55.04(15) . . . . ?
 O4 C8 C9 C14 -122.86(12) . . . . ?
 N1 C3 C4 O2 -60.41(14) . . . . ?
 N1 C3 C4 C5 4.35(15) . . . . ?
 N1 C6 C7 O3 -24.62(18) . . . . ?
 N1 C6 C7 O4 159.95(10) . . . . ?
 C2 N1 C3 C4 -172.33(12) . . . . ?
 C2 N1 C6 C5 173.00(11) . . . . ?
 C2 N1 C6 C7 -68.87(14) . . . . ?
 C3 N1 C2 O1 169.91(13) . . . . ?
 C3 N1 C2 C1 -9.13(19) . . . . ?
 C3 N1 C6 C5 6.15(14) . . . . ?
 C3 N1 C6 C7 124.28(12) . . . . ?
 C3 C4 C5 O2 -105.84(12) . . . . ?
 C3 C4 C5 C6 -0.85(15) . . . . ?
 C4 O2 C5 C6 -99.25(13) . . . . ?
 C4 C5 C6 N1 -3.06(14) . . . . ?
 C4 C5 C6 C7 -123.03(11) . . . . ?
 C5 O2 C4 C3 100.49(12) . . . . ?
 C5 C6 C7 O3 90.28(16) . . . . ?
 C5 C6 C7 O4 -85.15(12) . . . . ?
 C6 N1 C2 O1 4.88(18) . . . . ?
 C6 N1 C2 C1 -174.17(12) . . . . ?
 C6 N1 C3 C4 -6.63(15) . . . . ?
 C7 O4 C8 C9 -103.50(12) . . . . ?
 C8 O4 C7 O3 -11.93(19) . . . . ?
 C8 O4 C7 C6 163.52(10) . . . . ?
 C8 C9 C10 C11 -177.88(11) . . . . ?
 C8 C9 C14 C13 178.72(12) . . . . ?
 C9 C10 C11 C12 -0.73(19) . . . . ?
 C10 C9 C14 C13 0.79(18) . . . . ?
 C10 C11 C12 C13 0.6(2) . . . . ?
 C11 C12 C13 C14 0.3(2) . . . . ?
 C12 C13 C14 C9 -0.96(19) . . . . ?
 C14 C9 C10 C11 0.05(18) . . . . ?

_shelx_SHELXL_version_number      '2014/7'
_olex2_date_sample_submission     2016-05-04
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder silicon oil'
_olex2_submission_original_sample_id 'GJH-49 Sputz '
_olex2_submission_special_instructions 'No special instructions were received'
