#------------------------------------------------------------------------------
#$Date: 2021-10-07 17:27:16 +0300 (Thu, 07 Oct 2021) $
#$Revision: 269852 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/30/06/2300680.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2300680
loop_
_publ_author_name
'Saunders, Lucy K.'
'Yeung, Hamish H.-M.'
'Warren, Mark R.'
'Smith, Peter'
'Gurney, Stuart'
'Dodsworth, Stephen F.'
'Vitorica-Yrezabal, Inigo J.'
'Wilcox, Adrian'
'Hathaway, Paul V.'
'Preece, Geoff'
'Roberts, Paul'
'Barnett, Sarah A.'
'Allan, David R.'
_publ_section_title
;
 An electric field cell for performing in situ single-crystal
 synchrotron X-ray diffraction
;
_journal_coeditor_code           OC5009
_journal_issue                   5
_journal_name_full               'Journal of Applied Crystallography'
_journal_page_first              1349
_journal_page_last               1359
_journal_paper_doi               10.1107/S1600576721007469
_journal_volume                  54
_journal_year                    2021
_chemical_formula_moiety         'C4 H O4, C10 H9 N2'
_chemical_formula_sum            'C14 H10 N2 O4'
_chemical_formula_weight         270.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-10
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.05.22 svn.r1d9e7f8d for OlexSys, GUI svn.r6115)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.272(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.80060(10)
_cell_length_b                   11.2125(3)
_cell_length_c                   27.4464(7)
_cell_measurement_reflns_used    8249
_cell_measurement_temperature    298
_cell_measurement_theta_max      20.76084559407034
_cell_measurement_theta_min      1.4664333493907515
_cell_volume                     1168.69(5)
_computing_cell_refinement
'DIALS 2theta refinement, DIALS 3.0.4-g47491215a-release'
_computing_data_collection       'GDA - generic data acquisition software'
_computing_data_reduction
;
DIALS 3.0.4-g47491215a-release (Winter, G. et al., 2018)
dials.scale (Beilsten-Edmands, J. et al., 2020)
XIA2 0.7.50-gf263449d-dials-3.0 (Winter, G., 2010)
;
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            'Dectris PILATUS 300K'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       '4-circle κ-geometry diffractometer'
_diffrn_measurement_device_type  'Newport IS4CCD'
_diffrn_measurement_method       'shutterless scans'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_wavelength     0.534
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            15333
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        18.687
_diffrn_reflns_theta_max         20.793
_diffrn_reflns_theta_min         1.116
_diffrn_source                   Synchrotron
_diffrn_source_details           'Nowell et al. (2012)'
_diffrn_source_type              'Diamond Light Source Beamline I19-2'
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.999590000075973
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
DIALS 3.0.4-g47491215a-release
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          2.0
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0418
_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)+(0.0673P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2159
_reflns_number_total             2791
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oc5009sup1.cif
_cod_data_source_block           SQABPY_before_voltage_0V
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 2300680--2300682.cif.
;
_cod_database_code               2300680
_cod_database_fobs_code          2300680
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_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
O2 O 0.0629(3) 0.87501(8) 0.55273(3) 0.0420(3) Uani 1 1 d . . . . .
O4 O -0.3954(3) 0.60504(8) 0.65785(4) 0.0483(3) Uani 1 1 d . . . . .
O1 O -0.2815(3) 0.89163(8) 0.65817(3) 0.0471(3) Uani 1 1 d . . . . .
O3 O -0.0267(3) 0.58927(9) 0.55291(4) 0.0556(3) Uani 1 1 d . . . . .
N2 N 0.3440(3) 0.79559(10) 0.47411(4) 0.0348(3) Uani 1 1 d . . . . .
N1 N 0.9662(3) 0.67444(10) 0.24155(4) 0.0402(3) Uani 1 1 d . . . . .
C7 C 0.6122(3) 0.74910(10) 0.38452(4) 0.0280(3) Uani 1 1 d . . . . .
C10 C 0.7412(3) 0.72423(11) 0.33518(4) 0.0295(3) Uani 1 1 d . . . . .
C14 C 0.8946(4) 0.61552(11) 0.32435(4) 0.0328(3) Uani 1 1 d . . . . .
C2 C -0.0594(4) 0.80016(11) 0.58212(4) 0.0321(3) Uani 1 1 d . . . . .
C8 C 0.5200(4) 0.65642(11) 0.41554(4) 0.0333(3) Uani 1 1 d . . . . .
C4 C -0.2665(4) 0.67641(11) 0.62968(4) 0.0333(3) Uani 1 1 d . . . . .
C1 C -0.2128(4) 0.80399(11) 0.62816(4) 0.0321(3) Uani 1 1 d . . . . .
C6 C 0.5716(4) 0.86596(11) 0.40082(4) 0.0351(3) Uani 1 1 d . . . . .
C3 C -0.0999(4) 0.66863(11) 0.58107(4) 0.0352(3) Uani 1 1 d . . . . .
C13 C 1.0063(4) 0.59539(12) 0.27773(5) 0.0366(3) Uani 1 1 d . . . . .
C11 C 0.7055(4) 0.80765(12) 0.29774(4) 0.0384(3) Uani 1 1 d . . . . .
C5 C 0.4338(4) 0.88627(12) 0.44550(5) 0.0375(3) Uani 1 1 d . . . . .
C9 C 0.3857(4) 0.68179(12) 0.46029(4) 0.0354(3) Uani 1 1 d . . . . .
C12 C 0.8174(4) 0.77922(13) 0.25183(5) 0.0434(4) Uani 1 1 d . . . . .
H13 H 1.114(4) 0.5215(14) 0.2696(5) 0.045(4) Uiso 1 1 d . . . . .
H14 H 0.931(4) 0.5513(13) 0.3490(5) 0.048(4) Uiso 1 1 d . . . . .
H8 H 0.547(4) 0.5737(13) 0.4063(5) 0.041(4) Uiso 1 1 d . . . . .
H9 H 0.305(4) 0.6227(12) 0.4825(5) 0.038(4) Uiso 1 1 d . . . . .
H5 H 0.401(4) 0.9672(14) 0.4575(5) 0.047(4) Uiso 1 1 d . . . . .
H12 H 0.789(4) 0.8347(15) 0.2248(6) 0.054(4) Uiso 1 1 d . . . . .
H11 H 0.600(4) 0.8860(13) 0.3033(5) 0.048(4) Uiso 1 1 d . . . . .
H6 H 0.635(4) 0.9348(14) 0.3808(5) 0.045(4) Uiso 1 1 d . . . . .
H2 H 0.230(6) 0.8178(18) 0.5083(7) 0.084(6) Uiso 1 1 d . . . . .
H1 H -0.389(6) 0.8533(19) 0.6908(7) 0.095(7) 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 0.0012 0.0008 '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 0.0027 0.0017 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0054 0.0032 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 108.1(11) . . ?
C5 N2 C9 121.40(11) . . ?
C5 N2 H2 117.2(11) . . ?
C9 N2 H2 121.4(11) . . ?
C13 N1 C12 117.56(11) . . ?
C8 C7 C10 121.07(11) . . ?
C6 C7 C10 120.91(11) . . ?
C6 C7 C8 118.00(11) . . ?
C14 C10 C7 121.11(11) . . ?
C14 C10 C11 117.47(11) . . ?
C11 C10 C7 121.40(11) . . ?
C10 C14 H14 122.5(9) . . ?
C13 C14 C10 119.23(11) . . ?
C13 C14 H14 118.2(9) . . ?
O2 C2 C1 136.47(11) . . ?
O2 C2 C3 133.45(11) . . ?
C1 C2 C3 90.08(10) . . ?
C7 C8 H8 121.4(9) . . ?
C9 C8 C7 120.02(12) . . ?
C9 C8 H8 118.6(9) . . ?
O4 C4 C1 136.31(12) . . ?
O4 C4 C3 135.58(12) . . ?
C1 C4 C3 88.10(9) . . ?
O1 C1 C2 133.00(11) . . ?
O1 C1 C4 133.59(11) . . ?
C2 C1 C4 93.41(10) . . ?
C7 C6 H6 121.7(9) . . ?
C5 C6 C7 119.60(12) . . ?
C5 C6 H6 118.7(9) . . ?
O3 C3 C2 135.45(12) . . ?
O3 C3 C4 136.15(12) . . ?
C2 C3 C4 88.40(9) . . ?
N1 C13 C14 123.34(13) . . ?
N1 C13 H13 116.1(9) . . ?
C14 C13 H13 120.5(9) . . ?
C10 C11 H11 121.0(8) . . ?
C12 C11 C10 119.54(13) . . ?
C12 C11 H11 119.4(8) . . ?
N2 C5 C6 120.94(12) . . ?
N2 C5 H5 118.1(9) . . ?
C6 C5 H5 121.0(9) . . ?
N2 C9 C8 120.00(12) . . ?
N2 C9 H9 115.7(8) . . ?
C8 C9 H9 124.2(8) . . ?
N1 C12 C11 122.82(12) . . ?
N1 C12 H12 115.8(9) . . ?
C11 C12 H12 121.4(9) . . ?
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
O2 C2 1.2653(15) . ?
O4 C4 1.2281(15) . ?
O1 C1 1.3151(14) . ?
O1 H1 1.09(2) . ?
O3 C3 1.2182(15) . ?
N2 C5 1.3372(17) . ?
N2 C9 1.3424(17) . ?
N2 H2 1.08(2) . ?
N1 C13 1.3352(17) . ?
N1 C12 1.3386(19) . ?
C7 C10 1.4848(17) . ?
C7 C8 1.3970(17) . ?
C7 C6 1.3951(17) . ?
C10 C14 1.3885(17) . ?
C10 C11 1.3922(17) . ?
C14 C13 1.3826(17) . ?
C14 H14 0.994(14) . ?
C2 C1 1.4130(17) . ?
C2 C3 1.4829(18) . ?
C8 C9 1.3782(17) . ?
C8 H8 0.967(15) . ?
C4 C1 1.4458(18) . ?
C4 C3 1.5017(18) . ?
C6 C5 1.3712(18) . ?
C6 H6 0.983(16) . ?
C13 H13 0.955(16) . ?
C11 C12 1.3831(18) . ?
C11 H11 0.981(16) . ?
C5 H5 0.975(15) . ?
C9 H9 0.959(14) . ?
C12 H12 0.971(16) . ?
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 C2 C1 O1 -0.9(3) . . . . ?
O2 C2 C1 C4 178.88(17) . . . . ?
O2 C2 C3 O3 1.5(3) . . . . ?
O2 C2 C3 C4 -178.93(16) . . . . ?
O4 C4 C1 O1 1.4(3) . . . . ?
O4 C4 C1 C2 -178.41(17) . . . . ?
O4 C4 C3 O3 -2.0(3) . . . . ?
O4 C4 C3 C2 178.46(17) . . . . ?
C7 C10 C14 C13 179.02(12) . . . . ?
C7 C10 C11 C12 -177.62(13) . . . . ?
C7 C8 C9 N2 -0.1(2) . . . . ?
C7 C6 C5 N2 1.3(2) . . . . ?
C10 C7 C8 C9 -177.00(12) . . . . ?
C10 C7 C6 C5 176.45(12) . . . . ?
C10 C14 C13 N1 -1.9(2) . . . . ?
C10 C11 C12 N1 -1.1(2) . . . . ?
C14 C10 C11 C12 0.9(2) . . . . ?
C8 C7 C10 C14 -23.67(19) . . . . ?
C8 C7 C10 C11 154.77(13) . . . . ?
C8 C7 C6 C5 -2.1(2) . . . . ?
C1 C2 C3 O3 -178.83(18) . . . . ?
C1 C2 C3 C4 0.75(10) . . . . ?
C1 C4 C3 O3 178.84(18) . . . . ?
C1 C4 C3 C2 -0.73(10) . . . . ?
C6 C7 C10 C14 157.88(13) . . . . ?
C6 C7 C10 C11 -23.7(2) . . . . ?
C6 C7 C8 C9 1.5(2) . . . . ?
C3 C2 C1 O1 179.44(16) . . . . ?
C3 C2 C1 C4 -0.78(11) . . . . ?
C3 C4 C1 O1 -179.45(16) . . . . ?
C3 C4 C1 C2 0.77(10) . . . . ?
C13 N1 C12 C11 -0.1(2) . . . . ?
C11 C10 C14 C13 0.5(2) . . . . ?
C5 N2 C9 C8 -0.7(2) . . . . ?
C9 N2 C5 C6 0.1(2) . . . . ?
C12 N1 C13 C14 1.7(2) . . . . ?
