#------------------------------------------------------------------------------
#$Date: 2019-10-04 03:45:33 +0300 (Fri, 04 Oct 2019) $
#$Revision: 219081 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/43/7234356.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_7234356
loop_
_publ_author_name
'Devogelaer, Jan-Joris'
'Brugman, Sander J.T.'
'meekes, hugo'
'Tinnemans, Paul T.'
'Vlieg, Elias'
'de Gelder, Rene'
_publ_section_title
;
 Cocrystal design by network-based link prediction
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C9CE01110B
_journal_year                    2019
_chemical_formula_moiety         'C12 H12 N2, C2 O4, 6(H2 O)'
_chemical_formula_sum            'C14 H24 N2 O10'
_chemical_formula_weight         380.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-07-16 deposited with the CCDC.    2019-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 123.4486(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.3686(5)
_cell_length_b                   6.9285(2)
_cell_length_c                   9.5207(3)
_cell_measurement_reflns_used    6262
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.2
_cell_measurement_theta_min      2.6
_cell_volume                     900.92(5)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex3
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_detector       Photon100
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11525
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.167
_diffrn_reflns_theta_min         2.564
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0365
_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)+(0.0637P)²+0.2738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1629
_reflns_number_total             1850
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01110b2.cif
_cod_data_source_block           p1914b
_cod_original_cell_volume        900.91(5)
_cod_database_code               7234356
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O01 O 0.62427(5) 0.500000 0.65874(9) 0.0273(2) Uani 1 2 d S T P
O02 O 0.49370(5) 0.500000 0.67762(9) 0.02429(18) Uani 1 2 d S T P
O03 O 0.78793(7) 0.500000 0.98202(11) 0.0324(2) Uani 1 2 d S T P
H03A H 0.7317(17) 0.500000 0.888(3) 0.049(5) Uiso 1 2 d S . P
H03B H 0.8204(19) 0.590(4) 0.987(3) 0.035(6) Uiso 0.5 1 d . . P
O04 O 0.93049(6) 0.75576(12) 1.03916(9) 0.03729(18) Uani 1 1 d . . .
H04A H 0.9478(12) 0.831(2) 1.120(2) 0.057(4) Uiso 1 1 d . . .
H04B H 0.973(2) 0.744(4) 1.025(3) 0.036(6) Uiso 0.5 1 d . . P
H04C H 0.889(2) 0.690(5) 1.020(4) 0.048(8) Uiso 0.5 1 d . . P
N05 N 0.71032(6) 0.500000 0.48040(11) 0.01935(17) Uani 1 2 d S T P
H05 H 0.6528(19) 0.500000 0.490(3) 0.069(7) Uiso 1 2 d S . P
C06 C 0.95282(6) 0.500000 0.43635(11) 0.01759(18) Uani 1 2 d S T P
H06 H 0.938190 0.500000 0.324930 0.021 Uiso 1 2 calc R U P
C07 C 0.87055(6) 0.500000 0.45715(11) 0.01562(17) Uani 1 2 d S T P
C08 C 0.53445(6) 0.500000 0.59750(11) 0.01690(18) Uani 1 2 d S T P
C09 C 0.88219(7) 0.500000 0.61442(12) 0.02054(19) Uani 1 2 d S T P
H09 H 0.945867 0.500000 0.714909 0.025 Uiso 1 2 calc R U P
C10 C 0.77538(7) 0.500000 0.31273(12) 0.02099(19) Uani 1 2 d S T P
H10 H 0.765077 0.500000 0.204283 0.025 Uiso 1 2 calc R U P
C11 C 0.80058(7) 0.500000 0.62226(13) 0.02157(19) Uani 1 2 d S T P
H11 H 0.808166 0.500000 0.728637 0.026 Uiso 1 2 calc R U P
C12 C 0.69666(7) 0.500000 0.32861(13) 0.0224(2) Uani 1 2 d S T P
H12 H 0.631996 0.500000 0.230559 0.027 Uiso 1 2 calc R U P
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
H03A O03 H03B 110.7(19) . .
H03A O03 H03B 110.7(19) . 6_565
H03B O03 H03B 102(4) . 6_565
H04A O04 H04B 110(2) . .
H04A O04 H04C 114(2) . .
H04B O04 H04C 132(3) . .
C12 N05 C11 121.55(8) . .
C12 N05 H05 119.8(14) . .
C11 N05 H05 118.6(14) . .
C06 C06 C07 124.43(10) 5_766 .
C06 C06 H06 117.8 5_766 .
C07 C06 H06 117.8 . .
C10 C07 C09 118.18(8) . .
C10 C07 C06 118.41(8) . .
C09 C07 C06 123.41(8) . .
O01 C08 O02 126.71(9) . .
O01 C08 C08 116.81(9) . 5_666
O02 C08 C08 116.48(9) . 5_666
C11 C09 C07 119.52(9) . .
C11 C09 H09 120.2 . .
C07 C09 H09 120.2 . .
C12 C10 C07 119.63(9) . .
C12 C10 H10 120.2 . .
C07 C10 H10 120.2 . .
N05 C11 C09 120.45(9) . .
N05 C11 H11 119.8 . .
C09 C11 H11 119.8 . .
N05 C12 C10 120.67(9) . .
N05 C12 H12 119.7 . .
C10 C12 H12 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O01 C08 1.2477(10) .
O02 C08 1.2600(10) .
O03 H03A 0.86(2) .
O03 H03B 0.80(3) .
O03 H03B 0.80(3) 6_565
O04 H04A 0.842(17) .
O04 H04B 0.78(2) .
O04 H04C 0.75(4) .
N05 C12 1.3349(13) .
N05 C11 1.3443(13) .
N05 H05 1.00(2) .
C06 C06 1.3383(17) 5_766
C06 C07 1.4653(12) .
C06 H06 0.9500 .
C07 C10 1.3986(13) .
C07 C09 1.4013(13) .
C08 C08 1.5526(18) 5_666
C09 C11 1.3784(12) .
C09 H09 0.9500 .
C10 C12 1.3778(12) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 H12 0.9500 .
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
C06 C06 C07 C10 180.000(0) 5_766
C06 C06 C07 C09 0.000(0) 5_766
C10 C07 C09 C11 0.000(0) .
C06 C07 C09 C11 180.000(0) .
C09 C07 C10 C12 0.000(0) .
C06 C07 C10 C12 180.000(0) .
C12 N05 C11 C09 0.000(0) .
C07 C09 C11 N05 0.000(0) .
C11 N05 C12 C10 0.000(0) .
C07 C10 C12 N05 0.000(0) .
