#------------------------------------------------------------------------------
#$Date: 2019-10-04 02:45:33 +0200 (vie 04 de oct de 2019) $
#$Revision: 219081 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/43/7234357.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_7234357
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 H11.56 N2, 2(C8 H5.22 O4)'
_chemical_formula_sum            'C28 H22 N2 O8'
_chemical_formula_weight         514.47
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.176(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.0785(6)
_cell_length_b                   4.9373(2)
_cell_length_c                   18.7535(9)
_cell_measurement_reflns_used    7336
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.0
_cell_measurement_theta_min      3.2
_cell_volume                     1163.02(9)
_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 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0378
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23067
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.180
_diffrn_reflns_theta_min         2.262
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6369
_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            orange
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0789P)²+0.2765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3359
_reflns_number_total             4443
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01110b2.cif
_cod_data_source_block           p1910a
_cod_database_code               7234357
_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   0.950
_shelx_estimated_absorpt_t_max   0.994
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
O01 O 0.28469(6) 0.8816(2) 0.10663(7) 0.0457(3) Uani 1 1 d . . .
H01 H 0.3327(17) 0.759(5) 0.1483(13) 0.068 Uiso 1 1 d . U .
O02 O 0.29387(6) 1.2112(2) 0.03143(5) 0.0369(2) Uani 1 1 d . . .
C03 C 0.33937(8) 1.0503(2) 0.07875(6) 0.0229(2) Uani 1 1 d . . .
C04 C 0.46018(7) 1.0463(2) 0.10566(5) 0.01592(18) Uani 1 1 d . . .
C05 C 0.50737(8) 1.2323(2) 0.06832(6) 0.0248(2) Uani 1 1 d . . .
H05 H 0.462610 1.341312 0.030588 0.030 Uiso 1 1 calc R U .
C06 C 0.61637(8) 1.2642(2) 0.08398(7) 0.0245(2) Uani 1 1 d . . .
H06 H 0.645475 1.392120 0.057218 0.029 Uiso 1 1 calc R U .
C07 C 0.68251(7) 1.1083(2) 0.13888(6) 0.0200(2) Uani 1 1 d . . .
H07 H 0.757602 1.128352 0.150485 0.024 Uiso 1 1 calc R U .
C08 C 0.63821(7) 0.9227(2) 0.17677(6) 0.01816(19) Uani 1 1 d . . .
H08 H 0.684273 0.816527 0.214573 0.022 Uiso 1 1 calc R U .
C09 C 0.52781(7) 0.88491(18) 0.16161(5) 0.01389(17) Uani 1 1 d . . .
C10 C 0.49575(7) 0.6691(2) 0.20880(5) 0.01710(18) Uani 1 1 d . . .
O11 O 0.40028(6) 0.59773(18) 0.19884(5) 0.0281(2) Uani 1 1 d . . .
O12 O 0.57015(7) 0.56546(19) 0.25859(5) 0.0294(2) Uani 1 1 d . . .
H12 H 0.552(7) 0.46(3) 0.288(6) 0.05(3) Uiso 0.22(4) 1 d . . P
N13 N 0.52307(7) 0.18781(18) 0.33672(5) 0.01844(17) Uani 1 1 d . . .
H13 H 0.5364(16) 0.327(5) 0.3063(12) 0.022 Uiso 0.78(4) 1 d . U P
C14 C 0.60554(8) 0.0826(2) 0.38867(6) 0.01908(19) Uani 1 1 d . . .
H14 H 0.675342 0.148853 0.393517 0.023 Uiso 1 1 calc R U .
C15 C 0.42340(8) 0.1038(2) 0.32928(6) 0.0216(2) Uani 1 1 d . . .
H15 H 0.366146 0.184251 0.292708 0.026 Uiso 1 1 calc R U .
C16 C 0.59048(7) -0.1203(2) 0.43512(6) 0.01745(18) Uani 1 1 d . . .
H16 H 0.649406 -0.194089 0.471683 0.021 Uiso 1 1 calc R U .
C17 C 0.40293(8) -0.0980(2) 0.37411(6) 0.0199(2) Uani 1 1 d . . .
H17 H 0.331901 -0.156197 0.368535 0.024 Uiso 1 1 calc R U .
C18 C 0.48715(7) -0.21677(19) 0.42785(5) 0.01444(17) Uani 1 1 d . . .
C19 C 0.46308(7) -0.43057(18) 0.47473(5) 0.01540(18) Uani 1 1 d . . .
H19 H 0.390411 -0.473545 0.468929 0.018 Uiso 1 1 calc R U .
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
C03 O01 H01 112.8(12) .
O02 C03 O01 120.02(10) .
O02 C03 C04 120.23(10) .
O01 C03 C04 119.75(9) .
C05 C04 C09 117.99(8) .
C05 C04 C03 112.85(8) .
C09 C04 C03 129.16(8) .
C06 C05 C04 122.78(9) .
C06 C05 H05 118.6 .
C04 C05 H05 118.6 .
C07 C06 C05 119.35(9) .
C07 C06 H06 120.3 .
C05 C06 H06 120.3 .
C06 C07 C08 119.20(9) .
C06 C07 H07 120.4 .
C08 C07 H07 120.4 .
C07 C08 C09 122.61(9) .
C07 C08 H08 118.7 .
C09 C08 H08 118.7 .
C08 C09 C04 118.07(8) .
C08 C09 C10 114.27(8) .
C04 C09 C10 127.66(8) .
O12 C10 O11 121.81(9) .
O12 C10 C09 115.94(8) .
O11 C10 C09 122.24(9) .
C10 O12 H12 116(6) .
C15 N13 C14 121.27(9) .
C15 N13 H13 120.3(12) .
C14 N13 H13 118.4(12) .
N13 C14 C16 120.91(9) .
N13 C14 H14 119.5 .
C16 C14 H14 119.5 .
N13 C15 C17 120.67(9) .
N13 C15 H15 119.7 .
C17 C15 H15 119.7 .
C14 C16 C18 119.28(9) .
C14 C16 H16 120.4 .
C18 C16 H16 120.4 .
C15 C17 C18 119.71(9) .
C15 C17 H17 120.1 .
C18 C17 H17 120.1 .
C17 C18 C16 118.13(9) .
C17 C18 C19 118.54(8) .
C16 C18 C19 123.31(8) .
C19 C19 C18 124.16(10) 3_646
C19 C19 H19 117.9 3_646
C18 C19 H19 117.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O01 C03 1.2989(14) .
O01 H01 1.05(2) .
O02 C03 1.2160(13) .
C03 C04 1.5189(13) .
C04 C05 1.3984(14) .
C04 C09 1.4145(13) .
C05 C06 1.3820(14) .
C05 H05 0.9500 .
C06 C07 1.3799(14) .
C06 H06 0.9500 .
C07 C08 1.3819(14) .
C07 H07 0.9500 .
C08 C09 1.4042(12) .
C08 H08 0.9500 .
C09 C10 1.5169(13) .
C10 O12 1.2547(12) .
C10 O11 1.2602(12) .
O12 H12 0.85(14) .
N13 C15 1.3377(13) .
N13 C14 1.3406(13) .
N13 H13 0.94(3) .
C14 C16 1.3769(14) .
C14 H14 0.9500 .
C15 C17 1.3771(14) .
C15 H15 0.9500 .
C16 C18 1.4034(13) .
C16 H16 0.9500 .
C17 C18 1.3980(13) .
C17 H17 0.9500 .
C18 C19 1.4630(13) .
C19 C19 1.3383(18) 3_646
C19 H19 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_4
O02 C03 C04 C05 -2.57(16) .
O01 C03 C04 C05 177.64(12) .
O02 C03 C04 C09 177.23(12) .
O01 C03 C04 C09 -2.56(18) .
C09 C04 C05 C06 -0.12(18) .
C03 C04 C05 C06 179.71(11) .
C04 C05 C06 C07 -0.32(19) .
C05 C06 C07 C08 0.30(18) .
C06 C07 C08 C09 0.16(17) .
C07 C08 C09 C04 -0.59(15) .
C07 C08 C09 C10 179.30(10) .
C05 C04 C09 C08 0.55(15) .
C03 C04 C09 C08 -179.24(10) .
C05 C04 C09 C10 -179.32(10) .
C03 C04 C09 C10 0.88(17) .
C08 C09 C10 O12 4.85(14) .
C04 C09 C10 O12 -175.28(10) .
C08 C09 C10 O11 -175.19(10) .
C04 C09 C10 O11 4.68(17) .
C15 N13 C14 C16 1.47(16) .
C14 N13 C15 C17 -1.30(16) .
N13 C14 C16 C18 -0.20(16) .
N13 C15 C17 C18 -0.12(17) .
C15 C17 C18 C16 1.33(15) .
C15 C17 C18 C19 179.96(10) .
C14 C16 C18 C17 -1.17(15) .
C14 C16 C18 C19 -179.73(10) .
C17 C18 C19 C19 176.29(12) 3_646
C16 C18 C19 C19 -5.15(18) 3_646
