#------------------------------------------------------------------------------
#$Date: 2019-10-28 09:23:29 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/82/2108213.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_2108213
loop_
_publ_author_name
'Perera, Manomi D.'
'Sinha, Abhijeet S.'
'Aakeröy, Christer B.'
_publ_section_title
;
 Using structural mimics for accessing and exploring structural landscapes
 of poorly soluble molecular solids
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              42
_journal_page_last               48
_journal_paper_doi               10.1107/S2052520617017371
_journal_volume                  74
_journal_year                    2018
_chemical_formula_moiety         '2(C18 H15 N3 O2), C8 H14 O4'
_chemical_formula_sum            'C44 H44 N6 O8'
_chemical_formula_weight         784.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                86.153(19)
_cell_angle_beta                 83.38(2)
_cell_angle_gamma                69.517(18)
_cell_formula_units_Z            1
_cell_length_a                   7.889(4)
_cell_length_b                   9.157(4)
_cell_length_c                   14.832(7)
_cell_measurement_reflns_used    2665
_cell_measurement_temperature    130.(2)
_cell_measurement_theta_max      24.43
_cell_measurement_theta_min      2.38
_cell_volume                     996.6(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      130.(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15029
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         25.60
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blocks
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3506
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0490
_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)+(0.0759P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1510
_reflns_number_gt                2377
_reflns_number_total             3506
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao5034sup1.cif
_cod_data_source_block           MP1611
_cod_depositor_comments
;

2019-10-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C22 H22 N3 O4'
_cod_original_formula_weight         392.42
_cod_original_formula_moiety         'C18 H15 N3 O2, 0.5(C8 H14 O4)'
_cod_original_formula_units_Z            2
_cod_database_code               2108213
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
N N1 0.5049(3) 0.6611(2) 0.62907(12) 0.0233(5) Uani d . . 1
C C2 0.4289(3) 0.7651(3) 0.56568(16) 0.0225(6) Uani d . . 1
H H2 0.3233 0.8496 0.5856 0.027 Uiso calc U R 1
N N3 0.4840(2) 0.7643(2) 0.47696(12) 0.0215(5) Uani d . . 1
C C4 0.6265(3) 0.6404(3) 0.44643(15) 0.0192(5) Uani d . . 1
C C5 0.8736(3) 0.3863(3) 0.48137(15) 0.0193(6) Uani d . . 1
H H5 0.9162 0.3721 0.4189 0.023 Uiso calc U R 1
C C6 0.9591(3) 0.2779(3) 0.54546(15) 0.0213(6) Uani d . . 1
C C7 0.9013(3) 0.3019(3) 0.64031(15) 0.0230(6) Uani d . . 1
C C8 0.7531(3) 0.4288(3) 0.66750(15) 0.0238(6) Uani d . . 1
H H8 0.7138 0.444 0.7302 0.029 Uiso calc U R 1
C C9 0.6595(3) 0.5364(3) 0.60203(15) 0.0201(6) Uani d . . 1
C C10 0.7220(3) 0.5187(3) 0.50867(14) 0.0174(5) Uani d . . 1
H H11 0.752(3) 0.532(3) 0.3311(15) 0.031(7) Uiso d . . 1
N N11 0.6772(3) 0.6318(2) 0.35628(12) 0.0187(5) Uani d . . 1
C C12 0.6008(3) 0.7479(3) 0.28883(14) 0.0188(5) Uani d . . 1
C C13 0.5686(3) 0.6988(3) 0.20754(14) 0.0205(6) Uani d . . 1
H H13 0.5911 0.5912 0.2 0.025 Uiso calc U R 1
C C14 0.5034(3) 0.8064(3) 0.13660(15) 0.0220(6) Uani d . . 1
C C15 0.4714(3) 0.9632(3) 0.14857(16) 0.0275(6) Uani d . . 1
H H15 0.4277 1.0376 0.1013 0.033 Uiso calc U R 1
C C16 0.5035(3) 1.0109(3) 0.22978(16) 0.0280(6) Uani d . . 1
H H16 0.4802 1.1185 0.2376 0.034 Uiso calc U R 1
C C17 0.5691(3) 0.9048(3) 0.30013(16) 0.0230(6) Uani d . . 1
H H17 0.5918 0.9393 0.355 0.028 Uiso calc U R 1
C C18 0.4684(3) 0.7559(3) 0.05265(16) 0.0272(6) Uani d . . 1
C C19 0.4407(3) 0.7144(3) -0.01672(17) 0.0345(7) Uani d . . 1
H H19 0.4186 0.6813 -0.0722 0.041 Uiso calc U R 1
O O20 1.1032(2) 0.14567(19) 0.52593(10) 0.0281(4) Uani d . . 1
C C21 1.1560(3) 0.1125(3) 0.43072(16) 0.0320(7) Uani d . . 1
H H21A 1.0515 0.109 0.4022 0.048 Uiso calc U R 1
H H21B 1.2548 0.0116 0.4247 0.048 Uiso calc U R 1
H H21C 1.1974 0.1945 0.4008 0.048 Uiso calc U R 1
O O22 1.0030(2) 0.1916(2) 0.69722(10) 0.0319(5) Uani d . . 1
C C23 0.9730(4) 0.2246(4) 0.79337(16) 0.0411(8) Uani d . . 1
H H23A 0.982 0.3267 0.8018 0.062 Uiso calc U R 1
H H23B 1.0651 0.144 0.8258 0.062 Uiso calc U R 1
H H23C 0.8517 0.2251 0.8174 0.062 Uiso calc U R 1
H H24 0.384(5) 0.677(4) 0.7194(18) 0.099(13) Uiso d . D 1
O O24 0.3148(2) 0.7039(2) 0.78516(11) 0.0325(5) Uani d . D 1
O O25 0.0956(2) 0.6337(2) 0.73686(11) 0.0302(5) Uani d . . 1
C C26 0.1490(3) 0.7026(3) 0.79021(16) 0.0248(6) Uani d . . 1
C C27 0.0194(3) 0.7900(3) 0.86841(16) 0.0288(6) Uani d . . 1
H H27A -0.0722 0.8842 0.8439 0.035 Uiso calc U R 1
H H27B 0.0886 0.8247 0.9088 0.035 Uiso calc U R 1
C C28 -0.0786(3) 0.6909(3) 0.92413(16) 0.0302(6) Uani d . . 1
H H28A -0.1681 0.7567 0.9704 0.036 Uiso calc U R 1
H H28B -0.1464 0.6553 0.8834 0.036 Uiso calc U R 1
C C29 0.0493(3) 0.5487(3) 0.97159(16) 0.0291(6) Uani d . . 1
H H29A 0.1186 0.5841 1.0116 0.035 Uiso calc U R 1
H H29B 0.1376 0.4819 0.9252 0.035 Uiso calc U R 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 N1 C9 . . 117.6(2)
N1 C2 N3 . . 127.3(2)
N1 C2 H2 . . 116.3
N3 C2 H2 . . 116.3
C2 N3 C4 . . 117.3(2)
N3 C4 N11 . . 118.4(2)
N3 C4 C10 . . 120.8(2)
N11 C4 C10 . . 120.8(2)
C6 C5 C10 . . 119.9(2)
C6 C5 H5 . . 120.0
C10 C5 H5 . . 120.0
O20 C6 C5 . . 124.3(2)
O20 C6 C7 . . 115.17(19)
C5 C6 C7 . . 120.5(2)
O22 C7 C8 . . 125.0(2)
O22 C7 C6 . . 115.0(2)
C8 C7 C6 . . 120.0(2)
C7 C8 C9 . . 119.8(2)
C7 C8 H8 . . 120.1
C9 C8 H8 . . 120.1
N1 C9 C8 . . 119.9(2)
N1 C9 C10 . . 119.6(2)
C8 C9 C10 . . 120.5(2)
C9 C10 C5 . . 119.1(2)
C9 C10 C4 . . 117.2(2)
C5 C10 C4 . . 123.8(2)
C4 N11 C12 . . 126.0(2)
C4 N11 H11 . . 119.3(14)
C12 N11 H11 . . 113.3(14)
C17 C12 C13 . . 119.9(2)
C17 C12 N11 . . 121.9(2)
C13 C12 N11 . . 118.1(2)
C12 C13 C14 . . 120.8(2)
C12 C13 H13 . . 119.6
C14 C13 H13 . . 119.6
C15 C14 C13 . . 118.9(2)
C15 C14 C18 . . 120.2(2)
C13 C14 C18 . . 120.9(2)
C16 C15 C14 . . 119.8(2)
C16 C15 H15 . . 120.1
C14 C15 H15 . . 120.1
C15 C16 C17 . . 121.6(2)
C15 C16 H16 . . 119.2
C17 C16 H16 . . 119.2
C12 C17 C16 . . 119.0(2)
C12 C17 H17 . . 120.5
C16 C17 H17 . . 120.5
C19 C18 C14 . . 179.5(3)
C18 C19 H19 . . 180.0
C6 O20 C21 . . 116.38(17)
O20 C21 H21A . . 109.5
O20 C21 H21B . . 109.5
H21A C21 H21B . . 109.5
O20 C21 H21C . . 109.5
H21A C21 H21C . . 109.5
H21B C21 H21C . . 109.5
C7 O22 C23 . . 117.3(2)
O22 C23 H23A . . 109.5
O22 C23 H23B . . 109.5
H23A C23 H23B . . 109.5
O22 C23 H23C . . 109.5
H23A C23 H23C . . 109.5
H23B C23 H23C . . 109.5
C26 O24 H24 . . 112.4(19)
O25 C26 O24 . . 124.0(2)
O25 C26 C27 . . 120.0(2)
O24 C26 C27 . . 116.1(2)
C26 C27 C28 . . 112.8(2)
C26 C27 H27A . . 109.0
C28 C27 H27A . . 109.0
C26 C27 H27B . . 109.0
C28 C27 H27B . . 109.0
H27A C27 H27B . . 107.8
C29 C28 C27 . . 113.5(2)
C29 C28 H28A . . 108.9
C27 C28 H28A . . 108.9
C29 C28 H28B . . 108.9
C27 C28 H28B . . 108.9
H28A C28 H28B . . 107.7
C28 C29 C29 . 2_567 113.4(3)
C28 C29 H29A . . 108.9
C29 C29 H29A 2_567 . 108.9
C28 C29 H29B . . 108.9
C29 C29 H29B 2_567 . 108.9
H29A C29 H29B . . 107.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C2 . 1.327(3)
N1 C9 . 1.387(3)
C2 N3 . 1.337(3)
C2 H2 . 0.95
N3 C4 . 1.347(3)
C4 N11 . 1.350(3)
C4 C10 . 1.448(3)
C5 C6 . 1.377(3)
C5 C10 . 1.416(3)
C5 H5 . 0.95
C6 O20 . 1.360(3)
C6 C7 . 1.435(3)
C7 O22 . 1.361(3)
C7 C8 . 1.372(3)
C8 C9 . 1.410(3)
C8 H8 . 0.95
C9 C10 . 1.416(3)
N11 C12 . 1.429(3)
N11 H11 . 0.97(3)
C12 C17 . 1.388(3)
C12 C13 . 1.394(3)
C13 C14 . 1.405(3)
C13 H13 . 0.95
C14 C15 . 1.387(3)
C14 C18 . 1.445(3)
C15 C16 . 1.387(3)
C15 H15 . 0.95
C16 C17 . 1.392(3)
C16 H16 . 0.95
C17 H17 . 0.95
C18 C19 . 1.189(3)
C19 H19 . 0.95
O20 C21 . 1.447(3)
C21 H21A . 0.98
C21 H21B . 0.98
C21 H21C . 0.98
O22 C23 . 1.453(3)
C23 H23A . 0.98
C23 H23B . 0.98
C23 H23C . 0.98
O24 C26 . 1.305(3)
O24 H24 . 1.06(2)
O25 C26 . 1.237(3)
C26 C27 . 1.520(3)
C27 C28 . 1.532(3)
C27 H27A . 0.99
C27 H27B . 0.99
C28 C29 . 1.526(3)
C28 H28A . 0.99
C28 H28B . 0.99
C29 C29 2_567 1.531(5)
C29 H29A . 0.99
C29 H29B . 0.99
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O24 H24 N1 . 1.06(2) 1.54(3) 2.583(3) 168.(3)
N11 H11 O25 2_666 0.97(3) 1.85(3) 2.804(3) 168.(2)
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_site_symmetry_4
_geom_torsion
C9 N1 C2 N3 . 0.1(3)
N1 C2 N3 C4 . 4.1(3)
C2 N3 C4 N11 . 175.64(19)
C2 N3 C4 C10 . -3.8(3)
C10 C5 C6 O20 . 178.7(2)
C10 C5 C6 C7 . -3.0(3)
O20 C6 C7 O22 . 2.2(3)
C5 C6 C7 O22 . -176.24(19)
O20 C6 C7 C8 . -177.7(2)
C5 C6 C7 C8 . 3.8(3)
O22 C7 C8 C9 . 179.3(2)
C6 C7 C8 C9 . -0.8(3)
C2 N1 C9 C8 . 175.46(19)
C2 N1 C9 C10 . -4.4(3)
C7 C8 C9 N1 . 177.2(2)
C7 C8 C9 C10 . -3.0(3)
N1 C9 C10 C5 . -176.38(19)
C8 C9 C10 C5 . 3.8(3)
N1 C9 C10 C4 . 4.4(3)
C8 C9 C10 C4 . -175.47(19)
C6 C5 C10 C9 . -0.8(3)
C6 C5 C10 C4 . 178.4(2)
N3 C4 C10 C9 . -0.2(3)
N11 C4 C10 C9 . -179.63(19)
N3 C4 C10 C5 . -179.4(2)
N11 C4 C10 C5 . 1.2(3)
N3 C4 N11 C12 . 4.3(3)
C10 C4 N11 C12 . -176.24(19)
C4 N11 C12 C17 . 45.9(3)
C4 N11 C12 C13 . -138.1(2)
C17 C12 C13 C14 . -0.3(3)
N11 C12 C13 C14 . -176.40(19)
C12 C13 C14 C15 . 0.1(3)
C12 C13 C14 C18 . -179.4(2)
C13 C14 C15 C16 . -0.2(3)
C18 C14 C15 C16 . 179.3(2)
C14 C15 C16 C17 . 0.6(4)
C13 C12 C17 C16 . 0.6(3)
N11 C12 C17 C16 . 176.6(2)
C15 C16 C17 C12 . -0.8(4)
C5 C6 O20 C21 . -6.0(3)
C7 C6 O20 C21 . 175.57(18)
C8 C7 O22 C23 . -11.4(3)
C6 C7 O22 C23 . 168.65(19)
O25 C26 C27 C28 . 50.7(3)
O24 C26 C27 C28 . -128.2(2)
C26 C27 C28 C29 . 63.3(3)
C27 C28 C29 C29 2_567 179.1(3)

_cod_database_fobs_code 2108213
