A three dimensional hydrogen bonded organic framework assembled through antielectrostatic hydrogen bonds.
Cullen, Duncan A.; Gardiner, Michael G.; White, Nicholas G.; Chemical communications (Cambridge, England) 55 (2019) 12020–12023; doi:10.1039/c9cc06707h

data_7125415
_publ_section_title
;
 A three dimensional hydrogen bonded organic framework assembled through
 antielectrostatic hydrogen bonds.
;
_journal_issue                   80
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12020
_journal_page_last               12023
_journal_paper_doi               10.1039/c9cc06707h
_journal_volume                  55
_journal_year                    2019
_chemical_formula_moiety         '4(C H O3), C29 H32 N8, 3(O)'
_chemical_formula_sum            'C33 H36 N8 O15'
_chemical_formula_weight         784.70
_space_group_crystal_system      tetragonal
_space_group_IT_number           133
_space_group_name_Hall           '-P 4ac 2b'
_space_group_name_H-M_alt        'P 42/n b c :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-26 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.38177(8)
_cell_length_b                   13.38177(8)
_cell_length_c                   21.75010(18)
_cell_measurement_reflns_used    12480
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.5640
_cell_measurement_theta_min      3.9020
_cell_volume                     3894.83(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -21.00  29.00   1.00    2.00    --  -36.95  57.00   0.00   50
  2  \w    -27.00  50.00   1.00    2.00    --   36.95 -57.00 -90.00   77
  3  \w     58.00  90.00   1.00    2.00    --   36.95-125.00  60.00   32
  4  \w     36.00  88.00   1.00    2.00    --   36.95-125.00 150.00   52
  5  \w     31.00  75.00   1.00    2.00    --   36.95-125.00-120.00   44
  6  \w    -29.00  34.00   1.00    2.00    --   36.95 -58.00  17.00   63
  7  \w     37.00  65.00   1.00    2.00    --   36.95-125.00  30.00   28
  8  \w     50.00 108.00   1.00    2.00    --   36.95  19.00   0.00   58
  9  \w     33.00  85.00   1.00    2.00    --   36.95-125.00   0.00   52
 10  \w     84.00 117.00   1.00   16.00    --  111.00  12.00 -90.00   33
 11  \w     47.00  72.00   1.00   16.00    --  111.00 -92.00  30.00   25
 12  \w     52.00  78.00   1.00   16.00    --  111.00 -50.00  90.00   26
 13  \w     80.00 106.00   1.00   16.00    --  111.00 -92.00  30.00   26
 14  \w     42.00 129.00   1.00   16.00    --  111.00 -38.00   0.00   87
 15  \w     81.00 107.00   1.00   16.00    --  111.00-111.00  60.00   26
 16  \w     65.00  91.00   1.00   16.00    --  111.00 -92.00   0.00   26
 17  \w    150.00 175.00   1.00   16.00    --  111.00 111.00 120.00   25
 18  \w    109.00 143.00   1.00   16.00    --  111.00 111.00 120.00   34
 19  \w    104.00 144.00   1.00   16.00    --  111.00  77.00 -90.00   40
 20  \w     43.00 105.00   1.00   16.00    --  111.00 -92.00 -60.00   62
 21  \w     75.00 101.00   1.00   16.00    --  111.00  12.00  60.00   26
 22  \w     45.00  70.00   1.00   16.00    --  111.00-111.00  60.00   25
 23  \w     47.00 122.00   1.00   16.00    --  111.00 -64.00  60.00   75
 24  \w    109.00 175.00   1.00   16.00    --  111.00  77.00  90.00   66
 25  \w     96.00 125.00   1.00   16.00    --  111.00 -50.00  90.00   29
 26  \w     44.00  76.00   1.00   16.00    --  111.00 -92.00 -90.00   32
 27  \w     53.00 103.00   1.00   16.00    --  111.00 -92.00-120.00   50
 28  \w     42.00  70.00   1.00   16.00    --  111.00-111.00 120.00   28
 29  \w     83.00 109.00   1.00   16.00    --  111.00-111.00 120.00   26
 30  \w    138.00 174.00   1.00   16.00    --  111.00  50.00  60.00   36
 31  \w     97.00 124.00   1.00   16.00    --  111.00  50.00-120.00   27
 32  \w    141.00 170.00   1.00   16.00    --  111.00  12.00 -90.00   29
 33  \w     79.00 105.00   1.00   16.00    --  111.00 -50.00  30.00   26
 34  \w     47.00 114.00   1.00   16.00    --  111.00 -38.00  90.00   67
 35  \w     66.00 114.00   1.00   16.00    --  111.00 -77.00 150.00   48
 36  \w     76.00 102.00   1.00   16.00    --  111.00 -32.00-164.66   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1047584000
_diffrn_orient_matrix_UB_12      -0.0475480000
_diffrn_orient_matrix_UB_13      0.0016613000
_diffrn_orient_matrix_UB_21      -0.0363668000
_diffrn_orient_matrix_UB_22      -0.0755115000
_diffrn_orient_matrix_UB_23      0.0485411000
_diffrn_orient_matrix_UB_31      -0.0308915000
_diffrn_orient_matrix_UB_32      -0.0726465000
_diffrn_orient_matrix_UB_33      -0.0516123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24851
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.704
_diffrn_reflns_theta_min         4.065
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.36a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             1640
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Water'
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1976
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0810
_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/[\s^2^(Fo^2^)+(0.1677P)^2^+2.9553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2398
_refine_ls_wR_factor_ref         0.2466
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1812
_reflns_number_total             1976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06707h2.cif
_cod_data_source_block           1HCO3
_cod_original_cell_volume        3894.83(6)
_cod_original_sg_symbol_H-M      'P 42/n b c'
_cod_database_code               7125415
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C33 H44 N8 O16'
_reflns_odcompleteness_completeness 98.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C21-O21 = C21-O23
 1.31 with sigma of 0.01
 C21-O22
 1.24 with sigma of 0.01
3. Others
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C9)=Sof(H9)=Sof(C8)=Sof(H8)=1-FVAR(1)
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=FVAR(1)
 Fixed Sof: H11(0.5) O22(0.5) O21(0.5) O23(0.5) C21(0.5) O101(0.5) O111(0.25)
4.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19), C5(H5), C6(H6), C9(H9), C8(H8)
4.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B)
4.c Idealised tetrahedral OH refined as rotating group:
 O11(H11)
;
_shelx_res_checksum              20557
_ins_header
;
TITL NGW386 in P4(2)/nbc 
REM P4(2)/nbc (#133 in standard setting)
CELL 1.54184  13.381771  13.381771  21.750096  90.0000  90.0000  90.0000
ZERR    4.00   0.000077   0.000077   0.000182   0.0000   0.0000   0.0000
LATT  1
SYMM -x+1/2,-y+1/2, z 
SYMM -y+1/2, x, z+1/2 
SYMM  y,-x+1/2, z+1/2 
SYMM -x+1/2, y,-z 
SYMM  x,-y+1/2,-z 
SYMM  y, x,-z+1/2 
SYMM -y+1/2,-x+1/2,-z+1/2 
SFAC C H N O
UNIT 132.00 176.00 32.00 64.00
TREF
HKLF 4
END
;
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.496