The influence of hydrogen bonding on the planar arrangement of melamine in crystal structures of its solvates, cocrystals and salts
Vella-Zarb, Liana; Braga, Dario; Guy Orpen, A.; Baisch, Ulrich; CrystEngComm 16 (2014) 8147–; doi:10.1039/C4CE00748D

data_7218002
_publ_section_title
;
 The influence of hydrogen bonding on the planar arrangement of melamine
 in crystal structures of its solvates, cocrystals and salts
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              8147
_journal_paper_doi               10.1039/C4CE00748D
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C3 H6 N6, 3(C7 H8 N4 O2)'
_chemical_formula_sum            'C24 H30 N18 O6'
_chemical_formula_weight         666.66
_chemical_name_systematic        'tri-theobromine melamine'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-04-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.388(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3308(8)
_cell_length_b                   16.2228(10)
_cell_length_c                   13.1104(10)
_cell_measurement_reflns_used    2894
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      66.5936
_cell_measurement_theta_min      4.2536
_cell_volume                     2875.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega  -20.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       39.8381  -38.0000   60.0000 84

  2 omega   20.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       39.8381   38.0000   60.0000 92

  3 omega  131.00  165.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000   30.0000 34

  4 omega  103.00  163.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000   90.0000 60

  5 omega   39.00   73.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -60.0000 34

  6 omega   20.00   47.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000    0.0000 27

  7 omega   16.00   48.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   90.0000 32

  8 omega   24.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -60.0000 51

  9 omega   32.00   69.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000    0.0000 37

 10 omega   65.00  112.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -30.0000 47

 11 omega   22.00   50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -120.0000 28

 12 omega   57.00   83.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -120.0000 26

 13 omega   90.00  117.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000   30.0000 27

 14 omega   37.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   90.0000 38

 15 omega   20.00   67.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  150.0000 47

 16 omega   58.00   85.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -52.0000  -19.0000 27

 17 omega   14.00   49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -180.0000 35

 18 omega   21.00  122.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  -57.0000 101

 19 omega -114.00  -10.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.8381  -57.0000 -180.0000 104

 20 omega  -69.00   34.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.8381   57.0000  -30.0000 103

 21 omega -119.00   -6.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.8381  -77.0000  -60.0000 113

 22 omega   63.00   88.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -30.0000 25

 23 omega   41.00  176.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   17.0000  -95.0000 135
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0903049000
_diffrn_orient_matrix_UB_12      -0.0215783000
_diffrn_orient_matrix_UB_13      0.0337700000
_diffrn_orient_matrix_UB_21      -0.0662758000
_diffrn_orient_matrix_UB_22      0.0003127000
_diffrn_orient_matrix_UB_23      -0.1196428000
_diffrn_orient_matrix_UB_31      0.0208595000
_diffrn_orient_matrix_UB_32      -0.0924782000
_diffrn_orient_matrix_UB_33      -0.0081661000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10236
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.704
_diffrn_reflns_theta_min         4.257
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.990
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.3657
_exptl_crystal_size_mid          0.1922
_exptl_crystal_size_min          0.0903
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0685
_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^)+(0.1351P)^2^+3.2614P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2050
_refine_ls_wR_factor_ref         0.2244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1916
_reflns_number_total             2523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_duplicate_entry             7216833
_cod_data_source_file            c4ce00748d2.cif
_cod_data_source_block           2_995318_MelTheobr
_cod_original_cell_volume        2875.2(3)
_cod_database_code               7218002
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C24 H30 N18 O6'
_reflns_odcompleteness_completeness 94.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_refinement_special_details      'both theobromine molecules disordered'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{N13, C13}
{C15, N15}
{C33, N33}
3. Uiso/Uaniso restraints and constraints
Uanis(N13) = Uanis(C13)
Uanis(C15) = Uanis(N15)
Uanis(C18) = Uanis(C18A)
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C33) = Uanis(N33)
4. Others
 Fixed Sof: N13(0.75) C13(0.25) C15(0.75) N15(0.25) N17(0.75) N17A(0.25)
 C18(0.75) H18(0.75) C18A(0.25) H18A(0.25) C22(0.75) H22A(0.75) H22B(0.75)
 H22C(0.75) C22A(0.25) H22D(0.25) H22E(0.25) H22F(0.25) C23(0.75) H23A(0.75)
 H23B(0.75) H23C(0.75) C23A(0.25) H23D(0.25) H23E(0.25) H23F(0.25) C33(0.5)
 N33(0.5) N35(0.5) C36(0.5) H36(0.5) C39(0.5) H39A(0.5) H39B(0.5) H39C(0.5)
 C40(0.5) H40A(0.5) H40B(0.5) H40C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 N11(H11), C18(H18), C18A(H18A), N31(H31), C36(H36)
5.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
5.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F), C23(H23A,H23B,H23C), C23A(H23D,
 H23E,H23F), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C)
;