Polymorphism control of an active pharmaceutical ingredient beneath calixarene-based Langmuir monolayers
Ludovico G. Tulli; Negar Moridi; Wenjie Wang; Kaisa Helttunen; Markus Neuburger; David Vaknin; Wolfgang Meier; Patrick Shahgaldian; Chem.Commun. 50 (2014) 3938–; doi:10.1039/C4CC00928B

data_7112198
_publ_section_title
;
 Polymorphism control of an active pharmaceutical ingredient beneath
 calixarene-based Langmuir monolayers
;
_journal_name_full               Chem.Commun.
_journal_page_first              3938
_journal_paper_doi               10.1039/C4CC00928B
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C80 H120 O12, 5(C5 H5 N)'
_chemical_formula_sum            'C105 H145 N5 O12'
_chemical_formula_weight         1669.26
_chemical_name_common
;             
5,11,17,23-tetra-carboxy-25,26,27,28-tetradodecyloxycalix[4]arene
;
_chemical_name_systematic
;
 ? 
;
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-22
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                96.255(2)
_cell_angle_beta                 94.2284(19)
_cell_angle_gamma                98.8577(19)
_cell_formula_units_Z            2
_cell_length_a                   12.0887(3)
_cell_length_b                   12.9462(3)
_cell_length_c                   32.3959(8)
_cell_measurement_reflns_used    14879
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.7860
_cell_measurement_theta_min      3.4910
_cell_volume                     4958.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details
;
  1 omega -113.00  -14.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7426  -57.0000   30.0000 99

  2 omega -116.00  -17.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7426  -37.0000   90.0000 99

  3 omega  -70.00   31.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7426   57.0000 -120.0000 101

  4 omega    2.00   82.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       41.7426  -99.0000  -30.0000 80

  5 omega   36.00   91.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 55

  6 omega   36.00  116.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  120.0000 80

  7 omega   40.00   89.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 49

  8 omega   42.00   99.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 57

  9 omega   54.00   87.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 33

 10 omega   42.00   98.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 56

 11 omega   62.00  145.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -60.0000 83

 12 omega   36.00  145.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 109

 13 omega   30.00   62.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 32

 14 omega   81.00  109.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 28

 15 omega   26.00  175.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000  -30.0000 149
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0808027000
_diffrn_orient_matrix_UB_12      -0.0251223000
_diffrn_orient_matrix_UB_13      -0.0329225000
_diffrn_orient_matrix_UB_21      -0.0515682000
_diffrn_orient_matrix_UB_22      0.0712411000
_diffrn_orient_matrix_UB_23      -0.0285611000
_diffrn_orient_matrix_UB_31      0.0871149000
_diffrn_orient_matrix_UB_32      0.0949589000
_diffrn_orient_matrix_UB_33      0.0202126000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            33020
_diffrn_reflns_theta_full        76.00
_diffrn_reflns_theta_max         76.58
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1812
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.837
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1287
_refine_ls_number_reflns         19903
_refine_ls_number_restraints     677
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0839
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1705P)^2^+1.5015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2611
_refine_ls_wR_factor_ref         0.2780
_reflns_number_gt                15009
_reflns_number_total             19903
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc00928b2.cif
_cod_data_source_block           1
_cod_database_code               7112198
_reflns_odcompleteness_completeness 98.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H12 of O12, H10 of O10, H6 of O6, {H134,H8,H5} of C134,
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  {H40A,H40B,H40C} of C40, {H52A,H52B,H52C} of C52, {H76A,H76B,H76C} of C76,
  H12B of O12B, {H64A,H64B,H64C} of C64
2. Restrained distances
 O12-H12
 0.82 with sigma of 0.02
 H10-O10
 0.82 with sigma of 0.02
 O8-H8
 0.82 with sigma of 0.02
 C24-C80B
 1.54 with sigma of 0.02
 O6-H6
 0.82 with sigma of 0.02
 O5-H5
 0.82 with sigma of 0.02
 C79-H10
 1.79 with sigma of 0.02
 C72-C71 = C73-C72 = C74-C73 = C76-C75 = C75-C74
 1.54 with sigma of 0.02
 C135-N130 \\sim C131-N130
 with sigma of 0.02
 C101-C102 \\sim C102-C103 \\sim C103-C104 \\sim C104-C105
 with sigma of 0.02
 N100-C101 \\sim N100-C105
 with sigma of 0.02
 C125-C126 \\sim C126-C127 \\sim C127-C128 \\sim C128-C129
 with sigma of 0.02
 C125-N124 \\sim C129-N124
 with sigma of 0.02
 C107-C108 \\sim C108-C109 \\sim C109-C110 \\sim C110-C111
 with sigma of 0.02
 N106-C107 \\sim N106-C111
 with sigma of 0.02
 C137-C138 \\sim C138-C139 \\sim C139-C140 \\sim C140-C141
 with sigma of 0.02
 N136-C137 \\sim N136-C141
 with sigma of 0.02
 C123-C122 \\sim C122-C121 \\sim C121-C120 \\sim C120-C119
 with sigma of 0.02
 N118-C123 \\sim N118-C119
 with sigma of 0.02
 O1-C29B \\sim O1-C29
 with sigma of 0.02
 C30B-C29B \\sim C30-C29 \\sim C30-C31 \\sim C30B-C31B \\sim C32-C31 \\sim C32-C31B
 with sigma of 0.02
 C32B-C33 \\sim C32-C33
 with sigma of 0.02
 C131-C132 \\sim C132-C133 \\sim C133-C134 \\sim C134-C135
 with sigma of 0.02
 C80B-C24 \\sim C80-C24
 with sigma of 0.02
 O11B-C80B \\sim O11-C80
 with sigma of 0.02
 O12B-C80B \\sim O12-C80
 with sigma of 0.02
 C116-C117 \\sim C117-C112 \\sim C112-C113 \\sim C113-C114
 with sigma of 0.02
 N115-C114 \\sim N115-C116
 with sigma of 0.02
 C68B-C67 \\sim C68-C67 \\sim C68-C69 \\sim C68B-C69 \\sim C70B-C69 \\sim C70-C69 \\sim C70-C71 \\sim C70B-
 C71
 with sigma of 0.02
3. Restrained planarity
 C125, N124, C126, C127, C128, C129
 with sigma of 0.1
 C109, C110, C111, N106, C107, C108
 with sigma of 0.1
 C138, C139, C140, C141, N136, C137
 with sigma of 0.1
 C120, C121, C122, C123, C119, N118
 with sigma of 0.1
 C133, C134, C135, N130, C131, C132
 with sigma of 0.1
 N115, C112, C113, C114, C116, C117
 with sigma of 0.1
4. Rigid bond restraints
 C102, C101, N100, C105, C104, C103
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C125, C126, C127, C128, C129, N124
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C138, C139, C140, C141, N136, C137
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C109, C110, C111, N106, C107, C108
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C120, N118, C119, C123, C122, C121
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C32, C32B, C31B, C31, C30B, C30, C29, C29B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C133, C132, C131, N130, C135, C134
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C65B, C65
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C70B, C70, C68B, C68, C69
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O11B, C80B, O12B, O11, C80, O12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N115, C112, C113, C114, C116, C117
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C102 \\sim C101 \\sim N100 \\sim C105 \\sim C104 \\sim C103: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C125 \\sim C126 \\sim C127 \\sim C128 \\sim C129 \\sim N124: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C138 \\sim C139 \\sim C140 \\sim C141 \\sim N136 \\sim C137: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C109 \\sim C110 \\sim C111 \\sim N106 \\sim C107 \\sim C108: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C120 \\sim N118 \\sim C119 \\sim C123 \\sim C122 \\sim C121: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C32B \\sim C32 \\sim C31 \\sim C31B \\sim C30 \\sim C30B \\sim C29B \\sim C29: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C133 \\sim C132 \\sim C131 \\sim N130 \\sim C135 \\sim C134: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C65B \\sim C65: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C70B \\sim C70 \\sim C69 \\sim C68B \\sim C68 \\sim C67: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
O11B \\sim C80B \\sim O12B \\sim O11 \\sim C80 \\sim O12: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
N115 \\sim C112 \\sim C113 \\sim C114 \\sim C116 \\sim C117: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C32B) = Uanis(C32)
Uanis(C65B) = Uanis(C65)
6. Others
 Sof(C65B)=Sof(H65C)=Sof(H65D)=Sof(H66C)=Sof(H66D)=1-FVAR(1)
 Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(H66A)=Sof(H66B)=FVAR(1)
 Sof(O11B)=Sof(O12B)=Sof(H12B)=Sof(C80B)=1-FVAR(2)
 Sof(O11)=Sof(O12)=Sof(H12)=Sof(C80)=FVAR(2)
 Sof(C29B)=Sof(H29C)=Sof(H29D)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=
 Sof(H31C)=Sof(H31D)=Sof(C32B)=Sof(H32C)=Sof(H32D)=Sof(H33C)=Sof(H33D)=1-FVAR(3)
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=
 Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H33A)=Sof(H33B)=FVAR(3)
 Sof(C138)=Sof(H138)=Sof(C139)=Sof(H139)=Sof(C140)=Sof(H140)=Sof(C141)=
 Sof(H141)=Sof(N136)=Sof(C137)=Sof(H137)=1-FVAR(4)
 Sof(C132)=Sof(H132)=Sof(N130)=Sof(C135)=Sof(H135)=Sof(C133)=Sof(H133)=
 Sof(C131)=Sof(H131)=Sof(C134)=Sof(H134)=FVAR(4)
 Sof(H67C)=Sof(H67D)=Sof(C68B)=Sof(H68C)=Sof(H68D)=Sof(H69C)=Sof(H69D)=
 Sof(C70B)=Sof(H70C)=Sof(H70D)=Sof(H71C)=Sof(H71D)=1-FVAR(5)
 Sof(H67A)=Sof(H67B)=Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(H69A)=Sof(H69B)=Sof(C70)=
 Sof(H70A)=Sof(H70B)=Sof(H71A)=Sof(H71B)=FVAR(5)
 Sof(C120)=Sof(H120)=Sof(C121)=Sof(H121)=Sof(C122)=Sof(H122)=Sof(C123)=
 Sof(H123)=Sof(N118)=Sof(C119)=Sof(H119)=1-FVAR(6)
 Sof(C125)=Sof(H125)=Sof(C126)=Sof(H126)=Sof(C127)=Sof(H127)=Sof(C128)=
 Sof(H128)=Sof(C129)=Sof(H129)=Sof(N124)=FVAR(6)
 Fixed Sof: H6(0.5) C102(0.5) H102(0.5) C101(0.5) H101(0.5) N100(0.5)
 C105(0.5) H105(0.5) C104(0.5) H104(0.5) C103(0.5) H103(0.5) C109(0.5)
 H109(0.5) C110(0.5) H110(0.5) C111(0.5) H111(0.5) N106(0.5) C107(0.5)
 H107(0.5) C108(0.5) H108(0.5) H5(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C21(H21A,H21B), C28(H28A,H28B), C29(H29A,H29B),
 C29B(H29C,H29D), C30(H30A,H30B), C30B(H30C,H30D), C31(H31A,H31B), C31B(H31C,
 H31D), C32(H32A,H32B), C32B(H32C,H32D), C33(H33A,H33B), C33(H33C,H33D),
 C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B),
  C39(H39A,H39B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,
 H44B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B),
 C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B), C53(H53A,H53B), C54(H54A,H54B),
  C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,
 H59B), C60(H60A,H60B), C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B),
 C65(H65A,H65B), C65B(H65C,H65D), C66(H66A,H66B), C66(H66C,H66D), C67(H67C,
 H67D), C67(H67A,H67B), C68(H68A,H68B), C68B(H68C,H68D), C69(H69C,H69D),
 C69(H69A,H69B), C70(H70A,H70B), C70B(H70C,H70D), C71(H71C,H71D), C71(H71A,
 H71B), C72(H72A,H72B), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,H75B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C9(H9), C11(H11), C16(H16), C18(H18), C23(H23), C25(H25),
 C102(H102), C101(H101), C105(H105), C104(H104), C103(H103), C109(H109),
 C110(H110), C111(H111), C107(H107), C108(H108), C114(H114), C113(H113),
 C112(H112), C117(H117), C116(H116), C125(H125), C126(H126), C127(H127),
 C128(H128), C129(H129), C120(H120), C121(H121), C122(H122), C123(H123),
 C119(H119), C132(H132), C138(H138), C139(H139), C140(H140), C141(H141),
 C135(H135), C137(H137), C133(H133), C131(H131), C134(H134)
7.c Fitted hexagon refined as free rotating group:
 C102(C101,N100,C105,C104,C103), C120(C121,C122,C123,N118,C119)
7.d Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C52(H52A,H52B,H52C), C64(H64A,H64B,H64C), C76(H76A,H76B,
 H76C)
7.e Idealised tetrahedral OH refined as rotating group:
 O12B(H12B)
;