Versatile solid modifications of icariin: structure, properties and form transformation
Jia, Lina; Zhang, Qi; Wang, Jian-Rong; Mei, Xuefeng; CrystEngComm 17 (2015) 7500–; doi:10.1039/C5CE01422K

data_7221962
_publ_section_title
;
 Versatile solid modifications of icariin: structure, properties and form
 transformation
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              7500
_journal_paper_doi               10.1039/C5CE01422K
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C33 H40 O15, C3 H8 O'
_chemical_formula_sum            'C36 H48 O16'
_chemical_formula_weight         736.74
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-08-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-07-19 deposited with the CCDC.
2015-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.7400(3)
_cell_length_b                   22.9011(7)
_cell_length_c                   31.3079(9)
_cell_measurement_reflns_used    6874
_cell_measurement_temperature    130
_cell_measurement_theta_max      67.987
_cell_measurement_theta_min      2.390
_cell_volume                     6983.4(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XLMP (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            46294
_diffrn_reflns_theta_full        69.60
_diffrn_reflns_theta_max         69.60
_diffrn_reflns_theta_min         2.39
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.932
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1462 before and 0.0706 after correction.
The Ratio of minimum to maximum transmission is 0.8590.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     965
_refine_ls_number_reflns         12619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.058
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0943P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                10509
_reflns_number_total             12619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce01422k2.cif
_cod_data_source_block           cu_dm14467_0m
_cod_depositor_comments
'Adding full bibliography for 7221958--7221966.cif.'
_cod_database_code               7221962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
 C30(H30), C31(H31), C32(H32), C22A(H22A), C23A(H23A), C24A(H24A), C25A(H25A),
 C26A(H26A), C28A(H28A), C29A(H29A), C30A(H30A), C31A(H31A), C32A(H32A)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C33(H33A,H33B), C16A(H16C,H16D), C33A(H33C,H33D), C1S(H1SA,
 H1SB), C2S(H2SA,H2SB), C4S(H4SA,H4SB), C5S(H5SA,H5SB)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C12(H12A), C14(H14A), C15(H15A), C17(H17), C5A(H5A),
 C11A(H11A), C12A(H12C), C14A(H14C), C15A(H15C), C17A(H17A)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C27(H27A,H27B,
 H27C), C19A(H19D,H19E,H19F), C20A(H20D,H20E,H20F), C21A(H21D,H21E,H21F),
 C27A(H27D,H27E,H27F), C3S(H3SA,H3SB,H3SC), C6S(H6SA,H6SB,H6SC)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O7(H7), O8(H8), O9(H9), O12(H12), O13(H13), O14(H14), O15(H15),
 O3A(H3A), O7A(H7A), O8A(H8A), O9A(H9A), O12A(H12B), O13A(H13A), O14A(H14B),
 O15A(H15B), O1S(H1S), O2S(H2S)
;
_olex2_submission_special_instructions 'No special instructions were received'