pH-Switchable vitamin B<sub>9</sub> gels for stoichiometry-controlled spherical co-crystallization.
Wang, Jian-Rong; Bao, Junjie; Fan, Xiaowu; Dai, Wenjuan; Mei, Xuefeng; Chemical communications (Cambridge, England) 52 (2016) 13452–13455; doi:10.1039/c6cc07701c

data_7125217
_publ_section_title
;
 pH-Switchable vitamin B<sub>9</sub> gels for stoichiometry-controlled
 spherical co-crystallization.
;
_journal_issue                   92
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13452
_journal_page_last               13455
_journal_paper_doi               10.1039/c6cc07701c
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C6 H8 O6, C6 H6 N2 O, C H4 O'
_chemical_formula_sum            'C13 H18 N2 O8'
_chemical_formula_weight         330.29
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-07-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-09-21 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                84.757(4)
_cell_angle_beta                 85.752(4)
_cell_angle_gamma                81.727(4)
_cell_formula_units_Z            2
_cell_length_a                   5.0892(3)
_cell_length_b                   7.5329(5)
_cell_length_c                   19.7851(12)
_cell_measurement_reflns_used    5368
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.441
_cell_measurement_theta_min      2.741
_cell_volume                     746.03(8)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9818
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.035
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1019 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.8354.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.177
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_coef       0.121(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         4853
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.1080
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1573P)^2^+5.7268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3047
_refine_ls_wR_factor_ref         0.3099
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4579
_reflns_number_total             4853
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07701c2.cif
_cod_data_source_block           mo_2015514_0m
_cod_database_code               7125217
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1(2) 0(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 O1S-H1S
 0.95 with sigma of 0.001
 C1S-H1S
 1.9 with sigma of 0.02
 C1S-H1S
 1.9 with sigma of 0.001
 C1S-O1S
 1.54 with sigma of 0.02
 C1S-O1S
 1.45 with sigma of 0.001
4. Rigid bond restraints
 O2, C1, C2, O3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(C20) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C4) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
6.a Ternary CH refined with riding coordinates:
 C4(H4A), C5(H5A), C16(H16), C17(H17)
6.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C18(H18A,H18B)
6.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10A), C11(H11A), C8(H8), C21(H21), C22(H22), C23(H23), C20(H20)
6.d Tetrahedral OH refined with riding coordinates:
 O3(H3), O4(H4), O5(H5), O6(H6), O10(H10), O11(H11), O12(H12), O13(H13)
6.e X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4B,H4C)
6.f Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC), C1S(H1SA,H1SB,H1SC)
6.g Idealised tetrahedral OH refined as rotating group:
 O2S(H2S)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'