Synthesis and crystal structure of pyrroloquinoline quinol (PQQH~2~) and pyrroloquinoline quinone (PQQ)
Ikemoto, Kazuto; Mori, Shigeki; Mukai, Kazuo; Acta Crystallographica Section B 73 (2017) 489–497; doi:10.1107/S2052520617002281

data_2108052
_publ_section_title
;
 Synthesis and crystal structure of pyrroloquinoline quinol (PQQH~2~) and
 pyrroloquinoline quinone (PQQ)
;
_journal_coeditor_code           XK5034
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              489
_journal_page_last               497
_journal_paper_doi               10.1107/S2052520617002281
_journal_volume                  73
_journal_year                    2017
_chemical_formula_moiety         'C14 H6 N2 O8, 3(C2 H6 O S)'
_chemical_formula_sum            'C20 H24 N2 O11 S3'
_chemical_formula_weight         564.59
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.901(5)
_cell_length_b                   12.371(8)
_cell_length_c                   28.674(18)
_cell_measurement_reflns_used    7223
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.28
_cell_measurement_theta_min      2.17
_cell_volume                     2448(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            41911
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.175
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.428
_refine_diff_density_min         -0.781
_refine_ls_abs_structure_details
;
 Flack x determined using 1648 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0801P)^2^+4.9734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1852
_reflns_number_gt                4968
_reflns_number_total             5885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            xk5034sup1.cif
_cod_data_source_block           II
_cod_database_code               2108052
_cod_database_fobs_code          2108052
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.993
_shelx_hkl_checksum              29939
_shelx_res_checksum              28943