Novel phenazine crystals enable direct electron transfer to methanogens in anaerobic digestion by redox potential modulation
Beckmann, Sabrina; Welte, Cornelia; Li, Xiaomin; Oo, Yee M.; Kroeninger, Lena; Heo, Yooun; Zhang, Miaomiao; Ribeiro, Daniela; Lee, Matthew; Bhadbhade, Mohan; Marjo, Christopher E.; Seidel, Jan; Deppenmeier, Uwe; Manefield, Mike; Energy Environ. Sci. 9 (2016) 644–; doi:10.1039/C5EE03085D

data_1540724
_publ_section_title
;
 Novel phenazine crystals enable direct electron transfer to methanogens
 in anaerobic digestion by redox potential modulation
;
_journal_issue                   2
_journal_name_full               'Energy Environ. Sci.'
_journal_page_first              644
_journal_paper_doi               10.1039/C5EE03085D
_journal_volume                  9
_journal_year                    2016
_chemical_formula_moiety         'C15 H16 N4, 4(H2 O)'
_chemical_formula_sum            'C15 H24 N4 O4'
_chemical_formula_weight         324.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2014-08-21 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.27(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4300(19)
_cell_length_b                   4.7380(9)
_cell_length_c                   18.556(4)
_cell_measurement_temperature    100
_cell_volume                     828.9(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Australian Synchrotron'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10069
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_min         1.098
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.004
_refine_diff_density_max         2.485
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.250
_refine_ls_abs_structure_details
;
 Flack x determined using 1109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.728
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2809
_refine_ls_number_restraints     131
_refine_ls_restrained_S_all      2.678
_refine_ls_R_factor_all          0.2255
_refine_ls_R_factor_gt           0.2218
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4964
_refine_ls_wR_factor_ref         0.5053
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                2660
_reflns_number_total             2809
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ee03085d2.cif
_cod_data_source_block           p21_trial1
_cod_depositor_comments          'Adding full bibliography for 1540724.cif.'
_cod_database_code               1540724
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H4WA-N2
 2.2 with sigma of 0.02
 H1WB-N3
 2 with sigma of 0.02
 H3WA-O4W
 1.9 with sigma of 0.02
 H2WB-O1W
 1.9 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.9A with sigma of 0.02 and sigma
for terminal atoms of 0.04
4.a Free rotating group:
 O1W(H1WA,H1WB), O3W(H3WA,H3WB), O2W(H2WA,H2WB), O4W(H4WA,H4WB)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C10(H10), C1(H1)
4.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
4.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              71486
_olex2_exptl_crystal_mounting_method
'One of the extremely thin ribbon like crystals was mounted on the cryo loop with paraffin oil.'
_olex2_submission_original_sample_id 'Neutral Red Dye'
_olex2_submission_special_instructions 'No special instructions were received'