# Supplementary Material (ESI) for Energy & Environmental Science
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               'Energy Environ.Sci.'

_journal_coden_Cambridge         1148
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Jeffrey Long'
_publ_contact_author_email       JRLONG@BERKELEY.EDU

_publ_section_title              
;
Hydrogen Storage in Water-Stable Metal-Organic
Frameworks Incorporating 1,3- and 1,4-Benzenedipyrazolate

;
loop_
_publ_author_name
'Jeffrey Long'
'Hye Jin Choi.'
'Anne Dailly'
'Mircea Dinc'

# Attachment '2.cif'

data_Co(1,3-bdp)
_database_code_depnum_ccdc_archive 'CCDC 745475'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 Co N5 O1.50'
_chemical_formula_weight         377.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   I4(1)/amd

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z+1/2'
'x, -y, -z'
'y+1/4, x+3/4, -z+1/4'
'-y+1/4, -x+1/4, -z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1'
'x+1/2, -y+1/2, -z+1/2'
'y+3/4, x+5/4, -z+3/4'
'-y+3/4, -x+3/4, -z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z-1/2'
'-x, y, z'
'-y-1/4, -x-3/4, z-1/4'
'y-1/4, x-1/4, z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
'-y+1/4, -x-1/4, z+1/4'
'y+1/4, x+1/4, z-1/4'

_cell_length_a                   22.847(15)
_cell_length_b                   22.847(15)
_cell_length_c                   12.458(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6503(10)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    85
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      18.86

_exptl_crystal_description       rod
_exptl_crystal_colour            purple
_exptl_crystal_size_max          .04
_exptl_crystal_size_mid          .015
_exptl_crystal_size_min          .015
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3136
_exptl_absorpt_coefficient_mu    1.074
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.793714
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.77490
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source station 11.3.1'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker Platinum 200 CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10681
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         19.14
_reflns_number_total             559
_reflns_number_gt                468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX 2'
_computing_cell_refinement       'Bruker SAINT v7.34'
_computing_data_reduction        'Bruker SAINT v7.34'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0010(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         559
_refine_ls_number_parameters     81
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1748
_refine_ls_wR_factor_gt          0.1642
_refine_ls_goodness_of_fit_ref   1.339
_refine_ls_restrained_S_all      1.341
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.28659(6) 0.53659(6) -1.6250 0.0451(14) Uani 1 2 d S . .
N1 N 0.3087(3) 0.5755(5) -1.4893(7) 0.047(3) Uani 1 1 d . . .
N2 N 0.3073(4) 0.5473(4) -1.3936(9) 0.048(3) Uani 1 1 d . . .
C1 C 0.3189(5) 0.6318(6) -1.4683(10) 0.061(3) Uani 1 1 d . . .
H1 H 0.3223 0.6608 -1.5204 0.074 Uiso 1 1 calc R . .
C2 C 0.3238(6) 0.6418(6) -1.3577(11) 0.076(4) Uani 1 1 d . . .
C3 C 0.3158(5) 0.5868(7) -1.3158(10) 0.070(4) Uani 1 1 d . . .
H3 H 0.3162 0.5781 -1.2429 0.084 Uiso 1 1 calc R . .
C4 C 0.3289(7) 0.7500 -1.3547(11) 0.073(5) Uani 1 2 d SD . .
H4 H 0.2971 0.7500 -1.4012 0.087 Uiso 1 2 calc SR A 1
C5 C 0.3539(11) 0.6972(9) -1.3182(17) 0.043(9) Uiso 0.400(16) 1 d PD . 1
C6 C 0.3918(12) 0.6978(13) -1.2294(19) 0.111(13) Uiso 0.400(16) 1 d PD . 1
H6 H 0.4063 0.6626 -1.2026 0.133 Uiso 0.400(16) 1 calc PR . 1
C7 C 0.4080(19) 0.7500 -1.181(3) 0.095(16) Uiso 0.400(16) 2 d SPD . 1
H7 H 0.4293 0.7500 -1.1178 0.114 Uiso 0.400(16) 2 calc SPR . 1
C5' C 0.3185(9) 0.6970(8) -1.2928(15) 0.057(6) Uiso 0.600(16) 1 d PD . 2
C7' C 0.3219(11) 0.7500 -1.123(2) 0.077(9) Uiso 0.600(16) 2 d SPD . 2
H7' H 0.3230 0.7500 -1.0481 0.092 Uiso 0.600(16) 2 calc SPR . 2
C6' C 0.3209(8) 0.6975(8) -1.1811(13) 0.068(7) Uiso 0.600(16) 1 d PD . 2
H6' H 0.3220 0.6621 -1.1443 0.081 Uiso 0.600(16) 1 calc PR . 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0490(15) 0.0490(15) 0.0372(19) -0.0024(7) 0.0024(7) 0.0040(11)
N1 0.062(7) 0.038(8) 0.041(8) 0.003(7) -0.007(4) 0.001(5)
N2 0.067(7) 0.047(7) 0.030(6) 0.005(7) -0.012(5) -0.001(5)
C1 0.091(9) 0.046(11) 0.048(10) 0.018(7) -0.026(6) 0.002(8)
C2 0.141(13) 0.033(11) 0.053(11) 0.005(8) -0.038(7) -0.008(8)
C3 0.112(11) 0.049(11) 0.048(9) -0.006(10) -0.032(7) 0.011(8)
C4 0.110(15) 0.044(12) 0.065(10) 0.000 -0.037(10) 0.000

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 1.975(9) . ?
Co1 N1 1.975(9) 15_441 ?
Co1 N2 1.987(10) 11_544 ?
Co1 N2 1.987(10) 6_562 ?
N1 C1 1.335(13) . ?
N1 N2 1.356(10) . ?
N2 C3 1.338(13) . ?
N2 Co1 1.987(10) 12_454 ?
C1 C2 1.402(13) . ?
C2 C3 1.374(15) . ?
C2 C5' 1.50(2) . ?
C2 C5 1.52(3) . ?
C4 C5 1.410(17) 29_565 ?
C4 C5 1.410(17) . ?
C4 C5' 1.454(19) 29_565 ?
C4 C5' 1.454(19) . ?
C5 C6 1.405(18) . ?
C6 C7 1.385(19) . ?
C7 C6 1.385(19) 29_565 ?
C5' C6' 1.39(2) . ?
C7' C6' 1.403(18) 29_565 ?
C7' C6' 1.403(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co1 N1 120.2(6) . 15_441 ?
N1 Co1 N2 103.8(4) . 11_544 ?
N1 Co1 N2 105.8(3) 15_441 11_544 ?
N1 Co1 N2 105.8(3) . 6_562 ?
N1 Co1 N2 103.8(4) 15_441 6_562 ?
N2 Co1 N2 118.3(5) 11_544 6_562 ?
C1 N1 N2 106.9(8) . . ?
C1 N1 Co1 130.3(9) . . ?
N2 N1 Co1 122.2(9) . . ?
C3 N2 N1 108.2(9) . . ?
C3 N2 Co1 126.9(10) . 12_454 ?
N1 N2 Co1 124.5(8) . 12_454 ?
N1 C1 C2 111.3(9) . . ?
C3 C2 C1 102.3(10) . . ?
C3 C2 C5' 123.6(14) . . ?
C1 C2 C5' 131.2(14) . . ?
C3 C2 C5 134.3(14) . . ?
C1 C2 C5 119.3(15) . . ?
C5' C2 C5 33.4(9) . . ?
N2 C3 C2 111.2(10) . . ?
C5 C4 C5 118(2) 29_565 . ?
C5 C4 C5' 35.3(10) 29_565 29_565 ?
C5 C4 C5' 127.4(14) . 29_565 ?
C5 C4 C5' 127.4(14) 29_565 . ?
C5 C4 C5' 35.3(10) . . ?
C5' C4 C5' 112.6(18) 29_565 . ?
C6 C5 C4 120(2) . . ?
C6 C5 C2 122.8(18) . . ?
C4 C5 C2 115.2(16) . . ?
C7 C6 C5 121(4) . . ?
C6 C7 C6 119(4) . 29_565 ?
C6' C5' C4 121.1(17) . . ?
C6' C5' C2 122.7(16) . . ?
C4 C5' C2 113.6(14) . . ?
C6' C7' C6' 118(2) 29_565 . ?
C5' C6' C7' 121.6(19) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        19.14
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.066
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.015 0.000 -0.003 2281 350 ' '
_platon_squeeze_details          
;
The unit cell contains 8 N,N-diethylformamide and 4 water molecules
which have been treated as a diffuse contribution to the overall
scattering without specific atom positions by SQUEEZE/PLATON.
;