#------------------------------------------------------------------------------
#$Date: 2015-12-09 13:49:30 +0200 (Wed, 09 Dec 2015) $
#$Revision: 170976 $
#$URL: svn://www.crystallography.net/cod/cif/1/53/10/1531041.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1531041
loop_
_publ_author_name
'Gazi, Sarifuddin'
'Hung Ng, Wilson Kwok'
'Ganguly, Rakesh'
'Putra Moeljadi, Adhitya Mangala'
'Hirao, Hajime'
'Soo, Han Sen'
_publ_section_title
;
 Selective photocatalytic C--C bond cleavage under ambient conditions with
 earth abundant vanadium complexes
;
_journal_issue                   12
_journal_name_full               'Chem. Sci.'
_journal_page_first              7130
_journal_paper_doi               10.1039/C5SC02923F
_journal_volume                  6
_journal_year                    2015
_chemical_formula_sum            'C30 H44 N2 O8 V2'
_chemical_formula_weight         662.55
_chemical_properties_physical    'Light-sensitive, Photo-sensitive'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2015-04-10 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.8835(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1706(6)
_cell_length_b                   11.0345(5)
_cell_length_c                   23.8844(12)
_cell_measurement_reflns_used    4220
_cell_measurement_temperature    133.(2)
_cell_measurement_theta_max      30.4199
_cell_measurement_theta_min      2.5122
_cell_volume                     3149.9(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      133.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18722
_diffrn_reflns_theta_full        31.04
_diffrn_reflns_theta_max         31.04
_diffrn_reflns_theta_min         2.55
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.434
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         5001
_refine_ls_number_restraints     83
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0409
_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/[σ²(Fo²)+(0.0418P)²+2.8598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                3899
_reflns_number_total             5001
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5sc02923f2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 1531040--1531042.cif.'
_cod_database_code               1531041
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V V1 0.13740(2) 0.98492(2) 0.02923(2) 0.01615(8) Uani d . . . 1.0 . .
C C1 0.12344(13) 0.79535(13) 0.11642(7) 0.0160(3) Uani d . . . 1.0 . .
C C2 0.13581(14) 0.77544(14) 0.17617(7) 0.0174(3) Uani d . . . 1.0 . .
C C3 0.20419(15) 0.86260(14) 0.21965(7) 0.0193(3) Uani d . . . 1.0 . .
C C4 0.32630(16) 0.86241(18) 0.21177(8) 0.0278(4) Uani d . . . 1.0 . .
H H4A 0.3698 0.919 0.2389 0.042 Uiso calc U . R 1.0 . .
H H4B 0.3298 0.8874 0.1728 0.042 Uiso calc U . R 1.0 . .
H H4C 0.3574 0.7806 0.2186 0.042 Uiso calc U . R 1.0 . .
C C5 0.15698(17) 0.99264(15) 0.21245(8) 0.0263(4) Uani d . . . 1.0 . .
H H5A 0.2014 1.0457 0.241 0.039 Uiso calc U . R 1.0 . .
H H5B 0.079 0.9925 0.2176 0.039 Uiso calc U . R 1.0 . .
H H5C 0.1606 1.0223 0.1742 0.039 Uiso calc U . R 1.0 . .
C C6 0.20294(18) 0.82519(17) 0.28130(8) 0.0294(4) Uani d . . . 1.0 . .
H H6A 0.2377 0.7452 0.2887 0.044 Uiso calc U . R 1.0 . .
H H6B 0.1255 0.8218 0.2872 0.044 Uiso calc U . R 1.0 . .
H H6C 0.2449 0.8847 0.3074 0.044 Uiso calc U . R 1.0 . .
C C7 0.08627(16) 0.67190(15) 0.19359(8) 0.0242(4) Uani d . . . 1.0 . .
H H7 0.0927 0.6573 0.2333 0.029 Uiso calc U . R 1.0 . .
C C8 0.02752(17) 0.58863(17) 0.15516(9) 0.0300(4) Uani d . . . 1.0 . .
H H8 -0.0065 0.5199 0.1687 0.036 Uiso calc U . R 1.0 . .
C C9 0.01916(16) 0.60665(16) 0.09771(8) 0.0253(4) Uani d . . . 1.0 . .
H H9 -0.0191 0.5491 0.0715 0.03 Uiso calc U . R 1.0 . .
C C10 0.06670(14) 0.70943(14) 0.07759(7) 0.0183(3) Uani d . . . 1.0 . .
C C11 0.06946(15) 0.71693(14) 0.01713(7) 0.0203(3) Uani d . . . 1.0 . .
H H11 0.0424 0.6488 -0.0057 0.024 Uiso calc U . R 1.0 . .
C C12 0.1294(6) 0.7867(7) -0.0664(3) 0.0223(12) Uani d U P D 0.631(5) A 1
H H12A 0.1068 0.7031 -0.0785 0.027 Uiso calc U P R 0.631(5) A 1
H H12B 0.2111 0.7933 -0.0644 0.027 Uiso calc U P R 0.631(5) A 1
C C13 0.0705(3) 0.8749(3) -0.11144(12) 0.0241(7) Uani d U P D 0.631(5) A 1
H H13A 0.1004 0.8638 -0.1469 0.029 Uiso calc U P R 0.631(5) A 1
H H13B -0.0103 0.8555 -0.1201 0.029 Uiso calc U P R 0.631(5) A 1
C C14 -0.0852(12) 0.9943(12) 0.0930(4) 0.0228(19) Uani d U P D 0.631(5) A 1
H H14A -0.0431 0.9421 0.1234 0.027 Uiso calc U P R 0.631(5) A 1
H H14B -0.1653 0.9725 0.0881 0.027 Uiso calc U P R 0.631(5) A 1
C C12A 0.1061(12) 0.7899(13) -0.0696(5) 0.025(2) Uani d U P D 0.369(5) A 2
H H12C 0.0291 0.7728 -0.09 0.03 Uiso calc U P R 0.369(5) A 2
H H12D 0.1532 0.7189 -0.0744 0.03 Uiso calc U P R 0.369(5) A 2
C C13A 0.1505(5) 0.9002(4) -0.0960(2) 0.0248(12) Uani d U P D 0.369(5) A 2
H H13C 0.1549 0.8815 -0.136 0.03 Uiso calc U P R 0.369(5) A 2
H H13D 0.2274 0.9173 -0.0753 0.03 Uiso calc U P R 0.369(5) A 2
C C14A -0.0791(18) 0.986(2) 0.0948(6) 0.018(3) Uani d U P D 0.369(5) A 2
H H14C -0.0112 0.9925 0.1249 0.022 Uiso calc U P R 0.369(5) A 2
H H14D -0.1219 0.9144 0.1031 0.022 Uiso calc U P R 0.369(5) A 2
C C15 0.2182(2) 1.2206(2) 0.07130(10) 0.0484(6) Uani d . . . 1.0 . .
H H15A 0.2796 1.1972 0.0523 0.073 Uiso calc U . R 1.0 . .
H H15B 0.2474 1.2347 0.1119 0.073 Uiso calc U . R 1.0 . .
H H15C 0.1833 1.2951 0.0539 0.073 Uiso calc U . R 1.0 . .
N N1 0.10507(12) 0.80688(12) -0.00823(6) 0.0186(3) Uani d . . D 1.0 . .
O O1 0.25800(11) 0.99207(11) 0.01211(6) 0.0245(3) Uani d . . . 1.0 . .
O O2 0.16815(10) 0.89304(10) 0.09743(5) 0.0173(2) Uani d . . . 1.0 . .
O O3 -0.04698(10) 0.97128(10) 0.04054(5) 0.0173(2) Uani d . . D 1.0 . .
O O4 0.13822(11) 1.12748(10) 0.06525(5) 0.0231(3) Uani d . . . 1.0 . .
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'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 V1 O4 . . 99.06(6)
O1 V1 O3 . 5_575 99.95(6)
O4 V1 O3 . 5_575 98.58(5)
O1 V1 O2 . . 101.80(6)
O4 V1 O2 . . 94.29(5)
O3 V1 O2 5_575 . 152.58(5)
O1 V1 N1 . . 92.47(6)
O4 V1 N1 . . 168.40(6)
O3 V1 N1 5_575 . 80.59(5)
O2 V1 N1 . . 81.99(5)
O1 V1 O3 . . 171.98(6)
O4 V1 O3 . . 85.34(5)
O3 V1 O3 5_575 . 72.65(5)
O2 V1 O3 . . 84.45(5)
N1 V1 O3 . . 83.37(5)
O2 C1 C10 . . 120.18(15)
O2 C1 C2 . . 119.73(14)
C10 C1 C2 . . 120.06(14)
C7 C2 C1 . . 117.17(15)
C7 C2 C3 . . 121.39(15)
C1 C2 C3 . . 121.41(14)
C6 C3 C4 . . 107.67(15)
C6 C3 C2 . . 112.19(14)
C4 C3 C2 . . 109.24(13)
C6 C3 C5 . . 106.66(14)
C4 C3 C5 . . 109.68(15)
C2 C3 C5 . . 111.30(14)
C3 C4 H4A . . 109.5
C3 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C3 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
C3 C5 H5A . . 109.5
C3 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
C3 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
C3 C6 H6A . . 109.5
C3 C6 H6B . . 109.5
H6A C6 H6B . . 109.5
C3 C6 H6C . . 109.5
H6A C6 H6C . . 109.5
H6B C6 H6C . . 109.5
C2 C7 C8 . . 122.72(17)
C2 C7 H7 . . 118.6
C8 C7 H7 . . 118.6
C9 C8 C7 . . 119.63(17)
C9 C8 H8 . . 120.2
C7 C8 H8 . . 120.2
C8 C9 C10 . . 120.27(17)
C8 C9 H9 . . 119.9
C10 C9 H9 . . 119.9
C9 C10 C1 . . 120.09(16)
C9 C10 C11 . . 118.44(15)
C1 C10 C11 . . 120.95(15)
N1 C11 C10 . . 125.99(15)
N1 C11 H11 . . 117.0
C10 C11 H11 . . 117.0
N1 C12 C13 . . 114.4(5)
N1 C12 H12A . . 108.7
C13 C12 H12A . . 108.7
N1 C12 H12B . . 108.7
C13 C12 H12B . . 108.7
H12A C12 H12B . . 107.6
C14 C13 C12 5_575 . 113.0(6)
C14 C13 H13A 5_575 . 109.0
C12 C13 H13A . . 109.0
C14 C13 H13B 5_575 . 109.0
C12 C13 H13B . . 109.0
H13A C13 H13B . . 107.8
O3 C14 C13 . 5_575 112.5(8)
O3 C14 H14A . . 109.1
C13 C14 H14A 5_575 . 109.1
O3 C14 H14B . . 109.1
C13 C14 H14B 5_575 . 109.1
H14A C14 H14B . . 107.8
N1 C12A C13A . . 112.4(9)
N1 C12A H12C . . 109.1
C13A C12A H12C . . 109.1
N1 C12A H12D . . 109.1
C13A C12A H12D . . 109.1
H12C C12A H12D . . 107.9
C12A C13A C14A . 5_575 113.7(10)
C12A C13A H13C . . 108.8
C14A C13A H13C 5_575 . 108.8
C12A C13A H13D . . 108.8
C14A C13A H13D 5_575 . 108.8
H13C C13A H13D . . 107.7
O3 C14A C13A . 5_575 111.4(13)
O3 C14A H14C . . 109.4
C13A C14A H14C 5_575 . 109.4
O3 C14A H14D . . 109.4
C13A C14A H14D 5_575 . 109.4
H14C C14A H14D . . 108.0
O4 C15 H15A . . 109.5
O4 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
O4 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C11 N1 C12A . . 116.0(5)
C11 N1 C12 . . 118.0(3)
C11 N1 V1 . . 124.03(11)
C12A N1 V1 . . 119.3(5)
C12 N1 V1 . . 117.9(3)
C1 O2 V1 . . 134.59(10)
C14A O3 V1 . 5_575 124.0(9)
C14 O3 V1 . 5_575 119.7(6)
C14A O3 V1 . . 122.3(9)
C14 O3 V1 . . 124.7(6)
V1 O3 V1 5_575 . 107.34(5)
C15 O4 V1 . . 129.28(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
V1 O1 . 1.5984(13)
V1 O4 . 1.7920(12)
V1 O3 5_575 1.8787(12)
V1 O2 . 1.8950(11)
V1 N1 . 2.1639(14)
V1 O3 . 2.3152(12)
C1 O2 . 1.3254(18)
C1 C10 . 1.412(2)
C1 C2 . 1.424(2)
C2 C7 . 1.392(2)
C2 C3 . 1.539(2)
C3 C6 . 1.532(2)
C3 C4 . 1.533(3)
C3 C5 . 1.543(2)
C4 H4A . 0.98
C4 H4B . 0.98
C4 H4C . 0.98
C5 H5A . 0.98
C5 H5B . 0.98
C5 H5C . 0.98
C6 H6A . 0.98
C6 H6B . 0.98
C6 H6C . 0.98
C7 C8 . 1.397(3)
C7 H7 . 0.95
C8 C9 . 1.371(3)
C8 H8 . 0.95
C9 C10 . 1.399(2)
C9 H9 . 0.95
C10 C11 . 1.453(2)
C11 N1 . 1.280(2)
C11 H11 . 0.95
C12 N1 . 1.490(7)
C12 C13 . 1.526(7)
C12 H12A . 0.99
C12 H12B . 0.99
C13 C14 5_575 1.510(13)
C13 H13A . 0.99
C13 H13B . 0.99
C14 O3 . 1.439(7)
C14 C13 5_575 1.510(13)
C14 H14A . 0.99
C14 H14B . 0.99
C12A N1 . 1.480(11)
C12A C13A . 1.516(13)
C12A H12C . 0.99
C12A H12D . 0.99
C13A C14A 5_575 1.53(2)
C13A H13C . 0.99
C13A H13D . 0.99
C14A O3 . 1.434(12)
C14A C13A 5_575 1.53(2)
C14A H14C . 0.99
C14A H14D . 0.99
C15 O4 . 1.404(2)
C15 H15A . 0.98
C15 H15B . 0.98
C15 H15C . 0.98
O3 V1 5_575 1.8787(12)
