#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/59/1515953.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_1515953
loop_
_publ_author_name
'Hoijemberg, Pablo Ariel'
'Karlen, Steven D.'
'Sanramé, Carlos Norberto'
'Aramendía, Pedro Francisco'
'García-Garibay, Miguel Angel'
_publ_section_title
;
 Photolysis of an asymmetrically substituted diazene in solution and in
 the crystalline state.
;
_journal_issue                   7
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              961
_journal_page_last               969
_journal_paper_doi               10.1039/b902272d
_journal_volume                  8
_journal_year                    2009
_chemical_formula_sum            'C31 H30 O'
_chemical_formula_weight         418.55
_chemical_name_systematic
;
?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.416(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1279(9)
_cell_length_b                   6.3065(7)
_cell_length_c                   22.035(2)
_cell_measurement_reflns_used    6856
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.249
_cell_measurement_theta_min      2.578
_cell_volume                     1120.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9614
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9723
_exptl_absorpt_correction_T_min  0.9456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0551P)²+0.2940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                2461
_reflns_number_total             2720
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b902272d.txt
_cod_data_source_block           gg1404sm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-Scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2/n
_cod_database_code               1515953
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'
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
O1 O 0.7500 0.25171(16) 0.7500 0.0279(2) Uani 1 2 d S
C1 C 0.30192(13) 1.00442(16) 0.97779(5) 0.0245(2) Uani 1 1 d .
H1 H 0.3512 1.1149 0.9570 0.029 Uiso 1 1 calc R
C2 C 0.23487(13) 1.04986(17) 1.03116(5) 0.0268(2) Uani 1 1 d .
H2 H 0.2393 1.1905 1.0467 0.032 Uiso 1 1 calc R
C3 C 0.16144(13) 0.89101(17) 1.06183(4) 0.0257(2) Uani 1 1 d .
H3 H 0.1169 0.9218 1.0986 0.031 Uiso 1 1 calc R
C4 C 0.15353(13) 0.68640(17) 1.03833(5) 0.0254(2) Uani 1 1 d .
H4 H 0.1017 0.5773 1.0588 0.030 Uiso 1 1 calc R
C5 C 0.22120(12) 0.64049(15) 0.98497(4) 0.0222(2) Uani 1 1 d .
H5 H 0.2151 0.5000 0.9693 0.027 Uiso 1 1 calc R
C6 C 0.29794(12) 0.79835(15) 0.95416(4) 0.0196(2) Uani 1 1 d .
C7 C 0.37646(12) 0.74580(15) 0.89877(4) 0.0192(2) Uani 1 1 d .
C8 C 0.45310(12) 0.54879(15) 0.89357(4) 0.0199(2) Uani 1 1 d .
H8 H 0.4581 0.4507 0.9265 0.024 Uiso 1 1 calc R
C9 C 0.52185(11) 0.49426(15) 0.84126(4) 0.0195(2) Uani 1 1 d .
H9 H 0.5712 0.3585 0.8387 0.023 Uiso 1 1 calc R
C10 C 0.51984(11) 0.63562(14) 0.79224(4) 0.0184(2) Uani 1 1 d .
C11 C 0.44882(13) 0.83483(15) 0.79820(4) 0.0223(2) Uani 1 1 d .
H11 H 0.4490 0.9355 0.7662 0.027 Uiso 1 1 calc R
C12 C 0.37761(12) 0.88857(15) 0.85033(4) 0.0219(2) Uani 1 1 d .
H12 H 0.3290 1.0247 0.8530 0.026 Uiso 1 1 calc R
C13 C 0.58339(12) 0.56363(15) 0.73280(4) 0.0188(2) Uani 1 1 d .
C14 C 0.7500 0.4443(2) 0.7500 0.0188(3) Uani 1 2 d S
C15 C 0.45412(13) 0.40658(17) 0.70121(5) 0.0245(2) Uani 1 1 d .
H15A H 0.3469 0.4784 0.6919 0.037 Uiso 1 1 calc R
H15B H 0.4425 0.2864 0.7285 0.037 Uiso 1 1 calc R
H15C H 0.4908 0.3552 0.6632 0.037 Uiso 1 1 calc R
C16 C 0.60042(12) 0.74691(15) 0.68792(4) 0.0217(2) Uani 1 1 d .
H16A H 0.6483 0.6933 0.6523 0.032 Uiso 1 1 calc R
H16B H 0.6730 0.8565 0.7084 0.032 Uiso 1 1 calc R
H16C H 0.4908 0.8076 0.6745 0.032 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 120.95(9) . .
C2 C1 H1 119.5 . .
C6 C1 H1 119.5 . .
C3 C2 C1 120.31(9) . .
C3 C2 H2 119.8 . .
C1 C2 H2 119.8 . .
C2 C3 C4 119.47(9) . .
C2 C3 H3 120.3 . .
C4 C3 H3 120.3 . .
C3 C4 C5 120.27(9) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C4 C5 C6 120.84(9) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C5 C6 C1 118.14(9) . .
C5 C6 C7 120.43(9) . .
C1 C6 C7 121.41(9) . .
C12 C7 C8 117.52(8) . .
C12 C7 C6 121.98(9) . .
C8 C7 C6 120.50(8) . .
C9 C8 C7 121.24(8) . .
C9 C8 H8 119.4 . .
C7 C8 H8 119.4 . .
C8 C9 C10 121.17(9) . .
C8 C9 H9 119.4 . .
C10 C9 H9 119.4 . .
C11 C10 C9 117.69(8) . .
C11 C10 C13 122.31(8) . .
C9 C10 C13 119.86(8) . .
C12 C11 C10 121.16(9) . .
C12 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
C11 C12 C7 121.17(9) . .
C11 C12 H12 119.4 . .
C7 C12 H12 119.4 . .
C10 C13 C16 113.19(8) . .
C10 C13 C15 106.85(7) . .
C16 C13 C15 107.74(8) . .
C10 C13 C14 108.27(6) . .
C16 C13 C14 111.89(7) . .
C15 C13 C14 108.71(8) . .
O1 C14 C13 118.98(5) . 2_656
O1 C14 C13 118.98(6) . .
C13 C14 C13 122.04(11) 2_656 .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C13 C16 H16A 109.5 . .
C13 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C13 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C14 1.2149(17) .
C1 C2 1.3884(14) .
C1 C6 1.3989(14) .
C1 H1 0.9500 .
C2 C3 1.3858(15) .
C2 H2 0.9500 .
C3 C4 1.3888(15) .
C3 H3 0.9500 .
C4 C5 1.3914(13) .
C4 H4 0.9500 .
C5 C6 1.3966(13) .
C5 H5 0.9500 .
C6 C7 1.4858(13) .
C7 C12 1.3973(13) .
C7 C8 1.4012(13) .
C8 C9 1.3877(13) .
C8 H8 0.9500 .
C9 C10 1.3989(13) .
C9 H9 0.9500 .
C10 C11 1.3958(13) .
C10 C13 1.5372(12) .
C11 C12 1.3932(13) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C16 1.5390(13) .
C13 C15 1.5430(13) .
C13 C14 1.5527(11) .
C14 C13 1.5527(11) 2_656
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.45(16) .
C1 C2 C3 C4 -0.82(16) .
C2 C3 C4 C5 1.04(16) .
C3 C4 C5 C6 -0.01(16) .
C4 C5 C6 C1 -1.22(15) .
C4 C5 C6 C7 177.26(9) .
C2 C1 C6 C5 1.45(15) .
C2 C1 C6 C7 -177.01(9) .
C5 C6 C7 C12 146.49(10) .
C1 C6 C7 C12 -35.08(14) .
C5 C6 C7 C8 -33.67(14) .
C1 C6 C7 C8 144.76(10) .
C12 C7 C8 C9 -2.46(14) .
C6 C7 C8 C9 177.69(9) .
C7 C8 C9 C10 1.19(14) .
C8 C9 C10 C11 1.08(14) .
C8 C9 C10 C13 -174.73(8) .
C9 C10 C11 C12 -2.03(15) .
C13 C10 C11 C12 173.67(9) .
C10 C11 C12 C7 0.74(16) .
C8 C7 C12 C11 1.51(15) .
C6 C7 C12 C11 -178.65(9) .
C11 C10 C13 C16 14.15(13) .
C9 C10 C13 C16 -170.24(9) .
C11 C10 C13 C15 -104.28(10) .
C9 C10 C13 C15 71.33(11) .
C11 C10 C13 C14 138.79(9) .
C9 C10 C13 C14 -45.60(11) .
C10 C13 C14 O1 99.94(6) .
C16 C13 C14 O1 -134.64(6) .
C15 C13 C14 O1 -15.78(7) .
C10 C13 C14 C13 -80.06(6) 2_656
C16 C13 C14 C13 45.36(6) 2_656
C15 C13 C14 C13 164.22(7) 2_656
