#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:46:15 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179595 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/59/4505917.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_4505917
loop_
_publ_author_name
'Cole, Jacqueline M.'
'Waddell, Paul G.'
'Jayatilaka, Dylan'
_publ_section_title
;
 Solid-State Dilution of Dihydroxybenzophenones with 4,13-Diaza-18-crown-6
 for Photocrystallographic Studies
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2277
_journal_paper_doi               10.1021/cg201558h
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C12 H26 N2 O4, C13 H10 O3'
_chemical_formula_sum            'C25 H36 N2 O7'
_chemical_formula_weight         476.56
_chemical_name_systematic
;
 4,4'-dihydroxybenzophenone, 4,13-diaza-18-crown-6
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.4906(11)
_cell_angle_beta                 104.4329(11)
_cell_angle_gamma                111.0618(9)
_cell_formula_units_Z            2
_cell_length_a                   8.6935(2)
_cell_length_b                   10.3060(2)
_cell_length_c                   15.8548(2)
_cell_measurement_reflns_used    19541
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1276.19(4)
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1995)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40131
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SORTAV
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.184
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0387
_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)+(0.0487P)²+0.1858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                4580
_reflns_number_total             5848
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201558h_si_001.cif
_cod_data_source_block           pr0001
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4505917
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_occupancy
_atom_site_type_symbol
O1 0.64984(12) 0.08588(9) 0.83096(5) 0.0432(2) Uani d 1 O
O2 0.63217(13) 0.68875(9) 0.79964(6) 0.0423(2) Uani d 1 O
O3 0.24119(11) -0.26209(9) 0.46466(6) 0.0387(2) Uani d 1 O
C1 0.60059(14) 0.27823(11) 0.76954(7) 0.0277(2) Uani d 1 C
C2 0.62822(14) 0.36637(12) 0.70370(7) 0.0284(2) Uani d 1 C
C3 0.63898(14) 0.50291(12) 0.71527(7) 0.0298(2) Uani d 1 C
C4 0.62195(15) 0.55487(12) 0.79241(7) 0.0304(2) Uani d 1 C
C5 0.59804(17) 0.46871(13) 0.85899(8) 0.0350(3) Uani d 1 C
C6 0.58896(16) 0.33343(12) 0.84724(7) 0.0332(3) Uani d 1 C
C7 0.59003(14) 0.13082(11) 0.76390(7) 0.0301(2) Uani d 1 C
C8 0.50394(14) 0.03649(11) 0.68074(7) 0.0276(2) Uani d 1 C
C9 0.39267(14) 0.06323(12) 0.60893(7) 0.0289(2) Uani d 1 C
C10 0.30584(15) -0.03424(12) 0.53606(8) 0.0308(2) Uani d 1 C
C11 0.32799(14) -0.16136(12) 0.53362(7) 0.0308(2) Uani d 1 C
C12 0.44077(15) -0.18799(13) 0.60401(8) 0.0357(3) Uani d 1 C
C13 0.52546(15) -0.09090(12) 0.67667(8) 0.0333(3) Uani d 1 C
H2 0.6429(16) 0.3334(13) 0.6509(8) 0.031(3) Uiso d 1 H
H2O 0.606(2) 0.7109(19) 0.8519(12) 0.075(5) Uiso d 1 H
H3 0.6584(17) 0.5646(14) 0.6696(9) 0.037(3) Uiso d 1 H
H3O 0.126(3) -0.258(2) 0.4404(12) 0.084(6) Uiso d 1 H
H5 0.5867(17) 0.5019(14) 0.9126(9) 0.041(4) Uiso d 1 H
H6 0.5751(17) 0.2755(14) 0.8929(9) 0.041(4) Uiso d 1 H
H9 0.3720(16) 0.1500(13) 0.6082(8) 0.030(3) Uiso d 1 H
H10 0.2288(17) -0.0160(13) 0.4875(8) 0.033(3) Uiso d 1 H
H12 0.4559(18) -0.2735(15) 0.6022(9) 0.044(4) Uiso d 1 H
H13 0.5995(17) -0.1105(14) 0.7268(9) 0.038(3) Uiso d 1 H
N1 -0.07923(13) -0.26980(11) 0.41506(6) 0.0334(2) Uani d 1 N
N2 0.56273(13) 0.76906(10) 0.94628(6) 0.0317(2) Uani d 1 N
O4 -0.06306(12) -0.04239(9) 0.31735(5) 0.0407(2) Uani d 1 O
O5 0.10065(11) 0.24194(9) 0.40841(5) 0.0385(2) Uani d 1 O
O6 0.22151(10) 0.58699(8) 0.92617(5) 0.03394(19) Uani d 1 O
O7 0.17294(10) 0.29724(8) 0.94425(5) 0.03366(19) Uani d 1 O
C14 -0.17820(18) -0.38362(14) 0.45769(9) 0.0411(3) Uani d 1 C
C15 -0.14951(18) -0.28589(14) 0.31963(8) 0.0406(3) Uani d 1 C
C16 -0.0486(2) -0.16221(15) 0.28087(9) 0.0428(3) Uani d 1 C
C17 0.0166(2) 0.08099(15) 0.28102(9) 0.0433(3) Uani d 1 C
C18 -0.00587(18) 0.20191(15) 0.32113(8) 0.0402(3) Uani d 1 C
C19 0.09513(19) 0.36566(14) 0.44567(9) 0.0408(3) Uani d 1 C
C20 0.71836(17) 0.87622(13) 1.00258(9) 0.0379(3) Uani d 1 C
C21 0.41817(17) 0.81608(13) 0.92565(9) 0.0368(3) Uani d 1 C
C22 0.25755(18) 0.70019(14) 0.87460(8) 0.0396(3) Uani d 1 C
C23 0.07273(16) 0.47129(13) 0.88141(8) 0.0372(3) Uani d 1 C
C24 0.04199(16) 0.35280(13) 0.93620(9) 0.0372(3) Uani d 1 C
C25 0.13272(17) 0.17053(13) 0.98372(9) 0.0388(3) Uani d 1 C
H1N -0.0800(17) -0.1892(15) 0.4356(9) 0.038(4) Uiso d 1 H
H2N 0.5344(17) 0.6957(15) 0.9764(8) 0.037(3) Uiso d 1 H
H14A -0.299(2) -0.3891(14) 0.4464(9) 0.047(4) Uiso d 1 H
H14B -0.1820(19) -0.4727(16) 0.4311(9) 0.050(4) Uiso d 1 H
H15A -0.1400(17) -0.3708(14) 0.2974(8) 0.038(3) Uiso d 1 H
H15B -0.276(2) -0.3002(15) 0.3023(9) 0.049(4) Uiso d 1 H
H16A 0.074(2) -0.1518(15) 0.2951(9) 0.048(4) Uiso d 1 H
H16B -0.0968(18) -0.1735(15) 0.2152(10) 0.047(4) Uiso d 1 H
H17A -0.035(2) 0.0673(15) 0.2167(11) 0.052(4) Uiso d 1 H
H17B 0.136(2) 0.0998(15) 0.2910(9) 0.050(4) Uiso d 1 H
H18A 0.0249(18) 0.2822(15) 0.2859(9) 0.044(4) Uiso d 1 H
H18B -0.1256(19) 0.1790(14) 0.3206(8) 0.038(3) Uiso d 1 H
H19A 0.1559(18) 0.4476(15) 0.4175(9) 0.044(4) Uiso d 1 H
H19B -0.025(2) 0.3566(15) 0.4351(9) 0.048(4) Uiso d 1 H
H20A 0.7439(18) 0.9614(16) 0.9726(9) 0.047(4) Uiso d 1 H
H20B 0.7027(18) 0.8996(14) 1.0613(9) 0.045(4) Uiso d 1 H
H21A 0.4473(18) 0.8943(15) 0.8912(9) 0.045(4) Uiso d 1 H
H21B 0.3972(17) 0.8480(14) 0.9798(9) 0.037(3) Uiso d 1 H
H22A 0.1576(18) 0.7308(14) 0.8603(9) 0.042(4) Uiso d 1 H
H22B 0.2705(18) 0.6672(14) 0.8168(9) 0.043(4) Uiso d 1 H
H23A -0.0294(19) 0.5014(14) 0.8690(9) 0.043(4) Uiso d 1 H
H23B 0.0881(18) 0.4427(14) 0.8255(9) 0.043(4) Uiso d 1 H
H24A 0.0396(18) 0.3843(15) 0.9936(10) 0.045(4) Uiso d 1 H
H24B -0.0723(19) 0.2773(15) 0.9076(9) 0.045(4) Uiso d 1 H
H25A 0.1113(18) 0.1856(14) 1.0403(9) 0.043(4) Uiso d 1 H
H25B 0.0260(19) 0.0961(15) 0.9436(9) 0.043(4) Uiso d 1 H
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'
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
C4 O2 H2O 111.4(11) . .
C11 O3 H3O 108.3(11) . .
C6 C1 C2 117.96(10) . .
C6 C1 C7 117.52(10) . .
C2 C1 C7 124.47(10) . .
C3 C2 C1 120.48(10) . .
C3 C2 H2 119.4(8) . .
C1 C2 H2 120.1(8) . .
C2 C3 C4 120.68(10) . .
C2 C3 H3 120.7(8) . .
C4 C3 H3 118.6(8) . .
O2 C4 C5 122.81(10) . .
O2 C4 C3 118.00(10) . .
C5 C4 C3 119.18(10) . .
C6 C5 C4 119.75(11) . .
C6 C5 H5 119.4(8) . .
C4 C5 H5 120.9(8) . .
C5 C6 C1 121.91(11) . .
C5 C6 H6 119.8(8) . .
C1 C6 H6 118.3(8) . .
O1 C7 C8 119.81(10) . .
O1 C7 C1 118.59(10) . .
C8 C7 C1 121.56(9) . .
C13 C8 C9 118.13(10) . .
C13 C8 C7 117.85(10) . .
C9 C8 C7 123.83(10) . .
C10 C9 C8 120.93(11) . .
C10 C9 H9 117.3(7) . .
C8 C9 H9 121.8(7) . .
C9 C10 C11 120.04(11) . .
C9 C10 H10 120.6(8) . .
C11 C10 H10 119.3(8) . .
O3 C11 C12 118.39(10) . .
O3 C11 C10 122.10(11) . .
C12 C11 C10 119.50(10) . .
C13 C12 C11 120.05(11) . .
C13 C12 H12 120.5(8) . .
C11 C12 H12 119.4(8) . .
C12 C13 C8 121.32(11) . .
C12 C13 H13 120.5(8) . .
C8 C13 H13 118.2(8) . .
C14 N1 C15 113.19(10) . .
C14 N1 H1N 109.0(9) . .
C15 N1 H1N 107.1(8) . .
C20 N2 C21 111.92(10) . .
C20 N2 H2N 107.0(9) . .
C21 N2 H2N 107.2(9) . .
C17 O4 C16 112.91(10) . .
C18 O5 C19 111.63(10) . .
C22 O6 C23 111.84(9) . .
C25 O7 C24 111.12(9) . .
N1 C14 C19 110.76(11) . 2_556
N1 C14 H14A 111.0(8) . .
C19 C14 H14A 110.4(8) 2_556 .
N1 C14 H14B 107.5(9) . .
C19 C14 H14B 109.6(8) 2_556 .
H14A C14 H14B 107.5(12) . .
N1 C15 C16 110.41(11) . .
N1 C15 H15A 106.4(8) . .
C16 C15 H15A 109.9(8) . .
N1 C15 H15B 111.8(8) . .
C16 C15 H15B 110.7(8) . .
H15A C15 H15B 107.5(11) . .
O4 C16 C15 107.25(10) . .
O4 C16 H16A 110.2(8) . .
C15 C16 H16A 110.5(8) . .
O4 C16 H16B 109.3(8) . .
C15 C16 H16B 110.3(8) . .
H16A C16 H16B 109.3(11) . .
O4 C17 C18 110.05(11) . .
O4 C17 H17A 109.1(9) . .
C18 C17 H17A 110.3(9) . .
O4 C17 H17B 110.4(9) . .
C18 C17 H17B 109.4(9) . .
H17A C17 H17B 107.6(12) . .
O5 C18 C17 110.20(11) . .
O5 C18 H18A 109.4(8) . .
C17 C18 H18A 109.4(8) . .
O5 C18 H18B 110.0(8) . .
C17 C18 H18B 110.8(8) . .
H18A C18 H18B 106.8(11) . .
O5 C19 C14 108.39(11) . 2_556
O5 C19 H19A 109.7(8) . .
C14 C19 H19A 110.8(8) 2_556 .
O5 C19 H19B 109.3(9) . .
C14 C19 H19B 109.9(8) 2_556 .
H19A C19 H19B 108.7(12) . .
N2 C20 C25 110.52(10) . 2_667
N2 C20 H20A 107.7(8) . .
C25 C20 H20A 108.6(9) 2_667 .
N2 C20 H20B 111.9(8) . .
C25 C20 H20B 109.8(8) 2_667 .
H20A C20 H20B 108.2(11) . .
N2 C21 C22 110.64(10) . .
N2 C21 H21A 107.3(9) . .
C22 C21 H21A 110.1(8) . .
N2 C21 H21B 111.6(8) . .
C22 C21 H21B 108.4(8) . .
H21A C21 H21B 108.7(11) . .
O6 C22 C21 108.38(10) . .
O6 C22 H22A 108.6(8) . .
C21 C22 H22A 111.5(8) . .
O6 C22 H22B 109.4(8) . .
C21 C22 H22B 111.4(8) . .
H22A C22 H22B 107.4(11) . .
O6 C23 C24 110.40(10) . .
O6 C23 H23A 108.6(8) . .
C24 C23 H23A 109.2(8) . .
O6 C23 H23B 108.9(8) . .
C24 C23 H23B 110.4(8) . .
H23A C23 H23B 109.3(11) . .
O7 C24 C23 109.75(10) . .
O7 C24 H24A 110.5(8) . .
C23 C24 H24A 110.0(8) . .
O7 C24 H24B 109.2(8) . .
C23 C24 H24B 109.4(8) . .
H24A C24 H24B 108.1(12) . .
O7 C25 C20 108.60(10) . 2_667
O7 C25 H25A 109.8(8) . .
C20 C25 H25A 109.8(8) 2_667 .
O7 C25 H25B 109.5(8) . .
C20 C25 H25B 109.7(8) 2_667 .
H25A C25 H25B 109.4(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C7 . 1.2334(13)
O2 C4 . 1.3523(14)
O2 H2O . 0.96(2)
O3 C11 . 1.3596(14)
O3 H3O . 0.99(2)
C1 C6 . 1.3939(16)
C1 C2 . 1.3988(15)
C1 C7 . 1.4892(15)
C2 C3 . 1.3838(16)
C2 H2 . 0.955(13)
C3 C4 . 1.3932(16)
C3 H3 . 0.973(13)
C4 C5 . 1.3923(16)
C5 C6 . 1.3762(17)
C5 H5 . 0.955(14)
C6 H6 . 0.945(14)
C7 C8 . 1.4856(16)
C8 C13 . 1.3942(16)
C8 C9 . 1.3985(15)
C9 C10 . 1.3834(16)
C9 H9 . 0.973(13)
C10 C11 . 1.3926(16)
C10 H10 . 0.955(13)
C11 C12 . 1.3912(17)
C12 C13 . 1.3779(18)
C12 H12 . 0.937(14)
C13 H13 . 0.963(13)
N1 C14 . 1.4667(17)
N1 C15 . 1.4669(16)
N1 H1N . 0.893(14)
N2 C20 . 1.4677(16)
N2 C21 . 1.4686(16)
N2 H2N . 0.890(14)
O4 C17 . 1.4166(16)
O4 C16 . 1.4181(16)
O5 C18 . 1.4210(15)
O5 C19 . 1.4221(16)
O6 C22 . 1.4174(15)
O6 C23 . 1.4205(15)
O7 C25 . 1.4192(15)
O7 C24 . 1.4274(15)
C14 C19 2_556 1.500(2)
C14 H14A . 1.004(15)
C14 H14B . 0.994(16)
C15 C16 . 1.500(2)
C15 H15A . 0.979(14)
C15 H15B . 1.020(16)
C16 H16A . 0.994(15)
C16 H16B . 1.009(15)
C17 C18 . 1.490(2)
C17 H17A . 0.993(16)
C17 H17B . 0.957(16)
C18 H18A . 0.996(15)
C18 H18B . 0.979(14)
C19 C14 2_556 1.500(2)
C19 H19A . 0.998(15)
C19 H19B . 0.988(15)
C20 C25 2_667 1.5051(19)
C20 H20A . 0.982(15)
C20 H20B . 1.013(15)
C21 C22 . 1.5010(19)
C21 H21A . 0.971(15)
C21 H21B . 0.997(14)
C22 H22A . 1.003(14)
C22 H22B . 1.021(15)
C23 C24 . 1.4889(19)
C23 H23A . 1.017(14)
C23 H23B . 0.987(15)
C24 H24A . 0.972(15)
C24 H24B . 1.006(15)
C25 C20 2_667 1.5051(18)
C25 H25A . 0.983(15)
C25 H25B . 1.020(15)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2O N2 0.96(2) 1.78(2) 2.7351(13) 174.4(17)
O3 H3O N1 0.99(2) 1.69(2) 2.6705(13) 168.9(18)
