#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:16:31 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179658 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/11/4511137.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_4511137
loop_
_publ_author_name
'Tominaga, Masahide'
'Katagiri, Kosuke'
'Azumaya, Isao'
_publ_section_title
;
 Pseudopolymorph and Charge-Transfer Co-Crystal of Disubstituted
 Adamantane containing Dimethoxyphenol Moieties
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3692
_journal_paper_doi               10.1021/cg900404h
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C32 H38 O7'
_chemical_formula_weight         534.62
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 110.752(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.015(2)
_cell_length_b                   21.454(3)
_cell_length_c                   9.6703(14)
_cell_measurement_reflns_used    3875
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.40
_cell_volume                     2913.0(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7116
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.22
_diffrn_reflns_theta_min         1.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.384
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.383
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.2938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.1760
_reflns_number_gt                2576
_reflns_number_total             2956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg900404h_si_001.cif
_cod_data_source_block           Crystal_1_(type_II)
_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/ACS/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      C2/c
_cod_database_code               4511137
loop_
_symmetry_equiv_pos_as_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_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
C17 C 0.0318(4) 0.87453(13) 0.3225(4) 0.1191(16) Uani 1 1 d .
H17 H 0.0544 0.8362 0.3715 0.143 Uiso 1 1 calc R
C16 C 0.0611(2) 0.92818(14) 0.3925(3) 0.0783(8) Uani 1 1 d .
H16 H 0.1035 0.9283 0.4924 0.094 Uiso 1 1 calc R
C15 C 0.03007(17) 0.98306(11) 0.3202(3) 0.0617(6) Uani 1 1 d .
H15 H 0.0512 1.0215 0.3699 0.074 Uiso 1 1 calc R
O3 O 0.29691(7) 0.95119(5) 1.13061(11) 0.0309(3) Uani 1 1 d U
C10 C 0.0000 0.83146(8) 0.7500 0.0181(4) Uani 1 2 d S
H10A H 0.0023 0.8586 0.8339 0.022 Uiso 0.50 1 calc PR
H10B H -0.0023 0.8586 0.6661 0.022 Uiso 0.50 1 calc PR
O1 O 0.41502(7) 0.95229(5) 0.97441(11) 0.0280(3) Uani 1 1 d .
H1 H 0.4251 0.9667 1.0594 0.042 Uiso 1 1 calc R
C4 C 0.17786(9) 0.83457(6) 0.84029(14) 0.0192(3) Uani 1 1 d .
C5 C 0.23963(9) 0.83813(6) 0.76218(14) 0.0220(3) Uani 1 1 d .
H5 H 0.2284 0.8132 0.6764 0.026 Uiso 1 1 calc R
C1 C 0.33667(9) 0.91465(6) 0.93435(15) 0.0220(3) Uani 1 1 d .
C12 C 0.09357(9) 0.74907(6) 0.92468(14) 0.0222(3) Uani 1 1 d .
H12A H 0.1511 0.7224 0.9534 0.027 Uiso 1 1 calc R
H12B H 0.0968 0.7750 1.0110 0.027 Uiso 1 1 calc R
C3 C 0.19571(9) 0.87254(6) 0.96488(14) 0.0209(3) Uani 1 1 d .
H3 H 0.1538 0.8712 1.0189 0.025 Uiso 1 1 calc R
C6 C 0.31807(9) 0.87805(6) 0.80894(15) 0.0231(3) Uani 1 1 d .
C14 C 0.0000 0.66628(9) 0.7500 0.0281(5) Uani 1 2 d S
H14A H -0.0571 0.6393 0.7225 0.034 Uiso 0.50 1 calc PR
H14B H 0.0571 0.6393 0.7775 0.034 Uiso 0.50 1 calc PR
C9 C 0.09133(8) 0.79152(6) 0.79485(13) 0.0187(3) Uani 1 1 d .
C11 C 0.08504(10) 0.74906(6) 0.66282(14) 0.0225(3) Uani 1 1 d .
H11A H 0.0832 0.7751 0.5773 0.027 Uiso 1 1 calc R
H11B H 0.1424 0.7223 0.6896 0.027 Uiso 1 1 calc R
C2 C 0.27386(10) 0.91220(6) 1.01061(14) 0.0220(3) Uani 1 1 d .
C13 C 0.00422(10) 0.70788(6) 0.88069(15) 0.0247(3) Uani 1 1 d .
H13 H 0.0066 0.6811 0.9666 0.030 Uiso 1 1 calc R
O2 O 0.38345(8) 0.88418(6) 0.73996(11) 0.0356(3) Uani 1 1 d U
C7 C 0.24304(13) 0.94535(9) 1.22411(19) 0.0427(5) Uani 1 1 d U
H7A H 0.1773 0.9585 1.1705 0.064 Uiso 1 1 calc R
H7B H 0.2710 0.9717 1.3116 0.064 Uiso 1 1 calc R
H7C H 0.2435 0.9018 1.2548 0.064 Uiso 1 1 calc R
C8 C 0.36080(17) 0.85901(15) 0.5986(2) 0.0787(9) Uani 1 1 d U
H8A H 0.3636 0.8134 0.6051 0.118 Uiso 1 1 calc R
H8B H 0.4065 0.8739 0.5547 0.118 Uiso 1 1 calc R
H8C H 0.2964 0.8720 0.5368 0.118 Uiso 1 1 calc R
O4 O 0.5000 0.00476(6) 0.2500 0.0258(3) Uani 1 2 d S
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
C16 C17 C17 119.96(19) . 2
C16 C17 H17 120.0 . .
C17 C17 H17 120.0 2 .
C17 C16 C15 119.7(3) . .
C17 C16 H16 120.2 . .
C15 C16 H16 120.2 . .
C15 C15 C16 120.34(15) 2 .
C15 C15 H15 119.8 2 .
C16 C15 H15 119.8 . .
C2 O3 C7 117.14(11) . .
C9 C10 C9 112.55(14) 2_556 .
C9 C10 H10A 109.1 2_556 .
C9 C10 H10A 109.1 . .
C9 C10 H10B 109.1 2_556 .
C9 C10 H10B 109.1 . .
H10A C10 H10B 107.8 . .
C1 O1 H1 109.5 . .
C5 C4 C3 118.33(12) . .
C5 C4 C9 122.72(11) . .
C3 C4 C9 118.94(11) . .
C4 C5 C6 120.44(12) . .
C4 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
O1 C1 C6 117.98(12) . .
O1 C1 C2 123.42(12) . .
C6 C1 C2 118.59(12) . .
C13 C12 C9 110.46(10) . .
C13 C12 H12A 109.6 . .
C9 C12 H12A 109.6 . .
C13 C12 H12B 109.6 . .
C9 C12 H12B 109.6 . .
H12A C12 H12B 108.1 . .
C2 C3 C4 120.89(12) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
O2 C6 C1 114.38(12) . .
O2 C6 C5 124.56(12) . .
C1 C6 C5 121.05(13) . .
C13 C14 C13 108.63(15) . 2_556
C13 C14 H14A 110.0 . .
C13 C14 H14A 110.0 2_556 .
C13 C14 H14B 110.0 . .
C13 C14 H14B 110.0 2_556 .
H14A C14 H14B 108.3 . .
C4 C9 C12 110.62(10) . .
C4 C9 C10 109.03(10) . .
C12 C9 C10 108.52(10) . .
C4 C9 C11 113.05(10) . .
C12 C9 C11 107.58(10) . .
C10 C9 C11 107.90(9) . .
C13 C11 C9 110.98(11) 2_556 .
C13 C11 H11A 109.4 2_556 .
C9 C11 H11A 109.4 . .
C13 C11 H11B 109.4 2_556 .
C9 C11 H11B 109.4 . .
H11A C11 H11B 108.0 . .
O3 C2 C3 125.07(13) . .
O3 C2 C1 114.26(12) . .
C3 C2 C1 120.67(12) . .
C14 C13 C11 109.44(10) . 2_556
C14 C13 C12 109.94(10) . .
C11 C13 C12 109.71(10) 2_556 .
C14 C13 H13 109.2 . .
C11 C13 H13 109.2 2_556 .
C12 C13 H13 109.2 . .
C6 O2 C8 118.05(12) . .
O3 C7 H7A 109.5 . .
O3 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
O3 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O2 C8 H8A 109.5 . .
O2 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
O2 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C17 C16 1.329(4) .
C17 C17 1.389(8) 2
C17 H17 0.9500 .
C16 C15 1.364(3) .
C16 H16 0.9500 .
C15 C15 1.338(5) 2
C15 H15 0.9500 .
O3 C2 1.3716(16) .
O3 C7 1.4163(19) .
C10 C9 1.5431(15) 2_556
C10 C9 1.5431(15) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
O1 C1 1.3651(16) .
O1 H1 0.8400 .
C4 C5 1.3903(19) .
C4 C3 1.3994(18) .
C4 C9 1.5262(17) .
C5 C6 1.3956(19) .
C5 H5 0.9500 .
C1 C6 1.388(2) .
C1 C2 1.389(2) .
C12 C13 1.5353(18) .
C12 C9 1.5418(17) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C3 C2 1.3888(18) .
C3 H3 0.9500 .
C6 O2 1.3748(17) .
C14 C13 1.5301(18) .
C14 C13 1.5301(18) 2_556
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C9 C11 1.5439(17) .
C11 C13 1.5343(18) 2_556
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C13 C11 1.5343(18) 2_556
C13 H13 1.0000 .
O2 C8 1.395(2) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
