#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:00:20 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179608 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/72/4507288.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_4507288
loop_
_publ_author_name
'Masu, Hyuma'
'Tominaga, Masahide'
'Azumaya, Isao'
_publ_section_title
;
 Hydrogen-Bonded 1D Chains Formed from Adamantane-Based Bisphenols and
 Bispyridines: Influences of Substitution Groups on Phenol Ring
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              752
_journal_paper_doi               10.1021/cg301462v
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C22 H22 Cl2 O2, C12 H10 N2'
_chemical_formula_sum            'C34 H32 Cl2 N2 O2'
_chemical_formula_weight         571.52
_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                 96.602(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6272(14)
_cell_length_b                   11.462(2)
_cell_length_c                   32.491(6)
_cell_measurement_reflns_used    2877
_cell_measurement_temperature    200
_cell_measurement_theta_max      26.57
_cell_measurement_theta_min      2.52
_cell_volume                     2821.6(9)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       '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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            6804
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.25
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_correction_T_min  0.9489
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0331
_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)+(0.0418P)²+1.5106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                2429
_reflns_number_total             2881
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301462v_si_002.cif
_cod_data_source_block           a1009251tom
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2821.7(9)
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               4507288
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
C1 C 0.81767(19) 0.46882(14) 0.38394(4) 0.0310(3) Uani 1 1 d .
C2 C 0.92332(18) 0.39390(13) 0.36410(4) 0.0267(3) Uani 1 1 d .
C3 C 0.85452(18) 0.31741(13) 0.33318(4) 0.0254(3) Uani 1 1 d .
H3 H 0.9316 0.2664 0.3209 0.030 Uiso 1 1 calc R
C4 C 0.67463(18) 0.31451(12) 0.32002(4) 0.0244(3) Uani 1 1 d .
C5 C 0.56890(19) 0.39135(14) 0.33962(5) 0.0304(3) Uani 1 1 d .
H5 H 0.4454 0.3922 0.3312 0.036 Uiso 1 1 calc R
C6 C 0.6369(2) 0.46582(15) 0.37056(5) 0.0346(4) Uani 1 1 d .
H6 H 0.5596 0.5162 0.3831 0.041 Uiso 1 1 calc R
C7 C 0.59235(17) 0.23460(12) 0.28561(4) 0.0242(3) Uani 1 1 d .
C8 C 0.5000 0.30990(17) 0.2500 0.0226(4) Uani 1 2 d S
H8A H 0.4114 0.3607 0.2610 0.027 Uiso 0.50 1 calc PR
H8B H 0.5886 0.3607 0.2390 0.027 Uiso 0.50 1 calc PR
C9 C 0.72804(19) 0.15609(13) 0.26738(5) 0.0291(3) Uani 1 1 d .
H9A H 0.8181 0.2053 0.2562 0.035 Uiso 1 1 calc R
H9B H 0.7885 0.1065 0.2896 0.035 Uiso 1 1 calc R
C10 C 0.45214(19) 0.15523(13) 0.30203(4) 0.0292(3) Uani 1 1 d .
H10A H 0.5091 0.1052 0.3246 0.035 Uiso 1 1 calc R
H10B H 0.3625 0.2040 0.3136 0.035 Uiso 1 1 calc R
C11 C 0.3622(2) 0.07840(13) 0.26729(5) 0.0325(3) Uani 1 1 d .
H11 H 0.2717 0.0281 0.2785 0.039 Uiso 1 1 calc R
C12 C 0.5000 0.00096(19) 0.2500 0.0387(5) Uani 1 2 d S
H12A H 0.4421 -0.0496 0.2278 0.046 Uiso 0.50 1 calc PR
H12B H 0.5579 -0.0496 0.2722 0.046 Uiso 0.50 1 calc PR
C13 C 0.8066(2) 0.14554(16) 0.43105(5) 0.0382(4) Uani 1 1 d .
H13 H 0.7735 0.1539 0.4021 0.046 Uiso 1 1 calc R
C14 C 0.9658(2) 0.19112(15) 0.44753(5) 0.0343(4) Uani 1 1 d .
H14 H 1.0407 0.2281 0.4300 0.041 Uiso 1 1 calc R
C15 C 1.01717(19) 0.18292(13) 0.48992(5) 0.0287(3) Uani 1 1 d .
C16 C 0.9004(2) 0.12710(14) 0.51333(5) 0.0321(3) Uani 1 1 d .
H16 H 0.9280 0.1202 0.5425 0.038 Uiso 1 1 calc R
C17 C 0.7440(2) 0.08168(14) 0.49403(5) 0.0342(4) Uani 1 1 d .
H17 H 0.6675 0.0425 0.5106 0.041 Uiso 1 1 calc R
C18 C 1.1842(2) 0.23047(14) 0.50981(5) 0.0318(3) Uani 1 1 d .
H18 H 1.1996 0.2336 0.5392 0.038 Uiso 1 1 calc R
Cl1 Cl 1.15186(5) 0.39612(4) 0.377305(12) 0.03618(13) Uani 1 1 d .
N1 N 0.69527(17) 0.09010(12) 0.45334(4) 0.0363(3) Uani 1 1 d .
O1 O 0.87242(15) 0.54513(12) 0.41455(4) 0.0449(3) Uani 1 1 d .
H1 H 0.9810 0.5361 0.4217 0.067 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'
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'
Cl Cl 0.1484 0.1585 '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
O1 C1 C2 126.52(13) . .
O1 C1 C6 117.02(14) . .
C2 C1 C6 116.46(14) . .
C1 C2 C3 122.38(13) . .
C1 C2 Cl1 119.59(11) . .
C3 C2 Cl1 118.02(11) . .
C4 C3 C2 120.97(13) . .
C4 C3 H3 119.5 . .
C2 C3 H3 119.5 . .
C3 C4 C5 116.50(13) . .
C3 C4 C7 123.29(12) . .
C5 C4 C7 120.21(12) . .
C6 C5 C4 122.43(13) . .
C6 C5 H5 118.8 . .
C4 C5 H5 118.8 . .
C5 C6 C1 121.24(14) . .
C5 C6 H6 119.4 . .
C1 C6 H6 119.4 . .
C4 C7 C9 113.28(11) . .
C4 C7 C10 110.09(11) . .
C9 C7 C10 108.12(12) . .
C4 C7 C8 109.10(12) . .
C9 C7 C8 107.86(10) . .
C10 C7 C8 108.25(10) . .
C7 C8 C7 112.16(16) 2_655 .
C7 C8 H8A 109.2 2_655 .
C7 C8 H8A 109.2 . .
C7 C8 H8B 109.2 2_655 .
C7 C8 H8B 109.2 . .
H8A C8 H8B 107.9 . .
C11 C9 C7 110.89(12) 2_655 .
C11 C9 H9A 109.5 2_655 .
C7 C9 H9A 109.5 . .
C11 C9 H9B 109.5 2_655 .
C7 C9 H9B 109.5 . .
H9A C9 H9B 108.0 . .
C11 C10 C7 110.70(11) . .
C11 C10 H10A 109.5 . .
C7 C10 H10A 109.5 . .
C11 C10 H10B 109.5 . .
C7 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
C10 C11 C12 109.63(12) . .
C10 C11 C9 109.42(12) . 2_655
C12 C11 C9 109.63(12) . 2_655
C10 C11 H11 109.4 . .
C12 C11 H11 109.4 . .
C9 C11 H11 109.4 2_655 .
C11 C12 C11 109.13(17) . 2_655
C11 C12 H12A 109.9 . .
C11 C12 H12A 109.9 2_655 .
C11 C12 H12B 109.9 . .
C11 C12 H12B 109.9 2_655 .
H12A C12 H12B 108.3 . .
N1 C13 C14 123.89(15) . .
N1 C13 H13 118.1 . .
C14 C13 H13 118.1 . .
C13 C14 C15 119.73(14) . .
C13 C14 H14 120.1 . .
C15 C14 H14 120.1 . .
C14 C15 C16 116.58(13) . .
C14 C15 C18 122.87(14) . .
C16 C15 C18 120.55(13) . .
C17 C16 C15 119.84(14) . .
C17 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
N1 C17 C16 123.30(15) . .
N1 C17 H17 118.3 . .
C16 C17 H17 118.3 . .
C18 C18 C15 125.49(18) 7_756 .
C18 C18 H18 117.3 7_756 .
C15 C18 H18 117.3 . .
C17 N1 C13 116.64(13) . .
C1 O1 H1 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.3539(18) .
C1 C2 1.386(2) .
C1 C6 1.398(2) .
C2 C3 1.390(2) .
C2 Cl1 1.7468(14) .
C3 C4 1.3898(19) .
C3 H3 0.9500 .
C4 C5 1.396(2) .
C4 C7 1.5238(19) .
C5 C6 1.374(2) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C9 1.540(2) .
C7 C10 1.5451(19) .
C7 C8 1.5467(17) .
C8 C7 1.5466(17) 2_655
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C11 1.535(2) 2_655
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.530(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.531(2) .
C11 C9 1.535(2) 2_655
C11 H11 1.0000 .
C12 C11 1.531(2) 2_655
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 N1 1.338(2) .
C13 C14 1.373(2) .
C13 H13 0.9500 .
C14 C15 1.391(2) .
C14 H14 0.9500 .
C15 C16 1.392(2) .
C15 C18 1.466(2) .
C16 C17 1.384(2) .
C16 H16 0.9500 .
C17 N1 1.335(2) .
C17 H17 0.9500 .
C18 C18 1.327(3) 7_756
C18 H18 0.9500 .
O1 H1 0.8400 .
