#------------------------------------------------------------------------------
#$Date: 2019-11-28 16:05:11 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244081 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/81/7238143.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_7238143
loop_
_publ_author_name
'Mondal, Raju'
'Howard, Judith A. K.'
_publ_section_title
;
 Polymorphism study of a three-component system showing encapsulation of
 ion pairs and a zwitterion
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              3786
_journal_paper_doi               10.1039/b917956a
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C26 H29 Cl2 N O4'
_chemical_formula_weight         490.40
_chemical_name_common
;1,5-dichloro-trans-9,10-diethynyl-9,10-dihydroxy-9,10-
dihydroanthracene
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/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                 102.8960(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6450(5)
_cell_length_b                   11.5719(4)
_cell_length_c                   15.0033(5)
_cell_measurement_reflns_used    6235
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.406
_cell_measurement_theta_min      2.24
_cell_volume                     2478.48(15)
_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_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 6K CCD area detector'
_diffrn_measurement_method       '/w 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  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26485
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0647P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                4269
_reflns_number_total             5684
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b917956a.txt
_cod_data_source_block           03rmd082
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7238143
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cl1 Cl 0.64202(3) 0.13025(4) 1.24507(3) 0.02663(12) Uani 1 1 d .
Cl1' Cl 0.51000(4) 0.15018(4) 0.54537(3) 0.03461(13) Uani 1 1 d .
O1 O 0.47139(8) 0.18765(9) 1.09114(8) 0.0203(3) Uani 1 1 d .
H1 H 0.4795(16) 0.212(2) 1.0453(16) 0.049(7) Uiso 1 1 d .
O1' O 0.45020(8) 0.36901(10) 0.62359(8) 0.0225(3) Uani 1 1 d .
H1' H 0.4668(16) 0.3610(19) 0.6792(17) 0.045(7) Uiso 1 1 d .
C1 C 0.65619(12) 0.06094(13) 1.14593(10) 0.0200(3) Uani 1 1 d .
N1 N 0.67583(12) 0.40250(13) 0.98180(10) 0.0254(3) Uani 1 1 d .
H111 H 0.6268(14) 0.3675(17) 0.9692(14) 0.028(6) Uiso 1 1 d .
C1' C 0.49431(12) 0.25620(14) 0.46075(11) 0.0236(4) Uani 1 1 d .
O2 O 0.51736(9) 0.35242(11) 0.80493(8) 0.0316(3) Uani 1 1 d .
C2 C 0.74642(12) 0.03309(14) 1.14121(12) 0.0231(4) Uani 1 1 d .
H2 H 0.7952(13) 0.0547(16) 1.1871(13) 0.028(5) Uiso 1 1 d .
C2' C 0.47800(13) 0.21680(16) 0.37215(12) 0.0287(4) Uani 1 1 d .
H2' H 0.4815(14) 0.1370(17) 0.3635(14) 0.035(5) Uiso 1 1 d .
O3 O 0.50835(8) 0.29338(10) 0.94276(7) 0.0252(3) Uani 1 1 d .
C3 C 0.76224(12) -0.02700(15) 1.06621(12) 0.0256(4) Uani 1 1 d .
H3A H 0.8215(14) -0.0511(16) 1.0607(13) 0.032(5) Uiso 1 1 d .
C3' C 0.46268(13) 0.29447(16) 0.30044(12) 0.0293(4) Uani 1 1 d .
H3' H 0.4497(13) 0.2702(16) 0.2421(14) 0.028(5) Uiso 1 1 d .
C4 C 0.68781(12) -0.05607(14) 0.99681(12) 0.0219(3) Uani 1 1 d .
H4 H 0.7001(12) -0.0981(16) 0.9436(12) 0.025(5) Uiso 1 1 d .
C4' C 0.46239(12) 0.41144(15) 0.31877(11) 0.0245(4) Uani 1 1 d .
H4' H 0.4514(12) 0.4683(15) 0.2712(12) 0.020(4) Uiso 1 1 d .
C9 C 0.47906(11) 0.06547(13) 1.08145(10) 0.0170(3) Uani 1 1 d .
C9' C 0.51979(11) 0.41564(13) 0.58103(10) 0.0184(3) Uani 1 1 d .
C11 C 0.57825(11) 0.03285(13) 1.07529(10) 0.0165(3) Uani 1 1 d .
C11' C 0.49708(11) 0.37541(13) 0.48202(10) 0.0185(3) Uani 1 1 d .
C12 C 0.59646(11) -0.02606(13) 1.00053(10) 0.0169(3) Uani 1 1 d .
C12' C 0.47969(11) 0.45206(13) 0.40888(10) 0.0181(3) Uani 1 1 d .
C15 C 0.45629(11) 0.00907(14) 1.16288(10) 0.0202(3) Uani 1 1 d .
C15' C 0.61485(12) 0.37422(14) 0.62685(11) 0.0232(4) Uani 1 1 d .
C16 C 0.43510(14) -0.04619(16) 1.22120(12) 0.0312(4) Uani 1 1 d .
H16 H 0.4166(16) -0.089(2) 1.2659(16) 0.055(7) Uiso 1 1 d .
C16' C 0.69032(15) 0.34397(18) 0.66615(13) 0.0343(4) Uani 1 1 d .
H16' H 0.7526(18) 0.320(2) 0.6996(17) 0.061(7) Uiso 1 1 d .
C19 C 0.6510(2) 0.4125(2) 1.14090(14) 0.0443(6) Uani 1 1 d .
H19C H 0.6370(16) 0.498(2) 1.1384(14) 0.052(7) Uiso 1 1 d .
H19B H 0.5936(18) 0.378(2) 1.1231(17) 0.060(8) Uiso 1 1 d .
H19A H 0.6762(15) 0.3837(19) 1.2027(16) 0.047(6) Uiso 1 1 d .
C20 C 0.71561(16) 0.37840(17) 1.08084(13) 0.0361(5) Uani 1 1 d .
H2OC H 0.7775(15) 0.4182(17) 1.0985(13) 0.032(5) Uiso 1 1 d .
H20A H 0.7289(14) 0.2948(19) 1.0849(14) 0.042(6) Uiso 1 1 d .
C21 C 0.64940(14) 0.52718(16) 0.96205(13) 0.0307(4) Uani 1 1 d .
H21B H 0.6238(13) 0.5293(16) 0.8971(14) 0.032(5) Uiso 1 1 d .
H21A H 0.6016(13) 0.5502(16) 0.9971(13) 0.031(5) Uiso 1 1 d .
C22 C 0.73044(18) 0.61083(18) 0.98660(18) 0.0446(5) Uani 1 1 d .
H22C H 0.7782(17) 0.588(2) 0.9523(16) 0.057(7) Uiso 1 1 d .
H22B H 0.7616(19) 0.608(2) 1.0556(19) 0.071(8) Uiso 1 1 d .
H22A H 0.7023(16) 0.686(2) 0.9675(15) 0.051(6) Uiso 1 1 d .
C23 C 0.73658(15) 0.35883(16) 0.92109(14) 0.0313(4) Uani 1 1 d .
H23A H 0.7068(13) 0.3837(16) 0.8605(14) 0.030(5) Uiso 1 1 d .
H23B H 0.7973(15) 0.4002(17) 0.9367(13) 0.037(5) Uiso 1 1 d .
C24 C 0.74607(17) 0.22862(18) 0.92434(17) 0.0387(5) Uani 1 1 d .
H24B H 0.7726(16) 0.2080(19) 0.8771(16) 0.046(6) Uiso 1 1 d .
H24A H 0.7825(16) 0.2051(19) 0.9840(16) 0.049(6) Uiso 1 1 d .
H24C H 0.6843(16) 0.1951(18) 0.9154(14) 0.040(6) Uiso 1 1 d .
C25 C 0.38464(14) 0.24003(17) 0.81696(14) 0.0279(4) Uani 1 1 d .
H25C H 0.381(3) 0.154(4) 0.827(4) 0.035(12) Uiso 0.50 1 d P
H25B H 0.397(3) 0.180(5) 0.779(3) 0.040(12) Uiso 0.50 1 d P
H25A H 0.340(3) 0.260(4) 0.859(3) 0.032(11) Uiso 0.50 1 d P
H25F H 0.365(3) 0.249(3) 0.749(3) 0.015(8) Uiso 0.50 1 d P
H25E H 0.359(3) 0.195(5) 0.859(3) 0.034(12) Uiso 0.50 1 d P
H25D H 0.339(3) 0.288(3) 0.789(3) 0.024(10) Uiso 0.50 1 d P
C26 C 0.47608(12) 0.29926(14) 0.85681(11) 0.0220(3) Uani 1 1 d .
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'
Cl Cl 0.1484 0.1585 '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'
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_3
C9 O1 H1 103.7(17) .
C9' O1' H1' 114.8(16) .
C2 C1 C11 122.14(15) .
C2 C1 Cl1 116.74(13) .
C11 C1 Cl1 121.10(12) .
C23 N1 C20 112.90(16) .
C23 N1 C21 111.43(14) .
C20 N1 C21 113.58(14) .
C23 N1 H111 107.8(14) .
C20 N1 H111 105.5(14) .
C21 N1 H111 105.0(14) .
C2' C1' C11' 122.12(15) .
C2' C1' Cl1' 115.91(13) .
C11' C1' Cl1' 121.97(12) .
C1 C2 C3 119.69(16) .
C1 C2 H2 119.8(12) .
C3 C2 H2 120.5(12) .
C1' C2' C3' 120.01(16) .
C1' C2' H2' 117.3(12) .
C3' C2' H2' 122.6(12) .
C4 C3 C2 119.43(16) .
C4 C3 H3A 117.3(12) .
C2 C3 H3A 123.3(12) .
C2' C3' C4' 119.32(16) .
C2' C3' H3' 121.2(12) .
C4' C3' H3' 119.4(12) .
C3 C4 C12 121.03(16) .
C3 C4 H4 118.6(11) .
C12 C4 H4 120.4(11) .
C3' C4' C12' 120.88(16) .
C3' C4' H4' 122.1(10) .
C12' C4' H4' 117.0(10) .
O1 C9 C15 108.29(12) .
O1 C9 C11 110.43(12) .
C15 C9 C11 109.43(12) .
O1 C9 C12 108.54(12) 3_657
C15 C9 C12 105.99(12) 3_657
C11 C9 C12 113.93(12) 3_657
O1' C9' C15' 111.12(13) .
O1' C9' C11' 107.43(13) .
C15' C9' C11' 109.31(13) .
O1' C9' C12' 108.75(12) 3_666
C15' C9' C12' 106.96(13) 3_666
C11' C9' C12' 113.32(12) 3_666
C12 C11 C1 116.79(14) .
C12 C11 C9 121.89(13) .
C1 C11 C9 121.31(13) .
C12' C11' C1' 116.96(14) .
C12' C11' C9' 122.51(13) .
C1' C11' C9' 120.52(14) .
C11 C12 C4 120.88(14) .
C11 C12 C9 124.17(14) 3_657
C4 C12 C9 114.93(13) 3_657
C11' C12' C4' 120.67(15) .
C11' C12' C9' 124.17(13) 3_666
C4' C12' C9' 115.15(14) 3_666
C16 C15 C9 172.50(17) .
C16' C15' C9' 177.41(18) .
C15 C16 H16 178.1(15) .
C15' C16' H16' 178.8(15) .
C20 C19 H19C 112.6(12) .
C20 C19 H19B 111.7(16) .
H19C C19 H19B 105(2) .
C20 C19 H19A 109.0(13) .
H19C C19 H19A 113.6(18) .
H19B C19 H19A 105(2) .
N1 C20 C19 112.97(18) .
N1 C20 H2OC 107.9(11) .
C19 C20 H2OC 112.1(11) .
N1 C20 H20A 105.8(12) .
C19 C20 H20A 111.3(12) .
H2OC C20 H20A 106.4(16) .
N1 C21 C22 114.33(17) .
N1 C21 H21B 104.4(11) .
C22 C21 H21B 109.7(11) .
N1 C21 H21A 109.3(11) .
C22 C21 H21A 107.7(11) .
H21B C21 H21A 111.4(16) .
C21 C22 H22C 108.1(14) .
C21 C22 H22B 111.8(15) .
H22C C22 H22B 108(2) .
C21 C22 H22A 104.0(13) .
H22C C22 H22A 112.5(19) .
H22B C22 H22A 112(2) .
N1 C23 C24 112.30(16) .
N1 C23 H23A 105.6(11) .
C24 C23 H23A 110.3(11) .
N1 C23 H23B 108.5(11) .
C24 C23 H23B 113.7(12) .
H23A C23 H23B 105.8(16) .
C23 C24 H24B 106.7(14) .
C23 C24 H24A 109.7(13) .
H24B C24 H24A 113.6(19) .
C23 C24 H24C 108.6(12) .
H24B C24 H24C 109.5(19) .
H24A C24 H24C 108.6(18) .
C26 C25 H25C 118(3) .
C26 C25 H25B 108(3) .
H25C C25 H25B 52(3) .
C26 C25 H25A 107(2) .
H25C C25 H25A 94(4) .
H25B C25 H25A 140(4) .
C26 C25 H25F 112.4(19) .
H25C C25 H25F 103(3) .
H25B C25 H25F 60(3) .
H25A C25 H25F 122(3) .
C26 C25 H25E 116(3) .
H25C C25 H25E 48(3) .
H25B C25 H25E 99(4) .
H25A C25 H25E 47(3) .
H25F C25 H25E 132(3) .
C26 C25 H25D 114(2) .
H25C C25 H25D 128(3) .
H25B C25 H25D 113(4) .
H25A C25 H25D 69(3) .
H25F C25 H25D 56(3) .
H25E C25 H25D 107(4) .
O2 C26 O3 122.42(16) .
O2 C26 C25 119.24(15) .
O3 C26 C25 118.34(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.7425(16) .
Cl1' C1' 1.7435(17) .
O1 C9 1.4283(18) .
O1 H1 0.78(2) .
O1' C9' 1.4241(18) .
O1' H1' 0.82(2) .
C1 C2 1.377(2) .
C1 C11 1.411(2) .
N1 C23 1.496(2) .
N1 C20 1.496(2) .
N1 C21 1.506(2) .
N1 H111 0.81(2) .
C1' C2' 1.375(2) .
C1' C11' 1.414(2) .
O2 C26 1.2489(19) .
C2 C3 1.386(2) .
C2 H2 0.910(19) .
C2' C3' 1.381(3) .
C2' H2' 0.936(19) .
O3 C26 1.2723(19) .
C3 C4 1.371(2) .
C3 H3A 0.93(2) .
C3' C4' 1.381(2) .
C3' H3' 0.898(19) .
C4 C12 1.395(2) .
C4 H4 0.985(18) .
C4' C12' 1.400(2) .
C4' H4' 0.958(17) .
C9 C15 1.487(2) .
C9 C11 1.524(2) .
C9 C12 1.529(2) 3_657
C9' C15' 1.488(2) .
C9' C11' 1.521(2) .
C9' C12' 1.538(2) 3_666
C11 C12 1.388(2) .
C11' C12' 1.389(2) .
C12 C9 1.529(2) 3_657
C12' C9' 1.538(2) 3_666
C15 C16 1.180(2) .
C15' C16' 1.184(3) .
C16 H16 0.92(2) .
C16' H16' 0.98(3) .
C19 C20 1.498(3) .
C19 H19C 1.01(2) .
C19 H19B 0.92(3) .
C19 H19A 0.98(2) .
C20 H2OC 1.00(2) .
C20 H20A 0.99(2) .
C21 C22 1.512(3) .
C21 H21B 0.96(2) .
C21 H21A 1.001(19) .
C22 H22C 0.99(2) .
C22 H22B 1.03(3) .
C22 H22A 0.98(2) .
C23 C24 1.513(3) .
C23 H23A 0.96(2) .
C23 H23B 0.99(2) .
C24 H24B 0.91(2) .
C24 H24A 0.97(2) .
C24 H24C 0.97(2) .
C25 C26 1.504(3) .
C25 H25C 1.01(5) .
C25 H25B 0.94(5) .
C25 H25A 1.02(4) .
C25 H25F 1.00(4) .
C25 H25E 0.97(5) .
C25 H25D 0.89(4) .
