#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/44/4504402.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_4504402
loop_
_publ_author_name
'Imai, Yoshitane'
'Kawaguchi, Kakuhiro'
'Murata, Katuzo'
'Sato, Tomohiro'
'Kuroda, Reiko'
'Matsubara, Yoshio'
_publ_section_title
;
 Tunable Two-Component Host System with Multiple Chiral Points Composed of
 Cyclohexanediamine and 1,1‘-Binaphthyl-2,2‘-dicarboxylic
 Acid
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1676
_journal_paper_doi               10.1021/cg070507m
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C29 H34 N2 O6'
_chemical_formula_weight         506.58
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9189(5)
_cell_length_b                   10.2904(5)
_cell_length_c                   27.9198(14)
_cell_measurement_reflns_used    5432
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      1.46
_cell_volume                     2562.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SAMRT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0413
_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       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            22726
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9598
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0563P)²+0.2540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                5432
_reflns_number_total             5949
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg070507m-file001.cif
_cod_data_source_block           imai74_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4504402
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
C11 C 0.69826(18) 0.05928(15) 0.15009(5) 0.0129(3) Uani 1 1 d .
C12 C 0.78489(18) 0.16616(15) 0.16066(5) 0.0143(3) Uani 1 1 d .
C13 C 0.73754(19) 0.25669(16) 0.19600(6) 0.0171(3) Uani 1 1 d .
H13 H 0.7993 0.3292 0.2034 0.020 Uiso 1 1 calc R
C14 C 0.60535(19) 0.24098(17) 0.21938(6) 0.0184(4) Uani 1 1 d .
H14 H 0.5770 0.3012 0.2435 0.022 Uiso 1 1 calc R
C15 C 0.3654(2) 0.12248(18) 0.22942(6) 0.0198(4) Uani 1 1 d .
H15 H 0.3355 0.1815 0.2538 0.024 Uiso 1 1 calc R
C16 C 0.2693(2) 0.02627(18) 0.21546(6) 0.0207(4) Uani 1 1 d .
H16 H 0.1726 0.0203 0.2295 0.025 Uiso 1 1 calc R
C17 C 0.31323(19) -0.06376(17) 0.18037(6) 0.0189(4) Uani 1 1 d .
H17 H 0.2458 -0.1300 0.1705 0.023 Uiso 1 1 calc R
C18 C 0.45359(19) -0.05626(15) 0.16022(6) 0.0162(3) Uani 1 1 d .
H18 H 0.4831 -0.1195 0.1373 0.019 Uiso 1 1 calc R
C19 C 0.55542(18) 0.04397(15) 0.17294(6) 0.0140(3) Uani 1 1 d .
C20 C 0.50912(19) 0.13569(17) 0.20810(6) 0.0167(3) Uani 1 1 d .
C12A C 0.93189(19) 0.19289(15) 0.13539(6) 0.0156(3) Uani 1 1 d .
O12 O 1.03837(13) 0.23303(13) 0.16131(4) 0.0233(3) Uani 1 1 d .
O13 O 0.93776(15) 0.17833(12) 0.09093(4) 0.0209(3) Uani 1 1 d .
C1 C 0.75820(17) -0.04985(15) 0.11991(6) 0.0133(3) Uani 1 1 d .
C2 C 0.73609(18) -0.05814(15) 0.07109(6) 0.0147(3) Uani 1 1 d .
C3 C 0.79592(19) -0.16447(16) 0.04491(6) 0.0168(3) Uani 1 1 d .
H3 H 0.7816 -0.1683 0.0112 0.020 Uiso 1 1 calc R
C4 C 0.87334(19) -0.26101(17) 0.06722(6) 0.0187(4) Uani 1 1 d .
H4 H 0.9103 -0.3323 0.0491 0.022 Uiso 1 1 calc R
C5 C 0.9771(2) -0.35640(17) 0.14165(7) 0.0219(4) Uani 1 1 d .
H5 H 1.0125 -0.4296 0.1243 0.026 Uiso 1 1 calc R
C6 C 1.0015(2) -0.34859(18) 0.18990(7) 0.0228(4) Uani 1 1 d .
H6 H 1.0545 -0.4162 0.2057 0.027 Uiso 1 1 calc R
C7 C 0.9492(2) -0.24159(18) 0.21626(6) 0.0202(4) Uani 1 1 d .
H7 H 0.9672 -0.2371 0.2497 0.024 Uiso 1 1 calc R
C8 C 0.87229(19) -0.14385(17) 0.19397(6) 0.0171(3) Uani 1 1 d .
H8 H 0.8377 -0.0719 0.2122 0.021 Uiso 1 1 calc R
C9 C 0.84320(18) -0.14819(16) 0.14385(6) 0.0149(3) Uani 1 1 d .
C10 C 0.89919(18) -0.25590(16) 0.11736(6) 0.0166(3) Uani 1 1 d .
C2A C 0.64977(18) 0.04375(15) 0.04386(6) 0.0144(3) Uani 1 1 d .
O2 O 0.53870(13) 0.09536(11) 0.06319(4) 0.0175(3) Uani 1 1 d .
O3 O 0.69384(13) 0.06837(12) 0.00132(4) 0.0188(3) Uani 1 1 d .
C21 C 0.33067(18) 0.37787(16) 0.10474(6) 0.0147(3) Uani 1 1 d .
H21 H 0.2535 0.4254 0.0856 0.018 Uiso 1 1 calc R
C22 C 0.48156(18) 0.38975(15) 0.07903(6) 0.0149(3) Uani 1 1 d .
H22 H 0.5573 0.3371 0.0970 0.018 Uiso 1 1 calc R
C23 C 0.5350(2) 0.53061(16) 0.07767(6) 0.0203(4) Uani 1 1 d .
H23A H 0.6354 0.5347 0.0626 0.024 Uiso 1 1 calc R
H23B H 0.4651 0.5829 0.0580 0.024 Uiso 1 1 calc R
C24 C 0.5429(2) 0.58730(17) 0.12801(7) 0.0233(4) Uani 1 1 d .
H24A H 0.5750 0.6793 0.1263 0.028 Uiso 1 1 calc R
H24B H 0.6180 0.5389 0.1471 0.028 Uiso 1 1 calc R
C25 C 0.3904(2) 0.57891(18) 0.15246(7) 0.0216(4) Uani 1 1 d .
H25A H 0.3977 0.6146 0.1853 0.026 Uiso 1 1 calc R
H25B H 0.3166 0.6317 0.1345 0.026 Uiso 1 1 calc R
C26 C 0.33728(19) 0.43852(16) 0.15467(6) 0.0181(4) Uani 1 1 d .
H26A H 0.2365 0.4352 0.1695 0.022 Uiso 1 1 calc R
H26B H 0.4066 0.3876 0.1750 0.022 Uiso 1 1 calc R
N21 N 0.28278(16) 0.23872(13) 0.10913(5) 0.0166(3) Uani 1 1 d .
H21A H 0.3579 0.1916 0.1227 0.025 Uiso 1 1 calc R
H21B H 0.2620 0.2063 0.0795 0.025 Uiso 1 1 calc R
H21C H 0.1994 0.2338 0.1278 0.025 Uiso 1 1 calc R
N22 N 0.46866(16) 0.33606(13) 0.02931(5) 0.0154(3) Uani 1 1 d .
H22A H 0.3812 0.3635 0.0159 0.023 Uiso 1 1 calc R
H22B H 0.4697 0.2477 0.0305 0.023 Uiso 1 1 calc R
H22C H 0.5473 0.3644 0.0113 0.023 Uiso 1 1 calc R
O31 O 0.21756(14) 0.08742(12) 0.02396(4) 0.0193(3) Uani 1 1 d .
H31 H 0.2883 0.0843 0.0041 0.029 Uiso 1 1 calc R
C32 C 0.2011(2) -0.03691(17) 0.04662(7) 0.0243(4) Uani 1 1 d .
H32A H 0.1773 -0.1027 0.0224 0.036 Uiso 1 1 calc R
H32B H 0.1198 -0.0328 0.0702 0.036 Uiso 1 1 calc R
H32C H 0.2949 -0.0602 0.0628 0.036 Uiso 1 1 calc R
O41 O 0.42584(16) 0.09115(14) -0.04414(5) 0.0216(3) Uani 1 1 d .
H41B H 0.425(3) 0.163(3) -0.0607(9) 0.047(7) Uiso 1 1 d .
H41A H 0.517(3) 0.084(3) -0.0350(10) 0.053(8) Uiso 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'
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
C12 C11 C19 119.44(14)
C12 C11 C1 121.19(14)
C19 C11 C1 118.93(13)
C11 C12 C13 120.39(15)
C11 C12 C12A 122.11(14)
C13 C12 C12A 117.50(14)
C14 C13 C12 120.93(16)
C13 C14 C20 120.66(16)
C16 C15 C20 121.06(16)
C15 C16 C17 120.16(16)
C18 C17 C16 120.16(16)
C17 C18 C19 121.42(16)
C18 C19 C20 117.96(15)
C18 C19 C11 122.50(14)
C20 C19 C11 119.47(14)
C14 C20 C15 121.78(15)
C14 C20 C19 118.98(15)
C15 C20 C19 119.19(15)
O13 C12A O12 125.15(16)
O13 C12A C12 118.47(15)
O12 C12A C12 116.33(14)
C2 C1 C9 119.59(14)
C2 C1 C11 123.34(14)
C9 C1 C11 117.08(14)
C1 C2 C3 120.16(15)
C1 C2 C2A 121.90(14)
C3 C2 C2A 117.94(14)
C4 C3 C2 121.17(15)
C3 C4 C10 120.45(15)
C6 C5 C10 120.42(17)
C5 C6 C7 120.63(16)
C8 C7 C6 120.33(16)
C7 C8 C9 121.04(16)
C10 C9 C8 118.12(15)
C10 C9 C1 119.61(15)
C8 C9 C1 122.26(15)
C5 C10 C4 121.60(16)
C5 C10 C9 119.42(16)
C4 C10 C9 118.97(15)
O2 C2A O3 124.25(15)
O2 C2A C2 118.95(14)
O3 C2A C2 116.76(14)
N21 C21 C26 109.05(13)
N21 C21 C22 111.42(13)
C26 C21 C22 111.18(13)
N22 C22 C23 110.56(14)
N22 C22 C21 109.73(12)
C23 C22 C21 111.23(13)
C24 C23 C22 110.81(15)
C23 C24 C25 110.50(15)
C26 C25 C24 110.47(14)
C25 C26 C21 111.26(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C11 C12 1.376(2)
C11 C19 1.433(2)
C11 C1 1.502(2)
C12 C13 1.421(2)
C12 C12A 1.514(2)
C13 C14 1.357(2)
C14 C20 1.418(2)
C15 C16 1.366(3)
C15 C20 1.420(2)
C16 C17 1.404(3)
C17 C18 1.375(2)
C18 C19 1.419(2)
C19 C20 1.423(2)
C12A O13 1.252(2)
C12A O12 1.263(2)
C1 C2 1.380(2)
C1 C9 1.430(2)
C2 C3 1.420(2)
C2 C2A 1.507(2)
C3 C4 1.361(2)
C4 C10 1.420(2)
C5 C6 1.367(3)
C5 C10 1.419(2)
C6 C7 1.404(3)
C7 C8 1.367(2)
C8 C9 1.424(2)
C9 C10 1.423(2)
C2A O2 1.247(2)
C2A O3 1.276(2)
C21 N21 1.499(2)
C21 C26 1.529(2)
C21 C22 1.530(2)
C22 N22 1.498(2)
C22 C23 1.526(2)
C23 C24 1.523(2)
C24 C25 1.524(2)
C25 C26 1.521(2)
O31 C32 1.435(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145508
