#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/71/7217185.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_7217185
loop_
_publ_author_name
'Qureshi, Naseem'
'Yufit, Dimitri S.'
'Steed, Kirsty M.'
'Howard, Judith A. K.'
'Steed, Jonathan W.'
_publ_section_title
;
 Hydrogen bonding effects in anion binding calixarenes
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              8413
_journal_paper_doi               10.1039/C4CE01240B
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C36 H34 N2 O4, C H2 Cl2'
_chemical_formula_sum            'C37 H36 Cl2 N2 O4'
_chemical_formula_weight         643.58
_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                   10.0646(11)
_cell_length_b                   15.6235(17)
_cell_length_c                   20.246(2)
_cell_measurement_temperature    120(2)
_cell_volume                     3183.6(6)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    X-Seed
_computing_publication_material  X-Seed
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SMART 1k'
_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  0.0937
_diffrn_reflns_av_sigmaI/netI    0.0754
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21304
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.836786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         4585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0470
_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)+(0.0297P)²+0.9149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                3616
_reflns_number_total             4585
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01240b2.cif
_cod_data_source_block           ng48sad
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 

 Adding full bibliography for 7217180--7217187.cif.
;
_cod_original_cell_volume        3183.5(6)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7217185
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
Cl1 Cl 0.29631(11) 0.67079(6) 0.86204(5) 0.0347(3) Uani 1 1 d .
Cl2 Cl 0.27749(11) 0.77298(7) 0.74173(5) 0.0343(3) Uani 1 1 d .
O1 O 0.3978(2) 0.43481(15) 0.65319(12) 0.0237(6) Uani 1 1 d .
O2 O 0.1816(3) 0.42732(18) 0.73676(13) 0.0230(7) Uani 1 1 d .
O3 O -0.0438(2) 0.50232(15) 0.66725(11) 0.0182(6) Uani 1 1 d .
O4 O 0.1901(3) 0.54750(16) 0.60551(13) 0.0223(7) Uani 1 1 d .
N5 N 0.1141(4) 0.2223(2) 0.51439(17) 0.0382(10) Uani 1 1 d .
N6 N -0.2543(5) 0.4837(3) 0.4624(2) 0.0685(15) Uani 1 1 d .
C1 C 0.4697(4) 0.4984(2) 0.68566(18) 0.0206(9) Uani 1 1 d .
C2 C 0.5002(3) 0.5733(2) 0.65174(18) 0.0196(9) Uani 1 1 d .
C3 C 0.5723(4) 0.6360(3) 0.68571(19) 0.0275(10) Uani 1 1 d .
H3 H 0.5957 0.6877 0.6639 0.033 Uiso 1 1 calc R
C4 C 0.6098(4) 0.6236(3) 0.7506(2) 0.0286(10) Uani 1 1 d .
H4 H 0.6606 0.6661 0.7728 0.034 Uiso 1 1 calc R
C5 C 0.5738(4) 0.5494(3) 0.7836(2) 0.0290(11) Uani 1 1 d .
H5 H 0.5990 0.5419 0.8284 0.035 Uiso 1 1 calc R
C6 C 0.5016(4) 0.4861(2) 0.75217(19) 0.0212(9) Uani 1 1 d .
C7 C 0.4507(4) 0.4092(2) 0.79071(19) 0.0267(10) Uani 1 1 d .
H7A H 0.4295 0.3625 0.7594 0.032 Uiso 1 1 calc R
H7B H 0.5219 0.3886 0.8205 0.032 Uiso 1 1 calc R
C8 C 0.3287(4) 0.4294(2) 0.83121(18) 0.0217(10) Uani 1 1 d .
C9 C 0.2040(4) 0.4397(2) 0.80271(16) 0.0185(9) Uani 1 1 d .
C10 C 0.0925(4) 0.4604(2) 0.84077(17) 0.0180(9) Uani 1 1 d .
C11 C 0.1081(4) 0.4716(2) 0.90782(18) 0.0221(10) Uani 1 1 d .
H11 H 0.0330 0.4852 0.9343 0.027 Uiso 1 1 calc R
C12 C 0.2330(4) 0.4633(2) 0.93757(18) 0.0270(10) Uani 1 1 d .
H12 H 0.2430 0.4726 0.9837 0.032 Uiso 1 1 calc R
C13 C 0.3414(4) 0.4414(2) 0.89935(19) 0.0252(10) Uani 1 1 d .
H13 H 0.4258 0.4345 0.9196 0.030 Uiso 1 1 calc R
C14 C -0.0430(4) 0.4713(2) 0.80808(18) 0.0209(9) Uani 1 1 d .
H14A H -0.0538 0.4274 0.7732 0.025 Uiso 1 1 calc R
H14B H -0.1136 0.4622 0.8414 0.025 Uiso 1 1 calc R
C15 C -0.0586(3) 0.5597(2) 0.77782(17) 0.0162(9) Uani 1 1 d .
C16 C -0.0691(4) 0.6314(2) 0.81791(18) 0.0198(9) Uani 1 1 d .
H16 H -0.0724 0.6244 0.8645 0.024 Uiso 1 1 calc R
C17 C -0.0749(4) 0.7129(3) 0.79124(19) 0.0235(10) Uani 1 1 d .
H17 H -0.0853 0.7610 0.8194 0.028 Uiso 1 1 calc R
C18 C -0.0655(3) 0.7244(2) 0.72359(18) 0.0211(9) Uani 1 1 d .
H18 H -0.0673 0.7805 0.7057 0.025 Uiso 1 1 calc R
C19 C -0.0533(4) 0.6540(2) 0.68150(18) 0.0169(9) Uani 1 1 d .
C20 C -0.0542(3) 0.5730(2) 0.70965(17) 0.0165(9) Uani 1 1 d .
C21 C -0.0336(4) 0.6681(2) 0.60806(18) 0.0226(9) Uani 1 1 d .
H21A H -0.0939 0.7142 0.5930 0.027 Uiso 1 1 calc R
H21B H -0.0577 0.6151 0.5841 0.027 Uiso 1 1 calc R
C22 C 0.1097(4) 0.6924(2) 0.59102(17) 0.0204(9) Uani 1 1 d .
C23 C 0.1411(4) 0.7770(3) 0.57493(18) 0.0272(10) Uani 1 1 d .
H23 H 0.0729 0.8190 0.5739 0.033 Uiso 1 1 calc R
C24 C 0.2695(4) 0.8001(2) 0.56062(18) 0.0307(11) Uani 1 1 d .
H24 H 0.2894 0.8579 0.5496 0.037 Uiso 1 1 calc R
C25 C 0.3696(4) 0.7401(3) 0.56212(18) 0.0295(11) Uani 1 1 d .
H25 H 0.4578 0.7570 0.5519 0.035 Uiso 1 1 calc R
C26 C 0.3444(4) 0.6555(2) 0.57819(17) 0.0219(10) Uani 1 1 d .
C27 C 0.2123(4) 0.6327(2) 0.59251(16) 0.0187(9) Uani 1 1 d .
C28 C 0.4545(4) 0.5896(3) 0.58134(18) 0.0257(10) Uani 1 1 d .
H28A H 0.5309 0.6098 0.5547 0.031 Uiso 1 1 calc R
H28B H 0.4226 0.5353 0.5618 0.031 Uiso 1 1 calc R
C29 C 0.4785(4) 0.3678(2) 0.62495(19) 0.0245(10) Uani 1 1 d .
H29A H 0.5402 0.3446 0.6585 0.029 Uiso 1 1 calc R
H29B H 0.5314 0.3904 0.5876 0.029 Uiso 1 1 calc R
C30 C 0.3852(4) 0.2989(2) 0.60132(19) 0.0246(10) Uani 1 1 d .
H30A H 0.3271 0.2805 0.6382 0.029 Uiso 1 1 calc R
H30B H 0.4369 0.2487 0.5863 0.029 Uiso 1 1 calc R
C31 C 0.3001(4) 0.3324(2) 0.54455(18) 0.0298(10) Uani 1 1 d .
H31A H 0.2584 0.3873 0.5575 0.036 Uiso 1 1 calc R
H31B H 0.3570 0.3431 0.5055 0.036 Uiso 1 1 calc R
C32 C 0.1951(5) 0.2697(3) 0.52710(18) 0.0260(10) Uani 1 1 d .
C33 C -0.1701(4) 0.4666(2) 0.64782(19) 0.0231(9) Uani 1 1 d .
H33A H -0.2216 0.5091 0.6222 0.028 Uiso 1 1 calc R
H33B H -0.2223 0.4505 0.6874 0.028 Uiso 1 1 calc R
C34 C -0.1426(4) 0.3886(2) 0.60615(19) 0.0250(10) Uani 1 1 d .
H34A H -0.2268 0.3569 0.5998 0.030 Uiso 1 1 calc R
H34B H -0.0808 0.3507 0.6305 0.030 Uiso 1 1 calc R
C35 C -0.0837(4) 0.4080(3) 0.5392(2) 0.0339(11) Uani 1 1 d .
H35A H -0.0038 0.4442 0.5450 0.041 Uiso 1 1 calc R
H35B H -0.0553 0.3538 0.5182 0.041 Uiso 1 1 calc R
C36 C -0.1774(5) 0.4518(3) 0.4954(2) 0.0395(12) Uani 1 1 d .
C1S C 0.2677(4) 0.6696(2) 0.77609(17) 0.0265(10) Uani 1 1 d .
H1S1 H 0.3343 0.6322 0.7546 0.032 Uiso 1 1 calc R
H1S2 H 0.1786 0.6454 0.7673 0.032 Uiso 1 1 calc R
H2O H 0.241(5) 0.422(3) 0.713(2) 0.055(18) Uiso 1 1 d .
H4O H 0.117(5) 0.533(3) 0.620(3) 0.08(2) 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'
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
C1 O1 C29 114.3(3)
C20 O3 C33 113.9(3)
C2 C1 O1 118.8(3)
C2 C1 C6 122.7(4)
O1 C1 C6 118.4(4)
C1 C2 C3 117.4(3)
C1 C2 C28 122.5(3)
C3 C2 C28 120.1(4)
C4 C3 C2 120.7(4)
C3 C4 C5 120.3(4)
C6 C5 C4 121.0(4)
C5 C6 C1 117.7(4)
C5 C6 C7 120.4(4)
C1 C6 C7 121.7(4)
C8 C7 C6 112.8(3)
C9 C8 C13 118.5(3)
C9 C8 C7 122.2(3)
C13 C8 C7 119.3(3)
O2 C9 C8 122.5(4)
O2 C9 C10 115.9(4)
C8 C9 C10 121.5(3)
C11 C10 C9 118.7(4)
C11 C10 C14 121.0(3)
C9 C10 C14 120.3(3)
C10 C11 C12 121.0(4)
C13 C12 C11 119.4(3)
C12 C13 C8 120.9(4)
C15 C14 C10 111.6(3)
C16 C15 C20 117.4(3)
C16 C15 C14 120.4(3)
C20 C15 C14 122.0(3)
C17 C16 C15 121.2(3)
C16 C17 C18 120.1(4)
C17 C18 C19 120.5(4)
C20 C19 C18 117.8(3)
C20 C19 C21 122.4(3)
C18 C19 C21 119.7(3)
C19 C20 C15 122.8(3)
C19 C20 O3 117.8(3)
C15 C20 O3 119.3(3)
C19 C21 C22 112.4(3)
C27 C22 C23 118.1(4)
C27 C22 C21 121.9(3)
C23 C22 C21 120.0(4)
C24 C23 C22 120.8(4)
C23 C24 C25 120.3(4)
C24 C25 C26 121.5(4)
C25 C26 C27 117.6(4)
C25 C26 C28 121.7(4)
C27 C26 C28 120.7(3)
O4 C27 C22 122.2(4)
O4 C27 C26 116.0(3)
C22 C27 C26 121.8(3)
C26 C28 C2 112.0(3)
O1 C29 C30 107.0(3)
C29 C30 C31 110.1(3)
C32 C31 C30 110.7(3)
N5 C32 C31 179.1(5)
O3 C33 C34 107.7(3)
C33 C34 C35 114.3(3)
C36 C35 C34 112.6(4)
N6 C36 C35 177.1(5)
Cl2 C1S Cl1 111.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1S 1.764(4)
Cl2 C1S 1.761(4)
O1 C1 1.394(4)
O1 C29 1.443(4)
O2 C9 1.368(4)
O3 C20 1.403(4)
O3 C33 1.443(4)
O4 C27 1.376(4)
N5 C32 1.131(5)
N6 C36 1.138(5)
C1 C2 1.392(5)
C1 C6 1.398(5)
C2 C3 1.399(5)
C2 C28 1.519(5)
C3 C4 1.381(5)
C4 C5 1.386(6)
C5 C6 1.382(5)
C6 C7 1.520(5)
C7 C8 1.510(5)
C8 C9 1.390(5)
C8 C13 1.398(5)
C9 C10 1.400(5)
C10 C11 1.378(5)
C10 C14 1.525(5)
C11 C12 1.400(5)
C12 C13 1.381(5)
C14 C15 1.520(5)
C15 C16 1.387(5)
C15 C20 1.396(5)
C16 C17 1.384(5)
C17 C18 1.385(5)
C18 C19 1.396(5)
C19 C20 1.388(5)
C19 C21 1.516(5)
C21 C22 1.531(5)
C22 C27 1.392(5)
C22 C23 1.398(5)
C23 C24 1.372(5)
C24 C25 1.377(5)
C25 C26 1.384(5)
C26 C27 1.407(5)
C26 C28 1.513(5)
C29 C30 1.507(5)
C30 C31 1.526(5)
C31 C32 1.483(6)
C33 C34 1.508(5)
C34 C35 1.511(5)
C35 C36 1.464(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198920
