#------------------------------------------------------------------------------
#$Date: 2019-11-23 19:13:22 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234596 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/63/4036355.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_4036355
loop_
_publ_author_name
'Ren, Wen-Sheng'
'Zhao, Liang'
'Wang, Mei-Xiang'
_publ_section_title
;
 Selective Formylation of Azacalixpyridine Macrocycles and Their
 Transformation to Molecular Semicages.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9272
_journal_page_last               9278
_journal_paper_doi               10.1021/acs.joc.5b01722
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C H Cl3, 2(C30 H26 N6)'
_chemical_formula_sum            'C61 H53 Cl3 N12'
_chemical_formula_weight         1060.50
_space_group_crystal_system      tetragonal
_space_group_IT_number           102
_space_group_name_Hall           'P 4n -2n'
_space_group_name_H-M_alt        'P 42 n m'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.890(3)
_cell_length_b                   19.890(3)
_cell_length_c                   6.3216(13)
_cell_measurement_reflns_used    8116
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4819
_cell_measurement_theta_min      1.0238
_cell_volume                     2500.9(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2013)'
_computing_structure_solution
;
'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0079
_diffrn_orient_matrix_UB_12      0.0190
_diffrn_orient_matrix_UB_13      0.1569
_diffrn_orient_matrix_UB_21      0.0501
_diffrn_orient_matrix_UB_22      0.0037
_diffrn_orient_matrix_UB_23      0.0021
_diffrn_orient_matrix_UB_31      -0.0034
_diffrn_orient_matrix_UB_32      0.0498
_diffrn_orient_matrix_UB_33      -0.0062
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            19317
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.290
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       plate
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2974
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0682P)²+1.1711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2914
_reflns_number_total             2974
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo5b01722_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        2500.9(9)
_cod_database_code               4036355
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_diffrn_number_total             5772
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: C17(0.25) H17(0.25)
4.a Riding coordinates:
 C17(H17)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C11(H11), C13(H13)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/2'
'-x, -y, z'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'-y, -x, z'
'x+1/2, -y+1/2, z+1/2'
'y, x, z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cl1 Cl 0.44983(12) 0.44983(12) 0.1154(9) 0.1592(18) Uani 1 2 d S T P
Cl2 Cl 0.5000 0.5000 0.5015(7) 0.1205(17) Uani 1 4 d S T P
N1 N 0.04873(13) 0.21455(15) 0.3342(5) 0.0332(6) Uani 1 1 d . . .
N2 N 0.12508(13) 0.12508(13) 0.3683(7) 0.0291(8) Uani 1 2 d S T P
N3 N 0.21897(16) 0.38360(13) 0.3497(5) 0.0335(7) Uani 1 1 d . . .
N4 N 0.30724(13) 0.30724(13) 0.3916(7) 0.0300(8) Uani 1 2 d S T P
C1 C 0.06599(17) 0.28117(17) 0.2770(6) 0.0322(7) Uani 1 1 d . . .
C2 C 0.01831(19) 0.3293(2) 0.2193(7) 0.0450(9) Uani 1 1 d . . .
H2 H -0.0264 0.3174 0.1986 0.054 Uiso 1 1 calc R . .
C3 C 0.0392(2) 0.3954(2) 0.1934(8) 0.0497(10) Uani 1 1 d . . .
H3 H 0.0082 0.4271 0.1468 0.060 Uiso 1 1 calc R . .
C4 C 0.1045(2) 0.41583(18) 0.2346(7) 0.0447(9) Uani 1 1 d . . .
H4 H 0.1164 0.4610 0.2272 0.054 Uiso 1 1 calc R . .
C5 C 0.15185(17) 0.36722(16) 0.2873(5) 0.0316(7) Uani 1 1 d . . .
C6 C 0.13291(16) 0.30052(16) 0.2883(5) 0.0288(7) Uani 1 1 d . . .
H6 H 0.1660 0.2675 0.2967 0.035 Uiso 1 1 calc R . .
C7 C 0.09779(15) 0.17983(17) 0.4556(5) 0.0289(7) Uani 1 1 d . . .
C8 C 0.11835(15) 0.20528(16) 0.6536(5) 0.0295(7) Uani 1 1 d . . .
C9 C 0.16736(15) 0.16736(15) 0.7560(7) 0.0280(9) Uani 1 2 d S T P
H9 H 0.1751 0.1751 0.8990 0.034 Uiso 1 2 calc RS T P
C10 C 0.10468(17) 0.27437(17) 0.7337(5) 0.0320(7) Uani 1 1 d . . .
H10 H 0.0617 0.2847 0.7812 0.038 Uiso 1 1 calc R . .
C11 C 0.15251(18) 0.32251(17) 0.7399(6) 0.0337(7) Uani 1 1 d . . .
H11 H 0.1413 0.3647 0.7923 0.040 Uiso 1 1 calc R . .
C12 C 0.22308(16) 0.31022(16) 0.6650(5) 0.0296(7) Uani 1 1 d . . .
C13 C 0.25981(15) 0.25981(15) 0.7649(8) 0.0305(9) Uani 1 2 d S T P
H13 H 0.2502 0.2502 0.9057 0.037 Uiso 1 2 calc RS T P
C14 C 0.25097(17) 0.33368(15) 0.4743(5) 0.0283(7) Uani 1 1 d . . .
C15 C 0.00899(19) 0.1755(2) 0.1843(7) 0.0477(10) Uani 1 1 d . . .
H15A H -0.0283 0.2020 0.1361 0.072 Uiso 1 1 calc GR . .
H15B H -0.0074 0.1356 0.2523 0.072 Uiso 1 1 calc GR . .
H15C H 0.0365 0.1632 0.0657 0.072 Uiso 1 1 calc GR . .
C16 C 0.2600(2) 0.41560(17) 0.1851(7) 0.0411(8) Uani 1 1 d . . .
H16A H 0.2713 0.3830 0.0791 0.062 Uiso 1 1 calc GR . .
H16B H 0.3004 0.4332 0.2471 0.062 Uiso 1 1 calc GR . .
H16C H 0.2350 0.4516 0.1214 0.062 Uiso 1 1 calc GR . .
C17 C 0.5200(4) 0.4800(4) 0.240(3) 0.057(3) Uani 0.5 2 d S TU P
H17 H 0.5542 0.4458 0.2387 0.068 Uiso 0.5 2 d RS T P
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'
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_1
_geom_angle_site_symmetry_3
C17 Cl1 C17 38.5(7) 3_665 .
C17 Cl2 C17 37.6(8) 3_665 .
C1 N1 C7 115.2(3) . .
C1 N1 C15 117.6(3) . .
C7 N1 C15 117.7(3) . .
C7 N2 C7 119.4(4) . 8
C5 N3 C16 115.0(3) . .
C14 N3 C5 114.4(3) . .
C14 N3 C16 116.6(3) . .
C14 N4 C14 120.1(4) . 8
C2 C1 N1 123.0(3) . .
C6 C1 N1 118.6(3) . .
C6 C1 C2 118.3(3) . .
C1 C2 H2 120.7 . .
C3 C2 C1 118.5(4) . .
C3 C2 H2 120.7 . .
C2 C3 H3 118.8 . .
C4 C3 C2 122.4(3) . .
C4 C3 H3 118.8 . .
C3 C4 H4 120.8 . .
C3 C4 C5 118.4(3) . .
C5 C4 H4 120.8 . .
C4 C5 N3 122.7(3) . .
C6 C5 N3 118.2(3) . .
C6 C5 C4 119.0(3) . .
C1 C6 H6 119.0 . .
C5 C6 C1 121.9(3) . .
C5 C6 H6 119.0 . .
N2 C7 N1 116.9(3) . .
N2 C7 C8 122.8(3) . .
C8 C7 N1 120.3(3) . .
C7 C8 C10 125.4(3) . .
C9 C8 C7 114.9(3) . .
C9 C8 C10 118.0(3) . .
C8 C9 C8 122.9(4) . 8
C8 C9 H9 118.6 8 .
C8 C9 H9 118.6 . .
C8 C10 H10 118.8 . .
C11 C10 C8 122.4(3) . .
C11 C10 H10 118.8 . .
C10 C11 H11 118.9 . .
C10 C11 C12 122.3(3) . .
C12 C11 H11 118.9 . .
C13 C12 C11 117.7(3) . .
C13 C12 C14 114.9(3) . .
C14 C12 C11 125.8(3) . .
C12 C13 C12 123.3(4) 8 .
C12 C13 H13 118.3 . .
C12 C13 H13 118.3 8 .
N4 C14 N3 115.6(3) . .
N4 C14 C12 122.2(3) . .
C12 C14 N3 122.1(3) . .
N1 C15 H15A 109.5 . .
N1 C15 H15B 109.5 . .
N1 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
N3 C16 H16A 109.5 . .
N3 C16 H16B 109.5 . .
N3 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
Cl1 C17 Cl1 111.1(9) . 3_665
Cl1 C17 Cl2 109.2(5) 3_665 .
Cl1 C17 Cl2 109.2(5) . .
Cl1 C17 H17 109.1 . .
Cl1 C17 H17 109.0 3_665 .
Cl2 C17 H17 109.2 . .
C17 C17 Cl1 70.8(4) 3_665 .
C17 C17 Cl1 70.8(4) 3_665 3_665
C17 C17 Cl2 71.2(4) 3_665 .
C17 C17 H17 179.6 3_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C17 1.711(9) .
Cl1 C17 1.711(9) 3_665
Cl2 C17 1.748(16) .
Cl2 C17 1.748(16) 3_665
N1 C1 1.416(5) .
N1 C7 1.421(4) .
N1 C15 1.458(5) .
N2 C7 1.336(4) 8
N2 C7 1.336(4) .
N3 C5 1.430(5) .
N3 C14 1.418(4) .
N3 C16 1.467(5) .
N4 C14 1.343(4) 8
N4 C14 1.343(4) .
C1 C2 1.396(5) .
C1 C6 1.387(5) .
C2 H2 0.9300 .
C2 C3 1.388(6) .
C3 H3 0.9300 .
C3 C4 1.387(6) .
C4 H4 0.9300 .
C4 C5 1.390(5) .
C5 C6 1.379(5) .
C6 H6 0.9300 .
C7 C8 1.411(5) .
C8 C9 1.392(4) .
C8 C10 1.490(5) .
C9 C8 1.392(4) 8
C9 H9 0.9300 .
C10 H10 0.9300 .
C10 C11 1.350(5) .
C11 H11 0.9300 .
C11 C12 1.501(5) .
C12 C13 1.392(4) .
C12 C14 1.407(5) .
C13 C12 1.392(4) 8
C13 H13 0.9300 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 Cl1 1.711(9) 3_665
C17 C17 1.13(2) 3_665
C17 H17 0.9597 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 171.5(4) . .
N1 C1 C6 C5 -163.5(3) . .
N1 C7 C8 C9 -179.1(3) . .
N1 C7 C8 C10 -14.2(5) . .
N2 C7 C8 C9 -2.6(5) . .
N2 C7 C8 C10 162.3(3) . .
N3 C5 C6 C1 165.2(3) . .
C1 N1 C7 N2 -117.0(4) . .
C1 N1 C7 C8 59.7(4) . .
C1 C2 C3 C4 -3.8(7) . .
C2 C1 C6 C5 13.5(5) . .
C2 C3 C4 C5 5.2(7) . .
C3 C4 C5 N3 -174.6(4) . .
C3 C4 C5 C6 2.6(5) . .
C4 C5 C6 C1 -12.1(5) . .
C5 N3 C14 N4 119.4(3) . .
C5 N3 C14 C12 -56.5(4) . .
C6 C1 C2 C3 -5.4(6) . .
C7 N1 C1 C2 -159.1(4) . .
C7 N1 C1 C6 17.7(4) . .
C7 N2 C7 N1 167.5(3) 8 .
C7 N2 C7 C8 -9.1(6) 8 .
C7 C8 C9 C8 15.2(6) . 8
C7 C8 C10 C11 -104.6(4) . .
C8 C10 C11 C12 0.4(5) . .
C9 C8 C10 C11 59.9(5) . .
C10 C8 C9 C8 -150.9(3) . 8
C10 C11 C12 C13 -59.8(5) . .
C10 C11 C12 C14 104.9(4) . .
C11 C12 C13 C12 150.9(3) . 8
C11 C12 C14 N3 13.2(5) . .
C11 C12 C14 N4 -162.4(3) . .
C13 C12 C14 N3 178.2(3) . .
C13 C12 C14 N4 2.6(5) . .
C14 N3 C5 C4 156.2(3) . .
C14 N3 C5 C6 -21.1(4) . .
C14 N4 C14 N3 -166.6(3) 8 .
C14 N4 C14 C12 9.3(6) 8 .
C14 C12 C13 C12 -15.4(6) . 8
C15 N1 C1 C2 55.1(5) . .
C15 N1 C1 C6 -128.0(4) . .
C15 N1 C7 N2 28.8(5) . .
C15 N1 C7 C8 -154.6(3) . .
C16 N3 C5 C4 -64.9(4) . .
C16 N3 C5 C6 117.8(3) . .
C16 N3 C14 N4 -18.8(4) . .
C16 N3 C14 C12 165.4(3) . .
C17 Cl1 C17 Cl1 -59.4(8) 3_665 3_665
C17 Cl1 C17 Cl2 61.1(6) 3_665 .
C17 Cl2 C17 Cl1 -60.9(5) 3_665 .
C17 Cl2 C17 Cl1 60.9(5) 3_665 3_665
