#------------------------------------------------------------------------------
#$Date: 2019-11-24 01:30:07 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236009 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/37/1553772.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_1553772
loop_
_publ_author_name
'Liang, Dong-Dong'
'Wang, Mei-Xiang'
_publ_section_title
;
 Synthesis and conformational structure of hydrazo-bridged homo
 calix[2]pyridine[2]triazines
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1425
_journal_paper_doi               10.1039/C7QO00221A
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         '0.17(C32 H60 Co2 N16 O8), 0.67(Cl O4)'
_chemical_formula_sum            'C5.33 H10 Cl0.67 Co0.33 N2.67 O4'
_chemical_formula_weight         218.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-02-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-03-20 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.734(4)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   11.9766(4)
_cell_length_b                   19.3355(5)
_cell_length_c                   12.7804(4)
_cell_measurement_reflns_used    4256
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.5370
_cell_measurement_theta_min      4.6440
_cell_volume                     2688.09(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -93.00  -8.00   1.00    1.71    --  -40.81 125.00-180.00   85
  2  ω   -113.00 -16.00   1.00    1.71    --  -40.81 -38.00-120.00   97
  3  ω      2.00  60.00   1.00    1.71    --   40.81 -99.00 150.00   58
  4  ω     49.00  76.00   1.00    1.71    --   40.81-125.00 -60.00   27
  5  ω    145.00 172.00   1.00   15.00    --  111.58  77.00-120.00   27
  6  ω    135.00 178.00   1.00   15.00    --  111.58 125.00-180.00   43
  7  ω     39.00 130.00   1.00   15.00    --  111.58 -45.00  90.00   91
  8  ω     65.00  98.00   1.00   15.00    --  111.58 -95.00 -60.00   33
  9  ω     30.00  57.00   1.00   15.00    --  111.58 -95.00 -60.00   27
 10  ω     98.00 167.00   1.00   15.00    --  111.58  45.00-120.00   69
 11  ω     60.00 129.00   1.00   15.00    --  111.58 -61.00-180.00   69
 12  ω     97.00 166.00   1.00   15.00    --  111.58  30.00 -30.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0491445000
_diffrn_orient_matrix_UB_12      0.0424606000
_diffrn_orient_matrix_UB_13      -0.1122890000
_diffrn_orient_matrix_UB_21      -0.1282973000
_diffrn_orient_matrix_UB_22      -0.0323942000
_diffrn_orient_matrix_UB_23      -0.0351551000
_diffrn_orient_matrix_UB_31      -0.0349584000
_diffrn_orient_matrix_UB_32      0.0590856000
_diffrn_orient_matrix_UB_33      0.0613253000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10664
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.560
_diffrn_reflns_theta_min         4.064
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.495
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_description       plate
_exptl_crystal_F_000             1356
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.314
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.092
_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     360
_refine_ls_number_reflns         5464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0627
_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)+(0.1050P)²+1.1930P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.1785
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4633
_reflns_number_total             5464
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7qo00221a2.cif
_cod_data_source_block           exp_874
_cod_original_cell_volume        2688.08(17)
_cod_database_code               1553772
_shelxl_version_number           2013-2
_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.
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O2(H2A,H2B), O3(H3A,H3B), O4(H4A,H4B)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2C,H2D,H2E), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C11(H11A,H11B,H11C)
;
_olex2_date_sample_data_collection 2017-02-12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.698
_oxdiff_exptl_absorpt_empirical_full_min 0.677
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Co1 Co 0.43331(5) 0.38472(3) 0.76529(4) 0.03653(18) Uani 1 1 d .
O1 O 0.6932(2) 0.44984(15) 0.9346(2) 0.0445(6) Uani 1 1 d .
O2 O 0.3418(3) 0.33911(15) 0.6001(2) 0.0496(6) Uani 1 1 d .
H2A H 0.3934 0.3302 0.5685 0.074 Uiso 1 1 d GR
H2B H 0.2841 0.3667 0.5524 0.074 Uiso 1 1 d GR
O3 O 0.5450(3) 0.29742(16) 0.7991(2) 0.0540(7) Uani 1 1 d .
H3A H 0.6002 0.2982 0.8693 0.081 Uiso 1 1 d GR
H3B H 0.5816 0.2966 0.7535 0.081 Uiso 1 1 d GR
O4 O 0.5270(3) 0.44227(16) 0.6948(2) 0.0526(7) Uani 1 1 d .
H4A H 0.5182 0.4252 0.6271 0.079 Uiso 1 1 d GR
H4B H 0.6075 0.4434 0.7393 0.079 Uiso 1 1 d GR
N1 N 0.2516(3) 0.43460(16) 0.7332(2) 0.0400(6) Uani 1 1 d .
N2 N 0.3141(3) 0.33486(15) 0.8343(2) 0.0407(6) Uani 1 1 d .
N3 N 0.3536(3) 0.35541(16) 0.9517(2) 0.0399(6) Uani 1 1 d .
N4 N 0.5030(3) 0.39946(15) 1.1163(2) 0.0385(6) Uani 1 1 d .
N5 N 0.5207(3) 0.40868(15) 0.9380(2) 0.0360(6) Uani 1 1 d .
N6 N 0.6871(3) 0.44360(16) 1.1110(2) 0.0394(6) Uani 1 1 d .
N7 N 0.6616(3) 0.43875(16) 1.2803(2) 0.0427(7) Uani 1 1 d .
N8 N 0.7875(3) 0.45260(17) 1.3390(2) 0.0470(7) Uani 1 1 d .
C1 C 0.2974(5) 0.2590(2) 0.8198(4) 0.0525(9) Uani 1 1 d .
H1A H 0.2745 0.2471 0.7406 0.079 Uiso 1 1 calc GR
H1B H 0.2340 0.2445 0.8424 0.079 Uiso 1 1 calc GR
H1C H 0.3731 0.2362 0.8672 0.079 Uiso 1 1 calc GR
C2 C 0.2788(4) 0.3377(2) 1.0132(3) 0.0476(8) Uani 1 1 d .
H2C H 0.2900 0.2897 1.0343 0.071 Uiso 1 1 calc GR
H2D H 0.1938 0.3463 0.9644 0.071 Uiso 1 1 calc GR
H2E H 0.3035 0.3656 1.0814 0.071 Uiso 1 1 calc GR
C3 C 0.4623(3) 0.38890(16) 1.0034(3) 0.0356(7) Uani 1 1 d .
C4 C 0.6338(3) 0.43368(17) 0.9992(3) 0.0363(7) Uani 1 1 d .
C5 C 0.6148(3) 0.42624(17) 1.1648(3) 0.0364(7) Uani 1 1 d .
C6 C 0.8214(4) 0.4726(3) 0.9942(4) 0.0533(9) Uani 1 1 d .
H6A H 0.8295 0.5036 1.0568 0.064 Uiso 1 1 calc R
H6B H 0.8449 0.4978 0.9409 0.064 Uiso 1 1 calc R
C7 C 0.9054(4) 0.4112(3) 1.0414(4) 0.0651(12) Uani 1 1 d .
H7A H 0.8785 0.3853 1.0917 0.078 Uiso 1 1 calc R
H7B H 0.9879 0.4279 1.0878 0.078 Uiso 1 1 calc R
C8 C 0.9099(6) 0.3624(4) 0.9491(6) 0.0834(17) Uani 1 1 d .
H8A H 0.9495 0.3858 0.9066 0.100 Uiso 1 1 calc R
H8B H 0.8266 0.3512 0.8952 0.100 Uiso 1 1 calc R
C9 C 0.9802(8) 0.2945(4) 1.0008(11) 0.125(4) Uani 1 1 d .
H9A H 0.9904 0.2685 0.9414 0.187 Uiso 1 1 calc GR
H9B H 0.9343 0.2676 1.0324 0.187 Uiso 1 1 calc GR
H9C H 1.0595 0.3054 1.0605 0.187 Uiso 1 1 calc GR
C10 C 0.6033(5) 0.4109(2) 1.3511(3) 0.0558(10) Uani 1 1 d .
H10A H 0.5156 0.4125 1.3087 0.084 Uiso 1 1 calc GR
H10B H 0.6270 0.4380 1.4200 0.084 Uiso 1 1 calc GR
H10C H 0.6289 0.3639 1.3711 0.084 Uiso 1 1 calc GR
C11 C 0.8660(5) 0.3901(2) 1.3641(4) 0.0624(12) Uani 1 1 d .
H11A H 0.8227 0.3514 1.3764 0.094 Uiso 1 1 calc GR
H11B H 0.9404 0.3978 1.4320 0.094 Uiso 1 1 calc GR
H11C H 0.8858 0.3805 1.3001 0.094 Uiso 1 1 calc GR
C12 C 0.8294(4) 0.5142(2) 1.3175(3) 0.0439(8) Uani 1 1 d .
C13 C 0.9563(4) 0.5247(3) 1.3474(3) 0.0552(10) Uani 1 1 d .
H13 H 1.0125 0.4896 1.3828 0.066 Uiso 1 1 calc R
C14 C 0.9957(4) 0.5867(3) 1.3241(4) 0.0591(11) Uani 1 1 d .
H14 H 1.0794 0.5943 1.3473 0.071 Uiso 1 1 calc R
C15 C 0.9125(4) 0.6384(3) 1.2661(3) 0.0545(10) Uani 1 1 d .
H15 H 0.9374 0.6806 1.2480 0.065 Uiso 1 1 calc R
C16 C 0.7914(4) 0.62353(19) 1.2372(3) 0.0424(8) Uani 1 1 d .
Cl1 Cl 0.67363(10) 0.27243(5) 0.60116(8) 0.0502(2) Uani 1 1 d .
O5 O 0.5453(5) 0.2888(4) 0.5496(4) 0.1094(19) Uani 1 1 d .
O6 O 0.6959(4) 0.2249(3) 0.5277(3) 0.0870(13) Uani 1 1 d .
O7 O 0.7396(8) 0.3324(3) 0.6147(6) 0.149(3) Uani 1 1 d .
O8 O 0.7021(5) 0.2405(2) 0.7090(4) 0.0816(12) Uani 1 1 d .
Cl2 Cl 0.26886(9) 0.05917(5) 0.85491(8) 0.0502(2) Uani 1 1 d .
O9 O 0.3926(4) 0.0541(4) 0.9407(3) 0.109(2) Uani 1 1 d .
O10 O 0.2649(6) 0.1039(2) 0.7675(4) 0.0998(16) Uani 1 1 d .
O11 O 0.2305(5) -0.0067(2) 0.8047(5) 0.0944(14) Uani 1 1 d .
O12 O 0.1927(4) 0.0838(3) 0.9092(4) 0.0837(13) 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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O2 Co1 N1 86.53(11) . .
O2 Co1 N2 93.74(12) . .
O3 Co1 O2 83.62(12) . .
O3 Co1 N1 150.58(13) . .
O3 Co1 N2 91.73(12) . .
O4 Co1 O2 86.43(12) . .
O4 Co1 O3 96.28(13) . .
O4 Co1 N1 110.72(12) . .
O4 Co1 N2 171.96(13) . .
O4 Co1 N5 102.94(12) . .
N2 Co1 N1 61.29(12) . .
N5 Co1 O2 168.12(12) . .
N5 Co1 O3 88.03(12) . .
N5 Co1 N1 96.76(11) . .
N5 Co1 N2 78.02(12) . .
C4 O1 C6 117.6(3) . .
C12 N1 Co1 147.9(3) 3_667 .
C12 N1 C16 117.6(3) 3_667 3_667
C16 N1 Co1 92.6(2) 3_667 .
N3 N2 Co1 108.4(2) . .
N3 N2 C1 112.0(3) . .
N3 N2 C16 109.0(3) . 3_667
C1 N2 Co1 117.5(3) . .
C16 N2 Co1 92.6(2) 3_667 .
C16 N2 C1 115.7(3) 3_667 .
N2 N3 C2 119.5(3) . .
C3 N3 N2 118.4(3) . .
C3 N3 C2 122.1(3) . .
C5 N4 C3 114.1(3) . .
C3 N5 Co1 115.9(2) . .
C4 N5 Co1 130.0(2) . .
C4 N5 C3 113.6(3) . .
C4 N6 C5 113.1(3) . .
N8 N7 C10 115.3(3) . .
C5 N7 N8 118.4(3) . .
C5 N7 C10 121.3(3) . .
N7 N8 C11 113.8(3) . .
C12 N8 N7 117.6(3) . .
C12 N8 C11 120.1(4) . .
N4 C3 N3 116.4(3) . .
N4 C3 N5 125.3(3) . .
N5 C3 N3 118.3(3) . .
O1 C4 N5 113.2(3) . .
N6 C4 O1 119.9(3) . .
N6 C4 N5 126.9(3) . .
N4 C5 N6 126.6(3) . .
N4 C5 N7 117.0(3) . .
N6 C5 N7 116.4(3) . .
O1 C6 C7 110.4(4) . .
C6 C7 C8 114.2(4) . .
C7 C8 C9 112.4(7) . .
N1 C12 N8 119.2(4) 3_667 .
N1 C12 C13 119.9(4) 3_667 .
N8 C12 C13 121.0(4) . .
C14 C13 C12 119.8(4) . .
C13 C14 C15 120.8(4) . .
C16 C15 C14 115.9(4) . .
N1 C16 N2 107.7(3) 3_667 3_667
N1 C16 C15 125.6(4) 3_667 .
C15 C16 N2 126.7(4) . 3_667
O6 Cl1 O5 107.5(3) . .
O7 Cl1 O5 108.8(5) . .
O7 Cl1 O6 112.0(5) . .
O7 Cl1 O8 110.7(4) . .
O8 Cl1 O5 108.7(3) . .
O8 Cl1 O6 109.0(3) . .
O9 Cl2 O12 108.3(2) . .
O10 Cl2 O9 109.5(4) . .
O10 Cl2 O11 107.3(3) . .
O10 Cl2 O12 111.4(3) . .
O11 Cl2 O9 108.8(4) . .
O11 Cl2 O12 111.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 O2 2.121(3) .
Co1 O3 2.084(3) .
Co1 O4 2.038(3) .
Co1 N1 2.255(3) .
Co1 N2 2.191(3) .
Co1 N5 2.061(3) .
O1 C4 1.333(4) .
O1 C6 1.468(5) .
N1 C12 1.348(5) 3_667
N1 C16 1.354(5) 3_667
N2 N3 1.428(4) .
N2 C1 1.482(5) .
N2 C16 1.453(5) 3_667
N3 C2 1.458(5) .
N3 C3 1.353(5) .
N4 C3 1.331(4) .
N4 C5 1.322(5) .
N5 C3 1.351(5) .
N5 C4 1.339(5) .
N6 C4 1.312(4) .
N6 C5 1.354(5) .
N7 N8 1.401(5) .
N7 C5 1.365(4) .
N7 C10 1.456(5) .
N8 C11 1.482(5) .
N8 C12 1.363(5) .
C6 C7 1.510(7) .
C7 C8 1.529(8) .
C8 C9 1.550(10) .
C12 N1 1.348(5) 3_667
C12 C13 1.419(6) .
C13 C14 1.366(7) .
C14 C15 1.387(7) .
C15 C16 1.369(6) .
C16 N1 1.354(5) 3_667
C16 N2 1.453(5) 3_667
Cl1 O5 1.431(5) .
Cl1 O6 1.417(4) .
Cl1 O7 1.372(5) .
Cl1 O8 1.415(4) .
Cl2 O9 1.431(4) .
Cl2 O10 1.398(4) .
Cl2 O11 1.413(4) .
Cl2 O12 1.439(4) .
