#------------------------------------------------------------------------------
#$Date: 2017-02-04 04:28:05 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191398 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/49/1544937.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_1544937
loop_
_publ_author_name
'Díaz-Moscoso, Alejandro'
'Hernández-Alonso, Daniel'
'Escobar, Luis'
'Arroyave, Frank A.'
'Ballester, Pablo'
_publ_section_title
;
 Stereoselective Synthesis of Lower and Upper Rim Functionalized Tetra-α
 Isomers of Calix[4]pyrroles.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              226
_journal_page_last               229
_journal_paper_doi               10.1021/acs.orglett.6b03505
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C60 H58 Br4 Cl4 N6'
_chemical_formula_weight         1324.56
_space_group_IT_number           85
_space_group_name_Hall           '-P 4a'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-P 4a'
_symmetry_space_group_name_H-M   'P 4/n :2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.2293(2)
_cell_length_b                   14.2293(2)
_cell_length_c                   14.5334(4)
_cell_measurement_reflns_used    19573
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.4110
_cell_measurement_theta_min      2.0030
_cell_volume                     2942.62(10)
_computing_cell_refinement
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            53682
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.677
_diffrn_reflns_theta_min         2.024
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_current           24
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    2.960
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.010
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         4347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0342
_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)+(0.0628P)²+1.5185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3786
_reflns_number_total             4347
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b03505_si_004.cif
_cod_data_source_block           CADM17aaa_twin1_hklf4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1544936--1544937.cif.
;
_cod_original_cell_volume        2942.62(12)
_cod_original_sg_symbol_H-M      P4/n
_cod_database_code               1544937
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.665
_shelx_estimated_absorpt_t_max   0.943
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z'
'y, -x+1/2, z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z'
'-y, x-1/2, -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
Br1 Br 0.18233(2) 0.97602(2) 1.12815(2) 0.02495(8) Uani 1 1 d . . .
C1 C 0.25479(10) 1.03275(10) 0.66681(10) 0.0129(3) Uani 1 1 d . . .
C2 C 0.30675(11) 0.98624(11) 0.60160(11) 0.0171(3) Uani 1 1 d . . .
H2 H 0.2850 0.9375 0.5624 0.020 Uiso 1 1 calc R U .
C3 C 0.39930(11) 1.02438(11) 0.60339(11) 0.0167(3) Uani 1 1 d . . .
H3 H 0.4502 1.0056 0.5653 0.020 Uiso 1 1 calc R U .
C4 C 0.15552(10) 1.01787(10) 0.70179(10) 0.0123(3) Uani 1 1 d . . .
C5 C 0.15947(10) 1.00896(10) 0.80741(10) 0.0134(3) Uani 1 1 d . . .
C6 C 0.09469(11) 1.05201(11) 0.86598(10) 0.0154(3) Uani 1 1 d . . .
H6 H 0.0448 1.0879 0.8404 0.019 Uiso 1 1 calc R U .
C7 C 0.10178(11) 1.04337(11) 0.96129(11) 0.0176(3) Uani 1 1 d . . .
H7 H 0.0585 1.0749 1.0003 0.021 Uiso 1 1 calc R U .
C8 C 0.17259(11) 0.98840(12) 0.99852(12) 0.0180(3) Uani 1 1 d . . .
C9 C 0.23633(11) 0.94166(12) 0.94180(12) 0.0194(3) Uani 1 1 d . . .
H9 H 0.2838 0.9028 0.9676 0.023 Uiso 1 1 calc R U .
C10 C 0.22944(11) 0.95278(11) 0.84721(12) 0.0172(3) Uani 1 1 d . . .
H10 H 0.2732 0.9216 0.8085 0.021 Uiso 1 1 calc R U .
C11 C 0.09295(10) 1.09782(10) 0.66976(10) 0.0128(3) Uani 1 1 d . . .
C12 C 0.11794(10) 0.92390(10) 0.66154(11) 0.0144(3) Uani 1 1 d . . .
H12A H 0.1090 0.9313 0.5944 0.017 Uiso 1 1 calc R U .
H12B H 0.1657 0.8743 0.6712 0.017 Uiso 1 1 calc R U .
C13 C 0.02507(11) 0.89197(11) 0.70449(12) 0.0182(3) Uani 1 1 d . . .
H13A H 0.0373 0.8700 0.7680 0.022 Uiso 1 1 calc R U .
H13B H -0.0179 0.9466 0.7083 0.022 Uiso 1 1 calc R U .
C14 C -0.02298(12) 0.81433(12) 0.65154(13) 0.0234(3) Uani 1 1 d . . .
H14A H -0.0389 0.8374 0.5892 0.028 Uiso 1 1 calc R U .
H14B H -0.0824 0.7976 0.6830 0.028 Uiso 1 1 calc R U .
C1S C 0.2500 0.2500 0.9427(3) 0.0211(6) Uani 1 4 d S T P
C2S C 0.2500 0.2500 1.0434(3) 0.0303(8) Uani 1 4 d S T P
H2S1 H 0.3040 0.2139 1.0659 0.045 Uiso 0.25 1 calc R U P
H2S2 H 0.1918 0.2213 1.0659 0.045 Uiso 0.25 1 calc R U P
H2S3 H 0.2543 0.3148 1.0659 0.045 Uiso 0.25 1 calc R U P
C1T C 0.2500 0.2500 0.4238(3) 0.0202(6) Uani 1 4 d S T P
C2T C 0.2500 0.2500 0.5236(3) 0.0327(8) Uani 1 4 d S T P
H2T1 H 0.3009 0.2097 0.5461 0.049 Uiso 0.25 1 calc R U P
H2T2 H 0.1897 0.2260 0.5461 0.049 Uiso 0.25 1 calc R U P
H2T3 H 0.2594 0.3142 0.5461 0.049 Uiso 0.25 1 calc R U P
Cl1 Cl 0.04936(4) 0.71030(3) 0.64146(3) 0.02940(12) Uani 1 1 d . . .
N1 N 0.31308(8) 1.09897(8) 0.70674(9) 0.0126(2) Uani 1 1 d . . .
H1 H 0.2958 1.1392 0.7496 0.015 Uiso 1 1 calc R U .
N1S N 0.2500 0.2500 0.8641(2) 0.0212(6) Uani 1 4 d S T P
N1T N 0.2500 0.2500 0.3457(2) 0.0279(6) Uani 1 4 d S 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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 '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
C2 C1 N1 107.17(13) . .
C2 C1 C4 131.78(13) . .
N1 C1 C4 120.88(13) . .
C1 C2 C3 107.57(13) . .
C11 C3 C2 108.13(13) 3_665 .
C1 C4 C11 109.82(12) . .
C1 C4 C5 108.15(12) . .
C11 C4 C5 112.86(12) . .
C1 C4 C12 108.33(12) . .
C11 C4 C12 109.12(12) . .
C5 C4 C12 108.46(12) . .
C6 C5 C10 117.88(14) . .
C6 C5 C4 123.16(13) . .
C10 C5 C4 118.93(13) . .
C7 C6 C5 121.27(14) . .
C8 C7 C6 119.37(15) . .
C7 C8 C9 120.76(16) . .
C7 C8 Br1 119.56(13) . .
C9 C8 Br1 119.68(12) . .
C10 C9 C8 119.04(15) . .
C9 C10 C5 121.61(15) . .
C3 C11 N1 106.89(13) 4_465 4_465
C3 C11 C4 130.91(13) 4_465 .
N1 C11 C4 122.20(13) 4_465 .
C13 C12 C4 113.51(12) . .
C14 C13 C12 113.60(14) . .
C13 C14 Cl1 112.48(12) . .
N1S C1S C2S 180.0 . .
N1T C1T C2T 180.0 . .
C11 N1 C1 110.20(12) 3_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C8 1.8973(18) .
C1 C2 1.372(2) .
C1 N1 1.3829(18) .
C1 C4 1.516(2) .
C2 C3 1.425(2) .
C3 C11 1.373(2) 3_665
C4 C11 1.518(2) .
C4 C5 1.541(2) .
C4 C12 1.5543(19) .
C5 C6 1.396(2) .
C5 C10 1.402(2) .
C6 C7 1.394(2) .
C7 C8 1.385(2) .
C8 C9 1.394(2) .
C9 C10 1.387(2) .
C11 C3 1.373(2) 4_465
C11 N1 1.3796(18) 4_465
C12 C13 1.530(2) .
C13 C14 1.510(2) .
C14 Cl1 1.8090(19) .
C1S N1S 1.142(5) .
C1S C2S 1.464(5) .
C1T N1T 1.135(5) .
C1T C2T 1.451(5) .
N1 C11 1.3796(18) 3_665
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_4
N1 C1 C2 C3 1.00(17) .
C4 C1 C2 C3 -174.19(15) .
C1 C2 C3 C11 0.28(19) 3_665
C2 C1 C4 C11 -110.00(18) .
N1 C1 C4 C11 75.35(17) .
C2 C1 C4 C5 126.45(17) .
N1 C1 C4 C5 -48.20(17) .
C2 C1 C4 C12 9.1(2) .
N1 C1 C4 C12 -165.56(13) .
C1 C4 C5 C6 137.65(14) .
C11 C4 C5 C6 15.95(19) .
C12 C4 C5 C6 -105.08(16) .
C1 C4 C5 C10 -44.37(17) .
C11 C4 C5 C10 -166.07(13) .
C12 C4 C5 C10 72.90(16) .
C10 C5 C6 C7 3.1(2) .
C4 C5 C6 C7 -178.93(13) .
C5 C6 C7 C8 -2.2(2) .
C6 C7 C8 C9 -0.2(2) .
C6 C7 C8 Br1 -179.79(12) .
C7 C8 C9 C10 1.6(2) .
Br1 C8 C9 C10 -178.80(12) .
C8 C9 C10 C5 -0.7(2) .
C6 C5 C10 C9 -1.6(2) .
C4 C5 C10 C9 -179.70(13) .
C1 C4 C11 C3 106.37(18) 4_465
C5 C4 C11 C3 -132.88(17) 4_465
C12 C4 C11 C3 -12.2(2) 4_465
C1 C4 C11 N1 -72.73(17) 4_465
C5 C4 C11 N1 48.01(18) 4_465
C12 C4 C11 N1 168.66(13) 4_465
C1 C4 C12 C13 169.99(12) .
C11 C4 C12 C13 -70.47(16) .
C5 C4 C12 C13 52.84(16) .
C4 C12 C13 C14 166.54(14) .
C12 C13 C14 Cl1 59.13(17) .
C2 C1 N1 C11 -1.95(17) 3_665
C4 C1 N1 C11 173.88(13) 3_665
