#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/94/2009482.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009482
loop_
_publ_author_name
'Kobayashi, K.'
'Tsuboyama, S.'
'Tsuboyama, K.'
'Sakurai, T.'
_publ_section_title
;
 HBF₄ and HBr salts of new chiral cyclens
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              306
_journal_page_last               312
_journal_paper_doi               10.1107/S0108270193007139
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C44 H61 N4 , B1 F4'
_chemical_formula_sum            'C44 H61 B F4 N4'
_chemical_formula_weight         732.78
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 114.94(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   23.386(5)
_cell_length_b                   9.690(2)
_cell_length_c                   20.367(5)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293
_cell_measurement_theta_max      11
_cell_measurement_theta_min      9
_cell_volume                     4185.0(18)
_diffrn_measurement_device       'Rigaku AFC-4'
_diffrn_measurement_method       'ω and ω/2θ (2θ>30°)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9612
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        -1.5
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_meas      1.162
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.33
_refine_ls_goodness_of_fit_obs   1.50
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     722
_refine_ls_number_reflns         5168
_refine_ls_R_factor_obs          0.060
_refine_ls_shift/esd_max         '0.75 [N(4); z]'
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/(a|Fₒ|² + b|Fₒ| + c)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.055
_reflns_number_observed          5168
_reflns_number_total             5709
_reflns_observed_criterion       |F~o~|>3\s(|F~o~|)
_cod_data_source_file            oh1033.cif
_cod_data_source_block           oh1033_structure_1_of_4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/(a|F~o~|^2^ + b|F~o~| + c)'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = 1/(a|F~o~|^2^ +
b|F~o~| + c)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        4185(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C44 H61 B1 F4 N4'
_cod_database_code               2009482
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
N(1) .31750(10) .3593(2) .45430(10)
N(4) .32380(10) .1226(2) .54220(10)
N(7) .30660(10) -.0604(2) .41960(10)
N(10) .23260(10) .1692(2) .31820(10)
C(2) .26710(10) .3343(3) .4784(2)
C(3) .2946(2) .2568(3) .5497(2)
C(5) .27450(10) .0090(3) .51480(10)
C(6) .2988(2) -.1079(3) .4835(2)
C(8) .24660(10) -.0787(3) .3540(2)
C(9) .2402(2) .0278(3) .2962(2)
C(11) .28790(10) .2558(3) .33030(10)
C(12) .2921(2) .3845(2) .3759(2)
C(1)1 .3605(2) .4726(4) .4947(2)
C(1)2 .4233(2) .4663(6) .4892(3)
C(4)1 .3810(2) .0851(4) .6108(2)
C(4)2 .4375(2) .1714(6) .6210(3)
C(7)1 .3610(2) -.1224(4) .4121(2)
C(7)2 .4225(2) -.0593(8) .4621(3)
C(10)1 .1723(2) .2303(4) .2690(2)
C(10)2 .1164(2) .1600(7) .2741(4)
C(2)1 .2323(2) .4639(3) .4862(2)
C(2)2 .16990(10) .4310(3) .4882(2)
C(2)3 .1175(2) .4058(4) .4242(2)
C(2)4 .0594(2) .3773(4) .4244(4)
C(2)5 .0531(3) .3754(4) .4878(4)
C(2)6 .1042(3) .3994(5) .5513(4)
C(2)7 .1631(2) .4275(4) .5525(2)
C(5)1 .25190(10) -.0386(3) .5718(2)
C(5)2 .18240(10) -.0739(3) .5357(2)
C(5)3 .1613(2) -.2087(3) .5234(2)
C(5)4 .0979(2) -.2386(4) .4862(3)
C(5)5 .0543(2) -.1357(4) .4619(2)
C(5)6 .0742(2) -.0006(4) .4749(3)
C(5)7 .1374(2) .0291(4) .5107(2)
C(8)1 .2382(2) -.2273(3) .3242(2)
C(8)2 .1710(2) -.2741(3) .2819(2)
C(8)3 .1502(2) -.3198(5) .2119(2)
C(8)4 .0900(3) -.3734(6) .1755(3)
C(8)5 .0502(3) -.3799(6) .2082(3)
C(8)6 .0694(2) -.3323(6) .2774(3)
C(8)7 .1298(2) -.2806(5) .3142(2)
C(11)1 .2937(2) .3004(4) .2601(2)
C(11)2 .3590(2) .3508(3) .2758(2)
C(11)3 .3726(2) .4910(4) .2761(2)
C(11)4 .4336(2) .5355(5) .2935(2)
C(11)5 .4812(2) .4433(6) .3100(2)
C(11)6 .4693(2) .3037(5) .3102(2)
C(11)7 .4081(2) .2582(4) .2927(2)
B .3485(2) -.1230(4) .1886(2)
F(1) .39290(10) -.1245(3) .25800(10)
F(2) .36500(10) -.2010(3) .1440(2)
F(3) .29490(10) -.1779(4) .1878(2)
F(4) .3394(2) .0077(3) .1665(2)
H(N4) .337(2) .137(4) .503(2)
H(1)1 .371(2) .462(4) .547(2)
H(1)2 .337(2) .567(4) .474(2)
H(1)3 .419(2) .477(4) .443(3)
H(1)4 .451(2) .536(5) .517(3)
H(1)5 .446(2) .375(5) .508(2)
H(2)1 .236(2) .274(4) .440(2)
H(2)2 .258(2) .515(4) .531(2)
H(2)3 .224(2) .521(4) .446(2)
H(2)4 .119(2) .411(4) .379(2)
H(2)5 .025(2) .365(4) .377(2)
H(2)6 .012(2) .358(4) .487(2)
H(2)7 .102(2) .400(4) .597(2)
H(2)8 .198(2) .449(4) .596(2)
H(3)1 .262(2) .233(4) .567(2)
H(3)2 .327(2) .306(4) .587(2)
H(4)1 .367(2) .099(4) .647(2)
H(4)2 .389(2) -.014(4) .608(2)
H(4)3 .446(2) .172(5) .579(2)
H(4)4 .473(2) .138(4) .659(2)
H(4)5 .430(2) .262(5) .631(2)
H(5)1 .237(2) .055(4) .473(2)
H(5)2 .277(2) -.115(4) .599(2)
H(5)3 .258(2) .035(4) .607(2)
H(5)4 .193(2) -.283(4) .541(2)
H(5)5 .084(2) -.326(5) .479(2)
H(5)6 .008(2) -.156(4) .437(2)
H(5)7 .043(2) .070(5) .457(2)
H(5)8 .152(2) .122(4) .520(2)
H(6)1 .266(2) -.188(4) .472(2)
H(6)2 .339(2) -.139(4) .519(2)
H(7)1 .355(2) -.104(4) .365(2)
H(7)2 .364(2) -.230(5) .417(2)
H(7)3 .455(2) -.101(4) .451(2)
H(7)4 .422(2) .045(6) .454(3)
H(7)5 .432(2) -.077(5) .512(3)
H(8)1 .213(2) -.058(4) .371(2)
H(8)2 .261(2) -.234(4) .295(2)
H(8)3 .258(2) -.293(4) .366(2)
H(8)4 .177(2) -.311(5) .190(2)
H(8)5 .077(2) -.405(5) .125(3)
H(8)6 .009(2) -.416(5) .184(3)
H(8)7 .041(2) -.334(5) .302(2)
H(8)8 .142(2) -.251(4) .361(2)
H(9)1 .202(2) .002(4) .251(2)
H(9)2 .277(2) .018(4) .284(2)
H(10)1 .167(2) .231(4) .219(2)
H(10)2 .172(2) .331(5) .281(2)
H(10)3 .120(2) .165(5) .327(3)
H(10)4 .078(2) .209(5) .245(3)
H(10)5 .109(2) .064(5) .257(3)
H(11)1 .325(2) .195(4) .358(2)
H(11)2 .262(2) .370(4) .236(2)
H(11)3 .282(2) .220(4) .225(2)
H(11)4 .339(2) .555(5) .263(2)
H(11)5 .443(2) .633(5) .294(2)
H(11)6 .525(2) .470(4) .321(2)
H(11)7 .500(2) .236(5) .321(2)
H(11)8 .401(2) .163(5) .293(2)
H(12)1 .318(2) .448(4) .367(2)
H(12)2 .248(2) .432(4) .358(2)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(12) N(1) C(2) 111.9(2) yes
N(1) C(2) C(3) 108.8(2) yes
C(2) C(3) N(4) 111.0(3) yes
C(3) N(4) C(5) 110.9(2) yes
N(4) C(5) C(6) 109.5(3) yes
C(5) C(6) N(7) 110.3(2) yes
C(6) N(7) C(8) 109.7(3) yes
N(7) C(8) C(9) 111.2(3) yes
C(8) C(9) N(10) 112.3(3) yes
C(9) N(10) C(11) 111.7(3) yes
N(10) C(11) C(12) 113.0(3) yes
C(11) C(12) N(1) 114.6(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) C(2) 1.477(5) yes
C(2) C(3) 1.517(4) yes
C(3) N(4) 1.505(4) yes
N(4) C(5) 1.519(3) yes
C(5) C(6) 1.522(5) yes
C(6) N(7) 1.463(5) yes
N(7) C(8) 1.484(3) yes
C(8) C(9) 1.525(5) yes
C(9) N(10) 1.476(4) yes
N(10) C(11) 1.474(4) yes
C(11) C(12) 1.533(4) yes
C(12) N(1) 1.471(4) yes
N(1) C(1)1 1.481(4) yes
C(2) C(2)1 1.541(5) yes
N(4) C(4)1 1.517(3) yes
C(5) C(5)1 1.536(5) yes
N(7) C(7)1 1.473(5) yes
C(8) C(8)1 1.543(4) yes
N(10) C(10)1 1.466(4) yes
C(11) C(11)1 1.552(5) yes
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_publ_flag
C(11) C(12) N(1) C(2) -93.9(3) yes
C(12) N(1) C(2) C(3) 158.3(3) yes
N(1) C(2) C(3) N(4) -58.1(3) yes
C(2) C(3) N(4) C(5) -85.3(3) yes
C(3) N(4) C(5) C(6) 160.7(2) yes
N(4) C(5) C(6) N(7) -64.8(3) yes
C(5) C(6) N(7) C(8) -88.0(3) yes
C(6) N(7) C(8) C(9) 151.3(3) yes
N(7) C(8) C(9) N(10) -67.4(3) yes
C(8) C(9) N(10) C(11) 112.1(3) yes
C(9) N(10) C(11) C(12) -161.2(3) yes
N(10) C(11) C(12) N(1) 79.6(3) yes
