#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/94/2009485.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_2009485
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 H62 N4 , 2Br1'
_chemical_formula_sum            'C44 H62 Br2 N4'
_chemical_formula_weight         806.78
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   17.243(3)
_cell_length_b                   17.873(2)
_cell_length_c                   14.156(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     4362.7(11)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5542
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        -10.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.871
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      1.220
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.08
_refine_diff_density_min         -0.63
_refine_ls_goodness_of_fit_obs   5.83
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     699
_refine_ls_number_reflns         2275
_refine_ls_R_factor_obs          0.099
_refine_ls_shift/esd_max         '0.48 [C(10)3; \b~13~]'
_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         0.112
_reflns_number_observed          2275
_reflns_number_total             2560
_reflns_observed_criterion       |F~o~|>4\s(|F~o~|)
_cod_data_source_file            oh1033.cif
_cod_data_source_block           oh1033_structure_4_of_4
_cod_depositor_comments
;
 Adding the _atom_site_type_symbol data item.

 Antanas Vaitkus,
 2017-01-19

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        4363.0(10)
_cod_database_code               2009485
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
Br(1) Br -.0356(2) .69810(10) .2615(2)
Br(2) Br .0349(2) .5911(2) -.3017(2)
N(1) N .0810(10) .5690(10) .0130(10)
C(2) C .0300(10) .6260(10) -.0300(10)
C(3) C -.050(2) .6200(10) .011(2)
N(4) N -.0870(10) .5440(10) -.0010(10)
C(5) C -.1550(10) .5290(10) .0630(10)
C(6) C -.1300(10) .5110(10) .162(2)
N(7) N -.0740(10) .4460(10) .1650(10)
C(8) C -.0350(10) .4390(10) .2540(10)
C(9) C .0370(10) .4870(10) .2570(10)
N(10) N .0910(10) .4680(10) .1780(10)
C(11) C .1510(10) .5280(10) .159(2)
C(12) C .1150(10) .5920(10) .1030(10)
C(2)1 C .0570(10) .7100(10) -.016(2)
C(2)2 C .0220(10) .7590(10) -.092(2)
C(5)1 C -.2120(10) .5960(10) .063(2)
C(5)2 C -.293(2) .572(2) .100(3)
C(8)1 C -.082(2) .460(2) .342(2)
C(8)2 C -.040(4) .431(3) .436(3)
C(11)1 C .1940(10) .5530(10) .247(2)
C(11)2 C .277(2) .576(2) .233(2)
C(1)7 C .2090(10) .5880(10) -.0730(10)
C(1)2 C .2040(10) .6500(10) -.130(2)
C(1)3 C .269(2) .698(2) -.139(2)
C(1)4 C .331(2) .689(2) -.090(2)
C(1)5 C .338(2) .629(2) -.033(2)
C(1)6 C .2770(10) .5800(10) -.023(2)
C(1)1 C .1390(10) .5390(10) -.0540(10)
C(4)7 C -.117(2) .4450(10) -.123(2)
C(4)2 C -.051(3) .404(2) -.138(2)
C(4)3 C -.063(3) .327(3) -.152(4)
C(4)4 C -.128(4) .298(3) -.151(3)
C(4)5 C -.197(3) .333(3) -.141(2)
C(4)6 C -.194(3) .414(3) -.126(2)
C(4)1 C -.105(2) .5290(10) -.1060(10)
C(7)7 C -.1790(10) .3440(10) .193(2)
C(7)2 C -.167(2) .2990(10) .274(2)
C(7)3 C -.228(2) .2780(10) .326(2)
C(7)4 C -.300(2) .296(2) .303(2)
C(7)5 C -.3160(10) .3420(10) .224(2)
C(7)6 C -.255(2) .3670(10) .168(2)
C(7)1 C -.1100(10) .3730(10) .135(2)
C(10)7 C .169(2) .3660(10) .102(2)
C(10)2 C .250(2) .3730(10) .093(2)
C(10)3 C .281(3) .348(2) .010(3)
C(10)4 C .237(4) .310(2) -.060(3)
C(10)5 C .157(3) .306(2) -.042(2)
C(10)6 C .123(2) .3280(10) .034(2)
C(10)1 C .129(2) .3900(10) .191(2)
HN4 H -.049(14) .504(13) .013(16)
HN10 H .058(13) .460(13) .118(17)
H2 H .033(13) .615(11) -.097(15)
H31 H -.087(14) .660(14) -.024(18)
H32 H -.053(12) .634(11) .075(16)
H5 H -.176(16) .481(18) .04(2)
H61 H -.179(13) .489(11) .208(15)
H62 H -.097(12) .560(12) .193(16)
H8 H -.021(14) .382(13) .261(18)
H91 H .068(12) .482(12) .316(17)
H92 H .021(13) .540(14) .257(19)
H11 H .188(14) .501(13) .110(17)
H121 H .071(14) .610(13) .136(17)
H122 H .156(13) .632(13) .099(16)
H211 H .119(15) .713(14) -.015(18)
H212 H .035(15) .724(12) .050(17)
H221 H .042(15) .810(15) -.087(16)
H222 H .032(17) .740(13) -.156(19)
H223 H -.038(18) .754(14) -.089(18)
H511 H -.222(16) .618(15) -.00(2)
H512 H -.183(12) .640(13) .104(16)
H521 H -.330(17) .615(17) .10(2)
H522 H -.31(2) .52(3) .06(3)
H523 H -.287(15) .554(15) .17(2)
H811 H -.136(16) .436(14) .388(18)
H812 H -.088(16) .521(18) .36(2)
H821 H -.080(17) .443(16) .49(2)
H282 H -.045(19) .372(17) .43(2)
H823 H .02(2) .46(2) .44(3)
H1111 H .186(14) .511(14) .296(18)
H1112 H .158(16) .590(16) .28(2)
H1121 H .306(15) .596(14) .29(2)
H1122 H .305(15) .530(17) .208(19)
H1123 H .283(18) .618(17) .18(2)
H12 H .155(16) .659(14) -.170(18)
H13 H .262(14) .741(15) -.187(19)
H14 H .378(18) .731(17) -.09(2)
H15 H .391(15) .618(15) .01(2)
H16 H .283(15) .532(16) .02(2)
H111 H .107(13) .532(13) -.115(18)
H112 H .156(15) .484(17) -.031(19)
H42 H .004(15) .430(15) -.13(2)
H43 H -.015(18) .296(18) -.16(2)
H44 H -.132(18) .24(2) -.17(2)
H45 H -.253(16) .310(17) -.14(2)
H46 H -.24(2) .443(19) -.10(3)
H411 H -.058(16) .544(16) -.15(2)
H412 H -.160(16) .563(16) -.12(2)
H72 H -.108(16) .280(13) .282(18)
H73 H -.223(17) .243(16) .39(2)
H74 H -.346(15) .271(14) .347(19)
H75 H -.372(16) .362(14) .203(18)
H76 H -.263(16) .399(16) .10(2)
H711 H -.062(14) .334(13) .129(17)
H712 H -.128(16) .379(16) .07(2)
H102 H .284(16) .396(15) .14(2)
H103 H .343(17) .363(16) -.00(2)
H104 H .258(14) .294(15) -.12(2)
H105 H .125(16) .279(16) -.09(2)
H106 H .061(15) .319(13) .052(17)
H1011 H .085(14) .351(14) .216(19)
H1012 H .168(16) .397(15) .25(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) 114.0(10) yes
N(1) C(2) C(3) 111.0(10) yes
C(2) C(3) N(4) 114(2) yes
C(3) N(4) C(5) 115(2) yes
N(4) C(5) C(6) 112(2) yes
C(5) C(6) N(7) 112(2) yes
C(6) N(7) C(8) 112(2) yes
N(7) C(8) C(9) 111(2) yes
C(8) C(9) N(10) 112(2) yes
C(9) N(10) C(11) 114(2) yes
N(10) C(11) C(12) 110(2) yes
C(11) C(12) N(1) 113(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) 1.48(2) yes
C(2) C(3) 1.50(3) yes
C(3) N(4) 1.51(2) yes
N(4) C(5) 1.50(3) yes
C(5) C(6) 1.50(3) yes
C(6) N(7) 1.50(3) yes
N(7) C(8) 1.44(3) yes
C(8) C(9) 1.50(3) yes
C(9) N(10) 1.50(3) yes
N(10) C(11) 1.51(3) yes
C(11) C(12) 1.53(3) yes
C(12) N(1) 1.46(3) yes
N(1) C(1)1 1.48(2) yes
C(2) C(2)1 1.60(2) yes
N(4) C(4)1 1.54(3) yes
C(5) C(5)1 1.54(3) yes
N(7) C(7)1 1.51(3) yes
C(8) C(8)1 1.53(4) yes
N(10) C(10)1 1.55(3) yes
C(11) C(11)1 1.52(3) 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) 165(2) yes
C(12) N(1) C(2) C(3) -84(2) yes
N(1) C(2) C(3) N(4) -57(2) yes
C(2) C(3) N(4) C(5) 162(2) yes
C(3) N(4) C(5) C(6) -77(2) yes
N(4) C(5) C(6) N(7) -55(2) yes
C(5) C(6) N(7) C(8) 166(2) yes
C(6) N(7) C(8) C(9) -87(2) yes
N(7) C(8) C(9) N(10) -56(2) yes
C(8) C(9) N(10) C(11) 163(2) yes
C(9) N(10) C(11) C(12) -78.0(10) yes
N(10) C(11) C(12) N(1) -58(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139057049
