#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:12:14 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228818 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/90/1549059.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_1549059
loop_
_publ_author_name
'Nievergelt, Philipp P.'
'Babor, Martin'
'Čejka, Jan'
'Spingler, Bernhard'
_publ_section_title
;
 A high throughput screening method for the nano-crystallization of salts
 of organic cations.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              3716
_journal_page_last               3722
_journal_paper_doi               10.1039/c8sc00783g
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H4 O12 Sb2, 2(C17 H19 N2 O), 2(H2 O)'
_chemical_formula_sum            'C42 H46 N4 O16 Sb2'
_chemical_formula_weight         1106.34
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2017-11-15 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 130.585(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   22.3684(7)
_cell_length_b                   8.41560(10)
_cell_length_c                   15.6852(4)
_cell_measurement_reflns_used    19256
_cell_measurement_temperature    160
_cell_measurement_theta_max      79
_cell_measurement_theta_min      4
_cell_volume                     2242.36(19)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      160
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22761
_diffrn_reflns_theta_full        77.394
_diffrn_reflns_theta_max         78.973
_diffrn_reflns_theta_min         3.711
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.200
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1111.995
_exptl_crystal_recrystallization_method 'Vapour diffusion'
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.011
_refine_diff_density_max         2.37
_refine_diff_density_min         -0.68
_refine_ls_abs_structure_details 'Flack (1983), 2095 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.010(9)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9417
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4676
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.0003471
_refine_ls_shift/su_mean         0.0000159
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.11P)² + 5.88P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1194
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1194
_reflns_limit_h_max              21
_reflns_limit_h_min              -28
_reflns_limit_k_max              10
_reflns_limit_k_min              -9
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                4563
_reflns_number_total             4676
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.20
_oxford_diffrn_Wilson_scale      0.30
_oxford_refine_ls_r_factor_ref   0.0458
_oxford_refine_ls_scale          1.799(14)
_oxford_reflns_number_all        4676
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c8sc00783g2.cif
_cod_data_source_block           I_CCDC9
_cod_depositor_comments
'Adding full bibliography for 1549042--1549063.cif.'
_cod_original_cell_volume        2242.35(19)
_cod_original_sg_symbol_H-M      'C 1 2 1 '
_cod_database_code               1549059
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y+1/2,z
-x,y,-z
-x+1/2,y+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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
N1 N 0.5148(3) 0.2301(5) 0.3765(4) 0.0317 1.0000 Uani D
C2 C 0.4675(3) 0.2349(7) 0.2525(5) 0.0334 1.0000 Uani .
C3 C 0.5186(3) 0.2011(7) 0.2223(4) 0.0336 1.0000 Uani .
C4 C 0.5883(3) 0.3081(7) 0.2785(5) 0.0327 1.0000 Uani .
C5 C 0.6644(3) 0.2682(7) 0.3625(5) 0.0359 1.0000 Uani .
N6 N 0.7118(3) 0.3978(6) 0.3941(4) 0.0365 1.0000 Uani .
C7 C 0.6666(3) 0.5251(7) 0.3301(5) 0.0315 1.0000 Uani .
C8 C 0.5870(3) 0.4730(6) 0.2542(4) 0.0300 1.0000 Uani .
C9 C 0.6870(3) 0.6805(11) 0.3311(4) 0.0356 1.0000 Uani .
C10 C 0.6276(4) 0.7872(7) 0.2570(6) 0.0382 1.0000 Uani .
C11 C 0.5481(4) 0.7367(8) 0.1789(6) 0.0358 1.0000 Uani .
C12 C 0.5269(3) 0.5813(7) 0.1763(5) 0.0292 1.0000 Uani .
O13 O 0.4967(3) 0.8560(5) 0.1112(4) 0.0434 1.0000 Uani .
C14 C 0.4155(4) 0.8214(8) 0.0235(6) 0.0429 1.0000 Uani .
C15 C 0.3724(3) 0.9775(8) -0.0211(5) 0.0380 1.0000 Uani .
C16 C 0.3235(4) 1.0256(8) 0.0011(6) 0.0449 1.0000 Uani .
C17 C 0.2900(3) 1.1760(16) -0.0306(5) 0.0550 1.0000 Uani .
C18 C 0.3002(4) 1.2769(10) -0.0889(7) 0.0563 1.0000 Uani .
C19 C 0.3479(5) 1.2293(9) -0.1129(6) 0.0490 1.0000 Uani .
C20 C 0.3838(4) 1.0813(8) -0.0784(5) 0.0420 1.0000 Uani .
Sb21 Sb 0.420014(14) 0.67703(12) 0.289087(19) 0.0285 1.0000 Uani D
O22 O 0.4970(2) 0.8780(4) 0.3503(3) 0.0322 1.0000 Uani .
O23 O 0.5233(2) 0.5787(4) 0.4089(3) 0.0275 1.0000 Uani .
C24 C 0.5913(2) 0.6745(9) 0.4639(4) 0.0280 1.0000 Uani .
C25 C 0.5702(3) 0.8473(7) 0.4233(5) 0.0304 1.0000 Uani .
O26 O 0.6219(2) 0.9485(5) 0.4632(4) 0.0350 1.0000 Uani .
O27 O 0.3796(2) 0.4731(5) 0.3170(3) 0.0347 1.0000 Uani D
O28 O 0.3950(2) 0.7706(4) 0.3784(3) 0.0309 1.0000 Uani .
C29 C 0.6391(2) 0.6691(10) 0.5916(4) 0.0285 1.0000 Uani .
C30 C 0.3570(3) 0.4970(6) 0.3740(5) 0.0319 1.0000 Uani .
O31 O 0.3338(3) 0.3908(5) 0.4000(4) 0.0420 1.0000 Uani .
O32 O 0.3956(4) 0.1161(6) 0.3704(6) 0.0724 1.0000 Uani D
H241 H 0.6242 0.6327 0.4478 0.0340 1.0000 Uiso R
H91 H 0.7394 0.7134 0.3810 0.0430 1.0000 Uiso R
H32 H 0.5388 0.0941 0.2457 0.0398 1.0000 Uiso R
H31 H 0.4859 0.2109 0.1408 0.0399 1.0000 Uiso R
H101 H 0.6399 0.8936 0.2597 0.0462 1.0000 Uiso R
H291 H 0.6930 0.7055 0.6292 0.0339 1.0000 Uiso R
H161 H 0.3130 0.9558 0.0367 0.0537 1.0000 Uiso R
H141 H 0.4079 0.7634 -0.0365 0.0511 1.0000 Uiso R
H142 H 0.3958 0.7580 0.0532 0.0511 1.0000 Uiso R
H191 H 0.3552 1.2984 -0.1525 0.0588 1.0000 Uiso R
H171 H 0.2593 1.2085 -0.0128 0.0660 1.0000 Uiso R
H51 H 0.6820 0.1680 0.3950 0.0425 1.0000 Uiso R
H201 H 0.4157 1.0500 -0.0943 0.0501 1.0000 Uiso R
H22 H 0.4425 0.3382 0.2234 0.0400 1.0000 Uiso R
H21 H 0.4274 0.1540 0.2200 0.0399 1.0000 Uiso R
H121 H 0.4741 0.5500 0.1250 0.0346 1.0000 Uiso R
H181 H 0.2760 1.3765 -0.1112 0.0678 1.0000 Uiso R
H61 H 0.7621 0.3993 0.4478 0.0440 1.0000 Uiso R
H13 H 0.4842 0.2087 0.3921 0.0482 1.0000 Uiso R
H12 H 0.5381 0.3227 0.4061 0.0481 1.0000 Uiso R
H11 H 0.5514 0.1566 0.4070 0.0477 1.0000 Uiso R
H321 H 0.3988 0.1688 0.4170 0.1091 1.0000 Uiso DR
H322 H 0.3961 0.0190 0.3726 0.1091 1.0000 Uiso DR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
Sb -0.0562 5.8946 19.6418 5.3034 19.0455 0.4607 5.0371 27.9074 2.6827 75.2825
4.5909 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 H13 . 110.3 no
C2 . N1 H12 . 109.7 no
H13 . N1 H12 . 109.4 no
C2 . N1 H11 . 110.3 no
H13 . N1 H11 . 108.9 no
H12 . N1 H11 . 108.2 no
N1 . C2 C3 . 111.2(5) yes
N1 . C2 H22 . 109.9 no
C3 . C2 H22 . 109.9 no
N1 . C2 H21 . 107.2 no
C3 . C2 H21 . 109.4 no
H22 . C2 H21 . 109.2 no
C2 . C3 C4 . 114.2(5) yes
C2 . C3 H32 . 108.4 no
C4 . C3 H32 . 106.7 no
C2 . C3 H31 . 108.5 no
C4 . C3 H31 . 109.0 no
H32 . C3 H31 . 110.0 no
C3 . C4 C5 . 126.5(5) yes
C3 . C4 C8 . 126.4(5) yes
C5 . C4 C8 . 107.1(5) yes
C4 . C5 N6 . 110.1(5) yes
C4 . C5 H51 . 125.2 no
N6 . C5 H51 . 124.8 no
C5 . N6 C7 . 109.3(5) yes
C5 . N6 H61 . 125.2 no
C7 . N6 H61 . 125.5 no
N6 . C7 C8 . 107.4(5) yes
N6 . C7 C9 . 130.9(5) yes
C8 . C7 C9 . 121.7(5) yes
C4 . C8 C7 . 106.2(5) yes
C4 . C8 C12 . 134.2(5) yes
C7 . C8 C12 . 119.6(5) yes
C7 . C9 C10 . 118.4(5) yes
C7 . C9 H91 . 121.1 no
C10 . C9 H91 . 120.6 no
C9 . C10 C11 . 120.7(6) yes
C9 . C10 H101 . 119.6 no
C11 . C10 H101 . 119.7 no
C10 . C11 C12 . 121.5(6) yes
C10 . C11 O13 . 113.5(5) yes
C12 . C11 O13 . 125.0(6) yes
C8 . C12 C11 . 118.0(5) yes
C8 . C12 H121 . 121.4 no
C11 . C12 H121 . 120.5 no
C11 . O13 C14 . 120.0(5) yes
O13 . C14 C15 . 107.4(5) yes
O13 . C14 H141 . 110.4 no
C15 . C14 H141 . 109.4 no
O13 . C14 H142 . 109.8 no
C15 . C14 H142 . 110.2 no
H141 . C14 H142 . 109.6 no
C14 . C15 C16 . 120.1(6) yes
C14 . C15 C20 . 121.2(6) yes
C16 . C15 C20 . 118.6(6) yes
C15 . C16 C17 . 120.0(7) yes
C15 . C16 H161 . 120.2 no
C17 . C16 H161 . 119.8 no
C16 . C17 C18 . 121.2(7) yes
C16 . C17 H171 . 119.4 no
C18 . C17 H171 . 119.4 no
C17 . C18 C19 . 119.2(8) yes
C17 . C18 H181 . 120.0 no
C19 . C18 H181 . 120.8 no
C18 . C19 C20 . 120.0(7) yes
C18 . C19 H191 . 119.4 no
C20 . C19 H191 . 120.6 no
C15 . C20 C19 . 120.9(6) yes
C15 . C20 H201 . 119.3 no
C19 . C20 H201 . 119.8 no
O22 . Sb21 O23 . 78.66(14) yes
O22 . Sb21 O27 . 151.02(15) yes
O23 . Sb21 O27 . 81.71(15) yes
O22 . Sb21 O28 . 83.32(15) yes
O23 . Sb21 O28 . 100.78(15) yes
O27 . Sb21 O28 . 79.65(15) yes
Sb21 . O22 C25 . 115.5(3) yes
Sb21 . O23 C24 . 118.0(3) yes
O23 . C24 C25 . 111.6(4) yes
O23 . C24 C29 . 109.7(4) yes
C25 . C24 C29 . 109.5(5) yes
O23 . C24 H241 . 109.1 no
C25 . C24 H241 . 108.2 no
C29 . C24 H241 . 108.7 no
C24 . C25 O22 . 115.8(4) yes
C24 . C25 O26 . 120.7(5) yes
O22 . C25 O26 . 123.4(5) yes
Sb21 . O27 C30 . 115.3(3) yes
C29 3_656 O28 Sb21 . 117.2(4) yes
C24 . C29 C30 3_656 108.6(6) yes
C24 . C29 O28 3_656 110.3(4) yes
C30 3_656 C29 O28 3_656 112.0(4) yes
C24 . C29 H291 . 108.2 no
C30 3_656 C29 H291 . 108.5 no
O28 3_656 C29 H291 . 109.2 no
C29 3_656 C30 O27 . 115.6(4) yes
C29 3_656 C30 O31 . 120.7(5) yes
O27 . C30 O31 . 123.7(5) yes
H321 . O32 H322 . 120.8 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.492(7) yes
N1 H13 . 0.882 no
N1 H12 . 0.884 no
N1 H11 . 0.879 no
C2 C3 . 1.521(7) yes
C2 H22 . 0.972 no
C2 H21 . 0.967 no
C3 C4 . 1.493(8) yes
C3 H32 . 0.967 no
C3 H31 . 0.979 no
C4 C5 . 1.352(8) yes
C4 C8 . 1.434(8) yes
C5 N6 . 1.371(7) yes
C5 H51 . 0.930 no
N6 C7 . 1.363(8) yes
N6 H61 . 0.861 no
C7 C8 . 1.423(7) yes
C7 C9 . 1.382(11) yes
C8 C12 . 1.412(8) yes
C9 C10 . 1.383(10) yes
C9 H91 . 0.931 no
C10 C11 . 1.418(10) yes
C10 H101 . 0.929 no
C11 C12 . 1.382(8) yes
C11 O13 . 1.367(8) yes
C12 H121 . 0.935 no
O13 C14 . 1.423(8) yes
C14 C15 . 1.506(9) yes
C14 H141 . 0.973 no
C14 H142 . 0.981 no
C15 C16 . 1.406(9) yes
C15 C20 . 1.390(9) yes
C16 C17 . 1.387(14) yes
C16 H161 . 0.940 no
C17 C18 . 1.371(14) yes
C17 H171 . 0.934 no
C18 C19 . 1.402(11) yes
C18 H181 . 0.933 no
C19 C20 . 1.387(10) yes
C19 H191 . 0.939 no
C20 H201 . 0.934 no
Sb21 O22 . 2.144(4) yes
Sb21 O23 . 1.976(3) yes
Sb21 O27 . 2.115(4) yes
Sb21 O28 . 1.979(4) yes
O22 C25 . 1.272(7) yes
O23 C24 . 1.415(6) yes
C24 C25 . 1.534(9) yes
C24 C29 . 1.540(6) yes
C24 H241 . 0.985 no
C25 O26 . 1.231(7) yes
O27 C30 . 1.296(7) yes
O28 C29 3_656 1.414(7) yes
C29 C30 3_656 1.529(10) yes
C29 H291 . 0.985 no
C30 O31 . 1.229(7) yes
O32 H321 . 0.817 no
O32 H322 . 0.818 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 H91 O31 2_555 143 0.93 2.44 3.234(10) yes
N6 H61 O26 4_646 161 0.86 2.03 2.862(10) yes
N1 H13 O32 . 157 0.88 1.94 2.776(10) yes
N1 H12 O23 . 147 0.88 2.18 2.963(10) yes
N1 H12 O31 3_656 130 0.88 2.54 3.184(10) yes
N1 H11 O26 1_545 169 0.88 2.13 2.994(10) yes
O32 H321 N1 3_656 144 0.82 2.52 3.216(10) yes
O32 H321 O31 . 132 0.82 2.27 2.881(10) yes
O32 H322 O28 1_545 179 0.82 2.09 2.911(10) yes
