#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:19:57 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263854 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157946.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_7157946
loop_
_publ_author_name
'Goodwin, Rosemary J.'
'Blyth, Mitchell T.'
'Fung, Alfred K. K.'
'Smith, Leesa M.'
'Norcott, Philip L.'
'Tanovic, Sara'
'Coote, Michelle L.'
'White, Nicholas G.'
_publ_section_title
;
 Simple acyclic molecules containing a single charge-assisted O-H group
 can recognize anions in acetonitrile : water mixtures.
;
_journal_issue                   12
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2794
_journal_page_last               2803
_journal_paper_doi               10.1039/d1ob00282a
_journal_volume                  19
_journal_year                    2021
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C17 H14 N O, C2 H3 N, Br'
_chemical_formula_sum            'C19 H17 Br N2 O'
_chemical_formula_weight         369.26
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.141(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8904(2)
_cell_length_b                   7.3341(2)
_cell_length_c                   22.6009(7)
_cell_measurement_reflns_used    15860
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.7
_cell_measurement_theta_min      3.76
_cell_volume                     1626.69(8)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31725
_diffrn_reflns_theta_full        26.361
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_min         3.319
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             751.997
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9504
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0219
_refine_ls_shift/su_max          0.0036282
_refine_ls_shift/su_mean         0.0000626
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 790. 0.118E+04 690. 290. 29.6 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0438
_refine_ls_wR_factor_gt          0.0428
_refine_ls_wR_factor_ref         0.0438
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                3098
_reflns_number_total             3332
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   1.93
_oxford_diffrn_Wilson_scale      0.07
_oxford_refine_ls_r_factor_ref   0.0247
_oxford_refine_ls_scale          4.38(3)
_oxford_reflns_number_all        3321
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            d1ob00282a2.cif
_cod_data_source_block           4Br
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157935--7157948.cif.
;
_cod_original_cell_volume        1626.69(5)
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_original_formula_sum        'C19 H17 Br1 N2 O1'
_cod_database_code               7157946
_iucr_refine_instructions_details_constraints
;
#
# Punched on 10/10/16 at 10:14:53
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   ( 103,X'S) H   (1031,X'S) H   (1032,X'S) H   (1033,X'S) 
END
;
_iucr_refine_instructions_details_restraints
;                                                                         
#
# Punched on 10/10/16 at 10:14:53
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.73536(13) 0.26057(18) 0.57365(5) 0.0176 1.0000 Uani . . . . . .
C2 C 0.84019(16) 0.3041(2) 0.54459(7) 0.0236 1.0000 Uani . . . . . .
C3 C 0.82301(18) 0.3412(3) 0.48371(7) 0.0275 1.0000 Uani . . . . . .
C4 C 0.69531(18) 0.3386(2) 0.45336(7) 0.0258 1.0000 Uani . . . . . .
C5 C 0.58319(17) 0.2889(2) 0.48252(7) 0.0207 1.0000 Uani . . . . . .
C6 C 0.60424(15) 0.2446(2) 0.54404(7) 0.0173 1.0000 Uani . . . . . .
C7 C 0.44991(18) 0.2809(2) 0.45144(7) 0.0256 1.0000 Uani . . . . . .
C8 C 0.34285(18) 0.2322(2) 0.47993(8) 0.0284 1.0000 Uani . . . . . .
C9 C 0.36382(17) 0.1847(2) 0.54057(8) 0.0251 1.0000 Uani . . . . . .
C10 C 0.49158(16) 0.1860(2) 0.57233(7) 0.0192 1.0000 Uani . . . . . .
O11 O 0.51135(11) 0.11305(15) 0.62864(5) 0.0206 1.0000 Uani . . . . . .
C12 C 0.47857(16) 0.2320(2) 0.67578(7) 0.0219 1.0000 Uani . . . . . .
C13 C 0.56285(15) 0.4031(2) 0.68168(6) 0.0170 1.0000 Uani . . . . . .
C14 C 0.50632(16) 0.5569(2) 0.70538(7) 0.0206 1.0000 Uani . . . . . .
C15 C 0.58061(17) 0.7171(2) 0.71519(7) 0.0227 1.0000 Uani . . . . . .
C16 C 0.71236(16) 0.7261(2) 0.70001(7) 0.0213 1.0000 Uani . . . . . .
C17 C 0.76895(15) 0.5746(2) 0.67572(6) 0.0190 1.0000 Uani . . . . . .
C18 C 0.69594(14) 0.4129(2) 0.66694(6) 0.0160 1.0000 Uani . . . . . .
C19 C 0.76420(15) 0.2530(2) 0.64058(6) 0.0179 1.0000 Uani . . . . . .
N101 N -0.03624(19) -0.0793(3) 0.60166(10) 0.0518 1.0000 Uani . . . . . .
C102 C 0.06261(19) -0.0807(3) 0.63284(9) 0.0326 1.0000 Uani . . . . . .
C103 C 0.18950(18) -0.0824(3) 0.67283(8) 0.0319 1.0000 Uani . . . . . .
Br1 Br 0.126901(15) 0.42285(2) 0.660257(8) 0.0253 1.0000 Uani . . . . . .
H21 H 0.9259 0.3136 0.5681 0.0287 1.0000 Uiso R . . . . .
H31 H 0.9023 0.3707 0.4645 0.0335 1.0000 Uiso R . . . . .
H41 H 0.6802 0.3694 0.4115 0.0308 1.0000 Uiso R . . . . .
H71 H 0.4396 0.3088 0.4127 0.0309 1.0000 Uiso R . . . . .
H81 H 0.2554 0.2248 0.4595 0.0352 1.0000 Uiso R . . . . .
H91 H 0.2920 0.1471 0.5616 0.0314 1.0000 Uiso R . . . . .
H121 H 0.4927 0.1589 0.7116 0.0268 1.0000 Uiso R . . . . .
H122 H 0.3777 0.2648 0.6701 0.0275 1.0000 Uiso R . . . . .
H141 H 0.4091 0.5522 0.7134 0.0245 1.0000 Uiso R . . . . .
H151 H 0.5384 0.8185 0.7318 0.0280 1.0000 Uiso R . . . . .
H161 H 0.7647 0.8370 0.7053 0.0261 1.0000 Uiso R . . . . .
H171 H 0.8607 0.5805 0.6656 0.0234 1.0000 Uiso R . . . . .
H191 H 0.8613 0.2620 0.6495 0.0238 1.0000 Uiso R . . . . .
H192 H 0.7325 0.1345 0.6541 0.0222 1.0000 Uiso R . . . . .
H1031 H 0.2021 0.0292 0.6931 0.0503 1.0000 Uiso R . . . . .
H1032 H 0.1978 -0.1828 0.7013 0.0520 1.0000 Uiso R . . . . .
H1033 H 0.2692 -0.0974 0.6491 0.0498 1.0000 Uiso R . . . . .
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
C 0.0033 0.0016 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'
N 0.0061 0.0033 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'
O 0.0106 0.0060 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'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 '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_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C6 . 121.33(13) yes
C2 . N1 . C19 . 116.24(13) yes
C6 . N1 . C19 . 122.02(12) yes
N1 . C2 . C3 . 121.79(15) yes
N1 . C2 . H21 . 116.0 no
C3 . C2 . H21 . 122.2 no
C2 . C3 . C4 . 119.16(16) yes
C2 . C3 . H31 . 118.8 no
C4 . C3 . H31 . 122.0 no
C3 . C4 . C5 . 120.26(15) yes
C3 . C4 . H41 . 120.8 no
C5 . C4 . H41 . 119.0 no
C4 . C5 . C6 . 119.38(15) yes
C4 . C5 . C7 . 121.19(15) yes
C6 . C5 . C7 . 119.42(15) yes
C5 . C6 . N1 . 117.89(14) yes
C5 . C6 . C10 . 118.92(14) yes
N1 . C6 . C10 . 123.19(14) yes
C5 . C7 . C8 . 120.67(15) yes
C5 . C7 . H71 . 117.6 no
C8 . C7 . H71 . 121.8 no
C7 . C8 . C9 . 120.01(15) yes
C7 . C8 . H81 . 120.9 no
C9 . C8 . H81 . 119.1 no
C8 . C9 . C10 . 121.54(16) yes
C8 . C9 . H91 . 122.3 no
C10 . C9 . H91 . 116.1 no
C6 . C10 . C9 . 119.32(15) yes
C6 . C10 . O11 . 120.45(13) yes
C9 . C10 . O11 . 119.87(15) yes
C10 . O11 . C12 . 115.42(12) yes
O11 . C12 . C13 . 113.37(12) yes
O11 . C12 . H121 . 105.1 no
C13 . C12 . H121 . 111.6 no
O11 . C12 . H122 . 110.9 no
C13 . C12 . H122 . 109.8 no
H121 . C12 . H122 . 105.9 no
C12 . C13 . C14 . 117.69(13) yes
C12 . C13 . C18 . 123.35(14) yes
C14 . C13 . C18 . 118.90(15) yes
C13 . C14 . C15 . 121.07(14) yes
C13 . C14 . H141 . 118.8 no
C15 . C14 . H141 . 120.1 no
C14 . C15 . C16 . 119.64(15) yes
C14 . C15 . H151 . 118.3 no
C16 . C15 . H151 . 122.0 no
C15 . C16 . C17 . 119.77(15) yes
C15 . C16 . H161 . 121.0 no
C17 . C16 . H161 . 119.2 no
C16 . C17 . C18 . 120.78(14) yes
C16 . C17 . H171 . 119.8 no
C18 . C17 . H171 . 119.4 no
C13 . C18 . C17 . 119.82(14) yes
C13 . C18 . C19 . 122.22(14) yes
C17 . C18 . C19 . 117.95(13) yes
C18 . C19 . N1 . 109.23(12) yes
C18 . C19 . H191 . 110.4 no
N1 . C19 . H191 . 105.6 no
C18 . C19 . H192 . 112.8 no
N1 . C19 . H192 . 108.4 no
H191 . C19 . H192 . 110.2 no
N101 . C102 . C103 . 179.9(2) yes
C102 . C103 . H1031 . 110.4 no
C102 . C103 . H1032 . 114.4 no
H1031 . C103 . H1032 . 110.0 no
C102 . C103 . H1033 . 109.9 no
H1031 . C103 . H1033 . 106.7 no
H1032 . C103 . H1033 . 105.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.333(2) yes
N1 . C6 . 1.3883(19) yes
N1 . C19 . 1.5053(18) yes
C2 . C3 . 1.392(2) yes
C2 . H21 . 0.945 no
C3 . C4 . 1.360(2) yes
C3 . H31 . 0.967 no
C4 . C5 . 1.407(2) yes
C4 . H41 . 0.965 no
C5 . C6 . 1.418(2) yes
C5 . C7 . 1.416(2) yes
C6 . C10 . 1.418(2) yes
C7 . C8 . 1.354(3) yes
C7 . H71 . 0.892 no
C8 . C9 . 1.404(2) yes
C8 . H81 . 0.930 no
C9 . C10 . 1.374(2) yes
C9 . H91 . 0.943 no
C10 . O11 . 1.3719(18) yes
O11 . C12 . 1.4448(19) yes
C12 . C13 . 1.503(2) yes
C12 . H121 . 0.966 no
C12 . H122 . 1.018 no
C13 . C14 . 1.396(2) yes
C13 . C18 . 1.399(2) yes
C14 . C15 . 1.389(2) yes
C14 . H141 . 1.001 no
C15 . C16 . 1.390(2) yes
C15 . H151 . 0.953 no
C16 . C17 . 1.387(2) yes
C16 . H161 . 0.964 no
C17 . C18 . 1.390(2) yes
C17 . H171 . 0.965 no
C18 . C19 . 1.512(2) yes
C19 . H191 . 0.959 no
C19 . H192 . 0.985 no
N101 . C102 . 1.132(3) yes
C102 . C103 . 1.453(3) yes
C103 . H1031 . 0.938 no
C103 . H1032 . 0.975 no
C103 . H1033 . 1.013 no
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-1 2 2 x .
0 0 6 x .
