#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/61/2016102.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_2016102
loop_
_publ_author_name
'Guzei, Ilia A.'
'Keter, Frankline K.'
'Spencer, Lara C.'
'Darkwa, James'
_publ_section_title
;
 Constructor graph description of hydrogen bonding in a supramolecular
 assembly of
 (3,5-dimethyl-1H-pyrazol-4-ylmethyl)isopropylammonium chloride
 monohydrate
;
_journal_coeditor_code           SF3043
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o481
_journal_page_last               o483
_journal_paper_doi               10.1107/S0108270107031952
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H18 N3 + , Cl - , H2 O'
_chemical_formula_moiety         'C9 H18 N3 + , Cl - , H2 O'
_chemical_formula_sum            'C9 H20 Cl N3 O'
_chemical_formula_weight         221.73
_chemical_name_systematic
;
(3,5-dimethyl-1H-pyrazol-4-ylmethyl)isopropylammonium chloride
monohydrate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7944(9)
_cell_length_b                   9.3494(7)
_cell_length_c                   10.0269(7)
_cell_measurement_reflns_used    5373
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.70
_cell_volume                     1199.42(15)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'SHELXTL and Mercury (Macrae et al., 2006)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD-1000 area-detector'
_diffrn_measurement_method       '0.30° ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9296
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.9298
_exptl_absorpt_correction_T_min  0.8688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.127
_refine_ls_abs_structure_details 'Flack (1983), with how many Friedel pairs?'
_refine_ls_abs_structure_Flack   -0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2446
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0230
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0356P)²+0.1541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0591
_reflns_number_gt                2305
_reflns_number_total             2446
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3043.cif
_cod_data_source_block           I
_cod_database_code               2016102
_cod_database_fobs_code          2016102
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cl Cl1 0.32941(2) 0.40622(3) 0.04588(3) 0.01824(10) Uani d 1
O O1 0.18064(9) 0.55564(14) 0.83667(13) 0.0267(3) Uani d 1
H H1W 0.2067(15) 0.533(2) 0.765(2) 0.028(5) Uiso d 1
H H2W 0.2218(18) 0.527(2) 0.890(3) 0.044(6) Uiso d 1
N N1 0.28910(10) 0.60977(14) 0.49639(13) 0.0182(3) Uani d 1
H H1 0.2529(14) 0.6870(19) 0.5031(16) 0.016(4) Uiso d 1
N N2 0.26978(10) 0.50390(13) 0.58606(12) 0.0191(3) Uani d 1
N N3 0.46303(9) 0.26535(13) 0.28239(12) 0.0146(2) Uani d 1
H H3A 0.4179(13) 0.2033(18) 0.3114(19) 0.017(4) Uiso d 1
H H3B 0.4280(15) 0.317(2) 0.218(2) 0.027(5) Uiso d 1
C C1 0.40797(14) 0.67902(17) 0.31000(16) 0.0245(3) Uani d 1
H H1A 0.3719(16) 0.774(2) 0.317(2) 0.041(5) Uiso d 1
H H1B 0.3904(15) 0.6443(19) 0.223(2) 0.028(5) Uiso d 1
H H1C 0.4844(16) 0.687(2) 0.315(2) 0.029(5) Uiso d 1
C C2 0.36886(11) 0.57901(15) 0.41389(15) 0.0178(3) Uani d 1
C C3 0.40342(11) 0.44410(15) 0.44989(15) 0.0181(3) Uani d 1
C C4 0.33915(10) 0.40197(14) 0.55701(19) 0.0178(3) Uani d 1
C C5 0.34046(14) 0.26431(17) 0.63350(18) 0.0236(3) Uani d 1
H H5A 0.3282(14) 0.281(2) 0.725(2) 0.029(5) Uiso d 1
H H5B 0.2889(15) 0.200(2) 0.597(2) 0.031(5) Uiso d 1
H H5C 0.4069(14) 0.2199(19) 0.6295(18) 0.022(4) Uiso d 1
C C6 0.49447(12) 0.36645(17) 0.39168(16) 0.0201(3) Uani d 1
H H6A 0.5437(14) 0.434(2) 0.3539(19) 0.025(5) Uiso d 1
H H6B 0.5318(13) 0.3099(18) 0.4550(18) 0.018(4) Uiso d 1
C C7 0.55434(11) 0.19055(16) 0.21634(14) 0.0174(3) Uani d 1
H H7 0.6009(14) 0.2645(19) 0.186(2) 0.027(5) Uiso d 1
C C8 0.51322(13) 0.10621(16) 0.09817(17) 0.0211(3) Uani d 1
H H8A 0.4770(14) 0.1669(19) 0.040(2) 0.027(4) Uiso d 1
H H8B 0.5722(13) 0.0670(18) 0.054(2) 0.022(4) Uiso d 1
H H8C 0.4665(15) 0.032(2) 0.131(2) 0.034(5) Uiso d 1
C C9 0.61188(14) 0.09658(19) 0.31428(18) 0.0275(4) Uani d 1
H H9A 0.6458(16) 0.154(2) 0.388(2) 0.032(5) Uiso d 1
H H9B 0.5659(17) 0.022(2) 0.345(2) 0.044(6) Uiso d 1
H H9C 0.6661(14) 0.051(2) 0.275(2) 0.028(5) Uiso d 1
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'
O O 0.0106 0.0060 '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
H1W O1 H2W 103(2)
C2 N1 N2 112.89(13)
C2 N1 H1 129.5(11)
N2 N1 H1 117.5(11)
C4 N2 N1 104.75(12)
C6 N3 C7 113.77(11)
C6 N3 H3A 110.7(12)
C7 N3 H3A 110.6(11)
C6 N3 H3B 108.3(11)
C7 N3 H3B 108.1(12)
H3A N3 H3B 104.9(16)
C2 C1 H1A 110.4(13)
C2 C1 H1B 110.2(11)
H1A C1 H1B 105.1(18)
C2 C1 H1C 110.1(11)
H1A C1 H1C 112.9(16)
H1B C1 H1C 108.0(16)
N1 C2 C3 106.07(13)
N1 C2 C1 123.50(13)
C3 C2 C1 130.41(14)
C2 C3 C4 105.49(12)
C2 C3 C6 126.21(14)
C4 C3 C6 128.18(14)
N2 C4 C3 110.79(13)
N2 C4 C5 120.60(15)
C3 C4 C5 128.60(13)
C4 C5 H5A 110.7(12)
C4 C5 H5B 109.6(11)
H5A C5 H5B 111.0(17)
C4 C5 H5C 111.4(11)
H5A C5 H5C 105.3(16)
H5B C5 H5C 108.7(15)
C3 C6 N3 112.50(12)
C3 C6 H6A 109.9(11)
N3 C6 H6A 107.5(11)
C3 C6 H6B 113.6(10)
N3 C6 H6B 105.7(10)
H6A C6 H6B 107.3(15)
C9 C7 N3 111.14(12)
C9 C7 C8 112.00(13)
N3 C7 C8 108.30(12)
C9 C7 H7 108.7(11)
N3 C7 H7 106.5(10)
C8 C7 H7 110.1(12)
C7 C8 H8A 110.0(11)
C7 C8 H8B 106.7(11)
H8A C8 H8B 110.0(16)
C7 C8 H8C 108.9(12)
H8A C8 H8C 109.7(15)
H8B C8 H8C 111.5(15)
C7 C9 H9A 112.0(12)
C7 C9 H9B 109.2(13)
H9A C9 H9B 114.6(18)
C7 C9 H9C 111.5(12)
H9A C9 H9C 103.9(17)
H9B C9 H9C 105.4(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 H1W 0.82(2)
O1 H2W 0.80(3)
N1 C2 1.345(2)
N1 N2 1.3599(18)
N1 H1 0.860(18)
N2 C4 1.3346(19)
N3 C6 1.5020(18)
N3 C7 1.5141(17)
N3 H3A 0.868(18)
N3 H3B 0.92(2)
C1 C2 1.487(2)
C1 H1A 1.00(2)
C1 H1B 0.96(2)
C1 H1C 0.98(2)
C2 C3 1.384(2)
C3 C4 1.409(2)
C3 C6 1.492(2)
C4 C5 1.498(2)
C5 H5A 0.94(2)
C5 H5B 0.97(2)
C5 H5C 0.948(17)
C6 H6A 0.972(19)
C6 H6B 0.954(18)
C7 C9 1.509(2)
C7 C8 1.517(2)
C7 H7 0.961(19)
C8 H8A 0.94(2)
C8 H8B 0.946(19)
C8 H8C 0.97(2)
C9 H9A 1.01(2)
C9 H9B 0.96(2)
C9 H9C 0.90(2)
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
C2 N1 N2 C4 -1.01(16)
N2 N1 C2 C3 0.84(16)
N2 N1 C2 C1 -177.81(13)
N1 C2 C3 C4 -0.32(15)
C1 C2 C3 C4 178.20(15)
N1 C2 C3 C6 -176.63(14)
C1 C2 C3 C6 1.9(2)
N1 N2 C4 C3 0.77(16)
N1 N2 C4 C5 -178.46(14)
C2 C3 C4 N2 -0.29(17)
C6 C3 C4 N2 175.92(14)
C2 C3 C4 C5 178.86(15)
C6 C3 C4 C5 -4.9(3)
C2 C3 C6 N3 -95.51(17)
C4 C3 C6 N3 89.01(19)
C7 N3 C6 C3 176.99(13)
C6 N3 C7 C9 63.24(17)
C6 N3 C7 C8 -173.33(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133130
