The synthesis and characterisation of coordination and hydrogen-bonded networks based on 4-(3,5-dimethyl-1H-pyrazol-4-yl)benzoic acid.
Bryant, Macguire R.; Burrows, Andrew D.; Fitchett, Christopher M.; Hawes, Chris S.; Hunter, Sally O.; Keenan, Luke L.; Kelly, David J.; Kruger, Paul E.; Mahon, Mary F.; Richardson, Christopher; Dalton transactions (Cambridge, England : 2003) 44 (2015) 9269–9280; doi:10.1039/c5dt00011d

data_7035103
_publ_section_title
;
 The synthesis and characterisation of coordination and hydrogen-bonded
 networks based on 4-(3,5-dimethyl-1H-pyrazol-4-yl)benzoic acid.
;
_journal_issue                   19
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9269
_journal_page_last               9280
_journal_paper_doi               10.1039/c5dt00011d
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C12 H12 N2 O2'
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24
_chemical_name_systematic        '4-(3,5-dimethyl-1H-pyrazol-4-yl)benzoic acid'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-03-12 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                91.284(4)
_cell_angle_beta                 101.971(4)
_cell_angle_gamma                102.808(4)
_cell_formula_units_Z            8
_cell_length_a                   9.6538(5)
_cell_length_b                   10.4193(6)
_cell_length_c                   21.9388(14)
_cell_measurement_reflns_used    2540
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      2.63
_cell_volume                     2099.6(2)
_computing_data_reduction        'SAINT v7.53A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XLMP (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.1106
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27642
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.15
_diffrn_reflns_theta_min         0.95
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0680 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.8540.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     609
_refine_ls_number_reflns         10151
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0540
_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/[\s^2^(Fo^2^)+(0.0460P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                5096
_reflns_number_total             10151
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt00011d2.cif
_cod_data_source_block           csh75
_cod_depositor_comments
'Adding full bibliography for 7035103--7035111.cif.'
_cod_database_code               7035103
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.045) H1(0.035) H2A(0.028) H3(0.028) H5(0.025) H6(0.025)
 H31D(0.043) H31E(0.043) H31F(0.043) H51D(0.045) H51E(0.045) H51F(0.045)
 H2B(0.05) H1B(0.034) H2BA(0.028) H3B(0.027) H5B(0.026) H6B(0.028) H31A(0.042)
 H31B(0.042) H31C(0.042) H51A(0.047) H51B(0.047) H51C(0.047) H2AA(0.045)
 H1A(0.034) H2AB(0.029) H3A(0.028) H5A(0.031) H6A(0.032) H31J(0.046)
 H31K(0.046) H31L(0.046) H51J(0.047) H51K(0.047) H51L(0.047) H2C(0.051)
 H1C(0.031) H2CA(0.028) H3C(0.028) H5C(0.026) H6C(0.026) H31G(0.039)
 H31H(0.039) H31I(0.039) H51G(0.04) H51H(0.04) H51I(0.04)
 Fixed X: H2A(0.0546) H3(-0.041) H5(0.096) H6(0.1973) H31D(0.1721)
 H31E(0.2271) H31F(0.1396) H51D(-0.3881) H51E(-0.3002) H51F(-0.268) H2BA(0.455)
 H3B(0.4774) H5B(0.4581) H6B(0.4443) H31A(0.5632) H31B(0.7032) H31C(0.6881)
 H51A(0.4277) H51B(0.3123) H51C(0.2854) H2AB(0.4406) H3A(0.345) H5A(0.7532)
 H6A(0.8474) H31J(0.7687) H31K(0.6932) H31L(0.6783) H51J(0.1823) H51K(0.2825)
 H51L(0.1751) H2CA(0.7623) H3C(0.7599) H5C(1.1514) H6C(1.1509) H31G(1.2032)
 H31H(1.051) H31I(1.1037) H51G(0.7323) H51H(0.8857) H51I(0.8172)
 Fixed Y: H2A(0.0421) H3(0.0403) H5(0.4381) H6(0.439) H31D(0.4284)
 H31E(0.3836) H31F(0.498) H51D(0.0504) H51E(0.0784) H51F(-0.03) H2BA(0.933)
 H3B(0.9282) H5B(0.536) H6B(0.5428) H31A(0.4606) H31B(0.531) H31C(0.572)
 H51A(0.9999) H51B(0.9248) H51C(0.8946) H2AB(0.1934) H3A(0.207) H5A(0.3327)
 H6A(0.3272) H31J(0.4191) H31K(0.51) H31L(0.5144) H51J(0.1167) H51K(0.0138)
 H51L(0.0376) H2CA(0.7944) H3C(0.7939) H5C(0.6967) H6C(0.6944) H31G(0.6134)
 H31H(0.5182) H31I(0.5251) H51G(0.9134) H51H(1.0138) H51I(0.9986)
 Fixed Z: H2A(0.2953) H3(0.1889) H5(0.1974) H6(0.3031) H31D(0.0347)
 H31E(0.1031) H31F(0.0943) H51D(0.0726) H51E(0.1437) H51F(0.0992) H2BA(0.2042)
 H3B(0.3114) H5B(0.2986) H6B(0.1918) H31A(0.3967) H31B(0.449) H31C(0.3785)
 H51A(0.4114) H51B(0.4491) H51C(0.3752) H2AB(0.3172) H3A(0.2119) H5A(0.1834)
 H6A(0.289) H31J(0.089) H31K(0.125) H31L(0.051) H51J(0.1198) H51K(0.118)
 H51L(0.0554) H2CA(0.1822) H3C(0.2876) H5C(0.3228) H6C(0.2172) H31G(0.4221)
 H31H(0.3883) H31I(0.4627) H51G(0.3716) H51H(0.3746) H51I(0.4353)
;
_olex2_submission_special_instructions 'No special instructions were received'