#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/26/7052636.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_7052636
loop_
_publ_author_name
'Olguín, Juan'
'Brooker, Sally'
_publ_section_title
;
 Synthesis of 3- and 5-formyl-4-phenyl-1H-pyrazoles: promising head
 units for the generation of asymmetric imine ligands and mixed metal
 polynuclear complexes
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1242
_journal_paper_doi               10.1039/c0nj00774a
_journal_volume                  35
_journal_year                    2011
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.229(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0556(5)
_cell_length_b                   16.6586(9)
_cell_length_c                   7.7010(4)
_cell_measurement_reflns_used    2605
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      25.435
_cell_measurement_theta_min      2.3885
_cell_volume                     1273.31(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      88(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa Apex II area detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14804
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE (Bruker AXS Inc.)'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0486
_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)+(0.0501P)²+0.4093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                2031
_reflns_number_total             2617
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0nj00774a.txt
_cod_data_source_block           jl185
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1273.31(11)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7052636
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.86886(14) 0.84539(9) 0.25534(18) 0.0214(3) Uani 1 1 d . . .
N2 N 0.78408(14) 0.90176(9) 0.29807(19) 0.0247(4) Uani 1 1 d . . .
C1 C 0.66963(17) 0.86274(11) 0.3054(2) 0.0237(4) Uani 1 1 d . . .
H1 H 0.5907 0.8876 0.3334 0.028 Uiso 1 1 calc R . .
C2 C 0.67868(17) 0.78064(11) 0.2670(2) 0.0213(4) Uani 1 1 d . . .
C3 C 0.80955(17) 0.77150(10) 0.2341(2) 0.0198(4) Uani 1 1 d . . .
C4 C 0.87366(17) 0.69972(11) 0.1760(2) 0.0216(4) Uani 1 1 d . . .
H4 H 0.8225 0.6515 0.1674 0.026 Uiso 1 1 calc R . .
O1 O 0.98592(12) 0.69583(8) 0.13771(15) 0.0252(3) Uani 1 1 d . . .
C5 C 0.57152(17) 0.71984(11) 0.2561(2) 0.0210(4) Uani 1 1 d . . .
C6 C 0.44141(17) 0.73856(11) 0.1724(2) 0.0237(4) Uani 1 1 d . . .
H6 H 0.4225 0.7909 0.1257 0.028 Uiso 1 1 calc R . .
C7 C 0.33950(18) 0.68145(12) 0.1567(2) 0.0268(4) Uani 1 1 d . . .
H7 H 0.2510 0.6952 0.1016 0.032 Uiso 1 1 calc R . .
C8 C 0.36642(18) 0.60467(11) 0.2212(2) 0.0256(4) Uani 1 1 d . . .
H8 H 0.2975 0.5651 0.2068 0.031 Uiso 1 1 calc R . .
C9 C 0.49426(17) 0.58592(11) 0.3066(2) 0.0250(4) Uani 1 1 d . . .
H9 H 0.5125 0.5335 0.3528 0.030 Uiso 1 1 calc R . .
C10 C 0.59610(17) 0.64291(11) 0.3255(2) 0.0237(4) Uani 1 1 d . . .
H10 H 0.6831 0.6295 0.3861 0.028 Uiso 1 1 calc R . .
C11 C 1.00475(16) 0.86541(11) 0.2283(2) 0.0211(4) Uani 1 1 d . . .
H11 H 1.0650 0.8188 0.2666 0.025 Uiso 1 1 calc R . .
C12 C 1.06240(18) 0.93942(11) 0.3273(2) 0.0255(4) Uani 1 1 d . . .
H12A H 1.0660 0.9316 0.4554 0.031 Uiso 1 1 calc R . .
H12B H 1.0051 0.9867 0.2904 0.031 Uiso 1 1 calc R . .
C13 C 1.20430(18) 0.95270(12) 0.2852(2) 0.0258(4) Uani 1 1 d . . .
H13A H 1.2417 1.0033 0.3400 0.031 Uiso 1 1 calc R . .
H13B H 1.2637 0.9081 0.3345 0.031 Uiso 1 1 calc R . .
C14 C 1.20023(18) 0.95683(12) 0.0870(2) 0.0265(4) Uani 1 1 d . . .
H14A H 1.1526 1.0062 0.0404 0.032 Uiso 1 1 calc R . .
H14B H 1.2933 0.9592 0.0604 0.032 Uiso 1 1 calc R . .
C15 C 1.12869(17) 0.88399(12) -0.0017(2) 0.0258(4) Uani 1 1 d . . .
H15A H 1.1216 0.8895 -0.1308 0.031 Uiso 1 1 calc R . .
H15B H 1.1823 0.8352 0.0348 0.031 Uiso 1 1 calc R . .
O2 O 0.99670(11) 0.87517(7) 0.04307(15) 0.0227(3) Uani 1 1 d . . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C3 112.14(14) . . ?
N2 N1 C11 121.49(14) . . ?
C3 N1 C11 126.30(14) . . ?
C1 N2 N1 104.82(15) . . ?
N2 C1 C2 112.39(16) . . ?
N2 C1 H1 123.8 . . ?
C2 C1 H1 123.8 . . ?
C3 C2 C1 103.91(15) . . ?
C3 C2 C5 128.40(16) . . ?
C1 C2 C5 127.63(16) . . ?
N1 C3 C2 106.73(15) . . ?
N1 C3 C4 124.61(15) . . ?
C2 C3 C4 128.55(16) . . ?
O1 C4 C3 126.24(17) . . ?
O1 C4 H4 116.9 . . ?
C3 C4 H4 116.9 . . ?
C10 C5 C6 118.48(16) . . ?
C10 C5 C2 121.82(15) . . ?
C6 C5 C2 119.70(16) . . ?
C7 C6 C5 120.67(17) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 120.20(16) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 119.56(17) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.65(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 120.40(16) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
O2 C11 N1 105.42(12) . . ?
O2 C11 C12 111.51(14) . . ?
N1 C11 C12 114.03(14) . . ?
O2 C11 H11 108.6 . . ?
N1 C11 H11 108.6 . . ?
C12 C11 H11 108.6 . . ?
C11 C12 C13 107.80(15) . . ?
C11 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
C11 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.5 . . ?
C14 C13 C12 110.08(14) . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C13 110.49(15) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
O2 C15 C14 111.40(15) . . ?
O2 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
O2 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C11 O2 C15 110.29(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.344(2) . ?
N1 C3 1.366(2) . ?
N1 C11 1.454(2) . ?
N2 C1 1.331(2) . ?
C1 C2 1.405(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(2) . ?
C2 C5 1.471(2) . ?
C3 C4 1.462(2) . ?
C4 O1 1.213(2) . ?
C4 H4 0.9500 . ?
C5 C10 1.395(2) . ?
C5 C6 1.398(2) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 O2 1.425(2) . ?
C11 C12 1.515(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.529(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.522(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O2 1.431(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 C1 0.51(18) . . . . ?
C11 N1 N2 C1 177.71(14) . . . . ?
N1 N2 C1 C2 -0.16(19) . . . . ?
N2 C1 C2 C3 -0.22(19) . . . . ?
N2 C1 C2 C5 -177.53(15) . . . . ?
N2 N1 C3 C2 -0.66(18) . . . . ?
C11 N1 C3 C2 -177.70(14) . . . . ?
N2 N1 C3 C4 175.67(15) . . . . ?
C11 N1 C3 C4 -1.4(3) . . . . ?
C1 C2 C3 N1 0.51(17) . . . . ?
C5 C2 C3 N1 177.79(15) . . . . ?
C1 C2 C3 C4 -175.63(16) . . . . ?
C5 C2 C3 C4 1.7(3) . . . . ?
N1 C3 C4 O1 -0.7(3) . . . . ?
C2 C3 C4 O1 174.82(16) . . . . ?
C3 C2 C5 C10 44.7(3) . . . . ?
C1 C2 C5 C10 -138.62(18) . . . . ?
C3 C2 C5 C6 -134.50(18) . . . . ?
C1 C2 C5 C6 42.2(2) . . . . ?
C10 C5 C6 C7 -0.8(3) . . . . ?
C2 C5 C6 C7 178.40(16) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C6 C7 C8 C9 2.2(3) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C8 C9 C10 C5 -1.0(3) . . . . ?
C6 C5 C10 C9 1.9(2) . . . . ?
C2 C5 C10 C9 -177.29(16) . . . . ?
N2 N1 C11 O2 -96.28(16) . . . . ?
C3 N1 C11 O2 80.51(19) . . . . ?
N2 N1 C11 C12 26.4(2) . . . . ?
C3 N1 C11 C12 -156.85(15) . . . . ?
O2 C11 C12 C13 -60.54(18) . . . . ?
N1 C11 C12 C13 -179.79(14) . . . . ?
C11 C12 C13 C14 54.49(19) . . . . ?
C12 C13 C14 C15 -52.8(2) . . . . ?
C13 C14 C15 O2 55.26(19) . . . . ?
N1 C11 O2 C15 -171.87(13) . . . . ?
C12 C11 O2 C15 63.88(18) . . . . ?
C14 C15 O2 C11 -60.30(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139175989
