#------------------------------------------------------------------------------
#$Date: 2022-04-15 04:22:45 +0300 (Fri, 15 Apr 2022) $
#$Revision: 274547 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/47/7244789.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_7244789
loop_
_publ_author_name
'Scheepers, Matthew C.'
'Fernandes, Manuel A.'
'Lemmerer, Andreas'
_publ_section_title
;
 Chains or rings? Polymorphism of an isoniazid derivative derivatized with
 diacetone alcohol
;
_journal_issue                   19
_journal_name_full               'RSC Advances'
_journal_page_first              11658
_journal_page_last               11664
_journal_paper_doi               10.1039/D2RA02057B
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C12 H17 N3 O2'
_chemical_formula_sum            'C12 H17 N3 O2'
_chemical_formula_weight         235.28
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2021-09-02T14:28:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2022-01-10 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.465(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.8108(4)
_cell_length_b                   7.0776(2)
_cell_length_c                   18.1625(5)
_cell_measurement_reflns_used    3359
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.16
_cell_measurement_theta_min      2.44
_cell_measurement_wavelength     0.71073
_cell_volume                     2509.90(13)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1191
_diffrn_reflns_av_unetI/netI     0.0858
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            37052
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         2.086
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1008
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.863
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0527P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0
_reflns_number_gt                1696
_reflns_number_total             3065
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra02057b4.cif
_cod_data_source_block           iz4h4m2pFormI
_cod_original_cell_volume        2509.90(12)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7244789
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.987
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'
'-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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.60221(9) 0.2622(3) 0.76509(11) 0.0468(5) Uani 1 1 d . . . . .
H1 H 0.611019 0.130905 0.775307 0.056 Uiso 1 1 calc R U . . .
C2 C 0.55179(8) 0.3160(2) 0.68884(10) 0.0384(4) Uani 1 1 d . . . . .
H2 H 0.526761 0.22371 0.648663 0.046 Uiso 1 1 calc R U . . .
C3 C 0.53841(7) 0.5058(2) 0.67205(9) 0.0274(4) Uani 1 1 d . . . . .
C4 C 0.57599(8) 0.6326(3) 0.73409(10) 0.0402(4) Uani 1 1 d . . . . .
H4 H 0.5683 0.764676 0.725735 0.048 Uiso 1 1 calc R U . . .
C5 C 0.62478(9) 0.5635(3) 0.80823(11) 0.0490(5) Uani 1 1 d . . . . .
H5 H 0.649798 0.65235 0.850124 0.059 Uiso 1 1 calc R U . . .
C6 C 0.48736(7) 0.5849(2) 0.59129(9) 0.0278(3) Uani 1 1 d . . . . .
C7 C 0.34125(7) 0.4196(2) 0.42602(9) 0.0258(3) Uani 1 1 d . . . . .
C8 C 0.29375(8) 0.4738(2) 0.33900(9) 0.0358(4) Uani 1 1 d . . . . .
H8A H 0.314879 0.573755 0.320683 0.054 Uiso 1 1 calc R U . . .
H8B H 0.25043 0.51962 0.336375 0.054 Uiso 1 1 calc R U . . .
H8C H 0.284987 0.363252 0.30319 0.054 Uiso 1 1 calc R U . . .
C9 C 0.31780(8) 0.26478(19) 0.46494(9) 0.0268(3) Uani 1 1 d . . . . .
H9A H 0.267575 0.251657 0.432658 0.032 Uiso 1 1 calc R U . . .
H9B H 0.326709 0.307145 0.520768 0.032 Uiso 1 1 calc R U . . .
C10 C 0.34978(7) 0.0681(2) 0.47271(9) 0.0276(4) Uani 1 1 d . . . . .
C11 C 0.35095(10) 0.0048(2) 0.39391(10) 0.0409(4) Uani 1 1 d . . . . .
H11A H 0.37811 0.094054 0.379291 0.061 Uiso 1 1 calc R U . . .
H11B H 0.304041 0.000716 0.349673 0.061 Uiso 1 1 calc R U . . .
H11C H 0.371449 -0.121274 0.401642 0.061 Uiso 1 1 calc R U . . .
C12 C 0.31135(9) -0.0719(2) 0.50013(11) 0.0394(4) Uani 1 1 d . . . . .
H12A H 0.332887 -0.196557 0.507687 0.059 Uiso 1 1 calc R U . . .
H12B H 0.263627 -0.079933 0.458187 0.059 Uiso 1 1 calc R U . . .
H12C H 0.31274 -0.029577 0.552228 0.059 Uiso 1 1 calc R U . . .
N1 N 0.63921(7) 0.3819(2) 0.82511(9) 0.0481(4) Uani 1 1 d . . . . .
N2 N 0.44071(6) 0.46296(19) 0.54094(8) 0.0271(3) Uani 1 1 d . . . . .
N3 N 0.39595(6) 0.51890(17) 0.46101(7) 0.0277(3) Uani 1 1 d . . . . .
O1 O 0.48910(5) 0.75362(14) 0.57574(7) 0.0400(3) Uani 1 1 d . . . . .
O2 O 0.41883(5) 0.08361(16) 0.53655(7) 0.0386(3) Uani 1 1 d . . . . .
H2A H 0.4411(9) 0.343(3) 0.5550(10) 0.044(5) Uiso 1 1 d . . . . .
H2B H 0.4381(11) -0.021(3) 0.5391(13) 0.063(7) Uiso 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 0 '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 0.006 '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
N1 C1 C2 124.41(17) . . ?
C3 C2 C1 119.02(16) . . ?
C2 C3 C4 117.40(14) . . ?
C2 C3 C6 124.85(13) . . ?
C4 C3 C6 117.74(14) . . ?
C5 C4 C3 118.84(17) . . ?
N1 C5 C4 124.68(16) . . ?
O1 C6 N2 124.12(14) . . ?
O1 C6 C3 120.05(13) . . ?
N2 C6 C3 115.80(13) . . ?
N3 C7 C8 115.72(13) . . ?
N3 C7 C9 126.83(13) . . ?
C8 C7 C9 117.31(13) . . ?
C7 C9 C10 117.77(13) . . ?
O2 C10 C11 109.43(14) . . ?
O2 C10 C12 108.56(12) . . ?
C11 C10 C12 111.25(13) . . ?
O2 C10 C9 105.92(11) . . ?
C11 C10 C9 112.36(12) . . ?
C12 C10 C9 109.12(13) . . ?
C5 N1 C1 115.63(15) . . ?
C6 N2 N3 119.61(13) . . ?
C7 N3 N2 115.10(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
C1 N1 1.332(2) . ?
C1 C2 1.384(2) . ?
C2 C3 1.379(2) . ?
C3 C4 1.387(2) . ?
C3 C6 1.500(2) . ?
C4 C5 1.381(2) . ?
C5 N1 1.326(3) . ?
C6 O1 1.2318(17) . ?
C6 N2 1.3365(19) . ?
C7 N3 1.2829(18) . ?
C7 C8 1.503(2) . ?
C7 C9 1.511(2) . ?
C9 C10 1.535(2) . ?
C10 O2 1.4382(17) . ?
C10 C11 1.511(2) . ?
C10 C12 1.518(2) . ?
N2 N3 1.3980(17) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O2 0.95 2.53 3.4084(19) 153.9 . yes
C9 H9B N1 0.99 2.61 3.594(2) 172.7 2_656 yes
N2 H2A O2 0.888(19) 1.888(19) 2.7220(18) 155.7(16) . yes
O2 H2B O1 0.84(2) 1.89(2) 2.7088(15) 164(2) 1_545 yes
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
N1 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C1 C2 C3 C6 177.50(16) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C6 C3 C4 C5 -178.08(16) . . . . ?
C3 C4 C5 N1 0.4(3) . . . . ?
C2 C3 C6 O1 -164.22(16) . . . . ?
C4 C3 C6 O1 14.5(2) . . . . ?
C2 C3 C6 N2 17.6(2) . . . . ?
C4 C3 C6 N2 -163.74(15) . . . . ?
N3 C7 C9 C10 -80.9(2) . . . . ?
C8 C7 C9 C10 103.71(15) . . . . ?
C7 C9 C10 O2 72.41(16) . . . . ?
C7 C9 C10 C11 -47.03(18) . . . . ?
C7 C9 C10 C12 -170.90(13) . . . . ?
C4 C5 N1 C1 -1.0(3) . . . . ?
C2 C1 N1 C5 0.4(3) . . . . ?
O1 C6 N2 N3 8.9(2) . . . . ?
C3 C6 N2 N3 -173.01(13) . . . . ?
C8 C7 N3 N2 -177.96(13) . . . . ?
C9 C7 N3 N2 6.6(2) . . . . ?
C6 N2 N3 C7 -159.91(14) . . . . ?
