#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/29/1572991.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_1572991
loop_
_publ_author_name
'Khamrang, Themmila'
'Kannan, A.'
'Hemamalini, Madhukar'
'Tahir, Muhammad Nawaz'
'Antony, G. Jerald Maria'
'Saravanan, Dhandayutham'
_publ_section_title
;
 (1H-Benzodiazol-2-ylmethyl)diethylamine
;
_journal_coeditor_code           HB4488
_journal_issue                   10
_journal_name_full               IUCrData
_journal_page_first              x241006
_journal_paper_doi               10.1107/S241431462401006X
_journal_volume                  9
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C12 H17 N3'
_chemical_formula_moiety         'C12 H17 N3'
_chemical_formula_sum            'C12 H17 N3'
_chemical_formula_weight         203.28
_chemical_name_systematic
;
(1H-Benzodiazol-2-ylmethyl)diethylamine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9290(7)
_cell_length_b                   15.3027(15)
_cell_length_c                   10.0486(6)
_cell_measurement_reflns_used    9307
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.359
_cell_measurement_theta_min      3.477
_cell_volume                     1219.25(18)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device_type  'Agilent Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3304
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.655
_diffrn_reflns_theta_min         3.534
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.5778
_exptl_absorpt_correction_T_min  0.5069
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colouress
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.295
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.101
_refine_ls_abs_structure_details
;
Flack x determined using 249 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2135
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0388P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                1138
_reflns_number_total             2135
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4488.cif
_cod_data_source_block           I
_cod_database_code               1572991
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.980
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.2389(4) 0.3102(2) 0.0373(3) 0.0597(10) Uani d 1 . .
H H1 0.284732 0.301682 0.113816 0.072 Uiso calc 1 . .
N N2 0.1987(4) 0.3027(3) -0.1813(3) 0.0659(11) Uani d 1 . .
N N3 0.5022(5) 0.1850(4) 0.0249(4) 0.0951(15) Uani d 1 . .
C C1 0.0952(5) 0.3570(3) 0.0120(3) 0.0515(11) Uani d 1 . .
C C2 -0.0116(6) 0.4053(3) 0.0930(4) 0.0648(13) Uani d 1 . .
H H2 0.005609 0.408829 0.184357 0.078 Uiso calc 1 . .
C C3 -0.1425(6) 0.4474(3) 0.0331(5) 0.0761(14) Uani d 1 . .
H H3 -0.216070 0.480461 0.084546 0.091 Uiso calc 1 . .
C C4 -0.1685(6) 0.4418(3) -0.1041(4) 0.0791(15) Uani d 1 . .
H H4 -0.259316 0.471219 -0.141747 0.095 Uiso calc 1 . .
C C5 -0.0640(6) 0.3942(3) -0.1845(4) 0.0739(14) Uani d 1 . .
H H5 -0.083221 0.390253 -0.275557 0.089 Uiso calc 1 . .
C C6 0.0716(5) 0.3521(3) -0.1255(3) 0.0570(13) Uani d 1 . .
C C7 0.2952(5) 0.2799(3) -0.0819(4) 0.0643(12) Uani d 1 . .
C C8 0.4587(6) 0.2325(4) -0.0949(4) 0.0909(17) Uani d 1 . .
H H8A 0.451582 0.191793 -0.168709 0.109 Uiso calc 1 . .
H H8B 0.547429 0.274120 -0.114689 0.109 Uiso calc 1 . .
C C9 0.3974(11) 0.1078(5) 0.0413(6) 0.131(2) Uani d 1 . .
H H9A 0.436683 0.062760 -0.019218 0.158 Uiso calc 1 . .
H H9B 0.282447 0.122226 0.016695 0.158 Uiso calc 1 . .
C C10 0.3979(10) 0.0716(5) 0.1815(7) 0.165(3) Uani d 1 . .
H H10A 0.386626 0.118764 0.243885 0.248 Uiso calc 1 . .
H H10B 0.502133 0.041431 0.197381 0.248 Uiso calc 1 . .
H H10C 0.305414 0.031777 0.192073 0.248 Uiso calc 1 . .
C C11A 0.6923(15) 0.1942(10) 0.0568(12) 0.099(5) Uani d 0.582(15) A 1
H H11A 0.722510 0.255582 0.058529 0.118 Uiso calc 0.582(15) A 1
H H11B 0.714977 0.169826 0.144064 0.118 Uiso calc 0.582(15) A 1
C C12A 0.797(2) 0.1479(12) -0.0451(15) 0.136(6) Uani d 0.582(15) A 1
H H12A 0.756247 0.089389 -0.056573 0.205 Uiso calc 0.582(15) A 1
H H12B 0.912622 0.146040 -0.015698 0.205 Uiso calc 0.582(15) A 1
H H12C 0.790966 0.178585 -0.128247 0.205 Uiso calc 0.582(15) A 1
C C11B 0.6574(15) 0.1307(12) 0.0073(17) 0.096(6) Uani d 0.418(15) A 2
H H11C 0.664688 0.106808 -0.081926 0.116 Uiso calc 0.418(15) A 2
H H11D 0.662348 0.083481 0.071549 0.116 Uiso calc 0.418(15) A 2
C C12B 0.793(3) 0.1976(13) 0.032(3) 0.121(8) Uani d 0.418(15) A 2
H H12D 0.789364 0.241313 -0.036326 0.181 Uiso calc 0.418(15) A 2
H H12E 0.901286 0.169560 0.031495 0.181 Uiso calc 0.418(15) A 2
H H12F 0.774788 0.224638 0.117173 0.181 Uiso calc 0.418(15) A 2
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C1 . . 106.7(3) ?
C7 N1 H1 . . 126.7 ?
C1 N1 H1 . . 126.7 ?
C7 N2 C6 . . 105.3(3) ?
C8 N3 C9 . . 111.5(5) ?
C8 N3 C11B . . 112.1(7) ?
C9 N3 C11B . . 91.9(7) ?
C8 N3 C11A . . 111.0(6) ?
C9 N3 C11A . . 127.4(7) ?
N1 C1 C2 . . 132.6(4) ?
N1 C1 C6 . . 105.6(3) ?
C2 C1 C6 . . 121.8(4) ?
C3 C2 C1 . . 117.2(4) ?
C3 C2 H2 . . 121.4 ?
C1 C2 H2 . . 121.4 ?
C2 C3 C4 . . 121.3(4) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C5 C4 C3 . . 121.8(5) ?
C5 C4 H4 . . 119.1 ?
C3 C4 H4 . . 119.1 ?
C4 C5 C6 . . 117.7(4) ?
C4 C5 H5 . . 121.1 ?
C6 C5 H5 . . 121.1 ?
N2 C6 C5 . . 130.4(3) ?
N2 C6 C1 . . 109.5(4) ?
C5 C6 C1 . . 120.2(4) ?
N2 C7 N1 . . 113.0(3) ?
N2 C7 C8 . . 124.9(3) ?
N1 C7 C8 . . 121.9(4) ?
N3 C8 C7 . . 112.2(3) ?
N3 C8 H8A . . 109.2 ?
C7 C8 H8A . . 109.2 ?
N3 C8 H8B . . 109.2 ?
C7 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
N3 C9 C10 . . 113.6(6) ?
N3 C9 H9A . . 108.8 ?
C10 C9 H9A . . 108.8 ?
N3 C9 H9B . . 108.8 ?
C10 C9 H9B . . 108.8 ?
H9A C9 H9B . . 107.7 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12A C11A N3 . . 111.0(13) ?
C12A C11A H11A . . 109.4 ?
N3 C11A H11A . . 109.4 ?
C12A C11A H11B . . 109.4 ?
N3 C11A H11B . . 109.4 ?
H11A C11A H11B . . 108.0 ?
C11A C12A H12A . . 109.5 ?
C11A C12A H12B . . 109.5 ?
H12A C12A H12B . . 109.5 ?
C11A C12A H12C . . 109.5 ?
H12A C12A H12C . . 109.5 ?
H12B C12A H12C . . 109.5 ?
N3 C11B C12B . . 101.0(16) ?
N3 C11B H11C . . 111.6 ?
C12B C11B H11C . . 111.6 ?
N3 C11B H11D . . 111.6 ?
C12B C11B H11D . . 111.6 ?
H11C C11B H11D . . 109.4 ?
C11B C12B H12D . . 109.5 ?
C11B C12B H12E . . 109.5 ?
H12D C12B H12E . . 109.5 ?
C11B C12B H12F . . 109.5 ?
H12D C12B H12F . . 109.5 ?
H12E C12B H12F . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C7 . 1.360(5) ?
N1 C1 . 1.369(5) ?
N1 H1 . 0.8600 ?
N2 C7 . 1.306(5) ?
N2 C6 . 1.379(5) ?
N3 C8 . 1.448(6) ?
N3 C9 . 1.453(8) ?
N3 C11B . 1.496(15) ?
N3 C11A . 1.547(13) ?
C1 C2 . 1.388(5) ?
C1 C6 . 1.396(4) ?
C2 C3 . 1.362(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.396(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.367(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.387(5) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.491(6) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.513(8) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11A C12A . 1.498(10) ?
C11A H11A . 0.9700 ?
C11A H11B . 0.9700 ?
C12A H12A . 0.9600 ?
C12A H12B . 0.9600 ?
C12A H12C . 0.9600 ?
C11B C12B . 1.505(11) ?
C11B H11C . 0.9700 ?
C11B H11D . 0.9700 ?
C12B H12D . 0.9600 ?
C12B H12E . 0.9600 ?
C12B H12F . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 4 0.86 2.06 2.873(4) 157 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C2 . . . . -176.9(4) ?
C7 N1 C1 C6 . . . . 0.1(5) ?
N1 C1 C2 C3 . . . . 177.3(4) ?
C6 C1 C2 C3 . . . . 0.7(6) ?
C1 C2 C3 C4 . . . . 0.2(7) ?
C2 C3 C4 C5 . . . . -0.1(8) ?
C3 C4 C5 C6 . . . . -0.9(7) ?
C7 N2 C6 C5 . . . . 178.8(4) ?
C7 N2 C6 C1 . . . . -0.7(5) ?
C4 C5 C6 N2 . . . . -177.7(5) ?
C4 C5 C6 C1 . . . . 1.8(7) ?
N1 C1 C6 N2 . . . . 0.4(5) ?
C2 C1 C6 N2 . . . . 177.8(4) ?
N1 C1 C6 C5 . . . . -179.2(4) ?
C2 C1 C6 C5 . . . . -1.8(7) ?
C6 N2 C7 N1 . . . . 0.8(5) ?
C6 N2 C7 C8 . . . . -174.1(5) ?
C1 N1 C7 N2 . . . . -0.6(5) ?
C1 N1 C7 C8 . . . . 174.5(4) ?
C9 N3 C8 C7 . . . . 73.2(6) ?
C11B N3 C8 C7 . . . . 174.5(8) ?
C11A N3 C8 C7 . . . . -138.7(6) ?
N2 C7 C8 N3 . . . . -155.9(5) ?
N1 C7 C8 N3 . . . . 29.6(7) ?
C8 N3 C9 C10 . . . . -162.1(5) ?
C11B N3 C9 C10 . . . . 83.2(9) ?
C11A N3 C9 C10 . . . . 56.2(10) ?
C8 N3 C11A C12A . . . . -68.0(13) ?
C9 N3 C11A C12A . . . . 73.8(14) ?
C8 N3 C11B C12B . . . . 83.4(15) ?
C9 N3 C11B C12B . . . . -162.5(14) ?
