#------------------------------------------------------------------------------
#$Date: 2020-04-10 08:11:13 +0300 (Fri, 10 Apr 2020) $
#$Revision: 250603 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/20/2022024.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_2022024
loop_
_publ_author_name
'Jha, Kunal Kumar'
'Gruza, Barbara'
'Kumar, Prashant'
'Chodkiewicz, Michal Leszek'
'Dominiak, Paulina Maria'
_publ_section_title
;
 TAAM: a reliable and user friendly tool for hydrogen-atom location using
 routine X-ray diffraction data
;
_journal_issue                   3
_journal_name_full
'Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials'
_journal_paper_doi               10.1107/S2052520620002917
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C16 H11 N O3'
_chemical_formula_sum            'C16 H11 N O3'
_chemical_formula_weight         265.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_audit_creation_date             2019-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.925(3)
_cell_length_b                   8.273(2)
_cell_length_c                   23.954(5)
_cell_measurement_temperature    100(2)
_cell_volume                     2561.4(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_diffrn_measurement_device_type  'Huber diffractometer'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6000
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14716
_diffrn_reflns_theta_full        52.1557
_diffrn_reflns_theta_max         52.16
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_density_diffrn    1.3757
_exptl_crystal_F_000             1104.6098
_refine_diff_density_max         0.3648
_refine_diff_density_min         -0.4589
_refine_diff_density_rms         0.0589
_refine_ls_d_res_high            0.4500
_refine_ls_d_res_low             11.9770
_refine_ls_goodness_of_fit_ref   1.0595
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     280
_refine_ls_number_reflns         14716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0595
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0521P)²+0.0184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0856
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              28
_reflns_limit_h_min              0
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              53
_reflns_limit_l_min              0
_reflns_number_gt                12628
_reflns_number_total             14716
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            11_TAAM_ANIS_max.cif
_cod_data_source_block           11_TAAM_ANIS_max
_cod_original_cell_volume        2561.36(90)
_cod_database_code               2022024
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-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_refinement_flags_posn
O(1) O 0.727729(12) 0.26797(2) 0.146140(7) 0.01814(3) Uani 1.000000 .
O(2) O 0.682691(13) 0.25156(2) 0.234206(7) 0.01835(3) Uani 1.000000 .
O(4) O 0.456719(14) 0.06112(3) 0.091919(7) 0.02126(3) Uani 1.000000 .
N(1) N 0.411943(15) -0.00977(3) 0.194680(8) 0.02128(3) Uani 1.000000 .
H(1a H 0.3894(6) 0.0017(9) 0.1534(3) 0.0458(18) Uani 1.000000 .
H(1b H 0.3686(5) -0.0777(8) 0.2226(2) 0.0381(16) Uani 1.000000 .
C(31 C 0.502184(13) 0.05232(2) 0.209352(7) 0.01487(3) Uani 1.000000 .
C14 C 0.567027(13) 0.12813(2) 0.168555(7) 0.01430(2) Uani 1.000000 .
C13 C 0.658541(13) 0.21631(2) 0.186270(8) 0.01473(2) Uani 1.000000 .
C15 C 0.538970(15) 0.12247(2) 0.109863(8) 0.01559(3) Uani 1.000000 .
C(5) C 0.598190(19) 0.18362(3) 0.011828(9) 0.01977(3) Uani 1.000000 .
H(5) H 0.5238(5) 0.1314(8) -0.0021(2) 0.0356(16) Uani 1.000000 .
C(6) C 0.67410(2) 0.23764(3) -0.024934(10) 0.02301(4) Uani 1.000000 .
H(6) H 0.6618(5) 0.2334(8) -0.0717(3) 0.0396(17) Uani 1.000000 .
C(7) C 0.76798(2) 0.29973(3) -0.004095(11) 0.02373(4) Uani 1.000000 .
H(7) H 0.8298(5) 0.3422(9) -0.0328(3) 0.0491(19) Uani 1.000000 .
C(8) C 0.785210(19) 0.30789(3) 0.053433(11) 0.02114(3) Uani 1.000000 .
H(8) H 0.8560(5) 0.3536(9) 0.0690(3) 0.0480(19) Uani 1.000000 .
C(9) C 0.707870(16) 0.25336(2) 0.089848(8) 0.01643(3) Uani 1.000000 .
C(10 C 0.614738(15) 0.18981(2) 0.069913(8) 0.01585(3) Uani 1.000000 .
C1 C 0.530382(13) 0.02973(2) 0.269330(7) 0.01449(2) Uani 1.000000 .
C2 C 0.620306(15) -0.05588(3) 0.283580(9) 0.01795(3) Uani 1.000000 .
H2 H 0.6721(4) -0.1039(8) 0.2519(3) 0.0369(15) Uani 1.000000 .
C3 C 0.64260(2) -0.08696(3) 0.339663(11) 0.02307(4) Uani 1.000000 .
H3 H 0.7137(5) -0.1554(9) 0.3500(3) 0.051(2) Uani 1.000000 .
C4 C 0.57628(3) -0.03052(4) 0.381725(10) 0.02553(4) Uani 1.000000 .
H4 H 0.5955(6) -0.0564(11) 0.4248(3) 0.058(2) Uani 1.000000 .
C11 C 0.48638(3) 0.05472(3) 0.367378(10) 0.02473(4) Uani 1.000000 .
H11 H 0.4337(6) 0.0987(10) 0.3988(3) 0.054(2) Uani 1.000000 .
C12 C 0.462603(18) 0.08364(3) 0.311131(9) 0.01923(3) Uani 1.000000 .
H12 H 0.3916(5) 0.1511(8) 0.2995(3) 0.0398(16) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C C 0.00347 0.00161
'Clementi & Roetti, C., At. Data Nucl. Data Tables 1974, 14, (177-478); Clementi & Raimondi, J. Chem. Phys., 1963, 38, (2686-2689)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H H 0.00000 0.00000
'Clementi & Roetti, C., At. Data Nucl. Data Tables 1974, 14, (177-478); Clementi & Raimondi, J. Chem. Phys., 1963, 38, (2686-2689)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N N 0.00653 0.00323
'Clementi & Roetti, C., At. Data Nucl. Data Tables 1974, 14, (177-478); Clementi & Raimondi, J. Chem. Phys., 1963, 38, (2686-2689)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O O 0.01158 0.00611
'Clementi & Roetti, C., At. Data Nucl. Data Tables 1974, 14, (177-478); Clementi & Raimondi, J. Chem. Phys., 1963, 38, (2686-2689)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C(9) O(1) C13 122.241(16) . . ?
H(1b N(1) H(1a 120.8(5) . . ?
C(31 N(1) H(1a 117.9(4) . . ?
C(31 N(1) H(1b 121.0(3) . . ?
C14 C(31 N(1) 120.335(17) . . ?
C1 C(31 N(1) 114.980(16) . . ?
C1 C(31 C14 124.631(15) . . ?
C13 C14 C(31 119.800(15) . . ?
C15 C14 C(31 120.017(15) . . ?
C15 C14 C13 120.133(16) . . ?
O(2) C13 O(1) 114.445(16) . . ?
C14 C13 O(1) 118.640(15) . . ?
C14 C13 O(2) 126.915(18) . . ?
C14 C15 O(4) 123.806(17) . . ?
C(10 C15 O(4) 119.491(17) . . ?
C(10 C15 C14 116.680(16) . . ?
C(6) C(5) H(5) 123.2(3) . . ?
C(10 C(5) H(5) 116.4(3) . . ?
C(10 C(5) C(6) 120.41(2) . . ?
H(6) C(6) C(5) 121.2(4) . . ?
C(7) C(6) C(5) 119.99(2) . . ?
C(7) C(6) H(6) 118.8(4) . . ?
H(7) C(7) C(6) 121.0(4) . . ?
C(8) C(7) C(6) 120.28(2) . . ?
C(8) C(7) H(7) 118.7(4) . . ?
H(8) C(8) C(7) 120.2(3) . . ?
C(9) C(8) C(7) 118.98(2) . . ?
C(9) C(8) H(8) 120.8(3) . . ?
C(8) C(9) O(1) 116.618(19) . . ?
C(10 C(9) O(1) 121.855(17) . . ?
C(10 C(9) C(8) 121.52(2) . . ?
C(5) C(10 C15 121.678(18) . . ?
C(9) C(10 C15 119.417(17) . . ?
C(9) C(10 C(5) 118.810(18) . . ?
C2 C1 C(31 119.943(16) . . ?
C12 C1 C(31 119.616(17) . . ?
C12 C1 C2 120.262(18) . . ?
H2 C2 C1 121.6(3) . . ?
C3 C2 C1 119.83(2) . . ?
C3 C2 H2 118.5(3) . . ?
H3 C3 C2 118.7(4) . . ?
C4 C3 C2 120.21(2) . . ?
C4 C3 H3 121.1(4) . . ?
H4 C4 C3 118.5(5) . . ?
C11 C4 C3 119.85(2) . . ?
C11 C4 H4 121.6(5) . . ?
H11 C11 C4 121.4(4) . . ?
C12 C11 C4 120.19(2) . . ?
C12 C11 H11 118.4(4) . . ?
C11 C12 C1 119.64(2) . . ?
H12 C12 C1 119.8(3) . . ?
H12 C12 C11 120.5(3) . . ?
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
O(1) C13 1.3807(2) . ?
O(1) C(9) 1.3779(3) . ?
O(2) C13 1.2251(2) . ?
O(4) C15 1.2540(2) . ?
N(1) H(1a 1.034(6) . ?
N(1) H(1b 1.038(6) . ?
N(1) C(31 1.3220(2) . ?
C(31 C14 1.4321(3) . ?
C(31 C1 1.4939(2) . ?
C14 C13 1.4531(2) . ?
C14 C15 1.4527(2) . ?
C15 C(10 1.4782(3) . ?
C(5) H(5) 1.105(6) . ?
C(5) C(6) 1.3921(3) . ?
C(5) C(10 1.4086(3) . ?
C(6) H(6) 1.133(6) . ?
C(6) C(7) 1.4090(4) . ?
C(7) H(7) 1.111(7) . ?
C(7) C(8) 1.3975(4) . ?
C(8) H(8) 1.058(7) . ?
C(8) C(9) 1.4013(3) . ?
C(9) C(10 1.3976(3) . ?
C1 C2 1.4032(3) . ?
C1 C12 1.4032(3) . ?
C2 H2 1.087(6) . ?
C2 C3 1.3978(3) . ?
C3 H3 1.108(7) . ?
C3 C4 1.4028(4) . ?
C4 H4 1.082(7) . ?
C4 C11 1.4020(5) . ?
C11 H11 1.078(7) . ?
C11 C12 1.4025(3) . ?
C12 H12 1.109(6) . ?
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
N(1) H(1a O(4) 1.034(6) 1.781(7) 2.5958(3) 132.7(6) .
