Persistence of a self-complementary N‒H⋯N tape motif in chloro-s-triazine crystals: crystal structures of simazine and atrazine herbicides and their polymorphic and inclusion behaviour
Le, Thanh; Bhadbhade, Mohan; Gao, Jiabin; Hook, James M.; Marjo, Christopher E.; CrystEngComm 18 (2016) 962–; doi:10.1039/C5CE02206A

data_7223727
_publ_section_title
;
 Persistence of a self-complementary N--H&#x22EF;N tape motif in
 chloro-s-triazine crystals: crystal structures of simazine and atrazine
 herbicides and their polymorphic and inclusion behaviour
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              962
_journal_paper_doi               10.1039/C5CE02206A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         '2(C8 H14 Cl N5)'
_chemical_formula_sum            'C16 H28 Cl2 N10'
_chemical_formula_weight         431.38
_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_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-11-06 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.847(4)
_cell_length_b                   9.6160(19)
_cell_length_c                   23.793(5)
_cell_measurement_temperature    100
_cell_volume                     4540.9(16)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Australian Synchrotron'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1568
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_laue_measured_fraction_full 0.997
_diffrn_reflns_laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_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            34417
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        21.325
_diffrn_reflns_theta_max         21.325
_diffrn_reflns_theta_min         1.712
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       needle
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.015
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         2548
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1520
_refine_ls_R_factor_gt           0.1101
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+40.7579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2366
_refine_ls_wR_factor_ref         0.2566
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1657
_reflns_number_total             2548
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ce02206a2.cif
_cod_data_source_block           atrazine_pca21_a
_cod_depositor_comments
'Adding full bibliography for 7223725--7223728.cif.'
_cod_database_code               7223727
_olex2_refinement_description
;
1. Shared sites
{H4AA, H4A}
{H5AA, H5A}
{C4A, C6A'}
{C7A', C5A}
{C4A', C6A}
{H4AE, H6A}
{C5A', C7A}
2. Others
 Fixed Sof: Cl1"(0.5) Cl1B(0.5) C4B(0.6) H4BA(0.6) H4BB(0.6) C5B(0.6)
 H5BA(0.6) H5BB(0.6) H5BC(0.6) C4B'(0.4) H4BC(0.4) H4BD(0.4) C5B'(0.4)
 H5BD(0.4) H5BE(0.4) H5BF(0.4) H4A(0.5) H4AA(0.5) H5A(0.5) C4A(0.5) H4AB(0.5)
 H4AC(0.5) C6A'(0.5) C5A(0.5) H5AB(0.5) H5AC(0.5) H5AD(0.5) C6A(0.5) H6A(0.5)
 C7A(0.5) H7AA(0.5) H7AB(0.5) H7AC(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5) H8AC(0.5)
 C4A'(0.5) H4AD(0.5) H4AE(0.5) C5A'(0.5) H5AE(0.5) H5AF(0.5) H5AG(0.5)
 C7A'(0.5) H7AD(0.5) H7AE(0.5) H7AF(0.5) C8A'(0.5) H8AD(0.5) H8AE(0.5) H8AF(0.5)
 Fixed Uiso: H4B(0.081) H5B(0.081) H4BA(0.053) H4BB(0.053) H5BA(0.096)
 H5BB(0.096) H5BC(0.096) H6B(0.089) H7BA(0.155) H7BB(0.155) H7BC(0.155)
 H8BA(0.13) H8BB(0.13) H8BC(0.13) H4BC(0.102) H4BD(0.102) H5BD(0.208)
 H5BE(0.208) H5BF(0.208) H4A(0.078) H4AA(0.078) H5A(0.072) H5AA(0.072)
 H4AB(0.089) H4AC(0.089) H5AB(0.144) H5AC(0.144) H5AD(0.144) H6A(0.08)
 H7AA(0.139) H7AB(0.139) H7AC(0.139) H8AA(0.121) H8AB(0.121) H8AC(0.121)
 H4AD(0.08) H4AE(0.08) H5AE(0.139) H5AF(0.139) H5AG(0.139) H7AD(0.144)
 H7AE(0.144) H7AF(0.144) H8AD(0.177) H8AE(0.177) H8AF(0.177)
 Fixed X: H4B(1.0599) H5B(1.0539) H4BA(0.9426) H4BB(0.9482) H5BA(0.9468)
 H5BB(0.9439) H5BC(0.8812) H6B(0.9364) H7BA(0.9495) H7BB(0.8825) H7BC(0.9486)
 H8BA(0.9576) H8BB(0.8854) H8BC(0.946) H4BC(0.9516) H4BD(0.9329) H5BD(0.9029)
 H5BE(0.9815) H5BF(0.9491) H4A(1.1779) H4AA(1.1779) H5A(1.1883) H5AA(1.1883)
 H4AB(1.2522) H4AC(1.2548) H5AB(1.3585) H5AC(1.325) H5AD(1.3243) H6A(1.2642)
 H7AA(1.3325) H7AB(1.3279) H7AC(1.3677) H8AA(1.228) H8AB(1.3071) H8AC(1.2542)
 H4AD(1.2632) H4AE(1.2642) H5AE(1.3512) H5AF(1.3589) H5AG(1.318) H7AD(1.3172)
 H7AE(1.3563) H7AF(1.3343) H8AD(1.2403) H8AE(1.2882) H8AF(1.2087)
 Fixed Y: H4B(0.7809) H5B(0.7465) H4BA(0.6954) H4BB(0.7147) H5BA(0.943)
 H5BB(0.9546) H5BC(0.8918) H6B(0.7047) H7BA(0.9508) H7BB(0.9003) H7BC(0.9372)
 H8BA(0.6905) H8BB(0.6658) H8BC(0.5604) H4BC(0.8769) H4BD(0.7378) H5BD(0.9459)
 H5BE(0.978) H5BF(0.8437) H4A(0.6517) H4AA(0.6517) H5A(0.6611) H5AA(0.6611)
 H4AB(0.4741) H4AC(0.4524) H5AB(0.5302) H5AC(0.6609) H5AD(0.6511) H6A(0.466)
 H7AA(0.6625) H7AB(0.6938) H7AC(0.5596) H8AA(0.398) H8AB(0.4246) H8AC(0.537)
 H4AD(0.4862) H4AE(0.4668) H5AE(0.6202) H5AF(0.5796) H5AG(0.7162) H7AD(0.6795)
 H7AE(0.5356) H7AF(0.6271) H8AD(0.5251) H8AE(0.4011) H8AF(0.3927)
 Fixed Z: H4B(0.4427) H5B(0.1879) H4BA(0.3871) H4BB(0.454) H5BA(0.3778)
 H5BB(0.4449) H5BC(0.411) H6B(0.2503) H7BA(0.2422) H7BB(0.2107) H7BC(0.1751)
 H8BA(0.1312) H8BB(0.1594) H8BC(0.172) H4BC(0.384) H4BD(0.4172) H5BD(0.4659)
 H5BE(0.4733) H5BF(0.5024) H4A(0.1919) H4AA(0.1919) H5A(-0.0612) H5AA(-0.0612)
 H4AB(0.2045) H4AC(0.1378) H5AB(0.1672) H5AC(0.198) H5AD(0.1309) H6A(-0.0039)
 H7AA(0.0059) H7AB(-0.06) H7AC(-0.0381) H8AA(-0.0868) H8AB(-0.094) H8AC(-
 0.1167) H4AD(-0.0711) H4AE(-0.0042) H5AE(-0.0681) H5AF(-0.0032) H5AG(-0.0208)
 H7AD(0.1416) H7AE(0.1507) H7AF(0.2038) H8AD(0.2507) H8AE(0.2303) H8AF(0.2197)
;
_shelx_res_checksum              62446
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'