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_7223728
_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), 2(C2 H2 Cl4)'
_chemical_formula_sum            'C20 H32 Cl10 N10'
_chemical_formula_weight         767.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 105.86(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.908(3)
_cell_length_b                   19.374(7)
_cell_length_c                   15.441(5)
_cell_measurement_reflns_used    956
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      18.106
_cell_measurement_theta_min      2.510
_cell_volume                     3426.7(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      150.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2258
_diffrn_reflns_av_unetI/netI     0.2638
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29241
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.140
_diffrn_reflns_theta_min         2.754
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.7158.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.035
_refine_diff_density_max         2.225
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         7506
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.2937
_refine_ls_R_factor_gt           0.1058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1698P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2634
_refine_ls_wR_factor_ref         0.3773
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2371
_reflns_number_total             7506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ce02206a2.cif
_cod_data_source_block           atraziene_tce_a
_cod_depositor_comments
'Adding full bibliography for 7223725--7223728.cif.'
_cod_original_cell_volume        3426.7(18)
_cod_database_code               7223728
_olex2_refinement_description
;
1. Others
 Fixed Sof: Cl2D(0.5) Cl3D(0.5) Cl1D(0.5) Cl4D(0.5) C1D(0.5) H1D(0.5) C2D(0.5)
 H2D(0.5) Cl0A(0.5) Cl3A(0.5) Cl3(0.5) Cl2(0.5) C2(0.5) H2(0.5) C8(0.5) H8(0.5)
 Fixed Uiso: H4B(0.046) H5B(0.049) H4BA(0.057) H4BB(0.057) H6B(0.051)
 H7BA(0.077) H7BB(0.077) H7BC(0.077) H8BA(0.088) H8BB(0.088) H8BC(0.088)
 H5BA(0.194) H5BB(0.194) H5BC(0.194) H4A(0.052) H5A(0.048) H4AA(0.065)
 H4AB(0.065) H5AA(0.102) H5AB(0.102) H5AC(0.102) H6A(0.072) H7AA(0.12)
 H7AB(0.12) H7AC(0.12) H8AA(0.099) H8AB(0.099) H8AC(0.099) H1C(0.079)
 H2C(0.062) H1D(0.092) H2D(0.073) H2(0.056) H8(0.1)
 Fixed X: H4B(1.1133) H5B(0.6018) H4BA(1.1217) H4BB(0.9834) H6B(0.686)
 H7BA(0.5074) H7BB(0.4507) H7BC(0.4831) H8BA(0.7193) H8BB(0.6234) H8BC(0.584)
 H5BA(0.9592) H5BB(1.0174) H5BC(1.0969) H4A(0.6313) H5A(0.1279) H4AA(0.6542)
 H4AB(0.519) H5AA(0.6257) H5AB(0.564) H5AC(0.6993) H6A(0.2577) H7AA(0.0748)
 H7AB(0.0117) H7AC(0.0863) H8AA(0.1429) H8AB(0.28) H8AC(0.1918) H1C(1.2672)
 H2C(1.1296) H1D(0.618) H2D(0.8196) H2(0.6354) H8(0.8147)
 Fixed Y: H4B(0.6761) H5B(0.6738) H4BA(0.5582) H4BB(0.5541) H6B(0.5885)
 H7BA(0.6406) H7BB(0.611) H7BC(0.5597) H8BA(0.5256) H8BB(0.4885) H8BC(0.5307)
 H5BA(0.6137) H5BB(0.5392) H5BC(0.607) H4A(0.6956) H5A(0.6848) H4AA(0.5845)
 H4AB(0.5727) H5AA(0.5166) H5AB(0.5809) H5AC(0.5848) H6A(0.5676) H7AA(0.5741)
 H7AB(0.5701) H7AC(0.5059) H8AA(0.584) H8AB(0.5737) H8AC(0.5115) H1C(0.6412)
 H2C(0.7268) H1D(0.8375) H2D(0.8612) H2(0.8139) H8(0.8284)
 Fixed Z: H4B(0.4247) H5B(0.4125) H4BA(0.3997) H4BB(0.3851) H6B(0.302)
 H7BA(0.2343) H7BB(0.3094) H7BC(0.2387) H8BA(0.4333) H8BB(0.3538) H8BC(0.4297)
 H5BA(0.2482) H5BB(0.2492) H5BC(0.262) H4A(-0.0297) H5A(-0.015) H4AA(-0.05)
 H4AB(-0.0573) H5AA(0.0675) H5AB(0.1008) H5AC(0.1039) H6A(-0.0249) H7AA(-
 0.1324) H7AB(-0.0533) H7AC(-0.0722) H8AA(0.1114) H8AB(0.1253) H8AC(0.088)
 H1C(0.6346) H2C(0.6191) H1D(0.0932) H2D(0.1505) H2(0.1067) H8(0.1641)
;
_shelx_res_checksum              17606
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'