#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:27:03 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180435 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/04/7210451.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_7210451
loop_
_publ_author_name
'Deadman, Benjamin J.'
'Battilocchio, Claudio'
'Sliwinski, Eric'
'Ley, Steven V.'
_publ_section_title
;
 A prototype device for evaporation in batch and flow chemical processes
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              2050
_journal_paper_doi               10.1039/c3gc40967h
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C8 H6 Cl N O2'
_chemical_formula_sum            'C8 H6 Cl N O2'
_chemical_formula_weight         183.59
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.452(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3073(3)
_cell_length_b                   7.1368(3)
_cell_length_c                   15.6263(7)
_cell_measurement_reflns_used    4702
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.00
_cell_volume                     814.66(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5569
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         3.99
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.968
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0831P)²+0.3534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1594
_reflns_number_gt                1917
_reflns_number_total             2309
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3gc40967h.txt
_cod_data_source_block           sl1305
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7210451
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.57167(7) 0.04497(8) 0.66361(3) 0.0472(2) Uani 1 1 d .
C1 C 0.6495(2) 0.2343(3) 0.60364(11) 0.0347(4) Uani 1 1 d .
C2 C 0.6875(3) 0.4016(3) 0.64380(12) 0.0403(4) Uani 1 1 d .
H2 H 0.6726 0.4147 0.7037 0.048 Uiso 1 1 calc R
C3 C 0.7477(3) 0.5502(3) 0.59554(13) 0.0403(4) Uani 1 1 d .
H3 H 0.7760 0.6659 0.6229 0.048 Uiso 1 1 calc R
C4 C 0.7677(2) 0.5340(3) 0.50726(12) 0.0346(4) Uani 1 1 d .
C5 C 0.7285(3) 0.3604(3) 0.46814(11) 0.0365(4) Uani 1 1 d .
H5 H 0.7419 0.3464 0.4082 0.044 Uiso 1 1 calc R
C6 C 0.6707(2) 0.2100(3) 0.51635(11) 0.0366(4) Uani 1 1 d .
H6 H 0.6459 0.0923 0.4902 0.044 Uiso 1 1 calc R
C7 C 0.8305(2) 0.6971(3) 0.45918(13) 0.0380(4) Uani 1 1 d .
H7 H 0.8720 0.8033 0.4907 0.046 Uiso 1 1 calc R
C8 C 0.8330(3) 0.7060(3) 0.37497(13) 0.0428(4) Uani 1 1 d .
H8 H 0.7916 0.6023 0.3416 0.051 Uiso 1 1 calc R
N1 N 0.8993(2) 0.8750(3) 0.33261(12) 0.0456(4) Uani 1 1 d .
O1 O 0.8948(3) 0.8656(3) 0.25381(11) 0.0652(5) Uani 1 1 d .
O2 O 0.9513(3) 1.0099(3) 0.37322(13) 0.0580(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0452(3) 0.0534(3) 0.0430(3) 0.0167(2) 0.0001(2) 0.0019(2)
C1 0.0289(8) 0.0427(9) 0.0323(8) 0.0063(7) -0.0015(6) 0.0043(7)
C2 0.0405(9) 0.0481(11) 0.0322(8) -0.0040(8) -0.0001(7) 0.0093(8)
C3 0.0408(10) 0.0379(10) 0.0420(10) -0.0068(7) -0.0021(7) 0.0073(8)
C4 0.0284(8) 0.0360(9) 0.0392(9) 0.0039(7) -0.0007(6) 0.0057(7)
C5 0.0388(9) 0.0410(10) 0.0297(8) 0.0011(7) 0.0009(7) 0.0025(7)
C6 0.0392(9) 0.0366(9) 0.0337(8) -0.0005(7) -0.0028(7) -0.0005(7)
C7 0.0339(9) 0.0377(9) 0.0424(9) 0.0025(7) -0.0001(7) 0.0058(7)
C8 0.0403(10) 0.0439(11) 0.0444(10) 0.0046(8) 0.0023(8) 0.0017(8)
N1 0.0387(8) 0.0503(10) 0.0482(9) 0.0124(8) 0.0089(7) 0.0065(8)
O1 0.0792(12) 0.0701(12) 0.0469(9) 0.0140(8) 0.0118(8) -0.0079(10)
O2 0.0609(10) 0.0452(9) 0.0682(11) 0.0029(8) 0.0063(8) 0.0015(8)
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 122.10(18)
C2 C1 Cl1 119.46(14)
C6 C1 Cl1 118.44(15)
C1 C2 C3 118.82(17)
C1 C2 H2 120.6
C3 C2 H2 120.6
C2 C3 C4 121.26(18)
C2 C3 H3 119.4
C4 C3 H3 119.4
C3 C4 C5 118.50(17)
C3 C4 C7 118.87(18)
C5 C4 C7 122.63(17)
C6 C5 C4 120.52(16)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 118.78(18)
C5 C6 H6 120.6
C1 C6 H6 120.6
C8 C7 C4 124.2(2)
C8 C7 H7 117.9
C4 C7 H7 117.9
C7 C8 N1 120.3(2)
C7 C8 H8 119.9
N1 C8 H8 119.9
O2 N1 O1 124.6(2)
O2 N1 C8 121.47(19)
O1 N1 C8 113.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.748(2)
C1 C2 1.374(3)
C1 C6 1.388(2)
C2 C3 1.380(3)
C2 H2 0.9500
C3 C4 1.396(3)
C3 H3 0.9500
C4 C5 1.407(3)
C4 C7 1.465(3)
C5 C6 1.384(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.318(3)
C7 H7 0.9500
C8 N1 1.465(3)
C8 H8 0.9500
N1 O2 1.209(3)
N1 O1 1.233(2)
